JP4668801B2 - Pigment dispersant and use thereof - Google Patents
Pigment dispersant and use thereof Download PDFInfo
- Publication number
- JP4668801B2 JP4668801B2 JP2006029662A JP2006029662A JP4668801B2 JP 4668801 B2 JP4668801 B2 JP 4668801B2 JP 2006029662 A JP2006029662 A JP 2006029662A JP 2006029662 A JP2006029662 A JP 2006029662A JP 4668801 B2 JP4668801 B2 JP 4668801B2
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- JP
- Japan
- Prior art keywords
- group
- pigment
- parts
- color filter
- acid
- 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.)
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- 239000000049 pigment Substances 0.000 title claims description 163
- 239000002270 dispersing agent Substances 0.000 title claims description 87
- 239000000203 mixture Substances 0.000 claims description 102
- 239000011347 resin Substances 0.000 claims description 69
- 229920005989 resin Polymers 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000002966 varnish Substances 0.000 claims description 36
- 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 claims description 35
- 125000001174 sulfone group Chemical group 0.000 claims description 34
- 238000004040 coloring Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 17
- -1 amine salt Chemical class 0.000 claims description 14
- 125000002091 cationic group Chemical group 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000001054 red pigment Substances 0.000 claims description 9
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 6
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 claims description 6
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229950000244 sulfanilic acid Drugs 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229960003080 taurine Drugs 0.000 claims description 4
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 claims description 3
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 claims description 3
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims description 3
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 claims description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 3
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 claims description 3
- XOAPGFZLHVPMBT-UHFFFAOYSA-N 3-amino-2-chloro-6-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(Cl)=C1S(O)(=O)=O XOAPGFZLHVPMBT-UHFFFAOYSA-N 0.000 claims description 3
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 claims description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 3
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 claims description 3
- DFFMMDIDNCWQIV-UHFFFAOYSA-N 4-amino-3-methoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1N DFFMMDIDNCWQIV-UHFFFAOYSA-N 0.000 claims description 3
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 claims description 3
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 claims description 3
- JGSAMPZLJLDOKW-UHFFFAOYSA-N 5-amino-2-chloro-4-sulfobenzoic acid Chemical compound NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O JGSAMPZLJLDOKW-UHFFFAOYSA-N 0.000 claims description 3
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 claims description 3
- CYJJLCDCWVZEDZ-UHFFFAOYSA-N 8-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 CYJJLCDCWVZEDZ-UHFFFAOYSA-N 0.000 claims description 3
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims description 3
- 125000005543 phthalimide group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000004992 toluidines Chemical class 0.000 claims description 3
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical group C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 23
- 238000003860 storage Methods 0.000 description 17
- 239000006185 dispersion Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 13
- 238000007639 printing Methods 0.000 description 12
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 239000004925 Acrylic resin Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000976 ink Substances 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000001052 yellow pigment Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 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 3
- 238000004070 electrodeposition Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- ZEHOVWPIGREOPO-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-[2-(4,5,6,7-tetrachloro-1,3-dioxoinden-2-yl)quinolin-8-yl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1C(C1=N2)=CC=CC1=CC=C2C1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O ZEHOVWPIGREOPO-UHFFFAOYSA-N 0.000 description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical group C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 125000005263 alkylenediamine group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009499 grossing Methods 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229940067265 pigment yellow 138 Drugs 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BSDIXHJWVBVLNE-UHFFFAOYSA-N 1-[[4-[(9,10-dioxoanthracen-1-yl)amino]-6-(2-methylanilino)-1,3,5-triazin-2-yl]amino]anthracene-9,10-dione Chemical compound CC1=CC=CC=C1NC1=NC(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C=CC=2)=NC(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C=CC=2)=N1 BSDIXHJWVBVLNE-UHFFFAOYSA-N 0.000 description 1
- ACJSMQZKXAMMRA-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyrrol-5-one Chemical compound N1C=CC2=NC(=O)C=C21 ACJSMQZKXAMMRA-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-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
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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Description
本発明は、顔料分散剤、液晶カラーディスプレイや撮像素子などの製造に使用されるカラーフィルター用着色組成物およびこれを用いたカラーフィルターに関する。さらに詳しくは、顔料分散性、透明性、流動性や貯蔵安定性に優れたカラーフィルター用着色組成物およびこれを用いたカラーフィルターに関する。 The present invention relates to a coloring composition for a color filter used for producing a pigment dispersant, a liquid crystal color display, an imaging device, and the like, and a color filter using the same. More specifically, the present invention relates to a coloring composition for a color filter excellent in pigment dispersibility, transparency, fluidity and storage stability, and a color filter using the same.
液晶ディスプレイなどに使用されるカラーフィルターは、現在フォトレジストに顔料を分散させた着色組成物を、スピンコート法、コーティング法、或いは転写法により基板に塗布後、フォトマスクを介して光、エネルギー線露光および現像して画素を形成させることにより主に作製されている。その際、赤色画素形成用の顔料として、通常、ジケトピロロピロール顔料が用いられているが、該顔料を樹脂および溶剤などとともに、通常の分散機で分散させるだけでは、顔料が充分に分散しないことから、該分散液（「カラーフィルター用着色組成物」を意味する場合がある）をカラーフィルターの着色画素（以下単に「画素」という）の形成に使用すると、得られる赤色画素は透明性に欠け、該画素は、カラーフィルター用画素として透過率が不十分であり、上記赤色顔料はカラーフィルター用着色組成物用の顔料としては不満足なものであった。 Color filters used in liquid crystal displays, etc. are currently applied to a substrate by spin coating, coating, or transfer methods with a colored composition in which a pigment is dispersed in a photoresist, and then light and energy rays are passed through a photomask. It is mainly produced by forming pixels by exposure and development. At that time, a diketopyrrolopyrrole pigment is usually used as a pigment for forming a red pixel, but the pigment is not sufficiently dispersed only by dispersing the pigment together with a resin and a solvent with a normal disperser. Therefore, when the dispersion (which may mean “color composition for color filter”) is used for forming a color pixel (hereinafter simply referred to as “pixel”) of a color filter, the resulting red pixel is made transparent. This pixel was insufficient in transmittance as a color filter pixel, and the red pigment was unsatisfactory as a pigment for a color filter coloring composition.
また、フォトレジストに使用される樹脂としては、アルカリ水溶液がパターニングの現像液に使用できることから、酸価が高いアクリル系ポリマーが主に採用されている。しかしながら、上記の顔料と高酸価のアクリル系樹脂からなる顔料分散液では、顔料粒子の凝集が起こり、顔料分散液の粘度が高くなりやすく、また、経時で顔料分散液が増粘するので、顔料分散液の貯蔵安定性の悪い場合が多い。 In addition, as the resin used for the photoresist, an acrylic polymer having a high acid value is mainly employed because an alkaline aqueous solution can be used as a patterning developer. However, in a pigment dispersion composed of the above-mentioned pigment and a high acid value acrylic resin, aggregation of pigment particles occurs, the viscosity of the pigment dispersion tends to increase, and the viscosity of the pigment dispersion increases with time. The storage stability of the pigment dispersion is often poor.
以上のような困難さを伴う顔料分散液によりカラーフィルターを作製する場合、顔料分散液をスピンコート法により基板に塗布および成膜し、その後に着色膜を画素化するが、顔料分散液の粘度が高かったり、顔料が粒子凝集してカラーフィルター用着色組成物がチクソトロピックな粘性を示す場合には、画素化前の塗布層の中央部が盛り上がるため、大画面のカラーフィルターを作製する際には基板の中央部に形成した画素と周辺部に形成した画素とは色相差や濃度差が発生する原因となっている。 When preparing a color filter with a pigment dispersion with the above difficulties, the pigment dispersion is applied to a substrate by spin coating and film formation is performed, and then the colored film is pixelated. When the color filter composition is thick or the color composition for the color filter has a thixotropic viscosity, the central part of the coating layer before pixelation rises. This causes a hue difference or a density difference between the pixel formed in the central portion of the substrate and the pixel formed in the peripheral portion.
従って、カラーフィルター用着色組成物（顔料分散液）は、通常、顔料濃度が５〜２０質量％の高濃度範囲にあるにも拘らず、その分散状態は顔料粒子同士が凝集せず、かつ一般的な常乾塗料や焼き付け塗料に比べて粘度が低く（例えば、５〜２０ｍＰａ・ｓ程度）、かつ貯蔵安定性に優れたものでなければならない。 Therefore, although the coloring composition for color filters (pigment dispersion) is usually in a high concentration range where the pigment concentration is 5 to 20% by mass, the dispersion state is such that the pigment particles are not aggregated with each other. It must be low in viscosity (for example, about 5 to 20 mPa · s) and excellent in storage stability as compared with typical ordinary dry paints and baking paints.
上記の要求を満たすために、従来、赤色顔料がジケトピロロピロール顔料（例えば、Ｃ．Ｉ．ピグメントレッド２５４）の場合には、スルホン化度が１分子当たり１以上のジケトピロロピロールスルホン酸を上記顔料に添加したり、または上記顔料を上記スルホン化物で処理することなどが提案されている（特許文献１）。
一方、液晶表示装置の用途もパーソナルコンピューターのモニターからカラーテレビジョンのカラーディスプレー用にと拡大し、カラーフィルターに対してもさらなる性能向上の要請が高まり、画素の透明性の改善や、画素の透過光のコントラストのアップや、画素中の顔料濃度を高める必要が生じてきた。 On the other hand, the use of liquid crystal display devices has been expanded from monitors for personal computers to color displays for color televisions, and there has been a growing demand for further improvements in color filters, improving pixel transparency and transmitting pixels. It has become necessary to increase the contrast of light and increase the pigment concentration in the pixel.
しかしながら、上記スルホン化物を使用する方法では、顔料の分散性向上による画素の透明性の改良や、顔料濃度が高くなることによる顔料分散液の粘度の増大および貯蔵安定性の低下を防止することは困難であり、また、ジケトピロロピロール顔料をスルホン化する際の反応の制御が難しく、スルホン基が多く導入されたスルホン化物を顔料分散剤として使用した場合、得られる顔料分散液中に異物が発生することがあり、これらの改善が要望されている。 However, in the method using the sulfonated product, it is possible to improve the transparency of the pixel by improving the dispersibility of the pigment, and to prevent an increase in the viscosity of the pigment dispersion and a decrease in storage stability due to an increase in the pigment concentration. It is difficult, and it is difficult to control the reaction when diketopyrrolopyrrole pigment is sulfonated. When a sulfonated product having a large number of sulfonic groups introduced therein is used as a pigment dispersant, foreign matter is not contained in the resulting pigment dispersion. There is a need to improve these.
本発明者らは、高顔料濃度カラーフィルター用着色組成物における上記スルホン化ジケトピロロピロール顔料を使用した場合の上記の問題点を解決し、カラーフィルター用着色組成物の色品位の向上、低粘度化および異物の発生防止を可能にするべく鋭意研究した結果、スルホン基数を０．０５〜０．５に制御したスルホン化ジケトピロロピロール顔料複合体を顔料分散剤として使用することにより、カラーフィルター用着色組成物の低粘度化が達成でき、かつ貯蔵時の該着色用組成物の増粘ゲル化を防止でき、かつ異物の発生を防止するとともに、カラーフィルターとして最も重要な画素の透明性も向上させることができることを見い出し、本発明を完成するに至った。 The present inventors have solved the above-mentioned problems when using the sulfonated diketopyrrolopyrrole pigment in the coloring composition for high pigment concentration color filters, and improved the color quality of the coloring composition for color filters. As a result of diligent research to make it possible to prevent the occurrence of viscosity and foreign matter, the use of a sulfonated diketopyrrolopyrrole pigment complex with the number of sulfone groups controlled to 0.05 to 0.5 as a pigment dispersant The viscosity of the coloring composition for filters can be lowered, the thickening gelation of the coloring composition during storage can be prevented, the generation of foreign matters is prevented, and the transparency of the most important pixel as a color filter Has been found to be improved, and the present invention has been completed.
上記目的は以下の本発明によって達成される。すなわち、本発明は、下記（ａ）成分と下記（ｂ）成分とを含むことを特徴とする顔料分散剤を提供する。この場合は、（ａ）成分と（ｂ）成分との質量比はａ：ｂ＝１０：９０〜９０：１０であることが好ましい。 The above object is achieved by the present invention described below. That is, the present invention provides a pigment dispersing agent which comprises a lower Symbol (a) component and the following component (b). In this case, the mass ratio of the component (a) to the component (b) is preferably a: b = 10: 90 to 90:10.
（ａ）成分；スルホン基を有するジケトピロロピロール顔料とスルホン基を有さないジケトピロロピロール顔料との顔料複合体であって、該複合体におけるジケトピロロピロール顔料分子１個あたりのスルホン基の数が０．０５〜０．５である顔料複合体であり、ジケトピロロピロール顔料は、下記一般式（Ｖ）で表される。
（ｂ）成分；下記の一般式（Ｉ）、一般式（II）、一般式（III）または一般式（IV）で表される化合物、その金属塩、アンモニウム塩および／またはアミン塩である。
上記本発明の顔料分散剤においては、スルホン基を有するジケトピロロピロール顔料のスルホン基が、フリーのスルホン基、スルホン基の金属塩、アミン塩およびアンモニウム塩から選ばれる少なくとも１種であることが好ましい。 In the pigment dispersing agent of the present invention, it diketopyrrolopyrrole sulfonic group of a pigment having a scan sulfone group is at least one selected free sulfonic group, a metal salt of a sulfonic group, amine salts and ammonium salts Is preferred .
また、上記本発明の顔料分散剤においては、一般式（Ｉ）のＲ2 −ＳＯ 3 Ｈが、タウリン、Ｎ−メチルタウリン、ｏ−アミノベンゼンスルホン酸、ｍ−アミノベンゼンスルホン酸、スルファニル酸、４−クロロアニリン−３−スルホン酸、２−ニトロアニリン−４−スルホン酸、２−アミノフェノール−４−スルホン酸、ｏ−アニシジン−５−スルホン酸、ｐ−アニシジン−５−スルホン酸、ｏ−トルイジン−４−スルホン酸、ｍ−トルイジン−４−スルホン酸、ｐ−トルイジン−２−スルホン酸、２−クロロ−ｐ−トルイジン−３−スルホン酸、３−アミノ−６−クロロ−４−スルホ安息香酸、１−アミノ−８−ナフタレンスルホン酸、２−アミノ−１−ナフタレンスルホン酸、５−アミノ−１−ナフタレンスルホン酸、６−アミノ−１−ナフタレンスルホン酸および５−アミノ−３−ナフタレンスルホン酸から選ばれるアミンからアミノ基を除いた基由来のものであることが好ましい。 In the pigment dispersant of the present invention, R 2 —SO 3 H of the general formula (I) is taurine, N-methyltaurine, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, sulfanilic acid, 4-chloroaniline-3-sulfonic acid, 2-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-anisidine-5-sulfonic acid, p-anisidine-5-sulfonic acid, o- Toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, 2-chloro-p-toluidine-3-sulfonic acid, 3-amino-6-chloro-4-sulfobenzoic acid Acid, 1-amino-8-naphthalenesulfonic acid, 2-amino-1-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, 6-amino-1- It is preferable that the amine is selected from the lid sulfone acid and 5-amino-3-naphthalenesulfonic acid group derived by removing an amino group.
また、上記本発明の顔料分散剤においては、一般式（II）のＲ2が、アニリン、Ｎ−メチルアニリン、トルイジン（ｏ−、ｍ−またはｐ−）、アニシジン（ｏ−、ｍ−またはｐ−）、クロロアニリン（ｏ−、ｍ−またはｐ−）、ジフェニルアミン、１−ナフチルアミンおよび２−ナフチルアミンから選ばれるアミンからアミノ基を除いた基であることが好ましい。 In the pigment dispersant of the present invention, R 2 in the general formula (II) is aniline, N-methylaniline, toluidine (o-, m- or p-), anisidine (o-, m- or p). A group obtained by removing an amino group from an amine selected from-), chloroaniline (o-, m- or p-), diphenylamine, 1-naphthylamine and 2-naphthylamine is preferable.
また、本発明は、赤色顔料と前記本発明の顔料分散剤と樹脂分散剤と樹脂ワニスとを含むことを特徴とするカラーフィルター用着色組成物を提供する。該赤色顔料はＣ．Ｉ．ピグメントレッド２５４であること；および樹脂分散剤が、カチオン系樹脂分散剤であることが好ましい。 The present invention also provides a color composition for a color filter comprising a red pigment, the pigment dispersant of the present invention, a resin dispersant, and a resin varnish. The red pigment is C.I. I. Pigment Red 254; and the resin dispersant is preferably a cationic resin dispersant.
また、本発明は、カラーフィルター用基板に着色画素を形成する工程を含むカラーフィルターの製造方法において、上記着色画素を、前記本発明のカラーフィルター用着色組成物を使用して形成することを特徴とするカラーフィルターの製造方法、該方法で製造されたことを特徴とするカラーフィルター、該カラーフィルターを含んでいることを特徴とする画像表示装置、該画像表示装置を含んでいることを特徴とする情報伝達機器を提供する。 Further, the present invention is a method for producing a color filter comprising a step of forming a colored pixel on a color filter substrate, wherein the colored pixel is formed using the colored composition for a color filter of the present invention. A color filter manufacturing method, a color filter manufactured by the method, an image display device including the color filter, and an image display device including the image display device Provide information transmission equipment.
以上の本発明によれば、特定の顔料分散剤をカラーフィルターの赤色画素形成用着色組成物の顔料分散剤として使用することにより、カラーフィルター用着色組成物を安定に製造することができ、異物の発生を防止し、また、最終的にカラーフィルター用着色組成物として使用される際にも、優れた分光カーブ特性を有し、鮮明で冴えた、透明感の高い、しかも耐光性、耐熱性、耐溶剤性、耐薬品性および耐水性などの諸堅牢性に優れた画素を有するカラーフィルターを得ることができる。 According to the present invention as described above, by using a specific pigment dispersant as a pigment dispersant for a color filter red color forming composition, a color filter coloring composition can be stably produced, and foreign matter In addition, when used as a coloring composition for color filters, it has excellent spectral curve characteristics, is clear and crisp, has high transparency, and is light and heat resistant. A color filter having pixels excellent in various fastnesses such as solvent resistance, chemical resistance and water resistance can be obtained.
次に発明を実施するための最良の形態を挙げて本発明をさらに詳細に説明する。本発明の顔料分散剤は、前記の（ａ）成分と前記の（ｂ）成分とからなる。
（ａ）成分は、スルホン基を有するジケトピロロピロール顔料とスルホン基を有さないジケトピロロピロール顔料との顔料複合体であって、該複合体におけるジケトピロロピロール顔料分子１個あたりのスルホン基の数が０．０５〜０．５である顔料複合体である。
Next, the present invention will be described in more detail with reference to the best mode for carrying out the invention. The pigment dispersant of the present invention comprises the component ( a) and the component (b).
The component (a) is a pigment complex of a diketopyrrolopyrrole pigment having a sulfone group and a diketopyrrolopyrrole pigment not having a sulfone group, and the component per diketopyrrolopyrrole pigment molecule in the complex It is a pigment composite in which the number of sulfone groups is 0.05 to 0.5.
上記（ａ）成分の調製方法としては、下記一般式（Ｖ）で表されるスルホン基を有さないジケトピロロピロール顔料、例えば、Ｃ．Ｉ．ピグメントレッド２５４を発煙硫酸などのスルホン化剤でスルホン化させる際に、そのスルホン化条件を調節してジケトピロロピロール顔料に導入されるスルホン基の数を上記範囲にする。 The above is the preparation how the component (a), diketopyrrolopyrrole pigments having no sulfonic group represented by the following general formula (V), for example, C. I. When the Pigment Red 254 is sulfonated with a sulfonating agent such as fuming sulfuric acid, the sulfonation conditions are adjusted so that the number of sulfone groups introduced into the diketopyrrolopyrrole pigment is within the above range.
上記スルホン化物の１分子あたりのスルホン基個数が、０．５個よりも多くなった場合には、平均スルホン基個数が０．０５〜０．５の範囲になるようにスルホン化されていないジケトピロロピロール顔料を上記スルホン化物に混合し、該混合物を濃硫酸中に溶解させ、該溶液を氷水中に注入して、複合体を析出させ、水洗および乾燥することにより、目的とする顔料分散剤を得ることができる。 When the number of sulfonate groups per molecule of the sulfonated product is more than 0.5, the disulfonate that is not sulfonated so that the average number of sulfonate groups is in the range of 0.05 to 0.5. Ketopyrrolopyrrole pigment is mixed with the sulfonated product, the mixture is dissolved in concentrated sulfuric acid, the solution is poured into ice water, the complex is precipitated, washed with water and dried to obtain the desired pigment dispersion. An agent can be obtained.
スルホン基個数が０．０５〜０．５に調整された複合体は、水や溶媒に対する親和性や溶解性が著しく低下し、実質的に不溶ないし難溶性の顔料的挙動を示す。これはスルホン化したジケトピロロピロール顔料分子に添加したスルホン化していないジケトピロロピロール顔料分子が、スルホン化したジケトピロロピロール分子に重積（共晶または混合）化し、スルホン化したジケトピロロピロール分子の水に対する親和性や溶解性が低下したものと考えられる。 A complex in which the number of sulfone groups is adjusted to 0.05 to 0.5 significantly decreases the affinity and solubility in water and solvent, and exhibits a substantially insoluble or hardly soluble pigment-like behavior. This is because non-sulfonated diketopyrrolopyrrole pigment molecules added to the sulfonated diketopyrrolopyrrole pigment molecules stack (eutectic or mixed) with the sulfonated diketopyrrolopyrrole molecules, and the sulfonated diketo. It is considered that the affinity and solubility of pyrrolopyrrole molecules in water are reduced.
上記ジケトピロロピロール顔料複合体のスルホン基はフリーでもよいし、塩基との塩でもよい。塩を形成する金属としては、例えば、Ｌｉ、ＮａおよびＫなどのアルカリ金属、Ｃａ、Ｂａ、Ａｌ、Ｍｎ、Ｓｒ、ＭｇおよびＮｉなどの多価金属が挙げられる。また、アミン塩またはアンモニウム塩を形成するアミンとしては、例えば、（モノ、ジまたはトリ）アルキルアミン類、置換または未置換のアルキレンジアミン類、アルカノールアミン類、アルキルアンモニウムクロライドおよびアンモニアなどが挙げられる。 The sulfone group of the diketopyrrolopyrrole pigment complex may be free or a salt with a base. Examples of the metal forming the salt include alkali metals such as Li, Na, and K, and polyvalent metals such as Ca, Ba, Al, Mn, Sr, Mg, and Ni. Examples of the amine that forms an amine salt or an ammonium salt include (mono, di, or tri) alkylamines, substituted or unsubstituted alkylenediamines, alkanolamines, alkylammonium chloride, and ammonia.
（ｂ）成分は、前記一般式（Ｉ）、一般式（II）、一般式（III）または一般式（IV）で表される化合物、その金属塩、アンモニウム塩および／またはアミン塩であることが好ましい。
前記一般式（Ｉ）で表される化合物は、置換基を有していてもよい１−アミノアントラキノン１モルと、置換基を有していてもよいアニリンまたは置換基を有していてもよいフェノールまたは置換基を有していてもよい１−アミノアントラキノンのいずれか１モルと、塩化シアヌル１モルとをｏ−ジクロルベンゼンなどの不活性な溶媒中、１３０℃〜１７０℃で２〜６時間反応させ、さらにスルホン基を１個有する脂肪族アミンまたは芳香族アミン１モルを１５０℃〜１７０℃で３〜４時間反応させることによって得ることができる。
The component ( b) is a compound represented by the general formula (I), general formula (II), general formula (III) or general formula (IV), a metal salt, an ammonium salt and / or an amine salt thereof. Is preferred.
The compound represented by the general formula (I) may have 1 mol of 1-aminoanthraquinone which may have a substituent and aniline which may have a substituent or a substituent. Either 1 mol of phenol or 1-aminoanthraquinone optionally having substituent (s) and 1 mol of cyanuric chloride in an inert solvent such as o-dichlorobenzene, 2 to 6 at 130 ° C to 170 ° C. It can be obtained by reacting for 1 hour and further reacting 1 mol of an aliphatic amine or aromatic amine having one sulfone group at 150 ° C. to 170 ° C. for 3 to 4 hours.
前記一般式（Ｉ）の化合物の製造に使用されるスルホン基を１個有する脂肪族アミンまたは芳香族アミンとしては、例えば、タウリン、Ｎ−メチルタウリン、ｏ−アミノベンゼンスルホン酸、ｍ−アミノベンゼンスルホン酸、スルファニル酸、４−クロロアニリン−３−スルホン酸、２−ニトロアニリン−４−スルホン酸、２−アミノフェノール−４−スルホン酸、ｏ−アニシジン−５−スルホン酸、ｐ−アニシジン−５−スルホン酸、ｏ−トルイジン−４−スルホン酸、ｍ−トルイジン−４−スルホン酸、ｐ−トルイジン−２−スルホン酸、２−クロロ−ｐ−トルイジン−３−スルホン酸、３−アミノ−６−クロロ−４−スルホ安息香酸、１−アミノ−８−ナフタレンスルホン酸、２−アミノ−１−ナフタレンスルホン酸、５−アミノ−１−ナフタレンスルホン酸、６−アミノ−１−ナフタレンスルホン酸および５−アミノ−３−ナフタレンスルホン酸などが挙げられる。 Examples of the aliphatic amine or aromatic amine having one sulfone group used for the production of the compound of the general formula (I) include taurine, N-methyltaurine, o-aminobenzenesulfonic acid, m-aminobenzene. Sulfonic acid, sulfanilic acid, 4-chloroaniline-3-sulfonic acid, 2-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-anisidine-5-sulfonic acid, p-anisidine-5 -Sulfonic acid, o-toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, 2-chloro-p-toluidine-3-sulfonic acid, 3-amino-6- Chloro-4-sulfobenzoic acid, 1-amino-8-naphthalenesulfonic acid, 2-amino-1-naphthalenesulfonic acid, 5-amino-1 Naphthalenesulfonic acid, 6-amino-1-naphthalenesulfonic acid and 5-amino-3-naphthalenesulfonic acid.
また、前記一般式（II）で表される化合物は、置換基を有していてもよい１−アミノアントラキノン２モルと、塩化シアヌル１モルとをｏ−ジクロルベンゼンなどの不活性な溶媒中、１３０℃〜１７０℃で２〜６時間反応させ、さらにスルホン基を持たない芳香族アミン１モルを添加して１５０℃〜１７０℃で３〜４時間反応させ、次いで生成物を発煙硫酸などのスルホン化剤でスルホン化させることによって得ることができる。 Moreover, the compound represented by the said general formula (II) is 1-aminoanthraquinone which may have a substituent, and 1 mol of cyanuric chloride in inert solvents, such as o-dichlorobenzene. The reaction is carried out at 130 ° C. to 170 ° C. for 2 to 6 hours, 1 mol of an aromatic amine having no sulfone group is added, and the reaction is carried out at 150 ° C. to 170 ° C. for 3 to 4 hours. It can be obtained by sulfonation with a sulfonating agent.
前記一般式（II）の化合物の製造に使用される芳香族アミンとしては、例えば、アニリン、Ｎ−メチルアニリン、トルイジン（ｏ−、ｍ−またはｐ−）、アニシジン（ｏ−、ｍ−またはｐ−）、クロロアニリン（ｏ−、ｍ−またはｐ−）、ジフェニルアミン、１−ナフチルアミンおよび２−ナフチルアミンなどが挙げられる。 Examples of the aromatic amine used for the production of the compound of the general formula (II) include aniline, N-methylaniline, toluidine (o-, m- or p-), anisidine (o-, m- or p). -), Chloroaniline (o-, m- or p-), diphenylamine, 1-naphthylamine, 2-naphthylamine and the like.
前記一般式（III）で表わされる化合物は、置換基を有していてもよい無水フタル酸と置換基を有していてもよいキナルジンから容易に合成できるキノフタロン化合物を、発煙硫酸などのスルホン化剤でスルホン化させることによって得ることができる。 The compound represented by the general formula (III) is a quinophthalone compound that can be easily synthesized from phthalic anhydride which may have a substituent and quinaldine which may have a substituent. It can be obtained by sulfonation with an agent.
前記の一般式（III）のＲ1は、水素原子、ハロゲン原子、水酸基、アルキル基、無置換または置換のアリール基、無置換または置換のフタルイミド基であり、Ｒ2は、水素原子または水酸基であり、Ｒ3は、ハロゲン原子であり、ｍは０〜４の整数を表わし、ｎは化合物へのスルホン基の平均導入個数であり、０．５〜４の数である。上記アルキル基とは、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｔ−ブチル基などの直鎖または分岐のある炭素数が１〜８程度のアルキル基を示し、アリール基とは、例えば、フェニル基、ナフチル基、ビフェニル基、アントラニル基、フェナントリル基などの芳香族炭化水素基を示し、これは無置換でも置換されていても構わない。置換基としては、例えば、ハロゲン原子、水酸基、アルキル基などが挙げられるが、特に限定されない。 R 1 in the general formula (III) is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted phthalimide group, and R 2 is a hydrogen atom or a hydroxyl group. R 3 represents a halogen atom, m represents an integer of 0 to 4, n represents the average number of sulfone groups introduced into the compound, and is a number of 0.5 to 4. The alkyl group is a linear or branched alkyl group having about 1 to 8 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group. An aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, or a phenanthryl group, which may be unsubstituted or substituted. Examples of the substituent include, but are not limited to, a halogen atom, a hydroxyl group, and an alkyl group.
前記一般式（IV）で表される化合物は、置換基を有していてもよい３−ヒドロキシ−２−ナフトエ酸の酸クロライド化物を、２，５位に置換基を有していてもよい１，４−フェニレンジアミンまたは３，３’位に置換基を有していてもよいベンジジンとをニトロベンゼンなどの不活性な溶媒中、１３０〜１３５℃で反応させ、次いで置換基を有していてもよいアミノベンゼンスルホン酸および置換基を有していてもよいアニリンをそれぞれ常法によりジアゾ化し、カップリングさせることによって得ることができる。 The compound represented by the general formula (IV) may have an acid chloride of 3-hydroxy-2-naphthoic acid which may have a substituent, and may have a substituent at the 2,5-position. 1,4-phenylenediamine or benzidine which may have a substituent at the 3,3′-position is reacted at 130 to 135 ° C. in an inert solvent such as nitrobenzene, and then has a substituent. It can be obtained by diazotizing and coupling the aminobenzene sulfonic acid which may be further substituted and the aniline which may have a substituent, by a conventional method.
また、前記一般式（Ｉ）〜一般式（IV）で示される化合物と金属塩を形成する金属としては、例えば、Ｌｉ、ＮａおよびＫなどのアルカリ金属、Ｃａ、Ｂａ、Ａｌ、Ｍｎ、Ｓｒ、ＭｇおよびＮｉなどの多価金属が挙げられる。また、一般式（Ｉ）〜一般式（IV）で示される化合物とアミン塩を形成するアミンとしては、例えば、（モノ、ジまたはトリ）アルキルアミン類、置換または未置換のアルキレンジアミン類、アルカノールアミン類およびアルキルアンモニウムクロライドなどが挙げられる。 Moreover, as a metal which forms a metal salt with the compound shown by the said general formula (I)-general formula (IV), for example, alkali metals, such as Li, Na, and K, Ca, Ba, Al, Mn, Sr, Multivalent metals such as Mg and Ni are listed. Examples of amines that form amine salts with the compounds represented by formulas (I) to (IV) include (mono, di, or tri) alkylamines, substituted or unsubstituted alkylenediamines, and alkanols. Examples include amines and alkyl ammonium chlorides.
前記（ａ）成分は、前記一般式（Ｉ）〜一般式（IV）のうちの１つの式で表される化合物（（ｂ）成分）と併用することができる。前記（ａ）成分と前記（ｂ）成分とを併用する場合の（ａ）成分と（ｂ）成分との質量比は、（ａ）成分：（ｂ）成分＝１０：９０〜９０：１０であり、好ましくは４０：６０〜６０：４０である。（ａ）成分の使用量が上記範囲から外れると分散液の粘度低下が不十分であり、また、分散液の経時安定性が低下する。 Before Symbol (a) component can be combined with the general formula (I) ~ compounds represented by one formula of the general formula (IV) ((b) component). When the component (a) and the component (b) are used in combination, the mass ratio of the component (a) to the component (b) is (a) component: (b) component = 10: 90 to 90:10. Yes, preferably 40:60 to 60:40. When the amount of component (a) used is outside the above range, the viscosity of the dispersion is insufficiently lowered, and the temporal stability of the dispersion is lowered.
本発明のカラーフィルター用着色組成物は、顔料、前記の顔料分散剤、樹脂分散剤（高分子化合物からなる顔料を分散させるための顔料分散剤）および樹脂ワニスから構成される。本発明で使用する顔料は、赤色顔料としてジケトピロロピロール系顔料が挙げられる。このような赤色顔料としては、Ｃ．Ｉ．ピグメントレッド２５４などが挙げられる。その際、色補正として、黄色顔料を配合させてともに分散させてもよい。このような黄色顔料としては、イソインドリン顔料（Ｃ．Ｉ．ピグメントイエロー１３９）などを用いることができる。上記赤色顔料の使用量は特に限定されないが、通常、後述の樹脂ワニスの樹脂バインダー１００質量部に対し５〜５００質量部の割合で使用される。 The coloring composition for a color filter of the present invention comprises a pigment, the above-described pigment dispersant, a resin dispersant (a pigment dispersant for dispersing a pigment made of a polymer compound), and a resin varnish. Examples of the pigment used in the present invention include a diketopyrrolopyrrole pigment as a red pigment. Such red pigments include C.I. I. Pigment red 254 and the like. At that time, as color correction, a yellow pigment may be blended and dispersed together. As such a yellow pigment, an isoindoline pigment (CI Pigment Yellow 139) or the like can be used. Although the usage-amount of the said red pigment is not specifically limited, Usually, it is used in the ratio of 5-500 mass parts with respect to 100 mass parts of resin binders of the below-mentioned resin varnish.
前記顔料分散剤の顔料に対する配合割合は、顔料１００質量部に対して、０．０５〜４０質量部の割合が好ましく、さらに好ましくは０．１〜１０質量部の割合である。顔料分散剤の配合割合が少なすぎると、目的とする顔料分散剤の効果が十分に得られにくくなる。また、顔料分散剤の配合割合が多すぎると、多く用いただけの効果が得られず、逆にその結果得られるカラーフィルター用着色組成物の諸物性の低下をもたらし、さらには、顔料分散剤自体の持つ色によって、分散されるべき顔料の色相が大きく変化してしまう。 The blending ratio of the pigment dispersant to the pigment is preferably 0.05 to 40 parts by mass, more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the pigment. When the blending ratio of the pigment dispersant is too small, it is difficult to sufficiently obtain the effect of the target pigment dispersant. In addition, if the blending ratio of the pigment dispersant is too large, the effect of using only a large amount cannot be obtained, and conversely, the resulting physical properties of the color filter coloring composition are lowered, and further the pigment dispersant itself. The hue of the pigment to be dispersed greatly changes depending on the color of the.
本発明で用いられる樹脂分散剤としては、公知の分散剤が使用でき、特にカチオン系樹脂分散剤が好ましい。カチオン系樹脂分散剤としては、例えば、ＢＹＫ（ビッグ）ケミー社（ドイツ）の商品名：DISPER BYK−１６０、同１６１、同１６２、同１６３、同１６４、同１６６、同１７１、同１８２、同１８４、同２０００、同２００１、同２０７０、同２１５０；ＥＦＫＡ社（オランダ）の商品名：EFKA-４４、同４６、同４７、同４８、同４０１０、同４０５０、同４０５５、同４０２０、同４０１５、同４０６０、同４３００、同４３３０、同４４００、同４４０６、同４５１０、同４８００；Ａｖｅｃｉａ社（イギリス）の商品名：SOLSPERS−２４０００、同３２５５０、ＮＢＺ−４２０４／１０；川研ファインケミカル社の商品名：ヒノアクトＴ−６０００、同７０００、同８０００；味の素社の商品名：アジスパーＰＢ−８２１、同８２２、同８２３；共栄社化学社の商品名：フローレンＤＯＰＡ−１７ＨＦ、同１５ＢＨＦ、同３３、同４４などが挙げられる。 As the resin dispersant used in the present invention, a known dispersant can be used, and a cationic resin dispersant is particularly preferable. Examples of the cationic resin dispersant include trade names of BYK (Big) Chemie (Germany): DISPER BYK-160, 161, 162, 163, 164, 166, 171, 182, and the like. 184, 2000, 2001, 2070, 2150; trade names of EFKA (Netherlands): EFKA-44, 46, 47, 48, 4010, 4050, 4055, 4020, 4015 4060, 4300, 4330, 4400, 4406, 4510, 4800; trade names of Avecia (UK): SOLSPERS-24000, 32550, NBZ-4204 / 10; products of Kawaken Fine Chemicals, Inc. Name: Hinoact T-6000, 7000, 8000; Ajinomoto Co. product names: Ajisper PB-821, 822, 8 3; Kyoeisha Chemical Co., Ltd. under the trade name: Flowlen DOPA-17HF, same 15BHF, the same 33, such as the 44, and the like.
本発明で用いる樹脂分散剤の添加量としては、特に限定されるわけではないが、好ましくは顔料１００質量部に対して２〜１００質量部であり、より好ましくは１０〜５０質量部である。樹脂分散剤の添加量が２質量部より少ないと良好な顔料分散安定性が得られず、１００質量部より多いと、得られるカラーフィルター用着色組成物から形成される被膜の現像性が不良となる場合がある。 The addition amount of the resin dispersant used in the present invention is not particularly limited, but is preferably 2 to 100 parts by mass, more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the pigment. When the addition amount of the resin dispersant is less than 2 parts by mass, good pigment dispersion stability cannot be obtained, and when it is more than 100 parts by mass, the developability of the film formed from the color composition for color filter obtained is poor. There is a case.
本発明において顔料を分散させる分散媒体として使用される樹脂ワニスとしては、従来からカラーフィルター用着色組成物に使用されている公知の樹脂ワニスがいずれも使用でき、特に限定されない。また、分散媒体として樹脂ワニスにおいて適切な溶剤または水系媒体が使用される。また、必要に応じて従来公知の添加剤、例えば、分散助剤、平滑化剤および密着化剤などが適宜添加使用される。 As the resin varnish used as a dispersion medium for dispersing the pigment in the present invention, any known resin varnish conventionally used in coloring compositions for color filters can be used and is not particularly limited. In addition, an appropriate solvent or aqueous medium is used as the dispersion medium in the resin varnish. In addition, conventionally known additives such as a dispersion aid, a smoothing agent, and an adhesive agent are appropriately added and used as necessary.
樹脂ワニスとしては、感光性の樹脂ワニスと非感光性樹脂ワニスが使用される。感光性樹脂ワニスとしては、例えば、紫外線硬化性インキや電子線硬化インキなどに用いられる感光性樹脂ワニスが挙げられ、非感光性樹脂ワニスとしては、例えば、凸版インキ、平版インキ、凹版グラビアインキおよび孔版スクリーンインキなどの印刷インキに使用する樹脂ワニス、インクジェットプリンティングに使用する樹脂ワニス、電着塗装に使用する樹脂ワニス、電子印刷や静電印刷の現像剤に使用する樹脂ワニス、熱転写フィルムまたはリボンに使用する樹脂ワニスなどが挙げられる。 As the resin varnish, a photosensitive resin varnish and a non-photosensitive resin varnish are used. Examples of the photosensitive resin varnish include photosensitive resin varnishes used for ultraviolet curable inks and electron beam curable inks. Non-photosensitive resin varnishes include, for example, letterpress ink, planographic ink, intaglio gravure ink, and the like. For resin varnishes used for printing inks such as stencil screen ink, resin varnishes used for inkjet printing, resin varnishes used for electrodeposition coating, resin varnishes used for developers of electronic printing and electrostatic printing, thermal transfer films or ribbons Examples of the resin varnish to be used.
感光性樹脂ワニスの具体例としては、例えば、感光性環化ゴム系樹脂、感光性フェノール系樹脂、感光性ポリアクリレート系樹脂、感光性ポリアミド系樹脂、感光性ポリイミド系樹脂など、より具体的には不飽和ポリエステル系樹脂、ポリエステルアクリレート系樹脂、ポリエポキシアクリレート系樹脂、ポリウレタンアクリレート系樹脂、ポリエーテルアクリレート系樹脂、ポリオールアクリレート系樹脂などのワニス、或いはこれらにさらに反応性希釈剤としてモノマーが加えられたワニスが挙げられる。上記感光性樹脂ワニスの中で好適な樹脂としては、分子中にフリーのカルボン酸基を有するアルカリ現像可能なアクリレート系の樹脂が望ましい。 Specific examples of the photosensitive resin varnish include, for example, a photosensitive cyclized rubber resin, a photosensitive phenol resin, a photosensitive polyacrylate resin, a photosensitive polyamide resin, and a photosensitive polyimide resin. Monomers are added as reactive diluents to varnishes such as unsaturated polyester resins, polyester acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, polyol acrylate resins. Varnish. As a suitable resin among the photosensitive resin varnish, an alkali-developable acrylate resin having a free carboxylic acid group in the molecule is desirable.
非感光性の樹脂ワニスの具体例としては、例えば、セルロースアセテート系樹脂、ニトロセルロース系樹脂、スチレン系（共）重合体、ポリビニルブチラール系樹脂、アミノアルキッド系樹脂、ポリエステル系樹脂、アミノ樹脂変性ポリエステル系樹脂、ポリウレタン系樹脂、アクリルポリオールウレタン系樹脂、可溶性ポリアミド系樹脂、可溶性ポリイミド系樹脂、可溶性ポリアミドイミド系樹脂、可溶性ポリエステルイミド系樹脂、ヒドロキシエチルセルロース、スチレン−マレイン酸エステル系共重合体の水溶性塩、（メタ）アクリル酸エステル系（共）重合体の水溶性塩、水溶性アミノポリエステル系樹脂および水溶性ポリアミド系樹脂などが挙げられ、これらは単独或いは２種以上を組み合わせて使用される。 Specific examples of the non-photosensitive resin varnish include, for example, a cellulose acetate resin, a nitrocellulose resin, a styrene (co) polymer, a polyvinyl butyral resin, an aminoalkyd resin, a polyester resin, and an amino resin modified polyester. Water-soluble resin, polyurethane resin, acrylic polyol urethane resin, soluble polyamide resin, soluble polyimide resin, soluble polyamideimide resin, soluble polyesterimide resin, hydroxyethyl cellulose, styrene-maleic acid ester copolymer Examples thereof include salts, water-soluble salts of (meth) acrylic acid ester-based (co) polymers, water-soluble aminopolyester resins, and water-soluble polyamide-based resins, and these are used alone or in combination of two or more.
本発明の上記の各成分から構成される着色組成物の製造方法は、特に制限されないが、例えば、下記の方法などが挙げられる。
（イ）硫酸などに顔料および顔料分散剤を溶解した後、水中に注入し、両者を固溶体にして、カチオン系樹脂分散剤とともに樹脂ワニスに添加して練肉する。
（ロ）水または有機溶媒中に顔料を均一に懸濁させ、該懸濁液に顔料分散剤を含有する溶液を添加し、上記顔料粒子表面に顔料分散剤を沈着させたものをカチオン系樹脂分散剤とともに樹脂ワニスに加えて練肉する。
（ハ）顔料、顔料分散剤およびカチオン系樹脂分散剤をアトライターやボールミルなどの湿式媒体分散機で微分散し、樹脂ワニスに添加して練肉する。
（ニ）樹脂ワニス中に顔料、顔料分散剤およびカチオン系樹脂分散剤をプレミキシング時に添加し、湿式媒体分散機で分散処理する。
Although the manufacturing method in particular of the coloring composition comprised from said each component of this invention is not restrict | limited, For example, the following method etc. are mentioned.
(A) After dissolving the pigment and the pigment dispersant in sulfuric acid or the like, the mixture is poured into water, both are made into a solid solution, added to the resin varnish together with the cationic resin dispersant, and kneaded.
(B) A cationic resin obtained by uniformly suspending a pigment in water or an organic solvent, adding a solution containing a pigment dispersant to the suspension, and depositing the pigment dispersant on the surface of the pigment particles. Add to resin varnish with dispersant and knead.
(C) A pigment, a pigment dispersant, and a cationic resin dispersant are finely dispersed with a wet medium disperser such as an attritor or a ball mill, and added to the resin varnish and kneaded.
(D) A pigment, a pigment dispersant, and a cationic resin dispersant are added to the resin varnish at the time of premixing, and are dispersed by a wet medium disperser.
本発明の着色組成物を用いてカラーフィルターを製造するに際しては、樹脂ワニスとして感光性の樹脂ワニスを使用する場合には、該組成物にベンゾインエチルエーテルやベンゾフェノンなどの従来公知の光重合開始剤を加え、従来公知の方法で練肉して感光性着色組成物を調製して使用する。また、上記の光重合開始剤に代えて熱重合開始剤を使用して熱重合性着色組成物として使用することもできる。 When a photosensitive resin varnish is used as the resin varnish when producing a color filter using the colored composition of the present invention, a conventionally known photopolymerization initiator such as benzoin ethyl ether or benzophenone is used in the composition. In addition, a photosensitive coloring composition is prepared and used by kneading by a conventionally known method. Moreover, it can replace with said photoinitiator and can also use it as a thermopolymerizable coloring composition using a thermal polymerization initiator.
上記の感光性着色組成物を用いて基板上にカラーフィルターの画素を形成する場合には、透明基板上に該感光性着色組成物を、例えば、スピンコーター、低速回転コーター、ロールコーターまたはナイフコーターなどを用いて全面コーティングを行うか、或いは各種の印刷方法のうちの好適な方法による全面印刷または画素よりやや大きな部分印刷を行い、予備乾燥後フォトマスクを透明基板のコートまたは印刷面に密着させ、超高圧水銀灯を使用して露光を行って画素を焼き付けする。次いで現像および洗浄を行い、必要に応じポストベークを行うことにより画素を形成することができる。これらの画素形成方法自体は公知であり、本発明においてはカラーフィルターの画素形成方法は特に限定されない。 When forming a pixel of a color filter on a substrate using the above photosensitive coloring composition, the photosensitive coloring composition is formed on a transparent substrate, for example, a spin coater, a low-speed rotation coater, a roll coater or a knife coater. The entire surface is coated by using a suitable method among various printing methods, or a partial printing slightly larger than the pixel is performed, and after pre-drying, the photomask is adhered to the coating or printing surface of the transparent substrate. Then, exposure is performed using an ultra-high pressure mercury lamp, and the pixels are printed. Next, development and washing are performed, and post-baking is performed as necessary to form pixels. These pixel forming methods are known per se, and the pixel forming method of the color filter is not particularly limited in the present invention.
非感光性の樹脂ワニスを使用した本発明の着色組成物（非感光性着色組成物）を用いてカラーフィルターの画素を形成する場合には、透明基板上に該非感光性着色組成物を、例えば、カラーフィルター用印刷インキとして上記した各種の印刷方法のうちの好適な方法にて印刷して直接基板に画素を形成する方法、水性電着塗装組成物として電着塗装法により塗布して基板に画素を形成する方法、インクジェット用インキとしてインクジェットプリンティング法により印刷して基板に画素を形成する方法、電子印刷方法や静電印刷方法を用いたり、或いは上記の方式のうちの１つの方式などで転写性基材に付与して一旦画素を形成させてからカラーフィルター用基板に転写する方法などが挙げられる。次いで常法に従い、必要に応じてベーキングを行ったり、表面平滑化のための研磨を行ったり、表面保護のためのトップコーティングを行う。また、常法に従いブラックマトリックスを形成させる。このようにして、ＲＧＢの各画素を有するカラーフィルターを得ることができる。これらのカラーフィルターの製造方法自体は公知であり、本発明においてはカラーフィルターの製造方法は特に限定されない。 When forming a pixel of a color filter using the colored composition of the present invention (non-photosensitive colored composition) using a non-photosensitive resin varnish, the non-photosensitive colored composition is formed on a transparent substrate, for example, A method for forming a pixel directly on a substrate by printing by a suitable method among the above-mentioned various printing methods as a printing ink for a color filter, and applying to a substrate by an electrodeposition coating method as an aqueous electrodeposition coating composition A method for forming pixels, a method for forming pixels on a substrate by printing by inkjet printing as inkjet ink, an electronic printing method or an electrostatic printing method, or transfer by one of the above methods For example, a method may be used in which a pixel is once formed by applying to a conductive substrate and then transferred to a color filter substrate. Then, according to a conventional method, baking is performed as necessary, polishing for smoothing the surface, or top coating for protecting the surface is performed. Further, a black matrix is formed according to a conventional method. In this way, a color filter having RGB pixels can be obtained. The manufacturing methods of these color filters are known per se, and the manufacturing method of the color filters is not particularly limited in the present invention.
次に合成例、実施例および比較例を挙げて本発明をさらに具体的に説明する。なお、文中の「部」または「％」とあるのは質量基準である。 Next, the present invention will be described more specifically with reference to synthesis examples, examples and comparative examples. In the text, “part” or “%” is based on mass.
［合成例Ａ１］
ジケトピロロピロール顔料（Ｃ．Ｉ．ピグメントレッド２５４）３０部を２０％発煙硫酸３００部に添加し、その後６０〜６５℃で６時間反応させる。冷却後、反応混合物を３，０００部の氷水中に析出させ、濾過および水洗し、水ペースト１１０部（純量２８部）を得た。この水ペーストを乾燥させ、硫黄の元素分析の結果より１分子当たり平均０．８個のスルホン基が導入されているジケトピロロピロール２８部（顔料分散剤Ａ１）を得た。
[Synthesis Example A1]
30 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254) are added to 300 parts of 20% fuming sulfuric acid, and then reacted at 60 to 65 ° C. for 6 hours. After cooling, the reaction mixture was precipitated in 3,000 parts of ice water, filtered and washed with water to obtain 110 parts of water paste (pure 28 parts). This water paste was dried, and 28 parts of diketopyrrolopyrrole (pigment dispersant A1) having an average of 0.8 sulfone groups introduced per molecule was obtained from the result of elemental analysis of sulfur.
また、５部の顔料分散剤Ａ１および５部のＣ．Ｉ．ピグメントレッド２５４を９５％濃硫酸１００部に添加し、室温で１時間撹拌する。冷却後、得られた濃硫酸溶液を１，０００部の氷水中に注入して複合体を析出させ、濾過および水洗し、水ペースト３９部（純量１０部）を得た。この水ペーストを乾燥させ、硫黄の元素分析の結果より１分子当たり平均０．４個のスルホン基が導入されているジケトピロロピロール１０部（顔料分散剤Ａ２）を得た。 Also 5 parts of pigment dispersant A1 and 5 parts of C.I. I. Pigment Red 254 is added to 100 parts of 95% concentrated sulfuric acid and stirred at room temperature for 1 hour. After cooling, the resulting concentrated sulfuric acid solution was poured into 1,000 parts of ice water to precipitate a composite, filtered and washed with water to obtain 39 parts of a water paste (pure 10 parts). This water paste was dried, and 10 parts of diketopyrrolopyrrole (pigment dispersant A2) having an average of 0.4 sulfone groups introduced per molecule was obtained from the result of elemental analysis of sulfur.
［合成例Ａ２］
３．７５部の合成例Ａ１の顔料分散剤Ａ１および６．２５部のＣ．Ｉ．ピグメントレッド２５４を９５％濃硫酸１００部に添加し、室温で１時間撹拌する。冷却後、得られた濃硫酸溶液を１，０００部の氷水中に注入して複合体を析出させ、濾過および水洗し、水ペースト３９部（純量１０部）を得た。この水ペーストを乾燥させ、硫黄の元素分析の結果より１分子当たり平均０．３個のスルホン基が導入されているジケトピロロピロール１０部（顔料分散剤Ａ３）を得た。
[Synthesis Example A2]
3.75 parts of Pigment Dispersant A1 of Synthesis Example A1 and 6.25 parts of C.I. I. Pigment Red 254 is added to 100 parts of 95% concentrated sulfuric acid and stirred at room temperature for 1 hour. After cooling, the resulting concentrated sulfuric acid solution was poured into 1,000 parts of ice water to precipitate a composite, filtered and washed with water to obtain 39 parts of a water paste (pure 10 parts). This water paste was dried, and 10 parts of diketopyrrolopyrrole (pigment dispersant A3) into which 0.3 sulfone groups on average were introduced per molecule was obtained from the result of elemental analysis of sulfur.
［合成例Ａ３］
２．５部の合成例Ａ１の顔料分散剤Ａ１および７．５部のＣ．Ｉ．ピグメントレッド２５４を使用し、合成例Ａ２と同様にして、硫黄の元素分析の結果より１分子当たり平均０．２個のスルホン基が導入されているジケトピロロピロール１０部（顔料分散剤Ａ４）を得た。
[Synthesis Example A3]
2.5 parts of Pigment Dispersant A1 of Synthesis Example A1 and 7.5 parts of C.I. I. Pigment Red 254 and 10 parts of diketopyrrolopyrrole in which an average of 0.2 sulfone groups are introduced per molecule from the result of elemental analysis of sulfur in the same manner as in Synthesis Example A2 (pigment dispersant A4) Got.
［合成例Ａ４］
ジケトピロロピロール顔料（Ｃ．Ｉ．ピグメントレッド２５４）３０部を２０％発煙硫酸３００部に添加し、その後４５〜５０℃で６時間反応させる。冷却後、反応混合物を３，０００部の氷水中に析出させ、濾過および水洗し、水ペースト１１０部（純量２８部）を得た。この水ペーストを乾燥させ、硫黄の元素分析の結果より１分子当たり平均０．４個のスルホン基が導入されているジケトピロロピロール２８部（顔料分散剤Ａ５）を得た。
[Synthesis Example A4]
30 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254) are added to 300 parts of 20% fuming sulfuric acid, and then reacted at 45-50 ° C. for 6 hours. After cooling, the reaction mixture was precipitated in 3,000 parts of ice water, filtered and washed with water to obtain 110 parts of water paste (pure 28 parts). This water paste was dried, and 28 parts of diketopyrrolopyrrole (pigment dispersant A5) having an average of 0.4 sulfone groups introduced per molecule was obtained from the result of elemental analysis of sulfur.
［参考例ａ１］
アクリル樹脂ワニス（メタクリル酸／ブチルアクリレート／スチレン／ヒドロキシエチルアクリレートを２５／５０／１５／１０のモル比で共重合させたもの、分子量１２，０００、固形分３０％）５０部にＣ．Ｉ．ピグメントレッド２５４の２０部、イソインドリンイエロー顔料（Ｃ．Ｉ．ピグメントイエロー１３９）４部、合成例Ａ１で得られた顔料分散剤Ａ２の１部、カチオン系樹脂分散剤（ディスパーＢＹＫ−２０００）４部および溶剤（プロピレングリコールモノメチルエーテルアセテート）（以下ＰＧＭＡｃと略す）を２０部配合し、プレミキシングの後、横型ビーズミルで分散し赤色の着色組成物を得た。
[ Reference Example a 1]
50 parts of acrylic resin varnish (methacrylic acid / butyl acrylate / styrene / hydroxyethyl acrylate copolymerized at a molar ratio of 25/50/15/10, molecular weight 12,000, solid content 30%) I. 20 parts of Pigment Red 254, 4 parts of isoindoline yellow pigment (CI Pigment Yellow 139), 1 part of Pigment Dispersant A2 obtained in Synthesis Example A1, Cationic Resin Dispersant (Disper BYK-2000) 4 20 parts of a solvent and a solvent (propylene glycol monomethyl ether acetate) (hereinafter abbreviated as PGMAc) were blended and dispersed by a horizontal bead mill after premixing to obtain a red colored composition.
［参考例ａ２〜ａ４］
参考例ａ１の顔料分散剤Ａ２の代わりにそれぞれ合成例Ａ２〜Ａ４で得られた顔料分散剤Ａ３〜Ａ５を使用し、その他は参考例ａ１と同様にして赤色の着色組成物を得た。
［比較例Ａ１］
参考例ａ１の顔料分散剤Ａ２の代わりに合成例Ａ１で得られた顔料分散剤Ａ１を使用し、参考例ａ１と同様にして赤色の着色組成物を得た。
[Reference Example a 2~ a 4]
Instead of pigment dispersant A2 of Reference Example a 1, pigment dispersants A3 to A5 obtained in Synthesis Examples A2 to A4 were used, respectively, and the other components were the same as Reference Example a 1 to obtain a red colored composition. .
[Comparative Example A1]
Instead of the pigment dispersant A2 in Reference Example a1, the pigment dispersant A1 obtained in Synthesis Example A1 was used, and a red colored composition was obtained in the same manner as in Reference Example a1 .
上記の参考例ａ１〜ａ４の着色組成物の流動性と展色面のグロスおよび異物発生の有無を比較例Ａ１の場合と比較した。各着色組成物の流動性と展色のグロスを下記の方法に従って測定し、異物発生の有無を下記の方法で観察した。参考例ａ１〜ａ４の着色組成物を室温で１ヶ月間貯蔵前後の、それらの測定の観察結果を、比較例Ａ１の場合と相対評価を行った。
流動性：Ｅ型粘度計を用い、各着色組成物を室温（２５℃）、ローターの回転数６ｒｐｍの条件で測定した。
It was compared to that of Comparative Example A1 the presence or absence of gloss and debris generated liquidity and Exhibition color surface of the above-described coloring composition of Example a. 1 to a 4. The fluidity and color gloss of each colored composition were measured according to the following method, and the presence or absence of foreign matter was observed by the following method. Before and after one month storage of the coloring composition of Example a. 1 to a 4 at room temperature, the observation results of these measurements were carried out when the relative evaluation of Comparative Example A1.
Flowability: Using an E-type viscometer, each colored composition was measured under conditions of room temperature (25 ° C.) and a rotor rotation speed of 6 rpm.
グロス：バーコーター（巻線の太さ０．４５ｍｍ）を使用して、それぞれの着色組成物を別々にポリプロピレンフィルムに展色し、展色面のグロスを目視およびグロスメーターにて比較した。なお、グロスの高いものを良好と評価し、比較結果を下記の評価指標で表示した。
○：良好
△：やや良好
×：不良
異物観察：各着色組成物をスピンナーでガラス基板に塗布し、９０℃で２分乾燥して成膜後、被膜を顕微鏡を用いて２００倍で、異物の有無について観察し、観察結果を下記の評価指標で表示した。
○：異物なし
△：わずかに異物あり
×：かなり異物あり
以上の測定および評価の結果を表Ａ１に示す。
Gloss: Using a bar coater (winding thickness: 0.45 mm), each colored composition was separately developed on a polypropylene film, and the gloss of the developed surface was compared visually and with a gloss meter. In addition, the thing with high gloss was evaluated as favorable, and the comparison result was displayed with the following evaluation index.
○: Good Δ: Slightly good ×: Observation of defective foreign matter: Each colored composition was applied to a glass substrate with a spinner, dried at 90 ° C. for 2 minutes, and formed into a film. The presence or absence was observed, and the observation results were displayed with the following evaluation indices.
○: No foreign matter Δ: Slightly foreign matter ×: Very foreign matter The results of the above measurement and evaluation are shown in Table A1.
表Ａ１から明らかなように、顔料分散剤Ａ２〜Ａ５を使用した参考例ａ１〜ａ４の着色組成物は、顔料分散剤Ａ１を使用した比較例Ａ１の該組成物に比べて、貯蔵後の粘度（１ヶ月後）が低く、グロスも良好で、貯蔵前も貯蔵後も異物の発生がなく、着色組成物として優れた性質を有していた。 As is apparent from Table A1, the colored compositions of Reference Examples a 1 to a 4 using pigment dispersants A2 to A5 were after storage compared to the composition of Comparative Example A1 using pigment dispersant A1. The product had a low viscosity (after 1 month), good gloss, no generation of foreign matter before and after storage, and had excellent properties as a colored composition.
［参考例Ａ１］
参考例ａ１で使用したものと同じ種類のアクリル樹脂ワニス５０部に臭塩素化フタロシアニングリーン（Ｃ．Ｉ．ピグメントグリーン３６）１７部、キノフタロンイエロー顔料（Ｃ．Ｉ．ピグメントイエロー１３８）１３部、顔料分散剤としてモノスルホン化キノフタロンイエロー２部、カチオン系樹脂分散剤（ディスパーＢＹＫ−２０００）４部およびＰＧＭＡｃ２０部配合し、プレミキシングの後、横型ビーズミルで分散し、緑色の着色組成物を得た。
[Reference Example A1]
50 parts of the same kind of acrylic resin varnish used in Reference Example a 1 17 parts of odor chlorinated phthalocyanine green (CI Pigment Green 36), 13 parts of quinophthalone yellow pigment (CI Pigment Yellow 138), As a pigment dispersant, 2 parts of monosulfonated quinophthalone yellow, 4 parts of cationic resin dispersant (Disper BYK-2000) and 20 parts of PGMAc were blended and dispersed by a horizontal bead mill after premixing to obtain a green colored composition. .
［参考例Ａ２］
参考例ａ１で使用したものと同じ種類のアクリル樹脂ワニス５０部にε型銅フタロシアニンブルー（Ｃ．Ｉ．ピグメントブルー１５：６）１６部、ジオキサジンバイオレット（Ｃ．Ｉ．ピグメントバイオレット２３）４部、顔料分散剤としてモノスルホン化フタロシアニンブルー２部、モノスルホン化インダントロン１部、カチオン系樹脂分散剤（ディスパーＢＹＫ−２０００）４部およびＰＧＭＡｃ２０部配合し、プレミキシングの後、横型ビーズミルで分散し、青色の着色組成物を得た。
[Reference Example A2]
50 parts of the same kind of acrylic resin varnish used in Reference Example a 1, 16 parts of ε-type copper phthalocyanine blue (CI Pigment Blue 15: 6), dioxazine violet (CI Pigment Violet 23) 4 1 part, 1 part of monosulfonated phthalocyanine blue, 1 part of monosulfonated indanthrone, 4 parts of cationic resin dispersant (Disper BYK-2000) and 20 parts of PGMAc as a pigment dispersant, premixed and dispersed with a horizontal bead mill And a blue colored composition was obtained.
［参考例ａ５］
ＲＧＢのカラーフィルターを作製するために、下記の表Ａ２の配合処方によりＲ、ＧおよびＢの着色組成物を得た。
[ Reference Example a5 ]
In order to produce RGB color filters, colored compositions of R, G, and B were obtained according to the formulation of Table A2 below.
シランカップリング剤処理を行ったガラス基板をスピンコーターにセットし、表Ａ２のＲの着色組成物を最初３００ｒｐｍで５秒間、次いで１，２００ｒｐｍで５秒間の条件でスピンコートした。次いで８０℃で１０分間プリベークを行い、モザイク状の画素パターンを有するフォトマスクをプリベークしたフィルムに密着させ、超高圧水銀灯を用い１００ｍＪ／ｃｍ2の光量で露光を行った。次いで専用現像液および専用リンスで現像および洗浄を行い、ガラス基板上に赤色のモザイク状画素を形成させた。引き続いて緑色モザイク状画素および青色モザイク状画素を表Ａ２のＧおよびＢの着色組成物を用いて上記の方法に準じて塗布および焼き付けを行って形成し、ＲＧＢの各画素を有するカラーフィルターを得た。得られたカラーフィルターは優れた分光カーブ特性を有し、各画素の耐光性や耐熱性などの堅牢性に優れ、また、光の透過性にも優れた液晶カラーディスプレイ用カラーフィルターとして優れた性質を示した。 The glass substrate treated with the silane coupling agent was set on a spin coater, and the colored composition of R in Table A2 was first spin-coated at 300 rpm for 5 seconds and then at 1200 rpm for 5 seconds. Subsequently, prebaking was performed at 80 ° C. for 10 minutes, a photomask having a mosaic pixel pattern was brought into close contact with the prebaked film, and exposure was performed with an ultrahigh pressure mercury lamp at a light amount of 100 mJ / cm 2 . Next, development and washing were performed with a dedicated developer and a dedicated rinse to form red mosaic pixels on the glass substrate. Subsequently, a green mosaic pixel and a blue mosaic pixel are formed by applying and baking in accordance with the above method using the colored compositions of G and B in Table A2 to obtain a color filter having RGB pixels. It was. The resulting color filter has excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance of each pixel, and excellent properties as a color filter for liquid crystal color displays with excellent light transmission showed that.
［合成例Ｂ１］
ニトロベンゼン１，０００部に、７２部の１−アミノアントラキノンと３０部の塩化シアヌルとを加え、１７０℃で５時間攪拌する。冷却後、４１部のタウリンと２３部の炭酸カリウムを添加して１８０℃で８時間攪拌する。冷却後析出物を濾過し、アルコール洗浄し、次いで水に解膠して塩酸酸性にした。析出物を濾過により集め、水で洗浄および乾燥して、下記の化合物Ｂ１の９４部を得た。
[Synthesis Example B1]
To 1,000 parts of nitrobenzene, 72 parts of 1-aminoanthraquinone and 30 parts of cyanuric chloride are added and stirred at 170 ° C. for 5 hours. After cooling, 41 parts taurine and 23 parts potassium carbonate are added and stirred at 180 ° C. for 8 hours. After cooling, the precipitate was filtered, washed with alcohol, then peptized into water and made acidic with hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to obtain 94 parts of the following compound B1.
［合成例Ｂ２］
ニトロベンゼン１，０００部に、７２部の１−アミノアントラキノンと３０部の塩化シアヌルとを加え、１７０℃で５時間攪拌する。冷却後、５６部のスルファニル酸と２３部の炭酸カリウムを添加して１８０℃で１２時間攪拌する。冷却後濾過し、アルコール洗浄し、次いで水に解膠して塩酸酸性にした後水で洗浄および乾燥して、下記の化合物Ｂ２の１０１部を得た。
[Synthesis Example B2]
To 1,000 parts of nitrobenzene, 72 parts of 1-aminoanthraquinone and 30 parts of cyanuric chloride are added and stirred at 170 ° C. for 5 hours. After cooling, 56 parts sulfanilic acid and 23 parts potassium carbonate are added and stirred at 180 ° C. for 12 hours. After cooling, it was filtered, washed with alcohol, then peptized into water to make it acidic with hydrochloric acid, washed with water and dried to obtain 101 parts of the following compound B2.
［合成例Ｂ３］
ｏ−ジクロロベンゼン１，１００部に、７３部の１−アミノアントラキノンと３０部の塩化シアヌルを加え、１７０℃で５時間攪拌する。冷却後、３５部のｏ−トルイジンを添加して１８０℃で５時間攪拌する。冷却後濾過し、アルコール洗浄、次いで水で洗浄および乾燥して、２，４−ビス（１−アントラキノニルアミノ）−６−トリルアミノ−１，３，５−トリアジン９４部を得た。次いで、この化合物９４部を５％発煙硫酸８００部に１０℃以下で添加し、その後３０℃で５時間反応させる。冷却後、反応混合物を２，５００部の氷水中に析出させ、濾過および水洗し、硫黄の元素分析の結果より１分子当たり平均０．９個のスルホン基が導入されている下記の化合物Ｂ３の１０２部を得た。
[Synthesis Example B3]
73 parts of 1-aminoanthraquinone and 30 parts of cyanuric chloride are added to 1,100 parts of o-dichlorobenzene and stirred at 170 ° C. for 5 hours. After cooling, 35 parts of o-toluidine is added and stirred at 180 ° C. for 5 hours. After cooling, it was filtered, washed with alcohol, then washed with water and dried to obtain 94 parts of 2,4-bis (1-anthraquinonylamino) -6-tolylamino-1,3,5-triazine. Next, 94 parts of this compound is added to 800 parts of 5% fuming sulfuric acid at 10 ° C. or lower, and then reacted at 30 ° C. for 5 hours. After cooling, the reaction mixture was precipitated in 2,500 parts of ice water, filtered and washed with water. From the result of elemental analysis of sulfur, an average of 0.9 sulfone groups per molecule was introduced. 102 parts were obtained.
［実施例Ｂ１］
アクリル樹脂ワニス（メタクリル酸／ブチルアクリレート／スチレン／ヒドロキシエチルアクリレートを２５／５０／１５／１０のモル比で共重合させたもの、分子量１２，０００、固形分３０％）５０部にジケトピロロピロール顔料（Ｃ．Ｉ．ピグメントレッド２５４）２０部、イソインドリンイエロー顔料（Ｃ．Ｉ．ピグメントイエロー１３９）４部、合成例Ｂ１で得られた化合物Ｂ１の１部、前記合成例Ａ４で得られた顔料分散剤Ａ５の１部、カチオン系樹脂分散剤（ディスパーＢＹＫ−２０００）４部およびＰＧＭＡｃ２０部を配合し、プレミキシングの後、横型ビーズミルで分散し、赤色の着色組成物を得た。
[Example B1]
Diketopyrrolopyrrole in 50 parts of acrylic resin varnish (copolymerized methacrylic acid / butyl acrylate / styrene / hydroxyethyl acrylate in a molar ratio of 25/50/15/10, molecular weight 12,000, solid content 30%) 20 parts of pigment (CI Pigment Red 254), 4 parts of isoindoline yellow pigment (CI Pigment Yellow 139), 1 part of Compound B1 obtained in Synthesis Example B1, obtained in Synthesis Example A4 One part of the pigment dispersant A5, 4 parts of a cationic resin dispersant (Disper BYK-2000) and 20 parts of PGMAc were blended, and after premixing, the mixture was dispersed with a horizontal bead mill to obtain a red colored composition.
［実施例Ｂ２］
化合物Ｂ１の代わりに合成例Ｂ２の化合物Ｂ２を使用する以外は実施例Ｂ１と同様にして赤色の着色組成物を得た。
[Example B2]
A red colored composition was obtained in the same manner as in Example B1, except that Compound B2 of Synthesis Example B2 was used instead of Compound B1.
［実施例Ｂ３］
化合物Ｂ１の代わりに合成例Ｂ３の化合物Ｂ３を使用する以外は実施例Ｂ１と同様にして赤色の着色組成物を得た。
[Example B3]
A red colored composition was obtained in the same manner as in Example B1, except that Compound B3 of Synthesis Example B3 was used instead of Compound B1.
［比較例Ｂ１］
顔料分散剤Ａ５を使用せず、化合物Ｂ１のみを使用した以外は、実施例Ｂ１と同様にして赤色の着色組成物を得た。
[Comparative Example B1]
A red colored composition was obtained in the same manner as in Example B1, except that only the compound B1 was used without using the pigment dispersant A5.
［比較例Ｂ２］
顔料分散剤Ａ５を使用せず、化合物Ｂ２のみを使用しした以外は、実施例Ｂ１と同様にして赤色の着色組成物を得た。
[Comparative Example B2]
A red colored composition was obtained in the same manner as in Example B1 except that only the compound B2 was used without using the pigment dispersant A5.
［比較例Ｂ３］
顔料分散剤Ａ５を使用せず、化合物Ｂ３のみを使用しした以外は、実施例Ｂ１と同様にして赤色の着色組成物を得た。
[Comparative Example B3]
A red colored composition was obtained in the same manner as in Example B1 except that only the compound B3 was used without using the pigment dispersant A5.
上記の実施例Ｂ１〜Ｂ３の着色組成物の流動性と展色面のグロスを比較例Ｂ１〜Ｂ３の場合と比較した。各着色組成物の流動性および展色面のグロス（１ケ月間貯蔵後）を、前記と同じ方法に従って測定し、前記と同様にして比較例Ｂ１〜Ｂ３の場合と相対評価を行った。以上の測定および評価結果を表Ｂ１に示す。 The fluidity and color gloss of the colored compositions of Examples B1 to B3 described above were compared with those of Comparative Examples B1 to B3. The fluidity of each colored composition and the gloss (after one month storage) of the color development surface were measured according to the same method as described above, and the relative evaluation was performed in the same manner as in Comparative Examples B1 to B3. The above measurement and evaluation results are shown in Table B1.
表Ｂ１から明らかなように、化合物Ｂ１〜Ｂ３および顔料分散剤Ａ５を併用した実施例Ｂ１〜Ｂ３の着色組成物は、化合物Ｂ１〜Ｂ３を単独で使用した比較例Ｂ１〜Ｂ３の該組成物に比べて、貯蔵前および貯蔵後の粘度（１ヶ月後）が低く、グロスも良好で着色組成物として優れた性質を有していた。 As is apparent from Table B1, the colored compositions of Examples B1 to B3 using the compounds B1 to B3 and the pigment dispersant A5 in combination with the compositions of Comparative Examples B1 to B3 using the compounds B1 to B3 alone. In comparison, the viscosity before storage and after storage (after one month) was low, the gloss was good, and the coloring composition had excellent properties.
［実施例Ｂ４］
ＲＧＢの各画素を有するカラーフィルターを作製するために、下記の表Ｂ２の配合処方によりＲ、ＧおよびＢの着色組成物を得た。
[Example B4]
In order to produce a color filter having each pixel of RGB, colored compositions of R, G and B were obtained according to the formulation of Table B2 below.
以下参考例ａ５と同様にしてＲＧＢの各画素を有するカラーフィルターを得た。得られたカラーフィルターは優れた分光カーブ特性を有し、耐光性や耐熱性などの堅牢性に優れ、また、光の透過性にも優れ、液晶カラーディスプレイ用カラーフィルターとして優れた性質を示した。 Thereafter, a color filter having RGB pixels was obtained in the same manner as in Reference Example a5 . The obtained color filter had excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance, and excellent light transmission, and showed excellent properties as a color filter for liquid crystal color display. .
［合成例Ｃ１］
テトラクロロキノフタロン５０部を２０％発煙硫酸２５０部に添加し、その後８０℃で６時間反応させる。冷却後、反応混合物を２，０００部の氷水中に析出させ、濾過および水洗し、下記の化合物Ｃ１の水ペースト２８０部（純量５５部）を得た。この水ペーストを乾燥させ、硫黄の元素分析の結果より１分子あたり平均１．３個のスルホン基が導入されている化合物Ｃ１の５５部を得た。
[Synthesis Example C1]
50 parts of tetrachloroquinophthalone are added to 250 parts of 20% fuming sulfuric acid and then reacted at 80 ° C. for 6 hours. After cooling, the reaction mixture was precipitated in 2,000 parts of ice water, filtered and washed with water to obtain 280 parts (pure 55 parts) of an aqueous paste of the following compound C1. This water paste was dried, and 55 parts of Compound C1 into which an average of 1.3 sulfone groups were introduced per molecule were obtained from the results of elemental analysis of sulfur.
［合成例Ｃ２］
合成例Ｃ１の化合物Ｃ１のペースト９０部（純量１８部）に水２４０部を加え２５℃で１時間攪拌した。これにテトラブチルアンモニウムクロライド７部を加え１時間攪拌した。析出物を濾過、水洗および乾燥し、下記の化合物Ｃ２の１７部を得た。
[Synthesis Example C2]
240 parts of water was added to 90 parts (pure amount: 18 parts) of the compound C1 paste of Synthesis Example C1, and the mixture was stirred at 25 ° C. for 1 hour. To this, 7 parts of tetrabutylammonium chloride was added and stirred for 1 hour. The precipitate was filtered, washed with water and dried to obtain 17 parts of the following compound C2.
［合成例Ｃ３］
テトラクロロキノフタロン５０部の代わりにＣ．Ｉ．Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｗ １３８の５０部を用いる以外は、合成例Ｃ１と同様な操作を行ない、硫黄の元素分析の結果より１分子あたり平均０．９個のスルホン基が導入されている下記の化合物Ｃ３の５６部を得た。
[Synthesis Example C3]
Instead of 50 parts of tetrachloroquinophthalone, C.I. I. Except for using 50 parts of Pigment Yellow 138, the same operation as in Synthesis Example C1 was performed, and an average of 0.9 sulfone groups per molecule was introduced from the result of elemental analysis of sulfur. Got a part.
［合成例Ｃ４］
合成例Ｃ１の化合物Ｃ１の水ペースト９０部の代わりに合成例Ｃ３の化合物Ｃ３の水ペースト９０部を用いる以外は、合成例Ｃ２と同様な操作を行ない、下記の化合物Ｃ４の１８部を得た。
[Synthesis Example C4]
The same operation as in Synthesis Example C2 was carried out except that 90 parts of the water paste of Compound C3 of Synthesis Example C3 was used instead of 90 parts of the water paste of Compound C1 of Synthesis Example C1, and 18 parts of the following Compound C4 was obtained. .
［実施例Ｃ１］
アクリル樹脂ワニス（メタクリル酸／ブチルアクリレート／スチレン／ヒドロキシエチルアクリレートを２５／５０／１５／１０のモル比で共重合させたもの、分子量１２，０００、固形分３０％）５０部にジケトピロロピロール顔料（Ｃ．Ｉ．ピグメントレッド２５４）２０部、イソインドリンイエロー顔料（Ｃ．Ｉ．ピグメントイエロー１３９）４部、合成例Ｃ１で得られた化合物Ｃ１の１部、前記合成例Ａ４で得られた顔料分散剤Ａ５の１部、カチオン系樹脂分散剤（アジスパーＰＢ−８２１）４部およびＰＧＭＡｃを２０部配合し、プレミキシングの後、横型ビーズミルで分散し、赤色の着色組成物を得た。
[Example C1]
Diketopyrrolopyrrole in 50 parts of acrylic resin varnish (copolymerized methacrylic acid / butyl acrylate / styrene / hydroxyethyl acrylate in a molar ratio of 25/50/15/10, molecular weight 12,000, solid content 30%) 20 parts of pigment (CI Pigment Red 254), 4 parts of isoindoline yellow pigment (CI Pigment Yellow 139), 1 part of Compound C1 obtained in Synthesis Example C1, obtained in Synthesis Example A4 One part of pigment dispersant A5, 4 parts of cationic resin dispersant (Ajisper PB-821) and 20 parts of PGMAc were blended, and after premixing, the mixture was dispersed by a horizontal bead mill to obtain a red colored composition.
［実施例Ｃ２］
化合物Ｃ１の代わりに合成例Ｃ２の化合物Ｃ２を使用する以外は実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Example C2]
A red colored composition was obtained in the same manner as in Example C1, except that Compound C2 of Synthesis Example C2 was used instead of Compound C1.
［実施例Ｃ３］
化合物Ｃ１の代わりに合成例Ｃ３の化合物Ｃ３を使用する以外は実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Example C3]
A red colored composition was obtained in the same manner as in Example C1, except that Compound C3 of Synthesis Example C3 was used instead of Compound C1.
［実施例Ｃ４］
化合物Ｃ１の代わりに合成例Ｃ４の化合物Ｃ４を使用する以外は実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Example C4]
A red colored composition was obtained in the same manner as in Example C1, except that Compound C4 of Synthesis Example C4 was used instead of Compound C1.
［比較例Ｃ１］
顔料分散剤Ａ５を使用せず、化合物Ｃ１のみを使用した以外は、実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Comparative Example C1]
A red colored composition was obtained in the same manner as in Example C1, except that the pigment dispersant A5 was not used and only the compound C1 was used.
［比較例Ｃ２］
顔料分散剤Ａ５を使用せず、化合物Ｃ２のみを使用した以外は、実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Comparative Example C2]
A red colored composition was obtained in the same manner as in Example C1, except that the pigment dispersant A5 was not used and only the compound C2 was used.
［比較例Ｃ３］
顔料分散剤Ａ５を使用せず、化合物Ｃ３のみを使用した以外は、実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Comparative Example C3]
A red colored composition was obtained in the same manner as in Example C1 except that only the compound C3 was used without using the pigment dispersant A5.
［比較例Ｃ４］
顔料分散剤Ａ５を使用せず、化合物Ｃ４のみを使用した以外は、実施例Ｃ１と同様にして赤色の着色組成物を得た。
[Comparative Example C4]
A red colored composition was obtained in the same manner as in Example C1 except that only the compound C4 was used without using the pigment dispersant A5.
上記の実施例Ｃ１〜Ｃ４の着色組成物の流動性と展色面のグロスを比較例Ｃ１〜Ｃ４の場合と比較した。各着色組成物の流動性および展色面のグロス（１ケ月間貯蔵後）を、前記と同じ方法に従って測定し、比較例Ｃ１〜Ｃ４の場合と相対評価を行った。以上の測定および評価結果を表Ｃ１に示す。 The fluidity of the coloring compositions of Examples C1 to C4 and the gloss of the color development surface were compared with those of Comparative Examples C1 to C4. The fluidity of each coloring composition and the gloss of the color-extended surface (after storage for 1 month) were measured according to the same method as described above, and the relative evaluation was performed with Comparative Examples C1 to C4. The above measurement and evaluation results are shown in Table C1.
表Ｃ１から明らかなように、化合物Ｃ１〜Ｃ４および顔料分散剤Ａ５を併用した実施例Ｃ１〜Ｃ４の着色組成物は、化合物Ｃ１〜Ｃ４を単独で使用した比較例Ｃ１〜Ｃ４の該組成物に比べて、貯蔵前および貯蔵後の粘度（１ヶ月後）が低く、グロスも良好で着色組成物として優れた性質を有していた。 As is clear from Table C1, the colored compositions of Examples C1 to C4 using the compounds C1 to C4 and the pigment dispersant A5 in combination with the compositions of Comparative Examples C1 to C4 using the compounds C1 to C4 alone. In comparison, the viscosity before storage and after storage (after one month) was low, the gloss was good, and the coloring composition had excellent properties.
［実施例Ｃ５］
ＲＧＢの各画素を有するカラーフィルターを作製するために、下記の表Ｃ２の配合処方によりＲ、ＧおよびＢの着色組成物を得た。
[Example C5]
In order to produce a color filter having RGB pixels, colored compositions of R, G, and B were obtained according to the formulation of Table C2 below.
以下参考例ａ５と同様にしてＲＧＢの各画素を有するカラーフィルターを得た。得られたカラーフィルターは優れた分光カーブ特性を有し、耐光性や耐熱性などの堅牢性に優れ、また、光の透過性にも優れ、液晶カラーディスプレイ用カラーフィルターとして優れた性質を示した。 Thereafter, a color filter having RGB pixels was obtained in the same manner as in Reference Example a5 . The obtained color filter had excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance, and excellent light transmission, and showed excellent properties as a color filter for liquid crystal color display. .
［合成例Ｄ１］
常法により、３−ヒドロキシ−２−ナフトエ酸６０部をニトロベンゼン４００部中、塩化チオニル４０部を用いて酸クロライド化し、２，５−ジクロロ−１，４−フェニレンジアミン２５部を加え１３０〜１３５℃で５時間加熱する。冷却後、メタノール２００部を加え、精製した析出物をろ過しメタノール、次いで水で洗浄、乾燥し、反応物６０部を得た。このうちの１０部に、メタノール１００部、水酸化ナトリウム３部、酢酸ナトリウム３水和物１１部を加えて下漬液とする。ｐ−アミノベンゼンスルホン酸３．５部を常法によりジアゾ化し、上記下漬液にカップリングさせ、１時間後、２−クロロ−５−トリフルオロメチルアニリンを４．３部を常法によりジアゾ化し、カップリングさせ硫黄の元素分析の結果より１分子あたり平均１個のスルホン基が導入されている下記の化合物Ｄ１の１１部を得た。
[Synthesis Example D1]
According to a conventional method, 60 parts of 3-hydroxy-2-naphthoic acid was acidified with 40 parts of thionyl chloride in 400 parts of nitrobenzene, and 25 parts of 2,5-dichloro-1,4-phenylenediamine was added to add 130 to 135. Heat at 5 ° C. for 5 hours. After cooling, 200 parts of methanol was added, and the purified precipitate was filtered, washed with methanol and then with water, and dried to obtain 60 parts of a reaction product. To 10 parts of this, 100 parts of methanol, 3 parts of sodium hydroxide, and 11 parts of sodium acetate trihydrate are added to prepare a submerged solution. 3.5 parts of p-aminobenzenesulfonic acid is diazotized by a conventional method and coupled to the above-described submerged solution. After 1 hour, 4.3 parts of 2-chloro-5-trifluoromethylaniline is diazotized by a conventional method. From the result of elemental analysis of sulfur, 11 parts of the following compound D1 in which an average of one sulfone group was introduced per molecule were obtained.
［合成例Ｄ２］
合成例Ｄ１の２，５−ジクロロ−１，４−フェニレンジアミン２５部の代わりに３，３’−ジクロロベンジジン３５部を使用する以外は合成例Ｄ１と同様にして、硫黄の元素分析の結果より１分子あたり平均１個のスルホン基が導入されている下記の化合物Ｄ２の１１部を得た。
[Synthesis Example D2]
From the result of elemental analysis of sulfur in the same manner as in Synthesis Example D1, except that 35 parts of 3,3′-dichlorobenzidine is used instead of 25 parts of 2,5-dichloro-1,4-phenylenediamine in Synthesis Example D1. 11 parts of the following compound D2 into which an average of one sulfone group was introduced per molecule were obtained.
［実施例Ｄ１］
アクリル樹脂ワニス（メタクリル酸／ブチルアクリレート／スチレン／ヒドロキシエチルアクリレートを２５／５０／１５／１０のモル比で共重合させたもの、分子量１２，０００、固形分３０％）５０部にジケトピロロピロール顔料（Ｃ．Ｉ．ピグメントレッド２５４）２０部、イソインドリンイエロー顔料（Ｃ．Ｉ．ピグメントイエロー１３９）４部、合成例Ｄ１で得られた化合物Ｄ１の１部、前記合成例Ａ４で得られた顔料分散剤Ａ５の１部、カチオン系樹脂分散剤（ソルスパース−２４０００）４部およびＰＧＭＡｃを２０部配合し、プレミキシングの後、横型ビーズミルで分散し、赤色の着色組成物を得た。
[Example D1]
Diketopyrrolopyrrole in 50 parts of acrylic resin varnish (copolymerized methacrylic acid / butyl acrylate / styrene / hydroxyethyl acrylate in a molar ratio of 25/50/15/10, molecular weight 12,000, solid content 30%) 20 parts of pigment (CI Pigment Red 254), 4 parts of isoindoline yellow pigment (CI Pigment Yellow 139), 1 part of Compound D1 obtained in Synthesis Example D1, obtained in Synthesis Example A4 One part of the pigment dispersant A5, 4 parts of a cationic resin dispersant (Solsperse-24000) and 20 parts of PGMAc were blended, and after premixing, the mixture was dispersed with a horizontal bead mill to obtain a red colored composition.
［実施例Ｄ２］
化合物Ｄ１の代わりに合成例Ｄ２の化合物Ｄ２を使用する以外は実施例Ｄ１と同様にして赤色の着色組成物を得た。
[Example D2]
A red colored composition was obtained in the same manner as in Example D1, except that Compound D2 of Synthesis Example D2 was used instead of Compound D1.
［比較例Ｄ１］
顔料分散剤Ａ５を使用せず、化合物Ｄ１のみを使用した以外は、実施例Ｄ１と同様にして赤色の着色組成物を得た。
[Comparative Example D1]
A red colored composition was obtained in the same manner as in Example D1, except that only the compound D1 was used without using the pigment dispersant A5.
［比較例Ｄ２］
顔料分散剤Ａ５を使用せず、化合物Ｄ２のみを使用した以外は、実施例Ｄ１と同様にして赤色の着色組成物を得た。
[Comparative Example D2]
A red colored composition was obtained in the same manner as in Example D1, except that the pigment dispersant A5 was not used and only the compound D2 was used.
上記の実施例Ｄ１〜Ｄ２の着色組成物の流動性と展色面のグロスを比較例Ｄ１〜Ｄ２の場合と比較した。各着色組成物の流動性および展色面のグロス（１ケ月間貯蔵後）を、前記と同じ方法に従って測定し、比較例の場合と相対評価を行った。以上の測定および評価結果を表Ｄ１に示す。 The fluidity of the coloring compositions of the above Examples D1 to D2 and the gloss of the color development surface were compared with those of Comparative Examples D1 to D2. The fluidity of each coloring composition and the gloss of the color-extended surface (after storage for 1 month) were measured according to the same method as described above, and the relative evaluation was performed as in the comparative example. The above measurement and evaluation results are shown in Table D1.
表Ｄ１から明らかなように、化合物Ｄ１〜Ｄ２および顔料分散剤Ａ５を併用した実施例Ｄ１〜Ｄ２の着色組成物は、化合物Ｄ１〜２を単独で使用した比較例Ｄ１〜Ｄ２の該組成物に比べて、貯蔵前および貯蔵後の粘度（１ヶ月後）が低く、グロスも良好で着色組成物として優れた性質を有していた。 As is clear from Table D1, the coloring compositions of Examples D1 to D2 using the compounds D1 to D2 and the pigment dispersant A5 in combination with the compositions of Comparative Examples D1 to D2 using the compounds D1 and 2 alone. In comparison, the viscosity before storage and after storage (after one month) was low, the gloss was good, and the coloring composition had excellent properties.
［実施例Ｄ３］
ＲＧＢの各画素を有するカラーフィルターを作製するために、下記の表Ｄ２の配合処方によりＲ、ＧおよびＤの着色組成物を得た。
[Example D3]
In order to produce a color filter having RGB pixels, colored compositions of R, G, and D were obtained according to the formulation of Table D2 below.
以下参考例ａ５と同様にしてＲＧＢの各画素を有するカラーフィルターを得た。得られたカラーフィルターは優れた分光カーブ特性を有し、耐光性や耐熱性などの堅牢性に優れ、また、光の透過性にも優れ、液晶カラーディスプレイ用カラーフィルターとして優れた性質を示した。 Thereafter, a color filter having RGB pixels was obtained in the same manner as in Reference Example a5 . The obtained color filter had excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance, and excellent light transmission, and showed excellent properties as a color filter for liquid crystal color display. .
本発明によれば、特定の顔料分散剤をカラーフィルターの赤色画素形成用着色組成物の顔料分散剤として併用することによる相乗効果により、それぞれを単独で使用する場合より特異的に顔料粒子の凝集を防止することが可能となる。従って着色組成物も安定に製造することができ、異物の発生を防止し、また、最終的に着色組成物として使用される際にも、優れた分光カーブ特性を有し、鮮明で冴えた色調を出すことが可能で、透明感の高い、しかも耐光性、耐熱性、耐溶剤性、耐薬品性および耐水性などの諸堅牢性に優れた画素を有するカラーフィルターを得ることができる。 According to the present invention, due to the synergistic effect of using a specific pigment dispersant as a pigment dispersant for the color pixel forming color composition of the color filter, the aggregation of pigment particles more specifically than when each is used alone. Can be prevented. Therefore, the colored composition can also be stably produced, and the occurrence of foreign matters can be prevented. Also, when used as a colored composition, the colored composition has excellent spectral curve characteristics and has a clear and brilliant color tone. A color filter having a pixel with excellent transparency and high fastness such as light resistance, heat resistance, solvent resistance, chemical resistance and water resistance can be obtained.
Claims (12)
（ａ）成分；スルホン基を有するジケトピロロピロール顔料とスルホン基を有さないジケトピロロピロール顔料との顔料複合体であって、該複合体におけるジケトピロロピロール顔料分子１個あたりのスルホン基の数が０．０５〜０．５である顔料複合体であり、ジケトピロロピロール顔料は、下記一般式（Ｖ）で表される。
（ｂ）成分；下記の一般式（Ｉ）、一般式（II）、一般式（III）または一般式（IV）で表される化合物、その金属塩、アンモニウム塩および／またはアミン塩である。
Component (a): a pigment complex of a diketopyrrolopyrrole pigment having a sulfone group and a diketopyrrolopyrrole pigment having no sulfone group, the sulfone per molecule of the diketopyrrolopyrrole pigment in the complex It is a pigment complex having 0.05 to 0.5 groups, and the diketopyrrolopyrrole pigment is represented by the following general formula (V).
Component (b): a compound represented by the following general formula (I), general formula (II), general formula (III) or general formula (IV), a metal salt, an ammonium salt and / or an amine salt thereof.
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| JP2006321979A (en) * | 2005-04-19 | 2006-11-30 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant and its use |
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| JP2006265528A (en) | 2006-10-05 |
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