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Voltage/ 33O Current Source U.S US007 18301 OB2 (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 X O. O25 S 9 O.O2O 3.3% SS &N OO15 GS 17% O. O1O SSS (/) (f) () r O 4OO 45O 5OO 55O 6OO 650 7OO WAVELENGTH, nrn w s 4OO 450 500 550 6OO 650 700 WAVELENGTH, nnn FIG 9 U.S. Patent Feb. 27, 2007 Sheet 5 of 8 US 7,183,010 B2 4OO 450 5OO 55O 6OO 65O 7OO WAVELENGTH, nrn FIG 10 4OO 45O 5OO 55O 6OO 65O 7OO WAVELENGTH, nrn FIG. I. I U.S. Patent Feb. 27, 2007 Sheet 6 of 8 US 7,183,010 B2 4OO 45O 5OO 55O 6OO 65O 7OO WAVELENGTH, nrn FIG. I2 O. O14 X O. O12 O. O1 O O2 O. OO3 s 132 O. OO6 O. OO4 3O2 O. OO2 4OO 45O 5OO 550 6OO 65O 7OO WAVELENGTH, nrn FIG. I.3 U.S. Patent Feb. 27, 2007 Sheet 7 of 8 US 7,183,010 B2 O O1 5 4OO 45O 5OO 55O 6OO 65O 7OO WAVELENGTH,nrn FIG. 14 4OO 45O 5OO 55O 6OO 65O 7OO WAVELENGTH, nrn FIG 15 U.S. Patent Feb. 27, 2007 Sheet 8 of 8 US 7,183,010 B2 O2 O. O15 2.3% O. Of O (/ 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.
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