KR20120136618A - Novel compounds for organic electronic material and organic electroluminescence device using the same - Google Patents
Novel compounds for organic electronic material and organic electroluminescence device using the same Download PDFInfo
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- KR20120136618A KR20120136618A KR1020110055657A KR20110055657A KR20120136618A KR 20120136618 A KR20120136618 A KR 20120136618A KR 1020110055657 A KR1020110055657 A KR 1020110055657A KR 20110055657 A KR20110055657 A KR 20110055657A KR 20120136618 A KR20120136618 A KR 20120136618A
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- 239000012776 electronic material Substances 0.000 title claims abstract description 24
- 238000005401 electroluminescence Methods 0.000 title description 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- -1 cyano, carbazolyl Chemical group 0.000 claims description 25
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000004927 fusion Effects 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 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
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 4
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 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 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
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- 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 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
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 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
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-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
- 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
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- QWKFYAGZLGBCIE-UHFFFAOYSA-N OC(C(BC=C1)=C1C1=COC=C1)=O Chemical compound OC(C(BC=C1)=C1C1=COC=C1)=O QWKFYAGZLGBCIE-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 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
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
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Abstract
본 발명은 신규한 유기 전자재료용 화합물 및 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 상세하게는 본 발명에 따른 유기 전자재료용 화합물은 하기 화학식 1로 표시된다.
[화학식 1]
상기 화학식 1에서 R1 내지 R5, Y1, Y2, Y3, X1, L1 내지 L2, a, b, c, d 및 e는 각각 발명의 상세한 설명에서 정의한 바와 같다.
본 발명에 따른 유기 전자재료용 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to a novel compound for an organic electronic material and an organic electroluminescent device comprising the same. Specifically, the compound for an organic electronic material according to the present invention is represented by the following formula (1).
[Formula 1]
In Formula 1, R 1 to R 5 , Y 1 , Y 2 , Y 3 , X 1 , L 1 to L 2, a, b, c, d, and e are as defined in the detailed description of the invention, respectively.
The compound for an organic electronic material according to the present invention has a high electron transfer efficiency, which not only prevents crystallization during device fabrication but also has a good layer formation to improve the current characteristics of the device, thereby lowering the driving voltage of the device and at the same time improving the power efficiency. There is an advantage to manufacture.
Description
본 발명은 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel compound for organic electronic materials and an organic electroluminescent device comprising the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2, Ir(ppy)3 및 Firpic 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다. The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) 2 , Ir (ppy) 3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.
인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있고, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용해 고성능의 OLED을 개발한 바 있다.CBP is the most widely known host material for phosphorescent emitters to date, and high-efficiency OLEDs using hole blocking layers such as BCP and BAlq are known. I've done it.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 단점을 갖고 있다. OLED에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력효율은 전압에 반비례하고, 따라서 OLED의 소비 전력을 낮으려면 전력 효율을 높여야 한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 사용되던 BAlq 또는 CBP와 같은 종래재료의 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. 또한, OLED 소자에 사용할 경우 수명 측면에서도 결코 만족스럽지 못하였다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the OLED, power efficiency = [(π / voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). Also, when used in OLED devices, they were never satisfactory in terms of lifetime.
한편, 국제특허공보 제WO 2006/049013호에는 축합 이환기를 골격으로 하는 유기 전기 발광 소재용 화합물을 언급하고 있다. 그러나, 상기 문헌에는 융합된 카바졸골격에 방향족 고리가 융합된 헤테로시클로알킬 또는 시클로알킬이 치환된 질소함유 축합이환기를 모두 겸비한 화합물을 구체적으로 개시하고 있지 않다.
On the other hand, International Patent Publication No. WO 2006/049013 mentions a compound for an organic electroluminescent material having a condensed bicyclic group as a skeleton. However, this document does not specifically disclose a compound having both a heterocycloalkyl in which an aromatic ring is fused to a fused carbazole skeleton or a nitrogen-containing condensed bicyclic group substituted with a cycloalkyl.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 전자재료용 화합물을 제공하는 것이며 둘째로, 상기 유기 전자재료용 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide a compound for organic electronic material having a good skeleton having an excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems. It is to provide a high efficiency and long life organic electroluminescent element employing a compound for a material as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 전자재료용 화합물은 기존 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to a compound for an organic electronic material represented by the following formula (1) and an organic electroluminescent device comprising the same, the compound for an organic electronic material according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional material The driving life of the device is very excellent and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.
[화학식 1] [Formula 1]
상기 화학식 1에서,In Formula 1,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C5-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C6-C30)시클로알킬렌이고;L 1 and L 2 are each independently a single bond, a substituted or unsubstituted (C5-C30) heteroarylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C6-C30) Cycloalkylene;
X1은 CH 또는 N이며;X 1 is CH or N;
Y1은 -O-, -S-, -CR6R7- 또는 -NR8-이고;Y 1 is -O-, -S-, -CR 6 R 7 -or -NR 8- ;
Y2 및 Y3는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며;Y 2 and Y 3 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ;
단, Y2 와 Y3가 동시에 존재하는 경우는 없고,However, Y 2 and Y 3 do not exist at the same time,
R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxy, substituted or unsubstituted (C3-C30) with or without adjacent substituents and fused rings Alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and the monocyclic or polycyclic aromatic ring The carbon atom may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R6 내지 R8 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 인접한 치환체와 스피로고리 또는 융합된 스피로 고리를 형성할 수 있고, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;R 6 to R 8 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, with spirogyls or fusions with adjacent substituents Formed spiro ring, and the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c, e는 각각 독립적으로 1 내지 4의 정수이며, a, b, c 및 e가 2이상의 정수인 경우 동일하거나 상이할 수 있고;a, b, c, e are each independently an integer of 1 to 4, and may be the same or different when a, b, c and e are integers of 2 or more;
d은 1 내지 3의 정수이며, d가 2이상의 정수인 경우 동일하거나 상이할 수 있고;d is an integer of 1 to 3, and may be the same or different when d is an integer of 2 or more;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]Wherein said heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로서 페닐, 나프틸, 비페닐, 터페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등이 있다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로서 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴, 다이벤조퓨란닐, 다이벤조싸이오페닐 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 들수 있다.Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. There is this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Means an aryl group, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso Thiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnaolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenantri Polycyclic heteroaryls such as dinyl, benzodioxyl, dibenzofuranyl, dibenzothiophenyl and their corresponding N-oxides (e.g. pyridyl N-oxides, quinolyl N-oxides), Quaternary salts;
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 바람직하게는 (C1-C20)알킬이고, 더 바람직하게는 (C1-C10)알킬이며, ‘(C6-C30)아릴’기는 바람직하게는 (C6-C20)아릴이다. ‘(C3-C30)헤테로아릴’기는 바람직하게는 (C3-C20)헤테로아릴이다. ‘(C3-C30)시클로알킬’기는 바람직하게는 (C3-C20)시클로알킬이고, 더 바람직하게는 (C3-C7)시클로알킬이다. ‘(C2-C30)알케닐 또는 알키닐’기는 바람직하게는 (C2-C20)알케닐 또는 알키닐이고, 더 바람직하게는 (C2-C10)알케닐 또는 알키닐이다.Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl. The '(C3-C30) heteroaryl' group is preferably (C3-C20) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 L1, L2, R1 내지 R5, R6 내지 R8 및 R11 내지 R17에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴, (C6-C30)알킬이 치환된 (C5-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C5-C30)헤테로아릴, (C3-C30)시클로알킬, 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' means a case where is further substituted with an unsubstituted substituent, the L 1 , L 2 , R 1 to R 5 , R 6 to R 8 And the substituents further substituted for R 11 to R 17 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 3 -C 30) heteroaryl, ( (C5-C30) heteroaryl substituted with C6-C30) alkyl, (C5-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, heterocycloalkyl, tri (C1-C30) ) Alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl , (C2-C30) alkynyl, cyano, carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6 -C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1 -C30) alkyl (C6-C30) aryl, car It means one or more selected from the group consisting of carboxyl, nitro and hydroxy.
구체적으로, 상기 L1 및 L2은 각각 독립적으로 단일결합, (C3-C30)헤테로아릴렌, (C6-C30)아릴렌, 또는 (C6-C30)시클로알킬렌이고; X1은 CH 또는 N이며; Y1은 -O-, -S-, -CR6R7- 또는 -NR8-이고; Y2 및 Y3는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며, 단, Y2 와 Y3가 동시에 존재하는 경우는 없고; R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴, N-카바졸릴, -NR11R12 또는 -SiR13R14R15이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R6 내지 R8는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며, 인접한 치환체와 스피로고리 또는 융합된 스피로 고리를 형성할 수 있고; R11 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이고; 상기 L1 및 L2의 아릴렌, 헤테로아릴렌 및 시클로알킬렌, R1 내지 R5 및 R11 내지 R15의 알킬, 아릴, 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C3-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C3-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Specifically, L 1 and L 2 are each independently a single bond, (C3-C30) heteroarylene, (C6-C30) arylene, or (C6-C30) cycloalkylene; X 1 is CH or N; Y 1 is -O-, -S-, -CR 6 R 7 -or -NR 8- ; Y 2 and Y 3 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- , provided that Y 2 and Y 3 are not present at the same time; R 1 to R 5 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR 11 R 12 or -SiR A cycloaliphatic ring which is linked to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene which is 13 R 14 R 15 or with or without adjacent substituents and fused rings; May form a monocyclic or polycyclic aromatic ring, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R 6 to R 8 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl and form a spirogory or fused spiro ring with adjacent substituents Can do it; R 11 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl; Arylene, heteroarylene and cycloalkylene of L 1 and L 2 , R 1 to R 5 And alkyl, aryl, heteroaryl of R 11 to R 15 are each deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 1 -C 30) alkyl (C6-C30) aryl, (C3-C30) heteroaryl, (C6-C30) aryl substituted (C3-C30) heteroaryl, (C3-C30) cycloalkyl and (C6-C30) ar (C1-C30) It may be further substituted with one or more substituents selected from the group consisting of alkyl.
상기 L1 및 L2은 각각 독립적으로 단일결합, 페닐렌, 나프틸렌, 비페닐렌, 터페닐렌, 안트릴렌, 인데닐렌, 플루오레닐렌, 페난트릴렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 크라이세닐렌, 나프타세닐렌, 플루오란텐일, 시클로프로필렌, 시클로부틸렌, 시클로펜틸렌, 시클로헥실렌, 시클로헵틸렌, 시클로옥틸렌, 퓨릴렌, 티오페닐렌, 피롤릴렌, 이미다졸릴렌, 피라졸릴렌, 티아졸릴렌, 티아디아졸릴렌, 이소티아졸릴렌, 이속사졸릴렌, 옥사졸릴렌, 옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 테트라졸릴렌, 퓨라잔일렌, 피리딜렌, 피라진일렌, 피리미딘일렌, 피리다진일렌, 벤조퓨란일렌, 벤조티오펜일렌, 이소벤조퓨란일렌, 벤조이미다졸릴렌, 벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 이소인돌릴렌, 인돌릴렌, 인다졸릴렌, 벤조티아디아졸릴렌, 퀴놀릴렌, 이소퀴놀릴렌, 신놀리닐렌, 퀴나졸리닐렌, 퀴녹살리닐렌, 카바졸릴렌, 페난트리딘일렌, 벤조디옥솔릴렌, 다이벤조퓨란닐렌 및 다이벤조싸이오페닐렌으로 이루어진 군에서 선택되는 것이 바람직하며, 상기 L1 및 L2는 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C3-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C3-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.L 1 and L 2 are each independently a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthylene, indenylene, fluorenylene, phenanthryl, triphenylenylene, pylenylene, Peryleneylene, Chrysenylene, Naphthacelene, Fluoranthenyl, Cyclopropylene, Cyclobutylene, Cyclopentylene, Cyclohexylene, Cycloheptylene, Cyclooctylene, Purylene, Thiophenylene, Pyrrylene, Al Dazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, tetrazolyl Ylene, furazanthylene, pyridylene, pyrazinylene, pyrimidineylene, pyridazineylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazoylene , Benzoisoxazolylene, benzooxazolylene, isoindoleylene, Indolylene, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolylene, cinnolinylene, quinazolinyl, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxylene, dibenzo It is preferably selected from the group consisting of furanylene and dibenzothiophenylene, wherein L 1 and L 2 are each deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted with halogen, ( C6-C30) aryl, (C1-C30) alkyl (C6-C30) aryl, (C3-C30) heteroaryl, (C6-C30) aryl substituted (C3-C30) heteroaryl, (C3-C30) cyclo It may be further substituted with one or more substituents selected from the group consisting of alkyl and (C6-C30) ar (C1-C30) alkyl.
더욱 구체적으로 상기
본 발명에 따른 유기 전자재료용 화합물로는 대표적으로 하기의 화합물을 들 수 있다. Typical compounds for organic electronic materials according to the present invention include the following compounds.
본 발명에 따른 유기 전자재료용 화합물은 하기 반응식에 나타난 바와 같이 제조될 수 있다.The compound for an organic electronic material according to the present invention can be prepared as shown in the following scheme.
[반응식 1][Reaction Scheme 1]
[반응식 2]Scheme 2
[상기 반응식 1 내지 2에서, R1 내지 R5, Y1, Y2, Y3, X1, L1 내지 L2, a, b, c, d 및 e는 화학식 1에서의 정의와 동일하다.][In the above Reaction Schemes 1 to 2, R 1 to R 5 , Y 1 , Y 2 , Y 3, X 1 , L 1 to L 2, a, b, c, d and e are the same as defined in Formula 1.]
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖는 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다. 또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 화합물을 호스트 물질로 사용할 수 있다. In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound represented by Chemical Formula 1. The organic material layer may include a light emitting layer, and the compound of Formula 1 may be used as a host material in the light emitting layer.
또한 본 발명에 따른 호스트와 함께 사용되는 유기 전계 발광 소자용 인광 도판트에는 대표적으로 하기 화학식 2의 화합물이 있다. In addition, a phosphorescent dopant for an organic electroluminescent device used with a host according to the present invention typically includes a compound represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
M1L101L102L103 M 1 L 101 L 102 L 103
[상기 화학식 2에서,[In the formula (2)
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고;Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os;
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는
구체적으로 상기 화학식 2의 도판트 화합물로서 다음과 같은 화합물을 사용하는 것이 바람직하다. Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.
본 발명의 유기 전계 발광 소자는 화학식 1의 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention includes a compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고,나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, the organic material layer is selected from the group consisting of Group 1, Group 2, Group 4, Period 5 transition metals, Lanthanide series metals and organic metals of d-transition elements in addition to the compound of Formula 1 One or more metal or complex compounds may be further included. Furthermore, the organic material layer may further include a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 전자재료용 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. In addition, the organic material layer may include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the compound for organic electronic materials to form an organic light emitting device that emits white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO X (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 전자재료용 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. 또한, 본 발명에 따른 유기 전자재료용 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The compound for an organic electronic material according to the present invention has an advantage of manufacturing an OLED device having excellent luminous efficiency and excellent lifespan characteristics of the device, and having excellent driving life of the device. In addition, the compound for an organic electronic material according to the present invention has high electron transfer efficiency, which prevents crystallization during device fabrication and improves current characteristics of the device due to good layer formation, thereby lowering the driving voltage of the device and improving power efficiency. There is an advantage to manufacture an OLED device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전자 재료용 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of a device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.
[제조예 1] 화합물 2의 제조Preparation Example 1 Preparation of Compound 2
화합물 1-1의 제조Preparation of Compound 1-1
2-아이오도벤젠 30g(120.4mmol), 4-브로모페닐보로닉산 26g(132.5mmol), Pd(PPh3)4 6.9g(6.02mmol), 2M Na2CO3 150mL, 톨루엔 500mL에 넣고 100℃에서 가열하였다. 4시간 후 상온으로 냉각시키고 에틸아세테이트로 추출하였다. 증류수로 씻어 주고 MgSO4로 건조시킨 후 감압 증류하고 컬럼 분리하여 화합물 1-1 28g(100.68mmol, 83,33%) 을 얻었다. 30 g (120.4 mmol) of 2-iodobenzene, 26 g (132.5 mmol) of 4-bromophenylboronic acid, 6.9 g (6.02 mmol) of Pd (PPh 3 ) 4 , 150 mL of 2M Na 2 CO 3 , 500 mL of toluene Heated at ° C. After 4 hours, the mixture was cooled to room temperature and extracted with ethyl acetate. The mixture was washed with distilled water, dried over MgSO 4 , distilled under reduced pressure, and column separated to obtain compound 1-1 28g (100.68 mmol, 83,33%).
화합물 1-2의 제조Preparation of Compound 1-2
화합물 1-1 28g(100.68mmol) 을 트리에틸포스파이트 300mL 에 섞고 150℃에서 6시간 동안 교반하였다. 상온으로 냉각한 뒤 감압 증류하고 에틸아세테이트로 추출한 후 증류수로 씻어주었다. MgSO4로 건조시킨 후 감압 증류하고 컬럼 분리하여 화합물 1-2 11g(44.69mmol, 44.38%) 을 얻었다.28 g (100.68 mmol) of Compound 1-1 were mixed with 300 mL of triethylphosphite and stirred at 150 ° C. for 6 hours. After cooling to room temperature, the mixture was distilled under reduced pressure, extracted with ethyl acetate, and washed with distilled water. After drying over MgSO 4 , distillation under reduced pressure and column separation yielded Compound 1-2 (11 g, 44.69 mmol, 44.38%).
화합물 1-3의 제조Preparation of Compound 1-3
화합물 1-2 30g(101.29mmol), 아이오도벤젠 41.3g(202.59mmol), CuI 9.6g(50.64mmol), Cs2CO3 82.5g(253.2mmol), 톨루엔 600mL 을 섞고 50℃에서 가열한 뒤, 에틸렌다이아민 6.8mL(101.29mmol)을 넣고 환류 교반하였다. 14시간 후 상온으로 냉각하고 증류수를 넣었다. 에틸아세테이트로 추출하고 MgSO4로 건조한 뒤, 감압 증류하고 컬럼 분리하여 화합물 1-3 32g(85.96mmol, 84.86%) 을 얻었다. Compound 1-2 30g (101.29mmol), iodobenzene 41.3g (202.59mmol), CuI 9.6g (50.64mmol), Cs 2 CO 3 82.5g (253.2mmol), toluene 600mL was mixed and heated at 50 ℃, 6.8 mL (101.29 mmol) of ethylenediamine was added thereto, and the mixture was stirred under reflux. After 14 hours, it was cooled to room temperature and distilled water was added. Extraction with ethyl acetate, drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 1-3 (32 g, 85.96 mmol, 84.86%).
화합물 1-4의 제조Preparation of Compound 1-4
화합물 1-3 32g(85.96mmol) 을 THF 300mL 에 녹이고 -78℃에서 n-부틸리튬 37.8mL(94.55mmol, 2.5M in hexane)을 천천히 넣었다. 1시간 후 트리메틸보레이트 12.4mL(111.7mmol)을 넣었다. 상온에서 12시간 교반 후 증류수를 넣었다. 에틸아세테이트로 추출하고 MgSO4로 건조한 뒤, 감압 증류하고 컬럼 분리하여 화합물 1-4 20g(59.31mmol, 69.00%) 을 얻었다. 32 g (85.96 mmol) of Compound 1-3 were dissolved in 300 mL of THF, and 37.8 mL (94.55 mmol, 2.5 M in hexane) of n-butyllithium was slowly added at -78 ° C. After 1 hour trimethyl borate 12.4 mL (111.7 mmol) was added. After stirring for 12 hours at room temperature, distilled water was added. Extraction with ethyl acetate, drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 1-4 20g (59.31 mmol, 69.00%).
화합물 1-5의 제조Preparation of Compound 1-5
화합물 1-4 20g(59.31mmol), 1-브로모-2-니트로벤젠 14.3g(71.17mmol), Pd(PPh3)4 2.7g(2.37mmol), 2M Na2CO3 75mL , 톨루엔 300mL, 에탄올 70mL 를 섞고 환류 교반하였다. 5시간 후 상온으로 냉각하고 증류수를 넣었다. 에틸아세테이트로 추출하고 MgSO4로 건조한 뒤, 감압 증류하고 컬럼 분리하여 화합물 1-5 20g(48.25mmol, 81.36%)을 얻었다. Compound 1-4 20 g (59.31 mmol), 1-bromo-2-nitrobenzene 14.3 g (71.17 mmol), Pd (PPh 3 ) 4 2.7 g (2.37 mmol), 2 M Na 2 CO 3 75 mL, toluene 300 mL, ethanol 70 mL was mixed and stirred at reflux. After 5 hours, cooled to room temperature and distilled water was added. Extraction with ethyl acetate, drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 1-5 20g (48.25mmol, 81.36%).
화합물 1-6의 제조Preparation of Compound 1-6
화합물 1-5 20g(48.25mmol)에 트리에틸포스파이트 200mL을 150℃에서 6시간동안 교반한 뒤, 상온으로 냉각하고 감압 증류하였다. 에틸아세테이트로 추출하고 증류수로 씻어주었다. MgSO4 건조하고 감압 증류한 뒤, 컬럼 분리하여 화합물 1-6 7g(18.30mmol, 37.93%)을 얻었다. 20 mL (48.25 mmol) of Compound 1-5 were stirred with 200 mL of triethylphosphite at 150 ° C. for 6 hours, cooled to room temperature and distilled under reduced pressure. Extracted with ethyl acetate and washed with distilled water. MgSO 4 was dried and distilled under reduced pressure, followed by column separation to obtain compound 1-6 7g (18.30 mmol, 37.93%).
화합물 1-7의 제조 Preparation of Compound 1-7
2,4-dichloroquinazoline (30 g, 151 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (15.6 g, 75.3 mmol), Pd(PPh3)4 (2.6 g, 2.3 mmol), Na2CO3 (16g,150mmol)을 Toluene (300ml), 증류수 (75 ml)에 녹인 후 90 oC로 2시간 동안 교반하였다. 유기층을 감압증류한 후 MeOH로 trituration 하였다. 얻어진 고체를 MC에 녹여 silica filter한 후 MC와 헥산으로 trituration하여 화합물 1-7(9.3g, 51.4 %)를 얻었다. 2,4-dichloroquinazoline (30 g, 151 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (15.6 g, 75.3 mmol), Pd (PPh 3 ) 4 (2.6 g, 2.3 mmol), Na 2 CO 3 (16 g, 150 mmol) was dissolved in Toluene (300 ml) and distilled water (75 ml) and stirred at 90 ° C. for 2 hours. The organic layer was distilled under reduced pressure and triturated with MeOH. The obtained solid was dissolved in MC, filtered through silica, and triturated with MC and hexane to obtain compound 1-7 (9.3 g, 51.4%).
화합물 2의 제조Preparation of Compound 2
화합물 1-6 (4.9 g, 14.7mmol), 화합물 1-7 (5 g, 15.8 mmol)을 DMF 80mL에 현탁한 뒤 60% NaH (948 mg, 22mmol)를 상온에서 투입 하였다. 12시간 동안 교반하였다. 정제수(1L) 투입 후 감압여과하였다. 얻어진 고체를 MeOH/EA로 trituration 하고 MC로 녹여 silica filter한 후 MC/n-Hexane 으로 trituration하여 화합물 3 (5.3g, 51.5%)을 얻었다.Compound 1-6 (4.9 g, 14.7 mmol) and Compound 1-7 (5 g, 15.8 mmol) were suspended in 80 mL of DMF, and 60% NaH (948 mg, 22 mmol) was added at room temperature. Stir for 12 hours. Purified water (1L) and filtered under reduced pressure. The obtained solid was triturated with MeOH / EA, dissolved in MC, silica filtered, and triturated with MC / n-Hexane to obtain compound 3 (5.3 g, 51.5%).
MS/FAB found 702, calculated 701.81MS / FAB found 702, calculated 701.81
[제조예 2] 화합물 34의 제조Preparation Example 2 Preparation of Compound 34
화합물 2-1의 제조Preparation of Compound 2-1
1L 2-구 RBF에 1-브로모-2-니트로벤젠 15g (0.074mol)을 넣고 9,9-다이메틸-9H-플루오렌-2-일보로닉산 23g(0.096mol), Pd(PPh3)4 4.2g(0.003mol), Na2CO3(2M) 111mL, 에탄올 111mL을 넣고, 톨루엔 200mL를 첨가한 후 120℃에서 3시간 동안 가열 교반하였다. 반응이 종결되면 증류수로 씻어주고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 2-1 22g (95%)를 얻었다.15 g (0.074 mol) of 1-bromo-2-nitrobenzene was added to 1 L 2-neck RBF, and 23 g (0.096 mol) of 9,9-dimethyl-9H-fluorene-2-ylboronic acid and Pd (PPh 3 ) 4 4.2 g (0.003 mol), 111 mL of Na 2 CO 3 (2M) and 111 mL of ethanol were added thereto, and 200 mL of toluene was added thereto, followed by heating and stirring at 120 ° C. for 3 hours. After the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain 22 g (95%) of Compound 2-1.
화합물 2-2의 제조Preparation of Compound 2-2
1L 2-구 RBF 에 화합물 2-1 24g (0.076mol)을 넣고, 트리에틸포스파이트 200mL, 1,2-디클로로벤젠 200mL를 첨가한 후 140℃에서 12시간 동안 가열 교반하였다. 반응이 종결되면 용매를 증류한 뒤, 증류수로 씻어주고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 2-2 7g (33%)를 얻었다.24 g (0.076 mol) of Compound 2-1 was added to 1 L 2-sphere RBF, 200 mL of triethylphosphite and 200 mL of 1,2-dichlorobenzene were added thereto, followed by heating and stirring at 140 ° C. for 12 hours. After the reaction was completed, the solvent was distilled off, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain compound 2-2 7g (33%).
화합물 2-3의 제조Preparation of Compound 2-3
2,4-디클로로퀴나졸린 50 g (251 mmol) 과 디벤조[b,d]퓨란-4-일보로산 53.2 g (251 mmol)을 톨루엔 1 L, 물 200 mL 혼합용액에 녹인 후 테트라키스트리페닐포스핀 팔라듐 14.5 g (12.5 mmol)과 탄산나트륨 80 g (755 mmol)을 첨가하여 준다. 이 혼합물을 80℃에서 20시간 동안 교반하여 준다. 반응 혼합물을 상온으로 시키고 염화암모늄 수용액 200 mL로 반응을 종결 시킨 시킨 후 에틸아세테이트 1 L 로 추출한 후, 수층은 다시 디클로로메탄 1 L로 추출한다. 유기층을 무수황산마그네슘으로 건조하고, 유기용매는 감압하에서 제거하였다. 얻어진 고체는 실리카겔 로 여과 후 용매는 감압하에서 제게하였다. 얻어진 고체를 EtOAc 100 mL 로 씻어주어 화합물 2-3 (50 g, 74%)을 얻었다. 50 g (251 mmol) of 2,4-dichloroquinazoline and 53.2 g (251 mmol) of dibenzo [b, d] furan-4-ylborolic acid were dissolved in a mixed solution of 1 L of toluene and 200 mL of water, followed by tetrakistri. 14.5 g (12.5 mmol) of phenylphosphine palladium and 80 g (755 mmol) of sodium carbonate are added. The mixture is stirred at 80 ° C. for 20 hours. The reaction mixture was cooled to room temperature, the reaction was terminated with 200 mL of aqueous ammonium chloride solution, extracted with 1 L of ethyl acetate, and the aqueous layer was extracted with 1 L of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The obtained solid was filtered through silica gel, and the solvent was removed under reduced pressure. The obtained solid was washed with 100 mL of EtOAc to give compound 2-3 (50 g, 74%).
화합물 34의 제조Preparation of Compound 34
화합물 2-2 34.6 g (122 mmol) 을 DMF에 녹인 후 60% NaH 5.9 (148 mmol) 을 천천히 첨가하여 준다. 이 반응 혼합물을 상온에서 1시간동안 교반한 후 화합물 2-3 51 g (147 mmol)을 첨가한다. 전체 반응 혼합물을 상온에서 20 시간 교반하여 준다. 반응 혼합물에 얼음물을 천천히 적가하여 반응을 종결 시킨 후 생성된 고체를 여과하여 얻는다. 얻어진 고체를 물 1 L로 세척하고, MeOH 1 L로 세척하여 준다. 고체를 건조한 후 후 CHCl34L에 녹인 후 실리카겔 여과를 하여 무기물을 제거 하였다. 얻어진 용액은 감압하에서 용매를 제거 하여 고체를 얻었다. 얻어진 고체는 DMF 에서 재결정하여 목적화합물 34 (41 g, 58%) 을 얻었다.34.6 g (122 mmol) of Compound 2-2 was dissolved in DMF, and 60% NaH 5.9 (148 mmol) was slowly added thereto. The reaction mixture is stirred at room temperature for 1 hour and then 51 g (147 mmol) of compound 2-3 are added. The whole reaction mixture is stirred at room temperature for 20 hours. Ice water is slowly added dropwise to the reaction mixture to terminate the reaction, and the resulting solid is filtered off. The solid obtained is washed with 1 L of water and washed with 1 L of MeOH. After drying the solid was dissolved in 4L CHCl 3 and the silica gel was filtered to remove the inorganic matter. The obtained solution removed the solvent under reduced pressure to obtain a solid. The obtained solid was recrystallized in DMF to obtain the target compound 34 (41 g, 58%).
MS/FAB found 578, calculated 577.67MS / FAB found 578, calculated 577.67
[제조예 3] 화합물 80의 제조Preparation Example 3 Preparation of Compound 80
화합물 3-1의 제조Preparation of Compound 3-1
화합물 2-2 (9.7g, 34.3mmol)과 1-Bromo-4-iobenzene(48.5g, 171.4mmol), CuI(3.3 g, 17.1mmol), K3PO4(21.8 g, 102.9 mmol), EDA(2.3 ml, 34.3 mmol)을 Toluene 500ml 에 투입 후 하룻동안 환류교반하였다. EA로 추출 후 감압증류한 후 MC/Hex으로 column하여 화합물 3-1 (12.0 g, 80.1 %)를 얻었다. Compound 2-2 (9.7 g, 34.3 mmol) with 1-Bromo-4-iobenzene (48.5 g, 171.4 mmol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol), EDA (2.3 ml, 34.3 mmol) was added to 500 ml of Toluene and stirred under reflux for one day. After extraction with EA and distillation under reduced pressure, Compound 3-1 (12.0 g, 80.1%) was obtained by column extraction with MC / Hex.
화합물 3-2의 제조Preparation of Compound 3-2
화합물 3-1(12.1g, 27.5mmol)을 THF(250ml)에 녹이고 -78oC에서 2.5 M n-BuLi in Hexane (17.6 ml, 44 mmol)을 첨가한 후 한 시간 동안 교반하였다. B(Oi-Pr)3(12.6ml, 55 mmol)을 천천히 첨가하여 2시간 동안 교반하였다. 2M HCl을 첨가하여 quenching 한 후 증류수와 EA로 추출하였다. MC와 Hex으로 재결정하여 화합물 3-2 (6.7g, 60 %)를 얻었다. Compound 3-1 (12.1 g, 27.5 mmol) was dissolved in THF (250 ml) and 2.5 M n-BuLi in Hexane (17.6 ml, 44 mmol) was added at -78 ° C., followed by stirring for 1 hour. B (Oi-Pr) 3 (12.6 ml, 55 mmol) was added slowly and stirred for 2 hours. 2M HCl was added and quenched, followed by extraction with distilled water and EA. Recrystallization from MC and Hex afforded compound 3-2 (6.7 g, 60%).
화합물 80의 제조Preparation of compound 80
화합물 2-3(3.2 g, 9.2 mmol), 화합물 3-2(3.7 g, 9.2 mmol), Pd(PPh3)4(532mg, 0.46 mmol), Na2CO3(2.9g,27.6mmol)을 Toluene(55ml), EtOH(14ml), 증류수(14 ml)에 녹인 후 90 oC로 2시간 동안 교반하였다. 증류수와 EA로 추출한 후 MC와 헥산으로 column 하여 목적화합물 80 (4.5g, 75 %)을 얻었다. Toluene compound 2-3 (3.2 g, 9.2 mmol), compound 3-2 (3.7 g, 9.2 mmol), Pd (PPh 3 ) 4 (532 mg, 0.46 mmol), Na 2 CO 3 (2.9 g, 27.6 mmol) (55ml), EtOH (14ml), dissolved in distilled water (14ml) and stirred at 90 ° C for 2 hours. Extracted with distilled water and EA and columned with MC and hexane to obtain the target compound 80 (4.5g, 75%).
MS/FAB found 654, calculated 653.77
MS / FAB found 654, calculated 653.77
[실시예1] 본 발명에 따른 유기 전자 재료용 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using a Compound for Organic Electronic Materials According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4- diphenylbenzene-1,4-diamine) 을 넣고 챔버 내의 진공도가 10E-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-di(4-biphenyl) -N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 화합물 5를 넣고, 또 다른 셀에는 도판트로서 화합물 D-11을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4%중량으로 도핑 함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl- 1H-benzo[d]imidazole을 넣고, 또다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 50%중량으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 Lithium quinolate를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10E-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ' -([1,1'-biphenyl] -4,4'-diyl) bis (N 1 Add-(naphthalen-1-yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) and evacuate until the vacuum in the chamber reaches 10E-6 torr. A 60 nm thick hole injection layer was deposited on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was added to another cell in the vacuum deposition apparatus, and the cell was applied with a current to evaporate. A 20 nm thick hole transport layer was deposited on the hole injection layer. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 5 was added as a host to one cell in a vacuum deposition apparatus, and compound D-11 was added as a dopant to another cell, and the materials were evaporated at different rates to be doped at 4% by weight to 30 nm on the hole transport layer. A light emitting layer of thickness was deposited. Then one cell as the electron transporting layer on the light emitting layer, followed by one cell as the electron transporting layer on the light emitting layer, 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 -phenyl-1H-benzo [d] imidazole was added, and another cell was charged with lithium quinolate, and the materials were evaporated at the same rate to be doped at 50% by weight to deposit a 30 nm electron transport layer. It was. Subsequently, Lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device. Each compound was used by vacuum sublimation purification under 10E-6 torr.
그 결과, 5.1V의 전압에서 15.2 mA/cm2의 전류가 흘렀으며, 1135 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는데 걸린 시간이 70시간 이상이었다. As a result, a current of 15.2 mA / cm 2 flowed at a voltage of 5.1 V, and red light emission of 1135 cd / m 2 was confirmed. It took more than 70 hours for the light emission to drop to 90% at a brightness of 5000 nits.
[실시예2] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 11, 도판트에는 화합물 D-11을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다. An OLED device was manufactured in the same manner as in Example 1, except that Compound 11 was used as a light emitting material and Compound D-11 was used as a dopant.
그 결과, 4.9 V의 전압에서 12.2 mA/cm2의 전류가 흘렀으며, 1010 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는데 걸린 시간이 80시간 이상이었다.As a result, a current of 12.2 mA / cm 2 flowed at a voltage of 4.9 V, and red light emission of 1010 cd / m 2 was confirmed. It took more than 80 hours for the light emission to drop to 90% at a brightness of 5000 nits.
[실시예3] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 34, 도판트에는 화합물 D-7을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 34 was used as a light emitting material and Compound D-7 was used as a dopant.
그 결과, 6.0 V의 전압에서 7.3 mA/cm2의 전류가 흘렀으며, 1090 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는데 걸린 시간이 140시간 이상이었다.As a result, a current of 7.3 mA / cm 2 flowed at a voltage of 6.0 V, and red light emission of 1090 cd / m 2 was confirmed. It took more than 140 hours for the light emission to drop to 90% at a brightness of 5000 nits.
[실시예4] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 4 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 80, 도판트에는 화합물 D-7 을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 80 was used as a light emitting material and Compound D-7 was used as a dopant.
그 결과, 5.8 V의 전압에서 7.9 mA/cm2의 전류가 흘렀으며, 1180 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는데 걸린 시간이 100시간 이상이었다.As a result, a current of 7.9 mA / cm 2 flowed at a voltage of 5.8 V, and red light emission of 1180 cd / m 2 was confirmed. It took more than 100 hours for the light emission to drop to 90% at a brightness of 5000 nits.
[실시예5] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 5 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 103, 도판트에는 화합물 D-6을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 103 was used as a light emitting material and Compound D-6 was used as a dopant.
그 결과, 5.1 V의 전압에서 16.4 mA/cm2의 전류가 흘렀으며, 1100 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는데 걸린 시간이 90시간 이상이었다.As a result, a current of 16.4 mA / cm 2 flowed at a voltage of 5.1 V, and red emission of 1100 cd / m 2 was confirmed. It took more than 90 hours for the light emission to drop to 90% at a brightness of 5000 nits.
[비교예1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Conventional OLED element fabrication using a light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-dicarbazole-biphenyl, 도판트로는 화합물 D-11을 사용하고, 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate을 10nm 두께로 증착한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl as a light emitting material and compound D-11 as a dopant were used. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer, and aluminum (III) was used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that bis (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm.
그 결과, 8.2 V의 전압에서 20.0 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다. 5000nit의 휘도에서 발광이 90%로 떨어지는 시간이 10시간 이상이었다.
As a result, a current of 20.0 mA / cm 2 flowed at a voltage of 8.2 V, and red light emission of 1000 cd / m 2 was confirmed. At the luminance of 5000 nits, the time when the light emission dropped to 90% was 10 hours or more.
본 발명에서 개발한 유기 전자 재료용 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전자 재료용 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention showed superior characteristics compared to the conventional materials. In addition, the device using the organic electronic material compound according to the present invention as a light emitting host material was excellent in the light emitting characteristics, it was possible to improve the power consumption by inducing the increase in power efficiency by lowering the driving voltage.
Claims (10)
[화학식 1]
상기 화학식 1에서,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C5-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C6-C30)시클로알킬렌이고;
X1은 CH 또는 N이며;
Y1은 -O-, -S-, -CR6R7- 또는 -NR8-이고;
Y2 및 Y3는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며;
단, Y2 와 Y3가 동시에 존재하는 경우는 없고,
R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
R6 내지 R8 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 인접한 치환체와 스피로고리 또는 융합된 스피로 고리를 형성할 수 있고, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
a, b, c, e는 각각 독립적으로 1 내지 4의 정수이며, a, b, c 및 e가 2이상의 정수인 경우 동일하거나 상이할 수 있고;
d은 1 내지 3의 정수이며, d가 2이상의 정수인 경우 동일하거나 상이할 수 있고;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.
A compound for an organic electronic material represented by Formula 1 below:
[Formula 1]
In Chemical Formula 1,
L 1 and L 2 are each independently a single bond, a substituted or unsubstituted (C5-C30) heteroarylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C6-C30) Cycloalkylene;
X 1 is CH or N;
Y 1 is -O-, -S-, -CR 6 R 7 -or -NR 8- ;
Y 2 and Y 3 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ;
However, Y 2 and Y 3 do not exist at the same time,
R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxy, substituted or unsubstituted (C3-C30) with or without adjacent substituents and fused rings Alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and the monocyclic or polycyclic aromatic ring The carbon atom may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R 6 to R 8 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, with spirogyls or fusions with adjacent substituents Formed spiro ring, and the carbon atoms of the formed alicyclic ring and monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c, e are each independently an integer of 1 to 4, and may be the same or different when a, b, c and e are integers of 2 or more;
d is an integer of 1 to 3, and may be the same or different when d is an integer of 2 or more;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.
상기 L1, L2, R1 내지 R5, R6 내지 R8 및 R11 내지 R17에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴, (C6-C30)알킬이 치환된 (C5-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C5-C30)헤테로아릴, (C3-C30)시클로알킬, 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 것인 유기 전자재료용 화합물.
The method of claim 1,
Substituents further substituted with L 1 , L 2 , R 1 to R 5 , R 6 to R 8 and R 11 to R 17 are deuterium, halogen, (C1-C30) alkyl, and halogen-substituted (C1-C30) Alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, (C6-C30) alkyl substituted (C5-C30) heteroaryl, (C6-C30) aryl substituted (C5-C30) heteroaryl , (C3-C30) cycloalkyl, heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30 ) Alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino , (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylbo A compound for organic electronic materials, selected from the group consisting of ronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy.
상기 L1 및 L2은 각각 독립적으로 단일결합, (C3-C30)헤테로아릴렌, (C6-C30)아릴렌, 또는 (C6-C30)시클로알킬렌이고;
X1은 CH 또는 N이며;
Y1은 -O-, -S-, -CR6R7- 또는 -NR8-이고;
Y2 및 Y3는 각각 독립적으로 -O-, -S-, -CR6R7- 또는 -NR8-이며;
단, Y2 와 Y3가 동시에 존재하는 경우는 없고;
R1 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴, N-카바졸릴, -NR11R12 또는 -SiR13R14R15이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R6 내지 R8는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며, 인접한 치환체와 스피로고리 또는 융합된 스피로 고리를 형성할 수 있고;
R11 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이고;
상기 L1 및 L2의 아릴렌, 헤테로아릴렌 및 시클로알킬렌, R1 내지 R5 및 R11 내지 R15의 알킬, 아릴, 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알킬(C6-C30)아릴, (C3-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C3-C30)헤테로아릴, (C3-C30)시클로알킬 및 (C6-C30)아르(C1-C30)알킬로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것인 유기 전자재료용 화합물.
The method of claim 1,
L 1 and L 2 are each independently a single bond, (C3-C30) heteroarylene, (C6-C30) arylene, or (C6-C30) cycloalkylene;
X 1 is CH or N;
Y 1 is -O-, -S-, -CR 6 R 7 -or -NR 8- ;
Y 2 and Y 3 are each independently -O-, -S-, -CR 6 R 7 -or -NR 8- ;
Provided that Y 2 and Y 3 do not exist simultaneously;
R 1 to R 5 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, N-carbazolyl, -NR 11 R 12 or -SiR A cycloaliphatic ring which is linked to a substituted or unsubstituted (C3-C30) alkylene or a substituted or unsubstituted (C3-C30) alkenylene which is 13 R 14 R 15 or with or without adjacent substituents and fused rings; May form a monocyclic or polycyclic aromatic ring, and the carbon atoms of the alicyclic ring and the monocyclic or polycyclic aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R 6 to R 8 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl and form a spirogory or fused spiro ring with adjacent substituents Can do it;
R 11 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl;
Arylene, heteroarylene and cycloalkylene of L 1 and L 2 , R 1 to R 5 And alkyl, aryl, heteroaryl of R 11 to R 15 are each deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 1 -C 30) alkyl (C6-C30) aryl, (C3-C30) heteroaryl, (C6-C30) aryl substituted (C3-C30) heteroaryl, (C3-C30) cycloalkyl and (C6-C30) ar (C1-C30) A compound for organic electronic materials that may be further substituted with one or more substituents selected from the group consisting of alkyl.
상기
The method of claim 1,
remind
하기 화합물로부터 선택되는 유기 전자재료용 화합물.
A compound for organic electronic materials selected from the following compounds.
An organic electroluminescent device comprising the compound for organic electronic material of any one of claims 1 to 5.
상기 유기 전계 발광 소자가 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 이 유기물층이 상기 유기 전자 재료용 화합물 중 하나 이상과 하기 화학식 2로 표시되는 인광 도판트 중 하나 이상을 포함하는 것인 유기 전계 발광 소자:
[화학식 2]
M1L101L102L103
상기 화학식 2에서,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는
The method according to claim 6,
The organic electroluminescent device comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one of the compounds for organic electronic materials and at least one phosphorescent dopant represented by Formula 2 below. Organic electroluminescent element:
(2)
M 1 L 101 L 102 L 103
In Formula 2,
Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is
상기 인광 도판트는 하기 화합물로부터 선택되는 것인 유기 전계 발광 소자.
8. The method of claim 7,
The phosphorescent dopant is selected from the following compounds.
상기 유기물층이 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물(A); 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 금속을 포함하는 착체화합물(B); 또는 이들의 혼합물을 포함하는 것인 유기 전계 발광 소자.
8. The method of claim 7,
At least one amine compound (A) wherein the organic material layer is selected from the group consisting of an arylamine compound or a styrylarylamine compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
상기 유기물층이 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것인 유기 전계 발광 소자.8. The method of claim 7,
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.
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| KR1020110055657A KR20120136618A (en) | 2011-06-09 | 2011-06-09 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| CN201280036650.0A CN103703003A (en) | 2011-06-09 | 2012-06-08 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| TW101120632A TW201305313A (en) | 2011-06-09 | 2012-06-08 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| PCT/KR2012/004530 WO2012169821A1 (en) | 2011-06-09 | 2012-06-08 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| JP2014514806A JP2014518900A (en) | 2011-06-09 | 2012-06-08 | Novel compounds for organic electronic materials and organic electroluminescent devices using the same compounds |
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| KR1020110055657A KR20120136618A (en) | 2011-06-09 | 2011-06-09 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
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| KR (1) | KR20120136618A (en) |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103703003A (en) | 2014-04-02 |
| TW201305313A (en) | 2013-02-01 |
| JP2014518900A (en) | 2014-08-07 |
| WO2012169821A1 (en) | 2012-12-13 |
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