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(12) United States Patent (10) Patent No.: US 8,951,647 B2 Parham Et Al

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(12) United States Patent (10) Patent No.: US 8,951,647 B2 Parham Et Al US008951647B2 (12) United States Patent (10) Patent No.: US 8,951,647 B2 Parham et al. (45) Date of Patent: Feb. 10, 2015 (54) ORGANICELECTROLUMINESCENCE (56) References Cited DEVICE U.S. PATENT DOCUMENTS (75) Inventors: Amir Hossain Parham, Frankfurt am 2004/0028944 A1 2/2004 Mori et al. .................... 428,691 Main (DE); Joachim Kaiser, Darmstadt 2004/0147742 A1* 7/2004 Wong et al. ... 544,230 (DE); Anja Gerhard, Egelsbach (DE); 2004/01708.63 A1* 9, 2004 Kim et al. ..................... 428,690 Jonas Valentin Kroeber, Frankfurt (DE) 2006/O115679 A1 6/2006 Chun et al. 2006/0147752 A1* 7/2006 Lee et al. ...................... 428,690 (73) Assignee: Merck Patent GmbH, Darmstadt (DE) 2006, O199038 A1 9, 2006 Lee 2007/0051944 A1 3/2007 Vestweber et al. (*) Notice: Subject to any disclaimer, the term of this 2009,0302752 A1 12/2009 Parham et al. patent is extended or adjusted under 35 U.S.C. 154(b) by 472 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 12/999,792 JP 2003-109767 A 4/2003 JP 2003-109768 4/2003 ............. HOSB 33/22 JP 2003-109768 A 4/2003 (22) PCT Filed: Jul. 8, 2009 JP 2006-156941 A 6, 2006 JP 2006-245565. A 9, 2006 (86). PCT No.: PCT/EP2009/004954 JP 2007-223,928 A 9, 2007 JP 2009-184987. A 8, 2009 S371 (c)(1), JP 2009-266927. A 11, 2009 (2), (4) Date: Dec. 17, 2010 WO WO-2005/053055 A1 6, 2005 WO WO-2008/086851 A1 T 2008 (87) PCT Pub. No.: WO2010/015306 OTHER PUBLICATIONS PCT Pub. Date: Feb. 11, 2010 Wu et al., Highy Bright Blue Organic Light-Emitting Devices using (65) Prior Publication Data Spirobifluorene-Cored Conjugated Compounds, 2002, Applied US 2011 FO121274 A1 May 26, 2011 Physics Letters, vol. 81, No. 4, pp. 577-579.* Wu et al., Highly bright blue organic light-emitting devices using (30) Foreign Application Priority Data spirobifluoreene-cored conjugated compounds, 2002, Applied Phys ics Letters, vol. 81, No. 4, pp. 577-579.* Aug. 8, 2008 (DE) ......................... 10 2008 O36982 Shen. J.Y., et al., “High Tg blue emitting materials for electroluminescent devices.” J. Mater. Chem. 2005, vol. 15, pp. 2455 (51) Int. Cl. 2463. HOIL 5L/50 (2006.01) Lee, R.-H... et al., “Efficient fluorescent red, green, and blue organic HOIL 5L/00 (2006.01) light-emitting devices with a blue host of spirobifluorene derivative.” C09B 57/00 (2006.01) Thin Solid Films 2008, vol. 516, pp. 5062-5068. (52) U.S. Cl. CPC ........ HOIL 51/0067 (2013.01); HOIL 51/0058 * cited by examiner (2013.01); C09B 57/00 (2013.01); HOIL 5 1/5016 (2013.01); Y10S 428/917 (2013.01) Primary Examiner — Gregory Clark USPC ........... 428/690; 428/917; 313/504; 313/505; (74) Attorney, Agent, or Firm — Drinker Biddle & Reath 313/506; 257/40; 257/E51.05; 257/E51.026; LLP 257/E51.032:546/18: 546/24:546/79: 546/81; 54.6/101: 548/304.1: 548/418; 548/440: 548/444 (57) ABSTRACT (58) Field of Classification Search The present invention relates to organic electroluminescent USPC .................. 428/690,917; 313/504,505, 506; devices which comprise fluorene derivatives and spirobifluo 257/40, E51.026, E51.05, E51.032: rene derivatives as matrix material for phosphorescent emit 546/18, 24, 79, 81, 101: 544/234: ters. 548/413, 440, 304.1, 41 See application file for complete search history. 20 Claims, No Drawings US 8,951,647 B2 1. 2 ORGANICELECTROLUMNESCENCE in particular spirobifluorene derivatives, are very highly suit DEVICE able as matrix materials for phosphorescent emitters and result, in this use, in OLEDs which simultaneously have high CROSS-REFERENCE TO RELATED efficiencies, long lifetimes and low operating Voltages, APPLICATIONS including with phosphorescent emitters which contain ketoketonate ligands. This application is a national stage application (under 35 U.S. Pat. No. 6,229,012 and U.S. Pat. No. 6,225,467 dis close the use of fluorene derivatives which are substituted by U.S.C. S371) of PCT/EP2009/004954, filed Jul. 8, 2009, triazine groups as electron-transport material in OLEDS. which claims benefit of German application 10 2008 036 However, the application does not reveal that these materials 982.9, filed Aug. 8, 2008. 10 are also suitable as matrix materials for phosphorescent emit ters. BACKGROUND OF THE INVENTION WO 05/053055 discloses the use of triazine derivatives, in particular spirobifluorene derivatives, which are substituted The present invention relates to phosphorescent organic by triazine groups as hole-blocking material in phosphores electroluminescent devices which comprise fluorene and 15 cent OLEDs. However, the application does not reveal that spirobifluorene derivatives as matrix materials. these materials are also Suitable as matrix materials for phos Organic semiconductors are being developed for a number phorescent emitters. of electronic applications of different types. The structure of organic electroluminescent devices (OLEDs) in which these BRIEF SUMMARY OF THE INVENTION organic semiconductors are employed as functional materials is described, for example, in U.S. Pat. No. 4,539,507, U.S. The invention thus relates to an organic electroluminescent Pat. No. 5,151,629, EP 0676461 and WO 98/27136. How device comprising, in at least one emitting layer, ever, further improvements are still necessary. Thus, there is (A) at least one phosphorescent compound and still a need for improvement, in particular with respect to the (B) at least one compound of the formula (1) or formula (2): lifetime, efficiency and operating Voltage of organic elec 25 troluminescent devices. It is furthermore necessary for the compounds to have high thermal stability and a high glass formula (1) transition temperature and to be capable of sublimation with out decomposition. Especially in the case of phosphorescent electrolumines 30 cent devices, improvements in the above-mentioned proper ties are still necessary. In particular, there is a need for improvement in the case of matrix materials for phosphores cent emitters which simultaneously result in good efficiency, a long lifetime and a low operating Voltage. These very prop 35 erties of the matrix materials are frequently limiting for the lifetime and efficiency of the organic electroluminescent device. In accordance with the prior art, carbazole derivatives, for example bis-(carbazolyl)biphenyl, are frequently used as 40 where the following applies to the symbols and indices used: matrix materials. There is still a need for improvement here, Ar is on each occurrence, identically or differently, a het in particular with respect to the lifetime and glass-transition eroaryl group selected from the group consisting of triaz temperature of the materials. ine, pyrazine, pyrimidine, pyridazine, pyridine, pyrazole, Furthermore, ketones (WO 04/093207), phosphine oxides imidazole, oxazole, oxadiazole and thiazole, each of which and sulfones (WO 05/003253) are used as matrix materials 45 may be substituted by one or more groups R'; for phosphorescent emitters. Low operating Voltages and X is on each occurrence, identically or differently, a group of long lifetimes are achieved, in particular, with ketones. There is still a need for improvement here, in particular with respect the formula (3), where the dashed bond in each case indi to the efficiency and compatibility with metal complexes cates the bonding to the two benzene rings: which contain ketoketonate ligands, for example acetylaceto 50 nate. Furthermore, metal complexes, for example BAlqor bis(2- formula (3) (2-benzothiazole)phenolate Zinc(II), are used as matrix YA). materials for phosphorescent emitters. There is still a need for 2 improvement here, in particular with respect to the operating 55 Voltage and the chemical stability. Purely organic compounds 2. are frequently more stable than these metal complexes. Thus, Some of these metal complexes are hydrolysis-sensitive, which makes handling of the complexes more difficult. or X is, identically or differently on each occurrence, a In particular, there is still a need for improvement in the 60 divalent bridge selected from B(R'), C(R'), Si(R'), case of matrix materials for phosphorescent emitters which C=C(R), O, S, S=O, SO, N(R'), P(R') and P(=O) simultaneously result in high efficiencies, long lifetimes and R; low operating Voltages and which are also compatible with R" is on each occurrence, identically or differently, H. D. F. phosphorescent emitters which carry ketoketonate ligands. Cl, Br, I, CHO, N(Ar), C(=O)Ar", P(=O)(Ar"), Surprisingly, it has been found that fluorene derivatives and 65 S(=O)Ar", S(=O)Ar", CR-CRAr', CN, NO, corresponding heterocyclic derivatives which are substituted Si(R), B(OR), B(R), B(N(R).), OSOR, a by triazine or other electron-deficient nitrogen heterocycles, straight-chain US 8,951,647 B2 3 4 alkyl, alkoxy or thioalkoxy group having 1 to 40 Catoms or dine, pyrimidine, thiophene, etc., or a condensed aryl or het a straight-chain alkenyl or alkynyl group having 2 to 40 C eroaryl group, for example naphthalene, anthracene, pyrene, atoms or a branched or cyclic alkyl, alkenyl, alkynyl, quinoline, isoquinoline, etc. alkoxy or thioalkoxy group having 3 to 40C atoms, each of For the purposes of this invention, an aromatic ring system which may be substituted by one or more radicals R. 5 contains at least 6 C atoms in the ring system. For the pur where one or more, preferably non-adjacent CH2 groups poses of this invention, a heteroaromatic ring system contains may be replaced by RC—CR, C=C, Si(R), Ge(R). at least2C atoms and at least 1 heteroatom in the ring system, Sn(R), C=O, C-S, C=Se, C=NR, P(=O)(R), SO, with the proviso that the sum of C atoms and heteroatoms is SO, NR’, O.S or CONR and where one or more Hatoms at least 5.
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