WO2022050051A1 - 化合物 - Google Patents
化合物 Download PDFInfo
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- WO2022050051A1 WO2022050051A1 PCT/JP2021/030239 JP2021030239W WO2022050051A1 WO 2022050051 A1 WO2022050051 A1 WO 2022050051A1 JP 2021030239 W JP2021030239 W JP 2021030239W WO 2022050051 A1 WO2022050051 A1 WO 2022050051A1
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- WIPO (PCT)
- Prior art keywords
- group
- formula
- substituent
- carbon atoms
- meth
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 157
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 43
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 40
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 91
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 239000011347 resin Substances 0.000 claims description 71
- 229920005989 resin Polymers 0.000 claims description 71
- 239000011342 resin composition Substances 0.000 claims description 46
- 239000003505 polymerization initiator Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- -1 3,3-dimethylbutyl group Chemical group 0.000 description 218
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 72
- 150000002430 hydrocarbons Chemical group 0.000 description 50
- 239000002904 solvent Substances 0.000 description 46
- 239000000049 pigment Substances 0.000 description 38
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 33
- 238000000034 method Methods 0.000 description 26
- 239000000975 dye Substances 0.000 description 25
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000003086 colorant Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000010408 film Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 13
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 150000004292 cyclic ethers Chemical group 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000002270 dispersing agent Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000001018 xanthene dye Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- ZXXUPZWDQJEEQW-UHFFFAOYSA-N [[3-cyclohexyl-1-oxo-1-(4-phenylsulfanylphenyl)propan-2-ylidene]amino] acetate Chemical compound C(C)(=O)ON=C(C(=O)C1=CC=C(C=C1)SC1=CC=CC=C1)CC1CCCCC1 ZXXUPZWDQJEEQW-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 3
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WDQIDQYSOAQPNJ-UHFFFAOYSA-N 3,4-epoxytricyclo[5.2.1.02,6]decyl acrylate Chemical compound C12CC3OC3C2C2(OC(=O)C=C)CC1CC2 WDQIDQYSOAQPNJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].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 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
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- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- WERQPPCVTFSKSO-UHFFFAOYSA-N 3a,7a-dimethyl-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1CC=CC2(C)C(=O)OC(=O)C21C WERQPPCVTFSKSO-UHFFFAOYSA-N 0.000 description 2
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 2
- DOWVFPAIJRADGF-UHFFFAOYSA-N 4-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=CC2=C1C(=O)OC2=O DOWVFPAIJRADGF-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- OHMDZMAJDUVGHO-UHFFFAOYSA-N 5-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=C2C(=O)OC(=O)C2=C1 OHMDZMAJDUVGHO-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 0 CCN(C(C(C1)=C2C=C=C1F)=C(C)C*P(*)(*)=*C)C2=NC(C(C1)=C2C=CC1F)=*C2=Nc1c(cc(cc2)F)c2c2[n]1NC(C(C=C1)=C3CC1F)=NC3N2 Chemical compound CCN(C(C(C1)=C2C=C=C1F)=C(C)C*P(*)(*)=*C)C2=NC(C(C1)=C2C=CC1F)=*C2=Nc1c(cc(cc2)F)c2c2[n]1NC(C(C=C1)=C3CC1F)=NC3N2 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QGOKIEUFWNCGFO-UHFFFAOYSA-N propanoic acid;pyrrole-2,5-dione Chemical compound CCC(O)=O.O=C1NC(=O)C=C1 QGOKIEUFWNCGFO-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YEOUFHBJWTZWCZ-UHFFFAOYSA-M sulforhodamine G Chemical compound [Na+].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O YEOUFHBJWTZWCZ-UHFFFAOYSA-M 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6596—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Definitions
- the present invention relates to a compound, a colored resin composition, a color filter and a display device.
- Optical filters used in liquid crystal display devices, electroluminescence display devices, display devices such as plasma displays, and solid-state image pickup devices such as CCDs and CMOS sensors are manufactured from colored resin compositions.
- Aluminum phthalocyanine pigments are known as colorants for such colored resin compositions.
- Patent Document 1 an aluminum phthalocyanine pigment having a specific structure as a colorant is used, and while having high brightness when used in a color filter, it is not only resistant to NMP (N-methylpyrrolidone), but also developable and coating. It is described that a coloring composition for a color filter having excellent flatness is provided.
- the aluminum phthalocyanine pigment described in Patent Document 1 may have a large color difference before and after post-baking. Therefore, the present invention provides a novel compound capable of reducing the color difference before and after post-baking.
- R 1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent.
- R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond connecting Z 3 and R 1 .
- Y 1 and Z 1 independently represent an oxygen atom or a sulfur atom, respectively.
- Z 2 and Z 3 independently represent a single bond, an oxygen atom or a sulfur atom. However, at least one of Y 1 , Z 1 , Z 2 and Z 3 represents a sulfur atom.
- X 1 to X 4 each independently represent a sulfamoyl group which may have -R 4 , -OR 4 , -SR 4 , a halogen atom, a nitro group or a substituent.
- R 4 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- n1 to n4 each independently represent an integer of 0 to 4.
- R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent.
- Y 2 and Z 4 independently represent an oxygen atom or a sulfur atom, respectively.
- Z 5 represents a single bond, an oxygen atom or a sulfur atom.
- Y 2 , Z 4 and Z 5 represents a sulfur atom.
- X 5 to X 12 each independently represent a sulfamoyl group which may have -R 5 , -OR 5 , -SR 5 , a halogen atom, a nitro group or a substituent.
- R 5 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- n5 to n12 each independently represent an integer of 0 to 4.
- the color difference before and after post-baking can be reduced.
- the present invention will be described in more detail with reference to the partial structure of the compound represented by the formula (I) or the formula (II).
- the color difference before and after post-baking can be reduced in the color filter formed from the colored resin composition containing the novel compound.
- the change in transmittance between 500 nm and 650 nm before and after post-baking can be reduced.
- the compound represented by the formula (I) includes a compound having a resonance structure represented by the formula (Ia) or a compound having an equilibrium relationship represented by the formula (Ib), and is represented by the formula (II).
- the compound represented by the formula (IIa) includes a compound having a resonance structure represented by the formula (IIa) or a compound having an equilibrium relationship represented by the formula (IIb).
- R 1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent.
- R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a single bond connecting Z 3 and R 1 .
- Y 1 and Z 1 independently represent an oxygen atom or a sulfur atom, respectively.
- Z 2 and Z 3 independently represent a single bond, an oxygen atom or a sulfur atom. However, at least one of Y 1 , Z 1 , Z 2 and Z 3 represents a sulfur atom.
- X 1 to X 4 each independently represent a sulfamoyl group which may have -R 4 , -OR 4 , -SR 4 , a halogen atom, a nitro group or a substituent.
- R 4 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- n1 to n4 each independently represent an integer of 0 to 4.
- R 3 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent.
- Y 2 and Z 4 independently represent an oxygen atom or a sulfur atom, respectively.
- Z 5 represents a single bond, an oxygen atom or a sulfur atom.
- Y 2 , Z 4 and Z 5 represents a sulfur atom.
- X 5 to X 12 each independently represent a sulfamoyl group which may have -R 5 , -OR 5 , -SR 5 , a halogen atom, a nitro group or a substituent.
- R 5 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- n5 to n12 each independently represent an integer of 0 to 4.
- the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 5 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated. It may be chain-like or cyclic (lipid ring-type hydrocarbon group).
- Saturated or unsaturated chain hydrocarbon groups represented by R 1 to R 5 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group and a decyl group.
- Undecyl group Undecyl group, Dodecyl group, Tridecyl group, Tetradecyl group, Pentadecyl group, Hexadecyl group, Heptadecyl group, Octadecyl group, Nonadecil group, Icosyl group and other linear alkyl groups; Propyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethyl Propyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2-propylpentyl group, 1-ethyl-1 , 2-dimethylpropyl group, 1-methylp
- the saturated chain hydrocarbon group represented by R 1 to R 5 (that is, a linear alkyl group or a branched alkyl group) preferably has 1 to 10 carbon atoms, more preferably 1 to 7 carbon atoms. It is more preferably 1 to 5.
- the unsaturated chain hydrocarbon group represented by R 1 to R 5 (that is, an alkenyl group or an alkynyl group) preferably has 2 to 10 carbon atoms, more preferably 2 to 7 carbon atoms, and even more preferably 2 to 7 carbon atoms. It is 2 to 5.
- Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R 1 to R 5 include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a 1-methylcyclohexyl.
- Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl group, norbornenyl group, adamantyl group and bicyclo [2.2.2] octyl group; And so on.
- the saturated or unsaturated alicyclic hydrocarbon group represented by R 1 to R 5 has preferably 3 to 10 carbon atoms.
- the aromatic hydrocarbon groups represented by R 1 to R 5 include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group and a 4-ethyl group.
- Phenyl group 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group , 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3 , 5-di (tert-butyl) phenyl group, 3,5-di (tert-butyl) -4-methylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis (1-methyl) Ethyl) phenyl group, 2,4,6-tris (1-methylethyl)
- the hydrocarbon group represented by R 1 to R 5 is a combination of the above-mentioned hydrocarbon groups (for example, an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group). It may be a hydrocarbon, Benzyl group, (2-methylphenyl) methyl group, (3-methylphenyl) methyl group, (4-methylphenyl) methyl group, (2-ethylphenyl) methyl group, (3-ethylphenyl) methyl group, (4) -Ethylphenyl) methyl group, (2- (tert-butyl) phenyl) methyl group, (3- (tert-butyl) phenyl) methyl group, (4- (tert-butyl) phenyl) methyl group, (3,5) -Alkyl group such as (dimethylphenyl) methyl group, 1-phenylethyl group, 1-methyl-1-phenylethyl group, 1,1-diphen
- Arylalkenyl groups such as 1-phenylethenyl group, 2-phenylethenyl group (phenylvinyl group), 2,2-diphenylethenyl group, 2-phenyl-2- (1-naphthyl) ethenyl group;
- Aryl alkynyl groups such as phenylethynyl groups;
- a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; Examples thereof include a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl (phenyl) methyl) phenyl group.
- the number of these carbon atoms is preferably 7 to 18, and more preferably 7 to 15.
- the groups represented by R 1 to R 5 are, for example, a cyclopropylmethyl group and a cyclopropylethyl group as a group in which the above-mentioned hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) are combined.
- One or more alicyclic hydrocarbons such as group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl) methyl group, cyclohexylethyl group, adamantylmethyl group, etc. It may be an alkyl group to which a hydrogen group is bonded. The number of these carbon atoms is preferably 4 to 15, and more preferably 4 to 10.
- the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 5 may have a substituent.
- a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 5 a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, ⁇ OR a1 and the like. Examples thereof include -CO 2 R a1 , -SR a1 , -SO 2 R a1 , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a 2 .
- R a1 and R a2 independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
- the hydrocarbon groups having 1 to 20 carbon atoms represented by R a1 and R a2 are the same as the above-mentioned hydrocarbon groups having 1 to 20 carbon atoms represented by R 1 to R 5 .
- the heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 5 may be a monocyclic ring or a polycyclic ring, and preferably has a ring structure. It is a heterocycle containing a heteroatom as an element. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like. Heterocycles containing only nitrogen atoms as heteroatomes include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, piperazine; pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4.
- -5-membered ring-based unsaturated heterocycles such as triazole
- 6-membered ring-based unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine
- indazole indolin, isoindrin, isoindrin-1 , 3-Dione, Indol, Indolidine, Benmidazole, Kinolin, Isoquinolin, Kinoxalin, Kinazoline, Synnoline, Phthalazine, Naftilidine, Purine, Pteridine, Benpyrazole, Bentopiperidine and other fused bicyclic heterocycles
- Carbazole, Acrydin, Phenazine Such as fused tricyclic heterocycles; etc.
- heterocycle containing only an oxygen atom as a hetero atom examples include monocyclic saturated heterocycles such as oxylane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; 1,4-dioxaspiro [4.
- Bicyclic saturated heterocycles such as decane and 1,4-dioxaspiro [4.5] nonane; lactone-based heterocycles such as ⁇ -acetlactone, ⁇ -propiolactone, ⁇ -butyrolactone and ⁇ -valerolactone; 5-membered ring-based unsaturated heterocycle such as furan; 6-membered ring-based unsaturated heterocycle such as 2H-pyran, 4H-pyran; Heterocycles; fused tricyclic heterocycles such as xanthene and dibenzofuran; and the like.
- lactone-based heterocycles such as ⁇ -acetlactone, ⁇ -propiolactone, ⁇ -butyrolactone and ⁇ -valerolactone
- 5-membered ring-based unsaturated heterocycle such as furan
- 6-membered ring-based unsaturated heterocycle such as 2H-pyran, 4H-pyran
- Heterocycles fused tricyclic
- heterocycle containing only a sulfur atom as a hetero atom examples include a 5-membered ring-based saturated heterocycle such as dithiolane; a 6-membered ring-based saturated heterocycle such as thiane and 1,3-dithian; and a 5-membered ring-based unsaturated heterocycle such as thiophene.
- Heterocycle; 6-membered ring-based unsaturated heterocycle such as 4H-thiopyran; benzothiopyran such as benzotetrahydrothiopyran, fused bicyclic heterocycle such as benzothiophene; fused tricyclic heterocycle such as thianthene, dibenzothiophene; And so on.
- heterocycle containing a nitrogen atom and an oxygen atom as a heteroatom examples include a monocyclic saturated heterocycle such as morpholine, 2-pyrrolidone and 2-piperidone; a monocyclic unsaturated heterocycle such as oxazole and isooxazole; benzoxazole, Examples thereof include a fused bicyclic heterocycle such as benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; and a condensed tricyclic heterocycle such as phenoxazine;.
- a monocyclic saturated heterocycle such as morpholine, 2-pyrrolidone and 2-piperidone
- a monocyclic unsaturated heterocycle such as oxazole and isooxazole
- benzoxazole examples thereof include a fused bicyclic heterocycle such as benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline;
- heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms examples include a monocyclic heterocycle such as thiazole; a fused bicyclic heterocycle such as benzothiazole; a condensed tricyclic heterocycle such as phenothiazine; and the like.
- the heterocyclic group preferably has 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20 carbon atoms.
- the heterocyclic group may have a substituent, and the substituents include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , -SO 2 R a1 , and-.
- Examples thereof include SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 (however, R a1 and R a 2 are the same as described above).
- the bond position of the heterocycle is a portion where an arbitrary hydrogen atom contained in each ring is eliminated.
- Examples of the halogen atom used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 5 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- R 1 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and a part or all of R 1 is *-.
- the bond formed by sharing a pair of electrons with 3 corresponds to a single bond represented by R 2 .
- Examples of the halogen atom represented by X 1 to X 12 include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and a fluorine atom is preferable.
- the sulfamoyl group represented by X 1 to X 12 is represented by * -SO 2 -NH 2 (* means a bond).
- the sulfamoyl group represented by X 1 to X 12 may have a substituent.
- an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent and a heterocyclic group which may have a substituent may be used.
- the heterocyclic group and the halogen atom which may have a substituent and which are used as the substituent of the sulfamoyl group represented by X 1 to X 12 have 1 carbon atoms represented by R 1 to R 5 . Examples thereof include heterocyclic groups and halogen atoms which may have a substituent and are used as substituents of the hydrocarbon groups of to 20, and the preferred embodiments thereof are also the same.
- the aromatic hydrocarbon group preferably has 6 to 10 carbon atoms, and more preferably 6 to 8 carbon atoms.
- the aromatic hydrocarbon group may have a substituent, and the substituents include a halogen atom, a nitro group, a cyano group, -OR a1 , -CO 2 R a1 , -SR a1 , and -SO 2 R a1 . , -SO 3 R a1 , -SO 2 NR a1 R a2 and -NR a1 R a2 , etc. (however, R a1 and R a 2 are the same as described above).
- -R 4 represented by X 1 to X 4 and -R 5 represented by X 5 to X 12 are preferably aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and are saturated chains having 1 to 20 carbon atoms. Hydrocarbon groups are more preferred, saturated chain hydrocarbon groups having 1 to 10 carbon atoms are even more preferred, branched alkyl groups having 1 to 5 carbon atoms are even more preferred, and tert-butyl groups are particularly preferred.
- R 1 is An aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have a substituent, is preferable.
- R 2 is An unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferable.
- An unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is more preferable.
- An unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is more preferable.
- An alkenyl group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is more preferable.
- An ethenyl group which may have a substituent or a phenyl group which may have a substituent is particularly preferable.
- n1 to n4 are independently, preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.
- X 1 to X 4 are preferably ⁇ R 4 or a halogen atom.
- At least one of Y 1 , Z 1 , Z 2 and Z 3 represents a sulfur atom, where Y 1 is a sulfur atom and Z 1 is an oxygen atom, Y 1 is an oxygen atom and Z 1 is a sulfur atom. It is preferable to satisfy at least one aspect of the above-mentioned aspect and the aspect in which Z 2 and Z 3 are sulfur atoms. However, when R 2 is an unsaturated hydrocarbon group, Z 2 and Z 3 are preferably single bonds.
- Z 1 is a sulfur atom and Z 1 is an oxygen atom
- Z 2 is a single bond, an oxygen atom or a sulfur atom
- Z 3 is a single bond.
- R 1 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent
- R 2 may have a substituent and has 6 to 20 carbon atoms.
- R 2 is an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent
- Z 2 is a single bond
- Z 3 is a single bond
- R 1 is used.
- R 2 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent
- Z 2 is a single bond
- Z 3 is a single bond
- R 1 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent
- R 2 has a substituent. It is more preferably an unsaturated hydrocarbon group having 2 to 7 carbon atoms which may be used.
- Z 2 and Z 3 are sulfur atoms
- Y 1 is an oxygen atom or a sulfur atom
- Z 1 is an oxygen atom or a sulfur atom
- R 1 may have a substituent and has 6 to 20 carbon atoms.
- R 2 is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent
- Y 1 is an oxygen atom
- Z 1 is oxygen.
- R 1 is an atomic
- R 1 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent
- R 2 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent. It is more preferably a hydrocarbon group.
- R 3 is An unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferable.
- An unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is more preferable.
- An unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is more preferable.
- n5 to n12 are independently, preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.
- X 5 to X 12 each of -R 5 or a halogen atom is preferable.
- At least one of Y 2 , Z 4 and Z 5 represents a sulfur atom.
- R 3 is an unsaturated hydrocarbon group
- Z 5 is preferably a single bond.
- Z 5 is a single bond or an oxygen atom and R 3 has a substituent. It may be an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an unsaturated hydrocarbon group having 2 to 20 carbon atoms in which Z 5 is a single bond and R 3 may have a substituent.
- Z 5 is a single bond and R 3 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent, or Z 5 is a single bond and R 3 Is more preferably an unsaturated hydrocarbon group having 2 to 7 carbon atoms which may have a substituent.
- Z 5 is a single bond or an oxygen atom and R 3 may have a substituent. It may be an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an unsaturated hydrocarbon group having 2 to 20 carbon atoms in which Z 5 is a single bond and R 3 may have a substituent.
- Z 5 is a single bond and R 3 is an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent, or Z 5 is a single bond and R 3 is a substituent.
- it is an unsaturated hydrocarbon group having 2 to 7 carbon atoms which may have 2 to 7 carbon atoms, where Z 5 is a single bond and R 3 may have a substituent. It is more preferably an unsaturated hydrocarbon group of.
- Examples of the compound represented by the formula (I) include compounds represented by the formulas (IA) to (IE).
- R 1 , R 2 , Y 1 , Z 1 , Z 2 and Z 3 are the same as described above. ]
- Examples of the compound represented by the formula (IA) include compounds represented by the formulas (IA-1) to (IA-24) shown in Table 1.
- Examples of the compound represented by the formula (IB) include compounds represented by the formulas (IB-1) to (IB-24) shown in Table 2.
- Examples of the compound represented by the formula (IC) include compounds represented by the formulas (IC-1) to (IC-24) shown in Table 3.
- Examples of the compound represented by the formula (ID) include compounds represented by the formulas (ID-1) to (ID-24) shown in Table 4.
- Examples of the compound represented by the formula (IE) include compounds represented by the formulas (IE-1) to (IE-24) shown in Table 5.
- "i-1" represents a phenyl group
- "i-2" represents an ethenyl group.
- the compound to be used is preferable.
- Compounds represented by the formula (ID-1), the formula (ID-13), the formula (ID-21), the formula (ID-23), and the formula (ID-24) are more preferable.
- Examples of the compound represented by the formula (II) include compounds represented by the formulas (IIA) to (IIE).
- Examples of the compound represented by the formula (IIA) include compounds represented by the formulas (IIA-1) to (IIA-13) shown in Table 6.
- Examples of the compound represented by the formula (IIB) include compounds represented by the formulas (IIB-1) to (IIB-13) shown in Table 7.
- Examples of the compound represented by the formula (IIC) include compounds represented by the formulas (IIC-1) to (IIC-13) shown in Table 8.
- Examples of the compound represented by the formula (IID) include compounds represented by the formulas (IID-1) to (IID-13) shown in Table 9.
- Examples of the compound represented by the formula (IIE) include compounds represented by the formulas (IIE-1) to (IIE-13) shown in Table 10. In Tables 6 to 10, "i-1" represents a phenyl group and "i-2" represents an ethenyl group.
- the compound represented by the formula (IIA) includes Compounds represented by the formulas (IIA-1), formula (IIA-2), formula (IIA-8), formula (IIA-9), formula (IIA-12), and formula (IIA-13) are preferable. Compounds represented by the formula (IIA-1), the formula (IIA-8), the formula (IIA-12), and the formula (IIA-13) are more preferable.
- Compounds represented by the formula (IIB) As the compound represented by the formula (IIB), Compounds represented by the formula (IIB-1), the formula (IIB-2), the formula (IIB-8), the formula (IIB-9), the formula (IIB-12), and the formula (IIB-13) are preferable. Compounds represented by the formula (IIB-1), the formula (IIB-8), the formula (IIB-12), and the formula (IIB-13) are more preferable.
- Compounds represented by the formula (IIC-1), the formula (IIC-2), the formula (IIC-8), the formula (IIC-9), the formula (IIC-12), and the formula (IIC-13) are preferable.
- Compounds represented by the formula (IIC-1), the formula (IIC-8), the formula (IIC-12), and the formula (IIC-13) are more preferable.
- Compounds represented by the formula (IIE-1), the formula (IIE-2), the formula (IIE-8), the formula (IIE-9), the formula (IIE-12), and the formula (IIE-13) are preferable.
- Compounds represented by the formula (IIE-1), the formula (IIE-8), the formula (IIE-12), and the formula (IIE-13) are more preferable.
- the compound represented by the formula (I) can be produced, for example, by appropriately reacting the compound represented by the formula (III) with the compound represented by the formula (IV). Further, the compound represented by the formula (II) can be produced, for example, by appropriately reacting the compound represented by the formulas (IIIa) and (IIIb) with the compound represented by the formula (V).
- R 1 , R 2 , Y 1 , Z 1 , Z 2 , Z 3 , X 1 to X 4 and n1 to n 4 are the same as described above.
- the present invention includes a colored resin composition containing the above-mentioned compound represented by the formula (I) or the formula (II) and a resin (hereinafter, may be referred to as a resin (B)).
- the present invention also includes a colored resin composition containing a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). do.
- a compound represented by the above-mentioned formula (I) and / or formula (II) (hereinafter, may be referred to as a colorant (A1)) is used as a colorant (hereinafter, a colorant (A). ) May be included.
- the colored resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as a solvent (E)).
- the colored resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as a leveling agent (F)).
- the compounds exemplified as each component may be used alone or in combination of a plurality of kinds unless otherwise specified.
- the content of the colorant (A1) is preferably 0.5 to 70% by mass, more preferably 1 to 55% by mass, still more preferably 2 to 50% by mass, based on the total solid content of the colored resin composition. More preferably, it is 5 to 40% by mass.
- the "total amount of solid content” means the total amount of the components excluding the solvent from the colored resin composition of the present invention.
- the total amount of solid content and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography and gas chromatography.
- the content of the colorant (A1) is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 40 to 100% by mass, based on the total amount of the colorant (A). be.
- the colorant (A) may further contain a colorant different from the colorant (A1) (hereinafter, may be referred to as a colorant (A2)).
- the colorant (A2) may be either a dye or a pigment.
- the dye examples include compounds classified as having a hue other than pigments in the Color Index (The Society of Dyers and Colorists), and known dyes described in dyeing notes (Color Dyeing Co., Ltd.). Be done. Xanthene dyes are particularly preferred.
- the xanthene dye is a dye containing a compound having a xanthene skeleton in the molecule.
- examples of the xanthene dye include C.I. I. Acid Red 51 (hereinafter, the description of CI Acid Red is omitted and only the number is described. The same applies to the others), 52, 87, 92, 94, 289, 388, C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C.I. I. Basic Violet 10 (Rhodamine B), 11, C.I. I. Solvent Red 218, C.I. I. Modant Red 27, C.I. I.
- Examples thereof include reactive red 36 (rose bengal B), sulforhodamine G, xanthene dyes described in JP-A-2010-322999, and xanthene dyes described in Japanese Patent No. 4492760. Those that dissolve in an organic solvent are preferable.
- xanthene dye As the xanthene dye, a commercially available xanthene dye (for example, "Chugai Aminol Fast Pink R-H / C” manufactured by Chugai Pharmaceutical Co., Ltd., “Rhodamine 6G” manufactured by Taoka Chemical Industry Co., Ltd.) can be used. .. Further, it is also possible to synthesize using a commercially available xanthene dye as a starting material with reference to Japanese Patent Application Laid-Open No. 2010-32999.
- dyes include azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridin dyes, Stylyl dyes, coumarin dyes, quinoline dyes, nitro dyes and the like may be used, and known dyes are used. Specific examples of such dyes include C.I. I. Solvent Yellow 4 (Hereinafter, the description of CI Solvent Yellow is omitted and only the number is described.
- Solvent Blue 4 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.
- Solvent Green 1 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; etc.
- Solvent dye C. I.
- Acid dye C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; C. I.
- I. Direct dye C. I. Disperse Yellow 51, 54, 76; C. I. Disperse Violet 26, 27; C. I. Disperse Blue 1, 14, 56, 60; etc.
- I. Disperse dye C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C. I. Basic Violet 2; C. I. Basic Red 9; C. I. Basic Green 1; etc. C.I. I.
- C.I. I. Vat dyes and the like can be mentioned.
- these dyes one dye or a plurality of dyes may be used for each color, or dyes of each color may be combined.
- pigments classified as pigments in the Color Index (The Society of Dyers and Colorists Publishing), and the following pigments can be exemplified.
- Green pigment C.I. I. Pigment Green 7, 36, 58, etc.
- Yellow pigment C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.
- Orange pigment C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.
- Red pigment C.I. I.
- These pigments may use one pigment or a plurality of pigments for each color, or may combine pigments of each color.
- the pigment is treated with a rosin, a surface treatment using a pigment derivative having an acidic group or a basic group introduced therein, a graft treatment on the pigment surface with a polymer compound or the like, and atomization by a sulfuric acid atomization method or the like.
- Treatment, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, or the like may be performed.
- the particle size of the pigment is preferably substantially uniform.
- the pigment can be made into a pigment dispersion liquid in a state of being uniformly dispersed in the pigment dispersant solution by containing a pigment dispersant and performing a dispersion treatment.
- the pigments may be dispersed individually or may be mixed and dispersed.
- the pigment dispersant examples include a surfactant and the like, and any of a cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These pigment dispersants may be used alone or in combination of two or more.
- KP manufactured by Shin-Etsu Chemical Co., Ltd.
- Floren manufactured by Kyoeisha Chemical Co., Ltd.
- Solsperse registered trademark
- EFKA registered trademark
- BASF Azisper
- Disperbyk registered trademark
- BYK registered trademark
- the amount used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 15 parts by mass or more and 180 parts by mass or less, and further preferably 20 parts by mass with respect to 100 parts by mass of the pigment. More than 160 parts by mass or less.
- the amount of the pigment dispersant used is within the above range, a pigment dispersion liquid in a more uniform dispersed state tends to be obtained when two or more kinds of pigments are used.
- the content of the colorant (A2) is preferably 1 to 80% by mass, more preferably 1 to 70% by mass, based on the total amount of the colorant (A). , More preferably 1 to 60% by mass.
- the content of the colorant (A) in the colored resin composition is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, still more preferably 2 to 55% by mass with respect to the total amount of solid content. %.
- the content of the compound is within the above range, it becomes easier to obtain the desired spectroscopy and color density.
- the resin (B) is not particularly limited, but is preferably an alkali-soluble resin.
- the resin (B) include the following resins [K1] to [K6].
- Resin [K1] a structural unit derived from at least one (a) (hereinafter sometimes referred to as “(a)”) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and 2 carbon atoms.
- a polymer having a cyclic ether structure of ⁇ 4 and a structural unit derived from a monomer (b) having an ethylenically unsaturated bond (hereinafter, may be referred to as “(b)”); Resin [K2]; Structural unit derived from (a), structural unit derived from (b), and monomer (c) copolymerizable with (a) (however, (a) and (b) are A copolymer having a structural unit derived from (different) (hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]; A copolymer having a structural unit derived from (a) with (b) added and a structural unit derived from (c); Resin [K5]; A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b)
- (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexendicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-e, 5-
- Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule such as ⁇ - (hydroxymethyl) acrylic acid; and the like.
- acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerizability and solubility of the obtained resin in an alkaline aqueous solution.
- (B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
- a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group is preferable.
- (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate” have the same meaning.
- Examples of (b) include a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single having an oxetanyl group and an ethylenically unsaturated bond.
- a metric (b2) hereinafter sometimes referred to as "(b2)
- b3 a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond
- (b1) for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”). There is), a monomer (b1-2) having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter, may be referred to as “(b1-2)”).
- Examples of (b1-1) include glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p.
- Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, seroxide 2000; manufactured by Daicel Co., Ltd.), and 3,4-epoxycyclohexylmethyl (meth) acrylate (for example,).
- Cyclomer A400 manufactured by Dycel Co., Ltd.
- 3,4-epoxycyclohexylmethyl (meth) acrylate for example, Cyclomer M100; manufactured by Dycel Co., Ltd.
- 3,4-epoxytricyclo [5.2.1. 0 2,6 ] decyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyloxyethyl (meth) acrylate and the like can be mentioned.
- (b2) a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.
- Examples of (b2) include 3-methyl-3-methacrylloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, and 3-ethyl-3-acryloyloxymethyloxetane.
- (b3) a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable.
- Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscort V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.
- (b1) is preferable in that the reliability of the obtained optical filter such as heat resistance and chemical resistance can be further improved. Further, (b1-2) is more preferable in that the storage stability of the colored resin composition is excellent.
- Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
- Tricyclo [5.2.1.0 2,6 ] decene-8-yl (meth) acrylate (in the art, it is commonly referred to as "dicyclopentenyl (meth) acrylate”).
- Dicyclopentanyloxyethyl (meth) acrylate isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl ( (Meta) acrylic acid esters such as meth) acrylate; Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid; Bi
- styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are selected from the viewpoint of copolymerization reactivity and heat resistance. preferable.
- the ratio of the structural units derived from each is the ratio of all the structural units constituting the resin [K1].
- the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be excellent. be.
- the resin [K1] is, for example, the method described in the document "Experimental Method for Polymer Synthesis” (written by Takayuki Otsu, Kagaku-Dojin Co., Ltd., 1st edition, 1st print, published on March 1, 1972) and the relevant document. It can be manufactured with reference to the cited documents described in.
- a predetermined amount of (a) and (b), a polymerization initiator, a solvent and the like are placed in a reaction vessel, and for example, oxygen is replaced with nitrogen to create a deoxidized atmosphere, and the mixture is stirred. Examples thereof include a method of heating and keeping warm.
- the polymerization initiator, solvent and the like used here are not particularly limited, and those usually used in the art can be used.
- an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.
- the solvent any solvent may be used as long as it dissolves each monomer, and examples of the solvent (E) include a solvent described later.
- the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or the copolymer is taken out as a solid (powder) by a method such as reprecipitation. You may use the one.
- the solvent contained in the colored resin composition as the solvent in this polymerization, the solution after the reaction can be used as it is for the preparation of the colored resin composition, so that the colored resin composition can be produced. The process can be simplified.
- the ratio of the structural units derived from each is the ratio of all the structural units constituting the resin [K2].
- the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance and heat resistance of the obtained optical filter and the heat resistance It tends to have excellent mechanical strength.
- the resin [K2] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].
- the ratio of the structural units derived from each is the ratio of all the structural units constituting the resin [K3].
- the resin [K3] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].
- the resin [K4] is a carboxylic acid and / or a carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms having (b) obtained by obtaining a copolymer of (a) and (c). It can be manufactured by adding to.
- the copolymer of (a) and (c) is produced in the same manner as the method described as the method for producing the resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that mentioned in the resin [K3].
- the cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or the carboxylic acid anhydride derived from (a) in the copolymer.
- the atmosphere in the flask was replaced with air from nitrogen, and (b) a reaction catalyst of carboxylic acid or carboxylic acid anhydride and cyclic ether (for example, Tris (for example, Tris).
- Resin [K4] can be produced by putting (dimethylaminomethyl) phenol etc.) and a polymerization inhibitor (for example, hydroquinone etc.) in a flask and reacting at 60 to 130 ° C.
- the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, based on 100 mol of (a). Within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance between the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern tend to be improved. .. Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K4], and (b1-1) is more preferable.
- the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c).
- the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c).
- the reaction conditions such as the charging method, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization and the like. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization, and the like.
- the resin [K5] obtains a copolymer of (b) and (c) in the same manner as in the above-mentioned method for producing the resin [K1].
- the obtained copolymer may be a solution after the reaction as it is, a concentrated or diluted solution may be used, or a solid (powder) may be used by a method such as reprecipitation. You may use the one taken out as.
- the ratio of the structural units derived from (b) and (c) is, respectively, with respect to the total number of moles of all the structural units constituting the copolymer.
- the carboxylic acid or carboxylic acid anhydride of (a) is added to the cyclic ether derived from (b) of the copolymer of (b) and (c).
- the resin [K5] can be obtained by reacting an object.
- the amount of (a) used to react with the copolymer is preferably 5 to 80 mol with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K5], and (b1-1) is more preferable.
- the resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride.
- the carboxylic acid anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride.
- carboxylic acid anhydride examples include maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride and the like.
- the amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mol with respect to 1 mol of the amount used in (a).
- Specific resin (B) includes 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ].
- Resin such as decyl acrylate / (meth) acrylic acid copolymer [K1]; 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl acrylate / benzyl (meth) acrylate / (meth) acrylic Acid copolymer, glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl acrylate / (meth) acrylic acid / N-cyclohexylmaleimide
- the resin (B) has a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, a cyclic ether structure having 2 to 4 carbon atoms, and an ethylenically unsaturated bond. It is preferably a copolymer containing a structural unit (resin [K1] or resin [K2]), and more preferably resin [K2].
- the polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 500 to 100,000, more preferably 700 to 50,000, and even more preferably 900 to 30,000.
- the molecular weight is within the above range, the hardness of the optical filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the coloring pattern tends to be improved.
- the degree of dispersion [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
- the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g in terms of solid content.
- the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution. ..
- the content of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, and further preferably 17 to 70% by mass with respect to the total amount of solid content.
- the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tend to be improved.
- the polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, which is preferable. Is a (meth) acrylic acid ester compound.
- the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
- examples of such polymerizable compounds include trimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa ().
- the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.
- the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of solid content. be.
- the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the chemical resistance of the optical filter tend to be improved.
- the polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, and a known polymerization initiator can be used.
- Examples of the polymerization initiator that generates an active radical include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound.
- the O-acyloxime compound is a compound having a partial structure represented by the formula (d1).
- * represents a bond.
- O-acyloxym compound examples include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane.
- O-acyloxym compounds are N-acetyloxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl).
- O-acyloxime compounds there is a tendency to obtain a high-brightness optical filter.
- the alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3).
- the benzene ring may have a substituent.
- Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4).
- -Morholinophenyl) -2-benzylbutane-1-one 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one
- Commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF) may be used.
- Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1- [4- (2). -Hydroxyethoxy) phenyl] Propane-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one oligomer, ⁇ , ⁇ -diethoxy Examples thereof include acetophenone and benzyldimethylketal.
- the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2).
- triazine compound examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-). Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy) Styryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethyla
- acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
- Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.
- biimidazole compound examples include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl)-.
- a phenyl group at the 4,4'5,5'-position is substituted with a carboalkoxy group.
- examples thereof include imidazole compounds (see, for example, Japanese Patent Laid-Open No. 7-10913).
- benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, o-methyl benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzoyl compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthlenquinone, Kinon compounds such as 2-ethylanthraquinone and camphorquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methylphenylglycoxylate, titanosen compounds and the like. These are preferably used in combination with the polymerization initiation aid (D1) (particularly amines), particularly amines, benzyl,
- Examples of the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, and 4-acetoxy.
- Onium salts such as phenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyltosylate.
- phenylmethylbenzylsulfonium hexafluoroantimonate triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyltosylate.
- a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound is preferable, and an O-acyloxy is preferable.
- a polymerization initiator containing a compound is more preferable.
- the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is a mass part.
- the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the optical filter is improved.
- the polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
- Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
- Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 -2-Ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis Examples thereof include (ethylmethylamino) benzophenone, and among them, 4,4'-bis (diethylamino) benzophenone is preferable. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.
- alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-di. Examples thereof include butoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.
- thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichloromethanexanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
- carboxylic acid compound examples include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, and dichlorophenylsulfanylacetic acid.
- Examples thereof include N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
- the content thereof is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass.
- the amount of the polymerization initiation aid (D1) is within this range, a coloring pattern can be formed with higher sensitivity, and the productivity of the optical filter tends to be improved.
- the solvent (E) is not particularly limited, and a solvent usually used in the art can be used.
- a solvent usually used in the art can be used.
- ester solvent solvent containing -COO- in the molecule and not containing -O-
- ether solvent solvent containing -O- in the molecule and not containing -COO-
- ether ester solvent solvent in the molecule.
- Solvent containing -COO- and -O- Solvent containing -COO- and -O-), Ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule, -O-,- CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.
- Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, ⁇ -butyrolactone and the like.
- ether solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether.
- ether ester solvent examples include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy.
- Ethyl propionate methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate.
- Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.
- alcohol solvent examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
- aromatic hydrocarbon solvent examples include benzene, toluene, xylene, mesitylene and the like.
- amide solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
- the solvent is preferably one or more selected from the group consisting of an ether solvent, an ether ester solvent and an amide solvent, more preferably containing an ether solvent, an ether ester solvent and an amide solvent, and diethylene glycol methyl ethyl ether and propylene. It is more preferable to contain glycol monomethyl ether acetate and N-methylpyrrolidone.
- the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition.
- the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
- Leveling agent (F) examples include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
- the silicone-based surfactant examples include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324.
- TSF400 TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK) and the like. ..
- fluorine-based surfactant examples include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554.
- R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (made by AGC Inc. (formerly Asahi Glass Co., Ltd.)) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).
- silicone-based surfactant having a fluorine atom examples include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafuck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).
- the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, still more preferably, with respect to the total amount of the colored resin composition. It is 0.005 to 0.05% by mass.
- the content of the pigment dispersant is not included in this content.
- the colored resin composition may contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.
- the colored resin composition is, for example, a compound represented by the formula (I) and / or the formula (II), a resin (B), a polymerizable compound (C) used as necessary, and a polymerization initiator (D).
- the solvent (E), the leveling agent (F), the polymerization initiator (D1) and other components can be mixed.
- the compound represented by the formula (I) or the formula (II) may be contained in the pigment dispersion liquid in advance.
- the desired colored resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid so as to have a predetermined concentration.
- the dye When the dye is contained, the dye may be dissolved in a part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution with a filter having a pore size of about 0.01 to 1 ⁇ m. It is preferable to filter the mixed colored resin composition with a filter having a pore size of about 0.01 to 10 ⁇ m.
- Examples of the method for producing a colored pattern of a color filter from the colored resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable.
- the photolithography method is a method in which the colored resin composition is applied to a substrate and dried to form a composition layer, and the composition layer is exposed and developed through a photomask.
- a colored coating film which is a cured product of the composition layer can be formed by not using a photomask at the time of exposure and / or not developing the photomask.
- the film thickness of the color filter (cured film) is, for example, 30 ⁇ m or less, preferably 20 ⁇ m or less, more preferably 6 ⁇ m or less, still more preferably 3 ⁇ m or less, still more preferably 1.5 ⁇ m or less, and particularly preferably 0.5 ⁇ m or less. It is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
- the substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate.
- a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate.
- Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass.
- Another color filter layer, resin layer, transistor, circuit and the like may be formed on these substrates.
- a substrate obtained by subjecting the silicon substrate to HMDS treatment may be used.
- each color pixel by the photolithography method can be performed by a known or conventional device or condition.
- it can be produced as follows.
- the colored resin composition is applied onto a substrate and dried by heating and drying (pre-baking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth composition layer.
- the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
- the temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C.
- the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
- the film thickness of the composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.
- the composition layer is exposed via a photomask to form the desired coloring pattern.
- the pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
- a light source used for exposure a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like.
- a reduced projection exposure device such as a mask aligner and a stepper or a proximity exposure device.
- a colored pattern is formed on the substrate.
- a developing solution for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable.
- concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.
- the developer may contain a surfactant.
- the developing method may be any of a paddle method, a dipping method, a spray method and the like.
- the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water.
- the post-bake temperature is preferably 80 to 250 ° C, more preferably 100 to 245 ° C.
- the post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.
- the colored pattern and the colored coating film thus obtained are useful as a color filter, and the color filter can be used for a display device (for example, a liquid crystal display device, an organic EL device, etc.), an electronic paper, a solid-state image pickup element, or the like. It is useful as a color filter used.
- Example 1 Compound represented by formula (1) (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.0 part, compound represented by formula (2) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 0.41 part, triethylamine Mix 0.18 parts (manufactured by Tokyo Chemical Industry Co., Ltd.) and 5.0 parts of N-methylpyrrolidone (NMP) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) at room temperature and raise the temperature to 120 ° C. The mixture was stirred for 6 hours. After cooling the reaction solution to room temperature, 50 parts of ion-exchanged water was added.
- NMP N-methylpyrrolidone
- the obtained precipitate was obtained as a residue of suction filtration, washed with 50 parts of ion-exchanged water, and dried under reduced pressure under heating at 60 ° C. to obtain 1.23 parts of the compound represented by the formula (3).
- the yield was 92%.
- Comparative Example 1 The compound represented by the formula (4) was obtained by the synthetic method described in JP-A-2016-75837.
- Resin synthesis example 1 An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring.
- the solution was kept at 80 ° C. for 3 hours, cooled to room temperature, and measured with a B-type viscometer (23 ° C.) to have a viscosity of 137 mPa ⁇ s and a solid content of 36.8% by weight.
- a polymer (resin (B-1)) solution was obtained.
- the polystyrene-equivalent weight average molecular weight of the produced copolymer was 1.0 ⁇ 103 , the dispersity was 1.97, and the acid value in terms of solid content was 111 mg-KOH / g.
- the resin (B-1) has the following structural units.
- Dispersion liquid preparation example 1 5 parts of the compound represented by the formula (3) obtained in Example 1, 4 parts of the dispersant (BYKLPN-6919 manufactured by BYK) (solid content conversion), resin (B-1) (solid content conversion). 4 parts and 87 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 ⁇ m zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain a dispersion liquid (A-1).
- Dispersion liquid preparation example 2 5 parts of the compound represented by the formula (4) obtained in Comparative Example 1, 8 parts of the dispersant (BYKLPN-6919 manufactured by BYK) (solid content conversion), resin (B-1) (solid content conversion). 8 parts and 79 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 ⁇ m zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain a dispersion liquid (A-2).
- the colored resin composition 1 was obtained by mixing the following components. Dispersion liquid (A-1) 432 parts Resin (B-1) 43 parts (solid conversion) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9550: Manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts Polymerizable compound (C-2): Trimethylol propantriacrylate: Trade name A- TMPT: Shin-Nakamura Chemical Industry Co., Ltd.
- the comparative colored resin composition 1 was obtained by mixing the following components. Dispersion liquid (A-2) 517 parts Resin (B-1) 19 parts (solid conversion) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9550: Manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 20 parts Polymerizable compound (C-2): Trimethylol propantriacrylate: Trade name A- TMPT: Shin-Nakamura Chemical Industry Co., Ltd.
- the colored resin composition prepared with the colored resin composition 1 and the comparative colored resin composition 1 is applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes. To obtain a colored coating film.
- the xy chromaticity coordinates (x, y) and the stimulus value Y were measured by the same method as described above.
- the color difference ⁇ Eab was calculated from the measured values before and after post-baking. ⁇ Eab means that the smaller the color, the smaller the color change.
- Table 11 the transmittance of the colored coating film after post-baking was measured.
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Abstract
Description
[1] 式(I)又は式(II)で表される化合物。
[式(I)中、
R1は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
R2は、水素原子、置換基を有してもよい炭素数1~20の炭化水素基又はZ3とR1とを結ぶ単結合を表す。
Y1及びZ1は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z2及びZ3は、それぞれ独立に、単結合、酸素原子又は硫黄原子を表す。
ただし、Y1、Z1、Z2及びZ3のうち少なくとも1つは硫黄原子を表す。
X1~X4は、それぞれ独立に、-R4、-OR4、-SR4、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R4は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n1~n4は、それぞれ独立に、0~4の整数を表す。
式(II)中、
R3は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
Y2及びZ4は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z5は、単結合、酸素原子又は硫黄原子を表す。
ただし、Y2、Z4及びZ5のうち少なくとも1つは硫黄原子を表す。
X5~X12は、それぞれ独立に、-R5、-OR5、-SR5、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R5は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n5~n12は、それぞれ独立に、0~4の整数を表す。]
[2] [1]に記載の化合物と樹脂とを含む着色樹脂組成物。
[3] 重合性化合物と重合開始剤とを含む[2]に記載の着色樹脂組成物。
[4] [2]又は[3]に記載の着色樹脂組成物から形成されるカラーフィルタ。
[5] [4]に記載のカラーフィルタを含む表示装置。
以下、式(I)又は式(II)で表される化合物の部分構造を挙げて本発明をより具体的に説明する。本発明に係る式(I)又は式(II)で表される新規化合物によれば、該新規化合物を含む着色樹脂組成物から形成されるカラーフィルタにおいて、ポストベーク前後での色差を小さくできる。更に、本発明の一態様では、該新規化合物を含む着色樹脂組成物から形成されるカラーフィルタにおいて、ポストベーク前後での500nm~650nmにおける透過率の変化を小さくできる。なお、式(I)で表される化合物には、式(Ia)で表される共鳴構造を有する化合物、又は式(Ib)で表される平衡関係にある化合物が含まれ、式(II)で表される化合物には、式(IIa)で表される共鳴構造を有する化合物、又は式(IIb)で表される平衡関係にある化合物が含まれる。
R1は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
R2は、水素原子、置換基を有してもよい炭素数1~20の炭化水素基又はZ3とR1とを結ぶ単結合を表す。
Y1及びZ1は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z2及びZ3は、それぞれ独立に、単結合、酸素原子又は硫黄原子を表す。
ただし、Y1、Z1、Z2及びZ3のうち少なくとも1つは硫黄原子を表す。
X1~X4は、それぞれ独立に、-R4、-OR4、-SR4、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R4は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n1~n4は、それぞれ独立に、0~4の整数を表す。
式(II)、式(IIa)及び式(IIb)中、
R3は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
Y2及びZ4は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z5は、単結合、酸素原子又は硫黄原子を表す。
ただし、Y2、Z4及びZ5のうち少なくとも1つは硫黄原子を表す。
X5~X12は、それぞれ独立に、-R5、-OR5、-SR5、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R5は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n5~n12は、それぞれ独立に、0~4の整数を表す。]
イソプロピル基、イソブチル基、sec-ブチル基、tert-ブチル基、2-エチルブチル基、3,3-ジメチルブチル基、1,1,3,3-テトラメチルブチル基、1-メチルブチル基、1-エチルプロピル基、3-メチルブチル基、ネオペンチル基、1,1-ジメチルプロピル基、2-メチルペンチル基、3-エチルペンチル基、1,3-ジメチルブチル基、2-プロピルペンチル基、1-エチル-1,2-ジメチルプロピル基、1-メチルペンチル基、4-メチルペンチル基、4-メチルヘキシル基、5-メチルヘキシル基、2-エチルヘキシル基、1-メチルヘキシル基、1-エチルペンチル基、1-プロピルブチル基、3-エチルヘプチル基、2,2-ジメチルヘプチル基、1-メチルヘプチル基、1-エチルヘキシル基、1-プロピルペンチル基、1-メチルオクチル基、1-エチルヘプチル基、1-プロピルヘキシル基、1-ブチルペンチル基、1-メチルノニル基、1-エチルオクチル基、1-プロピルヘプチル基及び1-ブチルヘキシル基等の分枝鎖状アルキル基;
エテニル基(ビニル基)、プロペニル基(例えば、1-プロペニル基、2-プロペニル基(アリル基))、1-メチルエテニル基、ブテニル基(例えば、1-ブテニル基、2-ブテニル基、3-ブテニル基)、3-メチル-1-ブテニル基、1-メチル-1-ブテニル基、3-メチル-2-ブテニル基、1,3-ブタジエニル基、3-メチル-1,2-ブタジエニル基、1-(2-プロペニル)エテニル基、1-(1-メチルエテニル)エテニル基、1,1-ジメチル-2-プロペニル基、1,2-ジメチル-1-プロペニル基、1-エチル-2-プロペニル基、ペンテニル基(例えば、1-ペンテニル基、2-ペンテニル基、3-ペンテニル基、4-ペンテニル基)、1-(1,1-ジメチルエチル)エテニル基、1,3-ジメチル-1-ブテニル基、ヘキセニル基(例えば、1-ヘキセニル基、5-ヘキセニル基)、ヘプテニル基(例えば、1-ヘプテニル基、6-ヘプテニル基)、オクテニル基(例えば、1-オクテニル基、7-オクテニル基)、ノネニル基(例えば、1-ノネニル基、8-ノネニル基)、デセニル基(例えば、1-デセニル基、9-デセニル基)、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、イコセニル基等のアルケニル基;
エチニル基、プロピニル基(例えば、1-プロピニル基、2-プロピニル基)、ブチニル基(例えば、1-ブチニル基、2-ブチニル基、3-ブチニル基)、ペンチニル基、ヘキシニル基、ヘプチニル基、オクチニル基(例えば、1-オクチニル基、7-オクチニル基)、ノニニル基、デシニル基、ウンデシニル基、ドデシニル基、トリデシニル基、テトラデシニル基、ペンタデシニル基、ヘキサデシニル基、ヘプタデシニル基、オクタデシニル基、ノナデシニル基及びイコシニル基等のアルキニル基;
等が挙げられる。
R1~R5で表される飽和鎖状炭化水素基(すなわち、直鎖状アルキル基、分枝鎖状アルキル基)の炭素数は、好ましくは1~10であり、より好ましくは1~7であり、さらに好ましくは1~5である。
R1~R5で表される不飽和鎖状炭化水素基(すなわち、アルケニル基、アルキニル基)の炭素数は、好ましくは2~10であり、より好ましくは2~7であり、さらに好ましくは2~5である。
シクロヘキセニル基(例えば、シクロヘキサ-1-エン-1-イル基、シクロヘキサ-2-エン-1-イル基、シクロヘキサ-3-エン-1-イル基)、シクロヘプテニル基及びシクロオクテニル基等のシクロアルケニル基;
ノルボルニル基、ノルボルネニル基、アダマンチル基及びビシクロ[2.2.2]オクチル基等の飽和又は不飽和多環式炭化水素基;
等が挙げられる。
R1~R5で表される飽和又は不飽和脂環式炭化水素基の炭素数は、好ましくは3~10である。
R1~R5で表される芳香族炭化水素基の炭素数は、好ましくは6~20であり、より好ましくは6~10であり、さらに好ましくは6~8である。
ベンジル基、(2-メチルフェニル)メチル基、(3-メチルフェニル)メチル基、(4-メチルフェニル)メチル基、(2-エチルフェニル)メチル基、(3-エチルフェニル)メチル基、(4-エチルフェニル)メチル基、(2-(tert-ブチル)フェニル)メチル基、(3-(tert-ブチル)フェニル)メチル基、(4-(tert-ブチル)フェニル)メチル基、(3,5-ジメチルフェニル)メチル基、1-フェニルエチル基、1-メチル-1-フェニルエチル基、1,1-ジフェニルエチル基、(1-ナフチル)メチル基及び(2-ナフチル)メチル基等のアラルキル基;
1-フェニルエテニル基、2-フェニルエテニル基(フェニルビニル基)、2,2-ジフェニルエテニル基、2-フェニル-2-(1-ナフチル)エテニル基等のアリールアルケニル基;
フェニルエチニル基等のアリールアルキニル基;
ビフェニリル基、ターフェニリル基等の1つ以上のフェニル基が結合したフェニル基;
シクロヘキシルメチルフェニル基、ベンジルフェニル基、(ジメチル(フェニル)メチル)フェニル基等が挙げられる。
これらの炭素数は、好ましくは7~18であり、より好ましくは7~15である。
これらの炭素数は、好ましくは4~15であり、より好ましくは4~10である。
R1~R5で表される炭素数1~20の炭化水素基の置換基としては、置換基を有していてもよい複素環基、ハロゲン原子、ニトロ基、シアノ基、-ORa1、-CO2Ra1、-SRa1、-SO2Ra1、-SO3Ra1、-SO2NRa1Ra2及び-NRa1Ra2等が挙げられる。
ここで、Ra1及びRa2は、それぞれ独立に、水素原子又は炭素数1~20の炭化水素基を表す。Ra1及びRa2で表される炭素数1~20の炭化水素基は、前述のR1~R5で表される炭素数1~20の炭化水素基と同じである。
窒素原子のみをヘテロ原子として含む複素環としては、アジリジン、アゼチジン、ピロリジン、ピペリジン、ピペラジン等の単環系飽和複素環;ピロール、ピラゾール、イミダゾール、1,2,3-トリアゾール、1,2,4-トリアゾール等の5員環系不飽和複素環;ピリジン、ピリダジン、ピリミジン、ピラジン、1,3,5-トリアジン等の6員環系不飽和複素環;インダゾール、インドリン、イソインドリン、イソインドリン-1,3-ジオン、インドール、インドリジン、ベンゾイミダゾール、キノリン、イソキノリン、キノキサリン、キナゾリン、シンノリン、フタラジン、ナフチリジン、プリン、プテリジン、ベンゾピラゾール、ベンゾピペリジン等の縮合二環系複素環;カルバゾール、アクリジン、フェナジン等の縮合三環系複素環;等が挙げられる。
酸素原子のみをヘテロ原子として含む複素環としては、オキシラン、オキセタン、テトラヒドロフラン、テトラヒドロピラン、1,3-ジオキサン、1,4-ジオキサン等の単環系飽和複素環;1,4-ジオキサスピロ[4.5]デカン、1,4-ジオキサスピロ[4.5]ノナン等の二環系飽和複素環;α-アセトラクトン、β-プロピオラクトン、γ-ブチロラクトン、δ-バレロラクトン等のラクトン系複素環;フラン等の5員環系不飽和複素環;2H-ピラン、4H-ピラン等の6員環系不飽和複素環;1-ベンゾフラン、ベンゾピラン、ベンゾジオキソール、クロマン、イソクロマン等の縮合二環系複素環;キサンテン、ジベンゾフラン等の縮合三環系複素環;等が挙げられる。
硫黄原子のみをヘテロ原子として含む複素環としては、ジチオラン等の5員環系飽和複素環;チアン、1,3-ジチアン等の6員環系飽和複素環;チオフェン等の5員環系不飽和複素環;4H-チオピラン等の6員環系不飽和複素環;ベンゾテトラヒドロチオピラン等のベンゾチオピラン、ベンゾチオフェン等の縮合二環系複素環等;チアントレン、ジベンゾチオフェン等の縮合三環系複素環;等が挙げられる。
窒素原子及び酸素原子をヘテロ原子として含む複素環としては、モルホリン、2-ピロリドン、2-ピペリドン等の単環系飽和複素環;オキサゾール、イソオキサゾール等の単環系不飽和複素環;ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾオキサジン、ベンゾジオキサン、ベンゾイミダゾリン等の縮合二環系複素環;フェノキサジン等の縮合三環系複素環;等が挙げられる。
窒素原子及び硫黄原子をヘテロ原子として含む複素環としては、チアゾール等の単環系複素環;ベンゾチアゾール等の縮合二環系複素環;フェノチアジン等の縮合三環系複素環;等が挙げられる。
該複素環基の炭素数は、好ましくは2~30であり、より好ましくは3~22であり、さらに好ましくは3~20である。
該複素環基は置換基を有していてもよく、置換基としては、ハロゲン原子、ニトロ基、シアノ基、-ORa1、-CO2Ra1、-SRa1、-SO2Ra1、-SO3Ra1、-SO2NRa1Ra2及び-NRa1Ra2等が挙げられる(ただし、Ra1及びRa2は前記に同じ)。
なお、該複素環の結合位は、各環に含まれる任意の水素原子が脱離した部分である。
X1~X12で表されるスルファモイル基は置換基を有していてもよい。X1~X12で表されるスルファモイル基の置換基としては、置換基を有していてもよい炭素数6~20の芳香族炭化水素基、置換基を有していてもよい複素環基、ハロゲン原子、ニトロ基、シアノ基、-ORa1、-CO2Ra1、-SRa1、-SO2Ra1、-SO3Ra1、-SO2NRa1Ra2及び-NRa1Ra2等が挙げられる(ただし、Ra1及びRa2は前記に同じ)。なお、X1~X12で表されるスルファモイル基の置換基として用いられる、置換基を有していてもよい複素環基及びハロゲン原子としては、R1~R5で表される炭素数1~20の炭化水素基の置換基として用いられる、置換基を有していてもよい複素環基及びハロゲン原子と同様のものが挙げられ、その好ましい態様も同様である。
フェニル基、o-トリル基、m-トリル基、p-トリル基、2-エチルフェニル基、3-エチルフェニル基、4-エチルフェニル基、2,3-ジメチルフェニル基、2,4-ジメチルフェニル基、2,5-ジメチルフェニル基、2,6-ジメチルフェニル基、3,4-ジメチルフェニル基、3,5-ジメチルフェニル基、4-ビニルフェニル基、o-イソプロピルフェニル基、m-イソプロピルフェニル基、p-イソプロピルフェニル基、o-tert-ブチルフェニル基、m-tert-ブチルフェニル基、p-tert-ブチルフェニル基、3,5-ジ(tert-ブチル)フェニル基、3,5-ジ(tert-ブチル)-4-メチルフェニル基、4-ブチルフェニル基、4-ペンチルフェニル基、2,6-ビス(1-メチルエチル)フェニル基、2,4,6-トリス(1-メチルエチル)フェニル基、4-シクロヘキシルフェニル基、2,4,6-トリメチルフェニル基、4-オクチルフェニル基、4-(1,1,3,3-テトラメチルブチル)フェニル基、1-ナフチル基、2-ナフチル基、6-メチル-2-ナフチル基、5,6,7,8-テトラヒドロ-1-ナフチル基、5,6,7,8-テトラヒドロ-2-ナフチル基、フルオレニル基、フェナントリル基、アントリル基、2-ドデシルフェニル基、3-ドデシルフェニル基、4-ドデシルフェニル基、ペリレニル基、クリセニル基及びピレニル基等の芳香族炭化水素基;等が挙げられる。
該芳香族炭化水素基の炭素数は、好ましくは6~10であり、より好ましくは6~8である。
該芳香族炭化水素基は置換基を有していてもよく、置換基としては、ハロゲン原子、ニトロ基、シアノ基、-ORa1、-CO2Ra1、-SRa1、-SO2Ra1、-SO3Ra1、-SO2NRa1Ra2及び-NRa1Ra2等が挙げられる(ただし、Ra1及びRa2は前記に同じ)。
R1は、
置換基を有していてもよい炭素数6~20の芳香族炭化水素基が好ましく、
置換基を有していてもよい炭素数6~10の芳香族炭化水素基がより好ましく、
置換基を有していてもよい炭素数6~8の芳香族炭化水素基がさらに好ましく、
置換基を有していてもよいフェニル基が特に好ましい。
R2は、
置換基を有していてもよい炭素数2~20の不飽和炭化水素基又は置換基を有していてもよい炭素数6~20の芳香族炭化水素基が好ましく、
置換基を有していてもよい炭素数2~10の不飽和鎖状炭化水素基又は置換基を有していてもよい炭素数6~10の芳香族炭化水素基がより好ましく、
置換基を有していてもよい炭素数2~7の不飽和鎖状炭化水素基又は置換基を有していてもよい炭素数6~8の芳香族炭化水素基がさらに好ましく、
置換基を有していてもよい炭素数2~7のアルケニル基又は置換基を有していてもよい炭素数6~8の芳香族炭化水素基がよりさらに好ましく、
置換基を有していてもよいエテニル基又は置換基を有していてもよいフェニル基が特に好ましい。
n1~n4は、それぞれ独立に、好ましくは0~2、より好ましくは0~1、さらに好ましくは0である。
X1~X4は、それぞれ独立に、-R4又はハロゲン原子が好ましい。
Y1、Z1、Z2及びZ3のうち少なくとも1つは硫黄原子を表し、Y1が硫黄原子でありZ1が酸素原子である態様、Y1が酸素原子でありZ1が硫黄原子である態様及びZ2とZ3とが硫黄原子である態様のうち少なくとも1つの態様を満足することが好ましい。ただし、R2が不飽和炭化水素基である場合には、Z2及びZ3は単結合であることが好ましい。
Z2及びZ3が硫黄原子の場合、Y1が酸素原子又は硫黄原子であり、Z1が酸素原子又は硫黄原子であり、R1が置換基を有していてもよい炭素数6~20の芳香族炭化水素基であり、R2が置換基を有していてもよい炭素数6~20の芳香族炭化水素基であることが好ましく、Y1が酸素原子であり、Z1が酸素原子であり、R1が置換基を有していてもよい炭素数6~8の芳香族炭化水素基であり、R2が置換基を有していてもよい炭素数6~8の芳香族炭化水素基であることがより好ましい。
R3は、
置換基を有していてもよい炭素数2~20の不飽和炭化水素基又は置換基を有していてもよい炭素数6~20の芳香族炭化水素基が好ましく、
置換基を有していてもよい炭素数2~10の不飽和鎖状炭化水素基又は置換基を有していてもよい炭素数6~10の芳香族炭化水素基がより好ましく、
置換基を有していてもよい炭素数2~7の不飽和鎖状炭化水素基又は置換基を有していてもよい炭素数6~8の芳香族炭化水素基がさらに好ましく、
置換基を有していてもよい炭素数2~7のアルケニル基又は置換基を有していてもよい炭素数6~8の芳香族炭化水素基がよりさらに好ましく、
置換基を有していてもよいエテニル基又は置換基を有していてもよいフェニル基が特に好ましい。
n5~n12は、それぞれ独立に、好ましくは0~2、より好ましくは0~1、さらに好ましくは0である。
X5~X12は、それぞれ独立に、-R5又はハロゲン原子が好ましい。
Y2、Z4及びZ5のうち少なくとも1つは硫黄原子を表す。ただし、R3が不飽和炭化水素基である場合には、Z5は単結合であることが好ましい。
Y2が酸素原子でZ4が硫黄原子の場合、及びY2及びZ4が硫黄原子の場合は、Z5が単結合又は酸素原子であり、R3が置換基を有していてもよい炭素数6~20の芳香族炭化水素基であるか、Z5が単結合であり、R3が置換基を有していてもよい炭素数2~20の不飽和炭化水素基であることが好ましく、Z5が単結合であり、R3が置換基を有していてもよい炭素数6~8の芳香族炭化水素基であるか、Z5が単結合であり、R3が置換基を有していてもよい炭素数2~7の不飽和炭化水素基であることがより好ましく、Z5が単結合であり、R3が置換基を有していてもよい炭素数2~7の不飽和炭化水素基であることがさらに好ましい。
式(IB)で表される化合物としては、例えば、表2に示す式(IB-1)~式(IB-24)で表される化合物が挙げられる。
式(IC)で表される化合物としては、例えば、表3に示す式(IC-1)~式(IC-24)で表される化合物が挙げられる。
式(ID)で表される化合物としては、例えば、表4に示す式(ID-1)~式(ID-24)で表される化合物が挙げられる。
式(IE)で表される化合物としては、例えば、表5に示す式(IE-1)~式(IE-24)で表される化合物が挙げられる。
なお、表1~表5の「i-1」はフェニル基を、「i-2」はエテニル基を表す。
式(IA-1)~式(IA-6)、式(IA-13)~式(IA-18)、式(IA-21)、式(IA-22)~式(IA-24)で表される化合物が好ましく、
式(IA-1)、式(IA-13)、式(IA-21)、式(IA-23)、式(IA-24)で表される化合物がより好ましい。
式(IB-1)~式(IB-6)、式(IB-13)~式(IB-18)、式(IB-21)、式(IB-22)~式(IB-24)で表される化合物が好ましく、
式(IB-1)、式(IB-13)、式(IB-21)、式(IB-23)、式(IB-24)で表される化合物がより好ましい。
式(IC-1)~式(IC-6)、式(IC-13)~式(IC-18)、式(IC-21)、式(IC-22)~式(IC-24)で表される化合物が好ましく、
式(IC-1)、式(IC-13)、式(IC-21)、式(IC-23)、式(IC-24)で表される化合物がより好ましい。
式(ID-1)~式(ID-6)、式(ID-13)~式(ID-18)、式(ID-21)、式(ID-22)~式(ID-24)で表される化合物が好ましく、
式(ID-1)、式(ID-13)、式(ID-21)、式(ID-23)、式(ID-24)で表される化合物がより好ましい。
式(IE-1)~式(IE-6)、式(IE-13)~式(IE-18)、式(IE-21)、式(IE-22)~式(IE-24)で表される化合物が好ましく、
式(IE-1)、式(IE-13)、式(IE-21)、式(IE-23)、式(IE-24)で表される化合物がより好ましい。
式(IIB)で表される化合物としては、例えば、表7に示す式(IIB-1)~式(IIB-13)で表される化合物が挙げられる。
式(IIC)で表される化合物としては、例えば、表8に示す式(IIC-1)~式(IIC-13)で表される化合物が挙げられる。
式(IID)で表される化合物としては、例えば、表9に示す式(IID-1)~式(IID-13)で表される化合物が挙げられる。
式(IIE)で表される化合物としては、例えば、表10に示す式(IIE-1)~式(IIE-13)で表される化合物が挙げられる。
なお、表6~表10中の「i-1」はフェニル基を、「i-2」はエテニル基を表す。
式(IIA-1)、式(IIA-2)、式(IIA-8)、式(IIA-9)、式(IIA-12)、式(IIA-13)で表される化合物が好ましく、
式(IIA-1)、式(IIA-8)、式(IIA-12)、式(IIA-13)で表される化合物がより好ましい。
式(IIB-1)、式(IIB-2)、式(IIB-8)、式(IIB-9)、式(IIB-12)、式(IIB-13)で表される化合物が好ましく、
式(IIB-1)、式(IIB-8)、式(IIB-12)、式(IIB-13)で表される化合物がより好ましい。
式(IIC-1)、式(IIC-2)、式(IIC-8)、式(IIC-9)、式(IIC-12)、式(IIC-13)で表される化合物が好ましく、
式(IIC-1)、式(IIC-8)、式(IIC-12)、式(IIC-13)で表される化合物がより好ましい。
式(IID-1)、式(IID-2)、式(IID-8)、式(IID-9)、式(IID-12)、式(IID-13)で表される化合物が好ましく、
式(IID-1)、式(IID-8)、式(IID-12)、式(IID-13)で表される化合物がより好ましい。
式(IIE-1)、式(IIE-2)、式(IIE-8)、式(IIE-9)、式(IIE-12)、式(IIE-13)で表される化合物が好ましく、
式(IIE-1)、式(IIE-8)、式(IIE-12)、式(IIE-13)で表される化合物がより好ましい。
また式(II)で表される化合物は、例えば、式(IIIa)及び式(IIIb)で表される化合物と、式(V)で表される化合物を適宜反応させることにより製造できる。
本発明は、前述した式(I)又は式(II)で表される化合物と、樹脂(以下、樹脂(B)という場合がある)を含む着色樹脂組成物を包含する。
また本発明は、重合性化合物(以下、重合性化合物(C)という場合がある)と、重合開始剤(以下、重合開始剤(D)という場合がある)とを含む着色樹脂組成物を包含する。
本発明の着色樹脂組成物は、前述した式(I)及び/又は式(II)で表される化合物(以下、着色剤(A1)という場合がある)を着色剤(以下、着色剤(A)という場合がある)として含むことが好ましい。
本発明の着色樹脂組成物は、さらに溶剤(以下、溶剤(E)という場合がある)を含むことが好ましい。
本発明の着色樹脂組成物は、レベリング剤(以下、レベリング剤(F)という場合がある)を含んでいてもよい。
本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組合せて使用することができる。
着色剤(A1)の含有率は、着色樹脂組成物の固形分の総量中、好ましくは0.5~70質量%、より好ましくは1~55質量%、さらに好ましくは2~50質量%、よりさらに好ましくは5~40質量%である。
なお、本明細書において「固形分の総量」とは、本発明の着色樹脂組成物から溶剤を除いた成分の合計量をいう。固形分の総量及びこれに対する各成分の含有量は、例えば、液体クロマトグラフィー、ガスクロマトグラフィー等の公知の分析手段により測定することができる。
このような染料としては、具体的には、C.I.ソルベントイエロー4(以下、C.I.ソルベントイエローの記載を省略し番号のみの記載とする。他も同様である)、14、15、23、24、38、62、63、68、82、94、98、99、117、162、163、167、189;
C.I.ソルベントレッド45、49、111、125、130、143、145、146、150、151、155、168、169、172、175、181、207、222、227、230、245、247;
C.I.ソルベントオレンジ2、7、11、15、26、56、77、86;
C.I.ソルベントバイオレット11、13、14、26、31、36、37、38、45、47、48、51、59、60;
C.I.ソルベントブルー4、5、14、18、35、36、37、45、58、59、59:1、63、67、68、69、70、78、79、83、90、94、97、98、100、101、102、104、105、111、112、122、128、132、136、139;
C.I.ソルベントグリーン1、3、4、5、7、28、29、32、33、34、35;等のC.I.ソルベント染料、
C.I.アシッドイエロー1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251;
C.I.アシッドレッド1、4、8、14、17、18、26、27、29、31、33、34、35、37、40、42、44、50、57、66、73、76、80、88、91、95、97、98、103、106、111、114、129、133、134、138、143、145、150、151、155、158、160、172、176、182、183、195、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、418、422、426;
C.I.アシッドオレンジ6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169、173;
C.I.アシッドバイオレット6B、7、15、16、17、19、21、23、24、25、34、38、49、72;
C.I.アシッドブルー1、3、5、7、9、11、13、15、17、18、22、23、24、25、26、27、29、34、38、40、41、42、43、45、48、51、54、59、60、62、70、72、74、75、78、80、82、83、86、87、88、90、90:1、91、92、93、93:1、96、99、100、102、103、104、108、109、110、112、113、117、119、120、123、126、127、129、130、131、138、140、142、143、147、150、151、154、158、161、166、167、168、170、171、175、182、183、184、187、192、199、203、204、205、210、213、229、234、236、242、243、256、259、267、269、278、280、285、290、296、315、324:1、335、340;
C.I.アシッドグリーン1、3、5、6、7、8、9、11、13、14、15、16、22、25、27、28、41、50、50:1、58、63、65、80、104、105、106、109;等のC.I.アシッド染料、
C.I.ダイレクトイエロー2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141;
C.I.ダイレクトレッド79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250;
C.I.ダイレクトオレンジ26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107;
C.I.ダイレクトバイオレット47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104;
C.I.ダイレクトブルー1、2、3、6、8、15、22、25、28、29、40、41、42、47、52、55、57、71、76、77、78、80、81、84、85、86、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、120、137、149、150、153、155、156、158、159、160、161、162、163、164、165、166、167、168、170、171、172、173、188、189、190、192、193、194、195、196、198、199、200、201、202、203、207、209、210、212、213、214、222、225、226、228、229、236、237、238、242、243、244、245、246、247、248、249、250、251、252、256、257、259、260、268、274、275、293;
C.I.ダイレクトグリーン25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82;等のC.I.ダイレクト染料、
C.I.ディスパースイエロー51、54,76;
C.I.ディスパースバイオレット26、27;
C.I.ディスパースブルー1、14、56、60;等のC.I.ディスパース染料、
C.I.ベーシックブルー1、3、5、7、9、19、21、22、24、25、26、28、29、40、41、45、47、54、58、59、60、64、65、66、67、68、81、83、88、89;
C.I.ベーシックバイオレット2;
C.I.ベーシックレッド9;
C.I.ベーシックグリーン1;等のC.I.ベーシック染料、
C.I.リアクティブイエロー2,76,116;
C.I.リアクティブオレンジ16;
C.I.リアクティブレッド36;等のC.I.リアクティブ染料、
C.I.モーダントイエロー5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;
C.I.モーダントレッド1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、29、30、32、33、36、37、38、39、41、42、43、45、46、48、52、53、56、62、63、71、74、76、78、85、86、88、90、94、95;
C.I.モーダントオレンジ3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48;
C.I.モーダントバイオレット1、1:1、2、3、4、5、6、7、8、10、11、14、15、16、17、18、19、21、22、23、24、27、28、30、31、32、33、36、37、39、40、41、44、45、47、48、49、53、58;
C.I.モーダントブルー1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83、84;
C.I.モーダントグリーン1、3、4、5、10、13、15、19、21、23、26、29、31、33、34、35、41、43、53;等のC.I.モーダント染料、
C.I.バットグリーン1等のC.I.バット染料等が挙げられる。
これらの染料は、各色について1種の染料又は複数の染料を使用してもよく、各色の染料を組み合わせてもよい。
黄色顔料:C.I.ピグメントイエロー1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、129、137、138、139、147、148、150、153、154、166、173、185、194、214等
オレンジ色顔料:C.I.ピグメントオレンジ13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等
赤色顔料:C.I.ピグメントレッド9、97、105、122、123、144、149、166、168、176、177、180、192、209、215、216、224、242、254、255、264、265等
青色顔料:C.I.ピグメントブルー15、15:3、15:4、15:6、60等
紫色顔料:C.I.ピグメントバイオレット1、19、23、29、32、36、38等
これらの顔料は、各色について1種の顔料又は複数の顔料を使用してもよく、各色の顔料を組み合わせてもよい。
樹脂(B)は、特に限定されないが、アルカリ可溶性樹脂であることが好ましい。樹脂(B)としては、以下の樹脂[K1]~[K6]等が挙げられる。
樹脂[K1];不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種(a)(以下「(a)」という場合がある)に由来する構造単位と、炭素数2~4の環状エーテル構造及びエチレン性不飽和結合を有する単量体(b)(以下「(b)」という場合がある)に由来する構造単位とを有する共重合体;
樹脂[K2];(a)に由来する構造単位と(b)に由来する構造単位と、(a)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる)(以下「(c)」という場合がある)に由来する構造単位とを有する共重合体;
樹脂[K3];(a)に由来する構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K4];(a)に由来する構造単位に(b)を付加させた構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K5];(b)に由来する構造単位に(a)を付加させた構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K6];(b)に由来する構造単位に(a)を付加させ、カルボン酸無水物をさらに付加させた構造単位と(c)に由来する構造単位とを有する共重合体。
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3-ビニルフタル酸、4-ビニルフタル酸、3,4,5,6-テトラヒドロフタル酸、1,2,3,6-テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸、1,4-シクロヘキセンジカルボン酸等の不飽和ジカルボン酸類;
メチル-5-ノルボルネン-2,3-ジカルボン酸、5-カルボキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-エチルビシクロ[2.2.1]ヘプト-2-エン等のカルボキシ基を含有するビシクロ不飽和化合物類;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等の不飽和ジカルボン酸類無水物;
こはく酸モノ〔2-(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2-(メタ)アクリロイルオキシエチル〕等の2価以上の多価カルボン酸の不飽和モノ〔(メタ)アクリロイルオキシアルキル〕エステル類;
α-(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和アクリレート類;等が挙げられる。
これらのうち、共重合反応性の点や得られる樹脂のアルカリ水溶液への溶解性の点から、アクリル酸、メタクリル酸、無水マレイン酸等が好ましい。
尚、本明細書において、「(メタ)アクリル酸」とは、アクリル酸及びメタクリル酸よりなる群から選ばれる少なくとも1種を表す。「(メタ)アクリロイル」及び「(メタ)アクリレート」等の表記も、同様の意味を有する。
2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル類;
マレイン酸ジエチル、フマル酸ジエチル、イタコン酸ジエチル等のジカルボン酸ジエステル;
ビシクロ[2.2.1]ヘプト-2-エン、5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチルビシクロ[2.2.1]ヘプト-2-エン、5-(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5-メトキシビシクロ[2.2.1]ヘプト-2-エン、5-エトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジメトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジエトキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチル-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-tert-ブトキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-フェノキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(tert-ブトキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン等のビシクロ不飽和化合物類;
N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、N-スクシンイミジル-3-マレイミドベンゾエート、N-スクシンイミジル-4-マレイミドブチレート、N-スクシンイミジル-6-マレイミドカプロエート、N-スクシンイミジル-3-マレイミドプロピオネート、N-(9-アクリジニル)マレイミド等のジカルボニルイミド誘導体類;
スチレン、α-メチルスチレン、m-メチルスチレン、p-メチルスチレン、ビニルトルエン、p-メトキシスチレン、アクリロニトリル、メタクリロニトリル、塩化ビニル、塩化ビニリデン、アクリルアミド、メタクリルアミド、酢酸ビニル、1,3-ブタジエン、イソプレン、2,3-ジメチル-1,3-ブタジエン等が挙げられる。
これらのうち、共重合反応性及び耐熱性の点から、スチレン、ビニルトルエン、N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、ビシクロ[2.2.1]ヘプト-2-エン等が好ましい。
(a)に由来する構造単位;2~60モル%
(b)に由来する構造単位;40~98モル%
であることが好ましく、
(a)に由来する構造単位;10~50モル%
(b)に由来する構造単位;50~90モル%
であることがより好ましい。
樹脂[K1]の構造単位の比率が、上記の範囲にあると、着色樹脂組成物の保存安定性、着色パターンを形成する際の現像性、及び得られる光学フィルタの耐溶剤性に優れる傾向がある。
(a)に由来する構造単位;2~45モル%
(b)に由来する構造単位;2~95モル%
(c)に由来する構造単位;1~65モル%
であることが好ましく、
(a)に由来する構造単位;5~40モル%
(b)に由来する構造単位;5~80モル%
(c)に由来する構造単位;5~60モル%
であることがより好ましい。
樹脂[K2]の構造単位の比率が、上記の範囲にあると、着色樹脂組成物の保存安定性、着色パターンを形成する際の現像性、並びに得られる光学フィルタの耐溶剤性、耐熱性及び機械強度に優れる傾向がある。
(a)に由来する構造単位;2~60モル%
(c)に由来する構造単位;40~98モル%
であることが好ましく、
(a)に由来する構造単位;10~50モル%
(c)に由来する構造単位;50~90モル%
であることがより好ましい。
樹脂[K3]は、例えば、樹脂[K1]の製造方法として記載した方法と同様に製造することができる。
まず(a)と(c)との共重合体を、樹脂[K1]の製造方法として記載した方法と同様に製造する。この場合、それぞれに由来する構造単位の比率は、樹脂[K3]で挙げたもの同じ比率であることが好ましい。
(a)と(c)との共重合体の製造に引き続き、フラスコ内雰囲気を窒素から空気に置換し、(b)、カルボン酸又はカルボン酸無水物と環状エーテルとの反応触媒(例えばトリス(ジメチルアミノメチル)フェノール等)及び重合禁止剤(例えばハイドロキノン等)等をフラスコ内に入れて、例えば、60~130℃で、1~10時間反応することにより、樹脂[K4]を製造することができる。
(b)の使用量は、(a)100モルに対して、5~80モルが好ましく、より好ましくは10~75モルである。この範囲にすることにより、着色樹脂組成物の保存安定性、パターンを形成する際の現像性、並びに得られるパターンの耐溶剤性、耐熱性、機械強度及び感度のバランスが良好になる傾向がある。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K4]に用いる(b)としては(b1)が好ましく、さらに(b1-1)が好ましい。
前記反応触媒の使用量は、(a)、(b)及び(c)の合計量100質量部に対して0.001~5質量部が好ましい。前記重合禁止剤の使用量は、(a)、(b)及び(c)の合計量100質量部に対して0.001~5質量部が好ましい。
仕込方法、反応温度及び時間等の反応条件は、製造設備や重合による発熱量等を考慮して適宜調整することができる。なお、重合条件と同様に、製造設備や重合による発熱量等を考慮し、仕込方法や反応温度を適宜調整することができる。
(b)及び(c)に由来する構造単位の比率は、前記の共重合体を構成する全構造単位の合計モル数に対して、それぞれ、
(b)に由来する構造単位;5~95モル%
(c)に由来する構造単位;5~95モル%
であることが好ましく、
(b)に由来する構造単位;10~90モル%
(c)に由来する構造単位;10~90モル%
であることがより好ましい。
前記の共重合体に反応させる(a)の使用量は、(b)100モルに対して、5~80モルが好ましい。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K5]に用いる(b)としては(b1)が好ましく、さらに(b1-1)が好ましい。
カルボン酸無水物としては、無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等が挙げられる。カルボン酸無水物の使用量は、(a)の使用量1モルに対して、0.5~1モルが好ましい。
重合性化合物(C)は、重合開始剤(D)から発生した活性ラジカル及び/又は酸によって重合しうる化合物であり、例えば、重合性のエチレン性不飽和結合を有する化合物等が挙げられ、好ましくは(メタ)アクリル酸エステル化合物である。
中でも、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート及びジペンタエリスリトールヘキサ(メタ)アクリレートが好ましい。
重合開始剤(D)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始しうる化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。活性ラジカルを発生する重合開始剤としては、例えば、アルキルフェノン化合物、トリアジン化合物、アシルホスフィンオキサイド化合物、O-アシルオキシム化合物及びビイミダゾール化合物が挙げられる。
感度の点で、アルキルフェノン化合物としては、式(d2)で表される部分構造を有する化合物が好ましい。
重合開始助剤(D1)は、重合開始剤によって重合が開始された重合性化合物の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(D1)を含む場合、通常、重合開始剤(D)と組み合わせて用いられる。
重合開始助剤(D1)としては、アミン化合物、アルコキシアントラセン化合物、チオキサントン化合物及びカルボン酸化合物等が挙げられる。
溶剤(E)は、特に限定されず、当該分野で通常使用される溶剤を用いることができる。例えば、エステル溶剤(分子内に-COO-を含み、-O-を含まない溶剤)、エーテル溶剤(分子内に-O-を含み、-COO-を含まない溶剤)、エーテルエステル溶剤(分子内に-COO-と-O-とを含む溶剤)、ケトン溶剤(分子内に-CO-を含み、-COO-を含まない溶剤)、アルコール溶剤(分子内にOHを含み、-O-、-CO-及び-COO-を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等が挙げられる。
レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
シリコーン系界面活性剤としては、分子内にシロキサン結合を有する界面活性剤等が挙げられる。具体的には、トーレシリコーンDC3PA、同SH7PA、同DC11PA、同SH21PA、同SH28PA、同SH29PA、同SH30PA、同SH8400(商品名:東レ・ダウコーニング(株)製)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化学工業(株)製)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452及びTSF4460(モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製)等が挙げられる。
着色樹脂組成物は、必要に応じて、充填剤、他の高分子化合物、密着促進剤、酸化防止剤、光安定剤、連鎖移動剤等、当該技術分野で公知の添加剤を含んでもよい。
着色樹脂組成物は、例えば、式(I)及び/又は式(II)で表される化合物、樹脂(B)、並びに必要に応じて用いられる重合性化合物(C)、重合開始剤(D)、溶剤(E)、レベリング剤(F)、重合開始助剤(D1)及びその他の成分を混合することにより調製できる。
式(I)又は式(II)で表される化合物は、予め顔料分散液に含ませてもよい。顔料分散液に、残りの成分を、所定の濃度となるように混合することにより、目的の着色樹脂組成物を調製できる。
染料を含む場合の染料は、予め溶剤(E)の一部又は全部に溶解させて溶液を調製してもよい。該溶液を、孔径0.01~1μm程度のフィルタでろ過することが好ましい。
混合後の着色樹脂組成物を、孔径0.01~10μm程度のフィルタでろ過することが好ましい。
本発明の着色樹脂組成物からカラーフィルタの着色パターンを製造する方法としては、フォトリソグラフ法、インクジェット法、印刷法等が挙げられる。中でも、フォトリソグラフ法が好ましい。フォトリソグラフ法は、前記着色樹脂組成物を基板に塗布し、乾燥させて組成物層を形成し、フォトマスクを介して該組成物層を露光して、現像する方法である。フォトリソグラフ法において、露光の際にフォトマスクを用いないこと、及び/又は現像しないことにより、前記組成物層の硬化物である着色塗膜を形成することができる。
現像後は、水洗することが好ましい。
式(1)で表される化合物(東京化成工業(株)製)1.0部、式(2)で表される化合物(富士フイルム和光純薬工業(株)製)0.41部、トリエチルアミン(東京化成工業(株)製)0.18部、N-メチルピロリドン(NMP)(富士フイルム和光純薬工業(株)製)5.0部を室温で混合し、120℃に昇温して6時間撹拌した。反応液を室温まで冷却後、イオン交換水50部を投入した。得られた析出物を吸引濾過の残渣として取得し、イオン交換水50部で洗浄後、60℃の加熱下減圧乾燥し、式(3)で表される化合物1.23部を得た。収率は92%であった。
(質量分析)イオン化モード=ESI+: m/z= [M+H]+ 773.2
Exact Mass: 772.2
特開2016-75837号公報に記載の合成法にて式(4)で表される化合物を得た。
還流冷却器、滴下ロート及び撹拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート340部を入れ、撹拌しながら80℃まで加熱した。次いで、アクリル酸57部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)54部、ベンジルメタクリレート239部、プロピレングリコールモノメチルエーテルアセテート73部の混合溶液を5時間かけて滴下した。一方、重合開始剤2,2-アゾビス(2,4-ジメチルバレロニトリル)40部をプロピレングリコールモノメチルエーテルアセテート197部に溶解した溶液を6時間かけて滴下した。重合開始剤含有溶液の滴下終了後、80℃で3時間保持した後、室温まで冷却して、B型粘度計(23℃)で測定した粘度137mPa・s、固形分36.8重量%の共重合体(樹脂(B-1))溶液を得た。生成した共重合体のポリスチレン換算の重量平均分子量は1.0×103、分散度は1.97、固形分換算の酸価は111mg-KOH/gであった。樹脂(B-1)は、以下の構造単位を有する。
実施例1で得られた式(3)で表される化合物を5部、分散剤(BYK社製 BYKLPN-6919)(固形分換算)を4部、樹脂(B-1)(固形分換算)を4部、プロピレングリコールモノメチルエーテルアセテート87部を混合し、0.2μmのジルコニアビーズ300部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液(A-1)を得た。
比較例1で得られた式(4)で表される化合物を5部、分散剤(BYK社製 BYKLPN-6919)(固形分換算)を8部、樹脂(B-1)(固形分換算)を8部、プロピレングリコールモノメチルエーテルアセテート79部を混合し、0.2μmのジルコニアビーズ300部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液(A-2)を得た。
下記の成分を混合することにより、着色樹脂組成物1を得た。
分散液(A-1) 432部
樹脂(B-1) 43部(固形換算)
重合性化合物(C-1):ジペンタエリスリトールポリアクリレート:商品
名A-9550:新中村化学工業(株)製 20部
重合性化合物(C-2):トリメチロールプロパントリアクリレート:商品
名A-TMPT:新中村化学工業(株)製 20部
重合開始剤(D):N-アセチルオキシ-1-(4-フェニルスルファニル
フェニル)-3-シクロヘキシルプロパン-1-オン-2-イミン:商品名
PBG-327:O-アシルオキシム化合物;常州強力電子新材料(株)製
5.0部
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
680部
レベリング剤(F):ポリエーテル変性シリコーンオイル:商品名トーレシ
リコーンSH8400:東レダウコーニング(株)製 0.1部
下記の成分を混合することにより、比較着色樹脂組成物1を得た。
分散液(A-2) 517部
樹脂(B-1) 19部(固形換算)
重合性化合物(C-1):ジペンタエリスリトールポリアクリレート:商品
名A-9550:新中村化学工業(株)製 20部
重合性化合物(C-2):トリメチロールプロパントリアクリレート:商品
名A-TMPT:新中村化学工業(株)製 20部
重合開始剤(D):N-アセチルオキシ-1-(4-フェニルスルファニル
フェニル)-3-シクロヘキシルプロパン-1-オン-2-イミン:商品名
PBG-327:O-アシルオキシム化合物:常州強力電子新材料(株)製
5.0部
溶剤(E):プロピレングリコールモノメチルエーテルアセテート
855部
レベリング剤(F):ポリエーテル変性シリコーンオイル:商品名トーレシ
リコーンSH8400:東レダウコーニング(株)製 0.1部
5cm角のガラス基板(イーグル2000;コーニング社製)上に、着色樹脂組成物1及び比較着色樹脂組成物1で調製した着色樹脂組成物をスピンコート法で塗布した後、100℃で3分間プリベークして着色塗膜を得た。
プリベーク後の着色塗膜について、測色機(OSP-SP-200;オリンパス(株)製)を用いて分光を測定し、C光源の特性関数を用いてCIEのXYZ表色系におけるxy色度座標(x、y)と刺激値Yとを測定した。またプリベーク後の着色塗膜について透過率を測定した。
その後、プリベーク後の着色塗膜を230℃で10分間ポストベークした。
ポストベーク後の着色塗膜について、上記と同様の方法にて、xy色度座標(x、y)と刺激値Yを測定した。ポストベーク前後の測定値から色差△Eabを計算した。△Eabは小さいほど色変化が小さいことを意味する。結果を表11に示す。
またポストベーク後の着色塗膜について、透過率を測定した。ある波長λにおけるポストベーク前の透過率をXλ、ポストベーク後の透過率をYλとしたときに、透過率の変化の大きさ|(1-Yλ/Xλ)×100|(%)を500nm~650nmまで5nm間隔で計算し、得られた値の平均値を「500nm~650nmの透過率の変化率」とした。結果を表11に示す。
Claims (5)
- 式(I)又は式(II)で表される化合物。
[式(I)中、
R1は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
R2は、水素原子、置換基を有してもよい炭素数1~20の炭化水素基又はZ3とR1とを結ぶ単結合を表す。
Y1及びZ1は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z2及びZ3は、それぞれ独立に、単結合、酸素原子又は硫黄原子を表す。
ただし、Y1、Z1、Z2及びZ3のうち少なくとも1つは硫黄原子を表す。
X1~X4は、それぞれ独立に、-R4、-OR4、-SR4、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R4は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n1~n4は、それぞれ独立に、0~4の整数を表す。
式(II)中、
R3は、水素原子又は置換基を有してもよい炭素数1~20の炭化水素基を表す。
Y2及びZ4は、それぞれ独立に、酸素原子又は硫黄原子を表す。
Z5は、単結合、酸素原子又は硫黄原子を表す。
ただし、Y2、Z4及びZ5のうち少なくとも1つは硫黄原子を表す。
X5~X12は、それぞれ独立に、-R5、-OR5、-SR5、ハロゲン原子、ニトロ基又は置換基を有してもよいスルファモイル基を表す。
R5は、置換基を有していてもよい炭素数1~20の炭化水素基を表す。
n5~n12は、それぞれ独立に、0~4の整数を表す。] - 請求項1に記載の化合物と樹脂とを含む着色樹脂組成物。
- 重合性化合物と重合開始剤とを含む請求項2に記載の着色樹脂組成物。
- 請求項2又は3に記載の着色樹脂組成物から形成されるカラーフィルタ。
- 請求項4に記載のカラーフィルタを含む表示装置。
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