WO2014122895A1 - ジアザトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 - Google Patents
ジアザトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2014122895A1 WO2014122895A1 PCT/JP2014/000415 JP2014000415W WO2014122895A1 WO 2014122895 A1 WO2014122895 A1 WO 2014122895A1 JP 2014000415 W JP2014000415 W JP 2014000415W WO 2014122895 A1 WO2014122895 A1 WO 2014122895A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 148
- QKHBRTOZTSOCKN-UHFFFAOYSA-N phenanthro[9,10-c]pyridazine Chemical group N1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 QKHBRTOZTSOCKN-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 79
- 230000003111 delayed effect Effects 0.000 claims abstract description 30
- 239000012044 organic layer Substances 0.000 claims abstract description 14
- 239000000470 constituent Substances 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims description 137
- 125000004432 carbon atom Chemical group C* 0.000 claims description 136
- -1 di-substituted amino group Chemical group 0.000 claims description 117
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 108
- 239000010410 layer Substances 0.000 claims description 105
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 91
- 125000003277 amino group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004104 aryloxy group Chemical group 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- 125000004431 deuterium atom Chemical group 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 26
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000004434 sulfur atom Chemical group 0.000 claims description 24
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 22
- 238000005401 electroluminescence Methods 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 12
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 52
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 16
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 238000009423 ventilation Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 11
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 10
- 125000004623 carbolinyl group Chemical group 0.000 description 10
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 10
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 125000002541 furyl group Chemical group 0.000 description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 10
- 125000001041 indolyl group Chemical group 0.000 description 10
- 125000005956 isoquinolyl group Chemical group 0.000 description 10
- 125000001725 pyrenyl group Chemical group 0.000 description 10
- 125000004076 pyridyl group Chemical group 0.000 description 10
- 125000000168 pyrrolyl group Chemical group 0.000 description 10
- 125000005493 quinolyl group Chemical group 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 125000001544 thienyl group Chemical group 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 125000003226 pyrazolyl group Chemical group 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 8
- 238000007872 degassing Methods 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000005561 phenanthryl group Chemical group 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 7
- 229940125773 compound 10 Drugs 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 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 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 5
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 5
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 5
- PODXMJZWPPXECD-UHFFFAOYSA-N 6,11-dibromophenanthro[9,10-b]pyrazine Chemical group C1=CN=C2C3=CC(Br)=CC=C3C3=CC=C(Br)C=C3C2=N1 PODXMJZWPPXECD-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 229940125797 compound 12 Drugs 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 229940125846 compound 25 Drugs 0.000 description 5
- 229940125877 compound 31 Drugs 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- LZCWFVGKBUCTOU-UHFFFAOYSA-N 7,10-dibromophenanthro[9,10-b]pyrazine Chemical group C1=CN=C2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C3C2=N1 LZCWFVGKBUCTOU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003609 aryl vinyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical group C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 3
- 150000004322 quinolinols Chemical class 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000005580 triphenylene group Chemical group 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
- ZABORCXHTNWZRV-UHFFFAOYSA-N 10-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]phenoxazine Chemical compound O1C2=CC=CC=C2N(C2=CC=C(C=C2)C2=NC(=NC(=N2)C2=CC=CC=C2)C2=CC=CC=C2)C2=C1C=CC=C2 ZABORCXHTNWZRV-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 description 2
- LTZIIBSPYWTOQV-UHFFFAOYSA-N 2,7-dibromophenanthrene-9,10-dione Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3C(=O)C(=O)C2=C1 LTZIIBSPYWTOQV-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- WPEJBJRFPBMVGJ-UHFFFAOYSA-N 3,6-dibromophenanthrene-9,10-dione Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3C(=O)C(=O)C2=C1 WPEJBJRFPBMVGJ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
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- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical class C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
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- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- 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
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
1993年にプリンストン大学のM.A.Baldoらは、イリジウム錯体を用いた燐光発光素子によって8%の外部量子効率を実現させた。
また、熱活性化遅延蛍光(TADF)による発光を利用する素子も開発されている。2011年に九州大学の安達らは、熱活性化遅延蛍光材料を用いた素子によって5.3%の外部量子効率を実現させた(例えば、非特許文献1参照)。
そこで、遅延蛍光を示す材料を利用する有機エレクトロルミネッセンス素子が考えられる。ある種の蛍光物質は、系間交差などにより励起三重項状態へとエネルギーが遷移した後、三重項-三重項消滅あるいは熱エネルギーの吸収により、励起一重項状態に逆系間交差され蛍光を放射する。有機エレクトロルミネッセンス素子においては、後者の熱活性化型の遅延蛍光を示す材料が特に有用であると考えられる。ここで、有機エレクトロルミネッセンス素子に遅延蛍光材料を利用した場合、励起一重項状態の励起子は通常通り蛍光を放射する。一方、励起三重項状態の励起子は、デバイスが発する熱を吸収して励起一重項へ系間交差され蛍光を放射する。この場合、励起一重項からの発光であるため蛍光と同波長での発光でありながら、励起三重項状態から励起一重項状態への逆系間交差により、生じる光の寿命、すなわち発光寿命は通常の蛍光や燐光よりも長くなるため、これらよりも遅延した蛍光として観察される。これを遅延蛍光として定義できる。このような熱活性化型の励起子移動機構を用いること、すなわち、キャリア注入後に熱エネルギーの吸収を経ることにより、通常は25%しか生成しなかった励起一重項状態の化合物の比率を25%以上に引き上げることが可能となる。100℃未満の低い温度でも強い蛍光および遅延蛍光を発する化合物を用いれば、デバイスの熱で充分に励起三重項状態から励起一重項状態への系間交差が生じ、遅延蛍光を放射することから、発光効率が飛躍的に向上する(例えば、特許文献1および特許文献2参照)。
また、これらの基が有する置換基としては、カルバゾリル基、芳香族炭化水素基で置換されたジ置換アミノ基が好ましく、カルバゾリル基、ジフェニルアミノ基がより好ましい。
また、これらの基が有する置換基としては、カルバゾリル基、芳香族炭化水素基で置換されたジ置換アミノ基が好ましく、カルバゾリル基、ジフェニルアミノ基がより好ましい。
また、9,10-フェナントレンキノンとエチレンジアミンを反応させることによって、ジアザトリフェニレンをまず合成した後に、N-ブロモコハク酸イミドなどによるブロモ化を行うことによって、ブロモ基を有するジアザトリフェニレン誘導体を合成し、上記同様、Suzukiカップリングなどのクロスカップリング反応もしくはブッフバルド・ハートウィッグ反応などの縮合反応を行うことによって、本発明のジアザトリフェニレン環構造を有する化合物を合成することができる。
尚、ブロモ化の試薬、条件を変更することによって、置換位置の異なるブロモ置換体を得ることができる。
<6,11-ビス(フェノキサジン-10-イル)-1,4-ジアザトリフェニレン(化合物1)の合成>
窒素置換した反応容器に、9,10-フェナントレンキノン10g、濃硫酸100mLを加え、窒素を通気した。N-ブロモコハク酸イミド18gを加え、室温で2時間攪拌した。水50mLを加えた後、氷水600mLに加えた。析出する固体をろ過によって採取し、酢酸エチル100mLを用いた加熱還流洗浄を行った後、真空乾燥を行うことによって、2,7-ジブロモ-9,10-フェナントレンキノンの黄色固体(収率73%)を得た。
<6,11-ビス(フェノチアジン-10-イル)-1,4-ジアザトリフェニレン(化合物2)の合成>
実施例1で合成した6,11-ジブロモ-1,4-ジアザトリフェニレン2.0g、炭酸カリウム3.0g、フェノチアジン3.2g、トリ-tert-ブチルホスフィン0.1g、トルエン60mLを窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、酢酸パラジウム60mgを加え、攪拌しながら加熱し、還流を20時間行った。放冷した後、析出する固体をろ過によって採取し、メタノールを用いた加熱還流洗浄、続いて、アセトンを用いた加熱還流洗浄を行った後、真空乾燥を行うことによって、6,11-ビス(フェノチアジン-10-イル)-1,4-ジアザトリフェニレン(化合物2)の灰色固体(収率76%)を得た。
<6,11-ビス(9,9-ジメチルアクリダン-10-イル)-1,4-ジアザトリフェニレン(化合物4)の合成>
実施例1で合成した6,11-ジブロモ-1,4-ジアザトリフェニレン0.9g、炭酸カリウム0.9g、10-H-9,9-ジメチルアクリダン1.0g、トリ-tert-ブチルホスフィン0.05g、トルエン20mLを窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、酢酸パラジウム30mgを加え、攪拌しながら加熱し、還流を18時間行った。放冷した後、析出する固体をろ過によって採取し、メタノールを用いた加熱還流洗浄、続いて、アセトンを用いた加熱還流洗浄を行った後、1,2-ジクロロベンゼンを用いた再結晶による精製を行うことによって、6,11-ビス(9,9-ジメチルアクリダン-10-イル)-1,4-ジアザトリフェニレン(化合物4)の灰色粉末(収率30%)を得た。
<6,11-ビス{3-(ジフェニルアミノ)カルバゾール-9-イル}-1,4-ジアザトリフェニレン(化合物25)の合成>
実施例1で合成した6,11-ジブロモ-1,4-ジアザトリフェニレン1.0g、炭酸カリウム0.7g、3-(ジフェニルアミノ)カルバゾール2.1g、トリ-tert-ブチルホスフィン0.05g、トルエン50mLを窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、酢酸パラジウム30mgを加え、攪拌しながら加熱し、還流を7時間行った。放冷した後、析出する固体をろ過によって採取し、シリカゲルカラムクロマトグラフィーによる精製を行うことによって、6,11-ビス{3-(ジフェニルアミノ)カルバゾール-9-イル}-1,4-ジアザトリフェニレン(化合物25)の黄色粉末(収率70%)を得た。
<7,10-ビス{3-(ジフェニルアミノ)カルバゾール-9-イル}-1,4-ジアザトリフェニレン(化合物31)の合成>
窒素置換した反応容器に、9,10-フェナントレンキノン50g、過酸化ベンゾイル2.5g、ニトロベンゼン250mLを加え、窒素を通気した。臭素83gを加えて加熱し、還流下で2時間攪拌した。放冷後、エタノール250mLを加え、析出する固体をろ過によって採取した。固体をエタノールを用いて洗浄した後、真空乾燥を行うことによって、3,6-ジブロモ-9,10-フェナントレンキノンの黄色固体(収率70%)を得た。
<7,10-ビス(フェノキサジン-10-イル)-1,4-ジアザトリフェニレン(化合物10)の合成>
実施例5で合成した7,10-ジブロモ-1,4-ジアザトリフェニレン1.0g、ナトリウム-tert-ブトキシド0.7g、フェノキサジン1.4g、トリ-tert-ブチルホスフィン0.05g、トルエン60mLを窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、トリス(ジベンジリデンアセトン)ジパラジウムクロロホルム接合体0.06gを加え、攪拌しながら加熱し、還流を24時間行った。放冷した後、析出する固体をろ過によって採取し、シリカゲルカラムクロマトグラフィーによる精製を行うことによって、7,10-ビス(フェノキサジン-10-イル)-1,4-ジアザトリフェニレン(化合物10)の黄色粉末(収率90%)を得た。
<7,10-ビス(9,9-ジメチルアクリダン-10-イル)-1,4-ジアザトリフェニレン(化合物12)の合成>
実施例5で合成した7,10-ジブロモ-1,4-ジアザトリフェニレン1.0g、ナトリウム-tert-ブトキシド0.6g、10-H-9,9-ジメチルアクリダン1.6g、トリ-tert-ブチルホスフィン0.07g、トルエン80mL窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、トリス(ジベンジリデンアセトン)ジパラジウムクロロホルム接合体0.07gを加え、攪拌しながら加熱し、還流を18時間行った。放冷した後、析出する固体をろ過によって採取し、シリカゲルカラムクロマトグラフィーによる精製を行うことによって、7,10-ビス(9,9-ジメチルアクリダン-10-イル)-1,4-ジアザトリフェニレン(化合物12)の黄色粉末(収率60%)を得た。
<6,11-ビス(9-カルバゾリル)-1,4-ジアザトリフェニレン(比較化合物A)の合成>
実施例1で合成した6,11-ジブロモ-1,4-ジアザトリフェニレン1.5g、炭酸カリウム1.3g、カルバゾール1.8g、トリ-tert-ブチルホスフィン0.08g、トルエン40mLを窒素置換した反応容器に加え、窒素を通気した。減圧脱気した後、酢酸パラジウム40mgを加え、攪拌しながら加熱し、還流を17時間行った。放冷した後、析出する固体をろ過によって採取し、メタノールを用いた加熱還流洗浄、続いて、アセトンを用いた加熱還流洗浄を行った後、真空乾燥を行うことによって、下記構造式の6,11-ビス(9-カルバゾリル)-1,4-ジアザトリフェニレン(比較化合物A)の灰色粉末(収率74%)を得た。
本発明の化合物を用いて、ITO基板の上に膜厚100nmの蒸着膜を作製して、大気中光電子分光装置(理研計器製、AC-3型)で仕事関数を測定した。
仕事関数
本発明実施例1の化合物 5.60eV
本発明実施例3の化合物 5.80eV
本発明実施例5の化合物 5.70eV
本発明実施例6の化合物 5.70eV
本発明実施例7の化合物 5.90eV
CBP 6.00eV
本発明実施例1の化合物(化合物1)について、10-5mol/Lのトルエン溶液を調製した。このトルエン溶液について、窒素を通気しながら300Kで紫外光を照射したところ、ピーク波長が547nmの蛍光を観測した。
また、このトルエン溶液について、窒素の通気前後における小型蛍光寿命測定装置(浜松ホトニクス(株)製Quantaurus-tau)を用いた時間分解スペクトルを測定したところ、発光寿命が0.055μsの蛍光、そして発光寿命が0.703μsおよび9.25μsの遅延蛍光を観測した。
また、このトルエン溶液について、窒素の通気前後におけるフォトルミネッセンス量子効率を絶対PL量子収率測定装置(浜松ホトニクス(株)製Quantaurus-QY)を用いて、300Kで測定したところ、窒素通気前で3.5%(4.0%)、窒素通気後で14.0%(23.9%)であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例2の化合物(化合物2)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が564nmの蛍光を観測し、発光寿命が0.01μsの蛍光と、発光寿命が0.052μsおよび4.2μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で1.9%、窒素通気後で7.5%であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例3の化合物(化合物4)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が503nmの蛍光を観測し、発光寿命が0.047μsの蛍光と、発光寿命が14.3μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で6.8%、窒素通気後で25.8%であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例4の化合物(化合物25)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が544nmの蛍光を観測し、発光寿命が0.046μsの蛍光と、発光寿命が1.21μsおよび12.77μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で10.4%、窒素通気後で47.4%であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例5の化合物(化合物31)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が532nmの蛍光を観測し、発光寿命が0.05μsの蛍光と、発光寿命が18.10μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で29.3%、窒素通気後で77.1%であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例6の化合物(化合物10)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が545nmの蛍光を観測し、発光寿命が0.04μsの蛍光と、発光寿命が3.42μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で3.7%、窒素通気後で30.2%であった。
実施例9において、本発明実施例1の化合物(化合物1)に代えて本発明実施例7の化合物(化合物12)の10-5mol/Lのトルエン溶液を調製し、同様の操作で特性評価を行った。その結果、ピーク波長が490nmの蛍光を観測し、発光寿命が0.04μsの蛍光と、発光寿命が22.8μsの遅延蛍光を観測した。
また、PL量子効率は、窒素通気前で10.2%、窒素通気後で35.6%であった。
有機EL素子は、図9に示すように、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔輸送層3、発光層4、電子輸送層5、電子注入層6、陰極(アルミニウム電極)7の順に蒸着して作製した。
続いて、透明陽極2を覆うように正孔輸送層3として、NPDを蒸着速度2.0Å/secで膜厚35nmとなるように形成した。この正孔輸送層3の上に、発光層4としてCBPと本発明実施例1の化合物(化合物1)を、蒸着速度比がCBP:本発明実施例1の化合物(化合物1)=95:5となる蒸着速度で二元蒸着を行い、膜厚15nmとなるように形成した。この発光層4の上に、電子輸送層5として前記TPBIを蒸着速度2.0Å/secで膜厚65nmとなるように形成した。この電子輸送層5の上に、電子注入層6としてフッ化リチウムを蒸着速度0.1Å/secで膜厚0.8nmとなるように形成した。最後に、アルミニウムを膜厚70nmとなるように蒸着して陰極7を形成した。作製した有機EL素子について、大気中、常温で特性測定を行った。
実施例16において、発光層4の材料を、CBPと本発明実施例1の化合物(化合物1)からmCPと本発明実施例6の化合物(化合物10)に代え、蒸着速度比がmCP:本発明実施例6の化合物(化合物10)=95:5となる蒸着速度で二元蒸着を行った以外は、同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行った。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例16における発光層4の材料を、実施例1の化合物(化合物1)から比較合成例1の化合物(比較化合物A)に代え、実施例16と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行った。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
2 透明陽極
3 正孔輸送層
4 発光層
5 電子輸送層
6 電子注入層
7 陰極
Claims (15)
- 下記一般式(1)で表されるジアザトリフェニレン環構造を有する化合物。
(式中、Xは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、Yは水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、R1~R8は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) - 下記一般式(1-1)で表される請求項1記載のジアザトリフェニレン環構造を有する化合物。
(式中、Xは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、Yは水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、R1~R8は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) - 下記一般式(1-2)で表される請求項1記載のジアザトリフェニレン環構造を有する化合物。
(式中、Xは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、Yは水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、R1~R8は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) - 下記一般式(1-3)で表される請求項1記載のジアザトリフェニレン環構造を有する化合物。
(式中、Xは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、Yは水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、R1~R8は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) - 下記一般式(1-4)で表される請求項1記載のジアザトリフェニレン環構造を有する化合物。
(式中、Xは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、Yは水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表し、R1~R8は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。) - 前記一般式(1)において、Xが置換もしくは無置換のフェノキサジニル基、フェノチアジニル基、アクリジニル基、フェナジニル基、または芳香族炭化水素基もしくは縮合多環芳香族基で置換されたジ置換アミノ基を置換基として有するカルバゾリル基から選ばれる1価基である、請求項1記載のジアザトリフェニレン環構造を有する化合物。
- 前記一般式(1)において、Yが置換もしくは無置換のフェノキサジニル基、フェノチアジニル基、アクリジニル基、フェナジニル基、または芳香族炭化水素基もしくは縮合多環芳香族基で置換されたジ置換アミノ基を置換基として有するカルバゾリル基から選ばれる1価基である、請求項1記載のジアザトリフェニレン環構造を有する化合物。
- 前記一般式(1)において、XおよびYが置換もしくは無置換のフェノキサジニル基、フェノチアジニル基、アクリジニル基、フェナジニル基、または芳香族炭化水素基もしくは縮合多環芳香族基で置換されたジ置換アミノ基を置換基として有するカルバゾリル基から選ばれる1価基である、請求項1記載のジアザトリフェニレン環構造を有する化合物。
- 前記請求項1に記載のジアザトリフェニレン環構造を有する化合物からなる発光材料。
- 遅延蛍光を放射する請求項9に記載の発光材料。
- 一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、前記請求項1に記載のジアザトリフェニレン環構造を有する化合物が、少なくとも1つの有機層の構成材料として用いられている有機エレクトロルミネッセンス素子。
- 前記した有機層が発光層である請求項11記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が遅延蛍光を放射する請求項11記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が電子輸送層である請求項11記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が正孔阻止層である請求項11記載の有機エレクトロルミネッセンス素子。
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US11101440B2 (en) | 2015-07-01 | 2021-08-24 | Kyushu University, National University Corporation | Organic electroluminescent device |
JP2017054972A (ja) * | 2015-09-10 | 2017-03-16 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置、照明装置、π共役系化合物、及び発光性薄膜 |
US11335872B2 (en) | 2016-09-06 | 2022-05-17 | Kyulux, Inc. | Organic light-emitting device |
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WO2023053835A1 (ja) | 2021-09-28 | 2023-04-06 | 株式会社Kyulux | 化合物、組成物、ホスト材料、電子障壁材料および有機発光素子 |
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CN105121428B (zh) | 2019-12-24 |
US20160064676A1 (en) | 2016-03-03 |
JP5614568B1 (ja) | 2014-10-29 |
CN105121428A (zh) | 2015-12-02 |
US10032995B2 (en) | 2018-07-24 |
TW201434828A (zh) | 2014-09-16 |
JPWO2014122895A1 (ja) | 2017-01-26 |
TWI641604B (zh) | 2018-11-21 |
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