JP5922792B2 - 有機発光化合物及びこれを用いた有機電界発光素子 - Google Patents
有機発光化合物及びこれを用いた有機電界発光素子 Download PDFInfo
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- JP5922792B2 JP5922792B2 JP2014545825A JP2014545825A JP5922792B2 JP 5922792 B2 JP5922792 B2 JP 5922792B2 JP 2014545825 A JP2014545825 A JP 2014545825A JP 2014545825 A JP2014545825 A JP 2014545825A JP 5922792 B2 JP5922792 B2 JP 5922792B2
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- 150000001875 compounds Chemical class 0.000 title claims description 252
- 239000000126 substance Substances 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 239000010410 layer Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 239000012044 organic layer Substances 0.000 claims description 45
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000005264 aryl amine group Chemical group 0.000 claims description 19
- 125000005104 aryl silyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 6
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 849
- 238000003786 synthesis reaction Methods 0.000 description 849
- 238000002360 preparation method Methods 0.000 description 200
- 238000005160 1H NMR spectroscopy Methods 0.000 description 99
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- -1 indole compound Chemical class 0.000 description 62
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 43
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 39
- 238000004440 column chromatography Methods 0.000 description 39
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 37
- RHUICOIYTTZMKP-UHFFFAOYSA-N 5-(2-nitrophenyl)-1-phenylindole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(N(C=C2)C=3C=CC=CC=3)C2=C1 RHUICOIYTTZMKP-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- OVNPUJOZNPAVJQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OVNPUJOZNPAVJQ-UHFFFAOYSA-N 0.000 description 24
- INJYATWDDJSOIP-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyridine Chemical compound N=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 INJYATWDDJSOIP-UHFFFAOYSA-N 0.000 description 24
- NRDZHTMNMSJGKG-UHFFFAOYSA-N 5-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(NC=C2)C2=C1 NRDZHTMNMSJGKG-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 23
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000000746 purification Methods 0.000 description 20
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 19
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 19
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005401 electroluminescence Methods 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- JSVPPCUHRRGCCL-UHFFFAOYSA-N 6-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(C=CN2)C2=C1 JSVPPCUHRRGCCL-UHFFFAOYSA-N 0.000 description 13
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 12
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- FATPQDPUKVVCLT-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(NC=C2)C2=C1 FATPQDPUKVVCLT-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 8
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 8
- XGOWHPSXPPZWAH-UHFFFAOYSA-N 5-bromo-2-phenyl-1h-indole Chemical compound C=1C2=CC(Br)=CC=C2NC=1C1=CC=CC=C1 XGOWHPSXPPZWAH-UHFFFAOYSA-N 0.000 description 8
- QHYNPLOZCBHGNX-UHFFFAOYSA-N 6-(2-bromophenyl)-7-chloro-1h-indole Chemical compound C1=CC=2C=CNC=2C(Cl)=C1C1=CC=CC=C1Br QHYNPLOZCBHGNX-UHFFFAOYSA-N 0.000 description 8
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- IOPQERQQZZREDR-UHFFFAOYSA-N 1-bromo-3,5-diphenylbenzene Chemical compound C=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 IOPQERQQZZREDR-UHFFFAOYSA-N 0.000 description 6
- YASXBDJBCBUIHT-UHFFFAOYSA-N 2,4-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC(C=2C=CC=CC=2)=C1 YASXBDJBCBUIHT-UHFFFAOYSA-N 0.000 description 6
- OOHRWLAEJIWHQB-UHFFFAOYSA-N 2-(3-bromo-5-phenylphenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C(N=1)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 OOHRWLAEJIWHQB-UHFFFAOYSA-N 0.000 description 6
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 6
- YTYIMDRWPTUAHP-UHFFFAOYSA-N 6-Chloroindole Chemical compound ClC1=CC=C2C=CNC2=C1 YTYIMDRWPTUAHP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 5
- IYERRTIEAMZWGN-UHFFFAOYSA-N 4-(2-nitrophenyl)-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=CC2=C1C=CN2 IYERRTIEAMZWGN-UHFFFAOYSA-N 0.000 description 5
- BWABEHDYBGCBHQ-UHFFFAOYSA-N 5-(2-nitrophenyl)-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(OC=C2)C2=C1 BWABEHDYBGCBHQ-UHFFFAOYSA-N 0.000 description 5
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 5
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- 238000000605 extraction Methods 0.000 description 5
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- YKFRPCRADQOKOA-UHFFFAOYSA-N 10-(4-bromophenyl)-9,9-dimethylacridine Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1C1=CC=C(Br)C=C1 YKFRPCRADQOKOA-UHFFFAOYSA-N 0.000 description 4
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- BHJFLOOHSMTNSJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,6-diphenylpyrimidine Chemical compound ClC1=CC=CC(C=2N=C(C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BHJFLOOHSMTNSJ-UHFFFAOYSA-N 0.000 description 4
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- WNOHGVLVECBDRM-UHFFFAOYSA-N (8-bromodibenzothiophen-2-yl)-trimethylsilane Chemical compound C[Si](C)(C)c1ccc2sc3ccc(Br)cc3c2c1 WNOHGVLVECBDRM-UHFFFAOYSA-N 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 3
- FBQFCXDBCPREBP-UHFFFAOYSA-N 2-(4-bromophenyl)pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=N1 FBQFCXDBCPREBP-UHFFFAOYSA-N 0.000 description 3
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- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
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- 239000004332 silver Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- H10K50/15—Hole 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Description
[化1]
式中、R1及びR2は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基及びC6〜C60のアリールアミン基からなる群から選択され、
Y1〜Y4は、それぞれ独立に、N又はCR3であり、Y1とY2、Y2とY3、又はY3とY4のうちのいずれか1つは、下記化2で示される縮合環を形成し、
[化2]
式中、Y5〜Y8は、それぞれ独立に、N又はCR4であり、点線は、上記化1の化合物と縮合される部位を意味し、
X1及びX2は、それぞれ独立に、O、S、Se、N(Ar1)、C(Ar2)(Ar3)及びSi(Ar4)(Ar5)からなる群から選択され、X1及びX2の少なくとも1つは、N(Ar1)であり、
R3及びR4は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記Ar1〜Ar5は、それぞれ独立に、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記R1〜R4及びAr1〜Ar5におけるC1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基は、それぞれ独立に、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1つ以上の置換基で置換されることができる。
本発明において使用されるアルキルとしては、炭素数1〜40の直鎖又は側鎖の飽和炭化水素であり、例えば、メチル、エチル、プロピル、イソブチル、sec−ブチル、ペンチル、iso−アミル、ヘキシルなどが挙げられる。
また、本発明において使用されるアリールとは、単環又は二つ以上の環が組み合わされた炭素数6〜60の芳香族部位を意味し、2以上の環が互いに単にペンダント又は縮合された形態で結合されることができる。このようなアリールとしては、例えば、フェニル、インデニル、ナフチル、アントラセニル、フルオレニル、フェナントリル、ピレニル、クリセニルなどが挙げられる。
また、本発明において使用されるヘテロアリールとは、核原子数5〜60のモノヘテロサイクリック又はポリヘテロサイクリック芳香族部位を意味し、環中の1つ以上の炭素、好ましくは、1〜3個の炭素が、N、O、S、Si又はSeのようなヘテロ原子に置換される。このようなヘテロアリールは、2以上の環が互いに単にペンダント又は縮合された形態で結合することができ、さらには、アリール基との縮合された形態を含むものと解釈される。ヘテロアリールとしては、例えば、ピラゾリル、イミダゾリル、オキサゾリル、チアゾリル、トリアゾリル、テトラゾリル、オキサジアゾリル、ピリジニル、ピリミジニル、トリアジニル、カルバゾリル、インドリル、キノリニル、イソキノリニルなどが挙げられる。
[化1a]
[化1b]
[化1c]
[化1d]
[化1e]
[化1f]
式中、R1、R2、X1、X2及びY1〜Y8は、上記で定義した通りである。
[化3]
式中、R1、R2及びY1〜Y4は、上記で定義した通りであり、Y1とY2、Y2とY3、又はY3とY4のうちのいずれか1つは、下記化4で示される縮合環を形成し、
[化4]
式中、Y5〜Y8は、上記で定義した通りであり、点線は、前記化3で示される化合物と縮合される部位を意味し、Ar1は、C6〜C60のアリール基、又は核原子数5〜60のヘテロアリール基であり、Ra及びRbは、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基及びC6〜C60のアリールアミン基からなる群から選択され、
前記Ra及びRbにおけるC1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基は、それぞれ独立に、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1つ以上の置換基で置換されることができ、n及びmは、それぞれ独立に、0〜5の整数であり、但し、n+mは、少なくとも1以上である。ここで、前記化3の構造からみて、Ar1は、C6〜C60のアリーレン、又は核原子数5〜60のヘテロアリーレンのような二価の官能基と解釈されることもできる。
[化5]
式中、R1、R2及びY1〜Y4は、上記で定義した通りであり、Y1とY2、Y2とY3、又はY3とY4のうちのいずれか1つは、下記化6で示される縮合環を形成し、
[化6]
式中、Y5〜Y8は、上記で定義した通りであり、点線は、前記化5の化合物と縮合される部位を意味し、Z1〜Z6は、それぞれ独立に、N又はCAr6であり、前記Ar6、A及びBは、それぞれ独立に、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、r及びsは、それぞれ0〜5の整数(但し、r+sは、少なくとも1以上)であり、p及びqは、それぞれ0〜3の整数である。
[化5a]
[化5b]
[化5c]
[化5d]
[化5e]
[化5f]
式中、R1、R2、Y1〜Y8、Z1〜Z6、A、B、r、s、p及びqは、上記で定義した通りである。
[化6a]
[化6b]
[化6c]
[化6d]
[化6e]
[化6f]
[化6g]
[化6h]
[化6i]
[化6j]
[化6k]
[化6l]
式中、R1、R2、Y1〜Y8及びAr1は、上記で定義した通りである。
本発明に係る有機電界発光素子の構造としては、例えば、基板、陽極、正孔注入層、正孔輸送層、発光層、電子輸送層及び陰極が順に積層された構造であることができるが、これに制限されない。この時、正孔注入層、正孔輸送層、電子注入層、電子輸送層及び発光層のうちのいずれか1つ以上は、前記化1で示される化合物を1種以上含むことができる。また、本発明の化1で示される化合物は、発光層の燐光ホストとして使用されることができる。前記電子輸送層の上には、電子注入層が位置することもできる。
<ステップ1>5−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−1H−インドールの合成
1H−NMR:δ1.24(s,12H),6.45(d,1H),7.27(d,1H),7.42(d,1H),7.52(d,1H),7.95(s,1H),8.21(s,1H)
1H−NMR:δ6.47(d,1H),7.25(d,1H),7.44(d,1H),7.53(d,1H),7.65(t,1H),7.86(t,1H),7.95(s,1H),8.00(d,1H),8.09(t,1H),8.20(s,1H)
1H−NMR:δ6.48(d,1H),7.26(d,1H),7.45(m,3H),7.55(m,4H),7.63(t,1H),7.84(t,1H),7.93(s,1H),8.01(d,1H),8.11(t,1H)
IC−1aに関する1H−NMR:δ6.51(d,1H),7.28(d,1H),7.46(m,3H),7.51(s,1H),7.56(m,3H),7.64(t,1H),7.85(m,2H),8.08(t,1H),8.24(s,1H)
IC−1bに関する1H−NMR:δ6.53(d,1H),7.27(d,1H),7.45(m,3H),7.50(d,1H),7.55(m,3H),7.67(t,1H),7.89(m,2H),8.12(t,1H),8.25(s,1H)
<ステップ1>4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−1H−インドールの合成
1H NMR:δ1.26(s,12H),6.43(d,1H),7.26(t,1H),7.48(d,1H),7.74(d,1H),7.85(d,1H),8.23(s,1H)
1H NMR:δ6.45(d,1H),7.27(t,1H),7.50(d,1H),7.66(t,1H),7.75(d,1H),7.89(m,2H),7.99(d,1H),8.04(d,1H),8.24(s,1H)
1H NMR:δ6.47(d,1H),7.28(t,1H),7.47(m,2H),7.52(m,2H),7.60(m,2H),7.67(t,1H),7.75(d,1H),7.89(m,2H),8.00(d,1H),8.06(d,1H)
1H NMR:δ6.49(d,1H),7.29(t,1H),7.46(m,2H),7.54(m,2H),7.61(d,1H),7.69(t,1H),7.74(d,1H),7.88(m,2H),8.01(d,1H),8.04(d,1H),8.23(s,1H)
<ステップ1>7−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−1H−インドールの合成
1H NMR:δ1.25(s,12H),6.43(d,1H),7.25(d,1H),7.45(t,1H),7.56(d,1H),7.71(d,1H),8.22(s,1H)
1H NMR:δ6.42(d,1H),7.24(d,1H),7.43(t,1H),7.55(d,1H),7.70(m,2H),7.88(t,1H),8.01(d,1H),8.11(d,1H),8.23(s,1H)
1H NMR:δ6.43(d,1H),7.26(d,1H),7.44(m,3H),7.56(m,4H),7.71(m,2H),7.89(t,1H),8.02(d,1H),8.10(d,1H)
1H NMR:δ6.45(d,1H),7.24(d,1H),7.45(m,3H),7.57(m,3H),7.63(d,1H),7.70(d,1H),7.88(t,1H),8.00(d,1H),8.09(d,1H),8.22(s,1H)
<ステップ1>5−(1−ニトロナフタレン−2−イル)−1H−インドールの合成
1H NMR:δ6.44(d,1H),7.26(d,1H),7.43(d,1H),7.53(d,1H),7.64(m,3H),7.80(m,3H),7.94(s,1H),8.23(s,1H)
1H NMR:δ6.44(d,1H),7.26(d,1H),7.43(m,3H),7.53(m,4H),7.64(m,3H),7.80(m,3H),7.94(s,1H)
IC−4aに関する1H−NMR:δ6.44(d,1H),7.26(m,2H),7.43(s,1H),7.53(m,4H),7.64(m,3H),7.71(s,1H),7.80(m,3H),8.20(s,1H)
IC−4bに関する1H−NMR:δ6.43(d,1H),7.27(m,2H),7.42(d,1H),7.55(m,4H),7.65(d,1H),7.72(m,3H),7.82(m,3H),8.20(s,1H)
<ステップ1>5−(2−ニトロナフタレン−1−イル)−1H−インドールの合成
1H NMR:δ6.43(d,1H),7.25(d,1H),7.44(d,1H),7.55(d,1H),7.67(m,2H),7.81(d,1H),7.96(m,2H),8.00(d,1H),8.05(d,1H),8.23(s,1H)
1H NMR:δ6.45(d,1H),7.26(d,1H),7.45(m,2H),7.54(m,2H),7.66(m,3H),7.80(d,1H),7.96(m,2H),8.01(m,2H),8.06(m,2H)
IC−5aに関する1H−NMR:δ6.45(d,1H),7.26(d,1H),7.45(s,1H),7.54(s,1H),7.66(m,2H),7.80(m,3H),7.96(m,2H),8.01(m,2H),8.06(m,2H),8.21(s,1H)
IC−5bに関する1H−NMR:δ6.43(d,1H),7.25(d,1H),7.46(d,1H),7.57(d,1H),7.65(m,2H),7.81(m,3H),7.95(m,2H),8.00(m,2H),8.05(m,2H),8.21(s,1H)
<ステップ1>5−(5−ブロモ−2−ニトロフェニル)−1H−インドールの合成
1H NMR:δ6.45(d,1H),7.26(d,1H),7.45(d,1H),7.55(d,1H),7.64(d,1H),7.85(d,1H),7.96(s,1H),8.13(s,1H),8.21(s,1H)
1H NMR:δ6.44(d,1H),7.25(d,1H),7.46(m,3H),7.56(m,4H),7.65(d,1H),7.86(d,1H),7.95(s,1H),8.11(s,1H)
IC−6aに関する1H−NMR:δ6.44(d,1H),7.25(d,1H),7.39(m,2H),7.46(s,1H),7.50(s,1H),7.58(m,3H),7.65(d,1H),7.86(d,1H),8.11(s,1H),8.22(s,1H)
IC−6bに関する1H−NMR:δ6.45(d,1H),7.26(d,1H),7.38(m,2H),7.45(d,1H),7.51(d,1H),7.57(m,3H),7.64(d,1H),7.85(d,1H),8.10(s,1H),8.23(s,1H)
<ステップ1>1−(4,6−ジフェニルピリジン−2−イル)−4−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:467.16g/mol、測定値:467g/mol)
GC−Mass(理論値:435.17g/mol、測定値:435g/mol)
<ステップ1>1−(4,6−ジフェニルピリジン−2−イル)−7−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:467.16g/mol、測定値:467g/mol)
GC−Mass(理論値:435.17g/mol、測定値:435g/mol)
<ステップ1>1−(2,3’−ビピリジン−6−イル)−4−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:392.13g/mol、測定値:392g/mol)
GC−Mass(理論値:360.14g/mol、測定値:360g/mol)
<ステップ1>6−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−1H−インドールの合成
1H−NMR:δ1.25(s,12H),6.52(d,1H),7.16(d,1H),7.21(d,1H),7.49(d,1H),7.53(s,1H),8.15(s,1H)
1H−NMR:δ6.57(d,1H),7.07(d,1H),7.24(d,1H),7.35(s,1H),7.43(t,1H),7.50(d,1H),7.58(t,1H),7.66(d,1H),7.78(d,1H),8.19(s,1H)
1H−NMR:δ6.81(d,1H),7.12(t,1H),7.22(t,1H),7.35(s,1H),7.43(d,1H),7.51(m,3H),7.56(m,2H),7.62(m,2H),7.85(d,1H),8.02(d,1H)
1H−NMR:δ6.80(d,1H),7.11(t,1H),7.23(t,1H),7.42(d,1H),7.50(m,3H),7.57(m,2H),7.63(m,2H),7.86(d,1H),8.03(d,1H),9.81(s,1H)
<ステップ1>6−(5−ブロモ−2−ニトロフェニル)−1H−インドールの合成
1H−NMR:δ6.51(d,1H),7.31(d,1H),7.50(d,1H),7.60(d,1H),7.69(d,1H),7.90(d,1H),8.01(s,1H),8.14(s,1H),8.25(s,1H)
1H NMR:δ6.49(d,1H),7.30(d,1H),7.51(m,3H),7.61(m,4H),7.70(d,1H),7.91(d,1H),8.00(s,1H),8.16(s,1H)
1H−NMR:δ6.47(d,1H),7.28(d,1H),7.40(m,2H),7.47(d,1H),7.53(d,1H),7.59(m,3H),7.66(d,1H),7.87(d,1H),8.12(s,1H),8.25(s,1H)
<ステップ1>5−(2−ニトロフェニル)−1−o−トリル−1H−インドールの合成
1H−NMR:δ1.92(s,3H),6.47(d,1H),7.25(d,1H),7.46(m,3H),7.56(m,3H),7.64(t,1H),7.85(t,1H),7.94(s,1H),8.00(d,1H),8.12(t,1H)
1H−NMR:δ1.93(s,3H),6.98(d,1H),7.11(t,1H),7.28(t,1H),7.31(d,1H),7.42(t,1H),7.51(d,1H),7.61(m,4H),7.86(d,1H),8.01(d,1H),10.58(s,1H)
<ステップ1>1−(ビフェニル−4−イル)−5−(2−ニトロフェニル)−1H−インドールの合成
1H−NMR:δ6.73(d,1H),7.18(d,1H),7.39(m,2H),7.47(m,3H),7.54(d,1H),7.59(m,3H),7.64(m,4H),7.75(d,2H),7.82(d,1H)
1H−NMR:δ6.75(d,1H),7.20(d,1H),7.42(m,2H),7.51(m,3H),7.56(d,1H),7.62(m,3H),7.68(m,3H),7.76(d,2H),7.85(d,1H),10.45(s,1H)
<ステップ1>IC−14−1の合成
1H−NMR:δ6.98(d,1H),7.11(t,1H),7.24(t,1H),7.38(t,2H),7.46(m,6H),7.58(d,1H),7.81(d,4H),7.87(m,4H),7.93(d,1H),7.99(d,1H)
1H−NMR:δ6.97(d,1H),7.10(t,1H),7.23(t,1H),7.37(t,2H),7.45(m,6H),7.58(d,1H),7.80(d,4H),7.86(m,3H),7.92(d,1H),7.98(d,1H),10.60(s,1H)
<ステップ1>5−(2−ニトロフェニル)−1−(2−(トリフルオロメチル)フェニル)−1H−インドールの合成
1H−NMR:δ6.48(d,1H),7.26(d,1H),7.47(m,3H),7.57(m,3H),7.63(t,1H),7.84(t,1H),7.95(s,1H),8.01(d,1H),8.13(t,1H)
1H−NMR:δ6.97(d,1H),7.12(t,1H),7.29(t,1H),7.32(d,1H),7.41(t,1H),7.52(d,1H),7.60(m,4H),7.85(d,1H),8.01(d,1H),10.57(s,1H)
<ステップ1>1−(ビフェニル−3−イル)−5−(2−ニトロフェニル)−1H−インドールの合成
1H−NMR:δ6.75(d,1H),7.19(d,1H),7.38(m,2H),7.48(m,3H),7.52(d,1H),7.58(m,3H),7.65(m,4H),7.76(m,2H),7.85(d,1H)
1H−NMR:δ6.74(d,1H),7.21(d,1H),7.41(m,2H),7.52(m,3H),7.56(d,1H),7.61(m,3H),7.69(m,3H),7.77(m,2H),7.86(d,1H),10.44(s,1H)
<ステップ1>1−(ビフェニル−3−イル)−6−(2−ニトロフェニル)−1H−インドールの合成
1H−NMR:δ6.76(d,1H),7.18(d,1H),7.37(m,2H),7.47(m,3H),7.51(d,1H),7.57(m,3H),7.64(m,4H),7.75(m,2H),7.86(d,1H)
1H−NMR:δ6.75(d,1H),7.20(d,1H),7.40(m,2H),7.51(m,3H),7.57(d,1H),7.62(m,3H),7.70(m,3H),7.76(m,2H),7.85(d,1H),10.43(s,1H)
<ステップ1>1−(ビフェニル−4−イル)−6−(2−ニトロフェニル)−1H−インドールの合成
1H−NMR:δ6.74(d,1H),7.19(d,1H),7.40(m,2H),7.46(m,3H),7.55(d,1H),7.58(m,3H),7.63(m,4H),7.75(d,2H),7.83(d,1H)
1H−NMR:δ6.74(d,1H),7.19(d,1H),7.43(m,2H),7.52(m,3H),7.57(d,1H),7.63(m,3H),7.69(m,3H),7.75(d,2H),7.86(d,1H),10.46(s,1H)
<ステップ1>IC−19−1の合成
1H−NMR:δ6.98(d,1H),7.11(t,1H),7.24(t,1H),7.38(m,2H),7.45(m,6H),7.57(d,1H),7.80(d,4H),7.86(m,4H),7.92(d,1H),7.98(d,1H)
1H−NMR:δ6.97(d,1H),7.10(t,1H),7.23(t,1H),7.37(t,2H),7.45(m,6H),7.58(d,1H),7.80(d,4H),7.86(m,3H),7.92(d,1H),7.98(d,1H),10.59(s,1H)
<ステップ1>6−(2−ニトロフェニル)−1−(3−(トリフルオロメチル)フェニル)−1H−インドールの合成
1H−NMR:δ6.80(d,1H),7.11(t,1H),7.21(t,1H),7.36(s,1H),7.42(s,1H),7.50(m,2H),7.55(m,2H),7.63(m,2H),7.86(d,1H),8.01(d,1H)
1H−NMR:δ6.81(d,1H),7.12(t,1H),7.24(t,1H),7.43(d,1H),7.51(m,2H),7.58(m,2H),7.64(m,2H),7.85(d,1H),8.02(d,1H),9.82(s,1H)
<ステップ1>3−(5−(2−ニトロフェニル)−1H−インドール−1−イル)−9−フェニル−9H−カルバゾールの合成
GC−Mass(理論値:476.16g/mol、測定値:479g/mol)
GC−Mass(理論値:447.17g/mol、測定値:447g/mol)
<ステップ1>9−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−3−(5−(2−ニトロフェニル)−1H−インドール−1−イル)−9H−カルバゾールの合成
GC−Mass(理論値:634.21g/mol、測定値:634g/mol)
GC−Mass(理論値:602.22g/mol、測定値:602g/mol)
<ステップ1>5−ブロモ−2−フェニル−1H−インドールの合成
1H−NMR:δ6.89(dd,1H),7.20(dd,1H),7.34(m,1H),7.36(d,1H),7.47(t,2H),7.71(d,1H),7.86(dd,2H),11.74(s,1H)
1H−NMR:δ6.88(dd,1H),7.21(dd,1H),7.32(m,1H),7.34(d,1H),7.46(m,3H),7.64(m,2H),7.77(d,2H),8.02(d,2H),11.73(s,1H)
GC−Mass(理論値:390.14g/mol、測定値:390g/mol)
GC−Mass(理論値:358.15g/mol、測定値:358g/mol)
<ステップ1>6−クロロ−2−フェニル−1H−インドールの合成
1H−NMR:δ6.92(d,1H),7.02(dd,1H),7.33(t,1H),7.41(s,1H),7.47(t,2H),7.54(d,1H),7.85(d,2H),11.68(s,1H)
1H−NMR:δ6.91(d,1H),7.03(d,1H),7.31(t,1H),7.42(s,1H),7.48(m,3H),7.53(d,1H),7.76(m,3H),8.01(d,2H),11.66(s,1H)
GC−Mass(理論値:390.14g/mol、測定値:390g/mol)
GC−Mass(理論値:358.15g/mol、測定値:358g/mol)
<ステップ1>6−クロロ−3−フェニル−1H−インドールの合成
1H−NMR:δ7.10(dd,1H),7.25(m,1H),7.43(t,2H),7.49(d,1H),7.67(dd,2H),7.73(d,1H),7.85(d,1H),11.49(s,1H)
1H−NMR:δ7.11(d,1H),7.26(m,1H),7.44(t,2H),7.48(m,2H),7.55(m,3H),7.61(d,1H),7.73(d,1H),8.00(d,2H),11.48(s,1H)
GC−Mass(理論値:390.14g/mol、測定値:390g/mol)
GC−Mass(理論値:358.15g/mol、測定値:358g/mol)
<ステップ1>5−ブロモ−2,3−ジフェニル−1H−インドールの合成
1H−NMR:δ7.23(d,1H),7.31(t,2H),7.43(m,6H),7.67(d,1H),7.71(d,1H),7.84(d,2H),11.34(s,1H)
GC−Mass(理論値:390.14g/mol、測定値:390g/mol)
GC−Mass(理論値:466.17g/mol、測定値:466g/mol)
GC−Mass(理論値:434.18g/mol、測定値:434g/mol)
<ステップ1>6−クロロ−2,3−ジフェニル−1H−インドールの合成
1H−NMR:δ7.18(d,1H),7.29(t,2H),7.50(m,6H),7.62(d,1H),7.75(d,1H),7.89(d,2H),11.35(s,1H)
GC−Mass(理論値:390.14g/mol、測定値:390g/mol)
GC−Mass(理論値:466.17g/mol、測定値:466g/mol)
GC−Mass(理論値:434.18g/mol、測定値:434g/mol)
<ステップ1>1−(3−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)フェニル)−6−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:545.19g/mol、測定値:545g/mol)
GC−Mass(理論値:513.20g/mol、測定値:513g/mol)
<ステップ1>1−(3−(4,6−ジフェニルピリミジン−2−イル)フェニル)−6−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:544.19g/mol、測定値:544g/mol)
GC−Mass(理論値:512.20g/mol、測定値:512g/mol)
<ステップ1>1−(3−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)フェニル)−5−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:545.19g/mol、測定値:545g/mol)
GC−Mass(理論値:513.20g/mol、測定値:513g/mol)
<ステップ1>1−(3−(4,6−ジフェニルピリミジン−2−イル)フェニル)−5−(2−ニトロフェニル)−1H−インドールの合成
GC−Mass(理論値:544.19g/mol、測定値:544g/mol)
GC−Mass(理論値:512.20g/mol、測定値:512g/mol)
GC−Mass(理論値:511.20g/mol、測定値:511g/mol)
GC−Mass(理論値:436.17g/mol、測定値:436g/mol)
GC−Mass(理論値:513.20g/mol、測定値:513g/mol)
GC−Mass(理論値:464.13g/mol、測定値:464g/mol)
GC−Mass(理論値:512.20g/mol、測定値:512g/mol)
GC−Mass(理論値:523.20g/mol、測定値:523g/mol)
GC−Mass(理論値:525.22g/mol、測定値:525g/mol)
GC−Mass(理論値:436.17g/mol、測定値:436g/mol)
GC−Mass(理論値:485.19g/mol、測定値:485g/mol)
GC−Mass(理論値:487.18g/mol、測定値:487g/mol)
GC−Mass(理論値:562.22g/mol、測定値:562g/mol)
GC−Mass(理論値:627.24g/mol、測定値:627g/mol)
GC−Mass(理論値:639.24g/mol、測定値:639g/mol)
GC−Mass(理論値:486.18g/mol、測定値:486g/mol)
GC−Mass(理論値:600.23g/mol、測定値:600g/mol)
GC−Mass(理論値:638.25g/mol、測定値:638g/mol)
GC−Mass(理論値:512.20g/mol、測定値:512g/mol)
GC−Mass(理論値:562.22g/mol、測定値:562g/mol)
GC−Mass(理論値:587.24g/mol、測定値:587g/mol)
GC−Mass(理論値:663.27g/mol、測定値:663g/mol)
GC−Mass(理論値:676.26g/mol、測定値:676g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:829.32g/mol、測定値:829g/mol)
GC−Mass(理論値:587.24g/mol、測定値:587g/mol)
GC−Mass(理論値:591.22g/mol、測定値:591g/mol)
GC−Mass(理論値:514.19g/mol、測定値:514g/mol)
GC−Mass(理論値:434.18g/mol、測定値:434g/mol)
GC−Mass(理論値:435.17g/mol、測定値:435.17g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:591.22g/mol、測定値:591g/mol)
GC−Mass(理論値:603.24g/mol、測定値:603g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:657.21g/mol、測定値:657g/mol)
GC−Mass(理論値:664.26g/mol、測定値:664g/mol)
GC−Mass(理論値:678.25g/mol、測定値:678g/mol)
GC−Mass(理論値:522.23g/mol、測定値:522g/mol)
GC−Mass(理論値:542.19g/mol、測定値:542g/mol)
GC−Mass(理論値:616.23g/mol、測定値:616g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:434.18g/mol、測定値:434g/mol)
GC−Mass(理論値:435.17g/mol、測定値:435g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:591.22g/mol、測定値:591g/mol)
GC−Mass(理論値:603.24g/mol、測定値:603g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:590.22g/mol、測定値:590g/mol)
GC−Mass(理論値:664.26g/mol、測定値:664g/mol)
GC−Mass(理論値:678.25g/mol、測定値:678g/mol)
GC−Mass(理論値:522.23g/mol、測定値:522g/mol)
GC−Mass(理論値:542.19g/mol、測定値:542g/mol)
GC−Mass(理論値:616.23g/mol、測定値:616g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:830.32g/mol、測定値:830g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:983.37g/mol、測定値:983g/mol)
GC−Mass(理論値:603.24g/mol、測定値:603g/mol)
GC−Mass(理論値:679.27g/mol、測定値:679g/mol)
GC−Mass(理論値:775.30g/mol、測定値:775g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:664.26g/mol、測定値:664g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:817.32g/mol、測定値:817g/mol)
GC−Mass(理論値:664.26g/mol、測定値:664g/mol)
GC−Mass(理論値:830.32g/mol、測定値:830g/mol)
GC−Mass(理論値:657.21g/mol、測定値:657g/mol)
GC−Mass(理論値:657.21g/mol、測定値:657g/mol)
GC−Mass(理論値:656.22g/mol、測定値:656g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:817.32g/mol、測定値:817g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
[合成例80]Inv−80の合成
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:657.21g/mol、測定値:657g/mol)
GC−Mass(理論値:733.25g/mol、測定値:733g/mol)
GC−Mass(理論値:754.28g/mol、測定値:754g/mol)
GC−Mass(理論値:843.31g/mol、測定値:843g/mol)
IC−1bと、3−ブロモビフェニルの代わりに、IC−22と、ヨードベンゼンを使用する以外は、上述の合成例27と同様にして、目的化合物であるInv−87(1.62g、 収率48%)を得た。
GC−Mass(理論値:678.25g/mol、測定値:678g/mol)
GC−Mass(理論値:830.32g/mol、測定値:830g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665.26g/mol)
GC−Mass(理論値:817.32g/mol、測定値:817g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:664.26g/mol、測定値:664g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:817.32g/mol、測定値:817g/mol)
GC−Mass(理論値:587.24g/mol、測定値:587g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:589.23g/mol、測定値:589g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665.26g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
GC−Mass(理論値:740.29g/mol、測定値:740g/mol)
GC−Mass(理論値:741.29g/mol、測定値:741g/mol)
GC−Mass(理論値:588.23g/mol、測定値:588g/mol)
<ステップ1>2−(ベンゾ[b]チオフェン−5−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランの合成
1H NMR:δ1.24(s,12H),7.65(d,1H),7.85(d,1H),7.98(d,1H),8.07(d,1H),8.12(s,1H)
1H NMR:δ7.67(m,2H),7.88(m,2H),7.98(d,1H),8.00(d,1H),8.07(m,2H),8.13(s,1H)
IC−32aの1H−NMR:δ7.29(t,1H),7.59(m,3H),7.79(m,3H),8.11(d,1H),8.26(s,1H)
IC−32bの1H−NMR:δ7.29(t,1H),7.53(m,2H),7.81(m,3H),8.12(m,2H),8.25(s,1H)
<ステップ1>4−(2−イソプロピルフェニル)−1H−インドールの合成
1H NMR:δ1.21(s,6H),2.87(m,1H),6.43(d,1H),7.26(t,1H),7.35(m,3H),7.48(d,1H),7.74(m,2H),7.85(d,1H),8.23(s,1H)
1H NMR:δ1.20(s,6H),6.45(d,1H),7.25(d,1H),7.37(m,3H),7.49(d,1H),7.75(d,1H),7.86(d,1H),8.22(s,1H)
<ステップ1>4−(2−ベンズヒドリルフェニル)−1H−インドールの合成
1H NMR:δ2.88(m,1H),6.44(d,1H),7.27(m,6H),7.34(m,8H),7.47(d,1H),7.75(m,2H),7.86(d,1H),8.21(s,1H)
1H NMR:δ6.43(d,1H),7.26(m,5H),7.34(m,8H),7.46(d,1H),7.76(m,2H),7.85(d,1H),8.20(s,1H)
<ステップ1>6−(2−ブロモフェニル)−7−クロロ−1H−インドールの合成
1H−NMR:δ6.45(d,1H),7.35(m,3H),7.74(m,3H),8.06(d,1H),8.64(s,1H)
1H−NMR:δ1.29(t,3H),2.58(t,2H),3.12(t,2H),4.12(q,2H),6.25(d,1H),7.37(m,4H),7.70(m,2H),8.06(d,1H),8.60(s,1H)
1H−NMR:δ6.44(d,1H),7.25(d,1H),7.51(m,3H),8.00(m,2H),8.40(d,1H),8.63(s,1H)
<ステップ1>5−(2−ブロモフェニル)−6−クロロ−1H−インドールの合成
1H−NMR:δ6.44(d,1H),7.34(m,4H),7.61(m,3H),8.59(s,1H)
1H−NMR:δ1.29(t,3H),2.58(t,2H),3.17(t,2H),4.13(q,2H),6.35(d,1H),7.39(m,5H),7.70(m,2H),8.64(s,1H)
1H−NMR:δ6.50(d,1H),7.51(m,3H),7.71(d,1H),8.01(m,2H),8.45(d,1H),8.68(s,1H)
<ステップ1>4−(2−ブロモフェニル)−5−クロロ−1H−インドールの合成
1H−NMR:δ6.48(d,1H),7.39(m,4H),7.62(m,3H),8.61(s,1H)
1H−NMR:δ1.28(t,3H),2.58(t,2H),3.11(t,2H),4.12(q,2H),6.27(d,1H),7.27(m,4H),7.55(m,3H),8.61(s,1H)
1H−NMR:δ6.50(d,1H),7.31(m,2H),7.51(m,2H),8.01(m,2H),8.44(d,1H),8.58(s,1H)
<ステップ1>7−(2−ブロモフェニル)−6−クロロ−1H−インドールの合成
1H−NMR:δ6.48(d,1H),7.06(d,1H),7.33(m,3H),7.62(m,2H),8.01(d,1H),8.71(s,1H)
1H−NMR:δ1.29(t,3H),2.58(t,2H),3.13(t,2H),4.12(q,2H),6.24(d,1H),7.06(d,1H),7.27(m,3H),7.70(m,2H),8.00(d,1H),8.61(s,1H)
1H−NMR:δ6.44(d,1H),7.51(m,4H),7.89(m,2H),8.48(d,1H),8.68(s,1H)
<ステップ1>6−(2−ブロモフェニル)−5−クロロ−1H−インドールの合成
1H−NMR:δ6.45(d,1H),7.29(m,3H),7.62(m,4H),8.71(s,1H)
1H−NMR:δ1.29(t,3H),2.58(t,2H),3.12(t,2H),4.13(q,2H),6.26(d,1H),7.37(m,4H),7.66(m,3H),8.61(s,1H)
1H−NMR:δ6.45(d,1H),7.31(d,1H),7.50(m,2H),7.81(m,2H),8.01(d,1H),8.48(d,1H),8.68(s,1H)
<ステップ1>5−(2−ブロモフェニル)−4−クロロ−1H−インドールの合成
1H−NMR:δ6.44(d,1H),7.38(m,3H),7.59(m,3H),7.82(d,1H),8.71(s,1H)
1H−NMR:δ1.30(t,3H),2.58(t,2H),3.12(t,2H),4.11(q,2H),6.25(d,1H),7.33(m,4H),7.65(m,3H),8.61(s,1H)
1H−NMR:δ6.43(d,1H),7.33(m,2H),7.51(m,2H),7.99(m,2H),8.48(d,1H),8.68(s,1H)
<ステップ1>7−(2−ニトロフェニル)ベンゾ[b]チオフェンの合成
1H−NMR:δ7.63(m,5H),7.96(m,3H),8.21(d,1H)
1H−NMR:δ7.37(t,1H),7.46(m,5H),7.87(d,1H),8.20(d,1H),8.24(s,1H)
<ステップ1>6−(2−ニトロフェニル)ベンゾ[b]チオフェンの合成
1H−NMR:δ7.68(m,3H),7.98(m,6H)
IC−42aの1H−NMR:δ7.27(t,1H),7.53(m,4H),7.78(d,1H),7.92(d,1H),8.10(d,1H),8.25(s,1H)
IC−42bの1H−NMR:δ7.29(t,1H),7.63(m,3H),7.79(m,3H),8.11(d,1H),8.25(s,1H)
<ステップ1>4−(2−ニトロフェニル)ベンゾ[b]チオフェンの合成
1H−NMR:δ7.68(m,4H),7.89(m,3H),8.01(m,2H)
1H−NMR:δ7.31(m,2H),7.73(m,4H),7.96(d,1H),8.10(d,1H),8.26(s,1H)
<ステップ1>(6−ブロモジベンゾ[b,d]チオフェン−4−イル)トリメチルシランの合成
1H−NMR:δ0.27(s,9H),7.48(m,4H),8.41(m,2H)
1H−NMR:δ0.26(s,9H),5.27(s,2H),6.89(d,1H),7.29(t,1H),7.52(m,2H),7.81(d,1H),8.39(d,1H)
1H−NMR:δ0.26(s,9H),6.45(d,1H),7.28(d,1H),7.56(m,3H),8.09(d,1H),8.41(d,1H),8.65(s,1H)
1H−NMR:δ6.45(d,1H),7.27(d,1H),7.54(m,3H),8.05(d,1H),8.40(d,1H),8.65(s,1H)
<ステップ1>(8−ブロモジベンゾ[b,d]チオフェン−2−イル)トリメチルシランの合成
1H−NMR:δ0.25(s,9H),7.48(m,2H),7.96(m,4H)
1H−NMR:δ0.26(s,9H),5.26(s,2H),7.48(m,3H),7.79(d,1H),7.96(d,1H),8.01(s,1H)
IC−45a−1の1H−NMR:δ0.26(s,9H),6.45(d,1H),7.27(d,1H),7.56(d,1H),7.82(m,2H),8.02(m,2H),8.65(s,1H)
IC−45b−1の1H−NMR:δ0.26(s,9H),6.44(d,1H),7.29(m,2H),7.53(d,1H),8.01(m,3H),8.65(s,1H)
1H−NMR:δ6.44(d,1H),7.28(t,1H),7.42(d,1H),7.83(m,4H),8.63(s,1H)
1H−NMR:δ6.45(d,1H),7.30(m,2H),7.45(d,1H),7.92(m,3H),8.61(s,1H)
<ステップ1>2−(ベンゾフラン−5−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランの合成
1H−NMR:δ1.25(s,12H),6.46(d,1H),7.28(d,1H),7.43(d,1H),7.53(d,1H),7.98(s,1H)
1H−NMR:δ6.45(d,1H),7.26(d,1H),7.42(d,1H),7.52(d,1H),7.66(t,1H),7.85(t,1H),7.96(s,1H),8.01(d,1H),8.06(t,1H)
1H−NMR:δ6.51(d,1H),7.27(d,1H),7.43(d,1H),7.54(d,1H),7.68(t,1H),7.86(t,1H),8.00(d,1H),8.05(t,1H),10.58(s,1H)
<ステップ1>2−(ベンゾフラン−6−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランの合成
1H−NMR:δ1.25(s,12H),6.46(d,1H),7.28(d,1H),7.43(d,1H),7.53(d,1H),7.98(s,1H)
1H−NMR:δ6.45(d,1H),7.26(d,1H),7.42(d,1H),7.52(d,1H),7.66(t,1H),7.85(t,1H),7.96(s,1H),8.01(d,1H),8.06(t,1H)
1H−NMR:δ6.51(d,1H),7.27(d,1H),7.43(d,1H),7.54(d,1H),7.68(t,1H),7.86(t,1H),8.00(d,1H),8.05(t,1H),10.58(s,1H)
<ステップ1>ジベンゾ[b,d]フラン−3−アミンの合成
1H−NMR:δ5.32(s,2H),6.33(d,1H),7.34(m,2H),7.43(s,1H),7.65(d,2H),7.89(d,1H)
1H−NMR:δ6.45(d,1H),7.13(d,1H),7.27(d,1H),7.35(m,2H),7.66(d,1H),7.88(d,2H),10.46(s,1H)
<ステップ1>5,5−ジメチル−5H−ジベンゾ[b,d]シロール−3−アミンの合成
1H−NMR:δ0.68(s,6H),5.31(s,2H),6.68(d,1H),6.80(s,1H),7.33(t,1H),7.52(d,1H),7.61(t,1H),7.64(d,1H),7.91(d,1H)
1H−NMR:δ0.66(s,6H),6.45(d,1H),7.27(d,1H),7.33(t,1H),7.52(d,1H),7.61(t,1H),7.79(d,1H),7.89(d,1H),7.97(d,1H),10.42(s,1H)
<ステップ1>5,5−ジフェニル−5H−ジベンゾ[b,d]シロール−3−アミンの合成
1H−NMR:δ5.33(s,2H),6.67(d,1H),6.81(s,1H),7.31(t,1H),7.37(m,4H),7.46(m,4H),7.54(m,3H),7.62(t,1H),7.66(d,1H),7.92(d,1H)
1H−NMR:δ6.44(d,1H),7.26(d,1H),7.35(m,5H),7.47(m,4H),7.53(m,3H),7.62(t,1H),7.78(d,1H),7.90(d,1H),7.96(d,1H),10.41(s,1H)
<ステップ1>IC−51の合成
1H−NMR:δ6.47(d,1H),7.15(d,1H),7.26(d,1H),7.36(m,2H),7.67(d,1H),7.89(d,2H),10.45(s,1H)
<ステップ1>2−(ベンゾ[b]セレノフェン−5−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランの合成
1H−NMR:δ1.26(s,12H),6.45(d,1H),7.27(d,1H),7.43(d,1H),7.54(d,1H),8.00(s,1H)
1H−NMR:δ6.44(d,1H),7.27(d,1H),7.43(d,1H),7.51(d,1H),7.65(t,1H),7.84(t,1H),7.94(s,1H),8.00(d,1H),8.05(t,1H)
1H−NMR:δ6.52(d,1H),7.26(d,1H),7.44(d,1H),7.55(d,1H),7.69(t,1H),7.85(t,1H),7.96(d,1H),8.03(t,1H),10.56(s,1H)
<ステップ1>2−(ベンゾ[b]セレノフェン−6−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランの合成
1H−NMR:δ1.24(s,12H),6.45(d,1H),7.28(d,1H),7.44(d,1H),7.57(d,1H),7.96(s,1H)
1H−NMR:δ6.46(d,1H),7.26(d,1H),7.43(d,1H),7.54(d,1H),7.67(t,1H),7.86(t,1H),7.93(s,1H),8.02(d,1H),8.08(t,1H)
1H−NMR:δ6.52(d,1H),7.27(d,1H),7.43(d,1H),7.52(d,1H),7.67(t,1H),7.85(t,1H),8.01(d,1H),8.09(t,1H),10.55(s,1H)
GC−Mass(理論値:452.13g/mol、測定値:452g/mol)
GC−Mass(理論値:378.09g/mol、測定値:378g/mol)
GC−Mass(理論値:436.19g/mol、測定値:436g/mol)
GC−Mass(理論値:586.24g/mol、測定値:586g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:452.57g/mol、測定値:452g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:454.55g/mol、測定値:454g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:682.83g/mol、測定値:682g/mol)
Inv−151−1の代わりに、Inv−155−1(2.58g、6.88mmol)を使用する以外は、合成例151と同様にして、目的化合物であるInv−155(3.99g、収率:85%)を得た。
GC−Mass(理論値:682.83g/mol、測定値:682g/mol)
GC−Mass(理論値:758.93g/mol、測定値:758g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:758.93g/mol、測定値:758g/mol)
GC−Mass(理論値:530.64g/mol、測定値:530g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:606.74g/mol、測定値:606g/mol)
GC−Mass(理論値:758.93g/mol、測定値:758g/mol)
GC−Mass(理論値:449.56g/mol、測定値:449g/mol)
2−ブロモフェニレンの代わりに、2−(4−ブロモフェニル)トリフェニレン(11.50g、30.0mmol)を使用する以外は、合成例165と同様にして、Inv−166(7.04g、収率:67%)を得た。
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:481.63g/mol、測定値:481g/mol)
GC−Mass(理論値:506.66g/mol、測定値:506g/mol)
GC−Mass(理論値:496.64g/mol、測定値:496g/mol)
GC−Mass(理論値:480.58g/mol、測定値:480g/mol)
GC−Mass(理論値:555.69g/mol、測定値:555g/mol)
GC−Mass(理論値:449.56g/mol、測定値:449g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:481.63g/mol、測定値:481g/mol)
GC−Mass(理論値:506.66g/mol、測定値:506g/mol)
GC−Mass(理論値:496.64g/mol、測定値:496g/mol)
GC−Mass(理論値:480.58g/mol、測定値:480g/mol)
GC−Mass(理論値:555.69g/mol、測定値:555g/mol)
GC−Mass(理論値:449.56g/mol、測定値:449g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:481.63g/mol、測定値:481g/mol)
GC−Mass(理論値:506.66g/mol、測定値:506g/mol)
GC−Mass(理論値:496.64g/mol、測定値:496g/mol)
GC−Mass(理論値:480.58g/mol、測定値:480g/mol)
GC−Mass(理論値:555.69g/mol、測定値:555g/mol)
GC−Mass(理論値:449.56g/mol、測定値:449g/mol)
GC−Mass(理論値:525.66g/mol、測定値:525g/mol)
GC−Mass(理論値:601.76g/mol、測定値:601g/mol)
GC−Mass(理論値:557.73g/mol、測定値:557g/mol)
GC−Mass(理論値:506.66g/mol、測定値:506g/mol)
GC−Mass(理論値:496.64g/mol、測定値:496g/mol)
GC−Mass(理論値:632.77g/mol、測定値:632g/mol)
GC−Mass(理論値:707.88g/mol、測定値:707g/mol)
GC−Mass(理論値:677.85g/mol、測定値:677g/mol)
GC−Mass(理論値:753.95g/mol、測定値:753g/mol)
GC−Mass(理論値:677.85g/mol、測定値:677g/mol)
GC−Mass(理論値:709.92g/mol、測定値:709g/mol)
GC−Mass(理論値:582.76g/mol、測定値:582g/mol)
GC−Mass(理論値:572.74g/mol、測定値:572g/mol)
GC−Mass(理論値:556.67g/mol、測定値:556g/mol)
GC−Mass(理論値:707.88g/mol、測定値:707g/mol)
GC−Mass(理論値:514.18g/mol、測定値:514g/mol)
GC−Mass(理論値:514.18g/mol、測定値:514g/mol)
GC−Mass(理論値:514.18g/mol、測定値:514g/mol)
GC−Mass(理論値:556.21g/mol、測定値:556g/mol)
GC−Mass(理論値:680.24g/mol、測定値:680g/mol)
GC−Mass(理論値:578.10g/mol、測定値:578g/mol)
GC−Mass(理論値:578.10g/mol、測定値:578g/mol)
GC−Mass(理論値:578.10g/mol、測定値:578g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
C−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:665.26g/mol、測定値:665g/mol)
GC−Mass(理論値:705.29g/mol、測定値:705g/mol)
GC−Mass(理論値:695.21g/mol、測定値:695g/mol)
GC−Mass(理論値:754.28g/mol、測定値:754g/mol)
合成例1〜26及び111〜114で合成した化合物Inv−1〜Inv26及びInv−111〜Inv114を、常法で高純度昇華精製を行った後、次の過程に応じて緑色有機電界発光素子を製作した。
発光層の形成時に、発光ホスト材料として、化合物Inv−1の代わりにCBPを使用する以外は、実施例1と同様にして、緑色有機電界発光素子を製作した。
実施例1〜30及び比較例1で製作したそれぞれの緑有機電界発光素子に関して、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表1に示す。
合成例27〜110で合成した化合物Inv−27〜Inv110を、常法で高純度昇華精製を行った後、上述の実施例1と同様にして、緑色有機電界発光素子を製作した。
実施例31〜114及び上述の比較例1で製作したそれぞれの緑色有機電界発光素子に関して、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表2に示す。
合成例115〜212で合成した化合物Inv−115〜Inv212を、常法で高純度昇華精製を行った後、次の過程に応じて赤色有機電界発光素子を製作した。
発光層の形成時に、発光ホスト材料として、化合物Inv−115の代わりに、CBPを使用する以外は、実施例115と同様にして、赤色有機電界発光素子を製作した。
実施例115〜212及び比較例2で製作したそれぞれの赤色有機電界発光素子に関して、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表3に示す。
合成例115〜219で合成した化合物Inv−115〜Inv219を、常法で高純度昇華精製を行った後、上述の実施例1と同様にして、緑色有機電解発光素子を製作した。
実施例213〜317及び比較例1で製作したそれぞれの緑色有機電界発光素子に関して、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表4に示す。
Claims (13)
- 下記化1で示される化合物:
式中、R1及びR2は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基及びC6〜C60のアリールアミン基からなる群から選択され、
Y1 及びY 2 は、下記化2で示される縮合環を形成し、Y 3 及びY4は、それぞれ独立に、CR3であり、
式中、Y5〜Y8は、それぞれ独立に、CR4であり、点線は、上記化1の化合物と縮合される部位を意味し、
X1及びX2は、それぞれ独立に、O、S、Se、及びN(Ar1 )からなる群から選択され、X1及びX2の少なくとも1つは、N(Ar1)であり、
R3及びR4は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記Ar 1 は、C 6〜C60のアリール基、及び、核原子数5〜60のヘテロアリール基からなる群から選択され、
前記R1〜R4 におけるC1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基、ならびに、Ar 1 におけるC 6 〜C 60 のアリール基及び核原子数5〜60のヘテロアリール基は、それぞれ独立に、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1つ以上の置換基で置換されることができる。 - 前記化1で示される化合物は、下記化1a及び1fで示される化学物からなる群から選択されるものであることを特徴とする請求項1に記載の化合物:
- 前記R1〜R4は、それぞれ独立に、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基及びC6〜C60のアリールアミン基からなる群から選択されるものであることを特徴とする請求項1に記載の化合物。
- 前記X1及びX2は、いずれもN(Ar1)であることを特徴とする請求項1に記載の化合物。
- 前記化1で示される化合物は、下記化3で示される化合物であることを特徴とする請求項4に記載の化合物:
式中、R1、R2及びY 3 〜Y4は、請求項1での定義と同じであり、Y1とY 2 は、下記化4で示される縮合環を形成し、
式中、Y5〜Y8は、請求項1での定義と同じであり、点線は、前記化3の化合物と縮合される部位を意味し、
Ar1は、請求項1での定義と同じであり、
Ra及びRbは、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記Ra及びRbにおけるC1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基は、それぞれ独立に、重水素、ハロゲン、シアノ基、ニトロ基、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1つ以上の置換基で置換されることができ、
n及びmは、それぞれ独立に、0〜5の整数であり、但し、n+mは、少なくとも1以上である。 - 前記化1で示される化合物は、下記化5で示される化合物であることを特徴とする請求項4に記載の化合物:
式中、R1、R2及びY 3 〜Y4は、請求項1での定義と同じであり、Y1とY 2 は、下記化6で示される縮合環を形成し、
式中、Y5〜Y8は、請求項1での定義と同じであり、点線は、前記化5の化合物と縮合される部位を意味し、
Z1〜Z6は、それぞれ独立に、N又はCAr6であり、
前記Ar6、A及びBは、それぞれ独立に、C1〜C40のアルキル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C3〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C2〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
r及びsは、それぞれ、0〜5の整数(但し、r+sは、少なくとも1以上)であり、
p及びqは、それぞれ、0〜3の整数である。 - 前記化5で示される化合物は、下記化5a及び5fで示される化合物からなる群から選択されるものであることを特徴とする請求項6に記載の化合物:
- 前記Ar6、A及びBは、それぞれ独立に、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基及びC6〜C60のアリールアミン基からなる群から選択されるものであることを特徴とする請求項6に記載の化合物。
- 前記X1がSである時、X2は、N(Ar1)であり、前記X2がSである時、X1は、N(Ar1)であることを特徴とする請求項1に記載の化合物。
- 前記化1で示される化合物は、下記化6a、6f、6g及び6lで示される化合物からなる群から選択されるものであることを特徴とする請求項9に記載の化合物。
- (i)陽極、(ii)陰極、及び(iii)前記陽極と陰極との間に介在した1層以上の有機物層を含む有機電界発光素子であって、
前記有機物層のうちの少なくとも1つは、請求項1〜10のいずれか1項に記載の化合物を含むことを特徴とする有機電界発光素子。 - 前記化合物を含む有機物層は、正孔注入層、正孔輸送層、電子注入層、電子輸送層及び発光層からなる群から選択されるものであることを特徴とする請求項11に記載の有機電界発光素子。
- 前記化合物は、発光層の燐光ホストとして使用されることを特徴とする請求項11に記載の有機電界発光素子。
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Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102080299B1 (ko) * | 2012-02-14 | 2020-02-21 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US9260436B2 (en) * | 2012-06-22 | 2016-02-16 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound |
JP6022690B2 (ja) * | 2012-08-10 | 2016-11-09 | ドゥーサン コーポレイション | 新規な化合物及びこれを含む有機電界発光素子 |
KR101452579B1 (ko) | 2012-08-17 | 2014-10-21 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101537436B1 (ko) * | 2012-08-17 | 2015-07-17 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2014082705A1 (de) * | 2012-11-30 | 2014-06-05 | Merck Patent Gmbh | Elektronische vorrichtung |
KR101506793B1 (ko) * | 2013-07-16 | 2015-03-27 | 주식회사 두산 | 유기 전계 발광 소자 |
CN105408448B (zh) | 2013-07-30 | 2018-11-02 | 默克专利有限公司 | 用于电子器件的材料 |
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KR101571597B1 (ko) * | 2013-08-05 | 2015-11-24 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101571596B1 (ko) * | 2013-08-05 | 2015-11-24 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101742359B1 (ko) * | 2013-12-27 | 2017-05-31 | 주식회사 두산 | 유기 전계 발광 소자 |
KR102201319B1 (ko) * | 2014-01-14 | 2021-01-11 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
WO2015165563A1 (de) * | 2014-04-30 | 2015-11-05 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR102364220B1 (ko) | 2014-12-03 | 2022-02-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN105845831B (zh) | 2015-01-30 | 2019-07-05 | 三星显示有限公司 | 有机发光装置 |
KR102456076B1 (ko) * | 2015-09-03 | 2022-10-19 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102507373B1 (ko) * | 2015-12-21 | 2023-03-08 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR102589223B1 (ko) * | 2016-11-29 | 2023-10-16 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
KR101864663B1 (ko) * | 2017-11-17 | 2018-07-13 | 덕산네오룩스 주식회사 | 오원자 헤테로 고리를 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
KR102095837B1 (ko) * | 2018-06-28 | 2020-04-01 | 영남대학교 산학협력단 | 카바졸 유도체의 신규한 제조방법, 이로 제조된 신규한 카바졸 유도체, 이들을 포함하는 조성물 및 유기 발광 다이오드 소재 |
KR102606283B1 (ko) * | 2018-07-09 | 2023-11-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN109970748A (zh) * | 2019-04-22 | 2019-07-05 | 吉林奥来德光电材料股份有限公司 | 一种有机发光化合物及其制备方法和器件 |
CN112480077B (zh) * | 2020-11-17 | 2022-04-12 | 上海和辉光电股份有限公司 | 一种用于有机发光的化合物及其应用 |
CN115304622A (zh) * | 2022-08-08 | 2022-11-08 | 南昌航空大学 | 一种芴类分子锁小分子阴极界面层及其制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2012626A1 (en) | 1990-03-20 | 1991-09-20 | Kenneth W. Bair | Hetero polycyclic biocidal compounds, their synthesis and intermediates therefor, formulations containing them, and their use in medicine |
JP3260310B2 (ja) * | 1997-11-04 | 2002-02-25 | ティーディーケイ株式会社 | シート型電極・電解質構造体の製造方法 |
JP3924869B2 (ja) | 1997-11-05 | 2007-06-06 | 東レ株式会社 | 有機積層薄膜発光素子 |
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DE102005040411A1 (de) | 2005-08-26 | 2007-03-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
FR2933409B1 (fr) * | 2008-07-03 | 2010-08-27 | Centre Nat Rech Scient | NOUVEAUX PYRROLO °2,3-a! CARBAZOLES ET LEUR UTILISATION COMME INHIBITEURS DES KINASES PIM |
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EP2415773B1 (en) * | 2009-03-30 | 2016-02-17 | Duk San Neolux Co., Ltd. | Organic electronic device, compounds for same, and terminal |
KR20100131271A (ko) | 2009-06-05 | 2010-12-15 | 덕산하이메탈(주) | 카바졸과 플루오렌이 결합하여 고리를 형성한 화합물 및 이를 이용한 유기전기소자, 그 단말 |
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KR20110117549A (ko) * | 2010-04-21 | 2011-10-27 | 덕산하이메탈(주) | 다이벤조사이오펜과 아릴아민 유도체를 가지는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
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JP2015531758A (ja) * | 2012-08-10 | 2015-11-05 | ドゥーサン コーポレイション | 有機発光化合物及びこれを用いた有機電界発光素子 |
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KR101488565B1 (ko) | 2015-02-03 |
JP2016040292A (ja) | 2016-03-24 |
US10038146B2 (en) | 2018-07-31 |
JP2015502953A (ja) | 2015-01-29 |
US20140374724A1 (en) | 2014-12-25 |
JP6320360B2 (ja) | 2018-05-09 |
KR20130064001A (ko) | 2013-06-17 |
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