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(12) United States Patent (10) Patent No.: US 7,183,010 B2 Jarikov (45) Date of Patent: Feb. 27, 2007

(54) ORGANIC LIGHT-EMITTING DIODE (58) Field of Classification Search ...... 428/690, DEVICES WITH IMPROVED OPERATIONAL 428/917; 313/504,506 STABILITY See application file for complete search history. (75) Inventor: Viktor V. Jarikov, Rochester, NY (US) (56) References Cited (73) Assignee: Eastman Kodak Corporation, U.S. PATENT DOCUMENTS Rochester, NY (US) 5,281,489 A * 1/1994 Mori et al...... 428,690 5,294.870 A * 3/1994 Tang et al...... 313,504 (*) Notice: Subject to any disclaimer, the term of this 5,405,709 A * 4/1995 Littman et al...... 428,690 patent is extended or adjusted under 35 6,740,429 B2 * 5/2004 Aziz et al...... 428,690 U.S.C. 154(b) by 58 days. 2004/0021415 A1* 2/2004 Vong et al...... 313,509 (21) Appl. No.: 10/634,324 * cited by examiner Primary Examiner Dawn Garrett (22) Filed: Aug. 5, 2003 (74) Attorney, Agent, or Firm—Raymond L. Owens (65) Prior Publication Data (57) ABSTRACT US 2004/0076853 A1 Apr. 22, 2004 An organic light-emitting device includes a Substrate, an Related U.S. Application Data anode and a cathode disposed over the Substrate, and a (63) Continuation-in-part of application No. 10/131,801, luminescent layer disposed between the anode and the filed on Apr. 24, 2002, now abandoned. cathode wherein the luminescent layer includes a host and at least one dopant. The host of the luminescent layer is (51) Int. Cl. selected to include a solid organic material comprising a H05B 33/14 (2006.01) mixture of at least two components, one of which is capable HOIL 5L/50 (2006.01) of forming both monomer State and an aggregate state. (52) U.S. Cl...... 428/690: 428/917; 313/504; 313/506 108 Claims, 8 Drawing Sheets

VOLTAGE/ 33O CURRENT SOURCE U.S. Patent Feb. 27, 2007 Sheet 1 of 8 US 7,183,010 B2

VOLTAGE/ CURRENT SOURCE

VOLTAGE/ CURRENT SOURCE

VOLTAGE/ CURRENT 33O SOURCE

U.S. Patent Feb. 27, 2007 Sheet 4 of 8 US 7,183,010 B2

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4OO 45O 5OO 55O 6OO 65O 7OO WAVELENGTH, nr. FIG 16 US 7,183,010 B2 1. 2 ORGANIC LIGHT-EMITTING DODE emitting host. They showed that a blue emitting OLED DEVICES WITH IMPROVED OPERATIONAL device with an improved operational stability was obtained. STABILITY In both disclosures, the incorporation of selected fluorescent dopants in the luminescent layer is found to improve Sub CROSS REFERENCE TO RELATED stantially the overall OLED device performance parameters. APPLICATIONS Co-doping of luminescent layer with anthracene derivatives results in devices with better stability as shown in JP This is a continuation-in-part of application Ser. No. 99273861 and JP 284.050. Doping the hole-transport layer 10/131,801, filed Apr. 24, 2002 now abandoned entitled with materials that impede hole-transport and co-doping “Organic Light-emitting Diode Devices With Improved 10 hole-transport materials into electron-transporting AlQ Operational Stability” by Viktor V. Jarikov. leads to the improved device lifetimes, Popovic et al. Thin Solid Films 2000, 363, 6: SPIE 1998, 3476, 68. FIELD OF THE INVENTION The most common formulation of the doped luminescent layer includes only a single dopant in a host matrix. How The present invention relates to organic light-emitting 15 ever, in a few instances, incorporation of more than one diode devices and more particularly to the design of the dopant in the luminescent layer was found to be beneficial composition of the organic layers for improvements in in improving stability. Using a luminescent layer containing operational stability. rubrene, a yellow emitting dopant, and DCJ, 4-(dicyanom ethylene)-2-methyl-6-2-(4-julolidyl)ethenyl]-4H-pyran, a BACKGROUND OF THE INVENTION red emitting dopant, in an AlQ host it is possible to produce a red emitting OLED device with improved operational Organic light-emitting diodes (OLED), also known as stability, Hamada et al. in Applied Phys. Lett. 75, 1682 organic electroluminescent (EL) devices, are a class of (1999); EP1162674. Here rubrene functions as a co-dopant electronic devices that emit light in response to an electrical in mediating energy transfer from the AlQ host to the DCJ current applied to the device. The structure of an OLED 25 emitter. Generally, in dual dopant systems, it has been noted device generally includes an anode, an organic EL medium, that the operational stability tends to increase compared to and a cathode. The term, organic EL medium, herein refers that of the single dopant systems. to organic materials or layers of organic materials disposed Although EL efficiency, color, and stability have been between the anode and the cathode in the OLED device. The improved significantly using doped luminescent layers of organic EL medium can include low molecular weight 30 various compositions, the problem of low operational sta compounds, high molecular weight polymers, oligimers of bility persists. Insufficient stability presents the greatest low molecular weight compounds, or biomaterials, in the obstacle for many desirable practical applications. form of a thin film or a bulk solid. The medium can be amorphous or crystalline. Organic electroluminescent media SUMMARY OF THE INVENTION of various structures have been described in the prior art. 35 Dresner, in RCA Review, 30, 322 (1969), described a It is an object of the present invention to provide OLED medium comprising a single layer of anthracene film. Tang devices with improved operational stability. et al., in Applied Physics Letters, 51,913 (1987), Journal of It is another object of the present invention to provide Applied Physics, 65, 3610 (1989), and commonly assigned OLED devices with improved luminance efficiency. U.S. Pat. No. 4,769,292, reported an EL medium with a 40 It is another object of the present invention to provide a multi-layer structure of organic thin films, and demonstrated color OLED device with improved color chromaticity. highly efficient OLED devices using such a medium. In It is a further object of the present invention to provide some OLED device structures the multi-layer EL medium specifically OLED devices with improved operational sta includes a hole-transport layer adjacent to the anode, an bility, luminance efficiency, and chromaticity. electron-transport layer adjacent to the cathode, and dis 45 These objects are achieved in an organic light-emitting posed in between these two layers, a luminescent layer. device comprising a Substrate, an anode and a cathode Furthermore, in some preferred device structures, the lumi disposed over the Substrate, and a luminescent layer dis nescent layer is constructed of a doped organic film com posed between the anode and the cathode wherein the prising an organic material as the host and a small concen luminescent layer includes a host and at least one dopant, the tration of a fluorescent compound as the dopant. 50 host of the luminescent layer is selected to include a solid Improvements in EL efficiency, chromaticity, and Stability organic material comprising a mixture of at least two com have been obtained in these doped OLED devices by select ponents, one of which is capable of forming both monomer ing an appropriate dopant-host composition. The dopant, State and an aggregate state. being the dominant emissive center, is selected to produce These objects are further achieved in an organic light the desirable EL colors. Examples of the doped luminescent 55 emitting device, comprising: layer reported by Tang et al. in commonly assigned U.S. Pat. a) a Substrate; No. 4,769,292 and by Chen et al. in commonly assigned U.S. b) an anode and a cathode disposed over the Substrate; Pat. No. 5,908,581 are: tris(8-quinolinol)aluminum (AlO) c) aluminescent layer disposed between the anode and the host doped with coumarin dyes for green emitting OLEDs; cathode wherein the luminescent layer includes a host and AlQ doped with 4-dicyanomethylene-4H-pyrans 60 and at least one dopant; (DCMs) for orange-red emitting OLEDs. Shi et al., in d) the host of the luminescent layer being selected to commonly assigned U.S. Pat. No. 5,593,788, disclosed that include a solid organic material comprising a mixture a long operational life was obtained in an OLED device by of at least two components wherein: using a quinacridone compound as the dopant in an AlQ i) the first component of the mixture is an organic host. Bryan et al., in commonly assigned U.S. Pat. No. 65 compound that is capable of transporting either elec 5,141,671, disclosed a luminescent layer containing trons or holes or both and is capable of forming both perylene or a perylene derivative as a dopant in a blue monomer State and an aggregate state and further is US 7,183,010 B2 3 4 capable of forming the aggregate State either in the FIG. 12 shows electroluminescence spectra of an OLED ground electronic state or in the excited electronic device where the light-emitting layer is composed of coro state that results in a different absorption or emission nene and TBADN; current density is 20 mA/cm; spectrum or both relative to the absorption or emis FIG. 13 shows electroluminescence spectra of an OLED sion spectrum or both of the monomer State, respec- 5 device where the light-emitting layer is composed of deca tively, or the first component of the mixture is cyclene and AlQa; current density is 20 mA/cm; capable of forming the aggregate state whose pres FIG. 14 shows electroluminescence spectra of an OLED ence results in a quantum yield of luminescence of device where the light-emitting layer is composed of the monomer state being different relative to the dibenzob.defchrysene and TBADN; current density is 20 quantum yield of luminescence of the monomer state 10 mA/cm; in the absence of the aggregate state, and FIG. 15 shows electroluminescence spectra of an OLED ii) the second component of the mixture is an organic device where the light-emitting layer is composed of pero compound that upon mixing with the first host com ponent is capable of forming a continuous and Sub pyrene and TBADN; current density is 20 mA/cm; and stantially pin-hole-free layer; and 15 FIG. 16 shows electroluminescence spectra of an OLED e) the dopant of the luminescent layer being selected to device where the light-emitting layer is composed of produce light from the light-emitting device. perylene and TBADN; current density is 20 mA/cm. Another advantage of the present invention is that it provides OLED devices with high operational stability, DETAILED DESCRIPTION OF THE lower drive Voltage, excellent luminance efficiency and INVENTION color chromaticity, and with luminance efficiency and color chromaticity essentially independent of the current density. FIG. 1 illustrates the structure of an OLED device of the Another advantage of the present invention is that it simplest construction practiced in the present invention. In provides OLED devices that are suitable for high-brightness this structure, OLED device 100 includes an anode 120, an and long-lifetime lighting and display applications. 25 EL medium 130, and a cathode 140, disposed upon a Substrate 110. In operation, an electrical current is passed BRIEF DESCRIPTION OF THE DRAWINGS through the OLED by connecting an external current or voltage source with electrical conductors 10 to the anode The drawings are necessarily of a schematic nature, since and the cathode, causing light to be emitted from the EL the individual layers are too thin and the thickness differ 30 medium. The light can exit through either the anode or the ences of the various elements too great to permit depiction cathode or both as desired and depending on their optical to scale or to permit convenient proportionate scaling. transparencies. The EL medium includes a single layer or a FIG. 1 is schematic structure of an OLED with an organic multi-layer of organic materials. EL medium; FIG. 2 illustrates the structure of another OLED device of FIG. 2 and FIG. 3 are two schematic OLED structures 35 the present invention. In this structure, OLED device 200 showing two different configurations of the organic EL includes a substrate 210 and an EL medium 230, disposed medium; between anode 220 and cathode 240. EL medium 230 FIG. 4 shows photoluminescence spectra of an OLED includes a hole-transport layer 231 adjacent to the anode, an device where the light-emitting layer is composed of naph electron-transport layer 233 adjacent to the cathode, and a tho2,3-alpyrene and AlQ, excitation wavelength is 430 40 luminescent layer 232 disposed between the hole-transport nm, layer and the electron-transport layer. In operation, an elec FIG. 5 shows photoluminescence spectra of the same trical current is passed through the OLED device by con OLED device where the light-emitting layer is composed of necting an external current or Voltage source with electrical naphtho2,3-alpyrene and AlQ; excitation wavelength is conductors 10 to the anode and the cathode. This electrical 470 nm, 45 current, passing through the EL medium, causes light to be FIG. 6 shows electroluminescence spectra of the same emitted primarily from the luminescent layer 232. Hole OLED device where the light-emitting layer is composed of transport layer 231 carries the holes, that is, positive elec naphtho2,3-alpyrene and AlQ; current density is 20 tronic charge carriers, from the anode to the luminescent mA/cm; layer. Electron-transport layer 233 carries the electrons, that FIG. 7 shows electroluminescence spectra of an OLED 50 is, negative electronic charge carriers, from the cathode to device where the light-emitting layer is composed of naph the luminescent layer 232. The recombination of holes and tho2,3-alpyrene and TBADN; current density is 20 electrons produces light emission, that is, electrolumines mA/cm; cence, from the luminescent layer 232. FIG. 8 shows electroluminescence spectra of an OLED FIG.3 illustrates yet another structure of an OLED device device where the light-emitting layer is composed of 55 of the present invention. In this structure, OLED device 300 dibenzob.kperylene and AlQ; current density is 20 includes a substrate 310 and an EL medium 330 disposed mA/cm; between anode 320 and cathode 340. EL medium 330 FIG. 9 shows electroluminescence spectra of an OLED includes a hole-injection layer 331, a hole-transport layer device where the light-emitting layer is composed of 332, a luminescent layer 333, an electron-transport layer dibenzob.kperylene and TBADN; current density is 20 60 334, and an electron-injection layer 335. Similarly to OLED mA/cm; device 200 of FIG. 2, the recombination of electrons and FIG. 10 shows electroluminescence spectra of an OLED holes produces emission primarily from the luminescent device where the light-emitting layer is composed of benzo layer 333. The provision of the hole-injection layer 331 and alpyrene and TBADN; current density is 20 mA/cm; the electron-injection layer 335 serves to reduce the barriers FIG. 11 shows electroluminescence spectra of an OLED 65 for carrier injection from the respective electrodes. Conse device where the light-emitting layer is composed of benzo quently, the drive voltage required for the OLED device can Ighilperylene and TBADN; current density is 20 mA/cm; be reduced. US 7,183,010 B2 5 6 FIG. 4 shows representative absolute photoluminescence are composed of the emission spectrum of benzoapyrene in (PL) spectra of an OLED device where the light-emitting its aggregate state and the emission spectrum of TBADN. layer is composed of naphtho2,3-alpyrene and AlQ. It can FIG. 11 shows the absolute EL spectra of an OLED device be seen that the higher the volume '% of naphtho2.3-a where the light-emitting layer is composed of benzoghi pyrene in the layer the more emission spectrum is shifted to perylene and TBADN. The EL spectra signal that formation the red. This signals formation of the aggregate state the of an aggregate state of benzoghilperylene occurs. With concentration of which and the average size of which increasing concentration of benzoghilperylene the aggre increases with increasing Volume 96 of naphtho2.3alpyrene. gate contribution to the overall EL increases. The EL spectra The excitation wavelength is 430 nm and thus both AlQ and are composed primarily of the emission spectrum of benzo naphtho2,3-alpyrene are excited resulting in an emission 10 Ighilperylene in its aggregate state with some contribution spectrum composed of the photoluminescence of both AlQ of the monomer state emission and possibly little emission and naphtho2,3-alpyrene, the latter being in the monomer of TBADN. state or the aggregate state or both. FIG. 12 shows the absolute EL spectra of an OLED device FIG. 5 shows representative absolute photoluminescence where the light-emitting layer is composed of coronene and (PL) spectra of the OLED device of FIG. 4 obtained with the 15 TBADN. The EL spectra signal that formation of an aggre excitation wavelength of 470 nm. Here primarily naphtho gate state of coronene occurs. With increasing concentration 2,3-alpyrene is excited resulting in an emission spectrum of coronene the aggregate contribution to the overall EL composed almost exclusively of the photoluminescence of increases. The EL spectra are composed primarily of the naphtho2.3alpyrene in its monomer state or aggregate State emission spectrum of coronene in its aggregate state with or both. some contribution of the emission of TBADN. FIG. 6 shows the corresponding absolute electrolumines FIG. 13 shows the absolute EL spectra of an OLED device cence (EL) spectra of the OLED device of FIG. 4 and FIG. where the light-emitting layer is composed of decacyclene 5. It can be seen that the EL spectra resemble the PL spectra and AlQ. The EL spectra signal that formation of an of FIG. 4 closely. This signals that the singlet excites states aggregate State of decacyclene occurs. With increasing con of both AlQ and naphtho2,3-alpyrene are produced in an 25 centration of decacyclene the aggregate contribution to the operating device. Thus, the EL spectrum is composed of the overall EL increases. The EL spectra are composed prima luminescence of both AlQ and naphtho2,3-alpyrene, the rily of the emission spectrum of decacyclene in its aggregate latter being in its monomer State or aggregate state or both state with some contribution of the emission of AlQ. depending on the Volume '% of naphtho2,3-alpyrene in the FIG. 14 shows the absolute EL spectra of an OLED device luminescent layer. 30 where the light-emitting layer is composed of dibenzob. FIG. 7 shows the absolute EL spectra of an OLED device defchrysene and TBADN. The EL spectra signal that for where the light-emitting layer is composed of naphtho2.3- mation of an aggregate state of dibenzob.defchrysene apyrene and TBADN. It can be seen that the EL spectra occurs. With increasing concentration of dibenzob.def behave similarly to those of FIG. 6. This signals that chrysene the aggregate contribution to the overall EL dras formation of an aggregate state of naphtho2,3-alpyrene 35 tically increases. The EL spectra are composed of the occurs in a nonpolar TBADN environment as well as in emission spectrum of dibenzob.defchrysene in its mono polar AlQ environment. With increasing concentration of mer state and the emission of its aggregate state. naphtho2,3-alpyrene the aggregate contribution to the over FIG. 15 shows the absolute EL spectra of an OLED device all EL drastically increases. Thus, the EL spectrum is where the light-emitting layer is composed of peropyrene composed primarily of the emission spectrum of naphtho2. 40 (dibenzocci.lmperylene) and TBADN. The EL spectra sig 3-alpyrene in its monomer state in the 2% case, while in the nal that formation of an aggregate State of peropyrene 20% case the emission is almost solely that of naphtho2. occurs. With increasing concentration of peropyrene the 3-alpyrene in its aggregate state. aggregate contribution to the overall EL drastically FIG. 8 shows the absolute EL spectra of an OLED device increases. The EL spectra are composed primarily of the where the light-emitting layer is composed of dibenzob.k 45 emission spectrum of peropyrene in its aggregate state. perylene and AlQ. It can be seen that the EL spectra signal FIG.16 shows the absolute EL spectra of an OLED device major involvement of an aggregate State of dibenzob.k where the light-emitting layer is composed of perylene and perylene in EL production. Thus, the EL spectrum is com TBADN. The EL spectra signal that formation of an aggre posed primarily of the emission spectrum of dibenzob.k gate state of perylene occurs. With increasing concentration perylene in its aggregate state while a small portion of EL 50 of perylene the aggregate contribution to the overall EL comes from the emission of AlQ. drastically increases. The EL spectra are composed prima FIG.9 shows the absolute EL spectra of an OLED device rily of the emission spectrum of perylene in its aggregate where the light-emitting layer is composed of dibenzob.k State. perylene and TBADN. The EL spectra signal that formation According to the present invention, the luminescent layer of an aggregate state of dibenzob.kperylene occurs in a 55 (either layer 232 of FIG. 2 or layer 333 of FIG. 3) is nonpolar TBADN environment as well as in polar AlQ primarily responsible for the electroluminescence emitted environment. With increasing concentration of dibenzob.k from the OLED device. One of the most commonly used perylene the aggregate contribution to the overall EL dras formulations for this luminescent layer is an organic thin tically increases. Thus, the EL spectrum is composed pri film including a host and one or more dopants. The host marily of the emission spectrum of dibenzob.kperylene in 60 serves as the Solid medium or matrix for the transport and its monomer state in the 0.5% case, while in the 8% case the recombination of charge carriers injected from the anode emission is almost solely that of dibenzob.kperylene in its and the cathode. The dopant, usually homogeneously dis aggregate State. tributed in the host in Small quantity, provides the emission FIG. 10 shows the absolute EL spectra of an OLED device centers where light is generated. Following the teaching of where the light-emitting layer is composed of benzoa 65 the prior art, the present invention uses a luminescent layer pyrene and TBADN. The EL spectra signal that formation of including a host and a dopant, but it distinguishes over the an aggregate state of benzoapyrene occurs. The EL specra prior art that the host of the present invention is a mixture US 7,183,010 B2 7 8 having at least two components, each component having molecule, or one having a flat and rigid part, has a propensity specific electronic properties. The selection of these host to undergo aggregation and form an aggregate state and as components and compatible dopant materials is in accor such is included in the list of preferred materials for the first dance with the following criteria: host component of the luminescent layer of this invention. 1. The host is a Solid organic thin film comprising a Possible exceptions include compounds that undergo known mixture of at least two components; unfavorable chemical reactions either thermally, photo 2. The first component of the mixture is an organic chemically, or upon electrochemical oxidation or reduction compound that is capable of transporting either electrons or in an OLED device. For example, 1,3-diphenylisobenzofu holes or both; ran readily undergoes Diels-Alder reactions as well as 3. The first component of the mixture is capable of 10 rearrangement and condensation reactions; truXenes, fluo forming both monomer state and an aggregate state; renes, and other compounds having Aryl-CH2-Aryl' or Aryl 4. The first component of the mixture is capable of CH(Aryl")-Aryl' bridges have labile hydrogen atoms; esters forming the aggregate state either in the ground electronic undergo dissociation and decarboxylation reactions, alco state or in the excited electronic state; hols and acids undergo deprotonation, etc. Another example 5. The first component of the mixture is capable of 15 of an exception that depends on the nature of the use of the forming the aggregate state that results in a different absorp material in an OLED device can include certain heterocyclic tion or emission spectrum or both relative to the absorption molecules such as imidazoles, triazoles, oxadiazoles, or emission spectrum or both of the monomer state, respec pyridines, phenanthrolines, and others which are known to tively (the aggregate state can emit or absorb or both to the undergo certain chemical transformations in an OLED red or to the blue of the emission or absorption spectrum or device upon their electrochemical oxidation (hole injection) both of the monomer state, respectively): that leads to short operational lifetimes. Another example of 6. The first component of the mixture is capable of possible exception includes molecules containing chloro-, forming the aggregate state whose presence results in a bromo-, or iodo-Substituents which upon electrochemical quantum yield of luminescence of the monomer State being oxidation or reduction undergo possible cleavage or disso different relative to the quantum yield of luminescence of the 25 ciation reactions that lead to short operational stabilities of monomer state in the absence of the aggregate states (the an OLED device. Benzenoid and heterocyclic compounds quantum yield of luminescence for the monomer state can be absorbing light in the UV, near UV, and visible region up to either enhanced or reduced); 450 nm are preferred materials for the first host component 7. The second component of the mixture is an organic of a blue-emitting OLED device and blue layer of a white compound that upon mixing with the first host component is 30 emitting OLED device. Benzenoid and heterocyclic com capable of forming a continuous and Substantially pin-hole pounds absorbing light in the UV, near UV, and visible free layer; region up to 490 nm are preferred materials for the first host 8. The dopant is an organic luminescent compound component of a blue-green-emitting OLED device and blue capable of accepting the energy released from the recombi green layer of a white-emitting OLED device. Benzenoid nation of electrons and holes in either the first or second host 35 and heterocyclic compounds absorbing light in the UV, near components, and emitting the energy as light. UV, and visible region up to 520 nm are preferred materials Following the selection criteria of this invention, OLED for the first host component of a green-emitting OLED devices have been constructed having excellent operational device and green layer of a white-emitting OLED device. stability. Importantly, for red devices the luminance effi Benzenoid and heterocyclic compounds absorbing light in ciency measured in candelas per ampere significantly 40 the UV, near UV, and visible region up to 580 nm are increases, compared to the system without the first compo preferred materials for the first host component of a yellow nent, and remains constant over a large range of brightness orange-emitting OLED device and yellow-orange layer of a or current densities. In addition, the color chromaticity is white-emitting OLED device. Benzenoid and heterocyclic greatly improved and the drive Voltage is reduced. This is a compounds absorbing light in the UV, near UV, and visible distinct advantage over the prior art, where such operational 45 region up to 630 nm are preferred materials for the first host stability improvements over comparative examples com component of a red-emitting OLED device and red layer of bined with such long lifetimes have never been demon a white-emitting OLED device. strated, the luminance efficiency often decreases, or other The list of simple PAH useful as building blocks and wise varies, with increasing brightness or current density, parent structures for benzenoid compounds or derivatives color chromaticity is often compromised, and drive Voltage 50 thereof includes: often increases. Another important advantage is that the 1. Benzene chromaticity also remains essentially constant, independent 2. Naphthalene of the brightness or current density. Thus, the problem of . Phenanthrene color shift with brightness in an OLED device is also . Chrysene eliminated. 55 . Anthracene Preferred materials for the first host component of the . Naphthacene luminescent layer of this invention include a class of com . Pentacene pounds which, for the purpose of this invention, will be . Hexacene referred to as benzenoid compounds and N—, O— Si . Heptacene B-, P , and S-atom containing heterocyclic compounds. 60 10. Pyrene The benzenoid compounds comprise polycyclic hydrocar 11. Perylene bons (PAH), combinations of two or more PAH which are 12. BenZoghilperylene chemically linked, and combinations of two or more PAH 13. Benzoaperylene which are not chemically linked. Non-benzenoid aromatic 14. Benzo(bperylene hydrocarbons such as aZulene and its derivatives are 65 15. Coronene included in the list of preferred materials for the first host 16. Fluoranthene component also. Essentially any more or less flat and rigid 17. Fluorene US 7,183,010 B2 10 18. Tetraphene 83. Quinoline 19. Pentaphene 84. Isoquinoline 20. Hexaphene 85. Cinnoline 21. Aceanthrylene 86. Quinazoline 22. Acepyrene 87. 1,8-Naphthyridine 23. Aceperylene 88. 1,7-Naphthyridine 24. Anthanthrene 89. 1,6-Naphthyridine 25. Indene 90. 1.5-Naphthyridine 26. Triphenylene 91. Benzoxazine 27. Biphenyl 10 92. Carbazole 28. Terphenyl 93. Xanthene 29. Quarterphenyl 94. Acridine 30. Quinqephenyl 95. Purine 31. Sexiphenyl 96. Dibenzof,hquinoline (1-Azatriphenylene) 32. Binaphthyl 15 97. Dibenzof,hquinoxaline (1,4-Diazatriphenylene) 33. Picene 98. Phenanthridine 34. Pyranthrene 99. 1,7-Phenanthroline 35. Bisanthrene (bisanthene) 36. Ovalene 100. 1,10-Phenanthroline 37. Peropyrene 101. 4.7-Phenanthroline 38. Triptycene 102. Phenazine 39. Phenalene The list of preferred benzenoid compounds or alkyl, The list of simple heterocycles useful as building blocks alkenyl, alkynyl, aryl, Substituted aryl, silyl, ace, indeno, for heterocyclic compounds or derivatives thereof includes: 1.2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-an 40. Pyrrole 25 thraceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP. 41. Pyrazole 1,12-Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1,2- 42. Imidazole PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2- 43. 1,2,3-Triazole FlAn, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. 44. 1,2,4-Triazole 45. 1,2-Dithiole 30 46. 1,3-Dithiole 47. 12-Oxathiole 48. Isoxazole 49. Oxazole 50. Thiazole 35 51. Isothiazole 52. 1,2,4-Oxadiazole 2,2'-BP, 4,5-PhAn, 53. 1,2,5-Oxadiazole 54. 1,3,4-Oxadiazole 55. 1,2,3,4-Oxatriazole 40 56. 1,2,3,5-Oxatriazole 57. 1,2,3-Dioxazole 58. 1,2,4-Dioxazole 59. 1,3,2-Dioxazole 60. 1,3,4-Dioxazole 45 61. 1,2,5-Oxathiazole 62. 1,3-Oxathiole 63. Pyridine 1,12-TriP, 1,12-Per 64. Pyridazine 65. Pyrimidine 50 66. Pyrazine 67. 1,3,5-Triazine 68. 1,2,4-Triazine 69. 1,2,3-Triazine 70. Furan 55 1.9-An, 71. Dibenzofuran 9,10-PhAn, 72. Benzofuran 73. Isobenzofuran 74. Thiophene 75. Dibenzothiophene 60 76. Benzobthiophene 77. Benzocthiophene 78. Indole 79. Pyrano3,4-bipyrrole 80. Indazole 65 1,10-PhAn, 81. Indoxazine 82. Benzoxazole US 7,183,010 B2 12

-continued -continued 5 ( . ) ( )

10

1.2-PhAn, 1,10-Pyr, 2,3-TriP, 12-TriP

15 (where bonds that do not form a cycle indicate points of attachment), fluoro, cyano, alkoxy, aryloxy, amino, aza, OXo, thia, heterocyclic, keto, and dicyanomethyl derivatives thereof as materials for the first host component of the luminescent layer of this invention includes: 103. Picene 104. BenZoalanthracene 105. BenZoghilperylene 106. BenZoapyrene 107. Benzoepyrene 1,2-Pyr, 25 2,3-Per, 108. Benzoanaphthacene 109. Naphtho2,3-alpyrene 110. Naphtho2,3-epyrene 111. Rubicene 112. Anthanthrene 30 113. Fluoranthene 114. BenZoacoronene 115. Dibenzob.defchrysene 116. Naphtho2,3-acoronene 117. Dibenzoca limperylene 35 118. BenZoghi naphthocaelperylene 119. Benzob.perylene 120. BenZoapentacene 121. Benzoaperylene 3,4-FAn, 2.3-FAn, 122. Naphtho8,1,2-bcdperylene 40 123. Dibenzob.kperylene 124. Dibenzob.nperylene 125. Naphtho1,2-alpyrene 126. Naphtho1.2-epyrene 127. BenZorstpentaphene 45 128. Dibenzo defpchrysene 129. Dibenzofg.opnaphthacene 130. Dibenzohrstipentaphene 131. Terrylene 132. Aceanthrylene 50 133. Acenaphth 1.2-alanthracene 134. Acenaphth 1.2-blanthracene 1,2-F1An, 3,4-Per, 135. Acenaphthalene 136. Acenaphthene 137. Acenaphtho1.2.3-cdelpyrene 55 138. Acenaphtho1.2-bphenanthrene 139. Acenaphtho1.2fluoranthene 140. Acenaphtho1.2-kicyclopentacdfluoranthene 141. Acenaphtho1.2-kfluoranthene 60 142. 13H-Acenaphtho1.8-abphenanthrene 143. Acenaphthylene 144. Aceperylene 145. Acephenanthrene 146. Acepyrene 7,8-F|An, 65 147. Acepyrylene 8.9-FIAn, 148. 6 Annulene 149. Anthanthrene US 7,183,010 B2 13 14 150 . Anthra 1.2.3,4-rstpentaphene 216. 1H-Benzfgaceanthrylene 151 . Anthra 1,2-alaceanthrylene 217. 5H-Benz fgacenaphthylene 152 . Anthra 1,2-alanthracene 218. 1OH-Benzgindeno2, 1-alphenanthrene 153 . Anthra 1,2-abenZanthracene 219. BenZiaceanthrylene 154 . Anthra 12-anaphthacene 220. BenZjacephenanthrylene 155 . Anthra 1,2-bphenanthrene 221. BenZklacephenanthrylene 156 ... Anthra 1.9.8-abcdbenzohicoronene 222. Benzlaceanthrylene 157. Anthra 2, 19.8-stuva benzoopnaphtho2,1,8.7-hijk 223. Benzlacephenanthrylene pentacene 224. BenZmnoaceanthrylene 158. Anthra 2, 1,9,8,7-defghibenzooplpentacene 10 225. Benzmnoindeno1,7,6,5-cdefchrysene 159. Anthra 2, 1,9,8,7-defghibenzo stipentacene 226. Benzmnoindeno5,6,7,1-defgchrysene 16O. Anthra 2, 1,9,8,7-defghibenzouvpentacene 227. 2,3-Benzanthracene 161. Anthra 2, 19.8-defgh benzorstpentaphene 228. 12:5,6-Benzanthracene 162. Anthra 2, 19.8-defghpentaphene 229. 1.2-BenZanthracene 163. Anthra2.19.8-opqranaphthacene 15 23O. 1.2-Benzanthrene 164. Anthra2.19.8-stuvapentacene 231. 1H-meso-Benzanthrene 165. Anthra2.1.9-qranaphthacene 232. Benzanthrene 166. Anthra2.1-alaceanthrylene 233. Benzanthreno-BZ-1.BZ-2:2.3-naphthalene 167. Anthra2.1-anaphthacene 234. 9,101',2'-Benzenoanthracene, 9,10-dihydro 168. Anthra 2,3-acoronene 235. 7,8-Benzfluoranthene 169. Anthra2.3-anaphthacene 236. 2,3-Benzidene 170. Anthra 3.2.1.9.8-rstuva benzoijpentaphene 237. 1,10-(peri)-Benzo-1,5-dihydropyrene 171. Anthra3.2.1.9-pdrabenzocaperylene 238. 2,3-Benzo-6,7-naphthoanthracene 172. Anthra7,8,9,1,2,3-rstuvwx hexaphene 239. 1.14-Benzobisanthene 173. Anthra8,9,1,2-cdefgbenzoanaphthacene 25 240. 1.14-Benzodinaphtho1'.7".24.7". 1", 11.13bisan 174. Anthra8,9,1,2-lmnoplbenzoanaphthacene thene 175. Anthra9,1,2-abccoronene 241. Benzo 1,2-a,3,4-a'.5,6-a"triacenaphthylene 176. Anthra 9.1.2-bcdperylene 242. BenZo 1.2-a,4,5-a'diacenaphthylene 177. Anthra 9.1.2-cdebenzorstpentaphene 243. Benzo.2.1-a:3,4-a'dianthracene 178. Anthra 9.1-bcfluorene 30 244. Benzo(3,4phenanthro2,1,10,9,8,7-pdrstuVpen 179. Anthracene taphene 18O. Anthraceno-1,2,1,2-anthracene 245. Benzo 6.7phenanthro4.3-bichrysene 181. Anthraceno.2.1-alanthracene 246. Benzoalanthanthrene 182. Anthrodianthrene 247. BenZoacoronene 183. 4.5-Benz-10.11-(1,2'-naphtha)chrysene 35 248. 1H-Benzoacyclopenthanthracene 184. Benz4.10anthra 1.9.8-abcdcoronene 249. 9H-Benzoacyclopentilanthracene 185. 15H-Benz4.5indeno 1.2-1 phenanthrene 250. BenZoacyclopentadelnaphthacene 186. 9H-Benz 4.5indeno.2.1-cphenanthrene 251. BenZoacyclopentafgnaphthacene 187. 7H-Benz 5.6 indeno1,2-alphenanthrene 252. BenZoacyclopentahilnaphthacene 188. Benz 5.6 indeno2,1-alphenalene 40 253. BenZoacyclopentamnnaphthacene 189. 7H-Benz 5.6 indeno2, 1-alphenanthrene 254. BenZoacyclopentalopnaphthacene 190. 9H-Benz 5.6 indeno.2.1-cphenanthrene 255. Benzoafluoranthene 191. BenZalaceanthrylene 256. 11H-Benzoafluorene 192. BenZalacenaphthylene 257. Benzoafluorene 193. BenZalacephenanthrylene 45 258. BenZoaheptacene 194. 12:5,6-Benzaanthracene 259. Benzoa hexacene 195. BenZaanthracene 26O. Benzoa hexaphene 196. Benzaindeno1,2-cfluorene 261. Benzoanaphth 2,1-anthracene 197. BenZaindeno.2.1-cnaphthalene 262. Benzoanaphthacene 198. Benzaindeno.5,6-gfluorene 50 263. Benzoanaphtho1.2.3,4-ghilperylene 199. Benzalovalene 264. Benzoanaphtho1.2-cnaphthacene 2OO. Benzbanthracene 265. Benzoanaphtho1.2-hlanthracene 2O1. Benz bindeno.2.1-hfluorene 266. Benzoanaphtho1.2-naphthacene 2O2. 11H-Benzbcaceanthrylene 267. Benzoanaphtho1.2-lnaphthacene 2O3. Benzcindeno2,1-afluorene 55 268. Benzoanaphtho2, 1,8-cdeperylene 204. Benzdaceanthrylene 269. Benzoanaphtho2, 1.8-hijnaphthacene 205. Benzdovalene 270. Benzoanaphtho2, 1.8-lmniperylene 2O6. 1H-Benz delanthracene 271. Benzoanaphtho2, 1-hpyrene 207. Benz delindeno2, 1-banthracene 272. Benzoanaphtho2.1-naphthacene 2O8. Benz defindeno1,2,3-hichrysene 60 273. Benzoanaphtho2.1-lnaphthacene 209. Benz defindeno 1.2.3-qrchrysene 274. Benzoanaphtho7.8.1.2.3-pdrstpentaphene 210. Benzelaceanthrylene 275. Benzoanaphtho8.1.2-cdenaphthacene 211. 3,4-Benzelacephenanthrylene 276. Benzoanaphtho8, 1.2-klimperylene 212. BenZeacephenanthrylene 277. Benzoanaphtho8.1.2-lmnnaphthacene 213. 3H-Benzeindene 65 278. BenZoapentacene 214 . 1H-Benzeindene 279. BenZoapentaphene 215 . 1H-Benz findene 28O. Benzoaperylene US 7,183,010 B2 15 16 281. Benzoaphenanthrene 348. Benzo defcyclopentaqrchrysene 282. Benzoapicene 349. Benzodeffluorene 283. Benzoapyranthrene 350. Benzo defphenanthrene 284. Benzoapyrene 351. Benzo defpyranthrene 285. Benzoblanthanthrene 352. Benzoelanthanthrene 286. Benzobichrysene 353. BenZoecyclopentajkpyrene 287. 5H-Benzobicyclopentadefchrysene 354. BenZoecyclopentajkpyrene 288. 13H-Benzobicyclopenta deftriphenylene 355. Benzoelfluoranthene 289. Benzobicyclopentahichrysene 356. BenZoephenanthro1,10,9,8-opqraperylene 29O. 4H-Benzobicyclopentajkltriphenylene 10 357. BenZoephenanthro2.3.4.5-pdrabperylene 291. 4H-Benzobicyclopentamnochrysene 358. Benzoepyrene 292. BenZobicyclopentaqrchrysene 359. Benzoefphenaleno 9,1,2-abccoronene 293. Benzobifluoranthene 360. BenZocphenanthrene 2.94. 11 H-Benzob fluorene 361. Benzofpentahelicene 295. Benzobnaphthacene 15 362. Benzofpicene 296. BenZobnaphtho1.2.3.4-pdrperylene 363. BenZofgcyclopentalanthracene 297. Benzobnaphtho1.2-kchrysene 364. BenZofgnaphtho1,2,3-opnaphthacene 298. Benzobnaphtho1.2-lchrysene 365. Benzo fghdinaphtho1,2,3,4-pdr: 1,2',3',4'-Zalblitri 299. BenZobnaphtho2.1-gchrysene naphthylene 3OO. Benzobnaphtho2.1-kchrysene 366. Benzogchrysene 301. Benzobnaphtho2,1-pchrysene 367. 8H-Benzogcyclopentamnochysene 3O2. BenZobnaphtho2.3-gchrysene 368. Benzognaphtho2.1-bichrysene 3O3. Benzobnaphtho2.3-chrysene 369. Benzognaphtho8,1,2-abccoronene 3O4. Benzobnaphtho2.3-lchrysene 370. BenZoghi cyclopentacdperylene 305. BenZobnaphtho8.1.2-pdr chrysene 25 371. 1H-BenZoghi cyclopentapqrperylene 306. Benzo(bpentahelicene 372. Benzoghifluoranthene 307. Benzo(bpentaphene 373. BenZoghinaphtho1.2-bperylene 3O8. Benzo(bperylene 374. BenZoghinaphtho2,1-aperylene 309. Benzo(bphenanthrene 375. BenZoghinaphtho2.1-bperylene 31 O. Benzo(bpicene 30 376. Benzoghinaphtho2", 1",8,7":5,6,7aceanthryleno.10, 3.11. Benzob triphenylene 1.2-abcdperylene (Circumanthracene) 312. Benzobcnaphtho1,2,3-efcoronene 377. Benzoghilperylene 313. Benzobcnaphtho3.2.1-efcoronene 378. BenZohnaphtho1.2.3,4-rstpentaphene 3.14. Benzocchrysene 379. BenZohnaphtho7.8.1.2.3-pdrstpentaphene 315. BenZoccyclopentahichrysene 35 380. BenZohpentaphene 316. 4H-Benzoccyclopentamnochrysene 381. Benzohphenanthro2,1,10,9,8,7-pdrstuvpentaphene 317. BenZoccyclopentaqrchrysene 382. 7H-Benzo[hichrysene 3.18. Benzocfluorene 383. 4H-Benzo[hichrysene 3.19. 7H-Benzocfluorene 384. Benzoilpentahelicene 32O. Benzochexaphene 40 385. Benzoijdinaphtho2, 1,8,7-defg:7",8,1,2',3'-pdrst 321. BenZocnaphtho1.2-1 chrysene pentaphene 322. BenZocnaphtho2.1-mipentaphene 386. Benzo inaphtho2.18.7-defgpentaphene 323. BenZocnaphtho2.1-pchrysene 387. Benzobenzo[2,1-a:3,4-adianthracene 324. Benzocinaphtho2.3-lchrysene 388. Benzo fluoranthene 325. BenZocnaphtho7.8.1.2.3-pdrstpentaphene 45 389. BenZonaphtho8,1,2-abccoronene 326. BenZocnaphtho8.1.2-ghichrysene 390. Benzokfluorene 327. BenZoenaphtho2,3-alpyrene 391. Benzokfluoranthene 328. Benzocpentahelicene 392. Benzoklnaphtho2, 1,8,7-defgpentaphene 3.29. BenZocpentaphene 393. BenZolicyclopentacdpyrene 330. Benzocphenanthrene 50 394. Benzollfluoranthene 331. BenZocpicene 395. BenzolnaphthoI 1.2-bichrysene 332. Benzoctetraphene 396. BenzolnaphthoI2,1-bichrysene 333. 1H-Benzocafluoranthene 397. Benzolphenanthrene 334. Benzocanaphtho3.2.1.8-pdraperylene 398. Benzolminaphtho1.8-abperylene 335. 6H-Benzoca pyrene 55 399. Benzolmphenanthro5.4.3-abcdperylene 336. 3H-Benzoca pyrene 400. BenZolmnnaphtho2, 1.8-qraperylene 337. 5H-Benzoca pyrene 4O1. Benzomdiphenanthro1, 10.9-abc:1'10'.9'-ghicoro 338. 2H-Benzoca pyrene 339. BenZodecyclopentalanthracene 402. BenZom naphtho8,1,2-abccoronene 340. Benzodecyclopent banthracene 60 403. Benzomnofluoranthene 341. BenZodenaphtho2, 1,8,7-qrstpentacene 404. BenZomnonaphtho1.2-cchrysene 342. BenZodenaphtho3.2.1-mnnaphthacene 405. BenZomnonaphtho2.1-cchrysene 343. Benzodenaphtho8,1,2,3-stuvpicene 406. Benzoohexaphene 344. 7H-Benzo depentacene 4O7. 8H-Benzopicyclopenta defchrysene 345. Benzo defchrysene 65 408. BenZophexaphene 346. Benzo defcyclopentahichrysene 409. Benzopnaphtho1.2-bichrysene 347. 4H-Benzo defcyclopentamnochrysene 410. Benzopnaphtho1,8.7-ghichrysene US 7,183,010 B2 17 18 411 . Benzopnaphtho2,1-bichrysene 476. 2,3:1',8-Binaphthylene 412. BenZopnaphtho8,1,2-abccoronene 477. 3,4-(o.o'-Biphenylene)cyclopentadiene 413. Benzopardinaphtho8, 1,2-bcd:2', 1.8-lmnip erylene 478. 3,4-(o-o'-Biphenylene)fluorene 414. BenZopqrnaphtho1.2-bperylene 479. o-Biphenylenemethane 415. BenZopqrnaphtho2, 1.8-deflpicene 480. Biphenylenephenanthrene 416. BenZopqrnaphtho2, 1-bperylene 481. o-Biphenylmethane 417. Benzoparnaphtho8,1,2-bcdperylene 482. Bisanthrene 418. BenZopqrnaphtho8, 1.2-cdepicene 483. Ceranthrene 419. BenZopqrpicene 484. homeo-Cerodianthrene 420. BenZoqhexaphene 10 485. Cholanthrene 421. BenZoqrnaphtho2, 18.7-defgpentacene 486. Cholanthrylene 422. BenZoqrnaphtho2, 18.7-fghilpentacene 487. Chrysene 423. BenZoqrnaphtho3.2.1.8-defgchrysene 488. Chryseno 2,1-bipicene 424. Benzoqrsnaphtho3.2.1.8,7-defghpyranthrene 489. Chrysofluorene 425. Benzors dinaphtho2, 18.7-klmn:3'2", 1",8,7'-Vw.xyz 15 490. Corannulene hexaphene 491. Coronene 426 . Benzorstdinaphtho8,1,2-cde:2.1".8-klm pentaphene 492. 1.2-Cyclo-delta 1',3'-pentadienophenanthrene 427 . BenZorstdinaphthodefg.ijklpentaphene 493. 1.2-Cyclo-delta 1',4'-pentadienophenanthrene 428 . BenZrstanthracdepentaphene 494. Cyclohexatriene 429 . BenZorstnaphtho2, 1.8-fgh pentaphene 495. 1H-Cyclopentalanthracene 430 . BenZorstnaphtho8.1.2-cdepentaphene 496. 1H-Cyclopent banthracene 431 . BenZorstpentaphene 497. Cyclopent bindeno4.5-glphenanthrene 432. BenZorstphenaleno 1,2,3-depentaphene (Violan 498. Cyclopent bindenoS,6-glphenanthrene threne C) 499. CyclopentiindenoS,6-alanthracene 433. Benzorstphenanthro1,10,9-cdepentaphene 25 500. Cyclopenta 1,2-a:3,4,5-b'c'dicoronene 434. Benzorstphenanthro10,1,2-cdepentaphene 5O1. 17H-Cyclopentalaphenanthrene 435. Benzorst pyreno 1,10,9-cdepentaphene 502. 15H-Cyclopentalaphenanthrene 436. BenZospicene 503. 1H-Cyclopentaapyrene 437. BenZost naphtho2, 1,8,7-defgpentacene 504. 11H-Cyclopentaatriphenylene 438. Benzotuvnaphtho2,1-bipicene 30 505. 8H-Cyclopentablphenanthrene 439. BenZouvnaphtho2, 18.7-defgpentacene 506. Cyclopentacdperylene 440. Benzouvnaphtho2,18,7-defgpentaphene 507. Cyclopentacdpyrene 441. Benzov wx hexaphene 508. Cyclopentadellanthracene 442. 1.2-Benzoacenaphthylene 509. Cyclopentadenaphthacene 443. Benzobenzanthrene 35 51O. Cyclopentadenaphthalene 444. 2,3-Benzochrysene 511. Cyclopentadelpentacene 445. 15, 16-Benzodehydrocholanthrene 512. Cyclopenta depentaphene 446. o-meso-Benzodianthrene 513. Cyclopentadelpicene 447. p-meso-Benzodianthrene 514. 4H-Cyclopenta defchrysene 448. 11, 12-Benzofluoranthene 40 515. 4H-Cyclopenta defphenanthrene 449. 2,13-BenZofluoranthene 516. 4H-Cyclopenta deftriphenylene 450. BenZofluoranthene 517. 1H-Cyclopentaelpyrene 451. 7,10-BenZofluoranthene 518. Cyclopentafgnaphthacene 452. 8.9-Benzofluoranthene 519. Cyclopentafgpentacene 453. 10, 11-Benzofluoranthene 45 520. Cyclopentafgpentaphene 454. 3,4-Benzofluoranthene 521. 11H-Cyclopentaghiperylene 455. 2,3-Benzofluoranthene 522. 6H-Cyclopentaghipicene 456. 1.2-Benzofluorene 523. Cyclopentahichrysene 457. 2,3-Benzofluorene 524. Cyclopentakkphenanthrene 458. 3,4-Benzofluorene 50 525. 1H-Cyclopental phenanthrene 459. 1H-Benzonaphthene 526. 2H-Cyclopental phenanthrene 460. 1,12-Benzoperylene 527. Cyclopentapapentaphene 461. 1.2-Benzoperylene 528. 13H-Cyclopentapqrpicene 462. 2,3-Benzoperylene 529. 13H-Cyclopentarstpentaphene 463. 1.2-Benzophenanthrene 55 530. Cyclopentaphenanthrene 464. 2,3-Benzophenanthrene 531. Decacyclene 465. 3,4-Benzophenanthrene 532. Dehydro-8.9-trimethylene-1,2-benzanthracene 466. 9,10-Benzophenanthrene 533. 3.4.1,6-DiC1.8-naphthylene)benzene 467. 2,3-Benzopicene 534. 1.9.5,10-Di(peri-naphthylene)anthracene 468. 6.7-Benzopyrene 60 535. Di-beta-naphthofluorene 469. 3,4-Benzopyrene 536. Dibenza,canthracene 470. 3,4-Benzotetraphene 537. Dibenza,eaceanthrylene 471. 1.2-Benzperylene 538. Dibenza,eacephenanthrylene 472. 1.2-Benzpyrene 539. Dibenza.hanthracene 473. 4.5-Benzpyrene 65 540. Dibenzalaceanthrylene 474. 2,3-Benztriphenylene 541. Dibenza, anthracene 475 . 1,1'-Bicoronene 542. Dibenza.klacephenanthrylene US 7,183,010 B2 19 20 543. 7H-Dibenza.klanthracene 609. Dibenzoal fluoranthene 544. 1H-Dibenza.klanthracene 610. Dibenzoa.lnaphthacene 545. 4H-Dibenza.klanthracene 611. Dibenzoa.lpentacene 546. Dibenza, laceanthrylene 612. Dibenzoa.lpyrene 547. Dibenza,ntriphenylene 613. Dibenzoa.mpentaphene 548. 13H-Dibenzbcaceanthrylene 614. Dibenzoa.mtetraphene 549. 13H-Dibenzbc.laceanthrylene 615. Dibenzoa.npentacene 550. Dibenzde.klanthracene 616. Dibenzoa.nperylene 551. Dibenzeghiindeno1,2,3,4-pdraperylene 617. Dibenzoa.nlpicene 552. Dibenze.jaceanthrylene 10 618. Dibenzoa.opentaphene 553. Dibenze.kacephenanthrylene 619. Dibenzoa,operylene 554. Dibenzellaceanthrylene 62O. Dibenzoa,olpicene 555. Dibenzellacephenanthrylene 621. Dibenzoa.pchrysene 556. 12:3,4-Dibenzanthracene 622. Dibenzoa.pqrpicene 557. 3,4,5,6-Dibenzanthracene 15 623. Dibenzoa.rst benzo 5,6phenanthro9,10,1-klimpen 558. 2,3:6,7-Dibenzanthracene taphene 559. 1,2,7,8-Dibenzanthracene 624. Dibenzoa.rst naphtho8.1.2-cdepentaphene 560. beta,beta'-Dibenzanthracene 625. Dibenzoa.rstpentaphene 561. 12,6,7-Dibenzanthracene 626. Dibenzob.defchrysene 562. 1,2,3,4-Dibenznaphthalene 627. Dibenzobefluoranthene 563. 3.4.11.12-Dibenzobisanthene 628. Dibenzob.fpicene 564. Dibenzo-1,2,7,8-anthracene 629. 8H-Dibenzob.fgpyrene 565. Dibenzo-2,3,11,12-fluoranthene 630. Dibenzob.gchrysene 566. 1,2,7,8-Dibenzo-4,5-phenanthrylenemethane 631. 7H-Dibenzo[b,g fluorene 567. Dibenzoa,cchrysene 25 632. Dibenzob.gphenanthrene 568. 13H-Dibenzoa.cfluorene 633. Dibenzob.ghifluoranthene 569. Dibenzoa.cnaphthacene 634. Dibenzob.g.hiperylene 570. Dibenzoa.cpentacene 635. 12H-Dibenzob.hfluorene 571. Dibenzoa.cpentaphene 636. Dibenzob.hphenanthrene 572. Dibenzoa.cpicene 30 637. Dibenzob.h]pyrene 573. Dibenzoa,ctetraphene 638. Dibenzobifluoranthene 574. Dibenzoa,ctriphenylene 639. Dibenzob.jplcene 575. Dibenzoa.cdnaphtho8,1,2,3-fghilperylene 640. Dibenzobjkfluorene 576. Dibenzoa.dcoronene 641. Dibenzob.kchrysene 577. 13H-Dibenzoa.delnaphth 2,3-hanthracene 35 642. Dibenzob.kfluoranthene 578. 4H-Dibenzoa.delnaphthacene 643. Dibenzob.kperylene 579. 4H-Dibenzoa.depentacene 644. Dibenzob.lchrysene 580. Dibenzoa,efluoranthene 645. Dibenzob.lfluoranthene 581. Dibenzoa,elpyrene 646. Dibenzob.mpicene 582. Dibenzoa.ffluoranthene 40 647. 8H-Dibenzob.mniphenanthrene 583. Dibenzoa,fperylene 648. 13H-Dibenzob.mniphenanthrene 584. Dibenzoa.fpiceiie 649. Dibenzob.mnofluoranthene 585. Dibenzoaftetraphene 650. Dibenzob.npentaphene 586. Dibenzoa.gcoronene 651. Dibenzob.nperylene 587. 13H-Dibenzoag fluorene 45 652. Dibenzob.nlpicene 588. Dibenzoaghinaphtho2, 1,8-cdeperylene 653. Dibenzob.pchrysene 589. Dibenzoaghinaphtho2, 1.8-lmniperylene 654. Dibenzob.pqrperylene 590. Dibenzoaghinaphtho8, 1.2-klimperylene 655. Dibenzob.drnaphtho3.2.1.8-defgchrysene 591. Dibenzoaghiperylene 656. Dibenzob.spicene 592. 13H-Dibenzoa.hfluorene 50 657. Dibenzob.tuvnaphtho2.1-mpicene 593. Dibenzoa.hpentaphene 658. Dibenzob.tuvpicene 594. Dibenzoa.hphenanthrene 659. Dibenzolm,yzpyranthrene 595. Dibenzoa.hpyrene 660. Dibenzob.c.efcoronene 596. 13H-Dibenzoa.ifluorene 661. Dibenzobc.klcoronene 597. Dibenzoa.ipyrene 55 662. Dibenzoc,ftetraphene 598. Dibenzoa, coronene 663. Dibenzoc.gchrysene 599. Dibenzoa, difluoreno.2.1.9-cde:2.1".9-lmniperylene 664. 7H-Dibenzoc.gfluorene 6OO. Dibenzoa, fluoranthene 665. Dibenzoc.gphenanthrene 6O1 Dibenzoanaphthacene 666. Dibenzochpentaphene 6O2. Dibenzoaperylene 60 667. Dibenzochinaphtho3.2.1.8-mnopchrysene 603. Dibenzoa.jplcene 668. Dibenzoc,icyclopentaafluorene 604. Dibenzoatetracene 669. Dibenzoc.ktetraphene 605. Dibenzoak fluorine 670. Dibenzoc.lchrysene 606. Dibenzoakphenanthro8,9,10,1,2-cdefghpyran 671. Dibenzoc.lmfluorene threne 65 672. Dibenzoic.mipentaphene 6O7. Dibenzoa.kfluoranthene 673. Dibenzoic.mpicene 608. Dibenzoa.ktetraphene 674. Dibenzoc.mtetraphene US 7,183,010 B2 21 22 675. 5H-Dibenzoc.mniphenanthrene 738. Dibenzoh.speropyrene 676. Dibenzoic.mnochrysene 739. Dibenzoij.rst naphtho2, 18.7-defgpentaphene 677. Dibenzoc.pchrysene 740. Dibenzoij.rstphenanthro9,10,1,2-defgpentaphene 678. Dibenzoc.pqrpicene 741. Dibenzoijk.tuViperopyrene 679. Dibenzoic.rstpentaphene 742. Dibenzoil fluoranthene 68O. Dibenzoc, Spicene 743. Dibenzoilm naphtho1.8-abperylene 681. Dibenzocclfganthanthrene 744. Dibenzolmphenanthro5.4.3-abcdperylene 682. Dibenzocchianthanthrene 745. Dibenzoklnonaphtho8,1,2-abccoronene 683. Dibenzocaikpyrene 746. Dibenzoklrst naphtho2, 1,8,7-defgpentaphene 684. Dibenzoca.knaphtho3.2.1.8-pdraperylene 10 747. Dibenzoilm naphthoabperylene 685. Dibenzocallmanthanthrene 748. Dibenzomn.qrfluoreno.2, 1,9,8,7-defghinaphthacene 686. Dibenzocalimperylene 749. Dibenzoo.rstdinaphtho2,1-a:8'1',2'-cdepentaphene 687. Dibenzocannaphtho3.2.1.8-pdraperylene 750. DibenzopduVpentaphene 688. Dibenzode.ijnaphtho3.2.1.8.7-rstuVpentaphene 751. Dibenzoq VWXhexaphene 689. Dibenzode.ijnaphtho7.8.1.2.3-pdrstpentaphene 15 752. Dibenzors,Vwxnaphtho2, 1,8.7-klmnhexaphene 690. Dibenzode.ipentaphene 753. Dibenzouv.alblbenzo 5.6naphthaceno.2,1,12,11,10. 691. Dibenzodeij phenanthro2,1,10,9,8,7-pdrstuvpen 9fghijklm heptacene taphene 754. 2,3,6,7-Dibenzoanthracene 692. Dibenzode.klpentaphene 755. 1,2,5,6-Dibenzoanthracene 693. Dibenzode.mnnaphthacene 756. 2,3,8.9-Dibenzocoronene 694. Dibenzode.nmnaphtho2, 1.8-qranaphthacene 757. 2,3,4,5-Dibenzocoronene 695. Dibenzode.opnaphthacene 758. vic-diperi-Dibenzocoronene 696. Dibenzode.drnaphthacene 759. anti-diperi-Dibenzocoronene 697. Dibenzode.drpentacene 76O. 2,3,5,6-Dibenzofluoranthene 698. Dibenzode.drtetracene 25 761. 1,2,3,4-Dibenzofluorene 699. Dibenzode.stpentacene 762. 2,3,6,7-Dibenzofluorene 700. Dibenzode.uvpentacene 763. 1,2,7,8-Dibenzofluorene 701. Dibenzode.uvpentaphene 764. 1,2,5,6-Dibenzofluorene 702. Dibenzo definaphtho8,1,2-vwxpyranthrene 765. 2.3.10.11-Dibenzoperylene 703. Dibenzo defimnochrysene 30 766. 2.38.9-Dibenzoperylene 704. Dibenzo defimnocyclopentahichrysene 767. 1.12.2.3-Dibenzoperylene 705. Dibenzo defpchrysene 768. 1.124.5-Dibenzoperylene 7O6. Dibenzoeghiperylene 769. 1,2,5,6-Dibenzophenanthrene 707. Dibenzoe.lpyrene 770. 2.3.7,8-Dibenzophenanthrene 708. Dibenzoefhinaphtho8,1,2-abccoronene 35 771. beta.beta'-Dibenzophenanthrene 709. Dibenzoefnonaphtho8,1,2-abccoronene 772. 3,4,5,6-Dibenzophenanthrene 710. Dibenzof naphtho1,2,3,4-pdrpicene 773. gammagamma'-Dibenzophenanthrene 711. Dibenzofpicene 774. 2,3,6,7-Dibenzophenanthrene 712. Dibenzofim tetraphene 775. 4.5,9,10-Dibenzopyrene 713. Dibenzoftpdrpicene 40 776. 2.3:4,5-Dibenzopyrene 714. Dibenzo fspicene 777. 3,4:8,9-Dibenzopyrene 715. Dibenzofg.ibenzo 9.10pyreno5.4.3.2.1-pdrstpen 778. 1.2:4,5-Dibenzopyrene taphene 779. 4,5,6,7-Dibenzopyrene 716. Dibenzofg, inaphtho2, 1.8-uVapentaphene 780. 3.4:9,10-Dibenzopyrene 717. Dibenzofg, inaphtho7.8.1.2.3-pdrstpentaphene 45 781. 12:9,10-Dibenzopyrene 718. Dibenzofg.ipentaphene 782. 4.5.8.9-Dibenzopyrene 719. Dibenzofg.iphenanthro2,1,10,9,8,7-pdrstuvpen 783. 1.2.9.10-Dibenzotetracene taphene 784. 1.2.7.8-Dibenzotetracene 720. Dibenzofg.iphenanthro9,10,1,2,3-pdrstpentaphene 785. 1.2.5.6-Dibenzotetraphene 721. Dibenzofg.itriphenyleno 1,2,3,4-rstpentaphene 50 786. 1.2:7,8-Dibenzphenanthrene 722. Dibenzofg.oplanthanthrene 787. 3,4:8,9-Dibenzpyrene 723. Dibenzofg.opnaphthacene 788. 1.2:3,4-Dibenzpyrene 724. Dibenzofg.crpentacene 789. 1.2:7,8-Dibenzpyrene 725. Dibenzofg, sthexacene 790. 1.2:6,7-Dibenzpyrene 726. Dibenzofgh.pqrtrinaphthylene 55 791. Dicoronylene 727. Dibenzog.pchrysene 792. Dicyclopentaa.cnaphthacene 728. Dibenzoghilminaphtho1.8-abperylene 793. Dicyclopentaa, coronene 729. Dibenzoghimnofluoranthene 794. Difluorenylene 730. Dibenzoghinnaphtho8,1,2-bcdperylene 795. Di-fluorantheno3.5.4.6.4.6'.9.11 coronene 731. Dibenzoghi.pqrperylene 60 796. 1,2-Dihydroacenaphthylene 732. Dibenzob.nperylene 797. 1,2-Dihydrobenaceanthrylene 733. Dibenzohrstipentaphene 798. 3,4-Dihydrocyclopentacdpyrene 734. 12H-Dibenzoa.fgnaphthacene 799. 10, 15-Dihydrotribenzoa.fktrindene 735. Dibenzohi.klnaphtho8,1,2-abccoronene 800. Diindeno1,2,3-cd: 1'd',3'-jk]pyrene 736. Dibenzohiopdinaphtho8,1,2-cde:2.1".8'-uvapenta 65 8O1. Dindeno1,2,3-de, 1,2',3'-klanthracene C 8O2. Dinaphth 1,2-a: 1,2'-hanthracene 737. Dibenzohidranthanthrene 8O3. Dinaphth 1,2-a:2', 1'-janthracene US 7,183,010 B2 23 24 804. Dinaphth 2,3-a,2',3'-canthracene 870. Hexahelicene 805. peri-Dinaphthalene 871. Hexaphene 806. lin-Dinaphthanthracene 872. Idryl 807. Dinaphtho1.2-b:2', 1'-nperylene 873. as-Indacene 8O8. Dinaphtho1,2,3-cd.1'2',3'-lmperylene 874. S-Indacene 809. Dinaphtho1,2,3-cd,3'2", 1'-lmperylene 875. as-Indaceno.2,3-alphenanthrene 810. Dinaphtho1,2,3-fg:1'2',3'-qrpentacene 876. 1H-Indene 811. Dinaphtho1.2.3-fg:3', 2', 1'-qrpentacene 877. Indene 812. Dinaphtho1.2-b.2, 1'-nperylene 878. Indeno-2',3'-3,4-pyrene 813. Dinaphtho1.2-b: 1,2'-kchrysene 10 879. Indeno1,2,3-cdfluoranthene 814. Dinaphtho1.8-ab:8'1'.2',3'-fghilperylene 880. Indeno1,2,3-cdperylene 815. Dinaphtho1.8-bc:1,8-mnlpicene 881. Indeno1.2.3-cdpyrene 816. Dinaphtho2,1-a:2', 1'-perylene 882. Indeno1,2,3-denaphthacene 817. Dinaphtho2, 1,8,7-defg:2", 1",8,7'-ijklpentaphene 883. Indeno1.2.3-fgnaphthacene 818. Dinaphtho2, 1,8,7-defg:2", 1",8,7'-opdrpentacene 15 884. Indeno1,2,3-hichrysene 819. Dinaphtho2, 1,8,7-defg:2", 1",8,7-qrstpentacene 885. 8H-Indeno1,2-alanthracene 82O. Dinaphtho2, 1,8-cde.2.1".8-lmniperylene 886. Indeno1,2-alphenalene 821. Dinaphtho2, 1,8-fgh:3'2", 1",8,7'-rstuVpentaphene 887. 7H-Indeno1,2-alphenanthrene 822. Dinaphtho2, 1,8-fgh:7",8,1'2',3'-pdrstpentaphene 888. 7H-Indeno1,2-alpyrene 823. Dinaphtho2, 1,8,7-hijk:2", 1",8,7'-wxyZheptacene 889. 11 H-Indeno1,2-altriphenylene 824. Dinaphtho2, 1.8-kl:2.1".8'-uvapentacene 890. 13H-Indeno1,2-banthracene 825. Dinaphtho2,1-a: 1,2'-lnaphthacene 891. 12H-Indeno1,2-bphenanthrene 826. Dinaphtho2, 1-a:2, 1'-naphthacene 892. 13H-Indeno1.2-cphenanthrene 827. Dinaphtho2,1-c 1,2'-glphenanthrene 893. 9H-Indeno1.2-epyrene 828. Dinaphtho2.3-c:2',3'-mpentaphene 25 894. 13H-Indeno1.2-lphenanthrene 829. Dinaphtho3.2.1-fg:1'2',3'-ilpentaphene 895. Indeno1,7,6,5-cdefchrysene 830. Dinaphtho3.2.1-fg:3', 2', 1'-qrpentacene 896. Indeno1.7-abchrysene 831. Dinaphtho2,3-a:2,3-epyrene 897. Indeno1.7-abpyrene 832. Dinaphtho8,1,2-abc:2', 1,8-efgcoronene 898. Indeno1.7-abtriphenylene 833. Dinaphtho8,1,2-abc:2', 1,8-hijcoronene 30 899. Indeno1.7a-alphenanthrene 834. Dinaphtho8,1,2-abc:2', 1.8-klm coronene 900. 3H-Indeno2, 1.7-cdelpyrene 835. Dinaphtho8,1,2-abc:2', 1.8-nopcoronene 901. 11 H-Indeno2, 1.7-cdelpyrene 836. Dinaphtho8,1,2-abc:8'1',2'-ghicoronene 902. 13H-Indeno2, 1,7-qranaphthacene 837. Dinaphtho8,1,2-abc:8'1',2'-jklcoronene 903. 13H-Indeno2,1-alanthracene 838. Dinaphtho8,1,2-cde:7",8,1,2',3'-pdrstpentaphene 35 904. 5H-Indeno2,1-achrysene 839. Dinaphtho8, 1.2-lmn:2', 1.8-qranaphthacene 905. Indeno2,1-alphenalene 840. alpha,alpha'-Dinaphthofluorene 906. 11 H-Indeno2, 1-alphenanthrene 841 . 2.3.7.8-Di-(peri-naphthylene)-pyrene 907. 11 H-Indeno2, 1-alpyrene 842. Diphenaleno.4.3.2.1.9-hijklm:4',3'.2.1".9'-tuvwxaru 908. 8H-Indeno.2.1-biphenanthrene bicene 40 909. 9H-Indeno.2.1-cphenanthrene 843. Diphenanthro3,4-c:4',3'-glphenanthrene 910. Indeno3.2.1.7-defgchrysene 844. Diphenanthro5.4.3-abcd:5',4',3'-jklimperylene 911. Indeno4.3.2.1-cdefchrysene 845. 2,7-Diphenylbenzoghifluoranthene 912. Indeno5,6,7,1-defgchrysene 846. 2.9-Diphenylcoronene 913. IndenoS.6.7.1-pdraperylene 847. Diphenylenemethane 45 914. Indeno.6.7.1.2-defgnaphthacene 848. 9,10-Diphenylenephenanthrene 915. 1H-Indeno6.7.1-mnalanthracene 849. Dipyreno.1'.3'.4.6.10'.2.9.11 coronene 916. Indeno.7.1.2.3-cdefchrysene 850. 2.3.3'2'-Dipyrenylene 917. 4H-Indeno.7.1.2-ghichrysene 851. 1.8-Ethylenenaphthalene 918. Indeno7,1-abnaphthacene 852. Fluoranthene 50 919. Indeno7,1-abtriphenylene 853. Fluorantheno8.9-btriphenylene 920. Indeno7.1-bclchrysene 854. 9H-Fluorene 921. Isochrysene 855. Fluorene 922. Isochrysofluorene 856. Fluoreno.2.1-afluorene 923. Isonaphthofluorene 857. Fluoreno 2,3-afluorene 55 924. Isorubicene 858. Fluoreno.3.2.1.9-defgchrysene 925. IsotruXene 859. Fluoreno 3.2-bifluorene 926. Isoviolanthrene 86O. Fluoreno3,4-bifluorene 927. 1.9-Methylene-1,2,5,6-dibenzanthracene 861. Fluoreno 4,3,2-delanthracene 928. 1.9-Methylene-1,2-benzanthracene 862. Fluoreno 4.3-c fluorene 60 929. 2,2'-Methylenebiphenyl 863. Fluoreno 9,1-ab triphenylene 930. 4.5-Methylenephenanthrene 864. 6 Helicene 931. 19.8-(diperi)-Naphth-2,9-dihydroanthracene 865. Heptacene 932. Naphth 1'.2:5.6 indeno1,2,3-cdpyrene 866. Heptaphene 933. Naphth 1,2-alaceanthrylene 867. Hexabenzobenzene 65 934. Naphth 1,2-alacephenanthrylene 868. 1.12.2.3.4.5.6.7.8.9.10.11-Hexabenzocoronene 935. Naphth 1,2-alanthracene 869. Hexacene 936. Naphth 1,2-dacenaphthylene US 7,183,010 B2 25 26 937. Naphth 1.2-eacephenanthrylene 10O3. Naphtho1.2-btriphenylene 938. Naphth 1,2-aceanthrylene 1004. Naphtho1.2-cchrysene 939. Naphth 1.2-kacephenanthrylene 1005. Naphtho1.2-cpentaphene 940. Naphth 2,1":4.5indeno1,2,3-cdpyrene 1006. Naphtho1.2-epyrene 941. Naphth 2, 1-alaceanthrylene 1007. Naphtho1.2-fpicene 942. Naphth 2, 1-alanthracene 10O8. Naphtho1.2-gchrysene 943. Naphth 2,1-dacenaphthylene 1009. Naphtho1.2-hpentaphene 944. Naphth 2,1-eaceanthrylene 1010. Naphtho1.2-fluoranthene 945. Naphth 2,1-eacephenanthrylene 1011. Naphtho1.2-kfluoranthene 946. Naphth 2, 1-kacephenanthrylene 10 1012. Naphtho1,8,7,6-cdeffluorene 947. Naphth 2,1-1aceanthrylene 1013. NaphthoI2',3':2.3 fluoranthene 948. Naphth 2,1-1acephenanthrylene 1014. NaphthoI2.1", 1.2 tetracene 949. Naphth 2, 1.8-uvalovalene 1015. NaphthoI2.3", 1.2pyrene 950. Naphth 2,3-alaceanthrylene 1016. NaphthoI2, 1.8-defpicene 951. Naphth 2,3-eacenaphthylene 15 1017. NaphthoI2, 1.8-fghpentaphene 952. Naphth 2,3-eacephenanthrylene 1018. NaphthoI2, 1.8-hijanthanthrene 953. Naphth 2.3-lacephenanthrylene 1019. Naphtho2, 1.8-qranaphthacene 954. Naphth2", 1",8,7":4,10.5 anthra 1,9.8-abcdcoronene 102O. NaphthoI2, 1.8-uvapentacene (Circobiphenyl) 1021. NaphthoI2, 1.8-uvapentaphene 955. 5H-Naphth 3.2.1-delanthrene 1022. NaphthoI2, 1.8-yZahexacene 956. 2', 1'-Naphtha-1,2-fluorene 1023. NaphthoI2,1-afluoranthene 957. 1',2'-Naphtha-2,3-fluorene 1024. 11H-Naphtho2,1-afluorene 958. 1',3'-Naphtha-3,4-pyrene 1025. Naphtho2,1-anaphthacene 959. Naphthacene 1026. Naphtho2,1-alpentaphene 960. Naphthaceno 2,1,12,11-opdranaphthacene 25 1027. NaphthoI2,1-aperylene 961. Naphthaceno.4,5,6,7,8-defghijnaphthacene 1028. NaphthoI2, 1-alpicene 962. peri-Naphthacenonaphthacene 1029. NaphthoI2, 1-alpyrene 963. Naphthalene 1030. NaphthoI2, 1-altetraphene 964. 1.2-(1,8-Naphthalenediyl)benzene 1031. NaphthoI2,1-bichrysene 965. Naphthanthracene 30 1032. NaphthoI2,1-bfluoranthene 966. Naphthanthracene 1033. NaphthoI2,1-bperylene 967. 8H-meso-alpha-Naphthanthrene 1034. NaphthoI2,1-bipicene 968. 1,8.9-Naphthanthrene 1035. NaphthoI2.1-c:7,8-c'diphenanthrene 969. Naphthanthrene 1036. NaphthoI2.1-cchrysene 970. lin-Naphthanthrene 35 1037. Naphtho2.1-cpentaphene 971. 13H-meso-alpha-Naphthanthrene 1038. NaphthoI2.1-cpicene 972. 1 H-alpha-Naphthindene 1039. NaphthoI2.1-citetraphene 973. 1 H-beta-Naphthindene 1040. NaphthoI2,1-fluoranthene 974. 3H-alpha-Naphthindene 1041. NaphthoI2,3-acoronene 975. Naphtho(2',3':7,8)fluoranthene 40 1042. NaphthoI2,3-afluoranthene 976. Naphtho(2',3':8,9)fluoranthene 1043. 13H-Naphtho2.3-afluorene 977. Naphtho-(23':4,5)pyrene 1044. NaphthoI2,3-alpentaphene 978. 1,2'-Naphtho-1,2-fluoranthene 1045. NaphthoI2,3-alpicene 979. Naphtho1'2', 1.2|anthracene 1046. NaphthoI2,3-alpyrene 980. Naphtho-2',3',1,2-anthracene 45 1047. NaphthoI2,3-altetraphene 981. Naphtho-2',3',1,2-phenanthrene 1048. NaphthoI2,3-bfluoranthene 982. Naphtho-2',3',2,3-phenanthrene 1049. NaphthoI2,3-bpicene 983. Naphtho-2',3',3,4-phenanthrene 1050. NaphthoI2,3-bipyrene 984. Naphtho 1,2,3,4-defchrysene 1051. NaphthoI2.3-cchrysene 985. Naphtho1,2,3,4-ghifluoranthene 50 1052. 8H-Naphtho2.3-c fluorene 986. Naphtho1,2,3,4-ghilperylene 1053. NaphthoI2.3-cpentaphene 987. Naphtho1,2,3,4-rstpentaphene 1054. NaphthoI2,3-epyrene 988.9H-Naphtho1,2,3-cdperylene 1055. NaphthoI2.3-gchrysene 989. 6H-Naphtho1,2,3-cdpyrene 1056. NaphthoI2,3-hpentaphene 990. Naphtho1,2-acoronene 55 1057. NaphthoI2.3-fluoranthene 991. Naphtho1,2-afluoranthene 1058. NaphthoI2.3-kfluoranthene 992. Naphtho1,2-anaphthacene 1059. NaphthoI2.3-spicene 993. Naphtho1,2-alpentacene 106O. NaphthoI2.8.2.4 coronene 994. Naphtho1,2-alpentaphene 1061. Naphtho3',4':3.4 pyrene 995. Naphtho1,2-alpyrene 60 1062. Naphtho3.2.1.8,7-defghpyranthrene 996. Naphtho1,2-a tetracene 1063. Naphtho3.2.1.8.7-vw.xyzhexaphene 997. Naphtho1,2-a tetraphene 1064. Naphtho3.2,1-jkfluorene 998. Naphtho1.2-bichrysene 1065. Naphtho4.5,6-abcaceanthrylene 999. Naphtho1,2-bifluoranthene 1066. Naphtho5.4.3-abccoronene 1000. 12H-Naphtho1,2-bifluorene 65 1067. Naphtho7,8,1,2,3-pdrstpentaphene 1001. Naphtho1.2-bperylene 1068. Naphtho7,8,1,2,3-tuvwxhexaphene 1002. Naphtho1.2-bpicene 1069. Naphtho8,1,2-abccoronene US 7,183,010 B2 27 28 1070. Naphtho8,1,2-cdenaphthacene 1136. Phenanthro9,10-anaphthacene 1071. Naphtho8,1,2-cdepentaphene 1137. Phenanthro9,10-blehrysene 1072. Naphtho8,1,2-efganthanthrene 1138. Phenanthro9,10-bitriphenylene 1073. Naphtho8.1.2-ghichrysene 1139. 4.5-Phenanthrylenemethane 1074. Naphthob'.bchrysene 5 1140. 7-Phenylbenzoacoronene 1075. Naphthodcoronene 1141. 2-Phenylbenzobfluoranthene 1076. Naphthobenzanthrene 1142. 2-Phenylbenzo fluoranthene 1077. lin-Naphthofluorene 1143. 5-Phenylbenzo fluoranthene 1078. 2,3-beta-Naphthofluorene 1144. 5,6-(1.2-Phenylene)naphthacene 1079. Nonacene 10 1145. 1,10-(1,2-Phenylene)pyrene 1080. Octacene 1146. 1,10-(o-Phenylene)pyrene 1081. Ovalene 1147. 2.3-(o-Phenylene)pyrene 1082. Paranaphthalene 1148. 19-Phenyleneanthracene 1083. Pentacene 1149.5,6-O-Phenylenenaphthacene 1084. peri-Pentacenopentacene 15 1150. 10,11-Phenylenenaphthacene 1085. Pentalene 1151. 2.3-Phenylenepyrene 1086. Pentaleno 1,2-b:4,5-b'Idinaphthalene 1152. o-Phenylenepyrene 1087. Pentanthrene 1153. Picene 1088. Pentanthrene 1154. Pyranthrene 1089. Pentaphene 20 1155. Pyrene 1090. Periflanthene 1156. peri-Pyrene-1,10(CH2)-indene 1091. Perinaphthene 1157. Pyrenindene 1092. 2.3-Peri-naphthylene-pyrene 1158. Pyreno. 1, 10.9-abccoronene 1093. Peropyrene 1159. Pyreno. 10,1,2-abccoronene 1094. Perylene 25 1160. Pyreno.2.1-bipicene 1095. Perylo 3.2.1.12-pdrabperylene 1161. Pyreno5.4.3.2.1-pdrstpentaphene 1096. 1H-Phenalene 1162. Rubicene 1097. Phenalene 1163. Rubrene 1098. Phenaleno 12.3.4-ghijperylene 1164. Quaterrylene 1099. 2',3'-Phenanthra-1,2-anthracene 30 1165. Terrylene 1100. 2',3'-Phenanthra-2,3-phenanthrene 1166. 1.2.3.4.5.6, 10.11-Tetrabenzanthanthrene 1101. Phenanthrene 1167. Tetrabenza,chanthracene 1102. Phenanthreno-9', 10:9,10phenanthrene-1,1'methyl- 1168. Tetrabenzoa,chimnnaphthacene C 1169. Tetrabenzoa.c.hiqrpentacene 1103. Phenanthrin 35 1170. Tetrabenzoa.c.jlnaphthacene 1104. Phenanthrindene 1171. Tetrabenzoa.c.l.npentacene 1105. Phenanthro1,10.9-abccoronene 1172. Tetrabenzoa.cd.iflimperylene 1106. Phenanthro1,10,9,8-opqraperylene 1173. Tetrabenzoa.cdl.lmperylene 1107. Phenanthro1,2,3,4-defchrysene 1174. Tetrabenzoa,e,j.operylene 1108. Phenanthro1,2,3,4-ghiperylene 40 1175. Tetrabenzoa.f. operylene .1176. Tetrabenzoafk.n 1109. Phenanthro1,2-anaphthacene perylene 1110. Phenanthro1,2-bichrysene 1177. Tetrabenzobc.efhi.klcoronene 1111. Phenanthro1,2-btriphenylene 1178. Tetrabenzobc.efklinocoronene 1112. Phenanthro10,1,2,3-cdeffluorene 1179. Tetrabenzode.h.klrstpentaphene 1113. Phenanthro10,1,2-abccoronene 45 1180. Tetrabenzode.hirn.cqrnaphthacene 1114. Phenanthro2,1,10,9,8,7-pdrstuVpentaphene 1181. Tetrabenzode.hiop, stipentacene 1115. Phenanthro2,1,10,9,8,7-tuvwxyZhexaphene 1182. Tetrabenzode.jkop,uVpentacene 1116. Phenanthro2.1-bichrysene 1183. Tetrabenzode.lm.uv.albl heptacene 1117. Phenanthro2.1-fpicene 1184. tetrabenzode.lm.stclal heptacene 1118. Phenanthro2,3,4,5-tuvabpicene 50 1185. Tetrabenzofg.i.pduVpentaphene 1119. Phenanthro2.3-cchrysene 1186. Tetrabenzoa.c.hiqrpentacene 1120. Phenanthro2.3-gchrysene 1187. Tetrabenzogh.jk.tu,wxpyranthrene 1121. Phenanthro3.2-bichrysene 1188. 1.2:34:5,6:7,8-Tetrabenzonaphthalene 1122. Phenanthro3.2-gchrysene 1189. Tetracene 1123. Phenanthro3,4-alanthracene 55 1190. Tetrahelicene 1124. Phenanthro3,4-anaphthacene 1191. 1.2.3.4.5.6.7.8-Tetra(peri-naphthylene)anthracene 1125. Phenanthro3,4-bichrysene 1192. Tetraphene 1126. Phenanthro3,4-btriphenylene 1193. N.N.N',N'-Tetraphenyl-tetrabenzoa.cdl.lmperylene 1127. Phenanthro3,4-cchrysene 1,10-diamine 1128. Phenanthro3,4-cphenanthrene 60 1194. Tribenza.c.hanthracene 1129. Phenanthro3,4,5,6-bcdefovalene 1195. 1,2,3,4,5,6-Tribenzanthracene 1130. Phenanthro4.3.2.1-defchrysene 1196. Tribenzoa.c.jnaphthacene 1131. Phenanthro4.3-alanthracene 1197.8H-Tribenzoa.cdl.lpyrene 1132. Phenanthro4,3-bichrysene 1198. Tribenzoa.cdl.limperylene 1133. Phenanthro5.4.3.2-abcdeperylene 65 1199. Tribenzoa,e.g.hiperylene 1134. Phenanthro9,10,1,2,3-pdrstpentaphene 1200. Tribenzoa,efhicoronene 1135. Phenanthro9.10.1-qranaphthacene 1201. Tribenzoa,efnocoronene US 7,183,010 B2 29 30 1202. Tribenzoa.fperylene 1255. Naphtho1.2-gquinoline 1203. Tribenzoaghi.kperylene 1256. Phenazine 1204. Tribenzoa.hi.klcoronene 1257. Benzobiphenazine 1205. Tribenzoa.himnnaphthacene 1258. Dibenzob.g. 1.5 naphthyridine 1206. Tribenzoa.i.lpyrene 5 1259. Dibenzob.g. 1.8 naphthyridine 1207. Tribenzoanjk.VIphenanthro8,9,10,1,2-cdefghpyran 1260. Dibenzoa,iphenazine threne 1261. Dibenzoa.hphenazine 1208. Tribenzo 12:4.5:8,9)pyrene 1262. Dibenzoa.jphenazine 1209. Tribenzob.defpchrysene 1263. Phenanthrazine 1210. Tribenzob.e.g.hiperylene 10 1264. BenZglisoquinoline 1211. Tribenzob.g.kchrysene 1265. BenZhisoquinoline 1212. Tribenzo[b,g,lchrysene 1266. BenZIf isoquinoline 1213. Tribenzob.g.pchrysene 1267. 1,10-Phenanthroline 1214. Tribenzob.n.pqrperylene 1268. 1,7-Phenanthroline 1215. Tribenzoc.g.mnochrysene 15 1269. 4.7-Phenanthroline 1216. Tribenzode.irstpentaphene 1270. Benzob1,10phenanthroline 1217. Tribenzode.klrstpentaphene 1271. Dibenzob.1,10phenanthroline 1218. Tribenzofgh.pqrzalblitrinaphthylene 1272. NaphthoI2.3-f 1,10phenanthroline 1219. Tribenzo fgijo benzo 5.6 naphthaceno. 10,11,12.1.2, 1273. Benzof 1,10phenanthroline 3-qrstuVWXhexaphene 1274. 1.9-Phenanthroline 1220. 1H-Tribenzofgjk.uvhexacene 1275. Benzoh-1,6-naphthyridine 1221. Tribenzo fg.dvwxbenzo 5.6naphthaceno.2,1,12,11, 1276. Phenaleno 1,2,3-dequinoline (3-Azaperylene) 10-ijklmnohexaphene 1277. Benzo[1,2,3-de:4,5,6-d'e'diquinoline (3.9-Diaza 1222. Tribenzojk,qr,uvnaphtho2, 1,8.7-defgpentacene perylene) 1223. Tribenzobicyclo[2.2.2]octatriene 25 1278. Dibenzo degh 1,10phenanthroline 1224. Trindeno2.3:2',3':2',3'benzene 1279. BenZIdeisoquino 1.8-ghduinoline 1225. Trinaphthylene 1280. Dibenzof higuinoline (1-AZatriphenylene) 1226. Trinaphthylenebenzene 1281. Dibenzof higuinoxaline (1,4-Diazatriphenylene) 1227. Triphenylene 1282. Pyrido2.3-f1.7phenanthroline 1228. Triptycene 30 1283. Dibenza.cacridine (1.2:3,4-Dibenzacridine) 1229. Truxene 1284. Tetrabenza.c.hacridine 1230. Zethrene 1285. 8,8-Biquinoline The list of preferred heterocyclic compounds or alkyl, 1286. 8,8-Biquinoline alkenyl, alkynyl, aryl, Substituted aryl, silyl, ace, indeno, 1287. 2,4'-Biquinoline 1.2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-an 35 1288. 2,2'-Biquinoline thraceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP. 1289. 3,3'-Bisoquinoline 1,12-Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1,2- 1290. Phenanthridine PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2- 1291. Benzoiphenanthridine FlAn, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP 1.2-TriP. fluoro, 1292. Benzobiphenanthridine cyano, alkoxy, aryloxy, amino, aza, oxo, thia, heterocyclic, 40 1293. Benzocphenanthridine (5-AZachrysene) keto, and dicyanomethyl derivatives thereofas materials for 1294. Thebenidine (4-Azapyrene) the first host component of the luminescent layer of this 1295. Naphth 2, 1.8-defisoquinoline (2-Azapyrene) invention includes: 1296. Naphtho2, 1.8-defquinoline (1-Azapyrene) 1231. Benzaacridine 1297. Benzolmin3,8phenanthroline (2,7-Diazapyrene) 1232. Benz blacridine 45 1298. Naphth 2, 1.8-mnalacridine 1233. Benzcacridine 1299. Benzogquinazoline 1234. Dibenza,cacridine 1300. Dibenzof higuinazoline 1235. Dibenza,iacridine 1301. 2,2'-Biquinazoline 1236. Dibenzc.hacridine 1302. 3,3'-Bicinnoline 1237. Dibenza.hacridine 50 1303. Benzoccinnoline 1238. Dibenzaacridine 1304. Dibenzoc.gcinnoline (Naphtho2.3-ccinnoline) 1239.7H-Benzoccarbazole 1305. Benzohnaphtho1.2-ccinnoline 1240. 1 1H-Benzoa carbazole 1306. 3-Phenyl-3H-naphth 1,2-diimidazole 1241. Dibenzoa.icarbazole 1307. Phenanthro9,10-dioxazole 1242. 7H-Dibenzoc.gcarbazole 55 1308. Anthra 2,3-dioxazole 1243. Benzobnaphtho2.3-dfuran 1309. 3-Phenyldibenzofuran 1244. Benzobnaphtho2,1-dfuran 1310. Benzo(1,2-b:4,5-b')bisbenzofuran 1245. Dinaphtho2,1-b:1'2'-dfuran 1311. 1,4-Diazatriphenylene 1246. Dinaphtho1.2-b:2', 1'-dfuran 1312. 5,12-Diazatriphenylene 1247. Dinaphtho1.2-b:2',3'-dfuran 60 1313. 2, 12-Dioxadibenzojk.uvbiscyclopenta3.4naphtho 1248. Dinaphtho2,1-b:2',3'-dfuran 2,18,7-defg:2", 1",8,7'-opdrpentacene 1249. Dinaphhto2,3-b:2',3'-dfuran 1314. Dinaphtho1'2':2,3:2", 1":10, 11 perylo 1,12] furan 1250. Benzo 1,2-b:3,4-b'bisbenzofuran 1315. Diphenaleno9'1',2':3.4,5:9", 1",2":9,10,11 coroneno 1251. Benzo 1.2-b:3,4-b'bisbenzofuran 1.2-c:7,8-c'difuran 1252. Benzo 1.2-b:4,5-b'bisbenzofuran 65 Any of the above listed PAH, and any benzenoid com 1253. Benzogquinoline pounds formed by the combination of one or more of the 1254. Naphtho2.3-gquinoline above listed PAH which may or may not be chemically US 7,183,010 B2 31 32 linked, are useful as the first host component, and impor 1.2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-an tantly, the compounds do not have to be film forming thraceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP. materials at room temperature. The mixture of the second 1,12-Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1,2- host component and the first host component must be PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2- capable of forming continuous amorphous films. FlAn, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 1,2-TriP. ace, or In benzenoid and heterocyclic compounds formed by indeno substituent are useful. combination of two or more PAH, two or more heterocyclic Particularly preferred materials for the first host compo compounds, or at least one PAH and at least one heterocycle, nent of the luminescent layer of this invention include the constituent PAHs and heterocycles may or may not be benzenoid compounds of the following structures: not chemically connected together via a single chemical 10 bond or linked via a saturated or unsaturated hydrocarbon (a) group or by a heteroatom N, O, or S. Examples of useful compounds formed by chemically connected combination of two or more the same or different PAH (aforementioned PAHs 1 through 39), two or more the same or different 15 heterocyclic compounds (aforementioned heterocycles 40 through 102), or at least one PAH 1 through 39 and at least one heterocycle 40 through 102 include: 1316. Pyrene-pyrene 1317. Pyrene-benzene-pyrene 1318. Perylene-benzene-perylene 1319. Perylene-perylene 1320. Pyrene-perylene wherein: 1321. Benzopyrene-benzopyrene Substituents R through Ra are each individually hydro 1322. Coronene-perylene 25 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 1323. BenZoghilperylene-pyrene lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 1324. Naphthopyrene-pyrene silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 1325. Perylene-naphthacene to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 1326. Naphthacene-pyrene alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 1327. Naphthacene-perylene 30 carbon atoms, Substituted aryl, heterocycle containing at 1328. Fluoranthene-benzopyrene least one nitrogen atom, or at least one oxygen atom, or at 1329. Fluoranthene-perylene least one sulfur atom, or at least one boron atom, or at least 1330. Anthanthrene-anthracene one phosphorus atom, or at least one silicon atom, or any 1331. Anthracene-perylene combination thereof, or any two adjacent R through Ra. 1332. Coronene-anthracene 35 Substituents form an annelated benzo-, naphtho-, anthra-, 1333. Triphenylene-anthracene phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 1334. Triphenylene-perylene peryleno-substituent or its alkyl or aryl substituted deriva 1335. Perylene-acridine tive; or any two R through R. Substituents form a 12 1336. Pyrene-carbazole benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra 1337. Anthracene-oxadiazole 40 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 1338. Perylene-imidazole Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1339. Triphenylene-pyridine 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 1340. Pyridine-perylene 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or 1341. Coronene-naphthyridine indeno substituent or their alkyl or aryl substituted deriva 1342. Quinoline-perylene 45 tive; or 1343. Quinoline-anthracene 1344. Furan-binaphthyl (b) 1345. Isoquinoline-anthanthrene In the above examples 1316 through 1345, a hyphen repre 50 sents a single chemical bond or a linkage via a saturated or unsaturated hydrocarbon group including alkenyl, alkynyl, PAH, and heterocycle or by a heteroatom N, O, or S between PAH moieties, heterocyclic moieties, or PAH and heterocy clic moieties. Useful benzenoid compounds include com 55 pounds such as PAH and/or heterocyclic groups linked by one or more linkage groups. Any of the above listed ben Zenoid compounds 1 through 1315 substituted with one or more fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 60 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl, alkenyl, wherein: alkynyl, aryl, Substituted aryl, heterocycle containing at least Substituents R through Ra are each individually hydro one nitrogen atom, or at least one oxygen atom, or at least gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky one Sulfur atom, or at least one boron atom, or at least one lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl phosphorus atom, or at least one silicon atom, or any 65 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 combination thereof, benzo-, naphtho-, anthra-, phenan to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, thro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 US 7,183,010 B2 33 34 carbon atoms, Substituted aryl, heterocycle containing at wherein: least one nitrogen atom, or at least one oxygen atom, or at Substituents R through R are each individually hydro least one Sulfur atom, or at least one boron atom, or at least gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through Ra. lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl Substituents form an annelated benzo-, naphtho-, anthra-, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, peryleno-substituent or its alkyl or aryl substituted deriva alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 tive; or any two R through R. Substituents form a 12 carbon atoms, Substituted aryl, heterocycle containing at benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra 10 least one nitrogen atom, or at least one oxygen atom, or at ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 least one Sulfur atom, or at least one boron atom, or at least Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, one phosphorus atom, or at least one silicon atom, or any 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, combination thereof, or any two adjacent R through R2 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or Substituents form an annelated benzo-, naphtho-, anthra-, indeno substituent or their alkyl or aryl substituted deriva 15 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or tive; or peryleno-substituent or its alkyl or aryl substituted deriva (c) tive; or any two R through R. Substituents form a 12 R11 R12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra R10 R ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 R Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, R3 R 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva 25 tive; or Rs R4

wherein: 30 Substituents R through R are each individually hydro (e) gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky R12 R R2 R3 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl R11 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 35 O R4 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 R16 Rs carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at Rs R7 R6 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any 40 combination thereof, or any two adjacent R through R2 Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva wherein: tive; or any two R through R. Substituents form a 12 45 Substituents R through R are each individually hydro benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 50 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 indeno substituent or their alkyl or aryl substituted deriva carbon atoms, Substituted aryl, heterocycle containing at tive; or least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least (d) one phosphorus atom, or at least one silicon atom, or any 55 combination thereof, or any two adjacent R through R2 Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 60 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 65 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or US 7,183,010 B2 35 36 one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R.

(f) Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 10 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or 15 (h) wherein: R12 R Substituents R through Ro are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky R11 R2 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 R10 R3 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 R R4 carbon atoms, Substituted aryl, heterocycle containing at 25 least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least Rs Rs one phosphorus atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R10 R7 R6 Substituents form an annelated benzo-, naphtho-, anthra-, 30 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or wherein: peryleno-substituent or its alkyl or aryl substituted deriva substituents R through R are each individually hydro tive; or any two R through Rio Substituents form a 12 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 35 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or carbon atoms, Substituted aryl, heterocycle containing at indeno substituent or their alkyl or aryl substituted deriva least one nitrogen atom, or at least one oxygen atom, or at tive; or 40 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R2 (g) Substituents form an annelated benzo-, naphtho-anthra-, R12 R phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 45 peryleno-substituent or its alkyl or aryl substituted deriva R11 R tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra R10 R3 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 50 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, Ro R4 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva Rs Rs tive; or R R6 55 wherein: Substituents R through R are each individually hydro R10 R gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 60 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl Ro silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at 65 least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least US 7,183,010 B2 37 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky (k) lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at 10 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 15 peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, wherein: 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or Substituents R through Ra are each individually hydro indeno substituent or their alkyl or aryl substituted deriva gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky tive; or lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 25 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at () 30 least one nitrogen atom, or at least one oxygen atom, or at R13 R14 R least one Sulfur atom, or at least one boron atom, or at least R12 R one phosphorus atom, or at least one silicon atom, or any R11 combination thereof, or any two adjacent R through Ra. Substituents form an annelated benzo-, naphtho-, anthra-, R10 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or R3 35 peryleno-substituent or its alkyl or aryl substituted deriva R4 tive; or any two R through R. Substituents form a 12 R Rs benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra R8 R7 R6 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 40 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or wherein: 45 Substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky (l) lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl R R2 R3 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 R10 R4 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 50 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at R6 Rs least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least Rs R R6 one phosphorus atom, or at least one silicon atom, or any 55 combination thereof, or any two adjacent R through Ra. Substituents form an annelated benzo-, naphtho-, anthra-, wherein: phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or Substituents R through Ro are each individually hydro peryleno-substituent or its alkyl or aryl substituted deriva gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky tive; or any two R through R. Substituents form a 12 60 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, carbon atoms, Substituted aryl, heterocycle containing at 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 65 least one nitrogen atom, or at least one oxygen atom, or at indeno substituent or their alkyl or aryl substituted deriva least one Sulfur atom, or at least one boron atom, or at least tive; or one phosphorus atom, or at least one silicon atom, or any US 7,183,010 B2 39 40 combination thereof, or any two adjacent R through Rio least one nitrogen atom, or at least one oxygen atom, or at Substituents form an annelated benzo-, naphtho-, anthra-, least one Sulfur atom, or at least one boron atom, or at least phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or one phosphorus atom, or at least one silicon atom, or any peryleno-substituent or its alkyl or aryl substituted deriva combination thereof, or any two adjacent R through Re tive; or any two R through Rio Substituents form a 12 Substituents form an annelated benzo-, naphtho-, anthra-, benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 peryleno-substituent or its alkyl or aryl substituted deriva Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, tive; or any two R through R. Substituents form a 12 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 10 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 indeno substituent or their alkyl or aryl substituted deriva Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, tive; or 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or (m) 15 indeno substituent or their alkyl or aryl substituted deriva R13 R14 R R2 R3 tive; or

(o) R12 O R4 R R R Rs R10 R3 R10 Ro Rs R R6 R9 wherein: N R4 25 Substituents R through Ra are each individually hydro Rs gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky Rs R6 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 R7 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 30 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 wherein: carbon atoms, Substituted aryl, heterocycle containing at substituents R through Ro are each individually hydro least one nitrogen atom, or at least one oxygen atom, or at gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky least one Sulfur atom, or at least one boron atom, or at least lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl one phosphorus atom, or at least one silicon atom, or any 35 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 combination thereof, or any two adjacent R through Ra. Substituents form an annelated benzo-, naphtho-, anthra-, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 peryleno-substituent or its alkyl or aryl substituted deriva carbon atoms, Substituted aryl, heterocycle containing at tive; or any two R through R. Substituents form a 12 least one nitrogen atom, or at least one oxygen atom, or at benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra 40 least one Sulfur atom, or at least one boron atom, or at least ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 one phosphorus atom, or at least one silicon atom, or any Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, combination thereof, or any two adjacent R through Rio 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, Substituents form an annelated benzo-, naphtho-, anthra-, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or indeno substituent or their alkyl or aryl substituted deriva 45 peryleno-substituent or its alkyl or aryl substituted deriva tive; or tive; or any two R through Rio Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 (n) Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 50 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, R14 R15 R16 R R2 R3 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or R13 R4 indeno substituent or their alkyl or aryl substituted deriva tive; or 55 R12 Rs (p) R R10 Ro Rs R R6 wherein: 60 Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 65 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at US 7,183,010 B2 41 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky (r) lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl R11 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 R10 R12 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, R alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 R carbon atoms, Substituted aryl, heterocycle containing at R6 least one nitrogen atom, or at least one oxygen atom, or at 10 Rs least one Sulfur atom, or at least one boron atom, or at least R3 one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. R4 Substituents form an annelated benzo-, naphtho-, anthra-, Ri Rs phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 15 R6 peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 wherein: benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra Substituents R through R are each individually hydro ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, indeno substituent or their alkyl or aryl substituted deriva alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 tive; or carbon atoms, Substituted aryl, heterocycle containing at 25 least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R.

(q) Substituents form an annelated benzo-, naphtho-, anthra-, 30 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 35 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or 40

(s) wherein: 45 Substituents R through Ro are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 50 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at wherein: least one nitrogen atom, or at least one oxygen atom, or at Substituents R through Ra are each individually hydro least one Sulfur atom, or at least one boron atom, or at least gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky one phosphorus atom, or at least one silicon atom, or any 55 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl combination thereof, or any two adjacent R through Rio silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 Substituents form an annelated benzo-, naphtho-, anthra-, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 peryleno-substituent or its alkyl or aryl substituted deriva carbon atoms, Substituted aryl, heterocycle containing at tive; or any two R through Rio Substituents form a 12 60 least one nitrogen atom, or at least one oxygen atom, or at benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra least one Sulfur atom, or at least one boron atom, or at least ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 one phosphorus atom, or at least one silicon atom, or any Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, combination thereof, or any two adjacent R through Ra. 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, Substituents form an annelated benzo-, naphtho-, anthra-, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 65 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or indeno substituent or their alkyl or aryl substituted deriva peryleno-substituent or its alkyl or aryl substituted deriva tive; or tive; or any two R through R. Substituents form a 12 US 7,183,010 B2 43 44 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1,2-anthra one phosphorus atom, or at least one silicon atom, or any ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP 1.12 combination thereof; or any two adjacent R through Ra Per 9, 10-PhAn, 1.9-An, 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, substituents form an annelated benzo-, naphtho-, anthra 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2-F1An, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 3,4-Per, 7,8-F1An, 8.9-F1An, 2.3-TriP 1.2-TriP. ace, or 5 peryleno-substituent or its alkyl or aryl substituted deriva indeno substituent or their alkyl or aryl substituted deriva tive; or any two R through Ra substituents form a 12 tive; or benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP. 1,12 (t) Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 10 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7,8-F1An, 8.9-F1An, 2.3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or

15

wherein: substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 25 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at wherein: least one sulfur atom, or at least one boron atom, or at least 30 substituents R through R are each individually hydro one phosphorus atom, or at least one silicon atom, or any gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky combination thereof; or any two adjacent R through R. lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl substituents form an annelated benzo-, naphtho-, anthra-, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, peryleno-substituent or its alkyl or aryl Substituted deriva 35 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 tive; or any two R through R. Substituents form a 1.2- carbon atoms, substituted aryl, heterocycle containing at benzo. 1.2-naphtho. 2.3-naphtho. 1.8-naphtho. 1.2-anthra least one nitrogen atom, or at least one oxygen atom, or at ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1.12-TriP 1.12 least one sulfur atom, or at least one boron atom, or at least Per 9,10-PhAn, 1.9-An, 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, one phosphorus atom, or at least one silicon atom, or any 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2-F1An, 40 combination thereof; or any two adjacent R through Rio 3,4-Per, 7,8-F1An, 8.9-F1An, 2.3-TriP 1.2-TriP. ace, or substituents form an annelated benzo-, naphtho-, anthra-, indeno substituent or their alkyl or aryl substituted deriva phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or tive; or peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 1.2- 45 benzo. 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1,2-anthra

(u) ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1.12-TriP 1.12 Per 9,10-PhAn, 1.9-An, 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2.3-TriP 1.2-TriP. ace, or 50 indeno substituent or their alkyl or aryl substituted deriva tive; or

(w) 55 wherein: substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 60 lamino, dialkylamino, trialkylsilyl, triarylsilyl diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at 65 least one nitrogen atom, or at least one oxygen atom, or at least one sulfur atom, or at least one boron atom, or at least US 7,183,010 B2 45 46 wherein:

Substituents R through Ra are each individually hydro (y) gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least 10 one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through Ra. Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva 15 tive; or any two R through R. Substituents form a 12 wherein: benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra Substituents R through R are each individually hydro ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, indeno substituent or their alkyl or aryl substituted deriva alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 tive; or carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at 25 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. (x) Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 30 peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 35 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or 40 (Z)

wherein: 45 Substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 50 alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any 55 combination thereof, or any two adjacent R through Ra. Substituents form an annelated benzo-, naphtho-, anthra-, wherein: phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or Substituents R through Rs are each individually hydro peryleno-substituent or its alkyl or aryl substituted deriva gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky tive; or any two R through R. Substituents form a 12 60 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, carbon atoms, Substituted aryl, heterocycle containing at 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 65 least one nitrogen atom, or at least one oxygen atom, or at indeno substituent or their alkyl or aryl substituted deriva least one Sulfur atom, or at least one boron atom, or at least tive; or one phosphorus atom, or at least one silicon atom, or any US 7,183,010 B2 47 48 combination thereof, or any two adjacent R through Ris lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl Substituents form an annelated benzo-, naphtho-, anthra-, silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, peryleno-substituent or its alkyl or aryl substituted deriva alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 tive; or any two R through Rs Substituents form a 12 carbon atoms, Substituted aryl, heterocycle containing at benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra least one nitrogen atom, or at least one oxygen atom, or at ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 least one Sulfur atom, or at least one boron atom, or at least Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, one phosphorus atom, or at least one silicon atom, or any 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, combination thereof, or any two adjacent R through Ra. 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 10 Substituents form an annelated benzo-, naphtho-, anthra-, indeno substituent or their alkyl or aryl substituted deriva phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or tive; or peryleno-substituent or its alkyl or aryl substituted deriva (aa) tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra 15 ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or (ac) PAH compounds that can be drawn using only fully aromatic benzene rings So as to form graphite-like segments in the following fashion:

25 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 30 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at 35 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through Re Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 40 peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 45 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive; or 50

(ab)

55

60

wherein: 65 Substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky

US 7,183,010 B2 53 54 just one molecule. The absence of the interaction can evolve e.g. due to the intrinsic lack of forces that enable the interaction, distances between the molecules being too large, improper geometry, Steric hindrance, and other reasons. The aggregate state is defined as a state formed by an interaction, for example such as commonly known in the art Van der o Waals forces or by commonly known in the art charge transfer interactions, of at least two molecules. It has physi cal and chemical properties different from those of the 10 monomer state. In particular, two or more molecules can participate in cooperative absorption or emission or both, that is absorption or emission or both can only be understood as arising from molecular complexes or molecular aggre COOO gates. When two or more molecules act cooperatively to 15 absorb a photon, it is said that the absorption aggregate CICIOOC exists in the ground electronic state. When two or more molecules act cooperatively to emit a photon, it is said that the exciplex, or a molecular complex or molecular aggre gate, exists in the excited electronic state. The absorption aggregate need not form an exciplex upon excitation and the exciplex need not emit to produce a ground state aggregate. Thus, the aggregate state can exist in either ground elec tronic state or excited electronic state or both. An aggregate state can be only weakly associated in the ground electronic 25 state (the energy of van der Waals interactions ~1–3 kcal/ OO mol) but more strongly associated in its excited electronic state (the energy of van der Waals interactions -3–10 kcal/mol). The simplest aggregate state in the ground elec wherein: tronic state is often called a dimer, that is an aggregate State Substituents in each position for each compound and 30 formed by two molecules in their ground electronic states. analogous compounds of the homological series are each The aggregate state in the excited electronic state is called an individually hydrogen, fluoro, cyano, alkoxy, aryloxy, dia excimer and in the simplest case is formed by two molecules rylamino, arylalkylamino, dialkylamino, trialkylsilyl, triar one of which prior to formation of the exciplex was in the ylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanom ground electronic state and the other was in the excited ethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 35 electronic state. One of the most commonly observed fea 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, tures of aggregate states is that either their absorption aryl of from 5 to 30 carbon atoms, substituted aryl, hetero spectrum or their emission spectrum or both are shifted cycle containing at least one nitrogen atom, or at least one compared to the absorption spectrum or emission spectrum oxygen atom, or at least one sulfur atom, or at least one or both, respectively, of the monomer state. The shift can boron atom, or at least one phosphorus atom, or at least one 40 occur to the red or to the blue. On the other hand, the silicon atom, or any combination thereof, or any two adja absorption or emission spectra or both of aggregate states cent Substituents form an annelated benzo-, naphtho can contain new features such as peaks and shoulders anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, positioned to either red or blue compared to the absorption or peryleno-substituent or its alkyl or aryl substituted deriva or emission spectrum or both of the monomer state, respec tive; or any two Substituents form a 1,2-benzo, 1.2-naphtho, 45 tively. Another most commonly observed characteristic of 2.3-naphtho. 1.8-naphtho. 1,2-anthraceno, 2.3-anthraceno, aggregate states is that the intensity and sometimes the 2,2'-BP, 4,5-PhAn, 1,12-TriP 1,12-Per, 9,10-PhAn, 1.9-An, position (wavelength) of the new or shifted absorption or 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, emission or both depend on concentration of molecules that 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7,8-F1An, 8.9-F1An, form the aggregate state. With increasing concentration, the 2,3-TriP 1.2-TriP. ace, or indeno substituent or their alkyl or 50 intensity of shifted absorption or emission features or both aryl substituted derivative; or can increase due to the increasing concentration of the (ad) any of the compounds 2 through 1315. aggregate states, while the position, or wavelength, can shift One particular selection criterion for the first host com too due to the increase in the size (number of molecules ponent is that the organic compound should have a molecu involved in the formation) of the aggregate states. Another lar structure that enables it to form both monomer state and 55 common characteristic of aggregate states which is observed aggregate state. The aggregate state can be formed by at least in the absence of readily detectable changes in the monomer two molecules of the same compound, Such as the first host absorption or emission spectrum or both is the change in the component, or by at least two molecules of two different intensity (quantum yield of luminescence) of the monomer compounds. Such as the first and second host components or emission. For reference, these definitions can be found in first component and the luminescent dopant. All these aggre 60 N.J. Turro, Modem Molecular Photochemistry, University gate states are useful in the present invention. However, the Science Books, Sausalito, Calif. 1991. following discussion will be focused on the first case. The For some organic compounds, their molecular structure is monomer State is defined as a state where molecules of the Such that their aggregates in excited electronic states are first host component do not interact with each other in either emissive, and thus can be readily observed by measuring ground or excited electronic state and thus behave as single 65 fluorescence emission spectra as a function of concentration, molecules in a solid solution of the second component. Thus, for example FIGS. 4-16; Table 1. Compounds that form in particular their absorption and emission processes involve emissive and highly emissive aggregate states are potentially US 7,183,010 B2 55 56 the most useful as first host components. However, there are Materials for the second host component of the lumines many organic compounds that form aggregate states which cent layer of the present invention include organic com are not emissive or only weakly emissive. Formation of pounds that are capable of forming a continuous and Sub completely or essentially non-emissive aggregate states (that stantially pin-hole-free thin film upon mixing with the first is those with the quantum yield of luminescence of Zero or host component. They can be polar, Such as (i) the common near Zero) can lead to a decrease in the efficiency of host for green, yellow, orange, and red OLEDS AlQ and electroluminescence and photoluminescence due to insuffi other oxinoid and OXinoid-like materials and metal com cient efficiency of electronic excitation energy transfer to the plexes, and (ii) common hosts of heterocyclic family for luminescent dopant. Nevertheless, for certain types of com blue, blue-green, green, yellow, orange, and red OLEDS pounds, especially the ones listed above, the quantum yield 10 Such as those based on oxadiazole, imidazole, pyridine, of luminescence of an aggregate State is most often found to phenanthroline, triazine, triazole, quinoline and other moi be non-zero. This can be sufficient to sustain a sufficient rate eties. They also can be nonpolar, Such as (i) the common of electronic excitation energy to the luminescent dopant, if hosts of anthracene family for blue, blue-green, green, the latter acts as a Sufficiently strong acceptor in the well yellow, orange, and red OLEDs, such as 2-(1,1-dimethyl known in the art Foerster energy transfer process. Therefore, 15 ethyl)-9,10-bis(2-naphthalenyl)anthracene (TBADN), 9,10 Such compounds would not compromise the electrolumines Bis4-(2,2-diphenylethenyl)phenylanthracene, and 10,10'- cence efficiency and could also be useful as first host Diphenyl-9.9-bianthracene; (ii) common hosts of rubrene components. Their use would result not only in improved family for yellow, orange, and red OLEDs, such as rubrene operational lifetimes but also in excellent EL efficiencies. and 5,6,11,12-tetrakis(2-naphthyl)tetracene; and (iii) com On the other hand, if the acceptor (luminescent dopant) of mon hosts of triarylamine family for blue, blue-green, green, the excitation energy transfer is strong and its concentration yellow, orange, and red OLEDs such as NPB, TNB, and is sufficiently high so that the quantum efficiency of the TPD. The second host component can have a bandgap that energy transfer is ~100% then even if the quantum yield of is less than, more than, or equal to that of the first host luminescence of the donor decreases by 10–15 times (given component in either its monomer state or aggregate state. that everything else remains equal) the quantum efficiency 25 The bandgap (or energy gap) is defined as the energy needed to bring an electron from the highest occupied molecular of the energy transfer, and thus of the acceptor lumines orbital to the lowest unoccupied molecular orbital of the cence, decreases only by ~10%. molecule. When the bandgap of the first host component in Another important criteria for selection of compounds as its monomer state is approximately equal to that of the first host components is that the aggregate States of this 30 second host component and the dopant is absent, the pho compound should have spectroscopic characteristics, toluminescence (PL) and electroluminescence (EL) spectra namely absorption and emission spectra, excited State life are composed of the emission spectra of both species. This time, quantum yield of luminescence, and oscillator can be seen in FIG. 4 and FIG. 6, the curves corresponding strength, such that efficient transfer of electronic excitation to 2% and 4% cases. This can be further seen in FIGS. 8, 10, energy to the luminescent dopant of appropriate color is 35 11, and 12. When the bandgap of the first host component in insured. its monomer state is approximately equal to that of the first Many of the benzenoid compounds found useful as the host component in its aggregate state and to that of the first host component in the present invention have a flat rigid second host component (while the dopant is absent), the PL geometry, which encourages formation of aggregate states. and EL spectra are composed of the emission spectra of all Many representative benzenoids, such as pyrene, perylene, 40 three species. This can be seen for example in FIG. 4 and coronene, naphthacene, anthracene, pentacene, FIG. 6, the curves corresponding to 6% and 10% cases. anthanthrene, picene, triphenylene, chrysene, fluoranthene, When the bandgap of the first host component in its aggre benZoghilperylene, ovalene, etc. and their mono- and poly gate state is Smaller than that of the second host component Substituted benzo, naphtho, anthra, phenanthro, triph and the dopant is absent, the PL and EL spectra are domi enyleno, and other derivatives have been shown in the 45 nated by the emission spectrum of the first host component common literature to possess a pronounced propensity for in its aggregate State. This can be seen in FIG. 4 and FIG. 6. aggregate state formation. The aggregate States of these the curves corresponding to 15% case. Note that in all these compounds are extensively characterized in common litera cases the composition of the PL and EL spectra is also a ture. If the PAH compound is emissive in its monomer state, Subject to concentration, particularly of the aggregates of the it is most often found to be emissive in its aggregate state 50 first host component, and to quantum yield of luminescence also, especially in the solid solutions and in the absence of and lifetime of the singlet excited states of all the species oxygen (exactly as found in an OLED device). Other organic involved. compounds meeting Such a planar geometry criteria are The necessary condition is that the bandgap of the lumi useful as well. nescent dopant be Smaller than the bandgap of the second Although aggregate states including two molecules are 55 host component, the bandgap of first host component in its most often found and described in the literature, often it is monomer state, and the bandgap of the first host component found that compounds such as disclosed in the present in its aggregate state. This ensures that electronic excitation invention are capable of forming aggregate states including energy transfer from the first and second host components, not only two molecules, but of three, four, five, ten, hundred, resulting from the recombination of electrons and holes in thousand and more molecules as the Volume '% increases. 60 the first and second host components, to the light-producing With sufficiently high number of molecules of the first host dopants is favorable. component participating in the formation of an aggregate Any one of the following three-second host component, state, a domain could be formed where certain degree of the first host component in its monomer state, and the first order or degree of crystallinity could be found. The size of host component in its aggregate state—can have the lowest these domains could be in the range of nanometers (nanoc 65 bandgap between the three. The lowest bandgap material can rystalline domain) or even micrometers (microcrystalline also serve as a hole trap, an electron trap, or both but so can domain). the species that does not necessarily have the lowest band US 7,183,010 B2 57 58 gap. Trapping injected and transported carriers directly on the molecules of a single host component can be beneficial as it promotes electron-hole recombination in this host component, shortcutting the need for carrier recombination in the other host component which can have implications for 5 R10 R4 the size, density distribution, and geometry of the recombi nation Zone as well as operational stability of OLED devices. Under this condition, the other host component is needed for carrier transport only and not for charge carrier recombination. 10 The first preferred class of materials for the second host component is the oXinoid compounds. Exemplary of con wherein templated oxinoid compounds are those satisfying the fol Substituents R and R, are each individually and indepen lowing structural formula: 15 dently alkenyl of from 1 to 24 carbonatoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur Z ) atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination (2) OR (2) 2O thereof; and substituents R through Ro excluding R and O / O / R, are of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 YMen YM in carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at 25 least one oxygenatom, or at least one Sulfur atom, or at least wherein: one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two Me represents a metal; adjacent R through Rio Substituents excluding R and R, n is an integer of from 1 to 3; and form an annelated benzo-, naphtho-, anthra-, phenanthro-, Z independently in each occurrence represents the atoms so fluorantheno-, pyreno-, triphenyleno-, or peryleno-Substitu completing a nucleus having at least two fused aromatic ent or its alkyl or aryl substituted derivative:or any two rings. adjacent R through Rio Substituents excluding R and R-7 From the foregoing it is apparent that the metal can be form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, monovalent, divalent, or trivalent metal. The metal can, for 1,2-anthraceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12 example, be an alkali metal. Such as lithium, Sodium, 35 TriP, 1,12-Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, form a 12 rubidium, cesium, or potassium; an alkaline earth metal, benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra Such as magnesium, strontium, barium, or calcium; or an ceno, 2,3-anthraceno, 3,4-Per, 7.8-FlAn, 8.9-FlAn, 2.3-TriP. earth metal. Such as boron or aluminum, gallium, and 1.2-TriP. ace, or indeno substituent or their alkyl or aryl indium. Generally any monovalent, divalent, or trivalent substituted derivative. metal known to be a useful chelating metal can be employed. 40 Illustrative of useful anthracene compounds and their Z completes a heterocyclic nucleus containing at least two abbreviated names are the following: fused aromatic rings, at least one of which is an azole or 2-(1,1-dimethylethyl)-9,10-bis(2-naphthalenyl)an azine ring. Additional rings, including both aliphatic and thracene (TBADN), aromatic rings, can be fused with the two required rings, if 9,10-bis(2-naphthalenyl)anthracene (ADN), required. To avoid adding molecular bulk without improving 45 9,10-bis(1-naphthalenyl)anthracene, on function the number of ring atoms is preferably main 9,10-bis(4-(2,2-diphenylethenyl)phenyl)anthracene, tained at 18 or less. 9,10-Bis(1,1':3", 1'-terphenyl-5-yl)anthracene, Illustrative of useful chelated oxinoid compounds and 9,9'-Bianthracene, their abbreviated names are the following: 10,10'-Diphenyl-9.9'-bianthracene, Tris(8-quinolinol)aluminum (AlO4) 50 10,10'-Bis(1,1':3'1"-terphenyl-5-yl)-9.9-bianthracene, Bis(8-quinolinol)magnesium (MgO) 2,2'-Bianthracene, Tris(8-quinolinol)gallium (GaQ) 9.9',10,10'-Tetraphenyl-2,2'-bianthracene, 8quinolinol lithium (LiO) 55 9,10-Bis(2-phenylethrnyl)anthracene, or The list further includes InC, ScC., ZnO, BeBd (bis(10 9-Phenyl-10-(phenylethynyl)anthracene. hydroxybenzohquinolinato)beryllium), Al(4-MeO), Al(2- Another class of materials useful as the second host MeO), Al(2.4-MeO), Ga(4-MeO), Ga(2-MeO), Ga(2. component includes structures having an amine moiety. 4-MeO), and Mg(2-MeO). The list of oxinoid compounds Exemplary of contemplated amino compounds are those further includes metal complexes with two bi-dentate go satisfying structural formula: ligands and one mono-dentate ligand, for example Al(2- MeO)(X) where X is any aryloxy, alkoxy, arylcaboxylate, and heterocyclic carboxylate group. Another class of materials useful as the second host component includes structures having an anthracene moiety. 65 Exemplary of contemplated anthracene compounds are those satisfying the following structural formula: US 7,183,010 B2 59 60 wherein: silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 Substituents Ra and Rs are each individually and indepen to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, dently aryl, or substituted aryl of from 5 to 30 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 heterocycle containing at least one nitrogen atom, or at least carbon atoms, substituted aryl, heterocycle containing at one oxygen atom, or at least one sulfur atom, or at least one least one nitrogen atom, or at least one oxygen atom, or at boron atom, or at least one phosphorus atom, or at least one least one sulfur atom, or at least one boronatom, or at least silicon atom, or any combination thereof; substituents R. one phosphorus atom, or at least one silicon atom, or any and Rs each or together (R-Rs) representing an aryl combination thereof; or any two adjacent R through Ras group Such as benzene, naphthalene, anthracene, tetracene, Substituents excluding R and Rio forman annelated benzo pyrene, perylene, chrysene, phenathrene, triphenylene, tet 10 naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno raphene, coronene, fluoranthene, pentaphene, ovalene, triphenyleno-, or peryleno-substituent or its alkyl or aryl picene, anthanthrene and their homologs and also their Substituted derivative; or any two R through Rs substitu 1.2-benzo. 1.2-naphtho. 2.3-naphtho. 1.8-naphtho. 1.2-an ents excluding Ro and Rio form a 1,2-benzo, 1.2-naphtho. thraceno. 2.3-anthraceno. 2,2'-BP, 4.5-PhAn, 1,12-TriP. 2.3-naphtho. 1.8-naphtho. 1.2-anthraceno. 2.3-anthraceno. 1,12-Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2.3-PhAn, 1,2- 15 2,2'-BP, 4.5-PhAn, 1,12-TriP. 1,12-Per, 9,10-PhAn, 1.9-An, Phan, 1.10-Pyr, 1.2-Pyr, 2.3-Per, 3.4-F1An, 2.3-F1An, 1,2- 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, FlAn, 3.4-Per, 7.8-F1An, 8.9-F1An, 2.3-TriP 1,2-TriP. ace, or 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, indeno substituted derivatives; and substituents R through 2,3-TriP 1.2-TriP. ace, or indeno substituent or their alkyl or R9 excluding R and Rs are each individually hydrogen, aryl Substituted derivative. silyl, alkyl of from 1 to 24 carbon atoms, aryl of from 5 to Illustrative of useful fluorene compounds and their abbre 30 carbon atoms, substituted aryl, heterocycle containing at viated names are the following: least one nitrogen atom, or at least one oxygen atom, or at 2,2',7,7-Tetraphenyl-9,9'-spirobi9H-fluorene, least one sulfur atom, or at least one boron atom, or at least 2.2.7.7"-Tetra-2-phenanthrenyl-9.9-spirobi9H-fluorene), one phosphorus atom, of at least one silicon atom, or any 2,2'-Bis (4-N,N-diphenylaminophenyl)-9.9-spirobi9H combination thereof. 25 fluorene (CAS 503307-40-2), Illustrative of useful amino compounds and their abbre 4'-Phenyl-spirofluorene-9,6'-6Hindeno1.2-fluoran viated names are the following: thene. N.N'-bis(1-naphthalenyl)-N,N'-diphenylbenzidine 2,3,4-Triphenyl-9.9'-spirobifluorene, (NPB), 11,11'-Spirobi 11H-benzobfluorene), N,N'-bis(1-naphthalenyl)-N,N'-bis(2-naphthalenyl)benzi 30 9.9'-Spirobi9H-fluorene-2,2'-diamine, dine (TNB), 9.9'-Spirobi9H-fluorene-2,2'-dicarbonitrile, N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine 2.7'-Bis(1,1'-biphenyl-4-yl)-N.N.N',N'-tetraphenyl-9, (TPD), or 9'-spirobi9H-fluorene-2,7-diamine, N,N'-Bis(N"N"-diphenylaminonaphthalen-5-yl)-N,N'- 9,9.9'.9'.9".9"-Hexaphenyl-2,2':7'2"-ter-9H-fluorene, diphenyl-1,5-diaminonaphthalene (CAS 503624-47-3). 35 2.7-Bis(1,1'-biphenyl-4-yl)-9.9-spirobi9H-fluorene), Another class of materials useful as the second host 2.2.7.7"-tetra-2-Naphthalenyl-9.9'-spirobi9H-fluorene), component includes structures having a fluorene moiety. Or Exemplary of contemplated fluorene compounds are those 9.9'-(2,7-Diphenyl-9H-fluoren-9-ylidene)di-4.1-phe satisfying the following structural formula: nylenebis-anthracene. 40 Another class of materials useful as the second host

component includes structures having a naphthacene moiety. Exemplary of contemplated naphthacene compounds are those satisfying the following structural formula: 45 R12 R R2 R3

50 R11 C C C R4 R10 Rs R9 Rs R R6

55 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl diarylalkyl 60 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at wherein: least one nitrogen atom, or at least one oxygen atom, or at Substituents R through Rs are each individually hydro 65 least one sulfur atom, or at least one boronatom, or at least gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky one phosphorus atom, or at least one silicon atom, or any lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl combination thereof; or any two adjacent R through R. US 7,183,010 B2 61 62 Substituents form an annelated benzo-, naphtho-, anthra-, ring; and R" is hydrogen; alkyl of from 1 to 24 carbon atoms; phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or oraryl of from 5 to 20 carbon atoms. These structures further peryleno-substituent or its alkyl or aryl substituted deriva include alkyl, alkenyl, alkynyl, aryl, Substituted aryl, benzo tive; or any two R through R. Substituents form a 12 naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra triphenyleno-, or peryleno-, 1.2-benzo, 1.2-naphtho, 2.3- ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, naphtho. 1.8-naphtho. 1.2-anthraceno. 2,3-anthraceno. 2,2'- 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, BP, 4,5-PhAn, 1,12-TriP, 1,12-Per, 9,10-PhAn, 1.9-An, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, indeno substituent or their alkyl or aryl substituted deriva 10 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7.8-F1An, 8.9-F1An, tive. 2,3-TriP 1.2-TriP. ace, indeno, fluoro, cyano, alkoxy, ary Illustrative of useful naphthacene compounds and their loxy, amino, aza, heterocyclic, keto, or dicyanomethyl abbreviated names are the following: derivatives thereof. 5,6,11,12-Tetraphenylnaphthacene (rubrene), The material selection criteria for the dopant in the 5, 12-Bis(2-naphthyl)-6,11-diphenyltetracene, 15 luminescent layer are: 1) the dopant molecule has a high 5, 12-Bis(2-mesityl)-6,11-diphenyltetracene, efficiency of fluorescence or phosphorescence in the lumi 5, 12-Bis(1-naphthyl)-6,11-diphenyltetracene, nescent layer, and 2) it has a bandgap (singlet bandgap for 5,6,11,12-Tetrakis(2-naphthyl)tetracene, the case of fluorescent dopants and triplet bandgap for the 10.10'-(6,11-Diphenyl-5,12-naphthacenediyl)di-4.1 phe case of phosphorescent dopants) Smaller than that of the nylenebis2,3,6,7-tetrahydro-1H,5H-benzothiazolo 5,6,7- both first and second host materials, the first component iquinolizine, being either in its monomer State or its aggregate state. 9,10,15, 16-Tetraphenyl-dibenzoa.cnaphthacene, For red-emitting OLEDs, a preferred class of dopants of 5,6,13,14-Tetraphenylpentacene, this invention is the DCM class and has the general formula: 4,4'-(8.9-Dimethyl-5,6,7,10,11,12-hexaphenyl-1,4-naph 25

thacenediyl)bis-benzonitrile, 4,4'-(8.9-Dimethoxy-5,6,7,10,11,12-hexaphenyl-1,4- naphthacenediyl)bis N,N-diphenylbenzenamine, 1,2,3,5,6,11,12-Heptaphenylnaphthacene, 1,4,5,6,7,10,11,12-Octaphenylnaphthacene, 30 6,11-diphenyl-5,12-bis(4-N,N-diphenylaminophenyl) naphthacene, 7.8, 15, 16-Tetraphenyl-benzoapentacene, 2,3,5,6,11,12-Hexaphenylnaphthacene, 6,11-diphenyl-5,12-bis(4-cyanophenyl)naphthacene, 35 6,11-diphenyl-5,12-bis(4-(2-thienyl)phenyl)naph thacene, or 9,10,19,20-Tetraphenyl-tetrabenzoa.cj.lnaphthacene. Another class of materials useful as the second host 40 component includes benzenoids that contain other hetero wherein: cyclic structures. These structures include benzoxazolyl, and R", R. R. and R are individually alkyl of from 1 to 10 thio and amino analogs of benzoxazolyl of following general carbon atoms; R is alkyl of from 2 to 20 carbon atoms, aryl, molecular structure: sterically hindered aryl, or heteroaryl; and R is alkyl of 45 from 1 to 10 carbon atoms, or a 5- or 6-membered carbocy clic, aromatic, or heterocyclic ring connecting with R. 2^- These materials possess fluorescence efficiencies as high as unity in solutions and emit in the orange and red spectral 50 region. Representative materials of this class and their CC abbreviated names include: wherein: DCM NC CN Z is O, NR" or S.; R and R', are individually hydrogen, 55 alkyl of from 1 to 24 carbon atoms, aryl or hetero-atom substituted aryl of from 5 to 20 carbon atoms, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, 60 alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus 65 atom, or at least one silicon atom, or any combination thereof, or atoms necessary to complete a fused aromatic US 7,183,010 B2 63 64

-continued -continued

NC CN

10 o 15

NC CN NC CN

25 s' 30 35 DCJTMes DCJTE NC CN NC CN

40

O g 45 50

DCTTP For red-emitting OLEDs, another preferred class of NC CN dopants of this invention comprises compounds having a periflanthene moiety: 55

R13 R14 R15 R16 R R 60 R11 O R2 3. R3 65 Rs R Rs US 7,183,010 B2 65 66 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least 10 one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or C-6 peryleno-substituent or its alkyl or aryl substituted deriva 15 tive; or any two R through R. Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva tive. These materials possess fluorescence efficiencies as high as unity in solutions and emit in the orange and red spectral 25 region. One representative material of this class is:

Red 2 30 Ph Ph

35 Ph Ph For green-emitting OLEDs, another class of fluorescent materials is useful as the dopants in the present invention, For green-emitting OLEDs, a class of fluorescent mate which includes compounds having a quinacridone moiety: rials is useful as the dopants in the present invention, which 40 includes compounds having a coumarin moiety:

R4 R5 R6 O R Rs N 45 R3 O CO R2 R R3 R O R7 Rs 50 wherein: substituents R through R, are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 55 lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 wherein: to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, X=S, O, or NR7; R and Rare individually alkyl of from alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 1 to 20 carbonatoms, aryl or carbocyclic systems; R and R. carbon atoms, Substituted aryl, heterocycle containing at are individually alkyl of from 1 to 10 carbon atoms, or a 60 least one nitrogen atom, or at least one oxygen atom, or at branched or unbranched 5 or 6 member substituent ring least one Sulfur atom, or at least one boron atom, or at least connecting with R and R, respectively; Rs and R are one phosphorus atom, or at least one silicon atom, or any individually alkyl of from 1 to 20 carbon atoms, which are combination thereof; or any two adjacent R through Ra. branched or unbranched; and R, is any alkyl or aryl group. Substituents form an annelated benzo-, naphtho-, anthra-, These materials possess fluorescence efficiencies as high 65 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or as unity in solutions. Representative materials of this class peryleno-substituent or its alkyl or aryl substituted deriva and their abbreviated names include: tive; or any two R through R. Substituents form a 12 US 7,183,010 B2 67 68 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra wherein: ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 substituents R through R are each individually hydro Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 indeno substituent or their alkyl or aryl substituted deriva to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, tive. alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 These materials possess fluorescence efficiencies as high carbon atoms, Substituted aryl, heterocycle containing at as unity in solutions. Representative materials of this class 10 least one nitrogen atom, or at least one oxygen atom, or at and their abbreviated names include: least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through Ro Quinacridone, QA Substituents form an annelated benzo-, naphtho-, anthra-, 15 H O phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or N peryleno-substituent or its alkyl or aryl substituted deriva tive; or any two R through Ro Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra N ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, O H 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, Dimethylquinacridone, DMQA 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or indeno substituent or their alkyl or aryl substituted deriva 25 tive. These materials possess fluorescence efficiencies as high as unity in solutions. Representative materials of this class include: 30

O Me DPMB1 Diphenylquinacridone, DPQA Ph O 35 N

DO 40 O Ph

CFDMQA

45

50

For green, green-yellow, and yellow emitting OLEDs, another class of fluorescent materials is useful as the dopants in the present invention, which includes compounds having a DPMB (dipyridinomethene borate) moiety:

60

65 For yellow- and orange-emitting OLEDs, a preferred class of dopants for this invention includes compounds having an indenoperylene moiety: US 7,183,010 B2 70 wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at 10 least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R2 Substituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or wherein: 15 peryleno-substituent or its alkyl or aryl substituted deriva Substituents R through Ra are each individually hydro tive; or any two R through R. Substituents form a 12 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or carbon atoms, Substituted aryl, heterocycle containing at indeno substituent or their alkyl or aryl substituted deriva least one nitrogen atom, or at least one oxygen atom, or at tive. least one Sulfur atom, or at least one boron atom, or at least These materials possess fluorescence efficiencies as high 25 as unity in Solutions and emit in the spectral region from one phosphorus atom, or at least one silicon atom, or any greenish-yellow to red. Representative materials of this class combination thereof, or any two adjacent R through Ra. and their abbreviated names include: Substituents form an annelated benzo-, naphtho-, anthra-, 5,6,11,12-Tetraphenylnaphthacene (rubrene), phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 2,2'-(6,11-diphenyl-5,12-naphthacenediyl)di-4,1-phe peryleno-substituent or its alkyl or aryl substituted deriva 30 nylenebis(6methylbenzothiazole) (Orange 2), tive; or any two R through R. Substituents form a 12 5,12-Bis(2-mesityl)-6,11-diphenyltetracene, benzo, 1,2-naphtho, 2.3-naphtho, 1.8-naphtho. 1,2-anthra 5,6,11,12-Tetrakis(2-naphthyl)tetracene, ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 10,10'-(6,11-Diphenyl-5,12-naphthacenediyl)di-4.1 phe Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, nylenebis2,3,6,7-tetrahydro-1H,5H-benzothiazolo 5,6,7- 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 35 iquinolizine, 3,4-Per, 7,8-F1An, 8.9-F1An, 2,3-TriP, 12-TriP. ace, or 5,6,13,14-Tetraphenylpentacene, indeno substituent or their alkyl or aryl substituted deriva 4,4'-(8.9-Dimethoxy- 5,6,7,10,11,12-hexaphenyl-1,4- tive. naphthacenediyl)bis N,N-diphenylbenzenenamine, These materials possess fluorescence efficiencies as high 6,11-diphenyl-5,12-bis(4'-N,N-diphenylaminophenyl) as unity in solutions. One representative material of this 40 naphthacene, class is: 7,8,15, 16-Tetraphenyl-benzoapentacene, or 6,11-diphenyl-5,12-bis(4-cyanophenyl)naphthacene. For green-blue, blue-green, and blue-emitting OLEDs, a Yellow-green 2 preferred class of dopants for this invention includes com 45 Ph pounds having a BASB (bisaminostyrylbenzene) moiety:

50

Ph

For yellow- and orange-emitting OLEDs, another pre ferred class of dopants for this invention includes com 55 pounds having a naphthacene moiety:

wherein: R12 R R2 R3 60 each double bond can be either E or Z independently of the other double bond; substituents R through Ra are each individually and independently alkyl of from 1 to 24 carbon R11n2 CO R4 atoms, aryl, or substituted aryl of from 5 to 30 carbon atoms, R10 Rs heterocycle containing at least one nitrogen atom, or at least 65 one oxygen atom, or at least one Sulfur atom, or at least one Ro Rs R R6 boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, and Substituents US 7,183,010 B2 71 72 Rs through Ro are each individually hydrogen, fluoro, to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, cyano, alkoxy, aryloxy, diarylamino, arylalkylamino, dialky alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 lamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylar carbon atoms, Substituted aryl, heterocycle containing at ylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon least one nitrogen atom, or at least one oxygen atom, or at atoms, alkenyl of from 1 to 24 carbonatoms, alkynyl of from least one Sulfur atom, or at least one boron atom, or at least 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, one phosphorus atom, or at least one silicon atom, or any Substituted aryl, heterocycle containing at least one nitrogen combination thereof, or any two adjacent R through R2 atom, or at least one oxygen atom, or at least one Sulfur Substituents form an annelated benzo-, naphtho-, anthra-, atom, or at least one boron atom, or at least one phosphorus phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or atom, or at least one silicon atom, or any combination 10 thereof, or any two adjacent Rs through Ro Substituents peryleno-substituent or its alkyl or aryl substituted deriva form an annelated benzo-, naphtho-, anthra-, phenanthro-, tive; or any two R through R. Substituents form a 12 fluorantheno-, pyreno-, triphenyleno-, or peryleno-Substitu benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ent or its alkyl or aryl substituted derivative; or any two Rs ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 through Ro Substituents form a 12-benzo, 1.2-naphtho, 15 Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, 2.3-naphtho. 1.8-naphtho. 1,2-anthraceno, 2.3-anthraceno, 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, 2,2'-BP, 4,5-PhAn, 1,12-TriP 1,12-Per, 9,10-PhAn, 1.9-An, 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or 1,10-PhAn, 2.3-PhAn, 1.2-PhAn, 1,10-Pyr, 1.2-Pyr, 2.3-Per, indeno substituent or their alkyl or aryl substituted deriva 3,4-F1An, 2.3-F1An, 1.2-F1An, 3,4-Per, 7,8-F1An, 8.9-F1An, tive. 2,3-TriP 1.2-TriP. ace, or indeno substituent or their alkyl or These materials possess fluorescence efficiencies as high aryl substituted derivative. as unity in solutions. Representative materials of this class These materials possess fluorescence efficiencies as high include: as unity in solutions. Representative materials of this class Perylene include: 4-(Diphenylamino)-4-4-(diphenylamino)styrylstilbene, 25 2,5,8,11-Tetra-tert-butylperylene (TBP) 4-(Di-p-Tolylamino)-4-(di-p-tolylamino)styrylstilbene 2.8-Di-tert-Butylperylene (Blue-green 2), Benzo(bperylene 4,4'-(2,5-Dimethoxy-1,4-phenylene)di-2,1-ethenediyl Dibenzob.kperylene bisN,N-bis(4-methylphenyl)benzenamine, 4,4'-(1,4-Naphthalenediyldi-2,1-ethenediyl)bis N,N-bis 30 For blue-emitting OLEDs, another preferred class of (4-methylphenyl)benzenamine, dopants for this invention includes compounds having a 3,3'-(1,4-Phenylenedi-2,1-ethenediyl)bis 9-(4-ethylphe ADPMB (aza-DPMB) moiety: nyl)-9H-carbazole, 4,4'-(1,4-Phenylenedi-2,1-ethenediyl)bis N,N-diphenyl 1-naphthalenamine, 35 Rs R 4,4'-1,4-Phenylenebis(2-phenyl-2,1-ethenediyl)bis N. R N R N-diphenylbenzenamine, "Nea N1S1 4,4',4'-(1,2,4-Benzenetriyltri-2,1-ethenediyl)tris N,N- diphenylbenzenamine, R6 N N N1 N 21 R3 9,10-Bisa-(di-p-tolylamino)styrylanthracene, or 40 / V C.C.'-(1,4-Phenylenedimethylidyne)bis 4-(dipheny Rs F F R4 lamino)-1-naphthaleneacetonitrile. For blue-emitting OLEDs, a preferred class of dopants for this invention includes compounds having a perylene moi wherein: ety: 45 Substituents R through Rs are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl R12 R silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 50 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, R11 R alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at R10 R3 least one Sulfur atom, or at least one boron atom, or at least Ro R4 55 one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through Rs Substituents form an annelated benzo-, naphtho-, anthra-, Rs Rs phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted deriva R R6 60 tive; or any two R through Rs Substituents form a 12 benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthra ceno, 2,3-anthraceno, 2,2'-BP, 4.5-PhAn, 1,12-TriP, 1,12 wherein: Per, 9,10-PhAn, 1.9-An, 1,10-PhAn, 2,3-PhAn, 1.2-PhAn, Substituents R through R are each individually hydro 1,10-Pyr, 1.2-Pyr, 2.3-Per, 3,4-F1An, 2.3-F1An, 1.2-F1An, gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, arylalky 65 3,4-Per, 7.8-F1An, 8.9-F1An, 2,3-TriP 1,2-TriP. ace, or lamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkyl indeno substituent or their alkyl or aryl substituted deriva silyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 tive. US 7,183,010 B2 73 74 These materials possess fluorescence efficiencies as high Another useful method for forming the luminescent layer as unity in solutions. Representative materials of this class of the present invention is by spin-coating or by ink-jet include: printing. This method is particularly useful for fabricating lower-cost OLED devices. Composition of the luminescent layer is determined by the concentration of each component Blue 2 in the Solutions being coated.

Returning to FIG. 2, hole-transport layer 231 and elec NN1 N tron-transport layer 233 provide the functions of transport ing holes and electrons, respectively, to the luminescent n-N 2 10 layer 232. The use of these layers and their material com positions in OLED devices have been disclosed by Tang et F F al. in commonly assigned U.S. Pat. No. 4,769,292, included herein by reference. A typical hole-transport layer includes the hole-transporting compounds such as N,N'-bis(1-naph 15 thyl)-N,N'-diphenylbenzidine (NPB), N,N'-bis(1-naphthyl)- ADPMB1 F F N,N'-bis(2-naphthyl)benzidine (TNB), and N,N'-bis(3- F F tolyl)-N,N'-diphenylbenzidine (TPD). N Returning to FIG. 3, hole-injection layer 331 and elec F N n N F tron-injection layer 335 provide the functions of improving the hole-injection from the anode and electron-injection 2 N-N from the cathode 340, respectively. The use of a hole / V injection layer in OLED devices has been disclosed by Van F F Slyke et al. in commonly assigned U.S. Pat. No. 4,720,432, ADPMB2 included herein by reference. The use of an electron-injec 25 tion layer has been disclosed by Hung et al. in commonly assigned U.S. Pat. No. 5,776,622, also included herein by N reference. 21 n WORKING EXAMPLES 1 19 S N-N 21 30 / V Electroluminescence of Aggregates of Various F F Materials OLED devices were prepared as follows. A glass substrate The composition of the luminescent layer of this inven 35 coated with about 850 A transparent indium-tin-oxide (ITO) tion is such that either the first host component or the second conductive layer was cleaned and dried using a commercial host component can constitute the largest Volume fraction of glass scrubber tool. The ITO surface was subsequently the luminescent layer. The dopant usually constitutes the treated with an oxidative plasma to condition the Surface as smallest volume fraction. The range for the first host com an anode. Over the ITO was deposited a 10 A thick hole ponent is from 1 to 99 volume % of the luminescent layer. 40 injecting layer of fluorocarbon (CFX) by plasma-assisted The preferred range for the first host component is from 5 to deposition of CHF. The following layers were deposited in 95% by volume. The range for the second host component the following sequence by sublimation from heated crucible is from 1 to 99 volume 96 of the luminescent layer. The boats in a conventional vacuum deposition chamber under a preferred range for the second host component is from 5 to vacuum of approximately 10 Torr: (1) a hole-transport 45 layer, 750 A thick, including NPB, (2) a luminescent layer, 95% by volume. The concentration range for the dopant is 350 A thick, including the first and second host components from 0.1% to 10% by volume. The preferred concentration in certain ratio (indicated in Table 1) and not containing range for the dopant is from 0.5% to 5% by volume. The luminescent dopants, (3) an electron-transport layer, 350 A thickness of the luminescent layer useful in this invention is thick, including AlQ, and (4) a cathode, approximately between 50 Angstroms and 5000 Angstroms. A thickness in 50 2200 A thick, including an alloy of magnesium and silver this range is sufficiently large to enable recombination of with a Mg: Ag volume ratio of about 10:1. Following that the charge carriers and, therefore, electroluminescence to take devices were encapsulated in nitrogen atmosphere along place exclusively in this layer. A preferred range is between with calcium Sulfate as a desiccant. 100 Angstroms and 1000 Angstroms, where the overall The EL characteristics of these devices were evaluated OLED device performance parameters, including drive volt 55 using a constant current source and a photometer. The drive age, are optimal. voltage, EL efficiency in cd/A and W/A, CIE coordinates, A useful method for forming the luminescent layer of the peak wavelength, w, full spectral width at half-maximum, present invention is by vapor deposition in a vacuum cham FWHM, and loss or gain in EL efficiency as current density, ber. This method is particularly useful for fabricating OLED J, increases from 0.5 to 100 mA/cm, A cd/A vs J, at current devices, where the layer structure, including the organic 60 densities ranging from relatively low, 0.5 mA/cm, to rela layers, can be sequentially deposited on a Substrate without tively high, 100 mA/cm, were measured. The EL efficiency significant interference among the layers. The thickness of in W/A, CIE coordinates, W, FWHM, and description of each individual layer and its composition can be precisely the EL color and spectrum at 20 mA/cm are given in Table controlled in the deposition process. To produce the desired 1. composition of the luminescent layer, the rate of deposition 65 As can be seen from Table 1 it is common for materials for each component is independently controlled using a luminescent in their monomer State to form the aggregate deposition rate monitor. states which are also luminescent in both polar and non US 7,183,010 B2 75 76 polar environments and electroluminescence for the aggre forward bias at 80 mA/cm alternating with the 0.5 ms of gate states of these materials is readily observed. It further reverse bias of -14V) and at room temperature and at can be seen that the range of aggregate electroluminescence average current density of 20 mA/cm (0.5 ms forward bias spans the whole visible spectrum and can be tuned by proper at 40 mA/cm alternating with the 0.5 ms of reverse bias of choice of materials. -14V) and at 70°C., and the effects of addition of the 1 host FIGS. 4 through 16 illustrate photoluminescence and component on the operational stability of the OLED devices. electroluminescence spectra for many of the Examples The devices were permitted to run for 250–2000 hours, after 1-19. which time the aging was stopped and if Tsoo was not

TABLE 1.

OLED data at 20 mA/cm: electroluminescence for aggregates of various materials (), is peak wavelength, nm: FWHM is full spectral width at half-maximum, nm)

1 host component (1. max hc)/2" host component Aggregate colorf spectrum FWHM Efficiency Example # (2"hc) % 1" he description CIE, CIE nm WA

1 Naphtho2,3-alpyrene? 15 greenish-yellow; wide (Alq O.361 O.S60 S36,100 O.O24 Alq like shape) 2 Naphtho2,3-alpyrene? 20 greenish-yellow; wide O4S1 O.S27 S60,104 O.O27 TBADN (DCJTB-like shape) 3 BenZoghiperylene 40 not readily visible in Alq ~same as Alq ~same as 1.3x Alq Alq higher than Alq 4 BenZoghiperylene 25 blue-green -0.200 0.300 480f-65 O.O33 TBADN 5 Coronene?TBADN 25 blue-green; long tail into the -0.300 0.400 510,-86 -0.012 red 6 Perylene Alq 25 green-yellowish O42O O.SSO S40,88 O.018 7 Perylene/TBADN 25 green; symmetric; pointy O.336 O.S72 S32.84 O.O2S 8 2,5,8,11-Tetra-tert- 40 blue-green; structured with -0.200 0.400 500-65 O.O17 butylperylene/TBADN long tail into the red 9 Peropyrene/TBADN 25 yellow; wide (DCJTB-like OSO4 O.487 Sf 6.108 O.O27 shape) O Benzoapyrenef 10 blue-green, low and wide ~480– O.O24 TBADN 1 Dibenzob.kperylene? 35 not clearly visible in Alq ~same as Alq narrower 1.2x Alq than Alq higher than Alq 2 Dibenzob.kperylene? 10 green, similar to perylene but O.268 O.S24 S12.88 O.O32 TBADN bluer 3 Dibenzob.defchrysene? 5 green O3SO O.S80 S28,86 O.O10 TBADN 4 B-Truxene, TBADN 30 blue-green; wide -0.300 0.400 508-110 --O.O15 5 Decacyclene, Alq 30 yellow; wide -0.450 0.450 570-100 -0.005 6 Decacyclene/TBADN 5 green-blue O.283 O.S31 S1688 O.O13 7 Rubicene, Alq 35 red; very wide -0.660 (0.340 650,136 O.OOS 8 Dibenzoalpentacene 40 red -0.650 0.350 640-100 O.OOS Alq 9 (ndeno1,2,3- 45 red -0.660 0.330 640-100 O.OO6 colperylene Alq

COMPARATIVE EXAMPLE 20 reached a plot of luminance versus time was fitted with 60 stretched exponential function of the following form: OLED device 20 was constructed similar to the devices of L-Loxexp(Axt), Examples 1–19, except that the luminescent layer (2) was 450 A thick, including AlQ, as the sole material. The EL where L, is luminance at time t, Lo is initial luminance, A and characteristics of device 20 are shown in Table 2. 65 B are empirical fit parameters, often found to be on the ragen Table 2 also contains values of lifetimes, which were of -0.011 and 0.59, respectively. Half-lifetime, Tso, of the measured at average current density of 40 mA/cm (0.5 ms device was found by calculating time at which L/Lo -0.5. US 7,183,010 B2 77 78 WORKING EXAMPLES 21 25 COMPARATIVE EXAMPLE 30

OLED devices 21–25 similar to the device of Compara An OLED device 30 such as that of Comparative tive Example 20 were constructed, except that in the lumi Example 20 was constructed. The EL characteristics of this nescent layer (2) naphtho2,3-alpyrene was used as the device are shown in Table 2. material for the first host component and AlQ as the material for the second host component. The relative WORKING EXAMPLES 31 33 amounts of naphtho2,3-alpyrene and AlQ on a volume basis were in the ratio 1:99, 2:98, 4:96, 10:90, and 15:85 for Examples 21, 22, 23, 24, and 25, respectively. The EL 10 OLED devices 31–33 similar to the device of Compara characteristics of the devices 21–25 are shown in Table 2. As tive Example 30 were constructed, except that in the lumi can be seen from Table 2, devices 21–25 demonstrate as nescent layer (2) naphthacene, was used as the material for Volume '% of naphtho2,3-alpyrene increases: 1) slight the first host component and AlQ, as the material for the decrease in luminance efficiency followed by an increase; 2) 15 second host component. The relative amounts of naph shift of the emission color from green to green-yellow; 3) thacene and AlQ on a volume basis were in the ratio 1:99, change in the A cod/A Vs J behavior from gain to larger loss 2:98, and 4:96 for Examples 31, 32 and 33, respectively. The followed by a smaller loss; 4) from 300% to 1,000% EL characteristics of the devices 31–33 are shown in Table improvement in lifetime relative to the Comparative Device 2. As can be seen, devices 131–33 demonstrate as volume 96 20. of naphthacene increases: 1) no significant change in the drive Voltage or luminance efficiency; 2) change in the A COMPARATIVE EXAMPLE 26 cd/A vs J behavior from gain to loss; 3) from 40% to 120% improvement in lifetime relative to the Comparative Device An OLED device 26 similar to that of Comparative 3O. Example 20 was constructed, except that the sole material of 25 the luminescent layer was TBADN. The EL characteristics COMPARATIVE EXAMPLE 34 of this device are shown in Table 2. An OLED device 34 such as that of Comparative WORKING EXAMPLES 27 29 30 Example 26 was constructed. The EL characteristics of this device are shown in Table 2. OLED devices 27–29 similar to the device of Compara tive Example 26 were constructed, except that in the lumi nescent layer (2) naphtho2,3-alpyrene was used as the WORKING EXAMPLES 35 38 material for the first host component and TBADN as the 35 material for the second host component. The relative amounts of naphtho2,3-alpyrene and TBADN on a volume OLED devices 35–38 similar to the device of Compara basis were in the ratio 2.98, 6:94, and 20:80 for Examples tive Example 34 were constructed, except that in the lumi 27, 28, and 29, respectively. The EL characteristics of the nescent layer (2) pyrene was used as the material for the first devices 27–29 are shown in Table 2. As can be seen, devices 40 host component and TBADN as the material for the second 27–29 demonstrate as volume 96 of naphtho2,3-alpyrene host component. The relative amounts of pyrene and increases: 1) about 15% decrease in the drive voltage; 2) no TBADN on a volume basis were in the ratio 2:98, 6:94, change in luminance efficiency; 3) shift in color of emission 13:87, and 33:77 for Examples 35, 36, 37, and 38, respec from blue-green to yellow; 4) change in the A cod/A Vs J tively. The EL characteristics of the devices 35–38 are behavior from loss first to larger loss and then to smaller 45 shown in Table 2. As can be seen, devices 35–38 demon loss; 5) from 550% to 1,700% improvement in lifetime strate from 150% to 180% improvement in lifetime relative relative to the Comparative Device 26. to the Comparative Device 34.

TABLE 2

Compositions and EL properties (at 20 mA/cm) of OLED devices of Examples 20–38"

First host Example component Second host A ca/A vs J, Tsoo, h (a)40 mA/cm, O N2,3-aP. component Dopant, Drive Efficiency, 2, FWHM, % from 0.5 AC, Device # vol% AlQs, vol% vol% voltage, V ca/A, WA CIEx CIEy ill to 100 mA/cm RT

2O O 100 O 8.2 2.43, 0.018 0.334 0.551 528, 104 +14 1,100 21 1 99 O 8.3 2.27, 0.017 O.309 0.552 520, 100 -20 3,200 22 2 98 O 8.4 2.03, 0.016 0.277 0.537 516,92 -31 4,700 23 4 96 O 8.3 2.33, 0.018 0.287 0.548 516,92 -40 7,000 24 10 90 O 8.4 3.14, 0.022 0.361 0.560 536, 108 -37 8,200 25 15 85 O 8.3 3.49, 0.024 0.402 0.551 548, 104 -31 10,000 US 7,183,010 B2 79 80

TABLE 2-continued

Compositions and EL properties (at 20 mA/cm) of OLED devices of Examples 20–38

First host Example component Second host A ccd/A vs J, Tso, h (a)40 mA/cm, O N2,3-aP. component Dopant, Drive Efficiency, FWHM, % from 0.5 AC, Device # vol% TBADN, vol% vol% voltage, V ca/A, WA CIEx CIEy ill to 100 mA/cm RT

26 O 100 O 8.5 1.20, 0.026 0.149 0.135 460, 68 -21 550 27 2 98 O 7.9 2.59, 0.024 0.229 0.458 476, 84 -37 36OO 28 6 94 O 7.4 3.21, 0.023 0.340 0.543 532, 104 -23 62OO 29 2O 8O O 7.5 3.73, 0.027 0.451 0.527 560, 104 -11 10,000

Example First host Second host A ca/A vs J, Tsoe. h (a)40 mA/cm, O component component Dopant, Drive Efficiency, J. FWHM, % from 0.5 AC, Device # N, vol% AlQ, vol% vol% voltage, V cod/A, WA CIEx CIEy ill to 100 mA/cm RT

30 O 100 O 7.6 2.96, 0.021 0.365 0.554 540, 108 +24 800 31 1 99 O 8.O 3.13, 0.022 0.308 0.592 532, 88 -25 1,100 32 2 98 O 8.2 3.09, 0.021 0.306 0.597 532, 84 -34 1,400 33 4 96 O 8.1 3.04, 0.021 0.311 0.600 532, 84 -35 1,700

First host Example component Second host A ccd/A vs J, Tso, h (a)40 mA/cm, O pyrene, component Dopant, Drive Efficiency, FWHM, % from 0.5 AC, Device # vol% TBADN, vol% vol% voltage, V ca/A, WA CIEx CIEy ill to 100 mA/cm’ RT

34 O 100 O 8.7 1.33, 0.026 0.166 0.163 460, 68 -12 225 35 2 98 O 9.0 1.28, 0.026 0.161 0.156 460, 68 -12 62O 36 6 94 O 9.2 1.30, 0.027 0.162 0.151 456, 68 -16 570 37 13 87 O 9.0 1.29, 0.027 0.162 0.152 460, 68 -13 570 38 33 77 O 9.4 1.24, 0.023 0.165 0.177 464, 72 -11 590

N2,3-a)P - naphtho2,3-alpyrene; N - naphthacene: W - peak wavelength, nm: FWHM - full spectral width at half-maximum, nm: A ccd/A vs J - loss or gain in EL efficiency as current density, J, increases from 0.5 to 100 mA/cm; RT - room temperature.

WORKING AND COMPARATIVE EXAMPLES with Orange 2 dopant served as a yellow-orange-emitting 39 -116 45 layer and TBADN doped with Blue-green 2 served as a blue-green-emitting layer. Stabilization Effects of Various Aggregate-Forming The values for CIE coordinates and EL efficiency in W/A Materials at 20 mA/cm and for operational stabilities expressed as values of Too, and Tso, at RT-40 mA/cm and 70° C.-20 For thicknesses and concentrations of materials in multi- 50 mA/cm for Working and Comparative Examples are shown component layers of each device see Table 3. OLED devices in Table 3. Table 3 further lists the effects of addition of the were prepared similar to Examples 1–38. The following 1 host component on the CIE coordinates, EL efficiency in organic layers were deposited in the following sequence by W/A, and operational stability for Working Examples rela sublimation from heated crucible boats in a conventional tive to the corresponding Comparative Examples. 55 vacuum deposition chamber under a vacuum of approxi Table 4 compiles various aging test data including aging mately 10 Torr: (1) a hole-transport layer, either 750 or at direct current conditions for Examples 47, 48, 49, 61, and 1,500 A thick, including NPB, (2) a luminescent layer, from 63-dibenzob.kperylene as a first host component for red 100 to 2,000 A thick, including the 1 host component, 2" and green OLEDs. host component, and most often a luminescent dopant, and go As can be seen from Tables 3 and 4, Working Examples (3) an electron-transport layer, from 0 to 500 A thick, demonstrate from 50% to 10,000% improvements in life including AlQs. In some cases 1 host component was added time relative to the respective Comparative Devices for a also to the NPB hole-transporting layer, whole or part of it wide range of materials as 1 host components, various 2" and with or without a luminescent dopant, or a part of the host components, various luminescent dopants of all colors, AlQ electron-transporting layer, or both. In the cases of 65 device configurations, compositions and thicknesses of white OLEDs, structure utilizing two emissive layers was emissive and charge-transporting layers, and testing condi used where a part of the NPB hole-transporting layer doped tions.

US 7,183,010 B2 99 100

SS NغJOY-KOOL US 7,183,010 B2 101 102

US 7,183,010 B2 105 106

US 7,183,010 B2 107 108

US 7,183,010 B2 109 110

US 7,183,010 B2 111 112

US 7,183,010 B2 113 114

US 7,183,010 B2 115 116

SS US 7,183,010 B2 117 118

US 7,183,010 B2 119 120

US 7,183,010 B2 121 122

US 7,183,010 B2 125 126

US 7,183,010 B2 131 132

TABLE 4-continued Device data: dibenzob.kperylene (DBP) as a 1 host component for red and green OLEDs - various aging conditions.*, * Example 63: 750 A NPBEML375 A Alq

Cell A. B C D E F EML 450 A Alq + 0.38% DPQA + 1.6% DBP AC-50% dc, T90% h 970: MHz, -14 V Tsoo, h 7,000–25,000* rb, RT, Effect --9x increase average mA/cm: resh cells DC- T90% h 15 00% duty Tsoo, h 10,000* cycle, RT, Effect ~10x increase

resh cells *fitted values; lifetimes were measured at average AC current density of 40 mA/cm (0.5 ms forward bias at 80 mA/cm alternating with the 0.5 ms of reverse bias of -14V) and at room temperature and the same way at 20 mA/cm and 70° C.; fitted Tso's are predicted values using stretched exponen ial fit procedure: the devices were run for some time, e.g. 250-1000 hours, after which time the aging was stopped and a plot of luminance versus time was fitted with stretched exponential function of the following form: L = Lox exp(Ax t), where L is luminance at time t, Lo is initial luminance, A and B are empirical fit parameters, found to be in the range of -0.011 and 0.59, respectively; half-lifetimes, Tsoo, were found by calculating time at which L/Lo = 0.5;for 60–80° C.-20 mA/cm stability data, Tsosometimes represent actually measured values; 2x extrapolation works well: that is, fitted Tsoo, values usually agree very well with the actually measured ones when measured decay curve (used for fitting) reaches at least 75% of initial EL; **the data are given at 20 mA/cm unless noted otherwise; OC - open circuit; DC - direct current; dc - duty cycle; rb - reverse bias; RT - room tem perature.

The invention has been described in detail with particular d) the host of the luminescent layer being selected to reference to certain preferred embodiments thereof, but it include a solid organic material comprising a mixture will be understood that variations and modifications can be 30 of at least two components wherein: effected within the spirit and scope of the invention. i) the first component of the mixture is an organic compound that is capable of transporting either elec PARTS LIST trons or holes or both and is capable of forming both monomer State and an aggregate state and further is 10 electrical conductors 35 capable of forming the aggregate State either in the 100 OLED device ground electronic state or in the excited electronic 110 Substrate state that results in a different absorption or emission 120 anode spectrum or both relative to the absorption or emis 130 EL medium sion spectrum or both of the monomer State, respec 140 cathode 40 tively, or the first component of the mixture is 200 OLED device capable of forming the aggregate state whose pres 210 Substrate ence results in a quantum yield of luminescence of 220 anode the monomer state being different relative to the 230 EL medium quantum yield of luminescence of the monomer state 231 hole-transport layer 45 in the absence of the aggregate state, and 232 luminescent layer ii) the second component of the mixture is an organic 233 electron-transport layer compound that upon mixing with the first host com ponent is capable of forming a continuous and Sub 240 cathode stantially pin-hole-free layer; 300 OLED device 50 310 Substrate iii) both the first and second components being selected 320 anode to transfer excitation energy to the dopant so that the dopant produces light while the first and second 330 EL medium components produce no light in the presence of the 331 hole-injection layer dopant; and 332 hole-transport layer 55 333 luminescent layer e) the dopant of the luminescent layer being selected to 334 electron-transport layer produce light from the light-emitting device. 335 electron-injection layer 2. The organic light-emitting device of claim 1 wherein 340 cathode the aggregate State is a dimer in either ground electronic 60 state or excited electronic state. What is claimed: 3. The organic light-emitting device of claim 1 wherein 1. An organic light-emitting device, comprising: the aggregate state is crystalline. a) a Substrate; 4. The organic light-emitting device of claim 3 wherein b) an anode and a cathode disposed over the Substrate; the aggregate state is a microcrystalline or nanocrystalline c) aluminescent layer disposed between the anode and the 65 domain. cathode wherein the luminescent layer includes a host 5. The organic light-emitting device of claim 1 wherein and at least one dopant; the first component is an organic compound that is nonpolar. US 7,183,010 B2 133 134 6. The organic light-emitting device of claim 1 wherein 33. The organic light-emitting device of claim 1 wherein the first component is an organic compound that includes a the first component is a dibenzopyrene or a derivative benzenoid hydrocarbon. thereof. 7. The organic light-emitting device of claim 1 wherein 34. The organic light-emitting device of claim 1 wherein the first component is an organic compound that includes a the first component is benzoperylene or a derivative thereof. heterocycle. 35. The organic light-emitting device of claim 1 wherein 8. The organic light-emitting device of claim 1 wherein the first component is a dibenzoperylene or a derivative the second component is an organic compound that is more thereof. polar than the first component. 36. The organic light-emitting device of claim 1 wherein 9. The organic light-emitting device of claim 1 wherein 10 the first component is tetraphene or a derivative thereof. the first component is an organic compound having an 37. The organic light-emitting device of claim 1 wherein energy gap greater than 1.5 electron Volts. the first component is pentaphene or a derivative thereof. 10. The organic light-emitting device of claim 1 wherein 38. The organic light-emitting device of claim 1 wherein the second component is an organic compound having an the first component is hexaphene or a derivative thereof. energy gap greater than 1.5 electron Volts. 15 39. The organic light-emitting device of claim 1 wherein 11. The organic light-emitting device of claim 1 wherein the first component is hexacene or a derivative thereof. the first component constitutes at least 1 volume 96 of the 40. The organic light-emitting device of claim 1 wherein luminescent layer. the first component is triphenylene or a derivative thereof. 12. The organic light-emitting device of claim 1 wherein 41. The organic light-emitting device of claim 1 wherein the second component constitutes at least 1 volume 96 of the the first component is a benzotriphenylene or a derivative luminescent layer. thereof. 13. The organic light-emitting device of claim 1 wherein 42. The organic light-emitting device of claim 1 wherein the dopant has an energy gap less than or equal to those of the first component is benzoacoronene or dibenZocoronene the first component and the second component. or tribenzocoronene or tetrabenZocoronene or pentabenzo 14. The organic light-emitting device of claim 1 wherein 25 coronene or hexabenzocoronene or a derivative thereof. the dopant is a fluorescent dye. 43. The organic light-emitting device of claim 1 wherein 15. The organic light-emitting device of claim 1 wherein the first component is picene or a derivative thereof. the dopant is a phosphorescent dye. 44. The organic light-emitting device of claim 1 wherein 16. The organic light-emitting device of claim 1 wherein the first component is fluorene or a derivative thereof. the dopant concentration in the luminescent layer is between 30 45. The organic light-emitting device of claim 1 wherein 0 and 10% by volume. the first component is a naphthoperylene or dinaphtho 17. The organic light-emitting device of claim 1 wherein perylene or a derivative thereof. the first component is pyrene or a derivative thereof. 46. The organic light-emitting device of claim 1 wherein 18. The organic light-emitting device of claim 1 wherein the first component is a PAH compound that can be drawn the first component is a benzopyrene or a derivative thereof. 35 using only frilly aromatic benzene rings so as to form 19. The organic light-emitting device of claim 1 wherein graphite-like segments or a derivative thereof. the first component is a naphthopyrene or a derivative 47. The organic light-emitting device of claim 1 wherein thereof. the first component includes a benzenoid hydrocarbon or a 20. The organic light-emitting device of claim 1 wherein derivative thereof substituted with a donor or an acceptor the first component is naphthacene or a derivative thereof. 40 moiety or both. 21. The organic light-emitting device of claim 1 wherein 48. The organic light-emitting device of claim 1 wherein the first component is pentacene or a derivative thereof. the second component includes a benzenoid hydrocarbon or 22. The organic light-emitting device of claim 1 wherein a derivative thereof substituted with a donor or an acceptor the first component is perylene or a derivative thereof. moiety or both. 45 49. The organic light-emitting device of claim 1 wherein 23. The organic light-emitting device of claim 1 wherein the second component includes an OXinoid compound. the first component is fluoranthene or a derivative thereof. 50. The organic light-emitting device of claim 49 wherein 24. The organic light-emitting device of claim 1 wherein the second component includes AlQ. the first component is anthracene or a derivative thereof. 51. The organic light-emitting device of claim 1 wherein 25. The organic light-emitting device of claim 1 wherein 50 the second component includes an anthracene moiety. the first component is anthanthrene or a derivative thereof. 52. The organic light-emitting device of claim 51 wherein 26. The organic light-emitting device of claim 1 wherein the second component includes: the first component is benzoghilperylene or a derivative 2-(1,1 -dimethylethyl)-9,10-bis(2-naphthalenyl)an thereof. thracene (TBADN), 27. The organic light-emitting device of claim 1 wherein 55 9,10-bis(2-naphthalenyl)anthracene (ADN), the first component is coronene or a derivative thereof. 9,10-bis(1-naphthalenyl)anthracene, 28. The organic light-emitting device of claim 1 wherein 9,10-Bisa-(2,2-diphenylethenyl)phenyl)anthracene, the first component is dibenzo calmperylene (peropyrene) 9,10-Bis(1,1':3", 1"-terphenyl-5-yl)anthracene, or a derivative thereof. 9,9'-Bianthracene, 29. The organic light-emitting device of claim 1 wherein 60 10,10'-Diphenyl-9.9'-bianthracene, the first component is rubicene or a derivative thereof. 10,10'-Bis(1,1':3'1"-terphenyl-5-yl)-9.9-bianthracene, 30. The organic light-emitting device of claim 1 wherein 2,2'-Bianthracene, the first component is chrysene or a derivative thereof. 9.9',10,10'-Tetraphenyl-2,2'-bianthracene, 31. The organic light-emitting device of claim 1 wherein 9,10-Bis(2-phenylethenyl)anthracene, or the first component is phenanthrene or a derivative thereof. 65 9-Phenyl-10-(phenylethynyl)anthracene. 32. The organic light-emitting device of claim 1 wherein 53. The organic light-emitting device of claim 1 wherein the first component is pyranthrene or a derivative thereof. the second component includes an amine moiety. US 7,183,010 B2 135 136 54. The organic light-emitting device of claim 53 wherein 60. The organic light-emitting device of claim 1 wherein the second component includes: the dopant includes a DCM moiety. N,N'-bis(1-naphthalenyl)-N,N'-diphenylbenzidine 61. The organic light-emitting device of claim 60 wherein (NPB), N,N'-bis(1-naphthalenyl)-N,N'-bis(2-naphthalenyl)benzi the dopant includes DCJTB. dine (TNB), 62. The organic light-emitting device of claim 1 wherein N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine the dopant includes a periflanthene moiety. (TPD), or 63. The organic light-emitting device of claim 62 wherein N,N'-Bis(N"N"-diphenylaminonaphthalen-5-yl)-N,N'- the dopant includes diphenyl-1,5-diaminonaphthalene (CAS 503624-47-3). 10 55. The organic light-emitting device of claim 1 wherein the second component includes a fluorene moiety. (Red 2) 56. The organic light-emitting device of claim 55 wherein Ph Ph the second component includes: 2,2',7,7-Tetraphenyl-9,9'-spirobi9H-fluorene, 15 2.2.7.7"-Tetra-2-phenanthrenyl-9.9'-spirobi9H-fluorene, 2,2'-Bis(4-N,N-diphenylaminophenyl)-9.9'-spirobi9H fluorene), (CAS 503307-40-2), 4'-Phenyl-spirofluorene-9,6'-6Hindeno1.2-fluoran Ph Ph thene. 2,3,4-Triphenyl-9.9'-spirobifluorene, 64. The organic light-emitting device of claim 1 wherein 11,11'-Spirobi 11H-benzobfluorene, the dopant includes a coumarin moiety. 9.9'-Spirobi9H-fluorene-2,2'-diamine, 9.9'-Spirobi9H-fluorene-2,2'-dicarbonitrile, 25 65. The organic light-emitting device of claim 64 wherein 2,7'-Bis(1,1'-biphenyl-4-yl)-N,N,N',N'-tetraphenyl-9, the dopant includes C-6, C-545T, or C-525T. 9'-spirobi9H-fluorene-2,7-diamine, 66. The organic light-emitting device of claim 1 wherein 9,9.9'.9'.9".9"-Hexaphenyl-2,2':7".2"-ter-9H-fluorene, the dopant includes a quinacridone moiety. 2.7-Bis(1,1'-biphenyl-4-yl)-9.9'-spirobi9H-fluorene, 30 67. The organic light-emitting device of claim 66 wherein 2.2.7.7'-tetra-2-Naphthalenyl-9.9-spirobi9H-fluorene, the dopant includes O 9.9'-(2,7-Diphenyl-9H-fluoren-9-ylidene)di-4,1-phe nylenelbis-anthracene. H O 57. The organic light-emitting device of claim 1 wherein 35 N the second component includes a naphthacene moiety. 58. The organic light-emitting device of claim 57 wherein the second component includes: 5,6,11,12-Tetraphenylnaphthacene (rubrene), 5, 12-Bis(2-naphthyl)-6,11-diphenyltetracene, 40 O H 5, 12-Bis(2-mesityl)-6,11-diphenyltetracene, Quinacridone, QA 5, 12-Bis(1-naphthyl)-6,11-diphenyltetracene, Me O 5,6,11,12-Tetrakis(2-naphthyl)tetracene, 10.10'-(6,11-Diphenyl-5,12-naphthacenediyl)di-4.1 phe nylenebis2,3,6,7-tetrahydro-1H,5H-benzothiazolo 5, 45 6.7-iquinolizine, 9,10,15, 16-Tetraphenyl-dibenzoa.cnaphthacene, O Me 5,6,13,14-Tetraphenylpentacene, Dimethylquinacridone, DMQA 4,4'-(8.9-Dimethyl-5,6,7,10,11,12-hexaphenyl-1,4naph 50 Ph O thacenediyl)bis-benzonitrile, 4,4'-(8.9-Dimethoxy-5,6,7,10,11,12-hexaphenyl-1, N 4naphthacenediyl)bisN,N-diphenylbenzenamine, 1,2,3,5,6,11,12-Heptaphenylnaphthacene, 1,4,5,6,7,10,11,12-Octaphenylnaphthacene, 55 6,11-diphenyl-5,12-bis(4-N,N-diphenylaminophenyl) O Ph naphthacene, Diphenylquinacridone, DPQA

7.8, 15, 16-Tetraphenyl-benzoapentacene, Me O 2,3,5,6,11,12-Hexaphenylnaphthacene, 6,11-diphenyl-5,12-bis(4-cyanophenyl)naphthacene, 60 6,11-diphenyl-5,12-bis(4-(2-thienyl)phenyl)naph thacene, or 9,10,19,20-Tetraphenyl-tetrabenzoa.cj.lnaphthacene. 59. The organic light-emitting device of claim 1 wherein 65 the second component includes a benzoxazolyl moiety or CFDMQA thio and amino analogs of benzoxazolyl moiety. US 7,183,010 B2 137 138 68. The organic light-emitting device of claim 1 wherein 73. The organic light-emitting device of claim 72 wherein the dopant includes a DPMB (dipyridinomethene borate) the dopant includes: moiety 5,6,11,12-Tetraphenylnaphthacene (rubrene), 2,2'-(6,11-diphenyl-5,12-naphthacenediyl)di-4,1-phe nylenebis(6-methylbenzothiazole) (Orange 2), 5,12-Bis(2-mesityl)-6,11-diphenyltetracene, 5,6,11,12-Tetrakis(2-naphthyl)tetracene, 10,10'-(6,11-Diphenyl-5,12-naphthacenediyl)di-4,1-phe nylenebis2,3,6,7-tetrahydro-1H,5H-benzothiazolo.5, 10 6,7-quinolizine, 5,6,13,14-Tetraphenylpentacene, 4,4'-(8.9-Dimethoxy-5,6,7,10,11,12-hexaphenyl-1,4- naphthacenediyl)bis N,N-diphenylbenzenamine, 69. The organic light-emitting device of claim 68 wherein 15 6,11-diphenyl-5,12-bis(4'-N,N-diphenylaminophenyl) the dopant includes naphthacene, 7,8,15, 16-Tetraphenyl-benzoapentacene, or (DPMB 1) 6,11-diphenyl-5,12-bis(4-cyanophenyl)naphthacene.

74. The organic light-emitting device of claim 1 wherein the dopant includes a BASB moiety. 75. The organic light-emitting device of claim 74 wherein the dopant includes: 4-Diphenylamino)-4-4-(diphenylamino)Styrylstilbene, 25 4-(Di-p-Tolylamino)-4-(di-p-tolylamino)styrylstilbene (Blue-green 2), 4,4'-(2,5-Dimethoxy-1,4-phenylene)di-2,1-ethenediyl (DPMB 2) bis N,N-bis(4-methylphenyl)benzenamine, 4,4'-(1,4-Naphthalenediyldi-2,1-ethenediyl)bis N,N-bis 30 (4-methylphenyl)benzenamine, 3,3'-(1,4-Phenylenedi-2,1-ethenediyl)bis 9-(4-ethylphe nyl)-9H-carbazole, 4,4'-(1,4-Phenylenedi-2,1-ethenediyl)bis N,N-diphenyl 35 1-naphthalenamine, 4,4'-1,4-Phenylenebis(2-phenyl-2,1-ethenediyl)bis N. N-diphenylbenzenamine, 44'4"-(1,2,4-Benzenetriyltri-2,1-ethenediyl)tris N.N- (DPMB3) diphenylbenzenamine, 40 9,10-Bisa-(di-p-tolylamino)styrylanthracene, or C.C.'-(1,4-Phenylenedimethylidyne)bis 4-(dipheny lamino)-1-naphthaleneacetonitrile. 76. The organic light-emitting device of claim 1 wherein 45 the dopant includes a perylene moiety. 77. The organic light-emitting device of claim 76 wherein the dopant includes: Perylene, 70. The organic light-emitting device of claim 1 wherein 50 2,5,8,11-Tetra-tert-butylperylene (TBP), the dopant includes an indenoperylene moiety. 2.8-Di-tert-Butylperylene, 71. The organic light-emitting device of claim 70 wherein Benzo(bperylene, or the dopant includes Dibenzob.kperylene. 78. The organic light-emitting device of claim 1 wherein 55 the dopant includes a ADPMB (aza-dipyridinomethene (Yellow-green 2) borate) moiety

( ) ( ) Ph 60

Ph

65 72. The organic light-emitting device of claim 1 wherein the dopant includes a naphthacene moiety. US 7,183,010 B2 139 140 79. The organic light-emitting device of claim 78 wherein a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, the dopant includes: 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-triphenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan (Blue 2) 5 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- Phan), 1.2- phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno 10 (2.3-F1An), 1.2- fluorantheno (1.2-F1An), 3,4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2.3 -triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or s their alkyl or aryl substituted derivative. (ADPMB 1) 15 81. The organic light-emitting device of claim 1 wherein the first component of the mixture is a benzenoid compound that has the formula:

(ADPMB2) 25

30

80. The organic light-emitting device of claim 1 wherein wherein: 35 Substituents R through Ra are each individually hydro the first component of the mixture is a benzenoid compound gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary that has the formula: lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, R13 R14 alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 40 to 24 carbon atoms, alkynyl of from 1 to 24 carbon R12 R atoms, aryl of from 5 to 30 carbon atoms, substituted R2 R3 aryl, heterocycle containing at least one nitrogen atom, R4 or at least one oxygen atom, or at least one Sulfur atom, R or at least one boron atom, or at least one phosphorus 45 atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R. Substitu R10 Rs ents form an annelated benzo-, naphtho-, anthra-, Ro Rs R R6 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted 50 derivative; or any two R through R. Substituents form wherein: a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, Substituents R through Ra are each individually hydro 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, 55 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- to 24 carbon atoms, alkynyl of from 1 to 24 carbon Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno atoms, aryl of from 5 to 30 carbon atoms, substituted (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- aryl, heterocycle containing at least one nitrogen atom, Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno or at least one oxygen atom, or at least one Sulfur atom, 60 (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno or at least one boron atom, or at least one phosphorus (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran atom, or at least one silicon atom, or any combination theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- thereof; or any two adjacent R through R. Substitu triphenyleno (1.2-TriP), ace, or indeno substituent or ents form an annelated benzo-, naphtho-, anthra-, their alkyl or aryl substituted derivative. phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 65 82. The organic light-emitting device of claim 1 wherein peryleno-substituent or its alkyl or aryl substituted the first component of the mixture is a benzenoid compound derivative; or any two R through R. Substituents form that has the formula: US 7,183,010 B2 141 142 atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R2 substitu ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted 10 derivative; or any two R through R substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1,2-anthraceno. 2,3-anthraceno. 2,2'-biphenylene (2,2'- wherein: BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno substituents R through R2 are each individually hydro (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 15 threno (9,10-PhAn), 1.9-anthraceno (1.9-An), 1.10 lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- diarylalkylsilyl dialkylarylsilyl. keto, dicyanomethyl, PhAn), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- to 24 carbon atoms, alkynyl of from 1 to 24 carbon Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno atoms, aryl of from 5 to 30 carbon atoms, substituted (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno aryl, heterocycle containing at least one nitrogen atom, (3.4-Per), 7,8-fluorantheno (7,8-F1An), 8.9-fluoran or at least one oxygen atom, or at least one sulfur atom, theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- or at least one boron atom, or at least one phosphorus triphenyleno (1.2-TriP), ace, or indeno substituent or atom, or at least one silicon atom, or any combination their alkyl or aryl substituted derivative. thereof; or any two adjacent R through R. Substitu 25 84. The organic light-emitting device of claim 1 wherein ents form an annelated benzo-, naphtho-, anthra-, the first component of the mixture is a benzenoid compound phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or that has the formula: peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R2 substituents form R12 R R2 R3 a 1,2-benzo, 1.2-naphtho. 2.3-naphtho. 1.8-naphtho. 30 R 1.2-anthraceno. 2,3-anthraceno. 2,2'-biphenylene (2,2'- 1In 2 R4 BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (1.9-An), 1,10- R10 Rs phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- 35 R9 Rs R R6 PhAn), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- wherein: Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno substituents R through R2 are each individually hydro (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3.4-peryleno gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary (3.4-Per), 7,8-fluorantheno (7.8-F1An), 8.9-fluoran- 40 lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, theno (8.9-FlAn), 2,3-triphenyleno (2,3-TriP), 1,2- diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, triphenyleno (1.2-TriP), ace, or indeno substituent or alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 their alkyl or aryl substituted derivative. to 24 carbon atoms, alkynyl of from 1 to 24 carbon 83. The organic light-emitting device of claim 1 wherein atoms, aryl of from 5 to 30 carbon atoms, substituted the first component of the mixture is a benzenoid compound 45 aryl, heterocycle containing at least one nitrogen atom, that has the formula: or at least one oxygen atom, or at least one sulfur atom,

or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R2 substitu 50 ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 55 1,2-anthraceno. 2,3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (1.9-An), 1.10 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- 60 PhAn), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno wherein: (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- substituents R through R are each individually hydro Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3.4-peryleno lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, (3.4-Per), 7,8-fluorantheno (7,8-F1An), 8.9-fluoran diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, 65 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 triphenyleno (1.2-TriP), ace, or indeno substituent or to 24 carbon atoms, alkynyl of from 1 to 24 carbon their alkyl or aryl substituted derivative. US 7,183,010 B2 143 144 85. The organic light-emitting device of claim 1 wherein wherein: the first component of the mixture is a benzenoid compound Substituents R through R are each individually hydro that has the formula: gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, R10 5 diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted Rs R2 aryl, heterocycle containing at least one nitrogen atom, 10 or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus R R3 atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, R6 R4 15 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or Rs peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form wherein: a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- Substituents R through Ro are each individually hydro- 2O BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary- (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan Rii,"SiSi"E"...MR.1arylal KylS1ly 1, d.1al Kylary IS11yl, Keto, d1cyanomelnyl, threnophenanthreno (9,10-PhAn), (1,10-PhAn), 1.9-anthraceno 2.3-phenanthreno (19-An), 1.10(2,3- alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno to 24 carbon atoms, alkynyl of from 1 to 24 carbon 25 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- atoms, aryl of from 5 to 30 carbon atoms, substituted Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno aryl, heterocycle containing at least one nitrogen atom, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno or at least one oxygen atom, or at least one Sulfur atom, 3. 4-Per) 7 8.fluorantheno 78-FiAn). s ONE or at least one boron atom, or at least one phosphorus theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- atom, orr. at least one silicon atom,s or any combination 30 triphenyleno (1.2-TriP), ace, or indeno substituent or thereof; or any two adjacent R through Rio Substitu- their alkyl or aryl substituted derivative. ts f lated b htho- thra entsphenanthro-, Iorm an fluorantheno-, annelated benzo-, pyreno-, napnuno-, triphenyleno-, anunra-, or 87. The organic light-emitting device of claim 1 wherein peryleno-substituent or its alkyl or aryl substituted the first component of the mixture is a benzenoid compound derivative; or any two R through Rio Substituents form that has the formula: a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 35 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan- R11 R2 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- 40 Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno R10 R3 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno 45 R R4 (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- Rs Rs triphenyleno (1.2-TriP), ace, or indeno substituent or their alkyl or aryl substituted derivative. 86. The organic light-emitting device of claim 1 wherein so the first component of the mixture is a benzenoid compound wherein: that has the formula: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, R12 R 55 diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, 60 or at least one oxygen atom, or at least one Sulfur atom, R9 R4 or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, 65 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or R7 R6 peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form US 7,183,010 B2 145 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno R13 R14 R (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan- R12 R2 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1,10- 5 R11 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno R3 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno R4 (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno 10 R Rs (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran- R8 R7 R6 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or their alkyl or aryl substituted derivative. 15 wherein: 88. The organic light-emitting device of claim 1 wherein Substituents R through Ra are each individually hydro the first component of the mixture is a benzenoid compound gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary that has the formula: lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, 2O alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, Ro 25 or at least one boron atom, or at least one phosphorus R3 atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R. Substitu R4 ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or R R6 Rs 30 peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, wherein: 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- Substituents R through R are each individually hydro BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary- 3s (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno to 24 carbon atoms, alkynyl of from 1 to 24 carbon (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- atoms, aryl of from 5 to 30 carbon atoms, substituted 40 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno aryl, heterocycle containing at least one nitrogen atom, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno or at least one oxygen atom, or at least one Sulfur atom, (3,4-Per), 7,8-fluorantheno (7,8-F1An), 8,9-fluoran or at least one boron atom, or at least one phosphorus theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- atom, or at least one silicon atom, or any combination triphenyleno (12-TriP), ace, Or indeno Substituent or thereof; or any two adjacent R through R. Substitu 45 their alkyl or aryl substituted derivative. ents form an annelated benzo-, naphtho-, anthra-, 90. The organic light-emitting device of claim 1 wherein phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or the first component of the mixture is a benzenoid compound peryleno-substituent or its alkyl or aryl substituted that has the formula: derivative; or any two R through R. Substituents form 50 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 55 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno 60 (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or their alkyl or aryl substituted derivative. 89. The organic light-emitting device of claim 1 wherein 65 the first component of the mixture is a benzenoid compound that has the formula: US 7,183,010 B2 147 148 wherein: Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno Substituents R through Ra are each individually hydro (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- to 24 carbon atoms, alkynyl of from 1 to 24 carbon triphenyleno (1.2-TriP), ace, or indeno substituent or atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, their alkyl or aryl substituted derivative. or at least one oxygen atom, or at least one Sulfur atom, 10 92. The organic light-emitting device of claim 1 wherein or at least one boron atom, or at least one phosphorus the first component of the mixture is a benzenoid compound atom, or at least one silicon atom, or any combination that has the formula: thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, R13 R14 R R2 R3 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 15 peryleno-substituent or its alkyl or aryl substituted R12 R4 derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno R Rs (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan R10 Ro Rs R R6 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- wherein: Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno Substituents R through Ra are each individually hydro (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- 25 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- to 24 carbon atoms, alkynyl of from 1 to 24 carbon triphenyleno (1.2-TriP), ace, or indeno substituent or 30 atoms, aryl of from 5 to 30 carbon atoms, substituted their alkyl or aryl substituted derivative. aryl, heterocycle containing at least one nitrogen atom, 91. The organic light-emitting device of claim 1 wherein or at least one oxygen atom, or at least one Sulfur atom, the first component of the mixture is a benzenoid compound or at least one boron atom, or at least one phosphorus that has the formula: atom, or at least one silicon atom, or any combination 35 thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, R R2 R3 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form 40 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, R10 OOC R4 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- R6 Rs BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno R8 R7 R6 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 wherein: 45 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- Substituents R through Ro are each individually hydro Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 50 (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran to 24 carbon atoms, alkynyl of from 1 to 24 carbon theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- atoms, aryl of from 5 to 30 carbon atoms, substituted triphenyleno (1.2-TriP), ace, or indeno substituent or aryl, heterocycle containing at least one nitrogen atom, their alkyl or aryl substituted derivative. or at least one oxygen atom, or at least one Sulfur atom, 93. The organic light-emitting device of claim 1 wherein or at least one boron atom, or at least one phosphorus 55 atom, or at least one silicon atom, or any combination the first component of the mixture is a benzenoid compound thereof, or any two adjacent R through Rio Substitu that has the formula: ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or R14 R15 R16 R R2 R3 peryleno-substituent or its alkyl or aryl substituted 60 derivative; or any two R through Rio Substituents form R13 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- O R4 BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno Rs (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan 65 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 R10 R6 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- US 7,183,010 B2 149 150 wherein: BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno Substituents R through R are each individually hydro (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno aryl, heterocycle containing at least one nitrogen atom, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno or at least one oxygen atom, or at least one Sulfur atom, 10 (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran or at least one boron atom, or at least one phosphorus theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- atom, or at least one silicon atom, or any combination triphenyleno (1.2-TriP), ace, or indeno substituent or thereof, or any two adjacent R through R. Substitu their alkyl or aryl substituted derivative. ents form an annelated benzo-, naphtho-, anthra-, 95. The organic light-emitting device of claim 1 wherein phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 15 peryleno-substituent or its alkyl or aryl substituted the first component of the mixture is a benzenoid compound derivative; or any two R through R. Substituents form that has the formula: a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- R R BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno 20 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan- R12 R3 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10- R11 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- R10 Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno N R4 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- 25 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno Rs (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran- R8 R7 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or 30 their alkyl or aryl substituted derivative. wherein: 94. The organic light-emitting device of claim 1 wherein Substituents R through R are each individually hydro the first component of the mixture is a benzenoid compound gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary that has the formula: lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, 35 diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl,

alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted 40 aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substitu 45 ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted wherein: derivative; or any two R through R. Substituents form Substituents R through Ro are each individually hydro- 50 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary- 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 to 24 carbon atoms, alkynyl of from 1 to 24 carbon 55 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- atoms, aryl of from 5 to 30 carbon atoms, substituted Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno aryl, heterocycle containing at least one nitrogen atom, (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- or at least one oxygen atom, or at least one Sulfur atom, Per) 3 4-fluorantheno (3. 4-F1An) s 2.3-fluorantheno or at least one boron atom, or at least one phosphorus (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno atom, or at least one silicon atom, or any combination 60 thereof, or any two adjacent R through Rio Substitu (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran ents form an annelated benzo-, naphtho-, anthra-, theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or triphenyleno (1.2-TriP), ace, or indeno substituent or peryleno-substituent or its alkyl or aryl substituted their alkyl or aryl substituted derivative. derivative; or any two R through Rio Substituents form 65 96. The organic light-emitting device of claim 1 wherein a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, the first component of the mixture is a benzenoid compound 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- that has the formula: US 7,183,010 B2 151 152 alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, 10 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, wherein: 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- 15 BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno Substituents R through Ro are each individually hydro (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- to 24 carbon atoms, alkynyl of from 1 to 24 carbon Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno atoms, aryl of from 5 to 30 carbon atoms, substituted (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno aryl, heterocycle containing at least one nitrogen atom, (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran or at least one oxygen atom, or at least one Sulfur atom, theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- or at least one boron atom, or at least one phosphorus 25 triphenyleno (1.2-TriP), ace, or indeno substituent or atom, or at least one silicon atom, or any combination their alkyl or aryl substituted derivative. thereof; or any two adjacent R through Rio Substitu 98. The organic light-emitting device of claim 1 wherein ents form an annelated benzo-, naphtho-, anthra-, the first component of the mixture is a benzenoid compound phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or that has the formula: peryleno-substituent or its alkyl or aryl substituted 30 derivative; or any two R through Rio Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan 35 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno 40 wherein: (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno Substituents R through Ra are each individually hydro (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, triphenyleno (1.2-TriP), ace, or indeno substituent or diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, their alkyl or aryl substituted derivative. 45 alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 97. The organic light-emitting device of claim 1 wherein to 24 carbon atoms, alkynyl of from 1 to 24 carbon the first component of the mixture is a benzenoid compound atoms, aryl of from 5 to 30 carbon atoms, substituted that has the formula: aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, R11 50 or at least one boron atom, or at least one phosphorus R10 R12 atom, or at least one silicon atom, or any combination R thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, R2 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or R 55 peryleno-substituent or its alkyl or aryl substituted R8 derivative; or any two R through R. Substituents form R3 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- R4 BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno R Rs 60 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan R6 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- wherein: Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno Substituents R through R are each individually hydro (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 65 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran US 7,183,010 B2 153 154 theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- wherein: triphenyleno (1.2-TriP), ace, or indeno substituent or Substituents R through Ra are each individually hydro their alkyl or aryl substituted derivative. gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 99. The organic light-emitting device of claim 1 wherein lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, the first component of the mixture is a benzenoid compound 5 diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, that has the formula: alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, 10 or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination R10 thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, 15 phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno wherein: (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan Substituents R through R are each individually hydro threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, 25 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno to 24 carbon atoms, alkynyl of from 1 to 24 carbon (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno atoms, aryl of from 5 to 30 carbon atoms, substituted (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran aryl, heterocycle containing at least one nitrogen atom, theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- or at least one oxygen atom, or at least one Sulfur atom, 30 triphenyleno (1.2-TriP), ace, or indeno substituent or or at least one boron atom, or at least one phosphorus their alkyl or aryl substituted derivative. atom, or at least one silicon atom, or any combination 101. The organic light-emitting device of claim 1 wherein thereof, or any two adjacent R through R. Substitu the first component of the mixture is a benzenoid compound ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 35 that has the formula: peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form R a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno 40 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- 45 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- wherein: triphenyleno (1.2-TriP), ace, or indeno substituent or 50 Substituents R through R are each individually hydro their alkyl or aryl substituted derivative. gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 100. The organic light-emitting device of claim 1 wherein lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, the first component of the mixture is a benzenoid compound diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, that has the formula: alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 55 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus 60 atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted 65 derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- US 7,183,010 B2 155 156 BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- 10 triphenyleno (1.2-TriP), ace, or indeno substituent or their alkyl or aryl substituted derivative. 102. The organic light-emitting device of claim 1 wherein the first component of the mixture is a benzenoid compound 15 that has the formula: wherein:

Substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 2O lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted 25 aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination 30 thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or wherein: peryleno-substituent or its alkyl or aryl substituted Substituents R through Ra are each individually hydro- derivative; or any two R through R. Substituents form gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary- 35 a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, 1,2-anthraceno, 2.3-anthraceno, 2,2'-biphenylene (2,2'- diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan to 24 carbon atoms, alkynyl of from 1 to 24 carbon threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 atoms, aryl of from 5 to 30 carbon atoms, substituted 40 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- aryl, heterocycle containing at least one nitrogen atom, Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno or at least one oxygen atom, or at least one Sulfur atom, (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- or at least one boron atom, or at least one phosphorus Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno atom, or at least one silicon atom, or any combination 45 (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno thereof, or any two adjacent R through R. Substitu (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran ents form an annelated benzo-, naphtho-, anthra-, theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or triphenyleno (1.2-TriP), ace, or indeno substituent or peryleno-substituent or its alkyl or aryl substituted their alkyl or aryl substituted derivative. derivative; or any two R through Ra substituents form so 104. The organic light-emitting device of claim 1 wherein a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, the first component of the mixture is a benzenoid compound 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- that has the formula: BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1,10- ss phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3.4-peryleno go (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or their alkyl or aryl substituted derivative. 103. The organic light-emitting device of claim 1 wherein 65 the first component of the mixture is a benzenoid compound that has the formula: US 7,183,010 B2 157 158 wherein: peryleno-substituent or its alkyl or aryl substituted substituents R through R are each individually hydro derivative; or any two R through Rs substituents form gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary a 1,2-benzo, 1.2-naphtho. 2.3-naphtho. 1.8-naphtho, lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, 1.2-anthraceno. 2.3-anthraceno. 2,2'-biphenylene (2,2'- diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan to 24 carbon atoms, alkynyl of from 1 to 24 carbon threno (9,10-PhAn), 1.9-anthraceno (19-An), 1,10 atoms, aryl of from 5 to 30 carbon atoms, substituted phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- aryl, heterocycle containing at least one nitrogen atom, Phan), 1,2-phenanthreno (1.2-PhAn), 1,10-pyreno or at least one oxygen atom, or at least one sulfur atom, 10 (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination Per), 3,4-fluorantheno (3,4-F1An), 2,3-fluorantheno thereof; or any two adjacent R through R substitu (2.3-FlAn), 1.2-fluorantheno (1.2-F1An), 3.4-peryleno ents form an annelated benzo-, naphtho-, anthra-, (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 15 theno (8.9-FlAn), 2,3-triphenyleno (2,3-TriP), 1,2- peryleno-substituent or its alkyl or aryl substituted triphenyleno (1.2-TriP), ace, or indeno substituent or derivative; or any two R through R substituents form their alkyl or aryl substituted derivative. a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 106. The organic light-emitting device of claim 1 wherein 1.2-anthraceno. 2.3-anthraceno. 2,2'-biphenylene (2,2'- the first component of the mixture is a benzenoid compound BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno 20 that has the formula: (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1,10 phenanthreno (1,10-PhAn), 2.3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- 25 Per), 3.4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-FlAn), 1.2-fluorantheno (1.2-F1An), 3.4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or 30 their alkyl or aryl substituted derivative. 105. The organic light-emitting device of claim 1 wherein the first component of the mixture is a benzenoid compound that has the formula: 35

wherein: Substituents R through R are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 40 lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted 45 aryl, heterocycle containing at least one nitrogen atom, or at least one oxygenatom, or at least one sulfur atom, or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof; or any two adjacent R through R substitu 50 ents form an annelated benzo-, naphtho-, anthra phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted wherein: derivative; or any two R through R substituents form Substituents R through Rs are each individually hydro a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary 55 1,2-anthraceno. 2,3-anthraceno. 2,2'-biphenylene (2,2'- lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 threno (9,10-PhAn), 1.9-anthraceno (19-An), 1,10 to 24 carbon atoms, alkynyl of from 1 to 24 carbon phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- atoms, aryl of from 5 to 30 carbon atoms, substituted 60 PhAn), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno aryl, heterocycle containing at least one nitrogen atom, (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- or at least one oxygen atom, or at least one sulfur atom, Per), 3,4-fluorantheno (3,4-F1An), 2,3-fluorantheno or at least one boron atom, or at least one phosphorus (2.3-FlAn), 1.2-fluorantheno (1.2-F1An), 34-peryleno atom, or at least one silicon atom, or any combination (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran thereof; or any two adjacent R through Rs substitu 65 theno (8.9-FlAn), 2,3-triphenyleno (2,3-TriP), 1,2- ents form an annelated benzo-, naphtho-, anthra triphenyleno (1.2-TriP), ace, or indeno substituent or phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or their alkyl or aryl substituted derivative. US 7,183,010 B2 159 160 107. The organic light-emitting device of claim 1 wherein the first component of the mixture is a benzenoid compound -continued that has the formula:

10

15

wherein: 2O Substituents R through Ra are each individually hydro gen, fluoro, cyano, alkoxy, aryloxy, diarylamino, ary lalkylamino, dialkylamino, trialkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon atoms, alkenyl of from 1 25 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one Sulfur atom, 30 or at least one boron atom, or at least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent R through R. Substitu ents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or 35 peryleno-substituent or its alkyl or aryl substituted derivative; or any two R through R. Substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho, 1.2-anthraceno, 2.3-anthraceno. 2,2'-biphenylene (2,2'- BP), 4.5-phenanthreno (4.5-PhAn), 1,12-trinhenyleno 40 (1,12-TriP), 1,12-peryleno (1,12-Per), 9,10-phenan threno (9,10-PhAn), 1.9-anthraceno (19-An), 1.10 phenanthreno (1,10-PhAn), 2,3-phenanthreno (2,3- Phan), 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3- 45 Per), 3,4-fluorantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1.2-fluorantheno (1.2-F1An), 3,4-peryleno (3.4-Per), 7.8-fluorantheno (7.8-F1An), 8.9-fluoran theno (8.9-F1An), 2,3-triphenyleno (2,3-TriP), 1,2- triphenyleno (1.2-TriP), ace, or indeno substituent or 50 their alkyl or aryl substituted derivative. 108. The organic light-emitting device of claim 1 wherein the first component of the mixture is a benzenoid compound that has the formula that can be drawn using only fully ss aromatic benzene rings so as to form graphite-like segments:

US 7,183,010 B2 163 164

-continued -continued

wherein: Substituents in each position for each compound and 50 analogous compounds of the homological series are each individually hydrogen, fluoro, cyano, alkoxy, ary loxy, diarylamino, arylalkylamino, dialkylamino, tri alkylsilyl, triarylsilyl, diarylalkylsilyl, dialkylarylsilyl, keto, dicyanomethyl, alkyl of from 1 to 24 carbon 55 atoms, alkenyl of from 1 to 24 carbon atoms, alkynyl of from 1 to 24 carbon atoms, aryl of from 5 to 30 carbon atoms, Substituted aryl, heterocycle containing at least one nitrogen atom, or at least one oxygen atom, or at least one sulfur atom, or at least one boron atom, or at 60 least one phosphorus atom, or at least one silicon atom, or any combination thereof, or any two adjacent Sub stituents form an annelated benzo-, naphtho-, anthra-, phenanthro-, fluorantheno-, pyreno-, triphenyleno-, or peryleno-substituent or its alkyl or aryl substituted 65 derivative; or any two substituents form a 1,2-benzo, 1.2-naphtho, 2.3-naphtho. 1.8-naphtho. 1.2-anthraceno, 2.3 -anthraceno, 2,2'-biphenylene (2,2'-BP), 4.5- US 7,183,010 B2 165 166 phenanthreno (4.5-PhAn), 1,12-triphenyleno (1,12- fluorantheno (1.2-F1An), 3,4-peryleno (3,4-Per), 7.8- TriP), 1,12-peryleno (1,12-Per), 9,10-phenanthreno fluorantheno (7.8-F1An), 8.9-fluorantheno (8.9-F1An), (9,10-PhAn), 1.9-anthraceno (19-An), 1,10-phenan- 2,3-triphenyleno (2,3-TriP), 1,2-triphenyleno (1,2- threno (1,10-PhAn), 2.3-phenanthreno (2,3-PhAn), TriP), ace, or indeno substituent or their alkyl or aryl 1.2-phenanthreno (1.2-PhAn), 1,10-pyreno (1,10-Pyr), 5 Substituted derivative. 1.2-pyreno (1.2-Pyr), 2,3-peryleno (2,3-Per), 3,4-fluo rantheno (3,4-F1An), 2.3-fluorantheno (2.3-F1An), 1,2- k . . . .