WO2011016648A1 - 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
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- WO2011016648A1 WO2011016648A1 PCT/KR2010/005017 KR2010005017W WO2011016648A1 WO 2011016648 A1 WO2011016648 A1 WO 2011016648A1 KR 2010005017 W KR2010005017 W KR 2010005017W WO 2011016648 A1 WO2011016648 A1 WO 2011016648A1
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- WIPO (PCT)
- Prior art keywords
- substituent
- alkyl
- organic electroluminescent
- aryl
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 97
- 125000001424 substituent group Chemical group 0.000 claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 239000010410 layer Substances 0.000 claims description 42
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 33
- -1 cyano, amino Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 description 37
- 239000000463 material Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 230000002829 reductive effect Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000002541 furyl group Chemical group 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-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
- 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 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol 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-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
- 238000006243 chemical reaction Methods 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 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
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- ODAXNYMENLFYMY-UHFFFAOYSA-N (2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC=C1B(O)O ODAXNYMENLFYMY-UHFFFAOYSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 0 *C=CC1=C(C=I)Nc(cccc2)c2N1 Chemical compound *C=CC1=C(C=I)Nc(cccc2)c2N1 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- QENIALCDPFDFHX-UHFFFAOYSA-N 1,4-dibromo-2,5-dimethylbenzene Chemical compound CC1=CC(Br)=C(C)C=C1Br QENIALCDPFDFHX-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
- 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
- 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
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-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
- BQVVAMSFUZXOKR-UHFFFAOYSA-N 6,6,12,12-tetraethylindeno[1,2-b]fluorene Chemical compound C(C)C1(C2=CC=CC=C2C2=CC=3C(C=4C=CC=CC4C3C=C21)(CC)CC)CC BQVVAMSFUZXOKR-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- OPROJCMACCUYOM-UHFFFAOYSA-N CCC1(CC)c(cc2-c3cc4c(-c(cc5)ccc5C#N)c(cccc5)c5c(-c(cc5)ccc5C#N)c4cc3C(CC)(CC)c2c2)c2-c2ccccc12 Chemical compound CCC1(CC)c(cc2-c3cc4c(-c(cc5)ccc5C#N)c(cccc5)c5c(-c(cc5)ccc5C#N)c4cc3C(CC)(CC)c2c2)c2-c2ccccc12 OPROJCMACCUYOM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- 229910018828 PO3H2 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-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
- 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
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- 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
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 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
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 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
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl 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
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-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
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
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- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same.
- the organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
- the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
- the organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode.
- HIL hole injection layer
- HTL hole transport layer
- EML emission material layer
- ETL electron transport layer
- EIL electron injection layer
- the electroluminescent materials may be divided into host materials and dopant materials.
- an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
- development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
- development of materials which are much superior to existing electroluminescent materials is urgently needed.
- tris(8-hydroxyquinoline)-aluminum(III) Alq
- Alq tris(8-hydroxyquinoline)-aluminum(III)
- a coumarin derivative, a quinacridone derivative, DPT, or the like are used as a dopant, with a doping concentration of several to tens %.
- the existing electroluminescent materials exhibit an initial luminescence efficiency that allows commercialization, the efficiency degrades quickly with time. Due to the lifetime problem, they are difficult to be employed in high-performance, large-sized panels.
- an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
- Another object of the present invention is to provide an organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
- the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device using the same.
- the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
- R 1 through R 14 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), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, amino, (C1-C30)alkylamino with or without substituent(s), (C6
- R 51 through R 58 and R 61 through R 63 are the same as defined in R 1 through R 14 ;
- R 21 through R 28 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),
- R a , R b , R c , and R d independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s),
- the Y represents S or O
- R e and R f represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s); and
- n an integer 1 or 2.
- 'alkyl' 'alkoxy' and other substituents containing 'alkyl' moiety include both linear and branched species.
- 'cycloalkyl' includes both adamantyl with or without substituent(s) and (C7-C30)bicycloalkyl with or without substituent(s).
- 'aryl' means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
- Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
- the naphthyl includes 1-naphthyl and 2-naphthyl
- the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
- the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- heteroaryl may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated.
- the heteroaryl includes more than one heteroaryls linked by single bond(s).
- the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
- monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, is
- the '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl.
- the '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
- the '(C2-C30)alkenyl or alkynyl' group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
- R 31 through R 38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
- the R 1 through R 14 , R 21 through R 28 , R 51 through R 58 , and R 61 through R 63 are independently selected from hydrogen, deuterium, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl
- heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., , or , but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
- R 1 through R 14 may be exemplified as following structures but are not limited thereto.
- R 41 through R 48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
- the R 1 through R 14 are exemplified as the following structures, but are not limited thereto.
- organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but is not limited thereto.
- the organic electroluminescent compound according to the present invention may be prepared as shown in following Reaction Scheme 1.
- R 1 through R 14 , X and Y are the same as defined in the Chemical Formula 1.
- an organic electroluminescent device which comprises 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) represented by Chemical Formula 1.
- the organic electroluminescent compound is used as a host material of the electroluminescent layer.
- the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more dopants besides one or more organic electroluminescent compounds of Chemical Formula 1.
- the dopant applied to the organic electroluminescent device of the present invention is not specifically limited.
- the dopant applied to the organic electroluminescent device of the present invention is selected from following Chemical Formulas 2 and 3.
- Ar 11 and Ar 12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar 11 and Ar 12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono
- Ar 13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1:
- Ar 13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2:
- Ar 14 and Ar 15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
- R 201 through R 203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
- d represents an integer from 1 to 4.
- e represents an integer 0 or 1.
- the meaning of the electroluminescent layer may be a single layer as a layer where the light is emitted or may be a multiple layer where two or more layers are laminated.
- the electroluminescent host of the present invention when host-dopant are used in mixture, it is confirmed that the luminous efficiency are remarkably improved by the electroluminescent host of the present invention. It may be configured at doping concentration of 0.5 to 10wt%.
- the electroluminescent host of the present invention has superior conductivity with respect to the hole and electron and excellent stability in material, thereby showing a characteristic of remarkably increasing its life span as well as improving the luminous efficiency.
- the dopant compound of Chemical Formula 3 may be exemplified as the compound described in KR Patent Application No. 10-2009-0023442, more preferably, be selected from the following structures. However, they are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
- the organic layer may include an electroluminescent layer and a charge generating layer.
- the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
- the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
- the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
- the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
- the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- the 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 an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
- a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
- the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
- the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent 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-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
- the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
- Compound 2-1 (30 g, 71.21 mmol), sulfuric acid (100 mL), and acetic acid (100 mL) were mixed and stirred under reflux at 120°C. 10 hours later, the mixture was cooled to room temperature and distilled water was added thereto. After filtering the produced solid under reduced pressure, recrystallization with methanol and EA yielded Compound 2-2 (4 g, 9.91 mmol, 13.95%).
- Compound 2-6 was obtained by combining Compound 2-5 in Preparation Example 1 according to the same method as preparation of Compound 1-3.
- Compound 28 (2.1 g, 2.95mmol, 53 %) was obtained by combining unrefined Compound 2-6 in Preparation Example 1 according to the same method as preparation of Compound 4 .
- 1,4-dimethyl-2,5-dibromobenzene (10 g, 37.88 mmol), 2-(methoxycarbonyl)phenylboronic acid (17 g, 94.71 mmol), Pd(PPh 3 ) 4 (2.18 g, 1.89 mmol), 2M K 2 CO 3 aqueous solution (60 mL), toluene (200 mL), and ethanol (100 mL) were mixed and stirred under reflux. 6 hours later, the mixture was cooled to room temperature. After adding distilled water and extracting with EA, the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 3-1 (11 g, 29.37 mmol, 77.55 %).
- Compound 3-2 (9 g, 24.03 mmol) was mixed with acetic acid (100 mL) and H 3 PO 4 (100 mL) and the mixture was heated at 120°C. 10 hours later, the mixture was cooled to room temperature and distilled water was added thereto. Filtering the produced solid under reduced pressure and washing with NaOH aqueous solution and methanol yielded Compound 3-3 (6 g, 17.72 mmol, 73.76 %).
- Compound 3-4 (6.3 g, 12.95 mmol, 73.1 %) was obtained by combining Compound 3-3 in Preparation Example 1 according to the same method as preparation of Compound 1-1.
- Compound 3-5 (4.3 g, 9.18 mmol, 70.1 %) was obtained by combining Compound 3-4 in Preparation Example 1 according to the same method as preparation of Compound 1-2 .
- Compound 3-6 was obtained by combining Compound 3-5 in Preparation Example 1 according to the same method as preparation of Compound 1-3.
- Organic electroluminescent Compounds 1 to 35 were prepared according to Preparation Example 1 and Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
- An OLED device was manufactured using the electroluminescent material according to the present invention.
- a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a 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.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- NPB N,N' -bis(a-naphthyl)- N,N' -diphenyl-4,4'-diamine
- an electroluminescent layer was formed thereon as follows.
- Compound 4 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound E was placed in another cell as a dopant.
- the two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 2 to 5 wt% based on host.
- Alq tris(8-hydroxyquinoline)-aluminum(III) having a following structure was vapor-deposited with a thickness of 20 nm as an electron transport layer. Then, after vapor-depositing lithium quinolate (Liq) of a following structure with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
- Liq lithium quinolate
- Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.
- An OLED device was manufactured in the same manner as Example 1 except that 9,10-di(naphthalen-3-yl)anthracene (DNA) was used on the electroluminescent layer as host material.
- DNA 9,10-di(naphthalen-3-yl)anthracene
- Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention manufactured in Example 1 and Comparative Example 1 and the conventional electroluminescent compound was measured at 5,000 cd/m 2 . The result is given in Table 2.
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Abstract
Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound disclosed herein exhibits good luminescent efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
Description
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same. The organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
[Chemical Formula 1]
In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
In general, the organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode. Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the emission material layer.
In functional aspect, the electroluminescent materials may be divided into host materials and dopant materials. In general, an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task. Especially, considering the level of EL performance required for medium-to-large sized OLED panels, development of materials which are much superior to existing electroluminescent materials is urgently needed.
For green fluorescent materials, tris(8-hydroxyquinoline)-aluminum(III) (Alq) is used as a host and a coumarin derivative, a quinacridone derivative, DPT, or the like are used as a dopant, with a doping concentration of several to tens %. Although the existing electroluminescent materials exhibit an initial luminescence efficiency that allows commercialization, the efficiency degrades quickly with time. Due to the lifetime problem, they are difficult to be employed in high-performance, large-sized panels.
Accordingly, development of host materials that can provide satisfactory operation life of OLED devices, better stability and excellent performance are required.
Accordingly, an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems. Another object of the present invention is to provide an organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
In one general aspect, the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device using the same. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
[Chemical Formula 1]
wherein
R1 through R14 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), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, amino, (C1-C30)alkylamino with or without substituent(s), (C6-C30)arylamino with or without substituent(s), NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro, , or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fuse ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
X, Y and W independently represent -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
R51 through R58 and R61 through R63 are the same as defined in R1 through R14;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
the R21 through R28 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),
the Ra, Rb, Rc, and Rd independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s),
the Y represents S or O,
the Re and Rf represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s); and
m represents an integer 1 or 2.
In the present invention, 'alkyl' 'alkoxy' and other substituents containing 'alkyl' moiety include both linear and branched species. In the present invention, 'cycloalkyl' includes both adamantyl with or without substituent(s) and (C7-C30)bicycloalkyl with or without substituent(s).
In the present invention, 'aryl' means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s). Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. In the present invention, 'heteroaryl' means an aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
The '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl. The '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The '(C2-C30)alkenyl or alkynyl' group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
In 'with or without substituent(s)', the substituent is further substituted by one or more substituent(s) selected from the 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 containing one or more selected from B, N, O, S, P(=O), Si and P, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-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, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (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 is linked to an adjacent substituent to form a ring, and
the R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
The R1 through R14, R21 through R28, R51 through R58, and R61 through R63 are independently selected from hydrogen, deuterium, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused with one or more aromatic ring such as benzopyrrolidino, benzopiperidino, dibenzomorpholino, dibenzoazepino, etc., amino substituted by aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc. or heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., , or , but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
More specifically, the R1 through R14 may be exemplified as following structures but are not limited thereto.
wherein
R71 through R132 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s), (C3-C30)heteroaryl, 5- to 7-memebered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring, and
the R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
The R1 through R14 are exemplified as the following structures, but are not limited thereto.
The organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but is not limited thereto.
The organic electroluminescent compound according to the present invention may be prepared as shown in following Reaction Scheme 1.
[Reaction Scheme 1]
wherein
R1 through R14, X and Y are the same as defined in the Chemical Formula 1.
Provided is an organic electroluminescent device, which comprises 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) represented by Chemical Formula 1. The organic electroluminescent compound is used as a host material of the electroluminescent layer.
In addition, the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more dopants besides one or more organic electroluminescent compounds of Chemical Formula 1. The dopant applied to the organic electroluminescent device of the present invention is not specifically limited.
Preferably, the dopant applied to the organic electroluminescent device of the present invention is selected from following Chemical Formulas 2 and 3.
[Chemical Formula 2]
[Chemical Formula 3]
wherein
Ar11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
Ar13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1:
Ar13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2:
Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
d represents an integer from 1 to 4; and
e represents an integer 0 or 1.
The meaning of the electroluminescent layer may be a single layer as a layer where the light is emitted or may be a multiple layer where two or more layers are laminated. In the configuration of the present invention, when host-dopant are used in mixture, it is confirmed that the luminous efficiency are remarkably improved by the electroluminescent host of the present invention. It may be configured at doping concentration of 0.5 to 10wt%. Compared to other host materials, the electroluminescent host of the present invention has superior conductivity with respect to the hole and electron and excellent stability in material, thereby showing a characteristic of remarkably increasing its life span as well as improving the luminous efficiency.
The dopant compound of Chemical Formula 3 may be exemplified as the compound described in KR Patent Application No. 10-2009-0023442, more preferably, be selected from the following structures. However, they are not limited thereto.
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
Further, the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device. The compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as 'surface layer') selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
The chalcogenide may be, for example, SiOx(1 ≤ x ≤2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the 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 an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent 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.
Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 4
Preparation of Compound
1-1
After 6,6,12,12-tetraethyl-6,12-dihydroindeno[1,2-b]fluorene (10 g, 27.28 mmol) and AlCl3 (7.27 g) were added into methylenechloride(MC) (500 mL) and phthalic anhydride (6.06 g, 40.92 mmol) was added thereto, the mixture was stirred under reflux at 40 ℃ for 12 hours. After slowly adding distilled water and adding hydrochloric acid thereto, the product was extracted with MC and the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 1-1 (12 g, 23.31 mmol, 85.47 %).
Preparation of Compound
1-2
After Compound 1-1 (12 g, 23.31 mmol) and acetic acid (60 mL) were added into sulfuric acid (60 mL), the mixture was stirred under reflux at 120 ℃ for 8 hours. After cooling to room temperature, adding distilled water and neutralizing with NaOH aqueous solution, the product was extracted with MC and the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 1-2 (3.5 g, 7.04 mmol, 30.23 %).
Preparation of Compound
1-3
After 2-bromonaphthalene (3.94 g, 19.02 mmol) was dissolved in THF (100 mL), and n-buLi (7.8 mL, 19.73 mmol, 2.5M in hexane) was slowly added at -78℃. 1 hour later, Compound 1-2 (3.5 g, 7.04 mmol) was added. The mixture was slowly heated and stirred under reflux at room temperature for 12 hours. After adding distilled water and extracting with ethyl acetate (EA), the remaining moisture was removed by using magnesium sulfate. Drying yielded Compound 1-3 (7 g) in a mixture state.
Preparation of Compound
4
Compound 1-3 (7 g, mixture), potassium iodide (KI) (4.4 g, 26.56 mmol), NaH2PO3H2O (5.6 g, 53.12 mmol), and acetic acid (60 mL) were mixed and stirred under reflux. 12 hours later, the mixture was cooled to room temperature. After adding distilled water, filtering the produced solid under reduced pressure, and washing the solid wiht NaOH aqueous solution, Compound 4 (3.2 g, 4.45 mmol) was obtained via column separation.
[Preparation Example 2] Preparation of Compound 28
Preparation of Compound
2-1
After 2-Bromo-9,9-dimethylfluorene (20 g, 73.21 mmol), AlCl3 (19.5 g, 146.4 mmol), and MC (500 mL) were mixed, Compound A was added thereto and stirred under reflux at 40 ℃. 12 hours later, distilled water and 1M HCl aqueous solution were added. After extracting with MC, distillation under reduced pressure followed by column separation yielded Compound 2-1 (30 g, 71.21 mmol, 97.21 %).
Preparation of Compound
2-2
Compound 2-1 (30 g, 71.21 mmol), sulfuric acid (100 mL), and acetic acid (100 mL) were mixed and stirred under reflux at 120℃. 10 hours later, the mixture was cooled to room temperature and distilled water was added thereto. After filtering the produced solid under reduced pressure, recrystallization with methanol and EA yielded Compound 2-2 (4 g, 9.91 mmol, 13.95%).
Preparation of Compound
2-3
Compound 2-2 (4.2 g, 10.37 mmol), 2-nitrophenylboronic acid (2 g, 12.49 mmol), Pd(PPh3)4 (0.59 g, 0.51 mmol), 3M K2CO3 aqueous solution (10 mL), toluene (70 mL), and ethanol (30 mL) were mixed and stirred under reflux. 12 hours later, the mixture was cooled to room temperature. After adding distilled water and extracting with EA, the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 2-3 (3.7 g, 8.30 mmol, 80.05%).
Preparation of Compound
2-4
Compound 2-3 (3.7 g, 8.30 mmol) was mixed with triethylphosphite (50 mL) and mixture was stirred under reflux. 10 hours later, the mixture was cooled to room temperature. Distillation followed by column separation yielded Compound 2-4 (2.5 g, 6.04 mmol, 72.84 %).
Preparation of Compound
2-5
Compound 2-4 (2.5 g, 6.04 mmol), iodobenzene (2.46 g, 12.09 mmol), CuI (1.72 g, 9.06 mmol), K2CO3 (2.50 g, 18.13 mmol), and 1.2-dichlorobenzene (50 mL) were mixed and heated at 190 ℃. 24 hours later, the mixture was cooled to room temperature and organic solvent was distilled under reduced pressure. After adding distilled water and extracting with EA, distillation under reduced pressure followed by column separation yielded Compound 2-5 (2.7g, 5.51mmol, 91.31%).
Preparation of Compound
2-6
Compound 2-6 was obtained by combining Compound 2-5 in Preparation Example 1 according to the same method as preparation of Compound 1-3.
Preparation of Compound
28
Compound 28 (2.1 g, 2.95mmol, 53 %) was obtained by combining unrefined Compound 2-6 in Preparation Example 1 according to the same method as preparation of Compound 4.
[Preparation Example 3] Preparation of Compound 30
Preparation of Compound
3-1
1,4-dimethyl-2,5-dibromobenzene (10 g, 37.88 mmol), 2-(methoxycarbonyl)phenylboronic acid (17 g, 94.71 mmol), Pd(PPh3)4 (2.18 g, 1.89 mmol), 2M K2CO3 aqueous solution (60 mL), toluene (200 mL), and ethanol (100 mL) were mixed and stirred under reflux. 6 hours later, the mixture was cooled to room temperature. After adding distilled water and extracting with EA, the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 3-1 (11 g, 29.37 mmol, 77.55 %).
Preparation of Compound
3-2
Compound 3-1 (11 g, 29.37 mmol) was dissolved in THF (400 mL) and methylmagnesium bromide (48.96 mL, 146.88 mmol, 3.0M in diehtyl ether) was slowly added thereto. The mixture was stirred under reflux at 60℃ for 12 hours and cooled to room temperature. After slowly adding distilled water and extracting with EA, the remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound 3-2 (9 g, 24.03 mmol, 81.82 %).
Preparation of Compound
3-3
Compound 3-2 (9 g, 24.03 mmol) was mixed with acetic acid (100 mL) and H3PO4 (100 mL) and the mixture was heated at 120℃. 10 hours later, the mixture was cooled to room temperature and distilled water was added thereto. Filtering the produced solid under reduced pressure and washing with NaOH aqueous solution and methanol yielded Compound 3-3 (6 g, 17.72 mmol, 73.76 %).
Preparation of Compound
3-4
Compound 3-4 (6.3 g, 12.95 mmol, 73.1 %) was obtained by combining Compound 3-3 in Preparation Example 1 according to the same method as preparation of Compound 1-1.
Preparation of Compound
3-5
Compound 3-5 (4.3 g, 9.18 mmol, 70.1 %) was obtained by combining Compound 3-4 in Preparation Example 1 according to the same method as preparation of Compound 1-2.
Preparation of Compound
3-6
Compound 3-6 was obtained by combining Compound 3-5 in Preparation Example 1 according to the same method as preparation of Compound 1-3.
Preparation of Compound
30
Compound 30 (2.3 g, 3.33 mmol, 37 %) was obtained by combining Compound 3-6 in Preparation Example 1 according to the same method as preparation of Compound 4.
Organic electroluminescent Compounds 1 to 35 were prepared according to Preparation Example 1 and Table 1 shows 1H NMR and MS/FAB of the prepared organic electroluminescent compounds.
[Table 1]
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material according to the present invention.
First, a transparent electrode ITO thin film (15 Ω/□) obtained from a 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 deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
Then, N,N'-bis(a-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound 4 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound E was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 2 to 5 wt% based on host.
Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) having a following structure was vapor-deposited with a thickness of 20 nm as an electron transport layer. Then, after vapor-depositing lithium quinolate (Liq) of a following structure with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED was purified by vacuum sublimation at 10-6torr.
[Comparative Example 1] Manufacture of OLED device using conventional electroluminescent material
An OLED device was manufactured in the same manner as Example 1 except that 9,10-di(naphthalen-3-yl)anthracene (DNA) was used on the electroluminescent layer as host material.
Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention manufactured in Example 1 and Comparative Example 1 and the conventional electroluminescent compound was measured at 5,000 cd/m2. The result is given in Table 2.
[Table 2]
As shown in Table 2, the result that the material of the present invention is applied to the green-light emitting device shows that driving voltage is lowered and luminous efficiency is improved while maintaining color purity the same as or higher than that of Comparative Example 1.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1:whereinR1 through R14 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), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, amino, (C1-C30)alkylamino with or without substituent(s), (C6-C30)arylamino with or without substituent(s), NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro, , or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fuse ring to form an alicylic ring or a mono- or polycyclic aromatic ring;X, Y and W independently represent -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;R51 through R58 and R61 through R63 are the same as defined in R1 through R14;the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; andthe R21 through R28 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),the Ra, Rb, Rc, and Rd independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s),the Y represents S or O,the Re and Rf represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s); andm represents an integer 1 or 2.
- The organic electroluminescent compound according to claim 1, wherein in 'with or without substituent(s)', the substituent of R1 through R14, R21 through R28, R51 through R58, and R61 through R63 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, (C3-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, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (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 is linked to an adjacent substituent to form a ring, andthe R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
- The organic electroluminescent compound according to claim 1, wherein R1 through R14 are selected from the following structures:whereinR71 through R132 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s), (C3-C30)heteroaryl, 5- to 7-memebered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring, andthe R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
- 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 comprises 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) according to any of claims 1 to 5 and one or more dopant(s) represented by Chemical Formula 2 or 3:whereinAr11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;Ar13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1:Ar13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2:Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);d represents an integer from 1 to 4; ande represents an integer 0 or 1.
- 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, or one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
- 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 wherein the organic layer comprises one or more organic compound layer(s) emitting red, green or blue light at the same time.
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KR1020090071577A KR20110013881A (en) | 2009-08-04 | 2009-08-04 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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WO2012159213A1 (en) * | 2011-05-25 | 2012-11-29 | American Dye Source, Inc. | Compounds with oxime ester and/or acyl groups |
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WO2021136064A1 (en) * | 2019-12-31 | 2021-07-08 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic apparatus |
CN113121364A (en) * | 2019-12-31 | 2021-07-16 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
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CN113004738B (en) * | 2019-12-19 | 2022-04-22 | 常州强力电子新材料股份有限公司 | Photo-curable composition and photo-curable ink |
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WO2012159213A1 (en) * | 2011-05-25 | 2012-11-29 | American Dye Source, Inc. | Compounds with oxime ester and/or acyl groups |
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TW201113238A (en) | 2011-04-16 |
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