JP5533863B2 - 電子輸送材料およびこれを用いた有機電界発光素子 - Google Patents
電子輸送材料およびこれを用いた有機電界発光素子 Download PDFInfo
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- JP5533863B2 JP5533863B2 JP2011516065A JP2011516065A JP5533863B2 JP 5533863 B2 JP5533863 B2 JP 5533863B2 JP 2011516065 A JP2011516065 A JP 2011516065A JP 2011516065 A JP2011516065 A JP 2011516065A JP 5533863 B2 JP5533863 B2 JP 5533863B2
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- 239000000463 material Substances 0.000 title claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 209
- -1 2,4′-bipyridin-6-yl Chemical group 0.000 claims description 115
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 6
- 150000002910 rare earth metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 2
- 150000008045 alkali metal halides Chemical class 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 167
- 239000010410 layer Substances 0.000 description 89
- 239000000243 solution Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 230000015572 biosynthetic process Effects 0.000 description 66
- 238000003786 synthesis reaction Methods 0.000 description 66
- 239000007787 solid Substances 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 49
- 239000000203 mixture Substances 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- 238000007740 vapor deposition Methods 0.000 description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 30
- 238000010992 reflux Methods 0.000 description 30
- 238000000967 suction filtration Methods 0.000 description 30
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 23
- 238000012360 testing method Methods 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- 229910052749 magnesium Inorganic materials 0.000 description 15
- 239000011777 magnesium Substances 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 229910000160 potassium phosphate Inorganic materials 0.000 description 15
- 235000011009 potassium phosphates Nutrition 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 229910052750 molybdenum Inorganic materials 0.000 description 13
- 239000011733 molybdenum Substances 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
- 230000008021 deposition Effects 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- 239000005457 ice water Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000007818 Grignard reagent Substances 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 150000004795 grignard reagents Chemical class 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- WEHCCWCYFYMBQX-UHFFFAOYSA-L zinc;n,n,n',n'-tetramethylethane-1,2-diamine;dichloride Chemical compound Cl[Zn]Cl.CN(C)CCN(C)C WEHCCWCYFYMBQX-UHFFFAOYSA-L 0.000 description 8
- WYJAVJXKAYECJZ-UHFFFAOYSA-N CC1(OB(OC1(C)C)C1=CC2=CC=C(C=C2C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=CC=C1)C Chemical compound CC1(OB(OC1(C)C)C1=CC2=CC=C(C=C2C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=CC=C1)C WYJAVJXKAYECJZ-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 5
- 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 5
- QKLQRGXULAUPSL-UHFFFAOYSA-N 9-(6-methoxynaphthalen-2-yl)-10-phenylanthracene Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1=CC=CC=C11)=C2C=CC=CC2=C1C1=CC=CC=C1 QKLQRGXULAUPSL-UHFFFAOYSA-N 0.000 description 5
- LUBXLGUQZVKOFP-UHFFFAOYSA-N 9-phenylanthracene Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LUBXLGUQZVKOFP-UHFFFAOYSA-N 0.000 description 5
- 238000006411 Negishi coupling reaction Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 5
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 4
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- LQBMPJSTUHWGDE-UHFFFAOYSA-N 1-bromo-3-ethoxybenzene Chemical compound CCOC1=CC=CC(Br)=C1 LQBMPJSTUHWGDE-UHFFFAOYSA-N 0.000 description 3
- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 3
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 description 3
- PAWSGKQRXZYKPA-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(10-naphthalen-2-ylanthracen-9-yl)-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 PAWSGKQRXZYKPA-UHFFFAOYSA-N 0.000 description 3
- IGZATAXBONXHQP-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-(10-naphthalen-2-ylanthracen-9-yl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=CC=CC=C3C(C=3C=C4C=CC=CC4=CC=3)=C3C=CC=CC3=2)C=C1 IGZATAXBONXHQP-UHFFFAOYSA-N 0.000 description 3
- SVPVFHXOPGWUQR-UHFFFAOYSA-N 4-(10-naphthalen-2-ylanthracen-9-yl)phenol Chemical compound C1=CC(O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 SVPVFHXOPGWUQR-UHFFFAOYSA-N 0.000 description 3
- LCTYNEHIFPECNL-UHFFFAOYSA-N 4-(3-bromophenyl)pyridine Chemical compound BrC1=CC=CC(C=2C=CN=CC=2)=C1 LCTYNEHIFPECNL-UHFFFAOYSA-N 0.000 description 3
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 3
- MPZMVUQGXAOJIK-UHFFFAOYSA-N 4-bromopyridine;hydron;chloride Chemical compound Cl.BrC1=CC=NC=C1 MPZMVUQGXAOJIK-UHFFFAOYSA-N 0.000 description 3
- PRNGIODVYLTUKH-UHFFFAOYSA-N 5-bromo-2-phenylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CC=C1 PRNGIODVYLTUKH-UHFFFAOYSA-N 0.000 description 3
- XWJFEVGXUAZAFS-UHFFFAOYSA-N 6-(10-phenylanthracen-9-yl)naphthalen-2-ol Chemical compound C1=CC2=CC(O)=CC=C2C=C1C(C1=CC=CC=C11)=C2C=CC=CC2=C1C1=CC=CC=C1 XWJFEVGXUAZAFS-UHFFFAOYSA-N 0.000 description 3
- ORLPQINCOCFGFG-UHFFFAOYSA-N 9-(3-ethoxyphenyl)-10-naphthalen-2-ylanthracene Chemical compound C(C)OC=1C=C(C=CC=1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC2=CC=CC=C2C=C1 ORLPQINCOCFGFG-UHFFFAOYSA-N 0.000 description 3
- VEHWKSSUQCLYQN-UHFFFAOYSA-N 9-(4-ethoxyphenyl)-10-naphthalen-2-ylanthracene Chemical compound C(C)OC1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC2=CC=CC=C2C=C1 VEHWKSSUQCLYQN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- NWUWLVCEYBABOV-UHFFFAOYSA-N [7-(trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate Chemical compound C1=CC(OS(=O)(=O)C(F)(F)F)=CC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C21 NWUWLVCEYBABOV-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N trimethylbenzene Natural products CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- SLMHHOVQRSSRCV-UHFFFAOYSA-N 2,3-dibromopyridine Chemical compound BrC1=CC=CN=C1Br SLMHHOVQRSSRCV-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 2
- GQEFTLCXNBTTMB-UHFFFAOYSA-N 3-(10-naphthalen-2-ylanthracen-9-yl)phenol Chemical compound C1=C(C=CC2=CC=CC=C12)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C=1C=C(C=CC1)O GQEFTLCXNBTTMB-UHFFFAOYSA-N 0.000 description 2
- AWCQJXPOCRXHNK-UHFFFAOYSA-N 3-bromo-5-phenylpyridine Chemical compound BrC1=CN=CC(C=2C=CC=CC=2)=C1 AWCQJXPOCRXHNK-UHFFFAOYSA-N 0.000 description 2
- ZKOZNFNWADATLB-UHFFFAOYSA-N 3-bromo-5-pyridin-2-ylpyridine Chemical compound BrC1=CN=CC(C=2N=CC=CC=2)=C1 ZKOZNFNWADATLB-UHFFFAOYSA-N 0.000 description 2
- ZKNBQZBRNLAVHS-UHFFFAOYSA-N 3-bromo-5-pyridin-4-ylpyridine Chemical compound BrC1=CN=CC(C=2C=CN=CC=2)=C1 ZKNBQZBRNLAVHS-UHFFFAOYSA-N 0.000 description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 2
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 2
- DDOFUHLLHDWGRW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-(10-naphthalen-2-ylanthracen-9-yl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(C=2C3=CC=CC=C3C(C=3C=C4C=CC=CC4=CC=3)=C3C=CC=CC3=2)=C1 DDOFUHLLHDWGRW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000123 polythiophene Chemical class 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Pyridine Compounds (AREA)
- Electroluminescent Light Sources (AREA)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011516065A JP5533863B2 (ja) | 2009-05-29 | 2010-05-28 | 電子輸送材料およびこれを用いた有機電界発光素子 |
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| JP2009130637 | 2009-05-29 | ||
| JP2009130637 | 2009-05-29 | ||
| JP2011516065A JP5533863B2 (ja) | 2009-05-29 | 2010-05-28 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| PCT/JP2010/059063 WO2010137678A1 (ja) | 2009-05-29 | 2010-05-28 | 電子輸送材料およびこれを用いた有機電界発光素子 |
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| JPWO2010137678A1 JPWO2010137678A1 (ja) | 2012-11-15 |
| JP5533863B2 true JP5533863B2 (ja) | 2014-06-25 |
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| JP2011516065A Active JP5533863B2 (ja) | 2009-05-29 | 2010-05-28 | 電子輸送材料およびこれを用いた有機電界発光素子 |
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| Country | Link |
|---|---|
| JP (1) | JP5533863B2 (ko) |
| KR (2) | KR101789339B1 (ko) |
| CN (3) | CN104311475A (ko) |
| WO (1) | WO2010137678A1 (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012126717A (ja) * | 2010-11-25 | 2012-07-05 | Jnc Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
| JPWO2012060374A1 (ja) * | 2010-11-04 | 2014-05-12 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI491602B (zh) * | 2009-12-03 | 2015-07-11 | Jnc Corp | 具有含吡啶取代基的苯并［ｃ］咔唑化合物及有機電激發光元件 |
| JP5807637B2 (ja) * | 2010-07-05 | 2015-11-10 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| WO2012070535A1 (ja) * | 2010-11-25 | 2012-05-31 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| TWI504722B (zh) * | 2010-12-03 | 2015-10-21 | Jnc Corp | 具有含吡啶取代基的苯并［ｃ］咔唑化合物及有機電激發光元件 |
| JP5819069B2 (ja) * | 2011-01-20 | 2015-11-18 | 株式会社Ｊｏｌｅｄ | 有機ｅｌ表示装置 |
| US9070885B2 (en) | 2011-01-27 | 2015-06-30 | Jnc Corporation | Anthracene compound and organic electroluminescence element using same |
| JP6070047B2 (ja) * | 2011-10-27 | 2017-02-01 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| CN103958471B (zh) | 2012-02-03 | 2016-08-17 | 捷恩智株式会社 | 蒽衍生物及使用其的有机电场发光组件、电子传输材料、显示装置及照明装置 |
| JP6136311B2 (ja) * | 2012-02-06 | 2017-05-31 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| US9105852B2 (en) * | 2012-02-17 | 2015-08-11 | Semiconductor Energy Laboratory Co., Ltd. | Bipyridine compound, light-emitting element material, organic semiconductor material, light-emitting element, display module, lighting module, light-emitting device, lighting device, display device and electronic device |
| JP2013227251A (ja) * | 2012-04-25 | 2013-11-07 | Jnc Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
| KR102030584B1 (ko) * | 2013-01-08 | 2019-10-10 | 에스에프씨주식회사 | 헤테로아릴 치환기를 갖는 페닐기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자 |
| KR102051952B1 (ko) * | 2013-01-08 | 2019-12-04 | 에스에프씨주식회사 | 헤테로아릴 치환기를 갖는 나프틸기를 포함하는 안트라센 유도체 및 이를 포함하는 유기 발광 소자 |
| KR102050484B1 (ko) | 2013-03-04 | 2019-12-02 | 삼성디스플레이 주식회사 | 안트라센 유도체 및 이를 포함하는 유기전계발광소자 |
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| KR102269131B1 (ko) | 2013-07-01 | 2021-06-25 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
| US10062850B2 (en) | 2013-12-12 | 2018-08-28 | Samsung Display Co., Ltd. | Amine-based compounds and organic light-emitting devices comprising the same |
| WO2015141608A1 (ja) * | 2014-03-17 | 2015-09-24 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| KR20150132795A (ko) | 2014-05-16 | 2015-11-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102332591B1 (ko) | 2014-06-09 | 2021-11-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102327086B1 (ko) | 2014-06-11 | 2021-11-17 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102343145B1 (ko) | 2015-01-12 | 2021-12-27 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
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| WO2004063159A1 (ja) * | 2003-01-10 | 2004-07-29 | Idemitsu Kosan Co., Ltd. | 含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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| WO2006067931A1 (ja) * | 2004-12-22 | 2006-06-29 | Idemitsu Kosan Co., Ltd. | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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| CN101219987A (zh) * | 2003-01-10 | 2008-07-16 | 出光兴产株式会社 | 含氮杂环衍生物以及使用该衍生物的有机电致发光元件 |
| CN101370905B (zh) * | 2006-01-13 | 2013-08-07 | Lg化学株式会社 | 发光材料及使用该材料的有机发光器件 |
| JP5353233B2 (ja) * | 2007-12-27 | 2013-11-27 | Ｊｎｃ株式会社 | ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子 |
| KR101058103B1 (ko) * | 2008-04-15 | 2011-08-24 | 삼성모바일디스플레이주식회사 | 바이피리딘계 화합물 및 이를 포함한 유기막을 구비한 유기발광 소자 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2004063159A1 (ja) * | 2003-01-10 | 2004-07-29 | Idemitsu Kosan Co., Ltd. | 含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
| WO2005091686A1 (ja) * | 2004-03-19 | 2005-09-29 | Chisso Corporation | 有機電界発光素子 |
| JP2006045503A (ja) * | 2004-07-09 | 2006-02-16 | Chisso Corp | 発光材料およびこれを用いた有機電界発光素子 |
| WO2006067931A1 (ja) * | 2004-12-22 | 2006-06-29 | Idemitsu Kosan Co., Ltd. | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012060374A1 (ja) * | 2010-11-04 | 2014-05-12 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| JP5737294B2 (ja) * | 2010-11-04 | 2015-06-17 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| JP2012126717A (ja) * | 2010-11-25 | 2012-07-05 | Jnc Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
Also Published As
| Publication number | Publication date |
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| CN104292152A (zh) | 2015-01-21 |
| CN102414179B (zh) | 2015-03-11 |
| CN104311475A (zh) | 2015-01-28 |
| JPWO2010137678A1 (ja) | 2012-11-15 |
| WO2010137678A1 (ja) | 2010-12-02 |
| KR101789339B1 (ko) | 2017-10-23 |
| KR20170096234A (ko) | 2017-08-23 |
| CN102414179A (zh) | 2012-04-11 |
| KR20120026513A (ko) | 2012-03-19 |
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