JP5607959B2 - カルバゾール誘導体、発光素子、発光装置および電子機器 - Google Patents
カルバゾール誘導体、発光素子、発光装置および電子機器 Download PDFInfo
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- JP5607959B2 JP5607959B2 JP2010060171A JP2010060171A JP5607959B2 JP 5607959 B2 JP5607959 B2 JP 5607959B2 JP 2010060171 A JP2010060171 A JP 2010060171A JP 2010060171 A JP2010060171 A JP 2010060171A JP 5607959 B2 JP5607959 B2 JP 5607959B2
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 114
- 239000000126 substance Substances 0.000 claims description 92
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- -1 R 21 to R 27 Chemical compound 0.000 claims description 39
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
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- 229910045601 alloy Inorganic materials 0.000 description 4
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
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- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
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- RIBQJGPEJUOLBP-UHFFFAOYSA-N N=C(c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)OC(c1cc2ccccc2cc1)=N Chemical compound N=C(c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(cc1c2c3cccc2)ccc1[n]3-c1ccccc1)OC(c1cc2ccccc2cc1)=N RIBQJGPEJUOLBP-UHFFFAOYSA-N 0.000 description 1
- CBWKNEJXXLDHNM-UHFFFAOYSA-N N=C(c1ccccc1)OC(c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(cc1c2c3ccc(-c(cc4)ccc4-c4ccccc4)c2)ccc1[n]3-c1ccccc1)=N Chemical compound N=C(c1ccccc1)OC(c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(cc1c2c3ccc(-c(cc4)ccc4-c4ccccc4)c2)ccc1[n]3-c1ccccc1)=N CBWKNEJXXLDHNM-UHFFFAOYSA-N 0.000 description 1
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- IGRQYDBSVFPIBR-UHFFFAOYSA-N N=C(c1ccccc1)OC(c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1c2c3ccc(-c4ccccc4)c2)ccc1[n]3-c1ccccc1)=N Chemical compound N=C(c1ccccc1)OC(c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1c2c3ccc(-c4ccccc4)c2)ccc1[n]3-c1ccccc1)=N IGRQYDBSVFPIBR-UHFFFAOYSA-N 0.000 description 1
- AEWIUJGFSICDOH-UHFFFAOYSA-N NC(c1ccccc1)OC(c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1c2c3ccc(-c4c(cccc5)c5ccc4)c2)ccc1[n]3-c1ccccc1)=N Chemical compound NC(c1ccccc1)OC(c(cc1)ccc1-[n](c1ccccc1c1c2)c1ccc2-c(cc1c2c3ccc(-c4c(cccc5)c5ccc4)c2)ccc1[n]3-c1ccccc1)=N AEWIUJGFSICDOH-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- NMVJSUIMAZOHJK-UHFFFAOYSA-K [Al+3].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-] Chemical compound [Al+3].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-].OC1=C(C=CC=C1)C1(OC(=NN1)C1=CC=CC=C1)C(=O)[O-] NMVJSUIMAZOHJK-UHFFFAOYSA-K 0.000 description 1
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- 150000001339 alkali metal compounds Chemical class 0.000 description 1
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- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 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 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
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- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
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- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SFSWXKUCNTZAPG-UHFFFAOYSA-N n,n-diphenyl-4-[3-[4-(n-phenylanilino)phenyl]quinoxalin-2-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C(=NC2=CC=CC=C2N=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 SFSWXKUCNTZAPG-UHFFFAOYSA-N 0.000 description 1
- LKRBRJVNQJYRHZ-UHFFFAOYSA-N n,n-diphenyl-4-[9-[4-(n-phenylanilino)phenyl]fluoren-9-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LKRBRJVNQJYRHZ-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- RFBDMIDJTYEWSG-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-9,9-dimethyl-n-phenylfluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RFBDMIDJTYEWSG-UHFFFAOYSA-N 0.000 description 1
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000005381 potential energy Methods 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/17—Passive-matrix OLED displays
- H10K59/173—Passive-matrix OLED displays comprising banks or shadow masks
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Description
本実施の形態では、本発明の一態様のヘテロ芳香環を有するカルバゾール誘導体について説明する。
(式中、Qは一般式Q1またはQ2で表される置換基である。また、Ar1乃至Ar3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。また、R28乃至R31は水素原子、または炭素数1乃至4のアルキル基を表す。また、R11乃至R15、及びR21乃至R27は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)アルキル基が導入された場合、本発明の一態様のヘテロ芳香環を有するカルバゾール誘導体の溶解性が向上する。
(式中、Qは一般式Q1またはQ2で表される置換基である。また、Ar2およびAr3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。また、R28乃至R31は水素原子、または炭素数1乃至4のアルキル基を表す。また、R11乃至R15、及びR21乃至R27、及びR41乃至R45は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
(式中、Qは一般式Q1またはQ2で表される置換基である。また、Ar2およびAr3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。また、R13、及びR21乃至R27、及びR41乃至R45は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
(式中、Qは一般式Q1またはQ2で表される置換基である。また、Ar2およびAr3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。また、R13は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
(式中、Qは一般式Q1−1またはQ2−1で表される置換基である。また、R13、及びR51乃至R55、及びR61乃至R65は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
(式中、Qは構造式Q1−2またはQ2−2で表される置換基である。また、R13は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
(式中、Qは一般式Q1またはQ2で表される置換基であり、Xはハロゲン原子である。また、Ar1乃至Ar3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。また、R28乃至R31は水素原子、または炭素数1乃至4のアルキル基を表す。また、R11乃至R15、及びR21乃至R27は水素原子、または炭素数が1乃至4のアルキル基、または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良い。なお、α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。)
なお、ハロゲン化されたヘテロ芳香環を有する化合物(B1)の置換基Xはハロゲン原子を表し、ヨウ素または、臭素が本合成スキーム(M1)において好ましい。
本実施の形態では、本発明の一態様のヘテロ芳香環を有するカルバゾール誘導体を燐光性化合物のホスト材料として用いた発光素子の一態様について、図1を用いて説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について図2(A)(B)を用いて説明する。
本実施の形態では、本発明の一態様のヘテロ芳香環を有するカルバゾール誘導体を用いた発光素子の一例として、複数の発光層を有する態様について、図3を用いて説明する。図3の発光素子は複数の発光層を有しており、複数の発光層が発する光を混合して利用できる。異なる発光層の光を混合することにより、例えば白色光を得ることができる。
本実施の形態では、本発明の一態様のヘテロ芳香環を有するカルバゾール誘導体を用いて作製された発光装置について図4および5を用いて説明する。なお、図4(A)は、発光装置を示す上面図、図4(B)は図4(A)をA−A’で切断した断面図である。点線で示された401は駆動回路部(ソース側駆動回路)、402は画素部、403は駆動回路部(ゲート側駆動回路)である。また、404は封止基板、405はシール材であり、シール材405で囲まれた内側は、空間407になっている。
本実施の形態では、実施の形態5に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態1に示したヘテロ芳香環を有するカルバゾール誘導体を含み、発光効率の高く、消費電力が低減され、長時間駆動可能な表示部を有する。また、色再現性に優れた表示部を有する。
本実施例では実施の形態1に構造式(1)として示したヘテロ芳香環を有するカルバゾール誘導体である4−(9−フェニル−9H−カルバゾール−3−イル)−4’−(3−フェニルキノキサリン−2−イル)トリフェニルアミン(略称:PCBA1PQ)の合成方法について説明する。
本実施例では実施の形態1に構造式(67)として示したヘテロ芳香環を有するカルバゾール誘導体である4−(5−フェニル−1,3,4−オキサジアゾール−2−イル)−4’−(9−フェニル−9H−カルバゾール−3−イル)トリフェニルアミン(略称:PCBAO11)の合成方法について説明する。
本実施例では実施の形態1に構造式(35)として示したヘテロ芳香環を有するカルバゾール誘導体である9−フェニル−9’−[4−(3−フェニルキノキサリン−2−イル)フェニル]−3,3’−ビ(9H−カルバゾール)(略称:PCC1PQ)の合成方法について説明する。
本実施例では実施の形態1に構造式(99)として示したヘテロ芳香環を有するカルバゾール誘導体である9−フェニル−9’−[4−(5−フェニル−1,3,4−オキサジアゾール−2−イル)フェニル]−3,3’−ビ(9H−カルバゾール)(略称:PCCO11)の合成方法について説明する。
まず、ガラス基板2100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極2101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
発光素子2では、発光素子1の第3の層2113にホスト材料として用いたPCBA1PQの代わりに、構造式(67)であらわされる4−(5−フェニル−1,3,4−オキサジアゾール−2−イル)−4’−(9−フェニル−9H−カルバゾール−3−イル)トリフェニルアミン(略称:PCBAO11)をホスト材料に用いた。すなわち、PCBAO11とIr(tppr)2acacとを共蒸着することにより、第2の層2112上に第3の層2113を発光層として形成した。ここで、PCBAO11とIr(tppr)2(acac)との重量比は、1:0.08(=PCBAO11:Ir(tppr)2acac)となるように調節した。また、第3の層2113の膜厚は40nmとした。第3の層2113以外は発光素子1と同様に作製した。
発光素子3では、発光素子1の第3の層2113にホスト材料として用いたPCBA1PQの代わりに、構造式(35)であらわされる9−フェニル−9’−[4−(3−フェニルキノキサリン−2−イル)フェニル]−3,3’−ビ(9H−カルバゾール)(略称:PCC1PQ)をホスト材料に用いた。すなわち、PCC1PQとIr(tppr)2acacとを共蒸着することにより、第2の層2112上に第3の層2113を発光層として形成した。ここで、PCC1PQとIr(tppr)2(acac)との重量比は、1:0.08(=PCC1PQ:Ir(tppr)2acac)となるように調節した。また、第3の層2113の膜厚は40nmとした。第3の層2113以外は発光素子1と同様に作製した。
発光素子4では、発光素子1の第3の層2113にホスト材料として用いたPCBA1PQの代わりに、構造式(99)であらわされる9−フェニル−9’−[4−(5−フェニル−1,3,4−オキサジアゾール−2−イル)フェニル]−3,3’−ビ(9H−カルバゾール)(略称:PCCO11)をホスト材料に用いた。すなわち、PCCO11とIr(tppr)2acacとを共蒸着することにより、第2の層2112上に第3の層2113を発光層として形成した。ここで、PCCO11とIr(tppr)2(acac)との重量比は、1:0.08(=PCCO11:Ir(tppr)2acac)となるように調節した。また、第3の層2113の膜厚は40nmとした。第3の層2113以外は発光素子1と同様に作製した。
まず、ガラス基板2100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極2101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
101 電極
102 電極
111 正孔注入層
112 正孔輸送層
113 発光層
113a 発光層
113b 発光層
114 電子輸送層
114a 電子キャリアの移動を制御する層
114b 電子輸送層
115 電子注入層
301 電極
302 電極
311 正孔注入層
312 正孔輸送層
313 発光層
314 電子輸送層
315 正孔輸送層
316 発光層
317 電子輸送層
318 電子注入層
321 N層
322 P層
401 ソース側駆動回路
402 画素部
403 ゲート側駆動回路
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 基板
411 スイッチング用TFT
412 電流制御用TFT
413 電極
414 絶縁物
416 発光物質を含む層
417 電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
951 基板
952 電極
953 絶縁層
954 隔壁層
955 発光物質を含む層
956 電極
1001 筐体
1002 表示部
1004 外部接続ポート
2001 筐体
2002 光源
2100 ガラス基板
2101 電極
2102 電極
2111 第1の層
2112 第2の層
2113 第3の層
2114 第4の層
2115 第5の層
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
9601 筐体
9602 液晶層
9603 バックライト
9604 筐体
9605 ドライバーIC
9606 端子
Claims (10)
- 一般式(G1)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは一般式Q2で表される置換基であり、
Ar1 及びAr3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
R28乃至R31は水素原子または炭素数1乃至4のアルキル基を表し、
R11乃至R15、及びR21乃至R27は、水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 一般式(G2)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは一般式Q2で表される置換基であり、
Ar3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
R28乃至R31は水素原子、または炭素数1乃至4のアルキル基を表し、
R11乃至R15、及びR21乃至R27、及びR41乃至R45は、水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 一般式(G3)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは一般式Q2で表される置換基であり、
Ar3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
R13、及びR21乃至R27、及びR41乃至R45は、水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 一般式(G4)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは一般式Q2で表される置換基であり、
Ar3は環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
R13は水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 一般式(G5)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは一般式Q2−1で表される置換基であり、
R13、及びR51乃至R55 は、水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 一般式(G6)で表されるヘテロ芳香環を有するカルバゾール誘導体。
(式中、Qは構造式Q2−2で表される置換基であり、
R13は水素原子または炭素数が1乃至4のアルキル基または環を形成する炭素数が6乃至10のアリール基であって、前記アリール基は置換基を有していても良く、
α位の炭素とβ位の炭素が直接結合してカルバゾール環を形成してもよい。) - 請求項1乃至6のいずれか一に記載のヘテロ芳香環を有するカルバゾール誘導体を一対の電極間に有する発光素子。
- 請求項1乃至6のいずれか一に記載のヘテロ芳香環を有するカルバゾール誘導体と発光物質とを含む発光層を一対の電極間に有する発光素子。
- 請求項1乃至6のいずれか一に記載のヘテロ芳香環を有するカルバゾール誘導体と燐光を発する物質とを含む発光層を一対の電極間に有する発光素子。
- 請求項1乃至6のいずれか一に記載のヘテロ芳香環を有するカルバゾール誘導体と発光物質とを含む発光層を一対の電極間に有する発光素子を用いた発光装置および電子機器。
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JP2019124733A Withdrawn JP2019220693A (ja) | 2009-03-20 | 2019-07-03 | 発光装置 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2016040287A (ja) * | 2009-03-20 | 2016-03-24 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体、発光素子、発光装置 |
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JP2019220693A (ja) | 2019-12-26 |
TWI480277B (zh) | 2015-04-11 |
US8530658B2 (en) | 2013-09-10 |
JP2015024997A (ja) | 2015-02-05 |
TW201105659A (en) | 2011-02-16 |
JP2016040287A (ja) | 2016-03-24 |
JP6553110B2 (ja) | 2019-07-31 |
KR101547876B1 (ko) | 2015-08-27 |
JP2021170645A (ja) | 2021-10-28 |
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TWI525089B (zh) | 2016-03-11 |
JP6113806B2 (ja) | 2017-04-12 |
CN101838262B (zh) | 2014-07-23 |
JP5820035B2 (ja) | 2015-11-24 |
US8247575B2 (en) | 2012-08-21 |
KR20100105501A (ko) | 2010-09-29 |
JP2017143284A (ja) | 2017-08-17 |
US20100237339A1 (en) | 2010-09-23 |
TW201531470A (zh) | 2015-08-16 |
CN101838262A (zh) | 2010-09-22 |
US20100237773A1 (en) | 2010-09-23 |
JP2010241801A (ja) | 2010-10-28 |
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