JP2018154782A - Methine compound, coloring resin composition containing the same, and color filter made from coloring resin composition - Google Patents
Methine compound, coloring resin composition containing the same, and color filter made from coloring resin composition Download PDFInfo
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- JP2018154782A JP2018154782A JP2017053986A JP2017053986A JP2018154782A JP 2018154782 A JP2018154782 A JP 2018154782A JP 2017053986 A JP2017053986 A JP 2017053986A JP 2017053986 A JP2017053986 A JP 2017053986A JP 2018154782 A JP2018154782 A JP 2018154782A
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- Prior art keywords
- resin composition
- acrylate
- pigment
- meth
- group
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 82
- -1 Methine compound Chemical class 0.000 title claims abstract description 78
- 238000004040 coloring Methods 0.000 title claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 239000000049 pigment Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- 239000011230 binding agent Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 14
- 239000004973 liquid crystal related substance Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 5
- 238000000059 patterning Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229940067265 pigment yellow 138 Drugs 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 239000000975 dye Substances 0.000 description 36
- 239000000178 monomer Substances 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- 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 4
- 0 CC1(C)c(cc(*)cc2)c2N=C1C Chemical compound CC1(C)c(cc(*)cc2)c2N=C1C 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-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
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- IXLDIJPRDDUUKL-UHFFFAOYSA-N (dimethylamino)methyl benzoate Chemical compound CN(C)COC(=O)C1=CC=CC=C1 IXLDIJPRDDUUKL-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SUDVPELGFZKOMD-UHFFFAOYSA-N 1,2-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)C)C(C(C)C)=CC=C3SC2=C1 SUDVPELGFZKOMD-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
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- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Optical Filters (AREA)
- Liquid Crystal (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
本発明は、メチン化合物、該化合物を含有するカラーフィルターの緑色画素を形成する際に用いられる着色樹脂組成物、該着色樹脂組成物を用いて形成されるカラーフィルター、並びに該カラーフィルターを用いて形成される液晶表示装置、撮像素子（ＣＣＤ、ＣＭＯＳ）及び有機ＥＬディスプレイ等の電子表示装置に関する。 The present invention relates to a methine compound, a colored resin composition used in forming a green pixel of a color filter containing the compound, a color filter formed using the colored resin composition, and the color filter. The present invention relates to an electronic display device such as a liquid crystal display device, an image sensor (CCD, CMOS), and an organic EL display.
ノートパソコンや液晶テレビ、携帯電話等に代表される液晶ディスプレイ（ＬＣＤ）や有機ＥＬディスプレイ等の液晶表示装置、及びデジタルカメラやカラーコピー機等の入力デバイスとして使用される撮像素子（ＣＣＤ、ＣＭＯＳ）のカラー化にはカラーフィルターが必要である。これら液晶表示装置や固体撮像素子に用いられるカラーフィルターを製造する方法としては、染色法、電着法、印刷法、顔料分散法等があるが、近年、パターニングの手法を用いた顔料分散法が主流となっている。パターニングの方法としてはフォトリソグラフィー法が代表的で、感光性樹脂組成物と顔料分散体との混合物を用いてカラーフィルターを形成している。また、最近では着色インキをインクジェットプリンターにより、マスクを介さずに直接基板上に塗布し、カラーフィルターを形成する方法も行われている。 Liquid crystal display devices such as notebook computers, liquid crystal televisions, mobile phones, and other liquid crystal displays (LCD), organic EL displays, and image sensors (CCD, CMOS) used as input devices for digital cameras, color copiers, etc. A color filter is required for colorization. Methods for producing color filters used in these liquid crystal display devices and solid-state imaging devices include dyeing methods, electrodeposition methods, printing methods, pigment dispersion methods, etc., but in recent years, pigment dispersion methods using patterning methods have been used. It has become mainstream. As a patterning method, a photolithography method is typical, and a color filter is formed using a mixture of a photosensitive resin composition and a pigment dispersion. Recently, a method of forming a color filter by applying colored ink directly on a substrate without using a mask by an ink jet printer is also performed.
カラーフィルターに求められる特性である、色純度、彩度、明度およびコントラストを向上させることは特に重要である。明度が向上することによってバックライトの光量を抑えることができ、結果的に消費電力が低減されるため、環境的にも必要な技術である。カラーフィルターの色純度を向上させるためには着色顔料の含有量を増やすことや、より良い分光波形の顔料を選択することが必要である。一方、明度を向上させるには、顔料濃度を減らすことや膜厚を薄くすることにより透過率を高くする必要がある。これらの相反する特性を両立するために顔料の微粒子化という方法が行われているが、感光性樹脂組成物の分散安定性、並びにカラーフィルターの光、熱又は溶剤に対する耐性及びコントラストの向上には限界があり、明度が向上しても耐性との両立が図れないのが現状である。 It is particularly important to improve color purity, saturation, brightness, and contrast, which are characteristics required for a color filter. Since the light intensity of the backlight can be suppressed by improving the lightness and the power consumption is reduced as a result, this is a technology that is also necessary from an environmental point of view. In order to improve the color purity of the color filter, it is necessary to increase the content of the color pigment or to select a pigment having a better spectral waveform. On the other hand, in order to improve the brightness, it is necessary to increase the transmittance by reducing the pigment concentration or reducing the film thickness. In order to achieve both of these contradictory properties, a method of making fine particles of a pigment has been carried out. However, in order to improve the dispersion stability of the photosensitive resin composition, the resistance of the color filter to light, heat or solvent and the contrast. At present, there is a limit, and even if the brightness is improved, it is not possible to achieve both resistance.
これらの問題を解決するための別のアプローチとして、染料を使用したカラーフィルターの検討が進められている。染料を用いれば、顔料では達成できない色純度と明度の両立や、粒子では無いことから光散乱を抑制出来るためコントラストも向上できるメリットがある。しかしながら、本発明者らの検討の結果、特許文献１乃至３に記載されているメチン化合物は蛍光を持ちコントラストが不十分であった。 As another approach for solving these problems, a color filter using a dye is being studied. If a dye is used, there is a merit that the contrast can be improved because the light purity can be suppressed because the color purity and lightness cannot be achieved by a pigment, and the particles are not particles. However, as a result of studies by the present inventors, the methine compounds described in Patent Documents 1 to 3 have fluorescence and insufficient contrast.
本発明は、メチン化合物、かつ該化合物を含有する着色樹脂組成物、および該着色樹脂組成物を用いて製造されたコントラストに優れたカラーフィルターを提供することを目的とする。 An object of the present invention is to provide a methine compound, a colored resin composition containing the compound, and a color filter excellent in contrast produced using the colored resin composition.
本発明者等は前記課題を解決すべく鋭意研究を行った結果、特定構造のメチン化合物（染料）を含む着色樹脂組成物を使用することによって上記課題を解決できることを見出し、本発明を完成させるに至った。
即ち、本発明は、
（１）下記式（１）
As a result of intensive studies to solve the above problems, the present inventors have found that the above problems can be solved by using a colored resin composition containing a methine compound (dye) having a specific structure, and the present invention is completed. It came to.
That is, the present invention
(1) The following formula (1)
（式（１）中、Ｒ1は水素原子、メチル基、カルボキシ基を、Ａｒ１は下記式（２）又は（３） (In the formula (1), R 1 represents a hydrogen atom, a methyl group or a carboxy group, and Ar 1 represents the following formula (2) or (3)
（式（２）中、Ｒ2は炭素数１乃至４のアルキル基を表す。） (In formula (2), R 2 represents an alkyl group having 1 to 4 carbon atoms.)
（式（３）中、Ｒ3は炭素数１乃至４のアルキル基を、Ｒ4は水素原子、ハロゲン原子、炭素数１乃至４のアルキル基、炭素数１乃至４のアルコキシ基、ニトロ基又はスルホ基を表す。）で示される基を表す。）で表される構造を有するメチン化合物、
（２）Ｒ1がメチル基である前項（１）に記載のメチン化合物、
（３）Ｒ2 及び Ｒ３がメチル基である前項（１）または前項（２）に記載のメチン化合物、
（４）下記式（４）または（５）
(In the formula (3), R 3 represents an alkyl group having 1 to 4 carbon atoms, R 4 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, or Represents a sulfo group). ) A methine compound having a structure represented by:
(2) The methine compound according to item (1), wherein R 1 is a methyl group,
(3) The methine compound according to (1) or (2) above, wherein R 2 and R 3 are methyl groups,
(4) The following formula (4) or (5)
で表される構造を有する前項（１）乃至（３）のいずれか一項に記載のメチン化合物、
（５）前項（１）乃至（４）のいずれか一項に記載のメチン化合物、バインダー樹脂及び硬化剤を含有する着色樹脂組成物、
（６）更に顔料を含有する前項（５）に記載の着色樹脂組成物、
（７）顔料がＣ．Ｉ．ピグメントグリーン５８、Ｃ．Ｉ．ピグメントグリーン５９、Ｃ．Ｉ．ピグメントグリーン７、Ｃ．Ｉ．ピグメントグリーン３６、Ｃ．Ｉ．ピグメントレッド２５４、Ｃ．Ｉ．ピグメントレッド１７７、Ｃ．Ｉ．ピグメントイエロー１５０、Ｃ．Ｉ．ピグメントイエロー１８５、及びＣ．Ｉ．ピグメントイエロー１３８からなる群から選ばれる一種以上である前項（６）に記載の着色樹脂組成物、
（８）更に光重合開始剤及び／または硬化促進剤を含有する前項（５）乃至（７）のいずれか一項に記載の着色樹脂組成物、
（９）前項（５）乃至（８）のいずれか一項に記載の着色樹脂組成物からなる着色硬化膜、
（１０）前項（９）に記載の着色硬化膜からなるカラーフィルター、
（１１）前項（１０）に記載のカラーフィルターを装着した液晶表示装置、有機ＥＬディスプレイ又は固体撮像素子、及び
（１２）前項（５）乃至（８）のいずれか一項に記載の着色樹脂組成物にパターニングを施す工程を含む着色硬化膜の製造方法、
に関する。
The methine compound according to any one of (1) to (3), having a structure represented by:
(5) A colored resin composition comprising the methine compound according to any one of (1) to (4), a binder resin, and a curing agent,
(6) The colored resin composition according to item (5), further containing a pigment,
(7) The pigment is C.I. I. Pigment green 58, C.I. I. Pigment green 59, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment red 254, C.I. I. Pigment red 177, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 185, and C.I. I. The colored resin composition according to item (6), which is at least one selected from the group consisting of CI Pigment Yellow 138;
(8) The colored resin composition according to any one of (5) to (7), further containing a photopolymerization initiator and / or a curing accelerator;
(9) A colored cured film comprising the colored resin composition according to any one of (5) to (8) above,
(10) A color filter comprising the colored cured film according to (9) above,
(11) A liquid crystal display device, an organic EL display, or a solid-state imaging device equipped with the color filter according to (10) above, and (12) the colored resin composition according to any one of (5) to (8) above A method for producing a colored cured film including a step of patterning an object,
About.
本発明のカラーフィルター用着色樹脂組成物を用いることにより、コントラストに優れたカラーフィルターを提供することができる。 By using the colored resin composition for a color filter of the present invention, a color filter excellent in contrast can be provided.
本発明のメチン化合物（以下、単に「式（１）で表される化合物」とも記載する）は、前記式（１）で表される構造を有する。 The methine compound of the present invention (hereinafter also simply referred to as “compound represented by the formula (1)”) has a structure represented by the formula (1).
式（１）中、Ｒ1は水素原子、メチル基又はカルボキシ基を表す。
式（１）のＲ1としては、水素原子またはメチル基が好ましく、メチル基であることがより好ましい。
In formula (1), R 1 represents a hydrogen atom, a methyl group or a carboxy group.
R 1 in the formula (1) is preferably a hydrogen atom or a methyl group, and more preferably a methyl group.
式（１）中、Ａｒ1は前記式（２）又は（３）で示される基を表す。
式（２）中、Ｒ2は炭素数１乃至４のアルキル基を表す。式（３）中、Ｒ3は炭素数１乃至４のアルキル基を、Ｒ4は水素原子、ハロゲン原子、炭素数１乃至４のアルキル基、炭素数１乃至４のアルコキシ基、ニトロ基又はスルホ基を表す。
式（２）のＲ2、式（３）のＲ3及びＲ4が表す炭素数１乃至４のアルキル基は、炭素数１乃至４のアルキル基であれば直鎖状または分岐鎖状の何れにも限定されない。また、該アルキル基は置換基を有していてもよい。
式（２）のＲ2、式（３）のＲ3及びＲ4が表す炭素数１乃至４のアルキル基の具体例としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｉｓｏ−ブチル基、ｓｅｃ−ブチル基及びｔ−ブチル基が挙げられる。
式（２）のＲ2、式（３）のＲ3及びＲ4が表すアルキル基が有していてもよい置換基としては、例えばハロゲン原子（フッ素原子、塩素原子、臭素原子及びヨウ素原子）、ヒドロキシ基及びアルコキシ基（例えば、メトキシ基、エトキシ基、ｉｓｏ−プロポキシ基、ｎ−プロポキシ基、ｎ−ブトキシ基、ｉｓｏ−ブトキシ基、ｓｅｃ−ブトキシ基及びｔ−ブトキシ基等）等が挙げられる。
In the formula (1), Ar 1 represents a group represented by the formula (2) or (3).
In formula (2), R 2 represents an alkyl group having 1 to 4 carbon atoms. In formula (3), R 3 represents an alkyl group having 1 to 4 carbon atoms, R 4 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, or a sulfo group. Represents a group.
The alkyl group having 1 to 4 carbon atoms represented by R 2 in formula ( 2 ) and R 3 and R 4 in formula (3) is either linear or branched as long as it is an alkyl group having 1 to 4 carbon atoms. It is not limited to. The alkyl group may have a substituent.
Specific examples of the alkyl group having 1 to 4 carbon atoms represented by R 2 in the formula ( 2 ), R 3 and R 4 in the formula (3) include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, Examples include n-butyl group, iso-butyl group, sec-butyl group and t-butyl group.
Examples of the substituent that the alkyl group represented by R 2 in formula ( 2 ) and R 3 and R 4 in formula (3) may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom). Hydroxy group and alkoxy group (for example, methoxy group, ethoxy group, iso-propoxy group, n-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, t-butoxy group, etc.) .
式（３）のＲ4が表すハロゲン原子の具体例としては、式（２）のＲ2、式（３）のＲ3及びＲ4が表すアルキル基が有していてもよい置換基としてのハロゲン原子と同じものが挙げられ、塩素原子であることが好ましい。
式（３）のＲ4が表す炭素数１乃至４のアルコキシ基の具体例としては、式（２）のＲ2、式（３）のＲ3及びＲ4が表すアルキル基が有していてもよい置換基としてのアルコキシ基と同じものが挙げられる。
式（２）におけるＲ2及び式（３）におけるＲ3としては、炭素数１乃至４の直鎖のアルキル基であることが好ましく、該炭素数１乃至４の直鎖のアルキル基が置換基を有さないことがより好ましく、メチル基またはエチル基であることが更に好ましく、メチル基であることが特に好ましい。
式（３）におけるＲ4としては、水素原子又は、塩素原子が好ましい。
Specific examples of the halogen atom represented by R 4 in the formula (3) include R 2 in the formula ( 2 ) and R 3 and R 4 in the formula (3) as the substituents that the alkyl group may represent. The same thing as a halogen atom is mentioned, It is preferable that it is a chlorine atom.
Specific examples of the alkoxy group having 1 to 4 carbon atoms represented by R 4 in the formula (3) include an alkyl group represented by R 2 in the formula ( 2 ) and R 3 and R 4 in the formula (3). The same thing as the alkoxy group as a good substituent is mentioned.
R 2 in the formula (2) and R 3 in the formula (3) are preferably a linear alkyl group having 1 to 4 carbon atoms, and the linear alkyl group having 1 to 4 carbon atoms is a substituent. Is more preferable, a methyl group or an ethyl group is more preferable, and a methyl group is particularly preferable.
R 4 in Formula (3) is preferably a hydrogen atom or a chlorine atom.
式（１）で表される化合物としては、上記Ｒ1乃至Ｒ4のそれぞれの好ましいものの組み合わせがより好ましく、より好ましいものの組み合わせが更に好ましい。
より具体的には、前記式（４）又は（５）で表される化合物が最も好ましい。
Examples of the compound represented by the formula (1), more preferably a combination of each of the preferred of the R 1 to R 4, more preferably a combination of more preferable ones.
More specifically, the compound represented by the formula (4) or (5) is most preferable.
本発明の式（１）で表される化合物は、種々の方法で製造されるが、例えばＧＢ１５２８５９０公報に記載の方法を参考に、定法で合成可能であり、市販品としても入手可能な下記式（ＡＡ）又は（Ａ’Ａ’）で表されるホルミル誘導体と、下記式（Ｂ）で表されるアニリン誘導体を酢酸やメタノール中で、反応させることにより得ることができる。なお下記式（ＡＡ）乃至（Ｂ）中のＲ1乃至Ｒ4は、それぞれ上記式（１）乃至（３）におけるＲ1乃至Ｒ4と同じ意味を表す。 The compound represented by the formula (1) of the present invention is produced by various methods. For example, with reference to the method described in GB1528590, it can be synthesized by a conventional method and can be obtained as a commercially available product. It can be obtained by reacting the formyl derivative represented by (AA) or (A′A ′) with the aniline derivative represented by the following formula (B) in acetic acid or methanol. R 1 to R 4 in the following formulas (AA) to (B) represent the same meaning as R 1 to R 4 in the above formulas (1) to (3), respectively.
本発明の式（１）で表される化合物の具体例を以下に示すが、本発明はこれらに限定されない。 Specific examples of the compound represented by the formula (1) of the present invention are shown below, but the present invention is not limited thereto.
本発明の着色樹脂組成物は上記式（１）で表されるメチン化合物、バインダー樹脂及び硬化剤を含有する。
本発明の着色樹脂組成物における式（１）で表される化合物の含有量は、本発明の着色樹脂組成物の全固形分（式（１）で表される化合物、バインダー樹脂及び硬化剤等、有機溶剤以外の固形分の総量を指す。以降も同義で用いられる。）１００質量部に対して、通常０．０１乃至５０質量部、好ましくは０．５乃至３０質量部、より好ましくは１乃至１０質量部である。この範囲よりも含有量が多い場合は、析出や凝集が発生したり、硬化不十分のために基板との密着性が低下したりする虞がある。一方、含有量が少ない場合は、色特性としては十分な色純度を得られない虞がある。
The colored resin composition of the present invention contains a methine compound represented by the above formula (1), a binder resin, and a curing agent.
The content of the compound represented by Formula (1) in the colored resin composition of the present invention is the total solid content of the colored resin composition of the present invention (compound represented by Formula (1), binder resin, curing agent, etc. The term refers to the total amount of solids other than organic solvents, and is used synonymously hereinafter.) With respect to 100 parts by mass, usually 0.01 to 50 parts by mass, preferably 0.5 to 30 parts by mass, more preferably 1 Thru | or 10 mass parts. When the content is larger than this range, precipitation or aggregation may occur, or adhesion with the substrate may decrease due to insufficient curing. On the other hand, when the content is small, there is a possibility that sufficient color purity cannot be obtained as color characteristics.
本発明の着色樹脂組成物が含有するバインダー樹脂は、式（１）で表される化合物や任意成分として用いられる顔料等の色材化合物の分散時の分散安定性のため、分散剤、分散助剤として機能するが、着色樹脂組成物がフォトリソグラフィー法で用いられる場合は、カラーフィルター製造時の現像処理工程において用いられるアルカリ性現像液に可溶であることが望ましい。良好な微細パターンを形成するためには、バインダー樹脂が硬化剤や任意成分として用い得る光重合開始剤、硬化促進剤及び光重合性モノマー等との十分な硬化特性を有していることが望ましく、また、バインダー樹脂が式（１）で表される化合物等の色材化合物や硬化剤、光重合開始剤、光重合性モノマー、顔料分散液等の構成材料と相溶性が良く、着色樹脂組成物が析出や凝集等を起こさないよう安定でなければならない。着色樹脂組成物がインクジェット法で用いられる場合は、特にアルカリ可溶性は必要ではないため、他の構成材料との相溶性の良いバインダー樹脂を選択すればよい。 The binder resin contained in the colored resin composition of the present invention contains a dispersant, a dispersion aid for dispersion stability during dispersion of a colorant compound such as a compound represented by formula (1) and a pigment used as an optional component. Although functioning as an agent, when the colored resin composition is used in a photolithography method, it is desirable that the colored resin composition be soluble in an alkaline developer used in a development processing step when producing a color filter. In order to form a good fine pattern, it is desirable that the binder resin has sufficient curing characteristics with a curing agent, a photopolymerization initiator that can be used as an optional component, a curing accelerator, a photopolymerizable monomer, and the like. In addition, the binder resin has good compatibility with constituent materials such as a colorant compound such as the compound represented by the formula (1), a curing agent, a photopolymerization initiator, a photopolymerizable monomer, and a pigment dispersion, and a colored resin composition It must be stable so that it does not precipitate or agglomerate. When the colored resin composition is used in the ink jet method, alkali solubility is not particularly required, and therefore a binder resin having good compatibility with other constituent materials may be selected.
バインダー樹脂としては公知の樹脂を使用することもできるが、より好ましくは以下に挙げる１個以上のカルボキシル基、または水酸基を有するエチレン性不飽和モノマーあるいは他の共重合可能な芳香族炭化水素基や脂肪族炭化水素基を有するエチレン性不飽和モノマー等の共重合体であることが望ましい。また、これらの側鎖もしくは末端等にエポキシ基を有したもの、さらにアクリレートを付加させたエポキシアクリレート樹脂も使用できる。これらのモノマー等は単独でも２種以上組み合わせても良い。 As the binder resin, known resins can be used, but more preferably, one or more of the following carboxyl groups, ethylenically unsaturated monomers having a hydroxyl group, or other copolymerizable aromatic hydrocarbon groups, A copolymer such as an ethylenically unsaturated monomer having an aliphatic hydrocarbon group is desirable. In addition, those having an epoxy group at the side chain or terminal, and epoxy acrylate resins to which acrylate is added can also be used. These monomers may be used alone or in combination of two or more.
バインダー樹脂の原料として使用し得る前記カルボキシル基含有不飽和モノマーとしては、例えば、アクリル酸、メタクリル酸、クロトン酸、α−クロルアクリル酸、エタクリル酸、けい皮酸等の不飽和モノカルボン酸類；マレイン酸、無水マレイン酸、フマル酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、メサコン酸等の不飽和ジカルボン酸（無水物）類；３価以上の不飽和多価カルボン酸（無水物）類、２−（メタ）アクリロイロキシエチルヘキサヒドロフタル酸、２−メタアクリロイロキシエチル２−ヒドロキシプロピルフタレート及び２−アクリロイロキシエチル２−ヒドロキシエチルフタル酸等を挙げることができる。これらのカルボキシル基を有するエチレン性不飽和モノマーは、単独で又は２種以上を混合して使用することができる。 Examples of the carboxyl group-containing unsaturated monomer that can be used as a raw material for the binder resin include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, ethacrylic acid, and cinnamic acid; Unsaturated dicarboxylic acids (anhydrides) such as acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid; trivalent or higher unsaturated polycarboxylic acids (anhydrides) ), 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl 2-hydroxypropyl phthalate, 2-acryloyloxyethyl 2-hydroxyethylphthalic acid, and the like. These ethylenically unsaturated monomers having a carboxyl group can be used alone or in admixture of two or more.
バインダー樹脂の原料として使用し得る前記水酸基含有不飽和モノマーとしては、例えば、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、３−ヒドロキシプロピル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、３−ヒドロキシブチル（メタ）アクリレート、５−ヒドロキシペンチル（メタ）アクリレート、４−ヒドロキシペンチル（メタ）アクリレート、３−ヒドロキシペンチル（メタ）アクリレート、６−ヒドロキシヘキシル（メタ）アクリレート、５−ヒドロキシヘキシル（メタ）アクリレート、４−ヒドロキシヘキシル（メタ）アクリレート、５−ヒドロキシ−３−メチル−ペンチル（メタ）アクリレート、シクロヘキサン−１，４−ジメタノール−モノ（メタ）アクリレート、２−（２−ヒドロキシエチルオキシ）エチル（メタ）アクリレート、グリセリンモノメタクリレート、ポリエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコールモノ（メタ）アクリレート及びポリ（エチレングリコール−プロピレングリコール）モノメタクリレート等の水酸基末端ポリアルキレングリコールモノ（メタ）アクリレート等を挙げることができる。これらの水酸基を有するエチレン性不飽和モノマーは、単独で又は２種以上を混合して使用することができる。 Examples of the hydroxyl group-containing unsaturated monomer that can be used as a raw material for the binder resin include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl. (Meth) acrylate, 3-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 4-hydroxypentyl (meth) acrylate, 3-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 5-hydroxyhexyl (meth) acrylate, 4-hydroxyhexyl (meth) acrylate, 5-hydroxy-3-methyl-pentyl (meth) acrylate, cyclohexane-1,4-dimethanol-mono (meth) Hydroxyl groups such as acrylate, 2- (2-hydroxyethyloxy) ethyl (meth) acrylate, glycerin monomethacrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate and poly (ethylene glycol-propylene glycol) monomethacrylate Examples include terminal polyalkylene glycol mono (meth) acrylate. These ethylenically unsaturated monomers having a hydroxyl group can be used alone or in admixture of two or more.
また、バインダー樹脂の原料として使用し得る前記以外の不飽和モノマーとしては、例えば、スチレン、α−メチルスチレン、ｏ−ビニルトルエン、ｍ−ビニルトルエン、ｐ−ビニルトルエン、ｏ−クロルスチレン、ｍ−クロルスチレン、ｐ−クロルスチレン、ｐ−メトキシスチレン等の芳香族ビニル化合物；メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、ｉ−プロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、ｉ−ブチル（メタ）アクリレート、ｓｅｃ−ブチル（メタ）アクリレート、ｔ−ブチル（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリレート、ベンジル（メタ）アクリレート、パラクミルフェノキシエチレングリコール（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、ｏ−フェニルフェノールグリシジルエーテル（メタ）アクリレート、ｏ−フェニルフェノール（メタ）アクリレートヒドロキシエチル化物及びフェノキシエチル（メタ）アクリレート等の不飽和カルボン酸エステル類；シクロペンチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、トリメチルシクロヘキシル（メタ）アクリレート、ノルボルニル（メタ）アクリレート、ノルボルニルメチル（メタ）アクリレート、フェニルノルボニル（メタ）アクリレート、シアノノルボルニル（メタ）アクリレート、イソボルニル（メタ）アクリレート、ボルニル（メタ）アクリレート、メンチル（メタ）アクリレート、フェンチル（メタ）アクリレート、アダマンチル（メタ）アクリレート、ジメチルアダマンチル（メタ）アクリレート、トリシクロ〔５．２．１．０2,6〕デカ−８−イル＝（メタ）アクリレート、トリシクロ〔５．２．１．０2,6〕デカ−４−メチル＝（メタ）アクリレート、シクロデシル（メタ）アクリレート、２−（メタ）アクリロイロキシエチルヘキサヒドロフタル酸及びｔ−ブチルシクロヘキシル（メタ）アクリレート等の脂環骨格類；ポリエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコールモノ（メタ）アクリレート及びポリ（エチレングリコール−プロピレングリコール）モノメタクリレート等の水酸基末端ポリアルキレングリコールモノ（メタ）アクリレート類；メトキシポリエチレングリコールモノメタクリレート、ラウロキシポリエチレングリコールモノ（メタ）アクリレート、オクトキシポリエチレングリコールポリプロピレングリコールモノ（メタ）アクリレート、ノニルフェノキシポリエチレングリコールモノアクリレート、ノニルフェノキシポリプロピレングリコールモノアクリレート及びアリロキシポリエチレングリコール−ポリプロピレングリコールモノ（メタ）アクリレート等のアルキル末端ポリアルキレングリコールモノ（メタ）アクリレート類；２−アミノエチルアクリレート、２−アミノエチルメタクリレート、２−アミノプロピルアクリレート、２−アミノプロピルメタクリレート、３−アミノプロピルアクリレート及び３−アミノプロピルメタクリレート等の不飽和カルボン酸アミノアルキルエステル類；グリシジルアクリレート、グリシジルメタクリレート、３，４−エポキシブチル(メタ)アクリレート、（３，４−エポキシシクロヘキシル）メチル（メタ）アクリレート及び４−ヒドロキシブチル（メタ）アクリレートグリシジルエーテル等の不飽和カルボン酸グリシジルエステル類；酢酸ビニル、プロピオン酸ビニル、酪酸ビニル及び安息香酸ビニル等のカルボン酸ビニルエステル類；ビニルメチルエーテル、ビニルエチルエーテル、アリルグリシジルエーテル及びメタリルグリシジルエーテル等の不飽和エーテル類；アクリロニトリル、メタクリロニトリル、α−クロロアクリロニトリル及びシアン化ビニリデン等のシアン化ビニル化合物；アクリルアミド、メタクリルアミド、α−クロロアクリルアミド、Ｎ−フェニルマレイミド、Ｎ−シクロヘキシルマレイミド、Ｎ−（メタ）アクリロイルフタルイミド、Ｎ−（２−ヒドロキシエチル）アクリルアミド、Ｎ−（２−ヒドロキシエチル）メタクリルアミド及びマレイミド等の不飽和アミドあるいは不飽和イミド類；１，３−ブタジエン、イソプレン及びクロロプレン等の脂肪族共役ジエン類；並びにポリスチレン、ポリメチルアクリレート、ポリメチルメタクリレート、ポリｎ−ブチルアクリレート、ポリｎ−ブチルメタクリレート及びポリシリコーン等の重合体分子鎖の末端にモノアクリロイル基あるいはモノメタクリロイル基を有するマクロモノマー類等を挙げることができる。これらの不飽和モノマーは、単独で又は２種以上を混合して使用することができる。 Examples of unsaturated monomers other than those that can be used as a raw material for the binder resin include, for example, styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, o-chlorostyrene, m- Aromatic vinyl compounds such as chlorostyrene, p-chlorostyrene, p-methoxystyrene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (Meth) acrylate, i-butyl (meth) acrylate, sec-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, benzyl (meth) acrylate, paracumylphenoxyethylene glycol ( (Meth) acrylate, Unsaturated carboxylic acid esters such as hydroxy-3-phenoxypropyl (meth) acrylate, o-phenylphenol glycidyl ether (meth) acrylate, o-phenylphenol (meth) acrylate hydroxyethylated product and phenoxyethyl (meth) acrylate; Cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, norbornyl (meth) acrylate, norbornylmethyl (meth) acrylate, phenylnorbornyl (meth) acrylate, cyanonorbornyl (meth) acrylate , Isobornyl (meth) acrylate, bornyl (meth) acrylate, menthyl (meth) acrylate, fentyl (meth) acrylate, adamantyl ( (Meth) acrylate, dimethyladamantyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] dec-8-yl = (meth) acrylate, tricyclo [5.2.1.0 2,6 ] deca Alicyclic skeletons such as 4-methyl = (meth) acrylate, cyclodecyl (meth) acrylate, 2- (meth) acryloyloxyethyl hexahydrophthalic acid and t-butylcyclohexyl (meth) acrylate; polyethylene glycol mono (meth) Hydroxyl-terminated polyalkylene glycol mono (meth) acrylates such as acrylate, polypropylene glycol mono (meth) acrylate and poly (ethylene glycol-propylene glycol) monomethacrylate; methoxypolyethylene glycol monomethacrylate, lauroxypolyethyleneglycol Alkyl-terminated polyalkylenes such as rumono (meth) acrylate, octoxy polyethylene glycol polypropylene glycol mono (meth) acrylate, nonylphenoxypolyethylene glycol monoacrylate, nonylphenoxypolypropylene glycol monoacrylate and allyloxypolyethylene glycol-polypropylene glycol mono (meth) acrylate Glycol mono (meth) acrylates; unsaturated amino acids such as 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 3-aminopropyl acrylate and 3-aminopropyl methacrylate Alkyl esters; glycidyl acrylate, glycidyl methacrylate, , 4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate glycidyl ethers and other unsaturated carboxylic acid glycidyl esters; vinyl acetate, vinyl propionate Carboxylic acid vinyl esters such as vinyl butyrate and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether and methallyl glycidyl ether; acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and cyanide Vinyl cyanide compounds such as vinylidene chloride; acrylamide, methacrylamide, α-chloroacrylamide, N-phenylmaleimide, N-cyclohexylmaleimide, N- (meth) acryloyl Unsaturated amides or unsaturated imides such as tarimide, N- (2-hydroxyethyl) acrylamide, N- (2-hydroxyethyl) methacrylamide and maleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene And macromonomers having a monoacryloyl group or a monomethacryloyl group at the end of the polymer molecular chain such as polystyrene, polymethyl acrylate, polymethyl methacrylate, poly n-butyl acrylate, poly n-butyl methacrylate and polysilicone. Can be mentioned. These unsaturated monomers can be used alone or in admixture of two or more.
バインダー樹脂（共重合体）を製造する場合は、重合開始剤を使用する。ここで共重合体を合成するときに使用される重合開始剤の具体例としては、例えば、α，α’−アゾビス（イソブチロニトリル）、２，２’−アゾビス（２−メチルブチロニトリル）、ｔ−ブチルパーオクトエート、ジ−ｔ−ブチルパーオキシド過酸化ベンゾイルメチルエチルケトンパーオキシド等を挙げることができる。重合開始剤の使用割合は、共重合体の合成に使用する全単量体１００質量部に対して、０．０１乃至２５質量部である。また、共重合体を合成する場合は、有機溶剤を使用するのが好ましいが、使用する単官能のモノマーや重合開始剤等に対して十分な溶解力を有するものを使用する。バインダー樹脂の製造に使用し得る有機溶剤としては、後述する本発明の着色樹脂組成物が含有する有機溶剤と同様のものが挙げられる。 When manufacturing binder resin (copolymer), a polymerization initiator is used. Specific examples of the polymerization initiator used when synthesizing the copolymer are, for example, α, α′-azobis (isobutyronitrile), 2,2′-azobis (2-methylbutyronitrile). ), T-butyl peroctoate, di-t-butyl peroxide benzoylmethyl ethyl ketone peroxide and the like. The ratio of the polymerization initiator used is 0.01 to 25 parts by mass with respect to 100 parts by mass of all monomers used for the synthesis of the copolymer. In the case of synthesizing a copolymer, it is preferable to use an organic solvent, but one having sufficient dissolving power for the monofunctional monomer and polymerization initiator to be used is used. As an organic solvent which can be used for manufacture of binder resin, the thing similar to the organic solvent which the colored resin composition of this invention mentioned later contains is mentioned.
共重合体を合成するときの反応温度は５０乃至１２０℃であることが好ましく、特に好ましくは８０乃至１００℃である。また、反応時間は１乃至６０時間であることが好ましく、より好ましくは３乃至２０時間である。共重合体の好ましい酸価は１０乃至３００（ｍｇＫＯＨ／ｇ）であり、好ましい水酸基価は１０乃至２００（ｍｇＫＯＨ／ｇ）である。酸価もしくは水酸基価が１０以下の場合は現像性が低下する。共重合体の重量平均分子量（Ｍｗ）は２０００乃至４０００００が好ましく、３０００乃至１０００００がより好ましい。重量平均分子量が２０００以下、あるいは４０００００以上では、感度および現像性等が低下する。
尚、本発明において、酸価はＪＩＳ Ｋ−２５０１に、水酸基価はＪＩＳ Ｋ−１５５７に準拠した方法で測定した値を意味する、また、重量平均分子量は、ＧＰＣ（ゲルパーミエイションクロマトグラフィー）の測定結果に基づいて、ポリスチレン換算で算出した値を意味する。
The reaction temperature when synthesizing the copolymer is preferably 50 to 120 ° C., particularly preferably 80 to 100 ° C. The reaction time is preferably 1 to 60 hours, more preferably 3 to 20 hours. The preferred acid value of the copolymer is 10 to 300 (mgKOH / g), and the preferred hydroxyl value is 10 to 200 (mgKOH / g). When the acid value or hydroxyl value is 10 or less, developability is lowered. The weight average molecular weight (Mw) of the copolymer is preferably 2000 to 400,000, and more preferably 3000 to 100,000. When the weight average molecular weight is 2000 or less, or 400000 or more, sensitivity, developability and the like are lowered.
In the present invention, the acid value is a value measured by a method according to JIS K-2501, and the hydroxyl value is a value measured by a method according to JIS K-1557, and the weight average molecular weight is GPC (gel permeation chromatography). Based on the measurement result, it means a value calculated in terms of polystyrene.
また、共重合体の側鎖に更に不飽和二重結合を導入した重合体もバインダー樹脂として有用である。例えば、無水マレイン酸と共重合可能なスチレン、ビニルフェノール、アクリル酸、アクリル酸エステル、アクリルアミド等との共重合物の無水マレイン酸部に、ヒドロキシエチルアクリレート等のアルコール性のヒドロキシル基を有するアクリレートやグリシジルメタクリレート等のエポキシ基を有するアクリレートを反応させハーフエステル化した化合物、およびアクリル酸やアクリル酸エステルとヒドロキシエチルアクリレート等のアルコール性のヒドロキシル基を有するアクリレートとの共重合体の水酸基にアクリル酸を反応せしめた化合物等が挙げられる。また、ウレタン樹脂やポリアミド、ポリイミド樹脂、ポリエステル樹脂、市販のＡＣＡ−２００Ｍ（ダイセル社製）、ＯＲＧＡ−３０６０（大阪有機化学製)、ＡＸ３−ＢＮＸ０２（日本触媒製）、ＵＸＥ−３０２４（日本化薬製）、ＵＸＥ−３０００（日本化薬製)、ＺＧＡ−２８７Ｈ（日本化薬製）、ＴＣＲ−１３３８Ｈ（日本化薬製）、ＺＸＲ−１７２２Ｈ（日本化薬製）、ＺＦＲ−１４０１Ｈ（日本化薬製）、ＺＣＲ−１６４２H（日本化薬製）もバインダー樹脂として使用することができる。 A polymer in which an unsaturated double bond is further introduced into the side chain of the copolymer is also useful as a binder resin. For example, an acrylate having an alcoholic hydroxyl group such as hydroxyethyl acrylate in the maleic anhydride portion of a copolymer with styrene, vinylphenol, acrylic acid, acrylic ester, acrylamide, or the like copolymerizable with maleic anhydride Acrylic acid is added to the hydroxyl group of a compound obtained by reacting an acrylate having an epoxy group, such as glycidyl methacrylate, and a copolymer of acrylic acid or an acrylate ester having an alcoholic hydroxyl group such as hydroxyethyl acrylate. Examples thereof include reacted compounds. In addition, urethane resin, polyamide, polyimide resin, polyester resin, commercially available ACA-200M (manufactured by Daicel), ORGA-3060 (manufactured by Osaka Organic Chemical), AX3-BNX02 (manufactured by Nippon Shokubai), UXE-3024 (Nippon Kayaku) Made), UXE-3000 (made by Nippon Kayaku), ZGA-287H (made by Nippon Kayaku), TCR-1338H (made by Nippon Kayaku), ZXR-1722H (made by Nippon Kayaku), ZFR-1401H (Nippon Kayaku) And ZCR-1642H (manufactured by Nippon Kayaku) can also be used as the binder resin.
バインダー樹脂は、本発明の着色樹脂組成物に単独で又は２種以上を混合して使用することができる。本発明の着色樹脂組成物におけるバインダー樹脂の含有量は、着色樹脂組成物の全固形分１００質量部に対して、通常、０．５乃至９９質量部、好ましくは５乃至５０質量部である。バインダー樹脂の含有量が０．５質量部未満の場合、アルカリ現像性が低下し、画素が形成される部分以外の領域での地汚れや膜残り等の問題が発生する場合がある。 Binder resin can be used individually or in mixture of 2 or more types in the colored resin composition of this invention. The content of the binder resin in the colored resin composition of the present invention is usually 0.5 to 99 parts by mass, preferably 5 to 50 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. When the content of the binder resin is less than 0.5 parts by mass, the alkali developability is deteriorated, and problems such as background contamination and film residue in areas other than the area where pixels are formed may occur.
本発明の着色樹脂組成物が含有する硬化剤としては、ラジカル重合の場合は光重合モノマー、イオン硬化の場合はエポキシ樹脂、その他にメラミン硬化剤等が挙げられる。これら硬化剤の具体例としては、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、２−エチルヘキシル（メタ）アクリレート、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコー（メタ）アクリレート、テトラエチレングリコール（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、ペンタエリスリトールジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、グリセロール（メタ）アクリレート、ビスフェノール−Ａ型エポキシジ（メタ）アクリレート、ビスフェノール−Ｆ型エポキシジ（メタ）アクリレート、ビスフェノール−フルオレン型エポキシジ（メタ）アクリレート、エトキシ化トリメチロールプロパントリ（メタ）アクリレート、プロポキシ化トリメチロールプロパントリ（メタ）アクリレート、エトキシ化グリセリントリ（メタ）アクリレート、エトキシ化イソシアヌル酸トリ（メタ）アクリレート、ジトリメチロールプロパンテトラ（メタ）アクリレート、エトキシ化ペンタエリスリトールテトラ（メタ）アクリレート、９,９−ビス〔４−（２−アクリロイルオキシエトキシ）フェニル〕フルオレン、カヤラッドＲＰ−１０４０（日本化薬製）、カヤラッドＤＰＣＡ−３０（日本化薬製）、ＵＡ−３３Ｈ（新中村化学製)、ＵＡ−５３Ｈ（新中村化学製)及びＭ−８０６０（東亞合成製)等の（メタ）アクリレートモノマー；ＴＥＭＰＩＣ（堺化学製)、ＴＭＭＰ（堺化学製)、ＰＥＭＰ（堺化学製）及びＤＰＭＰ（堺化学製）等のチオール系重合モノマー；日本化薬製品のＮＣ−６０００、ＮＣ−６３００、ＮＣ−６３００Ｈ、ＮＣ−３０００、ＥＯＣＮ−１０２０、ＸＤ−１０００、ＥＰＰＮ−５０１Ｈ、ＢＲＥＮ−Ｓ、ＮＣ−７３００Ｌ、ダイセル化学製品のセロキサイト２０２１Ｐ、ＥＨＰＥ３１５０、サイクロマーＭ１００、エポリードＰＢ３６００、ジャパンエポキシレジン製品のエピコート８２８、エピコートＹＸ８０００、エピコートＹＸ４０００、プリンテック製品のＶＧ−３１０１Ｌ、サイラエースＳ５１０（チッソ）、ＴＥＰＩＣ（日産化学工業）等のエポキシ樹脂；並びにメチロール化メラミン及びＭｗ−３０（三和ケミカル）等のメラミン硬化剤が挙げられるが、これらに限定されるものではない。 Examples of the curing agent contained in the colored resin composition of the present invention include a photopolymerization monomer in the case of radical polymerization, an epoxy resin in the case of ion curing, and a melamine curing agent. Specific examples of these curing agents include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, Triethyleneglycol (meth) acrylate, tetraethylene glycol (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, di Pentaerythritol hexa (meth) acrylate, glycerol (meth) acrylate, bisphenol-A type epoxy di (meth) acrylate, bisphenol F type epoxy di (meth) acrylate, bisphenol-fluorene type epoxy di (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, ethoxylated glycerin tri (meth) acrylate, ethoxy Isocyanuric acid tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, ethoxylated pentaerythritol tetra (meth) acrylate, 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene, Kayrad RP- 1040 (Nippon Kayaku), Kayrad DPCA-30 (Nippon Kayaku), UA-33H (Shin Nakamura Chemical), UA-53H (Shin Nakamura Chemical) and M-8060 (Toagosei) Me ) Acrylate monomer; thiol polymerization monomers such as TEMPIC (manufactured by Sakai Chemical), TMMP (manufactured by Sakai Chemical), PEMP (manufactured by Sakai Chemical) and DPMP (manufactured by Sakai Chemical); NC-6000 and NC-6300 of Nippon Kayaku products , NC-6300H, NC-3000, EOCN-1020, XD-1000, EPPN-501H, BREN-S, NC-7300L, Daicel Chemical's Celoxite 2021P, EHPE3150, Cyclomer M100, Epolide PB3600, Japan Epoxy Resin's Epicoat 828, Epicoat YX8000, Epicoat YX4000, Printec product VG-3101L, Silaace S510 (Nisso), TEPIC (Nissan Chemical Industries) and other epoxy resins; and methylolated melamine and Mw-30 (three Melamine curing agents such as Japanese Chemical), but are not limited thereto.
硬化剤は、本発明の着色樹脂組成物に、単独で又は２種以上を混合して使用することができる。硬化剤の含有量は、着色樹脂組成物の全固形分１００質量部に対して通常１乃至８０質量部、好ましくは５乃至５０質量部である。この範囲より少ない場合は耐溶剤性等の効果が小さくなり、多すぎる場合は現像性が低下し、現像できない場合があるため好ましくない。また、エポキシ樹脂を硬化させるための硬化促進剤との組合せが好ましい。 A hardening | curing agent can be used for the colored resin composition of this invention individually or in mixture of 2 or more types. The content of the curing agent is usually 1 to 80 parts by mass, preferably 5 to 50 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. When the amount is less than this range, the effects such as solvent resistance are reduced, and when the amount is too large, developability is lowered and development may not be possible. Moreover, the combination with the hardening accelerator for hardening an epoxy resin is preferable.
本発明の着色樹脂組成物は、光重合開始剤及び／又は硬化促進剤を含有してもよい。着色樹脂組成物が含有し得る光重合開始剤としては、露光光源として一般的に用いられる超高圧水銀灯から射出される紫外線に充分な感度を有するものが好ましく、ラジカル重合性の光ラジカル開始剤、イオン硬化性の光酸発生剤もしくは光塩基発生剤等のいずれをも用いることが出来る。また、より少ない露光エネルギーで硬化をさせるために、増感剤と呼ばれる重合促進剤の成分を組み合わせて使用することもできる。光重合開始剤の具体例としては、ベンジル、ベンゾインエーテル、ベンゾインブチルエーテル、ベンゾインプロピルエーテル、ベンゾフェノン、３，３’−ジメチル−４−メトキシベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸のエステル化物、４−ベンゾイル−４’−メチルジフェニルスルフィド、ベンジルジメチルケタール、２−ブトキシエチル−４−メチルアミノベンゾエート、クロロチオキサントン、メチルチオキサントン、エチルチオキサントン、イソプロピルチオキサントン、ジメチルチオキサントン、ジエチルチオキサントン、ジイソプロピルチオキサントン、ジメチルアミノメチルベンゾエート、１−（４−ドデシルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、１−ヒドロキシシクロヘキシルフェニルケトン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、メチルベンゾイルフォーメート、２−メチル−１−（４−メチルチオフェニル）−２−モルホリノプロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノン−１、２，４−ビス（トリクロロメチル）−６−（４−メトキシフェニル）−１，３，５−ｓ−トリアジン、２，４，６−トリス（トリクロロメチル）−１，３，５−ｓ−トリアジン、２，４−ビス（トリブロモメチル）−６−（４’−メトキシフェニル）−１，３，５−ｓ−トリアジン、２，４，６−トリス（トリブロモメチル）−１，３，５−ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−（１，３−ベンゾジオキソラン−５−イル）−１，３，５−ｓ−トリアジン、ベンゾフェノン、ベンゾイル安息香酸、１−（４−フェニルスルファニルフェニル）ブタン−１，２−ジオン−２−オキシム−Ｏ−ベンゾアート、１−（４−メチルスルファニルフェニル）ブタン−１，２−ジオン−２−オキシム−Ｏ−アセタート、１−（４−メチルスルファニルフェニル）ブタン−１−オンオキシム−Ｏ−アセタート、４，４’−ビス（ジエチルアミノ）ベンゾフェノン、Ｐ−ジメチルアミノ安息香酸イソアミルエステル、Ｐ−ジメチルアミノ安息香酸エチルエステル、２，２’−ビス（Ｏ−クロロフェニル）−４，４’，５，５’−テトラフェニル−１，２’−ビイミダゾール、ジアゾナフトキノン系開始剤、また市販のカヤキュアーＤＭＢＩ、カヤキュアーＢＤＭＫ、カヤキュアーＢＰ−１００、カヤキュアーＢＭＢＩ、カヤキュアーＤＥＴＸ−Ｓ、カヤキュアーＥＰＡ（いずれも日本化薬製）、ダロキュアー１１７３、ダロキュアー１１１６（いれもメルクジャパン製）、イルガキュアー９０７（ＢＡＳＦジャパン製）、イルガキュアー３６９（ＢＡＳＦジャパン製）、イルガキュアー３７９ＥＧ（ＢＡＳＦジャパン製）、イルガキュアーＯＸＥ−０１（ＢＡＳＦジャパン製）、イルガキュアーＯＸＥ−０２（ＢＡＳＦジャパン製）、イルガキュアーＰＡＧ１０３（ＢＡＳＦジャパン製）、ＴＭＥ−トリアジン（三和ケミカル製）、ビイミダゾール（黒金化成製）、ＳＴＲ−１１０、ＳＴＲ−１（いずれもレスペケミカル製）等が挙げられるが、これらに限定されるものではない。 The colored resin composition of the present invention may contain a photopolymerization initiator and / or a curing accelerator. As the photopolymerization initiator that can be contained in the colored resin composition, those having sufficient sensitivity to ultraviolet rays emitted from an ultra-high pressure mercury lamp generally used as an exposure light source are preferable, radical polymerizable photoradical initiators, Either an ion curable photoacid generator or a photobase generator can be used. Moreover, in order to harden | cure with less exposure energy, the component of the polymerization accelerator called a sensitizer can also be used in combination. Specific examples of the photopolymerization initiator include benzyl, benzoin ether, benzoin butyl ether, benzoin propyl ether, benzophenone, 3,3′-dimethyl-4-methoxybenzophenone, benzoylbenzoic acid, esterified benzoylbenzoic acid, 4-benzoyl -4′-methyldiphenyl sulfide, benzyldimethyl ketal, 2-butoxyethyl-4-methylaminobenzoate, chlorothioxanthone, methylthioxanthone, ethylthioxanthone, isopropylthioxanthone, dimethylthioxanthone, diethylthioxanthone, diisopropylthioxanthone, dimethylaminomethylbenzoate, 1 -(4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl Phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, methylbenzoyl formate, 2-methyl -1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-s-triazine, 2,4,6-tris (trichloromethyl) -1,3,5-s-triazine, 2,4-bis (tribromo Methyl) -6- (4′-methoxyphenyl) -1,3,5-s-triazine, 2,4,6-tris (tribromomethyl) -1,3,5-s-triazine 2,4-bis (trichloromethyl) -6- (1,3-benzodioxolan-5-yl) -1,3,5-s-triazine, benzophenone, benzoylbenzoic acid, 1- (4-phenylsulfanylphenyl) Butane-1,2-dione-2-oxime-O-benzoate, 1- (4-methylsulfanylphenyl) butane-1,2-dione-2-oxime-O-acetate, 1- (4-methylsulfanylphenyl) ) Butan-1-one oxime-O-acetate, 4,4′-bis (diethylamino) benzophenone, P-dimethylaminobenzoic acid isoamyl ester, P-dimethylaminobenzoic acid ethyl ester, 2,2′-bis (O-chlorophenyl) ) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, diazonaphthoquinone System initiators, commercially available Kayacure DMBI, Kayacure BDK, Kayacure BP-100, Kayacure BMBI, Kayacure DETX-S, Kayacure EPA (all manufactured by Nippon Kayaku), Darocur 1173, Darocure 1116 (Iremo Merck Japan) Irgacure 907 (made by BASF Japan), Irgacure 369 (made by BASF Japan), Irgacure 379EG (made by BASF Japan), Irgacure OXE-01 (made by BASF Japan), Irgacure OXE-02 (made by BASF Japan), Irga Cure PAG103 (manufactured by BASF Japan), TME-triazine (manufactured by Sanwa Chemical), biimidazole (manufactured by Kurokin Kasei), STR-110, STR-1 (all manufactured by Respe Chemical) It is, but not limited thereto.
光重合開始剤は、本発明の着色樹脂組成物に単独もしくは２種以上組み合わせて使用することができる。光重合開始剤の含有量は、着色樹脂性組成物の全固形分１００質量部に対して通常０．５乃至５０質量部、好ましくは１乃至２５質量部である。 A photoinitiator can be used individually or in combination of 2 or more types in the colored resin composition of the present invention. The content of the photopolymerization initiator is usually 0.5 to 50 parts by mass, preferably 1 to 25 parts by mass with respect to 100 parts by mass of the total solid content of the colored resinous composition.
本発明の着色樹脂組成物が含有し得る硬化促進剤は、イオン硬化を促進させる反応触媒であり、例えば、１級乃至３級のアミンやイミダゾール類等の窒素含有複素環化合物、酸無水物等が挙げられる。 The curing accelerator that can be contained in the colored resin composition of the present invention is a reaction catalyst that promotes ion curing, such as nitrogen-containing heterocyclic compounds such as primary to tertiary amines and imidazoles, acid anhydrides, and the like. Is mentioned.
アミンの具体例としてはトリエチルアミン、トリエタノールアミン、日本化薬製品のカヤハードＡ−Ａ、カヤボンドＣ−１００、カヤボンドＣ−２００Ｓ、カヤボンドＣ−３００Ｓ等が挙げられる。 Specific examples of amines include triethylamine, triethanolamine, Nippon Kayaku products Kayahard A-A, Kayabond C-100, Kayabond C-200S, Kayabond C-300S, and the like.
イミダゾールの具体例としては四国化成工業製品のキュアゾール２ＭＺ−Ｈ、キュアゾールＣ１１Ｚ、キュアゾールＣ１７Ｚ、キュアゾール１，２ＤＭＺ、キュアゾール２Ｅ４ＭＺ、キュアゾール２ＰＺ、キュアゾール２Ｐ４ＭＺ、キュアゾール１Ｂ２ＭＺ、キュアゾール１Ｂ２ＰＺ、キュアゾール２ＭＺ−ＣＮ、キュアゾールＣ１１Ｚ−ＣＮ、キュアゾール２Ｅ４ＭＺ−ＣＮ、キュアゾール２ＰＺ−ＣＮ、キュアゾールＣ１１Ｚ−ＣＮＳ、キュアゾール２ＰＺＣＮＳ−ＰＷ、キュアゾール２ＭＺ−Ａ、キュアゾールＣ１１Ｚ−Ａ、キュアゾール２Ｅ４ＭＺ−Ａ、キュアゾール２ＭＡ−ＯＫ、キュアゾール２ＰＺ−ＯＫ、キュアゾール２ＰＨＺ−ＰＷ、キュアゾール２Ｐ４ＭＨＺ−ＰＷ、キュアゾールＴＢＺ、キュアゾール２ＰＺＬ−Ｔ、キュアゾールＶＴ、キュアゾールＳＦＺ等が挙げられる。 Specific examples of imidazole include Shikoku Kasei Kogyo Co., Ltd. Cureazole 2MZ-H, Cureazole C11Z, Curesol C17Z, Cureazole 1,2DMZ, Curesol 2E4MZ, Cureazole 2PZ, Cureazole 2P4MZ, Cureazole 1B2MZ, Cureazole 1B2PZ, Cureazole 2MZ-CN, Cureazole 2MZ-CN CN, Curezol 2E4MZ-CN, Curezol 2PZ-CN, Curezol C11Z-CNS, Curezol 2PZCNS-PW, Curezol 2MZ-A, Curezol C11Z-A, Curezol 2E4MZ-A, Curezol 2MA-OK, Curezol 2PZ-OKZ PW, Curezol 2P4MHZ-PW, Curezol TBZ, Curezol 2PZL-T, Ki Azole VT, Curesol SFZ, and the like.
酸無水物の具体例としては無水マレイン酸、無水コハク酸、無水フタル酸、無水テトラヒドロフタル酸、無水ピロメリット酸、ビフェニルテトラカルボン酸二無水物、日本化薬製品のカヤハードＭＣＤ等が挙げられる。これらのうち、硬化促進剤としてはイミダゾール類が好ましく、キュアゾール１Ｂ２ＰＺ、キュアゾール２ＰＺ、キュアゾール１Ｂ２ＭＺ及びキュアゾール２Ｅ４ＭＺが反応性からより好ましい。 Specific examples of the acid anhydride include maleic anhydride, succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic dianhydride, Kayahard MCD of Nippon Kayaku products, and the like. Among these, imidazoles are preferable as the curing accelerator, and Curezol 1B2PZ, Curezol 2PZ, Curezol 1B2MZ and Curezol 2E4MZ are more preferable from the viewpoint of reactivity.
硬化促進剤の含有量は、着色樹脂組成物の全固形分１００質量部に対して通常０．０１乃至５０質量部、好ましくは０．０５乃至２０質量部である。硬化促進剤の含有量が０．０１質量部よりも少ない場合は、硬化性が低下する恐れがあり、５０質量部を超える場合は保存安定性が悪くなる恐れがある。 The content of the curing accelerator is usually 0.01 to 50 parts by mass, preferably 0.05 to 20 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition. When there is less content of a hardening accelerator than 0.01 mass part, there exists a possibility that sclerosis | hardenability may fall, and when it exceeds 50 mass parts, there exists a possibility that storage stability may worsen.
本発明の着色樹脂組成物には、任意成分として上記式（１）で表される化合物以外の色素を併用してもよい。任意成分として併用し得る色素は、染料や有機顔料、無機顔料の中から適宜選択すればよく、単独で用いても２種以上を混合して用いても構わないが、発明の着色樹脂組成物は赤色画素または緑色画素に関するものなので、公知の赤色染料やイエロー染料、または赤色顔料やイエロー顔料、公知の緑色染料やイエロー染料、または緑色顔料やイエロー顔料を用いることが好ましい。任意成分としての色素を併用する場合、その含有量は、本発明の着色樹脂組成物の全固形分１００質量部に対する必須成分である式（１）で表される化合物と任意成分である色素の含有量の合計が、通常０．０１乃至７０質量部、好ましくは０．５乃至５０質量部、より好ましくは１．０乃至４０質量部の範囲内であれば特に限定されない。 In the colored resin composition of the present invention, a dye other than the compound represented by the above formula (1) may be used in combination as an optional component. The pigment that can be used in combination as an optional component may be appropriately selected from dyes, organic pigments, and inorganic pigments, and may be used alone or in combination of two or more, but the colored resin composition of the invention Is related to a red pixel or a green pixel, and it is preferable to use a known red dye or yellow dye, or a red pigment or yellow pigment, a known green dye or yellow dye, or a green pigment or yellow pigment. When using together the pigment | dye as an arbitrary component, the content is the compound represented by Formula (1) which is an essential component with respect to 100 mass parts of total solids of the colored resin composition of this invention, and the pigment | dye which is an arbitrary component. There is no particular limitation as long as the total content is in the range of usually 0.01 to 70 parts by mass, preferably 0.5 to 50 parts by mass, more preferably 1.0 to 40 parts by mass.
式（１）で表される化合物に併用し得る色素としては、顔料が好ましい。
本発明の着色樹脂組成物に併用できる有機顔料に特に制限はなく、顔料の具体例としては、Ｃ．Ｉ．ピグメントレッド２、５、１７、３１、３２、４１、１２２、１２３、１４４、１４９、１６６、１６８、１７０、１７１、１７５、１７６、１７７、１７８、１７９、１８０、１８５、１８７、２０２、２０６、２０７、２０９、２１４、２２０、２２１、２２４、２４２、２４３、２５４、２５５、２６２、２６４、２７２等の赤色顔料、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、１３７、１３８、１３９、１４７、１４８、１５０、１５３、１５４、１６６、１７３、１９４、２１４等の黄色顔料、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等のオレンジ色顔料、Ｃ．Ｉ．ピグメントグリーン７、１０、３６、３７、５８、５９等の緑色顔料などがある。これらのうち、Ｃ．Ｉ．ピグメントレッド１７７、Ｃ．Ｉ．ピグメントレッド２５４、Ｃ．Ｉ．ピグメントイエロー１３８、Ｃ．Ｉ．ピグメントイエロー１５０、Ｃ．Ｉ．ピグメントイエロー１８５、Ｃ．Ｉ．ピグメントグリーン７、Ｃ．Ｉ．ピグメントグリーン３６、Ｃ．Ｉ．ピグメントグリーン５８及びＣ．Ｉ．ピグメントグリーン５９よりなる群から選ばれる少なくとも一種を併用することが好ましい。
As the dye that can be used in combination with the compound represented by the formula (1), a pigment is preferable.
There is no particular limitation on the organic pigment that can be used in combination with the colored resin composition of the present invention. Specific examples of the pigment include C.I. I. Pigment Red 2, 5, 17, 31, 32, 41, 122, 123, 144, 149, 166, 168, 170, 171, 175, 176, 177, 178, 179, 180, 185, 187, 202, 206, Red pigments such as C. 207, 209, 214, 220, 221, 224, 242, 243, 254, 255, 262, 264, 272; I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc., yellow pigments, C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc., orange pigments, C.I. I. And green pigments such as CI Pigment Green 7, 10, 36, 37, 58, and 59. Of these, C.I. I. Pigment red 177, C.I. I. Pigment red 254, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 185, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 58 and C.I. I. It is preferable to use at least one selected from the group consisting of CI Pigment Green 59.
本発明の着色樹脂組成物に併用できる無機顔料に特に制限はなく、その具体例としては、複合金属酸化物顔料、カーボンブラック、黒色低次酸化チタン、酸化チタン、硫酸バリウム、亜鉛華、硫酸鉛、黄色鉛、ベンガラ、群青、紺青、酸化クロム、アンチモン白、鉄黒、鉛丹、硫化亜鉛、カドミウムエロー、カドミウムレッド、亜鉛、マンガン紫、コバルト紫、硫酸バリウム、炭酸マグネシウム等の金属酸化物、金属硫化物、硫酸塩、金属水酸化物、金属炭酸塩等が挙げられる。 The inorganic pigment that can be used in combination with the colored resin composition of the present invention is not particularly limited, and specific examples thereof include composite metal oxide pigments, carbon black, black low-order titanium oxide, titanium oxide, barium sulfate, zinc white, lead sulfate. , Yellow lead, bengara, ultramarine, bitumen, chromium oxide, antimony white, iron black, red lead, zinc sulfide, cadmium yellow, cadmium red, zinc, manganese oxide, purple purple, cobalt purple, barium sulfate, magnesium carbonate, etc., Examples thereof include metal sulfides, sulfates, metal hydroxides, and metal carbonates.
本発明の着色樹脂組成物におけるこれら顔料の含有量は、本発明の着色樹脂組成物の必須成分である式（１）で表される化合物と任意成分である顔料の含有量の合計が、本発明の着色樹脂組成物の全固形分１００質量部に対して、通常０．０１乃至７０質量部、好ましくは０．５乃至５０質量部、より好ましくは１．０乃至４０質量部の範囲内であれば特に限定されないが、顔料単独の含有量が、本発明の着色樹脂組成物の全固形分１００質量部に対して、０．０１乃至６０質量部であることが好ましく、０．１乃至５０質量部であることがより好ましく、１．０乃至４０質量部であることが更に好ましい。この範囲よりも含有量が多い場合は、硬化不十分のために基板との密着性が低下したりする虞がある。 The content of these pigments in the colored resin composition of the present invention is the sum of the content of the compound represented by the formula (1) which is an essential component of the colored resin composition of the present invention and the pigment which is an optional component. In the range of usually 0.01 to 70 parts by weight, preferably 0.5 to 50 parts by weight, more preferably 1.0 to 40 parts by weight with respect to 100 parts by weight of the total solid content of the colored resin composition of the invention. Although there is no particular limitation as long as it is present, the content of the pigment alone is preferably 0.01 to 60 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition of the present invention. The amount is more preferably part by mass, and further preferably 1.0 to 40 parts by mass. When there is more content than this range, there exists a possibility that adhesiveness with a board | substrate may fall because hardening is inadequate.
本発明の着色樹脂組成物に併用できる染料に特に制限はなく、酸性染料、塩基性染料、直接染料、硫化染料、建染染料、ナフトール染料、反応染料、分散染料等が挙げられる。これら染料としては有機溶剤に可溶なものに限らず、有機溶剤に不溶な染料でも分散体とすることで使用することができる。
本発明の着色樹脂組成物におけるこれら染料の含有量は、本発明の着色樹脂組成物の必須成分である式（１）で表される化合物と任意成分である染料の含有量の合計が、本発明の着色樹脂組成物の全固形分１００質量部に対して、通常０．０１乃至７０質量部、好ましくは０．５乃至５０質量部、より好ましくは１．０乃至４０質量部の範囲内であれば特に限定されない。
There is no restriction | limiting in particular in the dye which can be used together with the colored resin composition of this invention, Acid dye, basic dye, direct dye, sulfur dye, vat dye, naphthol dye, reactive dye, disperse dye, etc. are mentioned. These dyes are not limited to those that are soluble in an organic solvent, and dyes that are insoluble in an organic solvent can be used as a dispersion.
The content of these dyes in the colored resin composition of the present invention is the sum of the content of the compound represented by formula (1), which is an essential component of the colored resin composition of the present invention, and the optional component dye. In the range of usually 0.01 to 70 parts by weight, preferably 0.5 to 50 parts by weight, more preferably 1.0 to 40 parts by weight with respect to 100 parts by weight of the total solid content of the colored resin composition of the invention. If there is no particular limitation.
本発明の着色樹脂組成物には、着色樹脂組成物の粘度を下げ、着色樹脂組成物塗布時作業性を改善する目的で有機溶剤を併用してもよい。有機溶剤としては、着色樹脂組成物の構成成分であるバインダー樹脂、光重合開始剤等に対して十分な溶解力を有し、バインダー樹脂の合成に用いる単官能のモノマーや重合開始剤等に対しても十分な溶解力を有するものが好ましく使用できる。また、顔料分散体を作成する際にも分散安定性を保つことができるものも好ましく使用できる。 In the colored resin composition of the present invention, an organic solvent may be used in combination for the purpose of decreasing the viscosity of the colored resin composition and improving workability when the colored resin composition is applied. As an organic solvent, it has sufficient dissolving power with respect to the binder resin, photopolymerization initiator, etc., which are constituents of the colored resin composition, and with respect to the monofunctional monomer and polymerization initiator used for the synthesis of the binder resin. However, those having sufficient dissolving power can be preferably used. Moreover, what can maintain dispersion stability can also be preferably used when preparing a pigment dispersion.
本発明の着色樹脂組成物が含有する有機溶剤の具体例としては、ベンゼン、トルエン及びキシレン等のベンゼン類；メチルセロソルブ、エチルセロソルブ及びブチルセロソルブ等のセロソルブ類；メチルセロソルブアセテート、エチルセロソルブアセテート及びブチルセロソルブアセテート等のセロソルブ酢酸エステル類；プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート及びプロピレングリコールモノブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテル酢酸エステル類；メトキシプロピオン酸メチル、メトキシプロピオン酸エチル、エトキシプロピオン酸メチル、エトキシプロピオン酸エチル等のプロピオン酸エステル類；乳酸メチル、乳酸エチル及び乳酸ブチル等の乳酸エステル類；ジエチレングリコールモノメチルエーテル及びジエチレングリコールモノエチルエーテル等のジエチレングリコール類；酢酸メチル、酢酸エチル及び酢酸ブチル等の酢酸エステル類；ジメチルエーテル、ジエチルエーテル、テトラヒドロフラン及びジオキサン等のエーテル類；アセトン、メチルエチルケトン、メチルブチルケトン及びシクロヘキサノン等のケトン類；並びにメタノール、エタノール、ブタノール、イソプロピルアルコール、ジアセトンアルコール及びベンジルアルコール等のアルコール類等が挙げられるが、これらに限定されるものではない。 Specific examples of the organic solvent contained in the colored resin composition of the present invention include benzenes such as benzene, toluene and xylene; cellosolves such as methyl cellosolve, ethyl cellosolve and butyl cellosolve; methyl cellosolve acetate, ethyl cellosolve acetate and butyl cellosolve acetate. Cellosolve acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate and propylene glycol monoalkyl ether acetates such as propylene glycol monobutyl ether acetate; methyl methoxypropionate, ethyl methoxypropionate, methyl ethoxypropionate , Propionic acid esters such as ethyl ethoxypropionate; methyl lactate, ethyl lactate and milk Lactic acid esters such as butyl; diethylene glycols such as diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; acetates such as methyl acetate, ethyl acetate and butyl acetate; ethers such as dimethyl ether, diethyl ether, tetrahydrofuran and dioxane; acetone, methyl ethyl ketone , Ketones such as methyl butyl ketone and cyclohexanone; and alcohols such as methanol, ethanol, butanol, isopropyl alcohol, diacetone alcohol and benzyl alcohol, but are not limited thereto.
有機溶剤は、本発明の着色樹脂組成物に単独もしくは２種以上組み合わせて使用することができる。本発明の着色樹脂組成物における有機溶剤の使用量は、着色樹脂組成物の全固形分１００質量部に対して通常１００００質量部以下、好ましくは１００乃至１０００質量部である。 The organic solvent can be used alone or in combination of two or more in the colored resin composition of the present invention. The amount of the organic solvent used in the colored resin composition of the present invention is usually 10000 parts by mass or less, preferably 100 to 1000 parts by mass with respect to 100 parts by mass of the total solid content of the colored resin composition.
前記式（１）で表される化合物および任意に併用される色素類の樹脂成分への溶解性が低い場合は、分散剤や分散助剤等を併用して分散させてもよく、これら分散剤等としては色素に対して良好な吸着性を有する色素系分散剤や樹脂系分散剤、界面活性剤等が用いられる。色素系分散剤としては、色素のスルホン化物あるいはその金属塩を色素と混和する方法や置換アミノメチル誘導体を混和する方法等が一般に知られている。樹脂系分散剤としては、無極性のノニオン系のものもあるが、良好な顔料吸着性を付す酸価、アミン価等を有する高分子樹脂が一般的であり、アクリル樹脂、ポリウレタン樹脂、ポリカルボン酸、ポリアミド樹脂、ポリエステル樹脂等が挙げられる。樹脂分散剤の市販品としては、例えば、ＥＤ２１１（楠本化成製）、アジスパーＰＢ８２１（味の素ファインテクノ製）ソルスパース７１０００（アビシア製）、Ｄｉｓｐｅｒｂｙｋ−２００１（ビックケミー・ジャパン製）等が挙げられる。 When the solubility of the compound represented by the formula (1) and optionally used pigments in the resin component is low, a dispersant or a dispersion aid may be used in combination, and these dispersants may be used. For example, a pigment-based dispersant, a resin-based dispersant, a surfactant, or the like having good adsorptivity to the pigment is used. As the dye-based dispersant, a method of mixing a sulfonated dye or a metal salt thereof with a dye, a method of mixing a substituted aminomethyl derivative, and the like are generally known. Some resin-based dispersants are nonpolar nonionic, but polymer resins having an acid value, an amine value, and the like that give good pigment adsorbability are common, such as acrylic resins, polyurethane resins, and polycarboxylic acids. Examples include acids, polyamide resins, and polyester resins. Examples of commercially available resin dispersants include ED211 (manufactured by Enomoto Kasei), Ajisper PB821 (manufactured by Ajinomoto Fine Techno), Solsperse 71000 (manufactured by Avicia), Disperbyk-2001 (manufactured by Big Chemie Japan), and the like.
また、例えば酸性染料や塩基性染料を併用する場合は、該染料類に有機アミン化合物（例えばｎ−プロピルアミン、エチルヘキシルプロピオン酸アミン等）を反応させアミン塩染料に変性するか、又はそのスルホン酸基に同有機アミン化合物を反応させてスルホンアミド基を有する染料等に変性することにより有機溶剤に可溶性とした上で、有機溶剤と併用する方法が知られている。それらアミン変性した染料も本発明の着色樹脂組成物に併用可能である。アミン変性可能な染料としては、カラーインデックスで、例えば、ソルベントブルー２、３、４、５、６、２３、３５、３６、３７、３８、４３、４８、５８、５９、６７、７０、７８、９８、１０２、１０４；ベーシックブルー７；アシッドブルー８０、８３、９０；バイオレット染料としてソルベントバイオレット８、９；バイオレット４、５、１４；ベーシックバイオレット１０等が挙げられる。 For example, when an acid dye or a basic dye is used in combination, an organic amine compound (for example, n-propylamine, ethylhexylpropionic acid amine or the like) is reacted with the dyes to modify the amine salt dye or the sulfonic acid thereof. There is known a method in which the same organic amine compound is reacted with a group to be modified with a dye having a sulfonamide group to make it soluble in an organic solvent and then used in combination with the organic solvent. These amine-modified dyes can also be used in combination with the colored resin composition of the present invention. Examples of amine-modifiable dyes include color indexes such as Solvent Blue 2, 3, 4, 5, 6, 23, 35, 36, 37, 38, 43, 48, 58, 59, 67, 70, 78, 98, 102, 104; Basic Blue 7; Acid Blue 80, 83, 90; Examples of violet dyes include Solvent Violet 8, 9; Violet 4, 5, 14; Basic Violet 10 and the like.
本発明の着色樹脂組成物は、必須成分である式（１）で表される化合物、バインダー樹脂及び硬化剤と、任意成分である光重合開始剤及び／または硬化促進剤等を、ディゾルバーやホモミキサー等により混合撹拌して製造される。また、必要に応じて他の顔料や染料を加えることもできるが、顔料や溶解性の低い染料である場合は、適当な分散剤を用いてペイントシェーカー等の分散機により分散体を得て、着色樹脂組成物に加えて混合される。 The colored resin composition of the present invention comprises a compound represented by the formula (1), which is an essential component, a binder resin, a curing agent, a photopolymerization initiator and / or a curing accelerator, which are optional components, and the like. Produced by mixing and stirring with a mixer or the like. In addition, other pigments and dyes can be added as necessary, but if the pigment or dye has low solubility, a dispersion is obtained by a disperser such as a paint shaker using an appropriate dispersant, In addition to the colored resin composition, it is mixed.
本発明の着色樹脂組成物には、必要に応じて、さらに各種添加剤、例えば、充填剤、界面活性剤、熱重合防止剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤等を添加することができる。又、本発明の着色樹脂組成物は、その調製後に異物等を取り除くためフィルター等で精密濾過することも出来る。 If necessary, the colored resin composition of the present invention may further contain various additives such as fillers, surfactants, thermal polymerization inhibitors, adhesion promoters, antioxidants, ultraviolet absorbers, anti-aggregation agents, etc. Can be added. In addition, the colored resin composition of the present invention can be microfiltered with a filter or the like in order to remove foreign matters after the preparation.
本発明の着色樹脂組成物を用いた着色硬化膜（以下、単に「着色硬化膜」ともいう）の製造方法としては、主にフォトリソグラフィー法とインクジェット法が挙げられ、前者には光重合開始剤を含有する現像性に優れた感光性着色樹脂組成物が用いられ、後者は必ずしも光重合開始剤を必要とせず、硬化促進剤を含有する熱硬化性着色樹脂組成物が用いられる。 Examples of a method for producing a colored cured film (hereinafter also simply referred to as “colored cured film”) using the colored resin composition of the present invention include a photolithography method and an ink jet method, and the former includes a photopolymerization initiator. The photosensitive coloring resin composition excellent in developability containing is used, and the latter does not necessarily require a photopolymerization initiator, and a thermosetting coloring resin composition containing a curing accelerator is used.
また、例えば本発明の着色樹脂組成物をインクジェット法等で用いる場合は、光重合開始剤に熱重合開始剤を併用しても良い。熱重合開始剤としてはアゾ系化合物や有機過酸化物系のものがあるが、例えば２，２’−アゾビスイソブチロニトリル、２，２’−アゾビス（２，４−ジメチルバレロニトリル)、２，２’−アゾビス（２−メチルブチロニトリル）、過酸化ジ−ｔ−ブチル、ジベンゾイルパーオキシド、クミルパーオキシネオデカノエート等が挙げられる。 For example, when using the colored resin composition of this invention by the inkjet method etc., you may use a thermal polymerization initiator together with a photoinitiator. Examples of the thermal polymerization initiator include azo compounds and organic peroxides, such as 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), Examples include 2,2′-azobis (2-methylbutyronitrile), di-t-butyl peroxide, dibenzoyl peroxide, cumylperoxyneodecanoate, and the like.
尚、熱重合開始剤を併用する場合は、光重合開始剤と熱重合開始剤の合計が上記の光重合開始剤の含有量の範囲内となる量を用いればよい。 In addition, when using a thermal polymerization initiator together, what is necessary is just to use the quantity from which the sum total of a photoinitiator and a thermal polymerization initiator becomes in the range of content of said photoinitiator.
次に本発明の着色樹脂組成物から着色硬化膜を調製する方法について説明する。先ず、本発明の着色樹脂組成物をガラス基板、シリコン基板等の基板上に、スピンコート法、ロールコート法、スリットアンドスピン法、ダイコート法、バーコート法等の方法で、膜厚が０．１乃至２０μｍ、好ましくは０．５乃至５μｍになるように塗布する。次いで、必要に応じて、減圧チャンバー内で通常２３乃至１５０℃で１乃至６０分間、好ましくは６０乃至１２０℃で１乃至１０分間の乾燥条件で減圧乾燥を行い、さらにホットプレートもしくはクリーンオーブン等でプリベーク処理を行い製膜する。次に一般的なフォトリソグラフィー法により所定のマスクパターンを通して放射線（例えば電子線や紫外線が挙げられ、紫外線が好ましい。）を照射し、界面活性剤水溶液、アルカリ水溶液、又は界面活性剤とアルカリ剤の混合水溶液で現像する。現像方式としては、ディップ法、スプレー法、シャワー法、パドル法、超音波現像法等が挙げられ、これらのいずれかを組み合わせてもよい。現像により未照射部を取り除き、水でリンスした後、通常１３０乃至３００℃で１乃至１２０分間、好ましくは１５０乃至２５０℃で１乃至３０分間の条件でポストベーク処理を行い、本発明の着色硬化膜を得る。 Next, a method for preparing a colored cured film from the colored resin composition of the present invention will be described. First, the colored resin composition of the present invention is formed on a substrate such as a glass substrate or a silicon substrate by a method such as a spin coating method, a roll coating method, a slit and spin method, a die coating method, or a bar coating method. It is applied so as to be 1 to 20 μm, preferably 0.5 to 5 μm. Then, if necessary, it is dried under reduced pressure in a reduced pressure chamber under a drying condition of usually 23 to 150 ° C. for 1 to 60 minutes, preferably 60 to 120 ° C. for 1 to 10 minutes, and further in a hot plate or a clean oven. Pre-baking is performed to form a film. Next, a general photolithography method is used to irradiate radiation (for example, an electron beam or ultraviolet rays, preferably ultraviolet rays) through a predetermined mask pattern, and a surfactant aqueous solution, an alkaline aqueous solution, or a surfactant and an alkaline agent. Develop with mixed aqueous solution. Examples of the development method include a dipping method, a spray method, a shower method, a paddle method, an ultrasonic development method, and the like, and any of these methods may be combined. After removing unirradiated portions by development and rinsing with water, post-baking is usually performed at 130 to 300 ° C. for 1 to 120 minutes, preferably 150 to 250 ° C. for 1 to 30 minutes, and the color curing of the present invention. Get a membrane.
上記において、界面活性剤としてはポリオキシエチレンアルキルエーテル、ポリオキシアルキレンアルキルエーテル等を用いることができる。又、アルカリ剤としては、炭酸ナトリウム、炭酸カリウム、水酸化ナトリウム、水酸化カリウム、ジエタノールアミン、テトラメチルアンモニウムハイドロオキサイド等を用いることができる。本発明においては、アルカリ剤と界面活性剤の両方を含む水溶液を用いることが好ましい。現像は、通常１０乃至５０℃で３０乃至６００秒、好ましくは２０乃至４０℃で３０乃至１２０秒の処理条件で行われる。 In the above, polyoxyethylene alkyl ether, polyoxyalkylene alkyl ether, etc. can be used as the surfactant. Moreover, as an alkali agent, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, diethanolamine, tetramethylammonium hydroxide, etc. can be used. In the present invention, it is preferable to use an aqueous solution containing both an alkali agent and a surfactant. Development is usually carried out at 10 to 50 ° C. for 30 to 600 seconds, preferably at 20 to 40 ° C. for 30 to 120 seconds.
本発明の着色硬化膜は、液晶表示装置、有機ＥＬディスプレイ、あるいはデジタルカメラ等に使用される固体撮像素子等に好適なカラーフィルターとして有用であり、該カラーフィルターは前記のようにして調製された本発明の着色硬化膜からなる緑色画素である。 The colored cured film of the present invention is useful as a color filter suitable for a solid-state imaging device used in a liquid crystal display device, an organic EL display, a digital camera or the like, and the color filter was prepared as described above. It is a green pixel which consists of a colored cured film of this invention.
本発明の液晶表示装置は、例えば、バックライト、偏光フィルム、表示電極、液晶、配向膜、共通電極、本発明のカラーフィルター、偏光フィルム等がこの順に積層した構造で作製される。また、有機ＥＬディスプレイについては多層の有機発光素子の上もしくは下のどちらか一方にカラーフィルターを形成して作製される。固体撮像素子については、例えば、転送電極、フォトダイオードを設けたシリコンウエーハーの上に、本発明のカラーフィルター層を設け、ついでマイクロレンズを積層することにより作製される。 The liquid crystal display device of the present invention is produced, for example, with a structure in which a backlight, a polarizing film, a display electrode, a liquid crystal, an alignment film, a common electrode, a color filter of the present invention, a polarizing film, and the like are laminated in this order. The organic EL display is manufactured by forming a color filter on either the upper or lower side of the multilayer organic light emitting element. The solid-state imaging device is manufactured, for example, by providing the color filter layer of the present invention on a silicon wafer provided with transfer electrodes and photodiodes, and then laminating microlenses.
以下に本発明を実施例によりさらに具体的に説明するが、本発明は実施例に限定されるものではない。なお、特別の記載のない限り、本文中「部」及び「％」とあるのは質量基準であり、また反応温度は内温である。合成したメチン化合物のうち、λｍａｘ（最大吸収波長）を測定したものについては、特に断りのない限りジメチルスルホキシド中、紫外可視分光光度計ＵＶ−３１５０（島津製作所社製）での測定値を記載した。 Examples The present invention will be described more specifically with reference to examples. However, the present invention is not limited to the examples. Unless otherwise specified, “part” and “%” in the text are based on mass, and the reaction temperature is the internal temperature. Among the synthesized methine compounds, those measured for λmax (maximum absorption wavelength) are described in dimethyl sulfoxide unless otherwise specified, and measured values with UV-visible spectrophotometer UV-3150 (manufactured by Shimadzu Corporation). .
実施例１（上記化合物Ｎｏ．４で表されるメチン化合物の合成）
（工程１−１）
硫酸３３部中に１０℃以下で３０％発煙硫酸７８部を添加した。その後下記式（６）で表される２−メチルインドリン１５部を１０℃以下で添加し、１０℃で２時間撹拌した。得られた溶液を水１３０部に注ぎ、３０分間撹拌した。析出した固体をろ過分取し、水洗後に乾燥することにより、下記式（７）で表されるアニリン化合物１８部を得た。
Example 1 (Synthesis of methine compound represented by Compound No. 4)
(Step 1-1)
To 33 parts of sulfuric acid, 78 parts of 30% fuming sulfuric acid at 10 ° C. or less was added. Thereafter, 15 parts of 2-methylindoline represented by the following formula (6) was added at 10 ° C. or lower and stirred at 10 ° C. for 2 hours. The resulting solution was poured into 130 parts of water and stirred for 30 minutes. The precipitated solid was collected by filtration, washed with water and dried to obtain 18 parts of an aniline compound represented by the following formula (7).
（工程１−２）
メタノール５７部と水６０部の混合溶液中に、下記式（８）で表されるアルデヒド中間体１４．１部、上記式（７）で表されるアニリン化合物１５．０部を添加し、６０℃で２時間撹拌した。得られた溶液を室温まで冷却した後、水を加え、析出した固体をろ過分取し、水洗後に乾燥することにより、上記化合物Ｎｏ．４で表される本発明のメチン化合物１５部を得た。該メチン系化合物の極大吸収波長は４２４ｎｍ（ジメチルスルホキシド）であった。
(Step 1-2)
In a mixed solution of 57 parts of methanol and 60 parts of water, 14.1 parts of an aldehyde intermediate represented by the following formula (8) and 15.0 parts of an aniline compound represented by the above formula (7) were added, Stir at 0 ° C. for 2 hours. After cooling the obtained solution to room temperature, water was added, the precipitated solid was collected by filtration, washed with water and dried, and then the above compound No. 1 was obtained. 15 parts of the methine compound of the invention represented by 4 were obtained. The maximum absorption wavelength of the methine compound was 424 nm (dimethyl sulfoxide).
実施例２（上記化合物Ｎｏ．１で表されるメチン化合物の合成）
メタノール１０部と水１０部の混合溶液中に、下記式（９）で表されるアルデヒド中間体０．７１部、上記式（７）で表されるアニリン化合物 ０．７０部及び３５％塩酸０．１部を添加し、５０℃で２時間撹拌した。得られた溶液を室温まで冷却した後、水を加え、析出した固体をろ過分取し、水洗後に乾燥することにより、上記化合物Ｎｏ．１で表される本発明のメチン化合物０．８部を得た。該メチン系化合物の極大吸収波長は４２９ｎｍ（ジメチルスルホキシド）であった。
Example 2 (Synthesis of methine compound represented by Compound No. 1)
In a mixed solution of 10 parts of methanol and 10 parts of water, 0.71 part of an aldehyde intermediate represented by the following formula (9), 0.70 part of an aniline compound represented by the above formula (7) and 0% of 35% hydrochloric acid .1 part was added and stirred at 50 ° C. for 2 hours. After cooling the obtained solution to room temperature, water was added, the precipitated solid was collected by filtration, washed with water and dried, and then the above compound No. 1 was obtained. 0.8 parts of the methine compound of the present invention represented by 1 was obtained. The maximum absorption wavelength of the methine compound was 429 nm (dimethyl sulfoxide).
合成例１（バインダー樹脂（共重合体（Ａ））の合成）
５００ｍｌの四つ口フラスコにメチルエチルケトン１６０部、メタクリル酸１０部、ベンジルメタクリレート３３部及びα，α’−アゾビス（イソブチロニトリル）１部を仕込み、攪拌しながら３０分間窒素ガスをフラスコ内に流入した。その後、８０℃まで昇温し、８０乃至８５℃でそのまま４時間攪拌した。反応終了後、室温まで冷却し、無色透明で均一な共重合体溶液を得た。これをイソプロピルアルコールと水の１：１混合溶液中で沈殿させ、濾過し、固形分を取り出し、乾燥し、共重合体（Ａ）を得た。得られた共重合体（Ａ）のポリスチレン換算重量平均分子量は１８０００であり、酸価は１５２（ｍｇＫＯＨ／ｇ）であった。
Synthesis Example 1 (Synthesis of binder resin (copolymer (A)))
A 500 ml four-necked flask is charged with 160 parts of methyl ethyl ketone, 10 parts of methacrylic acid, 33 parts of benzyl methacrylate and 1 part of α, α'-azobis (isobutyronitrile), and nitrogen gas is allowed to flow into the flask for 30 minutes while stirring. did. Then, it heated up to 80 degreeC and stirred for 4 hours as it was at 80 to 85 degreeC. After completion of the reaction, the reaction mixture was cooled to room temperature to obtain a colorless, transparent and uniform copolymer solution. This was precipitated in a 1: 1 mixed solution of isopropyl alcohol and water, filtered, and the solid content was taken out and dried to obtain a copolymer (A). The obtained copolymer (A) had a polystyrene equivalent weight average molecular weight of 18000 and an acid value of 152 (mgKOH / g).
実施例３（本発明の着色樹脂組成物１及び染料着色体１の作製）
Ｃ．Ｉ．ピグメントグリーン５９／実施例１で得られた上記化合物Ｎｏ．４表される化合物／Ｄｉｓｐｅｒｂｙｋ−２００１(ビックケミー・ジャパン製)／ＰＧＭＥＡ（プロピレングリコールモノメチルエーテルアセテート）／エトキシプロパノール／合成例１で得られたバインダー樹脂＝０．０６部／０．１３部／０．６２部／１９．０３部／１．２３部／３．９３部の組成比で混合した後、０．１ｍｍジルコニアビーズ１００部を添加し、ペイントシェーカーで９時間処理を行った。ビーズをろ過して除き、得られた着色組成物１をガラス基板にスピンコートし、９０℃で２．５分間乾燥した。その後、２３０℃で３０分間乾燥し、染料着色体１を作製した。
Example 3 (Preparation of colored resin composition 1 and dyed colored body 1 of the present invention)
C. I. Pigment Green 59 / Compound No. 1 obtained in Example 1 above. 4 Compound / Disperbyk-2001 (manufactured by Big Chemie Japan) / PGMEA (propylene glycol monomethyl ether acetate) / ethoxypropanol / binder resin obtained in Synthesis Example 1 = 0.06 parts / 0.13 parts / 0. After mixing at a composition ratio of 62 parts / 19.03 parts / 1.23 parts / 3.93 parts, 100 parts of 0.1 mm zirconia beads were added, and the mixture was treated with a paint shaker for 9 hours. The beads were removed by filtration, and the obtained colored composition 1 was spin-coated on a glass substrate and dried at 90 ° C. for 2.5 minutes. Then, it dried at 230 degreeC for 30 minute (s), and the dye coloring body 1 was produced.
実施例４（本発明の着色樹脂組成物２及び染料着色体２の作製）
実施例１で得られた上記化合物Ｎｏ．４で表される化合物を実施例２で得られた上記化合物Ｎｏ．１で表される化合物に変更したこと以外は実施例３と同様にして本発明の染料着色体２を得た。
Example 4 (Preparation of colored resin composition 2 and dyed colored body 2 of the present invention)
The above compound No. 1 obtained in Example 1 was used. 4 was changed to the compound No. 4 obtained in Example 2. Except having changed into the compound represented by 1, it carried out similarly to Example 3, and obtained the dye coloring body 2 of this invention.
比較例１（比較用染料着色体１の作製）
実施例１で得られた上記化合物Ｎｏ．４で表される化合物を特許文献１に記載の下記式（１０）で表される化合物に変更したこと以外は実施例３と同様にして比較用染料着色体１を得た。
Comparative Example 1 (Preparation of Comparative Dye Colored Product 1)
The above compound No. 1 obtained in Example 1 was used. A comparative dye-colored product 1 was obtained in the same manner as in Example 3 except that the compound represented by 4 was changed to the compound represented by the following formula (10) described in Patent Document 1.
比較例２（比較用染料着色体２の作製）
実施例１で得られた上記化合物Ｎｏ．４で表される化合物を特許文献３に記載の下記式（１１）で表される化合物に変更したこと以外は実施例３と同様にして比較用染料着色体２を得た。
Comparative Example 2 (Preparation of Comparative Dye Colored Product 2)
The above compound No. 1 obtained in Example 1 was used. A comparative dye-colored product 2 was obtained in the same manner as in Example 3 except that the compound represented by 4 was changed to the compound represented by the following formula (11) described in Patent Document 3.
（コントラスト評価）
上記評価用基板を用いて、コントラスト計（壷坂電機製ＣＴ−１）により、２枚の偏光板の平行時の輝度値（ｃｄ／ｃｍ２）と直交時の輝度値（ｃｄ／ｃｍ２）の比（平行時の輝度値/直交時の輝度値）から、コントラストを算出した。コントラスト比が３０００以上の場合は◎、２０００以上３０００未満の場合は○、２０００未満の場合を×として評価した。結果を表１に示した。
(Contrast evaluation)
Using the evaluation substrate, the contrast meter (fountain Saka Electric Ltd. CT-1), the luminance value at two parallel polarizing plates (cd / cm 2) and orthogonal when the luminance value (cd / cm 2) The contrast was calculated from the ratio (brightness value in parallel / brightness value in orthogonal). When the contrast ratio was 3000 or more, ◎, when 2000 or more and less than 3000, ○, and when less than 2000, × were evaluated. The results are shown in Table 1.
表１ コントラストの評価結果
コントラスト比
染料着色体１ ◎
染料着色体２ ◎
比較用染料着色体１ ×
比較用染料着色体２ ×
Table 1 Contrast evaluation results
Contrast ratio Dye coloring 1
Dye coloring body 2 ◎
Dye coloring for comparison 1 ×
Dye coloring for comparison 2 ×
表１の結果から、本発明の着色樹脂組成物を用いて得られた染料着色体１及び２は、比較用染料着色体１乃至２に比べて良好なコントラスト比を示した。 From the results of Table 1, dye colored bodies 1 and 2 obtained using the colored resin composition of the present invention showed a better contrast ratio than the comparative dye colored bodies 1 to 2.
以上より、本願発明のメチン化合物を含有する着色樹脂組成物を用いて得られた着色硬化膜は、従来の顔料分散型の着色樹脂組成物を用いて得られた着色硬化膜に比べて高コントラストのカラーフィルターとして有用であった。 From the above, the colored cured film obtained using the colored resin composition containing the methine compound of the present invention has a higher contrast than the colored cured film obtained using the conventional pigment-dispersed colored resin composition. It was useful as a color filter.
本発明のメチン化合物を含有する着色樹脂組成物を用いることにより、コントラストに優れた着色硬化膜（カラーフィルター）の緑色画素を提供することができる。
By using the colored resin composition containing the methine compound of the present invention, a green pixel of a colored cured film (color filter) excellent in contrast can be provided.
Claims (12)
The manufacturing method of a colored cured film including the process of patterning the colored resin composition as described in any one of Claims 5 thru | or 8.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20200106450A (en) | 2019-03-04 | 2020-09-14 | 닛뽄 가야쿠 가부시키가이샤 | Colored composition, color filter using same, and use thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20200106450A (en) | 2019-03-04 | 2020-09-14 | 닛뽄 가야쿠 가부시키가이샤 | Colored composition, color filter using same, and use thereof |
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