WO2010126234A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
- Publication number
- WO2010126234A1 WO2010126234A1 PCT/KR2010/002170 KR2010002170W WO2010126234A1 WO 2010126234 A1 WO2010126234 A1 WO 2010126234A1 KR 2010002170 W KR2010002170 W KR 2010002170W WO 2010126234 A1 WO2010126234 A1 WO 2010126234A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituent
- alkyl
- aryl
- organic electroluminescent
- halogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- 125000001424 substituent group Chemical group 0.000 claims description 160
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 54
- 239000010410 layer Substances 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000005104 aryl silyl group Chemical group 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- -1 cyano, carbazolyl Chemical group 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 238000005401 electroluminescence Methods 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 0 CN(C1=*)C(IB=*)=C([*-])C1=* Chemical compound CN(C1=*)C(IB=*)=C([*-])C1=* 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- QINDAMNVOZQXIA-UHFFFAOYSA-N C=N[n](c1ccccc11)c2c1c1cnccc1cn2 Chemical compound C=N[n](c1ccccc11)c2c1c1cnccc1cn2 QINDAMNVOZQXIA-UHFFFAOYSA-N 0.000 description 1
- ULCRQHQAPMAJOC-UHFFFAOYSA-N CC(CC=C(C=Cc1ccc2)c3c1c2c1c2ccccc22)c3c1[n]2N(C)C Chemical compound CC(CC=C(C=Cc1ccc2)c3c1c2c1c2ccccc22)c3c1[n]2N(C)C ULCRQHQAPMAJOC-UHFFFAOYSA-N 0.000 description 1
- DEUGIPUJHYYDFA-UHFFFAOYSA-N CC12N(C(C)=C)c3ncccc3C1=C1N=CC=CC1=CC2 Chemical compound CC12N(C(C)=C)c3ncccc3C1=C1N=CC=CC1=CC2 DEUGIPUJHYYDFA-UHFFFAOYSA-N 0.000 description 1
- SJDXORFWAXOTRQ-UHFFFAOYSA-N CN[n](c1ccccc11)c2c1c1ccccc1c1c2cccc1 Chemical compound CN[n](c1ccccc11)c2c1c1ccccc1c1c2cccc1 SJDXORFWAXOTRQ-UHFFFAOYSA-N 0.000 description 1
- CCMISVRQPQKDTD-UHFFFAOYSA-N CN[n](c1ncccc11)c2c1c1cnccc1cn2 Chemical compound CN[n](c1ncccc11)c2c1c1cnccc1cn2 CCMISVRQPQKDTD-UHFFFAOYSA-N 0.000 description 1
- IGYXTRFLXRENBT-UHFFFAOYSA-N C[n]1c2ncc(cccc3)c3c2c2c1cccc2 Chemical compound C[n]1c2ncc(cccc3)c3c2c2c1cccc2 IGYXTRFLXRENBT-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N Cc1nc(c2nc(C)cc(-c3ccccc3)c2cc2)c2c(-c2ccccc2)c1 Chemical compound Cc1nc(c2nc(C)cc(-c3ccccc3)c2cc2)c2c(-c2ccccc2)c1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-O [OH2+]c(cc1)ccc1-c1ccccc1 Chemical compound [OH2+]c(cc1)ccc1-c1ccccc1 YXVFYQXJAXKLAK-UHFFFAOYSA-O 0.000 description 1
- PZOXFBPKKGTQDZ-UHFFFAOYSA-O [OH2+]c(ccc1c2)cc1ccc2-c1ccccc1 Chemical compound [OH2+]c(ccc1c2)cc1ccc2-c1ccccc1 PZOXFBPKKGTQDZ-UHFFFAOYSA-O 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZFWIKJVMYVQJTF-UHFFFAOYSA-N c(cc1)ccc1[SiH-](c1ccccc1)(c1ccccc1)c1cc(-c2nc(-[n]3c(cccc4)c4c4c3cccc4)ncc2)ncc1 Chemical compound c(cc1)ccc1[SiH-](c1ccccc1)(c1ccccc1)c1cc(-c2nc(-[n]3c(cccc4)c4c4c3cccc4)ncc2)ncc1 ZFWIKJVMYVQJTF-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- the present invention relates to novel organic electroluminescent compounds, and organic electroluminescent devices comprising the same.
- the organic electroluminescent compounds according to the invention are represented by Chemical (l) or (2).
- electroluminescence (EL) devices being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate.
- Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
- an organic EL device when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair to provide an excitron. Light is emitted by using luminescence (phosphorescence or fluorescence) of excitrons when inactivated.
- the organic EL device emits polarization with about 10 V of voltage and about 100 ⁇ 10,000 cd/m 2 of luminance. By means of simple selection of fluorescent material, light can be emitted with broad spectrum from blue to red.
- the device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display.
- electroluminescent material The most important factor to determine luminous efficiency, lifetime or the like in an organic EL device is electroluminescent material.
- electroluminescent materials include that the material should have high luminescent quantum yield in solid state and high mobility of electrons and holes, is not easily decomposed during vapor-deposition in vacuo, and forms uniform and stable thin film.
- Organic electroluminescent materials can be generally classified into high-molecular materials and low-molecular materials.
- the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, in view of molecular structure.
- Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
- Electroluminescent materials can be functionally classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an electroluminescent layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional electroluminescent materials as considering EL properties required for medium to large sized OLED panels.
- host material serving as a solvent and energy conveyer in solid state
- desired properties for the host material are high purity and appropriate molecular weight to enable vapor-deposition in vacuo.
- glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability.
- the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other materials of adjacent layers but without interlayer migration.
- CBP 4,4'-N,N'-dicarbazole-biphenyl
- the materials in prior art are advantageous in view of light emitting property, they have low glass transition temperature and very poor thermal stability, so that the materials tend to be changed during the process of high temperature vapor-deposition in vacuo.
- power efficiency ( ⁇ /voltage) x current efficiency.
- the power efficiency is inversely proportional to the voltage, and the power efficiency should be higher in order to obtain lower power consumption of an OLED.
- an OLED employing phosphorescent electroluminescent (EL) material shows significantly higher current efficiency (cd/A) than an OLED employing fluorescent EL material.
- the object of the invention is to overcome the problems of conventional techniques as described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency and improved device life as well as appropriate color coordinate, as compared to conventional materials.
- Another object of the invention is to provide organic electroluminescent devices having high efficiency and long life, by employing those organic electroluminescent as electroluminescent material.
- the present invention relates to organic electroluminescent compounds represented by Chemical Formula (1) or (2), and organic electroluminescent devices comprising the same.
- organic electroluminescent compounds according to the invention exhibiting higher luminous efficiency and noticeably improved life properties of material, OLED s having very good operation life can be obtained.
- a 1 through A 5 and B 1 through B 8 independently represent N or CR 21 ; if two adjacent groups from A 1 through A 5 and B 1 through B 8 represent CR 21 , those R 21 groups may be linked together via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or poly cyclic aromatic ring; and the carbon atom(s) of the alkylene may be substituted by one or more heteroatom(s) selected from NR 3I , O and S, and the carbon atom of alkenylene may be substituted by N;
- L 1 and L 2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s), or (C3-C30)heteroarylene with or without substituent(s), provided that both L 1 and L 2 cannot represent chemical bonds at the same time;
- R 1 through R 3 , R 21 and R 31 independently representhydrogen, deuterium, halogen,
- R 41 through R 43 and R 51 through R 58 are defined as for R 1 through R 3 and R 21 above, and each of R 51 through R 58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or poly cyclic aromatic ring;
- n an integer 0, 1 or 2.
- R 43 and R 51 through R 58 independently represent (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or each of R 51 through R 58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
- alkyl substituted with substituents containing "alkyl” moiety described herein include both linear and branched species.
- aryl described herein represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
- An aryl group may be a monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through single bond(s) are also included.
- the naphthyl may be 1 -naphthyl or 2-naphthyl
- the anthryl may be 1 -anthryl, 2-anthryl or 9-anthryl
- the fluorenyl may be any one of 1 -fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
- the structures having one or more heteroaryl group(s) bonded through a single bond are also included.
- the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
- Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as ben- zofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, ben- siothiazolyl,
- alkyl groups in "(Cl-C30)alkyl, tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (Cl-C30)alkyloxy and (Cl-C30)alkylthio" described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10.
- the aryl groups in "(C6-C30)aryl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (C6-C30)aryloxy and (C6-C30)arylthio" may have restricted carbon number from 6 to 20, or from 6 to 12.
- the heteroaryl groups in “(C3-C30)heteroaryl” may have restricted carbon number from 4 to 20, or from 4 to 12.
- the cycloalkyl groups in "(C3-C30)cycloalkyl” may have restricted carbon number from 3 to 20, or from 3 to 7.
- the alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have restricted carbon number from 2 to 20, or from 2 to 10.
- substituent(s) independently selected from deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), a 5- to 7-membered heterocycloalkyl, a 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkyny
- R 2 i and R 3 i independently represent halogen, (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without sub- stituent(s), (C3-C30)heteroaryl with or without substituent(s), NRnRi 2 [wherein Rn and Ri 2 independently represent (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(Cl-C30)alkylsilyl with or without substituent(s), di(Cl-C30)alkyl(C6-C30)aryl
- W and R 43 are defined as for Chemical Formulas (1) and (2). [50] The groups
- R 1 through R 3 independently represent (Cl-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
- R 2 i represents hydrogen, halogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more(C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), NRnRi 2 [wherein R 11 through R 18 independently represent (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(Cl-C30)alkylsilyl with or without substituent(s), di(Cl-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or
- W and R 43 are defined as for Chemical Formulas (1) and (2).
- the organic electroluminescent compounds according to the present invention can be specifically exemplified by the following compounds, but they are not restricted thereto.
- the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1) or (2).
- the organic layer comprises an electroluminescent layer which comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1) or (2) as host, and one or more dopant(s).
- the dopant to be applied to the organic electroluminescent devices according to the invention are not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (3):
- M 1 is a metal selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 in the Periodic Table of Elements, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
- R 2O i through R 203 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s), or halogen;
- R 204 through R 219 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (Cl-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(Cl-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF 5 , tri(Cl-C30)alkylsilyl with or without substituent(s), di(Cl-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
- R 220 through R 223 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (Cl-C30)alkyl substituent(s);
- R 224 and R 225 independently represent hydrogen, (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R 224 and R 225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or poly cyclic aromatic ring;
- R 226 represents (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;
- R 227 through R 229 independently represent hydrogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
- R 231 through R 242 independently represent hydrogen, (Cl-C30)alkyl with or without halogen substituent(s), (Cl-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- the dopant compounds represented by Chemical Formula (3) may be exemplified by the following compounds, without restriction.
- the organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1) or (2).
- the arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d- transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the organic electroluminescent compound represented by Chemical Formula (1) or (2).
- the organic layer may comprise an electroluminescent layer and a charge generating layer.
- the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1) or (2), to form an organic electroluminescent device emitting white light.
- the compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- an organic electroluminescent device it is preferable to arrange one or more layer(s) (here-in-below, referred to as the "surface layer") selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to arrange a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer. As the result, stability in operation can be obtained.
- metal halides preferably include LiF, MgF 2 , CaF 2 , fluorides of rare earth metal or the like.
- metal oxides preferably include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.
- an organic electroluminescent device it is also preferable to arrange, on at least one surface of the pair of electrodes thus manufactured, a mixed region of electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
- Example 1 Manufacture of OLED's by using organic electroluminescent compounds according to the invention
- OLED devices were manufactured by using the electroluminescent material according to the invention.
- a transparent electrode ITO thin film (15 ⁇ /D) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in iso- propanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated to reach 1O 6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
- 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
- an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (12) according to the present invention as host material, and compound Ir(ppy) 3 (of which the structure is shown below) was charged to another cell as dopant material. Two substances were evaporated at different rates to provide vapor-deposition at a concentration of 4 to 10% by weight. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
- OLED's were manufactured according to the same procedure as described in Example 1 except the hole blocking layer.
- OLED's were manufactured according to the same procedure as described in Example 1 but using in the electroluminescent layer Compound (12) according to the present invention as host material and Compound (19) and (piq) 2 Ir(acac) instead of dopant Ir(ppy) 3 .
- OLED's were manufactured according to the same procedure as described in Example 3 except the hole blocking layer.
- the electroluminescent compounds developed by the present invention exhibited excellent features in terms of performances as compared to conventional material. Furthermore, the devices employing as host material the organic electroluminescent compounds according to the present invention not only exhibit excellent luminous properties, but also lowered operation voltage, confirming the improved luminous efficiency.
Abstract
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. Since the disclosed organic electroluminescent compounds have high luminous efficiency and excellent life property, OLED's having very good operation life can be manufactured therefrom.
Description
The present invention relates to novel organic electroluminescent compounds, and organic electroluminescent devices comprising the same. Specifically, the organic electroluminescent compounds according to the invention are represented by Chemical (1) or (2).
[Chemical Formula 1]
[Chemical Formula 2]
Among display devices, electroluminescence (EL) devices, being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate. Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair to provide an excitron. Light is emitted by using luminescence (phosphorescence or fluorescence) of excitrons when inactivated. The organic EL device emits polarization with about 10 V of voltage and about 100 ~ 10,000 cd/m2 of luminance. By means of simple selection of fluorescent material, light can be emitted with broad spectrum from blue to red. The device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display.
The most important factor to determine luminous efficiency, lifetime or the like in an organic EL device is electroluminescent material. Several properties required for such electroluminescent materials include that the material should have high luminescent quantum yield in solid state and high mobility of electrons and holes, is not easily decomposed during vapor-deposition in vacuo, and forms uniform and stable thin film.
Organic electroluminescent materials can be generally classified into high-molecular materials and low-molecular materials. The low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, in view of molecular structure. Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
In order to realize a full-colored OLED display, three electroluminescent materials (red, green and blue) are employed, and development of those electroluminescent materials having high efficiency and long life is a significant subject to enhance the features of the overall organic electroluminescence. Electroluminescent materials can be functionally classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an electroluminescent layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional electroluminescent materials as considering EL properties required for medium to large sized OLED panels.
From this point of view, development of host material is one of the most important issues to be settled. The desired properties for the host material (serving as a solvent and energy conveyer in solid state) are high purity and appropriate molecular weight to enable vapor-deposition in vacuo. In addition, glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability. Further, the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other materials of adjacent layers but without interlayer migration.
When an organic EL device is manufactured by using a doping technique, energy transfer from host molecules to dopant in excited state cannot be completely (100%) achieved, so that not only the dopant but also the host material would emit light. Particularly in case of a red electrololuminescent device, the host material emits light in a wavelength range of higher visibility than that of the dopant, so that color purity would be deteriorated owing to vague luminescence of the host material. For practical application, actual improvement in electroluminescent life and durability is required.
As a host material for phosphorescent light emitting material, 4,4'-N,N'-dicarbazole-biphenyl (CBP) has been most widely known up to the present, and OLED's having high efficiency to which a hole blocking layer (such as BCP and BAlq) had been applied have been developed. Pioneer (Japan) or the like reported OLED's of high performances which were developed by using bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III) (BAlq) derivatives as the host.
Though the materials in prior art are advantageous in view of light emitting property, they have low glass transition temperature and very poor thermal stability, so that the materials tend to be changed during the process of high temperature vapor-deposition in vacuo. In an OLED, it is defined that power efficiency = (π/voltage) x current efficiency. Thus, the power efficiency is inversely proportional to the voltage, and the power efficiency should be higher in order to obtain lower power consumption of an OLED. In practice, an OLED employing phosphorescent electroluminescent (EL) material shows significantly higher current efficiency (cd/A) than an OLED employing fluorescent EL material. However, in case that a conventional material such as BAlq and CBP was employed as host material of the phosphorescent material, no significant advantage could be obtained in terms of power efficiency (lm/w) because of higher operating voltage as compared to an OLED employing a fluorescent material.
Further, lifetime of the OLED's manufactured therefrom cannot be in satisfactory level by any means. Thus, development of host material having better stability and far improved performances is demanded.
The object of the invention is to overcome the problems of conventional techniques as described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency and improved device life as well as appropriate color coordinate, as compared to conventional materials.
Another object of the invention is to provide organic electroluminescent devices having high efficiency and long life, by employing those organic electroluminescent as electroluminescent material.
The present invention relates to organic electroluminescent compounds represented by Chemical Formula (1) or (2), and organic electroluminescent devices comprising the same. By using the organic electroluminescent compounds according to the invention, exhibiting higher luminous efficiency and noticeably improved life properties of material, OLED s having very good operation life can be obtained.
[Chemical Formula 1]
[Chemical Formula 2]
wherein,
A1 through A5 and B1 through B8 independently represent N or CR21; if two adjacent groups from A1 through A5 and B1 through B8 represent CR21, those R21 groups may be linked together via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; and the carbon atom(s) of the alkylene may be substituted by one or more heteroatom(s) selected from NR31, O and S, and the carbon atom of alkenylene may be substituted by N;
L1 and L2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s), or (C3-C30)heteroarylene with or without substituent(s), provided that both L1 and L2 cannot represent chemical bonds at the same time;
R1 through R3, R21 and R31 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more(C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), substituted or unsubstituted 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkyl fused with one or more aromatic ring(s), adamantyl with or without substituent(s), (C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), 
or 
;
W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
R41 through R43 and R51 through R58 are defined as for R1 through R3 and R21 above, and each of R51 through R58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
each of the heterocycloalkyl and heteroaryl contains one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
m represents an integer 0, 1 or 2.
Specifically, groups 
and 
may be exemplified by the following structures:
wherein, R43 and R51 through R58 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or each of R51 through R58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
The "alkyl", "alkoxy" and other substituents containing "alkyl" moiety described herein include both linear and branched species.
The term "aryl" described herein represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom. An aryl group may be a monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through single bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto. The naphthyl may be 1-naphthyl or 2-naphthyl, the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl, and the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
The term "heteroaryl" described herein means an aryl group containing from 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms. The heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated. The structures having one or more heteroaryl group(s) bonded through a single bond are also included. The heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like. Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl and benzodioxolyl; and corresponding N-oxides (for example, pyridyl N-oxide, quinolyl N-oxide) and quaternary salts thereof; but they are not restricted thereto.
The alkyl groups in "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy and (C1-C30)alkylthio" described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10. The aryl groups in "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy and (C6-C30)arylthio" may have restricted carbon number from 6 to 20, or from 6 to 12. The heteroaryl groups in "(C3-C30)heteroaryl" may have restricted carbon number from 4 to 20, or from 4 to 12. The cycloalkyl groups in "(C3-C30)cycloalkyl" may have restricted carbon number from 3 to 20, or from 3 to 7. The alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl" may have restricted carbon number from 2 to 20, or from 2 to 10.
The term "substituted or unsubstituted (or with or without substituent(s))" described herein means that each substituent L1, L2, R1 through R3, R11 through R18, R21 and R31 has one or more substituent(s) independently selected from deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), a 5- to 7-membered heterocycloalkyl, a 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR61R62, BR63R64, PR65R66, P(=O)R67R68[wherein R61 through R68 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl; or that the adjacent substituents are linked together to form a ring.
Group 
is selected from the following structures, but not restricted thereto.
In the chemical formulas above,
R21 and R31 independently represent halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), NR11R12 [wherein R11 and R12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), 
or 
; and
W and R43 are defined as for Chemical Formulas (1) and (2).
The groups 
and 
are independently selected from the following structures, but not restricted thereto.
In the chemical formulas above,
R1 through R3 independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
R21 represents hydrogen, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more(C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), NR11R12 [wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), 
or 
; and
W and R43 are defined as for Chemical Formulas (1) and (2).
The organic electroluminescent compounds according to the present invention can be specifically exemplified by the following compounds, but they are not restricted thereto.
The process for preparing the organic electroluminescent compounds according to the present invention is exemplified by Reaction Scheme (1), but not being restricted thereto.
[Reaction Scheme 1]
In the reaction scheme, A1 through A4, B1 through B8, L1, L2 and R1 through R3 are defined as for Chemical Formulas (1) and (2), and X represents halogen.
The present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1) or (2).
The organic layer comprises an electroluminescent layer which comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1) or (2) as host, and one or more dopant(s). The dopant to be applied to the organic electroluminescent devices according to the invention are not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (3):
[Chemical Formula 3]
M1L101L102L103
wherein,
M1 is a metal selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 in the Periodic Table of Elements, and ligands L101, L102 and L103
are independently selected from the following structures:
wherein,
R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s), or halogen;
R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(C1-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);
R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R224 and R225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;
R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;
Q represents 
, 
or 
, wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
The dopant compounds represented by Chemical Formula (3) may be exemplified by the following compounds, without restriction.
The organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1) or (2). The arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
In an organic electroluminescent device according to the present invention, the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the organic electroluminescent compound represented by Chemical Formula (1) or (2). The organic layer may comprise an electroluminescent layer and a charge generating layer.
The organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1) or (2), to form an organic electroluminescent device emitting white light. The compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
In an organic electroluminescent device according to the present invention, it is preferable to arrange one or more layer(s) (here-in-below, referred to as the "surface layer") selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to arrange a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer. As the result, stability in operation can be obtained.
Examples of chalcogenides preferably include SiOx (1=X=2), AlOx (1=X=1.5), SiON, SiAlON, or the like. Examples of metal halides preferably include LiF, MgF2, CaF2, fluorides of rare earth metal or the like. Examples of metal oxides preferably include Cs2O, Li2O, MgO, SrO, BaO, CaO, or the like.
In an organic electroluminescent device according to the present invention, it is also preferable to arrange, on at least one surface of the pair of electrodes thus manufactured, a mixed region of electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
A white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life properties of material, OLED's having very good operation life can be manufactured therefrom.
The present invention is further described by referring to representative compounds with regard to the organic electroluminescent compounds according to the invention, preparation thereof and luminescent properties of the devices manufactured therefrom, but those examples are provided for illustration of the embodiments only, not being intended to limit the scope of the invention by any means.
[Preparation Example 1] Preparation of Compound (10)
Preparation of Compound (1-1)
A solution of 1,3-dibromobenzene (20 g, 84.77 mmol) dissolved in THF (500 mL) was chilled to -78℃. To the solution, slowly added was n-BuLi (2.5 M, 33.9 mL, 84.77 mmol), and the mixture was stirred at -78℃ for 1 hour. A solution of chlorotriphenylsilane ((C6H5)3SiCl) (29.9 g) dissolved in THF (100 mL) was added to thereto. The mixture was slowly warmed to ambient temperature, and stirred for 12 hours. After extracting the mixture with ethyl acetate, the extract was washed with distilled water and aqueous NaCl solution, dried over anhydrous MgSO4, and distilled under reduced pressure. Recrystallization from methylene chloride and methanol (MC:MeOH = 1:10) gave Compound (1-1) (18 g, 95%).
Preparation of Compound (1-2)
A solution of Compound (1-1) (20 g, 90.06 mmol) dissolved in THF (600 mL) was chilled to -78℃. To the solution, slowly added was n-BuLi (2.5 M, 43.2 mL, 108.08 mmol), and the mixture was stirred at -78℃ for 1 hour. Trimethylborate (16.06 mL, 144.11 mmol) was added to thereto. The mixture was slowly warmed to ambient temperature, and stirred for 12 hours. After extracting the mixture with ethyl acetate, the extract was washed with distilled water and aqueous NaCl solution, dried over anhydrous MgSO4, and distilled under reduced pressure. Recrystallization from methylene chloride and hexane (1:10) gave Compound (1-2) (12 g, 35%).
Preparation of Compound (1-3)
Sodium hydride (NaH, 60% in mineral oil) (3.3 g, 83.90 mmol) was diluted in DMF (10 mL). A solution of carbazole (11.2 g, 67.12 mmol) dissolved in DMF (60 mL) was added thereto, and the mixture was stirred at ambient temperature for 1 hour. A solution of 2,4-dichloropyrimidine (10 g, 67.12 mmol) dissolved in DMF (60 mL) was added thereto, and the resultant mixture was stirred at ambient temperature for 4 hours. Then, distilled water (40 mL) was added thereto, and the mixture was extracted with methylene chloride. The extract was washed with distilled water and aqueous NaCl solution, dried over anhydrous MgSO4, and distilled under reduced pressure. Purification via column chromatography gave Compound (1-3) (4.0 g, 21%).
Preparation of Compound (10)
In a reaction vessel, a mixture of Compound (1-3) (3.8 g, 13.58 mmol), Compound (1-2) (6.2 g, 16.30 mmol), Pd(PPh3)4 (784 mg, 0.67 mmol), aqueous 2M Na2CO3 solution (70 mL), ethanol (50 mL) and toluene (200 mL) was stirred under reflux at 120℃ for 12 hours. After cooling to ambient temperature, the mixture was extracted with ethyl acetate, and the extract was washed with distilled water and aqueous NaCl solution. Recrystallization from ethyl acetate gave Compound (10) (5.5 g, 69%).
[Preparation Example 2] Preparation of Compound (16)
Preparation of Compound (2-1)
In a reaction vessel, a mixture of 2-chloro-3-nitropyridine (25 g, 157.6 mmol), phenylboronic acid (24.9 g, 204.9 mmol), Pd(PPh3)4 (5.4 g, 4.73 mmol), K2CO3 (54.48 g, 394.2 mmol), distilled water (150 mL), toluene (300 mL) and ethanol (100 mL) was stirred under reflux for 12 hours. Then the mixture was cooled to room temperature, and distilled water was added thereto. The resultant mixture was extracted with methylene chloride, and the extract was dried over MgSO4, and distilled under reduced pressure. Purification via column chromatography gave Compound (2-1) (30 g, 149.85 mmol, 95.45%).
Preparation of Compound (2-2)
Compound (2-1) (30 g, 149.85 mmol) was mixed with triethylphosphite (150 mL), and the mixture was stirred at 180℃ for 4 hours. After cooling to ambient temperature, the reaction mixture was distilled under reduced pressure. Purification via column chromatography gave Compound (2-2) (2.1 g, 12.48 mmol, 8.37%).
Preparation of Compound (2-3)
According to the same synthetic procedure for preparing Compound (1-3) in Preparation Example 1, Compound (2-3) (2.6 g, 7.99 mmol, 60.1%) was obtained.
Preparation of Compound (16)
According to the same synthetic procedure for preparing Compound (10) in Preparation Example 1, Compound (16) (3.1 g, 5.33 mmol, 67%) was obtained.
[Preparation Example 3] Preparation of Compound (19)
Preparation of Compound (3-1)
In a reaction vessel, a mixture of bromo-2-nitrobenzene (30 g, 148.5 mmol), 1-naphthaleneboronic acid (30.6 g, 178.2 mmol), Pd(PPh3)4 (5.14 g, 4.45 mmol), aqueous 2M K2CO3 solution (297.01 mmol), toluene (500 mL) and ethanol (200 mL) was stirred under reflux for 4 hours. Then the mixture was cooled to ambient temperature, and distilled water was added thereto. The resultant mixture was extracted with ethyl acetate, and the extract was dried over anhydrous MgSO4, and distilled under reduced pressure. Purification via column chromatography gave Compound (3-1) (31 g, 123.3 mmol, 84.03%).
Preparation of Compound (3-2)
In a reaction vessel, Compound (3-1) (31 g, 124.3 mmol) and triethylphosphite (300 mL) were stirred under reflux for 10 hours. Then the mixture was cooled to ambient temperature, and organic solvent was evaporated under reduced pressure. To the residue, distilled water was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4 and evaporated under reduced pressure. Purification via column chromatography gave Compound (3-2) (18 g, 82.84 mmol, 66.81%).
Preparation of Compound (3-3)
According to the same synthetic procedure for preparing Compound (1-3) in Preparation Example 1, Compound (3-3) (19 g, 51.04 mmol, 61.6%) was obtained.
Preparation of Compound (19)
According to the same synthetic procedure for preparing Compound (10) in Preparation Example 1, Compound (19) (16.3 g, 25.9 mmol, 50.1%) was obtained.
[Preparation Example 4] Preparation of Compound (61)
Preparation of Compound (4-1)
To a solution of Compound (19) (19 g, 42.54 mmol) dissolved in DMF (200 mL), added was NBS (8.33 g, 46.80 mmol). After stirring the mixture at ambient temperature for 10 hours, the organic solvent was evaporated under reduced pressure. To the residue, distilled water was added, and the resultant mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4, and distilled under reduced pressure. Purification via column chromatography gave Compound (4-1) (20 g, 38.06 mmol, 89.47%).
Preparation of Compound (4-2)
According to the same synthetic procedure for preparing Compound (1-2) in Preparation Example 1, Compound (4-2) (8 g, 16.31 mmol, 42.86%) was obtained.
Preparation of Compound (4-3)
According to the same synthetic procedure for preparing Compound (3-1) in Preparation Example 3, Compound (4-3) (7 g, 12.33 mmol, 75.62%) was obtained.
Preparation of Compound (4-4)
According to the same synthetic procedure for preparing Compound (3-2) in Preparation Example 3, Compound (4-4) (4 g, 7.46 mmol, 58.33%) was obtained.
Preparation of Compound (61)
A mixture of Compound (4-4) (4 g, 7.46 mmol), iodobenzene (1.25 mL, 11.20 mmol), copper (0.71 g, 11.20 mmol), 18-Crown-6 (0.15 g, 0.59 mmol), K2CO3 (3.1 g, 11.20 mmol) and 1,2-dichlorobenzene (100 mL) was stirred under reflux at 180℃ for 15 hours. After cooling to ambient temperature, the mixture was evaporated under reduced pressure, and extracted with ethyl acetate. The extract was washed with distilled water, dried over anhydrous MgSO4, and evaporated under reduced pressure. The residue was purified via column chromatography to obtain Compound (61) (3.6 g, 5.88 mmol, 78.88%).
[Preparation Example 5] Preparation of Compound (62)
Preparation of Compound (5-1)
According to the same synthetic procedure for preparing Compound (3-1) in Preparation Example 3 but using dibenzo[b,d]furan-4-ylboronic acid, Compound (5-1) (11 g, 38.02 mmol, 89.22%) was obtained.
Preparation of Compound (5-2)
According to the same synthetic procedure for preparing Compound (3-2) in Preparation Example 3, Compound (5-2) (8 g, 31.09 mmol, 81.78%) was obtained.
Preparation of Compound (5-3)
According to the same synthetic procedure for preparing Compound (1-3) in Preparation Example 1, Compound (5-3) (7.4 g, 20.11 mmol, 65.66%) was obtained.
Preparation of Compound (62)
According to the same synthetic procedure for preparing Compound (10) in Preparation Example 1, Compound (62) (5.8 g, 8.65 mmol, 43.28%) was obtained.
According to the same procedure as described in Preparation Examples 1 to 5, prepared were organic electroluminescent compounds (Compounds 1 to 70), of which 1H NMR and MS/FAB data are listed in Table 1.
[Table 1]
[Example 1] Manufacture of OLED's by using organic electroluminescent compounds according to the invention
OLED devices were manufactured by using the electroluminescent material according to the invention.
First, a transparent electrode ITO thin film (15 Ω/□) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated to reach 10-6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
Then, to another cell of the vacuum vapor-deposit device, charged was N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB), and electric current was applied to the cell to evaporate NPB, thereby providing vapor-deposit of a hole transport layer of 20 nm of thickness on the hole injection layer.
After forming the hole injecting layer and the hole transport layer, an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (12) according to the present invention as host material, and compound Ir(ppy)3 (of which the structure is shown below) was charged to another cell as dopant material. Two substances were evaporated at different rates to provide vapor-deposition at a concentration of 4 to 10% by weight. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
Then, on the electroluminescent layer, bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III) (BAlq) was vapor-deposited as a hole blocking layer in a thickness of 5 nm, tris(8-hydroxyquinoline)aluminum (III) (Alq) was vapor-deposited as an electron transport layer in a thickness of 20 nm, and then lithium quinolate (Liq) was vapor-deposited as an electron injecting layer in a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited in a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10-6 torr.
[Example 2] Manufacture of OLED's by using organic electroluminescent compounds according to the invention
OLED's were manufactured according to the same procedure as described in Example 1 except the hole blocking layer.
[Example 3] Manufacture of OLED's by using organic electroluminescent compounds according to the invention
OLED's were manufactured according to the same procedure as described in Example 1 but using in the electroluminescent layer Compound (12) according to the present invention as host material and Compound (19) and (piq)2Ir(acac) instead of dopant Ir(ppy)3.
[Example 4] Manufacture of OLED's by using organic electroluminescent compounds according to the invention
OLED's were manufactured according to the same procedure as described in Example 3 except the hole blocking layer.
[Comparative Example 1] Manufacture of an OLED by using conventional electroluminescent compound
An OLED was manufactured according to the same procedure as described in Example 1 but using CBP as host material in one cell of the vacuum vapor-deposit device, instead of the compound according to the invention.
[Comparative Example 2] Manufacture of an OLED by using conventional electroluminescent compound
An OLED was manufactured according to the same procedure as described in Example 3 but using CBP as host material in one cell of the vacuum vapor-deposit device, instead of the compound according to the invention.
The luminous efficiencies of the OLED's comprising the organic electroluminescent compounds according to the present invention (Examples 1 to 4) and conventional electroluminescent compounds (Comparative Examples 1 and 2) were measured at 1,000 cd/m2, respectively, and the results are shown in Table 2.
[Table 2]
As can be seen from Table 2, the electroluminescent compounds developed by the present invention exhibited excellent features in terms of performances as compared to conventional material. Furthermore, the devices employing as host material the organic electroluminescent compounds according to the present invention not only exhibit excellent luminous properties, but also lowered operation voltage, confirming the improved luminous efficiency.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula (1) or (2):[Chemical Formula 1]
[Chemical Formula 2]
wherein,A1 through A5 and B1 through B8 independently represent N or CR21; if two adjacent groups from A1 through A5 and B1 through B8 represent CR21, those R21 groups may be linked together via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; and the carbon atom(s) of the alkylene may be substituted by one or more heteroatom(s) selected from NR31, O and S, and the carbon atom of alkenylene may be substituted by N;L1 and L2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s), or (C3-C30)heteroarylene with or without substituent(s), provided that both L1 and L2 cannot represent chemical bonds at the same time;R1 through R3, R21 and R31 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more(C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), substituted or unsubstituted 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkyl fused with one or more aromatic ring(s), adamantyl with or without substituent(s), (C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s),or
;
W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;R41 through R43 and R51 through R58 are defined as for R1 through R3 and R21 above, and each of R51 through R58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;each of the heterocycloalkyl and heteroaryl contains one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; andm represents an integer 0, 1 or 2. - The organic electroluminescent compound according to claim 1, wherein each substituent of L1, L2, R1 through R3, R11 through R18, R21 and R31 is further substituted by one or more substituent(s) selected from a group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR61R62, BR63R64, PR65R66, P(=O)R67R68 [wherein R61 through R68 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s)or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or the adjacent substituents are linked each other to form a ring.
- The organic electroluminescent compound according to claim 1, whereinis selected from the following structures:
wherein,R21 and R31 independently represent halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), NR11R12 [wherein R11 and R12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s),or
; and
W and R43 are defined as in claim 1. - The organic electroluminescent compound according to claim 1, whereinor
is independently selected from the following structures:
wherein,R1 through R3 independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);R21 represents hydrogen, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more(C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), NR11R12 [wherein R11 through R18 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)aryloxy with or without substituent(s),or
; and
W and R43 are defined as in claim 1. - The organic electroluminescent compound according to claim 1, which is selected from the following compounds:
- An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 5.
- The organic electroluminescent device according to claim 6, which is comprised of a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) and one or more dopant(s) represented by Chemical Formula (3):[Chemical Formula 3]M1L101L102L103wherein,M1 is a metal selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 in the Periodic Table of Elements, and ligands L101, L102 and L103 are independently selected from the following structures:
wherein,R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s), or halogen;R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(C1-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R224 and R225 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), or halogen;R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), or halogen;Q represents,
or
, wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano, or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, and one or more metal(s) from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition metals in the Periodic Table of Elements.
- The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 7, which is a white light-emitting organic electroluminescent device comprising one or more additional organic electroluminescent layer(s) emitting blue, red or green light.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010800287228A CN102803436A (en) | 2009-04-29 | 2010-04-08 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2009-0037519 | 2009-04-29 | ||
| KR1020090037519A KR20100118700A (en) | 2009-04-29 | 2009-04-29 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2010126234A1 true WO2010126234A1 (en) | 2010-11-04 |
Family
ID=43032349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2010/002170 WO2010126234A1 (en) | 2009-04-29 | 2010-04-08 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR20100118700A (en) |
| CN (1) | CN102803436A (en) |
| TW (1) | TW201215658A (en) |
| WO (1) | WO2010126234A1 (en) |
Cited By (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2292604A3 (en) * | 2009-08-10 | 2011-03-30 | Samsung Mobile Display Co., Ltd. | Condensed-cyclic compound and organic light emitting diode having organic layer including the same |
| WO2011125020A1 (en) * | 2010-04-06 | 2011-10-13 | Basf Se | Substituted carbazole derivatives and use thereof in organic electronics |
| CN103102364A (en) * | 2011-11-14 | 2013-05-15 | 通用显示公司 | Triphenylene silane hosts |
| JP2013093432A (en) * | 2011-10-26 | 2013-05-16 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display and lighting system |
| JP2013100341A (en) * | 2011-07-22 | 2013-05-23 | Semiconductor Energy Lab Co Ltd | Compound |
| WO2013094999A2 (en) * | 2011-12-23 | 2013-06-27 | 주식회사 두산 | Organic compound, and organic electroluminescent device using same |
| WO2013108997A1 (en) * | 2012-01-18 | 2013-07-25 | 덕산하이메탈(주) | Compound for organic electronic device, and organic electronic device and electronic apparatus comprising same |
| WO2013133219A1 (en) * | 2012-03-05 | 2013-09-12 | 東レ株式会社 | Light emitting element |
| EP2687530A1 (en) * | 2011-03-16 | 2014-01-22 | Nippon Steel & Sumikin Chemical Co., Ltd. | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| CN103570737A (en) * | 2012-07-25 | 2014-02-12 | 三星显示有限公司 | Heterocyclic compounds, organic light-emitting device comprising the same and organic light-emitting display |
| WO2014030554A1 (en) * | 2012-08-21 | 2014-02-27 | 保土谷化学工業株式会社 | Compound having triphenylsilyl pyridyl group and carbazole ring structure and organic electroluminescence device |
| JP2014505678A (en) * | 2010-12-21 | 2014-03-06 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| WO2014050588A1 (en) * | 2012-09-28 | 2014-04-03 | 新日鉄住金化学株式会社 | Organic electroluminescent element material and organic electroluminescent element using same |
| WO2014092354A1 (en) * | 2012-12-10 | 2014-06-19 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| WO2014092362A1 (en) * | 2012-12-11 | 2014-06-19 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| WO2014157618A1 (en) * | 2013-03-29 | 2014-10-02 | コニカミノルタ株式会社 | Organic electroluminescent element, and lighting device and display device which are provided with same |
| WO2016021815A1 (en) * | 2014-08-06 | 2016-02-11 | 삼성에스디아이 주식회사 | Organic compound, organic optoelectronic element, and display device |
| EP2725080A4 (en) * | 2011-06-27 | 2016-03-02 | Lg Chemical Ltd | Novel compound and organic light-emitting device using same |
| US9373806B2 (en) | 2012-01-18 | 2016-06-21 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| TWI583772B (en) * | 2011-02-11 | 2017-05-21 | 環球顯示器公司 | Organic light emitting device and materials for use in same |
| US9705094B2 (en) | 2014-11-26 | 2017-07-11 | Samsung Electronics Co., Ltd. | Organic semiconductor compound, organic thin film including same, and electronic device including the organic thin film |
| JP2017522732A (en) * | 2014-07-17 | 2017-08-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Electron transport material and organic electroluminescent device containing the same |
| US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
| US9899604B2 (en) | 2013-02-13 | 2018-02-20 | Samsung Electronics Co., Ltd. | Compound for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode |
| US9899600B2 (en) | 2012-11-26 | 2018-02-20 | Heesung Material Ltd. | Multicyclic aromatic compound and organic light emitting device using the same |
| US9954190B2 (en) | 2011-06-16 | 2018-04-24 | Udc Ireland Limited | Organic electric-field light-emitting element, light-emitting material for organic electric-field light-emitting element, and light-emitting device, display device, and illumination device using same element |
| US9997723B2 (en) | 2014-05-23 | 2018-06-12 | Rohm And Haas Electronic Materials Korea Ltd | Organic electroluminescent compound and an organic electroluminescent device comprising the same |
| US10003031B2 (en) | 2012-12-11 | 2018-06-19 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| JP2018118981A (en) * | 2011-10-06 | 2018-08-02 | 株式会社半導体エネルギー研究所 | Organic compound |
| CN109952358A (en) * | 2016-12-07 | 2019-06-28 | 罗门哈斯电子材料韩国有限公司 | Electroluminescent organic material and Organnic electroluminescent device comprising it |
| US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210028376A1 (en) * | 2019-07-22 | 2021-01-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910577B2 (en) | 2017-03-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910570B2 (en) | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930864B2 (en) | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10941170B2 (en) | 2017-05-03 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10964904B2 (en) | 2017-01-20 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10998507B2 (en) | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038137B2 (en) | 2017-04-28 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11158820B2 (en) | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201299B2 (en) | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201300B2 (en) | 2018-07-31 | 2021-12-14 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including condensed cyclic compound |
| KR102349311B1 (en) * | 2021-08-20 | 2022-01-10 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US11228004B2 (en) | 2018-06-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11245080B2 (en) | 2015-04-06 | 2022-02-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11339182B2 (en) | 2018-06-07 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349081B2 (en) * | 2017-11-14 | 2022-05-31 | Beijing Summer Sprout Technology Co., Ltd. | Azaindolocarbazole compounds |
| US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11370809B2 (en) | 2019-02-08 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11437591B2 (en) | 2017-08-24 | 2022-09-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469383B2 (en) | 2018-10-08 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11512093B2 (en) | 2019-03-04 | 2022-11-29 | Universal Display Corporation | Compound used for organic light emitting device (OLED), consumer product and formulation |
| US11515489B2 (en) | 2018-11-28 | 2022-11-29 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557738B2 (en) | 2019-02-22 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11613550B2 (en) | 2019-04-30 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes |
| US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706972B2 (en) | 2015-09-08 | 2023-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11773320B2 (en) | 2019-02-21 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11812624B2 (en) | 2019-01-30 | 2023-11-07 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910699B2 (en) | 2017-08-10 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11920070B2 (en) | 2019-07-12 | 2024-03-05 | The University Of Southern California | Luminescent janus-type, two-coordinated metal complexes |
| US11957050B2 (en) | 2019-02-08 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889271B2 (en) | 2006-11-26 | 2014-11-18 | Duksan High Metal Co., Ltd. | Compound containing a 5-membered heterocycle and organic light-emitting diode using same, and terminal for same |
| DE102009053382A1 (en) * | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materials for electronic devices |
| KR101497123B1 (en) * | 2011-12-30 | 2015-03-09 | 덕산네오룩스 주식회사 | Compound Containing 5-Membered Heterocycle And Organic Electronic Element Using The Same, Terminal Thereof |
| KR101612154B1 (en) * | 2012-12-13 | 2016-04-14 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| KR102146105B1 (en) * | 2013-06-13 | 2020-08-20 | 엘지디스플레이 주식회사 | Blue Phosphorescent Compound and Organic Light Emitting Diode Devices Using The Same |
| KR20150070475A (en) * | 2013-12-16 | 2015-06-25 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
| CN109593080A (en) * | 2017-09-30 | 2019-04-09 | 上海自旭光电科技有限公司 | Fluorescent material |
| CN108409774B (en) * | 2017-12-19 | 2021-01-05 | 北京绿人科技有限责任公司 | Organic electroluminescent compound, application thereof and organic electroluminescent device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060177691A1 (en) * | 2005-02-05 | 2006-08-10 | Au Optronics Corp. | Compound and organic light-emitting diode and display utilizing the same |
| KR20070106082A (en) * | 2006-04-28 | 2007-11-01 | 동우 화인켐 주식회사 | Organosilane compounds, electroluminiscent materials comprising the same, and organic electroluminiscent device |
| WO2008120899A1 (en) * | 2007-03-29 | 2008-10-09 | Dongwoo Fine-Chem | Naphthyl carbazole derivatives, kl host material, the organic light emitting device employing the same, the display device and the illumination device employing the same |
| WO2008143387A1 (en) * | 2007-05-17 | 2008-11-27 | Cheil Industries Inc. | Vinyl-based polymer with silicon or/and tin and organic light emission diode using the same |
| KR20100025664A (en) * | 2008-08-28 | 2010-03-10 | 동우 화인켐 주식회사 | Organic thin film materials for organic electroluminescent device, and organic electroluminescent device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4411851B2 (en) * | 2003-03-19 | 2010-02-10 | コニカミノルタホールディングス株式会社 | Organic electroluminescence device |
| EP1917243B1 (en) * | 2005-07-14 | 2012-02-15 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, and light emitting element material, light emitting element, and electronic appliance obtained using the same |
| KR20080047209A (en) * | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | Organic light emitting compound and organic light emitting device comprising the same |
| KR101369662B1 (en) * | 2007-03-29 | 2014-03-06 | 동우 화인켐 주식회사 | New Compounds, KL Host Material And Organic Light Emitting Device |
-
2009
- 2009-04-29 KR KR1020090037519A patent/KR20100118700A/en not_active Application Discontinuation
-
2010
- 2010-04-08 WO PCT/KR2010/002170 patent/WO2010126234A1/en active Application Filing
- 2010-04-08 CN CN2010800287228A patent/CN102803436A/en active Pending
- 2010-04-29 TW TW099113629A patent/TW201215658A/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060177691A1 (en) * | 2005-02-05 | 2006-08-10 | Au Optronics Corp. | Compound and organic light-emitting diode and display utilizing the same |
| KR20070106082A (en) * | 2006-04-28 | 2007-11-01 | 동우 화인켐 주식회사 | Organosilane compounds, electroluminiscent materials comprising the same, and organic electroluminiscent device |
| WO2008120899A1 (en) * | 2007-03-29 | 2008-10-09 | Dongwoo Fine-Chem | Naphthyl carbazole derivatives, kl host material, the organic light emitting device employing the same, the display device and the illumination device employing the same |
| WO2008143387A1 (en) * | 2007-05-17 | 2008-11-27 | Cheil Industries Inc. | Vinyl-based polymer with silicon or/and tin and organic light emission diode using the same |
| KR20100025664A (en) * | 2008-08-28 | 2010-03-10 | 동우 화인켐 주식회사 | Organic thin film materials for organic electroluminescent device, and organic electroluminescent device |
Non-Patent Citations (3)
| Title |
|---|
| CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2009:768660 * |
| KANG, JAE-WOOK ET AL.: "A host material containing tetraphenylsilane for phosphorescent OLEDs with high efficiency and operational stability", ORGANIC ELECTRONICS, vol. 9, no. 4, 2008, pages 452 - 460 * |
| SHEN Q. ET AL.: "Synthesis of tetraarylsilanes and its usage as blue emitters in electroluniinescence", SYNTHETIC METALS, vol. 158, no. 21-24, 2008, pages 1054 - 1058 * |
Cited By (150)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2292604A3 (en) * | 2009-08-10 | 2011-03-30 | Samsung Mobile Display Co., Ltd. | Condensed-cyclic compound and organic light emitting diode having organic layer including the same |
| JP2013528929A (en) * | 2010-04-06 | 2013-07-11 | ビーエーエスエフ ソシエタス・ヨーロピア | Substituted carbazole derivatives and their use in organic electronics |
| WO2011125020A1 (en) * | 2010-04-06 | 2011-10-13 | Basf Se | Substituted carbazole derivatives and use thereof in organic electronics |
| CN102933582A (en) * | 2010-04-06 | 2013-02-13 | 巴斯夫欧洲公司 | Substituted carbazole derivatives and use thereof in organic electronics |
| EP2556075A1 (en) * | 2010-04-06 | 2013-02-13 | Basf Se | Substituted carbazole derivatives and use thereof in organic electronics |
| EP2556075A4 (en) * | 2010-04-06 | 2013-10-02 | Basf Se | Substituted carbazole derivatives and use thereof in organic electronics |
| JP2014505678A (en) * | 2010-12-21 | 2014-03-06 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| TWI583772B (en) * | 2011-02-11 | 2017-05-21 | 環球顯示器公司 | Organic light emitting device and materials for use in same |
| CN103582641B (en) * | 2011-03-16 | 2016-05-04 | 新日铁住金化学株式会社 | Nitrogen-containing aromatic compound and organic electroluminescent device |
| US9543526B2 (en) | 2011-03-16 | 2017-01-10 | Nippon Steel & Sumikin Chemical Co., Ltd. | Nitrogen-containing aromatic compounds and organic electroluminescent device |
| KR101941529B1 (en) * | 2011-03-16 | 2019-01-23 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| KR20140023316A (en) * | 2011-03-16 | 2014-02-26 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| JP5778756B2 (en) * | 2011-03-16 | 2015-09-16 | 新日鉄住金化学株式会社 | Nitrogen-containing aromatic compound and organic electroluminescence device |
| EP2687530A4 (en) * | 2011-03-16 | 2014-09-17 | Nippon Steel & Sumikin Chem Co | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| EP2687530A1 (en) * | 2011-03-16 | 2014-01-22 | Nippon Steel & Sumikin Chemical Co., Ltd. | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| CN103582641A (en) * | 2011-03-16 | 2014-02-12 | 新日铁住金化学株式会社 | Nitrogen-containing aromatic compounds and organic electroluminescent elements |
| US9954190B2 (en) | 2011-06-16 | 2018-04-24 | Udc Ireland Limited | Organic electric-field light-emitting element, light-emitting material for organic electric-field light-emitting element, and light-emitting device, display device, and illumination device using same element |
| EP2725080A4 (en) * | 2011-06-27 | 2016-03-02 | Lg Chemical Ltd | Novel compound and organic light-emitting device using same |
| US9728728B2 (en) | 2011-06-27 | 2017-08-08 | Lg Chem, Ltd. | Compound and organic light-emitting device using same |
| US9373793B2 (en) | 2011-06-27 | 2016-06-21 | Lg Chem, Ltd. | Compound and organic light-emitting device using same |
| JP2013100341A (en) * | 2011-07-22 | 2013-05-23 | Semiconductor Energy Lab Co Ltd | Compound |
| JP2018118981A (en) * | 2011-10-06 | 2018-08-02 | 株式会社半導体エネルギー研究所 | Organic compound |
| JP2013093432A (en) * | 2011-10-26 | 2013-05-16 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display and lighting system |
| CN106674266B (en) * | 2011-11-14 | 2021-10-29 | 通用显示公司 | Triphenylene silane hosts |
| JP2013103937A (en) * | 2011-11-14 | 2013-05-30 | Universal Display Corp | Triphenylene silane host |
| TWI629280B (en) * | 2011-11-14 | 2018-07-11 | 美商環球展覽公司 | Triphenylene silane hosts |
| US8652656B2 (en) * | 2011-11-14 | 2014-02-18 | Universal Display Corporation | Triphenylene silane hosts |
| CN103102364B (en) * | 2011-11-14 | 2017-03-01 | 通用显示公司 | Sanya phenylsilane main body |
| CN106674266A (en) * | 2011-11-14 | 2017-05-17 | 通用显示公司 | Triphenylene silane host |
| CN103102364A (en) * | 2011-11-14 | 2013-05-15 | 通用显示公司 | Triphenylene silane hosts |
| US9142788B2 (en) | 2011-11-14 | 2015-09-22 | Universal Display Corporation | Host materials for OLEDs |
| JP2016222683A (en) * | 2011-11-14 | 2016-12-28 | ユニバーサル ディスプレイ コーポレイション | Triphenylene silane hosts |
| TWI577689B (en) * | 2011-11-14 | 2017-04-11 | 環球展覽公司 | Triphenylene silane hosts |
| US20130119353A1 (en) * | 2011-11-14 | 2013-05-16 | Universal Display Corporation | Triphenylene silane hosts |
| WO2013094999A3 (en) * | 2011-12-23 | 2013-08-22 | 주식회사 두산 | Organic compound, and organic electroluminescent device using same |
| WO2013094999A2 (en) * | 2011-12-23 | 2013-06-27 | 주식회사 두산 | Organic compound, and organic electroluminescent device using same |
| KR101506761B1 (en) | 2011-12-23 | 2015-03-30 | 주식회사 두산 | Organic compound and organic electroluminescent devices using the same |
| US9373806B2 (en) | 2012-01-18 | 2016-06-21 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| WO2013108997A1 (en) * | 2012-01-18 | 2013-07-25 | 덕산하이메탈(주) | Compound for organic electronic device, and organic electronic device and electronic apparatus comprising same |
| WO2013133219A1 (en) * | 2012-03-05 | 2013-09-12 | 東レ株式会社 | Light emitting element |
| US9893301B2 (en) | 2012-07-25 | 2018-02-13 | Samsung Display Co., Ltd. | Heterocyclic compounds and organic light-emitting devices including the same |
| CN103570737A (en) * | 2012-07-25 | 2014-02-12 | 三星显示有限公司 | Heterocyclic compounds, organic light-emitting device comprising the same and organic light-emitting display |
| WO2014030554A1 (en) * | 2012-08-21 | 2014-02-27 | 保土谷化学工業株式会社 | Compound having triphenylsilyl pyridyl group and carbazole ring structure and organic electroluminescence device |
| JP5499227B1 (en) * | 2012-08-21 | 2014-05-21 | 保土谷化学工業株式会社 | Compound having triphenylsilylpyridyl group and carbazole ring structure and organic electroluminescence device |
| WO2014050588A1 (en) * | 2012-09-28 | 2014-04-03 | 新日鉄住金化学株式会社 | Organic electroluminescent element material and organic electroluminescent element using same |
| JPWO2014050588A1 (en) * | 2012-09-28 | 2016-08-22 | 新日鉄住金化学株式会社 | Material for organic electroluminescence device and organic electroluminescence device using the same |
| US9899600B2 (en) | 2012-11-26 | 2018-02-20 | Heesung Material Ltd. | Multicyclic aromatic compound and organic light emitting device using the same |
| WO2014092354A1 (en) * | 2012-12-10 | 2014-06-19 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| KR101571591B1 (en) | 2012-12-10 | 2015-11-24 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| WO2014092362A1 (en) * | 2012-12-11 | 2014-06-19 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| US10003031B2 (en) | 2012-12-11 | 2018-06-19 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| US9899604B2 (en) | 2013-02-13 | 2018-02-20 | Samsung Electronics Co., Ltd. | Compound for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode |
| WO2014157618A1 (en) * | 2013-03-29 | 2014-10-02 | コニカミノルタ株式会社 | Organic electroluminescent element, and lighting device and display device which are provided with same |
| US10135002B2 (en) | 2013-03-29 | 2018-11-20 | Konica Minolta, Inc. | Organic electroluminescent element, and lighting device and display device which are provided with same |
| JPWO2014157618A1 (en) * | 2013-03-29 | 2017-02-16 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENCE ELEMENT, LIGHTING DEVICE AND DISPLAY DEVICE HAVING THE SAME |
| US9997723B2 (en) | 2014-05-23 | 2018-06-12 | Rohm And Haas Electronic Materials Korea Ltd | Organic electroluminescent compound and an organic electroluminescent device comprising the same |
| US10186669B2 (en) | 2014-05-23 | 2019-01-22 | Rohm And Haas Electronic Materials Korea Ltd | Organic electroluminescent compound and an organic electroluminescent device comprising the same |
| JP2017522732A (en) * | 2014-07-17 | 2017-08-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Electron transport material and organic electroluminescent device containing the same |
| WO2016021815A1 (en) * | 2014-08-06 | 2016-02-11 | 삼성에스디아이 주식회사 | Organic compound, organic optoelectronic element, and display device |
| CN106661038B (en) * | 2014-08-06 | 2019-12-31 | 三星Sdi株式会社 | Organic compound, organic photoelectric device and display device |
| US10680190B2 (en) | 2014-08-06 | 2020-06-09 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectronic element, and display device |
| CN106661038A (en) * | 2014-08-06 | 2017-05-10 | 三星Sdi株式会社 | Organic compound, organic optoelectronic element, and display device |
| US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
| US9705094B2 (en) | 2014-11-26 | 2017-07-11 | Samsung Electronics Co., Ltd. | Organic semiconductor compound, organic thin film including same, and electronic device including the organic thin film |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11245080B2 (en) | 2015-04-06 | 2022-02-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11672175B2 (en) | 2015-04-06 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706972B2 (en) | 2015-09-08 | 2023-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11832456B2 (en) | 2015-11-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10998507B2 (en) | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11069864B2 (en) | 2016-11-11 | 2021-07-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3551721A4 (en) * | 2016-12-07 | 2020-07-01 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent material and organic electroluminescent device comprising the same |
| JP2020513685A (en) * | 2016-12-07 | 2020-05-14 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent material and organic electroluminescent device containing the same |
| JP7075402B2 (en) | 2016-12-07 | 2022-05-25 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent material and organic electroluminescent device containing it |
| CN109952358A (en) * | 2016-12-07 | 2019-06-28 | 罗门哈斯电子材料韩国有限公司 | Electroluminescent organic material and Organnic electroluminescent device comprising it |
| US10964904B2 (en) | 2017-01-20 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910577B2 (en) | 2017-03-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11158820B2 (en) | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910570B2 (en) | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038137B2 (en) | 2017-04-28 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10941170B2 (en) | 2017-05-03 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201299B2 (en) | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930864B2 (en) | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11731975B2 (en) | 2017-06-23 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910699B2 (en) | 2017-08-10 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11437591B2 (en) | 2017-08-24 | 2022-09-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349081B2 (en) * | 2017-11-14 | 2022-05-31 | Beijing Summer Sprout Technology Co., Ltd. | Azaindolocarbazole compounds |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11818946B2 (en) | 2018-01-11 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11339182B2 (en) | 2018-06-07 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228004B2 (en) | 2018-06-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201300B2 (en) | 2018-07-31 | 2021-12-14 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including condensed cyclic compound |
| US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469383B2 (en) | 2018-10-08 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11963441B2 (en) | 2018-11-26 | 2024-04-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706980B2 (en) | 2018-11-28 | 2023-07-18 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11515489B2 (en) | 2018-11-28 | 2022-11-29 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11812624B2 (en) | 2019-01-30 | 2023-11-07 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11957050B2 (en) | 2019-02-08 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11370809B2 (en) | 2019-02-08 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11773320B2 (en) | 2019-02-21 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11758807B2 (en) | 2019-02-22 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557738B2 (en) | 2019-02-22 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11512093B2 (en) | 2019-03-04 | 2022-11-29 | Universal Display Corporation | Compound used for organic light emitting device (OLED), consumer product and formulation |
| US11613550B2 (en) | 2019-04-30 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes |
| US11920070B2 (en) | 2019-07-12 | 2024-03-05 | The University Of Southern California | Luminescent janus-type, two-coordinated metal complexes |
| US20210028376A1 (en) * | 2019-07-22 | 2021-01-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11963438B2 (en) | 2020-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
| EP4137492A1 (en) * | 2021-08-20 | 2023-02-22 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR102349311B1 (en) * | 2021-08-20 | 2022-01-10 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US11597700B1 (en) | 2021-08-20 | 2023-03-07 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US11958825B2 (en) | 2023-01-31 | 2024-04-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102803436A (en) | 2012-11-28 |
| KR20100118700A (en) | 2010-11-08 |
| TW201215658A (en) | 2012-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2010126234A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2010114264A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2010114266A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2012050371A1 (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| WO2010114256A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2015084114A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2011010842A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2012050347A1 (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| WO2011019156A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2015099485A1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| WO2012011756A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent devices including the same | |
| WO2011010839A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2015012618A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015099486A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2010114253A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2013165189A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| EP3563437A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2011115378A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2018124697A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2013109030A1 (en) | Organic electroluminescent device comprising the organic electroluminescent compounds | |
| WO2010107244A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2012015265A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2010114263A2 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2011126224A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2013180478A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WWE | Wipo information: entry into national phase |
Ref document number: 201080028722.8 Country of ref document: CN |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10769879 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 10769879 Country of ref document: EP Kind code of ref document: A1 |