WO2010151011A1 - 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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- WO2010151011A1 WO2010151011A1 PCT/KR2010/003965 KR2010003965W WO2010151011A1 WO 2010151011 A1 WO2010151011 A1 WO 2010151011A1 KR 2010003965 W KR2010003965 W KR 2010003965W WO 2010151011 A1 WO2010151011 A1 WO 2010151011A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- aryl
- organic electroluminescent
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 239000000126 substance Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims description 67
- -1 cyano, carbazolyl Chemical group 0.000 claims description 43
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 37
- 239000010410 layer Substances 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
- 125000005104 aryl silyl 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
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000000739 C2-C30 alkenyl 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
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 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
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 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
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004020 luminiscence type Methods 0.000 abstract description 7
- 150000001454 anthracenes Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 238000001816 cooling Methods 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 4
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 239000000203 mixture Substances 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
- 239000000758 substrate Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 3
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 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
- 229940125961 compound 24 Drugs 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
- 238000000034 method Methods 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
- 238000010992 reflux Methods 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
- ODAXNYMENLFYMY-UHFFFAOYSA-N (2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC=C1B(O)O ODAXNYMENLFYMY-UHFFFAOYSA-N 0.000 description 2
- 0 *C(c(ccc1ccccc11)c1C(c1c2)=O)c1cc1c2N(*)c(ccc2c3cccc2)c3C1=O Chemical compound *C(c(ccc1ccccc11)c1C(c1c2)=O)c1cc1c2N(*)c(ccc2c3cccc2)c3C1=O 0.000 description 2
- 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
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229940125898 compound 5 Drugs 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- 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 2
- 229930195733 hydrocarbon Natural products 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
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 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
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-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
- 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
- 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
- GGZNEEWSGKFREZ-UHFFFAOYSA-N CC(C)(CCN1c2c3C(C)(C)CC1)c2cc(CC1c2nc4ccccc4[s]2)c3OC1=O Chemical compound CC(C)(CCN1c2c3C(C)(C)CC1)c2cc(CC1c2nc4ccccc4[s]2)c3OC1=O GGZNEEWSGKFREZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 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
- 229910021205 NaH2PO2 Inorganic materials 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
- 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
- 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 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
- 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
- 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-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
- 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
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 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
- 239000010408 film Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 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
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([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
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon 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
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 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 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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Definitions
- the present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.
- the organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
- electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
- Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
- an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and light is emitted as the electron-hole pair is extinguished.
- the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
- the organic EL device is drawing attentions as the next-generation, full-color display device since it can exhibit green, blue and red colors.
- 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) is used as a host and a coumarin derivative (Compound d, C545T), a quinacridone derivative (Compound e), DPT (Compound f), or the like are used as a dopant, with a doping concentration of several to tens %.
- a coumarin derivative Compound d, C545T
- a quinacridone derivative Compound e
- DPT Compound f
- 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 including 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 5 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C6-C30)aryl fused with one or more substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, cyano, NR 11 R 12 , BR 13 R 14 , PR 15 R 16
- R 21 through R 23 and R 31 through R 38 are the same as R 1 through R 3 , wherein each of R 31 through R 38 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 monocyclic or polycyclic aromatic ring;
- n an integer 0, 1 or 2.
- alkyl, alkoxy and other substituents containing alkyl moiety include both linear and branched species.
- cycloalkyl includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl.
- 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 alkyl moiety of (C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, or the like may have 1 20 carbon atoms, more specifically 1 to 10 carbon atoms.
- the aryl moiety of (C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
- the heteroaryl of (C3-C30)heteroaryl may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
- the cycloalkyl of (C3-C30)cycloalkyl may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
- the alkenyl or alkynyl of (C2-C30)alkenyl or alkynyl may have 2 20 carbon atoms, more specifically 2 to 10 carbon atoms.
- the phrase substituted or unsubstituted or with or without substituent(s) means that the substituents of R 1 through R 5 and R 11 through R 18 may be independently substituted with 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-
- R 1 through R 3 may independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted adamantyl, NR 11 R 12 [wherein R 11 and R 12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl] or R a R b R c Si- [wherein R a , R b and R c independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C
- R 1 through R 3 may be 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., heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc.,
- R 4 and R 5 may be independently selected from 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, etc., heteroaryl such as dibenzothienyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyrida
- organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but are not limited thereto:
- organic electroluminescent compound according to the present invention may be prepared by Scheme 1, without being limited thereto:
- the present invention provides an organic electroluminescent device including: 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 includes one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
- the organic layer may include one or more of the organic electroluminescent compound Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s).
- the dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 2 or Chemical Formula 3:
- Ar 11 and Ar 12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl, substituted or unsubstituted (C6-C30)arylamino, (C1-C30)alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, or Ar 11 and Ar 12 are linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an
- Ar 13 represents substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl or a substituent selected from the following structures, when c is 1:
- Ar 13 represents substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C4-C30)heteroarylene or a substituent selected from the following structures, when c is 2:
- Ar 14 and Ar 15 independently represent substituted or unsubstituted (C6-C30)arylene or substituted or unsubstituted (C4-C30)heteroarylene;
- R 101 through R 103 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl;
- d represents an integer from 1 to 4.
- e represents an integer 0 or 1.
- the dopant compound represented by Chemical Formula 2 or 3 may be exemplified by the following compounds, 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 compound(s) selected from a 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 a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
- 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, 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 Nos. 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 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. An operation stability may be attained therefrom.
- 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.
- 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 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. 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.
- Compound 1-2 (12 g, 32.42 mmol) was mixed with acetic acid (200 mL) and H 3 PO 4 (300 mL) and then stirred at 120 °C. 12 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO 4 , distillation under reduced pressure followed by column separation yielded Compound 1-3 (9 g, 25.56 mmol, 78.85 %).
- Compound 1-7 (3.2 g, 5.39 mmol) was mixed with acetic acid (50 mL) and H 3 PO 4 (50 mL) and stirred at 120 °C. 12 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO 4 , distillation under reduced pressure followed by column separation yielded Compound 1-8 (2.3 g, 4.13 mmol, 76.65 %).
- Compound 2-1 (4.7 g, 8.29 mmol, 79.96 %) was prepared in the same manner as preparation of Compound 1-6 in Preparation Example 1, except for using Compound 1-5 (5 g, 10.37 mmol) and 2-nitrophenylboronic acid (4.32 g, 25.92 mmol).
- Compound 2-4 was prepared in the same manner as preparation of Compound 1-9 in Preparation Example 1, except for using Compound 2-3 (2.7 g, 4.13 mmol). The resulting product was used in the following step without further purification.
- 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
- N , N '-bis(-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.
- an electroluminescent layer was formed thereon as follows.
- Compound 5 was placed in a cell of the 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 the host.
- Each compound used in the OLED had been purified by vacuum sublimation at 10 -6 torr.
- An OLED device was manufactured according to the procedure of Example 1 except for placing DNA as a host material in a cell of the vacuum vapor deposition apparatus instead of the compound of the present invention.
- the organic electroluminescent compounds of the present invention provide improved power efficiency over Comparative Example 1, while maintaining comparable or better color purity.
- the organic electroluminescent compound according to the present invention has good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
Abstract
Disclosed are organic electroluminescent compounds and organic electroluminescent devices employing said compounds. The organic electroluminescent compounds of the invention are substituted anthracene compounds defined by chemical formula (I). The compounds disclosed herein exhibit good luminescence efficiency and operational lifetime. OLEDs manufactured using compounds of formula (I) have a superior operational life.
Description
The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. The organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and light is emitted as the electron-hole pair is extinguished. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color. In addition, the organic EL device is drawing attentions as the next-generation, full-color display device since it can exhibit green, blue and red colors.
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 (Compound d, C545T), a quinacridone derivative (Compound e), DPT (Compound f), 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 is 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 including 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.
wherein
R1 through R5 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C6-C30)aryl fused with one or more substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl], substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, RdY- [wherein Y represents S or O, and Rd represents substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl], substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C2-C30)alkynyl,
or 
, except for the case where R4 and R5 are hydrogens or deuteriums at the same time;
W, X, Y and Z independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)- or -B(R38)-;
R21 through R23 and R31 through R38 are the same as R1 through R3, wherein each of R31 through R38 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 monocyclic or polycyclic aromatic ring;
the heterocycloalkyl and heteroaryl may contain 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.
In the present invention, alkyl, alkoxy and other substituents containing alkyl moiety include both linear and branched species. In the present invention, cycloalkyl includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl.
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.
In the present invention, the alkyl moiety of (C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, or the like may have 1 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl moiety of (C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The heteroaryl of (C3-C30)heteroaryl may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The cycloalkyl of (C3-C30)cycloalkyl may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The alkenyl or alkynyl of (C2-C30)alkenyl or alkynyl may have 2 20 carbon atoms, more specifically 2 to 10 carbon atoms.
And, in the present invention, the phrase substituted or unsubstituted or with or without substituent(s) means that the substituents of R1 through R5 and R11 through R18 may be independently substituted with 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, NR41R42, BR43R44, PR45R46, P(=O)R47R48 [wherein R41 through R48 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C3-C30)heteroaryl], (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 may be linked to an adjacent substituent to form a ring.
R1 through R3 may independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted adamantyl, NR11R12 [wherein R11 and R12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl]; and R4 and R5 may independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C6-C30)aryl fused with one or more substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring.
R1 through R3 may be 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., heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., adamantyl, amino such as mono- or di-phenylamino, mono- or di-methylamino, mono- or di-pyridylamino, etc., trialkylsilyl such as trimethylsilyl, triethylsilyl, dimethylethylsilyl, tributylsilyl, etc., dialkylarylsilyl such as dimethylphenylsilyl, etc., or triarylsilyl such as triphenylsilyl, trinaphthylsilyl, etc., but are not limited thereto. They may be substituted or unsubstituted as defined in Chemical Formula 1.
R4 and R5 may be independently selected from 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, etc., heteroaryl such as dibenzothienyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl such as morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, piperidinyl, piperidino, etc., 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) such as benzopiperidino, benzopyrrolidino, etc., cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., cycloalkyl fused with one or more aromatic ring(s) such as benzocyclohexyl, etc., adamantyl or bicycloalkyl such as bicyclo[2.2.1]heptyl, etc., but are not limited thereto. They may be substituted or unsubstituted as defined in Chemical Formula 1.
The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but are not limited thereto:
The organic electroluminescent compound according to the present invention may be prepared by Scheme 1, without being limited thereto:
[Scheme 1]
wherein X, Y, Z and R1 through R5 are the same as defined in Chemical Formula 1.
In another general aspect, the present invention provides an organic electroluminescent device including: 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 includes one or more organic electroluminescent compound(s) represented by Chemical Formula 1. The organic layer may include one or more of the organic electroluminescent compound Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s). The dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 2 or Chemical Formula 3:
wherein
Ar11 and Ar12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl, substituted or unsubstituted (C6-C30)arylamino, (C1-C30)alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, or Ar11 and Ar12 are linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;
Ar13 represents substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl or a substituent selected from the following structures, when c is 1:
Ar13 represents substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C4-C30)heteroarylene or a substituent selected from the following structures, when c is 2:
Ar14 and Ar15 independently represent substituted or unsubstituted (C6-C30)arylene or substituted or unsubstituted (C4-C30)heteroarylene;
R101 through R103 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl;
d represents an integer from 1 to 4; and
e represents an integer 0 or 1.
The dopant compound represented by Chemical Formula 2 or 3 may be exemplified by the following compounds, but 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 a 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 a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. 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, 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 Nos. 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 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. An 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 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 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.
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 3
Preparation of Compound
1-1
2-(Methoxycarbonyl)phenylboronic acid (10 g, 55.55 mmol), 1,3,5-tribromobenzene (19.2 g, 61.12 mmol), Pd(PPh3)4 (1.9 g, 0.03 mmol), 2 M K2CO3 aqueous solution (80 mL), toluene (200 mL) and ethanol (50 mL) were mixed and stirred under reflux. 5 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-1 (13.5 g, 36.38 mmol, 65.73 %).
Preparation of Compound
1-2
Compound 1-1 (13.5 g, 36.38 mmol) was dissolved in THF (300 mL). After slowly adding methylmagnesium bromide (36.48 mL, 109.44 mmol, 3.0 M in diethyl ether), the mixture was stirred at 60 ℃. 10 hours later, after cooling to room temperature, distilled water was slowly added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-2 (12 g, 32.42 mmol, 90.07 %).
Preparation of Compound
1-3
Compound 1-2 (12 g, 32.42 mmol) was mixed with acetic acid (200 mL) and H3PO4 (300 mL) and then stirred at 120 ℃. 12 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-3 (9 g, 25.56 mmol, 78.85 %).
Preparation of Compound
1-4
Compound 1-3 (9 g, 25.56 mmol) was dissolved in MC (100 mL). After adding AlCl3 (5.11 g, 38.34 mmol) and phthalic anhydride (3.7 g, 25.56 mmol), the mixture was stirred at 40 ℃ for 12 hours. After cooling to room temperature, distilled water was added. After extracting with MC, washing with HCl aqueous solution and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-4 (12 g, 23.99 mmol, 93.86 %).
Preparation of Compound
1-5
Compound 1-4 (12 g, 23.99 mmol) was mixed with acetic acid (50 mL) and sulfuric acid (50 mL) and then stirred at 100 ℃. 5 hours later, after cooling to room temperature, distilled water was added. After neutralizing with NaOH aqueous solution, extracting with MC and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-5 (3.6 g, 7.46 mmol, 31.12 %).
Preparation of Compound
1-6
2-(Methoxycarbonyl)phenylboronic acid (3.35 g, 18.66 mmol), Compound 1-5 (3.6 g, 7.46 mmol), Pd(PPh3)4 (0.43 g, 0.37 mmol), 2 M K2CO3 aqueous solution (11 mL), toluene (50 mL) and ethanol (25 mL) were mixed and stirred under reflux. 10 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-6 (4 g, 6.74 mmol, 90.47 %).
Preparation of Compound
1-7
Compound 1-6 (4 g, 6.74 mmol) was dissolved in THF (100 mL). After slowly adding methylmagnesium bromide (13.49 mL, 40.49 mmol, 3.0 M in diethyl ether), the mixture was stirred at 60 ℃. 10 hours later, after cooling to room temperature, distilled water was slowly added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-7 (3.2 g, 5.39 mmol, 80.11 %).
Preparation of Compound
1-8
Compound 1-7 (3.2 g, 5.39 mmol) was mixed with acetic acid (50 mL) and H3PO4 (50 mL) and stirred at 120 ℃. 12 hours later, after cooling to room temperature, distilled water was added. After extracting with EA and drying with anhydrous MgSO4, distillation under reduced pressure followed by column separation yielded Compound 1-8 (2.3 g, 4.13 mmol, 76.65 %).
Preparation of Compound
1-9
Bromobenzene (1.75 g, 11.15 mmol) was added to THF (40 mL) and then n-BuLi (4.6 mL, 11.56 mmol, 2.5 M in hexane) was slowly added at -78 ℃. One hour later, Compound 1-8 (2.3 g, 4.13 mmol) was added. After slowly heating to room temperature, distilled water was added 10 hours later. After extracting with EA drying with anhydrous MgSO4, distillation was carried out under reduced pressure. The resulting product was used in the following step without further purification.
Preparation of Compound
3
Crude Compound 1-9 (3.2 g) was mixed with KI (2.45 g, 14.81 mmol), NaH2PO2H2O (3.13 g, 29.62 mmol) and acetic acid (50 mL) and then heated to 120 ℃. 14 hours later, after cooling to room temperature, distilled water was added. Thus produced solid was filtered under reduced pressure and washed with NaOH aqueous solution. Column separation yielded Compound 3 (1.6 g, 2.35 mmol, 63.52 %).
[Preparation Example 2] Preparation of Compound 24
Preparation of Compound
2-1
Compound 2-1 (4.7 g, 8.29 mmol, 79.96 %) was prepared in the same manner as preparation of Compound 1-6 in Preparation Example 1, except for using Compound 1-5 (5 g, 10.37 mmol) and 2-nitrophenylboronic acid (4.32 g, 25.92 mmol).
Preparation of Compound
2-2
Compound 2-1 (4.7 g, 8.29 mmol) was mixed with triethyl phosphite (50 mL) and then stirred under reflux. 20 hours later, after cooling to room temperature and distilling under reduced pressure, column separation yielded Compound 2-2 (2.5 g, 4.97 mmol, 60.00 %).
Preparation of Compound
2-3
Compound 2-2 (2.5 g, 4.97 mmol), iodobenzene (2.21 mL, 19.89 mmol), CuI (1.89 g, 9.94 mmol), K2CO3 (2.75 g, 19.89 mmol) and 1,2-dichlorobenzene (50 mL) were mixed and then heated to 190 ℃. 24 hours later, after cooling to room temperature, the 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 2-3 (2.7 g, 4.12 mmol, 82.97 %).
Preparation of Compound
2-4
Compound 2-4 was prepared in the same manner as preparation of Compound 1-9 in Preparation Example 1, except for using Compound 2-3 (2.7 g, 4.13 mmol). The resulting product was used in the following step without further purification.
Preparation of Compound
24
Compound 24 (1.6 g, 2.05 mmol, 49.98 %) was prepared in the same manner as preparation of Compound 3 in Preparation Example 1, except for using crude Compound 2-4 (3.2 g).
Compounds 1 to 31 were prepared according to the procedure of Preparation Examples 1 to 4. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
[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(-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 5 was placed in a cell of the 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 the host.
Compound 5 Compound E
Thereafter, tris(8-hydroxyquinoline)aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer. Then, after vapor-depositing lithium quinolate (Liq) 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 had been purified by vacuum sublimation at 10-6torr.
[Comparative Example 1] Manufacture of OLED device using existing electroluminescent material
An OLED device was manufactured according to the procedure of Example 1 except for placing DNA as a host material in a cell of the vacuum vapor deposition apparatus instead of the compound of the present invention.
Power efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m2. The result is given in Table 2.
[Table 2]
As seen from Table 2, when employed in green-emitting electroluminescent devices, the organic electroluminescent compounds of the present invention provide improved power efficiency over Comparative Example 1, while maintaining comparable or better color purity.
Since the organic electroluminescent compound according to the present invention has good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1:(1)
whereinR1 through R5 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C6-C30)aryl fused with one or more substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl], substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, RdY- [wherein Y represents S or O, and Rd represents substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl], substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C2-C30)alkynyl,or
,except for the case where R4 and R5 are hydrogens or deuteriums at the same time;
W, X, Y and Z independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)- or -B(R38)-;R21 through R23 and R31 through R38 are the same as R1 through R3, wherein each of R31 through R38 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 monocyclic or polycyclic aromatic ring;the heterocycloalkyl and heteroaryl may contain 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 R1 through R3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted adamantyl, NR11R12 [wherein R11 and R12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl]; and R4 and R5 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C6-C30)aryl fused with one or more substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring.
- The organic electroluminescent compound according to claim 1 or 2, wherein the substituent of R1 through R5 and R11 through R18 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, NR41R42, BR43R44, PR45R46, P(=O)R47R48 [wherein R41 through R48 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl], (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.
- The organic electroluminescent compound according to claim 3, which is selected from the following compounds:
- An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 4.
- The organic electroluminescent device according to claim 5, 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 4 and one or more dopant(s) selected from the compound represented by Chemical Formula 2 or 3:(2)
(3)
whereinAr11 and Ar12 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl, substituted or unsubstituted (C6-C30)arylamino, (C1-C30)alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3-C30)cycloalkyl, or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic ring, or Ar11 and Ar12 are linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;Ar13 represents substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C4-C30)heteroaryl or a substituent selected from the following structures, when c is 1:
Ar13 represents substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C4-C30)heteroarylene or a substituent selected from the following structures, when c is 2:
Ar14 and Ar15 independently represent substituted or unsubstituted (C6-C30)arylene or substituted or unsubstituted (C4-C30)heteroarylene;R101 through R103 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl;d represents an integer from 1 to 4; ande represents an integer 0 or 1. - The organic electroluminescent device according to claim 6, wherein the organic layer comprises one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds.
- The organic electroluminescent device according to claim 6, wherein the organic layer further comprises 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 6, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 6, which is a white light-emitting organic electroluminescent device wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting red, green or blue light.
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| JP2015007036A (en) * | 2013-05-29 | 2015-01-15 | 出光興産株式会社 | Heterocyclic compound, material for organic electroluminescent element prepared using the same, and organic electroluminescent element and electronic apparatus prepared using the same |
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|---|---|---|---|---|
| KR101521790B1 (en) * | 2012-06-22 | 2015-05-20 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR101478990B1 (en) * | 2013-12-27 | 2015-01-06 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR102592175B1 (en) * | 2015-08-04 | 2023-10-19 | 베이징 이터널 머터리얼 테크놀로지 씨오., 엘티디 | Compounds and organic electroluminescent devices |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20100137188A (en) | 2010-12-30 |
| TW201109420A (en) | 2011-03-16 |
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