JP4456562B2 - Coloring composition and color filter using the same - Google Patents
Coloring composition and color filter using the same Download PDFInfo
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- JP4456562B2 JP4456562B2 JP2005359614A JP2005359614A JP4456562B2 JP 4456562 B2 JP4456562 B2 JP 4456562B2 JP 2005359614 A JP2005359614 A JP 2005359614A JP 2005359614 A JP2005359614 A JP 2005359614A JP 4456562 B2 JP4456562 B2 JP 4456562B2
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- organic solvent
- pigment
- coloring composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 100
- 238000004040 coloring Methods 0.000 title claims description 52
- 239000003960 organic solvent Substances 0.000 claims description 55
- 239000002216 antistatic agent Substances 0.000 claims description 18
- 229920000178 Acrylic resin Polymers 0.000 claims description 17
- 239000004925 Acrylic resin Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 15
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 13
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 13
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 13
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 12
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 11
- 229940117955 isoamyl acetate Drugs 0.000 claims description 6
- 238000002834 transmittance Methods 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 5
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 50
- 238000000576 coating method Methods 0.000 description 47
- 239000010408 film Substances 0.000 description 45
- 239000011248 coating agent Substances 0.000 description 39
- 239000000975 dye Substances 0.000 description 36
- 239000000758 substrate Substances 0.000 description 26
- 239000011347 resin Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- -1 polyoxyethylene Polymers 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 10
- 239000002270 dispersing agent Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 238000007607 die coating method Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 241000519995 Stachys sylvatica Species 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011362 coarse particle Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000001053 orange pigment Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001057 purple pigment Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- LRSLDYIFOCTRHR-UHFFFAOYSA-N (3-benzoyl-4-ethylphenyl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=C(CC)C(C(=O)C=2C=CC=CC=2)=C1 LRSLDYIFOCTRHR-UHFFFAOYSA-N 0.000 description 1
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- HDYFAPRLDWYIBU-UHFFFAOYSA-N 1-silylprop-2-en-1-one Chemical class [SiH3]C(=O)C=C HDYFAPRLDWYIBU-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 1
- DQMOHZLFVGYNAN-UHFFFAOYSA-N 2-(2-phenylethenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=CC=2C=CC=CC=2)=N1 DQMOHZLFVGYNAN-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
- MPNIGZBDAMWHSX-UHFFFAOYSA-N 2-(4-methylphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MPNIGZBDAMWHSX-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- XOSCOJBBKOVIOM-UHFFFAOYSA-N 2-aminoethanol;octadecanoic acid Chemical compound NCCO.CCCCCCCCCCCCCCCCCC(O)=O XOSCOJBBKOVIOM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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Description
本発明は、カラー液晶表示装置、カラー撮像管素子等に用いられるカラーフィルタの製造に使用される着色組成物、およびそれを用いたカラーフィルタに関する。 The present invention relates to a coloring composition used for producing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter using the same.
液晶ディスプレイ（ＬＣＤ）、カラー撮像管素子（ＣＣＤ）等を構成するカラーフィルタは、塗布液（着色組成物）を透明基板上に塗布・乾燥し、厚さが約１〜３μmの塗膜を形成することにより製造される。基板上への塗布方式は、スピンコート法やダイコート法等があり、その特徴に応じて適宜用いられている。
スピンコート法は、比較的小サイズの基板への薄膜形成に広く用いられている方法であり、透明基板を一定の回転数で回転させながら、透明基板中心部に塗布液を滴下し、遠心力によって塗布液を薄く延ばし、その塗布液に適した透明基板の回転数や回転時間等を制御することにより、所望の膜厚の塗膜を透明基板の表面に形成する塗布方法である。しかしながら、回転による遠心力を利用し塗膜を薄く延ばすという原理に起因し、透明基板の回転中心部分および周辺部分の塗布膜厚が、その中間部分に比べて厚くなりすぎるという欠点がある。
For color filters that make up liquid crystal displays (LCDs), color image pickup tube elements (CCDs), etc., a coating solution (colored composition) is applied to a transparent substrate and dried to form a coating film with a thickness of about 1 to 3 μm. It is manufactured by doing. Examples of the coating method on the substrate include a spin coating method and a die coating method, which are appropriately used depending on the characteristics.
The spin coating method is widely used for forming a thin film on a relatively small-sized substrate. While rotating the transparent substrate at a constant rotational speed, the coating solution is dropped onto the central portion of the transparent substrate and centrifugal force is applied. Is a coating method in which a coating film having a desired film thickness is formed on the surface of the transparent substrate by extending the coating solution thinly and controlling the number of revolutions and the rotation time of the transparent substrate suitable for the coating solution. However, due to the principle of extending the coating film thinly by utilizing the centrifugal force due to rotation, there is a drawback that the coating film thickness at the rotation center portion and the peripheral portion of the transparent substrate becomes too thick compared to the intermediate portion.
ダイコート法は、大サイズの基板への薄膜形成に適した方法であり、スリットから塗布液を吐出し、該スリットを移動しながら所望の膜厚の塗膜を透明基板の表面に形成する塗布方法である。しかしながら、その機構上スリットの進行方向にたいして垂直方向にスジ状のムラ（スジムラ）が発生しやすく、また、塗膜外周部が盛り上がり、基板中心部に比べて膜厚が厚くなるという欠点がある。
また、塗布方式によらず塗布液の乾燥性や表面張力が適切でないとピンホール（白抜け）が生じるといった問題が起こる。
こうしたスピンコート法やダイコート法における塗膜の不均一性の問題を解消すべく、種々の試みがなされている。例えば、特許文献１には、沸点や蒸気圧が特定の範囲内である溶剤を５０重量％以上含む組成物が、塗膜の表面平滑性に優れたスピンコート法用の組成物として開示されている。また、特許文献２には、ダイコート法において、塗布液の表面張力を一定範囲に調整し、塗工面のスジムラや膜厚ムラ等を低減する塗工液およびその塗工方法が開示されている。
The die coating method is a method suitable for forming a thin film on a large-sized substrate, and a coating method of discharging a coating liquid from a slit and forming a coating film having a desired film thickness on the surface of the transparent substrate while moving the slit. It is. However, due to the mechanism, stripe-like unevenness (straight unevenness) is likely to occur in a direction perpendicular to the direction of movement of the slit, and the outer peripheral portion of the coating film rises and the film thickness becomes thicker than the central portion of the substrate.
Further, there is a problem that pinholes (white spots) occur if the drying property and surface tension of the coating solution are not appropriate regardless of the coating method.
Various attempts have been made to solve the problem of non-uniformity of the coating film in the spin coating method and the die coating method. For example, Patent Document 1 discloses a composition containing 50% by weight or more of a solvent having a boiling point or vapor pressure within a specific range as a composition for a spin coating method having excellent surface smoothness of a coating film. Yes. Patent Document 2 discloses a coating solution and a coating method for adjusting the surface tension of the coating solution to a certain range in the die coating method to reduce unevenness of the coating surface, film thickness unevenness, and the like.
さらに、スピンコート方式やダイコート方式といったいずれの塗布方式においても、均一な薄膜を基板上に形成するためには、なるべく着色組成物の粘度が低いほうが好ましい。粘度が高い着色組成物を用いるほど、薄膜を形成することが難しくなる。また、顔料が有機溶剤中に分散された着色組成物で粘度が高いものには、動的な状態での粘度と静的な状態での粘度の差が大きくなる（チキソ性が高い）傾向のものもあり、そうした着色組成物を使用して薄膜を形成した場合、膜厚の均一性が悪い薄膜となる。
従って、できるだけ低粘度の着色組成物を作る必要があるが、その手段の一つとして、低粘度の溶剤を含有させる方法がある。しかし、カラーフィルタ用の着色組成物に使用可能な低粘度の溶剤は、誘電率や電導度が低いため帯電性が高くなるものが多く、帯電による塗布ムラを生じやすい。
これに対して、特許文献３には、着色組成物に導電性微粒子を添加し、着色組成物の導電率を一定以上に調整し、膜厚ムラを低減させる方法が開示されている。
Therefore, it is necessary to make a colored composition having as low a viscosity as possible. As one of the means, there is a method of containing a low-viscosity solvent. However, many low-viscosity solvents that can be used in the colored composition for color filters have high chargeability due to low dielectric constant and electrical conductivity, and are liable to cause coating unevenness due to charging.
On the other hand, Patent Document 3 discloses a method in which conductive fine particles are added to a colored composition, the electrical conductivity of the colored composition is adjusted to a certain level or more, and film thickness unevenness is reduced.
スピンコート法やダイコート法といった塗布方式と、それに用いる塗布液の性状（上述の帯電性も含む。）とに起因して、塗膜には様々な欠点が観察され、それらの欠点を整理すると以下のようになる。
白抜け：「白抜け＝ピンホール状の欠点」
色ムラ：「端部色ムラ＝端部に観察される額縁状の色ムラであり、境界が比較的明瞭」と「全体の色ムラ＝基板全体に観察される境界の不鮮明な色ムラ」の２つに分類される。
膜厚ムラ：膜厚の均一性が不十分であることを意味し、「膜厚均一性（端部）＝端面部の膜厚均一性」と「膜厚均一性（端部以外）＝基板中央から端面手前までの均一性」の２つに分類される。
スジムラ：「スジムラ＝ダイコート方式においてスリットの進行方向にたいして垂直方向に発生するスジ状のムラ」
Various defects are observed in the coating film due to the coating method such as the spin coating method and the die coating method, and the properties of the coating liquid used for the coating method (including the above-mentioned charging property). become that way.
White spots: "White spots = pinhole-like defects"
Color unevenness: "Edge color unevenness = frame-like color unevenness observed at the edge, the boundary is relatively clear" and "Overall color unevenness = blurred color unevenness of the boundary observed over the entire substrate" There are two categories.
Unevenness of film thickness: Insufficient film thickness uniformity, “film thickness uniformity (edge) = film thickness uniformity of end face” and “film thickness uniformity (other than edge) = substrate It is classified into “uniformity from the center to the front of the end face”.
Stripe: “Striped unevenness that occurs in the direction perpendicular to the direction of slit movement in the striped die-die coating method”
こうした欠点をいかに低減するかが課題であるが、上記特許文献に記載されたような、特定の溶剤を選択する方法、表面張力や粘度を一定の範囲に調整した組成物を使用する方法、着色組成物に導電性微粒子を添加して着色組成物の導電率を一定以上に調整する方法だけでは十分でない。
本発明は、スピンコート法およびダイコート法により塗布した場合に、塗膜に観察される上記欠点を低減できる着色組成物の提供を目的とする。また、本発明は、上記塗膜欠点が殆ど認められないフィルタセグメントを具備するカラーフィルタの提供を目的とする。
The problem is how to reduce these drawbacks. However, as described in the above-mentioned patent document, a method of selecting a specific solvent, a method of using a composition in which the surface tension and viscosity are adjusted within a certain range, and coloring. It is not sufficient to add conductive fine particles to the composition to adjust the conductivity of the colored composition to a certain level or more.
An object of this invention is to provide the coloring composition which can reduce the said fault observed by a coating film, when apply | coating by the spin coat method and the die coat method. Another object of the present invention is to provide a color filter having a filter segment in which the above-mentioned coating film defects are hardly recognized.
本発明の着色組成物は、可視光領域の４００〜７００ｎｍの全波長領域において透過率が８０％以上のアクリル系樹脂、モノマーもしくはオリゴマーの混合物からなる色素担体と、色素と、有機溶剤と、帯電防止剤とを含有する着色組成物であって、
着色組成物中の色素１００重量部に対して、透明樹脂が２０〜４００重量部であり、モノマーもしくはオリゴマーが１０〜３００重量部であり、有機溶剤が８００〜４０００重量部であり、帯電防止剤が０．０１〜１０．００重量部であり、
該帯電防止剤が、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンであって、
かつ有機溶剤として２５℃における誘電率が10.0以下、２５℃における電導度が1nS/cm以下、かつ２５℃における粘度が1.5mPa・s以下の酢酸イソアミル、３−エトキシプロピオン酸エチル、プロピレングリコールモノメチルエーテルアセテートからなる群から選ばれる少なくとも１種の有機溶剤Ａを有機溶剤の全量を基準として５重量％以上の範囲で含有し、
該着色組成物の２５℃における誘電率が8.0以上、２５℃における電導度が100nS/cm以上、かつ２５℃における粘度が20mPa・s以下であることを特徴とする。
また、本発明のカラーフィルタは、本発明の着色組成物から形成されるフィルタセグメントを具備することを特徴とする。
The colored composition of the present invention comprises a dye carrier comprising a mixture of acrylic resin, monomer or oligomer having a transmittance of 80% or more in the entire wavelength region of 400 to 700 nm in the visible light region , a dye, an organic solvent, A coloring composition containing an inhibitor,
The transparent resin is 20 to 400 parts by weight, the monomer or oligomer is 10 to 300 parts by weight, the organic solvent is 800 to 4000 parts by weight, and the antistatic agent is 100 parts by weight of the coloring matter in the coloring composition. Is 0.01 to 10.00 parts by weight,
The antistatic agent is a dimethylpolysiloxane having a polyalkylene oxide unit,
As an organic solvent, isoamyl acetate, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether having a dielectric constant at 25 ° C. of 10.0 or less, conductivity at 25 ° C. of 1 nS / cm or less, and viscosity at 25 ° C. of 1.5 mPa · s or less Containing at least one organic solvent A selected from the group consisting of acetates in a range of 5% by weight or more based on the total amount of the organic solvent;
The coloring composition has a dielectric constant at 25 ° C. of 8.0 or more, an electric conductivity at 25 ° C. of 100 nS / cm or more, and a viscosity at 25 ° C. of 20 mPa · s or less.
Moreover, the color filter of this invention comprises the filter segment formed from the coloring composition of this invention, It is characterized by the above-mentioned.
本発明の着色組成物は、誘電率や電導度が低いため帯電性が高い低粘度の有機溶剤を含有しているにもかかわらず、帯電防止剤を含有させることにより、均一な薄膜形成に必要な着色組成物の低粘度化と帯電性の抑止との両立を達成し、塗膜の欠点が低減した均一な塗膜を形成できるようにしたものである。
従って、本発明の着色組成物を用いてフィルタセグメントを形成することにより、良質なカラーフィルタを提供することが可能となる。
Although the coloring composition of the present invention contains a low-viscosity organic solvent having high chargeability due to low dielectric constant and electrical conductivity, it is necessary for forming a uniform thin film by containing an antistatic agent. It is possible to achieve both a reduction in viscosity of a coloring composition and suppression of chargeability, and to form a uniform coating film with reduced defects of the coating film.
Therefore, it is possible to provide a good color filter by forming a filter segment using the colored composition of the present invention.
まず、本発明の着色組成物について具体的に説明する。
本発明の着色組成物は、可視光領域の４００〜７００ｎｍの全波長領域において透過率が８０％以上のアクリル系樹脂、モノマーもしくはオリゴマーの混合物からなる色素担体と、色素と、有機溶剤と、帯電防止剤とを含有する着色組成物であって、
着色組成物中の色素１００重量部に対して、透明樹脂が２０〜４００重量部であり、モノマーもしくはオリゴマーが１０〜３００重量部であり、有機溶剤が８００〜４０００重量部であり、帯電防止剤が０．０１〜１０．００重量部であり、
該帯電防止剤が、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンであって、
かつ有機溶剤として２５℃における誘電率が10.0以下、２５℃における電導度が1nS/cm以下、かつ２５℃における粘度が1.5mPa・s以下の酢酸イソアミル、３−エトキシプロピオン酸エチル、プロピレングリコールモノメチルエーテルアセテートからなる群から選ばれる少なくとも１種の有機溶剤Ａを有機溶剤の全量を基準として５重量％以上の範囲で含有し、
該着色組成物の２５℃における誘電率が8.0以上、２５℃における電導度が100nS/cm以上、かつ２５℃における粘度が20mPa・s以下であることを特徴とする。
First, the coloring composition of this invention is demonstrated concretely.
The colored composition of the present invention comprises a dye carrier comprising a mixture of acrylic resin, monomer or oligomer having a transmittance of 80% or more in the entire wavelength region of 400 to 700 nm in the visible light region , a dye, an organic solvent, A coloring composition containing an inhibitor,
The transparent resin is 20 to 400 parts by weight, the monomer or oligomer is 10 to 300 parts by weight, the organic solvent is 800 to 4000 parts by weight, and the antistatic agent is 100 parts by weight of the coloring matter in the coloring composition. Is 0.01 to 10.00 parts by weight,
The antistatic agent is a dimethylpolysiloxane having a polyalkylene oxide unit,
As an organic solvent, isoamyl acetate, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether having a dielectric constant at 25 ° C. of 10.0 or less, conductivity at 25 ° C. of 1 nS / cm or less, and viscosity at 25 ° C. of 1.5 mPa · s or less Containing at least one organic solvent A selected from the group consisting of acetates in a range of 5% by weight or more based on the total amount of the organic solvent;
The coloring composition has a dielectric constant at 25 ° C. of 8.0 or more, an electric conductivity at 25 ° C. of 100 nS / cm or more, and a viscosity at 25 ° C. of 20 mPa · s or less.
帯電を防止する目的から、着色組成物の２５℃における誘電率が8.0以上で、かつ、２５℃における電導度が100nS/cm以上であれば良く、特に上限は無い。但し、着色組成物は水系ではなく溶剤系であるので、その基本的な性質からして、誘電率や電導度は水にイオン成分が溶解したような高い値にはならず、２５℃における誘電率は概ね200以下であり、２５℃における電導度は概ね1×106nS/cm以下である。
また、塗膜の「白抜け」、「色ムラ」、「膜厚ムラ」および「スジムラ」を少なくするため、着色組成物の２５℃における粘度（Ｅ型粘度計を用いて回転数20rpmで測定した粘度）は20mPa・s以下であれば良く、特に下限は無い。但し、含有する有機溶剤の粘度を下回ることはなく概ね0.5mPa・s以上である。２５℃における粘度が20mPa・sを超えると、スピンコート法やダイコート法では安定した塗工が難しくなり、塗膜の均一性を確保しにくい。
For the purpose of preventing charging, it is sufficient that the coloring composition has a dielectric constant at 25 ° C. of 8.0 or more and a conductivity at 25 ° C. of 100 nS / cm or more, and there is no particular upper limit. However, since the coloring composition is not water-based but solvent-based, its dielectric properties and conductivity are not as high as when ionic components are dissolved in water. The rate is approximately 200 or less, and the conductivity at 25 ° C. is approximately 1 × 10 6 nS / cm or less.
Also, in order to reduce “white spots”, “color unevenness”, “film thickness unevenness” and “straightness unevenness” of the coating film, the viscosity of the colored composition at 25 ° C. (measured using an E-type viscometer at 20 rpm) The viscosity is not more than 20 mPa · s, and there is no particular lower limit. However, it does not fall below the viscosity of the organic solvent contained, and is generally 0.5 mPa · s or more. When the viscosity at 25 ° C. exceeds 20 mPa · s, stable coating becomes difficult by spin coating or die coating, and it is difficult to ensure the uniformity of the coating film.
着色組成物の粘度を上記範囲にコントロールするためには、２５℃における誘電率が10.0以下、２５℃における電導度が1nS/cm以下、かつ２５℃における粘度が1.5mPa・s以下の有機溶剤Ａを有機溶剤の全量を基準（１００重量％）として５重量％以上の範囲で含有させる。有機溶剤Ａの誘電率および電導度にも特に下限はないが、誘電率は概ね1.8以上であり、電導度は概ね１×10-3nS/cm以上である。また、有機溶剤Ａの粘度にも下限はないが、概ね0.5mPa・s以上である。
有機溶剤の全量を基準とする有機溶剤Ａの含有量が５重量％未満の場合には、有機溶剤Ａの特長である低粘度であるという利点を生かすことができない。
In order to control the viscosity of the coloring composition within the above range, an organic solvent A having a dielectric constant at 25 ° C. of 10.0 or less, an electrical conductivity at 25 ° C. of 1 nS / cm or less, and a viscosity at 25 ° C. of 1.5 mPa · s or less. In an amount of 5% by weight or more based on the total amount of the organic solvent (100% by weight). There is no particular lower limit to the dielectric constant and conductivity of the organic solvent A, but the dielectric constant is approximately 1.8 or more, and the conductivity is approximately 1 × 10 −3 nS / cm or more. Further, the viscosity of the organic solvent A is not limited, but is generally 0.5 mPa · s or more.
When the content of the organic solvent A based on the total amount of the organic solvent is less than 5% by weight, the advantage of low viscosity, which is a feature of the organic solvent A, cannot be utilized.
有機溶剤Ａとしては、誘電率、電導度および粘度が共に低く、また、沸点、蒸発速度、顔料や樹脂との親和性の面からみて、酢酸イソアミル、３−エトキシプロピオン酸エチル、プロピレングリコールモノメチルエーテルアセテートからなる群から選ばれる少なくとも１種の有機溶剤が特に好ましく用いられる。
The organic solvent A has low dielectric constant, electrical conductivity, and viscosity, and from the viewpoint of boiling point, evaporation rate, and affinity with pigments and resins, isoamyl acetate, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether At least one organic solvent selected from the group consisting of acetates is particularly preferably used.
本発明の着色組成物には、有機溶剤Ａ以外の有機溶剤を、有機溶剤全量を基準として９５％未満の範囲で含有させることができる。
有機溶剤Ａ以外の有機溶剤としては、シクロヘキサノン、プロピレングリコールジアセテート、プロピレングリコールモノメチルエーテル、ジエチレングリコールジエチルエーテル、メチルイソブチルケトン、ｎ−ブチルアルコール、ジプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノメチルエーテル、プロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメブチルエーテル、プロピレングリコールフェニルエーテル、ジプロピレングリコールモノメチルエーテルアセテート、1,3-ブチレングリコールジアセテート、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノブチルエーテルアセテート、3-メトキシブタノール、1,3-ブチレングリコール、トリアセチン、3,3,5-トリメチル-2-シクロヘキセン-1-オン、エチレングリコールモノエチルエーテル、γ−ブチロラクトン等が挙げられる。これらは、単独でまたは２種以上混合して用いられる。
有機溶剤（有機溶剤Ａと有機溶剤Ａ以外の有機溶剤）は、着色組成物中の色素１００重量部に対して、合計して８００〜４０００重量部、好ましくは１０００〜２５００重量部の量で用いることができる。
The colored composition of the present invention can contain an organic solvent other than the organic solvent A in a range of less than 95% based on the total amount of the organic solvent.
Organic solvents other than organic solvent A include cyclohexanone, propylene glycol diacetate, propylene glycol monomethyl ether, diethylene glycol diethyl ether, methyl isobutyl ketone, n-butyl alcohol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, propylene glycol mono Propyl ether, dipropylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monomethyl butyl ether, propylene glycol phenyl ether, dipropylene glycol monomethyl ether acetate, 1,3-butylene glycol diacetate, ethylene Glycol monobutyl A Ter, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, 3-methoxybutanol, 1,3-butylene glycol, triacetin, 3,3,5-trimethyl-2-cyclohexen-1-one, ethylene glycol mono Examples include ethyl ether and γ-butyrolactone. These may be used alone or in admixture of two or more.
The organic solvent (organic solvent other than organic solvent A and organic solvent A) is used in an amount of 800 to 4000 parts by weight, preferably 1000 to 2500 parts by weight, based on 100 parts by weight of the dye in the colored composition. be able to.
有機溶剤Ａは、粘度が低いという観点からは塗工ムラを少なくする能力を保持しているが、絶縁性が高いため帯電しやすく、着色組成物中に含有させた場合に帯電性を上げてしまうという弊害があり、その帯電効果により塗膜の端部に液が集まり易くなる。また、有機溶剤Ａは、色素が有機溶剤と逆極性に帯電すると、塗工ムラを助長させる原因になる場合もある。
従って、粘度が低いという長所を有する有機溶剤Ａを含有する着色組成物の帯電性を下げることは均一な塗膜を形成する上で重要なファクターであり、帯電防止剤の添加により着色組成物の２５℃における誘電率を8.0以上、２５℃における電導度を100ｎS/cm以上にする。
The organic solvent A retains the ability to reduce coating unevenness from the viewpoint of low viscosity, but is easy to be charged because of its high insulating property, and increases the chargeability when contained in a colored composition. The charging effect causes the liquid to easily collect at the edge of the coating film. In addition, the organic solvent A may cause coating unevenness when the dye is charged with a polarity opposite to that of the organic solvent.
Therefore, lowering the charging property of the coloring composition containing the organic solvent A having the advantage of low viscosity is an important factor in forming a uniform coating film. The dielectric constant at 25 ° C. is 8.0 or more, and the conductivity at 25 ° C. is 100 nS / cm or more.
帯電防止剤には、分子内に疎水基と親水基を有するいわゆる界面活性剤の一種で、親水基を有しながらも水に対する溶解性が小さく、着色組成物に添加した場合、その表面張力低下能が低いという特徴を有し、さらに表面張力低下能が低いにも拘らずガラス板への濡れ性が良好なものが有用であり、泡立ちによる塗膜の欠陥が出現しない添加量において十分に帯電性を抑止できるものが好ましく使用できる。
帯電防止剤としては、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンが好ましく使用できる。ポリアルキレンオキサイド単位としては、ポリエチレンオキサイド単位、ポリプロピレンオキサイド単位があり、ジメチルポリシロキサンは、ポリエチレンオキサイド単位とポリプロピレンオキサイド単位とを共に有していてもよい。
Antistatic agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule. It has a hydrophilic group but has low solubility in water. When added to a coloring composition, its surface tension is reduced. In addition, it is useful to have good wettability to the glass plate despite its low surface tension reducing ability, and it is sufficiently charged at an added amount that does not cause defects in the coating film due to foaming. Those that can suppress the property can be preferably used.
As the antistatic agent, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
また、ポリアルキレンオキサイド単位のジメチルポリシロキサンとの結合形態は、ポリアルキレンオキサイド単位がジメチルポリシロキサンの繰り返し単位中に結合したペンダント型、ジメチルポリシロキサンの末端に結合した末端変性型、ジメチルポリシロキサンと交互に繰り返し結合した直鎖状のブロックコポリマー型のいずれであっても良い。
ポリアルキレンオキサイド単位を有するジメチルポリシロキサンは、東レ・ダウコーニング株式会社から市販されており、例えば、FZ-2110、FZ-2122、FZ-2130、FZ-2166、FZ-2191、FZ-2203、FZ-2207が挙げられるが、これらに限定されるものではない。
In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used.
Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
帯電防止剤は、着色組成物中の色素１００重量部に対して、好ましくは０．０１〜１０．００重量部、より好ましくは０．０５〜５．００重量部の量で用いることができる。帯電防止剤の量が色素１００重量部に対して０．０１重量部より少ない場合、基板に形成した薄膜の「端部色ムラ長さ」が長くなる。また、色素１００重量部に対して１０．００重量部より多い場合、塗布液の泡立ちなどの弊害が発生する。 The antistatic agent can be used in an amount of preferably 0.01 to 10.00 parts by weight, more preferably 0.05 to 5.00 parts by weight with respect to 100 parts by weight of the dye in the coloring composition. When the amount of the antistatic agent is less than 0.01 parts by weight with respect to 100 parts by weight of the dye, the “end color unevenness length” of the thin film formed on the substrate becomes long. On the other hand, when the amount is more than 10.00 parts by weight with respect to 100 parts by weight of the dye, problems such as foaming of the coating solution occur.
帯電防止剤には、アニオン性、カチオン性、ノニオン性、または両性の界面活性剤を補助的に加えることも可能である。界面活性剤は、２種以上混合して使用しても構わない。
アニオン性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硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどが挙げられる。
An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the antistatic agent. Two or more kinds of surfactants may be mixed and used.
Examples of the anionic surfactant include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, monoethanolamine laurylsulfate , Lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, and the like.
カオチン性界面活性剤としては、アルキル４級アンモニウム塩やそれらのエチレンオキサイド付加物が挙げられる。
ノニオン性界面活性剤としては、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレートなどの；アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤、また、フッ素系やシリコーン系の界面活性剤が挙げられる。
Examples of chaotic surfactants include alkyl quaternary ammonium salts and their ethylene oxide adducts.
Nonionic surfactants include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, etc. And amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
本発明の着色組成物に含まれる色素担体は、可視光領域の４００〜７００ｎｍの全波長領域において透過率が８０％以上のアクリル系樹脂、モノマーもしくはオリゴマーの混合物により構成される。透明樹脂は、可視光領域の４００〜７００ｎｍの全波長領域において透過率が好ましくは８０％以上、より好ましくは９５％以上の樹脂である。透明樹脂としては、熱可塑性樹脂および感光性樹脂が挙げられ、モノマーもしくはオリゴマーとしては、放射線照射により硬化して透明樹脂を生成するモノマーもしくはオリゴマーが挙げられ、これらを単独で、または２種以上混合して用いることができる。
色素担体は、着色組成物中の色素１００重量部に対して、３０〜７００重量部、好ましくは６０〜４５０重量部の量で用いることができる。また、アクリル系樹脂とモノマーもしくはオリゴマーとの混合物を色素担体として用いる場合には、アクリル系樹脂は、着色組成物中の色素１００重量部に対して、２０〜４００重量部、好ましくは５０〜２５０重量部の量で用いることができる。また、モノマーもしくはオリゴマーは、着色組成物中の色素１００重量部に対して、１０〜３００重量部、好ましくは１０〜２００重量部の量で用いることができる。
The dye carrier contained in the coloring composition of the present invention is composed of a mixture of acrylic resin, monomer or oligomer having a transmittance of 80% or more in the entire wavelength region of 400 to 700 nm in the visible light region . The transparent resin is a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Examples of the transparent resin include a thermoplastic resin and a photosensitive resin, and examples of the monomer or oligomer include a monomer or an oligomer that is cured by irradiation with radiation to form a transparent resin. These may be used alone or in combination of two or more. Can be used.
The dye carrier can be used in an amount of 30 to 700 parts by weight, preferably 60 to 450 parts by weight, with respect to 100 parts by weight of the dye in the coloring composition. Moreover, when using the mixture of acrylic resin and a monomer or an oligomer as a pigment | dye carrier, acrylic resin is 20-400 weight part with respect to 100 weight part of pigment | dye in a coloring composition, Preferably it is 50-250. It can be used in parts by weight. In addition, the monomer or oligomer can be used in an amount of 10 to 300 parts by weight, preferably 10 to 200 parts by weight, with respect to 100 parts by weight of the dye in the colored composition.
熱可塑性樹脂としては、アクリル系樹脂が挙げられる。
Examples of the thermoplastic resin include acrylic resins.
感光性樹脂としては、水酸基、カルボキシル基、アミノ基等の反応性の置換基を有する線状高分子にイソシアネート基、アルデヒド基、エポキシ基等の反応性置換基を有する（メタ）アクリル化合物やケイヒ酸を反応させて、（メタ）アクリロイル基、スチリル基等の光架橋性基を該線状高分子に導入した樹脂が用いられる。また、スチレン−無水マレイン酸共重合物やα−オレフィン−無水マレイン酸共重合物等の酸無水物を含む線状高分子をヒドロキシアルキル（メタ）アクリレート等の水酸基を有する（メタ）アクリル化合物によりハーフエステル化したものも用いられる。 Examples of the photosensitive resin include (meth) acrylic compounds having a reactive substituent such as an isocyanate group, an aldehyde group, and an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, and an amino group. A resin obtained by reacting an acid and introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the linear polymer is used. Further, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified products are also used.
透明樹脂の前駆体であるモノマーおよびオリゴマーとしては、メチル（メタ）アクリレート、エチル（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、２−ヒドロキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、β−カルボキシエチル（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、１，６−ヘキサンジオールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（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トリ（メタ）アクリレート、１, ６−ヘキサンジオールジグリシジルエーテルジ（メタ）アクリレート、ビスフェノールＡジグリシジルエーテルジ（メタ）アクリレート、ネオペンチルグリコールジグリシジルエーテルジ（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、トリシクロデカニル（メタ）アクリレート、エステルアクリレート、メチロール化メラミンの（メタ）アクリル酸エステル、エポキシ（メタ）アクリレート、ウレタンアクリレート等の各種アクリル酸エステルおよびメタクリル酸エステル、（メタ）アクリル酸、スチレン、酢酸ビニル、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、（メタ）アクリルアミド、Ｎ−ヒドロキシメチル（メタ）アクリルアミド、Ｎ−ビニルホルムアミド、アクリロニトリル等が挙げられる。 Monomers and oligomers that are precursors of transparent resins include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, β -Carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylolpropane tri (Meth) acrylate, pentaerythritol tri (meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (me Acrylate), neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, (meth) acrylic acid ester of methylolated melamine, epoxy ( Various acrylic esters and methacrylic esters such as (meth) acrylate and urethane acrylate, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxy Examples include methyl (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.
本発明の着色組成物に含まれる色素としては、有機または無機の顔料を、単独でまたは２種類以上混合して用いることができる。顔料のなかでは、発色性が高く、且つ耐熱性の高い顔料、特に耐熱分解性の高い顔料が好ましく、通常は有機顔料が用いられる。
以下に、本発明の着色組成物に好ましく使用できる有機顔料の具体例を、カラーインデックス番号で示す。
赤色フィルタセグメントを形成するための赤色着色組成物には、例えばC.I. Pigment Red ７、９、１４、４１、４８：１、４８：２、４８：３、４８：４、８１：１、８１：２、８１：３、９７、１２２、１２３、１４６、１４９、１６８、１７７、１７８、１８０、１８４、１８５、１８７、１９２、２００、２０２、２０８、２１０、２１５、２１６、２１７、２２０、２２３、２２４、２２６、２２７、２２８、２４０、２４６、２５４、２５５、２６４、２７２等の赤色顔料を用いることができる。赤色着色組成物には、黄色顔料、オレンジ顔料を併用することができる。
As the dye contained in the colored composition of the present invention, organic or inorganic pigments can be used alone or in admixture of two or more. Among the pigments, pigments having high color developability and high heat resistance, particularly pigments having high heat decomposition resistance are preferred, and organic pigments are usually used.
Below, the specific example of the organic pigment which can be preferably used for the coloring composition of this invention is shown by a color index number.
Red pigmented compositions for forming red filter segments include, for example, CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2. 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224 Red pigments such as 226, 227, 228, 240, 246, 254, 255, 264, and 272 can be used. A yellow pigment and an orange pigment can be used in combination with the red coloring composition.
イエロー色フィルタセグメントを形成するためのイエロー色着色組成物には、例えばC.I. Pigment Yellow １、２、３、４、５、６、１０、１２、１３、１４、１５、１６、１７、１８、２０、２４、３１、３２、３４、３５、３５：１、３６、３６：１、３７、３７：１、４０、４２、４３、５３、５５、６０、６１、６２、６３、６５、７３、７４、７７、８１、８３、８６、９３、９４、９５、９７、９８、１００、１０１、１０４、１０６、１０８、１０９、１１０、１１３、１１４、１１５、１１６、１１７、１１８、１１９、１２０、１２３、１２５、１２６、１２７、１２８、１２９、１３７、１３８、１３９、１４７、１４８、１５０、１５１、１５２、１５３、１５４、１５５、１５６、１６１、１６２、１６４、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７９、１８０、１８１、１８２、１８５、１８７、１８８、１９３、１９４、１９９等の黄色顔料を用いることができる。 Examples of the yellow coloring composition for forming the yellow filter segment include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20. 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 16 It can be used yellow pigments such 168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199.
オレンジ色フィルタセグメントを形成するためのオレンジ色着色組成物には、例えばC.I. Pigment orange ３６、４３、５１、５５、５９、６１等のオレンジ色顔料を用いることができる。
緑色フィルタセグメントを形成するための緑色着色組成物には、例えばC.I. Pigment Green ７、１０、３６、３７等の緑色顔料を用いることができる。緑色着色組成物には黄色顔料を併用することができる。
青色フィルタセグメントを形成するための青色着色組成物には、例えばC.I. Pigment Blue １５、１５：１、１５：２、１５：３、１５：４、１５：６、１６、２２、６０、６４等の青色顔料を用いることができる。青色着色組成物には、C.I. Pigment Violet １、１９、２３、２７、２９、３０、３２、３７、４０、４２、５０等の紫色顔料を併用することができる。
シアン色フィルタセグメントを形成するためのシアン色着色組成物には、例えばC.I. Pigment Blue１５：１、１５：２、１５：４、１５：３、１５：６、１６、８１等の青色顔料を用いることができる。
For example, an orange pigment such as CI Pigment orange 36, 43, 51, 55, 59, 61 can be used as the orange coloring composition for forming the orange filter segment.
As the green coloring composition for forming the green filter segment, for example, a green pigment such as CI Pigment Green 7, 10, 36, 37 can be used. A yellow pigment can be used in combination with the green coloring composition.
Examples of blue coloring compositions for forming blue filter segments include CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. Blue pigments can be used. Purple pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used in combination with the blue coloring composition.
For example, CI Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, 81 or the like is used as a cyan coloring composition for forming a cyan filter segment. Can do.
マゼンタ色フィルタセグメントを形成するためのマゼンタ色着色組成物には、例えばC.I. Pigment Violet １、１９、C.I. Pigment Red１４４、１４６、１７７、１６９、８１等の紫色顔料および赤色顔料を用いることができる。マゼンタ色着色組成物には、黄色顔料を併用することができる。
また、無機顔料としては、硫酸バリウム、亜鉛華、硫酸鉛、黄色鉛、亜鉛黄、べんがら（赤色酸化鉄(III)）、カドミウム赤、群青、紺青、酸化クロム緑、コバルト緑、アンバー、酸化チタン、四酸化鉄などの金属酸化物粉や、金属硫化物粉や、金属粉等が挙げられる。無機顔料は、彩度と明度のバランスを取りつつ良好な塗布性、感度、現像性等を確保するために、有機顔料と組み合わせて用いられる。
本発明の着色組成物には、調色のため、耐熱性を低下させない範囲内で染料を含有させることができる。
For the magenta coloring composition for forming the magenta color filter segment, for example, purple pigments and red pigments such as CI Pigment Violet 1, 19, CI Pigment Red 144, 146, 177, 169, 81 can be used. A yellow pigment can be used in combination with the magenta colored composition.
Inorganic pigments include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber, titanium oxide. And metal oxide powders such as iron tetroxide, metal sulfide powders, metal powders and the like. Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.
The coloring composition of the present invention can contain a dye within a range that does not decrease heat resistance for color matching.
本発明の着色組成物には、該組成物を紫外線等の光照射により硬化する場合には、光重合開始剤が添加される。
光重合開始剤としては、４−フェノキシジクロロアセトフェノン、４−ｔ−ブチル−ジクロロアセトフェノン、ジエトキシアセトフェノン、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、１−ヒドロキシシクロヘキシルフェニルケトン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン等のアセトフェノン系光重合開始剤、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール等のベンゾイン系光重合開始剤、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メチル、４−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、４−ベンゾイル−４’−メチルジフェニルサルファイド等のベンゾフェノン系光重合開始剤、チオキサンソン、２−クロルチオキサンソン、２−メチルチオキサンソン、イソプロピルチオキサンソン、２，４−ジイソプロピルチオキサンソン等のチオキサンソン系光重合開始剤、２，４，６−トリクロロ−ｓ−トリアジン、２−フェニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−メトキシフェニル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−トリル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−ピペニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−スチリル−ｓ−トリアジン、２−（ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（４−メトキシ−ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−トリクロロメチル−（ピペロニル）−６−トリアジン、２，４−トリクロロメチル（４’−メトキシスチリル）−６−トリアジン等のトリアジン系光重合開始剤、ボレート系光重合開始剤、カルバゾール系光重合開始剤、イミダゾール系光重合開始剤等が用いられる。光重合開始剤は、着色組成物中の色素１００重量部に対して、５〜２００重量部、好ましくは１０〜１５０重量部の量で用いることができる。
When the composition is cured by irradiation with light such as ultraviolet rays, a photopolymerization initiator is added to the colored composition of the present invention.
Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Acetophenone photopolymerization initiators such as hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl Benzoin photopolymerization initiators such as ether and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzene Benzophenone photopolymerization initiators such as zoyl-4'-methyldiphenyl sulfide, thioxanthone light such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone Polymerization initiator, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloro) Methyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-pienyl-4,6-bis (trichloromethyl) -s-triazine, 2,4 -Bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (to Chloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine , 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine and other triazine photopolymerization initiators, borate photopolymerization initiators, carbazole photopolymerization initiators, imidazole photopolymerization initiators and the like are used. It is done. A photoinitiator can be used in the amount of 5-200 weight part with respect to 100 weight part of pigment | dyes in a coloring composition, Preferably it is 10-150 weight part.
上記光重合開始剤は、単独でまたは２種以上混合して用いることができるが、増感剤として、α−アシロキシムエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、９，１０−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、４，４’−ジエチルイソフタロフェノン、３，３’，４，４’−テトラ（ｔ−ブチルパーオキシカルボニル）ベンゾフェノン、４，４’−ジエチルアミノベンゾフェノン等の化合物を併用することもできる。増感剤は、着色組成物中の光重合開始剤１００重量部に対して、０．１〜６０重量部の量で用いることができる。 The above photopolymerization initiators can be used alone or in combination of two or more. As the sensitizer, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10- Phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 4,4'-diethylaminobenzophenone These compounds can also be used in combination. The sensitizer can be used in an amount of 0.1 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator in the colored composition.
本発明の着色組成物は、１種または２種以上の色素を、必要に応じて上記光重合開始剤と共に、色素担体および有機溶剤中に三本ロールミル、二本ロールミル、サンドミル、ニーダー、アトライター等の各種分散手段を用いて微細に分散して製造することができる。また、２種以上の色素を含む着色組成物は、各色素を別々に色素担体および有機溶剤中に微細に分散したものを混合して製造することもできる。色素を色素担体および有機溶剤中に分散する際には、適宜、樹脂型顔料分散剤、色素誘導体、界面活性剤等の色素分散剤が使用できる。色素分散剤は、顔料の分散に優れ、分散後の顔料の再凝集を防止する効果が大きいので、色素分散剤を用いて顔料を色素担体および有機溶剤中に分散してなる着色組成物を用いた場合には、透明性に優れたカラーフィルタが得られる。色素分散剤は、着色組成物中の色素１００重量部に対して、０．１〜４０重量部、好ましくは０．１〜３０重量部の量で用いることができる。 The coloring composition of the present invention comprises one or two or more dyes, if necessary, together with the above photopolymerization initiator, in a three-roll mill, two-roll mill, sand mill, kneader, attritor in a dye carrier and an organic solvent. It can be produced by finely dispersing using various dispersing means such as. Moreover, the coloring composition containing 2 or more types of pigment | dyes can also mix and manufacture what each disperse | distributed finely in the pigment | dye carrier and the organic solvent separately. When the dye is dispersed in the dye carrier and the organic solvent, a dye dispersant such as a resin-type pigment dispersant, a dye derivative, and a surfactant can be appropriately used. The pigment dispersant is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, a pigment composition in which the pigment is dispersed in a pigment carrier and an organic solvent using a pigment dispersant is used. If so, a color filter excellent in transparency can be obtained. A pigment | dye dispersing agent can be used in the quantity of 0.1-40 weight part with respect to 100 weight part of pigment | dyes in a coloring composition, Preferably it is 0.1-30 weight part.
樹脂型顔料分散剤は、顔料に吸着する性質を有する顔料親和性部位と、色素担体と相溶性のある部位とを有する樹脂であり、顔料に吸着して顔料の色素担体への分散を安定化する働きをするものである。樹脂型顔料分散剤として具体的には、ポリウレタン、ポリアクリレートなどのポリカルボン酸エステル、不飽和ポリアミド、ポリカルボン酸、ポリカルボン酸（部分）アミン塩、ポリカルボン酸アンモニウム塩、ポリカルボン酸アルキルアミン塩、ポリシロキサン、長鎖ポリアミノアマイドリン酸塩、水酸基含有ポリカルボン酸エステルや、これらの変性物、ポリ（低級アルキレンイミン）と遊離のカルボキシル基を有するポリエステルとの反応により形成されたアミドやその塩などの油性分散剤、（メタ）アクリル酸−スチレン共重合体、（メタ）アクリル酸−（メタ）アクリル酸エステル共重合体、スチレン−マレイン酸共重合体、ポリビニルアルコール、ポリビニルピロリドンなどの水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート系、エチレンオキサイド／プロピレンオキサイド付加化合物、燐酸エステル系等が用いられ、これらは単独でまたは２種以上を混合して用いることができる。 Resin-type pigment dispersants are resins that have a pigment-affinity part that has the property of adsorbing to the pigment, and a part that is compatible with the dye carrier. It works to do. Specific examples of resin-type pigment dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkyleneimines) with polyesters having free carboxyl groups, and the like Water-based dispersants such as oily dispersants such as salts, (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester Modified polyacrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more.
色素誘導体は、有機色素に置換基を導入した化合物である。このような有機色素には、一般に色素とは呼ばれていないナフタレン系、アントラキノン系等の淡黄色の芳香族多環化合物も含まれる。色素誘導体としては、特開昭６３−３０５１７３号公報、特公昭５７−１５６２０号公報、特公昭５９−４０１７２号公報、特公昭６３−１７１０２号公報、特公平５−９４６９号公報等に記載されているものを使用でき、これらは単独でまたは２種類以上を混合して用いることができる。
界面活性剤としては、先述の帯電防止剤に併用可能なものを用いることができる。
A pigment derivative is a compound in which a substituent is introduced into an organic pigment. Such organic dyes also include light yellow aromatic polycyclic compounds such as naphthalene and anthraquinone which are not generally called dyes. Examples of the dye derivatives are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. These can be used alone or in combination of two or more.
As the surfactant, those which can be used in combination with the above-mentioned antistatic agent can be used.
本発明の着色組成物には、組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。また、透明基板との密着性を高めるためにシランカップリング剤等の密着向上剤を含有させることもできる。
貯蔵安定剤としては、例えばベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの４級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、ｔ−ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。貯蔵安定剤は、着色組成物中の色素１００重量部に対して、０．１〜１０重量部の量で用いることができる。
The colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.
Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Examples thereof include phosphine and phosphite. The storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the dye in the coloring composition.
シランカップリング剤としては、ビニルトリス（β−メトキシエトキシ）シラン、ビニルエトキシシラン、ビニルトリメトキシシラン等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の（メタ）アクリルシラン類、β−（３，４−エポキシシクロヘキシル）エチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）エチルトリエトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、Ｎ−β（アミノエチル）γ−アミノプロピルトリメトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルトリエトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリエトキシシラン等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン等のチオシラン類等が挙げられる。シランカップリング剤は、着色組成物中の色素１００重量部に対して、０．０１〜１０重量部、好ましくは０．０５〜５重量部の量で用いることができる。 Examples of the silane coupling agent include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3 , 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) ) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β ( Aminoethyl) γ-aminopro Lutriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N Examples include aminosilanes such as -phenyl-γ-aminopropyltriethoxysilane, thiosilanes such as γ-mercaptopropyltrimethoxysilane, and γ-mercaptopropyltriethoxysilane. The silane coupling agent can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, with respect to 100 parts by weight of the dye in the coloring composition.
本発明の着色組成物は、グラビアオフセット用印刷インキ、水無しオフセット印刷インキ、シルクスクリーン印刷用インキ、溶剤現像型あるいはアルカリ現像型着色レジスト材として調製することができる。溶剤現像型あるいはアルカリ現像型着色レジスト材は、色素担体である熱可塑性樹脂、熱硬化性樹脂または感光性樹脂と、モノマーと、光重合開始剤と、表面調整剤、有機溶剤とを含有する組成物中に色素を分散させたものである。
本発明の着色組成物は、遠心分離、焼結フィルタ、メンブレンフィルタ等の手段にて、５μｍ以上の粗大粒子、好ましくは１μｍ以上の粗大粒子、さらに好ましくは０．５μｍ以上の粗大粒子および混入した塵の除去を行うことが好ましい。
The coloring composition of the present invention can be prepared as gravure offset printing ink, waterless offset printing ink, silk screen printing ink, solvent development type or alkali development type colored resist material. The solvent development type or alkali development type colored resist material is a composition containing a thermoplastic resin, thermosetting resin or photosensitive resin as a dye carrier, a monomer, a photopolymerization initiator, a surface conditioner, and an organic solvent. A pigment is dispersed in a product.
The coloring composition of the present invention is mixed with coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more and coarse particles by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove dust.
つぎに、本発明の着色組成物を用いたカラーフィルタの製造方法について説明する。
本発明のカラーフィルタは、基板上にフィルタセグメントを具備するものであり、例えば、ブラックマトリックスと、赤色、緑色、青色のフィルタセグメントとを備えることができる。前記フィルタセグメントは、スピンコート方式あるいはダイコート方式によって本発明の着色組成物を塗布することにより、基板上に形成される。
カラーフィルタの基板としては、可視光に対して透過率の高いソーダ石灰ガラス、低アルカリ硼珪酸ガラス、無アルカリアルミノ硼珪酸ガラスなどのガラス板や、ポリカーボネート、ポリメタクリル酸メチル、ポリエチレンテレフタレートなどの樹脂板が用いられる。また、ガラス板や樹脂板の表面には、パネル化後の液晶駆動のために、酸化インジウム、酸化錫などからなる透明電極が形成されていてもよい。
Below, the manufacturing method of the color filter using the coloring composition of this invention is demonstrated.
The color filter of the present invention includes a filter segment on a substrate, and can include, for example, a black matrix and red, green, and blue filter segments. The filter segment is formed on the substrate by applying the coloring composition of the present invention by a spin coat method or a die coat method.
Color filter substrates include glass plates such as soda-lime glass, low alkali borosilicate glass, and non-alkali aluminoborosilicate glass that have a high transmittance for visible light, and resins such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate. A plate is used. In addition, a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
現像に際しては、アルカリ現像液として炭酸ナトリウム、水酸化ナトリウム等の水溶液が使用され、ジメチルベンジルアミン、トリエタノールアミン等の有機アルカリを用いることもできる。また、現像液には、消泡剤や界面活性剤を添加することもできる。
現像処理方法としては、シャワー現像法、スプレー現像法、ディップ（浸漬）現像法、パドル（液盛り）現像法等を適用することができる。
なお、紫外線露光感度を上げるために、上記着色レジスト材を塗布乾燥後、水溶性あるいはアルカリ可溶性樹脂、例えばポリビニルアルコールや水溶性アクリル樹脂等を塗布乾燥し、酸素による重合阻害を防止する膜を形成した後、紫外線露光を行うこともできる。
In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
In order to increase the UV exposure sensitivity, the colored resist material is applied and dried, and then a water-soluble or alkali-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.
以下に、実施例により本発明をより具体的に説明するが、本発明はその要旨を超えない限り以下の実施例に限定されるものではない。
なお、実施例および比較例中、「部」および「％」とは「重量部」および「重量％」をそれぞれ意味する。
まず、実施例で用いた有機溶剤Ａの誘電率と電導度と粘度特性を以下の測定器により実測した結果を表１に示す。
誘電率：BROOKHAVEN INSTRUMENTS CORPORATION社製870 LIQUID DIELECTRIC CONSTANT METER
電導度：Scientifica社製 Conductivity Meter Model 645および627
粘度：Ｅ型粘度計（TOKI SANGYO社製TUE-20L型）、回転数１００ｒｐｍで測定。
Hereinafter, the present invention will be described more specifically by way of examples. However, the present invention is not limited to the following examples unless it exceeds the gist.
In the examples and comparative examples, “parts” and “%” mean “parts by weight” and “% by weight”, respectively.
First, Table 1 shows the results obtained by actually measuring the dielectric constant, conductivity, and viscosity characteristics of the organic solvent A used in the examples with the following measuring instrument.
Dielectric constant: 870 LIQUID DIELECTRIC CONSTANT METER manufactured by BROOKHAVEN INSTRUMENTS CORPORATION
Conductivity: Scientific Conductivity Meter Model 645 and 627
Viscosity: Measured with an E-type viscometer (TUE-20L type manufactured by TOKI SANGYO) at a rotation speed of 100 rpm.
次に、実施例および比較例で用いたアクリル樹脂溶液の調製について説明する。樹脂の分子量は、GPC（ゲルパーミエーションクロマトグラフィ）により測定したポリスチレン換算の重量平均分子量である。
（アクリル樹脂溶液の調製）
反応容器にシクロヘキサノン３７０部を入れ、容器に窒素ガスを注入しながら８０℃に加熱して、同温度で下記モノマーおよび熱重合開始剤の混合物を１時間かけて滴下して重合反応を行った。
メタクリル酸 ２０．０部
メチルメタクリレート １０．０部
ブチルメタクリレート ５５．０部
２‐ヒドロキシエチルメタクリレート １５．０部
アゾビスイソブチロニトリル ４．０部
滴下後さらに１００℃で３時間反応させた後、アゾビスイソブチロニトリル１．０部をシクロヘキサノン５０部で溶解させたものを添加し、さらに１００℃で１時間反応を続けてアクリル樹脂の溶液を得た。アクリル樹脂の重量平均分子量は、約４００００であった。
室温まで冷却した後、樹脂溶液約２ｇをサンプリングして１８０℃、２０分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が２０％になるようにシクロヘキサノンを添加してアクリル樹脂溶液を調製した。
Next, preparation of the acrylic resin solution used in Examples and Comparative Examples will be described. The molecular weight of the resin is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography).
(Preparation of acrylic resin solution)
370 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Methacrylic acid 20.0 parts
Methyl methacrylate 10.0 parts
Butyl methacrylate 55.0 parts
2-Hydroxyethyl methacrylate 15.0 parts
Azobisisobutyronitrile 4.0 parts After the addition, the mixture was further reacted at 100 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and further at 100 ° C. The reaction was continued for 1 hour to obtain an acrylic resin solution. The weight average molecular weight of the acrylic resin was about 40,000.
After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20%. An acrylic resin solution was prepared.
［実施例１］
下記の組成の混合物を均一に撹拌混合した後、直径１ｍｍのガラスビーズを用いて、サンドミルで５時間分散した後、５μｍのフィルタで濾過し銅フタロシアニン顔料分散体を作製した。
ε型銅フタロシアニン顔料(C.I. Pigment Blue 15:6) １２．０部
（ＢＡＳＦ製「ヘリオゲンブルーＬ−６７００Ｆ」）
色素分散剤（ゼネカ社製「ソルスパース２００００」） ２．４部
アクリル樹脂溶液 ２８．１部
有機溶剤１（シクロヘキサノン） ５７．５部
ついで、下記組成の混合物を均一になるように攪拌混合した後、１μｍのフィルタで濾過して、青色レジスト材として調整した着色組成物を得た。着色組成物の組成（着色組成物全量を１００とした重量比・右欄は顔料１００重量部に対する重量）を表２に示す。
銅フタロシアニン顔料分散体 ４５．０部
アクリル樹脂溶液 １２．５部
トリメチロールプロパントリアクリレート ４．８部
（新中村化学社製「ＮＫエステルＡＴＭＰＴ」）
光重合開始剤 ２．５部
（チバスペシャルティケミカルズ社製「イルガキュアー９０７」）
増感剤（保土ヶ谷化学社製「ＥＡＢ−Ｆ」） ０．２部
帯電防止剤Ａ ０．０９部
（ポリアルキレンオキサイド単位を有するジメチルポリシロキサン
：東レ・ダウコーニング社製「FZ-2122」）
有機溶剤１（シクロヘキサノン） ０．９１部
有機溶剤２（酢酸イソアミル） ３４．０部
[Example 1]
A mixture having the following composition was stirred and mixed uniformly, then dispersed with a sand mill for 5 hours using glass beads having a diameter of 1 mm, and then filtered with a 5 μm filter to prepare a copper phthalocyanine pigment dispersion.
ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) 12.0 parts (“Heliogen Blue L-6700F” manufactured by BASF)
Dye dispersant (“Solsperse 20000” manufactured by Zeneca) 2.4 parts Acrylic resin solution 28.1 parts Organic solvent 1 (cyclohexanone) 57.5 parts Then, the mixture of the following composition was stirred and mixed to be uniform, It filtered with a 1 micrometer filter and obtained the coloring composition adjusted as a blue resist material. Table 2 shows the composition of the colored composition (weight ratio with the total amount of the colored composition taken as 100 / the right column is the weight relative to 100 parts by weight of the pigment).
Copper phthalocyanine pigment dispersion 45.0 parts Acrylic resin solution 12.5 parts Trimethylol propane triacrylate 4.8 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator 2.5 parts ("Irgacure 907" manufactured by Ciba Specialty Chemicals)
Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 part Antistatic agent A 0.09 part (dimethylpolysiloxane having polyalkylene oxide units: "FZ-2122" manufactured by Toray Dow Corning)
Organic solvent 1 (cyclohexanone) 0.91 part Organic solvent 2 (isoamyl acetate) 34.0 parts
［実施例２〜６および比較例１〜３］
表２に示した各実施例および各比較例の色に相当する顔料と有機溶剤と帯電防止剤を以下の中から選択したこと、および、顔料、分散助剤、アクリル樹脂、モノマー、光重合開始剤、増感剤、有機溶剤、帯電防止剤の組成を表２に示す割合（着色組成物全量を１００とした重量比・右欄は顔料１００重量部に対する重量）に変更した以外は、実施例1と同様にして各色レジスト材として調整した着色組成物を得た。
[Examples 2-6 and Comparative Examples 1-3]
The pigment, the organic solvent, and the antistatic agent corresponding to the colors of the examples and comparative examples shown in Table 2 were selected from the following, and the pigment, dispersion aid, acrylic resin, monomer, and photopolymerization started Except that the composition of the colorant, sensitizer, organic solvent and antistatic agent was changed to the ratio shown in Table 2 (weight ratio with the total amount of the colored composition being 100, the right column is the weight with respect to 100 parts by weight of the pigment). In the same manner as in 1, a colored composition prepared as each color resist material was obtained.
赤用顔料：ジケトピロロピロール系顔料(C.I. Pigment Red 254) ５．０８部
（チバスペシャルティケミカルズ社製「イルガフォーレッドＢ−ＣＦ」）
アントラキノン系顔料(C.I. Pigment Red 177) ０．８２部
（チバスペシャルティケミカルズ社製「クロモフタールレッドＡ２Ｂ」）
アントラキノン系顔料(C.I. Pigment Yellow 199) ０．２０部
（チバスペシャルティケミカルズ社製「クロモフタールエローＧＴ-ＡＤ」）
計６．１０部
緑用顔料：ハロゲン化銅フタロシアニン系顔料(C.I. Pigment Green 36)３．６０部
（東洋インキ製造社製「リオノールグリーン６ＹＫ」）
ニッケルアゾ錯体系顔料(C.I. Pigment Yellow 150) ２．００部
（ランクセス社製「Ｅ４ＧＮ−ＧＴ」）
計５．６０部
青用顔料：ε型銅フタロシアニン顔料(C.I. Pigment Blue 15:6) ５．４０部
（ＢＡＳＦ製「ヘリオゲンブルーＬ−６７００Ｆ」）
有機溶剤１：シクロヘキサノン
有機溶剤２：酢酸イソアミル
有機溶剤３：３−エトキシプロピオン酸エチル
有機溶剤４：プロピレングリコールモノメチルエーテルアセテート
帯電防止剤Ａ：ポリアルキレンオキサイド単位を有するジメチルポリシロキサン
東レ・ダウコーニング社製「FZ-2122」
帯電防止剤Ｂ：ポリアルキレンオキサイド単位を有するジメチルポリシロキサン
東レ・ダウコーニング社製「FZ-2110」
界面活性剤Ｃ：アラルキル変性シリコーン系界面活性剤、ビックケミー社「BYK-323」
界面活性剤Ｄ：フッ素系界面活性剤、大日本インキ化学工業社製「BL-20」
Red pigment: 5.08 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254)
("Irga Four Red B-CF" manufactured by Ciba Specialty Chemicals)
Anthraquinone pigment (CI Pigment Red 177) 0.82 parts
("Chromophthal Red A2B" manufactured by Ciba Specialty Chemicals)
Anthraquinone pigment (CI Pigment Yellow 199) 0.20 parts
("Chromoval Yellow GT-AD" manufactured by Ciba Specialty Chemicals)
6.10 parts in total Green pigment: 3.60 parts of halogenated copper phthalocyanine pigment (CI Pigment Green 36)
("Rionol Green 6YK" manufactured by Toyo Ink Co., Ltd.)
Nickel azo complex pigment (CI Pigment Yellow 150) 2.00 parts
("E4GN-GT" manufactured by LANXESS)
5.60 parts in total Blue pigment: ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) 5.40 parts
(BASF "Heliogen Blue L-6700F")
Organic solvent 1: Cyclohexanone Organic solvent 2: Isoamyl acetate Organic solvent 3: Ethyl 3-ethoxypropionate Organic solvent 4: Propylene glycol monomethyl ether acetate Antistatic agent A: Dimethylpolysiloxane having polyalkylene oxide units
"FZ-2122" manufactured by Toray Dow Corning
Antistatic agent B: dimethylpolysiloxane having polyalkylene oxide units
"FZ-2110" manufactured by Toray Dow Corning
Surfactant C: Aralkyl-modified silicone surfactant, BYK-323 "BYK-323"
Surfactant D: Fluorosurfactant, “BL-20” manufactured by Dainippon Ink & Chemicals, Inc.
実施例１〜６および比較例１〜３で得られた各色レジスト材の２５℃における誘電率、電導度、粘度をそれぞれ以下の測定器、測定条件で測定した。
誘電率：BROOKHAVEN INSTRUMENTS CORPORATION社製870 LIQUID DIELECTRIC CONSTANT METER
電導度：Scientifica社製 Conductivity Meter Model 645および627
粘度：Ｅ型粘度計（TOKI SANGYO社製TUE-20L型）を用い回転数２０ｒｐｍで測定した。
また、ダイコート方式およびスピンコート方式の塗布装置を用いて、３６０ｍｍ×４６５ｍｍサイズのガラス基板上に平均膜厚が２．０μｍとなるようにそれぞれ塗布し、得られた塗布基板を７０℃で２０分間プレベークして乾燥塗膜を得た。以下、評価項目・内容および結果の表し方について記載する。
The dielectric constant, conductivity, and viscosity at 25 ° C. of each color resist material obtained in Examples 1 to 6 and Comparative Examples 1 to 3 were measured using the following measuring instruments and measurement conditions, respectively.
Dielectric constant: 870 LIQUID DIELECTRIC CONSTANT METER manufactured by BROOKHAVEN INSTRUMENTS CORPORATION
Conductivity: Scientific Conductivity Meter Model 645 and 627
Viscosity: Measured at a rotation speed of 20 rpm using an E-type viscometer (TUE-20L type manufactured by TOKI SANGYO).
In addition, using a die coating method and a spin coating method coating apparatus, coating was performed on a glass substrate having a size of 360 mm × 465 mm so as to have an average film thickness of 2.0 μm, and the resulting coated substrate was treated at 70 ° C. for 20 minutes. Pre-baked to obtain a dry coating film. The evaluation items / contents and how to express the results are described below.
（白抜け）
「白抜け」：塗布基板について、白色透過光にて目視によって基板全体を観察し、白抜けが無かった場合を○、白抜けが１〜３個であった場合を△、白抜けが４個以上観察された場合を×とした。
（色ムラ）
「端部色ムラ長さ」：塗工した面に白色光を透過させ、目視で塗膜の端部を観察しムラの境界の長さが5mm未満を○、5mm以上10mm未満を△、10mm以上を×とした。
「全体の色ムラ」：塗工した面に白色光を透過させ、目視で塗膜の端部を観察しムラの程度を評価した。ムラが無い場合○、僅かに観察される場合△、酷い場合×とした。
(Clear white)
“White blank”: For the coated substrate, the whole substrate was visually observed with white transmitted light. When there was no white void, “◯”, when the white void was 1 to 3, “Δ”, and four white voids. The case where it observed above was set as x.
(Color unevenness)
"Edge color unevenness length": White light is transmitted through the coated surface, the edge of the coating film is visually observed, and the length of the unevenness boundary is less than 5mm ○, 5mm or more and less than 10mm Δ, 10mm The above was set as x.
“Overall color unevenness”: White light was transmitted through the coated surface, and the edge of the coating film was visually observed to evaluate the degree of unevenness. When there was no unevenness, it was marked as ◯, when it was observed slightly, and when it was severe, it was marked as x.
（膜厚均一性）
「膜厚均一性（端部）」：塗布塗膜の短辺端中央より基板中心方向に５ｃｍまで５ｍｍおきに膜厚を測定した。最大膜厚をＴmax、最小膜厚をＴmin、平均膜厚をＴavgとし、下式（6）により膜厚均一性（端部）を算出した。
「膜厚均一性（端部以外）」：塗布基板の基板中央より対角線方向に２６ｃｍまで２ｃｍおきに膜厚を測定した。上記同様に下式（6）により膜厚均一性（端部以外）を算出した。
膜厚均一性[％]＝（（Ｔmax−Ｔmin）／（Ｔavg×２））×１００・・・・・・（6）
膜厚均一性[％]は、５％以下であることが好ましく、２％以下であれば均一性が十分高いと判断できる。
（スジムラ）
「スジムラ」：ダイコート塗布基板について、白色透過光にてスジムラ評価を行った。目視によってスジムラがない場合を○、スジムラが観察された場合を×とした。
それぞれの評価の結果を表３に示す
(Thickness uniformity)
“Thickness uniformity (edge)”: The film thickness was measured every 5 mm from the center of the short edge of the coated film to the center of the substrate up to 5 cm. The maximum film thickness was Tmax , the minimum film thickness was Tmin , the average film thickness was Tavg, and the film thickness uniformity (edge) was calculated by the following equation (6).
“Thickness uniformity (other than edge)”: The film thickness was measured every 2 cm from the center of the coated substrate to 26 cm in the diagonal direction. Similarly to the above, the film thickness uniformity (other than the end portion) was calculated by the following formula (6).
Film thickness uniformity [%] = ((T max −T min ) / (T avg × 2)) × 100 (6)
The film thickness uniformity [%] is preferably 5% or less, and if it is 2% or less, it can be judged that the uniformity is sufficiently high.
(Sujimura)
“Striped unevenness”: Evaluation was performed on the die-coated substrate using a white transmitted light. The case where there was no stripe unevenness by visual observation was marked with ○, and the case where stripe unevenness was observed was marked with ×.
The results of each evaluation are shown in Table 3.
実施例１〜６で得られた着色組成物は、誘電率が8.0以上であり、かつ電導度が100nS/cmを十分超えるため、いずれの評価においても良好な結果となった。
比較例１〜３で得られた着色組成物は、誘電率が8.0未満であり、電導度が100nS/cm未満なので、良好な薄膜を得ることができなかった。
Since the colored compositions obtained in Examples 1 to 6 had a dielectric constant of 8.0 or more and the conductivity sufficiently exceeded 100 nS / cm, good results were obtained in any evaluation.
Since the colored compositions obtained in Comparative Examples 1 to 3 have a dielectric constant of less than 8.0 and an electric conductivity of less than 100 nS / cm, a good thin film could not be obtained.
Claims (2)
着色組成物中の色素１００重量部に対して、アクリル系樹脂が２０〜４００重量部であり、モノマーもしくはオリゴマーが１０〜３００重量部であり、有機溶剤が８００〜４０００重量部であり、帯電防止剤が０．０１〜１０．００重量部であり、
該帯電防止剤が、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンであって、
かつ有機溶剤として２５℃における誘電率が10.0以下、２５℃における電導度が1nS/cm以下、かつ２５℃における粘度が1.5mPa・s以下の酢酸イソアミル、３−エトキシプロピオン酸エチル、プロピレングリコールモノメチルエーテルアセテートからなる群から選ばれる少なくとも１種の有機溶剤Ａを有機溶剤の全量を基準として５重量％以上の範囲で含有し、
該着色組成物の２５℃における誘電率が8.0以上、２５℃における電導度が100nS/cm以上、かつ２５℃における粘度が20mPa・s以下であることを特徴とする着色組成物。 A coloring composition containing a dye carrier made of a mixture of acrylic resin, monomer or oligomer having a transmittance of 80% or more in the entire wavelength region of 400 to 700 nm in the visible light region , a dye, an organic solvent, and an antistatic agent. A thing,
20 to 400 parts by weight of the acrylic resin, 10 to 300 parts by weight of the monomer or oligomer, and 800 to 4000 parts by weight of the organic solvent with respect to 100 parts by weight of the coloring matter in the coloring composition. The agent is 0.01 to 10.00 parts by weight,
The antistatic agent is a dimethylpolysiloxane having a polyalkylene oxide unit,
As an organic solvent, isoamyl acetate, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether having a dielectric constant at 25 ° C. of 10.0 or less, conductivity at 25 ° C. of 1 nS / cm or less, and viscosity at 25 ° C. of 1.5 mPa · s or less Containing at least one organic solvent A selected from the group consisting of acetates in a range of 5% by weight or more based on the total amount of the organic solvent;
A coloring composition having a dielectric constant at 25 ° C. of 8.0 or more, an electric conductivity at 25 ° C. of 100 nS / cm or more, and a viscosity at 25 ° C. of 20 mPa · s or less.
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