JP6735753B2 - 有機化合物及びこれを含む有機電界発光素子 - Google Patents
有機化合物及びこれを含む有機電界発光素子 Download PDFInfo
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- JP6735753B2 JP6735753B2 JP2017534340A JP2017534340A JP6735753B2 JP 6735753 B2 JP6735753 B2 JP 6735753B2 JP 2017534340 A JP2017534340 A JP 2017534340A JP 2017534340 A JP2017534340 A JP 2017534340A JP 6735753 B2 JP6735753 B2 JP 6735753B2
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- 150000002894 organic compounds Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 129
- 239000000126 substance Substances 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 23
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- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims 1
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- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 36
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000005647 linker group Chemical group 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- -1 Metal complex compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
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- 239000011368 organic material Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
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- BGKHQCLJYVUKNB-UHFFFAOYSA-N (9,9-dimethylfluoren-1-yl)boronic acid Chemical compound C1=CC(B(O)O)=C2C(C)(C)C3=CC=CC=C3C2=C1 BGKHQCLJYVUKNB-UHFFFAOYSA-N 0.000 description 10
- CPFALCJMNUHBHP-UHFFFAOYSA-N (9,9-diphenylfluoren-2-yl)boronic acid Chemical compound C12=CC(B(O)O)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 CPFALCJMNUHBHP-UHFFFAOYSA-N 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WDDLHUWVLROJLA-UHFFFAOYSA-N 9,9'-spirobi[fluorene]-2-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(B(O)O)C=C12 WDDLHUWVLROJLA-UHFFFAOYSA-N 0.000 description 9
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 6
- JTRWBBPLLGECJS-UHFFFAOYSA-N (9,9-dimethylfluoren-3-yl)boronic acid Chemical compound OB(O)C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 JTRWBBPLLGECJS-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- BPMSGKUGXMWVBH-UHFFFAOYSA-N 4-(3-bromophenyl)-2,6-diphenylpyrimidine Chemical compound BrC1=CC=CC(C=2N=C(N=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BPMSGKUGXMWVBH-UHFFFAOYSA-N 0.000 description 5
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 5
- 229940126086 compound 21 Drugs 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- YKCZGQXLXXMGNR-UHFFFAOYSA-N (9,9-dimethylfluoren-4-yl)boronic acid Chemical compound C1=CC=C(B(O)O)C2=C1C(C)(C)C1=CC=CC=C12 YKCZGQXLXXMGNR-UHFFFAOYSA-N 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 3
- BYDMGWHTARYHKO-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenylpyrimidine Chemical compound BrC1=CC=CC(C=2N=C(C=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BYDMGWHTARYHKO-UHFFFAOYSA-N 0.000 description 3
- CUDDLYMAQMEZDS-UHFFFAOYSA-N 2-[3-[3-(9,9-dimethylfluoren-2-yl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound CC1(C)C2=CC=CC=C2C2=C1C=C(C=C2)C1=CC=CC(=C1)C1=CC(=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 CUDDLYMAQMEZDS-UHFFFAOYSA-N 0.000 description 3
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- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
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- 125000000732 arylene group Chemical group 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- RHFORYDUXQKHCI-UHFFFAOYSA-N (9,9-diphenylfluoren-3-yl)boronic acid Chemical compound C1(=CC=CC=C1)C1(C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O)C1=CC=CC=C1 RHFORYDUXQKHCI-UHFFFAOYSA-N 0.000 description 2
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- OABSSTCHGCWNTP-UHFFFAOYSA-N 2,4-diphenyl-6-[3-(9,9'-spirobi[fluorene]-2-yl)phenyl]pyrimidine Chemical compound C1=C(C=CC=2C3=CC=CC=C3C3(C1=2)C1=CC=CC=C1C=1C=CC=CC=13)C=1C=C(C=CC=1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 OABSSTCHGCWNTP-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Description
(式中、
Ra及びRbは、互いに同一又は異なり、それぞれ独立に、C1〜C40のアルキル基、又はC6〜C60のアリール基であり、又は、互いに結合して縮合環を形成し、
R1〜R3は、互いに同一又は異なり、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキシド基、及びC6〜C60のアリールアミン基からなる群から選択され、又は、隣接した基と結合(具体的に、隣接するR1同士が結合、隣接するR2同士が結合、隣接するR3同士が結合、又は、R1とR2とが結合)して縮合環を形成し、
Lは、単結合、C6〜C18のアリーレン基(arylene)、核原子数5〜18のヘテロアリーレン基からなる群から選択され、
Z1〜Z5は、互いに同一又は異なり、それぞれ独立に、N又はC(R4)であり、この時、少なくとも1つは、Nであり、C(R4)が複数の場合、複数のC(R4)は、互いに同一又は異なり、
c、eは、それぞれ0〜4の整数であり、
dは、0〜3の整数であり、
m、nは、それぞれ1〜3の整数であり、
前記R4は、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキシド基、及びC6〜C60のアリールアミン基からなる群から選択され、又は、隣接した基と結合(具体的に、隣接するR4同士が結合)して縮合環を形成し、
前記Ra、Rbのアルキル基、アリール基と、前記R1〜R4のアルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキシド基、アリールアミン基と、前記Lのアリーレン基、ヘテロアリーレン基とは、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキシド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上の置換基で置換又は非置換であり、前記置換基が複数の場合、複数の置換基は、互いに同一又は異なる)
本発明の有機化合物は、フルオレンモイエティと6員ヘテロ環とが、リンカー基(フェニレン又はビフェニレン又はターフェニレン)により結合され、基本骨格をなす化合物であって、前記化1で示される。
(式中、
Ra、Rb、R1〜R3、Z1〜Z5、c、d及びeは、それぞれ前記化1における定義と同様である)
(*は、Lとの結合がなされる部位)で示される構造(置換体)は、下記のC−1〜C−15で示される構造(置換体)のいずれか1つに具体化されることが好ましい。
(式中、
R4は、化1における定義と同様であり、複数のR4は、互いに同一又は異なり、
R5は、水素、重水素、ハロゲン基、シアノ基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C6〜C60のアリールオキシ基、C1〜C40のアルキルオキシ基、C6〜C60のアリールアミン基、C1〜C40のアルキルシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキシド基、及びC6〜C60のアリールシリル基からなる群から選択され、又は、隣接する基と結合(具体的に、隣接するR5同士が結合、又は、R4とR5との結合)して縮合環を形成し、
pは、1〜4の整数であり、
前記R5のアルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アリールオキシ基、アルキルオキシ基、アリールアミン基、アルキルシリル基、アルキルボロン基、アリールボロン基、アリールホスフィン基、アリールホスフィンオキシド基、及びアリールシリル基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C6〜C60のアリールオキシ基、C1〜C40のアルキルオキシ基、C6〜C60のアリールアミン基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C1〜C40のアルキルシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C6〜C60のアリールホスフィン基、C6〜C60のアリールホスフィンオキシド基、及びC6〜60のアリールシリル基からなる群から選択された1種以上の置換基で置換又は非置換であり、この時、前記置換基が複数である場合、複数の置換基は、互いに同一又は異なる)
で示される構造は、前記C−4、C−6又はC−9で示される構造であることがさらに好ましい。具体的に、本発明の化1で示される化合物は、下記の化5〜化7で示される化合物であることができる。
(式中、
Ra、Rb、R1〜R4、L、c、d、e、m及びnは、それぞれ前記化1における定義と同様である)
なお、有機電界発光素子の特性を考慮して、前記化5で示される化合物において、R4は、互いに同一であることが好ましい。即ち、R4が同一であって対称構造をなしていることが好ましい。また、前記化6及び化7で示される化合物において、複数のR4のうちの少なくとも2つ以上は、互いに異なることが好ましい。
(*は、結合がなされる部位)で示される縮合環を形成することが好ましい。
(式中、
Ra、Rb、R1、R2、R4、Z3、c及びdは、それぞれ、前記化1における定義と同様である)
本発明は、前記化1で示される化合物を含む有機電界発光素子を提供する。
HRMS[M]+:501.62
HRMS[M]+:501.62
HRMS[M]+:625.76
HRMS[M]+:623.74
HRMS[M]+:500.63
HRMS[M]+:624.77
HRMS[M]+:622.75
HRMS[M]+:499.64
HRMS[M]+:623.78
HRMS[M]+:622.71
窒素気流下、2−(3−ブロモフェニル)−4,6−ジフェニル−[1,
3,5]トリアジン(12.0g、0.031mol)、3−クロロフェニルボロン酸(6.3g、0.040mol)、Pd(PPh3)4(1.15g、0.001mol)及び炭酸カリウム(12.85g、0.093mol)を混合した後、1,4−ジオキサン(100ml)及びH2O(25ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得られた中間体1−A(11.0g、0.026mol)、9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸(7.9g、0.033mol)、Pd(OAc)2(0.29g、0.001mol)、炭酸セシウム(25.4g、0.078mol)及びXphos(1.23g、0.003mol)を混合した後、トルエン(100ml)/エタノール(20ml)/H2O(20ml)で還流攪拌した。
HRMS[M]+:577.72
HRMS[M]+:577.72
HRMS[M]+:701.85
HRMS[M]+:701.85
HRMS[M]+:699.84
HRMS[M]+:699.84
合成例11の<ステップ1>で使用された2−(3−ブロモフェニル)−4,6−ジフェニル−[1,3,5]トリアジンの代わりに、4−(3−ブロモフェニル)−2,6−ジフェニル−ピリミジン(12.0g、0.031mol)を使用する以外は、上述の合成例11の<ステップ1>と同様にして中間体2−Aを得た。
合成例11の<ステップ2>で使用された中間体1−Aの代わりに、<ステップ1>で合成された中間体2−A(11.0g、0.026mol)を使用する以外は、上述の合成例11の<ステップ2>と同様にして化合物31を得た。
HRMS[M]+:576.73
HRMS[M]+:576.73
HRMS[M]+:687.85
HRMS[M]+:698.85
合成例11の<ステップ1>で使用された2−(3−ブロモフェニル)−4,6−ジフェニル−[1,3,5]−トリアジンの代わりに、4−(3−ブロモフェニル)−2,6−ジフェニル−ピリジン(12.0g、0.031mol)を使用する以外は、上述の合成例11の<ステップ1>と同様にして中間体3−Aを得た。
合成例11の<ステップ2>で使用された中間体1−Aの代わりに、上述のステップ<1>で合成された中間体3−A(11.0g、0.026mol)を使用する以外は、上述の合成例11の<ステップ2>と同様にして化合物45を得た。
HRMS[M]+:501.62
HRMS[M]+:699.88
HRMS[M]+:697.86
窒素気流化、中間体1−A(11.0g、0.026mol)、3−クロロフェニルボロン酸(4.8g、0.031mol)、Pd(OAc)2(0.29g、0.001mol)、炭酸セシウム(25.4g、0.078mol)及びXphos(0.3g、0.003mol)を混合した後、トルエン(100ml)/エタノール(20ml)/H2O(20ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得た中間体1−B(7.5g、0.015mol)、9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸(4.3g、0.018mol)、Pd(OAc)2(0.17g、0.75mmol)、炭酸セシウム(14.6g、0.045mmol)及びXphos(0.7g、1.5mmol)を混合した後、トルエン(60ml)/エタノール(15ml)/H2O(15ml)で還流攪拌した。
HRMS[M]+:653.83
HRMS[M]+:653.83
窒素気流化、中間体2−A(11.0g、0.026mol)、3−クロロフェニルボロン酸(4.8g、0.031mol)、Pd(OAc)2(0.29g、0.001mol)、炭酸セシウム(25.4g、0.078mol)及びXphos(0.3g、0.003mol)を混合した後、トルエン(100ml)/エタノール(20ml)/H2O(20ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得た中間体2−B(7.5g、0.015mol)、9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸(4.3g、0.018mol)、Pd(OAc)2(0.17g、0.75mmol)、炭酸セシウム(14.6g、0.045mmol)及びXphos(0.7g、1.5mmol)を混合した後、トルエン(60ml)/エタノール(15ml)/H2O(15ml)で還流攪拌した。
HRMS[M]+:652.84
HRMS[M]+:652.84
合成例11の<ステップ1>で使用された2(3−ブロモフェニル)−4,6−ジフェニル−1,3,5−トリアジンの代わりに、2−([1,1’−ビフェニル]−4−イル)−4−(3−ブロモフェニル)−6−フェニル−1,3,5−トリアジン(14.4g、0.031mol)を使用する以外は、上述の合成例11の<ステップ1>と同様にして中間体4−Aを得た。
合成例11の<ステップ2>で使用された9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸の代わりに、(9,9−ジフェニル−9H−フルオレン−2−イル)ボロン酸(11.9g、0.033mol)を使用する以外は、上述の合成例11の<ステップ2>と同様にして化合物200を得た。
HRMS[M]+:777.97
合成例11の<ステップ1>で使用された2(3−ブロモフェニル)−4,6−ジフェニル−1,3,5−トリアジンの代わりに、4−([1,1’−ビフェニル]−4−イル)−6−(3−ブロモフェニル)−2−フェニルピリミジン(14.3g、0.031mol)を使用する以外は、上述の合成例11の<ステップ1>と同様にして中間体5−Aを得た。
合成例11の<ステップ2>で使用された9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸の代わりに、(9,9−ジフェニル−9H−フルオレン−2−イル)−ボロン酸(11.9g、0.033mol)を使用する以外は、上述の合成例11の<ステップ2>と同様にして化合物206を得た。
HRMS[M]+:776.98
窒素気流下、2−(3−ブロモ−フェニル)−4,6−ジフェニル−[1,3,5]トリアジン(12.0g、0.031mol)、3−クロロフェニルボロン酸(6.3g、0.040mol)、Pd(PPh3)4(1.15g、0.001mol)及び炭酸カリウム(12.85g、0.093mol)を混合した後、1,4−ジオキサン(100ml)及びH2O(25ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得た中間体I−1(11.0g、0.026mol)、(9,9−ジメチル−9H−フルオレン−1−イル)ボロン酸(7.9g、0.033mol)、Pd(OAc)2(0.29g、0.001mol)及び炭酸セシウム(25.4g、0.078mol)及びXphos(1.23g、0.003mol)を混合した後、トルエン(100ml)、エタノール(20ml)及びH2O(20ml)で還流攪拌した。
HRMS[M]+:577.25
HRMS[M]+:701.28
HRMS[M]+:699.27
HRMS[M]+:577.25
HRMS[M]+:639.27
HRMS[M]+:627.27
HRMS[M]+:653.28
HRMS[M]+:749.28
HRMS[M]+:677.28
HRMS[M]+:729.31
HRMS[M]+:775.30
HRMS[M]+:500.23
HRMS[M]+:500.23
HRMS[M]+:624.26
HRMS[M]+:622.24
HRMS[M]+:622.24
窒素気流下、2−(3−ブロモフェニル)−4,6−ジフェニルピリミジン(12.0g、0.031mol)、3−クロロフェニルボロン酸(6.3g、0.040mol)、Pd(PPh3)4(1.15g、0.001mol)及び炭酸カリウム(12.85g、0.093mol)を混合した後、1,4−ジオキサン(100ml)及びH2O(25ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得た中間体1−A(11.0g、0.026mol)、9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸(7.9g、0.033mol)、Pd(OAc)2(0.29g、0.001mol)及び炭酸セシウム(25.4g、0.078mol)及びXphos(1.23g、0.003mol)を混合した後、トルエン(100ml)、エタノール(20ml)及びH2O(25ml)で還流攪拌した。
HRMS[M]+:576.26
HRMS[M]+:576.26
HRMS[M]+:700.29
HRMS[M]+:700.29
HRMS[M]+:698.27
HRMS[M]+:698.27
合成例47の<ステップ1>で使用された2−(3−ブロモフェニル)−4,6−ジフェニルピリミジンの代わりに、4−(3−ブロモフェニル)−2,6−ジフェニルピリミジン(12.0g、0.031mol)を使用する以外は、上述の合成例47の<ステップ1>と同様にして中間体2−Aを得た。
合成例47の<ステップ2>で使用された中間体1−Aの代わりに上述の<ステップ1>で合成された中間体2−A(11.0g、0.026mol)を、9,9−ジメチル−9H−フルオレン−2−イル−ボロン酸の代わりに(9,9−ジメチル−9H−フルオレン−4−イル)ボロン酸 (7.9g、0.033mol)を使用する以外は、上述の合成例47の<ステップ2>と同様にして化合物282を得た。
HRMS[M]+:576.26
HRMS[M]+:698.27
合成例53の<ステップ1>で使用された4−(3−ブロモ−フェニル)−2,6−ジフェニル−ピリミジンの代わりに、4−([1,1’−ビフェニル]−4−イル)−6−(3−ブロモフェニル)−2−フェニル−ピリミジン(14.4g、0.031mol)を使用する以外は、上述の合成例53の<ステップ1>と同様にして中間体3−Aを得た。
合成例53の<ステップ2>で使用された中間体2−Aの代わりに上述の<ステップ1>で合成された中間体3−A(12.9g、0.026mol)を、(9,9−ジメチル−9H−フルオレン−4−イル)ボロン酸の代わりに(9,9−ジメチル−9H−フルオレン−2−イル)ボロン酸を使用する以外は、上述の合成例53の<ステップ2>と同様にして化合物205を得た。
HRMS[M]+:652.29
HRMS[M]+:776.32
窒素気流下、中間体1−A(11.0g、0.026mol)、3−クロロフェニルボロン酸(4.8g、0.031mol)、Pd(OAc)2(0.29g、0.001mol)、炭酸セシウム(25.4g、0.078mol)及びXphos(0.3g、0.003mol)を混合した後、トルエン(100ml)、エタノール(20ml)及びH2O(20ml)で還流攪拌した。
窒素気流下、上述の<ステップ1>で得た中間体1−B(7.5g、0.015mol)、9,9−ジメチル−9H−フルオレン−3−イル−ボロン酸(4.3g、0.018mol)、Pd(OAc)2(0.17g、0.075mmol)、炭酸セシウム(14.6g、0.045mol)及びXphos(0.7g、1.5mmol)を混合した後、トルエン(60ml)、エタノール(15ml)及びH2O(15ml)で還流攪拌した。
HRMS[M]+:652.29
合成例で得られた化合物を、常法で高純度昇華精製を行った後、後述のように緑色有機電界発光素子を製造した。
合成例1で得られた化合物1の代わりに、下記のBCPを使用する以外は、実施例1と同様にして緑色有機電界発光素子を製造した。
合成例1で得られた化合物1の代わりに、下記の化合物Aを使用する以外は、実施例1と同様にして緑色有機電界発光素子を製造した。
合成例1で得られた化合物1の代わりに、下記の化合物Bを使用する以外は、実施例1と同様にして緑色有機電界発光素子を製造した
実施例1〜41及び比較例1〜3においてそれぞれ製造された緑色有機電界発光素子について、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表1にまとめた。
合成例で得られた化合物を、常法で高純度昇華精製を行った後、下記の表2に示されるような構造で青色蛍光有機電界発光素子を製造した。
電子輸送補助層を使用することなく電子輸送層を30nmに蒸着した以外は、実施例42と同様にして青色蛍光有機電界発光素子を製造した。
合成例1で得られた化合物1の代わりに下記のBCPを使用する以外は、実施例42と同様にして青色蛍光有機電界発光素子を製造した。
実施例42〜98及び比較例4〜5においてそれぞれ製造された青色蛍光有機電界発光素子について、電流密度10mA/cm2での駆動電圧、電流効率及び発光ピークを測定し、その結果を下記の表3にまとめた。
Claims (8)
- 下記の化1で示される化合物:
Ra及びRbは、互いに同一又は異なり、それぞれ独立に、C1〜C40のアルキル基、又はC6〜C60のアリール基であり、
R1〜R2は、互いに同一又は異なり、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキシド基、及びC6〜C60のアリールアミン基からなる群から選択され、
R3は、水素であり、
Lは、単結合であり、
Z1〜Z5は、互いに同一又は異なり、それぞれ独立に、N又はC(R4)であり、この時、少なくとも1つは、Nであり、C(R4)が複数の場合、複数のC(R4)は、互いに同一又は異なり、
c、eは、それぞれ0〜4の整数であり、
dは、0〜3の整数であり、
m、nは、それぞれ1〜3の整数であり、
前記R4は、水素、C1〜C40のアルキル基、及び、C6〜C12のアリール基からなる群から選択され、前記R4が複数の場合にはR4の少なくとも1つはアリール基であり、
Z1〜Z5に3つのNを含む場合、複数のR4は互いに同一であり、
前記Ra、Rbのアルキル基、アリール基と、前記R1、R2、及び、R4のアルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキシド基、アリールアミン基とは、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、及びC1〜C40のホスフィンオキシド基からなる群から選択される1種以上の置換基で置換又は非置換であり、前記置換基が複数の場合、複数の置換基は、互いに同一又は異なり、
ただし、フルオレン基は前記Ra、Rb、R1、及びR2から除外される)。
- 前記化1で示される化合物は、下記の化2〜化4で示される化合物からなる群から選択されるものである請求項1に記載の化合物。
Ra、Rb、R1〜R3、Z1〜Z5、c、d及びeは、それぞれ請求項1における定義と同様である) - 前記化1において、
R4は、請求項1における定義と同様である) - 前記化1で示される化合物は、下記の化5で示されるものである請求項3に記載の化合物。
Ra、Rb、R1〜R4、L、c、d、e、m及びnは、それぞれ、請求項1における定義と同様である) - 前記化5で示される化合物において、R4が互いに同一である請求項4に記載の化合物。
- 前記Ra及びRbは、それぞれ独立に、メチル基又はフェニル基である請求項1に記載の化合物。
- 前記
- 前記化1で示される化合物は、下記で示される化合物からなる群から選択されるものである請求項1に記載の化合物。
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KR20140188953 | 2014-12-24 | ||
KR10-2014-0188953 | 2014-12-24 | ||
KR10-2015-0171678 | 2015-12-03 | ||
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KR10-2015-0171639 | 2015-12-03 | ||
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