WO2012147330A1 - アクリダ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
アクリダ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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- WO2012147330A1 WO2012147330A1 PCT/JP2012/002789 JP2012002789W WO2012147330A1 WO 2012147330 A1 WO2012147330 A1 WO 2012147330A1 JP 2012002789 W JP2012002789 W JP 2012002789W WO 2012147330 A1 WO2012147330 A1 WO 2012147330A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 109
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical group C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000000463 material Substances 0.000 claims abstract description 60
- 238000002347 injection Methods 0.000 claims abstract description 26
- 239000007924 injection Substances 0.000 claims abstract description 26
- 239000012044 organic layer Substances 0.000 claims abstract description 25
- 239000000470 constituent Substances 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 96
- -1 biphenylyl group Chemical group 0.000 claims description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 20
- 238000005401 electroluminescence Methods 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004431 deuterium atom Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 239000010409 thin film Substances 0.000 abstract description 20
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 239000012043 crude product Substances 0.000 description 16
- 125000001544 thienyl group Chemical group 0.000 description 16
- 238000005259 measurement Methods 0.000 description 15
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 14
- 125000002541 furyl group Chemical group 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229940125898 compound 5 Drugs 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 8
- 125000005561 phenanthryl group Chemical group 0.000 description 8
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 7
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000004623 carbolinyl group Chemical group 0.000 description 7
- 229940126208 compound 22 Drugs 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- 125000001041 indolyl group Chemical group 0.000 description 7
- 230000001678 irradiating effect Effects 0.000 description 7
- 125000005956 isoquinolyl group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 7
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 7
- 125000003226 pyrazolyl group Chemical group 0.000 description 7
- 125000001725 pyrenyl group Chemical group 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000005493 quinolyl group Chemical group 0.000 description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 4
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 4
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006880 cross-coupling reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 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 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003609 aryl vinyl group Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 229940126179 compound 72 Drugs 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000004322 quinolinols Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 2
- LMSYNIQUNFATNO-UHFFFAOYSA-N 10-(9,9-dimethylfluoren-2-yl)-9,9-dimethyl-2,7-bis(4-phenylphenyl)acridine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C1=CC=2)C3=CC=C(C=4C=CC(=CC=4)C=4C=CC=CC=4)C=C3C(C)(C)C1=CC=2C(C=C1)=CC=C1C1=CC=CC=C1 LMSYNIQUNFATNO-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- MRQNYVWJDKMEDN-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethyl-10-(4-phenylphenyl)acridine Chemical compound C12=CC=C(Br)C=C2C(C)(C)C2=CC(Br)=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1 MRQNYVWJDKMEDN-UHFFFAOYSA-N 0.000 description 2
- 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 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
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- IKXSQGYLHMGILI-UHFFFAOYSA-N 9,9-dimethyl-2,7-diphenyl-10h-acridine Chemical compound C1=C2C(C)(C)C3=CC(C=4C=CC=CC=4)=CC=C3NC2=CC=C1C1=CC=CC=C1 IKXSQGYLHMGILI-UHFFFAOYSA-N 0.000 description 2
- LDRPUFYTGSQURN-UHFFFAOYSA-N 9,9-dimethyl-2-phenyl-7,10-bis(4-phenylphenyl)acridine Chemical compound C12=CC=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)C=C2C(C)(C)C2=CC(C=3C=CC=CC=3)=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1 LDRPUFYTGSQURN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UBASCOPZFCGGAV-UHFFFAOYSA-N 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 UBASCOPZFCGGAV-UHFFFAOYSA-N 0.000 description 2
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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
- 239000003960 organic solvent Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000000171 quenching effect Effects 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
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 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 1
Images
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Definitions
- the present invention relates to a compound suitable for an organic electroluminescence element, which is a self-luminous element suitable for various display devices, and to the element. Specifically, the present invention relates to a compound having an acridan ring structure, and organic electroluminescence using the compound. The present invention relates to a luminescence element.
- organic electroluminescence elements are self-luminous elements, they have been actively researched because they are brighter and more visible than liquid crystal elements, and can display clearly.
- organic electroluminescence elements using organic materials practical by developing a laminated structure element that shares various roles with each material. They are composed of a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, Was injected into the phosphor layer to emit light, whereby high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
- Non-Patent Document 2 the use of triplet excitons has been attempted for the purpose of further improving the luminous efficiency, and the use of phosphorescent emitters has been studied (for example, see Non-Patent Document 2).
- the light emitting layer can also be prepared by doping a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
- a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
- the light injected from both electrodes recombines in the light emitting layer to obtain light emission.
- Improve the probability of recombination of holes and electrons by increasing the hole injection property and blocking the electron injected from the cathode, and further confine excitons generated in the light emitting layer
- high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
- the heat resistance and amorphous nature of the material are important for the lifetime of the element.
- thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated.
- the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
- NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
- Amine derivatives have been known (see, for example, Patent Document 1 and Patent Document 2).
- NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-Patent Document 3).
- arylamine compounds having a substituted acridan structure represented by the following formula for example, Compound A and Compound B have been proposed. (For example, see Patent Documents 3 and 4).
- JP-A-8-48656 Japanese Patent No. 3194657 WO2006 / 033563 publication WO2007 / 110228 publication
- the object of the present invention is as a highly efficient and durable organic electroluminescent device material, excellent in hole injection / transport performance, electron blocking ability, high stability in a thin film state, and heat resistance It is another object of the present invention to provide an organic compound having excellent characteristics and to provide an organic electroluminescence device having high efficiency and high durability by using this compound.
- the physical characteristics that the organic compound to be provided by the present invention should have include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) The thin film state is stable, and (5) The heat resistance is excellent.
- the physical characteristics of the organic electroluminescent device to be provided by the present invention include (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical use. The drive voltage is low.
- the present inventors have that the aromatic tertiary amine structure has a high hole injection / transport capability and that the acridan ring structure has an electron blocking property.
- a compound having an acridan ring structure was designed and chemically synthesized, and various organic electroluminescence devices were prototyped using the compound. As a result of diligent evaluation of device characteristics, the present invention has been completed.
- the present invention is a compound having an acridan ring structure represented by the following general formula (1).
- Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group.
- R 1 to R 6 may be the same as or different from each other, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, or a substituent.
- a ring may be formed.
- the present invention is a compound having an acridan ring structure represented by the following general formula (2).
- Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group.
- R 1 to R 6 may be the same as or different from each other, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, or a substituent.
- a ring may be formed.
- this invention is a compound which has an acridan ring structure whose R ⁇ 7 > and R ⁇ 8 > is a methyl group in the said General formula (1).
- the present invention is a compound having an acridan ring structure, wherein Ar 1 in the general formula (1) is a substituted or unsubstituted biphenylyl group.
- the present invention also relates to a compound having an acridan ring structure, wherein Ar 1 in the general formula (1) is a substituted or unsubstituted 9,9′-dimethylfluorenyl group.
- the present invention also relates to a compound having an acridan ring structure, wherein Ar 1 in the general formula (1) is a 9-phenyl-9H-carbazolyl group.
- the present invention provides a compound having an acridan ring structure represented by the general formula (1) or the general formula (2) in an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween.
- an organic electroluminescence device characterized in that it is used as a constituent material of at least one organic layer.
- “straight or branched alkyl group having 1 to 6 atoms” “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms” Specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group Cyclohexyl
- a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 1 to R 8 in the general formulas (1) to (2), “a carbon atom having a substituent”
- a carbon atom having a substituent Specific examples of the “substituent” in the “cycloalkyl group having 5 to 10” or “straight or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, trifluoro A methyl group, a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a linear or branched group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, or a propyloxy group Alkoxy groups; alkenyl groups such as allyl groups; aryloxy groups such as phenoxy groups and
- Specific examples of the “cycloalkyloxy group” include a methyloxy group, an ethyloxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, and an n-hexyloxy group.
- Cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group and 2-adaman Or the like can be mentioned aryloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- Specific examples of the “substituent” in the “cycloalkyloxy group having 5 to 10 atoms” include deuterium atom, trifluoromethyl group, cyano group, nitro group; fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
- a straight or branched alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group and a propyloxy group; an alkenyl group such as an allyl group; an aryloxy group such as a phenoxy group and a tolyloxy group; Arylalkoxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthraceni Group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl group, furanyl group, pyranyl group, thienyl group , Furyl group, pyrrolyl group, thiophenyl group, quinolyl
- the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the substituted condensed polycyclic aromatic group specifically, a phenyl group, a biphenylyl group, a terphenylyl group, Naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thiophenyl, quinolyl, isoquinolyl, benzofuranyl, Benzothiophenyl group, indolyl group, carbazolyl group
- aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 6 in the general formulas (1) to (2) includes a thiophenyl group, a benzo Sulfur-containing aromatic heterocyclic groups such as a thiophenyl group, a benzothiazolyl group, and a dibenzothiophenyl group are preferred.
- substitution in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 1 to R 6 in the general formulas (1) to (2)
- group include deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group A linear or branched alkyl group having 1 to 6 carbon atoms, such as isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group and n-hexyl group Linear or branched alkoxy groups having 1 to 6 carbon atoms such as methoxy group, ethoxy group, and
- aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 1 to R 6 in the general formulas (1) to (2), specifically, phenoxy group, tolyloxy group, biphenyl Examples thereof include a aryloxy group, a terphenylyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- substituted aryloxy group represented by R 1 to R 6 in the general formulas (1) to (2)
- substituents include a deuterium atom, a trifluoromethyl group, a cyano group, Nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group Linear or branched alkyl groups having 1 to 6 carbon atoms such as isopentyl group, neopentyl group and n-hexyl group; straight chain having 1 to 6 carbon atoms such as methoxy group, ethoxy group and propyloxy group Or branched alkoxy groups; alkenyl groups such as allyl groups; aralkyl
- the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the substituted condensed polycyclic aromatic group specifically, a phenyl group, a biphenylyl group, a terphenylyl group, Naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thiophenyl, quinolyl, isoquinolyl, benzofuranyl, Benzothiophenyl, indolyl, carbazolyl, benzo
- the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 to Ar 3 in the general formulas (1) to (2) includes a thiophenyl group, a benzo
- a sulfur-containing aromatic heterocyclic group such as a thiophenyl group, a benzothiazolyl group, a dibenzothiophenyl group, or a carbazolyl group having a substituent at the 9-position is preferable.
- substitution in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 3 in the general formulas (1) to (2)
- group include deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group A linear or branched alkyl group having 1 to 6 carbon atoms, such as isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group and n-hexyl group A linear or branched alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy
- substituents may be further substituted. Further, these substituents are substituted with each other or with a “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 3. May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- R 7 and R 8 in the general formulas (1) to (2) are preferably a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a methyl group , Ethyl group and propyl group are particularly preferable.
- Ar 1 to Ar 3 in the general formulas (1) to (2) are “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted condensed polycyclic aromatic group” or “position 9
- a carbazolyl group having a substituent '' is preferred, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group,
- a 9,9′-dimethylfluorenyl group, a 9-phenyl-9H-carbazolyl group, a substituted or unsubstituted triphenylenyl group is particularly preferred.
- the compound having an acridan ring structure represented by the general formulas (1) to (2) of the present invention is a novel compound, and has a superior electron blocking ability than a conventional hole transport material, and an excellent amorphous And a thin film state is stable.
- the compound having an acridan ring structure represented by the general formulas (1) to (2) of the present invention is a hole injection layer and / or a hole transport layer of an organic electroluminescence device (hereinafter abbreviated as an organic EL device). It can be used as a constituent material of the layer.
- an organic EL device organic electroluminescence device
- the probability of recombination of holes and electrons can be improved, high luminous efficiency can be obtained, the driving voltage is lowered, and the durability of the organic EL element is improved.
- the compound having an acridan ring structure represented by the general formulas (1) to (2) of the present invention can also be used as a constituent material of an electron blocking layer of an organic EL device.
- the driving voltage is lowered and current resistance is maintained while having high luminous efficiency. Is improved and the maximum light emission luminance of the organic EL element is improved.
- the compound having an acridan ring structure represented by the general formulas (1) to (2) of the present invention can also be used as a constituent material of a light emitting layer of an organic EL device.
- the material of the present invention which has excellent hole transportability compared to conventional materials and has a wide band gap, is used as a host material for the light-emitting layer, and supports a fluorescent or phosphorescent emitter called a dopant to emit light. By using it as a layer, it has the effect
- the organic EL device of the present invention has a higher mobility of holes than conventional hole transport materials, an excellent electron blocking ability, an excellent amorphous property, and a stable thin film state. Since a compound having a structure is used, high efficiency and high durability can be realized.
- the compound having an acridan ring structure of the present invention is useful as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device, has an excellent electron blocking ability, and Amorphous property is good, thin film state is stable, and heat resistance is excellent.
- the organic EL device of the present invention has high luminous efficiency and high power efficiency, which can reduce the practical driving voltage of the device.
- FIG. 1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 5).
- FIG. 3 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 65).
- FIG. 3 is a 1 H-NMR chart of the compound of Example 3 of the present invention (Compound 22).
- FIG. 6 is a 1 H-NMR chart of the compound of Example 4 of the present invention (Compound 4).
- FIG. 6 is a 1 H-NMR chart of the compound of Example 5 of the present invention (Compound 66).
- FIG. 6 is a 1 H-NMR chart of the compound of Example 6 of the present invention (Compound 67).
- FIG. 3 is a 1 H-NMR chart of the compound of Example 7 of the present invention (Compound 68).
- FIG. 3 is a diagram showing EL element configurations of Examples 10 to 12 and Comparative Example 1.
- the compound having an acridan ring structure of the present invention is a novel compound, and these compounds can be synthesized as follows, for example.
- bromination of the corresponding 10-positioned acridan with an aryl group by bromination with bromine, N-bromosuccinimide or the like synthesizes a bromo-substituted product at the 2-position and / or 7-position (for example, Patent Document 3).
- a cross-coupling reaction such as Suzuki coupling between a boronic acid or a boronic acid ester (for example, see Non-patent Document 4) synthesized by a reaction of this bromo compound with pinacolborane, bis (pinacolato) diboron, etc.
- the compound which has an acridan ring structure is compoundable by performing nonpatent literature 5).
- the 7-position is brominated by performing bromination in the same manner, and the 7-position is substituted by the same cross-coupling reaction.
- the 2-position is brominated by the same bromination and the same cross-coupling reaction is performed. Can introduce a substituent at the 2-position.
- an acridan ring having a different substitution position by bromination of an acridan substituted with an aryl group at the 10-position, introducing a bromo group at positions other than the 2-position and the 7-position, and carrying out a similar cross-coupling reaction
- a compound having a structure can be synthesized.
- glass transition point (Tg), melting point and work function were measured.
- the glass transition point (Tg) is an index of stability in a thin film state
- the melting point is an index of vapor deposition
- the work function is an index of hole transportability.
- the glass transition point (Tg) and melting point were determined with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
- the work function was measured using an atmospheric photoelectron spectrometer (AC-3 type, manufactured by Riken Keiki Co., Ltd.) by forming a 100 nm thin film on the ITO substrate.
- the structure of the organic EL device of the present invention includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and between the anode and the hole transport layer. And those having an electron injection layer between the electron transport layer and the cathode.
- these multilayer structures several organic layers can be omitted.
- a structure having an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on a substrate can be used. .
- an electrode material having a large work function such as ITO or gold is used.
- a hole injection layer of the organic EL device of the present invention in addition to the compound having an acridan ring structure represented by the general formula (1) of the present invention, a porphyrin compound represented by copper phthalocyanine, a starburst type triphenylamine Derivatives, materials such as various triphenylamine tetramers, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- N, N′-diphenyl-N, N′-di (m- Tolyl) benzidine hereinafter abbreviated as TPD
- NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
- NPD N, N, N ′, N′— Benzidine derivatives such as tetrabiphenylylbenzidine, 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and tetramers, etc.
- TPD N, N′-diphenyl-N, N′-di (m- Tolyl) benzidine
- NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
- NPD N, N, N ′, N′— Benzidine derivatives such
- a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly (styrene sulfonate) (hereinafter abbreviated as PSS) is used. These polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- a material that is usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the like, or a TPD structure having a partial structure. Molecular compounds and the like can be used.
- TCTA N-carbazolyl triphenyl Amine
- mCP 1,3-bis (carbazol-9-yl) benzene
- Ad-Cz Carbazole derivatives such as 2,2-bis (4-carbazol-9-ylphenyl) adamantane
- Ad-Cz 9- [4- (carbazol-9-yl) phenyl] -9- [
- a compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure represented by 4- (triphenylsilyl) phenyl]
- These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- the light emitting layer of the organic EL device of the present invention various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc., in addition to metal complexes of quinolinol derivatives including Alq 3 can be used.
- the light emitting layer may be composed of a host material and a dopant material.
- the compound having an acridan ring structure represented by the general formula (1) of the present invention as the host material in addition to the light emitting material, thiazole Derivatives, benzimidazole derivatives, polydialkylfluorene derivatives and the like can be used.
- quinacridone coumarin, rubrene, perylene, and derivatives thereof
- benzopyran derivatives rhodamine derivatives, aminostyryl derivatives, and the like
- These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
- a phosphorescent material can be used as the light emitting material.
- a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
- Green phosphorescent emitters such as Ir (ppy) 3
- blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters
- Btp 2 Ir (acac) are used as the host material.
- carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, etc.
- a compound having an acridan ring structure represented can be used as a hole injection / transport host material.
- a compound having an acridan ring structure represented can be used.
- an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) can be used, and a high-performance organic EL device can be produced.
- the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
- BCP bathocuproine
- BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
- BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
- various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
- These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline as well as metal complexes of quinolinol derivatives including Alq 3 and BAlq.
- Derivatives, phenanthroline derivatives, silole derivatives and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- an alkali metal salt such as lithium fluoride and cesium fluoride
- an alkaline earth metal salt such as magnesium fluoride
- a metal oxide such as aluminum oxide
- an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
- Tetrakis (triphenylphosphine) palladium (0.17 g) was added and heated, followed by stirring at 68 ° C. for 6.5 hours. The mixture was allowed to cool to room temperature, 50 ml of methanol was added, and the precipitated crude product was collected by filtration. The crude product was dissolved in 100 ml of toluene and subjected to adsorption purification using 10 g of silica gel. After concentrating under reduced pressure, it was washed with 50 ml of methanol, and crystals were precipitated with a mixed solvent of toluene / methanol.
- Tetrakis (triphenylphosphine) palladium (0.23 g) was added and heated, followed by stirring at 68 ° C. for 6 hours. The mixture was allowed to cool to room temperature, and the organic layer was collected by a liquid separation operation. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain a brown crude product.
- Tetrakis (triphenylphosphine) palladium (0.10 g) was added and heated, followed by stirring at 68 ° C. for 3 hours. The mixture was allowed to cool to room temperature, and the organic layer was collected by a liquid separation operation. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain a brown crude product.
- Tetrakis (triphenylphosphine) palladium (0.58 g) was added and heated, followed by stirring at 68 ° C. for 4 hours. The mixture was allowed to cool to room temperature, and the organic layer was collected by a liquid separation operation. The organic layer was washed with 100 ml of water and then concentrated under reduced pressure. After dissolution by adding 445 ml of toluene, adsorption purification using silica gel was performed. After concentrating under reduced pressure, 12.1 g of crude product was obtained by crystallization with 300 ml of methanol.
- the mixture was allowed to cool to room temperature, 50 ml of methanol, 50 ml of water and 75 ml of toluene were added, insoluble matters were removed by filtration, and then the organic layer was collected by a liquid separation operation. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate, and concentrated under reduced pressure to obtain a brown crude product.
- Tetrakis (triphenylphosphine) palladium (0.20 g) was added and heated, followed by stirring at 72 ° C. for 5 hours. The mixture was allowed to cool to room temperature, and the organic layer was collected by a liquid separation operation. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. After the crude product is purified by column chromatography (carrier: silica gel, eluent: hexane / toluene), crystallization with a mixed solvent of toluene and methanol, crystallization with diisopropyl ether, and crystallization with a mixed solvent of THF and methanol are repeated.
- carrier silica gel, eluent: hexane / toluene
- crystallization with a mixed solvent of toluene and methanol crystallization with diisopropyl ether
- Tetrakis (triphenylphosphine) palladium (0.19 g) was added and heated, followed by stirring at 67 ° C. for 5.5 hours. The mixture was allowed to cool to room temperature, and the organic layer was collected by a liquid separation operation. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain a crude product. Toluene was added to the crude product for dissolution, and after purification by adsorption using silica gel, purification was performed by column chromatography (carrier: silica gel, eluent: hexane / toluene).
- the compound of the present invention has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable in the compound of the present invention.
- the compound of the present invention exhibits a suitable energy level as compared with the work function 5.4 eV of general hole transport materials such as NPD and TPD, and has a good hole transport capability.
- the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2 as shown in FIG. 6, an electron injection layer 7 and a cathode (aluminum electrode) 8 were deposited in this order.
- the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, a compound 71 having the following structural formula was formed to a thickness of 20 nm as the hole injection layer 3 so as to cover the transparent anode 2. On this hole injection layer 3, the compound (compound 5) of Example 1 of the present invention was formed as a hole transport layer 4 so as to have a film thickness of 40 nm.
- On this emitting layer 5 was formed to have the Alq 3 film thickness 30nm as an electron transport layer 6.
- lithium fluoride was formed as the electron injection layer 7 so as to have a film thickness of 0.5 nm.
- aluminum was deposited to a thickness of 150 nm to form the cathode 8.
- the characteristic measurement was performed at normal temperature in air
- Example 10 In Example 10, except that the compound (Compound 22) of Example 3 of the present invention was formed to a film thickness of 40 nm in place of the compound (Compound 5) of Example 1 of the present invention as the material for the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 10 except that the compound (Compound 67) of Example 6 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material of the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 10 For comparison, in Example 10, except that the compound 74 of the following structural formula was formed to a film thickness of 40 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material of the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- the driving voltage was 5.17 V for Compound 74, 5.20 V for Compound (Compound 5) of Example 1 of the present invention
- the compound of Example 3 (Compound 22) could be driven at a low voltage of 4.81 V
- the compound of Example 6 (Compound 67) could be driven at a low voltage equivalent to or higher than 5.09 V.
- the compound 74 of Example 74 of the present invention (Compound 5) is 6.07 lm / W compared to 5.49 lm / W of Compound 74, and the compound of Example 3 of the present invention (Compound 22).
- the compound of Example 6 (Compound 67) was greatly improved to 6.74 lm / W.
- the compound of the present invention was improved with respect to the compound 74 in both luminance and luminous efficiency.
- the organic EL device using the compound having an acridan ring structure of the present invention is improved in luminous efficiency and power efficiency as compared with the organic EL device using the compound 74, and It was found that a decrease in practical driving voltage can be achieved.
- the compound having a compound having an acridan ring structure of the present invention is excellent as a compound for an organic EL device because of its high hole transport ability, excellent amorphous property and stable thin film state.
- an organic EL device using the compound high luminous efficiency and power efficiency can be obtained, practical driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.
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Abstract
Description
ここで、一般式(1)~(2)中のR1~R6で表される「置換もしくは無置換の芳香族複素環基」における「芳香族複素環基」としては、チオフェニル基、ベンゾチオフェニル基、ベンゾチアゾリル基、ジベンゾチオフェニル基など含硫黄芳香族複素環基が好ましい。
ここで、一般式(1)~(2)中のAr1~Ar3で表される「置換もしくは無置換の芳香族複素環基」における「芳香族複素環基」としては、チオフェニル基、ベンゾチオフェニル基、ベンゾチアゾリル基、ジベンゾチオフェニル基など含硫黄芳香族複素環基、または9位に置換基を有するカルバゾリル基が好ましい。
ここで、2位がブロモ化されたモノブロモ置換体から合成したアクリダン環構造を有する化合物においては、同様にブロモ化を行うことによって7位をブロモ化し、同様のクロスカップリング反応によって7位に置換基を導入することができ、7位がブロモ化されたモノブロモ置換体から合成したアクリダン環構造を有する化合物においては、同様にブロモ化を行うことによって2位をブロモ化し、同様のクロスカップリング反応によって2位に置換基を導入することができる。
同様に、10位をアリール基で置換されたアクリダンのブロモ化によって、2位および7位以外の位置にブロモ基を導入し、同様のクロスカップリング反応を行うことによって置換位置の異なる、アクリダン環構造を有する化合物を合成することができる。
窒素雰囲気下、反応容器に、10-(ビフェニル-4-イル)-2,7-ジブロモ-9,9-ジメチルアクリダン3.90g、4-ビフェニルボロン酸1.64g、トルエン39ml、エタノール10ml、2M炭酸カリウム水溶液11mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.17gを加えて加熱し、68℃で6.5時間攪拌した。室温まで放冷し、メタノール50mlを加え、析出する粗製物をろ過によって採取した。粗製物をトルエン100mlに溶解し、シリカゲル10gを用いた吸着精製を行った。減圧下で濃縮した後、メタノール50mlで洗浄し、トルエン/メタノールの混合溶媒によって結晶を析出させた。さらに、1,2-ジクロロベンゼンを用いた再結晶、続いて、1,2-ジクロロベンゼン/酢酸エチルの混合溶媒による晶析を行った後、メタノールによる還流洗浄を行うことによって、2,7,10-トリス(ビフェニル-4-イル)-9,9-ジメチルアクリダン(化合物5)の白色粉体1.77g(収率35%)を得た。
窒素雰囲気下、反応容器に、10-(ビフェニル-4-イル)-2,7-ジブロモ-9,9-ジメチルアクリダン3.48g、2-(9,9-ジメチル-9H-フルオレン-2-イル)-4,4,5,5-テトラメチル-[1,3,2]ジオキサボロラン4.52g、トルエン52ml、エタノール13ml、2M炭酸カリウム水溶液10mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.23gを加えて加熱し、68℃で6時間攪拌した。室温まで放冷し、分液操作によって有機層を採取した。有機層を硫酸マグネシウムで乾燥させた後、減圧下で濃縮することによって褐色の粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ヘキサン/トルエン)によって精製した後、メタノールによる洗浄、ジイソプロピルエーテルによる洗浄を繰返すことによって、10-(ビフェニル-4-イル)-2,7-ビス(9,9-ジメチル-9H‐フルオレン-2-イル)-9,9-ジメチルアクリダン(化合物65)の白色粉体2.70g(収率54%)を得た。
窒素雰囲気下、反応容器に、10-(9,9-ジメチル-9H-フルオレン-2-イル)-2,7-ジブロモ-9,9-ジメチルアクリダン2.51g、4-ビフェニルボロン酸1.85g、トルエン25ml、エタノール6ml、2M炭酸カリウム水溶液7mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.10gを加えて加熱し、68℃で3時間攪拌した。室温まで放冷し、分液操作によって有機層を採取した。有機層を硫酸マグネシウムで乾燥させた後、減圧下で濃縮することによって褐色の粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ヘキサン/トルエン)によって精製した後、ジイソプロピルエーテルによる還流洗浄を行うことによって、2,7-ビス(ビフェニル-4-イル)-10-(9,9-ジメチル-9H-フルオレン-2-イル)-9,9-ジメチルアクリダン(化合物22)の白色粉体2.02g(収率64%)を得た。
窒素雰囲気下、反応容器に、10-(ビフェニル-4-イル)-2-ブロモ-9,9-ジメチル-7-フェニルアクリダン13.00g、4-ビフェニルボロン酸5.73g、トルエン195ml、エタノール50ml、2M炭酸カリウム水溶液19mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.58gを加えて加熱し、68℃で4時間攪拌した。室温まで放冷し、分液操作によって有機層を採取した。有機層を水100mlによる洗浄操作を行った後、減圧下で濃縮した。トルエン445mlを加えて溶解した後、シリカゲルを用いた吸着精製を行った。減圧下で濃縮した後、メタノール300mlによる晶析を行うことによって、粗製物12.1gを得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:トルエン)による精製を行うことによって、2,10-ビス(ビフェニル-4-イル)-9,9-ジメチル-7-フェニルアクリダン(化合物4)の白色粉体14.8g(収率100%)を得た。
窒素雰囲気下、反応容器に、2,7-ジブロモ-9,9-ジメチルアクリダン10.00g、フェニルボロン酸7.34g、トルエン150ml、2M炭酸カリウム水溶液40mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.63gを加えて加熱し、78℃で4.5時間攪拌した。フェニルボロン酸0.34gを追加し、さらに、78℃で2時間撹拌した。室温まで放冷し、不溶物をろ過によって除いた後、分液操作によって有機層を採取した。有機層を硫酸マグネシウムで乾燥させた後、減圧下で濃縮することによって褐色の粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ヘキサン/トルエン)によって精製した後、ヘキサンで結晶化させることによって、9,9-ジメチル-2,7-ジフェニルアクリダン5.10gを得た。
窒素雰囲気下、反応容器に、7-ブロモ-10-(9,9-ジメチル-9H-フルオレン-2-イル)-9,9-ジメチル-2-フェニルアクリダン2.79g、9-フェニル-3-(4,4,5,5-テトラメチル-[1,3,2]ジオキサボロラン-2-イル)-9H-カルバゾール3.98g、トルエン75ml、エタノール19ml、2M炭酸カリウム水溶液6.5mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.20gを加えて加熱し、72℃で5時間攪拌した。室温まで放冷し、分液操作によって有機層を採取した。有機層を水50mlによる洗浄操作を2回繰り返した後、硫酸マグネシウムで乾燥させ、減圧下で濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ヘキサン/トルエン)によって精製した後、トルエンとメタノールの混合溶媒による晶析、ジイソプロピルエーテルによる晶析、THFとメタノールの混合溶媒による晶析を繰り返すことによって、10-(9,9-ジメチル-9H-フルオレン-2-イル)-9,9-ジメチル-2-フェニル-7-(9-フェニル-9H-カルバゾール-3-イル)アクリダン(化合物67)の白色粉体3.38g(収率52%)を得た。
窒素雰囲気下、反応容器に、7-ブロモ-10-(9,9-ジメチル-9H-フルオレン-2-イル)-9,9-ジメチル-2-(ナフタレン-1-イル)アクリダン5.00g、9-フェニル-3-(4,4,5,5-テトラメチル-[1,3,2]ジオキサボロラン-2-イル)-9H-カルバゾール3.65g、トルエン75ml、エタノール19ml、2M炭酸カリウム水溶液6mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム0.19gを加えて加熱し、67℃で5.5時間攪拌した。室温まで放冷し、分液操作によって有機層を採取した。有機層を硫酸マグネシウムで乾燥させた後、減圧下で濃縮することによって粗製物を得た。粗製物にトルエンを加えて溶解し、シリカゲルを用いた吸着精製を行った後、カラムクロマトグラフ(担体:シリカゲル、溶離液:ヘキサン/トルエン)によって精製した。トルエンとヘキサンの混合溶媒による晶析、トルエンとジイソプロピルエーテルの混合溶媒による晶析を繰り返した後、メタノールによる還流洗浄を行うことによって、10-(9,9-ジメチル-9H-フルオレン-2-イル)-9,9-ジメチル-2-(ナフタレン-1-イル)-7-(9-フェニル-9H-カルバゾール-3-イル)アクリダン(化合物68)の白色粉体3.18g(収率50%)を得た。
融点 ガラス転移点
本発明実施例1の化合物 235℃ 129℃
本発明実施例2の化合物 168℃ 148℃
本発明実施例3の化合物 168℃ 141℃
本発明実施例4の化合物 134℃ 111℃
本発明実施例5の化合物 219℃ 132℃
本発明実施例6の化合物 179℃ 145℃
仕事関数
本発明実施例1の化合物 5.57eV
本発明実施例2の化合物 5.57eV
本発明実施例3の化合物 5.52eV
本発明実施例4の化合物 5.63eV
本発明実施例5の化合物 5.59eV
本発明実施例6の化合物 5.51eV
比較のために、実施例10において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて下記構造式の化合物74を膜厚40nmとなるように形成した以外は、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なった。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 正孔注入層
4 正孔輸送層
5 発光層
6 電子輸送層
7 電子注入層
8 陰極
Claims (11)
- 下記一般式(1)で表される、アクリダン環構造を有する化合物。
(式中、Ar1、Ar2、Ar3は相互に同一でも異なってもよく、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を表し、R1~R6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、トリフルオロメチル基、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または置換もしくは無置換のアリールオキシ基であって、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。R7、R8は相互に同一でも異なってもよく、トリフルオロメチル基、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(2)で表される、アクリダン環構造を有する化合物。
(式中、Ar1、Ar2、Ar3は相互に同一でも異なってもよく、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を表し、R1~R6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、トリフルオロメチル基、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または置換もしくは無置換のアリールオキシ基であって、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。R7、R8は相互に同一でも異なってもよく、トリフルオロメチル基、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、R7およびR8がメチル基である、請求項1記載のアクリダン環構造を有する化合物。
- 前記一般式(1)において、Ar1が置換もしくは無置換のビフェニリル基である、請求項1記載のアクリダン環構造を有する化合物。
- 前記一般式(1)において、Ar1が置換もしくは無置換の9,9’-ジメチルフルオレニル基である、請求項1記載のアクリダン環構造を有する化合物。
- 前記一般式(1)において、Ar1が9-フェニル-9H-カルバゾリル基である、請求項1記載のアクリダン環構造を有する化合物。
- 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1~2に記載のアクリダ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ことを特徴とする有機エレクトロルミネッセンス素子。
- 前記した有機層が正孔輸送層である請求項7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阻止層である請求項7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注入層である請求項7記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が発光層である請求項7記載の有機エレクトロルミネッセンス素子。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/113,280 US9905770B2 (en) | 2011-04-27 | 2012-04-24 | Compound having acridan ring structure, and organic electroluminescent device |
EP12776870.3A EP2703388A4 (en) | 2011-04-27 | 2012-04-24 | COMPOUND HAVING THE STRUCTURE OF AN ACRIDANE CYCLE, AND ORGANIC ELECTROLUMINESCENT ELEMENT |
CN201280020443.6A CN103619821A (zh) | 2011-04-27 | 2012-04-24 | 具有9,10-二氢吖啶环结构的化合物以及有机电致发光器件 |
JP2013511923A JP6158703B2 (ja) | 2011-04-27 | 2012-04-24 | アクリダ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 |
KR1020137031409A KR20140026536A (ko) | 2011-04-27 | 2012-04-24 | 아크리단환 구조를 가지는 화합물 및 유기 일렉트로루미네선스 소자 |
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JP (1) | JP6158703B2 (ja) |
KR (1) | KR20140026536A (ja) |
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Cited By (3)
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WO2014017844A1 (ko) * | 2012-07-26 | 2014-01-30 | 주식회사 동진쎄미켐 | 아크리딘 유도체를 포함하는 유기발광 화합물 및 이를 포함하는 유기발광소자 |
JP2014521593A (ja) * | 2011-05-05 | 2014-08-28 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
JP2019116588A (ja) * | 2017-12-27 | 2019-07-18 | 日立化成株式会社 | 電荷輸送性材料、該材料を用いたインク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
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KR102169273B1 (ko) * | 2012-07-26 | 2020-10-23 | 주식회사 동진쎄미켐 | 아크리딘 유도체를 포함하는 유기발광 화합물 및 이를 포함하는 유기발광소자 |
CN104292162A (zh) * | 2014-09-18 | 2015-01-21 | 吉林奥来德光电材料股份有限公司 | 二氢吖啶类化合物及其制备方法和由该化合物制得的有机发光器件 |
KR102386839B1 (ko) | 2014-12-22 | 2022-04-15 | 삼성전자주식회사 | 유기 발광 소자 |
CN107482132A (zh) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | 一种有机发光器件 |
WO2020205765A1 (en) * | 2019-03-29 | 2020-10-08 | Colorado State University Research Foundation | Carbazole and acridine photoredox catalysts for small molecule and macromolecular transformations |
CN113831340B (zh) * | 2021-10-18 | 2023-04-18 | 中国科学院化学研究所 | 一种杯[n]二氢吖啶大环及其制备方法 |
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- 2012-04-24 US US14/113,280 patent/US9905770B2/en not_active Expired - Fee Related
- 2012-04-24 KR KR1020137031409A patent/KR20140026536A/ko not_active Application Discontinuation
- 2012-04-24 CN CN201280020443.6A patent/CN103619821A/zh active Pending
- 2012-04-24 JP JP2013511923A patent/JP6158703B2/ja not_active Expired - Fee Related
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JP2014521593A (ja) * | 2011-05-05 | 2014-08-28 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
JP2016166221A (ja) * | 2011-05-05 | 2016-09-15 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
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WO2014017844A1 (ko) * | 2012-07-26 | 2014-01-30 | 주식회사 동진쎄미켐 | 아크리딘 유도체를 포함하는 유기발광 화합물 및 이를 포함하는 유기발광소자 |
JP2019116588A (ja) * | 2017-12-27 | 2019-07-18 | 日立化成株式会社 | 電荷輸送性材料、該材料を用いたインク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
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JP6158703B2 (ja) | 2017-07-05 |
JPWO2012147330A1 (ja) | 2014-07-28 |
CN103619821A (zh) | 2014-03-05 |
TW201305113A (zh) | 2013-02-01 |
CN107266364A (zh) | 2017-10-20 |
EP2703388A1 (en) | 2014-03-05 |
TWI537253B (zh) | 2016-06-11 |
US9905770B2 (en) | 2018-02-27 |
US20140042425A1 (en) | 2014-02-13 |
EP2703388A4 (en) | 2014-10-29 |
KR20140026536A (ko) | 2014-03-05 |
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