JP4333682B2 - Coloring composition for color filter and color filter using the same - Google Patents
Coloring composition for color filter and color filter using the same Download PDFInfo
- Publication number
- JP4333682B2 JP4333682B2 JP2006057479A JP2006057479A JP4333682B2 JP 4333682 B2 JP4333682 B2 JP 4333682B2 JP 2006057479 A JP2006057479 A JP 2006057479A JP 2006057479 A JP2006057479 A JP 2006057479A JP 4333682 B2 JP4333682 B2 JP 4333682B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- color filter
- coloring composition
- filter segment
- phthalocyanine
- 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.)
- Active
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- 239000000203 mixture Substances 0.000 title claims description 84
- 238000004040 coloring Methods 0.000 title claims description 41
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 110
- 239000000049 pigment Substances 0.000 claims description 96
- 229920005989 resin Polymers 0.000 claims description 38
- 239000011347 resin Substances 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 7
- 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 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- -1 phthalocyanine compound Chemical class 0.000 description 34
- 239000000463 material Substances 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- 238000000576 coating method Methods 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 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 10
- 239000011163 secondary particle Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000007639 printing Methods 0.000 description 9
- 239000004925 Acrylic resin Substances 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 8
- 239000001055 blue pigment Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 239000012860 organic pigment Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000001056 green pigment Substances 0.000 description 6
- 239000011362 coarse particle Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines 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
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- JRJLLXQDXANQEC-UHFFFAOYSA-N fastogen green y Chemical compound [Cu+2].[N-]1C(N=C2C3=C(Cl)C(Cl)=C(Br)C(Cl)=C3C(N=C3C4=C(Br)C(Cl)=C(Br)C(Cl)=C4C(=N4)[N-]3)=N2)=C(C(Br)=C(Cl)C(Br)=C2Cl)C2=C1N=C1C2=C(Cl)C(Cl)=C(Cl)C(Br)=C2C4=N1 JRJLLXQDXANQEC-UHFFFAOYSA-N 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
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PVMCQBPJKPMOKM-UHFFFAOYSA-N 1-cyclopentylpiperazine Chemical compound C1CCCC1N1CCNCC1 PVMCQBPJKPMOKM-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound 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
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- QYNZYUUXSVZDJO-UHFFFAOYSA-N n-propylbutan-2-amine Chemical compound CCCNC(C)CC QYNZYUUXSVZDJO-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 229940080117 triethanolamine sulfate Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、使用適性、特に流動性および分散安定性に優れるカラーフィルタ用着色組成物、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 for a color filter excellent in suitability for use, particularly fluidity and dispersion stability, and a color filter using the same.
カラーフィルタは、ガラス等の透明な基板の表面に2種以上の異なる色相の微細な帯(ストライプ)状のフィルタセグメントを平行または交差して配置した構成、あるいは微細なフィルタセグメントを一定の配列で配置した構成からなっている。フィルタセグメントは数ミクロン〜数100ミクロンと微細であり、色相毎に所定の配列で整然と配置されている。
一般にカラー液晶表示装置では、カラーフィルタの上に液晶を駆動させるための透明電極が蒸着あるいはスパッタリングにより形成され、さらにその上に液晶を一定方向に配向させるための配向膜が形成されている。これらの透明電極および配向膜の性能を充分に得るには、一般に200℃以上、好ましくは230℃以上の高温で形成する必要がある。このため、現在、カラーフィルタの製造方法は、耐光性、耐熱性に優れる顔料を顔料担体に分散させた組成物を用いてフィルタセグメントを形成する顔料分散法が主流となっている。
The color filter has a configuration in which two or more kinds of fine band (striped) filter segments of different hues are arranged in parallel or intersecting on the surface of a transparent substrate such as glass, or the fine filter segments are arranged in a fixed arrangement. It consists of an arranged configuration. The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.
In general, in a color liquid crystal display device, a transparent electrode for driving liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning liquid crystal in a certain direction is formed thereon. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, it is generally necessary to form them at a high temperature of 200 ° C or higher, preferably 230 ° C or higher. For this reason, at present, the color filter manufacturing method is mainly a pigment dispersion method in which a filter segment is formed using a composition in which a pigment having excellent light resistance and heat resistance is dispersed in a pigment carrier.
一方、近年カラーフィルタに対しては、色特性、すなわち明度や色純度の向上だけでなく、フィルタセグメントを形成する際の塗布均一性、感度、現像性、パターン形状などへの要求が高まっている。特に、ビデオカメラやデジタルカメラ、カラースキャナー等に使われている固体撮像素子用カラーフィルタに対しては、高精細化、高輝度化、高色再現性が要求されている。なかでも高精細化に関しては、フィルタセグメントに数ミクロンの異物が混入すると、誤った信号を撮像素子に送ってしまい、不良の原因となってしまう。異物の原因は主に顔料の二次粒子とされており、これまでは顔料の分散度を高めて二次粒子を減らしたり、適当な孔径のフィルタで濾過することにより異物の混入を防いできた。 On the other hand, in recent years, for color filters, there are increasing demands not only for improving color characteristics, that is, brightness and color purity, but also for coating uniformity, sensitivity, developability, and pattern shape when forming filter segments. . In particular, high definition, high luminance, and high color reproducibility are required for color filters for solid-state image sensors used in video cameras, digital cameras, color scanners, and the like. In particular, regarding high definition, if a foreign matter of several microns is mixed in the filter segment, an incorrect signal is sent to the image sensor, which causes a defect. The cause of foreign matters is mainly secondary particles of pigments, and until now it has been possible to prevent the inclusion of foreign matters by increasing the degree of dispersion of the pigment to reduce secondary particles or filtering with a filter with an appropriate pore size. .
しかし、顔料を過度に分散すると、二次粒子から一次粒子へ顔料の分散が進むのと並行して一次粒子の破砕が進み再凝集が起きるという問題があった。また、一次粒子あるいは二次粒子の微細化が進行した顔料は、一般に凝集し易く、微細化が進行し過ぎた場合には巨大な塊状の顔料固形物が形成される場合がある。さらに、微細化が進行した顔料は、樹脂などを含有する顔料担体中へ分散させて二次粒子を一次粒子にまで近づけて安定化させることが非常に困難であった。
また、微細化が進行した顔料を顔料担体に分散させた着色組成物は、時間と共に往々にして顔料粒子が凝集し、粗粒子が発生したり、高粘度化によりチキソトロピック性を示すようになる。このような着色組成物の粘度上昇、流動性不良は、製造作業上の問題や製品価値に種々の問題を引き起こす。例えば、流動性の不良はフィルタに対する濡れ性が悪化し、濾過速度を遅くする原因となる。
However, when the pigment is excessively dispersed, the primary particles are crushed and reaggregation occurs in parallel with the dispersion of the pigment from the secondary particles to the primary particles. In addition, pigments whose primary particles or secondary particles have been refined are generally easily aggregated, and when the refinement is excessively advanced, a huge lump of pigment solid may be formed. Furthermore, it has been very difficult to stabilize a pigment whose fineness has been advanced by dispersing it in a pigment carrier containing a resin or the like and bringing the secondary particles close to the primary particles.
In addition, a colored composition in which a pigment that has been refined is dispersed in a pigment carrier often aggregates with time to produce coarse particles, or exhibits thixotropic properties due to increased viscosity. . Such an increase in viscosity and poor fluidity of the colored composition causes various problems in production work and product value. For example, poor fluidity deteriorates the wettability with respect to the filter and causes a slow filtration rate.
フタロシアニン構造を有する有機顔料を分散させるために有機顔料を母体骨格として側鎖に酸性基や塩基性基を置換基として有する顔料誘導体を分散剤として混合する方法が、特許文献1〜2に提案されているが、高度な顔料分散が要求されるカラーフィルタ用途においては、十分な適性が得られていない。
そこで、本発明は、優れた流動性および分散安定性を持ち、フィルタセグメントを形成した時にフィルタセグメント中での顔料の二次粒子に起因する異物がきわめて少なく、透過率が高く色再現性に優れたカラーフィルタを形成し得るカラーフィルタ用着色組成物の提供を目的とする。
また、本発明は、フィルタセグメント中での顔料の二次粒子に起因する異物がきわめて少なく、透過率が高く色再現性に優れ、コントラストの高いカラーフィルタを提供することを目的とする。
Therefore, the present invention has excellent fluidity and dispersion stability, and when the filter segment is formed, there are very few foreign matters due to the secondary particles of the pigment in the filter segment, and the transmittance is high and the color reproducibility is excellent. Another object of the present invention is to provide a color filter coloring composition capable of forming a color filter.
Another object of the present invention is to provide a color filter having very little foreign matter due to secondary particles of pigment in the filter segment, high transmittance, excellent color reproducibility, and high contrast.
本発明のカラーフィルタ用着色組成物は、透明樹脂、その前駆体またはそれらの混合物からなる顔料担体と、顔料と、下記一般式(1)で示される置換基をフタロシアニン残基に対し1個有するフタロシアニン誘導体(D1)と、下記一般式(1)で示される置換基をフタロシアニン残基に対し2個有するフタロシアニン誘導体(D2)とを含有するカラーフィルタ用着色組成物であって、前記フタロシアニン誘導体(D1):前記フタロシアニン誘導体(D2)の重量比が85:15〜56:44であることを特徴とする。
一般式(1)
General formula (1)
また、本発明のカラーフィルタは、少なくとも1つの赤色フィルタセグメント、少なくとも1つの青色フィルタセグメント、および少なくとも1つの緑色フィルタセグメントを具備するカラーフィルタであって、前記青色フィルタセグメントおよび/または緑色フィルタセグメントが、本発明のカラーフィルタ用着色組成物から形成されていることを特徴とする。
また、本発明のカラーフィルタは、少なくとも1つのイエロー色フィルタセグメント、少なくとも1つのマゼンタ色フィルタセグメント、および少なくとも1つのシアン色フィルタセグメントを具備するカラーフィルタであって、前記シアン色フィルタセグメントが、本発明のカラーフィルタ用着色組成物から形成されていることを特徴とする。
The color filter of the present invention is a color filter comprising at least one red filter segment, at least one blue filter segment, and at least one green filter segment, wherein the blue filter segment and / or the green filter segment is provided. It is formed from the coloring composition for color filters of this invention.
The color filter of the present invention is a color filter comprising at least one yellow color filter segment, at least one magenta color filter segment, and at least one cyan color filter segment. It is formed from the coloring composition for color filters of the invention.
本発明のカラーフィルタ用着色組成物は、特定の塩基性置換基をフタロシアニン残基に対し1個有するフタロシアニン誘導体(D1)と、2個有するフタロシアニン誘導体(D2)とを特定の比率で用いて、顔料を顔料担体に分散しているため、顔料の二次粒子が極めて少なく、顔料の粒径が均一に揃い、顔料の高分散化が達成できている。そのため、本発明のカラーフィルタ用着色組成物を用いることにより、高精細で、透過率が高く色再現性に優れ、コントラストが高い青色フィルタセグメントや緑色フィルタセグメント、シアン色フィルタセグメントを形成することが可能となる。 The coloring composition for a color filter of the present invention uses a phthalocyanine derivative (D1) having one specific basic substituent with respect to a phthalocyanine residue and a phthalocyanine derivative (D2) having two specific substituents at a specific ratio, Since the pigment is dispersed in the pigment carrier, the secondary particle of the pigment is extremely small, the pigment particle size is uniform, and the pigment can be highly dispersed. Therefore, by using the coloring composition for a color filter of the present invention, it is possible to form a blue filter segment, a green filter segment, and a cyan filter segment with high definition, high transmittance, excellent color reproducibility, and high contrast. It becomes possible.
まず、好ましい実施の形態を挙げて、本発明のカラーフィルタ用着色組成物について詳細に説明する。
本発明のカラーフィルタ用着色組成物は、透明樹脂、その前駆体またはそれらの混合物からなる顔料担体と、顔料と、下記一般式(1)で示される置換基をフタロシアニン残基に対し1個有するフタロシアニン誘導体(D1)と、下記一般式(1)で示される置換基をフタロシアニン残基に対し2個有するフタロシアニン誘導体(D2)とを含有するカラーフィルタ用着色組成物であって、前記フタロシアニン誘導体(D1):前記フタロシアニン誘導体(D2)の重量比が85:15〜56:44、好ましくは65:35〜56:44であることを特徴とする。
一般式(1)
The coloring composition for a color filter of the present invention has a pigment carrier composed of a transparent resin, a precursor thereof or a mixture thereof, a pigment, and one substituent represented by the following general formula (1) with respect to the phthalocyanine residue. A coloring composition for a color filter comprising a phthalocyanine derivative (D1) and a phthalocyanine derivative (D2) having two substituents represented by the following general formula (1) with respect to the phthalocyanine residue, the phthalocyanine derivative ( D1): The weight ratio of the phthalocyanine derivative (D2) is 85:15 to 56:44, preferably 65:35 to 56:44.
General formula (1)
前記フタロシアニン誘導体(D1)と前記フタロシアニン誘導体(D2)とを共に用いても、前記フタロシアニン誘導体(D1)の比率が上記範囲より多い、または少ない場合には、分散後に顔料の凝集が発生して流動性が悪くなり、ろ過性の低下が発生する。また、分散安定性も悪くなるので、経時増粘や粗粒の発生が起こり、コントラストの低下などの原因となる。
前記フタロシアニン誘導体(D1)と前記フタロシアニン誘導体(D2)とは、カラーフィルタ用着色組成物中に含まれる顔料100重量部に対して、合計して1〜30重量部、好ましくは2.5〜15重量部の量で用いることができる。
Even when both the phthalocyanine derivative (D1) and the phthalocyanine derivative (D2) are used, if the ratio of the phthalocyanine derivative (D1) is more than or less than the above range, the aggregation of the pigment occurs after the dispersion The filterability deteriorates and the filterability decreases. Further, since the dispersion stability is deteriorated, thickening with time and generation of coarse particles occur, which causes a decrease in contrast.
The said phthalocyanine derivative (D1) and the said phthalocyanine derivative (D2) are 1-30 weight part in total with respect to 100 weight part of pigments contained in the coloring composition for color filters, Preferably it is 2.5-15. It can be used in parts by weight.
上記一般式(1)の置換基を有するフタロシアニン誘導体(D1)および(D2)は、種々の合成経路で合成することができる。例えば、フタロシアニン化合物に下記一般式(2)〜(5)で示される置換基を導入した後、アミン成分を反応させて上記一般式(1)の置換基を形成することによって合成することができる。
一般式(2) −SO2Cl
一般式(3) −COCl
一般式(4) −CH2Cl
一般式(5) −CH2NHCOCH2Cl
The phthalocyanine derivatives (D1) and (D2) having the substituent of the general formula (1) can be synthesized by various synthetic routes. For example, it can synthesize | combine by introduce | transducing the substituent shown by following General formula (2)-(5) to a phthalocyanine compound, and making an amine component react and forming the substituent of the said General formula (1). .
Formula (2) -SO 2 Cl
Formula (3) -COCl
Formula (4) —CH 2 Cl
Formula (5) —CH 2 NHCOCH 2 Cl
前記フタロシアニン誘導体(D1)と前記フタロシアニン誘導体(D2)の重量比は、以下のようにしてコントロールすることができる。
例えば、一般式(2)で示される置換基を導入する場合には、フタロシアニン化合物をクロルスルホン酸に溶解して、塩化チオニル等の塩素化剤を反応させるが、この時の反応温度、反応時間等の条件により、フタロシアニン化合物に導入する一般式(2)で示される置換基数をコントロールし、結果として前記フタロシアニン誘導体(D1)と前記フタロシアニン誘導体(D2)の重量比をコントロールすることができる。
The weight ratio of the phthalocyanine derivative (D1) and the phthalocyanine derivative (D2) can be controlled as follows.
For example, when the substituent represented by the general formula (2) is introduced, the phthalocyanine compound is dissolved in chlorosulfonic acid and reacted with a chlorinating agent such as thionyl chloride. The reaction temperature and reaction time at this time The number of substituents represented by the general formula (2) to be introduced into the phthalocyanine compound can be controlled by the above conditions, and as a result, the weight ratio of the phthalocyanine derivative (D1) and the phthalocyanine derivative (D2) can be controlled.
また、一般式(3)で示される置換基を導入する場合には、まず、カルボキシル基を有するフタロシアニン化合物を公知の方法に従って合成したのち、ベンゼン等の芳香族溶媒中で塩化チオニル等の塩素化剤を反応させる。フタロシアニン化合物は、一般には無水フタル酸、尿素および塩化第一銅をモリブデン酸アンモニウムのような触媒の存在下で、芳香族溶媒中で加熱することにより得られるが、無水フタル酸に一部、無水トリメリット酸あるいは無水ピロメリット酸を加えて同様に反応させることによって、カルボキシル基を有するフタロシアニン化合物を得ることができ、この時の無水フタル酸に対する無水トリメリット酸あるいは無水ピロメリット酸のモル比を調整することによって、フタロシアニン化合物に導入するカルボキシル基数(=一般式(3)で示される置換基数)をコントロールし、結果として前記フタロシアニン誘導体(D1)と前記フタロシアニン誘導体(D2)の重量比をコントロールすることができる。 In addition, when introducing the substituent represented by the general formula (3), first, a phthalocyanine compound having a carboxyl group is synthesized according to a known method, and then chlorinated such as thionyl chloride in an aromatic solvent such as benzene. React the agent. Phthalocyanine compounds are generally obtained by heating phthalic anhydride, urea and cuprous chloride in an aromatic solvent in the presence of a catalyst such as ammonium molybdate. By adding trimellitic acid or pyromellitic anhydride and reacting in the same manner, a phthalocyanine compound having a carboxyl group can be obtained, and the molar ratio of trimellitic anhydride or pyromellitic anhydride to phthalic anhydride at this time is determined. By adjusting, the number of carboxyl groups introduced into the phthalocyanine compound (= the number of substituents represented by the general formula (3)) is controlled, and as a result, the weight ratio of the phthalocyanine derivative (D1) and the phthalocyanine derivative (D2) is controlled. be able to.
フタロシアニン残基を構成するフタロシアニン化合物としては、銅、ニッケル、コバルト、アルミニウム、鉄、亜鉛、マンガンなどの中心金属を有する金属フタロシアニン、および無金属フタロシアニンが挙げられる。さらに、3価以上の原子価を有するハロゲン化金属であってもよい。所望により、塩素原子、臭素原子、場合によっては、スルホン酸基、カルボン酸基を有していてもよい。フタロシアニンの中心核として、3価以上の原子価を有するハロゲン化金属であってもよい。フタロシアニン化合物は、フタルイミド骨格の水素原子が所望により、塩素原子、臭素原子、場合によっては、スルホン酸基、カルボキシル基で置換されていてもよい。 Examples of the phthalocyanine compound constituting the phthalocyanine residue include metal phthalocyanines having a central metal such as copper, nickel, cobalt, aluminum, iron, zinc, manganese, and metal-free phthalocyanines. Further, it may be a metal halide having a valence of 3 or more. If desired, it may have a chlorine atom, a bromine atom, and optionally a sulfonic acid group or a carboxylic acid group. A metal halide having a valence of 3 or more may be used as the central nucleus of phthalocyanine. In the phthalocyanine compound, the hydrogen atom of the phthalimide skeleton may be optionally substituted with a chlorine atom, a bromine atom, or in some cases, a sulfonic acid group or a carboxyl group.
一般式(2)〜(5)で示される置換基と反応させて一般式(1)の置換基を形成するために使用されるアミン成分としては、例えば、ジメチルアミン、ジエチルアミン、N,N−エチルイソプロピルアミン、N,N−エチルプロピルアミン、N,N−メチルブチルアミン、N,N−メチルイソブチルアミン、N,N−ブチルエチルアミン、N,N−tert−ブチルエチルアミン、ジイソプロピルアミン、ジプロピルアミン、N,N−sec−ブチルプロピルアミン、ジブチルアミン、ジーsec−ブチルアミン、ジイソブチルアミン、N,N−イソブチル−sec−ブチルアミン、ジアミルアミン、ジイソアミルアミン、ジヘキシルアミン、ジ(2−エチルへキシル)アミン、ジオクチルアミン、N,N−メチルオクタデシルアミン、ジデシルアミン、ジアリルアミン、N,N−エチル−1,2−ジメチルプロピルアミン、N,N−メチルヘキシルアミン、ジオレイルアミン、ジステアリルアミン、N,N−ジメチルアミノメチルアミン、N,N−ジメチルアミノエチルアミン、N,N−ジメチルアミノアミルアミン、N,N−ジメチルアミノブチルアミン、N,N−ジエチルアミノエチルアミン、N,N−ジエチルアミノプロピルアミン、N,N−ジエチルアミノヘキシルアミン、N,N−ジエチルアミノブチルアミン、N,N−ジエチルアミノペンチルアミン、N,N−ジプロピルアミノブチルアミン、N,N−ジブチルアミノプロピルアミン、N,N−ジブチルアミノエチルアミン、N,N−ジブチルアミノブチルアミン、N,N−ジイソブチルアミノペンチルアミン、N,N−メチルーラウリルアミノプロピルアミン、N,N−エチルーヘキシルアミノエチルアミン、N,N−ジステアリルアミノエチルアミン、N,N−ジオレイルアミノエチルアミン、N,N−ジステアリルアミノブチルアミン、ピペリジン、2−ピペコリン、3−ピペコリン、4−ピペコリン、2,4−ルペチジン、2,6−ルペチジン、3,5−ルペチジン、3−ピペリジンメタノール、ピペコリン酸、イソニペコチン酸、イソニコペチン酸メチル、イソニコペチン酸エチル、2−ピペリジンエタノール、ピロリジン、3−ヒドロキシピロリジン、N−アミノエチルピペリジン、N−アミノエチル−4−ピペコリン、N−アミノエチルモルホリン、N−アミノプロピルピペリジン、N−アミノプロピル−2−ピペコリン、N−アミノプロピル−4−ピペコリン、N−アミノプロピルモルホリン、N−メチルピペラジン、N−ブチルピペラジン、N−メチルホモピペラジン、1−シクロペンチルピペラジン、1−アミノ−4−メチルピペラジン、1−シクロペンチルピペラジン等が挙げられる。 Examples of the amine component used for reacting with the substituents represented by the general formulas (2) to (5) to form the substituent of the general formula (1) include dimethylamine, diethylamine, N, N— Ethyl isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, dibutylamine, disec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, Dioctylamine, N, N-methyloctadecylamine, di Silamine, diallylamine, N, N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N -Diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, , N-methyl-laurylaminopropylamine, N, N-ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2 -Pipecoline, 3-Pipecoline, 4-Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinmethanol, Pipecolic acid, Isonipecotic acid, Methyl isonicopetinate, Ethyl isonicopetinate, 2- Piperidine ethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecholine, N-aminopro Pyr-4-pipecoline, N-aminopropylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine .
一般式(2)〜(5)で示される置換基と上記アミン成分との反応時には、一般式(2)〜(5)で示される置換基の一部が加水分解して、塩素が水酸基に置換することがある。その場合、一般式(2)で示される置換基はスルホン酸基となり、一般式(3)で示される置換基はカルボン酸基となるが、何れも遊離酸のままでもよく、また、1〜3価の金属または上記モノアミンと塩を形成していてもよい。 During the reaction of the substituents represented by the general formulas (2) to (5) with the amine component, a part of the substituents represented by the general formulas (2) to (5) are hydrolyzed to convert chlorine into hydroxyl groups. May be replaced. In that case, the substituent represented by the general formula (2) is a sulfonic acid group, and the substituent represented by the general formula (3) is a carboxylic acid group. A salt may be formed with a trivalent metal or the above monoamine.
本発明のカラーフィルタ用着色組成物に含有される顔料としては、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。使用することができる顔料としては、フタロシアニン系、アゾ系、アントラキノン系、キナクリドン系、ジオキサジン系、アンサンスロン系、インダンスロン系、ペリレン系、チオインジゴ系、イソインドリン系、キノフタロン系、ジケトピロロピロール系などの有機顔料が挙げられるが、前記フタロシアニン誘導体(D1)および(D2)はフタロシアニン骨格を有するため、C.I.Pigment Blue 15、15:1、15:2、15:3、15:4、15:6、C.I.Pigment Green 7、36から選ばれる少なくとも1種の顔料を使用すると、特に分散効果が高いことから好ましい。
以下に、本発明の着色組成物に使用可能な有機顔料の具体例を、カラーインデックス番号で示す。
As a pigment contained in the coloring composition for a color filter of the present invention, organic or inorganic pigments can be used alone or in admixture of two or more. The pigment is preferably a pigment having a high color developability and a high heat resistance, particularly a pigment having a high heat decomposition resistance, and an organic pigment is usually used. Examples of pigments that can be used include phthalocyanine, azo, anthraquinone, quinacridone, dioxazine, ansanthrone, indanthrone, perylene, thioindigo, isoindoline, quinophthalone, diketopyrrolopyrrole Organic pigments such as those based on phthalocyanine, but the phthalocyanine derivatives (D1) and (D2) have a phthalocyanine skeleton. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, C.I. I. It is preferable to use at least one pigment selected from Pigment Green 7 and 36 because the dispersion effect is particularly high.
Below, the specific example of the organic pigment which can be used for the coloring composition of this invention is shown with a color index number.
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。
また、無機顔料としては、酸化チタン、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、チタンブラック、合成鉄黒、カーボンブラック等が挙げられる。無機顔料は、色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ることができる。
Examples of the green coloring composition for forming the green filter segment include C.I. I. Pigment green 7, 10, 36, 37 or the like can be used. A yellow pigment can be used in combination with the green 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.
Inorganic pigments include titanium oxide, 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 black, synthetic iron black, carbon black and the like. Inorganic pigments can be used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while balancing chromaticity.
これらの顔料は、着色組成物中に1.5〜15重量%の割合で含有されることが好ましい。また、顔料は、最終フィルタセグメント中に好ましくは10〜60重量%、より好ましくは20〜55重量%の割合で含有され、その残部は、顔料担体により提供される樹脂質バインダーから実質的になる。
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。
These pigments are preferably contained in the coloring composition in a proportion of 1.5 to 15% by weight. Further, the pigment is preferably contained in the final filter segment in a proportion of 10 to 60% by weight, more preferably 20 to 55% by weight, and the balance substantially consists of a resinous binder provided by the pigment carrier. .
The coloring composition of the present invention can contain a dye within a range that does not decrease heat resistance for color matching.
本発明のカラーフィルタ用着色組成物に含有される顔料担体は、顔料を分散させるものであり、透明樹脂、その前駆体またはそれら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。
本発明のカラーフィルタ用着色組成物を用いて後述のフォトリソグラフィー法によりフィルタセグメントを形成する場合には、現像が一般にアルカリ水溶液で行われており、乾燥塗膜が現像時に全て除去され、いわゆる現像残渣が残らないようにするため、アルカリ可溶性の透明樹脂を配合することが好ましい。また、カラーフィルタとしての耐熱性や耐光性等の諸耐性を損なわないよう透明樹脂の種類および配合量を選択する必要がある。
透明樹脂には、熱可塑性樹脂、熱硬化性樹脂、および感光性樹脂があり、その前駆体には、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などがあり、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。顔料担体は、顔料100重量部に対して5〜200重量部の量で用いることができる。
The pigment carrier contained in the coloring composition for a color filter of the present invention is for dispersing a pigment, and is composed of a transparent resin, a precursor thereof, or a mixture thereof. 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.
When the filter segment is formed by the photolithography method described later using the coloring composition for a color filter of the present invention, development is generally performed with an alkaline aqueous solution, and the dry coating film is completely removed during development, so-called development. In order not to leave a residue, it is preferable to blend an alkali-soluble transparent resin. Further, it is necessary to select the type and blending amount of the transparent resin so as not to impair various resistances such as heat resistance and light resistance as the color filter.
The transparent resin includes a thermoplastic resin, a thermosetting resin, and a photosensitive resin, and its precursor includes a monomer or an oligomer that is cured by irradiation with radiation to generate a transparent resin. Alternatively, two or more kinds can be mixed and used. The pigment carrier can be used in an amount of 5 to 200 parts by weight with respect to 100 parts by weight of the pigment.
熱可塑性樹脂としては、例えば、ブチラール樹脂、スチレンーマレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、スチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリブタジエン、ポリイミド樹脂等が挙げられる。また、熱硬化性樹脂としては、例えば、エポキシ樹脂、ベンゾグアナミン樹脂、ロジン変性マレイン酸樹脂、ロジン変性フマル酸樹脂、メラミン樹脂、尿素樹脂、フェノール樹脂等が挙げられる。 Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, styrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol 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樹脂に、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。 As the photosensitive resin, a (meth) acrylic compound or cinnamic acid having a reactive substituent such as an isocyanate group, an aldehyde group, or an epoxy group is added to a resin having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group. Resins into which photocrosslinkable groups such as (meth) acryloyl groups and styryl groups have been introduced by reaction are 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、メラミン(メタ)アクリレート、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、これらを単独でまたは2種類以上混合して用いることができる。 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, melamine (meth) acrylate, epoxy (meth) acrylate, urethane Various acrylates and methacrylates such as acrylates, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide , N-vinylformamide, acrylonitrile and the like, and these can be used alone or in admixture of two or more.
カラーフィルタ用着色組成物には、該着色組成物を紫外線照射により硬化するときには、光重合開始剤等が添加される。
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−ピペロニル−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、着色組成物中の顔料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 colored composition is cured by ultraviolet irradiation, a photopolymerization initiator or the like is added to the colored composition for color filter.
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-piperonyl-4,6-bis (trichloromethyl) -s-triazine, 2,4 -Bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis ( Lichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, Triazine photopolymerization initiators such as 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, borate photopolymerization initiators, carbazole photopolymerization initiators, imidazole photopolymerization initiators, and the like are used. . A photoinitiator can be used in the amount of 5-200 weight part with respect to 100 weight part of pigments in a coloring composition, Preferably it is 10-150 weight part.
上記光重合開始剤は、単独であるいは2種以上混合して用いるが、増感剤として、α−アシロキシエステル、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 are used alone or in admixture of two or more. As sensitizers, α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrene. Compounds such as quinone, camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone Can also be used together. 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.
さらに、本発明のカラーフィルタ用着色組成物には、顔料を充分に顔料担体中に分散させ、ガラス基板等の透明基板上に乾燥膜厚が0.2〜5μmとなるように塗布してフィルタセグメントを形成することを容易にするために溶剤を含有させることができる。
溶剤としては、例えば1,2,3−トリクロロプロパン、1,3−ブタンジオール、1,3-ブチレングリコール、1,3-ブチレングリコールジアセテート、1,4−ジオキサン、2−ヘプタノン、2−メチル−1,3−プロパンジオール、3,5,5-トリメチル-2-シクロヘキセン-1-オン、3,3,5−トリメチルシクロヘキサノン、3−エトキシプロピオン酸エチル、3−メチル−1,3−ブタンジオール、3−メトキシ−3−メチル−1−ブタノール、3−メトキシ−3−メチルブチルアセテート、3-メトキシブタノール、3−メトキシブチルアセテート、4−ヘプタノン、m−キシレン、m−ジエチルベンゼン、m−ジクロロベンゼン、N,N−ジメチルアセトアミド、N,N−ジメチルホルムアミド、n−ブチルアルコール、n−ブチルベンゼン、n−プロピルアセテート、N−メチルピロリドン、o−キシレン、o−クロロトルエン、o−ジエチルベンゼン、o−ジクロロベンゼン、p−クロロトルエン、p−ジエチルベンゼン、sec−ブチルベンゼン、tert−ブチルベンゼン、γ―ブチロラクトン、イソブチルアルコール、イソホロン、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノターシャリーブチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノプロピルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、ジイソブチルケトン、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノエ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、ジエチレングリコールモノメチルエーテル、シクロヘキサノール、シクロヘキサノールアセテート、シクロヘキサノン、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、ジ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メチルエーテル、ダイアセトンアルコール、トリアセチン、トリ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チルエーテル、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フェニルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノプロピルエーテル、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メチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、ベンジルアルコール、メチルイソブチルケトン、メチルシクロヘキサノール、酢酸n−アミル、酢酸n−ブチル、酢酸イソアミル、酢酸イソブチル、酢酸プロピル、二塩基酸エステル等が挙げられ、これらを単独でもしくは混合して用いる。溶剤は、着色組成物中の顔料100重量部に対して、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。
Further, in the coloring composition for a color filter of the present invention, the pigment is sufficiently dispersed in a pigment carrier and applied to a transparent substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. A solvent can be included to facilitate the formation of the segments.
Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, and 2-methyl. -1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o- Xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene Glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol mono Hexyl ether, ethylene glycol monomethyl ether Ter, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone , Dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dip Pyrene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether , Propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, Isobutyl, propyl acetate, include dibasic acid esters such as, used alone or in combination. The solvent can be used in an amount of 800 to 4000 parts by weight, preferably 1000 to 2500 parts by weight with respect to 100 parts by weight of the pigment in the coloring composition.
本発明のカラーフィルタ用着色組成物には、さらに樹脂型顔料分散剤や界面活性剤を含有させても良い。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を有し、顔料に吸着して顔料の顔料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、これを用いて顔料を顔料担体中に分散した場合には、透明性に優れたカラーフィルタが得られる。樹脂型顔料分散剤としては、上記透明樹脂として用いられる樹脂以外のポリウレタン、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等が用いられる。また、(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、エチレンオキサイド/プロピレンオキサイド付加物、燐酸エステル等も用いられる。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。 The coloring composition for a color filter of the present invention may further contain a resin type pigment dispersant or a surfactant. The resin-type pigment dispersant has a pigment affinity portion having a property of adsorbing to the pigment, and functions to adsorb to the pigment and stabilize the dispersion of the pigment on the pigment carrier. Resin-type pigment dispersants are excellent in pigment dispersion and have a great effect of preventing re-aggregation of the pigment after dispersion. When this is used to disperse the pigment in the pigment carrier, it has excellent transparency. A filter is obtained. Examples of the resin-type pigment dispersant include polyurethanes other than the resins used as the transparent resin, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, and polycarboxylic acid ammonium salts. , Polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters and their modified products, poly lower alkylene imines and reaction with polyesters having free carboxyl groups. Amides and salts thereof are used. In addition, water-soluble resins such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, and water-soluble Polymer compounds, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, phosphate esters, and the like are also used. These can be used alone or in admixture of two or more.
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のアニオン性界面活性剤;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ノニオン性界面活性剤;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などのカオチン性界面活性剤;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が挙げられ、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。 Surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, lauryl sulfate monoethanolamine, lauryl Anionic surfactants such as triethanolamine sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more.
また、本発明のカラーフィルタ用着色組成物には、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。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、トリエチルホスフィン、トリフェニルホ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、着色組成物中の顔料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。 In addition, the colored composition for a color filter of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the composition. 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 ethers such as methyl ether, t-butylpyrocatechol, triethylphosphine, and triphenylphosphine. And phosphites. 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 pigment in the coloring composition.
本発明の着色組成物は、溶剤現像型あるいはアルカリ現像型着色レジスト材の形態で調整することができる。着色レジスト材は、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を含む顔料担体中に顔料を分散させたものであり、1種または2種以上の顔料を、フタロシアニン誘導体(D1)とフタロシアニン誘導体(D2)、および必要に応じて光重合開始剤と共に、顔料担体中に、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、本発明の着色組成物は、数種類の顔料を別々に顔料担体に分散したものを混合して製造することもできる。
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各種手段を用いて、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0.1μm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 colored composition of the present invention can be adjusted in the form of a solvent development type or alkali development type colored resist material. The colored resist material is obtained by dispersing a pigment in a pigment carrier containing a thermoplastic resin, a thermosetting resin or a photosensitive resin and a monomer, and one or two or more pigments are combined with a phthalocyanine derivative (D1). A phthalocyanine derivative (D2) and, if necessary, a photopolymerization initiator and finely dispersed in a pigment carrier using various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, a kneader, and an attritor. can do. The colored composition of the present invention can also be produced by mixing several types of pigments separately dispersed on a pigment carrier.
The colored composition of the present invention can be obtained by using various means such as centrifugation, sintered filter, membrane filter, etc., coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.1 μm or more, and It is preferable to remove the mixed dust.
次に、本発明のカラーフィルタについて説明する。
本発明のカラーフィルタは、透明基板上に、少なくとも1つの赤色フィルタセグメント、少なくとも1つの青色フィルタセグメント、および少なくとも1つの緑色フィルタセグメントを具備するカラーフィルタであって、前記青色フィルタセグメントおよび/または緑色フィルタセグメントが、本発明のカラーフィルタ用着色組成物から形成されているものである。
また、本発明のカラーフィルタは、透明基板上に、少なくとも1つのイエロー色フィルタセグメント、少なくとも1つのマゼンタ色フィルタセグメント、および少なくとも1つのシアン色フィルタセグメントを具備するカラーフィルタであって、前記シアン色フィルタセグメントが、本発明のカラーフィルタ用着色組成物から形成されているものである。
Next, the color filter of the present invention will be described.
The color filter of the present invention is a color filter comprising at least one red filter segment, at least one blue filter segment, and at least one green filter segment on a transparent substrate, wherein the blue filter segment and / or green color is provided. The filter segment is formed from the coloring composition for a color filter of the present invention.
The color filter of the present invention is a color filter comprising at least one yellow color filter segment, at least one magenta color filter segment, and at least one cyan color filter segment on a transparent substrate, wherein the cyan color The filter segment is formed from the coloring composition for a color filter of the present invention.
赤色、イエロー色、マゼンタ色のフィルタセグメントを形成するための着色組成物としては、本発明の着色組成物と同様に、透明樹脂、その前駆体またはそれらの混合物からなる顔料担体と、顔料と、必要に応じて、溶剤、光重合開始剤、増感剤、樹脂型顔料分散剤、界面活性剤等を含有するものを用いることができる。
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、207、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、下記の黄色顔料、オレンジ色顔料を併用することができる。
As a coloring composition for forming red, yellow, and magenta filter segments, as in the coloring composition of the present invention, a pigment carrier comprising a transparent resin, a precursor thereof, or a mixture thereof, and a pigment, If necessary, those containing a solvent, a photopolymerization initiator, a sensitizer, a resin-type pigment dispersant, a surfactant and the like can be used.
Examples of the red coloring composition for forming the red filter segment include C.I. 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, 207, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 246, 254, 255, Red pigments such as H.264 and 272 can be used. The following yellow pigment and 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等の黄色顔料や、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。
Examples of the yellow coloring composition for forming the yellow filter segment include C.I. 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, 1 And yellow pigments such as 5,176,177,179,180,181,182,185,187,188,193,194,199, for example C. I. Orange pigments such as pigment orange 36, 43, 51, 55, 59, 61 can be used.
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。
透明基板としては、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。
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方法としては、印刷法またはフォトリソグラフィー法、IJ法などがある。
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.
As the transparent substrate, glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali alumino borosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are 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.
Examples of a method for forming a filter segment using the colored composition of the present invention include a printing method, a photolithography method, and an IJ method.
印刷法による各色フィルタセグメントの形成は、上記各種の印刷インキとして調製した着色組成物の印刷と乾燥を繰り返すだけでパターン化ができるため、カラーフィルタの製造法としては、低コストで量産性に優れている。さらに、印刷技術の発展により高い寸法精度および平滑度を有する微細パターンの印刷を行うことができる。印刷を行うためには、印刷の版上にて、あるいはブランケット上にてインキが乾燥、固化しないような組成とすることが好ましい。また、印刷機上でのインキの流動性の制御も重要であり、分散剤や体質顔料によるインキ粘度の調整を行うこともできる。 The formation of each color filter segment by the printing method can be patterned simply by repeating the printing and drying of the colored composition prepared as the above various printing inks. Therefore, the color filter manufacturing method is low-cost and excellent in mass productivity. ing. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.
フォトリソグラフィー法により各色フィルタセグメントを形成する場合は、上記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した着色組成物を、透明基板上に、スプレーコートやスピンコート、スリットコート、ロールコート等の塗布方法により、乾燥膜厚が0.5〜3.0μmとなるように塗布する。必要により乾燥された膜には、この膜と接触あるいは非接触状態で設けられた所定のパターンを有するマスクを通して紫外線露光を行う。その後、溶剤またはアルカリ現像液に浸漬するかもしくはスプレーなどにより現像液を噴霧して未硬化部を除去して所望のパターンを形成したのち、同様の操作を他色について繰り返してカラーフィルタを製造することができる。さらに、着色レジスト材の重合を促進するため、必要に応じて加熱を施すこともできる。フォトリソグラフィー法によれば、上記印刷法より精度の高いカラーフィルタが製造できる。 When forming each color filter segment by a photolithography method, the colored composition prepared as the solvent developing type or alkali developing type colored resist material is applied on a transparent substrate, such as spray coating, spin coating, slit coating, roll coating, etc. By a coating method, coating is performed so that the dry film thickness is 0.5 to 3.0 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.
現像に際しては、安全性や環境問題からアルカリ水溶液を用いるのが一般的であり、アルカリ現像液として炭酸ナトリウム、炭酸水素ナトリウム、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。
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水溶性樹脂、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 alkali solution is generally used for safety and environmental issues, and an aqueous solution of sodium carbonate, sodium hydrogen carbonate, sodium hydroxide or the like is used as the alkaline developer, such as dimethylbenzylamine, triethanolamine, etc. The organic alkali can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
In order to increase the UV exposure sensitivity, after coating and drying the colored resist material, a water-soluble or alkaline water-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.
本発明の着色組成物は、上記方法の他に転写法などにより製造することができるが、本発明の着色組成物は、いずれの方法にも用いることができる。転写法は剥離性の転写ベースシートの表面に、あらかじめフィルタセグメント層を形成しておき、このフィルタセグメント層を所望の基板に転写させる方法である。 The colored composition of the present invention can be produced by a transfer method or the like in addition to the above method, but the colored composition of the present invention can be used in any method. The transfer method is a method in which a filter segment layer is formed in advance on the surface of a peelable transfer base sheet, and this filter segment layer is transferred to a desired substrate.
以下に、本発明を実施例に基づいて説明するが、本発明はこれによって限定されるもの
ではない。なお、実施例および比較例中、「部」とは「重量部」を意味する。
まず、実施例および比較例に用いたアクリル樹脂溶液およびフタロシアニン誘導体組成物(フタロシアニン誘導体(D1)およびフタロシアニン誘導体(D2)を含む組成物)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。
Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “parts” means “parts by weight”.
First, preparation of acrylic resin solutions and phthalocyanine derivative compositions (compositions containing phthalocyanine derivative (D1) and phthalocyanine derivative (D2)) 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).
(アクリル樹脂溶液の調製)
反応容器にシクロヘキサノン450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、メタクリル酸20.0部、メチルメタクリレート10.0部、n−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、2,2‘−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃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部に溶解させたものを添加し、さらに80℃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重量%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。
(Preparation of acrylic resin solution)
Put 450 parts of cyclohexanone in a reaction vessel, heat to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 20.0 parts of methacrylic acid, 10.0 parts of methyl methacrylate, 55.0 parts of n-butyl methacrylate A mixture of 15.0 parts of 2-hydroxyethyl methacrylate and 4.0 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin solution was obtained. 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, 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% by weight. To prepare an acrylic resin solution.
(フタロシアニン誘導体組成物の調製)
クロルスルホン酸300部中に銅フタロシアニン30部を仕込み、完全に溶解した後、塩化チオニル24部を加え、徐々に昇温して101℃で3時間反応させた。その反応液を氷水9000部中に注入し、撹拌後、濾過、水洗した。得られたプレスケーキを水300部でスラリーとした後、N,N−ジメチルアミノプロピルアミン15部を加え、室温で3時間、次いで、60℃で2時間撹拌した後、濾過、水洗、乾燥し、フタロシアニン誘導体組成物36部を得た。得られたフタロシアニン誘導体組成物について、Waters社製液体クロマトグラフ質量分析計プラットフォームLCZで組成分析したところ、3個以上置換基を有するものは含まれておらず、下記式(6)の置換基を1個有するフタロシアニン誘導体(D1)と下記式(6)の置換基を2個有するフタロシアニン誘導体(D2)の重量比は85:15であった。
(Preparation of phthalocyanine derivative composition)
After adding 30 parts of copper phthalocyanine to 300 parts of chlorosulfonic acid and completely dissolving it, 24 parts of thionyl chloride was added, and the temperature was gradually raised and reacted at 101 ° C. for 3 hours. The reaction solution was poured into 9000 parts of ice water, stirred, filtered and washed with water. The obtained press cake was made into a slurry with 300 parts of water, then 15 parts of N, N-dimethylaminopropylamine was added, and the mixture was stirred at room temperature for 3 hours, then at 60 ° C. for 2 hours, filtered, washed with water and dried. 36 parts of a phthalocyanine derivative composition were obtained. The obtained phthalocyanine derivative composition was subjected to a composition analysis using a liquid chromatograph mass spectrometer platform LCZ manufactured by Waters, and those having three or more substituents were not included. The weight ratio of the phthalocyanine derivative (D1) having one and the phthalocyanine derivative (D2) having two substituents of the following formula (6) was 85:15.
また、上記塩化チオニル24部を加えた後、反応温度を105℃、106℃、106.8℃、100℃、109.8℃にすることによって、下記式(6)の置換基を1個有するフタロシアニン誘導体(D1):下記式(6)の置換基を2個有するフタロシアニン誘導体(D2)の重量比がそれぞれ65:35、60:40、56:44、90:10、41:59のフタロシアニン誘導体組成物を得た。
一般式(6)
General formula (6)
(青色レジスト材)
[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0.5mmのジルコニアビーズを用いて、サンドミルで10時間分散した後、1.0μmのフィルタで濾過し青色レジスト材用銅フタロシアニン系顔料分散体を作製した。
ε型銅フタロシアニン青色顔料(C.I.pigment blue 15:6)
(BASF製「ヘリオゲンブルーL−6700F」) 10.0部
銅フタロシアニン誘導体組成物 1.0部
(フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=85:15)
リン酸エステル系顔料分散剤
(ビックケミー社製「BYK111」) 2.0部
アクリル樹脂溶液 47.0部
メトキシプロピルアセテート 40.0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、0.2μmのフィルタで濾過して、アルカリ現像型青色レジスト材を得た。
青色レジスト材用銅フタロシアニン系顔料分散体 45.0部
アクリル樹脂溶液 15.0部
トリメチロールプロパントリアクリレート 5.6部
(新中村化学社製「NKエステルATMPT」)
光重合開始剤 2.0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
メトキシプロピルアセテート 32.2部
(Blue resist material)
[Example 1]
A mixture of the following composition is stirred and mixed uniformly, then dispersed in a sand mill for 10 hours using zirconia beads having a diameter of 0.5 mm, filtered through a 1.0 μm filter, and a copper phthalocyanine pigment dispersion for a blue resist material. Was made.
ε-type copper phthalocyanine blue pigment (CI pigment blue 15: 6)
("Heliogen Blue L-6700F" manufactured by BASF) 10.0 parts Copper phthalocyanine derivative composition 1.0 part (phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 85:15)
Phosphate ester pigment dispersant ("BYK111" manufactured by Big Chemie) 2.0 parts Acrylic resin solution 47.0 parts Methoxypropyl acetate 40.0 parts Next, the mixture of the following composition was stirred and mixed to be uniform, Filtration through a 0.2 μm filter gave an alkali-developable blue resist material.
Copper phthalocyanine pigment dispersion for blue resist material 45.0 parts Acrylic resin solution 15.0 parts Trimethylolpropane triacrylate 5.6 parts ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.)
Photopolymerization initiator 2.0 parts ("Irgacure 907" manufactured by Ciba Specialty Chemicals)
Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 part Methoxypropyl acetate 32.2 parts
[実施例2]
銅フタロシアニン誘導体組成物を、フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=65:35の重量比のものに変えた以外は、実施例1と同様にしてアルカリ現像型青色レジスト材を得た。
[実施例3]
銅フタロシアニン誘導体組成物を、フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=60:40の重量比のものに変えた以外は、実施例1と同様にしてアルカリ現像型青色レジスト材を得た。
[実施例4]
銅フタロシアニン誘導体組成物を、フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=56:44の重量比のものに変えた以外は、実施例1と同様にしてアルカリ現像型青色レジスト材を得た。
[Example 2]
An alkali-developable blue resist material was obtained in the same manner as in Example 1 except that the copper phthalocyanine derivative composition was changed to a phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 65: 35.
[Example 3]
An alkali-developable blue resist material was obtained in the same manner as in Example 1 except that the copper phthalocyanine derivative composition was changed to one having a weight ratio of phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 60: 40.
[Example 4]
An alkali-developable blue resist material was obtained in the same manner as in Example 1 except that the copper phthalocyanine derivative composition was changed to one having a weight ratio of phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 56: 44.
[実施例5]
青色顔料を緑色顔料C.I.pigment green 7(大日本インキ化学工業社製「ファストゲングリーンS」)に変えた以外は、実施例1と同様にしてアルカリ現像型緑色レジスト材を得た。
[実施例6]
青色顔料を緑色顔料C.I.pigment green 7(大日本インキ化学工業社製「ファストゲングリーンS」)に変えた以外は、実施例4と同様にしてアルカリ現像型緑色レジスト材を得た。
[Example 5]
Blue pigment is green pigment C.I. I. An alkali-developing green resist material was obtained in the same manner as in Example 1 except that it was changed to pigment green 7 (“Fastgen Green S” manufactured by Dainippon Ink and Chemicals, Inc.).
[Example 6]
Blue pigment is green pigment C.I. I. An alkali-developable green resist material was obtained in the same manner as in Example 4 except that it was changed to pigment green 7 (“Fastgen Green S” manufactured by Dainippon Ink and Chemicals, Inc.).
[実施例7]
青色顔料を緑色顔料C.I.pigment green 36(東洋インキ製造社製「リオノールグリーン6YK」)に変えた以外は、実施例1と同様にしてアルカリ現像型緑色レジスト材を得た。
[実施例8]
青色顔料を緑色顔料C.I.pigment green 36(東洋インキ製造社製「リオノールグリーン6YK」)に変えた以外は実施例4と同様にしてアルカリ現像型緑色レジスト材を得た。
[Example 7]
Blue pigment is green pigment C.I. I. An alkali-developable green resist material was obtained in the same manner as in Example 1 except that it was changed to pigment green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Manufacturing Co., Ltd.).
[Example 8]
Blue pigment is green pigment C.I. I. An alkali-developable green resist material was obtained in the same manner as in Example 4 except that it was changed to pigment green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Manufacturing Co., Ltd.).
[比較例1]
銅フタロシアニン誘導体組成物を、フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=90:10の重量比のものに変えた以外は、実施例1と同様にしてアルカリ現像型青色レジスト材を得た。
[比較例2]
銅フタロシアニン誘導体組成物を、フタロシアニン誘導体(D1):フタロシアニン誘導体(D2)=41:59の重量比のものに変えた以外は、実施例1と同様にしてアルカリ現像型青色レジスト材を得た。
[Comparative Example 1]
An alkali-developable blue resist material was obtained in the same manner as in Example 1, except that the copper phthalocyanine derivative composition was changed to a weight ratio of phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 90: 10.
[Comparative Example 2]
An alkali-developable blue resist material was obtained in the same manner as in Example 1, except that the copper phthalocyanine derivative composition was changed to a phthalocyanine derivative (D1): phthalocyanine derivative (D2) = 41: 59.
[比較例3]
青色顔料を緑色顔料C.I.pigment green 7(大日本インキ化学工業社製「ファストゲングリーンS」)に変えた以外は、比較例1と同様にしてアルカリ現像型緑色レジスト材を得た。
[比較例4]
青色顔料を緑色顔料C.I.pigment green 36(東洋インキ製造社製「リオノールグリーン6YK」)に変えた以外は、比較例1と同様にしてアルカリ現像型緑色レジスト材を得た。
[Comparative Example 3]
Blue pigment is green pigment C.I. I. An alkali-developable green resist material was obtained in the same manner as in Comparative Example 1 except that it was changed to pigment green 7 (“Fastgen Green S” manufactured by Dainippon Ink and Chemicals, Inc.).
[Comparative Example 4]
Blue pigment is green pigment C.I. I. An alkali-developable green resist material was obtained in the same manner as in Comparative Example 1 except that it was changed to pigment green 36 (“Lionol Green 6YK” manufactured by Toyo Ink Manufacturing Co., Ltd.).
[実施例1]〜[実施例8]、[比較例1]〜[比較例4]で得られたレジスト材2kgについて、Whatman社製1.0μmGF/FディスクフィルターGlass Microfiber Media with Polypropyleneにて、フィルターが目詰まりするまでの最大ろ過量を測定した。また、各レジスト材を、スピンコート法により、100×100mmのガラス基板に1.2μmの膜厚(乾燥時)に塗布、乾燥後、KEYENCE社製 VH-Z450を用いて塗膜中に存在する1.0μm以上の粒子個数の測定を行った。また、各レジスト材について、粒度分布測定装置「日本ルフト社製「DT−1200」」にて粒度分布を測定し、平均粒径を算出した。更に、作製直後及び作成後40℃の環境で1週間保存した後の粘度をE型粘度計(東機産業社製「ELD型粘度計」)にて測定した。更に、スピンコート法により、各レジスト材をガラス基板に0.6μmの膜厚に塗布、乾燥後、日本電計社製「BM-5A LUMINANCE COLORMETER」にてコントラストの測定を行った。結果を表1および表2に示す。 With respect to 2 kg of the resist material obtained in [Example 1] to [Example 8] and [Comparative Example 1] to [Comparative Example 4], whatman 1.0 μm GF / F disk filter Glass Microfiber Media with Polypropylene The maximum amount of filtration until the filter was clogged was measured. In addition, each resist material is applied to a 100 × 100 mm glass substrate by a spin coating method to a film thickness of 1.2 μm (during drying), dried, and then present in the coating film using VH-Z450 manufactured by KEYENCE Corporation. The number of particles of 1.0 μm or more was measured. Moreover, about each resist material, the particle size distribution was measured with the particle size distribution measuring apparatus "Nippon Luft Co." DT-1200 ", and the average particle diameter was computed. Further, the viscosity after storage for 1 week in an environment of 40 ° C. immediately after preparation and after preparation was measured with an E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.). Further, each resist material was applied to a glass substrate to a thickness of 0.6 μm by a spin coating method, dried, and then subjected to contrast measurement with “BM-5A LUMINANCE COLORMETER” manufactured by Nippon Denki Co., Ltd. The results are shown in Tables 1 and 2.
[表1]に示すように、[実施例1]〜[実施例8]で得られたレジスト材は、1.0μmGF/Fディスクフィルターでろ過したときに目詰まりせず、塗膜中に存在する1.0μm以上の粒子の個数は5個程度であり、レジスト材中に含まれる顔料の平均粒径も0.2μm程度であり、1週間の経時で増粘もない。また、塗膜のコントラストも高い。何れも、一般式(1)で示される置換基を1個有するフタロシアニン誘導体(D1)と2個有するフタロシアニン誘導体(D2)とを85:15〜56:44の重量比の範囲内で用いて顔料を分散したことから、顔料の二次粒子が低減され、ろ過性が向上し、塗膜欠陥(抜け)が無いことから塗膜のコントラストも向上した。 As shown in [Table 1], the resist materials obtained in [Example 1] to [Example 8] do not clog when filtered through a 1.0 [mu] m GF / F disk filter and are present in the coating film. The number of particles having a size of 1.0 μm or more is about 5, the average particle size of the pigment contained in the resist material is about 0.2 μm, and there is no increase in viscosity over one week. Moreover, the contrast of a coating film is also high. Both are pigments using a phthalocyanine derivative (D1) having one substituent represented by the general formula (1) and a phthalocyanine derivative (D2) having two substituents within a weight ratio of 85:15 to 56:44. The secondary particles of the pigment were reduced, the filterability was improved, and the coating film contrast was improved because there were no coating film defects (missing).
これに対し、[比較例1]〜[比較例4]で得られたレジスト材は、1.0μmGF/Fディスクフィルターでろ過したときに120g程度で目詰まりが発生し、塗膜中に存在する1.0μm以上の粒子の個数も10〜24個と、実施例で得られたレジスト材の2倍以上であった。また、経時で増粘も発生し、塗膜のコントラストについても、実施例で得られたレジスト材の塗膜に比べて2000以上低かった。何れも、一般式(1)で示される置換基を1個有するフタロシアニン誘導体(D1)と2個有するフタロシアニン誘導体(D2)とを85:15〜56:44の重量比の範囲外で用いて顔料を分散したことから、顔料の二次粒子が増え、ろ過性が低下し、安定性も悪くなり、塗膜欠陥(抜け)が発生して塗膜のコントラストも低下した。 In contrast, the resist materials obtained in [Comparative Example 1] to [Comparative Example 4] are clogged at about 120 g when filtered through a 1.0 μm GF / F disk filter and are present in the coating film. The number of particles having a size of 1.0 μm or more was 10 to 24, which was more than twice the resist material obtained in the examples. Moreover, thickening also occurred over time, and the contrast of the coating film was 2000 or more lower than the coating film of the resist material obtained in the examples. In any case, the phthalocyanine derivative (D1) having one substituent represented by the general formula (1) and the phthalocyanine derivative (D2) having two substituents are used outside the weight ratio range of 85:15 to 56:44. As a result, the secondary particles of the pigment increased, the filterability decreased, the stability deteriorated, the coating film defect (missing) occurred, and the contrast of the coating film also decreased.
Claims (4)
一般式(1)
General formula (1)
3. A color filter comprising at least one yellow color filter segment, at least one magenta color filter segment, and at least one cyan color filter segment, wherein the cyan color filter segment is for a color filter according to claim 1 or 2. A color filter formed from a coloring composition.
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