JP6720675B2 - Quinophthalone compound, pigment dispersant using the quinophthalone compound, coloring composition for color filter and color filter - Google Patents
Quinophthalone compound, pigment dispersant using the quinophthalone compound, coloring composition for color filter and color filter Download PDFInfo
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- JP6720675B2 JP6720675B2 JP2016088815A JP2016088815A JP6720675B2 JP 6720675 B2 JP6720675 B2 JP 6720675B2 JP 2016088815 A JP2016088815 A JP 2016088815A JP 2016088815 A JP2016088815 A JP 2016088815A JP 6720675 B2 JP6720675 B2 JP 6720675B2
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- -1 Quinophthalone compound Chemical class 0.000 title claims description 185
- 239000000203 mixture Substances 0.000 title claims description 113
- 239000000049 pigment Substances 0.000 title claims description 107
- 238000004040 coloring Methods 0.000 title claims description 60
- 239000002270 dispersing agent Substances 0.000 title claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 111
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 79
- 239000003086 colorant Substances 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000011230 binding agent Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 description 162
- 238000006243 chemical reaction Methods 0.000 description 105
- 150000001875 compounds Chemical class 0.000 description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 238000004519 manufacturing process Methods 0.000 description 63
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 62
- 239000006185 dispersion Substances 0.000 description 62
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 48
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 239000000758 substrate Substances 0.000 description 39
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- 239000010408 film Substances 0.000 description 31
- 229950000244 sulfanilic acid Drugs 0.000 description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 30
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 description 28
- 239000000975 dye Substances 0.000 description 23
- 239000002253 acid Substances 0.000 description 22
- 238000001816 cooling Methods 0.000 description 22
- 238000011156 evaluation Methods 0.000 description 21
- 239000001052 yellow pigment Substances 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 19
- 238000000576 coating method Methods 0.000 description 19
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 18
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- 239000004925 Acrylic resin Substances 0.000 description 17
- 229920000178 Acrylic resin Polymers 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 238000009826 distribution Methods 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000001056 green pigment Substances 0.000 description 12
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910017053 inorganic salt Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- VUZFQYDNVUBSBS-UHFFFAOYSA-N 2-methyl-6-nitroquinolin-8-ol Chemical compound C1=C([N+]([O-])=O)C=C(O)C2=NC(C)=CC=C21 VUZFQYDNVUBSBS-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 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 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 7
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 6
- 229960004963 mesalazine Drugs 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 5
- PQIYSSSTRHVOBW-UHFFFAOYSA-N 3-bromopropan-1-amine;hydron;bromide Chemical compound Br.NCCCBr PQIYSSSTRHVOBW-UHFFFAOYSA-N 0.000 description 5
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000001054 red pigment Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 239000001043 yellow dye Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
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- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 4
- 239000001055 blue pigment Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
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- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
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- KRKXGCJUNKZXOY-UHFFFAOYSA-N 4-acetamidobenzoyl chloride Chemical compound CC(=O)NC1=CC=C(C(Cl)=O)C=C1 KRKXGCJUNKZXOY-UHFFFAOYSA-N 0.000 description 3
- DRNGLYHKYPNTEA-UHFFFAOYSA-N 4-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCC(C(O)=O)CC1 DRNGLYHKYPNTEA-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
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- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
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- 125000005484 neopentoxy group Chemical group 0.000 description 1
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- 239000001005 nitro dye Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
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- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- KXEMQEGRZWUKJS-QIYNHLNTSA-N tetraphylline Chemical class COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-QIYNHLNTSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 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
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
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- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Optical Filters (AREA)
Description
カラーフィルタの高コントラスト化、及び高明度化には、微細化処理された顔料を、より微細な状態で分散させること(良好な分散性)が求められている。しかしながら、微細化処理された顔料は表面積が大きくなるため、顔料粒子間の凝集力が強くなり、顔料の分散性が不充分である場合には、分散体が高粘度化し、カラーフィルタの、コントラストが著しく劣化したりするという問題がある。高度なレベルでの分散性とコントラストを両立することは、困難であることが多い。 In order to increase the contrast and brightness of the color filter, it is required to disperse the finely treated pigment in a finer state (good dispersibility). However, since the finely treated pigment has a large surface area, the cohesive force between the pigment particles becomes strong, and when the dispersibility of the pigment is insufficient, the dispersion becomes highly viscous and the contrast of the color filter Is significantly deteriorated. It is often difficult to achieve both high level dispersibility and contrast.
このような問題を解決するために、様々な色素誘導体が開発されている。例えば、特許文献1〜7には、キノフタロン化合物を色素誘導体として使用した着色組成物が提案されている。これらの特許文献で提案されているキノフタロン化合物では、微細化処理された顔料を分散するにあたって、明度、コントラスト、分散性、及び耐熱性のすべてを満たす着色組成物を得ることができず、新たなキノフタロン化合物の開発が望まれていた。また、特許文献8〜9には、スルホン酸が置換したフタルイミド基を持つキノフタロン化合物が実施例の中間体として記載されているが、カラーフィルタ用途での有用性について明細書に記載がされていない。 In order to solve such problems, various dye derivatives have been developed. For example, Patent Documents 1 to 7 propose coloring compositions using a quinophthalone compound as a dye derivative. With the quinophthalone compounds proposed in these patent documents, it is not possible to obtain a colored composition that satisfies all of the brightness, contrast, dispersibility, and heat resistance when dispersing the finely treated pigment, and a new Development of quinophthalone compounds has been desired. Further, in Patent Documents 8 to 9, quinophthalone compounds having a phthalimide group substituted with sulfonic acid are described as intermediates of Examples, but the utility in color filter applications is not described in the specification. ..
本発明の目的は、明度、コントラスト、分散性、及び耐熱性に優れたカラーフィルタ用着色組成物を提供することである。 An object of the present invention is to provide a coloring composition for a color filter which is excellent in brightness, contrast, dispersibility and heat resistance.
すなわち、本発明は、下記一般式(1)で表されるキノフタロン化合物(A)に関する。 That is, the present invention relates to a quinophthalone compound (A) represented by the following general formula (1).
一般式(1)
[一般式(1)中、R1〜R9は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、置換基を有してもよい炭素数20以下のアルキル基、置換基を有してもよい炭素数20以下のアルコキシ基、又は置換基を有してもよい炭素数20以下のアリール基を表し、隣接する置換基同士が結合して、脂肪族飽和炭化水素系もしくは芳香族系の環状構造を形成しても良い。
Q1は、2価の連結基を表す。
A1及びB1は、それぞれ独立に、ヒドロキシル基、塩素原子、下記一般式(2)又は、下記一般式(3)で表され、少なくとも1つは下記一般式(2)で表される基である。
[In the general formula (1), R 1 to R 9 each independently have a hydrogen atom, a halogen atom, a nitro group, an optionally substituted alkyl group having 20 or less carbon atoms, and a substituent. Represents an alkoxy group having 20 or less carbon atoms or an aryl group having 20 or less carbon atoms which may have a substituent, and adjacent substituents are bonded to each other to form an aliphatic saturated hydrocarbon-based or aromatic-based You may form a cyclic structure.
Q1 represents a divalent linking group.
A1 and B1 are each independently represented by a hydroxyl group, a chlorine atom, the following general formula (2) or the following general formula (3), and at least one is a group represented by the following general formula (2). ..
一般式(2) −X1−Z1
(一般式(2)中、X1は、−NH−又は−O−を表す。Z1は、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のアルキル基を表し、X1とZ1とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z1は、−COOH、−SO3H及び−OSO3Hから選ばれる少なくとも1つの置換基を有する。)
Formula (2) -X 1 -Z 1
(In the general formula (2), X 1 represents —NH— or —O—. Z 1 may have a substituent having 20 or less carbon atoms, or may have a substituent. Represents a good alkyl group having 20 or less carbon atoms, and X 1 and Z 1 represent an arylene group having 20 or less carbon atoms which may have a substituent, and a heteroari having 20 or less carbon atoms which may have a substituent. lane group, a substituted alkylene group having 20 or less carbon atoms which may have, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - S -, - selected from NH- and -O- May be linked by at least one divalent linking group.
However, Z 1 has at least one substituent selected from —COOH, —SO 3 H, and —OSO 3 H. )
一般式(3) −X2−Z2
(一般式(3)中、X2は、−NH−又はO−を表す。Z2は、置換基を有してもよい炭素(一般式(3)中、X2は、−NH−又は−O−を表す。Z2は、置換基を有してもよい炭素数20以下のアルキル基、置換基を有してもよい炭素数20以下のアルケニル基、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のヘテロアリール基を表し、X2とZ2とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z2は、置換基として−COOH、−SO3H又はOSO3Hを有しない。)]
Formula (3) -X 2 -Z 2
(In the general formula (3), X 2 represents —NH— or O—. Z 2 is a carbon that may have a substituent (in the general formula (3), X 2 is —NH— or Represents —O— Z 2 may have an alkyl group having 20 or less carbon atoms which may have a substituent, an alkenyl group having 20 or less carbon atoms which may have a substituent, and a substituent. It represents an aryl group having 20 or less carbon atoms or a heteroaryl group having 20 or less carbon atoms which may have a substituent, and X 2 and Z 2 are arylene having 20 or less carbon atoms which may have a substituent. Group, a heteroarylene group having 20 or less carbon atoms which may have a substituent, an alkylene group having 20 or less carbon atoms which may have a substituent, -NHSO 2 -, -NHCO-, -OSO 2 -, They may be linked by at least one divalent linking group selected from -OCO-, -S-, -NH- and -O-.
However, Z 2 has no -COOH, -SO 3 H at or OSO 3 H as a substituent. )]
また、本発明は、一般式(1)において、Q1が、下記一般式(4)で表される上記キノフタロン化合物(A)に関する。 The present invention also relates to the above-mentioned quinophthalone compound (A), in which Q 1 in the general formula (1) is represented by the following general formula (4).
一般式(4) −(X3)n−(Z3)m−X4−*
[一般式(4)中、X3は、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−NH−又は−O−を表す。
Z3は、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、又は置換基を有してもよい炭素数20以下のアルキレン基を表し、mが2以上のときは、複数のZ3は同一でも異なっていてもよく、複数のZ3同士は、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
X4は、−NH−又は−O−を表す。
nは、0又は1の整数を表し、mは、0〜5の整数を表す。
*はトリアジン環との連結手である。]
Formula (4) - (X 3) n - (Z 3) m -X 4 - *
[In the general formula (4), X 3 is, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - NH- or an -O-.
Z 3 is an arylene group having 20 or less carbon atoms which may have a substituent, a heteroarylene group having 20 or less carbon atoms which may have a substituent, or a carbon number 20 which may have a substituent. The following alkylene groups are represented, and when m is 2 or more, a plurality of Z 3's may be the same or different, and a plurality of Z 3's are —NHSO 2 —, —NHCO—, —OSO 2 —, —. They may be linked by at least one divalent linking group selected from OCO-, -S-, -NH- and -O-.
X 4 represents -NH- or -O-.
n represents an integer of 0 or 1, and m represents an integer of 0 to 5.
* Is a linking hand with the triazine ring. ]
また、本発明は、一般式(4)において、nが1であり、mが1である上記キノフタロン化合物(A)に関する。 The present invention also relates to the above quinophthalone compound (A) in which n is 1 and m is 1 in the general formula (4).
また、本発明は、上記キノフタロン化合物(A)を含む顔料分散剤に関する。 The present invention also relates to a pigment dispersant containing the quinophthalone compound (A).
また、本発明は、上記顔料分散剤、着色剤、有機溶剤及びバインダー樹脂を含有するカラーフィルタ用着色組成物に関する。 The present invention also relates to a coloring composition for a color filter containing the above pigment dispersant, a coloring agent, an organic solvent and a binder resin.
また、本発明は、さらに、光重合性単量体及び光重合開始剤から選ばれた少なくとも1種を含有する上記カラーフィルタ用着色組成物に関する。 The present invention also relates to the above coloring composition for a color filter, which further contains at least one selected from a photopolymerizable monomer and a photopolymerization initiator.
さらに、本発明は、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つの緑色フィルタセグメント及び少なくとも1つの青色フィルタセグメントを備えるカラーフィルタにおいて、少なくとも1つの緑色フィルタセグメントが、上記カラーフィルタ用着色組成物から形成されるカラーフィルタに関する。 Furthermore, the present invention provides a color filter comprising at least one red filter segment, at least one green filter segment and at least one blue filter segment, wherein at least one green filter segment is formed from the above color filter coloring composition. Color filters.
本発明の一般式(1)で表されるキノフタロン化合物を着色剤と併用することで、明度、コントラスト、耐熱性が良好かつ、異物の少ない低粘度なカラーフィルタ用着色組成物を提供することができる。 By using the quinophthalone compound represented by the general formula (1) of the present invention in combination with a coloring agent, it is possible to provide a low-viscosity colored composition for color filters, which has good lightness, contrast, heat resistance, and little foreign matter. it can.
以下、本発明を詳細に説明する。なお、本明細書における「C.I.」は、カラーインデックス(C.I.)を意味する。 Hereinafter, the present invention will be described in detail. In addition, "CI" in this specification means a color index (CI).
<一般式(1)で表されるキノフタロン化合物(A)>
本発明の下記一般式(1)で表されるキノフタロン化合物(A)について説明する。
<Quinophthalone compound (A) represented by the general formula (1)>
The quinophthalone compound (A) represented by the following general formula (1) of the present invention will be described.
一般式(1)
[一般式(1)中、R1〜R9は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、置換基を有してもよい炭素数20以下のアルキル基、置換基を有してもよい炭素数20以下のアルコキシ基、又は置換基を有してもよい炭素数20以下のアリール基を表し、隣接する置換基同士が結合して、脂肪族飽和炭化水素系もしくは芳香族系の環状構造を形成しても良い。
Q1は、2価の連結基を表す。
A1及びB1は、それぞれ独立に、ヒドロキシル基、塩素原子、下記一般式(2)又は、下記一般式(3)で表され、少なくとも1つは下記一般式(2)で表される基である。
[In the general formula (1), R 1 to R 9 each independently have a hydrogen atom, a halogen atom, a nitro group, an optionally substituted alkyl group having 20 or less carbon atoms, and a substituent. Represents an alkoxy group having 20 or less carbon atoms or an aryl group having 20 or less carbon atoms which may have a substituent, and adjacent substituents are bonded to each other to form an aliphatic saturated hydrocarbon-based or aromatic-based You may form a cyclic structure.
Q1 represents a divalent linking group.
A1 and B1 are each independently represented by a hydroxyl group, a chlorine atom, the following general formula (2) or the following general formula (3), and at least one is a group represented by the following general formula (2). ..
一般式(2) −X1−Z1
(一般式(2)中、X1は、−NH−又は−O−を表す。Z1は、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のアルキル基を表し、X1とZ1とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z1は、−COOH、−SO3H及び−OSO3Hから選ばれる少なくとも1つの置換基を有する。)
Formula (2) -X 1 -Z 1
(In the general formula (2), X 1 represents —NH— or —O—. Z 1 may have a substituent having 20 or less carbon atoms, or may have a substituent. Represents a good alkyl group having 20 or less carbon atoms, and X 1 and Z 1 represent an arylene group having 20 or less carbon atoms which may have a substituent, and a heteroari having 20 or less carbon atoms which may have a substituent. lane group, a substituted alkylene group having 20 or less carbon atoms which may have, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - S -, - selected from NH- and -O- May be linked by at least one divalent linking group.
However, Z 1 has at least one substituent selected from —COOH, —SO 3 H, and —OSO 3 H. )
一般式(3) −X2−Z2
(一般式(3)中、X2は、−NH−又は−O−を表す。Z2は、置換基を有してもよい炭素数20以下のアルキル基、置換基を有してもよい炭素数20以下のアルケニル基、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のヘテロアリール基を表し、X2とZ2とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z2は、置換基として−COOH、−SO3H又はOSO3Hを有しない。)]
Formula (3) -X 2 -Z 2
(In the general formula (3), X 2 represents —NH— or —O—. Z 2 may have a substituent having 20 or less carbon atoms, or may have a substituent. It represents an alkenyl group having 20 or less carbon atoms, an aryl group having 20 or less carbon atoms that may have a substituent, or a heteroaryl group having 20 or less carbon atoms that may have a substituent, and X 2 and Z 2 Is an arylene group having 20 or less carbon atoms, which may have a substituent, a heteroarylene group having 20 or less carbon atoms, which may have a substituent, and an alkylene having 20 or less carbon atoms, which may have a substituent. group, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - S -, - selected from NH- and -O- may be linked by at least one divalent linking group ..
However, Z 2 has no -COOH, -SO 3 H at or OSO 3 H as a substituent. )]
一般式(1)におけるQ1は、下記一般式(4)で表される連結基であることが好ましい。 Q1 in the general formula (1) is preferably a linking group represented by the following general formula (4).
一般式(4) −(X3)n−(Z3)m−X4−*
[一般式(4)中、X3は、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−NH−又は−O−を表す。
Z3は、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、又は置換基を有してもよい炭素数20以下のアルキレン基を表し、mが2以上のときは、複数のZ3は同一でも異なっていてもよく、複数のZ3同士は、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
X4は、−NH−又は−O−を表す。
nは、0又は1の整数を表し、mは、0〜5の整数を表す。
*はトリアジン環との連結手である。]
Formula (4) - (X 3) n - (Z 3) m -X 4 - *
[In the general formula (4), X 3 is, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - NH- or an -O-.
Z 3 is an arylene group having 20 or less carbon atoms which may have a substituent, a heteroarylene group having 20 or less carbon atoms which may have a substituent, or a carbon number 20 which may have a substituent. The following alkylene groups are represented, and when m is 2 or more, a plurality of Z 3's may be the same or different, and a plurality of Z 3's are —NHSO 2 —, —NHCO—, —OSO 2 —, —. They may be linked by at least one divalent linking group selected from OCO-, -S-, -NH- and -O-.
X 4 represents -NH- or -O-.
n represents an integer of 0 or 1, and m represents an integer of 0 to 5.
* Is a linking hand with the triazine ring. ]
一般式(1)〜(4)における各基について説明する。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
Each group in the general formulas (1) to (4) will be described.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
アルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ドデシル基、オクタデシル基、トリフルオロメチル基、イソプロピル基、イソブチル基、イソペンチル基、2−エチルヘキシル基、2−ヘキシルドデシル基、sec−ブチル基、tert−ブチル基、sec−ペンチル基、tert−ペンチル基、tert−オクチル基、ネオペンチル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、アダマンチル基、ノルボルニル基、ボロニル基、4−デシルシクロヘキシル基等を挙げることができるが、これらに限定されるものではない。 As the alkyl group, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, octadecyl group, trifluoromethyl group, isopropyl group, isobutyl Group, isopentyl group, 2-ethylhexyl group, 2-hexyldecyl group, sec-butyl group, tert-butyl group, sec-pentyl group, tert-pentyl group, tert-octyl group, neopentyl group, cyclopropyl group, cyclobutyl group Examples thereof include, but are not limited to, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a boronyl group and a 4-decylcyclohexyl group.
アルコキシ基とは、上述のアルキル基に酸素原子が結合した基である。 The alkoxy group is a group in which an oxygen atom is bonded to the above alkyl group.
アルケニル基としては直鎖状、分岐鎖状、単環状又は縮合多環状アルケニル基が挙げられる。それらは構造中に複数の炭素−炭素二重結合を有していてもよい。具体例としては、ビニル基、1−プロペニル基、アリル基、2−ブテニル基、3−ブテニル基、イソプロペニル基、イソブテニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基、シクロペンテニル基、シクロヘキセニル基、1,3−ブタジエニル基、シクロヘキサジエニル基、シクロペンタジエニル基等を挙げることができるが、これらに限定されるものではない。 Examples of the alkenyl group include a linear, branched, monocyclic or condensed polycyclic alkenyl group. They may have multiple carbon-carbon double bonds in the structure. As specific examples, vinyl group, 1-propenyl group, allyl group, 2-butenyl group, 3-butenyl group, isopropenyl group, isobutenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4- Pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, cyclopentenyl group, cyclohexenyl group, 1,3-butadienyl group, cyclohexadienyl group, cyclopenta group Examples thereof include, but are not limited to, a dienyl group and the like.
アリール基としては、フェニル基、ビフェニリル基、ターフェニリル基、クオーターフェニリル基、ペンタレニル基、インデニル基、ナフチル基、ビナフタレニル基、ターナフタレニル基、クオーターナフタレニル基、アズレニル基、ヘプタレニル基、ビフェニレニル基、インダセニル基、フルオランテニル基、アセフェナントリレニル基、アセアントリレニル基、フェナレニル基、フルオレニル基、アントリル基、ビアントラセニル基、ターアントラセニル基、クオーターアントラセニル基、アントラキノリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、ナフタセニル基、プレイアデニル基、ピセニル基、ペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、ヘプタフェニル基、ヘプタセニル基、ピラントレニル基、オバレニル基等を挙げることができるが、これらに限定されるものではない。 Examples of the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a quarterphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, a binaphthalenyl group, a tarnaphthalenyl group, a quarternaphthalenyl group, an azulenyl group, a heptenyl group, a biphenylenyl group, and an indacenyl group. Group, fluoranthenyl group, acephenanthrylenyl group, aceanthrylenyl group, phenalenyl group, fluorenyl group, anthryl group, bianthracenyl group, teranthracenyl group, quarter anthracenyl group, anthraquinolyl group, phenanthryl group, triphenylenyl group Group, pyrenyl group, chrysenyl group, naphthacenyl group, preadenyl group, picenyl group, perylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, Examples thereof include, but are not limited to, a heptaphenyl group, a heptacenyl group, a pyrantrenyl group, an ovalenyl group, and the like.
ヘテロアリール基としては、ピロール、ピラゾール、イミダゾール、オキサゾール、トリアゾール、オキサジアゾール、トリアゾール、チアジアゾール、ピラン、ピリジン、ピリジアジン、ピリミジン、トリアジン、ベンゾフラン、ベンゾチオフェン、インドール、ベンゾイミダゾール、ベンゾチアゾール、キノリン、イソキノリン、キノキサリン、カルバゾール等を挙げることができるが、これらに限定されるものではない。 Heteroaryl groups include pyrrole, pyrazole, imidazole, oxazole, triazole, oxadiazole, triazole, thiadiazole, pyran, pyridine, pyridiazine, pyrimidine, triazine, benzofuran, benzothiophene, indole, benzimidazole, benzothiazole, quinoline, isoquinoline. , Quinoxaline, carbazole, and the like, but are not limited thereto.
アリーレン基、ヘテロアリーレン基、アルキレン基とは、前述のアリール基、ヘテロアリール基、アルキル基から水素原子1個を取り除いた2価の連結基を表す。 The arylene group, heteroarylene group, and alkylene group represent a divalent linking group obtained by removing one hydrogen atom from the above aryl group, heteroaryl group, and alkyl group.
アルキル基、アルコキシ基、アルケニル基、アリール基、ヘテロアリール基、アリレーン基、ヘテロアリレーン基、アルキレン基の水素原子はさらに他の置換基で置換されていても良い。 The hydrogen atom of an alkyl group, an alkoxy group, an alkenyl group, an aryl group, a heteroaryl group, an arylene group, a heteroarylene group, or an alkylene group may be further substituted with another substituent.
そのような置換基としては、ハロゲン原子、アルキル基、ハロゲン原子で置換されたアルキル基、アリール基、ニトロ基、ヒドロキシル基、アルコキシ基、カルボキシル基、スルホ基等が挙げられ、これらのうち、ハロゲン原子、アルキル基、アリール基、アルコキシ基は前記記述と同義である。 Examples of such a substituent include a halogen atom, an alkyl group, an alkyl group substituted with a halogen atom, an aryl group, a nitro group, a hydroxyl group, an alkoxy group, a carboxyl group, a sulfo group, and the like. The atom, alkyl group, aryl group, and alkoxy group have the same meanings as described above.
一般式(1)において、R1〜R9としては、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、又は置換基を有してもよい炭素数20以下のアルコキシ基であることが好ましく、それぞれ独立に、水素原子又はハロゲン原子であることがより好ましい。隣接する置換基同士が結合して、脂肪族飽和炭化水素系もしくは芳香族系の環状構造を形成しても良い。中でも、R6〜R9がハロゲン原子である場合、R7及びR8がハロゲン原子である場合、又は、R7及びR8が一緒になって芳香環を形成する場合、が特に好ましい。 In the general formula (1), R 1 to R 9 are preferably each independently a hydrogen atom, a halogen atom, a nitro group, or an alkoxy group having 20 or less carbon atoms which may have a substituent, More preferably, each independently a hydrogen atom or a halogen atom. Adjacent substituents may combine with each other to form an aliphatic saturated hydrocarbon-based or aromatic-based cyclic structure. Among them, it is particularly preferable that R 6 to R 9 are halogen atoms, R 7 and R 8 are halogen atoms, or that R 7 and R 8 together form an aromatic ring.
一般式(2)において、X1は、NHであることが好ましく、Z1は、置換基を有してもよい炭素数20以下のアリール基であることが好ましく、アリール基としては、フェニル基又はナフチル基がより好ましい。有してもよい置換基としては、ヒドロキシ基が好ましい。またZ1は、−COOH、−SO3H及び−OSO3Hから選ばれる少なくとも1つの置換基を有する。このようなZ1としては、置換基を有してもよい芳香族スルホン酸、置換基を有してもよい芳香族カルボン酸等が挙げられ、好ましくはヒドロキシ安息香酸である。 In the general formula (2), X 1 is preferably NH, Z 1 is preferably an aryl group having 20 or less carbon atoms which may have a substituent, and the aryl group is a phenyl group. Or a naphthyl group is more preferable. As the substituent that may have, a hydroxy group is preferable. Z 1 has at least one substituent selected from —COOH, —SO 3 H and —OSO 3 H. Examples of Z 1 include an aromatic sulfonic acid which may have a substituent and an aromatic carboxylic acid which may have a substituent, and the like, and preferably hydroxybenzoic acid.
一般式(3)におけるZ2は、置換基を有してもよい炭素数20以下のアリール基であることが好ましく、アリール基としては、フェニル基が好ましい。また、Z2における有してもよい置換基に、−COOH、−SO3H及び−OSO3Hは含まない。 Z 2 in the general formula (3) is preferably an aryl group having a carbon number of 20 or less, which may have a substituent, and the aryl group is preferably a phenyl group. Further, the substituent which may be closed in Z 2, -COOH, does not include -SO 3 H and -OSO 3 H.
一般式(4)において、n及びmは、1であることが好ましく、X3は、−NHSO2−又は−OSO2−が好ましく、Z3は、炭素数20以下のアリレーン基又は炭素数20以下のアルキレン基が好ましく、炭素数20以下のアリレーン基がより好ましく、フェニレン基が特に好ましい。X4は、−NH−が好ましい。 In the general formula (4), n and m are preferably 1, X 3 is preferably —NHSO 2 — or —OSO 2 —, and Z 3 is an arylene group having 20 or less carbon atoms or 20 carbon atoms. The following alkylene group is preferable, an arylene group having 20 or less carbon atoms is more preferable, and a phenylene group is particularly preferable. X 4 is preferably -NH-.
一般式(1)のキノフタロン化合物(A)の具体例を下記に示すが、本発明はこれらに限定されるものではない。 Specific examples of the quinophthalone compound (A) of the general formula (1) are shown below, but the present invention is not limited thereto.
<着色剤>
一般式(1)で表されるキノフタロン化合物(A)に加えて、従来公知の種々の顔料、及び染料を着色材として任意に選択して含有することが出来る。本発明のキノフタロン化合物(A)は、黄色顔料(B)及びフタロシアニン顔料(C)から選ばれた少なくとも1種の顔料と組み合わせて用いることが好ましい。
以下、本発明に使用しうる代表的な顔料と染料を挙げる。
<Colorant>
In addition to the quinophthalone compound (A) represented by the general formula (1), various conventionally known pigments and dyes can be arbitrarily selected and contained as colorants. The quinophthalone compound (A) of the present invention is preferably used in combination with at least one pigment selected from the yellow pigment (B) and the phthalocyanine pigment (C).
Typical pigments and dyes that can be used in the present invention are listed below.
本発明で使用することができる黄色顔料(B)としては、C.I.ピグメントイエロー1、2、3、4、5、6、10、12、13、14、15、16、17、18、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、93、94、95、97、98、100、101、104、106、108、109、110、113、114、115、116、117、118、119、120、123、126、127、128、129、138、139、147、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、192、193、194、196、198、199、213、214、特許第4993026号公報に記載のキノフタロン系顔料等の黄色顔料を用いることができる。特にフィルタセグメントの耐熱性、耐光性、及び明度の観点から、黄色色素としては、C.I.ピグメントイエロー138、139、150及び185からなる群より選ばれた少なくとも1種であることが好ましい。 Examples of the yellow pigment (B) that can be used in the present invention include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 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, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 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, Yellow pigments such as quinophthalone pigments described in 192, 193, 194, 196, 198, 199, 213, 214 and Japanese Patent No. 4993026 can be used. Particularly, from the viewpoints of heat resistance, light resistance, and brightness of the filter segment, examples of the yellow dye include C.I. I. Pigment Yellow 138, 139, 150 and 185 is preferable.
黄色染料としては、アゾ染料、アゾ金属錯塩染料、アントラキノン染料、インジゴ染料、チオインジゴ染料、フタロシアニン染料、ジフェニルメタン染料、トリフェニルメタン染料、キサンテン染料、チアジン染料、カチオン染料、シアニン染料、ニトロ染料、キノリン染料、ナフトキノン染料、オキサジン染料が挙げられる。 As the yellow dye, azo dye, azo metal complex salt dye, anthraquinone dye, indigo dye, thioindigo dye, phthalocyanine dye, diphenylmethane dye, triphenylmethane dye, xanthene dye, thiazine dye, cationic dye, cyanine dye, nitro dye, quinoline dye. , Naphthoquinone dyes and oxazine dyes.
黄色染料の具体例としては、C.I.アシッド イエロー2、3、4、5、6、7、8、9、9:1、10、11、11:1、12、13、14、15、16、17、17:1、18、20、21、22、23、25、26、27、29、30、31、33、34、36、38、39、40、40:1、41、42、42:1、43、44、46、48、51、53、55、56、60、63、65、66、67、68、69、72、76、82、83、84、86、87、90、94、105、115、117、122、127、131、132、136、141、142、143、144、145、146、149、153、159、166、168、169,172、174、175、178、180、183、187、188、189、190、191、192、199等が挙げられる。 Specific examples of the yellow dye include C.I. I. Acid Yellow 2,3,4,5,6,7,8,9,9:1,10,11,11:1,12,13,14,15,16,17,17:1,18,20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40:1, 41, 42, 42:1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 199 and the like.
また、C.I.ダイレクト イエロー1、2、4、5、12、13、15、20、24、25、26、32、33、34、35、41、42、44、44:1、45、46、48、49、50、51、61、66、67、69、70、71、72、73、74、81、84、86、90、91、92、95、107、110、117、118、119、120、121、126、127、129、132、133、134等も挙げられる。 Also, C.I. I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44:1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134 etc. are also mentioned.
また、C.I.ベーシック イエロー1、2、5、11、13、14、15、19、21、24、25、28、29、37、40、45、49、51、57、79、87、90、96、103、105、106等が挙げられる。 Also, C.I. I. Basic Yellow 1, 2, 5, 11, 13, 14, 15, 19, 21, 24, 25, 28, 29, 37, 40, 45, 49, 51, 57, 79, 87, 90, 96, 103, 105, 106 and the like.
また、C.I.ソルベント イエロー2、3、4、7、8、10、11、12、13、14、15、16、18、19、21、22、25、27、28、29、30、32、33、34、40、42、43、44、45、47、48、56、62、64、68、69、71、72、73、77、79、81、82、83、85、88、89、90、93、94、98、104、107、114、116、117、124、130、131、133、135、138、141、143、145、146、147、157、160、162、163、167、172、174、175、176、177、179、181、182、183、184、185、186、187、188、190、191、192、194、195等も挙げられる。 Also, C.I. I. Solvent Yellow 2, 3, 4, 7, 8, 10, 11, 12, 13, 14, 15, 16, 18, 19, 21, 22, 25, 27, 28, 29, 30, 32, 33, 34, 40, 42, 43, 44, 45, 47, 48, 56, 62, 64, 68, 69, 71, 72, 73, 77, 79, 81, 82, 83, 85, 88, 89, 90, 93, 94, 98, 104, 107, 114, 116, 117, 124, 130, 131, 133, 135, 138, 141, 143, 145, 146, 147, 157, 160, 162, 163, 167, 172, 174, 175, 176, 177, 179, 181, 182, 183, 184, 185, 186, 187, 188, 190, 191, 192, 194, 195 and the like are also included.
また、C.I.ディスパーズ イエロー1、2、3、5、7、8、10、11、13、13、23、27、33、34、42、45、48、51、54、56、59、60、63、64、67、70、77、79、82、85、88、93、99、114、118、119、122、123、124、126、163、184、184:1、202、211、229、231、232、233、241、245、246、247、248、249、250、251等が挙げられる。 Also, C.I. I. Disperse Yellow 1, 2, 3, 5, 7, 8, 10, 11, 13, 13, 23, 27, 33, 34, 42, 45, 48, 51, 54, 56, 59, 60, 63, 64 , 67, 70, 77, 79, 82, 85, 88, 93, 99, 114, 118, 119, 122, 123, 124, 126, 163, 184, 184:1, 202, 211, 229, 231, 232. 233, 241, 245, 246, 247, 248, 249, 250, 251 and the like.
本発明で使用することができる赤色顔料は、例えば、C.I.ピグメントレッド1、2、3、4、5、6、7、8、9、10、14、17、22、23、31、38、41、48:1、48:2、48:3、48:4、49、49:1、49:2、57:1、81、81:1、81:2、81:3、81:4、83、88、90、105、112、119、122、123、144、146、149、150、155、166、168、169、170、171、172、175、176、177、178、179、184、185、187、188、190、200、202、206、207、208、209、210、216、220、221、224、226、242、246、254、255、264、269、270、272、273、274,276、277、278、279、280、281、282、283、284、285、286、287、又は特表2011−523433号公報に記載のジケトピロロピロール顔料等が挙げられるが、特にこれらに限定されない。また、キサンテン系、アゾ系、ジスアゾ系、アントラキノン系などの赤色染料も使用できる。具体的には、C.I.アシッドレッド52、87、92、289、338などのキサンテン系酸性染料の造塩化合物等が挙げられる。 Red pigments that can be used in the present invention include, for example, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48: 4, 49, 49:1, 49:2, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 221, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, or the diketopyrrolopyrrole pigment described in JP-A No. 2011-523433, but the invention is not particularly limited thereto. Further, red dyes such as xanthene-based, azo-based, disazo-based, and anthraquinone-based dyes can also be used. Specifically, C.I. I. Examples thereof include salt-forming compounds of xanthene-based acid dyes such as Acid Red 52, 87, 92, 289, 338.
本発明で使用することができる橙色顔料は、例えば、C.I.ピグメントオレンジ38、43、71、又は73等が挙げられるが、特にこれらに限定されない。 Orange pigments that can be used in the present invention include, for example, C.I. I. Pigment Orange 38, 43, 71, 73 and the like, but are not particularly limited thereto.
本発明で使用することができる緑色顔料(C)は、例えば、C.I.ピグメントグリーン7、10、36、37、58、59、特開2008−19383号公報、特開2007−320986号公報、特開2004−70342号公報等に記載の亜鉛フタロシアニン顔料等が挙げられるが、特にこれらに限定されない。 The green pigment (C) that can be used in the present invention is, for example, C.I. I. Pigment Green 7, 10, 36, 37, 58, 59, JP 2008-19383A, JP 2007-320986A, JP 2004-70342A, and the like, and the zinc phthalocyanine pigments and the like are listed, It is not particularly limited to these.
本発明で使用することができる青色顔料は、例えば、C.I.ピグメントブルー1、1:2、9、14、15、15:1、15:2、15:3、15:4、15:6、16、22、60、64、特開2004−333817号公報、特許第4893859号公報等に記載のアルミニウムフタロシアニン顔料等が挙げられるが、特にこれらに限定されない。 Blue pigments that can be used in the present invention include, for example, C.I. I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 60, 64, JP-A-2004-333817, Examples thereof include aluminum phthalocyanine pigments described in Japanese Patent No. 4893859 and the like, but are not particularly limited thereto.
黄色顔料(B)を含有する場合においては、一般式(1)で表されるキノフタロン化合物(A)は、黄色顔料(B)に対して5質量%以上、60質量%以下であることが好ましく、10質量%以上、50質量%以下であることがより好ましい。キノフタロン化合物(A)の比率が着色剤に対して少なすぎる場合は、明度、コントラスト、耐熱性、異物抑制、初期粘度、保存安定性の向上効果が小さくなる傾向がある。 When the yellow pigment (B) is contained, the quinophthalone compound (A) represented by the general formula (1) is preferably 5% by mass or more and 60% by mass or less with respect to the yellow pigment (B). It is more preferably 10% by mass or more and 50% by mass or less. If the ratio of the quinophthalone compound (A) is too small with respect to the colorant, the effect of improving the brightness, contrast, heat resistance, foreign matter suppression, initial viscosity and storage stability tends to be small.
また、着色剤のなかでも、キノフタロン化合物(A)の色特性との関係上、いずれかのフタロシアニン顔料(C)を1種単独、又は、2種以上をさらに組み合わせて用いることが好ましい。 Further, among the colorants, it is preferable to use any one of the phthalocyanine pigments (C) alone or in combination of two or more in view of the color characteristics of the quinophthalone compound (A).
上記フタロシアニン顔料(C)としては、ハロゲン化銅フタロシアニン顔料、ハロゲン化亜鉛フタロシアニン顔料、アルミニウムフタロシアニン顔料、又はハロゲン化アルミニウムフタロシアニン顔料が好ましい。より好ましくは、C.I.ピグメントグリーン58、又は一般式(8)で表されるハロゲン化アルミニウムフタロシアニン化合物である。 The phthalocyanine pigment (C) is preferably a halogenated copper phthalocyanine pigment, a halogenated zinc phthalocyanine pigment, an aluminum phthalocyanine pigment, or a halogenated aluminum phthalocyanine pigment. More preferably, C.I. I. Pigment Green 58 or a halogenated aluminum phthalocyanine compound represented by the general formula (8).
一般式(8)
[一般式(8)中、Eは、ハロゲン原子を表し、nは、4〜16の整数を表す。ただし、Eで表されるハロゲン原子の置換数の平均値が、6〜15であり、ハロゲン分布幅が、4以上である。
Gは、−OP(=O)R101R102、−OC(=O)R103、−OS(=O)2R104を表す。R101及びR102は、それぞれ独立に、水素原子、水酸基、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいアルコキシル基又は置換基を有してもよいアリールオキシ基を表す。
R103は、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいシクロアルキル基、置換基を有してもよいアリール基又は置換基を有してもよい複素環基を表す。
R104は、水酸基、置換基を有してもよいアルキル基、置換基を有してもよいアリール基又は置換基を有してもよい複素環基を表す。]
General formula (8)
[In general formula (8), E represents a halogen atom, and n represents an integer of 4 to 16. However, the average value of the substitution number of the halogen atom represented by E is 6 to 15, and the halogen distribution width is 4 or more.
G represents -OP (= O) R101R102, -OC (= O) R103, -OS (= O) 2 R104. R101 and R102 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent or a substituent. It represents an aryloxy group which may have.
R103 is a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, or a heterocycle which may have a substituent. Represents a group.
R104 represents a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. ]
一般式(8)におけるハロゲン原子としては、フッ素、臭素、塩素、ヨウ素が挙げられ、臭素及び塩素が好ましい。 Examples of the halogen atom in the general formula (8) include fluorine, bromine, chlorine and iodine, with bromine and chlorine being preferred.
一般式(8)で表されるハロゲン化アルミニウムフタロシアニン化合物において、Eで表されるハロゲン原子の置換数の平均値は、6〜15であり、色相、堅牢性の観点から8〜15が好ましい。又はロゲン分布幅は、4以上であり、4〜9が好ましい。ハロゲン分布幅が4以上であると、フタロシアニン分子同士の会合が著しく抑制されやすくなり、分子同士の会合に起因する粒径の増大、しいては低コントラスト化の抑制に大きく寄与することが明らかとなった。ここで「ハロゲン分布幅」とは、一般式(8)で表されるフタロシアニン顔料に置換しているハロゲン数の分布である。ハロゲン分布幅は質量分析して得られたマススペクトラムにおいて、各成分に相当する分子イオンピークの信号強度(各ピーク値)と、各ピーク値を積算した値(全ピーク値)とを算出し、全ピーク値に対する各ピーク値の割合が1%以上のピークの数をカウントし、ハロゲン分布幅とした。 In the halogenated aluminum phthalocyanine compound represented by the general formula (8), the average number of substitutions of the halogen atom represented by E is 6 to 15, and 8 to 15 is preferable from the viewpoint of hue and fastness. Alternatively, the width of the distribution of the logogen is 4 or more, preferably 4 to 9. When the halogen distribution width is 4 or more, the association between the phthalocyanine molecules is apt to be significantly suppressed, and it is clear that the particle size is increased due to the association between the molecules and, as a result, the reduction of the contrast is greatly suppressed. became. Here, the "halogen distribution width" is a distribution of the number of halogens substituted in the phthalocyanine pigment represented by the general formula (8). The halogen distribution width, in the mass spectrum obtained by mass spectrometry, the signal intensity (each peak value) of the molecular ion peak corresponding to each component, and the value obtained by integrating each peak value (total peak value), The number of peaks in which the ratio of each peak value to the total peak value was 1% or more was counted and used as the halogen distribution width.
一般式(8)におけるアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、tert−ブチル基、ネオペンチル基、n−へキシル基、n−オクチル基、ステアリル基、2−エチルへキシル基等の直鎖又は分岐アルキル基が挙げられ、炭素数1〜6のアルキル基が好ましい。
置換基を有するアルキル基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、メトキシ基等のアルコキシル基、フェニル基、トリル基等のアリール基、ニトロ基等が挙げられる。また、置換基は、複数あっても良い。したがって、置換基を有するアルキル基としては、例えば、トリクロロメチル基、トリフルオロメチル基、2,2,2−トリフルオロエチル基、2,2−ジブロモエチル基、2−エトキシエチル基、2−ブトキシエチル基、2−ニトロプロピル基、べンジル基、4−メチルべンジル基、4−tert−ブチルべンジル基、4−メトキシべンジル基、4−ニトロべンジル基、2,4−ジクロロべンジル基等が挙げられる。
Examples of the alkyl group in the general formula (8) include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group, stearyl group. , A linear or branched alkyl group such as a 2-ethylhexyl group, and an alkyl group having 1 to 6 carbon atoms is preferable.
Examples of the substituent of the alkyl group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkoxyl group such as a methoxy group, an aryl group such as a phenyl group and a tolyl group, and a nitro group. Further, there may be a plurality of substituents. Therefore, examples of the alkyl group having a substituent include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, and a 2-butoxy group. Ethyl group, 2-nitropropyl group, benzyl group, 4-methyl benzyl group, 4-tert-butyl benzyl group, 4-methoxy benzyl group, 4-nitro benzyl group, 2,4-dichloro benzyl group. Groups and the like.
一般式(8)におけるアリール基としては、フェニル基、p−トリル基等の単環芳香族炭化水素基や、ナフチル基、アンスリル基等の縮合芳香族炭化水素基が挙げられ、単環芳香族炭化水素基が好ましい。また、炭素数6〜12のアリール基が好ましい。
置換基を有するアリール基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、アルコキシル基、アミノ基、ニトロ基等が挙げられる。また、置換基は、複数あっても良い。したがって、置換基を有するアリール基としては、例えば、p−ブロモフェニル基、p−ニトロフェニル基、p−メトキシフェニル基、2,4−ジクロロフェニル基、ペンタフルオロフェニル基、2−ジメチルアミノフェニル基、2−メチル−4−クロロフェニル基、4−メトキシ−1−ナフチル基、6−メチル−2−ナフチル基、4,5,8−トリクロロ−2−ナフチル基、アントラキノニル基等が挙げられる。
Examples of the aryl group in the general formula (8) include a monocyclic aromatic hydrocarbon group such as a phenyl group and a p-tolyl group, and a condensed aromatic hydrocarbon group such as a naphthyl group and an anthryl group. Hydrocarbon groups are preferred. Further, an aryl group having 6 to 12 carbon atoms is preferable.
Examples of the substituent of the aryl group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkoxyl group, an amino group and a nitro group. Further, there may be a plurality of substituents. Therefore, examples of the aryl group having a substituent include a p-bromophenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a 2,4-dichlorophenyl group, a pentafluorophenyl group, a 2-dimethylaminophenyl group, Examples thereof include a 2-methyl-4-chlorophenyl group, a 4-methoxy-1-naphthyl group, a 6-methyl-2-naphthyl group, a 4,5,8-trichloro-2-naphthyl group and an anthraquinonyl group.
一般式(8)におけるアルコキシル基としては、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、n−ブトキシ基、イソブトキシ基、tert−ブトキシ基、ネオペンチルオキシ基、2,3−ジメチル−3−ペンチルオキシ基、n−へキシルオキシ基、n−オクチルオキシ基、ステアリルオキシ基、2−エチルへキシルオキシ基等の直鎖又は分岐アルコキシル基が挙げられ、炭素数1〜6のアルコキシル基が好ましい。
置換基を有するアルコキシル基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、アルコキシル基、フェニル基、トリル基等のアリール基、ニトロ基が挙げられる。また、置換基は、複数あっても良い。したがって、置換基を有するアルコキシル基としては、例えば、トリクロロメトキシ基、トリフルオロメトキシ基、2,2,2−トリフルオロエトキシ基、2,2,3,3−テトラフルオロプロポキシ基、2,2−ジトリフルオロメチルプロポキシ基、2−エトキシエトキシ基、2−ブトキシエトキシ基、2−ニトロプロポキシ基、ベンジルオキシ基等が挙げられる。
Examples of the alkoxyl group in the general formula (8) include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, and 2,3-dimethyl-3-. Examples thereof include linear or branched alkoxyl groups such as a pentyloxy group, an n-hexyloxy group, an n-octyloxy group, a stearyloxy group, and a 2-ethylhexyloxy group, and an alkoxyl group having 1 to 6 carbon atoms is preferable.
Examples of the substituent of the alkoxyl group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkoxyl group, an aryl group such as a phenyl group and a tolyl group, and a nitro group. Further, there may be a plurality of substituents. Therefore, examples of the alkoxyl group having a substituent include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2- Examples thereof include a ditrifluoromethylpropoxy group, a 2-ethoxyethoxy group, a 2-butoxyethoxy group, a 2-nitropropoxy group and a benzyloxy group.
一般式(8)におけるアリールオキシ基としては、フェノキシ基、p−メチルフェノキシ基等の単環芳香族炭化水素基からなるアリールオキシ基や、ナフタルオキシ基、アンスリルオキシ基等の縮合芳香族炭化水素基からなるアリールオキシ基が挙げられ、単環芳香族炭化水素基からなるアリールオキシ基が好ましい。また、炭素数6〜12のアリールオキシ基が好ましい。
置換基を有するアリールオキシ基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、アルキル基、アルコキシル基、アミノ基、ニトロ基等が挙げられる。また、置換基は、複数あっても良い。したがって、置換基を有するアリールオキシ基としては、例えば、p−ニトロフェノキシ基、p−メトキシフェノキシ基、2,4−ジクロロフェノキシ基、ペンタフルオロフェノキシ基、2−メチル−4−クロロフェノキシ基等が挙げられる。
The aryloxy group in the general formula (8) is an aryloxy group composed of a monocyclic aromatic hydrocarbon group such as a phenoxy group or a p-methylphenoxy group, or a condensed aromatic hydrocarbon such as a naphthaloxy group or an anthryloxy group. The aryloxy group consisting of a group is mentioned, and the aryloxy group consisting of a monocyclic aromatic hydrocarbon group is preferable. Further, an aryloxy group having 6 to 12 carbon atoms is preferable.
Examples of the substituent of the aryloxy group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkyl group, an alkoxyl group, an amino group and a nitro group. Further, there may be a plurality of substituents. Therefore, examples of the aryloxy group having a substituent include a p-nitrophenoxy group, a p-methoxyphenoxy group, a 2,4-dichlorophenoxy group, a pentafluorophenoxy group, and a 2-methyl-4-chlorophenoxy group. Can be mentioned.
一般式(8)におけるシクロアルキル基としては、シクロペンチル基、シクロへキシル基、2,5−ジメチルシクロペンチル基、4−tert−プチルシクロヘキシル基等の単環脂肪族炭化水素基や、ボルニル基やアダマンチル基等の縮合脂肪族炭化水素基が挙げられる。また、炭素数5〜12のシクロアルキル基が好ましい。
置換基を有するシクロアルキル基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、アルキル基、アルコキシル基、水酸基、アミノ基、ニトロ基等が挙げられる。また、置換基は、複数あっても良い。置換基を有するシクロアルキル基としては、例えば、2,5−ジクロロシクロペンチル基、4−ヒドロキシシクロヘキシル基等がある。
Examples of the cycloalkyl group in the general formula (8) include a monocyclic aliphatic hydrocarbon group such as a cyclopentyl group, a cyclohexyl group, a 2,5-dimethylcyclopentyl group, and a 4-tert-putylcyclohexyl group, a bornyl group, and an adamantyl group. And condensed aliphatic hydrocarbon groups such as groups. Moreover, a C5-C12 cycloalkyl group is preferable.
Examples of the substituent of the cycloalkyl group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkyl group, an alkoxyl group, a hydroxyl group, an amino group and a nitro group. Further, there may be a plurality of substituents. Examples of the cycloalkyl group having a substituent include a 2,5-dichlorocyclopentyl group and a 4-hydroxycyclohexyl group.
一般式(8)における複素環基としては、ピリジル基、ピラジル基、ピペリジノ基、ピラニル基、モルホリノ基、アクリジニル基等の脂肪族複素環基や芳香族複素環基が挙げられる。また、炭素数4〜12の複素環基が好ましく、環員数5〜13の複素環基が好ましい。
置換基を有する複素環基の置換基としては、塩素、フッ素、臭素等のハロゲン原子、アルキル基、アルコキシル基、水酸基、アミノ基、ニトロ基等が挙げられる。また、置換基は、複数あっても良い。置換基を有する複素環基としては、3−メチルピリジル基、N−メチルピペリジル基、N−メチルピロリル基等が挙げられる。
Examples of the heterocyclic group in the general formula (8) include an aliphatic heterocyclic group such as a pyridyl group, a pyrazyl group, a piperidino group, a pyranyl group, a morpholino group and an acridinyl group, and an aromatic heterocyclic group. Further, a heterocyclic group having 4 to 12 carbon atoms is preferable, and a heterocyclic group having 5 to 13 ring members is preferable.
Examples of the substituent of the heterocyclic group having a substituent include a halogen atom such as chlorine, fluorine and bromine, an alkyl group, an alkoxyl group, a hydroxyl group, an amino group and a nitro group. Further, there may be a plurality of substituents. Examples of the heterocyclic group having a substituent include a 3-methylpyridyl group, an N-methylpiperidyl group, an N-methylpyrrolyl group and the like.
一般式(8)で表されるハロゲン化アルミニウムフタロシアニン化合物としては、分散性や色特性の観点から、R101、R102のうちの少なくとも1つが、置換基を有してもよいアリール基又は置換基を有してもよいアリールオキシ基であることが好ましく、R101及びR102がいずれもアリール基、又はアリールオキシ基であることがより好ましく、R101及びR102がいずれもフェニル基又はフェノキシ基であることがさらに好ましい。また、R103及びR104が、置換基を有してもよいアリール基又は置換基を有してもよい複素環基であることが好ましい。 As the halogenated aluminum phthalocyanine compound represented by the general formula (8), from the viewpoint of dispersibility and color characteristics, at least one of R101 and R102 is an aryl group or a substituent which may have a substituent. It is preferably an aryloxy group which may have, more preferably both R101 and R102 are an aryl group or an aryloxy group, and it is further preferable that both R101 and R102 are a phenyl group or a phenoxy group. preferable. In addition, R103 and R104 are preferably an aryl group which may have a substituent or a heterocyclic group which may have a substituent.
一般式(1)で表されるキノフタロン化合物(A)を含む黄色色素に、緑色色素を併用する場合には、明度と色相の観点から、緑色色素/一般式(1)で表されるキノフタロン化合物(A)を含む黄色色素の質量比が10/90〜70/30の範囲が好ましい。 When a yellow dye containing the quinophthalone compound (A) represented by the general formula (1) is used in combination with a green dye, from the viewpoint of lightness and hue, green dye/quinophthalone compound represented by the general formula (1). The mass ratio of the yellow dye containing (A) is preferably in the range of 10/90 to 70/30.
(着色剤の微細化)
本発明の着色組成物に用いられる着色剤は、高い明度及び高いコントラストを得るため、必要に応じてソルトミリング処理等により、着色剤粒子の微細化を施すことにより、カラーフィルタ用着色剤として好適に使用することができる。着色剤の体積平均一次粒子径は、着色剤担体中への分散性を高めるために、10nm以上であることが好ましい。また、コントラストが高いフィルタセグメントを得るためには、80nm以下であることが好ましい。特に好ましい範囲は、20〜60nmの範囲である。
(Fine colorant miniaturization)
The colorant used in the coloring composition of the present invention is suitable as a colorant for a color filter by subjecting the colorant particles to miniaturization by salt milling treatment or the like, if necessary, in order to obtain high brightness and high contrast. Can be used for The volume average primary particle diameter of the colorant is preferably 10 nm or more in order to enhance dispersibility in the colorant carrier. Further, in order to obtain a filter segment with high contrast, it is preferably 80 nm or less. A particularly preferable range is 20 to 60 nm.
ソルトミリング処理とは、着色剤と水溶性無機塩と水溶性有機溶剤との混合物を、ニーダー、2本ロールミル、3本ロールミル、ボールミル、アトライター、サンドミル等の混練機を用いて、加熱しながら機械的に混練した後、水洗により水溶性無機塩と水溶性有機溶剤を除去する処理である。水溶性無機塩は、破砕助剤として働くものであり、ソルトミリング時に無機塩の硬度の高さを利用して着色剤が破砕される。着色剤をソルトミリング処理する際の条件を最適化することにより、体積平均一次粒子径が非常に微細であり、また、分布の幅がせまく、シャープな粒度分布をもつ着色剤を得ることができる。 The salt milling treatment is performed by heating a mixture of a colorant, a water-soluble inorganic salt and a water-soluble organic solvent with a kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor or a sand mill. This is a treatment for removing the water-soluble inorganic salt and the water-soluble organic solvent by washing with water after mechanically kneading. The water-soluble inorganic salt acts as a crushing aid, and the colorant is crushed by utilizing the high hardness of the inorganic salt during salt milling. By optimizing the conditions for the salt milling treatment of the colorant, it is possible to obtain a colorant having a very fine volume average primary particle size, a narrow distribution width, and a sharp particle size distribution. ..
水溶性無機塩としては、塩化ナトリウム、塩化バリウム、塩化カリウム、硫酸ナトリウム等を用いることができるが、価格の点から塩化ナトリウム(食塩)を用いるのが好ましい。水溶性無機塩は、処理効率と生産効率の両面から、顔料の全質量を基準(100質量%)として、50〜2000質量%用いることが好ましく、300〜1000質量%用いることが最も好ましい。 As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate or the like can be used, but it is preferable to use sodium chloride (salt) from the viewpoint of cost. From the viewpoint of both treatment efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000% by mass, and most preferably 300 to 1000% by mass, based on the total mass of the pigment (100% by mass).
水溶性有機溶剤は、着色剤及び水溶性無機塩を湿潤する働きをするものであり、水に溶解(混和)し、かつ用いる無機塩を実質的に溶解しないものであれば特に限定されない。ただし、ソルトミリング時に温度が上昇し、溶剤が蒸発し易い状態になるため、安全性の点から、沸点120℃以上の高沸点のものが好ましい。そのようなものとしては、例えば、2−メトキシエタノール、2−ブトキシエタノール、2−(イソペンチルオキシ)エタノール、2−(ヘキシルオキシ)エタノール、ジエチレングリコール、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液状のポリエチレングリコール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、液状のポリプロピレングリコール等が用いられる。これら水溶性有機溶剤は、着色剤の全質量を基準(100質量%)として、5〜1000質量%用いることが好ましく、50〜500質量%用いることが最も好ましい。 The water-soluble organic solvent has a function of wetting the colorant and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point of 120° C. or higher is preferable from the viewpoint of safety. Examples thereof include 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used. These water-soluble organic solvents are preferably used in an amount of 5 to 1000% by mass, and most preferably 50 to 500% by mass, based on the total mass of the colorant (100% by mass).
着色剤をソルトミリング処理する際には、必要に応じて樹脂を添加してもよい。ここで、用いられる樹脂の種類は特に限定されず、天然樹脂、変性天然樹脂、合成樹脂、天然樹脂で変性された合成樹脂等を用いることができる。用いられる樹脂は、室温で固体であり、水不溶性であることが好ましく、かつ上記水溶性有機溶剤に一部可溶であることがさらに好ましい。樹脂の使用量は、着色剤の全質量を基準(100質量%)として、2〜200質量%の範囲であることが好ましい。
また、着色剤をソルトミリング処理する際には、必要に応じて一般式(1)で表されるキノフタロン化合物(A)を添加してもよい。キノフタロン化合物(A)が顔料分散剤として作用し、微細化を促進する効果がある。
When salt-milling the colorant, a resin may be added as necessary. Here, the type of resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature and insoluble in water, and more preferably partially soluble in the water-soluble organic solvent. The amount of the resin used is preferably in the range of 2 to 200 mass% based on the total mass of the colorant (100 mass %).
Further, when the colorant is subjected to the salt milling treatment, the quinophthalone compound (A) represented by the general formula (1) may be added if necessary. The quinophthalone compound (A) acts as a pigment dispersant and has the effect of promoting miniaturization.
<バインダー樹脂>
バインダー樹脂は、顔料や色素などの着色剤及び一般式(1)で表されるキノフタロン化合物を分散するものであって、熱可塑性樹脂、熱硬化性樹脂等が挙げられる。
<Binder resin>
The binder resin disperses a colorant such as a pigment or a dye and a quinophthalone compound represented by the general formula (1), and examples thereof include a thermoplastic resin and a thermosetting resin.
バインダー樹脂としては、可視光領域の400〜700nmの全波長領域において分光透過率が好ましくは80%以上、より好ましくは95%以上の樹脂であることが好ましい。また、アルカリ現像型着色レジスト材の形態で用いる場合には、酸性基含有エチレン性不飽和単量体を共重合したアルカリ可溶性ビニル系樹脂を用いることが好ましい。また、さらに光感度を向上と耐溶剤の改善を目的に、エチレン性不飽和二重結合を有する活性エネルギー線硬化性樹脂を用いることもできる。 The binder resin is preferably a resin having a spectral transmittance of 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. When used in the form of an alkali development type colored resist material, it is preferable to use an alkali-soluble vinyl resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer. Further, an active energy ray-curable resin having an ethylenically unsaturated double bond can be used for the purpose of further improving photosensitivity and solvent resistance.
特に側鎖にエチレン性不飽和二重結合を有する活性エネルギー線硬化性樹脂をカラーフィルタ用アルカリ現像型レジストに用いることで、着色剤を塗布した後の塗膜異物が発生せず、レジスト材中の着色剤の安定性が改善され好ましい。側鎖にエチレン性不飽和二重結合を有さない直鎖状の樹脂を用いた場合は、樹脂と着色剤の混在する液中で着色剤が樹脂にトラップされにくく自由度を持っていることで着色剤成分が凝集・析出しやすいが、側鎖にエチレン性不飽和二重結合を有する活性エネルギー線硬化性樹脂を用いることで、樹脂と着色剤の混在する液中で着色剤が樹脂にトラップされ易いため、耐溶剤性試験において、色素が溶出しにくく、着色剤成分が凝集・析出しにくく、また、さらに活性エネルギー線で露光し膜を形成する際に樹脂が3次元架橋されることで着色剤分子が固定され、その後の現像工程で溶剤が除去されても着色剤成分が凝集・析出しにくくなると推定される。 In particular, by using an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain for an alkali-developing resist for color filters, no foreign matter is generated in the coating film after applying the colorant, and This is preferable because the stability of the colorant is improved. When a straight-chain resin that does not have an ethylenically unsaturated double bond in the side chain is used, the colorant should be difficult to be trapped in the resin in a liquid containing the resin and the colorant, and it should have a degree of freedom. Although the colorant component easily aggregates and precipitates in, the use of an active energy ray-curable resin that has an ethylenically unsaturated double bond in the side chain allows the colorant to become a resin in a liquid in which the resin and the colorant are mixed. Since it is easily trapped, the dye is less likely to elute in the solvent resistance test, the colorant component is less likely to aggregate/precipitate, and the resin is three-dimensionally crosslinked when exposed to active energy rays to form a film. It is presumed that the colorant molecules are fixed in the above step and the colorant component is less likely to aggregate/precipitate even if the solvent is removed in the subsequent developing step.
バインダー樹脂の重量平均分子量(Mw)は、着色剤を好ましく分散させるためには、5,000〜100,000の範囲が好ましく、より好ましくは5,000〜80,000の範囲である。また数平均分子量(Mn)は2,500〜50,000の範囲が好ましく、Mw/Mnの値は10以下であることが好ましい。 The weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 100,000, more preferably in the range of 5,000 to 80,000 in order to disperse the colorant preferably. The number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and the value of Mw/Mn is preferably 10 or less.
バインダー樹脂をカラーフィルタ用感光性着色組成物として使用する場合には、顔料の分散性、浸透性、現像性、及び耐熱性の観点から、着色剤吸着基及び現像時のアルカリ可溶基として働くカルボキシル基、着色剤担体及び溶剤に対する親和性基として働く脂肪族基及び芳香族基のバランスが、顔料の分散性、浸透性、現像性、さらには耐久性にとって重要であり、酸価20〜300mgKOH/gの樹脂を用いることが好ましい。酸価が、20mgKOH/g未満では、現像液に対する溶解性が悪く、微細パターン形成するのが困難である。300mgKOH/gを超えると、微細パターンが残らなくなる。 When the binder resin is used as a photosensitive coloring composition for a color filter, it functions as a colorant adsorbing group and an alkali-soluble group at the time of development, from the viewpoint of pigment dispersibility, penetrability, developability, and heat resistance. The balance of the carboxyl group, the aliphatic group and the aromatic group that act as the affinity group for the colorant carrier and the solvent is important for the dispersibility, penetrability, developability and durability of the pigment, and the acid value is 20 to 300 mgKOH. It is preferable to use /g of resin. When the acid value is less than 20 mgKOH/g, the solubility in a developing solution is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH/g, no fine pattern will remain.
バインダー樹脂は、成膜性及び諸耐性が良好なことから、着色剤の全質量100質量部に対し、30質量部以上の量で用いることが好ましく、着色剤濃度が高く、良好な色特性を発現できることから、500質量部以下の量で用いることが好ましい。 The binder resin is preferably used in an amount of 30 parts by mass or more with respect to 100 parts by mass of the total amount of the colorant because the film forming property and various resistances are good, and the colorant concentration is high and good color characteristics are obtained. Since it can be expressed, it is preferably used in an amount of 500 parts by mass or less.
(熱可塑性樹脂)
バインダー樹脂に用いる熱可塑性樹脂としては、例えば、アクリル樹脂、ブチラール樹脂、スチレン−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、ビニル系樹脂、アルキッド樹脂、ポリスチレン樹脂、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、ポリエチレン(HDPE、LDPE)、ポリブタジエン、及びポリイミド樹脂等が挙げられる。中でもアクリル樹脂を用いることが好ましい。
(Thermoplastic resin)
Examples of the thermoplastic resin used for the binder resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate. , Polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resins. .. Above all, it is preferable to use an acrylic resin.
酸性基含有エチレン性不飽和モノマーを共重合したビニル系アルカリ可溶性樹脂としては、例えば、カルボキシル基、スルホン基等の酸性基を有する樹脂が挙げられる。アルカリ可溶性樹脂として具体的には、酸性基を有するアクリル樹脂、α−オレフィン/(無水)マレイン酸共重合体、スチレン/スチレンスルホン酸共重合体、エチレン/(メタ)アクリル酸共重合体、又はイソブチレン/(無水)マレイン酸共重合体等が挙げられる。中でも、酸性基を有するアクリル樹脂、及びスチレン/スチレンスルホン酸共重合体から選ばれる少なくとも1種の樹脂、特に酸性基を有するアクリル樹脂は、耐熱性、透明性が高いため、好適に用いられる。 Examples of the vinyl-based alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group and a sulfone group. Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin/(anhydrous) maleic acid copolymer, a styrene/styrene sulfonic acid copolymer, an ethylene/(meth)acrylic acid copolymer, or Examples thereof include isobutylene/(anhydrous) maleic acid copolymer. Above all, at least one resin selected from an acrylic resin having an acidic group and a styrene/styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group is preferably used because it has high heat resistance and transparency.
エチレン性不飽和二重結合を有する活性エネルギー線硬化性樹脂としては、たとえば以下に示す(a)や(b)の方法により不飽和エチレン性二重結合を導入した樹脂が挙げられる。 Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include resins having an unsaturated ethylenic double bond introduced by the following methods (a) and (b).
[方法(a)]
方法(a)としては、例えば、エポキシ基を有する不飽和エチレン性単量体と、他の1種類以上の単量体とを共重合することによって得られた共重合体の側鎖エポキシ基に、不飽和エチレン性二重結合を有する不飽和一塩基酸のカルボキシル基を付加反応させ、更に、生成した水酸基に、多塩基酸無水物を反応させ、不飽和エチレン性二重結合及びカルボキシル基を導入する方法がある。
[Method (a)]
As the method (a), for example, a side chain epoxy group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having an epoxy group and one or more other monomers , An unsaturated ethylenic double bond having a carboxyl group of an unsaturated monobasic acid is subjected to an addition reaction, and the generated hydroxyl group is reacted with a polybasic acid anhydride to form an unsaturated ethylenic double bond and a carboxyl group. There is a way to introduce.
エポキシ基を有する不飽和エチレン性単量体としては、例えば、グリシジル(メタ)アクリレート、メチルグリシジル(メタ)アクリレート、2−グリシドキシエチル(メタ)アクリレート、3,4エポキシブチル(メタ)アクリレート、及び3,4エポキシシクロヘキシル(メタ)アクリレートが挙げられ、これらは、単独で用いても、2種類以上を併用してもかまわない。次工程の不飽和一塩基酸との反応性の観点で、グリシジル(メタ)アクリレートが好ましい。 Examples of the unsaturated ethylenic monomer having an epoxy group include glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4 epoxybutyl (meth)acrylate, And 3,4 epoxycyclohexyl (meth)acrylate, which may be used alone or in combination of two or more kinds. From the viewpoint of reactivity with the unsaturated monobasic acid in the next step, glycidyl (meth)acrylate is preferable.
不飽和一塩基酸としては、(メタ)アクリル酸、クロトン酸、o−、m−、p−ビニル安息香酸、(メタ)アクリル酸のα位ハロアルキル、アルコキシル、ハロゲン、ニトロ、シアノ置換体等のモノカルボン酸等が挙げられ、これらは、単独で用いても、2種類以上を併用してもかまわない。 Examples of the unsaturated monobasic acid include (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-position haloalkyl of (meth)acrylic acid, alkoxyl, halogen, nitro, and cyano-substituted compounds. Examples thereof include monocarboxylic acid, and these may be used alone or in combination of two or more kinds.
多塩基酸無水物としては、テトラヒドロ無水フタル酸、無水フタル酸、ヘキサヒドロ無水フタル酸、無水コハク酸、無水マレイン酸等が挙げられ、これらは単独で用いても、2種類以上を併用してもかまわない。カルボキシル基の数を増やす等、必要に応じて、トリメリット酸無水物等のトリカルボン酸無水物を用いたり、ピロメリット酸二無水物等のテトラカルボン酸二無水物を用いて、残った無水物基を加水分解すること等もできる。また、多塩基酸無水物として、不飽和エチレン性二重結合を有する、エトラヒドロ無水フタル酸、又は無水マレイン酸を用いると、更に不飽和エチレン性二重結合を増やすことができる。 Examples of polybasic acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, and the like. These may be used alone or in combination of two or more kinds. I don't care. If necessary, such as increasing the number of carboxyl groups, use a tricarboxylic acid anhydride such as trimellitic anhydride, or use a tetracarboxylic acid dianhydride such as pyromellitic dianhydride to leave the remaining anhydride. It is also possible to hydrolyze the group. Further, when etrahydrophthalic anhydride or maleic anhydride having an unsaturated ethylenic double bond is used as the polybasic acid anhydride, the unsaturated ethylenic double bond can be further increased.
方法(a)の類似の方法として、例えば、カルボキシル基を有する不飽和エチレン性単量体と、他の1種類以上の単量体とを共重合することによって得られた共重合体の側鎖カルボキシル基の一部に、エポキシ基を有する不飽和エチレン性単量体を付加反応させ、不飽和エチレン性二重結合及びカルボキシル基を導入する方法がある。 As a method similar to the method (a), for example, a side chain of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group and one or more other monomers There is a method of adding an unsaturated ethylenic monomer having an epoxy group to a part of the carboxyl group to introduce an unsaturated ethylenic double bond and a carboxyl group.
[方法(b)]
方法(b)としては、水酸基を有する不飽和エチレン性単量体を使用し、他のカルボキシル基を有する不飽和一塩基酸の単量体や、他の単量体とを共重合することによって得られた共重合体の側鎖水酸基に、イソシアネート基を有する不飽和エチレン性単量体のイソシアネート基を反応させる方法がある。
[Method (b)]
As the method (b), an unsaturated ethylenic monomer having a hydroxyl group is used, and a monomer of an unsaturated monobasic acid having another carboxyl group is copolymerized with another monomer. There is a method of reacting a side chain hydroxyl group of the obtained copolymer with an isocyanate group of an unsaturated ethylenic monomer having an isocyanate group.
水酸基を有する不飽和エチレン性単量体としては、2−ヒドロキシエチル(メタ)アクリレート、2−若しくは3−ヒドロキシプロピル(メタ)アクリレート、2−若しくは3−若しくは4−ヒドロキシブチル(メタ)アクリレート、グリセロール(メタ)アクリレート、又はシクロヘキサンジメタノールモノ(メタ)アクリレート等のヒドロキシアルキル(メタ)アクリレート類が挙げられ、これらは、単独で用いても、2種類以上を併用してもかまわない。また、上記ヒドロキシアルキル(メタ)アクリレートに、エチレンオキシド、プロピレンオキシド、及び/又はブチレンオキシド等を付加重合させたポリエーテルモノ(メタ)アクリレートや、(ポリ)γ−バレロラクトン、(ポリ)ε−カプロラクトン、及び/又は(ポリ)12−ヒドロキシステアリン酸等を付加した(ポリ)エステルモノ(メタ)アクリレートも使用できる。塗膜異物抑制の観点から、2−ヒドロキシエチル(メタ)アクリレート、又はグリセロール(メタ)アクリレートが好ましい。 As the unsaturated ethylenic monomer having a hydroxyl group, 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2- or 3- or 4-hydroxybutyl (meth)acrylate, glycerol Examples thereof include (meth)acrylates and hydroxyalkyl (meth)acrylates such as cyclohexanedimethanol mono(meth)acrylate, and these may be used alone or in combination of two or more kinds. Further, a polyether mono(meth)acrylate obtained by addition-polymerizing ethylene oxide, propylene oxide, and/or butylene oxide, etc. to the hydroxyalkyl(meth)acrylate, (poly)γ-valerolactone, (poly)ε-caprolactone And/or (poly)ester mono(meth)acrylate to which (poly)12-hydroxystearic acid or the like is added can also be used. From the viewpoint of suppressing foreign matter in the coating film, 2-hydroxyethyl (meth)acrylate or glycerol (meth)acrylate is preferable.
イソシアネート基を有する不飽和エチレン性単量体としては、2−(メタ)アクリロイルオキシエチルイソシアネート、又は1,1−ビス〔(メタ)アクリロイルオキシ〕エチルイソシアネート等が挙げられるが、これらに限定することなく、2種類以上併用することもできる。 Examples of the unsaturated ethylenic monomer having an isocyanate group include 2-(meth)acryloyloxyethylisocyanate, 1,1-bis[(meth)acryloyloxy]ethylisocyanate, and the like, but are not limited thereto. Alternatively, two or more types can be used together.
(熱硬化性樹脂)
バインダー樹脂に用いる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、カルド樹脂、及びフェノール樹脂等が挙げられる。
(Thermosetting resin)
Examples of the thermosetting resin used as the binder resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, cardo resin, and phenol resin.
熱硬化性樹脂としては、例えば、エポキシ化合物、ベンゾグアナミン化合物、ロジン変性マレイン酸化合物、ロジン変性フマル酸化合物、メラミン化合物、尿素化合物、カルド化合物、及びフェノール化合物といった、低分子化合物でもよく、本発明はこれに限定されるものではない。このような熱硬化性樹脂を含むことで、フィルタセグメントの焼成時に樹脂が反応し、塗膜の架橋密度を高め、耐熱性が向上し、フィルタセグメント焼成時の顔料凝集が抑えられるという効果が得られる。
これらの中でも、エポキシ樹脂、カルド樹脂、又はメラミン樹脂が好ましい。
The thermosetting resin may be, for example, a low molecular compound such as an epoxy compound, a benzoguanamine compound, a rosin-modified maleic acid compound, a rosin-modified fumaric acid compound, a melamine compound, a urea compound, a cardo compound, and a phenol compound. It is not limited to this. By including such a thermosetting resin, the resin reacts when the filter segment is fired, the crosslinking density of the coating film is increased, the heat resistance is improved, and the effect of suppressing pigment aggregation during firing of the filter segment is obtained. To be
Among these, epoxy resin, cardo resin, or melamine resin is preferable.
<有機溶剤>
本発明の着色組成物には、着色剤を充分にモノマー、樹脂などに溶解させ、ガラス基板等の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有機溶剤を含有させる。
<Organic solvent>
In the coloring composition of the present invention, a colorant is sufficiently dissolved in a monomer, a resin, etc., and is applied onto a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm to form a filter segment. An organic solvent is included to facilitate this.
有機溶剤としては、例えば、乳酸エチル、ベンジルアルコール、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、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る。これらの有機溶剤は、1種を単独で、若しくは2種以上を混合して用いることができる。 Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate and 1,4-dioxane. , 2-heptanone, 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, 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 monohexyl ether, ethylene glycol monomethyl ether, 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, dipropylene 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 Examples thereof include cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate and dibasic acid ester. These organic solvents can be used alone or in combination of two or more.
中でも、着色剤の分散性、浸透性、及び着色組成物の塗布性が良好なことから、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート、プロピ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メチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート等のグリコールアセテート類、ベンジルアルコール、ダイアセトンアルコール等のアルコール類やシクロヘキサノン等のケトン類を用いることが好ましい。 Among them, dispersibility of the colorant, penetrability, and good coatability of the coloring composition, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl It is preferable to use glycol acetates such as ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone.
また、有機溶剤は、着色組成物を適正な粘度に調節し、目的とする均一な膜厚のフィルタセグメントを形成できることから、着色剤の全質量100質量部に対し、500〜4000質量部の量で用いることが好ましい。 In addition, since the organic solvent can adjust the coloring composition to an appropriate viscosity and can form a filter segment having a desired uniform film thickness, an amount of 500 to 4000 parts by mass relative to 100 parts by mass of the total amount of the colorant. It is preferable to use.
<着色組成物の製造方法>
本発明の着色組成物は、一般式(1)で表されるキノフタロン化合物(A)を含む分散剤と前記着色剤と前記バインダー樹脂とを、必要に応じて溶剤とからなる着色剤担体中に、好ましくは色素誘導体などの分散助剤と一緒に、三本ロールミル、二本ロールミル、サンドミル、ニーダー、又は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、一般式(1)で表されるフタロシアニン顔料の溶解性が高い場合、具体的には使用する有機溶剤への溶解性が高く、攪拌により溶解、異物が確認されない状態であれば、上記のような微細に分散して製造する必要はない。
<Method for producing colored composition>
The coloring composition of the present invention comprises a dispersant containing the quinophthalone compound (A) represented by the general formula (1), the colorant, and the binder resin in a colorant carrier containing a solvent, if necessary. Preferably, it can be produced by finely dispersing it together with a dispersing aid such as a pigment derivative using various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, a kneader, or an attritor. Further, when the phthalocyanine pigment represented by the general formula (1) has high solubility, specifically, when the phthalocyanine pigment has high solubility in an organic solvent to be used and is not dissolved by stirring, and foreign matter is not confirmed, It is not necessary to manufacture it by finely dispersing it.
また、本発明の着色組成物は、顔料、一般式(1)で表されるキノフタロン化合物(A)及びその他の着色剤等を別々に着色剤担体に分散したものを混合して製造することもできる。 Further, the coloring composition of the present invention may be produced by mixing a pigment, the quinophthalone compound (A) represented by the general formula (1), other colorants, and the like separately dispersed in a colorant carrier. it can.
[分散助剤]
着色剤を着色剤担体中に分散する際には、適宜、色素誘導体、樹脂型分散剤、界面活性剤等の分散助剤を用いることができる。分散助剤は、着色剤の分散に優れ、分散後の着色剤の再凝集を防止する効果が大きいので、分散助剤を用いて着色剤を着色剤担体中に分散してなる着色組成物を用いた場合には、分光透過率の高いカラーフィルタが得られる。
[Dispersion aid]
When the colorant is dispersed in the colorant carrier, a dispersion aid such as a dye derivative, a resin type dispersant, or a surfactant can be used as appropriate. The dispersion aid is excellent in dispersing the colorant and has a large effect of preventing re-aggregation of the colorant after dispersion, so that a coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid is prepared. When used, a color filter having a high spectral transmittance can be obtained.
色素誘導体としては、有機顔料、アントラキノン、アクリドン又はトリアジンに、塩基性置換基、酸性置換基、又は置換基を有していても良いフタルイミドメチル基を導入した化合物があげられ、例えば、特開昭63−305173号公報、特公昭57−15620号公報、特公昭59−40172号公報、特公昭63−17102号公報、特公平5−9469号公報等に記載されているものを使用でき、これらは単独又は2種類以上を混合して用いることができる。 Examples of the dye derivative include organic pigments, anthraquinones, acridones, or triazines having a basic substituent, an acidic substituent, or a compound having a phthalimidomethyl group optionally having a substituent introduced therein. 63-305173, Japanese Patent Publication No. 57-15620, Japanese Patent Publication No. 59-40172, Japanese Patent Publication No. 63-17102, Japanese Patent Publication No. 5-9469, etc. can be used. A single type or a mixture of two or more types can be used.
色素誘導体の配合量は、分散性向上の点から、着色剤100質量部に対し、好ましくは0.5質量部以上、さらに好ましくは1質量部以上、最も好ましくは3質量部以上である。また、耐熱性、耐光性の観点から、着色剤100質量部に対し、好ましくは40質量部以下、最も好ましくは35質量部以下である。 From the viewpoint of improving dispersibility, the amount of the dye derivative is preferably 0.5 part by mass or more, more preferably 1 part by mass or more, and most preferably 3 parts by mass or more, relative to 100 parts by mass of the colorant. From the viewpoint of heat resistance and light resistance, the amount is preferably 40 parts by mass or less, and most preferably 35 parts by mass or less, relative to 100 parts by mass of the colorant.
樹脂型分散剤は、着色剤に吸着する性質を有する顔料親和性部位と、着色剤担体と相溶性のある部位とを有し、着色剤に吸着して着色剤担体への分散を安定化する働きをするものである。樹脂型分散剤として具体的には、ポリウレタン、ポリアクリレート等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の油性分散剤、(メタ)アクリル酸−スチレン共重合体、(メタ)アクリル酸−(メタ)アクリル酸エステル共重合体、スチレン−マレイン酸共重合体、ポリビニルアルコール、ポリビニルピロリドン等の水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート系、エチレンオキサイド/プロピレンオキサイド付加化合物、リン酸エステル系等が用いられ、これらは単独又は2種以上を混合して用いることができるが、必ずしもこれらに限定されるものではない。 The resin-type dispersant has a pigment-affinity part having a property of adsorbing to the colorant and a part compatible with the colorant carrier, and is adsorbed to the colorant to stabilize the dispersion in the colorant carrier. It works. Specific examples of the resin-type dispersant include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts. , Polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, amides formed by the reaction of poly(lower alkyleneimine) with polyester having a free carboxyl group, and salts thereof Water-soluble dispersants such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone, etc. Resins, water-soluble polymer compounds, polyester systems, modified polyacrylate systems, ethylene oxide/propylene oxide addition compounds, phosphoric acid ester systems and the like are used, and these can be used alone or in combination of two or more, It is not necessarily limited to these.
市販の樹脂型分散剤としては、ビックケミー・ジャパン社製のDisperbyk−101、103、107、108、110、111、116、130、140、154、161、162、163、164、165、166、170、171、174、180、181、182、183、184、185、190、2000、2001、2020、2025、2050、2070、2095、2150、2155、又はAnti−Terra−U、203、204、又はBYK−P104、P104S、220S、6919、又はLactimon、Lactimon−WS又はBykumen等、日本ルーブリゾール社製のSOLSPERSE−3000、9000、13000、13240、13650、13940、16000、17000、18000、20000、21000、24000、26000、27000、28000、31845、32000、32500、32550、33500、32600、34750、35100、36600、38500、41000、41090、53095、55000、76500等、BASF社製のEFKA−46、47、48、452、4008、4009、4010、4015、4020、4047、4050、4055、4060、4080、4400、4401、4402、4403、4406、4408、4300、4310、4320、4330、4340、450、451、453、4540、4550、4560、4800、5010、5065、5066、5070、7500、7554、1101、120、150、1501、1502、1503、等、味の素ファインテクノ社製のアジスパーPA111、PB711、PB821、PB822、PB824等が挙げられる。 As a commercially available resin type dispersant, Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170 manufactured by Big Chemie Japan Co., Ltd. , 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or Anti-Terra-U, 203, 204, or BYK. -P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykumen, etc., SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000 manufactured by Lubrizol Japan. , 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, EFKA-46, 47, 48, manufactured by BASF. 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., Azino PA111, PB711, PB821, PB822, PB824 manufactured by Ajinomoto Fine-Techno Co., Inc. Etc.
界面活性剤としては、ラウリル硫酸ナトリウム、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、ステアリン酸ナトリウム、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等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等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等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等のアルキルベタイン、アルキルイミダゾリン等の両性界面活性剤が挙げられ、これらは単独で又は2種以上を混合して用いることができるが、必ずしもこれらに限定されるものではない。 As the surfactant, sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate. Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, stearic acid monoethanolamine, styrene-acrylic acid copolymer monoethanolamine, and polyoxyethylene alkyl ether phosphate ester; Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; alkyl Chaotic surfactants such as quaternary ammonium salts and ethylene oxide adducts thereof; amphoteric surfactants such as alkylbetaine such as alkyldimethylaminoacetic acid betaine and alkylimidazoline; and these may be used alone or in combination of two or more. Although they can be used as a mixture, they are not necessarily limited thereto.
樹脂型分散剤、界面活性剤を添加する場合には、分散に対する効果の観点から、着色剤100質量部に対し、好ましくは0.1〜55質量部、さらに好ましくは0.1〜45質量部である。 When a resin-type dispersant and a surfactant are added, from the viewpoint of the effect on dispersion, it is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass, relative to 100 parts by mass of the colorant. Is.
本発明の着色組成物は、さらに光重合性単量体及び/又は光重合開始剤を添加し、カラーフィルタ用感光性着色組成物として使用することができる。さらに、本発明の着色組成物には、増感剤、多官能チオール、アミン系化合物、レベリング剤、硬化剤、硬化促進剤、その他の添加剤成分を含有させることができる。 The coloring composition of the present invention can be used as a photosensitive coloring composition for a color filter by further adding a photopolymerizable monomer and/or a photopolymerization initiator. Furthermore, the coloring composition of the present invention may contain a sensitizer, a polyfunctional thiol, an amine compound, a leveling agent, a curing agent, a curing accelerator, and other additive components.
<光重合開始剤>
本発明の着色組成物は、光重合開始剤を含有させることができる。光重合開始剤を使用する際の配合量は、着色剤の全質量を基準(100質量部)として、5〜400質量部であることが好ましく、光硬化性の観点から10〜300質量部であることがより好ましい。
<Photopolymerization initiator>
The coloring composition of the present invention may contain a photopolymerization initiator. The amount of the photopolymerization initiator used is preferably 5 to 400 parts by mass, based on the total mass of the colorant (100 parts by mass), and 10 to 300 parts by mass from the viewpoint of photocurability. More preferably.
光重合開始剤としては、従来公知の重合開始剤を用いることが可能である。具体的には、ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、ベンジルメチルケタール、4−(2−ヒドロキシエトキシ)フェニル−(2−ヒドロキシ−2−プロピル)ケトン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタン、オリゴ[2−ヒドロキシ−2−メチル−1−[4−(1−メチルビニル)フェニル]プロパノン]、2−ヒドロキシ−1−[4−[4−(2−ヒドロキシ−2−メチルプロピオニル)ベンジル]フェニル]−2−メチルプロパン−1−オン等のアセトフェノン類;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、ベンゾインイソブチルエーテル等のベンゾイン類;2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド等のホスフィン類;その他フェニルグリオキシリックメチルエステル等が挙げられる。より具体的には、イルガキュアー651、イルガキュアー184、ダロキュアー1173、イルガキュアー500、イルガキュアー1000、イルガキュアー2959、イルガキュアー907、イルガキュアー369、イルガキュアー379、イルガキュアー1700、イルガキュアー149、イルガキュアー1800、イルガキュアー1850、イルガキュアー819、イルガキュアー784、イルガキュアー261、イルガキュアーOXE−01、イルガキュアーOXE−02(BASF社)、アデカオプトマーN1717、アデカオプトマーN1919、アデカアークルズNCI−831(ADEKA社)、Esacure1001M(Lamberti社)、特公昭59−1281号公報、特公昭61−9621号公報ならびに特開昭60−60104号公報記載のトリアジン誘導体、特開昭59−1504号公報ならびに特開昭61−243807号公報記載の有機過酸化物、特公昭43−23684号公報、特公昭44−6413号公報、特公昭47−1604号公報ならびにUSP第3567453号明細書記載のジアゾニウム化合物公報、USP第2848328号明細書、USP第2852379号明細書ならびにUSP第2940853号明細書記載の有機アジド化合物、特公昭36−22062号公報、特公昭37−13109号公報、特公昭38−18015号公報ならびに特公昭45−9610号公報記載のオルト−キノンジアジド類、特公昭55−39162号公報、特開昭59−140203号公報ならびに「マクロモレキュルス(MACROMOLECULES)」、第10巻、第1307頁(1977年)記載のヨードニウム化合物をはじめとする各種オニウム化合物、特開昭59−142205号公報記載のアゾ化合物、特開平1−54440号公報、ヨーロッパ特許第109851号明細書、ヨーロッパ特許第126712号明細書、「ジャーナル・オブ・イメージング・サイエンス(J.IMAG.SCI.)」、第30巻、第174頁(1986年)記載の金属アレン錯体、特開昭61−151197号公報記載のチタノセン類、「コーディネーション・ケミストリー・レビュー(COORDINATION CHEMISTRY REVIEW)」、第84巻、第85〜第277頁(1988年)ならびに特開平2−182701号公報記載のルテニウム等の遷移金属を含有する遷移金属錯体、特開平3−209477号公報記載のアルミナート錯体、特開平2−157760号公報記載のホウ酸塩化合物、特開昭55−127550号公報ならびに特開昭60−202437号公報記載の2,4,5−トリアリールイミダゾール二量体、四臭化炭素や特開昭59−107344号公報記載の有機ハロゲン化合物、特開平5−255347号公報記載のスルホニウム錯体又はオキソスルホニウム錯体、特開昭54−99185号公報、特開昭63−264560号公報ならびに特開平10−29977記載のアミノケトン化合物、特開2001−264530号公報、特開2001−261761号公報、特開2000−80068号公報、特開2001−233842号公報、特表2004−534797号公報、特開2006−342166、特開2008−094770、特開2009−40762、特開2010−15025、特開2010−189279、特開2010−189280公報、特表2010−526846、特表2010−527338、特表2010−527339、USP3558309号明細書(1971年)、USP4202697号明細書(1980年)ならびに特開昭61−24558号公報記載のオキシムエステル化合物等が挙げられる。 A conventionally known polymerization initiator can be used as the photopolymerization initiator. Specifically, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzylmethylketal, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone , 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butane , Oligo[2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone], 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropionyl)benzyl ]Phenyl]-2-acetophenones such as 2-methylpropan-1-one; benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; 2,4,6-trimethylbenzoyl-diphenyl- Examples thereof include phosphines such as phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; and phenylglyoxylic methyl ester. More specifically, Irgacure 651, Irgacure 184, Darocur 1173, Irgacure 500, Irgacure 1000, Irgacure 2959, Irgacure 907, Irgacure 369, Irgacure 379, Irgacure 1700, Irgacure 149, Irgac Cure 1800, Irgacure 1850, Irgacure 819, Irgacure 784, Irgacure 261, Irgacure OXE-01, Irgacure OXE-02 (BASF), Adeka Optimer N1717, Adeka Optimer N1919, Adeka Arcules NCI-. 831 (ADEKA), Esacure 1001M (Lamberti), Japanese Patent Publication No. 59-1281, Japanese Patent Publication No. 61-9621 and Japanese Patent Publication No. 60-60104, and triazine derivatives described in Japanese Patent Publication No. 59-1504 and Organic peroxides described in JP-A-61-243807, JP-B-43-23684, JP-B-44-6413, JP-B-47-1604, and diazonium compound described in USP No. 3567453. , U.S. Pat. No. 2,848,328, U.S. Pat. No. 2,852,379, and U.S. Pat. No. 2,940,853, organic azide compounds, JP-B-36-22062, JP-B-37-13109, JP-B-38-18015. And ortho-quinone diazides described in JP-B-45-9610, JP-B-55-39162, JP-A-59-140203 and "MACROMOLECULES", Volume 10, p. 1307 ( (1977) various onium compounds including iodonium compounds, azo compounds described in JP-A-59-142205, JP-A-1-54440, EP-109851, EP-126712. , “Journal of Imaging Science (J.IMAG.SCI.)”, Volume 30, p. 174 (1986), metal allene complexes, and titanocenes described in JP-A-61-151197. Containing transition metals such as ruthenium described in "COORDINATION CHEMISTRY REVIEW", Vol. 84, pp. 85-277 (1988) and JP-A-2-182701. Transition metal complex, an aluminate complex described in JP-A-3-209477, a borate compound described in JP-A-2-157760, JP-A-55-127550 and JP-A-60-202437. 2,4,5-triarylimidazole dimer, carbon tetrabromide, an organic halogen compound described in JP-A-59-107344, a sulfonium complex or an oxosulfonium complex described in JP-A-5-255347, JP-A-54-99185, JP-A-63-264560 and JP-A-10-29977, aminoketone compounds, JP-A-2001-264530, JP-A-2001-261761 and JP-A-2000-80068. JP-A-2001-233842, JP-T-2004-534797, JP-A-2006-342166, JP-A-2008-094770, JP-A-2009-40762, JP-A-2010-15025, JP-A-2010-189279, JP-A-2010. -189280 publication, special table 2010-526846, special table 2010-527338, special table 2010-527339, USP3558309 specification (1971), USP4202697 specification (1980) and JP-A-61-255858. Examples include oxime ester compounds.
これらの光重合開始剤は1種又は必要に応じて任意の比率で2種以上混合して用いることができる。 These photopolymerization initiators may be used alone or as a mixture of two or more kinds at an arbitrary ratio according to need.
<光重合性単量体>
本発明の光重合性単量体には、紫外線や熱などにより硬化して透明樹脂を生成するモノマーもしくはオリゴマーが含まれ、これらを単独で、又は2種以上混合して用いることができる。
<Photopolymerizable monomer>
The photopolymerizable monomer of the present invention includes a monomer or oligomer that is cured by ultraviolet rays or heat to produce a transparent resin, and these can be used alone or in combination of two or more.
紫外線や熱などにより硬化して透明樹脂を生成するモノマー、オリゴマーとしては、例えば、ポリエチレングリコールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、エポキシ(メタ)アクリレート、EO変性ビスフェノールAジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、ポリエステル(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、トリス(アクリロキシエチル)イソシアヌレート、トリス(メタクリロキシエチル)イソシアヌレート、ジペンタエリスリトールペンタ(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、カプロラクトン変性ジペンタエリスリトールヘキサアクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、エポキシアクリレート、ペンタエリスリトールテトラ(メタ)アクリレート等の各種アクリル酸エステル及びメタクリル酸エステル、(メタ)アクリル酸、スチレン、酢酸ビニル、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、N−ビニルホルムアミド、アクリロニトリル等が挙げられるが、本発明の効果はこれらに限定されるものではない。 Examples of the monomer or oligomer that is cured by ultraviolet rays or heat to form a transparent resin include polyethylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, epoxy (meth). Acrylate, EO-modified bisphenol A di(meth)acrylate, 1,4-butanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth) Acrylate, polyester (meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(acryloxyethyl)isocyanurate, tris(methacryloxyethyl)isocyanurate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth) ) Acrylate, caprolactone-modified dipentaerythritol hexaacrylate, ditrimethylolpropane tetra(meth)acrylate, epoxy acrylate, pentaerythritol tetra(meth)acrylate, and various other acrylic acid esters and methacrylic acid esters, (meth)acrylic acid, styrene, acetic acid Examples thereof include vinyl, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl(meth)acrylamide, N-vinylformamide, acrylonitrile, but the effect of the present invention is not limited to these. It is not something that will be done.
また、光重合性単量体は酸基を含有してもよい。例えば、多価アルコールと(メタ)アクリル酸との遊離水酸基含有ポリ(メタ)アクリレート類と、ジカルボン酸類とのエステル化物;多価カルボン酸と、モノヒドロキシアルキル(メタ)アクリレート類とのエステル化物等を挙げることができる。具体例としては、トリメチロールプロパンジアクリレート、トリメチロールプロパンジメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリメタクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールペンタメタクリレート等のモノヒドロキシオリゴアクリレート又はモノヒドロキシオリゴメタクリレート類と、マロン酸、コハク酸、グルタル酸、テレフタル酸等のジカルボン酸類との遊離カルボキシル基含有モノエステル化物;プロパン−1,2,3−トリカルボン酸(トリカルバリル酸)、ブタン−1,2,4−トリカルボン酸、ベンゼン−1,2,3−トリカルボン酸、ベンゼン−1,3,4−トリカルボン酸、ベンゼン−1,3,5−トリカルボン酸等のトリカルボン酸類と、2−ヒドロキシエチルアクリレート、2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルアクリレート、2−ヒドロキシプロピルメタクリレート等のモノヒドロキシモノアクリレート又はモノヒドロキシモノメタクリレート類との遊離カルボキシル基含有オリゴエステル化物等が挙げられるが、本発明の効果はこれらに限定されるものではない。 Further, the photopolymerizable monomer may contain an acid group. For example, esterification products of free hydroxyl group-containing poly(meth)acrylates of polyhydric alcohols and (meth)acrylic acid with dicarboxylic acids; esterification products of polyhydric carboxylic acids with monohydroxyalkyl (meth)acrylates, etc. Can be mentioned. Specific examples include trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, and other monohydroxyoligoacrylates or monohydroxyoligomethacrylates. And a free carboxyl group-containing monoester of dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, and terephthalic acid; propane-1,2,3-tricarboxylic acid (tricarballylic acid), butane-1,2,4 -Tricarboxylic acids such as tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, benzene-1,3,5-tricarboxylic acid and 2-hydroxyethyl acrylate, 2- Examples include monohydroxy monoacrylates such as hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, and 2-hydroxypropyl methacrylate, and free carboxyl group-containing oligoesterification products with monohydroxy monomethacrylates, but the effect of the present invention is limited to these. It is not something that will be done.
光重合性単量体の含有量は、光硬化性及び現像性の観点から着色剤100質量部に対して、10〜300質量部であることが好ましく、さらに10〜200質量部の量で用いることが好ましい。 The content of the photopolymerizable monomer is preferably 10 to 300 parts by mass, and further 10 to 200 parts by mass with respect to 100 parts by mass of the colorant from the viewpoint of photocurability and developability. It is preferable.
<増感剤>
さらに、本発明の着色組成物には、増感剤を含有させることができる。
増感剤としては、ベンゾフェノン誘導体、カルコン誘導体やジベンザルアセトン等に代表される不飽和ケトン誘導体、ベンジルやカンファーキノンなどに代表される1,2−ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノ−ル誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体等を挙げることができるが、これらに限定されるものではない。
<Sensitizer>
Further, the coloring composition of the present invention may contain a sensitizer.
Examples of the sensitizer include benzophenone derivatives, chalcone derivatives, unsaturated ketone derivatives represented by dibenzalacetone, 1,2-diketone derivatives represented by benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives. , Anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonole derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, Indoline derivative, azulene derivative, azurenium derivative, squarylium derivative, porphyrin derivative, tetraphenylporphyrin derivative, triarylmethane derivative, tetrabenzoporphyrin derivative, tetrapyrazinoporphyrazine derivative, phthalocyanine derivative, tetraazaporphyrazine derivative, tetraquinoxalylo Examples include porphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyllin derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, and organic ruthenium complexes. However, the present invention is not limited to these.
さらに具体例には、大河原信ら編、「色素ハンドブック」(1986年、講談社)、大河原信ら編、「機能性色素の化学」(1981年、シーエムシー)、池森忠三朗ら編、「特殊機能材料」(1986年、シーエムシー)に記載の色素及び増感剤が挙げられるがこれらに限定されるものではなく、その他、紫外から近赤外域にかけての光に対して吸収を示す色素や増感剤が挙げられ、これらは必要に応じて任意の比率で二種以上用いてもかまわない。上記、増感剤の中でチオキサントン誘導体としては、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジクロロチオキサントン、2−イソプロピルチオキサントン、4−イソプロピルチオキサントン、1−クロロ−4−プロポキシチオキサントン等を挙げることができ、ベンゾフェノン類としては、ベンゾフェノン、4−メチルベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4,4'−ジメチルベンゾフェノン、4,4'−ジメトキシベンゾフェノン、4,4'−ビス(ジエチルアミノ)ベンゾフェノン等を挙げることができ、クマリン類としては、クマリン1、クマリン338、クマリン102等を挙げることができ、ケトクマリン類としては、3,3'−カルボニルビス(7−ジエチルアミノクマリン)等を挙げることができるが、これらに限定されるものではない。 More specific examples include Nobu Okawara et al., "Dye Handbook" (1986, Kodansha), Nobu Okawara et al., "Chemistry of Functional Dyes" (1981, CMC), Tadasaburo Ikemori et al., Special Functional materials" (1986, CMC), but are not limited to these, and other dyes and sensitizers that absorb light in the ultraviolet to near infrared region. Sensitizers may be mentioned, and two or more of them may be used in an arbitrary ratio as required. Among the above-mentioned sensitizers, thioxanthone derivatives include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone and 1-chloro-4-propoxythioxanthone. And the like. Examples of benzophenones include benzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzophenone, 4,4′-dimethylbenzophenone, 4,4′-dimethoxybenzophenone, 4,4′-bis. Examples thereof include (diethylamino)benzophenone, coumarins such as coumarin 1, coumarin 338, and coumarin 102. Examples of ketocoumarins include 3,3′-carbonylbis(7-diethylaminocoumarin). However, the present invention is not limited to these.
増感剤は、必要に応じて任意の比率で2種以上用いても構わない。増感剤を使用する際の配合量は、着色感光性組成物中に含まれる光重合開始剤(E)の全質量100質量部に対し、3〜60質量部であることが好ましく、光硬化性の観点から5〜50質量部であることがより好ましい。 Two or more kinds of sensitizers may be used in an arbitrary ratio, if necessary. The compounding amount of the sensitizer is preferably 3 to 60 parts by mass with respect to 100 parts by mass of the total mass of the photopolymerization initiator (E) contained in the colored photosensitive composition, and photocuring is performed. From the viewpoint of sex, it is more preferably 5 to 50 parts by mass.
<多官能チオール>
本発明の着色組成物は、連鎖移動剤としての働きをする多官能チオールを含有することができる。
多官能チオールは、チオール基を2個以上有する化合物であればよく、例えば、ヘキサンジチオール、デカンジチオール、1,4−ブタンジオールビスチオプロピオネート、1,4−ブタンジオールビスチオグリコレート、エチレングリコールビスチオグリコレート、エチレングリコールビスチオプロピオネート、トリメチロールプロパントリスチオグリコレート、トリメチロールプロパントリスチオプロピオネート、トリメチロールプロパントリス(5−メルカプトブチレート)、ペンタエリスリトールテトラキスチオグリコレート、ペンタエリスリトールテトラキスチオプロピオネート、トリメルカプトプロピオン酸トリス(2−ヒドロキシエチル)イソシアヌレート、1,4−ジメチルメルカプトベンゼン、2、4、6−トリメルカプト−s−トリアジン、2−(N,N−ジブチルアミノ)−4,6−ジメルカプト−s−トリアジン等が挙げられる。
これらの多官能チオールは、1種を単独で、又は必要に応じて任意の比率で2種以上混合して用いることができる。
<Multifunctional thiol>
The coloring composition of the present invention may contain a polyfunctional thiol that functions as a chain transfer agent.
The polyfunctional thiol may be a compound having two or more thiol groups, and examples thereof include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, and ethylene. Glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(5-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, Pentaerythritol tetrakisthiopropionate, tris(2-hydroxyethyl) isocyanurate trimercaptopropionate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2-(N,N- Dibutylamino)-4,6-dimercapto-s-triazine and the like can be mentioned.
These polyfunctional thiols can be used singly or as a mixture of two or more kinds at an arbitrary ratio according to need.
多官能チオールの含有量は、着色組成物の全固形分の質量を基準(100質量%)として好ましくは0.1〜30質量%であり、より好ましくは1〜20質量%である。多官能チオールの含有量が0.1質量%未満では多官能チオールの添加効果が不充分であり、30質量%を越えると感度が高すぎて逆に解像度が低下する。 The content of the polyfunctional thiol is preferably 0.1 to 30% by mass, and more preferably 1 to 20% by mass, based on the mass (100% by mass) of the total solid content of the coloring composition. If the content of the polyfunctional thiol is less than 0.1% by mass, the effect of adding the polyfunctional thiol is insufficient, and if it exceeds 30% by mass, the sensitivity is too high and the resolution is decreased.
<アミン系化合物>
また、本発明の着色組成物には、溶存している酸素を還元する働きのあるアミン系化合物を含有させることができる。このようなアミン系化合物としては、トリエタノールアミン、メチルジエタノールアミン、トリイソプロパノールアミン、4−ジメチルアミノ安息香酸メチル、4−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸イソアミル、安息香酸2−ジメチルアミノエチル、4−ジメチルアミノ安息香酸2−エチルヘキシル、及びN,N−ジメチルパラトルイジン等が挙げられる。
<Amine compound>
In addition, the coloring composition of the present invention may contain an amine compound having a function of reducing dissolved oxygen. Examples of such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine and the like can be mentioned.
<レベリング剤>
本発明の着色組成物には、透明基板上での組成物のレベリング性を良くするため、レベリング剤を添加することが好ましい。レベリング剤としては、主鎖にポリエーテル構造又はポリエステル構造を有するジメチルシロキサンが好ましい。主鎖にポリエーテル構造を有するジメチルシロキサンの具体例としては、東レ・ダウコーニング社製FZ−2122、ビックケミー社製BYK−333などが挙げられる。主鎖にポリエステル構造を有するジメチルシロキサンの具体例としては、ビックケミー社製BYK−310、BYK−370などが挙げられる。主鎖にポリエーテル構造を有するジメチルシロキサンと、主鎖にポリエステル構造を有するジメチルシロキサンとは、併用することもできる。レベリング剤の含有量は通常、着色組成物の合計100質量%中、0.003〜0.5質量%用いることが好ましい。
<Leveling agent>
In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the colored composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in its main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning Co., and BYK-333 manufactured by BYK Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used together. The content of the leveling agent is usually preferably 0.003 to 0.5 mass% in the total 100 mass% of the coloring composition.
レベリング剤として特に好ましいものとしては、分子内に疎水基と親水基を有するいわゆる界面活性剤の一種で、親水基を有しながらも水に対する溶解性が小さく、着色組成物に添加した場合、その表面張力低下能が低いという特徴を有し、さらに表面張力低下能が低いにも拘らずガラス板への濡れ性が良好なものが有用であり、泡立ちによる塗膜の欠陥が出現しない添加量において十分に帯電性を抑止できるものが好ましく使用できる。このような好ましい特性を有するレベリング剤として、ポリアルキレンオキサイド単位を有するジメチルポリシロキサンが好ましく使用できる。ポリアルキレンオキサイド単位としては、ポリエチレンオキサイド単位、ポリプロピレンオキサイド単位があり、ジメチルポリシロキサンは、ポリエチレンオキサイド単位とポリプロピレンオキサイド単位とを共に有していてもよい。 Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a small hydrophilicity even though having a hydrophilic group, when added to the coloring composition, It has the characteristic of low surface tension lowering ability, and it is useful that it has good wettability to the glass plate in spite of the low surface tension lowering ability. Those that can sufficiently suppress the charging property can be preferably used. As a leveling agent having such preferable properties, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Polyalkylene oxide units include polyethylene oxide units and polypropylene oxide units, and dimethylpolysiloxane may have both polyethylene oxide units and polypropylene oxide units.
また、ポリアルキレンオキサイド単位のジメチルポリシロキサンとの結合形態は、ポリアルキレンオキサイド単位がジメチルポリシロキサンの繰り返し単位中に結合したペンダント型、ジメチルポリシロキサンの末端に結合した末端変性型、ジメチルポリシロキサンと交互に繰り返し結合した直鎖状のブロックコポリマー型のいずれであってもよい。ポリアルキレンオキサイド単位を有するジメチルポリシロキサンは、東レ・ダウコーニング株式会社から市販されており、例えば、FZ−2110、FZ−2122、FZ−2130、FZ−2166、FZ−2191、FZ−2203、FZ−2207が挙げられるが、これらに限定されるものではない。 In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. It may be of a linear block copolymer type in which alternately and repeatedly bonded. Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. -207, but not limited thereto.
レベリング剤には、アニオン性、カチオン性、ノニオン性、又は両性の界面活性剤を補助的に加えることも可能である。界面活性剤は、2種以上混合して使用しても構わない。 Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
レベリング剤に補助的に加えるアニオン性界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどが挙げられる。 Examples of anionic surfactants that are supplementarily added to the leveling agent include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, and alkyldiphenyletherdisulfonic acid. Sodium, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples thereof include esters.
レベリング剤に補助的に加えるカオチン性界面活性剤としては、アルキル4級アンモニウム塩やそれらのエチレンオキサイド付加物が挙げられる。レベリング剤に補助的に加えるノニオン性界面活性剤としては、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレートなどの;アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤、また、フッ素系やシリコーン系の界面活性剤が挙げられる。 Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and ethylene oxide adducts thereof. Nonionic surfactants that are supplementarily added to the leveling agent include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate. Examples thereof include polyethylene glycol monolaurate and the like; amphoteric surfactants such as alkylbetaine such as alkyldimethylaminoacetic acid betaine and alkylimidazoline, and fluorine-based and silicone-based surfactants.
<硬化剤、硬化促進剤>
また本発明の着色組成物には、熱硬化性樹脂の硬化を補助するため、必要に応じて、硬化剤、硬化促進剤などを含んでいてもよい。硬化剤としては、フェノール系樹脂、アミン系化合物、酸無水物、活性エステル、カルボン酸系化合物、スルホン酸系化合物などが有効であるが、特にこれらに限定されるものではなく、熱硬化性樹脂と反応し得るものであれば、いずれの硬化剤を使用してもよい。また、これらの中でも、1分子内に2個以上のフェノール性水酸基を有する化合物、アミン系硬化剤が好ましく挙げられる。前記硬化促進剤としては、例えば、アミン化合物(例えば、ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等)、4級アンモニウム塩化合物(例えば、トリエチルベンジルアンモニウムクロリド等)、ブロックイソシアネート化合物(例えば、ジメチルアミン等)、イミダゾール誘導体二環式アミジン化合物及びその塩(例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等)、リン化合物(例えば、トリフェニルホスフィン等)、グアナミン化合物(例えば、メラミン、グアナミン、アセトグアナミン、ベンゾグアナミン等)、S−トリアジン誘導体(例えば、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等)などを用いることができる。これらは1種単独で使用してもよく、2種以上を併用してもよい。前記硬化促進剤の含有量としては、熱硬化性樹脂100質量部に対し、0.01〜15質量部が好ましい。
<Curing agent, curing accelerator>
Further, the coloring composition of the present invention may contain a curing agent, a curing accelerator, etc., if necessary, in order to assist the curing of the thermosetting resin. As the curing agent, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, etc. are effective, but are not particularly limited to these, and thermosetting resins Any curing agent may be used as long as it can react with. Among these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferable. Examples of the curing accelerator include amine compounds (eg, dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl). -N,N-dimethylbenzylamine etc.), quaternary ammonium salt compound (eg triethylbenzylammonium chloride etc.), blocked isocyanate compound (eg dimethylamine etc.), imidazole derivative bicyclic amidine compound and salts thereof (eg Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2- Ethyl-4-methylimidazole etc.), phosphorus compounds (eg triphenylphosphine etc.), guanamine compounds (eg melamine, guanamine, acetoguanamine, benzoguanamine etc.), S-triazine derivatives (eg 2,4-diamino-6). -Methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine/isocyanuric acid adduct, 2,4-diamino-6- Methacryloyloxyethyl-S-triazine/isocyanuric acid adduct) and the like can be used. These may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting resin.
<その他の添加剤成分>
本発明の着色組成物には、組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。また、透明基板との密着性を高めるためにシランカップリング剤等の密着向上剤を含有させることもできる。
<Other additive components>
The colored composition of the present invention may contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Further, an adhesion improver such as a silane coupling agent may be contained in order to improve the adhesion to the transparent substrate.
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及びそのメチルエーテル、t−ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。貯蔵安定剤は、着色剤の全量100質量部に対し、0.1〜10質量部の量で用いることができる。 Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, tetraphenylphosphine and the like. Examples thereof include organic phosphine and phosphite. The storage stabilizer can be used in an amount of 0.1 to 10 parts by mass based on 100 parts by mass of the total amount of the colorant.
密着向上剤としては、ビニルトリス(β−メトキシエトキシ)シラン、ビニルエトキシシラン、ビニルトリメトキシシラン等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の(メタ)アクリルシラン類、β−(5,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(5,4−エポキシシクロヘキシル)メチルトリメトキシシラン、β−(5,4−エポキシシクロヘキシル)エチルトリエトキシシラン、β−(5,4−エポキシシクロヘキシル)メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)γ−アミノプロピルトリエトキシシラン、N−β(アミノエチル)γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリエトキシシラン等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン等のチオシラン類等のシランカップリング剤が挙げられる。密着向上剤は、着色組成物中の着色剤の全量100質量部に対し、0.01〜10質量部、好ましくは0.05〜5質量部の量で用いることができる。 Examples of the adhesion improver include vinyl silanes such as vinyltris(β-methoxyethoxy)silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth)acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β-(5, 4-epoxycyclohexyl)ethyltrimethoxysilane, β-(5,4-epoxycyclohexyl)methyltrimethoxysilane, β-(5,4-epoxycyclohexyl)ethyltriethoxysilane, β-(5,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(amino Ethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-amino Examples of the silane coupling agent include aminosilanes such as propyltrimethoxysilane and N-phenyl-γ-aminopropyltriethoxysilane, and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the total amount of the coloring agent in the coloring composition.
<粗大粒子の除去>
本発明の着色組成物は、遠心分離、焼結フィルタ、メンブレンフィルタ等の手段にて、5μm以上の粗大粒子、好ましくは1μm以上の粗大粒子、さらに好ましくは0.5μm以上の粗大粒子及び混入した塵の除去を行うことが好ましい。このように着色組成物は、実質的に0.5μm以上の粒子を含まないことが好ましい。より好ましくは0.3μm以下であることが好ましい。
<Removal of coarse particles>
The colored composition of the present invention is mixed with coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more and coarse particles by means of centrifugation, a sintering filter, a membrane filter or the like. It is preferable to remove dust. As described above, it is preferable that the coloring composition does not substantially contain particles of 0.5 μm or more. It is more preferably 0.3 μm or less.
<カラーフィルタ>
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、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つの緑色フィルタセグメント、及び少なくとも1つの青色フィルタセグメントを具備する。
また、カラーフィルタは、さらにマゼンタ色フィルタセグメント、シアン色フィルタセグメント、及び黄色フィルタセグメントを具備するものであってもよい。
<Color filter>
Next, the color filter of the present invention will be described. The color filter of the present invention comprises at least one red filter segment, at least one green filter segment, and at least one blue filter segment.
Further, the color filter may further include a magenta color filter segment, a cyan color filter segment, and a yellow color filter segment.
カラーフィルタを構成する透明基板等の基材としては、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。 As a substrate such as a transparent substrate that constitutes a color filter, a glass plate such as soda lime glass, low alkali borosilicate glass, or alkali-free aluminoborosilicate glass, or a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate. 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 for driving the liquid crystal after paneling.
<カラーフィルタの製造方法>
本発明のカラーフィルタは、印刷法又はフォトリソグラフィー法により、製造することができる。
印刷法によるフィルタセグメントの形成は、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、低コストであり、かつ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及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制御も重要であり、分散剤や体質顔料によってインキ粘度の調整も行うことができる。
<Method of manufacturing color filter>
The color filter of the present invention can be manufactured by a printing method or a photolithography method.
Since the formation of the filter segment by the printing method can be patterned by simply printing and drying the coloring composition prepared as the printing ink, the manufacturing method of the color filter is low cost and excellent in mass productivity. There is. Furthermore, the development of printing technology enables printing of fine patterns having high dimensional accuracy and smoothness. For printing, it is preferable that the composition is such that the ink does not dry and solidify on the printing plate or on the blanket. Further, it is important to control the fluidity of the ink on the printing machine, and the ink viscosity can be adjusted by the dispersant and the extender pigment.
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0.2〜5μm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、溶剤又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 the filter segment is formed by a photolithography method, the coloring composition prepared as the solvent-developing or alkali-developing colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating, or the like. Depending on the method, it is applied so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern, which is provided in contact or non-contact with the film. Then, after immersing in a solvent or an alkaline developer or spraying a developer with a spray 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 carried out if necessary. According to the photolithography method, it is possible to manufacture a color filter with higher accuracy than the above printing method.
現像に際しては、アルカリ現像液として炭酸ナトリウム、水酸化ナトリウム等の水溶液が使用され、ジメチルベンジルアミン、トリエタノールアミン等の有機アルカリを用いることもできる。また、現像液には、消泡剤や界面活性剤を添加することもできる。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。 Upon development, an aqueous solution of sodium carbonate, sodium hydroxide or the like is used as an alkali developing solution, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added to the developing solution. In order to increase the UV exposure sensitivity, after coating and drying the above 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. After that, ultraviolet exposure can be performed.
本発明のカラーフィルタは、上記方法の他に電着法、転写法、インクジェット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。なお、電着法は、基板上に形成した透明導電膜を利用して、コロイド粒子の電気泳動により各色フィルタセグメントを透明導電膜の上に電着形成することでカラーフィルタを製造する方法である。また、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を形成しておき、このフィルタセグメントを所望の基板に転写させる方法である。 The color filter of the present invention can be produced by an electrodeposition method, a transfer method, an inkjet method or the like in addition to the above method, and the coloring composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by utilizing a transparent conductive film formed on a substrate to form each color filter segment on the transparent conductive film by electrophoretic deposition of colloidal particles. .. The transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet and the filter segment is transferred to a desired substrate.
透明基板あるいは反射基板上に各色フィルタセグメントを形成する前に、あらかじめブラックマトリクスを形成することができる。ブラックマトリクスとしては、クロムやクロム/酸化クロムの多層膜、窒化チタニウムなどの無機膜や、遮光剤を分散した樹脂膜が用いられるが、これらに限定されない。また、前記の透明基板あるいは反射基板上に薄膜トランジスター(TFT)をあらかじめ形成しておき、その後に各色フィルタセグメントを形成することもできる。また本発明のカラーフィルタ上には、必要に応じてオーバーコート膜や透明導電膜などが形成される。 A black matrix can be formed in advance before forming each color filter segment on the transparent substrate or the reflective substrate. As the black matrix, chromium, a chromium/chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light shielding agent is dispersed is used, but the black matrix is not limited thereto. It is also possible to previously form a thin film transistor (TFT) on the transparent substrate or the reflective substrate and then form each color filter segment. In addition, an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention as needed.
カラーフィルタは、シール剤を用いて対向基板と張り合わせ、シール部に設けられた注入口から液晶を注入したのち注入口を封止し、必要に応じて偏光膜や位相差膜を基板の外側に張り合わせることにより、液晶表示パネルが製造される。 The color filter is attached to the counter substrate using a sealant, liquid crystal is injected from the injection port provided in the sealing section, and then the injection port is sealed. If necessary, a polarizing film or a retardation film is placed on the outside of the substrate. A liquid crystal display panel is manufactured by pasting.
かかる液晶表示パネルは、ツイステッド・ネマティック(TN)、スーパー・ツイステッド・ネマティック(STN)、イン・プレーン・スイッチング(IPS)、ヴァーティカリー・アライメント(VA)、オプティカリー・コンベンセンド・ベンド(OCB)等のカラーフィルタを使用してカラー化を行う液晶表示モードに使用することができる。 Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convenced bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as.
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、例中、「部」及び「%」は、「質量部」及び「質量%」をそれぞれ表す。また、「PGMAC」とはプロピレングリコールモノメチルエーテルアセテートを意味する。 Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In addition, in an example, "part" and "%" represent a "mass part" and "mass %", respectively. Further, “PGMAC” means propylene glycol monomethyl ether acetate.
(樹脂の重合平均分子量(Mw))
樹脂の重合平均分子量(Mw)は、TSKgelカラム(東ソー社製)を用い、RI検出器を装備したGPC(東ソー社製、HLC−8120GPC)で、展開溶媒にTHFを用いて測定したポリスチレン換算の重量平均分子量(Mw)である。
(Polymerization average molecular weight (Mw))
The polymerization average molecular weight (Mw) of the resin is a polystyrene conversion measured by using TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent. It is a weight average molecular weight (Mw).
(樹脂の酸価)
樹脂溶液0.5〜1.0部に、アセトン80ml及び水10mlを加えて攪拌して均一に溶解させ、0.1mol/LのKOH水溶液を滴定液として、自動滴定装置(「COM−555」平沼産業製)を用いて滴定し、樹脂溶液の酸価を測定した。そして、樹脂溶液の酸価と樹脂溶液の固形分濃度から、樹脂の固形分あたりの酸価を算出した。
(Acid value of resin)
To 0.5 to 1.0 part of the resin solution, 80 ml of acetone and 10 ml of water were added and stirred to be uniformly dissolved, and a 0.1 mol/L KOH aqueous solution was used as a titration liquid to prepare an automatic titrator (“COM-555”). (Manufactured by Hiranuma Sangyo), and the acid value of the resin solution was measured. Then, the acid value per solid content of the resin was calculated from the acid value of the resin solution and the solid content concentration of the resin solution.
(顔料のハロゲン置換数)
顔料中のハロゲン置換数は、顔料を酸素燃焼フラスコ法にて燃焼させ、該燃焼物を水に吸収させた液体を、イオンクロマトグラフ(ICS−2000イオンクロマトグラフィー、DIONEX社製)により分析してハロゲン量を定量し、ハロゲン置換数に換算することで得た。
(Number of halogen substitution of pigment)
The number of halogen substitutions in the pigment was analyzed by ion chromatography (ICS-2000 ion chromatography, manufactured by DIONEX) of a liquid obtained by burning the pigment by an oxygen combustion flask method and absorbing the combustion product in water. It was obtained by quantifying the amount of halogen and converting it into the number of halogen substitutions.
(顔料のハロゲン分布幅)
顔料中のハロゲン分布幅は、飛行時間型質量分析装置(autoflexIII(TOF−MS)、ブルカー・ダルトニクス社製)を用いて決定した。ハロゲンの含有量は顔料粉末を質量分析して得られたマススペクトラムにおいて、各成分に相当する分子イオンピークの信号強度(各ピーク値)と、各ピーク値を積算した値(全ピーク値)とを算出し、全ピーク値に対する各ピーク値の割合より求めた。ハロゲン分布幅は、全ピーク値に対する各ピーク値の割合が1%以上のピークの数をカウントし、ハロゲン分布幅とした。
(Halogen distribution width of pigment)
The halogen distribution width in the pigment was determined using a time-of-flight mass spectrometer (autoflex III (TOF-MS), manufactured by Bruker Daltonics). In the mass spectrum obtained by mass spectrometric analysis of the pigment powder, the halogen content is the signal intensity of each molecular ion peak corresponding to each component (each peak value) and the value obtained by integrating each peak value (all peak values). Was calculated and calculated from the ratio of each peak value to the total peak value. The halogen distribution width was defined as the halogen distribution width by counting the number of peaks in which the ratio of each peak value to all peak values was 1% or more.
<バインダー樹脂の製造方法>
(アクリル樹脂溶液1の調整)
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けた反応容器にシクロヘキサノン70.0部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管よりn−ブチルメタクリレート13.3部、2−ヒドロキシエチルメタクリレート4.6部、メタクリル酸4.3部、パラクミルフェノールエチレンオキサイド変性アクリレート(東亞合成株式会社製「アロニックスM110」)7.4部、2,2’−アゾビスイソブチロニトリル0.4部の混合物を2時間かけて滴下した。滴下終了後、更に3時間反応を継続し、重量平均分子量(Mw)26000のアクリル樹脂の溶液を得た。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質量%になるようにプロピレングリコールモノエチルエーテルアセテートを添加してアクリル樹脂溶液1を調製した。
<Method for producing binder resin>
(Preparation of acrylic resin solution 1)
70.0 parts of cyclohexanone was charged into a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer in a separable four-necked flask, the temperature was raised to 80° C., the inside of the reaction vessel was replaced with nitrogen, and then a dropping tube From n-butyl methacrylate 13.3 parts, 2-hydroxyethyl methacrylate 4.6 parts, methacrylic acid 4.3 parts, paracumylphenol ethylene oxide modified acrylate (Toagosei Co., Ltd. "Aronix M110") 7.4 parts, A mixture of 0.4 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After the dropping was completed, the reaction was continued for another 3 hours to obtain a solution of an acrylic resin having a weight average molecular weight (Mw) of 26000. After cooling to room temperature, about 2 g of the resin solution was sampled and dried by heating at 180° C. for 20 minutes to measure the non-volatile content, and the non-volatile content was adjusted to 20% by mass in the resin solution synthesized above. Acrylic resin solution 1 was prepared by adding ether acetate.
(アクリル樹脂溶液2の調製)
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、滴下管及び撹拌装置を取り付けた反応容器にシクロヘキサノン207部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管より、メタクリル酸20部、パラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成社製アロニックスM110)20部、メタクリル酸メチル45部、2−ヒドロキシエチルメタクリレート8.5部、及び2,2'−アゾビスイソブチロニトリル1.33部の混合物を2時間かけて滴下した。滴下終了後、更に3時間反応を継続し、共重合体樹脂溶液を得た。次に得られた共重合体溶液全量に対して、窒素ガスを停止し乾燥空気を1時間注入しながら攪拌したのちに、室温まで冷却した後、2−メタクリロイルオキシエチルイソシアネート(昭和電工社製カレンズMOI)6.5部、ラウリン酸ジブチル錫0.08部、シクロヘキサノン26部の混合物を70℃で3時間かけて滴下した。滴下終了後、更に1時間反応を継続し、アクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約2部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2を調製した。重量平均分子量(Mw)は18000であった。
(Preparation of acrylic resin solution 2)
207 parts of cyclohexanone was charged into a reaction container equipped with a thermometer, a cooling pipe, a nitrogen gas introduction pipe, a dropping pipe and a stirring device in a separable 4-neck flask, heated to 80° C., and the inside of the reaction container was replaced with nitrogen, and then dropped. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2'-azobis. A mixture of 1.33 parts of isobutyronitrile was added dropwise over 2 hours. After the dropping was completed, the reaction was continued for another 3 hours to obtain a copolymer resin solution. Next, with respect to the total amount of the obtained copolymer solution, nitrogen gas was stopped, and after stirring while injecting dry air for 1 hour, the mixture was cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Karenzu manufactured by Showa Denko KK) A mixture of 6.5 parts of MOI), 0.08 part of dibutyltin laurate, and 26 parts of cyclohexanone was added dropwise at 70° C. over 3 hours. After the dropping was completed, the reaction was continued for another hour to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was sampled, dried by heating at 180° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the resin solution synthesized above so that the nonvolatile content became 20% by weight. Then, an acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18,000.
<樹脂型分散剤の調整>
(樹脂型分散剤1の調製)
市販の樹脂型分散剤であるビックケミー社製「BYK−21116」を、樹脂型分散剤1として用いた。
<Adjustment of resin type dispersant>
(Preparation of resin type dispersant 1)
A commercially available resin type dispersant “BYK-21116” manufactured by BYK Chemie was used as the resin type dispersant 1.
(樹脂型分散剤溶液2の調製)
市販の樹脂型分散剤であるBASF社製EFKA4300と、プロピレングリコールモノメチルエーテルアセテートとを混合して不揮発分40質量%溶液に調製し、樹脂型分散剤溶液2を得た。
(Preparation of resin type dispersant solution 2)
A commercially available resin-type dispersant, EFKA4300 manufactured by BASF Corp., and propylene glycol monomethyl ether acetate were mixed to prepare a solution having a nonvolatile content of 40% by mass to obtain a resin-type dispersant solution 2.
<キノフタロン化合物[A]の製造方法>
キノフタロン化合物の製造に先だって、本発明に用いたキノフタロン化合物の同定方法について説明する。
<Method for producing quinophthalone compound [A]>
Prior to the production of the quinophthalone compound, a method for identifying the quinophthalone compound used in the present invention will be described.
(キノフタロン化合物の同定方法)
本発明のキノフタロン化合物の同定は、Waters社ACQUITY UPLS H−Class(使用カラム:ACQUITY UPLC BEH C18 Column 130Å、 1.7μm、2.1mm × 50mm) / Ms TAP XEVO TQDから得られたマススペクトラムの分子イオンピークと、計算によって得られる質量数との一致をもって、得られた化合物の同定を行った。各々の理論値と測定値を表1にまとめた。
(Method for identifying quinophthalone compound)
The quinophthalone compound of the present invention was identified by ACQUITY UPLS H-Class (Water column: ACQUITY UPLC BEH C18 Column 130Å, 1.7 μm, 2.1 mm×50 mm)/Ms TAP XEVO TQD molecular mass spectrum. The obtained compound was identified based on the agreement between the ion peak and the mass number obtained by calculation. The theoretical value and measured value of each are summarized in Table 1.
[実施例1]
(キノフタロン化合物A−1の製造)
安息香酸メチル30部、安息香酸30部、8−アミノキナルジン10部、無水フタル酸20.6部加え、180℃に加熱し、水を留去しながら6時間攪拌を行った。室温まで冷却後、反応混合物をメタノール500部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、ケーキを得た。つづいて、上記ケーキに、イソブタノールを100部、ジメチルプロピルアミン14.9部加え、100℃に加熱し、メタノールを留去しながら6時間攪拌を行った。室温まで冷却後、反応混合物をメタノール500部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、減圧下で乾燥させ、中間体1を15.5部(収率85%)得た。
塩化シアヌル9.9部、アセトン1000部を加え、氷浴下で冷却しながら撹拌した。そこへ中間体1 15.5部をN−メチルピロリドン1000部に溶解させ、塩化シアヌルの溶液に1時間かけて滴下した。5℃〜15℃の間で3時間撹拌した後にスルファニル酸20.5部加え、85℃に加熱し、5時間撹拌を行った。室温まで冷却後、反応混合物を水3000部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらに水、メタノールで洗浄を行い、減圧下で乾燥させ、化合物A−1を24.5部(収率64%)得た。
[Example 1]
(Production of quinophthalone compound A-1)
Methyl benzoate (30 parts), benzoic acid (30 parts), 8-aminoquinaldine (10 parts) and phthalic anhydride (20.6 parts) were added, and the mixture was heated to 180° C. and stirred for 6 hours while distilling off water. After cooling to room temperature, the reaction mixture was added to 500 parts of methanol and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration and then washed with methanol to obtain a cake. Subsequently, 100 parts of isobutanol and 14.9 parts of dimethylpropylamine were added to the above cake, heated to 100° C., and stirred for 6 hours while distilling methanol off. After cooling to room temperature, the reaction mixture was added to 500 parts of methanol and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with methanol, and dried under reduced pressure to give Intermediate 1 (15.5 parts, yield 85%).
Cyanuric chloride (9.9 parts) and acetone (1000 parts) were added, and the mixture was stirred while cooling in an ice bath. Thereto, 15.5 parts of Intermediate 1 was dissolved in 1000 parts of N-methylpyrrolidone and added dropwise to a solution of cyanuric chloride over 1 hour. After stirring for 3 hours between 5°C and 15°C, 20.5 parts of sulfanilic acid was added, and the mixture was heated to 85°C and stirred for 5 hours. After cooling to room temperature, the reaction mixture was poured into 3000 parts of water and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with water and methanol, and dried under reduced pressure to obtain 24.5 parts (yield 64%) of compound A-1.
[実施例2]
(キノフタロン化合物A−2の製造)
中間体1の合成反応において、無水フタル酸20.6部を2,3−ナフタレンジカルボン酸無水物27.6部に変更した以外は同様に反応を行い、中間体2を19.5部(収率91%)得た。
塩化シアヌル10.6部、アセトン1000部を加え、氷浴下で冷却しながら撹拌した。そこへ中間体2 19.5部をN−メチルピロリドン1000部に溶解させ、塩化シアヌルの溶液に1時間かけて滴下した。5℃〜15℃の間で3時間撹拌した後にスルファニル酸10.0部加え、50℃に加熱し、3時間撹拌を行った。次いでアニリン6.5部加え、85℃に加熱し、2時間撹拌を行った。室温まで冷却後、反応混合物を水3000部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらに水、メタノールで洗浄を行い、減圧下で乾燥させ、化合物A−2を26.3部(収率67%)得た。
[Example 2]
(Production of quinophthalone compound A-2)
In the synthesis reaction of Intermediate 1, the same reaction was performed except that 20.6 parts of phthalic anhydride was changed to 27.6 parts of 2,3-naphthalenedicarboxylic anhydride, and 19.5 parts of Intermediate 2 The rate was 91%).
10.6 parts of cyanuric chloride and 1000 parts of acetone were added, and the mixture was stirred while cooling in an ice bath. Thereto, 19.5 parts of Intermediate 2 was dissolved in 1000 parts of N-methylpyrrolidone and added dropwise to a solution of cyanuric chloride over 1 hour. After stirring for 3 hours between 5°C and 15°C, 10.0 parts of sulfanilic acid was added, heated to 50°C, and stirred for 3 hours. Next, 6.5 parts of aniline was added, heated to 85° C., and stirred for 2 hours. After cooling to room temperature, the reaction mixture was poured into 3000 parts of water and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with water and methanol, and dried under reduced pressure to obtain 26.3 parts (yield 67%) of compound A-2.
[実施例3]
(キノフタロン化合物A−3の製造)
中間体1の合成反応において、8−アミノキナルジン10部を6−ブロモ−8−アミノキナルジン10部に、無水フタル酸20.6部を13.7部、ジメチルプロピルアミン14.9部を9.9部に変更した以外は同様に反応を行い、中間体3を13.6部(収率88%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体3 13.6部塩化シアヌル10.6部を6.8部、スルファニル酸10.0部を4−(アミノメチル)安息香酸5.6部、アニリン6.5部を8−ヒドロキシキナルジン7.1部に変更した以外は同様に反応を行い、化合物A−3を19.6部(収率70%)得た。
[Example 3]
(Production of quinophthalone compound A-3)
In the synthetic reaction of Intermediate 1, 10 parts of 8-aminoquinaldine was added to 10 parts of 6-bromo-8-aminoquinaldine, 13.7 parts of 20.6 parts of phthalic anhydride and 14.9 parts of dimethylpropylamine. The same reaction was performed except that the amount was changed to 9.9 parts to obtain 13.6 parts (yield 88%) of Intermediate 3.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted to 13.6 parts of Intermediate 3, 6.8 parts of 10.6 parts of cyanuric chloride, and 10.0 parts of sulfanilic acid were added to 4-(aminomethyl)benzoic acid. The same reaction was performed except that 5.6 parts of acid and 6.5 parts of aniline were changed to 7.1 parts of 8-hydroxyquinaldine to obtain 19.6 parts (yield 70%) of compound A-3.
[実施例4]
(キノフタロン化合物A−4の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体4 16.0部、塩化シアヌル10.6部を4.9部、スルファニル酸10.0部を4−メチルフェノール2.9部、アニリン6.5部を4−アミノフェノール3.5部に変更した以外は同様に反応を行い中間体5を16.9部(収率71%)得た。
中間体5 16.9部、水酸化ナトリウム0.9部、N−メチルピロリドン400部加え130℃に加熱し、そこへ1,3−プロパンスルトン2.8部加え、5時間加熱撹拌した。室温まで冷却後、反応混合物をメタノール800部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、減圧下で乾燥させ、化合物A−4を13.8部(収率72%)得た。
[Example 4]
(Production of quinophthalone compound A-4)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted to 16.0 parts of Intermediate 4, 10.6 parts of cyanuric chloride was 4.9 parts, and 10.0 parts of sulfanilic acid was added to 4-methylphenol.2. The same reaction was performed except that 9 parts and 6.5 parts of aniline were changed to 3.5 parts of 4-aminophenol to obtain 16.9 parts (yield 71%) of Intermediate 5.
Intermediate 5 (16.9 parts), sodium hydroxide (0.9 parts) and N-methylpyrrolidone (400 parts) were added, and the mixture was heated to 130° C., and 1,3-propanesultone (2.8 parts) was added, and the mixture was heated with stirring for 5 hours. After cooling to room temperature, the reaction mixture was added to 800 parts of methanol and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with methanol, and dried under reduced pressure to obtain 13.8 parts (yield 72%) of compound A-4.
[実施例5]
(キノフタロン化合物A−5の製造)
安息香酸メチル30部、安息香酸30部、6−ニトロ−8−ヒドロキシキナルジン10部、無水フタル酸8.7部加え、180℃に加熱し、水を留去しながら6時間攪拌を行った。室温まで冷却後、反応混合物をメタノール500部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、減圧下で乾燥させ、中間体6を14.4部(収率88%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体6 14.4部、塩化シアヌル9.9部を8.0部、スルファニル酸20.5部を4−アミノフタル酸17.2部に変更した以外は同様に反応を行い、化合物A−5を23.0部(収率70%)得た。
[Example 5]
(Production of quinophthalone compound A-5)
Methyl benzoate (30 parts), benzoic acid (30 parts), 6-nitro-8-hydroxyquinaldine (10 parts) and phthalic anhydride (8.7 parts) were added, and the mixture was heated to 180°C and stirred for 6 hours while distilling water. .. After cooling to room temperature, the reaction mixture was added to 500 parts of methanol and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with methanol, and dried under reduced pressure to obtain 14.4 parts (yield 88%) of intermediate 6.
In the synthetic reaction of Compound A-1, 15.5 parts of Intermediate 1 was 14.4 parts of Intermediate 6, 8.0 parts of 9.9 parts of cyanuric chloride, and 20.5 parts of sulfanilic acid were added to 4-aminophthalic acid. The same reaction was performed except for changing to 2 parts to obtain 23.0 parts (yield 70%) of Compound A-5.
[実施例6]
(キノフタロン化合物A−6の製造)
中間体6の合成反応において、6−ニトロ−8−ヒドロキシキナルジン10部を8−ヒドロキシキナルジン10部に、無水フタル酸20.6部を4,5−ジクロロフタル酸無水物16.4部に変更した以外は同様に反応を行い、中間体7を19.1部(収率85%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体7 16.4部、塩化シアヌル10.6部を9.9部、スルファニル酸10.0部を4−アミノフタル酸9.7部、アニリン6.5部を2−メトキシエタノール4.9部に変更した以外は同様に反応を行い、化合物A−6を26.2部(収率71%)得た。
[Example 6]
(Production of quinophthalone compound A-6)
In the synthetic reaction of Intermediate 6, 10 parts of 6-nitro-8-hydroxyquinaldine was added to 10 parts of 8-hydroxyquinaldine, and 20.6 parts of phthalic anhydride was added to 16.4 parts of 4,5-dichlorophthalic anhydride. The same reaction was carried out except that the above was changed to 1 to obtain 19.1 parts (yield 85%) of intermediate 7.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted into 16.4 parts of Intermediate 7, 10.6 parts of cyanuric chloride was 9.9 parts, and 10.0 parts of sulfanilic acid was added to 4-aminophthalic acid. The same reaction was performed except that 7 parts and 6.5 parts of aniline were changed to 4.9 parts of 2-methoxyethanol to obtain 26.2 parts (yield 71%) of compound A-6.
[実施例7]
(キノフタロン化合物A−7の製造)
中間体1の合成反応において、8−アミノキナルジン10部を中間体8 10部に、無水フタル酸20.6部をテトラクロロフタル酸無水物20.1部、ジメチルプロピルアミン14.9部を7.5部に変更した以外は同様に反応を行い、中間体9を16.5部(収率89%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体9 16.5部、塩化シアヌル9.9部を5.2部、スルファニル酸20.5部を5−アミノサリチル酸9.6部に変更した以外は同様に反応を行い、化合物A−7を22.4部(収率82%)得た。
[Example 7]
(Production of quinophthalone compound A-7)
In the synthesis reaction of Intermediate 1, 10 parts of 8-aminoquinaldine was added to 810 parts of Intermediate, 20.6 parts of phthalic anhydride was added to 20.1 parts of tetrachlorophthalic anhydride, and 14.9 parts of dimethylpropylamine. The same reaction was performed except that the amount was changed to 7.5 parts, and 16.5 parts (yield 89%) of intermediate 9 was obtained.
In the synthetic reaction of compound A-1, 15.5 parts of intermediate 1 was intermediate 16.5 parts, cyanuric chloride 9.9 parts was 5.2 parts, sulfanilic acid 20.5 parts was 5-aminosalicylic acid 9. The same reaction was performed except that the amount was changed to 6 parts to obtain 22.4 parts (yield: 82%) of compound A-7.
[実施例8]
(キノフタロン化合物A−8の製造)
中間体6の合成反応において、6−ニトロ−8−ヒドロキシキナルジン10部を中間体10 10部に、無水フタル酸8.7部をテトラクロロフタル酸無水物11.0部に変更した以外は同様に反応を行い、中間体11を16.9部(収率91%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体11 16.9部、塩化シアヌル9.9部を5.3部、スルファニル酸20.5部を4−ヒドロキシサリチル酸9.8部に変更した以外は同様に反応を行い、化合物A−7を18.1部(収率65%)得た。
[Example 8]
(Production of quinophthalone compound A-8)
In the synthesis reaction of intermediate 6, except that 10 parts of 6-nitro-8-hydroxyquinaldine was changed to 10 parts of intermediate 10 and 8.7 parts of phthalic anhydride was changed to 11.0 parts of tetrachlorophthalic anhydride. The same reaction was performed to obtain 16.9 parts (yield 91%) of Intermediate 11.
In the synthetic reaction of compound A-1, 15.5 parts of intermediate 1 was intermediated with 16.9 parts of intermediate 11, 5.3 parts of 9.9 parts of cyanuric chloride, and 20.5 parts of sulfanilic acid were added to 9 parts of 4-hydroxysalicylic acid. The same reaction was carried out except that the amount was changed to 8 parts to obtain 18.1 parts (yield 65%) of Compound A-7.
[実施例9]
(キノフタロン化合物A−9の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体9 15.0部、塩化シアヌル10.6部を4.8部、スルファニル酸10.0部を4.5部、アニリン6.5部を2.9部に変更した以外は同様に反応を行い、化合物A−9を19.5部(収率82%)得た。
[Example 9]
(Production of quinophthalone compound A-9)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted to 15.0 parts of Intermediate 9, 10.6 parts of cyanuric chloride was 4.8 parts, 10.0 parts of sulfanilic acid was 4.5 parts and aniline. The same reaction was performed except that 6.5 parts was changed to 2.9 parts to obtain 19.5 parts (yield: 82%) of compound A-9.
[実施例10]
(キノフタロン化合物A−10の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体9 15.0部、塩化シアヌル10.6部を4.8部、スルファニル酸10.0部を5−アミノサリチル酸4.0部、アニリン6.5部を4−アミノフェノール3.4部に変更した以外は同様に反応を行い、化合物A−10を19.7部(収率83%)得た。
[Example 10]
(Production of quinophthalone compound A-10)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was used as 15.0 parts of Intermediate 9, 10.6 parts of cyanuric chloride as 4.8 parts, and 10.0 parts of sulfanilic acid as 5-aminosalicylic acid. The same reaction was performed except that 0 parts and 6.5 parts of aniline were changed to 3.4 parts of 4-aminophenol to obtain 19.7 parts (yield 83%) of Compound A-10.
[実施例11]
(キノフタロン化合物A−11の製造)
化合物A−1の合成反応において、中間体1 15.5部を中間体12 15部、塩化シアヌル9.9部を6.2部、スルファニル酸20.5部を4−ヒドロキシ安息香酸10.3部に変更した以外は同様に反応を行い、化合物A−11を17.5部(収率65%)得た。
[Example 11]
(Production of quinophthalone compound A-11)
In the synthetic reaction of compound A-1, 15.5 parts of Intermediate 1 was converted into 15 parts of Intermediate 12, 6.2 parts of 9.9 parts of cyanuric chloride, 20.5 parts of sulfanilic acid and 10.3 of 4-hydroxybenzoic acid. The reaction was performed in the same manner except that the amount was changed to 1 part, and 17.5 parts (yield 65%) of compound A-11 was obtained.
[実施例12]
(キノフタロン化合物A−12の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体9 15.0部、塩化シアヌル10.6部を4.8部、スルファニル酸10.0部を5−アミノサリチル酸4.0部、アニリン6.5部を水30.0部に変更した以外は同様に反応を行い、化合物A−12を17.9部(収率84%)得た。
[Example 12]
(Production of quinophthalone compound A-12)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was used as 15.0 parts of Intermediate 9, 10.6 parts of cyanuric chloride as 4.8 parts, and 10.0 parts of sulfanilic acid as 5-aminosalicylic acid. The same reaction was performed except that 0 part and 6.5 parts of aniline were changed to 30.0 parts of water to obtain 17.9 parts (yield 84%) of Compound A-12.
[実施例13]
(キノフタロン化合物A−13の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体13 15.0部、塩化シアヌル10.6部を5.6部、スルファニル酸10.0部を5−アミノサリチル酸4.7部、アニリン6.5部をタウリン4.6部に変更した以外は同様に反応を行い、化合物A−13を21.9部(収率85%)得た。
[Example 13]
(Production of quinophthalone compound A-13)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was added with 15.0 parts of Intermediate 13, 5.6 parts of 10.6 parts of cyanuric chloride, 10.0 parts of sulfanilic acid and 5-aminosalicylic acid. The same reaction was performed except that 7 parts and 6.5 parts of aniline were changed to 4.6 parts of taurine, to obtain 21.9 parts (yield 85%) of Compound A-13.
[実施例14]
(キノフタロン化合物A−14の製造)
中間体9の合成反応において、中間体8 10部を中間体14 15部、テトラクロロ無水フタル酸11.0部を無水フタル酸13.5部、ジメチルプロピルアミン7.5部を9.7部に変更した以外は同様に反応を行い、中間体15を19.14部(収率94%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体15 15.0部、塩化シアヌル10.6部を5.6部、スルファニル酸10.0部をハイドロキノン一硫酸カリウム7.0部、アニリン6.5部を4-フェニルフェノール6.2部に変更した以外は同様に反応を行い、化合物A−14を12.7部(収率45%)得た。
[Example 14]
(Production of quinophthalone compound A-14)
In the synthetic reaction of Intermediate 9, 10 parts of Intermediate 8 were added, 15 parts of Intermediate 14 were added, 11.0 parts of tetrachlorophthalic anhydride were added with 13.5 parts of phthalic anhydride, and 7.5 parts of dimethylpropylamine were added with 9.7 parts. The same reaction was carried out except that the above was changed to 19.14 parts (yield 94%) of Intermediate 15.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was intermediated with 15.0 parts of Intermediate 15, 10.6 parts of cyanuric chloride was 5.6 parts, and 10.0 parts of sulfanilic acid was hydroquinone potassium monosulfate. The same reaction was performed except that 0 parts and 6.5 parts of aniline were changed to 6.2 parts of 4-phenylphenol to obtain 12.7 parts (yield 45%) of Compound A-14.
[実施例15]
(キノフタロン化合物A−15の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体9 15.0部、塩化シアヌル10.6部を4.8部、スルファニル酸10.0部を5−アミノサリチル酸4.0部、アニリン6.5部を硫酸水素2-アミノエチル4.4部に変更した以外は同様に反応を行い、化合物A−15を12.8部(収率52%)得た。
[Example 15]
(Production of quinophthalone compound A-15)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was used as 15.0 parts of Intermediate 9, 10.6 parts of cyanuric chloride as 4.8 parts, and 10.0 parts of sulfanilic acid as 5-aminosalicylic acid. 12.8 parts (yield 52%) of Compound A-15 was obtained by performing the same reaction except that 0 parts and 6.5 parts of aniline were changed to 4.4 parts of 2-aminoethyl hydrogen sulfate.
[実施例16]
(キノフタロン化合物A−16の製造)
中間体1の合成反応において、8−アミノキナルジン10部を中間体16 10部に、無水フタル酸20.6部を4,5−ジブロモフタル酸無水物21.9部、ジメチルプロピルアミン14.9部を7.7部に変更した以外は同様に反応を行い、中間体17を17.0部(収率88%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体17 17.0部、塩化シアヌル10.6部を5.3部、スルファニル酸10.0部を5.0部、アニリン6.5部を5−アミノ−2−メチルベンゾトリフルオリド6部に変更した以外は同様に反応を行い、化合物A−16を22.5部(収率77%)得た。
[Example 16]
(Production of quinophthalone compound A-16)
In the synthesis reaction of Intermediate 1, 10 parts of 8-aminoquinaldine was added to 10 parts of Intermediate 16, 20.6 parts of phthalic anhydride was added to 21.9 parts of 4,5-dibromophthalic anhydride, and dimethylpropylamine was added to 14. The same reaction was performed except that 9 parts was changed to 7.7 parts, and 17.0 parts (yield 88%) of Intermediate 17 was obtained.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted into 17.0 parts of Intermediate 17, 5.3 parts of 10.6 parts of cyanuric chloride, 5.0 parts of 10.0 parts of sulfanilic acid and aniline. The same reaction was performed except that 6.5 parts was changed to 6 parts of 5-amino-2-methylbenzotrifluoride to obtain 22.5 parts (yield 77%) of compound A-16.
[実施例17]
(キノフタロン化合物A−17の製造)
中間体1の合成反応において、8−アミノキナルジン10部を中間体18 10部に、無水フタル酸20.6部を2,3−ナフタレンジカルボン酸無水物13.5部、ジメチルプロピルアミン14.9部を7.3部に変更した以外は同様に反応を行い、中間体19を12.6部(収率81%)得た。
化合物A−2の合成反応において、中間体2 19.5部をA−19 12.6部、塩化シアヌル10.6部を4.6部、スルファニル酸10.0部を4.4部、アニリン6.5部を2−ペンテン−1−オール2.6部に変更した以外は同様に反応を行い、化合物A−17を13.5部(収率64%)得た。
[Example 17]
(Production of quinophthalone compound A-17)
In the synthesis reaction of Intermediate 1, 10 parts of 8-aminoquinaldine was added to 10 parts of Intermediate 18, 20.6 parts of phthalic anhydride was added to 13.5 parts of 2,3-naphthalenedicarboxylic acid anhydride, and dimethylpropylamine was added to 14. The same reaction was performed except that 9 parts was changed to 7.3 parts, and 12.6 parts (yield 81%) of Intermediate 19 was obtained.
In the synthesis reaction of compound A-2, 19.5 parts of Intermediate 2 was 12.6 parts of A-19, 4.6 parts of 10.6 parts of cyanuric chloride, 4.4 parts of 10.0 parts of sulfanilic acid, and aniline. The same reaction was performed except that 6.5 parts was changed to 2.6 parts of 2-penten-1-ol to obtain 13.5 parts (yield 64%) of compound A-17.
[実施例18]
(キノフタロン化合物A−18の製造)
中間体6の合成反応において、6−ニトロ−8−ヒドロキシキナルジン10部を8−ヒドロキシキナルジン5部、無水フタル酸8.7部をテトラクロロフタル酸無水物10.8部に変更した以外は同様に反応を行い、中間体20を12.8部(収率95%)得た。
中間体8の合成反応において、8−アミノキナルジン10部を中間体20 12.8部、メタノール100部をN−メチルピロリドン640部、炭酸ナトリウム5部を1,8−ジアザビシクロ[5,4,0]−7−ウンデセン5.5部、4−アセタミドベンゼンスルホニルクロライド17.7部を8.8部、水70部を0部、35%塩酸20部を190部に変更した以外は同様に反応を行い、中間体21を16.1部(収率85%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体21 16.1部、塩化シアヌル9.9部を5.1部、スルファニル酸20.5部を5−アミノサリチル酸9.3部に変更した以外は同様に反応を行い、化合物A−18を21.6部(収率81%)得た。
[Example 18]
(Production of quinophthalone compound A-18)
In the synthetic reaction of Intermediate 6, except that 10 parts of 6-nitro-8-hydroxyquinaldine was changed to 5 parts of 8-hydroxyquinaldine and 8.7 parts of phthalic anhydride was changed to 10.8 parts of tetrachlorophthalic anhydride. Was subjected to the same reaction to obtain 12.8 parts (yield 95%) of Intermediate 20.
In the synthesis reaction of Intermediate 8, 10 parts of 8-aminoquinaldine was 12.8 parts of Intermediate 20, 100 parts of methanol was 640 parts of N-methylpyrrolidone, and 5 parts of sodium carbonate was 1,8-diazabicyclo[5,4,4]. 0]-7-undecene 5.5 parts, 4-acetamidobenzenesulfonyl chloride 18.7 parts 8.8 parts, water 70 parts 0 parts, 35% hydrochloric acid 20 parts 190 parts To give 16.1 parts (yield 85%) of intermediate 21.
In the synthetic reaction of Compound A-1, 15.5 parts of Intermediate 1 was 16.1 parts of Intermediate 21, 5.1 parts of 9.9 parts of cyanuric chloride, and 20.5 parts of sulfanilic acid were added to 9.15 of 5-aminosalicylic acid. The same reaction was performed except that the amount was changed to 3 parts to obtain 21.6 parts (yield 81%) of compound A-18.
[実施例19]
(キノフタロン化合物A−19の製造)
中間体21の合成反応において、中間体20 12.8部を中間体22 9.7部に変更した以外は同様に反応を行い、中間体23を14.2部(収率88%)得た。
化合物2の合成反応において、中間体2 19.5部を中間体23 14.2部、塩化シアヌル10.6部を4.9部、スルファニル酸10.0部を4−ヒドロキシベンゼンスルホン酸ナトリウム5.3部、アニリン6.5部をフェノール3.1部に変更した以外は同様に反応を行い、化合物A−19を13.5部(収率64%)得た。
[Example 19]
(Production of quinophthalone compound A-19)
In the synthesis reaction of the intermediate 21, the same reaction was performed except that 12.8 parts of the intermediate 20 was changed to 9.7 parts of the intermediate 22 to obtain 14.2 parts (yield 88%) of the intermediate 23. ..
In the synthetic reaction of compound 2, 19.5 parts of Intermediate 2 was 14.2 parts of Intermediate 23, 10.6 parts of cyanuric chloride was 4.9 parts, and 10.0 parts of sulfanilic acid was sodium 4-hydroxybenzenesulfonate. 13.5 parts (yield 64%) of compound A-19 was obtained in the same manner as above except that 3.1 parts of phenol and 3.1 parts of aniline were changed to 3.1 parts.
[実施例20]
(キノフタロン化合物A−20の製造)
中間体21の合成反応において、中間体20 12.8部を中間体7 9.7部に変更した以外は同様に反応を行い、中間体24を14.2部(収率88%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体24 14.2部、塩化シアヌル10.6部を4.9部、スルファニル酸10.0部を4−ヒドロキシベンゼンスルホン酸ナトリウム5.3部、アニリン6.5部をフェノール3.1部に変更した以外は同様に反応を行い、化合物A−20を13.5部(収率64%)得た。
[Example 20]
(Production of quinophthalone compound A-20)
In the synthesis reaction of intermediate 21, the same reaction was performed except that 12.8 parts of intermediate 20 was changed to 9.7 parts of intermediate 7 to obtain 14.2 parts of intermediate 24 (yield 88%). ..
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was 14.2 parts of Intermediate 24, 4.9 parts of 10.6 parts of cyanuric chloride, and 10.0 parts of sulfanilic acid were added to 4-hydroxybenzenesulfonic acid. 13.5 parts (yield 64%) of compound A-20 was obtained by performing the same reaction except that 5.3 parts of sodium and 6.5 parts of aniline were changed to 3.1 parts of phenol.
[実施例21]
(キノフタロン化合物A−21の製造)
塩化シアヌル5.6部、アセトン250部を加え、氷浴下で冷却しながら撹拌した。そこへ中間体23 15部をN−メチルピロリドン1000部に溶解させ、塩化シアヌルの溶液に1時間かけて滴下した。5℃〜15℃の間で3時間撹拌した後にS酸7.3部加え、50℃に加熱し、3時間撹拌を行った。室温まで冷却後、反応混合物を水3000部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらに水、メタノールで洗浄を行い、減圧下で乾燥させ、化合物A−21を21.3(収率83%)得た。
[Example 21]
(Production of quinophthalone compound A-21)
5.6 parts of cyanuric chloride and 250 parts of acetone were added, and the mixture was stirred while cooling in an ice bath. Then, 15 parts of Intermediate 23 was dissolved in 1000 parts of N-methylpyrrolidone, and the solution was added dropwise to a solution of cyanuric chloride over 1 hour. After stirring for 3 hours between 5°C and 15°C, 7.3 parts of S acid was added, and the mixture was heated to 50°C and stirred for 3 hours. After cooling to room temperature, the reaction mixture was poured into 3000 parts of water and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with water and methanol, and dried under reduced pressure to give compound A-21 (21.3, yield 83%).
[実施例22]
(キノフタロン化合物A−22の製造)
中間体6の合成反応において、6−ニトロ−8−ヒドロキシキナルジン10部を8−ヒドロキシキナルジン5部、無水フタル酸8.7部をテトラフルオロフタル酸無水物8.3部に変更した以外は同様に反応を行い、中間体25を11部(収率97%)得た。
中間体21の合成反応において、中間体20 12.8部を中間体25 11部に変更した以外は同様に反応を行い、中間体26を14.8部(収率91%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体26 14.8部、塩化シアヌル10.6部を5.3部、スルファニル酸10.0部を4−アミノ安息香酸3.9部、アニリン6.5部を2,4−ジブロモアニリン8.6部に変更した以外は同様に反応を行い、化合物A−22を22.7部(収率81%)得た。
[Example 22]
(Production of quinophthalone compound A-22)
In the synthetic reaction of Intermediate 6, except that 10 parts of 6-nitro-8-hydroxyquinaldine was changed to 5 parts of 8-hydroxyquinaldine and 8.7 parts of phthalic anhydride was changed to 8.3 parts of tetrafluorophthalic anhydride. Was similarly reacted to obtain 11 parts of Intermediate 25 (yield 97%).
In the synthetic reaction of Intermediate 21, the same reaction was performed except that 12.8 parts of Intermediate 20 was changed to 11 parts of Intermediate 25, and 14.8 parts (Yield 91%) of Intermediate 26 was obtained.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was converted to 14.8 parts of Intermediate 26, 5.3 parts of 10.6 parts of cyanuric chloride, 10.0 parts of sulfanilic acid and 3 parts of 4-aminobenzoic acid. The same reaction was performed except that 2.9 parts and aniline 6.5 parts were changed to 2,4-dibromoaniline 8.6 parts to obtain 22.7 parts (yield 81%) of compound A-22.
[実施例23]
(キノフタロン化合物A−23の製造)
化合物A−2の合成反応において、中間体2 19.5部をA−21 16.1部、塩化シアヌル10.6部を5.1部、スルファニル酸10.0部を硫酸水素2−アミノエチル3.9部、アニリン6.5部を3.1部に変更した以外は同様に反応を行い、化合物A−23を21.0部(収率85%)得た。
[Example 23]
(Production of quinophthalone compound A-23)
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was A-1 16.1 parts, 10.6 parts of cyanuric chloride was 5.1 parts, and 10.0 parts of sulfanilic acid was 2-aminoethyl hydrogen sulfate. The same reaction was carried out except that 3.9 parts and 6.5 parts of aniline were changed to 3.1 parts to obtain 21.0 parts (yield 85%) of Compound A-23.
[実施例24]
(キノフタロン化合物A−24の製造)
化合物A−2の中間体2 19.5部を中間体27 16.4部、塩化シアヌル10.6部を5.5部、スルファニル酸10.0部を5.1部、アニリン6.5部をアリルアミン2.2部に変更した以外は同様に反応を行い、化合物A−24を17.1部(収率68%)得た。
[Example 24]
(Production of quinophthalone compound A-24)
Intermediate 2 19.5 parts of compound A-2, intermediate 27 16.4 parts, cyanuric chloride 10.6 parts 5.5 parts, sulfanilic acid 10.0 parts 5.1 parts, aniline 6.5 parts Was reacted in the same manner except that the allylamine was changed to 2.2 parts to obtain 17.1 parts (yield 68%) of Compound A-24.
[実施例25]
(キノフタロン化合物A−25の製造)
化合物A−2の合成反応において、中間体2 19.5部を中間体28 15部、塩化シアヌル10.6部を5.7部、スルファニル酸10.0部を4−プロピオン酸アニリン5.6部、アニリン6.5部を3.4部に変更した以外は同様に反応を行い、化合物A−25を21.2部(収率83%)得た。
[Example 25]
(Production of quinophthalone compound A-25)
In the synthesis reaction of compound A-2, 19.5 parts of Intermediate 2 was 15 parts of Intermediate 28, 10.6 parts of cyanuric chloride was 5.7 parts, and 10.0 parts of sulfanilic acid was aniline 4-propionate 5.6. And 6.5 parts of aniline were changed to 3.4 parts to carry out the same reaction to obtain 21.2 parts of compound A-25 (yield 83%).
[実施例26]
(キノフタロン化合物A−26の製造)
中間体1の合成反応において、無水フタル酸20.6部をテトラクロロフタル酸無水物39.8部に変更した以外は同様に反応を行い、中間体29を24.8部(収率92%)得た。
中間体29 24.8部、N−メチルピロリドン1860部、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン9.7部加え、120℃に加熱攪拌した。そこへ3−ブロモプロピルアミン臭化水素酸塩16.6部加え、4時間加熱攪拌を行った。室温まで冷却後、反応混合物をメタノール4000部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、減圧下で乾燥させ、中間体30を13.1部(収率43%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体30 13.1部、塩化シアヌル9.9部を5.0部、スルファニル酸20.5部を10.4部に変更した以外は同様に反応を行い、化合物A−26を21.9部(収率89%)得た。
[Example 26]
(Production of quinophthalone compound A-26)
In the synthesis reaction of Intermediate 1, the same reaction was performed except that 20.6 parts of phthalic anhydride was changed to 39.8 parts of tetrachlorophthalic anhydride, and 24.8 parts of Intermediate 29 (yield 92% )Obtained.
Intermediate 29 (24.8 parts), N-methylpyrrolidone (1860 parts) and 1,8-diazabicyclo[5,4,0]-7-undecene (9.7 parts) were added, and the mixture was heated with stirring at 120°C. 16.6 parts of 3-bromopropylamine hydrobromide was added thereto, and the mixture was heated and stirred for 4 hours. After cooling to room temperature, the reaction mixture was put into 4000 parts of methanol and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with methanol, and dried under reduced pressure to obtain 13.1 parts of Intermediate 30 (yield 43%).
In the synthetic reaction of compound A-1, 15.5 parts of Intermediate 1 was changed to 13.1 parts of Intermediate 30, 9.9 parts of cyanuric chloride was changed to 5.0 parts, and 20.5 parts of sulfanilic acid was changed to 10.4 parts. The same reaction was performed except that the above was performed to obtain 21.9 parts (yield 89%) of Compound A-26.
[実施例27]
(キノフタロン化合物A−27の製造)
中間体31 20.6部、4−アミノシクロヘキサンカルボン酸 8.3部、1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミド10.2部、4−ジメチルアミノピリジン1.2部、N−メチルピロリドン2000部加え、20〜25℃にて8時間攪拌した。反応混合物を水4000部に投入し、室温下にて1時間攪拌した。析出した結晶を濾別した後、さらにメタノールで洗浄を行い、減圧下で乾燥させ、中間体32を16.7部(収率65%)得た。
化合物A−2の合成反応において、中間体2 19.5部を中間体32 16.7部、塩化シアヌル10.6部を5.0部、スルファニル酸10.0部を4.6部、アニリン6.5部を3.0部に変更した以外は同様に反応を行い、化合物A−27を19.4部(収率75%)得た。
[Example 27]
(Production of quinophthalone compound A-27)
Intermediate 31 20.6 parts, 4-aminocyclohexanecarboxylic acid 8.3 parts, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 10.2 parts, 4-dimethylaminopyridine 1.2 parts, N- 2000 parts of methylpyrrolidone was added, and the mixture was stirred at 20 to 25°C for 8 hours. The reaction mixture was poured into 4000 parts of water and stirred at room temperature for 1 hour. The precipitated crystals were separated by filtration, washed with methanol, and dried under reduced pressure to obtain 16.7 parts (yield 65%) of intermediate 32.
In the synthetic reaction of compound A-2, 19.5 parts of Intermediate 2 was 16.7 parts of Intermediate 32, 10.6 parts of cyanuric chloride was 5.0 parts, 10.0 parts of sulfanilic acid was 4.6 parts, and aniline. The same reaction was performed except that 6.5 parts was changed to 3.0 parts to obtain 19.4 parts (yield 75%) of Compound A-27.
[実施例28]
(キノフタロン化合物A−28の製造)
中間体32の合成反応において、中間体31 20.6部を中間体33 15.5部、4−アミノシクロヘキサンカルボン酸 8.3部を6−アミノピコリン酸5.2部、1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミド10.2部を6.6部、4−ジメチルアミノピリジン1.2部を0.8部に変更した以外は同様に反応を行い、中間体34を13.3部(収率70%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体34 13.3部、塩化シアヌル9.9部を4.1部、スルファニル酸20.5部を8.5部に変更した以外は同様に反応を行い、化合物A−28を15.1部(収率67%)得た。
[Example 28]
(Production of quinophthalone compound A-28)
In the synthesis reaction of the intermediate 32, 20.6 parts of the intermediate 31 was added to 15.5 parts of the intermediate 33, 8.3 parts of 4-aminocyclohexanecarboxylic acid was added to 5.2 parts of 6-aminopicolinic acid, and 1-(3- Dimethylaminopropyl)-3-ethylcarbodiimide 10.2 parts were changed to 6.6 parts and 4-dimethylaminopyridine 1.2 parts were changed to 0.8 parts, and the same reaction was performed, and intermediate 34 was added to 13. 3 parts (yield 70%) were obtained.
In the synthetic reaction of compound A-1, 15.5 parts of Intermediate 1 was changed to 13.3 parts of Intermediate 34, 9.9 parts of cyanuric chloride was changed to 4.1 parts, and 20.5 parts of sulfanilic acid was changed to 8.5 parts. The same reaction was performed except that the above was performed to obtain 15.1 parts (yield 67%) of Compound A-28.
[実施例29]
(キノフタロン化合物A−29の製造)
中間体30の合成反応において、中間体29 24.8部を中間体35 14.2部、N−メチルピロリドン1860部を500部、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン9.7部を9.0部、3−ブロモプロピルアミン臭化水素酸塩16.6部をトリエチレングリコールモノクロロヒドリン12.4部に変更した以外は同様に反応を行い、中間体36を18.0部(収率87%)得た。
化合物A−2の中間体2 19.5部を中間体36 18.0部、塩化シアヌル10.6部を7.9部、スルファニル酸10.0部を7.4部、アニリン6.5部を4−アミノ安息香酸7.0部に変更した以外は同様に反応を行い、化合物A−29を24.5部(収率71%)得た。
Example 29
(Production of quinophthalone compound A-29)
In the synthesis reaction of the intermediate 30, 24.8 parts of the intermediate 29, 14.2 parts of the intermediate 35, 1860 parts of 1860 parts of N-methylpyrrolidone, 1,8-diazabicyclo[5,4,0]-7-undecene. Intermediate 36 was reacted in the same manner except that 9.7 parts was changed to 9.0 parts and 3-bromopropylamine hydrobromide 16.6 parts was changed to 12.4 parts of triethylene glycol monochlorohydrin. 18.0 parts (yield 87%) were obtained.
Intermediate 2 of Compound A-2 19.5 parts, Intermediate 36 18.0 parts, cyanuric chloride 10.6 parts 7.9 parts, sulfanilic acid 10.0 parts 7.4 parts, aniline 6.5 parts. Was changed to 7.0 parts of 4-aminobenzoic acid, and the same reaction was performed to obtain 24.5 parts (yield 71%) of compound A-29.
[実施例30]
(キノフタロン化合物A−30の製造)
中間体21の合成反応において、中間体20 12.8部を中間体17 10部、N−メチルピロリドン640部を500部、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン5.5部を4.3部、4−アセタミドベンゼンスルホニルクロライド17.7部を2,5−ジクロロ−4−アセタミドベンゼンスルホニルクロライド8.5部、35%塩酸190部を150部に変更した以外は同様に反応を行い、中間体37を13.7部(収率90%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体21 13.7部、塩化シアヌル9.9部を3.9部、スルファニル酸20.5部を4−アミノサリチル酸7.1部に変更した以外は同様に反応を行い、化合物A−30を18.3部(収率83%)得た。
[Example 30]
(Production of quinophthalone compound A-30)
In the synthetic reaction of the intermediate 21, 12.8 parts of the intermediate 20, 10 parts of the intermediate 17, 500 parts of 640 parts of N-methylpyrrolidone, 1,8-diazabicyclo[5,4,0]-7-undecene5. 5 parts to 4.3 parts, 4-acetamidobenzenesulfonyl chloride 17.7 parts to 2,5-dichloro-4-acetamidobenzenesulfonyl chloride 8.5 parts, 35% hydrochloric acid 190 parts to 150 parts The reaction was performed in the same manner as above, except that 13.7 parts (yield 90%) of Intermediate 37 was obtained.
In the synthetic reaction of compound A-1, 15.5 parts of Intermediate 1 was 13.7 parts of Intermediate 21, 9.9 parts of cyanuric chloride was 3.9 parts, and 20.5 parts of sulfanilic acid was 4-aminosalicylic acid. The same reaction was performed except that the amount was changed to 1 part, to obtain 18.3 parts (yield 83%) of compound A-30.
[実施例31]
(キノフタロン化合物A−31の製造)
中間体32の合成反応において、中間体31 20.6部を中間体38 10.9部、4−アミノシクロヘキサンカルボン酸 8.3部を2、5−ジヒドロキシ−1,4−ジチアン3.2部、1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミド10.2部を4.0部、4−ジメチルアミノピリジン1.2部を0.5部に変更した以外は同様に反応を行い、中間体39を7.7部(収率56%)得た。
化合物A−1の合成反応において、中間体1 15.5部を中間体39 7.7部、塩化シアヌル9.9部を2.2部、スルファニル酸20.5部を4−アミノ安息香酸3.5部に変更した以外は同様に反応を行い、化合物A−31を8.1部(収率69%)得た。
[Example 31]
(Production of quinophthalone compound A-31)
In the synthetic reaction of the intermediate 32, 20.6 parts of the intermediate 31 was added to 10.9 parts of the intermediate 38, 8.3 parts of 4-aminocyclohexanecarboxylic acid was added to 3.2 parts of 2,5-dihydroxy-1,4-dithiane. , 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 10.2 parts were changed to 4.0 parts and 4-dimethylaminopyridine was changed to 1.2 parts to 0.5 parts to carry out the same reaction, 7.7 parts (yield 56%) of intermediate 39 was obtained.
In the synthetic reaction of compound A-1, 15.5 parts of Intermediate 1 was added to 7.7 parts of Intermediate 39, 2.2 parts of 9.9 parts of cyanuric chloride, 20.5 parts of sulfanilic acid and 3 parts of 4-aminobenzoic acid. The same reaction was performed except that the amount was changed to 0.5 part to obtain 8.1 parts (yield 69%) of Compound A-31.
[実施例32]
(キノフタロン化合物A−32の製造)
中間体30の合成反応において、中間体29 24.8部を中間体22 5部、N−メチルピロリドン1860部を250部、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン9.7部を2.7部、3−ブロモプロピルアミン臭化水素酸塩16.6部を中間体40、41の混合体5.5部に変更した以外は同様に反応を行い、中間体42を7.4部(収率91%)得た。
化合物A−2の中間体2 19.5部を中間体42 7.4部、塩化シアヌル10.6部を2.5部、スルファニル酸10.0部を2.4部、アニリン6.5部を水10部に変更した以外は同様に反応を行い、化合物A−32を7.9部(収率72%)得た。
[Example 32]
(Production of quinophthalone compound A-32)
In the synthetic reaction of Intermediate 30, 24.8 parts of Intermediate 29, 250 parts of Intermediate 225, 250 parts of 1860 parts of N-methylpyrrolidone, 1,8-diazabicyclo[5,4,0]-7-undecene9. The same reaction was carried out except that 7 parts were changed to 2.7 parts, and 3-bromopropylamine hydrobromide 16.6 parts was changed to 5.5 parts of a mixture of intermediates 40 and 41. 7.4 parts (yield 91%) were obtained.
Intermediate 2 19.5 parts of compound A-2, intermediate 42 7.4 parts, cyanuric chloride 10.6 parts 2.5 parts, sulfanilic acid 10.0 parts 2.4 parts, aniline 6.5 parts Was reacted in the same manner except that 10 parts of water was used to obtain 7.9 parts (yield 72%) of Compound A-32.
キノフタロン化合物(A−1〜A−32)において、質量分析を行った結果を表1に示す。また、理論値は測定の性質上、化合物のHが脱離するため、計算値の質量数より−1となる。 Table 1 shows the results of mass spectrometry of the quinophthalone compounds (A-1 to A-32). In addition, the theoretical value is −1 from the calculated mass number because H of the compound is desorbed due to the nature of measurement.
<比較キノフタロン化合物の製造方法>
本発明の参考例では、実施例1〜32で製造したキノフタロン化合物に加え、比較例として、以下の製造方法により製造したキノフタロン化合物を使用した。
<Method for producing comparative quinophthalone compound>
In the reference example of the present invention, in addition to the quinophthalone compounds produced in Examples 1 to 32, a quinophthalone compound produced by the following production method was used as a comparative example.
(キノフタロン化合物(D−1)の製造)
特許第4585781号公報に記載の合成方法に従い、キノフタロン化合物(D−1)を得た。
(Production of quinophthalone compound (D-1))
A quinophthalone compound (D-1) was obtained according to the synthetic method described in Japanese Patent No. 4585781.
キノフタロン化合物(D−1)
(キノフタロン化合物(D−2)の製造)
特許4871634号に記載の合成方法に従い、キノフタロン化合物(D−2)を得た。
(Production of quinophthalone compound (D-2))
A quinophthalone compound (D-2) was obtained according to the synthetic method described in Japanese Patent No. 4871634.
キノフタロン化合物(D−2)
(キノフタロン化合物(D−3)の製造)
特開2014−199308号公報に記載の合成方法に従い、キノフタロン化合物(D−3)を得た。
(Production of quinophthalone compound (D-3))
A quinophthalone compound (D-3) was obtained according to the synthetic method described in JP-A-2014-199308.
キノフタロン化合物(D−3)
<黄色顔料[B]の製造方法>
(微細化黄色顔料(B−1)の製造)
キノフタロン系黄色顔料C.I.ピグメント イエロー138(BASF社製「Paliotol Yellow L 0962HD」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8リットルの温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、微細化黄色顔料(B−1)を得た。
<Production method of yellow pigment [B]>
(Production of micronized yellow pigment (B-1))
Quinophthalone yellow pigment C.I. I. Pigment Yellow 138 (“Paliotol Yellow L 0962HD” manufactured by BASF), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8 liters of warm water, stirred for 2 hours while heating to 80° C. to form a slurry, filtered, washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. A fine yellow pigment (B-1) was obtained.
(微細化黄色顔料(B−2)の製造)
イソインドリン系黄色顔料C.I.ピグメント イエロー 139(BASF社製「Paliotol Yellow L 2146HD」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8リットルの温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、微細化黄色顔料(B−2)を得た。
(Production of micronized yellow pigment (B-2))
Isoindoline yellow pigment C.I. I. Pigment Yellow 139 (“Palotoll Yellow L 2146HD” manufactured by BASF), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8 liters of warm water, stirred for 2 hours while heating to 80° C. to form a slurry, filtered, washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. A fine yellow pigment (B-2) was obtained.
(微細化黄色顔料(B−3)の製造)
特許第5267696号に記載の合成方法に従い、下記キノフタロン化合物(化53)を得た。前記着色剤(A−1)で使用したC.I.ピグメント イエロー138を、下記式(化53)のキノフタロン系顔料に変更した以外は、黄色顔料(B−1)と同様にして、着色剤(B−3)を得た。
(Production of micronized yellow pigment (B-3))
The following quinophthalone compound (Chemical Formula 53) was obtained according to the synthetic method described in Japanese Patent No. 5267696. The C.I. used in the colorant (A-1). I. Pigment Yellow 138 was changed to a quinophthalone-based pigment represented by the following formula (Formula 53) to obtain a colorant (B-3) in the same manner as in the yellow pigment (B-1).
<フタロシアニン顔料[C]の製造方法>
(微細化フタロシアニン顔料(C−1)の製造)
フタロシアニン系緑色顔料C.I.ピグメント グリーン58(DIC社製「FASTOGEN GREEN A110」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、微細化フタロシアニン顔料(C−1)を得た。
<Method for producing phthalocyanine pigment [C]>
(Production of micronized phthalocyanine pigment (C-1))
Phthalocyanine green pigment C.I. I. Pigment Green 58 (“FASTOGEN GREEN A110” manufactured by DIC), 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating at 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. A fine phthalocyanine pigment (C-1) was obtained.
(微細化フタロシアニン顔料(C−2)の製造)
98%硫酸500部、クロロアルミニウムフタロシアニン(P−1)50部、1,2−ジブロモ−5,5−ジメチルヒダントイン(DBDMH)129.3部を加え撹拌し、20℃、6時間、反応させた。その後、3℃の氷水5000部に上記反応混合物を注入し、析出した固体をろ取し、水洗した。ビーカーに2.5%水酸化ナトリウム水溶液500部、ろ取した残渣を加え、80℃、1時間撹拌した。その後、この混合物をろ取、水洗、乾燥して、フタロシアニン顔料(P−2)を57.3部(収率40%、ハロゲン原子置換数10.1、ハロゲン分布幅9)得た。
3口フラスコに、N−メチルピロリドンを500部、P−2を50部及びリン酸ジフェニル13.9部を加え、90℃に加熱し、8時間反応させた。これを室温まで冷却後、生成物をろ過し、メタノールで洗浄後、乾燥させて、フタロシアニン顔料(C−2)を51.6部(収率88%、ハロゲン原子置換数10.1、ハロゲン分布幅9)得た。
(Production of micronized phthalocyanine pigment (C-2))
500 parts of 98% sulfuric acid, 50 parts of chloroaluminum phthalocyanine (P-1), 129.3 parts of 1,2-dibromo-5,5-dimethylhydantoin (DBDMH) were added and stirred, and reacted at 20° C. for 6 hours. .. Then, the above reaction mixture was poured into 5000 parts of 3° C. ice water, and the precipitated solid was collected by filtration and washed with water. To a beaker, 500 parts of 2.5% aqueous sodium hydroxide solution and the residue collected by filtration were added, and the mixture was stirred at 80° C. for 1 hour. Then, this mixture was collected by filtration, washed with water, and dried to obtain 57.3 parts of phthalocyanine pigment (P-2) (yield 40%, halogen atom substitution number 10.1, halogen distribution width 9).
To a three-necked flask, 500 parts of N-methylpyrrolidone, 50 parts of P-2 and 13.9 parts of diphenyl phosphate were added, heated to 90° C. and reacted for 8 hours. After cooling this to room temperature, the product was filtered, washed with methanol and dried to give 51.6 parts of phthalocyanine pigment (C-2) (yield 88%, halogen atom substitution number 10.1, halogen distribution). Width 9) obtained.
<その他・微細化顔料の製造方法>
(微細化赤色顔料(PR254−1)の製造)
ジケトピロロピロール顔料C.I.ピグメント レッド254(BASF社製「B−CF」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、190部の微細化ジケトピロロピロール顔料(PR254−1)を得た。
<Others/Method for producing finely divided pigment>
(Production of micronized red pigment (PR254-1))
Diketopyrrolopyrrole pigment C.I. I. Pigment Red 254 (“B-CF” manufactured by BASF) (200 parts), sodium chloride (1400 parts), and diethylene glycol (360 parts) were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating at 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. , 190 parts of micronized diketopyrrolopyrrole pigment (PR254-1) was obtained.
(微細化赤色顔料(PR177−1)の製造)
アントラキノン系赤色顔料C.I.ピグメント レッド177(BASF社製「パリオゲンレッド L4039」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、アントラキノン系の微細化赤色顔料(PR177−1)を得た。
(Production of micronized red pigment (PR177-1))
Anthraquinone red pigment C.I. I. Pigment Red 177 (“Pariogen Red L4039” manufactured by BASF), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating at 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. , Anthraquinone-based micronized red pigment (PR177-1) was obtained.
(微細化青色顔料(PB15:6−1)の製造)
フタロシアニン系青色顔料C.I.ピグメント ブルー15:6(トーヨーカラー社製「LIONOL BLUE ES」、比表面積60m2/g)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、微細化青色顔料(PB15:6−1)を得た。
(Production of micronized blue pigment (PB15:6-1))
Phthalocyanine-based blue pigment C.I. I. Pigment Blue 15:6 (TOYOCOLOR "LIONOL BLUE ES", specific surface area 60 m 2 /g) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho), Kneading was carried out at 80° C. for 6 hours. Next, this kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating at 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. Thus, a finely divided blue pigment (PB15:6-1) was obtained.
(微細化紫色顔料(PV23−1)の製造)
ジオキサジン系紫色顔料C.I.ピグメント バイオレット23(トーヨーカラー社製「LIONOGEN VIOLET RL」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、紫色微細化紫色顔料(PV23−1)を得た。
(Production of micronized purple pigment (PV23-1))
Dioxazine-based purple pigment C.I. I. Pigment Violet 23 (“LIONOGEN VIOLET RL” manufactured by Toyo Color Co., Ltd.) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was poured into 8000 parts of warm water, stirred for 2 hours while heating at 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. overnight. A purple finely divided purple pigment (PV23-1) was obtained.
<その他顔料分散体の製造方法>
(フタロシアニン・顔料分散体(FP−1))
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM−250 MKII」)で3時間分散した後、孔径5.0μmのフィルタで濾過し、不揮発成分が20質量%の顔料分散体(FP−1)を作製した。
フタロシアニン顔料(C−1) :11.0部
アクリル樹脂溶液1 :17.5部
プロピレングリコールモノメチルエーテルアセテート :66.5部
樹脂型分散剤溶液2 : 5.0部
<Other method for producing pigment dispersion>
(Phthalocyanine/pigment dispersion (FP-1))
After the following mixture was stirred and mixed so as to be uniform, it was dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) for 3 hours using zirconia beads having a diameter of 0.5 mm, and then the pore size was 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (FP-1) having a nonvolatile content of 20% by mass.
Phthalocyanine pigment (C-1): 11.0 parts Acrylic resin solution 1: 17.5 parts Propylene glycol monomethyl ether acetate: 66.5 parts Resin type dispersant solution 2: 5.0 parts
(フタロシアニン・顔料分散体(FP−2))
フタロシアニン顔料(C−1)を(C−2)に変更した以外は、FP−1と同様の方法で顔料分散体(FP−2)を作製した。
(Phthalocyanine/pigment dispersion (FP-2))
A pigment dispersion (FP-2) was produced in the same manner as in FP-1, except that the phthalocyanine pigment (C-1) was changed to (C-2).
(PR254・顔料分散体(RP−1))
フタロシアニン顔料(C−1)をPR254−1に変更した以外は、FP−1と同様の方法でPR254・顔料分散体(RP−1)を作製した。
(PR254/Pigment dispersion (RP-1))
PR254/pigment dispersion (RP-1) was prepared in the same manner as FP-1, except that the phthalocyanine pigment (C-1) was changed to PR254-1.
(PR177・顔料分散体(RP−2))
フタロシアニン顔料(C−1)をPR177−1に変更した以外は、FP−1と同様の方法でPR177・顔料分散体(RP−2)を作製した。
(PR177/Pigment dispersion (RP-2))
A PR177/pigment dispersion (RP-2) was produced in the same manner as in FP-1, except that the phthalocyanine pigment (C-1) was changed to PR177-1.
(PB15:6・顔料分散体(BP−1))
フタロシアニン顔料(C−1)をPB15:6−1に変更した以外は、FP−1と同様の方法でPB15:6・顔料分散体(BP−1)を作製した。
(PB15:6 pigment dispersion (BP-1))
PB15:6.pigment dispersion (BP-1) was produced in the same manner as FP-1, except that the phthalocyanine pigment (C-1) was changed to PB15:6-1.
(PV23・顔料分散体(VP−1))
フタロシアニン顔料(C−1)をPV23−1に変更した以外は、FP−1と同様の方法でPV23・顔料分散体(VP−1)を作製した。
(PV23/pigment dispersion (VP-1))
PV23/pigment dispersion (VP-1) was produced in the same manner as in FP-1, except that the phthalocyanine pigment (C-1) was changed to PV23-1.
<黄色顔料分散体(着色組成物)の製造>
[実施例33]
(顔料分散体(YP−1))
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM−250 MKII」)で3時間分散した後、孔径5.0μmのフィルタで濾過し、不揮発成分が20質量%の顔料分散体(YP−1)を作製した。
キノフタロン化合物(A−1) : 1.8部
黄色顔料(B−1) :10.2部
アクリル樹脂溶液1 :10.5部
プロピレングリコールモノメチルエーテルアセテート :70.0部
樹脂型分散剤1 : 7.5部
<Production of yellow pigment dispersion (coloring composition)>
[Example 33]
(Pigment dispersion (YP-1))
After the following mixture was stirred and mixed so as to be uniform, it was dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) for 3 hours using zirconia beads having a diameter of 0.5 mm, and then the pore size was 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (YP-1) having a nonvolatile content of 20% by mass.
Quinophthalone compound (A-1): 1.8 parts Yellow pigment (B-1): 10.2 parts Acrylic resin solution 1: 10.5 parts Propylene glycol monomethyl ether acetate: 70.0 parts Resin type dispersant 1: 7 .5 copies
[実施例34〜72、比較例1〜5]
(顔料分散体(YP−2〜45))
キノフタロン化合物と、黄色顔料とを、表2に示す種類に変更した以外は、それぞれ実施例33と同様の方法で、顔料分散体(YP−2〜45)をそれぞれ作製した。
[Examples 34 to 72, Comparative Examples 1 to 5]
(Pigment dispersion (YP-2 to 45))
Pigment dispersions (YP-2 to 45) were produced in the same manner as in Example 33 except that the quinophthalone compound and the yellow pigment were changed to the types shown in Table 2.
<黄色顔料分散体(着色組成物)の評価>
得られた顔料分散体について、下記評価を行った。結果を表2に示す。
(コントラスト(CR)の評価)
液晶ディスプレー用バックライトユニットから出た光は、偏光板を通過して偏光され、ガラス基板上に塗布された着色組成物の塗膜を通過し、もう一方の偏光板に到達する。この際、偏光板と偏光板の偏光面が並行であれば、光は偏光板を透過するが、偏光面が直交している場合には光は偏光板により遮断される。しかし、偏光板によって偏光された光が着色組成物の塗膜を通過する際に、着色剤粒子によって散乱等が起こり、偏光面の一部にずれが生じると、偏光板が並行のときは透過する光量が減り、偏光板が直交のときは一部光が透過する。この透過光を偏光板上の輝度として測定し、偏光板が並行の際の輝度と、直交の際の輝度との比を、コントラスト比として算出した。
(コントラスト比)=(並行のときの輝度)/(直交のときの輝度)
従って、塗膜中の着色剤により散乱が起こると、並行のときの輝度が低下し、かつ直交のときの輝度が増加するため、コントラスト比が低くなる。
<Evaluation of yellow pigment dispersion (coloring composition)>
The following evaluation was performed on the obtained pigment dispersion. The results are shown in Table 2.
(Evaluation of contrast (CR))
The light emitted from the backlight unit for liquid crystal display passes through the polarizing plate and is polarized, passes through the coating film of the coloring composition applied on the glass substrate, and reaches the other polarizing plate. At this time, if the polarizing plate and the polarizing plane of the polarizing plate are parallel to each other, light passes through the polarizing plate, but if the polarizing planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to the colorant particles and a part of the plane of polarization is displaced, and the light is transmitted when the polarizing plates are parallel. When the polarizing plate is orthogonal, a part of light is transmitted. The transmitted light was measured as the brightness on the polarizing plate, and the ratio between the brightness when the polarizing plates were parallel and the brightness when the polarizing plates were orthogonal was calculated as the contrast ratio.
(Contrast ratio) = (Brightness when parallel)/(Brightness when orthogonal)
Therefore, when scattering occurs due to the colorant in the coating film, the brightness when parallel is decreased and the brightness when orthogonal is increased, so that the contrast ratio is decreased.
なお、輝度計としては色彩輝度計(トプコン社製「BM−5A」)、偏光板としては偏光板(日東電工社製「NPF−G1220DUN」)を用いた。測定に際しては、測定部分に1cm角の孔を開けた黒色マスクを介して測定した。 A color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate. At the time of measurement, the measurement was performed through a black mask having a 1 cm square hole formed in the measurement portion.
顔料分散体(YP−1〜45)を、100mm×100mm、1.1mm厚のガラス基板上に、スピンコーターを用いて、C光源においてx=0.420になるような塗布基板を得た。乾燥条件は、塗布後60℃で20分、さらに230℃で60分で行った。コントラスト比は、下記基準に従って判定した。
S:9000以上:極めて良好
A:6000以上〜9000未満:良好
B:3000以上〜6000未満:実用可能
C:3000未満:不良
The pigment dispersion (YP-1 to 45) was applied onto a glass substrate having a thickness of 100 mm×100 mm and a thickness of 1.1 mm by using a spin coater to obtain a coated substrate such that x=0.420 at a C light source. Drying conditions were 60° C. for 20 minutes after coating, and 230° C. for 60 minutes. The contrast ratio was judged according to the following criteria.
S: 9000 or more: Very good A: 6000 or more and less than 9000: Good B: 3000 or more and less than 6000: Practical C: Less than 3000: Poor
(耐熱性の評価)
顔料分散体(YP−1〜45)を、100mm×100mm、1.1mm厚のガラス基板上に、スピンコーターを用いて塗布し、次に60℃で20分乾燥し、ついで230℃で30分間加熱、放冷することで塗膜基板を作製した。作製した塗膜基板は、230℃での熱処理後で、1.5μmの膜厚に合うようにした。得られた塗膜のC光源での色度([L*(1)、a*(1)、b*(1)])を顕微分光光度計(オリンパス光学社製「OSP−SP100」)を用いて測定した。さらにその後、耐熱性試験として230℃で60分加熱し、C光源での色度([L*(2)、a*(2)、b*(2)])を測定し、下記計算式により、色差ΔEab*を求めた。
ΔEab* = √((L*(2)- L*(1))2+ (a*(2)- a*(1)) 2+( b*(2)- b*(1)) 2)
S:ΔEab*が3.0未満:極めて良好
A:ΔEab*が3.0以上、4.0未満:良好
B:ΔEab*が4.0以上、6.0未満:実用可能
C:ΔEab*が6.0以上の場合:不良
(Evaluation of heat resistance)
The pigment dispersion (YP-1 to 45) was applied onto a glass substrate having a thickness of 100 mm×100 mm and a thickness of 1.1 mm by using a spin coater, followed by drying at 60° C. for 20 minutes and then at 230° C. for 30 minutes. A coating substrate was prepared by heating and cooling. The manufactured coated substrate was heat-treated at 230° C. so as to have a film thickness of 1.5 μm. The chromaticity ([L*(1), a*(1), b*(1)]) of the obtained coating film with a C light source was measured by a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). It was measured using. After that, as a heat resistance test, it was heated at 230° C. for 60 minutes, and the chromaticity ([L*(2), a*(2), b*(2)]) with a C light source was measured and calculated by the following formula. , And the color difference ΔEab* was determined.
ΔEab* = √((L*(2)- L*(1)) 2 + (a*(2)- a*(1)) 2 +( b*(2)- b*(1)) 2 )
S: ΔEab* is less than 3.0: Very good A: ΔEab* is 3.0 or more and less than 4.0: Good B: ΔEab* is 4.0 or more and less than 6.0: Practical C: ΔEab* is In case of 6.0 or more: bad
(初期粘度の評価)
顔料分散体の粘度は、E型粘度計(東機産業社製「ELD型粘度計」)を用いて、25℃における初期粘度を測定した。
S:10mPa・s未満:極めて良好
A:10mPa・s以上、15mPa・s未満:良好
B:15mPa・s以上、20mPa・s未満:実用可能
C:20mPa・s以上の場合:不良
(Evaluation of initial viscosity)
Regarding the viscosity of the pigment dispersion, the initial viscosity at 25° C. was measured using an E-type viscometer (“ELD-type viscometer” manufactured by Toki Sangyo Co., Ltd.).
S: less than 10 mPa·s: extremely good A: 10 mPa·s or more, less than 15 mPa·s: good B: 15 mPa·s or more, less than 20 mPa·s: practical C: if 20 mPa·s or more: poor
(保存安定性の評価)
得られた顔料分散体について、40℃の恒温機に1週間保存して経時促進させた後、経時後の着色組成物の粘度を前記粘度測定と同じ方法で測定し、40℃で1週間保存した前後の粘度の変化率を計算し、以下の基準により2段階で評価した。
S:粘度変化率が±10%未満で、沈降物を生じなかった場合:極めて良好
A:粘度変化率が±10%以上15%未満で、沈降物を生じなかった場合:良好
B:粘度変化率が±15%以上20%未満で、沈降物を生じなかった場合:実用可能
C:粘度変化率が±20%を超える場合、又は粘度変化率が±20%以内であっても沈降物を生じていた場合:不良
(Evaluation of storage stability)
The obtained pigment dispersion was stored in a thermostat at 40° C. for 1 week to accelerate the aging, and then the viscosity of the coloring composition after aging was measured by the same method as the above-mentioned viscosity measurement, and stored at 40° C. for 1 week The rate of change in viscosity before and after was calculated, and evaluated in two stages according to the following criteria.
S: When the rate of change in viscosity is less than ±10% and no sediment is formed: Very good A: When the rate of change in viscosity is ±10% or more and less than 15% and no sediment is formed: Good B: Change in viscosity When the rate is ±15% or more and less than 20% and no sediment is formed: Practical C: When the rate of viscosity change exceeds ±20%, or when the rate of viscosity change is within ±20%, sediment is generated. If it has occurred: bad
表2に示す通り、本発明のキノフタロン骨格、トリアジン環、酸性基を有するキノフタロン化合物(A)を用いた顔料分散体YP−1〜40は、CR、耐熱性、初期粘度及び保存安定性において良好な評価結果となった。好ましくはキノフタロン化合物A−9、11、14、19〜23、26、30が良好であった。さらに好ましくはキノフタロン化合物A−7、8、10、12、13、15、18、30が最も良好な結果となった。一方、トリアジン環、酸性基を同時に含有しない従来品のキノフタロン化合物D−1〜3の顔料分散体YP−41〜45はCR、耐熱性、初期粘度及び保存安定性において本発明の実施例よりも著しく劣る結果となった。 As shown in Table 2, the pigment dispersions YP-1 to 40 using the quinophthalone compound (A) having a quinophthalone skeleton, a triazine ring and an acidic group of the present invention are good in CR, heat resistance, initial viscosity and storage stability. It was a good evaluation result. Preferably, the quinophthalone compound A-9, 11, 14, 19 to 23, 26, 30 was good. More preferably, the quinophthalone compound A-7,8,10,12,13,15,18,30 gave the best result. On the other hand, the pigment dispersions YP-41 to 45 of the conventional quinophthalone compounds D-1 to D3, which do not contain a triazine ring and an acidic group at the same time, are more excellent in CR, heat resistance, initial viscosity and storage stability than the examples of the present invention. The result was extremely inferior.
<緑色顔料分散体(着色組成物)の作製>
上記黄色顔料分散体(YP−1〜45)とフタロシアニン・顔料分散体(FP−1、2)を用いて緑色着色組成物の作製を行った。
<Preparation of green pigment dispersion (coloring composition)>
A green coloring composition was prepared using the yellow pigment dispersions (YP-1 to 45) and the phthalocyanine/pigment dispersions (FP-1, 2).
[実施例73]
(緑色顔料分散体(GP−1))
下記組成の混合物を均一になるように撹拌混合して、顔料分散体(GP−1)を作製した。
フタロシアニン・顔料分散体(FP−2) :22.2部
黄色顔料分散体(YP−1) :27.8部
Example 73
(Green pigment dispersion (GP-1))
A mixture having the following composition was stirred and mixed so as to be uniform to prepare a pigment dispersion (GP-1).
Phthalocyanine/pigment dispersion (FP-2): 22.2 parts Yellow pigment dispersion (YP-1): 27.8 parts
[実施例74〜124、比較例6〜15]
(緑色顔料分散体(GP−2〜62))
顔料分散体の合計の50部の内訳を、表3に示す種類・質量部にそれぞれ変更した以外は、実施例73と同様にして、それぞれ緑色顔料分散体(GP−1〜62)を得た。
[Examples 74 to 124, Comparative Examples 6 to 15]
(Green pigment dispersion (GP-2 to 62))
Green pigment dispersions (GP-1 to 62) were obtained in the same manner as in Example 73, except that the content of 50 parts in total of the pigment dispersion was changed to the types and parts by mass shown in Table 3. ..
<緑色顔料分散体(着色組成物)の評価>
得られた緑色顔料分散体について、下記評価を行った。また、耐熱性、初期粘度及び保存安定性は、黄色顔料分散体と同様に塗膜を作製し、同様な評価基準で評価を行った。結果を表3に示す。
<Evaluation of green pigment dispersion (coloring composition)>
The following evaluation was performed on the obtained green pigment dispersion. Further, heat resistance, initial viscosity and storage stability were evaluated by the same evaluation criteria by preparing a coating film in the same manner as the yellow pigment dispersion. The results are shown in Table 3.
(コントラストの評価)
顔料分散体(GP−1〜62)を、100mm×100mm、1.1mm厚のガラス基板上に、スピンコーターを用いて、C光源においてx=0.297、y=0.570になるような塗布基板を得た。乾燥条件は、塗布後60℃で20分、さらに230℃で60分で行った。コントラスト比は、下記基準に従って判定した。
S:9000以上:極めて良好
A:6000以上〜9000未満:良好
B:3000以上〜6000未満:実用可能
C:3000未満:不良
(Evaluation of contrast)
Pigment dispersions (GP-1 to 62) are applied on a glass substrate having a thickness of 100 mm×100 mm and a thickness of 1.1 mm using a spin coater such that x=0.297, y=0.570 in a C light source. A coated substrate was obtained. Drying conditions were 60° C. for 20 minutes after coating, and 230° C. for 60 minutes. The contrast ratio was judged according to the following criteria.
S: 9000 or more: Very good A: 6000 or more and less than 9000: Good B: 3000 or more and less than 6000: Practical C: Less than 3000: Poor
(異物評価)
顔料分散体(GP−1〜62)を、100mm×100mm、1.1mm厚のガラス基板上に、スピンコーターを用いて塗布し、次に60℃で20分乾燥し、230℃で60分間加熱、さらに250℃で60分間追加加熱を行い、放冷することで塗膜基板を作製した。作製した塗膜基板は、250℃での熱処理後で、1.5μmの膜厚に合うようにした。得られた塗膜基板の塗膜中の異物の数を計測した。評価はオリンパスシステム社製金属顕微鏡「BX60」)を用いて表面観察を行った。倍率は500倍とし、透過にて任意の5視野で観測可能な異物の数を計測した。
S:異物の数が3個未満:極めて良好
A:異物の数が3個以上、20個未満:良好
B:異物の数が21個以上、100個未満:実用可能
C:異物の数が100個以上:不良
(Foreign material evaluation)
The pigment dispersion (GP-1 to 62) is applied onto a glass substrate having a thickness of 100 mm×100 mm and a thickness of 1.1 mm by using a spin coater, then dried at 60° C. for 20 minutes and heated at 230° C. for 60 minutes. Further, additional heating was performed at 250° C. for 60 minutes, and the mixture was allowed to cool to prepare a coated substrate. The produced coated substrate was subjected to heat treatment at 250° C. so as to have a thickness of 1.5 μm. The number of foreign matters in the coating film of the obtained coating film substrate was measured. For the evaluation, the surface was observed using a metal microscope "BX60" manufactured by Olympus System Co., Ltd.). The magnification was set to 500 times, and the number of foreign substances observable in arbitrary 5 fields of view was measured.
S: The number of foreign matter is less than 3: Very good A: The number of foreign matter is 3 or more and less than 20: Good B: The number of foreign matter is 21 or more, less than 100: Practical C: The number of foreign matter is 100 More than one: defective
表3に示す通り本発明であるキノフタロン骨格、トリアジン環、酸性基を同時に有するキノフタロン化合物(A)を用いた顔料分散体GP−1〜40はCR、耐熱性、異物、初期粘度及び保存安定性において良好な評価結果となった。好ましくはキノフタロン化合物A−9〜13、15、19、26を用いた緑色顔料分散体が良好であった。さらに好ましくはキノフタロン化合物A−7,8,10、18、30を用いた緑色顔料分散体が最も良好な結果となった。一方、トリアジン環、酸性基を同時に含有しない従来品のキノフタロン化合物D−1〜3を用いた顔料分散体GP53〜62特に耐熱性、異物、初期粘度及び保存安定性において本発明の実施例よりも著しく劣る結果となった。 As shown in Table 3, the pigment dispersions GP-1 to GP40 using the quinophthalone compound (A) having the quinophthalone skeleton, the triazine ring and the acidic group at the same time according to the present invention are CR, heat resistance, foreign matter, initial viscosity and storage stability. The evaluation result was good. The green pigment dispersion using the quinophthalone compounds A-9 to 13, 15, 19, and 26 was preferable. More preferably, the green pigment dispersion using the quinophthalone compound A-7, 8, 10, 18, 30 gave the best result. On the other hand, pigment dispersions GP53 to 62 using conventional quinophthalone compounds D-1 to 3 which do not contain a triazine ring and an acidic group at the same time are more excellent than the examples of the present invention in heat resistance, foreign matter, initial viscosity and storage stability. The result was extremely inferior.
<感光性着色組成物の製造>
[実施例125]
(緑色感光性着色組成物(GR−1))
下記組成の混合物を均一になるように撹拌混合した後、孔径1μmのフィルタで濾過して、緑色感光性着色組成物(GR−1)を作製した。
緑色顔料分散体(GP−1) :50.0部
アクリル樹脂溶液1 : 7.5部
光重合性単量体(東亞合成社製「アロニックスM−402」) : 2.0部
ジペンタエリスリトールヘキサアクリレート
光重合開始剤(BASF社製「イルガキュアー907」) : 1.2部
増感剤(保土谷化学工業社製「EAB−F」) : 0.3部
シクロヘキサノン :39.0部
<Production of photosensitive coloring composition>
[Example 125]
(Green photosensitive coloring composition (GR-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered with a filter having a pore size of 1 μm to prepare a green photosensitive coloring composition (GR-1).
Green pigment dispersion (GP-1): 50.0 parts Acrylic resin solution 1: 7.5 parts Photopolymerizable monomer ("Aronix M-402" manufactured by Toagosei Co., Ltd.): 2.0 parts Dipentaerythritol hexa Acrylate Photopolymerization Initiator (“IRGACURE 907” manufactured by BASF): 1.2 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.): 0.3 parts Cyclohexanone: 39.0 parts
[実施例126〜176、比較例16〜25]
顔料分散体GP−1をGP−2〜GP−62に変更した以外は、実施例125と同様にして、それぞれ緑色感光性着色組成物(GR−2〜62)を得た。
[Examples 126 to 176, Comparative Examples 16 to 25]
Green photosensitive coloring compositions (GR-2 to 62) were obtained in the same manner as in Example 125, except that the pigment dispersion GP-1 was changed to GP-2 to GP-62.
<感光性着色組成物の評価>
得られた緑色顔料感光性着色組成物について、下記評価を行った。結果を表4に示す。
<Evaluation of photosensitive coloring composition>
The following evaluation was performed about the obtained green pigment photosensitive coloring composition. The results are shown in Table 4.
(明度の評価)
顔料分散体(GR−1〜62)を、100mm×100mm、1.1mm厚のガラス基板上に、スピンコーターを用いて、C光源においてx=0.297、y=0.570になるような塗布基板を得た。乾燥条件は、塗布後60℃で20分、さらに230℃で60分で行った。得られた基板の明度(Y)を顕微分光光度計(オリンパス光学社製「OSP−SP200」)で測定した。
(Evaluation of brightness)
Pigment dispersions (GR-1 to 62) are used on a glass substrate having a thickness of 100 mm×100 mm and a thickness of 1.1 mm by using a spin coater such that x=0.297, y=0.570 in a C light source. A coated substrate was obtained. Drying conditions were 60° C. for 20 minutes after coating, and 230° C. for 60 minutes. The brightness (Y) of the obtained substrate was measured with a microspectrophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).
(明度の評価)
明度測定に用いた塗膜基板の塗膜中の異物の数を計測した。評価はオリンパスシステム社製金属顕微鏡「BX60」)を用いて表面観察を行った。倍率は500倍とし、透過にて任意の5視野で観測可能な異物の数を計測した。
S:異物の数が3個未満:極めて良好
A:異物の数が3個以上、20個未満:良好
B:異物の数が21個以上、100個未満:実用可能
C:異物の数が100個以上:不良
(Evaluation of brightness)
The number of foreign matters in the coating film of the coating film substrate used for measuring the brightness was measured. For the evaluation, the surface was observed using a metal microscope "BX60" manufactured by Olympus System Co., Ltd.). The magnification was set to 500 times, and the number of foreign substances observable in arbitrary 5 fields of view was measured.
S: The number of foreign matter is less than 3: Very good A: The number of foreign matter is 3 or more and less than 20: Good B: The number of foreign matter is 21 or more, less than 100: Practical C: The number of foreign matter is 100 More than one: defective
(耐溶剤性の評価)
緑色感光性着色組成物(GR−1〜62)をスピンコート法により、予めブラックマトリックスが形成されているガラス基板に塗工した後、クリーンオーブン中で、70℃で20分間乾燥させた。次いで、この基板を室温に冷却した後、超高圧水銀ランプを用い、フォトマスクを介して紫外光を露光した。その後、この基板を23℃の0.2質量%の炭酸ナトリウム水溶液にて30秒間スプレー現像した後、イオン交換水で洗浄し、乾燥した。さらに、クリーンオーブン中で、230℃で30分間加熱処理を行い、基板上にストライプ状の着色画素層を形成した。得られたストライプ状の緑画素について、N−メチル−2−ピロリドン(NMP)及びメタノール(MeOH)に15分間浸漬し、浸漬前後での緑色画素部分の色差を測定した。色差の測定方法・算出方法・評価基準は、耐熱性と同様とした。
(Evaluation of solvent resistance)
The green photosensitive coloring composition (GR-1 to 62) was applied to a glass substrate on which a black matrix had been formed in advance by spin coating, and then dried in a clean oven at 70°C for 20 minutes. Then, after cooling this substrate to room temperature, it was exposed to ultraviolet light through a photomask using an ultrahigh pressure mercury lamp. Thereafter, this substrate was spray-developed for 30 seconds with a 0.2% by mass sodium carbonate aqueous solution at 23° C., washed with ion-exchanged water, and dried. Further, heat treatment was performed at 230° C. for 30 minutes in a clean oven to form a stripe-shaped colored pixel layer on the substrate. The obtained striped green pixel was immersed in N-methyl-2-pyrrolidone (NMP) and methanol (MeOH) for 15 minutes, and the color difference of the green pixel portion before and after the immersion was measured. The color difference measurement method, calculation method, and evaluation criteria were the same as those for heat resistance.
表4に示すように、本発明の一般式(1)で表されるキノフタロン化合物(A)を用いた着色組成物は、明度、異物及び耐溶剤性について良好な結果となった。一方、トリアジン環、酸性基を同時に含有しない従来のキノフタロン化合物D−1〜3を用いた着色組成物は異物、耐性において、本実施例化合物よりも明らかに劣る結果となった。 As shown in Table 4, the coloring composition using the quinophthalone compound (A) represented by the general formula (1) of the present invention gave good results in lightness, foreign matter and solvent resistance. On the other hand, the coloring composition using the conventional quinophthalone compounds D-1 to 3 which did not contain a triazine ring and an acidic group at the same time was clearly inferior to the compound of this example in foreign matter and resistance.
<カラーフィルタの作製>
(赤色感光性着色組成物(RR−1))
下記組成の混合物を均一になるように撹拌混合した後、孔径1μmのフィルタで濾過して、赤色感光性着色組成物(RR−1)を作製した。
PR254・顔料分散体(RP−1)・顔料分散体 :30.0部
PR177・顔料分散体(RP−2)・顔料分散体 :20.0部
アクリル樹脂溶液1 : 7.5部
光重合性単量体(東亞合成社製「アロニックスM−402」) : 2.0部
光重合開始剤(BASF社製「イルガキュアー907」) : 1.2部
増感剤(保土谷化学工業社製「EAB−F」) : 0.3部
シクロヘキサノン :39.0部
<Production of color filter>
(Red photosensitive coloring composition (RR-1))
The mixture having the following composition was stirred and mixed so as to be uniform, and then filtered with a filter having a pore size of 1 μm to prepare a red photosensitive coloring composition (RR-1).
PR254/Pigment dispersion (RP-1)/Pigment dispersion: 30.0 parts PR177/Pigment dispersion (RP-2)/Pigment dispersion: 20.0 parts Acrylic resin solution 1: 7.5 parts Photopolymerizable Monomer (“Aronix M-402” manufactured by Toagosei Co., Ltd.): 2.0 parts Photopolymerization initiator (“Irgacure 907” manufactured by BASF): 1.2 parts Sensitizer (“Hodogaya Chemical Co., Ltd.” EAB-F"): 0.3 part Cyclohexanone: 39.0 parts
(青色感光性着色組成物(BR−1))
下記組成の混合物を均一になるように撹拌混合した後、孔径1μmのフィルタで濾過して、青色感光性着色組成物(BR−1)を作製した。
PB15:6・顔料分散体(BP−1) :45.0部
PV23・顔料分散体(VP−1) : 5.0部
アクリル樹脂溶液1 : 7.5部
光重合性単量体(東亞合成社製「アロニックスM−402」) : 2.0部
光重合開始剤(BASF社製「イルガキュアー907」) : 1.2部
増感剤(保土谷化学工業社製「EAB−F」) : 0.3部
シクロヘキサノン :39.0部
(Blue photosensitive coloring composition (BR-1))
The mixture having the following composition was stirred and mixed so as to be uniform, and then filtered with a filter having a pore size of 1 μm to prepare a blue photosensitive coloring composition (BR-1).
PB15:6/Pigment dispersion (BP-1): 45.0 parts PV23/Pigment dispersion (VP-1): 5.0 parts Acrylic resin solution 1: 7.5 parts Photopolymerizable monomer (Toagosei) "Aronix M-402" manufactured by the company): 2.0 parts Photopolymerization initiator ("Irgacure 907" manufactured by BASF): 1.2 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.): 0.3 parts Cyclohexanone: 39.0 parts
赤色感光性着色組成物(RR−1)をスピンコート法により、予めブラックマトリックスが形成されているガラス基板に塗工した後、クリーンオーブン中で、70℃で20分間乾燥させた。次いで、この基板を室温に冷却した後、超高圧水銀ランプを用い、フォトマスクを介して紫外線を露光した。その後、この基板を23℃の0.2質量%の炭酸ナトリウム水溶液にて30秒間スプレー現像した後、イオン交換水で洗浄し、乾燥した。さらに、クリーンオーブン中で、230℃で30分間加熱処理を行い、基板上にストライプ状の着色画素層を形成した。次に、本発明の緑色感光性着色組成物(GR−2)を使用し、赤色着色画素層と同様にして緑色着色画素層を形成し、さらに青色感光性着色組成物(BR−1)を使用して青色着色画素層を形成し、カラーフィルタ(CF−1)を得た。各着色画素層の形成膜厚はいずれも2.0μmであった。 The red photosensitive coloring composition (RR-1) was applied by a spin coating method to a glass substrate on which a black matrix was previously formed, and then dried at 70° C. for 20 minutes in a clean oven. Then, after cooling this substrate to room temperature, it was exposed to ultraviolet rays through a photomask using an ultra-high pressure mercury lamp. Thereafter, this substrate was spray-developed for 30 seconds with a 0.2% by mass sodium carbonate aqueous solution at 23° C., washed with ion-exchanged water, and dried. Further, heat treatment was performed at 230° C. for 30 minutes in a clean oven to form a stripe-shaped colored pixel layer on the substrate. Next, using the green photosensitive coloring composition (GR-2) of the present invention, a green coloring pixel layer was formed in the same manner as the red coloring pixel layer, and a blue photosensitive coloring composition (BR-1) was further formed. A blue-colored pixel layer was formed using it to obtain a color filter (CF-1). The formed film thickness of each colored pixel layer was 2.0 μm.
本発明のキノフタロン化合物を含有した緑色着色組成物を使用したカラーフィルタは明度が高く、コントラスト比も優れた結果であり、本発明の効果が立証された。 The color filter using the green coloring composition containing the quinophthalone compound of the present invention has the high brightness and the excellent contrast ratio, which proves the effect of the present invention.
Claims (6)
一般式(1)
Q1は、下記一般式(4)で表される基である。
一般式(4) −(X 3 ) n −(Z 3 ) m −X 4 −*
(一般式(4)中、X 3 は、−NHSO 2 −、−NHCO−、−OSO 2 −、−OCO−、−NH−又は−O−を表す。
Z 3 は、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、又は置換基を有してもよい炭素数20以下のアルキレン基を表し、mが2以上のときは、複数のZ 3 は同一でも異なっていてもよく、複数のZ 3 同士は、−NHSO 2 −、−NHCO−、−OSO 2 −、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
X 4 は、−NH−又は−O−を表す。
nは、0又は1の整数を表し、mは、0〜5の整数を表す。
*はトリアジン環との連結手である。)
A1及びB1は、それぞれ独立に、ヒドロキシル基、塩素原子、下記一般式(2)又は、下記一般式(3)で表され、少なくとも1つは下記一般式(2)で表される基である。
一般式(2) −X1−Z1
(一般式(2)中、X1は、−NH−又は−O−を表す。Z1は、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のアルキル基を表し、X1とZ1とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z1は、−COOH、−SO3H及び−OSO3Hから選ばれる少なくとも1つの置換基を有する。)
一般式(3) −X2−Z2
(一般式(3)中、X2は、−NH−又は−O−を表す。Z2は、置換基を有してもよい炭素数20以下のアルキル基、置換基を有してもよい炭素数20以下のアルケニル基、置換基を有してもよい炭素数20以下のアリール基、又は置換基を有してもよい炭素数20以下のヘテロアリール基を表し、X2とZ2とは、置換基を有してもよい炭素数20以下のアリレーン基、置換基を有してもよい炭素数20以下のヘテロアリレーン基、置換基を有してもよい炭素数20以下のアルキレン基、−NHSO2−、−NHCO−、−OSO2−、−OCO−、−S−、−NH−及び−O−から選ばれる少なくとも1種の2価の連結基によって連結されていても良い。
ただし、Z2は、置換基として−COOH、−SO3H又はOSO3Hを有しない。)] A quinophthalone compound (A) represented by the following general formula (1).
General formula (1)
Q 1 is a group represented by the following general formula (4).
Formula (4) - (X 3) n - (Z 3) m -X 4 - *
(In the general formula (4), X 3 is, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - NH- or an -O-.
Z 3 is an arylene group having 20 or less carbon atoms which may have a substituent, a heteroarylene group having 20 or less carbon atoms which may have a substituent, or a carbon number 20 which may have a substituent. The following alkylene groups are represented, and when m is 2 or more, a plurality of Z 3's may be the same or different, and a plurality of Z 3's are —NHSO 2 —, —NHCO—, —OSO 2 —, —. They may be linked by at least one divalent linking group selected from OCO-, -S-, -NH- and -O-.
X 4 represents -NH- or -O-.
n represents an integer of 0 or 1, and m represents an integer of 0 to 5.
* Is a linking hand with the triazine ring. )
A1 and B1 are each independently represented by a hydroxyl group, a chlorine atom, the following general formula (2) or the following general formula (3), and at least one is a group represented by the following general formula (2). ..
Formula (2) -X 1 -Z 1
(In the general formula (2), X 1 represents —NH— or —O—. Z 1 may have a substituent having 20 or less carbon atoms, or may have a substituent. Represents a good alkyl group having 20 or less carbon atoms, and X 1 and Z 1 represent an arylene group having 20 or less carbon atoms which may have a substituent, and a heteroari having 20 or less carbon atoms which may have a substituent. lane group, a substituted alkylene group having 20 or less carbon atoms which may have, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - S -, - selected from NH- and -O- May be linked by at least one divalent linking group.
However, Z 1 has at least one substituent selected from —COOH, —SO 3 H, and —OSO 3 H. )
Formula (3) -X 2 -Z 2
(In the general formula (3), X 2 represents —NH— or —O—. Z 2 may have a substituent having 20 or less carbon atoms, or may have a substituent. It represents an alkenyl group having 20 or less carbon atoms, an aryl group having 20 or less carbon atoms that may have a substituent, or a heteroaryl group having 20 or less carbon atoms that may have a substituent, and X 2 and Z 2 Is an arylene group having 20 or less carbon atoms, which may have a substituent, a heteroarylene group having 20 or less carbon atoms, which may have a substituent, and an alkylene having 20 or less carbon atoms, which may have a substituent. group, -NHSO 2 -, - NHCO - , - OSO 2 -, - OCO -, - S -, - selected from NH- and -O- may be linked by at least one divalent linking group ..
However, Z 2 has no -COOH, -SO 3 H at or OSO 3 H as a substituent. )]
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