JP2012236970A - 高分子化合物及びそれを用いた発光素子 - Google Patents
高分子化合物及びそれを用いた発光素子 Download PDFInfo
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- JP2012236970A JP2012236970A JP2011279929A JP2011279929A JP2012236970A JP 2012236970 A JP2012236970 A JP 2012236970A JP 2011279929 A JP2011279929 A JP 2011279929A JP 2011279929 A JP2011279929 A JP 2011279929A JP 2012236970 A JP2012236970 A JP 2012236970A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 315
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 128
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 85
- 125000003118 aryl group Chemical group 0.000 claims abstract description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 68
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 62
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 48
- -1 2,7-fluorenediyl group Chemical group 0.000 claims description 212
- 229920000642 polymer Polymers 0.000 claims description 192
- 125000001424 substituent group Chemical group 0.000 claims description 163
- 239000000203 mixture Substances 0.000 claims description 111
- 239000000463 material Substances 0.000 claims description 64
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 47
- 125000003107 substituted aryl group Chemical group 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 41
- 230000005525 hole transport Effects 0.000 claims description 38
- 239000010409 thin film Substances 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
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- 125000000732 arylene group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000005649 substituted arylene group Chemical group 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 41
- 150000004982 aromatic amines Chemical class 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 198
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- 238000000034 method Methods 0.000 description 56
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- 125000004432 carbon atom Chemical group C* 0.000 description 47
- 238000002347 injection Methods 0.000 description 43
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 125000003277 amino group Chemical group 0.000 description 41
- 239000002244 precipitate Substances 0.000 description 33
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- 230000015572 biosynthetic process Effects 0.000 description 30
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- 125000002252 acyl group Chemical group 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 125000003710 aryl alkyl group Chemical group 0.000 description 24
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- 229910052799 carbon Inorganic materials 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
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- 125000003342 alkenyl group Chemical group 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
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- 239000003054 catalyst Substances 0.000 description 14
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- 239000007787 solid Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
- 238000012643 polycondensation polymerization Methods 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000002184 metal Chemical class 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 125000005018 aryl alkenyl group Chemical group 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 239000012300 argon atmosphere Substances 0.000 description 9
- 125000005015 aryl alkynyl group Chemical group 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 0 *c(cc1[C@@](CC(C2)(*3=CC3)O)(C3)[C@]22CC3=O)ccc1-c1c2cc(C2*=C2)cc1 Chemical compound *c(cc1[C@@](CC(C2)(*3=CC3)O)(C3)[C@]22CC3=O)ccc1-c1c2cc(C2*=C2)cc1 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229920001940 conductive polymer Polymers 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- KBXGMZXLKCUSEB-UHFFFAOYSA-M sodium;[ethyl(oxidosulfinothioyl)amino]ethane Chemical compound [Na+].CCN(CC)S([O-])=S KBXGMZXLKCUSEB-UHFFFAOYSA-M 0.000 description 8
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 8
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 8
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 8
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 6
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 229920005596 polymer binder Polymers 0.000 description 6
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 5
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 5
- JUHBYLSCAJAHEH-UHFFFAOYSA-N 1-bromo-3,5,5-trimethylhexane Chemical compound BrCCC(C)CC(C)(C)C JUHBYLSCAJAHEH-UHFFFAOYSA-N 0.000 description 5
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 5
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- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
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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 4
- 229910052725 zinc Inorganic materials 0.000 description 4
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- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 3
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
[式中、n1及びn2はそれぞれ独立に、1〜5の整数を示し、R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10はそれぞれ独立に、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、R1、R2、R3及びR4がそれぞれ複数存在するとき、複数存在するR1、R2、R3及びR4は互いに同一でも異なっていてもよく、R1、R2、R3及びR4のうち隣接する基同士は互いに連結して環構造を形成していてもよく、R7、R8、R9及びR10のうち隣接する基同士は互いに連結して環構造を形成していてもよい。]
[式中、a及びbはそれぞれ独立に0又は1を示し、Ar1、Ar2、Ar3及びAr4はそれぞれ独立に、非置換若しくは置換のアリーレン基、非置換若しくは置換の2価の複素環基、又は、アリーレン基及び2価の複素環基から選ばれる同一若しくは異なる2以上の基が連結した2価の基(該基は、置換基を有していてもよい。)を示し、RA、RB及びRCはそれぞれ独立に、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基又は非置換若しくは置換の1価の複素環基を示し、Ar1、Ar2、Ar3及びAr4はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と互いに連結して環構造を形成していてもよい。]
[式中、RDは水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基又は非置換若しくは置換の1価の複素環基を示し、X1は、単結合、酸素原子、硫黄原子又は−C(R11)2−で表される基(R11は、非置換若しくは置換のアルキル基又は非置換若しくは置換のアリール基を示し、複数存在するR11は互いに同一でも異なっていてもよい。)を示す。]
[式中、Ar5は非置換若しくは置換のアリーレン基、非置換若しくは置換の2価の複素環基、又は、アリーレン基及び2価の複素環基から選ばれる同一若しくは異なる2以上の基が連結した2価の基(該基は、置換基を有していてもよい。)を示す。但し、式(4)で表される構成単位は、前記式(1)で表される構成単位とは異なる。]
[式中、c1及びc2はそれぞれ独立に0〜4の整数を示し、c3は0〜5の整数を示し、R12、R13及びR14はそれぞれ独立に、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基、非置換若しくは置換の1価の複素環基、非置換若しくは置換のアルコキシカルボニル基、非置換若しくは置換のシリル基、ハロゲン原子、カルボキシル基又はシアノ基を示し、R12、R13及びR14がそれぞれ複数存在するとき、複数存在するR12、R13及びR14は互いに同一でも異なっていてもよい。]
[式中、c1及びc2はそれぞれ独立に0〜4の整数を示し、c3は0〜5の整数を示し、R12、R13及びR14はそれぞれ独立に、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基、非置換若しくは置換の1価の複素環基、非置換若しくは置換のアルコキシカルボニル基、非置換若しくは置換のシリル基、ハロゲン原子、カルボキシル基又はシアノ基を示し、R12、R13及びR14がそれぞれ複数存在するとき、複数存在するR12、R13及びR14は互いに同一でも異なっていてもよい。]
[式中、m1及びm2はそれぞれ独立に1又は2を示し、R21、R22、R23、R24、R25、R26、R27、R28、R29及びR30はそれぞれ独立に、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、X11、X12、X13及びX14はそれぞれ独立に、−C(R31)2−で表される基(R31は、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、複数存在するR31は互いに同一でも異なっていてもよい。)を示し、R27、R28、R29及びR30のうち隣接する基同士は互いに連結して環構造を形成していてもよく、Z1及びZ2はそれぞれ独立に、下記置換基群から選ばれる基を示す。但し、R21、R22、R23及びR24のうち少なくとも1個は、水素原子以外の基である。
<置換基群>
塩素原子、臭素原子、ヨウ素原子、−O−S(=O)2R41(R41は、アルキル基、又は、アルキル基、アルコキシ基、ニトロ基、フッ素原子若しくはシアノ基で置換されていてもよいアリール基、を示す。)で表される基、−B(OR42)2(R42は水素原子又はアルキル基を示し、複数存在するR42は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基、−BF4Q1(Q1は、Li+、Na+、K+、Rb+及びCs+からなる群より選ばれる1価の陽イオンを示す。)で表される基、−MgY1(Y1は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、−ZnY2(Y2は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、及び、−Sn(R43)3(R43は水素原子又はアルキル基を示し、複数存在するR43は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基。]
本実施形態に係る高分子化合物は、下記式(1)で表される第一構成単位及び下記式(2)で表される第二構成単位を有する。上記高分子化合物は、これらの構成単位を有することにより、発光効率に優れる発光素子の製造に有用なものとなる。
第一構成単位は、下記式(1)で表される構成単位である。
第二構成単位は、下記式(2)で表される構成単位である。
第三構成単位は、下記式(4)で表される構成単位である。
高分子化合物は、例えば、下記式(1M)で表される化合物(以下、場合により「化合物1M」という。)と、下記式(2M)で表される化合物(以下、場合により「化合物2M」という。)と、を縮合重合させることにより製造することができる。本明細書において、化合物1Mと化合物2Mと後述する化合物4Mを総称して、「モノマー」ということがある。
塩素原子、臭素原子、ヨウ素原子、−O−S(=O)2R41(R41は、アルキル基、又は、アルキル基、アルコキシ基、ニトロ基、フッ素原子若しくはシアノ基で置換されていてもよいアリール基を示す。)で表される基。
−B(OR42)2(R42は水素原子又はアルキル基を示し、複数存在するR42は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基、−BF4Q1(Q1は、Li+、Na+、K+、Rb+及びCs+からなる群より選ばれる1価の陽イオンを示す。)で表される基、−MgY1(Y1は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、−ZnY2(Y2は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、及び、−Sn(R43)3(R43は水素原子又はアルキル基を示し、複数存在するR43は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基。
ZT−ArT (1T)
本実施形態の組成物は、上記高分子化合物と、正孔輸送材料、電子輸送材料及び発光材料からなる群より選ばれる少なくとも一種と、を含有する。この組成物は、発光素子の製造に好適に使用でき、得られる発光素子は発光効率に優れたものとなる。
本実施形態の高分子化合物は、溶媒、好ましくは有機溶媒に溶解又は分散させて、液状組成物(溶液又は分散液)としてもよい。このような液状組成物は、インク、ワニスとも呼ばれる。発光素子に使用する有機薄膜を形成するためにこの液状組成物を用いる場合、液状組成物は、溶液であることが好ましい。
芳香族炭化水素系溶媒と脂肪族炭化水素系溶媒;
芳香族炭化水素系溶媒と芳香族エーテル系溶媒;
芳香族炭化水素系溶媒と脂肪族エーテル系溶媒;
芳香族炭化水素系溶媒と非プロトン性極性溶媒;
芳香族エーテル系溶媒と非プロトン性極性溶媒等。
また、単独溶媒又は混合溶媒に水を添加することもできる。
本実施形態の有機薄膜は、上記高分子化合物を含有する。本実施形態の有機薄膜は、上述のように上記液状組成物から容易に製造することができる。
本実施形態の発光素子は、上記有機薄膜を有する。
(a)陽極/発光層/陰極
(b)陽極/正孔輸送層/発光層/陰極
(c)陽極/発光層/電子輸送層/陰極
(d)陽極/正孔輸送層/発光層/電子輸送層/陰極
(e)陽極/電荷注入層/発光層/陰極
(f)陽極/発光層/電荷注入層/陰極
(g)陽極/電荷注入層/発光層/電荷注入層/陰極
(h)陽極/電荷注入層/正孔輸送層/発光層/陰極
(i)陽極/正孔輸送層/発光層/電荷注入層/陰極
(j)陽極/電荷注入層/正孔輸送層/発光層/電荷注入層/陰極
(k)陽極/電荷注入層/発光層/電荷輸送層/陰極
(l)陽極/発光層/電子輸送層/電荷注入層/陰極
(m)陽極/電荷注入層/発光層/電子輸送層/電荷注入層/陰極
(n)陽極/電荷注入層/正孔輸送層/発光層/電荷輸送層/陰極
(o)陽極/正孔輸送層/発光層/電子輸送層/電荷注入層/陰極
(p)陽極/電荷注入層/正孔輸送層/発光層/電子輸送層/電荷注入層/陰極
(q)陽極/絶縁層/発光層/陰極
(r)陽極/発光層/絶縁層/陰極
(s)陽極/絶縁層/発光層/絶縁層/陰極
(t)陽極/絶縁層/正孔輸送層/発光層/陰極
(u)陽極/正孔輸送層/発光層/絶縁層/陰極
(v)陽極/絶縁層/正孔輸送層/発光層/絶縁層/陰極
(w)陽極/絶縁層/発光層/電子輸送層/陰極
(x)陽極/発光層/電子輸送層/絶縁層/陰極
(y)陽極/絶縁層/発光層/電子輸送層/絶縁層/陰極
(z)陽極/絶縁層/正孔輸送層/発光層/電子輸送層/陰極
(aa)陽極/正孔輸送層/発光層/電子輸送層/絶縁層/陰極
(ab)陽極/絶縁層/正孔輸送層/発光層/電子輸送層/絶縁層/陰極
測定する高分子化合物を約0.05重量%の濃度になるようにテトラヒドロフランに溶解させ、GPCに10μL注入した。GPCの移動相としてテトラヒドロフランを用い、2.0mL/分の流速で流した。カラムとして、PLgel MIXED−B(ポリマーラボラトリーズ製)を用いた。検出器には示差屈折率検出器(島津製作所製、商品名:RID−10A)を用いた。
(化合物2の合成)
まず、化合物1を用いて、下記のとおり化合物2を合成した。
1H−NMR(CDCl3、300MHz)δ(ppm):0.87(6H、t)、1.20〜1.36(16H、m)、1.82〜1.97(4H、m)、2.57〜2.81(8H、m)、5.20(2H、br)、7.23〜7.32(4H、m)、7.41〜7.48(2H、m)、7.87〜7.90(2H、m).
次いで、化合物2を用いて、下記のとおり化合物3を合成した。
1H−NMR(CDCl3、300MHz)δ(ppm):0.66〜0.98(6H、m)、1.00〜2.22(34H、m)、7.13〜7.50(6H、m)、7.80〜7.98(2H、m).
次いで、化合物3を用いて、下記のとおり化合物4を合成した。
1H−NMR(CDCl3、300MHz)δ(ppm):0.66〜0.98(6H、m)、1.00〜2.20(34H、m)、7.22〜7.78(6H、m).
次いで、化合物4を用いて下記のとおり化合物5を合成した。
(1−ブロモ−3,5,5−トリメチルヘキサンの合成)
次いで、3,5,5−トリメチルヘキサノールを用いて、下記のとおり1−ブロモ−3,5,5−トリメチルヘキサンを合成した。
次いで、1−ブロモ−3,5,5−トリメチルヘキサンを用いて下記のとおり化合物6を合成した。
次いで、化合物6を用いて下記のとおり化合物7を合成した。
次いで、化合物7を用いて、下記のとおり化合物8を合成した。
次いで、化合物8を用いて、下記のとおり化合物9を合成した。
1H−NMR(CDCl3、300MHz)δ(ppm):0.75〜1.36(38H、m)、1.56〜1.82(5H、m)2.17〜2.24(5H、m)、7.33〜7.68(6H、m).
(化合物10の合成)
次いで、1,5−ナフチル ビス(トリフルオロメタンスルホネート)を用いて下記のとおり化合物10を合成した。
1H−NMR(300MHz、CDCl3)δ(ppm)0:.75〜1.00(12H,m),1.10〜1.50(16H,m),1.69〜1.85(2H,m),2.90〜3.05(4H,m),7.24〜7.38(3H,m),7.35〜7.44(3H,m),7.90〜7.95(3H,m).
次いで、化合物10を用いて、下記のとおり化合物11を合成した。
1H−NMR(300MHz、CDCl3)δ(ppm):0.85〜0.95(12H,m),1.24〜1.50(16H,m),1.66〜1.85(2H,m),2.90〜3.18(4H,m),7.60(2H,s),8.47(2H,s).
次いで、化合物11を用いて、下記のとおり化合物12を合成した。
1H−NMR(300MHz、CDCl3)δ(ppm):0.80〜0.98(12H,m),1.20〜1.44(16H,m),1.64〜1.80(2H,m),2.77〜2.95(4H,m),7.37(2H,s),8.00(2H,s).
下記式(K−1)で表される構成単位と、下記式(K−2)で表される構成単位と、下記式(K−3)で表される構成単位と、下記式(K−4)で表される構成単位を、20:50:25:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物A1)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、下記式(M−3−BR):
で表される化合物(0.548g、1.00mmol)と、下記式(M−4−BR):
で表される化合物(0.148g、0.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−5)で表される構成単位と、下記式(K−2)で表される構成単位と、下記式(K−6)で表される構成単位と、下記式(K−4)で表される構成単位を、20:50:25:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物A2)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、合成例1で合成した化合物12(0.510g、1.00mmol)と、下記式(M−4−BR):
で表される化合物(0.148g、0.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−1)で表される構成単位と、下記式(K−7)で表される構成単位と、下記式(K−4)で表される構成単位と、下記式(K−8)で表される構成単位を、50:45:3:2のモル比(仕込み原料による理論値)で有する重合体(高分子化合物A3)の合成を、下記のとおり行った。
で表される化合物(1.463g、1.80mmol)と、下記式(M−4−BR):
で表される化合物(0.089g、0.12mmol)と、下記式(M−8−BR):
で表される化合物(0.088g、0.08mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−1)で表される構成単位と、下記式(K−2)で表される構成単位と、下記式(K−3)で表される構成単位と、下記式(K−9)で表される構成単位を、50:25:20:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物A4)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、下記式(M−3−BR):
で表される化合物(0.548g、1.00mmol)と、下記式(M−9−BR):
で表される化合物(0.092g、0.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−1)で表される構成単位と、下記式(K−2)で表される構成単位と、下記式(K−10)で表される構成単位と、下記式(K−4)で表される構成単位を、20:60:15:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物A5)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、下記式(M−2−BR):
で表される化合物(0.258g、0.40mmol)と、下記式(M−10−BR):
で表される化合物(0.381g、0.60mmol)と、下記式(M−4−BR):
で表される化合物(0.148g、0.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−9)で表される構成単位と、下記式(K−10)で表される構成単位と、下記式(K−3)で表される構成単位を、42:8:50のモル比(仕込み原料による理論値)で有する重合体(高分子化合物AA)の合成を、下記のとおり行った。
で表される化合物(17.57g、33.13mmol)と、下記式(M−9−BR):
で表される化合物(12.88g、28.05mmol)と、下記式(M−10−BR):
で表される化合物(2.15mg、5.01mmol)と、酢酸パラジウム(II)(7.4mg)と、トリス(2−メチルフェニル)ホスフィン(70mg)、第四級アンモニウムクロライドの0.74Mトルエン溶液(アリクアト(Aliquat)(登録商標)336、シグマアルドリッチ社製、3g)と、トルエン(200g)を混合した。
スパッタ法により45nmの厚みでITO膜を付けたガラス基板に、ポリチオフェンスルホン酸のエチレングリコールモノブチルエーテル/水=3/2(体積比)の混合液(シグマアルドリッチ社、商品名:Plexcore OC 1200)を用いてスピンコートにより35nmの厚さで成膜し、ホットプレート上で170℃で15分間乾燥させた。
実施例8における高分子化合物A1に代えて高分子化合物A2を用いたこと以外は、実施例8と同様にして、発光素子2を作製した。得られた発光素子2に電圧を印加したところ、この素子から460nmにピークを有するEL発光が得られ、最大発光効率は9.0cd/Aであった。結果を表1に示す。
実施例8における高分子化合物A1に代えて高分子化合物A3を用いたこと以外は、実施例8と同様にして、発光素子3を作製した。得られた発光素子3に電圧を印加したところ、この素子から460nmにピークを有するEL発光が得られ、最大発光効率は8.8cd/Aであった。結果を表1に示す。
実施例8における高分子化合物A1に代えて高分子化合物A4を用いたこと以外は、実施例8と同様にして、発光素子4を作製した。得られた発光素子4に電圧を印加したところ、この素子から445nmにピークを有するEL発光が得られ、最大発光効率は5.1cd/Aであった。結果を表1に示す。
下記式(K−1)で表される構成単位と、下記式(K−2)で表される構成単位と、下記式(K−3)で表される構成単位を、20:50:30のモル比(仕込み原料による理論値)で有する重合体(高分子化合物B)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、下記式(M−3−BR):
で表される化合物(0.658g、1.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
下記式(K−2)で表される構成単位と、下記式(K−3)で表される構成単位と、下記式(K−4)で表される構成単位を、50:45:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物C)の合成を、下記のとおり行った。
で表される化合物(4.3884g、5.94mmol)と、下記式(M−3−BR):
で表される化合物(2.9621g、5.40mmol)と、下記式(M−4−BR):
で表される化合物(0.4430g、0.60mmol)と、パラジウムアセテート(3.24mg)、トリス(o−メトキシフェニル)ホスフィン(19.3mg)及びトルエン(67mL)を混合し、105℃に加熱した。
下記式(K−2)で表される構成単位と、下記式(K−3)で表される構成単位と、下記式(K−11)で表される構成単位と、下記式(K−4)で表される構成単位とを、50:25:20:5のモル比(仕込み原料による理論値)で有する重合体(高分子化合物D)の合成を、下記のとおり行った。
で表される化合物(1.477g、2.00mmol)と、下記式(M−3−BR):
で表される化合物(0.548g、1.00mmol)と、下記式(M−11−BR):
で表される化合物(0.472g、0.80mmol)と、下記式(M−4−BR):
で表される化合物(0.148g、0.20mmol)と、ジクロロビス(トリス(o−メトキシフェニル))ホスフィンパラジウム(1.77mg)と、トルエン(50mL)とを混合し、105℃で加熱した。
Claims (19)
- 下記式(1)で表される構成単位及び下記式(2)で表される構成単位を有する高分子化合物。
[式中、n1及びn2はそれぞれ独立に、1〜5の整数を示し、
R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10はそれぞれ独立に、
水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、
R1、R2、R3及びR4がそれぞれ複数存在するとき、複数存在するR1、R2、R3及びR4は互いに同一でも異なっていてもよく、R1、R2、R3及びR4のうち隣接する基同士は互いに連結して環構造を形成していてもよく、R7、R8、R9及びR10のうち隣接する基同士は互いに連結して環構造を形成していてもよい。]
[式中、a及びbはそれぞれ独立に0又は1を示し、
Ar1、Ar2、Ar3及びAr4はそれぞれ独立に、非置換若しくは置換のアリーレン基、非置換若しくは置換の2価の複素環基、又は、アリーレン基及び2価の複素環基から選ばれる同一若しくは異なる2以上の基が連結した2価の基(該基は、置換基を有していてもよい。)を示し、
RA、RB及びRCはそれぞれ独立に、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基又は非置換若しくは置換の1価の複素環基を示し、
Ar1、Ar2、Ar3及びAr4はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と互いに連結して環構造を形成していてもよい。] - 前記式(4)で表される構成単位の少なくとも1個が、非置換若しくは置換のフルオレンジイル基からなる構成単位である、請求項3に記載の高分子化合物。
- 前記式(4)で表される構成単位の少なくとも1個が、非置換若しくは置換の2,7−フルオレンジイル基からなる構成単位である、請求項4に記載の高分子化合物。
- 前記式(4)で表される構成単位の少なくとも1個が、非置換若しくは置換のフェニレン基、非置換若しくは置換のナフタレンジイル基、非置換若しくは置換のアントラセンジイル基、及び、下記式(5’)で表される基、からなる群より選ばれる少なくとも一種の基からなる構成単位である、請求項3〜5のいずれか一項に記載の高分子化合物。
[式中、c1及びc2はそれぞれ独立に0〜4の整数を示し、c3は0〜5の整数を示し、
R12、R13及びR14はそれぞれ独立に、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基、非置換若しくは置換の1価の複素環基、非置換若しくは置換のアルコキシカルボニル基、非置換若しくは置換のシリル基、ハロゲン原子、カルボキシル基又はシアノ基を示し、
R12、R13及びR14がそれぞれ複数存在するとき、複数存在するR12、R13及びR14は互いに同一でも異なっていてもよい。] - 前記式(1)で表される構成単位と、前記式(2)で表される構成単位と、非置換若しくは置換のフルオレンジイル基からなる構成単位と、非置換若しくは置換のフェニレン基からなる構成単位と、を有する、請求項6に記載の高分子化合物。
- 前記式(1)で表される構成単位と、前記式(2)で表される構成単位と、非置換若しくは置換のフルオレンジイル基からなる構成単位と、非置換若しくは置換のナフタレンジイル基からなる構成単位と、を有する、請求項6に記載の高分子化合物。
- 前記式(1)で表される構成単位と、前記式(2)で表される構成単位と、非置換若しくは置換のフルオレンジイル基からなる構成単位と、非置換若しくは置換のアントラセンジイル基からなる構成単位と、を有する、請求項6に記載の高分子化合物。
- 前記式(1)で表される構成単位と、前記式(2)で表される構成単位と、非置換若しくは置換のフルオレンジイル基からなる構成単位と、下記式(5)で表される構成単位と、を有する、請求項6に記載の高分子化合物。
[式中、c1及びc2はそれぞれ独立に0〜4の整数を示し、c3は0〜5の整数を示し、
R12、R13及びR14はそれぞれ独立に、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基、非置換若しくは置換の1価の複素環基、非置換若しくは置換のアルコキシカルボニル基、非置換若しくは置換のシリル基、ハロゲン原子、カルボキシル基又はシアノ基を示し、
R12、R13及びR14がそれぞれ複数存在するとき、複数存在するR12、R13及びR14は互いに同一でも異なっていてもよい。] - 前記式(1)におけるn1及びn2が、それぞれ独立に3又は4である、請求項1〜10のいずれか一項に記載の高分子化合物。
- 下記式(6)で表される化合物。
[式中、m1及びm2はそれぞれ独立に1又は2を示し、
R21、R22、R23、R24、R25、R26、R27、R28、R29及びR30はそれぞれ独立に、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、
X11、X12、X13及びX14はそれぞれ独立に、−C(R31)2−で表される基(R31は、水素原子、非置換若しくは置換のアルキル基、非置換若しくは置換のアルコキシ基、非置換若しくは置換のアリール基、非置換若しくは置換のアリールオキシ基又は非置換若しくは置換の1価の複素環基を示し、複数存在するR31は互いに同一でも異なっていてもよい。)を示し、
R27、R28、R29及びR30のうち隣接する基同士は互いに連結して環構造を形成していてもよく、
Z1及びZ2はそれぞれ独立に、下記置換基群から選ばれる基を示す。
但し、R21、R22、R23及びR24のうち少なくとも1個は、水素原子以外の基である。<置換基群>
塩素原子、臭素原子、ヨウ素原子、
−O−S(=O)2R41(R41は、アルキル基、又は、アルキル基、アルコキシ基、ニトロ基、フッ素原子若しくはシアノ基で置換されていてもよいアリール基を示す。)で表される基、
−B(OR42)2(R42は水素原子又はアルキル基を示し、複数存在するR42は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基、
−BF4Q1(Q1は、Li+、Na+、K+、Rb+及びCs+からなる群より選ばれる1価の陽イオンを示す。)で表される基、
−MgY1(Y1は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、
−ZnY2(Y2は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基、及び、
−Sn(R43)3(R43は水素原子又はアルキル基を示し、複数存在するR43は互いに同一でも異なっていてもよく、互いに連結して環構造を形成していてもよい。)で表される基。] - 請求項1〜11のいずれか一項に記載の高分子化合物と、
正孔輸送材料、電子輸送材料及び発光材料からなる群より選ばれる少なくとも一種と、を含有する組成物。 - 請求項1〜11のいずれか一項に記載の高分子化合物と、溶媒と、を含有する液状組成物。
- 請求項1〜11のいずれか一項に記載の高分子化合物を含有する有機薄膜。
- 請求項13に記載の組成物を用いてなる有機薄膜。
- 請求項15又は16に記載の有機薄膜を有する発光素子。
- 請求項17に記載の発光素子を有する面状光源。
- 請求項17に記載の発光素子を有する表示装置。
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JPWO2014157016A1 (ja) | 2013-03-28 | 2017-02-16 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
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