WO2019049965A1 - ピリミジ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
ピリミジ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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- WO2019049965A1 WO2019049965A1 PCT/JP2018/033140 JP2018033140W WO2019049965A1 WO 2019049965 A1 WO2019049965 A1 WO 2019049965A1 JP 2018033140 W JP2018033140 W JP 2018033140W WO 2019049965 A1 WO2019049965 A1 WO 2019049965A1
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- compound
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- pyrimidine ring
- ring structure
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 199
- 125000000714 pyrimidinyl group Chemical group 0.000 title claims abstract description 129
- -1 triphenylsilyl group Chemical group 0.000 claims abstract description 133
- 239000000463 material Substances 0.000 claims abstract description 92
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 61
- 230000000903 blocking effect Effects 0.000 claims abstract description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
- 238000002347 injection Methods 0.000 claims abstract description 37
- 239000007924 injection Substances 0.000 claims abstract description 37
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 26
- 125000004431 deuterium atom Chemical group 0.000 claims abstract description 12
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 12
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 148
- 125000001041 indolyl group Chemical group 0.000 claims description 24
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000005493 quinolyl group Chemical group 0.000 claims description 15
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 14
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 14
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- 239000010409 thin film Substances 0.000 abstract description 19
- 150000002894 organic compounds Chemical class 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000007740 vapor deposition Methods 0.000 description 45
- 239000000843 powder Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 27
- 239000012043 crude product Substances 0.000 description 26
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- 230000008021 deposition Effects 0.000 description 25
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 23
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 23
- 229940126657 Compound 17 Drugs 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000005259 measurement Methods 0.000 description 20
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- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
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- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 7
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
- 229940125844 compound 46 Drugs 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
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- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 6
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 6
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 229940125878 compound 36 Drugs 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- ZMOPTMAMHBQPGD-UHFFFAOYSA-N 2-chloro-4-(4-phenylphenyl)-6-pyridin-3-ylpyrimidine Chemical compound C1(=CC=C(C=C1)C1=CC(=NC(=N1)Cl)C=1C=NC=CC=1)C1=CC=CC=C1 ZMOPTMAMHBQPGD-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 150000004322 quinolinols Chemical class 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 150000001454 anthracenes Chemical class 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
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- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000006617 triphenylamine group Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PNVJKSUIZRZODR-UHFFFAOYSA-N 2,4-bis(4-naphthalen-1-ylphenyl)-6-pyridin-3-ylpyrimidine Chemical compound C1=2C=CC=C(C=2C=CC=C1)C1=CC=C(C2=NC(=NC(=C2)C2=CN=CC=C2)C2=CC=C(C3=CC=CC4=CC=CC=C34)C=C2)C=C1 PNVJKSUIZRZODR-UHFFFAOYSA-N 0.000 description 2
- CXBDKJHZYAQMLC-UHFFFAOYSA-N 2-chloro-4-(4-naphthalen-1-ylphenyl)-6-pyridin-3-ylpyrimidine Chemical compound ClC1=NC(=CC(=N1)C=1C=NC=CC=1)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 CXBDKJHZYAQMLC-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
- OFNXNFIYEYQMAA-UHFFFAOYSA-N 8-[2-chloro-6-(4-phenylphenyl)pyrimidin-4-yl]quinoline Chemical compound C1(=CC=C(C=C1)C1=CC(=NC(=N1)Cl)C=1C=CC=C2C=CC=NC=12)C1=CC=CC=C1 OFNXNFIYEYQMAA-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
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- 239000007983 Tris buffer Substances 0.000 description 2
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 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 2
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- 235000019798 tripotassium phosphate Nutrition 0.000 description 2
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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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 and an element suitable for an organic electroluminescent element (hereinafter referred to as an organic EL element) which is a self-emission element suitable for various display devices, and more specifically, a compound having a pyrimidine ring structure
- the present invention relates to an organic EL device using the compound.
- the organic EL element is a self light emitting element, it is brighter than the liquid crystal element and has excellent visibility and clear display, and therefore, active research has been conducted.
- Eastman Kodak Company C.I. W. Tang et al. Made a practical use of an organic EL element using an organic material by developing a laminated structure element in which various functions are shared by each material. They stack phosphors capable of transporting electrons and organic substances capable of transporting holes, and inject both charges into the phosphor layer to emit light, with a voltage of 10 V or less A high luminance of 1000 cd / m 2 or more can be obtained (see, for example, Patent Document 1 and Patent Document 2).
- Non-Patent Document 3 In addition, utilization of triplet excitons has been attempted for the purpose of further improvement of luminous efficiency, and utilization of phosphorescent compounds has been studied (see, for example, Non-Patent Document 2). And devices using light emission by thermally activated delayed fluorescence (TADF) have also been developed, and in 2011 Adachi et al. Of Kyushu University found that 5.3% of the external quantum is achieved by the device using thermally activated delayed fluorescent material. I realized the efficiency. (For example, refer to Non-Patent Document 3)
- the light emitting layer can also be produced by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
- a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
- the selection of the organic material in the organic EL element has a great influence on various characteristics such as the efficiency and durability of the element. (For example, refer to Non-Patent Document 2)
- the organic EL element although the charge injected from both electrodes is recombined in the light emitting layer to obtain light emission, it is important how efficiently both holes and electrons are transferred to the light emitting layer.
- the electron injection property is enhanced, and the mobility thereof is increased to improve the probability that holes and electrons recombine in the light emitting layer.
- the role of the electron transport material is important, and there is a need for an electron transport material having high electron injection properties, high electron mobility, high hole blocking properties, and high resistance to holes.
- the heat resistance and the amorphous property of the material are also important with respect to the lifetime of the element.
- the heat generated at the time of device operation causes thermal decomposition even at low temperatures, and the materials deteriorate.
- crystallization of a thin film occurs even for a short time, and the device is degraded. Therefore, the material to be used is required to have high heat resistance and good amorphousness.
- a typical light emitting material tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq3) is generally used also as an electron transport material, but its electron transfer is slow, and its work function is 5.6 eV, so it is positive. The hole blocking performance is not sufficient.
- TAZ 4-bis(triphenyl) -4-phenyl-5- (4-t-butylphenyl) -1,2,4-triazole
- TAZ has a large work function of 6.6 eV and high hole blocking ability, it has an electron-transporting hole blocking layer laminated on the cathode side of a fluorescent light emitting layer or a phosphorescent light emitting layer prepared by vacuum deposition or coating. And contributes to high efficiency of the organic EL element (see, for example, Non-Patent Document 4).
- Non-Patent Document 5 Low electron transportability is a major issue in TAZ, and it has been necessary to produce an organic EL device in combination with an electron transport material having higher electron transportability (see, for example, Non-Patent Document 5).
- BCP has a large work function of 6.7 eV and high hole blocking ability, it has a low glass transition point (Tg) of 83 ° C., so the thin film lacks stability and functions sufficiently as a hole blocking layer. I can not say that.
- An object of the present invention is an organic compound having excellent electron injection / transport performance, hole blocking ability, and excellent stability in a thin film state as a material for organic EL devices having high efficiency and high durability. It is another object of the present invention to provide a highly efficient and highly durable organic EL device using this compound.
- the physical properties that the organic compound to be provided by the present invention should have include (1) good electron injection characteristics, (2) high electron mobility, and (3) hole blocking ability. It can be mentioned that it is excellent, (4) that the thin film state is stable, and (5) that it is excellent in heat resistance. Further, the physical characteristics that the organic EL element to be provided by the present invention should have include (1) high luminous efficiency and high power efficiency, (2) low luminous initiation voltage, and (3) practical driving The low voltage and (4) long life can be mentioned.
- the present inventors pay attention to the ability of the nitrogen atom of the pyrimidine ring which is electron affinity to be coordinated to a metal and the excellent heat resistance. Then, a compound having a pyrimidine ring structure is designed and chemically synthesized, and various organic EL devices are produced on an experimental basis using the compound. As a result of intensive evaluation of the characteristics of the device, the present invention is completed.
- the present invention is a compound having a pyrimidine ring structure, which is represented by the following general formula (1).
- a 1 represents a substituted or unsubstituted aromatic heterocyclic group.
- Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group.
- Ar 2 represents a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group;
- M represents an integer of 1 to 3
- n represents an integer of 0 to 2
- o represents an integer of 1 to 2.
- m is an integer of 2 or more.
- a plurality of Ar 1 bonded to the same pyrimidine ring may be the same as or different from each other
- n is an integer of 2
- Ar 2 bonded to the same pyrimidine ring may be the same as or different from each other
- o is an integer of 2
- a 1 to several bind to the same pyrimidine ring may be the same or different from each other.
- the 4 within the integer of the sum of m and n and o. Note that, when n is 0, Ar 2 is hydrogen Shall represent an atom)
- the present invention is a compound having a pyrimidine ring structure according to the above [1], which is a compound having a pyrimidine ring structure represented by the following general formula (2).
- (2) (Wherein, A 2 represents a substituted or unsubstituted aromatic heterocyclic group.
- Ar 3 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group.
- Ar 4 represents a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; P represents an integer of 1 to 3 and q represents an integer of 0 to 2.
- a plurality of bonded to the same pyrimidine ring Ar 3 s may be identical to or different from each other
- q is an integer of 2
- a plurality of Ar 4 bonded to the same pyrimidine ring may be identical to or different from each other, provided that p is an integer of q
- the sum of is less than 3.
- the present invention is a compound having a pyrimidine ring structure according to the above [1], which is a compound having a pyrimidine ring structure represented by the following general formula (3).
- (3) (Wherein, A 3 represents a substituted or unsubstituted aromatic heterocyclic group.
- Ar 5 and Ar 6 represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted group
- Ar 7 represents a hydrogen atom, a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heteroaromatic group, or a substituted or unsubstituted fused polycyclic aromatic group Represents a ring group or a substituted or unsubstituted fused polycyclic aromatic group)
- the present invention is a compound having a pyrimidine ring structure according to the above [1], which is a compound having a pyrimidine ring structure represented by the following general formula (4). (4) (Wherein, A 4 represents a substituted or unsubstituted aromatic heterocyclic group.
- Ar 8 and Ar 9 represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted group Or an unsubstituted fused polycyclic aromatic group
- Ar 10 represents a hydrogen atom, a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic complex Represents a ring group or a substituted or unsubstituted fused polycyclic aromatic group)
- the present invention is also a compound having a pyrimidine ring structure according to the above-mentioned [1], which is represented by the following general formula (5). (5) (Wherein, A 5 represents a substituted or unsubstituted aromatic heterocyclic group.
- Ar 11 and Ar 12 represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted group Or an unsubstituted fused polycyclic aromatic group
- Ar 13 is a hydrogen atom, a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic complex Represents a ring group or a substituted or unsubstituted fused polycyclic aromatic group)
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [4], wherein the aromatic heterocyclic group of the A 4 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, And azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, or carbonyl group. And a compound having a pyrimidine ring structure represented by the general formula (4).
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [5], wherein the aromatic heterocyclic group of the A 5 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, An azafluorenyl group, a diazafluorenyl group, a quinoxalinyl group, a benzoimidazolyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, an azaspirobifluorenyl group, a diazaspirobifluorenyl group or a carbonyl group,
- the present invention is also a compound having a pyrimidine ring structure according to the above [4], wherein the Ar 10 is a hydrogen atom and has a pyrimidine ring structure represented by the general formula (4).
- the present invention is a compound having a pyrimidine ring structure according to the above [5], wherein the Ar 13 is a hydrogen atom and has a pyrimidine ring structure represented by the general formula (5).
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [4], wherein the aromatic heterocyclic group of the A 4 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, Azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, or a carbonyl group, And a compound having a pyrimidine ring structure represented by the general formula (4), wherein Ar 10 is a hydrogen atom.
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [5], wherein the aromatic heterocyclic group of the A 5 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, Azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, or a carbonyl group, And a compound having a pyrimidine ring structure, represented by the general formula (5), wherein the Ar 13 is a hydrogen atom.
- the present invention provides a compound having a pyrimidine ring structure according to the above-mentioned [4], wherein at least one of Ar 8 and Ar 9 is a fused polycyclic aromatic group, aromatic heterocyclic group or As a substituent, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group
- the present invention provides a compound having a pyrimidine ring structure according to the above-mentioned [5], wherein at least one of Ar 11 and Ar 12 is a fused polycyclic aromatic group, aromatic heterocyclic group, Or as a substituent, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzo
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [4], wherein the aromatic heterocyclic group of the A 4 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, Azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, or a carbonyl group,
- Ar 10 is a hydrogen atom
- at least one of Ar 8 and Ar 9 is a fused polycyclic aromatic group, an aromatic heterocyclic group or a phenanthrenyl group as a substituent, Spirobifluorenyl group, benzofuranyl group, benzothienyl group,
- the present invention is a compound having a pyrimidine ring structure of the above-mentioned [5], wherein the aromatic heterocyclic group of the A 5 is a pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, indolyl group, Azafluorenyl group, diazafluorenyl group, quinoxalinyl group, benzimidazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group or carborinyl group, And Ar 13 is a hydrogen atom, and at least one of Ar 11 and Ar 12 is a fused polycyclic aromatic group, aromatic heterocyclic group or a substituent such as phenanthrenyl group, fluorenyl group or spiro.
- the aromatic heterocyclic group of the A 5 is a pyri
- Bifluorenyl group benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, Nzookisazoriru group, benzothiazolyl group, quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group or a dibenzothienyl group, a compound having a pyrimidine ring structure represented by the general formula (5),.
- the present invention provides an organic EL device having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the pyrimidine ring structure according to any one of the above [1] to [15]
- the compound is used as a constituent material of at least one organic layer, which is an organic EL element characterized by the above-mentioned.
- the present invention is the organic EL device according to the above-mentioned [16], wherein the organic layer in which the compound having a pyrimidine ring structure is used is an electron transport layer.
- the present invention is the organic EL device according to the above-mentioned [16], wherein the organic layer in which the compound having a pyrimidine ring structure is used is a hole blocking layer.
- the present invention is the organic EL device according to the above [16], wherein the organic layer in which the compound having a pyrimidine ring structure is used is a light emitting layer.
- the present invention is the organic EL device according to the above-mentioned [16], wherein the organic layer in which the compound having a pyrimidine ring structure is used is an electron injection layer.
- the compound having a pyrimidine ring structure of the present invention has (1) good electron injection properties, (2) fast electron mobility, (3) excellent hole blocking ability, and (4) stable in thin film state (5) excellent in heat resistance, etc.
- the organic EL device of the present invention is (6) high in luminous efficiency, (7) low in light emission starting voltage, (8) practically driven It has such characteristics as low voltage and (9) long life.
- FIG. 2 is a view showing Compound-1 to Compound-15 having a pyrimidine ring structure of the present invention.
- FIG. 7 is a view showing Compound-16 to Compound-30 having a pyrimidine ring structure of the present invention.
- FIG. 5 is a view showing Compound-31 to Compound-45 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing Compound -46 to Compound -60 having a pyrimidine ring structure of the present invention.
- FIG. 6 is a view showing Compound-61 to Compound-75 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing Compound -76 to Compound -90 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing Compound-91 to Compound-105 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing Compound -106 to Compound -120 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a diagram showing a compound -121 to a compound -135 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing a compound -136 to a compound -150 having a pyrimidine ring structure of the present invention.
- FIG. 2 is a view showing Compound-151 to Compound-160 having a pyrimidine ring structure of the present invention. It is the figure which showed the organic EL element structure of Examples 20-36 and Comparative Examples 1 and 2.
- the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by A 1 to A 5 in the general formulas (1) to (5) is specifically a pyridyl group, Pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, imidazolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, azafluorenyl group, dia The fluorenyl group, azaspirobifluorenyl group, diazaspirobifluorenyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthro
- “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 to Ar 13 in the general formulas (1) to (5), or “substituted or unsubstituted Specific examples of the "aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the substituted fused polycyclic aromatic group include phenyl group, biphenylyl group, terphenylyl group, A naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group , Thienyl group, quino
- Substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” represented by A 1 to A 5 and Ar 1 to Ar 13 in the general formulas (1) to (5), “substituted fused polycyclic aromatic ring”
- substituents in the “group” include deuterium atoms, cyano groups, nitro groups; halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms and iodine atoms; trimethylsilyl groups, triphenylsilyl groups, etc.
- a silyl group a linear or branched alkyl group having 1 to 6 carbon atoms such as methyl, ethyl and propyl; and a straight or branched alkyl group having 1 to 6 carbon atoms such as methyloxy, ethyloxy and propyloxy.
- alkenyl group such as vinyl group and allyl group
- aryloxy group such as phenyloxy group and tolyloxy group
- benzyloxy group phenethyl oxy
- Arylalkyloxy group such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group,
- Aromatic hydrocarbon group or condensed polycyclic aromatic group such as triphenylenyl group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzo
- a benzene ring substituted with these substituents or a plurality of substituents substituted on the same benzene ring may form a ring as a single bond, and a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom They may be linked to each other to form a ring.
- the compound having a pyrimidine ring structure represented by the above general formula (1) which is suitably used for the organic EL device of the present invention, is used as a constituent material of the electron injection layer, electron transport layer or hole blocking layer of the organic EL device. It can be used. It is a compound having high electron mobility and a preferable material of the electron injection layer or the electron transport layer.
- the organic EL device of the present invention uses a material for an organic EL device which is excellent in electron injection / transport performance, thin film stability and durability, it can be seen from the electron transport layer as compared to conventional organic EL devices.
- the electron transport efficiency to the light emitting layer is improved, the light emission efficiency is improved, the drive voltage is lowered, and the durability of the organic EL element can be improved, and the organic EL with high efficiency, low drive voltage and long life It became possible to realize the device.
- the compound having a pyrimidine ring structure of the present invention has (1) good electron injection properties, (2) fast electron mobility, (3) excellent hole blocking ability, and (4) stable in thin film state (5) excellent in heat resistance, etc.
- the organic EL device of the present invention is (6) high in luminous efficiency, (7) low in light emission starting voltage, (8) practically driven It has such characteristics as low voltage and (9) long life.
- the compound having a pyrimidine ring structure of the present invention has a high electron injection / mobility, so that an electron injection layer and / or an electron transport layer prepared using the compound as an electron injection material and / or an electron transport material
- the electron transport efficiency to the light emitting layer is improved, the light emission efficiency is improved, and the driving voltage is lowered, whereby the durability of the organic EL element is improved.
- the compound having a pyrimidine ring structure of the present invention is excellent in the hole blocking ability and the electron transporting property, is stable even in a thin film state, and is characterized in that the compound generated in the light emitting layer is confined.
- An organic EL device having a hole blocking layer manufactured using a hole blocking material improves the probability that holes and electrons recombine, prevents thermal deactivation, has high luminous efficiency, and has a driving voltage The maximum light emission luminance is improved by lowering and improving the current resistance.
- the compound having a pyrimidine ring structure of the present invention is excellent in electron transportability and has a wide band gap, so that an organic EL device having a light emitting layer manufactured using the compound as a host material is a fluorescent emission called a dopant.
- an organic EL device having a light emitting layer manufactured using the compound as a host material is a fluorescent emission called a dopant.
- the compound having a pyrimidine ring structure of the present invention is useful as a material of the electron injection layer, the electron transport layer, the hole blocking layer or the light emitting layer of the organic EL device, and the luminous efficiency and driving voltage of the conventional organic EL device , And durability can be improved.
- the compounds having a pyrimidine ring structure of the present invention are novel compounds, but these compounds can be synthesized according to methods known per se (see, for example, Patent Document 5 and Non-Patent Document 6).
- Purification of the compound having a pyrimidine ring structure represented by the general formulas (1) to (5) is purification by column chromatography, adsorption purification by silica gel, activated carbon, activated clay or the like, recrystallization or crystallization method by solvent, sublimation purification It went by the law etc. Identification of the compounds was performed by NMR analysis. Melting point, glass transition point (Tg) and work function were measured as physical property values. The melting point is an index of vapor deposition property, the glass transition point (Tg) is an index of stability of the thin film state, and the work function is an index of hole transporting property or hole blocking property.
- the melting point and the glass transition point (Tg) were measured with a powder using a high sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS).
- the work function was obtained by preparing a thin film of 100 nm on an ITO substrate and using an ionization potential measurement device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
- the structure of the organic EL device of the present invention comprises, in order on the substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, and hole transport.
- Those having an electron blocking layer between the layer and the light emitting layer and those having a hole blocking layer between the light emitting layer and the electron transport layer can be mentioned.
- a structure which combines a hole injection layer and a hole transport layer a structure which combines an electron injection layer and an electron transport layer It can also be done.
- 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 a porphyrin compound represented by copper phthalocyanine, a starburst type triphenylamine derivative, having two or more triphenylamine structures or carbazolyl structures in the molecule,
- an acceptor heterocyclic compound such as hexacyanoazatriphenylene or a coated polymer material may be used. it can.
- These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
- NPD N, N'-diphenyl-N, N'-di (m-tolyl) -benzidine
- NPD N, N'-diphenyl-N Benzidine derivatives such as N, N'-di ( ⁇ -naphthyl) -benzidine (hereinafter abbreviated as NPD), N, N, N ', N'-tetrabiphenylyl benzidine, 1,1-bis [(di-4) -Tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), a molecule having two or more triphenylamine structures or carbazolyl structures in the molecule, each of which is a single bond or a divalent group having no hetero atom
- TAPC 1,1-bis [(di-4) -Tolylamino) phenyl] cyclohexane
- PEDOT poly (3,4-ethylenedioxythiophene)
- PSS poly (styrene sulfonate)
- a material in which trisbromophenylamine hexachloroantimony, a radialene derivative is further P-doped to a material usually used in the layer, A high molecular compound having a structure of a benzidine derivative such as TPD in its partial structure can be used.
- TCTA 4,4 ′, 4 ′ ′-tri (N-carbazolyl) triphenylamine
- TCTA 9,9-bis [4- (carbazole-) 9-yl) phenyl] fluorene
- mCP 1,3-bis (carbazol-9-yl) benzene
- Ad 2,2-bis (4-carbazol-9-ylphenyl) adamantane
- triphenylsilyl groups represented by 9- [4- (carbazol-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene.
- compounds having electron blocking activity such as compounds having a triarylamine structure.
- these may be formed separately, they may be used as a single layer formed by mixing with other materials, and layers formed separately by the above plurality of materials may be used together by the above plurality of materials.
- a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a single film of the above plurality of materials may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
- the light emitting layer of the organic EL device of the present invention in addition to the compound having a pyrimidine ring structure of the present invention, metal complexes of quinolinol derivatives including Alq 3 , various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, Pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives and the like can be used.
- the light emitting layer may be composed of a host material and a dopant material, and anthracene derivative is preferably used as the host material, but in addition to the above light emitting materials including the compound having a pyrimidine ring structure of the present invention.
- a heterocyclic compound having an indole ring as a partial structure of a fused ring a heterocyclic compound having a carbazole ring as a partial structure of a fused ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkyl fluorene derivative, and the like can be used.
- the dopant material quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives and the like can be used.
- these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed separately by the above plural materials, and by the above plural materials
- a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a single film of the above plurality of materials may be employed.
- a phosphorescence material as a light emitting material.
- a phosphorescence light emitter a phosphorescence light emitter of metal complex such as iridium and platinum can be used.
- a green phosphor such as Ir (ppy) 3
- a blue phosphor such as FIrpic or FIr 6
- a red phosphor such as Btp 2 Ir (acac), or the like may be used as the host material.
- the compound having a pyrimidine ring structure of the present invention in addition to 4,4'-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP) and carbazole derivatives such as TCTA and mCP as a hole injecting / transporting host material Can be used.
- UGH2 triphenylsilyl
- a -1H-benzimidazole) hereinafter abbreviated as TPBI
- TPBI -1H-benzimidazole
- Non-Patent Document 3 a material that emits delayed fluorescence such as PICCB, such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, as a light-emitting material.
- PICCB a material that emits delayed fluorescence
- CC2TA a material that emits delayed fluorescence
- PXZ-TRZ a material that emits delayed fluorescence
- 4CzIPN a material that emits delayed fluorescence
- These materials can be thin film-formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
- phenanthroline derivatives such as vasocuproin (hereinafter abbreviated as BCP) and metal complexes of quinolinol derivatives such as BAlq.
- BCP vasocuproin
- metal complexes of quinolinol derivatives such as BAlq.
- Compounds having hole blocking activity such as various rare earth complexes, oxazole derivatives, triazole derivatives and triazine derivatives can be used.
- These materials may double as the material of the electron transport layer. Although these may be formed separately, they may be used as a single layer formed by mixing with other materials, and layers formed separately by the above plurality of materials may be used together by the above plurality of materials.
- a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a single film of the above plurality of materials may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
- metal complexes of quinolinol derivatives including Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, as the electron transporting layer of the organic EL device of the present invention Oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like can be used.
- these may be formed separately, they may be used as a single layer formed by mixing with other materials, and layers formed separately by the above plurality of materials may be used together by the above plurality of materials.
- a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a single film of the above plurality of materials may be employed.
- These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
- alkali metal salts such as lithium fluoride and cesium fluoride
- alkaline earth metal salts such as magnesium fluoride
- lithium quinolinol And metal oxides of quinolinol derivatives metal oxides such as aluminum oxide, or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), cesium (Cs), etc.
- Yb ytterbium
- Sm samarium
- Ca calcium
- Cs cesium
- a material generally used in the layer may be further N-doped with a metal such as cesium.
- 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 an electrode material.
- the melting point and the glass transition point of the pyrimidine compound represented by the general formula (1) were measured by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). Melting point glass transition point The compound of Example 1 236 ° C 115 ° C Compound of Example 2 267 ° C 135 ° C Compound of Example 3 not observed 146 ° C Compound of Example 4 331 ° C 164 ° C Compound of Example 5 257 ° C 103 ° C The compound of Example 6 306 ° C 157 ° C The compound of Example 7 303 ° C 144 ° C Compound of Example 8 not observed 148 ° C. Compound of Example 9: 306 ° C., 151 ° C.
- the compound having a pyrimidine ring structure represented by the general formula (1) has a glass transition point of 100 ° C. or more, which indicates that the thin film state is stable.
- a deposited film having a film thickness of 100 nm is prepared on an ITO substrate, and an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS- The work function was measured by 202).
- Example 1 6.53 eV Compound of Example 2 6.57 eV Compound of Example 3 6.52 eV Compound of Example 4 6.40 eV Compound of Example 5 6.49 eV Compound of Example 6 6.53 eV Compound of Example 7 5.97 eV Compound of Example 8 6.43 eV Compound of Example 9 6.51 eV Compound of Example 10 6.51 eV Compound of Example 11 6.59 eV Compound of Example 12 6.58 eV Compound of Example 13 6.58 eV Compound of Example 14 6.51 eV Compound 6.56 eV of Example 15 Compound of Example 16 6.59 eV Compound of Example 17 6.07 eV
- the compound having a pyrimidine ring structure represented by the general formula (1) has a work function value higher than 5.5 eV possessed by general hole transport materials such as NPD and TPD, and has a large hole blocking ability. Have.
- the organic EL device has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a hole blocking layer on an ITO electrode previously formed as a transparent anode 2 on a glass substrate 1.
- the layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were sequentially deposited and manufactured.
- the glass substrate 1 on which ITO having a film thickness of 50 nm was formed was subjected to ultrasonic cleaning for 20 minutes in isopropyl alcohol and then dried for 10 minutes on a hot plate heated to 200 ° C. Thereafter, UV ozone treatment was carried out for 15 minutes, and then the ITO-attached glass substrate was mounted in a vacuum deposition machine, and the pressure was reduced to 0.001 Pa or less. Subsequently, an electron acceptor (Acceptor-1) of the following structural formula and a compound (HTM-1) of the following structural formula are used as the hole injection layer 3 so as to cover the transparent anode 2, and the deposition rate ratio is Acceptor-1: HTM.
- Binary vapor deposition was performed at a vapor deposition rate of -1: 3: 97 to form a film thickness of 10 nm.
- a compound (HTM-1) of the following structural formula was formed as a hole transport layer 4 to have a film thickness of 60 nm.
- EMD-1 a compound of the following structural formula
- EMH-1 5
- Binary vapor deposition was performed at a vapor deposition rate of 95 to form a film thickness of 20 nm.
- Lithium fluoride was formed as the electron injection layer 8 to a film thickness of 1 nm on the hole blocking and electron transporting layers 6 and 7.
- aluminum was deposited 100 nm to form a cathode 9.
- Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (compound -26) of Example 2 is used instead of the compound (compound -17) of Example 1 of the present invention as a material of the hole blocking layer-cum-electron transport layer 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-27) of Example 3 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-36) of Example 4 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-43) of Example 5 is used instead of the compound (Compound-17) of Example 1 of the present invention as a material of the hole blocking layer-cum-electron transport layer 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-46) of Example 6 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-149) of Example 7 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-151) of Example 8 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-152) of Example 9 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer-cum-electron transport layers 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-153) of Example 10 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layers 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-154) of Example 11 is used instead of the compound (Compound-17) of Example 1 of the present invention as a material of the hole blocking layer-cum-electron transport layer 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-155) of Example 12 is used instead of the compound (Compound-17) of Example 1 of the present invention as a material of the hole blocking layer-cum-electron transport layer 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-156) of Example 13 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer-cum-electron transport layer 6 and 7, and the deposition rate is
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-157) of Example 14 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-158) of Example 15 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layer 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-159) of Example 16 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer / electron transport layers 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 the compound (Compound-160) of Example 17 is used instead of the compound (Compound-17) of Example 1 of the present invention as the material of the hole blocking layer and electron transport layers 6 and 7 and the deposition rate is used.
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 a compound of the following structural formula (ETM-2) is used instead of the compound (Compound-17) of Example 1 of the present invention as a material of the hole blocking layer and electron transport layers 6 and 7
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- Example 20 For comparison, in Example 20, a compound of the following structural formula (ETM-3) is used instead of the compound (Compound-17) of Example 1 of the present invention as a material of the hole blocking layer and electron transport layers 6 and 7
- the characteristics of the produced organic EL device were measured in the air at normal temperature. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
- the device life was measured using the organic EL devices produced in Examples 20 to 36 and Comparative Examples 1 and 2, and the results are shown in Table 1.
- the device life is equivalent to 95% when the light emission luminance is 1900 cd / m 2 (when the initial luminance is 100% when constant current driving is performed with the light emission luminance at the start of light emission (initial luminance) 2000 cd / m 2 : The time to decay to 95%) was measured.
- the driving voltage when a current having a current density of 10 mA / cm 2 was passed was 3.82 of the organic EL elements of Comparative Examples 1 and 2 using the compounds ETM-2 and 3 of the above structural formula.
- the voltage was lowered to 3.42 to 3.72 V with respect to -4.01 V.
- the organic EL elements of Example 20 to Example 36 are 8.24 to 9.24 cd / A as compared with 6.59 to 8.05 cd / A of the organic EL elements of Comparative Examples 1 and 2.
- the organic EL elements of Examples 20 to 36 As compared with the organic EL elements of Comparative Examples 1 and 2 in the power efficiency of 5.16 to 6.62 lm / W, the organic EL elements of Examples 20 to 36 have 7.06 to 8. It greatly improved with 43 lm / W. In particular, in the element life (95% attenuation), the organic EL elements of Examples 20 to 36 have a significantly long operation time of 231 to 323 hours, as compared with 165 to 203 hours for the organic EL elements of Comparative Examples 1 and 2. It has reached the end of life.
- the organic EL device of the present invention is superior in light emission efficiency and power efficiency as compared with devices using the compounds ETM-2 and 3 of the above-mentioned structural formula, and can realize an organic EL device having a long life. all right.
- the compound having a specific pyrimidine ring structure of the present invention is excellent as a compound for an organic EL device because it has good electron injection properties, excellent hole blocking ability, and stable thin film state.
- By manufacturing an organic EL element using the compound high efficiency can be obtained, driving voltage can be reduced, and durability can be improved. For example, it has become possible to expand to home appliances and lighting applications.
Abstract
Description
そして、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おり、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3参照)
(式中、A1は置換または無置換の芳香族複素環基を表す。Ar1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を表す。Ar2は重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。mは1~3の整数を表し、nは0~2の整数を表し、oは1~2の整数を表す。mが2以上の整数である場合、同一のピリミジン環に複数個結合するAr1は相互に同一でも異なってもよい。nが2の整数である場合、同一のピリミジン環に複数個結合するAr2は相互に同一でも異なってもよい。oが2の整数である場合、同一のピリミジン環に複数個結合するA1は相互に同一でも異なってもよい。但し、mとnとoの整数の和を4以内とする。尚、nが0の場合、Ar2は水素原子を表すものとする。)
(式中、A2は置換または無置換の芳香族複素環基を表す。Ar3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を表す。Ar4は重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。pは1~3の整数を表し、qは0~2の整数を表す。pが2以上の整数である場合、同一のピリミジン環に複数個結合するAr3は相互に同一でも異なってもよい。qが2の整数である場合、同一のピリミジン環に複数個結合するAr4は相互に同一でも異なってもよい。但し、pとqの整数の和を3以内とする。)
(式中、A3は置換または無置換の芳香族複素環基を表す。Ar5、Ar6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を表す。Ar7は水素原子、重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。)
(式中、A4は置換または無置換の芳香族複素環基を表す。Ar8、Ar9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を表す。Ar10は水素原子、重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。)
(式中、A5は置換または無置換の芳香族複素環基を表す。Ar11、Ar12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を表す。Ar13は水素原子、重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。)
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(ピリジン-3-イル)-ピリミジン:7.5g、4-(フェナンスレン-9-イル)-フェニルボロン酸:7.2g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.5g、炭酸カリウム:6.0gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成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/酢酸エチル)によって精製を行うことで、6-(ビフェニル-4-イル)-2-{4-(フェナンスレン-9-イル)-フェニル}-4-(ピリジン-3-イル)-ピリミジン(化合物-17)の白色粉体:1.5g(収率12%)を得た。
1H-NMR(CDCl3)で以下の27個の水素のシグナルを検出した。
δ(ppm)=9.55(1H)、8.90(2H)、8.85(1H)、8.82(1H)、8.78(1H)、8.70(1H)、8.46(2H)、8.15(1H)、8.04(1H)、7.97(1H)、7.86(2H)、7.80(2H)、7.78-7.49(10H)、7.44(1H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(ピリジン-3-イル)-ピリミジン:5.0g、2-(9,9-ジフェニル[9H]フルオレン)ボロン酸:6.8g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.3g、炭酸カリウム:2.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成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/酢酸エチル)によって精製を行うことで、6-(ビフェニル-4-イル)-2-(9,9-ジフェニル[9H]フルオレン-2-イル)-4-(ピリジン-3-イル)-ピリミジン(化合物-26)の淡灰褐色粉体:6.6g(収率73%)を得た。
1H-NMR(DMSO-d6)で以下の31個の水素のシグナルを検出した。
δ(ppm)=9.63(1H)、8.81(2H)、8.77(1H)、8.69(2H)、8.58(2H)、8.19(1H)、8.08(1H)、7.96(2H)、7.84(2H)、7.68(1H)、7.54(3H)、7.45(3H)、7.39-7.21(10H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(ピリジン-3-イル)-ピリミジン:7.0g、2-(9,9'-スピロビ[9H]フルオレン)ボロン酸:8.1g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.5g、炭酸カリウム:3.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、6-(ビフェニル-4-イル)-4-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-2-イル)-ピリミジン(化合物-27)の白色粉体:5.5g(収率43%)を得た。
1H-NMR(CDCl3)で以下の29個の水素のシグナルを検出した。
δ(ppm)=9.37(1H)、8.85(1H)、8.75(1H)、8.46(1H)、8.26(2H)、8.06(1H)、8.05(1H)、7.94(4H)、7.77(2H)、7.69(2H)、7.55-7.37(7H)、7.16(3H)、6.83(2H)、6.75(1H)。
実施例3において、2-(9,9'-スピロビ[9H]フルオレン)ボロン酸に代えて、4-(9,9'-スピロビ[9H]フルオレン-2-イル)-フェニルボロン酸を用いて、同条件下で反応を行うことで、6-(ビフェニル-4-イル)-4-(ピリジン-3-イル)-2-{4-(9,9'-スピロビ[9H]フルオレン-2-イル)-フェニル}-ピリミジン(化合物-36)の白色粉体:6.4g(収率45%)を得た。
1H-NMR(CDCl3)で以下の33個の水素のシグナルを検出した。
δ(ppm)=9.48(1H)、8.80(1H)、8.69(2H)、8.60(1H)、8.38(2H)、8.06(1H)、7.98(1H)、7.91(1H)、7.90(2H)、7.82(2H)、7.76(1H)、7.71(2H)、7.64(2H)、7.52(3H)、7.46-7.37(4H)、7.16(3H)、7.09(1H)、6.84(2H)、6.78(1H)。
反応容器に2-クロロ-6-{4-(ナフタレン-1-イル)-フェニル}-4-(ピリジン-3-イル)-ピリミジン:8.0g、4-(ナフタレン-1-イル)-フェニルボロン酸:5.5g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.5g、炭酸カリウム:3.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にメタノールを加えて析出した固体を濾過して粗生成物を得た。得られた粗生成物をモノクロロベンゼン溶媒により再結晶精製を行うことで、2,6-ビス{4-(ナフタレン-1-イル)-フェニル}-4-(ピリジン-3-イル)-ピリミジン(化合物-43)の白色粉体:6.8g(収率60%)を得た。
1H-NMR(CDCl3)で以下の27個の水素のシグナルを検出した。
δ(ppm)=9.57(1H)、8.91(2H)、8.84(1H)、8.71(1H)、8.50(2H)、8.19(1H)、8.07-7.90(6H)、7.76(4H)、7.64-7.45(9H)。
反応容器に2-クロロ-6-{4-(ナフタレン-1-イル)-フェニル}-4-(ピリジン-3-イル)-ピリミジン:8.0g、2-(9,9'-スピロビ[9H]フルオレン)ボロン酸:8.1g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.5g、炭酸カリウム:3.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にメタノールを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をモノクロロベンゼン/アセトン混合溶媒により晶析精製を行うことで、6-{4-(ナフタレン-1-イル)-フェニル}-4-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-2-イル)-ピリミジン(化合物-46)の白色粉体:6.2g(収率45%)を得た。
1H-NMR(CDCl3)で以下の31個の水素のシグナルを検出した。
δ(ppm)=9.40(1H)、8.88(1H)、8.77(1H)、8.48(1H)、8.31(2H)、8.12-7.87(9H)、7.68(2H)、7.57(2H)、7.53-7.36(6H)、7.16(3H)、6.84(2H)、6.76(1H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(ピリジン-3-イル)-ピリミジン:6.0g、3-(10-フェニル-アントラセン-9-イル)フェニルボロン酸:7.8g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:4.8gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をモノクロロベンゼン溶媒により再結晶精製を行うことで、6-(ビフェニル-4-イル)-2-{3-(10-フェニル-アントラセン-9-イル)-フェニル}-4-(ピリジン-3-イル)-ピリミジン(化合物-149)の白色粉体:6.2g(収率56%)を得た。
1H-NMR(CDCl3)で以下の31個の水素のシグナルを検出した。
δ(ppm)=9.47(1H)、8.98(1H)、8.88(1H)、8.77(1H)、8.62(1H)、8.39(2H)、8.13(1H)、7.89-7.73(8H)、7.71-7.34(15H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(ピリジン-3-イル)-ピリミジン:5.0g、4-(9,9'-スピロビ[9H]フルオレン)ボロン酸:5.8g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.3g、炭酸カリウム:2.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成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)によって精製を行うことで、6-(ビフェニル-4-イル)-4-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-4-イル)-ピリミジン(化合物-151)の淡灰褐色粉体:4.0g(収率44%)を得た。
1H-NMR(DMSO-d6)で以下の29個の水素のシグナルを検出した。
δ(ppm)=9.75(1H)、8.97(1H)、8.87(1H)、8.82(1H)、8.65(2H)、8.07(2H)、7.92(2H)、7.84(3H)、7.68(1H)、7.64(1H)、7.54(2H)、7.45(3H)、7.33(1H)、7.20(2H)、7.13(2H)、6.77(1H)、6.76(2H)、6.65(1H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(キノリン-8-イル)-ピリミジン:6.0g、2-(9,9'-スピロビ[9H]フルオレン)ボロン酸:6.0g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:2.5gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にメタノールを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をモノクロロベンゼン溶媒により再結晶精製を行うことで、6-(ビフェニル-4-イル)-4-(キノリン-8-イル)-2-(9,9'-スピロビ[9H]フルオレン-2-イル)-ピリミジン(化合物-152)の白色粉体:6.5g(収率63%)を得た。
1H-NMR(DMSO-d6)で以下の31個の水素のシグナルを検出した。
δ(ppm)=8.94(1H)、8.80(1H)、8.55(1H)、8.52(1H)、8.32(2H)、8.27(1H)、8.18(2H)、8.14(1H)、8.07(2H)、7.88(2H)、7.78(4H)、7.63(1H)、7.51(3H)、7.43(3H)、7.18(3H)、6.72(2H)、6.63(1H)。
反応容器に6-(ビフェニル-4-イル)-2-クロロ-4-(キノリン-8-イル)-ピリミジン:6.0g、2-(9,9-ジフェニル[9H]フルオレン)ボロン酸:7.2g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:2.5gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成物をアセトン溶媒により再結晶精製を行うことで、6-(ビフェニル-4-イル)-2-(9,9-ジフェニル[9H]フルオレン-2-イル)-4-(キノリン-8-イル)-ピリミジン(化合物-153)の白色粉体:8.5g(収率83%)を得た。
1H-NMR(CDCl3)で以下の33個の水素のシグナルを検出した。
δ(ppm)=9.04(1H)、8.76(1H)、8.73(1H)、8.66(1H)、8.56(1H)、8.42(3H)、8.23(1H)、8.17(1H)、8.06(1H)、7.94(2H)、7.87(1H)、7.81(2H)、7.68(1H)、7.54(3H)、7.46(2H)、7.41(1H)、7.38-7.19(10H)。
反応容器に2-クロロ-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン:8.0g、2-(9,9-ジフェニル[9H]フルオレン)ボロン酸:7.6g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:5.4gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にメタノールを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、2-(9,9-ジフェニル[9H]フルオレン-2-イル)-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン(化合物-154)の白色粉体:3.9g(収率29%)を得た。
1H-NMR(CDCl3)で以下の35個の水素のシグナルを検出した。
δ(ppm)=9.47(1H)、8.81(1H)、8.80(2H)、8.57(1H)、8.37(2H)、8.05(1H)、7.96(1H)、7.88(3H)、7.78(4H)、7.68(2H)、7.56-7.23(17H)。
反応容器に2-クロロ-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン:8.0g、2-(9,9'-スピロビ[9H]フルオレン)ボロン酸:6.9g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:3.2gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、4-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-2-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン(化合物-155)の白色粉体:4.2g(収率32%)を得た。
1H-NMR(CDCl3)で以下の33個の水素のシグナルを検出した。
δ(ppm)=9.38(1H)、8.86(1H)、8.76(1H)、8.47(1H)、8.28(2H)、8.07(1H)、8.05(1H)、7.95(4H)、7.82(2H)、7.76(4H)、7.69(2H)、7.51(3H)、7.42(4H)、7.16(3H)、6.83(2H)、6.76(1H)。
反応容器に2-クロロ-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン:8.0g、3-(9,9-ジフェニル[9H]フルオレン)ボロン酸:7.6g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:5.3gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、2-(9,9-ジフェニル[9H]フルオレン-3-イル)-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン(化合物-156)の白色粉体:3.4g(収率25%)を得た。
1H-NMR(CDCl3)で以下の35個の水素のシグナルを検出した。
δ(ppm)=9.54(1H)、9.10(1H)8.83(1H)、8.67(2H)、8.45(2H)、8.12(1H)、8.03(1H)、7.90(2H)、7.79(4H)、7.70(2H)、7.62(1H)、7.56(2H)、7.54-7.23(15H)。
反応容器に2-クロロ-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン:5.5g、4-(9,9-ジフェニル[9H]フルオレン)ボロン酸:4.7g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.3g、炭酸カリウム:3.6gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、2-(9,9-ジフェニル[9H]フルオレン-4-イル)-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン(化合物-157)の白色粉体:3.2g(収率35%)を得た。
1H-NMR(CDCl3)で以下の35個の水素のシグナルを検出した。
δ(ppm)=9.50(1H)、8.81(1H)、8.64(1H)、8.43(2H)、8.30(1H)、7.86(3H)、7.77(4H)、7.68(2H)、7.60(1H)、7.58(1H)、7.54-7.21(17H)、7.10(1H)。
反応容器に2-クロロ-4-(ピリジン-3-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン:8.0g、4-(9,9'-スピロビ[9H]フルオレン)ボロン酸:6.9g、テトラキス(トリフェニルホスフィン)パラジウム(0):0.4g、炭酸カリウム:5.3gを仕込み、トルエン、エタノール、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、4-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-4-イル)-6-([1,1';4',1'']ターフェニル-4-イル)-ピリミジン(化合物-158)の白色粉体:3.7g(収率28%)を得た。
1H-NMR(CDCl3)で以下の33個の水素のシグナルを検出した。
δ(ppm)=9.55(1H)、8.83(1H)、8.70(1H)、8.48(2H)、8.33(1H)、7.90(5H)、7.79(4H)、7.75(1H)、7.69(2H)、7.54(1H)、7.51(2H)、7.43(3H)、7.28(1H)、7.18(2H)、7.11(2H)、6.91(2H)、6.88(1H)、6.78(1H)。
反応容器に5-クロロ-4-(フェナンスレン-9-イル)-2-(9,9'-スピロビ[9H]フルオレン-4-イル)-ピリミジン:5.0g、3-ピリジルボロン酸:1.2g、トリス(ジベンジリデンアセトン)ジパラジウム(0):0.4g、トリシクロヘキシルホスフィン:0.5gリン酸三カリウム:5.3gを仕込み、1,4-ジオキサン、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2Oを加え、分液操作にて有機層を抽出した後、減圧下濃縮した。得られた粗生成物をカラムクロマトグラフ(担体:シリカゲル、溶離液:ジクロロメタン/酢酸エチル)によって精製を行うことで、4-(フェナンスレン-9-イル)-5-(ピリジン-3-イル)-2-(9,9'-スピロビ[9H]フルオレン-4-イル)-ピリミジン(化合物-159)の白色粉体:1.7g(収率32%)を得た。
1H-NMR(CDCl3)で以下の29個の水素のシグナルを検出した。
δ(ppm)=δ(ppm)=8.84(1H)、8.70(2H)、8.67(1H)、8.47(1H)、8.33(1H)、7.98(1H)、7.96(1H)、7.91(1H)、7.87(2H)、7.78(1H)、7.70(1H)、7.61(4H)、7.46-7.26(5H)、7.14(3H)、6.94(1H)、6.80(2H)、6.75(1H)。
反応容器に4-(ビフェニル-4-イル)-5-クロロ-2-(10-フェニル-アントラセン-9-イル)-ピリミジン:5.0g、8-キノリンボロン酸:2.0g、トリス(ジベンジリデンアセトン)ジパラジウム(0):0.4g、トリシクロヘキシルホスフィン:0.5gリン酸三カリウム:6.1gを仕込み、1,4-ジオキサン、H2O混合溶媒下にて一晩還流撹拌した。放冷した後、系内にH2O、メタノールを加え、析出した固体を濾過して粗生成物を得た。得られた粗生成物をトルエン/アセトン混合溶媒による晶析精製を行うことで、4-(ビフェニル-4-イル)-2-(10-フェニル-アントラセン-9-イル)-5-(キノリン-8-イル)-ピリミジン(化合物-160)の淡黄色粉体:3.0g(収率51%)を得た。
1H-NMR(CDCl3)で以下の29個の水素のシグナルを検出した。
δ(ppm)=9.42(1H)、9.15(1H)、8.70(1H)、8.14(1H)、7.90(2H)、7.88-7.59(10H)、7.55-7.30(13H)。
融点 ガラス転移点
実施例1の化合物 236 ℃ 115 ℃
実施例2の化合物 267 ℃ 135 ℃
実施例3の化合物 観測されず 146 ℃
実施例4の化合物 331 ℃ 164 ℃
実施例5の化合物 257 ℃ 103 ℃
実施例6の化合物 306 ℃ 157 ℃
実施例7の化合物 303 ℃ 144 ℃
実施例8の化合物 観測されず 148 ℃
実施例9の化合物 306 ℃ 151 ℃
実施例10の化合物 観測されず 137 ℃
実施例11の化合物 282 ℃ 147 ℃
実施例12の化合物 274 ℃ 159 ℃
実施例13の化合物 326 ℃ 149 ℃
実施例14の化合物 275 ℃ 148 ℃
実施例15の化合物 観測されず 161 ℃
実施例16の化合物 観測されず 164 ℃
実施例17の化合物 観測されず 141 ℃
仕事関数
実施例1の化合物 6.53 eV
実施例2の化合物 6.57 eV
実施例3の化合物 6.52 eV
実施例4の化合物 6.40 eV
実施例5の化合物 6.49 eV
実施例6の化合物 6.53 eV
実施例7の化合物 5.97 eV
実施例8の化合物 6.43 eV
実施例9の化合物 6.51 eV
実施例10の化合物 6.51 eV
実施例11の化合物 6.59 eV
実施例12の化合物 6.58 eV
実施例13の化合物 6.58 eV
実施例14の化合物 6.51 eV
実施例15の化合物 6.56 eV
実施例16の化合物 6.59 eV
実施例17の化合物 6.07 eV
比較のために、実施例20において、正孔阻止層兼電子輸送層6および7の材料として本発明実施例1の化合物(化合物-17)に代えて、下記構造式の化合物(ETM-2)(例えば、特許文献6参照)を用い、蒸着速度比がETM-2:ETM-1=50:50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。
比較のために、実施例20において、正孔阻止層兼電子輸送層6および7の材料として本発明実施例1の化合物(化合物-17)に代えて、下記構造式の化合物(ETM-3)(例えば、特許文献8参照)を用い、蒸着速度比がETM-3:ETM-1=50:50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 正孔阻止層
7 電子輸送層
8 電子注入層
9 陰極
Claims (20)
- 下記一般式(1)で表される、ピリミジン環構造を有する化合物。
(式中、A1は置換または無置換の芳香族複素環基を表す。Ar1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を表す。Ar2は重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。mは1~3の整数を表し、nは0~2の整数を表し、oは1~2の整数を表す。mが2以上の整数である場合、同一のピリミジン環に複数個結合するAr1は相互に同一でも異なってもよい。nが2の整数である場合、同一のピリミジン環に複数個結合するAr2は相互に同一でも異なってもよい。oが2の整数である場合、同一のピリミジン環に複数個結合するA1は相互に同一でも異なってもよい。但し、mとnとoの整数の和を4以内とする。尚、nが0の場合、Ar2は水素原子を表すものとする。) - 請求項1記載のピリミジン環構造を有する化合物であって、
下記一般式(2)で表される、ピリミジン環構造を有する化合物
(式中、A2は置換または無置換の芳香族複素環基を表す。Ar3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を表す。Ar4は重水素原子、トリメチルシリル基、トリフェニルシリル基、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、または置換もしくは無置換の縮合多環芳香族基を表す。pは1~3の整数を表し、qは0~2の整数を表す。pが2以上の整数である場合、同一のピリミジン環に複数個結合するAr3は相互に同一でも異なってもよい。qが2の整数である場合、同一のピリミジン環に複数個結合するAr4は相互に同一でも異なってもよい。但し、pとqの整数の和を3以内とする。) - 請求項4記載のピリミジン環構造を有する化合物であって、
前記A4の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基、またはカルボニル基である、前記一般式(4)で表される
ピリミジン環構造を有する化合物。 - 請求項5記載のピリミジン環構造を有する化合物であって、
前記A5の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基、またはカルボニル基である、前記一般式(5)で表される
ピリミジン環構造を有する化合物。 - 請求項4記載のピリミジン環構造を有する化合物であって、
前記Ar10が水素原子である前記一般式(4)で表される
ピリミジン環構造を有する化合物。 - 請求項5記載のピリミジン環構造を有する化合物であって、
前記Ar13が水素原子である前記一般式(5)で表される
ピリミジン環構造を有する化合物。 - 請求項4記載のピリミジン環構造を有する化合物であって、
前記A4の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基、またはカルボニル基であり、かつ、前記Ar10が水素原子である前記一般式(4)で表される
ピリミジン環構造を有する化合物。 - 請求項5記載のピリミジン環構造を有する化合物であって、
前記A5の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基、またはカルボニル基であり、かつ、前記Ar13が水素原子である前記一般式(5)で表される
ピリミジン環構造を有する化合物。 - 請求項4記載のピリミジン環構造を有する化合物であって、
前記Ar8、Ar9の内、少なくとも1カ所が縮合多環芳香族基、芳香族複素環基または置換基として、フェナントレニル基、フルオレニル基、スピロビフルオレニル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、またはジベンゾチエニル基であり、かつ、前記Ar10が水素原子である、前記一般式(4)で表される
ピリミジン環構造を有する化合物。 - 請求項5記載のピリミジン環構造を有する化合物であって、
前記Ar11、Ar12の内、少なくとも1カ所が縮合多環芳香族基、芳香族複素環基、または置換基として、フェナントレニル基、フルオレニル基、スピロビフルオレニル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、またはジベンゾチエニル基であり、かつ、前記Ar13が水素原子である前記一般式(5)で表される
ピリミジン環構造を有する化合物。 - 請求項4記載のピリミジン環構造を有する化合物であって、
前記A4の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基、またはカルボニル基であり、かつ、前記Ar10が水素原子であり、かつ、前記Ar8、Ar9の内、少なくとも1カ所が縮合多環芳香族基、芳香族複素環基、または置換基として、フェナントレニル基、フルオレニル基、スピロビフルオレニル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、またはジベンゾチエニル基である前記一般式(4)で表される
ピリミジン環構造を有する化合物。 - 請求項5記載のピリミジン環構造を有する化合物であって、
前記A5の芳香族複素環基が、ピリジル基、ピリミジル基、キノリル基、イソキノリル基、インドリル基、アザフルオレニル基、ジアザフルオレニル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、アザスピロビフルオレニル基、ジアザスピロビフルオレニル基またはカルボリニル基であり、かつ、前記Ar13が水素原子であり、かつ、前記Ar11、Ar12の内、少なくとも1カ所が縮合多環芳香族基、芳香族複素環基、または置換基として、フェナントレニル基、フルオレニル基、スピロビフルオレニル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、またはジベンゾチエニル基である、前記一般式(5)で表される
ピリミジ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、請求項1~15のいずれか一項に記載のピリミジ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。 - 請求項16記載の有機エレクトロルミネッセンス素子であって、
前記ピリミジン環構造を有する化合物が用いられている前記有機層が電子輸送層である
有機エレクトロルミネッセンス素子。 - 請求項16記載の有機エレクトロルミネッセンス素子であって、
前記ピリミジン環構造を有する化合物が用いられている前記有機層が正孔阻止層である
有機エレクトロルミネッセンス素子。 - 請求項16記載の有機エレクトロルミネッセンス素子であって、
前記ピリミジン環構造を有する化合物が用いられている前記有機層が発光層である
有機エレクトロルミネッセンス素子。 - 請求項16記載の有機エレクトロルミネッセンス素子であって、
前記ピリミジン環構造を有する化合物が用いられている前記有機層が電子注入層である
有機エレクトロルミネッセンス素子。
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US16/646,108 US20200277272A1 (en) | 2017-09-11 | 2018-09-07 | Compound having pyrimidine ring structure and organic electroluminescence device |
JP2019541014A JP7159173B2 (ja) | 2017-09-11 | 2018-09-07 | ピリミジ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 |
CN201880059472.0A CN111094264A (zh) | 2017-09-11 | 2018-09-07 | 具有嘧啶环结构的化合物及有机电致发光元件 |
EP18854331.8A EP3683212A4 (en) | 2017-09-11 | 2018-09-07 | COMPOUND WITH A CYCLIC STRUCTURE OF PYRIMIDINE TYPE AND ORGANIC ELECTROLUMINESCENT ELEMENT |
KR1020207008115A KR102603365B1 (ko) | 2017-09-11 | 2018-09-07 | 피리미딘 고리 구조를 갖는 화합물 및 유기 일렉트로 루미네선스 소자 |
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US20220052268A1 (en) * | 2018-10-17 | 2022-02-17 | Hodogaya Chemical Co., Ltd. | Compound having pyrimidine ring structure and organic electroluminescent element |
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JP7159173B2 (ja) | 2022-10-24 |
TWI824763B (zh) | 2023-12-01 |
EP3683212A1 (en) | 2020-07-22 |
KR102603365B1 (ko) | 2023-11-16 |
TWI808095B (zh) | 2023-07-11 |
CN111094264A (zh) | 2020-05-01 |
EP3683212A4 (en) | 2021-06-09 |
US20200277272A1 (en) | 2020-09-03 |
KR20200051651A (ko) | 2020-05-13 |
TW201918478A (zh) | 2019-05-16 |
JPWO2019049965A1 (ja) | 2020-08-20 |
TW202304874A (zh) | 2023-02-01 |
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