DE112006001016T5 - Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung - Google Patents
Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung Download PDFInfo
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- DE112006001016T5 DE112006001016T5 DE112006001016T DE112006001016T DE112006001016T5 DE 112006001016 T5 DE112006001016 T5 DE 112006001016T5 DE 112006001016 T DE112006001016 T DE 112006001016T DE 112006001016 T DE112006001016 T DE 112006001016T DE 112006001016 T5 DE112006001016 T5 DE 112006001016T5
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 208
- 229920000642 polymer Polymers 0.000 title claims abstract description 189
- 125000001424 substituent group Chemical group 0.000 claims abstract description 77
- 125000003118 aryl group Chemical group 0.000 claims abstract description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 12
- 125000004429 atom Chemical group 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- -1 amino, substituted amino, silyl Chemical group 0.000 claims description 279
- 239000010410 layer Substances 0.000 claims description 186
- 239000000463 material Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 74
- 239000002904 solvent Substances 0.000 claims description 68
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
- 239000010408 film Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 19
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 18
- 125000005110 aryl thio group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
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- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
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- 150000004696 coordination complex Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 10
- 230000000379 polymerizing effect Effects 0.000 claims description 10
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
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- 239000007858 starting material Substances 0.000 claims description 6
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- 238000012643 polycondensation polymerization Methods 0.000 claims description 5
- 229910005965 SO 2 Inorganic materials 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
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- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 2
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 60
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- 0 Cc(c(*)c1*)c(*)c2c1[n](*)c(*)c2* Chemical compound Cc(c(*)c1*)c(*)c2c1[n](*)c(*)c2* 0.000 description 37
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- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
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- 150000005840 aryl radicals Chemical class 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
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- 230000000694 effects Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000004982 aromatic amines Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000012295 chemical reaction liquid Substances 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
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- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- 230000005685 electric field effect Effects 0.000 description 8
- 238000009413 insulation Methods 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- 238000007639 printing Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910052711 selenium Inorganic materials 0.000 description 7
- 239000011669 selenium Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229960003540 oxyquinoline Drugs 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
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- 239000002491 polymer binding agent Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 229920000123 polythiophene Polymers 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 229920000292 Polyquinoline Polymers 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
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- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
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- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 5
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- HAIGIJCTBFVMEP-UHFFFAOYSA-N 2-bromo-5-tert-butyl-1,3-dimethylbenzene Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1Br HAIGIJCTBFVMEP-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
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- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
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- KTLFENNEPHBKJD-UHFFFAOYSA-K benzyl(trimethyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 KTLFENNEPHBKJD-UHFFFAOYSA-K 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
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- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 230000001419 dependent effect Effects 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
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- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 238000010345 tape casting Methods 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- ABPDSMWWDSTGRM-UHFFFAOYSA-N 1-n,4-n-bis(4-bromophenyl)-1-n,4-n-bis(4-tert-butyl-2,6-dimethylphenyl)benzene-1,4-diamine Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1N(C=1C=CC(=CC=1)N(C=1C=CC(Br)=CC=1)C=1C(=CC(=CC=1C)C(C)(C)C)C)C1=CC=C(Br)C=C1 ABPDSMWWDSTGRM-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
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- 235000021190 leftovers Nutrition 0.000 description 1
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- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
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- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical group OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
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- 229910001415 sodium ion Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical group S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 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
- 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
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP2005131383 | 2005-04-28 | ||
JP2005-131383 | 2005-04-28 | ||
PCT/JP2006/309353 WO2006118345A1 (ja) | 2005-04-28 | 2006-04-28 | 高分子化合物およびそれを用いた高分子発光素子 |
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DE112006001016T5 true DE112006001016T5 (de) | 2008-04-03 |
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DE112006001016T Withdrawn DE112006001016T5 (de) | 2005-04-28 | 2006-04-28 | Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung |
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KR (1) | KR20080013926A (zh) |
CN (1) | CN101184789B (zh) |
DE (1) | DE112006001016T5 (zh) |
GB (1) | GB2440482A (zh) |
WO (1) | WO2006118345A1 (zh) |
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JP2006328387A (ja) * | 2005-04-28 | 2006-12-07 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
JP5095189B2 (ja) * | 2005-11-30 | 2012-12-12 | 住友化学株式会社 | 高分子系材料及びそれを用いた高分子発光素子 |
CN101316879B (zh) * | 2005-11-30 | 2011-10-05 | 住友化学株式会社 | 聚合物材料和使用该聚合物材料的聚合物发光器件 |
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JP5836970B2 (ja) | 2009-12-22 | 2015-12-24 | メルク パテント ゲーエムベーハー | 機能性材料を含む調合物 |
EP2517537B1 (en) | 2009-12-22 | 2019-04-03 | Merck Patent GmbH | Electroluminescent functional surfactants |
EP2517278B1 (en) | 2009-12-22 | 2019-07-17 | Merck Patent GmbH | Electroluminescent formulations |
DE102010009193B4 (de) | 2010-02-24 | 2022-05-19 | MERCK Patent Gesellschaft mit beschränkter Haftung | Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend |
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EP3309236B1 (en) | 2010-05-27 | 2019-11-27 | Merck Patent GmbH | Electroluminescent device comprising quantum dots and use of a formulation comprising quantum dots |
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JP2014527550A (ja) | 2011-07-25 | 2014-10-16 | メルク パテント ゲーエムベーハー | 機能性側鎖基を有するポリマーおよびオリゴマー |
US9178159B2 (en) | 2011-07-25 | 2015-11-03 | Merck Patent Gmbh | Copolymers with functionalized side chains |
DE102012016192A1 (de) | 2011-08-19 | 2013-02-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102011121022A1 (de) | 2011-12-13 | 2013-06-13 | Merck Patent Gmbh | Organische Sensibilisatoren für Up- Conversion |
CN105409022B (zh) | 2013-07-29 | 2018-06-19 | 默克专利有限公司 | 电光器件及其用途 |
JP6567519B2 (ja) | 2013-07-29 | 2019-08-28 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | エレクトロルミネッセンス素子 |
JP6695863B2 (ja) | 2014-09-05 | 2020-05-20 | メルク パテント ゲーエムベーハー | 調合物と電子素子 |
CN107406384B (zh) | 2014-12-04 | 2021-07-23 | 广州华睿光电材料有限公司 | 氘化的有机化合物、包含该化合物的混合物、组合物及有机电子器件 |
US10573827B2 (en) | 2014-12-11 | 2020-02-25 | Guangzhou Chinaray Optoelectronics Materials Ltd. | Organic metal complex, and polymer, mixture, composition and organic electronic device containing same and use thereof |
EP3241248A1 (de) | 2014-12-30 | 2017-11-08 | Merck Patent GmbH | Formulierungen und elektronische vorrichtungen |
WO2016112761A1 (zh) | 2015-01-13 | 2016-07-21 | 广州华睿光电材料有限公司 | 含乙炔基交联基团的共轭聚合物、包含其的混合物、组合物、有机电子器件及其应用 |
KR102570137B1 (ko) | 2015-03-30 | 2023-08-23 | 메르크 파텐트 게엠베하 | 실록산 용매를 포함하는 유기 기능성 재료의 제형 |
CN111477766B (zh) | 2015-06-12 | 2023-04-07 | 默克专利有限公司 | 作为用于oled制剂的溶剂的含有非芳族环的酯 |
US11046884B2 (en) | 2015-08-28 | 2021-06-29 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
WO2017080326A1 (zh) | 2015-11-12 | 2017-05-18 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
EP3387077B1 (en) | 2015-12-10 | 2023-10-18 | Merck Patent GmbH | Formulations containing ketones comprising non-aromatic cycles |
EP4084109A1 (en) | 2015-12-15 | 2022-11-02 | Merck Patent GmbH | Esters containing aromatic groups as solvents for organic electronic formulations |
EP3390549B1 (en) | 2015-12-16 | 2022-06-29 | Merck Patent GmbH | Formulations containing a solid solvent |
KR20180095028A (ko) | 2015-12-16 | 2018-08-24 | 메르크 파텐트 게엠베하 | 둘 이상의 상이한 용매의 혼합물을 함유하는 제형 |
EP3417033B1 (en) | 2016-02-17 | 2021-02-24 | Merck Patent GmbH | Formulation of an organic functional material |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
CN109153871A (zh) | 2016-06-16 | 2019-01-04 | 默克专利有限公司 | 有机功能材料的制剂 |
EP3472249B1 (en) | 2016-06-17 | 2022-02-02 | Merck Patent GmbH | Formulation of an organic functional material |
TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
JP6980757B2 (ja) | 2016-08-04 | 2021-12-15 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
JP7046938B2 (ja) | 2016-10-31 | 2022-04-04 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
EP3532566B1 (en) | 2016-10-31 | 2021-04-21 | Merck Patent GmbH | Formulation of an organic functional material |
EP3546532B1 (en) | 2016-11-23 | 2021-06-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink composition, preparation method therefor, and uses thereof |
CN110036498B (zh) | 2016-12-06 | 2023-04-18 | 默克专利有限公司 | 电子器件的制备方法 |
KR102486614B1 (ko) | 2016-12-13 | 2023-01-09 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光(el)元件之方法 |
JP7123967B2 (ja) | 2017-03-31 | 2022-08-23 | メルク パテント ゲーエムベーハー | 有機発光ダイオード(oled)のための印刷方法 |
JP7200128B2 (ja) | 2017-04-10 | 2023-01-06 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
CN110546236A (zh) | 2017-05-03 | 2019-12-06 | 默克专利有限公司 | 有机功能材料的制剂 |
WO2019016184A1 (en) | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL |
JP7293229B2 (ja) | 2017-12-15 | 2023-06-19 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
CN111712551A (zh) | 2018-02-26 | 2020-09-25 | 默克专利有限公司 | 有机功能材料的制剂 |
CN112236488A (zh) | 2018-06-15 | 2021-01-15 | 默克专利有限公司 | 有机功能材料的制剂 |
US20220013724A1 (en) | 2018-11-06 | 2022-01-13 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
CN115427521A (zh) | 2020-04-21 | 2022-12-02 | 默克专利有限公司 | 有机功能材料的制剂 |
CN115700058A (zh) | 2020-04-21 | 2023-02-03 | 默克专利有限公司 | 包含有机功能材料的乳液 |
KR20230114756A (ko) | 2020-12-08 | 2023-08-01 | 메르크 파텐트 게엠베하 | 잉크 시스템 및 잉크젯 인쇄를 위한 방법 |
JP2024515366A (ja) | 2021-04-23 | 2024-04-09 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
WO2023012084A1 (en) | 2021-08-02 | 2023-02-09 | Merck Patent Gmbh | A printing method by combining inks |
TW202349760A (zh) | 2021-10-05 | 2023-12-16 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
TW202411366A (zh) | 2022-06-07 | 2024-03-16 | 德商麥克專利有限公司 | 藉由組合油墨來印刷電子裝置功能層之方法 |
WO2024126635A1 (en) | 2022-12-16 | 2024-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
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JP3758694B2 (ja) * | 1994-10-13 | 2006-03-22 | 三星エスディアイ株式会社 | 有機薄膜el素子 |
GB9726810D0 (en) * | 1997-12-19 | 1998-02-18 | Zeneca Ltd | Compounds composition & use |
US20060094859A1 (en) * | 2004-11-03 | 2006-05-04 | Marrocco Matthew L Iii | Class of bridged biphenylene polymers |
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KR20080013926A (ko) | 2008-02-13 |
WO2006118345A1 (ja) | 2006-11-09 |
CN101184789B (zh) | 2012-05-30 |
GB0722483D0 (en) | 2007-12-27 |
GB2440482A (en) | 2008-01-30 |
CN101184789A (zh) | 2008-05-21 |
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