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(12) United States Patent (10) Patent No.: US 9,139,765 B2 Stoessel Et Al

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(12) United States Patent (10) Patent No.: US 9,139,765 B2 Stoessel Et Al US009139765B2 (12) United States Patent (10) Patent No.: US 9,139,765 B2 Stoessel et al. (45) Date of Patent: Sep. 22, 2015 (54) ORGANICELECTROLUMNESCENT (58) Field of Classification Search DEVICE CPC ... C07F 9/6584: CO9K11/06; H01L 51/0032: H01L 51/5064; H01L 51/5032; H05B 33/14 (75) Inventors: Philipp Stoessel, Frankfurt am Main USPC ............................................. 568/12: 428/917 (DE); Esther Breuning, Ober-Ramstadt See application file for complete search history. (DE); Dominik Joosten, Frankfurt am Main (DE) (56) References Cited (73) Assignee: Merck Patent GmbH (DE) U.S. PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this 2006/0208221 A1 9, 2006 Gerhard et al. patent is extended or adjusted under 35 2006/0255332 A1 11/2006 Becker et al. U.S.C. 154(b) by 23 days. 2011/O140043 A1 6, 2011 Stoessel et al. (21) Appl. No.: 13/643,615 FOREIGN PATENT DOCUMENTS DE 102008033943 A1 1, 2010 (22) PCT Filed: Mar. 24, 2011 WO WO-2005OO3253 A3 4/2005 WO WO-2004O932O7 A3 6, 2005 (86) OTHER PUBLICATIONS S371 (c)(1), (2), (4) Date: Oct. 26, 2012 Hulikal V., www.hwb.gov.in/htmldocs/nahwd2010/L15.pdf. Abstract p. 1, 2010.* (87) PCT Pub. No.: WO2011/134577 International Search Report for PCT/EP2011/001494 mailed Jul. 28, 2011. PCT Pub. Date: Nov. 3, 2011 Romanenko, E.A., et al., “The Investigation of the Intramolecular Prior Publication Data Transmission Effects in Cyclic Diazaphosphorines”, Journal of (65) Molecular Structure, vol. 83, (1982), pp. 337-340. US 2013/OO46094A1 Feb. 21, 2013 Döpp, H., et al., XP009149759, Science of Synthesis, (2004), pp. 223-355. (30) Foreign Application Priority Data Trupti, N.D., et al., XP002649740, Agnew. Chem., vol. 96, No. 12, (1984), pp.984-985. Apr. 27, 2010 (DE) ......................... 10 2010 O18 321 Schaefer, Werner, et al., “Nature of Bonding in 5-Phosphorins1”. XP002649741, Journal of the American Chemical Society, vol. 98. (51) Int. C. No. 15, (1976), pp. 4410-4418. C7F 9/6584 (2006.01) Kanter, Hartmut, et al., XP002649742, "1,1-Dihalogen-5- C09K II/06 (2006.01) Phosphorine”, Chem. Ber, vol. 110, (1977), pp. 395-422. H05B33/14 (2006.01) Schmidbaur, Hubert, et al., “Syntheses and Molecular Structures of HOIL 5/52 (2006.01) an Isoelectronic Series of (2-Hetero-) 1,3-Diphosphabenzenes', HOIL 5/54 (2006.01) XP002649743, Chem. Ber, vol. 124, (1991), pp. 1525-1530. C7F 9/46 (2006.01) C7F 9/6568 (2006.01) * cited by examiner C07F 9/6587 (2006.01) C09B 55/00 (2006.01) Primary Examiner — Venkataraman Balasubramanian C09B 57/00 (2006.01) (74) Attorney, Agent, or Firm — Drinker Biddle & Reath HOIL 51/50 (2006.01) LLP (52) U.S. C. CPC. C09K II/06 (2013.01); C07F 9/46 (2013.01); (57) ABSTRACT C07F 9/6584 (2013.01); C07F 9/6587 The present invention relates to electronic devices, in particu (2013.01); C07F 9/65686 (2013.01); C09B lar organic electroluminescent devices, which comprise com 55/006 (2013.01); C09B 55/009 (2013.01); pounds of the formula (1) or (2), and to the corresponding C09B 57/00 (2013.01); H05B33/14 (2013.01); compounds and to the use thereof in organic electrolumines C09K221 1/1096 (2013.01); C09K221 1/185 cent devices. (2013.01); HOIL 5 1/5016 (2013.01): HOIL 51/5052 (2013.01); HOIL 51/5096 (2013.01) 6 Claims, No Drawings US 9,139,765 B2 1. 2 ORGANICELECTROLUMNESCENT DEVICE formula (1) R. R. Y RELATED APPLICATIONS s: This application is a national stage application (under 35 Z na2Y U.S.C. S371) of PCT/EP2011/001494, filed Mar. 24, 2011, formula (2) which claims benefit of German Application No. 10 2010.018 R. R. R. R. 321.0, filed Apr. 27, 2010. 10 Y Y The present invention relates to organic electroluminescent x1 Nx x1 Nx devices and to materials for use in organic electroluminescent J 2 -A5 2 devices. na na The structure of organic electroluminescent devices 15 (OLEDs) in which organic semiconductors are employed as where the following applies to the symbols and indices used: functional materials is described, for example, in U.S. Pat. X, Y is on each occurrence, identically or differently, CR', No. 4,539,507, U.S. Pat. No. 5,151,629, EP 0676461 and WO N, Por PR: 98/27136. The emitting materials employed here, besides Z is on each occurrence, identically or differently, CR' or fluorescent emitters, are increasingly organometallic com N: plexes which exhibit phosphorescence (M. A. Baldo et al., Ar is on each occurrence, identically or differently, an Appl. Phys. Lett. 1999, 75, 4-6). For quantum-mechanical aromatic or heteroaromatic ring system having 5 to 60 aro reasons, an up to four-fold energy and power efficiency is matic ring atoms, which may be substituted by one or more possible using organometallic compounds as phosphorescent radicals R'; emitters. In general, there is still a need for improvement, in 25 R is on each occurrence, identically or differently, N(R), particular with respect to efficiency, operating Voltage and N(Ar), C(=O)R’, C(=O)Ar", P(=O)(Ar), S(=O)Ar", lifetime, both in the case of OLEDs which exhibit singlet S(=O)Ar", CR-CRAr', CN, Si(R), OSOR, a emission and also in the case of OLEDs which exhibit triplet straight-chain alkyl, alkoxy or thioalkoxy group having 1 to emission. This applies, in particular, to OLEDs which emit in 30 40C atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy the relatively short-wave region, i.e. green and in particular group having 3 to 40 C atoms, each of which may be substi blue. tuted by one or more radicals R, where one or more non The properties of OLEDs are not determined only by the adjacent CH groups may be replaced by RC=CR, C=C, emitters employed. In particular, the other materials used, Si(R), Ge(R). Sn(R), C=O, C-S, C-Se, C=NR, Such as matrix materials, hole-blocking materials, electron 35 transport materials, hole-transport materials and electron- or P(=O)(R), SO, SONR, O, S or CONR and where one or exciton-blocking materials, are also of particular importance more H atoms may be replaced by D, F, Cl, Br, I, CN or NO. here. Improvements in these materials can thus also result in or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted significant improvements in the OLED properties. by one or more radicals R, or an aryloxy or heteroaryloxy In accordance with the prior art, ketones (for example in 40 group having 5 to 40 aromatic ring atoms, which may be accordance with WO 2004/093207 or WO 2010/006680) or phosphine oxides (for example in accordance with WO 2005/ substituted by one or more radicals R, or an aralkyl or het 003253), interalia, are used as matrix materials for phospho eroaralkyl group having 5 to 40 aromatic ring atoms, which rescent emitters. However, there is still a need for improve may be substituted by one or more radicals R, or a combi ment, in particular with respect to the efficiency and lifetime 45 nation of these systems; two or more Substituents R together of the device, on use of these matrix materials, as in the case with the atoms to which they are bonded may also form a of other matrix materials. mono- or polycyclic aliphatic or aromatic ring system with The object of the present invention is the provision of one another here; compounds which are Suitable for use in a fluorescent or R" is on each occurrence, identically or differently, H. D. F. phosphorescent OLED, for example as matrix material or as 50 Cl, Br, I, N(R), N(Ar), C(=O)R, C(=O)Ar", P(=O) hole-transport/electron-blocking material or exciton-block (Ar), S(=O)Ar", S(=O)Ar", CR-CRAr', CN, NO, ing material or as electron-transport or hole-blocking mate Si(R), B(OR), OSOR, a straight-chain alkyl, alkoxy or rial, and which result in good device properties on use in an thioalkoxy group having 1 to 40 C atoms or a branched or OLED, and the provision of the corresponding electronic cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C 55 atoms, each of which may be substituted by one or more device. radicals R, where one or more non-adjacent CH groups may Surprisingly, it has been found that certain compounds be replaced by RC=CR, C=C, Si(R), Ge(R), Sn(R), described in greater detail below achieve this object and result C-O, C-S, C-Se, C-NR, P(=O)(R), SO, SO, NR, in good properties of the organic electroluminescent device, O, S or CONR and where one or more H atoms may be in particular with respect to the lifetime, efficiency and oper 60 replaced by D. F. Cl, Br, I, CN or NO, or an aromatic or ating Voltage. The present invention therefore relates to elec heteroaromatic ring system having 5 to 60 aromatic ring tronic devices, in particular organic electroluminescent atoms, which may in each case be substituted by one or more devices, which comprise compounds of this type, and to the radicals R. or an aryloxy or heteroaryloxy group having 5 to corresponding preferred compounds. 40 aromatic ring atoms, which may be substituted by one or The present invention relates to an electronic device com 65 more radicals R, or an aralkyl or heteroaralkyl group having prising at least one compound of the following formula (1) or 5 to 40 aromatic ring atoms, which may be substituted by one (2), or more radicals R, or a combination of these systems; US 9,139,765 B2 3 4 Ar' is on each occurrence, identically or differently, an penyl, butenyl, pentenyl, cyclopentenyl, hexenyl, aromatic or heteroaromatic ring system having 5 to 30 aro cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cycloocte matic ring atoms, which may be substituted by one or more nyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl radicals R; or octynyl.
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