JP2014059538A - Colored resin composition - Google Patents
Colored resin composition Download PDFInfo
- Publication number
- JP2014059538A JP2014059538A JP2012262167A JP2012262167A JP2014059538A JP 2014059538 A JP2014059538 A JP 2014059538A JP 2012262167 A JP2012262167 A JP 2012262167A JP 2012262167 A JP2012262167 A JP 2012262167A JP 2014059538 A JP2014059538 A JP 2014059538A
- Authority
- JP
- Japan
- Prior art keywords
- group
- resin composition
- color filter
- colored resin
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000011342 resin composition Substances 0.000 title claims abstract description 101
- -1 xanthene compound Chemical class 0.000 claims abstract description 101
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 239000011230 binding agent Substances 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000000049 pigment Substances 0.000 claims description 48
- 125000003277 amino group Chemical group 0.000 claims description 12
- 239000004973 liquid crystal related substance Substances 0.000 claims description 11
- 125000004093 cyano group Chemical class *C#N 0.000 claims description 10
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 9
- 238000003384 imaging method Methods 0.000 claims description 8
- 125000002252 acyl group Chemical class 0.000 claims description 6
- 125000003368 amide group Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 6
- 125000000565 sulfonamide group Chemical class 0.000 claims description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229940067265 pigment yellow 138 Drugs 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- 239000003999 initiator Substances 0.000 abstract description 12
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 238000000034 method Methods 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 20
- 239000000178 monomer Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- 229920001577 copolymer Polymers 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000003505 polymerization initiator Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002270 dispersing agent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000001054 red pigment Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 4
- 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000007513 acids Chemical class 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 class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- 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
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 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
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-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
- 238000005160 1H NMR spectroscopy Methods 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
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-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
- 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
- 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
- 239000002202 Polyethylene glycol Substances 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
- 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
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000000981 basic dye 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000010438 heat treatment Methods 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
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 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
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012860 organic pigment 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
- 238000000059 patterning Methods 0.000 description 2
- 230000000704 physical effect Effects 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
- 238000001556 precipitation Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 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
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 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
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
本発明は、カラーフィルターの赤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 colored resin composition used when forming a red pixel of a color filter, a color filter formed using the colored resin composition, a liquid crystal display device formed using the color filter, and imaging The present invention relates to an electronic display device such as an element (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色純度、彩度、明度およびコントラスト等の特性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 characteristics such as color purity, saturation, brightness and contrast required for the 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、その一方で、テレビ向け等の長期信頼性を必要とされる表示体用途には優れた耐光性や耐熱性が必要とされるが、染料は顔料よりも耐性が劣ることが一般的である。例えば、特許文献1はキサンテン化合物と樹脂とを組み合わせた赤色カラーフィルターに関するものであるが、同文献にはカラーフィルターの耐性(耐熱性)については何ら記載されていない。特許文献2、3は、色特性に優れるキサンテン化合物を含有する着色感光性樹脂組成物に関するものであるが、これらの文献で検討しているのは青色カラーフィルターについてのみであり、しかもカラーフィルターの耐性(耐熱性)については何ら記載されていない。即ち、液晶表示装置や固体撮像素子の分野において求められている、信頼性に優れた耐性の高い鮮明な赤色カラーフィルターは、ほとんど実用化されていないのが現状である。 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, on the other hand, for display applications that require long-term reliability for TVs and the like, excellent light resistance and heat resistance are required, but dyes are generally less resistant than pigments. is there. For example, Patent Document 1 relates to a red color filter in which a xanthene compound and a resin are combined, but the document does not describe any resistance (heat resistance) of the color filter. Patent Documents 2 and 3 relate to a colored photosensitive resin composition containing a xanthene compound having excellent color characteristics. However, these documents discuss only the blue color filter and the color filter. There is no description of resistance (heat resistance). That is, the current state is that a vivid red color filter having excellent reliability and high durability, which is required in the field of liquid crystal display devices and solid-state imaging devices, has hardly been put into practical use.
本発明は、明度や耐熱性に優れた高品位で高信頼の赤色カラーフィルターを製造することができる着色樹脂組成物、およびそれを用いて製造されたカラーフィルターの提供を目的とする。 An object of the present invention is to provide a colored resin composition capable of producing a high-quality and highly reliable red color filter excellent in lightness and heat resistance, and a color filter produced using the same.
本発明者は前記課題を解決すべく鋭意研究を行った結果、カラーフィルター画素に、色素として、少なくとも下記式(1)で表されるキサンテン骨格含有化合物(以下キサンテン骨格含有化合物をキサンテン化合物という)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。 As a result of intensive studies to solve the above problems, the present inventor has at least a xanthene skeleton-containing compound represented by the following formula (1) as a pigment in the color filter pixel (hereinafter referred to as a xanthene skeleton-containing compound). The present inventors have found that the above-described problems can be solved by using a colored resin composition containing the present invention, and have completed the present invention.
即ち、本発明は、
(1)下記式(1)
That is, the present invention
(1) The following formula (1)
(式(1)中、R1〜R4は、それぞれ独立に水素原子または炭素数1〜12のアルキル基を表し、該炭素数1〜12のアルキル基は、ハロゲン原子、ヒドロキシ基、アルコキシ基、アルコキシアルコキシ基、アリール基、アリールオキシ基、アシルオキシ基、アミノ基、アルキル置換アミノ基、シアノ基、ニトロ基、カルボキシル基、カルボンアミド基、アルコキシカルボニル基、アシル基、アミド基、スルホンアミド基またはスルホン酸基を置換基として有していてもよい。)
で表されるキサンテン化合物、バインダー樹脂、有機溶剤及び硬化剤、並びに光重合開始剤及び/または硬化促進剤を含有するカラーフィルター用着色樹脂組成物、
(2)式(1)におけるR1〜R4が、それぞれ独立にハロゲン原子、ヒドロキシ基、アルコキシ基、アルコキシアルコキシ基、アミノ基、アルキル置換アミノ基、シアノ基、ニトロ基、カルボキシル基、アシル基、アミド基、カルボアミド基またはスルホンアミド基を置換基として有していてもよい炭素数1〜6のアルキル基である上記(1)に記載の着色樹脂組成物、
(3)更に、顔料を含有する上記(1)または(2)に記載の着色樹脂組成物、
(4)顔料が、C.I.ピグメントレッド177、C.I.ピグメントレッド242、C.I.ピグメントレッド254、C.I.ピグメントイエロー150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上記(3)に記載の着色樹脂組成物、
(5)上記(1)乃至(4)のいずれか一項に記載の着色樹脂組成物を用い、パターニングされてなるカラーフィルター用着色硬化膜、
(6)上記(5)に記載のカラーフィルター用着色硬化膜からなるカラーフィルター、
(7)上記(6)に記載のカラーフィルターを装着した液晶表示装置、
(8)上記(6)に記載のカラーフィルターを装着した有機ELディスプレイ、
(9)上記(6)に記載のカラーフィルターを装着した固体撮像素子、
に関する。
(In Formula (1), R < 1 > -R < 4 > represents a hydrogen atom or a C1-C12 alkyl group each independently, and this C1-C12 alkyl group is a halogen atom, a hydroxy group, and an alkoxy group. , Alkoxyalkoxy group, aryl group, aryloxy group, acyloxy group, amino group, alkyl-substituted amino group, cyano group, nitro group, carboxyl group, carbonamido group, alkoxycarbonyl group, acyl group, amide group, sulfonamide group or (You may have a sulfonic acid group as a substituent.)
A colored resin composition for a color filter containing a xanthene compound represented by: a binder resin, an organic solvent and a curing agent, and a photopolymerization initiator and / or a curing accelerator,
(2) R 1 to R 4 in formula (1) are each independently a halogen atom, hydroxy group, alkoxy group, alkoxyalkoxy group, amino group, alkyl-substituted amino group, cyano group, nitro group, carboxyl group, acyl group The colored resin composition according to the above (1), which is an alkyl group having 1 to 6 carbon atoms which may have an amide group, carboamide group or sulfonamide group as a substituent,
(3) The colored resin composition according to (1) or (2), further containing a pigment,
(4) The pigment is C.I. I. Pigment red 177, C.I. I. Pigment red 242, C.I. I. Pigment red 254, C.I. I. Pigment yellow 150 and C.I. I. The colored resin composition according to the above (3), which is one or more selected from the group consisting of CI Pigment Yellow 138;
(5) A colored cured film for a color filter that is patterned using the colored resin composition according to any one of (1) to (4) above,
(6) A color filter comprising the colored cured film for a color filter according to (5) above,
(7) A liquid crystal display device equipped with the color filter according to (6) above,
(8) An organic EL display equipped with the color filter according to (6) above,
(9) A solid-state imaging device equipped with the color filter according to (6) above,
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、明度や耐熱性に優れた高品位で信頼性の高いカラーフィルターの赤色画素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, it is possible to provide a red pixel of a high-quality and highly reliable color filter excellent in lightness and heat resistance.
本発明のカラーフィルター用着色樹脂組成物(以下、単に「着色樹脂組成物」ともいう)は、前記式(1)で表されるキサンテン化合物を含有する。 The colored resin composition for color filters of the present invention (hereinafter also simply referred to as “colored resin composition”) contains a xanthene compound represented by the formula (1).
式(1)中、R1〜R4は、それぞれ独立に水素原子または炭素数1〜12のアルキル基を表し、該アルキル基は炭素数1〜12のアルキル基であれば直鎖状、分岐鎖状または環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。 In formula (1), R 1 to R 4 each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and the alkyl group is linear or branched if the alkyl group is an alkyl group having 1 to 12 carbon atoms. It is not limited to either chain or ring. The alkyl group may have a substituent.
炭素数1〜12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、t−ブチル基、n−ペンチル基、iso−ペンチル基、neo−ペンチル基、t−ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、イソプロピル基、シクロペンチル基、シクロヘキシル基、ビニル基、アリル基、プロペニル基、ペンチニル基、ブテニル基、ヘキセニル基、ヘキサジエニル基、イソプロペニル、イソへキセニル基、シクロへキセニル基、シクロペンタジエニル基、エチニル基、プロピニル基、へキシニル基、イソへキシニル基、シクロへキシニル基等が挙げられる。 Specific examples of the alkyl group having 1 to 12 carbon atoms include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, t-pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, isopropyl group, cyclopentyl group, cyclohexyl group, Vinyl group, allyl group, propenyl group, pentynyl group, butenyl group, hexenyl group, hexadienyl group, isopropenyl, isohexenyl group, cyclohexenyl group, cyclopentadienyl group, ethynyl group, propynyl group, hexynyl group, An isohexynyl group, a cyclohexynyl group, etc. are mentioned.
式(1)におけるR1〜R4としては、炭素数1〜10のアルキル基が好ましく、炭素数1〜8のアルキル基がより好ましく、炭素数1〜6のアルキル基が更に好ましく、炭素数1〜4のアルキル基が最も好ましい。 As R < 1 > -R < 4 > in Formula (1), a C1-C10 alkyl group is preferable, A C1-C8 alkyl group is more preferable, A C1-C6 alkyl group is still more preferable, Carbon number Most preferred are 1-4 alkyl groups.
式(1)のR1〜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、ヨウ素原子)、ヒドロキシ基、アルコキシ基(例えば、メトキシ基、エトキシ基、イソブトキシ基等)、アルコキシアルコキシ基(例えば、メトキシエトキシ基、エトキシエトキシ基、プロポキシエトキシ基等)、アリール基(例えば、フェニル基、ナフチル基等でこれらのアリール基はさらに置換基を有しても良い)、アリールオキシ基(例えば、フェノキシ等)、アシルオキシ基(例えば、アセチルオキシ基、ブチリルオキシ基、ヘキシリルオキシ基、ベンゾイルオキシ基等で、これらのアリールオキシ基はさらに置換基を有しても良い)、アミノ基、アルキル置換アミノ基(例えば、メチルアミノ基、エチルアミノ基、プロピルアミノ基、ジメチルアミノ基等)、シアノ基、ニトロ基、カルボキシル基、カルボアミド基、アルコキシカルボニル基(例えば、メトキシカルボニル基、エトキシカルボニル基等)、アシル基、アミド基(例えば、アセトアミド基等)、スルホンアミド基(例えば、メタンスルホンアミド基、エタンスルホンアミド基、プロパンスルホンアミド基等)、およびスルホン酸が挙げられる。 Examples of the substituent that the alkyl group represented by R 1 to R 4 in Formula (1) may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), a hydroxy group, and an alkoxy group (for example, Methoxy group, ethoxy group, isobutoxy group etc.), alkoxyalkoxy group (eg methoxyethoxy group, ethoxyethoxy group, propoxyethoxy group etc.), aryl group (eg phenyl group, naphthyl group etc.) Which may have a substituent), an aryloxy group (for example, phenoxy), an acyloxy group (for example, an acetyloxy group, a butyryloxy group, a hexyloxy group, a benzoyloxy group, etc.). May have a substituent), an amino group, an alkyl-substituted amino group (for example, a methylamino group) Ethylamino group, propylamino group, dimethylamino group, etc.), cyano group, nitro group, carboxyl group, carboamido group, alkoxycarbonyl group (eg, methoxycarbonyl group, ethoxycarbonyl group, etc.), acyl group, amide group (eg, Acetamido group, etc.), sulfonamido groups (eg methanesulfonamido group, ethanesulfonamido group, propanesulfonamido group, etc.), and sulfonic acid.
式(1)のR1〜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、ハロゲン原子、ヒドロキシ基、アルコキシ基、アルコキシアルコキシ基、アミノ基、アルキル置換アミノ基、シアノ基、ニトロ基、カルボキシル基、アシル基、アミド基、カルボアミド基またはスルホンアミド基であることが好ましく、ヒドロキシ基またはアルコキシ基であることがより好ましく、アルコキシ基であることが更に好ましく、炭素数1〜6のアルコキシ基であることが特に好ましく、炭素数1〜4のアルコキシ基であることが最も好ましい。また、該置換基の数は、1〜2個であることが好ましく、1個であることがより好ましく、該置換基の置換位置は、アルキル基中のR1及びR2、並びにR3及びR4が結合している窒素原子から最も離れた炭素原子であることが好ましい。 As the substituent that the alkyl group represented by R 1 to R 4 in Formula (1) may have, a halogen atom, a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an amino group, an alkyl-substituted amino group, a cyano group, It is preferably a nitro group, a carboxyl group, an acyl group, an amide group, a carboamide group or a sulfonamide group, more preferably a hydroxy group or an alkoxy group, still more preferably an alkoxy group, and 1 to 6 carbon atoms. Are particularly preferable, and an alkoxy group having 1 to 4 carbon atoms is most preferable. The number of the substituents is preferably 1 to 2, more preferably 1, and the substitution positions of the substituents are R 1 and R 2 in the alkyl group, and R 3 and R 4 is preferably the carbon atom farthest from the nitrogen atom to which R 4 is bonded.
本発明の着色樹脂組成物に用いられる式(1)で表されるキサンテン化合物としては、下記(i)、(ii)または(iii)の何れかの条件を満たす化合物が好ましい。
(i)式(1)におけるR1〜R4が、無置換の炭素数1〜6のアルキル基である化合物、より好ましくは無置換の炭素数1〜4のアルキル基である化合物。
(ii)式(1)におけるR1〜R4が、ヒドロキシ基を置換基として有する炭素数1〜6のアルキル基である化合物、より好ましくはヒドロキシ基を置換基として有する炭素数1〜4のアルキル基である化合物。
(iii)式(1)におけるR1〜R4が、炭素数1〜6、好ましくは炭素数1〜4のアルコキシ基を置換基として有する炭素数1〜6のアルキル基である化合物、より好ましくは炭素数1〜6、好ましくは炭素数1〜4のアルコキシ基を置換基として有する炭素数1〜4のアルキル基である化合物。
上記条件(i)、(ii)または(iii)の何れかの条件を満たす好ましい化合物の中でも、R1〜R4が全て同一である化合物がより好ましく、また、上記(ii)または(iii)の条件を満たす化合物の中でも、置換基の数が1個である化合物がより好ましく、1個の置換基が、アルキル基中の、R1及びR2、並びにR3及びR4が結合している窒素原子から最も離れた炭素原子に置換している化合物が更に好ましい。
上記条件(i)、(ii)または(iii)の条件を満たす化合物の中でも、(i)または(iii)の条件を満たす化合物が特に好ましい。
As the xanthene compound represented by the formula (1) used in the colored resin composition of the present invention, a compound that satisfies any of the following conditions (i), (ii), or (iii) is preferable.
(I) A compound in which R 1 to R 4 in formula (1) are an unsubstituted alkyl group having 1 to 6 carbon atoms, more preferably a compound that is an unsubstituted alkyl group having 1 to 4 carbon atoms.
(Ii) R 1 to R 4 in formula (1) are compounds having 1 to 6 carbon atoms having a hydroxy group as a substituent, more preferably 1 to 4 carbon atoms having a hydroxy group as a substituent. A compound that is an alkyl group.
(Iii) Compounds in which R 1 to R 4 in formula (1) are an alkyl group having 1 to 6 carbon atoms, preferably an alkoxy group having 1 to 4 carbon atoms as a substituent, more preferably Is a compound having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms having an alkoxy group having 1 to 4 carbon atoms as a substituent.
Among preferable compounds satisfying any one of the above conditions (i), (ii), and (iii), compounds in which R 1 to R 4 are all the same are more preferable, and the above (ii) or (iii) Among the compounds satisfying the above condition, a compound having one substituent is more preferable, and one substituent is bonded to R 1 and R 2 and R 3 and R 4 in the alkyl group. Further preferred is a compound substituted with a carbon atom farthest from the nitrogen atom.
Of the compounds satisfying the condition (i), (ii) or (iii), compounds satisfying the condition (i) or (iii) are particularly preferable.
本発明における式(1)で表されるキサンテン化合物は、後記式(100)で表されるフルオラン化合物に、式(1)のR1〜R4に対応する水素原子及び/またはアルキル基を有するアミン化合物を反応させることにより得ることができる。 The xanthene compound represented by the formula (1) in the present invention has a hydrogen atom and / or an alkyl group corresponding to R 1 to R 4 in the formula (1) in the fluorane compound represented by the following formula (100). It can be obtained by reacting an amine compound.
本発明のカラーフィルター用着色樹脂組成物における式(1)で表されるキサンテン化合物の含有量は、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、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0.01〜70質量部、好ましくは0.05〜30質量部、より好ましくは0.1〜20質量部、特に好ましくは0.5〜10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恐れがある。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恐れがある。 The content of the xanthene compound represented by formula (1) in the colored resin composition for color filters 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) The total amount of solids other than the organic solvent, such as a curing agent, etc., is used interchangeably hereinafter.) Usually 0.01 to 70 parts by weight, preferably 0.05 to 30 parts by weight, with respect to 100 parts by weight. More preferably, it is 0.1-20 mass parts, Most preferably, it is 0.5-10 mass parts. When the content is larger than this range, precipitation or aggregation may occur, or adhesion with the substrate may be lowered 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.
本発明のカラーフィルター用着色樹脂組成物が含有するバインダー樹脂は、式(1)で表されるキサンテン化合物および必要により添加される顔料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、バインダー樹脂が光重合開始剤、光重合性モノマー等との十分な硬化特性を有しているものが望ましく、また、バインダー樹脂が式(1)で表されるキサンテン化合物等の色材化合物、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 for a color filter of the present invention includes a dispersant and a dispersion aid for dispersion stability during dispersion of the xanthene compound represented by formula (1) and a pigment added as necessary. However, when the colored resin composition is used in a photolithography method, it is desirable that the colored resin composition is soluble in an alkaline developer used in a development processing step when producing a color filter. In order to form a fine pattern, it is desirable that the binder resin has sufficient curing characteristics with a photopolymerization initiator, a photopolymerizable monomer, etc., and the binder resin is represented by the formula (1). Good compatibility with constituent materials such as colorant compounds such as xanthene compounds, photopolymerization initiators, photopolymerizable monomers, pigment dispersions, and the like so long as the colored resin composition does not cause precipitation or aggregation Don't be. 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, octoxypolyethylene 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)を合成する際には、重合開始剤を使用する。ここで共重合体の合成に使用し得る重合開始剤の具体例としては、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、0.01〜25質量部である。また、共重合体を合成する際には、有機溶剤を使用するのが好ましいが、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。バインダー樹脂の合成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。
共重合体を合成する際の反応温度は50〜120℃であることが好ましく、特に好ましくは80〜100℃である。また、反応時間は1〜60時間であることが好ましく、より好ましくは3〜20時間である。共重合体の好ましい酸価は10〜300(mgKOH/g)であり、好ましい水酸基価は10〜200(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2000〜400000が好ましく、3000〜100000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。
When synthesizing the binder resin (copolymer), a polymerization initiator is used. Specific examples of the polymerization initiator that can be used for the synthesis of the copolymer here include α, α′-azobis (isobutyronitrile), 2,2′-azobis (2-methylbutyronitrile), t- Examples thereof include butyl peroctoate and di-t-butyl peroxide benzoylmethyl ethyl ketone peroxide. The usage-amount of a polymerization initiator is 0.01-25 mass parts with respect to 100 mass parts of all the monomers used for the synthesis | combination of a copolymer. In synthesizing the copolymer, it is preferable to use an organic solvent. However, a solvent having sufficient dissolving power for a monofunctional monomer or a polymerization initiator used for the synthesis is used. As an organic solvent which can be used for the synthesis | combination of binder resin, the thing similar to the organic solvent which the colored resin composition of this invention mentioned later contains is mentioned.
The reaction temperature for synthesizing the copolymer is preferably 50 to 120 ° C, particularly preferably 80 to 100 ° C. Moreover, it is preferable that reaction time is 1 to 60 hours, More preferably, it is 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. As for the weight average molecular weight (Mw) of a copolymer, 2000-400000 are preferable and 3000-100000 are more preferable. When the weight average molecular weight is 2000 or less, or 400000 or more, sensitivity, developability and the like are lowered.
In addition, in this invention, an acid value means the value measured by the method based on JIS K-2501 and hydroxyl value JIS K-1557, and a weight average molecular weight is GPC (gel permeation chromatography). It means a value calculated in terms of polystyrene based on the measurement result.
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) Manufactured), UXE-3000 (manufactured by Nippon Kayaku), ZGA-287H (manufactured by Nippon Kayaku), TCR-1338H (manufactured by Nippon Kayaku), ZXR-1722H (manufactured by Nippon Kayaku), ZFR-1401H (manufactured by 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、0.5〜99質量部、好ましくは5〜50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. Content of the binder resin in the colored resin composition of this invention is 0.5-99 mass parts normally with respect to 100 mass parts of total solids of a colored resin composition, Preferably it is 5-50 mass parts. 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.
本発明のカラーフィルター用着色樹脂組成物が含有する有機溶剤は、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が使用できる。 The organic solvent contained in the colored resin composition for a color filter of the present invention has sufficient dissolving power with respect to a binder resin, a photopolymerization initiator, and the like, which are components of the colored resin composition, and is used for the synthesis of the binder resin. Those having sufficient dissolving power for the monofunctional monomer and polymerization initiator used can be used. Moreover, what can maintain dispersion stability can also be 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 And ketones such as methyl butyl ketone and cyclohexanone; and alcohols such as methanol, ethanol, butanol, isopropyl 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。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40〜10000質量部、好ましくは100〜1000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 usage-amount of an organic solvent is 40-10000 mass parts normally with respect to 100 mass parts of total solid content of a colored resin composition, Preferably it is 100-1000 mass parts.
本発明のカラーフィルター用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 for a color filter 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1〜80質量部、好ましくは5〜50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. Content of a hardening | curing agent is 1-80 mass parts normally with respect to 100 mass parts of total solids of a colored resin composition, Preferably it is 5-50 mass parts. 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.
本発明のカラーフィルター用着色樹脂組成物は、光重合開始剤及び/又は硬化促進剤を含有する。
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 for a color filter of the present invention contains 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, methylbenzoylformate, 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 (tribromomethyl) ) -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) butane -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 initiator, Kayacure DMBI, Kayacure BDK, Kayacure BP-100, Kayacure BMBI, Kayacure DETX-S, Kayacure EPA (all manufactured by Nippon Kayaku), Darocure 1173, Darocure 1116 (Iremo Merck Japan), Irgacure 907 ( BASF Japan), Irgacure 369 (BASF Japan), Irgacure 379EG (BASF Japan), Irgacure OXE-01 (BASF Japan), Irgacure OXE-02 (BASF Japan), Irgacure PAG103 (BASF) Japan)), TME-triazine (manufactured by Sanwa Chemical), biimidazole (manufactured by Kurokin Kasei), STR-110, STR-1 (all manufactured by Respe Chemical), etc. The present invention is not limited to these.
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0.5〜50質量部、好ましくは1〜25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. Content of a photoinitiator is 0.5-50 mass parts normally with respect to 100 mass parts of total solids of a colored resinous composition, Preferably it is 1-25 mass parts.
本発明のカラーフィルター用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〜3級のアミンやイミダゾール類等のN含有複素環化合物、酸無水物等が挙げられる。
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。
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。
The curing accelerator that can be contained in the colored resin composition for a color filter of the present invention is a reaction catalyst that promotes ion curing, such as N-containing heterocyclic compounds such as primary to tertiary amines and imidazoles, acids, and the like. An anhydride etc. are mentioned.
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.
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。
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0.01〜50質量部、好ましくは0.05〜20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質量部よりも多すぎる場合は保存安定性が悪くなる恐れがある。
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.
Content of a hardening accelerator is 0.01-50 mass parts normally with respect to 100 mass parts of total solids of a colored resin composition, Preferably it is 0.05-20 mass parts. When the content of the curing accelerator is less than 0.01 parts by mass, the curability may be lowered, and when it is more than 50 parts by mass, the storage stability may be deteriorated.
本発明のカラーフィルター用着色樹脂組成物には、任意成分として上記式(1)で表されるキサンテン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、本発明の着色樹脂組成物は赤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キサンテン化合物と任意成分である色素の含有量の合計が、通常0.01〜70質量部、好ましくは0.5〜50質量部、より好ましくは1.0〜40質量部の範囲内であれば特に限定されない。 In the colored resin composition for a color filter of the present invention, a dye other than the xanthene 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. Since an object relates to a red pixel, it is preferable to use a known red dye or yellow dye, or a red pigment or yellow pigment. When the pigment as an optional component is used in combination, the total content of the xanthene compound as an essential component and the pigment as an optional component with respect to 100 parts by mass of the total solid content of the colored resin composition of the present invention is usually It will not be specifically limited if it exists in the range of 0.01-70 mass parts, Preferably it is 0.5-50 mass parts, More preferably, it is 1.0-40 mass parts.
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。 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.
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242および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よりなる群から選ばれる少なくとも一種を含有していることが好ましい。 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. Examples include orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73. Of these, C.I. I. Pigment red 177, C.I. I. Pigment red 242 and C.I. I. Pigment red 254, C.I. I. Pigment yellow 138, C.I. I. It is preferable to contain at least one selected from the group consisting of CI Pigment Yellow 150.
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、カドニウムエロー、カドニウムレッド、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 purple, cobalt purple, barium sulfate, magnesium carbonate and other metal oxides, Examples thereof include metal sulfides, sulfates, metal hydroxides, and metal carbonates.
前記式(1)で表されるキサンテン化合物および任意に併用される色素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。 In the case where the solubility of the xanthene compound represented by the formula (1) and the optionally used dye in the resin component is low, the dispersant may be used in combination with a dispersing agent or a dispersing aid. 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、有機溶剤に不溶な色素が、例えば酸性染料や塩基性染料の場合は、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することが知られている。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使用可能である。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。 When the pigment insoluble in the organic solvent is, for example, an acid dye or a basic dye, it is modified with an amine salt dye by reacting an organic amine compound (for example, n-propylamine, ethylhexylpropionic acid amine, etc.) It is known that the organic amine compound is reacted with a sulfonic acid group to be modified into a dye having a sulfonamide group to make it soluble in an organic solvent. These amine-modified dyes can also be used in 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、式(1)で表されるキサンテン化合物、バインダー樹脂、溶剤、光重合開始剤、硬化剤及び/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。 In the colored resin composition of the present invention, the xanthene compound represented by the formula (1), the binder resin, the solvent, the photopolymerization initiator, the curing agent and / or the curing accelerator are mixed and stirred by a dissolver or a homomixer. Manufactured. 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カラーフィルター用着色硬化膜(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 for a color filter (hereinafter also simply referred to as “colored cured film”) using the colored resin composition of the present invention include a photolithography method and an inkjet method. A photosensitive colored resin composition excellent in developability containing a polymerization initiator is used, and the latter does not necessarily require a photopolymerization initiator, and a thermosetting colored 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。
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。
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.
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0.1〜20μm、好ましくは0.5〜5μm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23〜150℃で1〜60分間、好ましくは60〜120℃で1〜10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130〜300℃で1〜120分間、好ましくは150〜250℃で1〜30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 vacuum chamber at 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 the non-irradiated part by development and rinsing with water, it is usually post-baked at 130 to 300 ° C. for 1 to 120 minutes, preferably at 150 to 250 ° C. for 1 to 30 minutes. 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10〜50℃で30〜600秒、好ましくは20〜40℃で30〜120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 performed 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赤色画素である。 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 red pixel consisting of the colored cured film of the present 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、実施例により本発明を更に詳細に説明するが、本発明は、これらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.
合成例1(下記式(2)で表されるキサンテン化合物の合成)
300ml四つ口フラスコに、下記式(100)のフルオラン化合物3.7部、2−プロパノール55部、ジブチルアミン(東京化成工業社製)7.7部を入れ、80℃で5時間還流させた。この反応液を減圧下で濃縮し、得られた残渣を17%メタノール水1200部に加え、2時間懸濁攪拌、ろ過、乾燥することにより、式(2)で表されるキサンテン化合物を3.1部得た。該化合物の極大吸収波長は561nm(メタノール)であった。
式(2)で表されるキサンテン化合物の物性データー
1H−NMR(400MHz、DMSO−d6)測定値:δ8.80(d、1H)、7.58(dt、2H)、7.19(d、1H)、7.02(m、4H)、6.92(s、2H)、3.56(m、8H)、1.58(m、8H)、1.38(m、8H)、0.92(m、12H)。
Synthesis Example 1 (Synthesis of xanthene compound represented by the following formula (2))
In a 300 ml four-necked flask, 3.7 parts of a fluorane compound of the following formula (100), 55 parts of 2-propanol, and 7.7 parts of dibutylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) were placed and refluxed at 80 ° C. for 5 hours. . The reaction solution was concentrated under reduced pressure, and the obtained residue was added to 1200 parts of 17% methanol water, suspended and stirred for 2 hours, filtered and dried, whereby the xanthene compound represented by the formula (2) was converted to 3. 1 part was obtained. The maximum absorption wavelength of the compound was 561 nm (methanol).
Physical property data of xanthene compound represented by formula (2)
1 H-NMR (400 MHz, DMSO-d6) measured values: δ 8.80 (d, 1H), 7.58 (dt, 2H), 7.19 (d, 1H), 7.02 (m, 4H), 6.92 (s, 2H), 3.56 (m, 8H), 1.58 (m, 8H), 1.38 (m, 8H), 0.92 (m, 12H).
合成例2(下記式(3)で表されるキサンテン化合物の合成)
500mlの四つ口フラスコに、上記式(100)のフルオラン化合物15部、スルホラン150部、ジイソブチルアミン(東京化成工業社製)24部、塩化亜鉛8部を入れ、85℃で6時間反応させた。この反応液を2M塩酸500部に加え、15分間懸濁撹拌、ろ過し、固形分をメタノール40部で溶解させた。この溶液を2M塩酸1000部に滴下し、撹拌、ろ過、乾燥することにより、式(3)で表されるキサンテン化合物を11.7部得た。該化合物の極大吸収波長は562nm(メタノール)であった。
Synthesis Example 2 (Synthesis of xanthene compound represented by the following formula (3))
In a 500 ml four-necked flask, 15 parts of the fluorane compound of the above formula (100), 150 parts of sulfolane, 24 parts of diisobutylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 8 parts of zinc chloride were placed and reacted at 85 ° C. for 6 hours. . This reaction solution was added to 500 parts of 2M hydrochloric acid, suspended and stirred for 15 minutes and filtered, and the solid content was dissolved in 40 parts of methanol. This solution was added dropwise to 1000 parts of 2M hydrochloric acid, stirred, filtered and dried to obtain 11.7 parts of a xanthene compound represented by the formula (3). The maximum absorption wavelength of the compound was 562 nm (methanol).
合成例3(下記式(4)で表されるキサンテン化合物の合成)
100ml四つ口フラスコに、上記式(100)のフルオラン化合物3.7部、スルホラン(純正化学社製)30部、ジエタノールアミン(東京化成工業社製)9.6部、塩化亜鉛(関東化学社製)1.9部を入れ、100℃で1時間、その後90℃で2時間加熱攪拌させた。反応液の温度を80℃に下げ、この反応液を水150部中へ注ぎ、塩45部を加え結晶を塩析、ろ取した。得られたウェットケーキを、水150部、メタノール230部の混合液中で懸濁攪拌し、ろ過後、得られたこのろ液に陰イオン交換樹脂ダイアイオンRTMSA10AOH50部及び陽イオン交換樹脂ダイアイオンRTMSK1BH30部(共に三菱化学社製)を適宜添加して、液のpHを5〜6に保持しながら、液温20〜30℃で1時間撹拌することにより脱塩を行なった。得られた液をろ過することによりイオン交換樹脂を除去した後、ろ液を減圧下で濃縮、残渣に水10部を加え、析出した結晶をろ過、乾燥することにより、式(4)で表されるキサンテン化合物を1.3部得た。該化合物の極大吸収波長は556nm(メタノール)であった。
式(4)で表されるキサンテン系酸性染料の物性データー
1H−NMR(400MHz、DMSO−d6)測定値:δ8.00(d、1H)、7.58(dt、2H)、7.19(d、1H)、7.11(m、2H)、7.00(m、4H)、4.97(s、4H)、3.78−3.68(m、16H)。
Synthesis Example 3 (Synthesis of xanthene compound represented by the following formula (4))
In a 100 ml four-necked flask, 3.7 parts of the fluorane compound of the above formula (100), 30 parts of sulfolane (manufactured by Junsei Chemical Co., Ltd.), 9.6 parts of diethanolamine (manufactured by Tokyo Chemical Industry Co., Ltd.), zinc chloride (manufactured by Kanto Chemical Co., Inc.) ) 1.9 parts was added and heated and stirred at 100 ° C. for 1 hour and then at 90 ° C. for 2 hours. The temperature of the reaction solution was lowered to 80 ° C., the reaction solution was poured into 150 parts of water, 45 parts of salt was added, and the crystals were salted out and collected by filtration. The obtained wet cake was suspended and stirred in a mixed solution of 150 parts of water and 230 parts of methanol, and after filtration, 50 parts of anion exchange resin Diaion RTMSA10AOH and cation exchange resin Diaion RTMSK1BH30 were added to the obtained filtrate. Part (both manufactured by Mitsubishi Chemical Corporation) was added as appropriate, and desalting was performed by stirring at a liquid temperature of 20 to 30 ° C. for 1 hour while maintaining the pH of the liquid at 5 to 6. After removing the ion-exchange resin by filtering the obtained liquid, the filtrate was concentrated under reduced pressure, 10 parts of water was added to the residue, and the precipitated crystals were filtered and dried to obtain the formula (4). 1.3 parts of xanthene compound was obtained. The maximum absorption wavelength of the compound was 556 nm (methanol).
Physical property data of xanthene acid dyes represented by formula (4)
1 H-NMR (400 MHz, DMSO-d6) measured values: δ 8.00 (d, 1H), 7.58 (dt, 2H), 7.19 (d, 1H), 7.11 (m, 2H), 7.00 (m, 4H), 4.97 (s, 4H), 3.78-3.68 (m, 16H).
合成例4(下記式(5)で表されるキサンテン化合物の合成)
300ml四つ口フラスコに、上記式(100)のフルオラン化合物3.7部、2−プロパノール55部、ジ(メトキシエチル)アミン(東京化成工業社製)7.2部を入れ、80℃で3時間還流させた。反応液の温度が50〜60℃の間で、この反応液をろ過し、得られたろ液を減圧下で濃縮した。得られた残渣を乾燥することにより、式(5)で表されるキサンテン化合物を1.1部得た。該化合物の極大吸収波長は556nm(メタノール)であった。
Synthesis Example 4 (Synthesis of xanthene compound represented by the following formula (5))
In a 300 ml four-necked flask, 3.7 parts of the fluorane compound of the above formula (100), 55 parts of 2-propanol, and 7.2 parts of di (methoxyethyl) amine (manufactured by Tokyo Chemical Industry Co., Ltd.) are placed. Reflux for hours. The reaction solution was filtered while the temperature of the reaction solution was 50 to 60 ° C., and the obtained filtrate was concentrated under reduced pressure. The obtained residue was dried to obtain 1.1 parts of a xanthene compound represented by the formula (5). The maximum absorption wavelength of the compound was 556 nm (methanol).
合成例5(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、80〜85℃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 5 (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 80-85 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1
C.I.ピグメントレッド254/C.I.ピグメントレッド177/合成例1で得られた式(2)で表されるキサンテン化合物/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)=10.1/4.3/0.6/4.0/81.0(質量比)の組成比で混合した後、0.3mmジルコニアビーズ400部を添加し、ペイントシェーカーで60分間処理を行い、ろ過することにより、赤色顔料分散液を得た。上記赤色分散液25部に、バインダー樹脂として合成例5で得られた共重合体(A)を5.5部、光重合性モノマーとしてカヤラッドDPHA(日本化薬製)を5.5部、光重合開始剤としてイルガキュアー907(BASFジャパン製)を1.0部、イルガキュアーOXE−02(BASFジャパン製)を0.1部、カヤキュアーDETX−S(日本化薬製)を0.5部及びプロピレングリコールモノメチルエーテルアセテートを30部混合し、本発明の着色樹脂組成物1を得た。
Example 1
C. I. Pigment red 254 / C.I. I. Pigment Red 177 / xanthene compound represented by Formula (2) obtained in Synthesis Example 1 / Disperbyk-2001 (manufactured by Big Chemie Japan) / PGMEA (propylene glycol monomethyl ether acetate) = 10.1 / 4.3 / 0 After mixing at a composition ratio of .6 / 4.0 / 81.0 (mass ratio), 400 parts of 0.3 mm zirconia beads are added, treated with a paint shaker for 60 minutes, and filtered to disperse the red pigment. A liquid was obtained. To 25 parts of the above red dispersion, 5.5 parts of the copolymer (A) obtained in Synthesis Example 5 as a binder resin, 5.5 parts of Kayrad DPHA (manufactured by Nippon Kayaku) as a photopolymerizable monomer, light As a polymerization initiator, 1.0 part of Irgacure 907 (BASF Japan), 0.1 part of Irgacure OXE-02 (BASF Japan), 0.5 part of Kayacure DETX-S (Nippon Kayaku) and 30 parts of propylene glycol monomethyl ether acetate was mixed to obtain a colored resin composition 1 of the present invention.
実施例2
合成例1で得られた式(2)で表されるキサンテン化合物/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)=4.0/4.0/92.0(質量比)の組成比で混合した後、0.3mmジルコニアビーズ400部を添加し、ペイントシェーカーで60分間処理を行い、ろ過することにより、赤色顔料分散液を得た。上記赤色分散液25部に、バインダー樹脂として合成例5で得られた共重合体(A)を5.5部、光重合性モノマーとしてカヤラッドDPHA(日本化薬製)を5.5部、光重合開始剤としてイルガキュアー907(BASFジャパン製)を1.0部、イルガキュアーOXE−02(BASFジャパン製)を0.1部およびカヤキュアーDETX−S(日本化薬製)を0.5部及びプロピレングリコールモノメチルエーテルアセテートを30部混合し、本発明の着色樹脂組成物2を得た。
Example 2
Xanthene compound represented by formula (2) obtained in Synthesis Example 1 / Disperbyk-2001 (manufactured by Big Chemie Japan) / PGMEA (propylene glycol monomethyl ether acetate) = 4.0 / 4.0 / 92.0 (mass) After mixing at a composition ratio of 400), 400 parts of 0.3 mm zirconia beads were added, treated with a paint shaker for 60 minutes, and filtered to obtain a red pigment dispersion. To 25 parts of the above red dispersion, 5.5 parts of the copolymer (A) obtained in Synthesis Example 5 as a binder resin, 5.5 parts of Kayrad DPHA (manufactured by Nippon Kayaku) as a photopolymerizable monomer, light As a polymerization initiator, 1.0 part of Irgacure 907 (manufactured by BASF Japan), 0.1 part of Irgacure OXE-02 (manufactured by BASF Japan) and 0.5 part of Kayacure DETX-S (manufactured by Nippon Kayaku) 30 parts of propylene glycol monomethyl ether acetate was mixed to obtain a colored resin composition 2 of the present invention.
実施例3
式(2)で表されるキサンテン化合物を、合成例2で得られた式(3)で表されるキサンテン化合物に変更したこと以外は実施例1に準じて、本発明の着色樹脂組成物3を得た。
Example 3
The colored resin composition 3 of the present invention is the same as in Example 1 except that the xanthene compound represented by formula (2) is changed to the xanthene compound represented by formula (3) obtained in Synthesis Example 2. Got.
実施例4
式(2)で表されるキサンテン化合物を、合成例3で得られた式(4)で表されるキサンテン化合物に変更したこと以外は実施例1に準じて、本発明の着色樹脂組成物4を得た。
Example 4
The colored resin composition 4 of the present invention is the same as in Example 1 except that the xanthene compound represented by the formula (2) is changed to the xanthene compound represented by the formula (4) obtained in Synthesis Example 3. Got.
実施例5
式(2)で表されるキサンテン化合物を、合成例4で得られた式(5)で表されるキサンテン化合物に変更したこと以外は実施例1に準じて、本発明の着色樹脂組成物5を得た。
Example 5
The colored resin composition 5 of the present invention is the same as in Example 1 except that the xanthene compound represented by the formula (2) is changed to the xanthene compound represented by the formula (5) obtained in Synthesis Example 4. Got.
比較例1
C.I.ピグメントレッド254/C.I.ピグメントレッド177/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)=7.5/7.5/4.0/81.0(質量比)の組成比で混合した後、0.3mmジルコニアビーズ400部を添加し、ペイントシェーカーで60分間処理を行い、ろ過することにより、赤色顔料分散液を得た。上記赤色分散液25部に、バインダー樹脂として合成例5で得られた共重合体(A)を5.5部、光重合性モノマーとしてカヤラッドDPHA(日本化薬製)を5.5部、光重合開始剤としてイルガキュアー907(BASFジャパン製)を1.0部、イルガキュアーOXE−02(BASFジャパン製)を0.1部、カヤキュアーDETX−S(日本化薬製)を0.5部及びプロピレングリコールモノメチルエーテルアセテートを30部混合し、比較用樹脂組成物1を得た。
Comparative Example 1
C. I. Pigment red 254 / C.I. I. After mixing at a composition ratio of CI Pigment Red 177 / Disperbyk-2001 (by Big Chemie Japan) / PGMEA (propylene glycol monomethyl ether acetate) = 7.5 / 7.5 / 4.0 / 81.0 (mass ratio), 400 parts of 0.3 mm zirconia beads were added, treated with a paint shaker for 60 minutes, and filtered to obtain a red pigment dispersion. To 25 parts of the above red dispersion, 5.5 parts of the copolymer (A) obtained in Synthesis Example 5 as a binder resin, 5.5 parts of Kayrad DPHA (manufactured by Nippon Kayaku) as a photopolymerizable monomer, light As a polymerization initiator, 1.0 part of Irgacure 907 (BASF Japan), 0.1 part of Irgacure OXE-02 (BASF Japan), 0.5 part of Kayacure DETX-S (Nippon Kayaku) and 30 parts of propylene glycol monomethyl ether acetate was mixed to obtain a comparative resin composition 1.
比較例2
式(2)で表されるキサンテン化合物を、C.I.Acid Red 52(東京化成製)に変更したこと以外は実施例1に準じて、比較用樹脂組成物2を得た。
Comparative Example 2
The xanthene compound represented by the formula (2) is C.I. I. Resin composition 2 for comparison was obtained according to Example 1 except that it was changed to Acid Red 52 (manufactured by Tokyo Chemical Industry Co., Ltd.).
比較例3
式(2)で表されるキサンテン化合物を、C.I.Acid Red 52(東京化成製)に変更したこと以外は実施例2に準じて、比較用樹脂組成物3を得た。
Comparative Example 3
The xanthene compound represented by the formula (2) is C.I. I. Resin composition 3 for comparison was obtained according to Example 2 except that it was changed to Acid Red 52 (manufactured by Tokyo Chemical Industry Co., Ltd.).
(現像性、解像度及び基板への密着性の評価)
上記で得られた本発明の着色樹脂組成物1〜5をガラス基板上に塗布し、80℃×100秒の条件でプリベークした後、マスクを介して露光による硬化を行い、界面活性剤を含有するアルカリ水溶液で現像し、水でリンス後、200℃×5分間加熱硬化して着色パターンを得た。得られたパターンは、ラインアンドスペースにて5μm角の解像性を持ち、残渣、画素の剥がれ等は確認されなかった。従って、固体撮像素子用の高解像度が要求されるカラーフィルター用途にも適用できることが分かった。
(Evaluation of developability, resolution and adhesion to the substrate)
After applying the colored resin compositions 1 to 5 of the present invention obtained above on a glass substrate and prebaking under conditions of 80 ° C. × 100 seconds, curing by exposure through a mask and containing a surfactant The resultant was developed with an aqueous alkaline solution, rinsed with water, and then heated and cured at 200 ° C. for 5 minutes to obtain a colored pattern. The obtained pattern had a resolution of 5 μm square in line and space, and no residue or peeling of pixels was confirmed. Therefore, it was found that the present invention can also be applied to color filter applications requiring high resolution for solid-state imaging devices.
マスク露光を全面露光に変更し、現像及びリンス処理を行わなかったこと以外は前記現像性等の評価と同様にして、評価用基板を作成したところ、本発明の着色樹脂組成物1〜5及び比較用樹脂組成物1〜3のいずれを用いた場合にも、鮮明な色特性を有するカラーフィルター基板が得られた。これらの評価用基板を用いて、以下に記載の方法で各評価を行った。 When the substrate for evaluation was prepared in the same manner as in the evaluation of the developability except that the mask exposure was changed to full exposure and development and rinsing were not performed, the colored resin compositions 1 to 5 of the present invention and When any one of the comparative resin compositions 1 to 3 was used, a color filter substrate having clear color characteristics was obtained. Each evaluation was performed by the method as described below using these evaluation substrates.
(明度評価)
本発明の着色樹脂組成物1、3、4、5及び比較用樹脂組成物1を用いて得られたカラーフィルター基板について、分光光度計(UV−2450:島津製作所(株))により評価用基板の分光透過率を測定し、C光源のCIEのXYZ表色系におけるx、y、色度座標と明度Yを評価した。結果を表1に示した。
(耐熱性評価)
本発明の着色樹脂組成物1〜5及び比較用樹脂組成物2〜3を用いて得られたカラーフィルター基板について、220℃で120分間加熱処理を行い、処理前後の評価用基板の分光透過率を測定し、熱処理前後の色差(ΔEab)を算出して評価した。結果を表2に示した。
(Brightness evaluation)
About the color filter substrate obtained by using the colored resin composition 1, 3, 4, 5 and the comparative resin composition 1 of the present invention, a substrate for evaluation using a spectrophotometer (UV-2450: Shimadzu Corporation) Were measured, and x, y, chromaticity coordinates and brightness Y in the CIE XYZ color system of the C light source were evaluated. The results are shown in Table 1.
(Heat resistance evaluation)
The color filter substrate obtained using the colored resin compositions 1 to 5 and the comparative resin compositions 2 to 3 of the present invention is subjected to heat treatment at 220 ° C. for 120 minutes, and the spectral transmittance of the evaluation substrate before and after the treatment. The color difference (ΔEab) before and after the heat treatment was calculated and evaluated. The results are shown in Table 2.
表1 着色樹脂組成物の明度評価結果
x y Y
着色樹脂組成物1 0.655 0.321 18.3
着色樹脂組成物3 0.655 0.321 18.5
着色樹脂組成物4 0.655 0.324 17.2
着色樹脂組成物5 0.655 0.321 18.4
比較用樹脂組成物1 0.655 0.321 18.0
Table 1 Brightness evaluation results of colored resin composition
x y Y
Colored resin composition 1 0.655 0.321 18.3
Colored resin composition 3 0.655 0.321 18.5
Colored resin composition 4 0.655 0.324 17.2
Colored resin composition 5 0.655 0.321 18.4
Comparative resin composition 1 0.655 0.321 18.0
表2 着色樹脂組成物の耐熱性評価結果
(ΔEab)
着色樹脂組成物1 1.7
着色樹脂組成物2 3.8
着色樹脂組成物3 1.1
着色樹脂組成物4 1.3
着色樹脂組成物5 2.2
比較用樹脂組成物2 6.8
比較用樹脂組成物3 8.6
Table 2 Evaluation results of heat resistance of colored resin composition
(ΔEab)
Colored resin composition 1 1.7
Colored resin composition 2 3.8
Colored resin composition 3 1.1
Colored resin composition 4 1.3
Colored resin composition 5 2.2
Comparative resin composition 2 6.8
Comparative resin composition 3 8.6
表1の結果から、本発明の着色樹脂組成物1および3〜5は、顔料単独の比較用樹脂組成物1に比べて良好な明度を示した。 From the results of Table 1, the colored resin compositions 1 and 3 to 5 of the present invention showed better brightness than the comparative resin composition 1 of the pigment alone.
表2の結果から、本発明の着色樹脂組成物1〜5の耐熱性は、比較用樹脂組成物2及び3よりも優れており、高い信頼性を有していた。 From the result of Table 2, the heat resistance of the colored resin compositions 1 to 5 of the present invention was superior to the comparative resin compositions 2 and 3, and had high reliability.
以上より、本願発明のカラーフィルター用着色樹脂組成物を用いて得られたカラーフィルターは、従来の顔料分散型の着色樹脂組成物を用いて得られたカラーフィルターと比べて同等以上の明度を有すると共に、高い耐熱性を有することから、耐熱性の必要なカラーフィルターの製造プロセスに耐えうる信頼性の高いカラーフィルターとしての有用である。 As described above, the color filter obtained using the colored resin composition for a color filter of the present invention has a brightness equal to or higher than that of a color filter obtained using a conventional pigment-dispersed colored resin composition. In addition, since it has high heat resistance, it is useful as a highly reliable color filter that can withstand the manufacturing process of a color filter that requires heat resistance.
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、高明度で耐熱性に優れた高品位で信頼性の高いカラーフィルターの赤色画素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, it is possible to provide a red pixel of a high-quality and highly reliable color filter that has high brightness and excellent heat resistance.
Claims (9)
で表されるキサンテン化合物、バインダー樹脂、有機溶剤及び硬化剤、並びに光重合開始剤及び/または硬化促進剤を含有するカラーフィルター用着色樹脂組成物。 Following formula (1)
The color resin composition for color filters containing the xanthene compound represented by these, a binder resin, an organic solvent, and a hardening | curing agent, and a photoinitiator and / or a hardening accelerator.
A solid-state imaging device equipped with the color filter according to claim 6.
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JP2017120379A (en) * | 2015-12-29 | 2017-07-06 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Colored photosensitive resin composition, color filter and image display device comprising the same |
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KR20200072468A (en) | 2017-10-24 | 2020-06-22 | 호도가야 가가쿠 고교 가부시키가이샤 | Coloring composition containing colorant compound composed of xanthene-based cationic dye and organic anion, colorant for color filter, and color filter |
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