KR101970416B1 - Compound - Google Patents
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- Publication number
- KR101970416B1 KR101970416B1 KR1020177011610A KR20177011610A KR101970416B1 KR 101970416 B1 KR101970416 B1 KR 101970416B1 KR 1020177011610 A KR1020177011610 A KR 1020177011610A KR 20177011610 A KR20177011610 A KR 20177011610A KR 101970416 B1 KR101970416 B1 KR 101970416B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- carbon atoms
- compound
- alkyl group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 198
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 107
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 40
- 125000005843 halogen group Chemical group 0.000 claims abstract description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- 239000011342 resin composition Substances 0.000 claims description 31
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 238000002835 absorbance Methods 0.000 abstract description 11
- -1 1-methylpentyl group Chemical group 0.000 description 112
- 239000011347 resin Substances 0.000 description 78
- 229920005989 resin Polymers 0.000 description 78
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 71
- 239000002904 solvent Substances 0.000 description 62
- 239000000203 mixture Substances 0.000 description 45
- 239000000049 pigment Substances 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 39
- 239000003505 polymerization initiator Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 29
- 239000000975 dye Substances 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000002430 hydrocarbons Chemical class 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 229930195734 saturated hydrocarbon Natural products 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 239000010949 copper Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 238000004040 coloring Methods 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- 239000003086 colorant Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000004292 cyclic ethers Chemical group 0.000 description 10
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 244000172533 Viola sororia Species 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 229940116333 ethyl lactate Drugs 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 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
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 4
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000980 acid dye Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012435 aralkylating agent Substances 0.000 description 4
- 229960004424 carbon dioxide Drugs 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000008399 tap water Substances 0.000 description 4
- 235000020679 tap water Nutrition 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 150000002941 palladium compounds Chemical class 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
Abstract
본 발명은, 흡광도가 우수한 화합물을 제공하는 것을 과제로 한다.
본 발명은, 식(A-I)으로 나타나는 화합물에 관한 것이다.
[R1a~R8a는, 수소 원자, 알킬기, SO3 -기 또는 SO3M기;R9a, R10a는, 수소 원자, 알킬기, 방향족 탄화수소기, 또는 아르알킬기;R11a~R20a는, 수소 원자, 알킬기, 할로겐 원자, SO3 -기 또는 SO3M기;R45a, R46a는, 수소 원자, 알킬기, 방향족 탄화수소기;R55a는, 수소 원자, 알킬기, 방향족 탄화수소기.]It is an object of the present invention to provide a compound having excellent absorbance.
The present invention relates to a compound represented by formula (A-I).
[R 1a ~ R 8a is a hydrogen atom, an alkyl group, an SO 3 - group or a SO 3 M group; R 9a, R 10a is a hydrogen atom, an alkyl group, an aromatic hydrocarbon group, or an aralkyl group; R 11a ~ R 20a is R 55a represents a hydrogen atom, an alkyl group, an aromatic hydrocarbon group, a halogen atom, an alkyl group, a halogen atom, an SO 3 - group or an SO 3 M group; R 45a and R 46a represent a hydrogen atom, an alkyl group or an aromatic hydrocarbon group;
Description
본 발명은, 색소로서 유용한 화합물에 관한 것이다.The present invention relates to a compound useful as a coloring matter.
액정 표시 장치 등이나 고체 촬상 소자 등에 포함되어 있는 칼라 필터용 청색 염료로서, 특허 문헌 1에, C.I. 애시드 블루 90이 기재되어 있다. 이 애시드 블루 90은, 하기에 나타내는 화학 구조를 갖고 있고, 상기 특허 문헌 1에서는 바람직한 염료로 분류되어 있다.As a blue dye for a color filter included in a liquid crystal display device or the like or a solid-state image pickup device, Patent Document 1 discloses a blue dye. Acid Blue 90 is described. This Acid Blue 90 has a chemical structure shown below, and is classified as a preferable dye in Patent Document 1.
<화학식 1>≪ Formula 1 >
본 발명의 목적은, 흡광도가 높은 화합물을 제공하는 것, 및 그러한 화합물을 포함하는 착색 경화성 수지 조성물을 제공하는 것에 있다.It is an object of the present invention to provide a compound having high absorbance and a colored curable resin composition containing such a compound.
본 발명은, 이하의 발명을 포함한다.The present invention includes the following inventions.
[1]식(A-I)로 나타나는 화합물.[1] A compound represented by the formula (A-I).
<화학식 2>(2)
[식(A-I) 중,[In the formula (A-I)
R1a, R2a, R3a, R4a, R5a, R6a, R7a 및 R8a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, SO3 -기 또는 SO3M기를 나타낸다.Each of R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a SO 3 - group or a SO 3 M group.
R9a 및 R10a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 치환되어 있어도 되는 방향족 탄화수소기, 또는 치환되어 있어도 되는 아르알킬기를 나타낸다.R 9a and R 10a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
R11a~R20a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 할로겐 원자, SO3 -기 또는 SO3M기를 나타낸다.R 11a to R 20a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a SO 3 - group or a SO 3 M group.
상기 R1a~R20a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.In the above-mentioned R 1a to R 20a , the alkyl group may have an oxygen atom inserted in the methylene period constituting the alkyl group.
R45a 및 R46a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.R 45a and R 46a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group.
R55a는, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
상기 R45a, R46a, 및 R55a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.In R 45a , R 46a and R 55a , the alkyl group may have oxygen atoms inserted into the constituent methylene period.
M은, 수소 이온, 금속 이온 또는 암모늄 이온을 나타낸다.M represents a hydrogen ion, a metal ion or an ammonium ion.
단, R1a~R20a, R45a, R46a 및 R55a는, 적어도 (1), (2) 및 (3)중 어느 1개의 요건과 (4)의 요건을 만족한다.Provided that R 1a to R 20a , R 45a , R 46a and R 55a satisfy at least one of the requirements of (1), (2) and (3) and the requirement of (4).
(1) R1a~R8a 및 R11a~R20a중 적어도 1개는, SO3 -기 또는 SO3M기이다.(1) At least one of R 1a to R 8a and R 11a to R 20a is an SO 3 - group or a SO 3 M group.
(2) R9a, R10a, R45a, R46a 및 R55a중 적어도 1개는, 치환기로서 SO3 -기 또는 SO3M기를 갖는 방향족 탄화수소기이다.(2) At least one of R 9a , R 10a , R 45a , R 46a and R 55a is an aromatic hydrocarbon group having a SO 3 - group or a SO 3 M group as a substituent.
(3) R9a 및 R10a중 적어도 1개는, 환상의 치환기로서 SO3 -기 또는 SO3M기를 갖는 아르알킬기이다.(3) At least one of R 9a and R 10a is an aralkyl group having a SO 3 - group or a SO 3 M group as a cyclic substituent.
(4) 식(A-I)로 나타나는 화합물이 갖는 SO3 -기의 수는 1이고, SO3M기의 수는 0~6이다.](4) The number of SO 3 - groups in the compound represented by the formula (A-I) is 1 and the number of SO 3 M groups is 0 to 6.]
[2]상기[1]기재의 식(A-I)로 나타나는 화합물을 포함하는 착색 경화성 수지 조성물.[2] A colored curable resin composition comprising a compound represented by the formula (A-I) described in [1] above.
[3]상기[2]기재의 착색 경화성 수지 조성물을 이용하여 형성되는 칼라 필터.[3] A color filter formed using the colored curable resin composition according to [2] above.
[4]상기[3]기재의 칼라 필터를 포함하는 표시 장치.[4] A display device comprising the color filter described in [3] above.
본 발명의 화합물은, 흡광도가 높다. 이와 같은 화합물을 포함하는 착색 경화성 수지 조성물을 이용하면, 착색제의 사용량을 억제할 수 있다.The compounds of the present invention have high absorbance. The use of the colored curable resin composition containing such a compound can suppress the amount of the coloring agent used.
본 발명의 화합물은, 식(A-I)로 나타나는 화합물(이하, 화합물(A-I)이라고 하는 경우가 있다)이다. 본 발명의 화합물에는, 그 호변 이성체나 그들 염도 포함된다.The compound of the present invention is a compound represented by the formula (A-I) (hereinafter sometimes referred to as a compound (A-I)). The compounds of the present invention also include tautomers and salts thereof.
<화학식 3>(3)
[식(A-I) 중,[In the formula (A-I)
R1a, R2a, R3a, R4a, R5a, R6a, R7a 및 R8a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, SO3 -기 또는 SO3M기를 나타낸다. Each of R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a SO 3 - group or a SO 3 M group.
R9a 및 R10a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 치환되어 있어도 되는 방향족 탄화수소기, 또는 치환되어 있어도 되는 아르알킬기를 나타낸다. R 9a and R 10a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
R11a~R20a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 할로겐 원자, SO3 -기 또는 SO3M기를 나타낸다. R 11a to R 20a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a SO 3 - group or a SO 3 M group.
상기 R1a~R20a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다. In the above-mentioned R 1a to R 20a , the alkyl group may have an oxygen atom inserted in the methylene period constituting the alkyl group.
R45a 및 R46a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다. R 45a and R 46a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group.
R55a는, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다. R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
상기 R45a, R46a, 및 R55a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다. In R 45a , R 46a and R 55a , the alkyl group may have oxygen atoms inserted into the constituent methylene period.
M은, 수소이온, 금속 이온 또는 암모늄 이온을 나타낸다.M represents a hydrogen ion, a metal ion or an ammonium ion.
단, R1a~R20a, R45a, R46a 및 R55a는, 적어도 (1), (2) 및 (3)중 어느 1개의 요건과, (4)의 요건을 만족한다. Provided that R 1a to R 20a , R 45a , R 46a and R 55a satisfy at least one of the requirements (1), (2) and (3) and the requirement (4).
(1) R1a~R8a 및 R11a~R20a중 적어도 1개는, SO3 -기 또는 SO3M기이다.(1) At least one of R 1a to R 8a and R 11a to R 20a is an SO 3 - group or a SO 3 M group.
(2) R9a, R10a, R45a, R46a 및 R55a중 적어도 1개는, 치환기로서 SO3 -기 또는 SO3M기를 갖는 방향족 탄화수소기이다. (2) At least one of R 9a , R 10a , R 45a , R 46a and R 55a is an aromatic hydrocarbon group having a SO 3 - group or a SO 3 M group as a substituent.
(3) R9a 및 R10a중 적어도 1개는, 환상의 치환기로서 SO3 -기 또는 SO3M기를 갖는 아르알킬기이다. (3) At least one of R 9a and R 10a is an aralkyl group having a SO 3 - group or a SO 3 M group as a cyclic substituent.
(4) 식(A-I)로 나타나는 화합물이 갖는 SO3 -기의 수는 1이고, SO3M기의 수는 0~6이다.] (4) The number of SO 3 - groups in the compound represented by the formula (A-I) is 1 and the number of SO 3 M groups is 0 to 6.]
식(A-I)의 화합물은, 가수가 0이다.The compound of formula (A-I) has a valence of zero.
R1a~R20a로 나타나는 알킬기는, 직쇄, 분기쇄 및 환상 중 어느 하나라도 된다. 직쇄 또는 분기쇄의 알킬기로서는, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 옥틸기, 노닐기, 데실기 등을 들 수 있다. 당해 알킬기는, 바람직하게는 탄소수 1~10이고, 보다 바람직하게는 탄소수 1~8이고, 더욱 바람직하게는 탄소수 1~6이다. The alkyl group represented by R 1a to R 20a may be any of linear, branched and cyclic. Examples of the straight chain or branched chain alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group and a decyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 6 carbon atoms.
R1a~R20a로 나타나는 환상의 알킬기는, 단환이라도 다환이라도 된다. 당해 환상의 알킬기로서는, 사이클로프로필기, 사이클로부틸기, 사이클로펜틸기, 사이클로헥실기, 아다만틸기 등을 들 수 있다. 당해 환상의 알킬기는, 바람직하게는 탄소수 3~10이고, 보다 바람직하게는 탄소수 6~10이다. The cyclic alkyl group represented by R 1a to R 20a may be monocyclic or polycyclic. Examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and an adamantyl group. The cyclic alkyl group preferably has 3 to 10 carbon atoms, more preferably 6 to 10 carbon atoms.
R1a~R20a로 나타나는 알킬기의 구체예로서, 메틸기, 에틸기, n-프로필기, n-부틸기, n-펜틸기, n-헥실기 등의 직쇄상 알킬기;이소프로필기, sec-부틸기, tert-부틸기, 이소펜틸기, 1-메틸펜틸기, 2-에틸부틸기 등의 분기쇄상 알킬기;사이클로프로필기, 사이클로부틸기, 사이클로펜틸기, 사이클로헥실기, 아다만틸기 등의 환상 알킬기;등을 들 수 있고, 예를 들면, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다.Specific examples of the alkyl group represented by R 1a to R 20a include straight chain alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group, , branched chain alkyl groups such as a tert-butyl group, an isopentyl group, a 1-methylpentyl group and a 2-ethylbutyl group, and cyclic alkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and adamantyl group ; And the like, for example, a group represented by the following formula can be mentioned. In the following formula, * denotes a binding hand.
<화학식 4>≪ Formula 4 >
R1a~R20a로 나타나는 기 중, 당해 알킬기를 구성하는 메틸렌기간에 산소 원자가 삽입되어 있는 기로서는, 예를 들면, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다.Of the groups represented by R 1a to R 20a , groups in which an oxygen atom is inserted into the methylene moiety constituting the alkyl group include groups represented by the following formulas, for example. In the following formula, * denotes a binding hand.
<화학식 5>≪ Formula 5 >
당해 알킬기를 구성하는 메틸렌기간에 산소 원자가 삽입되어 있는 기로서는, 탄소수 1~10의 기가 바람직하고, 탄소수 1~6의 기가 보다 바람직하다. 산소 원자가 삽입되는 알킬기는, 직쇄상 알킬기가 바람직하다. 또한 산소 원자간의 탄소수는, 1~4개가 바람직하고, 2~3개가 보다 바람직하다.The group having an oxygen atom inserted into the methylene group constituting the alkyl group is preferably a group having 1 to 10 carbon atoms and more preferably a group having 1 to 6 carbon atoms. The alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group. The number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
R9a~R10a에 있어서, 방향족 탄화수소기로서는, 페닐기, 나프틸기 등의 탄소수 6~10의 방향족 탄화수소기를 들 수 있다.In R 9a to R 10a , examples of the aromatic hydrocarbon group include an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group.
R9a~R10a에 있어서, 아르알킬기에 있어서의 방향족 탄화수소기로서는, 페닐기, 나프틸기 등을 들 수 있다. 아르알킬기의 탄소수는 7~20개가 바람직하다.In R 9a to R 10a , examples of the aromatic hydrocarbon group in the aralkyl group include a phenyl group and a naphthyl group. The number of carbon atoms of the aralkyl group is preferably 7 to 20.
R9a~R10a로 나타나는 기 중, 상기 방향족 탄화수소기 및 상기 아르알킬기에 있어서의 치환기로서는, 불소 원자, 염소 원자, 요오드 등의 할로겐 원자;메톡시기, 에톡시기 등의 탄소수 1~6의 알콕시기;하이드록시기;메틸기, 에틸기, 프로필기 등의 탄소수 1~6의 알킬기;술파모일기;메틸술포닐기 등의 탄소수 1~6의 알킬술포닐기;메톡시카보닐기, 에톡시카보닐기;-SO3H기;-SO3 -기;등의 탄소수 1~6의 알콕시카보닐기 등을 들 수 있다.Examples of the substituent in the aromatic hydrocarbon group and the aralkyl group represented by R 9a to R 10a include a halogen atom such as a fluorine atom, a chlorine atom and iodine, an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group A hydroxyl group, an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group and a propyl group, a sulfamoyl group, an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 3 H groups; and -SO 3 - groups; and the like.
치환되어 있어도 되는 방향족 탄화수소기의 구체예로서는, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다.Specific examples of the optionally substituted aromatic hydrocarbon group include groups represented by the following formulas. In the following formula, * denotes a binding hand.
치환되어 있어도 되는 아르알킬기의 구체예로서는, 하기 방향족 탄화수소기의 각 구체예의 결합손에 메틸렌기가 결합한 기를 들 수 있다.Specific examples of the aralkyl group which may be substituted include groups in which a methylene group is bonded at the bond of each specific example of the aromatic hydrocarbon group described below.
<화학식 6>(6)
<화학식 7>≪ Formula 7 >
R11a~R20a로 나타나는 기 중, 할로겐 원자로서는, 불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등을 들 수 있고, 불소 원자가 바람직하다.Of the groups represented by R 11a to R 20a , examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable.
R1a~R8a는, 합성의 용이함의 점에서, 각각 독립적으로, 수소 원자, 또는 탄소수 1~10의 알킬기인 것이 바람직하고, 수소 원자, 또는 메틸기인 것이 보다 바람직하다.Each of R 1a to R 8a is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is more preferably a hydrogen atom or a methyl group from the standpoint of ease of synthesis.
R9a~R10a는, 합성의 용이함의 점에서, 각각 독립적으로, 탄소수 1~10의 알킬기, 치환되어 있어도 되는 방향족 탄화수소기 또는 치환되어 있어도 되는 아르알킬기인 것이 바람직하고, 각각 독립적으로, 탄소수 1~8의 알킬기, 페닐기, 나프틸기, 메틸기를 갖는 페닐기, 메틸기를 갖는 나프틸기;무치환의, 또는 할로겐 원자, 메톡시기, 에톡시기, 술파모일기, 메틸술포닐기, 메톡시카보닐기, 및 에톡시카보닐기에서 선택되는 1종 이상, 특히 1종으로 치환된 아르알킬기인 것이 보다 바람직하고, 각각 독립적으로, 탄소수 1~4의 직쇄상 알킬기인 것이 더욱 바람직하다.Each of R 9a to R 10a is preferably an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group which may be substituted, or an aralkyl group which may be substituted, independently of each other, from the viewpoint of easiness of synthesis, A phenyl group, a naphthyl group, a phenyl group having a methyl group, a naphthyl group having a methyl group, an unsubstituted or halogen atom, a methoxy group, an ethoxy group, a sulfamoyl group, a methylsulfonyl group, a methoxycarbonyl group, and More preferably an aralkyl group substituted by at least one member selected from the group consisting of an alkyl group, an alkoxy group, and an alkoxy group.
R11a~R12a는, 내열성의 점에서, 적어도 어느 한쪽이 할로겐 원자 또는 탄소수 1~10의 알킬기인 것이 바람직하고, 적어도 어느 한쪽이 할로겐 원자 또는 탄소수 1~8의 알킬기인 것이 보다 바람직하고, 적어도 어느 한쪽이 불소 원자 또는 탄소수 1~4의 알킬기인 것이 더욱 바람직하다.In terms of heat resistance, at least one of R 11a to R 12a is preferably a halogen atom or an alkyl group having 1 to 10 carbon atoms, and at least one of R 11a to R 12a is more preferably a halogen atom or an alkyl group having 1 to 8 carbon atoms, And it is more preferable that either one of them is a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
R13a~R14a는, 내열성의 점에서, 적어도 어느 한쪽이 할로겐 원자 또는 탄소수 1~10의 알킬기인 것이 바람직하고, 적어도 어느 한쪽이 할로겐 원자 또는 탄소수 1~8의 알킬기인 것이 보다 바람직하고, 적어도 어느 한쪽이 불소 원자 또는 탄소수 1~4의 알킬기인 것이 더욱 바람직하다.In terms of heat resistance, at least one of R 13a to R 14a is preferably a halogen atom or an alkyl group having 1 to 10 carbon atoms, and at least one of R 13a to R 14a is more preferably a halogen atom or an alkyl group having 1 to 8 carbon atoms, And it is more preferable that either one of them is a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
R15a~R20a는, 합성의 용이함의 점에서, 각각 독립적으로, 수소 원자, 또는 탄소수 1~10의 알킬기인 것이 바람직하고, 수소 원자, 또는 탄소수 1~4의 알킬기인 것이 보다 바람직하고, 수소 원자, 또는 메틸기인 것이 더욱 바람직하다.Each of R 15a to R 20a is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, More preferably an atom, or a methyl group.
R45a 및 R46a에 있어서의 알킬기로서는, 각각 R1a~R20a에 있어서의 탄소수 1~10의 알킬기를 들 수 있다.Examples of the alkyl group for R 45a and R 46a include an alkyl group having 1 to 10 carbon atoms for R 1a to R 20a , respectively.
R45a 및 R46a에 있어서, 탄소수 1~10의 알킬기의 구체예로서는, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다. 그 중에서도, 탄소수 1~8의 알킬기가 바람직하고, 탄소수 1~6의 알킬기가 보다 바람직하고, 탄소수 1~4의 알킬기가 특히 바람직하다.In R 45a and R 46a , specific examples of the alkyl group having 1 to 10 carbon atoms include the groups represented by the following formulas. In the following formula, * denotes a binding hand. Among them, an alkyl group having 1 to 8 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
<화학식 8>(8)
R45a 및 R46a에 있어서, 당해 알킬기를 구성하는 메틸렌기간에 산소 원자가 삽입되어 있는 기로서는, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다. 산소 원자가 삽입되는 알킬기는, 직쇄상 알킬기가 바람직하다. 또한 산소 원자간의 탄소수는, 1~4개가 바람직하고, 2~3개가 보다 바람직하다.In R 45a and R 46a , groups in which an oxygen atom is inserted into the methylene moiety constituting the alkyl group include groups represented by the following formulas. In the following formula, * denotes a binding hand. The alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group. The number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
<화학식 9>≪ Formula 9 >
당해 알킬기를 구성하는 메틸렌기간에 산소 원자가 삽입되어 있는 기로서는, 탄소수 1~10의 기가 바람직하고, 탄소수 1~6의 기가 보다 바람직하다. 산소 원자가 삽입되는 알킬기는, 직쇄상 알킬기가 바람직하다. 또한 산소 원자간의 탄소수는 1~4개가 바람직하고, 2~3개가 보다 바람직하다. The group having an oxygen atom inserted into the methylene group constituting the alkyl group is preferably a group having 1 to 10 carbon atoms and more preferably a group having 1 to 6 carbon atoms. The alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group. The number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
R45a 및 R46a에 있어서, 방향족 탄화수소기로서는 페닐기, 나프틸기 등의 탄소수 6~10의 방향족 탄화수소기를 들 수 있다.Examples of the aromatic hydrocarbon group for R 45a and R 46a include an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group.
R45a 및 R46a로 나타나는 방향족 탄화수소기에 있어서, 치환기로서는, 불소 원자, 염소 원자, 요오드 등의 할로겐 원자;클로로메틸기, 트리플루오로메틸기 등의 탄소수 1~6의 할로알킬기;메톡시기, 에톡시기 등의 탄소수 1~6의 알콕시기;하이드록시기;메틸기, 에틸기, 프로필기 등의 탄소수 1~6의 알킬기;술파모일기;메틸술포닐기 등의 탄소수 1~6의 알킬술포닐기;메톡시카보닐기 등의 탄소수 1~6의 알콕시카보닐기;-SO3H기;-SO3 -기;등을 들 수 있다. Examples of the substituent for the aromatic hydrocarbon group represented by R 45a and R 46a include a halogen atom such as a fluorine atom, a chlorine atom and iodine, a haloalkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group, a methoxy group, An alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group and a propyl group, a sulfamoyl group, an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group, An alkoxycarbonyl group having 1 to 6 carbon atoms, such as -SO 3 H group, -SO 3 - group, and the like.
치환되어 있어도 되는 방향족 탄화수소기의 구체예로서는, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다.Specific examples of the optionally substituted aromatic hydrocarbon group include groups represented by the following formulas. In the following formula, * denotes a binding hand.
<화학식 10>≪ Formula 10 >
R45a 및 R46a는, 합성의 용이함의 점에서, 각각 독립적으로, 탄소수 1~10의 알킬기 또는 치환되어 있어도 되는 방향족 탄화수소기인 것이 바람직하고, 할로겐 원자, 탄소수 1~4의 할로알킬기, 탄소수 1~4의 알콕시기, 하이드록시기, 탄소수 1~4의 알킬기, 혹은 메틸술포닐기로 치환되어 있어도 되는 방향족 탄화수소기, 또는 탄소수 1~8의 알킬기인 것이 보다 바람직하고, 탄소수 1~8의 알킬기 또는 하기식으로 나타나는 방향족 탄화수소기인 것이 더욱 바람직하다. 하기식 중, *는 결합손을 나타낸다.R 45a and R 46a are preferably each independently an alkyl group having 1 to 10 carbon atoms or an aromatic hydrocarbon group which may be substituted in view of ease of synthesis, and is preferably a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, More preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group optionally substituted with a methylsulfonyl group, or an alkyl group having 1 to 8 carbon atoms, More preferably an aromatic hydrocarbon group represented by the formula: In the following formula, * denotes a binding hand.
<화학식 11>≪ Formula 11 >
R55a에 있어서의 알킬기로서는, 각각 R1a~R20a에 있어서의 알킬기를 들 수 있다. Examples of the alkyl group in R 55a include alkyl groups in R 1a to R 20a , respectively.
R55a에 있어서, 탄소수 1~10의 알킬기의 구체예로서는, 메틸기, 에틸기, n-프로필기, n-부틸기, n-펜틸기, n-헥실기, n-옥틸기, n-노닐기, n-데실기 등의 직쇄상 알킬기;이소프로필기, sec-부틸기, tert-부틸기, 이소펜틸기, 1-메틸펜틸기, 1-프로필부틸기 등의 분기쇄상 알킬기;사이클로프로필기, 사이클로부틸기, 사이클로펜틸기, 사이클로헥실기, 아다만틸기 등의 환상 알킬기;등을 들 수 있고, 예를 들면, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다. 그 중에서도, 탄소수 1~8의 알킬기가 바람직하고, 탄소수 1~6의 알킬기가 보다 바람직하고, 탄소수 1~4의 알킬기가 특히 바람직하다.Specific examples of the alkyl group having 1 to 10 carbon atoms in R 55a include a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n- Branched chain alkyl groups such as isopropyl, sec-butyl, tert-butyl, isopentyl, 1-methylpentyl and 1-propylbutyl groups, cyclopropyl, cyclobutyl And cyclic alkyl groups such as a cyclopentyl group, a cyclohexyl group and an adamantyl group, and the like, and examples thereof include the groups represented by the following formulas. In the following formula, * denotes a binding hand. Among them, an alkyl group having 1 to 8 carbon atoms is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
<화학식 12>≪ Formula 12 >
R55a에 있어서, 당해 알킬기를 구성하는 메틸렌기간에 산소 원자가 삽입되어 있는 기로서는, 예를 들면, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다. 산소 원자가 삽입되는 알킬기는, 직쇄상 알킬기가 바람직하다. 또한 산소 원자간의 탄소수는, 1~4개가 바람직하고, 2~3개가 보다 바람직하다.Examples of the group represented by R 55a in which an oxygen atom is inserted into the methylene moiety constituting the alkyl group include groups represented by the following formulas. In the following formula, * denotes a binding hand. The alkyl group into which the oxygen atom is inserted is preferably a linear alkyl group. The number of carbon atoms between oxygen atoms is preferably 1 to 4, more preferably 2 to 3.
<화학식 13>≪ Formula 13 >
R55a에 있어서, 방향족 탄화수소기로서는, 페닐기, 나프틸기 등의 탄소수 6~10의 방향족 탄화수소기를 들 수 있고, 페닐기가 바람직하다.In R 55a , examples of the aromatic hydrocarbon group include an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group, and a phenyl group is preferable.
R55a에 있어서, 방향족 탄화수소기에 있어서의 치환기로서는, 불소 원자, 염소 원자, 요오드 등의 할로겐 원자;클로로메틸기, 트리플루오로메틸기 등의 탄소수 1~6의 할로알킬기;메톡시기, 에톡시기 등의 탄소수 1~6의 알콕시기;하이드록시기;메틸기, 에틸기 등의 탄소수 1~6의 알킬기;술파모일기;메틸술포닐기 등의 탄소수 1~6의 알킬술포닐기;메톡시카보닐기 등의 탄소수 1~6의 알콕시카보닐기;-SO3H기;-SO3 -기;등을 들 수 있다. 치환되어 있어도 되는 방향족 탄화수소기의 구체예로서는, 하기식으로 나타나는 기를 들 수 있다. 하기식 중, *는 결합손을 나타낸다.In R 55a , examples of the substituent in the aromatic hydrocarbon group include halogen atoms such as fluorine, chlorine and iodine; haloalkyl groups having 1 to 6 carbon atoms such as chloromethyl and trifluoromethyl; An alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, an alkyl group having 1 to 6 carbon atoms such as a methyl group and an ethyl group, a sulfamoyl group, an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group, An alkoxycarbonyl group of 1 to 6 carbon atoms, an -SO 3 H group, and an -SO 3 - group. Specific examples of the optionally substituted aromatic hydrocarbon group include groups represented by the following formulas. In the following formula, * denotes a binding hand.
<화학식 14>≪ Formula 14 >
R55a는, 합성의 용이함의 점에서, 바람직하게는 탄소수 1~10의 알킬기 또는 치환되어 있어도 되는 방향족 탄화수소기이고, 보다 바람직하게는 탄소수 1~8의 알킬기 또는 할로겐 원자, 탄소수 1~4의 할로알킬기, 탄소수 1~4의 알콕시기, 하이드록시기, 탄소수 1~4의 알킬기, 혹은 메틸술포닐기로 치환되어 있어도 되는 방향족 탄화수소기이고, 더욱 바람직하게는 하기식으로 나타나는 방향족 탄화수소기이다. 하기식 중, *는 결합손을 나타낸다.R 55a is preferably an alkyl group having 1 to 10 carbon atoms or an aromatic hydrocarbon group which may be substituted, more preferably an alkyl group having 1 to 8 carbon atoms or a halogen atom, a halo of 1 to 4 carbon atoms An aromatic hydrocarbon group which may be substituted with an alkyl group, an alkoxy group of 1 to 4 carbon atoms, a hydroxyl group, an alkyl group of 1 to 4 carbon atoms, or a methylsulfonyl group, and more preferably an aromatic hydrocarbon group represented by the following formula. In the following formula, * denotes a binding hand.
<화학식 15>≪ Formula 15 >
M에 있어서, 금속 이온으로서는, 리튬 이온, 나트륨 이온, 칼륨 이온과 같은 알칼리 금속 이온을 들 수 있다.In M, examples of the metal ion include alkali metal ions such as lithium ion, sodium ion and potassium ion.
M에 있어서, 암모늄 이온으로서는, 테트라알킬암모늄 이온과 같은 4급 암모늄 이온 등이 바람직하다. 4급 암모늄 이온은, 착색 경화성 수지 조성물에 함유시키는 경우에 유용하다.In M, as the ammonium ion, quaternary ammonium ion such as tetraalkylammonium ion and the like are preferable. The quaternary ammonium ion is useful when it is contained in the colored curable resin composition.
M은, 흡광도의 점에서, 수소 이온 또는 알칼리 금속 이온이 바람직하고, 수소 이온이 보다 바람직하다.M is preferably a hydrogen ion or an alkali metal ion, more preferably a hydrogen ion, from the viewpoint of absorbance.
식(A-I)로 나타나는 화합물이 갖는 SO3 -기의 수는 1이다. 또한, SO3M기의 수는 0~6의 범위에서 적절히 설정되고, 보다 바람직하게는 1~3이고, 더욱 바람직하게는 1이다. 화합물(A-I)에 있어서, SO3 -기 및 SO3M기는, R1a~R8a 및 R11a~R20a로 나타나는 치환기로서 갖고 있어도 되고, 하기 (1a) 및 (2a)의 치환기로서 갖고 있어도 된다.The number of SO 3 - groups in the compound represented by the formula (A-I) is 1. The number of SO 3 M groups is suitably set in the range of 0 to 6, more preferably 1 to 3, and still more preferably 1. In the compound (A-I), the SO 3 - group and the SO 3 M group may be contained as substituents represented by R 1a to R 8a and R 11a to R 20a , and may be the substituents represented by the following formulas (1a) and .
(1a)R9a, R10a, R45a, R46a 및 R55a에 의해 나타나는 방향족 탄화수소기에 있어서의 치환기(1a) Substituents in the aromatic hydrocarbon group represented by R 9a , R 10a , R 45a , R 46a and R 55a
(2a)R9a 및 R10a에 의해 나타나는 아르알킬기에 있어서의 환 상의 치환기(2a) Substituents on the ring in the aralkyl group represented by R < 9a > and R <
SO3 -기 및 SO3M기는, 동일한 방향족환에 결합해도 되지만, 상이한 방향족환에 결합해 있는 쪽이 많다.The SO 3 - group and the SO 3 M group may be bonded to the same aromatic ring, but many of them are bonded to different aromatic rings.
화합물(A-I)은, 가수가 0, 즉 전기적으로 중성인 화합물이다.The compound (A-I) is a compound in which the valence is 0, i.e., an electrically neutral compound.
식(A-I)로 나타나는 화합물로서는, 식(A-I-1)로 나타나는 화합물 1~90을 들 수 있다.Examples of the compound represented by the formula (A-I) include the compounds 1 to 90 represented by the formula (A-I-1).
<화학식 16>≪ Formula 16 >
[식(A-I-1) 중, R9a~R20a, R45a, R46a 및 R55a는, 표 1~표 6과 같다. 단, 식(A-I-1)의 화합물은, R1a~R8a, R11a~R20a, (1a) 및 (2a)중 어느 하나의 치환기로서, SO3 -기 및 SO3H기 중 적어도 어느 1개를 갖는다.][In the formula (A-I-1), R 9a to R 20a , R 45a , R 46a and R 55a are as shown in Tables 1 to 6. In this formula, (A-I-1) compounds, R 1a ~ R 8a, R 11a ~ R 20a, (1a) and (2a) as any of the substituents of, SO 3 in-a group and a SO 3 H group At least one of them.]
표 1~표 6 중, Ph1~Ph5는, 각각 이하와 같다. 하기식 중, *는 결합손을 나타낸다.In Tables 1 to 6, Ph1 to Ph5 are respectively as follows. In the following formula, * denotes a binding hand.
<화학식 17>≪ Formula 17 >
그 중에서도, 식(A-I-1)로 나타나는 화합물로서는, 화합물 31~화합물 90이 바람직하고, 화합물 46~화합물 60이 보다 바람직하다.Among them, the compounds represented by the formula (A-I-1) are preferably the compounds 31 to 90, and the compounds 46 to 60 are more preferable.
화합물(A-I)은, 식(A-II)의 화합물(이하, 화합물(A-II)이라고 하는 경우가 있다)의 술폰화에 의해 제조할 수 있다. 화합물(A-II)로서는, 염산염, 인산염, 과염소산염, BF4염, PF6염 등을 들 수 있다.The compound (A-I) can be produced by sulfonation of a compound of the formula (A-II) (hereinafter sometimes referred to as a compound (A-II)). Examples of the compound (A-II) include hydrochloride, phosphate, perchlorate, BF 4 salt and PF 6 salt.
<화학식 18>≪ Formula 18 >
[식 중,[Wherein,
R1a, R2a, R3a, R4a, R5a, R6a, R7a 및 R8a는, 각각 독립적으로, 수소 원자, 또는 탄소수 1~10의 알킬기를 나타낸다.Each of R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
R9a 및 R10a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 치환되어 있어도 되는 방향족 탄화수소기, 또는 치환되어 있어도 되는 아르알킬기를 나타낸다.R 9a and R 10a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
R11a~R20a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 또는 할로겐 원자를 나타낸다.Each of R 11a to R 20a independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a halogen atom.
상기 R1a~R20a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.In the above-mentioned R 1a to R 20a , the alkyl group may have an oxygen atom inserted in the methylene period constituting the alkyl group.
R45a 및 R46a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.R 45a and R 46a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group.
R55a는, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
상기 R45a, R46a, 및 R55a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.In R 45a , R 46a and R 55a , the alkyl group may have oxygen atoms inserted into the constituent methylene period.
M1은, Cl-, 인산 이온, 과염소산염, BF4염이나 PF6염을 나타낸다.]M 1 represents Cl - , a phosphate ion, perchlorate, BF 4 salt or PF 6 salt.
술폰화의 방법으로서는 공지의 다양한 수법, 예를 들면, Journal of Organic Chemistry, (1994),vol.59,#11, p.3232-3236에 기재되어 있는 수법을 들 수 있다.As the method of sulfonation, various known methods can be mentioned, for example, the method described in Journal of Organic Chemistry, (1994), vol. 59, # 11, p. 3232-3236.
화합물(A-II)은, 예를 들면, 식(B-I)로 나타나는 화합물과 식(C-I)로 나타나는 화합물을, 반응시킴으로써 제조할 수 있다. 이러한 반응은, 유기 용매의 존재하에서 행해도 되고, 무용매하에서 행해도 된다.The compound (A-II) can be produced, for example, by reacting a compound represented by the formula (B-I) with a compound represented by the formula (C-I). This reaction may be carried out in the presence of an organic solvent or under no solvent.
<화학식 19>(19)
<화학식 20>(20)
[식(B-I) 및 식(C-I) 중, R1a~R20a, R45a, R46a 및 R55a는, 각각 상기와 동일한 의미를 나타낸다.][Wherein R 1a to R 20a , R 45a , R 46a and R 55a have the same meanings as defined above, respectively, in the formulas (B-I) and (C-I)
또한 화합물(A-II)은, 식(B-II)으로 나타나는 화합물과, 식(C-II) 및 식(C-III)으로 나타나는 화합물을, 반응시킴으로써 제조할 수 있다. 이러한 반응은, 유기 용매의 존재하에서 행해도 되고, 무용매하에서 행해도 된다.The compound (A-II) can be produced by reacting a compound represented by the formula (B-II) with a compound represented by the formula (C-II) and the formula (C-III). This reaction may be carried out in the presence of an organic solvent or under no solvent.
<화학식 21>≪ Formula 21 >
[식(B-II), 식(C-II), 및 식(C-III) 중, R1a~R20a, R45a, R46a 및 R55a는, 각각 상기와 동일한 의미를 나타낸다.][Wherein R 1a to R 20a , R 45a , R 46a and R 55a have the same meanings as defined above, in the formulas (B-II), (C-II)
식(C-II)으로 나타나는 화합물 및 식(C-III)으로 나타나는 화합물은, 동일한 것이 바람직하다.The compound represented by formula (C-II) and the compound represented by formula (C-III) are preferably the same.
식(B-I)으로 나타나는 화합물에 대하여, 식(C-I)으로 나타나는 화합물의 사용량은, 식(B-I)으로 나타나는 화합물 1몰에 대하여, 각각 바람직하게는 0.5몰 이상 8몰 이하이고, 보다 바람직하게는 1몰 이상 3몰 이하이다.The amount of the compound represented by the formula (C-I) to be used in the compound represented by the formula (B-I) is preferably 0.5 to 8 moles per mole of the compound represented by the formula (B-I) , More preferably 1 mole or more and 3 mole or less.
식(B-II)으로 나타나는 화합물에 대하여, 식(C-II)으로 나타나는 화합물 및 식(C-III)으로 나타나는 화합물의 합계의 사용량은, 식(B-II)으로 나타나는 화합물 1몰에 대하여, 바람직하게는 0.5몰 이상 8몰 이하이고, 보다 바람직하게는 1몰 이상 3몰 이하이다.The total amount of the compound represented by the formula (C-II) and the compound represented by the formula (C-III) is 1 mole or more relative to 1 mole of the compound represented by the formula (B-II) , Preferably not less than 0.5 mole and not more than 8 mole, and more preferably not less than 1 mole but not more than 3 mole.
반응 온도는, 30~180℃이 바람직하고, 80~130℃이 보다 바람직하다. 반응 시간은, 1시간~12시간이 바람직하고, 3시간~8시간이 보다 바람직하다.The reaction temperature is preferably 30 to 180 占 폚, more preferably 80 to 130 占 폚. The reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.
어느 반응이나, 수율의 점에서, 유기 용매 중에서 행하는 것이 바람직하다.From the standpoint of any reaction or yield, it is preferable to carry out the reaction in an organic solvent.
유기용매로서는, 톨루엔, 자일렌 등의 탄화수소 용매;클로로벤젠, 디클로로벤젠, 클로로포름 등의 할로겐화 탄화수소 용매;메탄올, 에탄올, 이소프로판올, 부탄올 등의 알코올 용매;니트로 벤젠 등의 니트로 탄화수소 용매;메틸이소부틸케톤 등의 케톤 용매;1-메틸-2-피롤리돈 등의 아미드 용매;등을 들 수 있다. 유기 용매의 사용량은, 식(B-I) 또는 식(B-II)으로 나타나는 화합물 1질량부에 대하여, 바람직하게는 1질량부 이상 20질량부 이하이고, 보다 바람직하게는 2질량부 이상 10질량부 이하이다.Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform, alcohol solvents such as methanol, ethanol, isopropanol and butanol, nitrohydrocarbon solvents such as nitrobenzene, And amide solvents such as 1-methyl-2-pyrrolidone; and the like. The amount of the organic solvent to be used is preferably not less than 1 part by mass and not more than 20 parts by mass, more preferably not less than 2 parts by mass, more preferably not less than 10 parts by mass based on 1 part by mass of the compound represented by the formula (B-I) Parts by mass or less.
상기 반응은, 수율의 점에서, 축합제의 존재하에 실시하는 것이 바람직하다. 축합제로서는, 인산, 폴리인산, 옥시염화인, 황산, 염화티오닐 등을 들 수 있다.The reaction is preferably carried out in the presence of a condensing agent in view of the yield. Examples of the condensing agent include phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, thionyl chloride and the like.
축합제의 사용량은, 식(B-I) 또는 식(B-II)으로 나타나는 화합물 1질량부에 대하여, 바람직하게는 0.1질량부 이상 20질량부 이하이고, 보다 바람직하게는 0.2질량부 이상 5질량부 이하이다.The amount of the condensing agent to be used is preferably not less than 0.1 part by mass and not more than 20 parts by mass, more preferably not less than 0.2 parts by mass, based on 1 part by mass of the compound represented by the formula (B-I) or (B-II) Parts by mass or less.
반응 혼합물로부터 화합물(A-II)을 취득하는 방법은 특별히 한정되지 않고, 공지의 여러 가지의 수법을 채용할 수 있다. 예를 들면, 반응 혼합물을 알코올(예를 들면, 메탄올 등) 등의 용매와 함께 혼합하고, 석출한 결정을 여과 취득하는 방법을 들 수 있다. 반응 혼합물은 상기 알코올 등의 용매에 첨가하는 것이 바람직하다. 반응 혼합물을 첨가할 때의 온도는, 바람직하게는 -100 이상 50 이하, 보다 바람직하게는 -80 이상 0 이하이다. 또한, 이 후, 동 온도로 0.5~2시간 정도 교반하는 것이 바람직하다. 여과 취득한 결정은, 물 등으로 세정하고, 이어서 건조하는 것이 바람직하다. 또한 필요에 따라서, 재결정 등의 공지의 수법에 의해 추가로 정제해도 된다.The method for obtaining the compound (A-II) from the reaction mixture is not particularly limited, and various known methods can be employed. For example, there can be mentioned a method of mixing the reaction mixture with a solvent such as alcohol (for example, methanol or the like), and filtering out the precipitated crystals. The reaction mixture is preferably added to a solvent such as the above-mentioned alcohol. The temperature at the time of adding the reaction mixture is preferably -100 to 50, more preferably -80 or more and 0 or less. Thereafter, stirring is preferably performed at the same temperature for about 0.5 to 2 hours. The crystals obtained by filtration are preferably washed with water or the like and then dried. If necessary, it may be further purified by a known method such as recrystallization.
화합물(B-I) 및 화합물(B-II)의 제조 방법으로서는, 공지의 여러 가지의 수법, 예를 들면, 서독일 특허출원 P3928243.0호에 기재되어 있는 수법을 들 수 있다.Examples of the method for producing the compound (B-I) and the compound (B-II) include various known methods, for example, the methods described in West German Patent Application No. P3928243.0.
화합물(C-II) 및 화합물(C-III)의 제조 방법으로서는, 국제공개 제2012/053211호에 기재되어 있는 수법 등의 공지의 여러 가지의 수법을 들 수 있다.Examples of the method for producing the compound (C-II) and the compound (C-III) include various known methods such as those described in International Publication No. 2012/053211.
화합물(C-I)은, R9a 및 R10a가 알킬기 또는 아르알킬기일 때는, 식(C-IV)로 나타나는 화합물(이하, 화합물(C-IV)이라고 한다)을 알킬화제 또는 아르알킬화제와 반응시킴으로써 제조할 수 있고, 이 화합물(C-IV)은 식(C-V)으로 나타나는 화합물(이하, 화합물(C-V)이라고 한다)과 식(C-VI)으로 나타나는 화합물(이하, 화합물(C-VI)이라고 한다)을 반응시킴으로써 제조할 수 있다. 또한 화합물(C-I)은, R9a 및 R10a의 종류에 의하지 않고, 화합물(C-V)과 화합물(C-VI)로부터 직접 제조할 수도 있다.The compound (C-I) is obtained by reacting a compound represented by the formula (C-IV) (hereinafter referred to as a compound (C-IV)) with an alkylating agent or an aralkylating agent when R 9a and R 10a are an alkyl group or an aralkyl group (Hereinafter, referred to as a compound (C)) represented by the formula (C-V) (hereinafter referred to as a compound -VI) ").≪ / RTI > The compound (C-I) can also be produced directly from the compound (C-V) and the compound (C-VI), regardless of the kind of R 9a and R 10a .
<화학식 22>(22)
(식 중, R1a~R20a는 상기와 동일하다. R1B는 R9a, R10a와 동일하고, R2B는 R11a, R13a와 동일하고, R3B는, R12a, R14a와 동일하고, R4B는 R15a, R18a와 동일하고, R5B는 R16a, R19a와 동일하고, R6B는 R17a, R20a와 동일하다. R7B, R8B는 할로겐 원자이다).(Wherein, R 1a ~ R 20a are the same as above. R 1B has is, R 12a, R 14a and the same R 9a, R 10a and the same and, R 2B is R 11a, R 13a and the same and, R 3B R 4B is the same as R 15a and R 18a , R 5B is the same as R 16a and R 19a , R 6B is the same as R 17a and R 20a, and R 7B and R 8b are halogen atoms.
알킬화제로서는, 할로겐화 알킬, 황산 에스테르 등의 공지의 알킬화제를 이용할 수 있고, 특히 입수의 용이함에서 할로겐화 알킬이 바람직하고, 합성의 용이함에서 1급의 요오드화 알킬이 특히 바람직하다. 아르알킬화제로서는, 할로겐화 벤질 등을 이용할 수 있다.As the alkylating agent, known alkylating agents such as alkyl halide and sulfuric acid ester can be used. In particular, alkyl halide is preferable in view of easiness to obtain. Particularly preferred is primary alkyl iodide because of easiness of synthesis. As the aralkylating agent, halogenated benzyl and the like can be used.
알킬화제의 예로서, 구체적으로는, 요오드화 메틸, 요오드화 에틸, 요오드화 노말 부틸, 브롬화 에틸, 브롬화 노말 부틸, 황산 디메틸, 황산 디에틸 등을 들 수 있다. 아르알킬화제의 예로서, 구체적으로는, 요오드화 벤질, 브롬화 벤질 등을 들 수 있다.Specific examples of the alkylating agent include methyl iodide, ethyl iodide, n-butyl iodide, ethyl bromide, n-butyl bromide, dimethyl sulfate, and diethyl sulfate. Specific examples of the aralkylating agent include benzyl iodide and benzyl bromide.
알킬화제 또는 아르알킬화제의 사용량은, 식(C-IV)으로 나타나는 화합물 1몰에 대하여, 각각 바람직하게는 2몰 이상 6몰 이하이고, 보다 바람직하게는 2몰 이상 4몰 이하이다.The amount of the alkylating agent or aralkylating agent to be used is preferably 2 mol or more and 6 mol or less, and more preferably 2 mol or more and 4 mol or less, per 1 mol of the compound represented by the formula (C-IV).
반응 온도는, 20~180℃가 바람직하고, 30~50℃가 보다 바람직하다. 반응 시간은, 10분~10시간이 바람직하고, 30분~2시간이 보다 바람직하다.The reaction temperature is preferably 20 to 180 占 폚, more preferably 30 to 50 占 폚. The reaction time is preferably 10 minutes to 10 hours, more preferably 30 minutes to 2 hours.
어느 반응이나, 수율의 점에서, 유기 용매 중에서 행하는 것이 바람직하다. 유기 용매로서는, 톨루엔, 자일렌 등의 탄화수소 용매;클로로 벤젠, 디클로로 벤젠, 클로로 포름 등의 할로겐화 탄화수소 용매;메탄놀, 에탄올, 이소프로판올, 부탄올 등의 알코올 용매;니트로벤젠 등의 니트로 탄화수소 용매;메틸이소부틸 케톤 등의 케톤 용매;N,N-디메틸포름아미드, N,N-디메틸아세토아미드, 1-메틸-2-피롤리돈 등의 아미드 용매;등을 들 수 있다. 유기 용매의 사용량은, 식(C-IV)으로 나타나는 화합물 1질량부에 대하여, 바람직하게는 1질량부 이상 20질량부 이하이고, 보다 바람직하게는 2질량부 이상 10질량부 이하이다.From the standpoint of any reaction or yield, it is preferable to carry out the reaction in an organic solvent. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform, alcohol solvents such as methanol, ethanol, isopropanol and butanol, nitrohydrocarbon solvents such as nitrobenzene, Ketone solvents such as butyl ketone; and amide solvents such as N, N-dimethylformamide, N, N-dimethylacetoamide and 1-methyl-2-pyrrolidone. The amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 2 parts by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by the formula (C-IV).
상기 반응은, 수율의 점에서, 알칼리성 물질의 존재하에 실시하는 것이 바람직하다. 알칼리성 물질로서는, 수소화 나트륨, LDA, DIBAL, t-부톡시칼륨 등을 들 수 있다.The reaction is preferably carried out in the presence of an alkaline substance in terms of yield. Examples of the alkaline substance include sodium hydride, LDA, DIBAL, t-butoxy potassium and the like.
염기성 물질의 사용량은, 식(C-IV)으로 나타나는 화합물 1몰에 대하여, 각각 바람직하게는 2몰 이상 6몰 이하이고, 보다 바람직하게는 2몰 이상 4몰 이하이다.The amount of the basic substance to be used is preferably 2 mol or more and 6 mol or less, and more preferably 2 mol or more and 4 mol or less, with respect to 1 mol of the compound represented by the formula (C-IV).
반응 혼합물로부터 화합물(C-I)을 취득하는 방법은 특별히 한정되지 않고, 공지의 여러 가지의 수법을 채용할 수 있다. 예를 들면, 반응 혼합물을 알코올(예를 들면, 메탄올 등) 등의 용매와 함께 혼합하고, 석출한 결정을 여과 취득하는 방법을 들 수 있다. 반응 혼합물은 상기 알코올 등의 용매에 첨가하는 것이 바람직하다. 반응 혼합물을 첨가할 때의 온도는, 바람직하게는 -100 이상 50 이하, 보다 바람직하게는 -80 이상 0 이하이다. 또한, 이 후, 동온도로 0.5~2시간 정도 교반하는 것이 바람직하다. 여과 취득한 결정은, 물 등으로 세정하고, 이어서 건조하는 것이 바람직하다. 또한 필요에 따라서, 재결정 등의 공지의 수법에 의해 추가로 정제해도 된다.The method of obtaining the compound (C-I) from the reaction mixture is not particularly limited, and various known methods may be employed. For example, there can be mentioned a method of mixing the reaction mixture with a solvent such as alcohol (for example, methanol or the like), and filtering out the precipitated crystals. The reaction mixture is preferably added to a solvent such as the above-mentioned alcohol. The temperature at the time of adding the reaction mixture is preferably -100 to 50, more preferably -80 or more and 0 or less. Thereafter, stirring is preferably performed at the same temperature for about 0.5 to 2 hours. The crystals obtained by filtration are preferably washed with water or the like and then dried. If necessary, it may be further purified by a known method such as recrystallization.
상기 화합물(C-IV)은, 상술한 바와 같이, 화합물(C-V)과 화합물(C-VI)을 반응시킴으로써 제조할 수 있다. 또한 상기 화합물(C-I)도, 상술한 바와 같이, 화합물(C-V)과 화합물(C-VI)을 반응시킴으로써 제조할 수 있다.The compound (C-IV) can be produced by reacting the compound (C-V) with the compound (C-VI) as described above. The compound (C-I) can also be produced by reacting the compound (C-V) with the compound (C-VI) as described above.
<화학식 23>≪ Formula 23 >
식(C-VI) 중, R7B, R8B로 나타나는 할로겐 원자로서는, 불소 원자, 염소 원자, 브롬 원자, 요오드 원자를 들 수 있고, 원료 입수의 용이함의 관점에서, 불소 원자, 염소 원자가 바람직하다. Examples of the halogen atom represented by R 7B and R 8B in the formula (C-VI) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom and a chlorine atom are preferable from the viewpoint of easiness of obtaining a raw material .
화합물(C-V)의 사용량은, 화합물(C-VI) 1몰에 대하여, 바람직하게는 2몰 이상 5몰 이하이고, 보다 바람직하게는 2몰 이상 3몰 이하이다.The amount of the compound (C-V) to be used is preferably 2 mol or more and 5 mol or less, and more preferably 2 mol or more and 3 mol or less, relative to 1 mol of the compound (C-VI).
반응 온도는, 20~180℃가 바람직하고, 30~50℃가 보다 바람직하다. 반응 시간은, 10분~10시간이 바람직하고, 30분~2시간이 보다 바람직하다.The reaction temperature is preferably 20 to 180 占 폚, more preferably 30 to 50 占 폚. The reaction time is preferably 10 minutes to 10 hours, more preferably 30 minutes to 2 hours.
어느 반응이나, 수율의 점에서, 유기 용매 중에서 행하는 것이 바람직하다. 유기 용매로서는, 톨루엔, 자일렌 등의 탄화수소 용매;클로로벤젠, 디클로로벤젠, 클로로포름 등의 할로겐화 탄화수소 용매;메탄올, 에탄올, 이소프로판올, 부탄올 등의 알코올 용매;니트로 벤젠 등의 니트로 탄화수소 용매;메틸이소부틸 케톤 등의 케톤 용매;N,N-디메틸포름아미드, N,N-디메틸아세토아미드, 1-메틸-2-피롤리돈 등의 아미드 용매;등을 들 수 있다. 유기 용매의 사용량은, 식(C-VI)으로 나타나는 화합물 1질량부에 대하여, 바람직하게는 1질량부 이상 20질량부 이하이고, 보다 바람직하게는 2질량부 이상 10질량부 이하이다.From the standpoint of any reaction or yield, it is preferable to carry out the reaction in an organic solvent. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform, alcohol solvents such as methanol, ethanol, isopropanol and butanol, nitrohydrocarbon solvents such as nitrobenzene, And amide solvents such as N, N-dimethylformamide, N, N-dimethylacetoamide and 1-methyl-2-pyrrolidone. The amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, and more preferably 2 parts by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by the formula (C-VI).
상기 반응은, 수율의 점에서, 팔라듐 화합물, 포스핀 화합물 및 염기성 물질의 존재하에 실시하는 것이 바람직하다.The above reaction is preferably carried out in the presence of a palladium compound, a phosphine compound and a basic substance in terms of yield.
팔라듐 화합물로서는, 아세트산 팔라듐(II), 염화 팔라듐(II), 브롬화 팔라듐(II), 비스(2,4-펜탄디오나트)팔라듐(II), 비스(디벤질리덴아세톤)팔라듐(0), 트리스(디벤질리덴아세톤)디팔라듐(0) 등을 들 수 있다.Examples of the palladium compound include palladium (II) acetate, palladium (II) chloride, palladium (II) bromide, bis (2,4-pentanedionato) palladium (II), bis (dibenzylideneacetone) palladium (Dibenzylideneacetone) dipalladium (0), and the like.
팔라듐 화합물의 사용량은, 화합물(C-VI) 1몰에 대하여, 각각 바람직하게는 0.0001몰 이상 0.5몰 이하이고, 보다 바람직하게는 0.001몰 이상 0.1몰 이하이다.The amount of the palladium compound to be used is preferably 0.0001 mol or more and 0.5 mol or less, and more preferably 0.001 mol or more and 0.1 mol or less, per 1 mol of the compound (C-VI).
포스핀 화합물로서는, dppf, Xantphos, BINAP, XPhos, SPhos, MePhos 등을 들 수 있다.Examples of the phosphine compound include dppf, Xantphos, BINAP, XPhos, SPhos, and MePhos.
포스핀 화합물의 사용량은, 화합물(C-VI) 1몰에 대하여, 각각 바람직하게는 0.001몰 이상 0.5몰 이하이고, 보다 바람직하게는 0.003몰 이상 0.1몰 이하이다.The amount of the phosphine compound to be used is preferably 0.001 mol or more and 0.5 mol or less, and more preferably 0.003 mol or more and 0.1 mol or less, per 1 mol of the compound (C-VI).
염기성 화합물로서는, 수산화 나트륨, 수산화 칼륨, 탄산 나트륨, 탄산 칼륨, 나트륨메톡시드, 칼륨메톡시드, t-부톡시나트륨, t-부톡시칼륨 등을 들 수 있다.Examples of the basic compound include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium methoxide, t-butoxy sodium and t-butoxy potassium.
알칼리성 화합물의 사용량은, 화합물(C-VI) 1몰에 대하여, 각각 바람직하게는 1몰 이상 5몰 이하이고, 보다 바람직하게는 1몰 이상 3몰 이하이다.The amount of the alkaline compound to be used is preferably 1 to 5 moles, and more preferably 1 to 3 moles, per 1 mole of the compound (C-VI).
반응 혼합물로부터 화합물(C-IV)을 취득하는 방법은 특별히 한정되지 않고, 공지의 여러 가지의 수법을 채용할 수 있다. 예를 들면, 반응 혼합물을 알코올(예를 들면, 메탄올 등) 등의 용매와 함께 혼합하고, 석출한 결정을 여과 취득하는 방법을 들 수 있다. 반응 혼합물은 상기 알코올 등의 용매에 첨가하는 것이 바람직하다. 반응 혼합물을 첨가할 때의 온도는, 바람직하게는 -100 이상 50 이하, 보다 바람직하게는 -80 이상 0 이하이다. 또한, 이 후, 동온도로 0.5~2시간 정도 교반하는 것이 바람직하다. 여과 취득한 결정은, 물 등으로 세정하고, 이어서 건조하는 것이 바람직하다. 또한 필요에 따라서, 재결정 등의 공지의 수법에 따라 추가로 정제해도 된다.The method for obtaining the compound (C-IV) from the reaction mixture is not particularly limited, and various known methods can be employed. For example, there can be mentioned a method of mixing the reaction mixture with a solvent such as alcohol (for example, methanol or the like), and filtering out the precipitated crystals. The reaction mixture is preferably added to a solvent such as the above-mentioned alcohol. The temperature at the time of adding the reaction mixture is preferably -100 to 50, more preferably -80 or more and 0 or less. Thereafter, stirring is preferably performed at the same temperature for about 0.5 to 2 hours. The crystals obtained by filtration are preferably washed with water or the like and then dried. If necessary, it may be further purified according to a known method such as recrystallization.
본 발명의 화합물(A-I)은, 섬유 제품에 적용할 수 있고, 예를 들면 섬유 재료에 집어넣어, 함침, 부착 등을 함으로써 섬유 재료를 착색할 수 있다. 또한 본 발명의 화합물(A-I)은, 착색제(이하 「착색제(A)」라고 하는 경우가 있다)의 염료로서 착색 경화성 수지 조성물에 포함된다. 이 착색 경화성 수지 조성물은, 추가로 수지(B)를 포함하는 것이 바람직하고, 더하여 중합성 화합물(C), 중합 개시제(D) 및 용제(E)를 포함하는 것이 보다 바람직하다. 또한 추가로 중합 개시 조제(D1), 레벨링제(F) 등을 포함하는 것도 바람직하다.The compound (A-I) of the present invention can be applied to a fiber product, and can be colored by, for example, inserting it into a fiber material and impregnating or attaching it. Further, the compound (A-I) of the present invention is contained in the colored curable resin composition as a dye of a colorant (hereinafter sometimes referred to as "colorant (A)"). The colored curable resin composition preferably further contains a resin (B), and more preferably a polymerizable compound (C), a polymerization initiator (D) and a solvent (E). It is also preferable to further include a polymerization initiator (D1), a leveling agent (F), and the like.
본 명세서에 있어서, 각 성분으로서 예시하는 화합물은, 특별히 언급이 없는 한, 단독으로 또는 복수종을 조합하여 사용할 수 있다.In the present specification, the compounds exemplified as respective components may be used singly or in combination of plural kinds, unless otherwise specified.
<착색제(A)>≪ Colorant (A) >
착색제(A)는, 본 발명의 화합물(A-I)을 유효 성분으로 하는 염료를 단독으로 이용해도 되지만, 조색을 위해, 즉 분광 특성을 조정하기 위해서, 추가로 다른 염료(A1), 안료(P), 또는 이들의 혼합물을 포함하고 있어도 된다.The colorant (A) may be used alone as a dye containing the compound (A-I) of the present invention as an active ingredient, but it may further contain other dyes (A1), pigments P), or a mixture thereof.
염료(A1)로서는, 유용성 염료, 산성 염료, 알칼리성 염료, 직접 염료, 매염 염료, 산성 염료의 아민염이나 산성 염료의 술폰 아미드 유도체 등의 염료를 들 수 있고, 예를 들면, 칼라 인덱스(The Society of Dyers and Colourists 출판)에서 염료로 분류되어 있는 화합물이나, 염색 노트(색염사)에 기재되어 있는 공지의 염료를 들 수 있다. 또한, 화학 구조에 의하면, 아조 염료, 시아닌 염료, 트리페닐메탄 염료, 잔텐 염료, 프탈로시아닌 염료, 나프토퀴논 염료, 퀴논이민 염료, 메틴 염료, 아조메틴 염료, 스쿠아릴륨 염료, 아크리딘 염료, 스티릴 염료, 쿠마린 염료, 퀴놀린 염료 및 니트로 염료 등을 들 수 있다. 이들 중, 유기 용제 가용성 염료가 바람직하게 이용된다.Examples of the dye (A1) include dyes such as oil-soluble dyes, acid dyes, alkaline dyes, direct dyes, mordant dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. of Dyers and Colourists) or known dyes listed in Dyeing Note (Color Dyeing). In addition, according to the chemical structure, it is also possible to use an azo dye, a cyanine dye, a triphenylmethane dye, a xanthine dye, a phthalocyanine dye, a naphthoquinone dye, a quinoneimine dye, a methine dye, an azomethine dye, a squarylium dye, Styryl dyes, coumarin dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferably used.
구체적으로는,Specifically,
C.I. 솔벤트 옐로우 4(이하, C.I. 솔벤트 옐로우의 기재를 생략하고, 번호만의 기재로 한다.), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;C.I. 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, and 83 were used as the solvent yellow 4 (hereinafter, the description of CI solvent yellow was omitted. 89, 94, 98, 99, 162;
C.I.솔벤트 레드 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172 , 175, 181, 207, 218, 222, 227, 230, 245, 247;
C.I.솔벤트 오렌지 2, 7, 11, 15, 26, 41, 54, 56, 99;C.I. solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C.I.솔벤트 블루 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, , 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C.I.솔벤트 그린 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35;등의 C.I.솔벤트 염료,C.I. Solvent Dyes such as C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34,
C.I.애시드 옐로우 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184 , 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C.I.애시드 레드 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 87, 88, 91 , 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217 , 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349 , 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C.I.애시드 오렌지 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C.I.애시드 바이올렛 6 B, 7, 9, 17, 19, 30, 102;C.I. Acid Violet 6 B, 7, 9, 17, 19, 30, 102;
C.I.애시드 블루 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335;CI Acid Blue 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103 , 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234 , 236, 242, 243, 256, 259, 267, 285, 296, 315, 335;
C.I.애시드 그린 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109 등의 C.I.애시드 염료,C.I. Acid dyes such as C.I. acid green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105,
C.I.다이렉트 옐로우 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129 , 136, 138, 141;
C.I.다이렉트 레드 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211 , 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C.I.애시드 오렌지 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C.I.애시드 레드 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;C. I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C.I.애시드 그린 3, 5, 9, 25, 27, 28, 41;C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C.I.애시드 바이올렛 34, 120;C.I. Acid Violet 34, 120;
C.I.애시드 블루 25, 27, 40, 45, 78, 80, 112;등의 C.I.애시드 염료,C.I. Acid dyes such as C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C.I.다이렉트 옐로우 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102 , 108, 109, 129, 132, 136, 138, 141;
C.I.다이렉트 오렌지 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C.I.다이렉트 바이올렛 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C.I.다이렉트 블루 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;CI Direct Blue 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99 , 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164 , 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210 , 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259 , 260, 268, 274, 275, 293;
C.I.다이렉트 그린 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 등의 C.I.다이렉트 염료,CI direct dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77,
C.I.디스퍼스 옐로우 51, 54, 76 등의 C.I.디스퍼스 염료,CI Disperse dyes such as C.I. Disperse Yellow 51, 54, 76,
C.I.베이직 레드 1, 10;C. I. Basic Red 1, 10;
C.I.베이직 블루 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68;C. I. Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68;
C.I.베이직 그린 1;등의 C.I.베이직 염료,C. I. Basic dye such as C. I. Basic Green 1;
C.I.리액티브 옐로우 2, 76, 116;C. I. Reactive Yellow 2, 76, 116;
C.I.리액티브 오렌지 16;C.I. Reactive Orange 16;
C.I.리액티브 레드 36;등의 C.I.리액티브 염료,C.I. Reactive Red 36; and the like,
C.I.모던트 옐로우 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;CI. Modern Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C.I.모던트 레드 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;CI Moderntrad 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 30, 32, 33, 36, 37, 38, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;
C.I.모던트 오렌지 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;C.I.Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C.I.모던트 바이올렛 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;C. I. Modern Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;
C.I.모던트 블루 1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61, 74, 77, 83, 84;1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61, 74, 77, 83, 84;
C.I.모던트 그린 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43, 53;등의 C.I.모던트 염료,C.I. Modified dyes such as C.I. Modern Green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43,
C.I.배트 그린 1 등의 C.I.배트 염료 등을 들 수 있다.And C.I. bat dyes such as C. I. Bat Green 1 and the like.
그 중에서도, 청색 염료, 바이올렛색 염료 및 적색 염료가 바람직하다.Among them, a blue dye, a violet dye and a red dye are preferable.
이들 염료는, 단독으로 이용해도 2종 이상을 병용해도 된다.These dyes may be used alone or in combination of two or more.
또한, 화학 구조에 의한 분류에서는, 잔텐 염료가 바람직하다. 잔텐 염료로서는, 공지의 물질을 이용할 수 있다. 예를 들면, 식(1)로 나타나는 화합물이 바람직하다. Further, in classification by chemical structure, a dyestuff dye is preferable. As the xanthine dye, known materials can be used. For example, a compound represented by the formula (1) is preferable.
<화학식 24>≪ EMI ID =
[식(1) 중, R1 및 R2는, 각각 독립적으로, 치환기를 갖고 있어도 되는 페닐기를 나타낸다.[In the formula (1), R 1 and R 2 each independently represent a phenyl group which may have a substituent.
R3 및 R4는, 각각 독립적으로, 탄소수 1~10의 1값의 포화탄화 수소기를 나타내고, 당해 포화 탄화수소기에 포함되는 수소 원자는 할로겐 원자로 치환되어 있어도 되고, 당해 포화 탄화수소기에 포함되는 -CH2-는, -O-, -CO- 또는 -NR11-로 치환되어도 된다.R 3 and R 4 each independently represent a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, and -CH 2 included in the saturated hydrocarbon group - may be substituted with -O-, -CO-, or -NR 11 -.
R1 및 R3은 서로 결합하여, 그들이 결합하는 질소 원자와 함께 되어 질소 원자를 포함하는 환을 형성해도 되고, R2 및 R4는 서로 결합하여, 그들이 결합하는 질소 원자와 함께 되어 질소 원자를 포함하는 환을 형성해도 좋다.R 1 and R 3 may be bonded to each other to form a ring containing a nitrogen atom together with the nitrogen atom to which they are bonded and R 2 and R 4 may be bonded to each other to form a nitrogen atom May be formed.
R5는, -OH, -SO3H, -SO3 -Z+, -CO2H,-CO2 -Z+, -CO2R8, -SO3R8 또는 -SO2NR9R10를 나타낸다.R 5 is, -OH, -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO 2 NR 9 R 10 .
R6 및 R7은, 각각 독립적으로, 수소 원자 또는 탄소수 1~6의 알킬기를 나타낸다.R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m은, 0~4의 정수를 나타낸다. m이 2 이상의 정수인 경우, 복수의 R5는 동일해도 상이해도 된다.m represents an integer of 0 to 4; When m is an integer of 2 or more, a plurality of R 5 s may be the same or different.
R8은, 탄소수 1~20의 1가의 포화 탄화수소기를 나타내고, 당해 포화 탄화수소기에 포함되는 수소 원자는, 할로겐 원자로 치환되어 있어도 된다.R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
Z+는, +N(R11)4, Na+ 또는 K+를 나타낸다.Z + represents + N (R < 11 >) 4 , Na + or K + .
R9 및 R10은, 각각 독립적으로, 수소 원자 또는 탄소수 1~20의 1가의 포화 탄화수소기를 나타내고, R9 및 R10은, 서로 결합하여 질소 원자와 함께 3~10원 함질소 복소환을 형성하고 있어도 된다.R 9 and R 10 are each independently a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms; R 9 and R 10 are bonded to each other to form a nitrogen heterocycle having from 3 to 10 members together with a nitrogen atom; .
R11은, 각각 독립적으로, 수소 원자, 탄소수 1~20의 1가의 포화 탄화수소기 또는 탄소수 7~10의 아르알킬기를 나타낸다.]And R < 11 > each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
R8, R9, R10 및 R11을 나타내는 탄소수 1~20의 1가의 포화 탄화수소기로서는, 예를 들면, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, 도데실기, 헥사데실기 및 이코실기 등의 탄소수 1~20의 직쇄상 알킬기;이소프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 이소펜틸기, 네오펜틸기 및 2-에틸헥실기 등의 탄소수 3~20의 분기 쇄상 알킬기;사이클로프로필기, 사이클로펜틸기, 사이클로헥실기, 사이클로헵틸기, 사이클로옥틸기 및 트리사이클로데실기 등의 탄소수 3~20의 지환식 포화 탄화수소기를 들 수 있다.Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which represent R 8 , R 9 , R 10 and R 11 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, , A straight chain alkyl group having 1 to 20 carbon atoms such as a nonyl group, a decyl group, a dodecyl group, a hexadecyl group and an icosyl group, an isopropyl group, an isobutyl group, a sec-butyl group, Branched chain alkyl groups having 3 to 20 carbon atoms such as cyclopentyl, cyclopentyl, cyclohexyl, cyclooctyl and tricyclodecyl groups, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and tricyclodecyl; And an alicyclic saturated hydrocarbon group.
-CO2R8로서는, 예를 들면, 메톡시카보닐기, 에톡시카보닐기, 프로폭시카보닐기, tert-부톡시카보닐기, 헥실옥시카보닐기 및 이코실옥시카보닐기 등을 들 수 있다.Examples of -CO 2 R 8 include a methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, hexyloxycarbonyl group, and eicosyloxycarbonyl group.
-SO3R8로서는, 예를 들면, 메톡시술포닐기, 에톡시술포닐기, 프로폭시술포닐기, tert-부톡시술포닐기, 헥실옥시술포닐기 및 이코실옥시술포닐기 등을 들 수 있다.Examples of -SO 3 R 8 include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group and an icosyloxysulfonyl group .
-SO2NR9R10으로서는, 예를 들면, 술파모일기;Examples of -SO 2 NR 9 R 10, for example, sulfamoyl group;
N-메틸술파모일기, N-에틸술파모일기, N-프로필술파모일기, N-이소프로필술파모일기, N-부틸술파모일기, N-이소부틸술파모일기, N-sec-부틸술파모일기, N-tert-부틸술파모일기, N-펜틸술파모일기, N-(1-에틸프로필)술파모일기, N-(1,1-디메틸프로필)술파모일기, N-(1,2-디메틸프로필)술파모일기, N-(2,2-디메틸프로필)술파모일기, N-(1-메틸부틸)술파모일기, N-(2-메틸부틸)술파모일기, N-(3-메틸부틸)술파모일기, N-사이클로펜틸술파모일기, N-헥실술파모일기, N-(1,3-디메틸부틸)술파모일기, N-(3,3-디메틸부틸)술파모일기, N-헵틸술파모일기, N-(1-메틸헥실)술파모일기, N-(1,4-디메틸펜틸)술파모일기, N-옥틸술파모일기, N-(2-에틸헥실)술파모일기, N-(1,5-디메틸헥실)술파모일기, N-(1,1,2,2-테트라메틸부틸)술파모일기 등의 N-1 치환 술파모일기;N-isopropylsulfamoyl group, N-methylsulfamoyl group, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, (1, 1-dimethylpropyl) sulfamoyl group, N- (1, 2-dimethylpropyl) sulfamoyl group, N-methylpyrrolyl group, N- (2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (3-methylbutyl) sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) Sulfamoyl group, N- (1,5-dimethylhexyl) sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group N-1 substituted sulfamoyl groups such as N-1 substituted sulfamoyl groups;
N,N-디메틸술파모일기, N,N-에틸메틸술파모일기, N,N-디에틸술파모일기, N,N-프로필메틸술파모일기, N,N-이소프로필메틸술파모일기, N,N-tert-부틸메틸술파모일기, N,N-부틸에틸술파모일기, N,N-비스(1-메틸프로필)술파모일기, N,N-헵틸메틸술파모일기 등의 N, N-2치환 술파모일기 등을 들 수 있다.N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-diethylamino groups such as N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N-2-substituted sulfamoyl group, and the like.
R9 및 R10은, 서로 결합하여 질소 원자와 함께 3~10원 함질소 복소환을 형성하고 있어도 된다. 당해 복소환으로서는, 예를 들면, 이하의 것을 들 수 있다.R 9 and R 10 may combine with each other to form a nitrogen heterocycle having from 3 to 10 members together with a nitrogen atom. Examples of the heterocyclic ring include the following.
<화학식 25>≪ Formula 25 >
R3 및 R4를 나타내는 탄소수 1~10의 1가의 포화 탄화수소기로서는, 상기 중 탄소수 1~10의 것을 들 수 있다. R3 및 R4를 나타내는 탄소수 1~10의 1가의 포화 탄화수소기에 포함되는 수소 원자는 할로겐 원자로 치환되어 있어도 되고, 당해 포화 탄화수소기에 포함되는 -CH2-는, -O-, -CO- 또는 -NR11-로 치환되어도 된다.Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms for R 3 and R 4 include those having 1 to 10 carbon atoms. The hydrogen atom contained in the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms which represents R 3 and R 4 may be substituted with a halogen atom, and -CH 2 - included in the saturated hydrocarbon group may be replaced by -O-, NR < 11 > -.
할로겐 원자로서는, 예를 들면, 불소 원자, 염소 원자, 브롬 원자 및 요오드 원자를 들 수 있다.Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
할로겐 원자로 치환된 포화 탄화수소기로서는, 예를 들면, 플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 퍼플루오로에틸기 및 클로로부틸기 등을 들 수 있다.The saturated hydrocarbon group substituted with a halogen atom includes, for example, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, and a chlorobutyl group.
R6 및 R7을 나타내는 탄소수 1~6의 알킬기로서는, 예를 들면, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 이소프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 이소펜틸기 및 네오펜틸기 등을 들 수 있다.Examples of the alkyl group having 1 to 6 carbon atoms for R 6 and R 7 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an isopropyl group, an isobutyl group, A butyl group, an isopentyl group, and a neopentyl group.
R11을 나타내는 탄소수 7~10의 아르알킬기로서는, 예를 들면, 벤질기, 페닐에틸기 및 페닐부틸기 등을 들 수 있다.Examples of the aralkyl group having 7 to 10 carbon atoms which represents R 11 include a benzyl group, a phenylethyl group and a phenylbutyl group.
Z+는, +N(R11)4, Na+ 또는 K+이고, 바람직하게는 +N(R11)4이다.Z + is a, + N (R 11) 4 , Na + or K +, preferably N + (R 11) 4.
상기 +N(R11)4로서는, 4개의 R11 중, 적어도 2개가 탄소수 5~20의 1가의 포화 탄화수소기인 것이 바람직하다. 또한, 4개의 R11의 합계 탄소수는 20~80이 바람직하고, 20~60이 보다 바람직하다.As the + N (R 11 ) 4 , it is preferable that at least two of the four R 11 s are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. The total number of carbon atoms of the four R < 11 > s is preferably 20 to 80, more preferably 20 to 60. [
R1 및 R2를 나타내는 페닐기는, 치환기를 갖고 있어도 된다. 당해 치환기로서는, 할로겐 원자, -R8, -OH, -OR8, -SO3H, -SO3 -Z+, -CO2H, -CO2R8, -SR8, -SO2R8, -SO3R8 및 -SO2NR9R10을 들 수 있다. 이들 치환기 중에서도, -R8이 바람직하고, 탄소수 1~10의 1가의 포화 탄화수소기가 보다 바람직하다. 이 경우의 -SO3 -Z+로서는, -SO3 -N+(R11)4가 바람직하다.The phenyl group representing R 1 and R 2 may have a substituent. As the substituent, halogen atoms, -R 8, -OH, -OR 8 , -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 R 8, -SR 8, -SO 2 R 8 , -SO 3 R 8 and -SO 2 NR 9 R 10 . Among these substituents, -R 8 is preferable, and a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms is more preferable. Examples of Z +, -SO 3 - - -SO 3 in this case is N + (R 11) 4 are preferred.
-OR8로서는, 예를 들면, 메톡시기, 에톡시기, 프로폭시기, 부톡시기, 펜틸옥시기, 헥실옥시기, 헵틸옥시기, 옥틸옥시기, 2-에틸헥실옥시기 및 이코실옥시기 등을 들 수 있다.Examples of -OR 8 include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, .
-SR8로서는, 예를 들면, 메틸술파닐기, 에틸술파닐기, 부틸술파닐기, 헥실술파닐기, 데실술파닐기 및 이코실술파닐기 등을 들 수 있다.Examples of -SR 8 include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group and an icosylsulfanyl group.
-SO2R8로서는, 예를 들면, 메틸술포닐기, 에틸술포닐기, 부틸술포닐기, 헥실술포닐기, 데실술포닐기 및 이코실술포닐기 등을 들 수 있다.Examples of -SO 2 R 8 include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group and an icosylsulfonyl group.
R3 및 R4로서는, 무치환의 탄소수 1~10의 1가의 포화 탄화수소기가 바람직하고, 탄소수 1~4의 1가의 포화 탄화수소기가 보다 바람직하고, 메틸기 및 에틸기가 더욱 바람직하다.As R 3 and R 4 , an unsubstituted monovalent saturated hydrocarbon group of 1 to 10 carbon atoms is preferable, a monovalent saturated hydrocarbon group of 1 to 4 carbon atoms is more preferable, and a methyl group and an ethyl group are more preferable.
R1 및 R3은 서로 결합하여, 그들이 결합하는 질소 원자와 함께 되어 질소 원자를 포함하는 환을 형성해도 되고, R2 및 R4는 서로 결합하여, 그들이 결합하는 질소 원자와 함께 되어 질소 원자를 포함하는 환을 형성해도 된다. 당해 질소 원자를 포함하는 환으로서는, 예를 들면, 이하의 것을 들 수 있다.R 1 and R 3 may be bonded to each other to form a ring containing a nitrogen atom together with the nitrogen atom to which they are bonded and R 2 and R 4 may be bonded to each other to form a nitrogen atom May be formed. The ring containing the nitrogen atom includes, for example, the following.
<화학식 26>(26)
R5로서는, -SO3H, -SO3 -Z+ 및 -SO2NR9R10이 바람직하다.As R 5, -SO 3 H, -SO 3 - Z + yi, and -SO 2 NR 9 R 10 are preferred.
R6 및 R7로서는, 수소 원자, 메틸기 및 에틸기가 바람직하고, 수소 원자가 보다 바람직하다.As R 6 and R 7 , a hydrogen atom, a methyl group and an ethyl group are preferable, and a hydrogen atom is more preferable.
m은, 0~2의 정수가 바람직하고, 0 또는 1인 것이 보다 바람직하다.m is preferably an integer of 0 to 2, more preferably 0 or 1.
화합물(1)로서는, 식(2)로 나타나는 화합물이 바람직하다.As the compound (1), a compound represented by the formula (2) is preferable.
<화학식 27>≪ Formula 27 >
[식(2) 중, R21, R22, R23 및 R24는, 각각 독립적으로, 탄소수 1~4의 알킬기를 나타낸다.[In the formula (2), R 21 , R 22 , R 23 and R 24 each independently represent an alkyl group having 1 to 4 carbon atoms.
p 및 q는, 각각 독립적으로, 0~5의 정수를 나타낸다. p가 2 이상인 경우, 복수의 R23은 동일해도 상이해도 되고, q가 2 이상인 경우, 복수의 R24는 동일해도 상이해도 된다.]p and q each independently represent an integer of 0 to 5; When p is 2 or more, plural R 23 s may be the same or different, and when q is 2 or more, plural R 24 s may be the same or different.]
R21, R22, R23 및 R24를 나타내는 탄소수 1~4의 알킬기로서는, 메틸기, 에틸기, 프로필기, 부틸기, 이소프로필기, 이소부틸기, sec-부틸기, tert-부틸기 등을 들 수 있다.Examples of the alkyl group having 1 to 4 carbon atoms for R 21 , R 22 , R 23 and R 24 include methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec- .
R21 및 R22는, 각각 독립적으로, 메틸기 및 에틸기인 것이 바람직하다. R23 및 R24는, 메틸기가 바람직하다.R 21 and R 22 are each independently preferably a methyl group and an ethyl group. R 23 and R 24 are preferably a methyl group.
p 및 q는, 0~2의 정수가 바람직하고, 0 또는 1인 것이 보다 바람직하다.p and q are preferably an integer of 0 to 2, more preferably 0 or 1.
화합물(1)로서는, 식(3)으로 나타내는 화합물이 바람직하다.As the compound (1), a compound represented by the formula (3) is preferable.
<화학식 28>(28)
[식(3) 중, R31 및 R32는, 각각 독립적으로, 탄소수 1~4의 알킬기를 나타낸다.[In the formula (3), R 31 and R 32 each independently represent an alkyl group having 1 to 4 carbon atoms.
R33 및 R34는, 각각 독립적으로, 수소 원자 또는 탄소수 1~4의 알킬기를 나타낸다.]R 33 and R 34 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
R31, R32, R33 및 R34를 나타내는 탄소수 1~4의 알킬기로서는, 상기와 동일한 것을 들 수 있다. R31 및 R32는, 각각 독립적으로, 메틸기 또는 에틸기인 것이 바람직하다. R33 및 R34는, 각각 독립적으로, 수소 원자 또는 메틸기인 것이 바람직하다.Examples of the alkyl group having 1 to 4 carbon atoms for R 31 , R 32 , R 33 and R 34 include the same groups as described above. R 31 and R 32 are each independently preferably a methyl group or an ethyl group. R 33 and R 34 are each independently preferably a hydrogen atom or a methyl group.
화합물(1)로서는, 예를 들면, 각각 식(1-1)~식(1-7)로 나타나는 화합물을 들 수 있다. 그 중에서도, 유기 용매에의 용해성이 우수한 점에서, 식(1-1)로 나타나는 화합물이 바람직하다.Examples of the compound (1) include compounds represented by the formulas (1-1) to (1-7), respectively. Among them, a compound represented by the formula (1-1) is preferable in that it is excellent in solubility in an organic solvent.
<화학식 29>(29)
안료(P)로서는, 특별히 한정되지 않고 공지의 안료를 사용할 수 있고, 예를 들면, 칼라 인덱스(The Society of Dyers and Colourists 출판)에서 안료로 분류되어 있는 안료를 들 수 있다.The pigment (P) is not particularly limited and a known pigment can be used. Examples thereof include pigments classified in the color index (The Society of Dyers and Colourists) as pigments.
안료로서는, 예를 들면,As the pigment, for example,
C.I.피그먼트 옐로우 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 등의 황색 안료;CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194 and 214;
C.I.피그먼트 오렌지 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 등의 오렌지색 안료;Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C.I.피그먼트 레드 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 등의 적색 안료;CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, Pigments;
C.I.피그먼트 블루 15, 15:3, 15:4, 15:6, 60 등의 청색 안료;Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;
C.I. 피그먼트 바이올렛 1, 19, 23, 29, 32, 36, 38 등의 바이올렛색 안료;C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C.I. 피그먼트 그린 7, 36, 58 등의 녹색 안료;C.I. Green pigments such as Pigment Green 7, 36, and 58;
C.I. 피그먼트 브라운 23, 25 등의 브라운색 안료;C.I. Brown pigments such as Pigment Brown 23 and 25;
C.I. 피그먼트 블랙 1, 7 등의 흑색 안료 등을 들 수 있다.C.I. Pigment black 1, pigment black 7, and the like.
안료(P)는, 바람직하게는, 프탈로시아닌 안료 및 디옥사진 안료이고, 보다 바람직하게는, C.I. 피그먼트 블루 15:6 및 피그먼트 바이올렛 23으로 이루어지는 군에서 선택되는 적어도 일종이다. 상기의 안료를 포함함으로써, 투과 스펙트럼의 최적화가 용이하고, 칼라 필터의 내광성 및 내약품성이 양호하게 된다.The pigment (P) is preferably a phthalocyanine pigment and a dioxazine pigment, more preferably a C.I. Pigment Blue 15: 6 and Pigment Violet 23. By including the above pigment, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter can be improved.
안료는, 필요에 따라서, 로진 처리, 산성기 또는 염기성기가 도입된 안료 유도체 등을 이용한 표면 처리, 고분자 화합물 등에 의한 안료 표면으로의 그래프트 처리, 황산 미립화법 등에 의한 미립화 처리, 또는 불순물을 제거하기 위한 유기 용제나 물 등에 의한 세정 처리, 이온성 불순물의 이온 교환법 등에 의한 제거 처리 등이 실시되어 있어도 된다. 안료는, 입경이 균일한 것이 바람직하다.If necessary, the pigment may be subjected to a surface treatment using a rosin treatment, a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment to a pigment surface with a polymer compound or the like, an atomization treatment with a sulfuric acid atomization method, A cleaning treatment with an organic solvent or water, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed. The pigment preferably has a uniform particle size.
안료는, 안료 분산제를 함유시켜 분산 처리를 행함으로써, 안료가 용액 중에서 균일하게 분산한 상태의 안료 분산액으로 할 수 있다. 안료는, 각각 단독으로 분산 처리해도 되고, 복수종을 혼합하여 분산 처리해도 된다.The pigment may be a pigment dispersion in which the pigment is uniformly dispersed in a solution by containing a pigment dispersant and performing a dispersion treatment. Each of the pigments may be dispersed singly or plural kinds may be mixed and dispersed.
상기 안료 분산제로서는, 예를 들면, 계면 활성제를 들 수 있고, 양이온계, 음이온계, 비이온계, 양성 중 어느 하나의 계면 활성제라도 된다. 구체적으로는, 폴리에스테르계, 폴리아민계, 아크릴계 등의 안료 분산제 등을 들 수 있다. 이들 안료 분산제는, 단독으로도 2종 이상을 조합하여 이용해도 된다. 안료 분산제로서는, 상품명으로 KP(신에츠화학공업(주) 제), 플로렌(쿄에이샤화학(주) 제), 솔스퍼스(등록상표)(제네카(주) 제), EFKA(등록상표)(BASF사 제), 아디스퍼(등록상표)(아지노모토파인테크노(주) 제), Disperbyk(등록상표)(빅케미사 제) 등을 들 수 있다.The pigment dispersant may be, for example, a surfactant, and may be a cationic, anionic, nonionic or amphoteric surfactant. Specific examples thereof include pigment dispersants such as polyester-based, polyamine-based, and acrylic-based pigments. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyowa Chemical Industry Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (registered trademark) (Manufactured by BASF), ADISPER (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (registered trademark) available from BICKEMISA CO., LTD.
안료 분산제를 이용하는 경우, 그 사용량은, 안료 100질량부에 대하여, 바람직하게는 100질량부 이하이고, 보다 바람직하게는 5질량부 이상 50질량부 이하이다. 안료 분산제의 사용량이 상기의 범위에 있으면, 균일한 분산 상태의 안료 분산액을 얻을 수 있는 경향이 있다.When a pigment dispersant is used, the amount thereof is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of the pigment. When the amount of the pigment dispersant is in the above range, there is a tendency to obtain a pigment dispersion in a uniformly dispersed state.
화합물(A-I)의 함유율은, 착색제(A)의 총량에 대하여, 바람직하게는 1질량% 이상 100질량% 이하이고, 보다 바람직하게는 10질량% 이상 100질량% 이하이다.The content of the compound (A-I) is preferably 1% by mass or more and 100% by mass or less, and more preferably 10% by mass or more and 100% by mass or less, based on the total amount of the colorant (A).
염료(A1)를 포함하는 경우, 그 함유율은, 착색제(A)의 총량에 대하여, 바람직하게는 0.5질량% 이상 80질량% 이하이고, 보다 바람직하게는 40질량% 이상 90질량% 이하이다. 안료(P)를 포함하는 경우, 그 함유율은, 착색제(A)의 총량에 대하여, 바람직하게는 35질량% 이상 99질량% 이하이고, 보다 바람직하게는 1질량% 이상 70질량% 이하이고, 보다 바람직하게는 1질량% 이상 50질량% 이하이다.When the dye (A1) is contained, its content is preferably 0.5% by mass or more and 80% by mass or less, and more preferably 40% by mass or more and 90% by mass or less, based on the total amount of the colorant (A). When the pigment (P) is contained, the content thereof is preferably 35 mass% or more and 99 mass% or less, more preferably 1 mass% or more and 70 mass% or less based on the total amount of the colorant (A) Preferably 1% by mass or more and 50% by mass or less.
착색제(A)의 함유율은, 고형분의 총량에 대하여, 바람직하게는 5질량% 이상 70질량% 이하이고, 보다 바람직하게는 5질량% 이상 60질량% 이하이고, 보다 바람직하게는 5질량% 이상 50질량% 이하이다. 착색제(A)의 함유율이 상기의 범위 내이면, 소망하는 분광도를 얻을 수 있다.The content of the colorant (A) is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and still more preferably 5% % Or less. If the content of the colorant (A) is within the above range, the desired spectral intensity can be obtained.
본 명세서에 있어서 「고형분의 총량」이란, 착색 경화성 수지 조성물로부터 용제(E)를 제외한 성분의 합계량을 말한다. 고형분의 총량 및 이에 대한 각 성분의 함유량은, 예를 들면, 액체 크로마토그래피 또는 가스 크로마토그래피 등의 공지의 분석 수단으로 측정할 수 있다.In the present specification, the "total amount of solid content" refers to the total amount of components excluding the solvent (E) from the colored curable resin composition. The total amount of the solid content and the content of each component can be measured by a known analytical means such as liquid chromatography or gas chromatography.
<수지(B)>≪ Resin (B) >
수지(B)는, 알칼리 가용성 수지(B)인 것이 바람직하다. 알칼리 가용성 수지(B)(이하 「수지(B)」라고 하는 경우가 있다)는, 불포화 카본산 및 불포화 카본산 무수물로 이루어지는 군에서 선택되는 적어도 일종의 단량체(Ba)에 유래하는 구조 단위를 포함하는 공중합체이다.The resin (B) is preferably an alkali-soluble resin (B). The alkali-soluble resin (B) (hereinafter also referred to as " resin (B) ") contains a structural unit derived from at least one monomer (Ba) selected from the group consisting of unsaturated carboxylic acids and unsaturated carbonic anhydrides Lt; / RTI >
이러한 수지(B)로서는, 이하의 수지[K1]~[K6]등을 들 수 있다.Examples of such a resin (B) include the following resins [K1] to [K6].
수지[K1]불포화 카본산 및 불포화 카본산 무수물로 이루어지는 군에서 선택되는 적어도 일종의 단량체(Ba)(이하 「(Ba)」이라고 하는 경우가 있다)와, 탄소수 2~4의 환상 에테르 구조와 에틸렌성 불포화 결합을 갖는 단량체(Bb)(이하 「(Bb)」이라고 하는 경우가 있다)의 공중합체;At least one kind of monomer (Ba) (hereinafter may be referred to as " Ba ") selected from the group consisting of a resin [K1] unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having 2 to 4 carbon atoms, A monomer (Bb) having an unsaturated bond (hereinafter sometimes referred to as " (Bb) ");
수지[K2](Ba)와 (Bb)와, (Ba)와 공중합 가능한 단량체(Bc)(단, (Ba) 및 (Bb)와는 상이하다.)(이하 「(Bc)」라고 하는 경우가 있다)의 공중합체;(Bc) which is copolymerizable with the resin (K2) (Ba) and (Bb) and (Ba) (note that this is different from (Ba) and (Bb)) );
수지[K3](Ba)와 (Bc)의 공중합체;Copolymers of resin [K3] (Ba) and (Bc);
수지[K4](Ba)와 (Bc)의 공중합체에 (Bb)를 반응시킴으로써 얻어지는 수지;A resin obtained by reacting (Bb) a copolymer of the resin [K4] (Ba) and (Bc);
수지[K5](Bb)와 (Bc)의 공중합체에 (Ba)를 반응시킴으로써 얻어지는 수지;Resin [K5] A resin obtained by reacting (Bb) and (Bc) with (Ba);
수지[K6](Bb)와 (Bc)의 공중합체에 (Ba)를 반응시키고, 추가로 카본산 무수물을 반응시킴으로써 얻어지는 수지.Resin [K6] A resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba) and further reacting with a carbonic anhydride.
(Ba)로서는, 구체적으로는, 예를 들면, 아크릴산, 메타크릴산, 크로톤산, o-, m-, p-비닐벤조산 등의 불포화 모노카본산류;(Ba) include, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m- and p-vinylbenzoic acid;
말레인산, 푸말산, 시트라콘산, 메사콘산, 이타콘산, 3-비닐프탈산, 4-비닐프탈산, 3,4,5,6-테트라하이드로프탈산, 1,2,3,6-테트라하이드로프탈산, 디메틸테트라하이드로프탈산, 1,4-사이클로헥센디카본산 등의 불포화 디카본 산류;Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;
메틸-5-노르보르넨-2,3-디카본산, 5-카복시바이사이클로[2.2.1]헵토-2-엔, 5,6-디카복시바이사이클로[2.2.1]헵토-2-엔, 5-카복시-5-메틸바이사이클로[2.2.1]헵토-2-엔, 5-카복시-5-에틸바이사이클로[2.2.1]헵토-2-엔, 5-카복시-6-메틸바이사이클로[2.2.1]헵토-2-엔, 5-카복시-6-에틸바이사이클로[2.2.1]헵토-2-엔 등의 카복시기를 함유하는 바이사이클로 불포화 화합물류;Carboxybicyclo [2.2.1] hepto-2-ene, 5,6-dicarboxybicyclo [2.2.1] hepto-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hepto-2-ene, 5-carboxy-6-methylbicyclo [ 2.2.1] hept-2-ene, and 5-carboxy-6-ethylbicyclo [2.2.1] hepto-2-ene;
무수 말레인산, 시트라콘산 무수물, 이타콘산 무수물, 3-비닐프탈산 무수물, 4-비닐프탈산 무수물, 3,4,5,6-테트라하이드로프탈산 무수물, 1,2,3,6-테트라하이드로프탈산 무수물, 디메틸테트라하이드로프탈산 무수물, 5,6-디카복시바이사이클로[2.2.1]헵토-2-엔 무수물 등의 불포화 디카본 산류 무수물;Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, Unsaturated dicarboxylic anhydrides such as dimethyl tetrahydrophthalic anhydride and 5,6-dicarboxybicyclo [2.2.1] hept-2-eno anhydride;
숙신산모노〔2-(메타)아크릴로일옥시에틸〕, 프탈산 모노〔2-(메타)아크릴로일옥시에틸〕등의 2가 이상의 다가 카본산의 불포화 모노〔(메타)아크릴로일옥시알킬〕에스테르류;Unsaturated mono [(meth) acryloyloxyalkyl] unsaturated monocarboxylic acids such as mono [2- (meth) acryloyloxyethyl] succinate, mono [2- (meth) acryloyloxyethyl] phthalate, Esters;
α-(하이드록시메틸)아크릴산과 같은, 동일 분자 중에 하이드록시기 및 카복시기를 함유하는 불포화 아크릴레이트류 등을 들 수 있다.and unsaturated acrylates containing a hydroxyl group and a carboxy group in the same molecule, such as? - (hydroxymethyl) acrylic acid.
이들 중, 공중합 반응성의 점이나 얻어지는 수지의 알칼리 수용액으로의 용해성의 점에서, 아크릴산, 메타크릴산, 무수 말레인산 등이 바람직하다.Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.
(Bb)는, 예를 들면, 탄소수 2~4의 환상 에테르 구조(예를 들면, 옥시란환, 옥세탄환 및 테트라하이드로푸란환으로 이루어지는 군으로부터 선택되는 적어도 1종)와 에틸렌성 불포화 결합을 갖는 중합성 화합물을 말한다.(Bb) is a compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond Refers to a polymerizable compound.
(Bb)는, 탄소수 2~4의 환상 에테르와 (메타)아크릴로일옥시기를 갖는 단량체가 바람직하다.(Bb) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
또한, 본 명세서에 있어서, 「(메타)아크릴산」이란, 아크릴산 및 메타크릴산으로 이루어지는 군으로부터 선택되는 적어도 1종을 나타낸다. 「(메타)아크릴로일」및「(메타)아크릴레이트」등의 표기도, 동일한 의미를 갖는다.In the present specification, "(meth) acrylic acid" means at least one kind selected from the group consisting of acrylic acid and methacrylic acid. The expressions such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.
(Bb)로서는, 예를 들면, 옥시라닐기와 에틸렌성 불포화 결합을 갖는 단량체(Bb1)(이하 「(Bb1)」이라고 하는 경우가 있다), 옥세타닐기와 에틸렌성 불포화 결합을 갖는 단량체(Bb2)(이하 「(Bb2)」이라고 하는 경우가 있다), 테트라하이드로프릴기와 에틸렌성 불포화 결합을 갖는 단량체(Bb3)(이하 「(Bb3)」이라고 하는 경우가 있다) 등을 들 수 있다.(Bb1) (hereinafter also referred to as "(Bb1)") having an oxiranyl group and an ethylenic unsaturated bond, a monomer (Bb2) having an oxetanyl group and an ethylenically unsaturated bond, (Hereinafter sometimes referred to as "(Bb2)"), and a monomer (Bb3) having a tetrahydropyrrole group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(Bb3)").
(Bb1)으로서는, 예를 들면, 직쇄상 또는 분기쇄상의 지방족 불포화 탄화수소가 에폭시화된 구조를 갖는 단량체(Bb1-1)(이하 「(Bb1-1)」이라고 하는 경우가 있다), 지환식 불포화 탄화수소가 에폭시화된 구조를 갖는 단량체(Bb1-2)(이하 「(Bb1-2)」이라고 하는 경우가 있다)를 들 수 있다.(Bb1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter may be referred to as "(Bb1-1)"), alicyclic unsaturated And a monomer (Bb1-2) having a structure in which a hydrocarbon is epoxidized (hereinafter sometimes referred to as "(Bb1-2)").
(Bb1-1)로서는, 글리시딜(메타)아크릴레이트, β-메틸글리시딜(메타)아크릴레이트, β-에틸글리시딜(메타)아크릴레이트, 글리시딜비닐에테르, o-비닐벤질글리시딜에테르, m-비닐벤질글리시딜에테르, p-비닐벤질글리시딜에테르, α-메틸-o-비닐벤질글리시딜에테르, α-메틸-m-비닐벤질글리시딜에테르, α-메틸-p-비닐벤질글리시딜에테르, 2,3-비스(글리시딜옥시메틸)스티렌, 2,4-비스(글리시딜옥시메틸)스티렌, 2,5-비스(글리시딜옥시메틸)스티렌, 2,6-비스(글리시딜옥시메틸)스티렌, 2,3,4-트리스(글리시딜옥시메틸)스티렌, 2,3,5-트리스(글리시딜옥시메틸)스티렌, 2,3,6-트리스(글리시딜옥시메틸)스티렌, 3,4,5-트리스(글리시딜옥시메틸)스티렌, 2,4,6-트리스(글리시딜옥시메틸)스티렌 등을 들 수 있다.(Bb1-1) include, for example, glycidyl (meth) acrylate,? -Methyl glycidyl (meth) acrylate,? -Ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, Vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? -Methyl-o-vinylbenzyl glycidyl ether,? Methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5- Styrenes such as 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, (Glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6-tris (glycidyloxymethyl) .
(Bb1-2)로서는, 비닐사이클로헥센모노옥사이드, 1,2-에폭시-4-비닐사이클로헥산(예를 들면, 셀록사이드(등록상표) 2000;(주) 다이셀 제), 3,4-에폭시사이클로헥실메틸(메타)아크릴레이트(예를 들면, 사이크로마(등록상표) A400;(주)다이셀 제), 3,4-에폭시사이클로헥실메틸(메타)아크릴레이트(예를 들면, 사이크로마 M100;(주)다이셀 제), 식(BI)으로 나타나는 화합물 및 식(BII)으로 나타나는 화합물 등을 들 수 있다.(Bb1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000 manufactured by Daicel Chemical Industries, Cyclohexylmethyl (meth) acrylate (e.g., Cyclomer (registered trademark) A400, manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth) acrylate (Manufactured by Daicel Co.), a compound represented by the formula (BI) and a compound represented by the formula (BII).
<화학식 30>(30)
[식(BI) 및 식(BII) 중, Ra 및 Rb는, 각각 독립적으로, 수소 원자, 또는 탄소수 1~4의 알킬기를 나타내고, 당해 알킬기에 포함되는 수소 원자는, 하이드록시기로 치환되어 있어도 된다.[Wherein, in formula (BI) and formula (BII), R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group .
Xa 및 Xb는, 단결합, *-Rc-, *-Rc-O-, *-Rc-S- 또는 *-Rc-NH-를 나타낸다.X a and X b represent a single bond, * -R c -, * -R c -O-, * -R c -S- or * -R c -NH-.
Rc는, 탄소수 1~6의 알칸디일기를 나타낸다.R c represents an alkanediyl group having 1 to 6 carbon atoms.
*는, O과의 결합손을 나타낸다.]* Indicates the binding hand with O.]
Ra, Rb의 탄소수 1~4의 알킬기로서는, 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, sec-부틸기, tert-부틸기 등을 들 수 있다.Examples of the alkyl group having 1 to 4 carbon atoms represented by R a and R b include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.
Ra, Rb의 수소 원자가 하이드록시로 치환된 알킬기로서는, 하이드록시메틸기, 1-하이드록시에틸기, 2-하이드록시에틸기, 1-하이드록시프로필기, 2-하이드록시프로필기, 3-하이드록시프로필기, 1-하이드록시-1-메틸에틸기, 2-하이드록시-1-메틸에틸기, 1-하이드록시부틸기, 2-하이드록시부틸기, 3-하이드록시부틸기, 4-하이드록시부틸기 등을 들 수 있다.Examples of the alkyl group in which the hydrogen atoms of R a and R b are substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, Propyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, And the like.
Ra 및 Rb로서는, 수소 원자, 탄소수 1~4의 알킬기, 또는 탄소수 1~4의 하이드록시알킬기가 바람직하고, 보다 바람직하게는 수소 원자, 또는 탄소수 1~4의 알킬기이고, 구체적으로, 바람직하게는 수소 원자, 메틸기, 에틸기, 하이드록시메틸기, 1-하이드록시에틸기, 2-하이드록시에틸기를 들 수 있고, 보다 바람직하게는 수소 원자, 메틸기를 들 수 있다.R a and R b are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Include a hydrogen atom, a methyl group, an ethyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, more preferably a hydrogen atom and a methyl group.
Rc의 알칸디일기로서는, 직쇄상 또는 분기쇄상의 알칸디일기를 들 수 있고, 구체적으로는, 메틸렌기, 에틸렌기, 프로판-1, 3-디일기, 부탄-1, 4-디일기, 펜탄-1, 5-디일기, 헥산-1, 6-디일기 등의 직쇄상 알칸디일기;프로판-1, 2-디일기 등의 분기쇄상 알칸디일기;를 들 수 있다.Examples of the alkanediyl group of R c include linear or branched alkanediyl groups. Specific examples thereof include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane- Straight chain alkanediyl groups such as a pentane-1, 5-diyl group, hexane-1, 6-diyl group and the like, and branched straight chain alkanediyl groups such as propane-1,2-diyl group.
Xa 및 Xb로서는, 단결합, *-Rc-, 또는 *-Rc-O-가 바람직하고, 보다 바람직하게는 단결합, 또는 *-Rc-O-이고, 특히 바람직하게는 단결합, 메틸렌기, 에틸렌기, *-CH2-O- 및 *-CH2CH2-O-를 들 수 있고, 보다 바람직하게는 단결합, *-CH2CH2-O-를 들 수 있다(*는 O와의 결합손을 나타낸다).X a and X b are preferably a single bond, * -R c -, or * -R c -O-, more preferably a single bond, or * -R c -O-, A methylene group, an ethylene group, * -CH 2 -O- and * -CH 2 CH 2 -O-, more preferably a single bond, * -CH 2 CH 2 -O- (* Denotes the binding hand with O).
식(BI)으로 나타내는 화합물로서는, 식(BI-1)~식(BI-15) 중 어느 하나로 나타나는 화합물 등을 들 수 있다. 그 중에서도, 식(BI-1), 식(BI-3), 식(BI-5), 식(BI-7), 식(BI-9) 또는 식(BI-11)~식(BI-15)으로 나타내는 화합물이 바람직하고, 식(BI-1), 식(BI-7), 식(BI-9) 또는 식(BI-15)으로 나타내는 화합물이 보다 바람직하다.Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI- ), And compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15) are more preferable.
<화학식 31>(31)
<화학식 32>(32)
식(BII)으로 나타나는 화합물로서는, 식(BII-1)~식(BII-15) 중 어느 하나로 나타나는 화합물 등을 들 수 있다. 그 중에서도, 식(BII-1), 식(BII-3), 식(BII-5), 식(BII-7), 식(BII-9) 또는 식(BII-11)~식(BII-15)으로 나타나는 화합물이 바람직하고, 식(BII-1), 식(BII-7), 식(BII-9) 또는 식(BII-15)으로 나타나는 화합물이 보다 바람직하다.Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15). (BII-1), BII-3, BII-5, BII-7, BII-9 or BII-11 to BII- ), And compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15) are more preferable.
<화학식 33>≪ Formula 33 >
<화학식 34>(34)
식(BI)로 나타나는 화합물 및 식(BII)으로 나타나는 화합물은, 각각 단독으로 이용해도, 식(BI)으로 나타나는 화합물과 식(BII)으로 나타나는 화합물을 병용 해도 된다. 이들을 병용하는 경우, 식(BI)으로 나타나는 화합물 및 식(BII)으로 나타나는 화합물의 함유 비율은 몰 기준으로, 바람직하게는 5:95~95:5, 보다 바람직하게는 10:90~90:10, 더욱 바람직하게는 20:80~80:20이다.The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of the compound represented by formula (BI) and the compound represented by formula (BII). When these compounds are used in combination, the content of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, , More preferably from 20:80 to 80:20.
(Bb2)로서는, 옥세타닐기와 (메타)아크릴로일옥시기를 갖는 단량체가 보다 바람직하다. (Bb2)로서는, 3-메틸-3-메타크릴로일옥시메틸옥세탄, 3-메틸-3-아크릴로일옥시메틸옥세탄, 3-에틸-3-메타크릴로일옥시메틸옥세탄, 3-에틸-3-아크릴로일옥시메틸옥세탄, 3-메틸-3-메타크릴로일옥시에틸옥세탄, 3-메틸-3-아크릴로일옥시에틸옥세탄, 3-에틸-3-메타크릴로일옥시에틸옥세탄, 3-에틸-3-아크릴로일옥시에틸옥세탄 등을 들 수 있다.(Bb2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. (Bb2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3 Ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3- 3-ethyl-3-acryloyloxyethyl oxetane, and the like.
(Bb3)으로서는, 테트라하이드로프릴기와 아크릴로일옥시기를 갖는 단량체가 보다 바람직하다. (Bb3)으로서는, 구체적으로는, 테트라하이드로퍼프릴아크릴레이트(예를 들면, 비스코트 V#150, 오사카 유기화학공업(주) 제), 테트라하이드로퍼프릴메타크릴레이트 등을 들 수 있다.As the monomer (Bb3), a monomer having a tetrahydropyryl group and an acryloyloxy group is more preferable. Specific examples of the compound (Bb3) include tetrahydroperfuryl acrylate (for example, Viscot V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.
(Bb)로서는, 얻어지는 칼라 필터의 내열성, 내약품성 등의 신뢰성을 보다 높게 할 수 있는 점에서, (Bb1)인 것이 바람직하다. 또한, 착색 경화성 수지 조성물의 보존 안정성이 우수하다고 하는 점에서, (Bb1-2)가 보다 바람직하다.(Bb) is preferably (Bb1) in that the color filter obtained can have higher reliability such as heat resistance, chemical resistance, and the like. Further, (Bb1-2) is more preferable because the storage stability of the colored curable resin composition is excellent.
(Bc)로서는, 예를 들면, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, n-부틸(메타)아크릴레이트, sec-부틸(메타)아크릴레이트, tert-부틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 도데실(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 스테아릴(메타)아크릴레이트, 사이클로펜틸(메타)아크릴레이트, 사이클로헥실(메타)아크릴레이트, 2-메틸사이클로헥실(메타)아크릴레이트, 트리사이클로[5.2.1.02,6]데칸-8-일(메타)아크릴레이트(당해 기술 분야에서는, 관용명으로서 「디사이클로펜타닐(메타)아크릴레이트」라고 불리고 있다. 또한, 「트리사이클로데실(메타)아크릴레이트」라고 하는 경우가 있다.), 트리사이클로[5.2.1.02,6]데센-8-일(메타)아크릴레이트(해당 기술 분야에서는, 관용명으로서 「디사이클로펜테닐(메타)아크릴레이트」라고 불리고 있다.), 디사이클로펜타닐옥시에틸(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 아다만틸(메타)아크릴레이트, 알릴(메타)아크릴레이트, 프로파르길(메타)아크릴레이트, 페닐(메타)아크릴레이트, 나프틸(메타)아크릴레이트, 벤질(메타)아크릴레이트 등의 (메타)아크릴산 에스테르류;(Meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, Acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, isopropyl (meth) acrylate, (Meth) acrylate, tricyclo [5.2.1.0 2,6 ] decan-8-yl (meth) acrylate (referred to in the art as "dicyclopentanyl (meth) (Also referred to as "tricyclodecyl (meth) acrylate"), tricyclo [5.2.1.0 2,6 ] decen-8-yl (meth) acrylate Quot; dicyclopentenyl (meth) acrylate " (Meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, (Meth) acrylates such as acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate and benzyl (meth) acrylate;
2-하이드록시에틸(메타)아크릴레이트, 2-하이드록시프로필(메타)아크릴레이트 등의 하이드록시기 함유(메타)아크릴산 에스테르류;Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
말레인산 디에틸, 푸말산 디에틸, 이타콘산 디에틸 등의 디카본산 디에스테르;Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate;
바이사이클로[2.2.1]헵토-2-엔, 5-메틸바이사이클로[2.2.1]헵토-2-엔, 5-에틸바이사이클로[2.2.1]헵토-2-엔, 5-하이드록시바이사이클로[2.2.1]헵토-2-엔, 5-하이드록시메틸바이사이클로[2.2.1]헵토-2-엔, 5-(2'-하이드록시에틸)바이사이클로[2.2.1]헵토-2-엔, 5-메톡시바이사이클로[2.2.1]헵토-2-엔, 5-에톡시바이사이클로[2.2.1]헵토-2-엔, 5,6-디하이드록시바이사이클로[2.2.1]헵토-2-엔, 5,6-디(하이드록시메틸)바이사이클로[2.2.1]헵토-2-엔, 5,6-디(2'-하이드록시에틸)바이사이클로[2.2.1]헵토-2-엔, 5,6-디메톡시바이사이클로[2.2.1]헵토-2-엔, 5,6-디에톡시바이사이클로[2.2.1]헵토-2-엔, 5-하이드록시-5-메틸바이사이클로[2.2.1]헵토-2-엔, 5-하이드록시-5-에틸바이사이클로[2.2.1]헵토-2-엔, 5-하이드록시메틸-5-메틸바이사이클로[2.2.1]헵토-2-엔, 5-tert-부톡시카보닐바이사이클로[2.2.1]헵토-2-엔, 5-사이클로헥실옥시카보닐바이사이클로[2.2.1]헵토-2-엔, 5-페녹시카보닐바이사이클로[2.2.1]헵토-2-엔, 5,6-비스(tert-부톡시카보닐)바이사이클로[2.2.1]헵토-2-엔, 5,6-비스(사이클로헥실옥시카보닐)바이사이클로[2.2.1]헵토-2-엔 등의 바이사이클로 불포화 화합물류;2,1-hept-2-ene, 5-methylbicyclo [2.2.1] 2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] 2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2.1 ] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] 2,6-dimethoxybicyclo [2.2.1] hepto-2-ene, 5,6-diethoxybicyclo [2.2.1] hepto-2-ene, 5-hydroxy- -Methylbicyclo [2.2.1] hepto-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1 2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hepto-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] 2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl Bicyclic unsaturated compounds such as bicyclo [2.2.1] hept-2-ene and 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-페닐말레이미드, N-사이클로헥실말레이미드, N-벤질말레이미드, N-숙신이미딜-3-말레이미드벤조에이트, N-숙신이미딜-4-말레이미드부틸레이트, N-숙신이미딜-6-말레이미드카프로에이트, N-숙신이미딜-3-말레이미드프로피오네이트, N-(9-아크리디닐)말레이미드 등의 디카보닐이미드 유도체류;N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N- Dicarbonylimide derivatives such as N-succinimidyl-3-maleimidepropionate and N- (9-acridinyl) maleimide;
스티렌, α-메틸스티렌, m-메틸스티렌, p-메틸스티렌, 비닐톨루엔, p-메톡시스티렌 등의 비닐기 함유 방향족 화합물;Vinyl group-containing aromatic compounds such as styrene,? -Methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene and p-methoxystyrene;
아크릴로니트릴, 메타크릴로니트릴 등의 비닐기 함유 니트릴;Vinyl group-containing nitriles such as acrylonitrile and methacrylonitrile;
염화 비닐, 염화 비닐리덴 등의 할로겐화 탄화수소;Halogenated hydrocarbons such as vinyl chloride and vinylidene chloride;
아크릴아미드, 메타크릴아미드 등의 비닐기 함유 아미드;Vinyl group-containing amides such as acrylamide and methacrylamide;
아세트산비닐 등의 에스테르;Esters such as vinyl acetate;
1,3-부타디엔, 이소프렌, 2,3-디메틸-1,3-부타디엔 등의 디엔;등을 들 수 있다.1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like.
이들 중, (Bc)로서는, 공중합 반응성 및 내열성의 점에서, 비닐기 함유 방향족 화합물, 디카보닐이미드 유도체류, 바이사이클로 불포화 화합물류가 바람직하다. 구체적으로는, 스티렌, 비닐톨루엔, N-페닐말레이미드, N-사이클로헥실말레이미드, N-벤질말레이미드, 바이사이클로[2.2.1]헵토-2-엔 등이 바람직하다.Of these, as the (Bc), a vinyl group-containing aromatic compound, a dicarbonylimide derivative and a bicyclo-unsaturated compound are preferable from the viewpoint of copolymerization reactivity and heat resistance. Specifically, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferable.
수지[K1]에 있어서, 각각에 유래하는 구조 단위의 비율은, 수지[K1]를 구성하는 전 구조 단위 중,In the resin [K1], the ratio of the structural units derived from each other is preferably such that, among all structural units constituting the resin [K1]
(Ba)에 유래하는 구조 단위;2~60몰%(Ba); 2 to 60 mol%
(Bb)에 유래하는 구조 단위;40~98몰%(Bb): 40 to 98 mol%
인 것이 바람직하고,, ≪ / RTI >
(Ba)에 유래하는 구조 단위;10~50몰%(Ba); a structural unit derived from 10 to 50 mol%
(Bb)에 유래하는 구조 단위;50~90몰%(Bb); 50 to 90 mol%
인 것이 보다 바람직하다.Is more preferable.
수지[K1]의 구조 단위의 비율이, 상기의 범위에 있으면, 착색 경화성 수지 조성물의 보존 안정성, 착색 패턴을 형성할 때의 현상성, 및 얻어지는 칼라 필터의 내용제성이 우수한 경향이 있다.When the ratio of the structural unit of the resin [K1] is within the above range, there is a tendency that storage stability of the colored curable resin composition, developability in forming a colored pattern, and solvent resistance of the resulting color filter are excellent.
수지[K1]는, 예를 들면, 문헌 「고분자 합성의 실험법」(오츠 타카유키저 발행소(주) 화학동인 제1판 제1쇄 1972년 3월 1일 발행)에 기재된 방법 및 해당 문헌에 기재된 인용 문헌을 참고로 하여 제조할 수 있다.The resin [K1] can be synthesized by a method described in, for example, "Experimental Method of Polymer Synthesis" (published by the Chemical Society of Japan, 1st Edition, 1st Edition, March 1, 1972, Can be prepared by reference to the literature.
구체적으로는, (Ba) 및 (Bb)의 소정량, 중합 개시제 및 용제 등을 반응 용기 안에 넣고, 예를 들면, 질소에 의해 산소를 치환함으로써, 탈산소 분위기로 하여, 교반하면서, 가열 및 보온하는 방법을 들 수 있다. 또한, 여기서 이용되는 중합 개시제 및 용제 등은, 특별히 한정되지 않고, 해당 분야에서 통상 사용되고 있는 것을 사용할 수 있다. 중합 개시제로서는, 예를 들면, 아조 화합물(2,2'-아조비스이소부티로니트릴, 2,2'-아조비스(2,4-디메틸발레로니트릴) 등)나 유기 과산화물(벤조일퍼옥시드 등)을 들 수 있고, 용제로서는, 각 모노머를 용해하는 것이면 되고, 본 발명의 착색 경화성 수지 조성물의 용제(E)로서 후술하는 용제 등을 들 수 있다.Specifically, a predetermined amount of (Ba) and (Bb), a polymerization initiator and a solvent are placed in a reaction vessel and oxygen is replaced by, for example, nitrogen, thereby forming a deoxidizing atmosphere, . The polymerization initiator, solvent and the like to be used herein are not particularly limited and those generally used in the field can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutylonitrile, 2,2'-azobis (2,4-dimethylvaleronitrile) and the like) and organic peroxides (such as benzoyl peroxide ). The solvent may be any one that dissolves the respective monomers. Examples of the solvent (E) of the colored curable resin composition of the present invention include solvents described later.
또한, 얻어진 공중합체는, 반응 후의 용액을 그대로 사용해도 되고, 농축 혹은 희석한 용액을 사용해도 되고, 재침전 등의 방법으로 고체(분체)로서 취출한 것을 사용해도 된다. 특히, 이 중합시에 용제로서, 본 발명의 착색 경화성 수지 조성물에 포함되는 용제를 사용함으로써, 반응 후의 용액을 그대로 본 발명의 착색 경화성 수지 조성물의 조제에 사용할 수 있기 때문에, 본 발명의 착색 경화성 수지 조성물의 제조 공정을 간략화할 수 있다.As the obtained copolymer, the solution after the reaction may be used as it is, or a concentrated or diluted solution may be used, or it may be taken out as a solid (powder) by a method such as re-precipitation. In particular, by using the solvent contained in the colored curable resin composition of the present invention as a solvent during the polymerization, the solution after the reaction can be used as it is for preparing the colored curable resin composition of the present invention, The manufacturing process of the composition can be simplified.
수지[K2]에 있어서, 각각 유래하는 구조 단위의 비율은, 수지[K2]를 구성하는 전 구조 단위 중,In the resin [K2], the ratio of the respective structural units derived from among all structural units constituting the resin [K2]
(Ba)에 유래하는 구조 단위;2~45몰%(Ba); 2 to 45 mol%
(Bb)에 유래하는 구조 단위;2~95몰%(Bb); 2 to 95 mol%
(Bc)에 유래하는 구조 단위;1~65몰%(Bc); 1 to 65 mol%
인 것이 바람직하고,, ≪ / RTI >
(Ba)에 유래하는 구조 단위;5~40몰%(Ba); 5 to 40 mol%
(Bb)에 유래하는 구조 단위;5~80몰%(Bb); 5 to 80 mol%
(Bc)에 유래하는 구조 단위;5~60몰%(Bc); 5 to 60 mol%
인 것이 보다 바람직하다.Is more preferable.
수지[K2]의 구조 단위의 비율이, 상기의 범위에 있으면, 착색 경화성 수지 조성물의 보존 안정성, 착색 패턴을 형성할 때의 현상성, 및, 얻어지는 칼라 필터의 내용제성, 내열성 및 기계 강도가 우수한 경향이 있다.When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored curable resin composition, developability in forming a colored pattern, and color filter having excellent solvent resistance, heat resistance and mechanical strength There is a tendency.
수지[K2]는, 예를 들면, 수지[K1]의 제조 방법으로서 기재한 방법과 동일하게 제조할 수 있다.The resin [K2] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].
수지[K3]에 있어서, 각각 유래하는 구조 단위의 비율은, 수지[K3]를 구성하는 전 구조 단위중,In the resin [K3], the proportions of the respective structural units derived from among the whole structural units constituting the resin [K3]
(Ba)에 유래하는 구조 단위;2~60몰%(Ba); 2 to 60 mol%
(Bc)에 유래하는 구조 단위;40~98몰%(Bc): 40 to 98 mol%
인 것이 바람직하고,, ≪ / RTI >
(Ba)에 유래하는 구조 단위;10~50몰%(Ba); a structural unit derived from 10 to 50 mol%
(Bc)에 유래하는 구조 단위;50~90몰%(Bc): 50 to 90 mol%
인 것이 보다 바람직하다.Is more preferable.
수지[K3]는, 예를 들면, 수지[K1]의 제조 방법으로서 기재한 방법과 동일하게 제조할 수 있다.The resin [K3] can be produced, for example, in the same manner as described for the method of producing the resin [K1].
수지[K4]는, (Ba)와 (Bc)의 공중합체를 얻고, (Bb)가 갖는 탄소수 2~4의 환상 에테르를 (Ba)가 갖는 카본산 및/또는 카본산 무수물에 부가시킴으로써 제조할 수 있다.The resin [K4] is obtained by obtaining a copolymer of (Ba) and (Bc) and adding a cyclic ether having 2 to 4 carbon atoms of (Bb) to a carbonic acid and / or a carbonic anhydride having (Ba) .
우선 (Ba)와 (Bc)의 공중합체를, 수지[K1]의 제조 방법으로서 기재한 방법과 동일하게 제조한다. 이 경우, 각각 유래하는 구조 단위의 비율은, 수지[K3]로 든 것과 동일한 비율인 것이 바람직하다.First, a copolymer of (Ba) and (Bc) is prepared in the same manner as described for the resin [K1]. In this case, the ratio of the respective derived structural units is preferably the same as that of the resin [K3].
다음으로, 상기 공중합체 중의 (Ba)에 유래하는 카본산 및/또는 카본산 무수물의 일부에, (Bb)가 갖는 탄소수 2~4의 환상 에테르를 반응시킨다.Next, a cyclic ether having 2 to 4 carbon atoms contained in (Bb) is reacted with a part of the carbonic acid and / or the carbonic acid anhydride derived from (Ba) in the copolymer.
(Ba)와 (Bc)의 공중합체의 제조에 연속하여, 플라스크 내 분위기를 질소로부터 공기로 치환하고, (Bb), 카본산 또는 카본산 무수물과 환상 에테르의 반응 촉매(예를 들면 트리스(디메틸아미노메틸)페놀 등) 및 중합 금지제(예를 들면 하이드로퀴논 등) 등을 플라스크 내에 넣고, 예를 들면, 60~130에서, 1~10시간 반응함으로써, 수지[K4]를 제조할 수 있다.Subsequently to the production of the copolymer of (Ba) and (Bc), the atmosphere in the flask is replaced by air from nitrogen, (Bb), a reaction catalyst of a carboxylic acid or a carbonic acid anhydride and a cyclic ether The resin [K4] can be produced by reacting, for example, at 60 to 130 for 1 to 10 hours with a polymerization inhibitor (for example, hydroquinone or the like) in a flask.
(Bb)의 사용량은, (Ba) 100몰에 대하여, 5~80몰이 바람직하고, 보다 바람직하게는 10~75몰이다. (Bb)의 사용량을 이 범위로 조정함으로써, 착색 경화성 수지 조성물의 보존 안정성, 패턴을 형성할 때의 현상성, 및, 얻어지는 패턴의 내용제성, 내열성, 기계 강도 및 감도의 밸런스가 양호하게 되는 경향이 있다. 환상 에테르의 반응성이 높고, 미반응의 (Bb)가 잔존하기 어려운 점에서, 수지[K4]에 이용하는 (Bb)로서는 (Bb1)이 바람직하고, 더욱 (Bb1-1)이 바람직하다.(Bb) is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (Ba). (Bb) is adjusted to this range, the balance between the storage stability of the colored curable resin composition, the developability in forming the pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern tends to be good . (Bb1) is preferable as the (Bb) used for the resin [K4], and (Bb1-1) is more preferable because the reactivity of the cyclic ether is high and unreacted (Bb)
상기 반응 촉매의 사용량은, (Ba), (Bb) 및 (Bc)의 합계량 100질량부에 대하여 0.001~5질량부가 바람직하다. 상기 중합 금지제의 사용량은, (Ba), (Bb) 및 (Bc)의 합계량 100질량부에 대하여 0.001~5질량부가 바람직하다.The amount of the reaction catalyst to be used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (Ba), (Bb) and (Bc). The amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (Ba), (Bb) and (Bc).
각 시제의 투입 방법, 반응 온도 및 반응 시간 등의 반응 조건은, 제조 설비나 중합에 의한 발열량 등을 고려하여 적절히 조정할 수 있다. 또한, 중합 조건과 동일하게, 제조 설비나 중합에 의한 발열량 등을 고려하여, 투입 방법이나 반응 온도를 적절히 조정할 수 있다.The reaction conditions such as the method of introduction of the respective reagents, the reaction temperature, and the reaction time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. In addition, in the same manner as in the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production facility or the amount of heat generated by polymerization.
수지[K5]를 제조할 때에는, 제1 단계로서, 상술한 수지[K1]의 제조 방법과 동일하게 하여, (Bb)와 (Bc)의 공중합체를 얻는다. 상기와 동일하게, 얻어진 공중합체는, 반응 후의 용액을 그대로 사용해도 되고, 농축 혹은 희석한 용액을 사용해도 되고, 재침전 등의 방법으로 고체(분체)로서 취출한 것을 사용해도 된다.When the resin [K5] is produced, a copolymer of (Bb) and (Bc) is obtained in the same manner as in the above-mentioned production of the resin [K1]. In the same way as the above, the solution obtained after the reaction may be used as it is, or a solution obtained by concentrating or diluting may be used, or a solid (powder) obtained by re-precipitation or the like may be used.
(Bb) 및 (Bc)에 유래하는 구조 단위의 비율은, 상기 (Bb)와 (Bc)의 공중합체를 구성하는 전 구조 단위의 합계 몰수에 대하여, 각각,The ratio of the structural units derived from the structural units (Bb) and (Bc) to the total structural units constituting the copolymer (Bb) and (Bc)
(Bb)에 유래하는 구조 단위;5~95몰%(Bb); 5 to 95 mol%
(Bc)에 유래하는 구조 단위;5~95몰%(Bc); 5 to 95 mol%
인 것이 바람직하고,, ≪ / RTI >
(Bb)에 유래하는 구조 단위;10~90몰%(Bb); a structural unit derived from 10 to 90 mol%
(Bc)에 유래하는 구조 단위;10~90몰%(Bc); a structural unit derived from 10 to 90 mol%
인 것이 보다 바람직하다.Is more preferable.
추가로, 제2 단계로서, 수지[K4]의 제조 방법과 동일한 조건으로, (Bb)와 (Bc)의 공중합체가 갖는 (Bb)에 유래하는 환상 에테르에, (Ba)가 갖는 카본산 또는 카본산 무수물을 반응시킴으로써, 수지[K5]를 얻을 수 있다.(Bb) and (Bb) in the copolymer of (Bb) and (Bc) in the same manner as in the production of the resin [K4] By reacting the carbonic acid anhydride, the resin [K5] can be obtained.
제2 단계에 있어서, 상기 (Bb)와 (Bc)의 공중합체에 반응시키는 (Ba)의 사용량은, (Bb) 100몰에 대하여, 5~80몰이 바람직하다. 환상 에테르의 반응성이 높고, 미반응의 (Bb)가 잔존하기 어려운 점에서, 수지[K5]에 이용하는 (Bb)로서는 (Bb1)이 바람직하고, 또한 (Bb1-1)이 바람직하다.In the second step, the amount of (Ba) to be reacted with the copolymer of (Bb) and (Bc) is preferably 5 to 80 moles per 100 moles of (Bb). (Bb1) is preferable and (Bb1-1) is preferable for (Bb) used for the resin [K5] from the viewpoint that the reactivity of the cyclic ether is high and unreacted (Bb)
수지[K6]는, 수지[K5]에, 추가로 카본산 무수물을 반응시킨 수지이다. 환상 에테르와 카본산 또는 카본산 무수물의 반응에 의해 발생하는 하이드록시기에, 카본산 무수물을 반응시킨다.Resin [K6] is a resin obtained by further reacting a resin [K5] with a carboxylic acid anhydride. A carboxylic acid anhydride is reacted with a hydroxyl group generated by the reaction of a cyclic ether and a carbonic acid or a carboxylic acid anhydride.
수지[K6]는, 수지[K5]에, 추가로 카본산 무수물을 반응시킴으로써 얻어지는 수지이고, 구체적으로는, (Bb)에 유래하는 환상 에테르와 (Ba)의 카본산 또는 카본산 무수물의 반응에 의해 발생하는 하이드록시기에, 카본산 무수물을 반응시킴으로써 제조할 수 있다.The resin [K6] is a resin obtained by reacting the resin [K5] with a carbonic acid anhydride. Concretely, the resin [K6] is a resin obtained by reacting a cyclic ether derived from (Bb) with a carboxylic acid or carbonic anhydride of Can be produced by reacting a carboxylic acid anhydride with a hydroxyl group generated by a hydroxyl group.
카본산 무수물로서는, 무수 말레인산, 시트라콘산 무수물, 이타콘산 무수물, 3-비닐프탈산 무수물, 4-비닐프탈산 무수물, 3,4,5,6-테트라하이드로프탈산 무수물, 1,2,3,6-테트라하이드로프탈산 무수물, 디메틸테트라하이드로프탈산 무수물, 5,6-디카복시바이사이클로[2.2.1]헵토-2-엔 무수물 등을 들 수 있다. 카본산 무수물의 사용량은, (Ba)의 사용량 1몰에 대하여, 0.5~1몰이 바람직하다.Examples of the carbonic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride. The amount of the carbonic anhydride to be used is preferably 0.5 to 1 mole based on 1 mole of the amount of (Ba).
수지(B)로서는, 구체적으로, 3,4-에폭시사이클로헥실메틸(메타)아크릴레이트/(메타)아크릴산 공중합체, 3,4-에폭시트리사이클로[5.2.1.02,6]데실(메타)아크릴레이트/(메타)아크릴산 공중합체 등의 수지[K1];글리시딜(메타)아크릴레이트/벤질(메타)아크릴레이트/(메타)아크릴산 공중합체, 글리시딜(메타)아크릴레이트/스티렌/(메타)아크릴산 공중합체, 3,4-에폭시트리사이클로[5.2.1.02,6]데실(메타)아크릴레이트/(메타)아크릴산/N-사이클로헥실말레이미드 공중합체, 3,4-에폭시트리사이클로[5.2.1.02,6]데실(메타)아크릴레이트/(메타)아크릴산/비닐톨루엔 공중합체, 3-메틸-3-(메타)아크릴로일옥시메틸옥세탄/(메타)아크릴산/스티렌 공중합체 등의 수지[K2];벤질(메타)아크릴레이트/(메타)아크릴산 공중합체, 스티렌/(메타)아크릴산 공중합체, 벤질(메타)아크릴레이트/트리사이클로데실(메타)아크릴레이트/(메타)아크릴산 공중합체 등의 수지[K3];벤질(메타)아크릴레이트/(메타)아크릴산 공중합체에 글리시딜(메타)아크릴레이트를 부가시킨 수지, 트리사이클로데실(메타)아크릴레이트/스티렌/(메타)아크릴산 공중합체에 글리시딜(메타)아크릴레이트를 부가시킨 수지, 트리사이클로데실(메타)아크릴레이트/벤질(메타)아크릴레이트/(메타)아크릴산 공중합체에 글리시딜(메타)아크릴레이트를 부가시킨 수지 등의 수지[K4];트리사이클로데실(메타)아크릴레이트/글리시딜(메타)아크릴레이트의 공중합체에 (메타)아크릴산을 반응시킨 수지, 트리사이클로데실(메타)아크릴레이트/스티렌/글리시딜(메타)아크릴레이트의 공중합체에 (메타)아크릴산을 반응시킨 수지 등의 수지[K5];트리사이클로데실(메타)아크릴레이트/글리시딜(메타)아크릴레이트의 공중합체에 (메타)아크릴산을 반응시킨 수지에 추가로 테트라하이드로프탈산 무수물을 반응시킨 수지 등의 수지[K6]등을 들 수 있다.Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) (Meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / benzyl (meth) acrylate / (Meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3,4- 5.2.1.0 2,6] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3-methyl-3- (meth) acryloyloxyethyl-methyl oxetane / (meth) acrylic acid / styrene copolymers, etc. (Meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer (K3) such as benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer and the like; a benzyl (meth) acrylate / (meth) ), A resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, a resin obtained by adding tricyclodecyl (meth) acrylate / benzyl (K4) such as a resin obtained by adding glycidyl (meth) acrylate to a (meth) acrylate / (meth) acrylic acid copolymer; a copolymer of tricyclodecyl (meth) acrylate / glycidyl (K5) such as a resin obtained by reacting (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) four (K6) such as a resin obtained by reacting a resin obtained by reacting (meth) acrylic acid with a copolymer of chlorodecyl (meth) acrylate / glycidyl (meth) acrylate with a tetrahydrophthalic anhydride .
수지(B)는, 바람직하게는, 수지[K1], 수지[K2]및 수지[K3]으로 이루어지는 군으로부터 선택되는 일종이며, 보다 바람직하게는, 수지[K2]및 수지[K3]로 이루어지는 군으로부터 선택되는 일종이다. 이들 수지이면 착색 경화성 수지 조성물은 현상성이 뛰어나다. 착색 패턴과 기판의 밀착성의 관점에서, 수지[K2]가 더욱 바람직하다.The resin (B) is preferably one selected from the group consisting of the resin [K1], the resin [K2] and the resin [K3], more preferably a resin [K2] Lt; / RTI > If these resins are used, the colored curable resin composition is excellent in developing property. From the viewpoint of the adhesion between the coloring pattern and the substrate, the resin [K2] is more preferable.
수지(B)의 폴리스티렌 환산의 중량 평균 분자량은, 바람직하게는 3,000~100,000이고, 보다 바람직하게는 5,000~50,000이고, 더욱 바람직하게는 5,000~30,000이다. 분자량이 상기의 범위에 있으면, 도막 경도가 향상하고, 잔막율도 높고, 미노광부의 현상액에 대한 용해성이 양호하고, 착색 패턴의 해상도가 향상하는 경향이 있다.The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility in the developing solution of the unexposed portion is good, and the resolution of the coloring pattern tends to be improved.
수지(B)의 분자량 분포[중량 평균 분자량(Mw)/수평균 분자량(Mn)]는, 바람직하게는 1.1~6이고, 보다 바람직하게는 1.2~4이다.The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
수지(B)의 산가는, 바람직하게는 50~170mg-KOH/g이고, 보다 바람직하게는 60~150mg-KOH/g, 더욱 바람직하게는 70~135mg-KOH/g이다. 여기서 산가는 수지(B) 1g을 중화하는에 필요한 수산화 칼륨의 양(mg)으로서 측정되는 값이고, 예를 들면 수산화 칼륨 수용액을 이용해 적정함으로써 구할 수 있다.The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be determined by titration using, for example, an aqueous potassium hydroxide solution.
수지(B)의 함유량은, 고형분의 총량에 대하여, 바람직하게는 7~65질량%이고, 보다 바람직하게는 13~60질량%이고, 더욱 바람직하게는 17~55질량%이다. 수지(B)의 함유량이, 상기의 범위에 있으면, 착색 패턴을 형성할 수 있고, 또한 착색 패턴의 해상도 및 잔막율이 향상하는 경향이 있다.The content of the resin (B) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total solid content. When the content of the resin (B) is in the above range, a coloring pattern can be formed, and the resolution and residual film ratio of the coloring pattern tends to be improved.
<중합성 화합물(C)>≪ Polymerizable compound (C) >
중합성 화합물(C)는, 중합 개시제(D)로부터 발생한 활성 라디칼 및/또는 산에 의해서 중합할 수 있는 화합물이고, 예를 들면, 중합성의 에틸렌성 불포화 결합을 갖는 화합물 등을 들 수 있고, 바람직하게는 (메타)아크릴산 에스테르 화합물이다.The polymerizable compound (C) is a compound capable of being polymerized by an active radical and / or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenic unsaturated bond, Is a (meth) acrylic acid ester compound.
에틸렌성 불포화 결합을 1개 갖는 중합성 화합물로서는, 예를 들면, 노닐페닐카비톨아크릴레이트, 2-하이드록시-3-페녹시프로필아크릴레이트, 2-에틸헥실카비톨아크릴레이트, 2-하이드록시에틸아크릴레이트, N-비닐피롤리돈 등, 및, 상술의 (Ba), (Bb) 및 (Bc)를 들 수 있다.Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxy Ethyl acrylate, N-vinyl pyrrolidone and the like, and (Ba), (Bb) and (Bc) described above.
에틸렌성 불포화 결합을 2개 갖는 중합성 화합물로서는, 예를 들면, 1,6-헥산디올디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 비스페놀 A의 비스(아크릴로일옥시에틸)에테르, 3-메틸펜탄디올디(메타)아크릴레이트 등을 들 수 있다.Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) Ethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.
그 중에서도, 중합성 화합물(C)는, 에틸렌성 불포화 결합을 3개 이상 갖는 중합성 화합물인 것이 바람직하다. 이러한 중합성 화합물로서는, 예를 들면, 트리메틸올프로판트리(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 디펜타에리트리톨펜타(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트, 트리펜타에리트리톨옥타(메타)아크릴레이트, 트리펜타에리트리톨헵타(메타)아크릴레이트, 테트라펜타에리트리톨데카(메타)아크릴레이트, 테트라펜타에리트리톨노나(메타)아크릴레이트, 트리스(2-(메타)아크릴로일옥시에틸)이소시아누레이트, 에틸렌 글리콜 변성 펜타에리트리톨테트라(메타)아크릴레이트, 에틸렌 글리콜 변성 디펜타에리트리톨헥사(메타)아크릴레이트, 프로필렌 글리콜 변성 펜타에리트리톨테트라(메타)아크릴레이트, 프로필렌 글리콜 변성 디펜타에리트리톨헥사(메타)아크릴레이트, 카프로락톤 변성 펜타에리트리톨테트라(메타)아크릴레이트, 카프로락톤 변성 디펜타에리트리톨헥사(메타)아크릴레이트 등을 들 수 있고, 그 중에서도, 디펜타에리트리톨펜타(메타)아크릴레이트 및 디펜타에리트리톨헥사(메타)아크릴레이트가 바람직하다.Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) , Dipentaerythritol hexa (metha) acrylate, tripentaerythritol octa (metha) acrylate, tripentaerythritol hepta (metha) acrylate, tetrapentaerythritol deca (metha) acrylate, tetrapentaerythritol nona (Meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa , Propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (metha) arc Caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate. Of these, dipentaerythritol penta (meth) acrylate and di Pentaerythritol hexa (meth) acrylate is preferable.
중합성 화합물(C)의 중량 평균 분자량은, 바람직하게는 150 이상 2,900 이하, 보다 바람직하게는 250~1,500 이하이다.The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 to 1,500 or less.
중합성 화합물(C)의 함유량은, 고형분의 총량에 대하여, 7~65질량%인 것이 바람직하고, 보다 바람직하게는 13~60질량%이고, 더욱 바람직하게는 17~55질량%이다. 중합성 화합물(C)의 함유량이, 상기의 범위 내에 있으면, 착색 패턴 형성시의 잔막율 및 칼라 필터의 내약품성이 향상하는 경향이 있다.The content of the polymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total solid content. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a color pattern and the chemical resistance of the color filter tend to be improved.
또한, 수지(B)와 중합성 화합물(C)의 함유량비〔수지(B):중합성 화합물(C)〕는 질량 기준으로, 바람직하게는 20:80~80:20이고, 보다 바람직하게는 35:65~80:20이다.The content ratio of the resin (B) to the polymerizable compound (C) (resin (B): polymerizable compound (C)) is preferably 20: 80 to 80:20, 35: 65-80: 20.
중합성 화합물(C)의 함유량이, 상기의 범위 내에 있으면, 착색 패턴 형성시의 잔막율 및 칼라 필터의 내약품성이 향상하는 경향이 있다.When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a color pattern and the chemical resistance of the color filter tend to be improved.
<중합 개시제(D)>≪ Polymerization initiator (D) >
중합 개시제(D)는, 빛이나 열의 작용에 의해 활성 라디칼, 산 등을 발생하고, 중합을 개시할 수 있는 화합물이면 특별히 한정되는 일 없이, 공지의 중합 개시제를 이용할 수 있다.The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical or an acid by the action of light or heat and capable of initiating polymerization, and a known polymerization initiator can be used.
중합 개시제(D)로서는, O-아실옥심 화합물, 알킬페논 화합물, 비이미다졸 화합물, 트리아진 화합물, 및 아실포스핀 옥사이드 화합물 등을 들 수 있다.Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, imidazole compounds, triazine compounds, and acylphosphine oxide compounds.
상기 O-아실옥심 화합물은, 식(Dd1)으로 나타나는 부분 구조를 갖는 화합물이다. 이하, *는 결합손을 나타낸다.The O-acyloxime compound is a compound having a partial structure represented by the formula (Dd1). Herein, * denotes a combined hand.
<화학식 35>≪ Formula 35 >
상기 O-아실옥심 화합물로서는, 예를 들면, N-벤조일옥시-1-(4-페닐술파닐페닐)부탄-1-온-2-이민, N-벤조일옥시-1-(4-페닐술파닐페닐)옥탄-1-온-2-이민, N-벤조일옥시-1-(4-페닐술파닐페닐)-3-사이클로펜틸프로판-1-온-2-이민, N-아세톡시-1-[9-에틸-6-(2-메틸벤조일)-9H-카바졸-3-일]에탄-1-이민, N-아세톡시-1-[9-에틸-6-{2-메틸-4-(3,3-디메틸-2,4-디옥사사이클로펜타닐메틸옥시)벤조일}-9H-카바졸-3-일]에탄-1-이민, N-아세톡시-1-[9-에틸-6-(2-메틸벤조일)-9H-카바졸-3-일]-3-사이클로펜틸프로판-1-이민, N-벤조일옥시-1-[9-에틸-6-(2-메틸벤조일)-9H-카바졸-3-일]-3-사이클로펜틸프로판-1-온-2-이민 등을 들 수 있다. 이르가큐어(등록상표) OXE01, OXE02(이상, BASF사 제), N-1919(ADEKA사 제) 등의 시판품을 이용해도 된다. 그 중에서도, O-아실옥심 화합물은, N-벤조일옥시-1-(4-페닐술파닐페닐)부탄-1-온-2-이민, N-벤조일옥시-1-(4-페닐술파닐페닐)옥탄-1-온-2-이민 및 N-벤조일옥시-1-(4-페닐술파닐페닐)-3-사이클로펜틸프로판-1-온-2-이민으로 이루어지는 군으로부터 선택되는 적어도 1종이 바람직하고, N-벤조일옥시-1-(4-페닐술파닐페닐)옥탄-1-온-2-이민이 보다 바람직하다.Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethan- 1-imine, N- acetoxy- 1- [ Benzoyl} -9H-carbazol-3-yl] ethan-1-imine, N-acetoxy- 1- [9-ethyl-6- ( Benzoyloxy) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole Yl] -3-cyclopentylpropan-1-one-2-imine and the like. A commercially available product such as Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF) and N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyloxime compound is preferably an N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan- 1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- , And N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine are more preferable.
상기 알킬페논 화합물은, 예를 들면, 식(Dd2)로 나타나는 부분 구조 또는 식(Dd3)으로 나타나는 부분 구조를 갖는 화합물이다. 이들 부분 구조 중, 벤젠환은 치환기를 갖고 있어도 된다.The alkylphenone compound is, for example, a compound having a partial structure represented by the formula (Dd2) or a partial structure represented by the formula (Dd3). Of these partial structures, the benzene ring may have a substituent.
<화학식 36>≪ EMI ID =
식(Dd2)으로 나타나는 부분 구조를 갖는 화합물로서는, 예를 들면, 2-메틸-2-몰포리노-1-(4-메틸술파닐페닐)프로판-1-온, 2-디메틸아미노-1-(4-몰포리노페닐)-2-벤질부탄-1-온, 2-(디메틸아미노)-2-[(4-메틸페닐)메틸]-1-[4-(4-몰포리닐)페닐]부탄-1-온 등을 들 수 있다. 이르가큐어 369, 907, 379(이상, BASF사 제) 등의 시판품을 이용해도 된다.Examples of the compound having a partial structure represented by the formula (Dd2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- (4-morpholinyl) phenyl] butane-1-one, 2- (dimethylamino) 1-on. IRGACURE 369, 907, 379 (manufactured by BASF Co., Ltd.) and the like may be used.
식(Dd3)으로 나타나는 부분 구조를 갖는 화합물로서는, 예를 들면, 2-하이드록시-2-메틸-1-페닐프로판-1-온, 2-하이드록시-2-메틸-1-〔4-(2-하이드록시에톡시)페닐〕프로판-1-온, 1-하이드록시사이클로헥실페닐케톤, 2-하이드록시-2-메틸-1-(4-이소프로페닐페닐)프로판-1-온의 올리고머, α,α-디에톡시아세토페논, 벤질디메틸케탈 등을 들 수 있다.Examples of the compound having a partial structure represented by the formula (Dd3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2- Hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1-one, 1-hydroxycyclohexyl phenyl ketone, ,?,? -diethoxyacetophenone, and benzyl dimethyl ketal.
감도의 점에서, 알킬페논 화합물로서는, 식(Dd2)으로 나타나는 부분 구조를 갖는 화합물이 바람직하다.From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by the formula (Dd2).
상기 비이미다졸 화합물은, 예를 들면, 식(Dd4)으로 나타나는 화합물을 들 수 있다.The non-imidazole compound may be, for example, a compound represented by the formula (Dd4).
<화학식 37>(37)
[식(Dd4) 중, Rd1~Rd6은, 치환기를 갖고 있어도 되는 탄소수 6~10의 아릴기를 나타낸다.][In the formula (Dd4), R d1 to R d6 represent an aryl group having 6 to 10 carbon atoms which may have a substituent.]
Rd1~Rd6의 탄소수 6~10의 아릴기로서는, 예를 들면, 페닐기, 톨릴기, 자일릴기, 에틸페닐기 및 나프틸기 등을 들 수 있고, 바람직하게는 페닐기이다.Examples of the aryl group having 6 to 10 carbon atoms represented by R d1 to R d6 include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group and a naphthyl group, and preferably a phenyl group.
상기 Rd1~Rd6의 아릴기를 치환하고 있어도 되는 치환기로서는, 예를 들면, 할로겐 원자, 탄소수 1~4의 알콕시기 등을 들 수 있다. 할로겐 원자로서는, 예를 들면, 불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등을 들 수 있고, 바람직하게는 염소 원자이다. 탄소수 1~4의 알콕시기로서는, 예를 들면, 메톡시기, 에톡시기, 프로폭시기, 부톡시기 등을 들 수 있고, 바람직하게는 메톡시기이다.Examples of the substituent which may be substituted for the aryl group of R d1 to R d6 include a halogen atom and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and preferably a chlorine atom. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like, preferably a methoxy group.
비이미다졸 화합물로서는, 예를 들면, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐비이미다졸(예를 들면, 일본공개특허 평6-75372호 공보, 일본공개특허 평6-75373호 공보 등 참조.), 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라페닐비이미다졸, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라(알콕시페닐)비이미다졸, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라(디알콕시페닐)비이미다졸, 2,2'-비스(2-클로로페닐)-4,4',5,5'-테트라(트리알콕시페닐)비이미다졸(예를 들면, 일본공개특허 소48-38403호 공보, 일본공개특허 소62-174204호 공보 등 참조.), 4,4',5,5'-위치의 페닐기가 카보알콕시기에 의해 치환되어 있는 이미다졸 화합물(예를 들면, 일본공개특허 평7-10913호 공보 등 참조.) 등을 들 수 있다. 그 중에서도, 하기식으로 나타나는 화합물 및 이들 혼합물이 바람직하다.Examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'- Dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A 6-75372 and JP-A 6-75373) Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis Tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra -Chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole (see, for example, JP-A-48-38403, JP-A-62-174204, etc. ), An imidazole compound in which the phenyl group at the 4,4 ', 5,5'-position is substituted by a carboalkoxy group (for example, see Japanese Patent Application Laid- Reference No. 10913, etc.) and the like. Among them, compounds represented by the following formulas and mixtures thereof are preferable.
<화학식 38>≪ Formula 38 >
상기 트리아진 화합물로서는, 예를 들면, 2,4-비스(트리클로로메틸)-6-(4-메톡시페닐)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시나프틸)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-피페로닐-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-(4-메톡시스티릴)-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-〔2-(5-메틸푸란-2-일)에테닐〕-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-〔2-(푸란-2-일)에테닐〕-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-〔2-(4-디에틸아미노-2-메틸페닐)에테닐〕-1,3,5-트리아진, 2,4-비스(트리클로로메틸)-6-〔2-(3,4-디메톡시페닐)에테닐〕-1,3,5-트리아진 등을 들 수 있다.Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4 Bis (trichloromethyl) -6- [2- (5-methylfuran-1-yl) 2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- Triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- Dimethyl-2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine, and the like.
상기 아실포스핀 옥사이드 화합물로서는, 2,4,6-트리메틸벤조일디페닐포스핀 옥사이드 등을 들 수 있다.Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.
추가로 중합 개시제(D)로서는, 벤조인, 벤조인 메틸에테르, 벤조인 에틸에테르, 벤조인 이소프로필에테르, 벤조인 이소부틸 에테르 등의 벤조인 화합물;벤조페논, o-벤조일벤조산 메틸, 4-페닐벤조페논, 4-벤조일-4'-메틸디페닐설파이드, 3,3',4,4'-테트라(tert-부틸퍼옥시카보닐)벤조페논, 2,4,6-트리메틸벤조페논 등의 벤조페논 화합물;9,10-페난트렌퀴논, 2-에틸안트라퀴논, 캠퍼퀴논 등의 퀴논 화합물;10-부틸-2-클로로아크리돈, 벤질, 페닐글리옥실산 메틸, 티타노센 화합물 등을 들 수 있다.Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4- Benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone and the like Benzophenone compounds, quinone compounds such as 9,10-phenanthrenequinone, 2-ethyl anthraquinone and camphorquinone, 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, .
이들은, 후술의 중합 개시 조제(D1)(특히 아민류)와 조합하여 이용하는 것이 바람직하다.These are preferably used in combination with the polymerization initiator D1 (particularly amines) described below.
산을 발생하는 중합 개시제로서는, 예를 들면, 4-하이드록시페닐디메틸술포늄-p-톨루엔술포나트, 4-하이드록시페닐디메틸술포늄헥사플루오로안티모네이트, 4-아세톡시페닐디메틸술포늄-p-톨루엔술포나트, 4-아세톡시페닐메틸벤질술포늄헥사플루오로안티모네이트, 트리페닐술포늄-p-톨루엔술포나트, 트리페닐술포늄헥사플루오로안티모네이트, 디페닐요오드늄-p-톨루엔술포나트, 디페닐요오드늄헥사플루오로안티모네이트 등의 오늄염류나, 니트로벤질토실레이트류, 벤조인토실레이트류 등을 들 수 있다.Examples of the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium-p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium P-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium-p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium- onium salts such as p-toluenesulfonate and diphenyliodonium hexafluoroantimonate, nitrobenzyltosylates, benzoin tosylates and the like.
중합 개시제(D)로서는, 활성 라디칼을 발생하는 중합 개시제가 바람직하고, 구체적으로는, 알킬페논 화합물, 트리아진 화합물, 아실포스핀 옥사이드 화합물, O-아실옥심 화합물 및 비이미다졸 화합물로 이루어지는 군으로부터 선택되는 적어도 일종을 포함하는 중합 개시제이고, 보다 바람직하게는, O-아실옥심 화합물을 포함하는 중합 개시제이다.As the polymerization initiator (D), a polymerization initiator that generates an active radical is preferable, and specifically, a polymerization initiator is added from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a non- Is a polymerization initiator containing at least one kind selected from the group consisting of O-acyloxime compounds. More preferably, it is a polymerization initiator comprising an O-acyloxime compound.
중합 개시제(D)의 함유량은, 수지(B) 및 중합성 화합물(C)의 합계량 100질량부에 대하여, 바람직하게는 0.1~40질량부이고, 보다 바람직하게는 1~30질량부이다.The content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass, and more preferably 1 to 30 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
<중합 개시 조제(D1)>≪ Polymerization initiator (D1) >
중합 개시 조제(D1)은, 중합 개시제에 의해 중합이 개시된 중합성 화합물의 중합을 촉진하기 위해서 이용되는 화합물, 혹은 증감제이다. 중합 개시 조제(D1)을 포함하는 경우, 통상, 중합 개시제(D)와 조합하여 이용된다.The polymerization initiator (D1) is a compound or a sensitizer used for promoting polymerization of a polymerizable compound initiated by polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).
중합 개시 조제(D1)로서는, 아민 화합물, 알콕시안트라센 화합물, 티옥산톤 화합물 및 카본산 화합물 등을 들 수 있다.Examples of the polymerization initiator (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carbonic acid compound.
상기 아민 화합물로서는, 트리에탄올아민, 메틸디에탄올아민, 트리이소프로판올아민 등의 알칸올아민;4-디메틸아미노벤조산 메틸, 4-디메틸아미노벤조산 에틸, 4-디메틸아미노벤조산 이소아밀, 벤조산2-디메틸아미노에틸, 4-디메틸아미노벤조산2-에틸헥실 등의 아미노벤조산 에스테르;N,N-디메틸파라톨루이딘;4,4'-비스(디메틸아미노)벤조페논(통칭 미히라즈케톤), 4,4'-비스(디에틸아미노)벤조페논, 4,4'-비스(에틸메틸아미노)벤조페논 등의 알킬아미노벤조페논;등을 들 수 있고, 그 중에서도, 알킬아미노벤조페논이 바람직하고, 4,4'-비스(디에틸아미노)벤조페논이 바람직하다. EAB-F(호도가야화학공업(주) 제) 등의 시판품을 이용해도 된다.Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine and triisopropanolamine; aliphatic amines such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, Aminobenzoic acid ester such as 4-dimethylaminobenzoic acid, 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (Diethylamino) benzophenone, and 4,4'-bis (ethylmethylamino) benzophenone; and among them, alkylaminobenzophenone is preferable, and 4,4'- Bis (diethylamino) benzophenone is preferred. And commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.
상기 알콕시안트라센 화합물로서는, 9,10-디메톡시안트라센, 2-에틸-9,10-디메톡시안트라센, 9,10-디에톡시안트라센, 2-에틸-9, 10-디에톡시안트라센, 9,10-디부톡시안트라센, 2-에틸-9,10-디부톡시안트라센 등을 들 수 있다.Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, Dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.
상기 티옥산톤 화합물로서는, 2-이소프로필티옥산톤, 4-이소프로필티옥산톤, 2,4-디에틸티옥산톤, 2,4-디클로로티옥산톤, 1-클로로-4-프로폭시티옥산톤 등을 들 수 있다.Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Citoxanthone and the like.
상기 카본산 화합물로서는, 페닐술파닐아세트산, 메틸페닐술파닐아세트산, 에틸페닐술파닐아세트산, 메틸에틸페닐술파닐아세트산, 디메틸페닐술파닐아세트산, 메톡시페닐술파닐아세트산, 디메톡시페닐술파닐아세트산, 클로로페닐술파닐아세트산, 디클로로페닐술파닐아세트산, N-페닐글리신, 페녹시아세트산, 나프틸티오아세트산, N-나프틸글리신, 나프톡시아세트산 등을 들 수 있다.Examples of the carbonic acid compound include phenylsulfanyl acetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chloro Phenylsulfanyl acetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
이들의 중합 개시 조제(D1)를 이용하는 경우, 그 함유량은, 수지(B) 및 중합성 화합물(C)의 합계량 100질량부에 대하여, 바람직하게는 0.1~30질량부, 보다 바람직하게는 1~20질량부이다. 중합 개시 조제(D1)의 양이 이 범위 내에 있으면, 더욱 고감도로 착색 패턴을 형성할 수 있어, 칼라 필터의 생산성이 향상하는 경향이 있다.When the polymerization initiator (D1) is used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 30 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) 20 parts by mass. When the amount of the polymerization initiator (D1) is within this range, it is possible to form a colored pattern with higher sensitivity, and the productivity of the color filter tends to be improved.
<용제(E)>≪ Solvent (E) >
용제(E)는, 특별히 한정되지 않고, 당해 분야에서 통상 사용되는 용제를 이용할 수 있다. 예를 들면, 에스테르 용제(분자 내에 -COO-를 포함하고, -O-를 포함하지 않는 용제), 에테르 용제(분자 내에 -O-를 포함하고, -COO-를 포함하지 않는 용제), 에테르에스테르 용제(분자 내에 -COO-와 -O-를 포함하는 용제), 케톤 용제(분자 내에 -CO-를 포함하고, -COO-를 포함하지 않는 용제), 알코올 용제(분자 내에 OH를 포함하고, -O-, -CO- 및 -COO-를 포함하지 않는 용제), 방향족 탄화수소 용제, 아미드 용제, 디메틸술폭시드 등을 들 수 있다.The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. For example, an ester solvent (a solvent containing -COO- in the molecule and containing no -O-), an ether solvent (a solvent containing -O- and no -COO- in the molecule), an ether ester (Solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not including -COO-), alcohol solvent (containing OH in the molecule, O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.
에스테르 용제로서는, 락트산 메틸, 락트산 에틸, 락트산 부틸, 2-하이드록시 이소부탄산 메틸, 아세트산 에틸, 아세트산n-부틸, 아세트산 이소부틸, 포름산 펜틸, 아세트산 이소펜틸, 프로피온산 부틸, 부티르산 이소프로필, 부티르산 에틸, 부티르산 부틸, 피루브산 메틸, 피루브산 에틸, 피루브산 프로필, 아세토아세트산 메틸, 아세토아세트산 에틸, 사이클로헥산올아세테이트, γ-부티로락톤 등을 들 수 있다.Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, Butyl propionate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.
에테르 용제로서는, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노프로필에테르, 에틸렌글리콜모노부틸에테르, 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르, 디에틸렌글리콜모노부틸에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르, 3-메톡시-1-부탄올, 3-메톡시-3-메틸부탄올, 테트라하이드로푸란, 테트라하이드로피란, 1,4-디옥산, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜메틸에틸에테르, 디에틸렌글리콜디프로필에테르, 디에틸렌글리콜디부틸에테르, 아니솔, 페네톨, 메틸아니솔 등을 들 수 있다.Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methyl anisole And the like.
에테르 에스테르 용제로서는, 메톡시아세트산 메틸, 메톡시아세트산 에틸, 메톡시아세트산 부틸, 에톡시아세트산 메틸, 에톡시아세트산 에틸, 3-메톡시프로피온산 메틸, 3-메톡시프로피온산 에틸, 3-에톡시프로피온산 메틸, 3-에톡시프로피온산 에틸, 2-메톡시프로피온산 메틸, 2-메톡시프로피온산 에틸, 2-메톡시프로피온산 프로필, 2-에톡시프로피온산 메틸, 2-에톡시프로피온산 에틸, 2-메톡시-2-메틸프로피온산 메틸, 2-에톡시-2-메틸프로피온산 에틸, 3-메톡시부틸아세테이트, 3-메틸-3-메톡시부틸아세테이트, 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트, 에틸렌글리콜모노메틸에테르아세테이트, 에틸렌글리콜모노에틸에테르아세테이트, 디에틸렌글리콜모노에틸에테르아세테이트, 디에틸렌글리콜모노부틸에테르아세테이트, 디프로필렌글리콜메틸에테르아세테이트 등을 들 수 있다.Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate , Ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, Methyl propionate, methyl propionate, methyl 2-ethoxy-2-methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono Propyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate , Di, and the like ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate.
케톤 용제로서는, 4-하이드록시-4-메틸-2-펜탄온, 아세톤, 2-부탄온, 2-헵탄온, 3-헵탄온, 4-헵탄온, 4-메틸-2-펜탄온, 사이클로펜탄온, 사이클로헥산온, 이소포론 등을 들 수 있다.Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, Pentanone, cyclohexanone, isophorone, and the like.
알코올 용제로서는, 메탄온, 에탄올, 프로판올, 부탄올, 헥산올, 사이클로헥산올, 에틸렌글리콜, 프로필렌글리콜, 글리세린 등을 들 수 있다.Examples of the alcohol solvent include methanone, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
방향족 탄화수소 용제로서는, 벤젠, 톨루엔, 자일렌, 메시틸렌 등을 들 수 있다.Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.
아미드 용제로서는, N,N-디메틸포름아미드, N,N-디메틸아세토아미드, N-메틸피롤리돈 등을 들 수 있다.Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetoamide and N-methylpyrrolidone.
이들 용제는, 단독으로 이용해도 2종 이상을 병용해도 된다.These solvents may be used alone or in combination of two or more.
그 중에서도, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노부틸에테르, 프로필렌글리콜모노메틸에테르, 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르, 프로필렌글리콜모노메틸에테르아세테이트, 디프로필렌글리콜메틸에테르아세테이트, 3-메톡시-1-부탄올, 3-메톡시부틸아세테이트, 3-에톡시프로피온산 에틸, 락트산 에틸, N-메틸피롤리돈, 4-하이드록시-4-메틸-2-펜탄온, N,N-디메틸포름아미드 등이 바람직하고, 에틸렌글리콜모노부틸에테르, 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노메틸에테르아세테이트, 디프로필렌글리콜메틸에테르아세테이트, 3-메톡시-1-부탄올, 3-메톡시부틸아세테이트, 3-에톡시프로피온산 에틸, 락트산 에틸, N-메틸피롤리돈이 보다 바람직하다.Among them, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3 Methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, N-methylpyrrolidone, 4-hydroxy-4-methyl-2-pentanone, N, N- Propyleneglycol monomethyl ether acetate, dipropyleneglycol methyl ether acetate, 3-methoxy-1-butanol, 3-methoxybutyl acetate, 3-methoxybutyl acetate, Ethyl 3-ethoxypropionate, ethyl lactate and N-methylpyrrolidone are more preferred.
용제(E)의 함유량은, 착색 경화성 수지 조성물의 총량에 대하여, 바람직하게는 70~95질량%이고, 보다 바람직하게는 75~92질량%이다. 바꾸어 말하면, 착색 경화성 수지 조성물의 고형분의 총량은, 바람직하게는 5~30질량%, 보다 바람직하게는 8~25질량%이다. 용제(E)의 함유량이 상기의 범위에 있으면, 도포시의 평탄성이 양호하게 되고, 또한 칼라 필터를 형성했을 때에 흡광도가 부족하지 않기 때문에 표시 특성이 양호해지는 경향이 있다.The content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition. In other words, the total amount of solids in the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and when the color filter is formed, the absorbance is not insufficient and the display characteristics tend to be good.
<레벨링제(F)>≪ Leveling agent (F) >
레벨링제(F)로서는, 실리콘계 계면 활성제, 불소계 계면 활성제 및 불소 원자를 갖는 실리콘계 계면 활성제 등을 들 수 있다. 이들은, 측쇄에 중합성기를 갖고 있어도 된다.Examples of the leveling agent (F) include a silicone surfactant, a fluorinated surfactant, and a silicon surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
실리콘계 계면 활성제로서는, 분자 내에 실록산 결합을 갖는 계면 활성제 등을 들 수 있다. 구체적으로는, 토레이실리콘 DC3PA, 동 SH7PA, 동 DC11PA, 동 SH21PA, 동 SH28PA, 동 SH29PA, 동 SH30PA, 동 SH8400(토레이·다우코닝(주) 제), KP321, KP322, KP323, KP324, KP326, KP340, KP341(신에츠화학공업(주) 제), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 및 TSF4460(모멘티브·퍼포먼스·머티리얼즈·재팬합동회사 제) 등을 들 수 있다.Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Concretely, Torei Silicon DC3PA, Copper SH7PA, Copper DC11PA, Copper SH21PA, Copper SH28PA, Copper SH29PA, Copper SH30PA, Copper SH8400 (manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340 , KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Momentive Performance Materials Japan Joint-Industrial Company).
상기의 불소계 계면 활성제로서는, 분자 내에 플루오로카본쇄를 갖는 계면 활성제 등을 들 수 있다. 구체적으로는, 플로라드(등록상표)FC430, 동 FC431(스미토모3M(주) 제), 메가팍스(등록상표) F142D, 동 F171, 동 F172, 동 F173, 동 F177, 동 F183, 동 F554, 동 R30, 동 RS-718-K(DIC(주) 제), 에프톱(등록상표) EF301, 동 EF303, 동 EF351, 동 EF352(미스비시머티리얼 전자화성(주) 제), 서프론(등록상표) S381, 동 S382, 동 SC101, 동 SC105(아사히유리(주) 제) 및 E5844((주) 다이킨정제화학제품연구소 제) 등을 들 수 있다.Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Concretely, it is possible to use a fluorine-containing resin such as FLORAD (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafox (registered trademark) F142D, copper F171, copper F172, copper F173, copper F177, copper F183, R30, RS-718-K (manufactured by DIC Corporation), Epson (registered trademark) EF301, EF303, EF351 and EF352 (manufactured by Misby Materials Electronic Co., S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Tablet Chemical Industry Co., Ltd.).
상기의 불소 원자를 갖는 실리콘계 계면 활성제로서는, 분자 내에 실록산 결합 및 플루오로카본쇄를 갖는 계면 활성제 등을 들 수 있다. 구체적으로는, 메가팍스(등록상표) R08, 동 BL20, 동 F475, 동 F477 및 동 F443(DIC(주) 제) 등을 들 수 있다.Examples of the silicon-containing surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafox (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC) can be mentioned.
레벨링제(F)를 함유하는 경우, 그 함유량은, 착색 경화성 수지 조성물의 총량에 대하여, 바람직하게는 0.001질량% 이상 0.2질량% 이하이고, 보다 바람직하게는 0.002질량% 이상 0.1질량% 이하, 더욱 바람직하게는 0.005질량% 이상 0.07질량% 이하이다. 레벨링제(F)의 함유량이 상기의 범위 내에 있으면, 칼라 필터의 평탄성을 양호하게 할 수 있다.When the leveling agent (F) is contained, the content thereof is preferably 0.001 mass% or more and 0.2 mass% or less, more preferably 0.002 mass% or more and 0.1 mass% or less, relative to the total amount of the colored curable resin composition, Preferably 0.005 mass% or more and 0.07 mass% or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
<그 외의 성분><Other components>
착색 경화성 수지 조성물은, 필요에 따라서, 충전제, 다른 고분자 화합물, 밀착 촉진제, 산화 방지제, 광 안정제, 연쇄 이동제 등, 당해 기술 분야에서 공지의 첨가제를 포함해도 된다.The colored curable resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, if necessary.
<착색 경화성 수지 조성물의 제조 방법>≪ Process for producing colored curable resin composition >
착색 경화성 수지 조성물은, 예를 들면, 착색제(A), 수지(B), 중합성 화합물(C), 중합 개시제(D), 및 용제(E), 필요에 따라서 이용되는, 레벨링제(F), 중합 개시 조제(D1) 및 그 외의 성분을 혼합함으로써 조제할 수 있다.The coloring curable resin composition may contain a coloring agent (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E) , The polymerization initiator (D1), and other components.
안료(P)를 포함하는 경우의 안료는, 미리 용제(E)의 일부 또는 전부와 혼합하여, 안료의 평균 입자 지름이 0.2μm 이하 정도가 될 때까지, 비즈 밀 등을 이용해 분산시키는 것이 바람직하다. 이 때, 필요에 따라서 상기 안료 분산제, 수지(B)의 일부 또는 전부를 배합해도 된다. 이와 같이 하여 얻어진 안료 분산액에, 나머지 성분을, 소정의 농도가 되도록 혼합함으로써, 목적의 착색 경화성 수지 조성물을 조제할 수 있다.The pigment in the case of containing the pigment (P) is preferably mixed with a part or the whole of the solvent (E) in advance and dispersed with a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 탆 or less . At this time, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. The desired colored curable resin composition can be prepared by mixing the remaining components in the thus obtained pigment dispersion to a predetermined concentration.
또한 화합물(A-I)을, 미리 용제(E)의 일부 또는 전부에 용해시켜 용액을 조제하는 것이 바람직하다. 추가로 당해 용액을, 공경 0.01~1μm 정도의 필터로 여과하는 것이 바람직하다.It is also preferable to prepare the solution by previously dissolving the compound (A-I) in a part or all of the solvent (E). Further, the solution is preferably filtered with a filter having a pore size of 0.01 to 1 mu m or so.
혼합 후의 착색 경화성 수지 조성물을, 공경 0.01~10μm 정도의 필터로 여과하는 것이 바람직하다.The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 mu m.
<칼라 필터의 제조 방법><Manufacturing Method of Color Filter>
본 발명의 착색 경화성 수지 조성물로부터 착색 패턴을 제조하는 방법으로서는, 포토리소그래프법, 잉크젯법, 인쇄법 등을 들 수 있다. 그 중에서도, 포토리소그래프법이 바람직하다. 포토리소그래프법은, 상기 착색 경화성 수지 조성물을 기판에 도포하고, 건조시켜 착색 조성물층을 형성하고, 포토마스크를 통하여 당해 착색 조성물층을 노광하여, 현상하는 방법이다. 포토리소그래프법에 있어서, 노광시에 포토마스크를 이용하지 않는 것, 및/또는 현상하지 않는 것에 의해, 상기 착색 조성물층의 경화물인 착색 도막을 형성할 수 있다. 이와 같이 형성한 착색 패턴이나 착색 도막이 본 발명의 칼라 필터이다.Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, a printing method, and the like. Among them, a photolithographic method is preferable. In the photolithographic method, the above-mentioned colored curable resin composition is applied to a substrate, followed by drying to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithographic method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask at the time of exposure and / or by not developing it. The coloring pattern or colored coating film thus formed is the color filter of the present invention.
제작하는 칼라 필터의 막두께는, 특별히 한정되지 않고, 목적이나 용도 등에 따라서 적절히 조정할 수 있고, 예를 들면, 0.1~30μm, 바람직하게는 0.1~20μm, 더욱 바람직하게는 0.5~6μm이다.The film thickness of the color filter to be produced is not particularly limited and can be suitably adjusted in accordance with the purpose and application, and is, for example, 0.1 to 30 탆, preferably 0.1 to 20 탆, more preferably 0.5 to 6 탆.
기판으로서는, 석영 유리, 붕규산 유리, 알루미나규산염 유리, 표면을 실리카 코팅한 소다 라임 유리 등의 유리판이나, 폴리카보네이트, 폴리메타크릴산 메틸, 폴리에틸렌텔레프탈레이트 등의 수지판, 실리콘, 상기 기판 상에 알루미늄, 은, 은/구리/팔라듐 합금 박막 등을 형성한 것이 이용된다. 이들 기판 상에는, 별도의 칼라 필터층, 수지층, 트랜지스터, 회로 등이 형성되어 있어도 된다.Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass and soda lime glass whose surface is coated with a silica, resin plates such as polycarbonate, polymethylmethacrylate and polyethylene terephthalate, silicon, , Silver, silver / copper / palladium alloy thin film, or the like is formed. A separate color filter layer, a resin layer, a transistor, a circuit, and the like may be formed on these substrates.
포토리소그래프법에 의한 각 색 화소의 형성은, 공지 또는 관용의 장치나 조건으로 행할 수 있다. 예를 들면, 하기와 같이 하여 제작할 수 있다.The formation of each color pixel by the photolithographic method can be performed by a known apparatus or condition. For example, it can be manufactured as follows.
먼저, 착색 경화성 수지 조성물을 기판 상에 도포하고, 가열 건조(프리베이킹) 및/또는 감압 건조함으로써 용제 등의 휘발 성분을 제거하여 건조시켜, 평활한 착색 조성물층을 얻는다.First, a colored curable resin composition is coated on a substrate and dried by heating (prebaking) and / or drying under reduced pressure to remove volatile components such as a solvent and drying to obtain a smooth colored composition layer.
도포 방법으로서는, 스핀 코팅법, 슬릿 코팅법, 슬릿 앤드 스핀 코팅법 등을 들 수 있다.Examples of the application method include a spin coating method, a slit coating method, and a slit and spin coating method.
가열 건조를 행하는 경우의 온도는, 30~120℃가 바람직하고, 50~110℃이 보다 바람직하다. 또한 가열 시간으로서는, 10초간~60분간인 것이 바람직하고, 30초간~30분간인 것이 보다 바람직하다.The temperature in the case of heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
감압 건조를 행하는 경우는, 50~150Pa의 압력하, 20~25℃의 온도 범위에서 행하는 것이 바람직하다.In the case of performing the reduced-pressure drying, it is preferably carried out at a temperature of 20 to 25 캜 under a pressure of 50 to 150 Pa.
착색 조성물층의 막두께는, 특별히 한정되지 않고, 목적으로 하는 칼라 필터의 막두께에 따라 적절히 선택하면 된다.The film thickness of the coloring composition layer is not particularly limited and may be suitably selected in accordance with the intended thickness of the color filter.
다음으로, 착색 조성물층은, 목적의 착색 패턴을 형성하기 위한 포토마스크를 통하여 노광된다. 당해 포토마스크 상의 패턴은 특별히 한정되지 않고, 목적으로 하는 용도에 따른 패턴이 이용된다.Next, the coloring composition layer is exposed through a photomask for forming a desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
노광에 이용되는 광원으로서는, 250~450nm의 파장의 빛을 발생하는 광원이 바람직하다. 예를 들면, 350nm 미만의 빛을, 이 파장역을 컷하는 필터를 이용하여 컷하거나 436nm 부근, 408nm 부근, 365nm 부근의 빛을, 이들 파장역을 취출하는 밴드 패스 필터를 이용하여 선택적으로 취출해도 된다. 구체적으로는, 광원으로서는, 수은등, 발광 다이오드, 메탈 할라이드 램프, 할로겐 램프 등을 들 수 있다.As a light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, if light having a wavelength of less than 350 nm is cut using a filter that cuts the wavelength region, or light around 436 nm, around 408 nm, or around 365 nm is selectively extracted using a bandpass filter for extracting these wavelength regions do. Specifically, examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.
노광면 전체에 균일하게 평행 광선을 조사하거나, 포토마스크와 착색 조성물층이 형성된 기판의 정확한 위치 맞춤을 행할 수 있기 때문에, 마스크 얼라이너 및 스테퍼 등의 노광 장치를 사용하는 것이 바람직하다.It is preferable to use an exposure apparatus such as a mask aligner and a stepper to uniformly irradiate the entire exposure surface with a parallel light beam or accurately align the substrate on which the coloring composition layer is formed.
노광 후의 착색 조성물층을 현상액에 접촉시켜 현상함으로써, 기판 상에 착색 패턴이 형성된다. 현상에 의해, 착색 조성물층의 미노광부가 현상액에 용해하여 제거된다. 현상액으로서는, 예를 들면, 수산화 칼륨, 탄산수소나트륨, 탄산나트륨, 수산화 테트라메틸암모늄 등의 알칼리성 화합물의 수용액이 바람직하다. 이들 알칼리성 화합물의 수용액 중의 농도는, 바람직하게는 0.01~10질량%이고, 보다 바람직하게는 0.03~5질량%이다. 또한, 현상액은, 계면 활성제를 포함하고 있어도 된다.The colored composition layer after exposure is brought into contact with a developing solution to develop a colored pattern on the substrate. By the development, the unexposed portion of the colored composition layer is dissolved and removed in the developer. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
현상 방법은, 패들법, 디핑법 및 스프레이법 등의 어느것이라도 된다. 또한 현상시에 기판을 임의의 각도로 기울여도 된다.The developing method may be any of a paddle method, a dipping method, and a spray method. Further, the substrate may be inclined at an arbitrary angle during development.
현상 후는, 물 세정하는 것이 바람직하다.After development, it is preferable to rinse with water.
또한, 얻어진 착색 패턴에, 포스트베이킹을 행하는 것이 바람직하다. 포스트베이킹 온도는, 150~250℃가 바람직하고, 160~235℃가 보다 바람직하다. 포스트베이킹 시간은, 1~120분간이 바람직하고, 10~60분간이 보다 바람직하다.In addition, post-baking is preferably performed on the obtained coloring pattern. The post-baking temperature is preferably 150 to 250 占 폚, more preferably 160 to 235 占 폚. The post baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.
본 발명의 화합물은, 흡광도가 높은 점에서, 이를 이용한 착색 경화성 수지 조성물에 의해, 특히 고명도인 칼라 필터를 제조할 수 있다. 당해 칼라 필터는, 표시 장치(예를 들면, 액정 표시 장치, 유기 EL 장치, 전자 페이퍼 등) 및 고체 촬상 소자에 이용되는 칼라 필터로서 유용하다.From the viewpoint of high absorbance, the compound of the present invention can produce a color filter with particularly high brightness by using the colored curable resin composition using the same. Such a color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.
본원은, 2014년 10월 31일에 출원된 일본 특허 출원 제2014-223768호에 기초하는 우선권의 이익을 주장하는 것이다. 2014년 10월 31일에 출원된 일본 특허 출원 제2014-223768호의 명세서의 전내용이, 본원에 참고를 위해 원용된다.This application claims the benefit of priority based on Japanese Patent Application No. 2014-223768, filed on October 31, 2014. The entire contents of the specification of Japanese Patent Application No. 2014-223768 filed on October 31, 2014 are incorporated herein by reference.
[실시예][Example]
이하, 실시예에 의해서 본 발명을 보다 상세하게 설명하는데, 본 발명은 이들 실시예에 의해서 한정되는 것은 아니다. 예 중, 함유량 내지 사용량을 나타내는 % 및 부는, 특별히 언급하지 않는 한 질량 기준이다.Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the examples,% and parts representing the content or amount are based on mass unless otherwise specified.
이하에 있어서, 화합물의 구조는 질량 분석(LC;Agilent제 1200형, MASS;Agilent 제 LC/MSD형), UV-VIS(일본 분광제 V-650)로 확인했다.In the following, the structure of the compound was confirmed by mass analysis (LC: Agilent 1200 type, MASS: Agilent LC / MSD type) and UV-VIS (Japanese Spectroscopic agent V-650).
〔실시예 1〕[Example 1]
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 티오시안산 칼륨 32.2부 및 아세톤 160.0부를 투입한 후, 실온하에서 30분 교반했다. 이어서, 2-플루오로벤조산 염화물(도쿄화성(주)사 제) 50.0부를 10분에 걸쳐 적하했다. 적하 종료 후, 추가로 실온하에서 2시간 교반했다. 이어서, 반응 혼합물을 빙랭한 후, N-에틸-o-톨루이딘(도쿄화성(주)사 제) 40.5부를 적하했다. 적하 종료 후, 추가로 실온하에서 30분 교반했다. 이어서, 반응 혼합물을 빙랭한 후, 30% 수산화 나트륨 수용액 34.2부를 적하했다. 적하 종료 후, 추가로 실온하에서 30분 교반했다. 이어서, 실온하에서 클로로아세트산 31.3부를 적하했다. 적하 종료 후, 가열 환류하에서 7시간 교반했다. 이어서, 반응 혼합물을 실온까지 방랭한 후, 반응 용액을 수도물 120.0부 중에 부은 후, 톨루엔 200부를 첨가하여 30분 교반했다. 이어서 교반을 정지하고, 30분 정치한 바, 유기층과 수층으로 분리되었다. 수층을 분액 조작으로 폐기한 후, 유기층을 1규정 염산 200부로 세정하고, 이어서 수도물 200부로 세정하고, 마지막에 포화 식염수 200부로 세정했다. 유기층에 적당량의 황산 나트륨을 첨가하여 30분 교반한 후, 여과하여 건조된 유기층을 얻었다. 얻어진 유기층을 이배퍼레이터로 용매 증류 제거하여, 담황색 액체를 얻었다. 얻어진 담황색 액체를 칼럼 크로마토그래피로 정제했다. 정제한 담황색 액체를 감압하 60에서 건조하여, 식(B-I-2)로 나타나는 화합물을 49.9부 얻었다. 수율 51%.The following reaction was carried out in a nitrogen atmosphere. A cooling tube and a stirrer, 32.2 parts of potassium thiocyanate and 160.0 parts of acetone were charged, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of 2-fluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of dropwise addition, the mixture was further stirred at room temperature for 2 hours. Subsequently, after the reaction mixture was ice-cooled, 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Then, after the reaction mixture was ice-cooled, 34.2 parts of 30% sodium hydroxide aqueous solution was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Subsequently, 31.3 parts of chloroacetic acid was added dropwise at room temperature. After completion of the dropwise addition, the mixture was stirred for 7 hours under reflux. Then, after the reaction mixture was cooled to room temperature, the reaction solution was poured into 120.0 parts of tap water, 200 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes, and the organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 200 parts of 1N hydrochloric acid, followed by 200 parts of tap water and finally with 200 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer, and the mixture was stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was subjected to solvent distillation with a diverter to obtain a pale yellow liquid. The resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried under reduced pressure at 60 to obtain 49.9 parts of a compound represented by the formula (B-I-2). Yield 51%.
<화학식 39>≪ EMI ID =
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에 N-메틸아닐린(도쿄화성(주)사 제) 15.3부 및 N,N-디메틸포름아미드 60부를 투입한 후, 혼합 용액을 빙랭했다. 빙랭하에 60% 수소화 나트륨(도쿄화성(주)사 제) 5.7부를 30분에 걸쳐 조금씩 첨가한 후, 실온으로 승온하면서 1시간 교반했다. 4,4'-디플루오로벤조페논(도쿄화성(주)사 제) 10.4부를 조금씩 반응액에 추가하여 실온에서 24시간 교반했다. 반응액을 빙수 200부에 조금씩 첨가한 후, 실온에서 15시간 정치하고, 물을 디캔테이션으로 제거하면 잔사로서 점조한 고체가 얻어졌다. 이 점조한 고체에 메탄올 60부를 추가한 후, 실온에서 15시간 교반했다. 석출한 고체를 여과 분별한 후, 칼럼 크로마토그래피로 정제했다. 정제한 담황색 고체를 감압하 60에서 건조하여, 식(C-I-2)으로 나타나는 화합물을 9.8부 얻었다. 수율 53%.The following reaction was carried out in a nitrogen atmosphere. 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N, N-dimethylformamide were added to a flask equipped with a cooling tube and a stirrer, and then the mixed solution was frozen. 5.7 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little over 30 minutes under ice-cooling, and the mixture was stirred for 1 hour while being warmed to room temperature. And 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) were added little by little to the reaction solution, followed by stirring at room temperature for 24 hours. The reaction solution was added to 200 parts of iced water, and the mixture was allowed to stand at room temperature for 15 hours. When water was removed by decantation, a viscous solid was obtained as a residue. After adding 60 parts of methanol to the thus-obtained solid, the mixture was stirred at room temperature for 15 hours. The precipitated solid was separated by filtration and then purified by column chromatography. The purified light yellow solid was dried under reduced pressure at 60 to obtain 9.8 parts of a compound represented by the formula (C-I-2). Yield 53%.
<화학식 40>≪ EMI ID =
이하의 반응은, 질소 분위기 하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 식(B-I-2)으로 나타나는 화합물 8.2부, 식(C-I-2)으로 나타나는 화합물 10.0부 및 톨루엔 20.0부를 투입한 후, 이어서, 옥시염화인 12.2부를 첨가하여 95~100에서 3시간 교반했다. 이어서, 반응 혼합물을 실온으로 냉각한 후, 이소프로판올 170.0부로 희석했다. 이어서, 희석한 반응 용액을 포화 식염수 300.0부 내에 부은 후, 톨루엔 100부를 첨가하여 30분 교반했다. 이어서 교반을 정지하여, 30분 정치한 바, 유기층과 수층으로 분리되었다. 수층을 분액 조작으로 폐기한 후, 유기층을 포화 식염수 300부로 세정했다. 유기층에 적당량의 황산 나트륨을 첨가하여 30분 교반한 후, 여과하여 유기층을 얻었다. 얻어진 유기층을 이배퍼레이터로 용매 증류 제거하여, 청자색 고체를 얻었다. 추가로 청자색 고체를 감압하 60에서 건조하여, 식(A-II-2)으로 나타나는 화합물을 18.4부 얻었다. 수율 100%.The following reaction was carried out in a nitrogen atmosphere. 8.2 parts of the compound represented by the formula (B-I-2), 10.0 parts of the compound represented by the formula (C-I-2) and 20.0 parts of toluene were charged into a flask equipped with a stirrer, Was added thereto, and the mixture was stirred at 95 to 100 for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170.0 parts of isopropanol. Subsequently, the diluted reaction solution was poured into 300.0 parts of saturated saline, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes, and the organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 300 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer, which was stirred for 30 minutes, and then filtered to obtain an organic layer. The obtained organic layer was subjected to solvent distillation with an equalizer to obtain a bluish green solid. Further, the bluish green solid was dried under reduced pressure at 60 to obtain 18.4 parts of a compound represented by the formula (A-II-2). Yield 100%.
<화학식 41>≪ EMI ID =
식(A-II-2)으로 나타나는 화합물의 동정Identification of the compound represented by the formula (A-II-2)
(질량 분석) 이온화 모드=ESI+:m/z=687.3[M-Cl]+ (Mass analysis) Ionization mode = ESI +: m / z = 687.3 [M-Cl] +
Exact Mass:722.3Exact Mass: 722.3
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 식(A-II-2)으로 나타나는 화합물 2.0부 및 디클로로메탄 7.3부를 투입한 후, 반응 용액을 빙랭했다. 이어서, 클로로술폰산(도쿄화성사 제) 1.6부를 첨가하여 실온으로 승온하면서 철야 교반했다. 이어서, 반응 용액을 빙랭하면서 N,N-디메틸포름아미드 34.0부로 희석했다. 이어서, 희석한 반응 용액을 톨루엔 140.0부 내에 부은 후, 30분 교반했다. 이어서 교반을 정지하여, 디캔테이션하여 청자색 점조 고체를 얻었다. 추가로 청자색 점조 고체를 감압하 60에서 건조하고, 식(A-I-2)으로 나타나는 화합물을 2.3부 얻었다. 수율 100%.The following reaction was carried out in a nitrogen atmosphere. 2.0 parts of the compound represented by the formula (A-II-2) and 7.3 parts of dichloromethane were put into a flask equipped with a cooling tube and a stirrer, and then the reaction solution was ice-cooled. Subsequently, 1.6 parts of chlorosulfonic acid (produced by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at room temperature overnight. Then, the reaction solution was diluted with 34.0 parts of N, N-dimethylformamide while ice-cooling. Subsequently, the diluted reaction solution was poured into 140.0 parts of toluene and stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was decanted to obtain a blue-violet colored solid. Further, the bluish purple colored solid was dried under reduced pressure at 60 to obtain 2.3 parts of a compound represented by the formula (A-I-2). Yield 100%.
<화학식 42>(42)
식(A-I-2)에 있어서, "-SO3 -" 및 "-SO3H"는, 6개의 페닐환의 적어도 1개에 있어서의 탄소 원자와 각각 결합하고 있는 것을 나타낸다.In the formula (A-I-2), "-SO 3 - " and "-SO 3 H" each represent a bond with carbon atoms in at least one of the six phenyl rings.
식(A-I-2)으로 나타나는 화합물의 동정Identification of compounds represented by formula (A-I-2)
(질량 분석) 이온화 모드=ESI+:m/z=847.3[M+H]+ (Mass analysis) Ionization mode = ESI +: m / z = 847.3 [M + H] +
ESI-:m/z=845.5[M-H]- ESI-: m / z = 845.5 [M-H] -
Exact Mass:846.2Exact Mass: 846.2
식(A-I-2)으로 나타나는 화합물 0.35g을 락트산 에틸에 용해하여 체적을 250㎤로 하고, 그 중의 2㎤를 락트산 에틸로 희석하여 체적을 100㎤로 하고(농도:0.028g/L), 분광 광도계(석영 셀, 광로 길이;1cm)를 이용하여 흡수 스펙트럼을 측정했다. 이 화합물은, λmax=627nm에서 흡광도 2.5(임의 단위)를 나타냈다.0.35 g of the compound represented by the formula (A-I-2) was dissolved in ethyl lactate to make the volume 250 cm 3, and 2 cm 3 of the compound was diluted with ethyl lactate to make the volume 100 cm 3 (concentration: 0.028 g / L) , And a spectrophotometer (quartz cell, optical path length: 1 cm). This compound exhibited an absorbance of 2.5 (arbitrary unit) at? Max = 627 nm.
〔비교예 1〕[Comparative Example 1]
C.I.애시드 블루 90(상품명;Daiwa BLUE 300, 다이와화성사 제) 0.35g을 락트산 에틸에 용해하여 체적을 250㎤로 하고, 그 중의 2㎤를 락트산 에틸로 희석하여 체적을 100㎤로 하고(농도:0.028g/L), 분광 광도계(석영 셀, 광로 길이;1cm)를 이용하여 흡수 스펙트럼을 측정했다. 이 화합물은, λmax=615nm에서 흡광도 2.2(임의 단위)를 나타냈다.0.35 g of CI Acid Blue 90 (trade name: Daiwa BLUE 300, manufactured by Daika Chemical Industry Co., Ltd.) was dissolved in ethyl lactate to make a volume of 250 cm 3, and 2 cm 3 of the solution was diluted with ethyl lactate to make a volume of 100 cm 3 (concentration: 0.028 g / L), and a spectrophotometer (quartz cell, optical path length: 1 cm). This compound exhibited an absorbance of 2.2 (arbitrary unit) at? Max = 615 nm.
실시예 1의 화합물(A-I-2)의 흡광도는, 비교예 1의 C.I.애시드 블루 90의 흡광도와 비교하여, 0.3크다(농도:0.028g/L).The absorbance of the compound (A-I-2) of Example 1 was 0.3 (concentration: 0.028 g / L) as compared with the absorbance of the CI Acid Blue 90 of Comparative Example 1.
〔실시예 2〕[Example 2]
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에 N-에틸아닐린(도쿄화성(주)사 제) 24.2부 및 N,N-디메틸포름아미드 240부를 투입한 후, 혼합 용액을 빙랭했다. 빙랭하에 60% 수소화 나트륨(도쿄화성(주)사 제) 8.0부를 30분에 걸쳐 조금씩 첨가한 후, 실온으로 승온하면서 1시간 교반했다. 4,4'-디플루오로벤조페논(도쿄화성(주)사 제) 14.4부를 조금씩 반응액에 추가하여 실온에서 72시간 교반했다. 반응액에 물을 첨가하여 디클로로메탄으로 추출하고, 포화 식염수로 3회 세정했다. 황산 마그네슘으로 건조하고, 여과 후 농축했다. 얻어진 조체(粗體)를 칼럼 크로마토그래피로 정제했다. 정제한 담황색 고체를 감압하 60에서 건조하여, 식(C-I-3)으로 나타나는 화합물을 7.4부 얻었다. 수율 27%.The following reaction was carried out in a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 24.2 parts of N-ethyl aniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 240 parts of N, N-dimethylformamide were added, and then the mixed solution was frozen. 8.0 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little over 30 minutes under ice-cooling, and the mixture was stirred for 1 hour while raising the temperature to room temperature. 14.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little to the reaction solution, and the mixture was stirred at room temperature for 72 hours. Water was added to the reaction solution, extracted with dichloromethane, and washed three times with saturated saline. Dried over magnesium sulfate, filtered and concentrated. The resulting crude product was purified by column chromatography. The purified light yellow solid was dried under reduced pressure at 60 to obtain 7.4 parts of a compound represented by the formula (C-I-3). Yield 27%.
<화학식 43>≪ Formula 43 >
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 식(B-I-2)으로 나타나는 화합물 7.6부, 식(C-I-3)으로 나타나는 화합물 10.0부 및 톨루엔 20.0부를 투입한 후, 이어서, 옥시염화인 11.4부를 첨가하여 95~100에서 3시간 교반했다. 이어서, 반응 혼합물을 실온으로 냉각한 후, 이소프로판올 170.0부로 희석했다. 이어서, 희석한 반응 용액을 포화 식염수 300.0부 내에 부은 후, 톨루엔 100부를 첨가하여 30분 교반했다. 이어서 교반을 정지하고, 30분 정치한 바, 유기층과 수층으로 분리되었다. 수층을 분액 조작으로 폐기한 후, 유기층을 포화 식염수 300부로 세정했다. 유기층에 적당량의 황산 나트륨를 첨가하여 30분 교반한 후, 여과하여 건조된 유기층을 얻었다. 얻어진 유기층을 이배퍼레이터로 용매 증류 제거하여, 청자색 고체를 얻었다. 얻어진 청자색 고체를 칼럼 크로마토그래피로 정제했다. 정제한 청자색 고체를 감압하 60에서 건조하고, 식(A-II-3)으로 나타나는 화합물을 17.8부 얻었다. 수율 100%.The following reaction was carried out in a nitrogen atmosphere. 7.6 parts of the compound represented by the formula (B-I-2), 10.0 parts of the compound represented by the formula (C-I-3) and 20.0 parts of toluene were introduced into a flask equipped with a stirrer, And the mixture was stirred at 95 to 100 for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170.0 parts of isopropanol. Subsequently, the diluted reaction solution was poured into 300.0 parts of saturated saline, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes, and the organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 300 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was subjected to solvent distillation with an equalizer to obtain a bluish green solid. The resulting violet solid was purified by column chromatography. The purified purple-violet solid was dried under reduced pressure at 60 to obtain 17.8 parts of a compound represented by the formula (A-II-3). Yield 100%.
<화학식 44>≪ Formula 44 >
식(A-II-3)으로 나타나는 화합물의 동정Identification of compounds represented by formula (A-II-3)
(질량 분석) 이온화 모드=ESI+:m/z=715.3[M-Cl]+ (Mass analysis) Ionization mode = ESI +: m / z = 715.3 [M-Cl] +
Exact Mass:750.3Exact Mass: 750.3
식(A-II-3)으로 나타나는 화합물을 실시예 1과 동일하게 술폰화하면, 식(A-I-3)으로 나타나는 화합물이 얻어진다.When the compound represented by the formula (A-II-3) is sulfonated in the same manner as in Example 1, a compound represented by the formula (A-I-3) is obtained.
<화학식 45><Formula 45>
식(A-I-3)에 있어서, "-SO3 -"및"-SO3H"는, 6개의 페닐환 중 적어도 1개에 있어서의 탄소 원자와 각각 결합하고 있는 것을 나타낸다.In the formula (A-I-3), "-SO 3 - " and "-SO 3 H" each represent a bond with carbon atoms in at least one of the six phenyl rings.
〔실시예 3〕[Example 3]
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 티오시안산 칼륨 28.9부 및 아세톤 160.0부를 투입한 후, 실온하에서 30분 교반했다. 이어서, 2,6-디플루오로벤조산 염화물(도쿄화성(주)사 제) 50.0부를 10분에 걸쳐 적하했다. 적하 종료 후, 추가로 실온하에서 2시간 교반했다. 이어서, 반응 혼합물을 빙랭한 후, N-에틸-o-톨루이딘(도쿄화성(주)사 제) 36.4부를 적하했다. 적하 종료 후, 투가로 실온하에서 30분 교반했다. 이어서, 반응 혼합물을 빙랭한 후, 30% 수산화 나트륨 수용액 34.2부를 적하했다. 적하 종료 후, 추가로 실온하에서 30분 교반했다. 이어서, 실온하 클로로아세트산 28.1부를 적하했다. 적하 종료 후, 가열 환류하에서 7시간 교반했다. 이어서, 반응 혼합물을 실온까지 방랭한 후, 반응 용액을 수도물 120.0부 내에 부은 후, 톨루엔 200부를 첨가하여 30분 교반했다. 이어서 교반을 정지하고, 30분 정치한 바, 유기층과 수층으로 분리되었다. 수층을 분액 조작으로 폐기한 후, 유기층을 1규정 염산 200부로 세정하고, 이어서 수도물 200부로 세정하고, 마지막에 포화 식염수 200부로 세정했다. 유기층에 적당량의 황산 나트륨을 첨가하여 30분 교반한 후, 여과하여 건조된 유기층을 얻었다. 얻어진 유기층을 이배퍼레이터로 용매 증류 제거하여, 담황색 액체를 얻었다. 얻어진 담황색 액체를 칼럼 크로마토그래피로 정제 했다. 정제한 담황색 액체를 감압하 60에서 건조하여, 식(B-I-3)으로 나타나는 화합물을 25.2부 얻었다. 수율 27%.The following reaction was carried out in a nitrogen atmosphere. In a flask equipped with a cooling tube and a stirrer, 28.9 parts of potassium thiocyanate and 160.0 parts of acetone were added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of 2,6-difluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of dropwise addition, the mixture was further stirred at room temperature for 2 hours. Subsequently, the reaction mixture was ice-cooled, and 36.4 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes. Then, after the reaction mixture was ice-cooled, 34.2 parts of 30% sodium hydroxide aqueous solution was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Subsequently, 28.1 parts of chloroacetic acid at room temperature was added dropwise. After completion of the dropwise addition, the mixture was stirred for 7 hours under reflux. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction solution was poured into 120.0 parts of tap water, 200 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes, and the organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 200 parts of 1N hydrochloric acid, followed by 200 parts of tap water and finally with 200 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer, and the mixture was stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was subjected to solvent distillation with a diverter to obtain a pale yellow liquid. The resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried under reduced pressure at 60 to obtain 25.2 parts of a compound represented by the formula (B-I-3). Yield 27%.
<화학식 46>≪ EMI ID =
이하의 반응은, 질소 분위기하에서 행했다. 냉각관 및 교반 장치를 구비한 플라스크에, 식(B-I-3)으로 나타나는 화합물 8.1부, 식(C-I-3)으로 나타나는 화합물 10.0부 및 톨루엔 20.0부를 투입한 후, 이어서, 옥시염화인 11.4부를 첨가하여 95~100에서 3시간 교반했다. 이어서, 반응 혼합물을 실온으로 냉각한 후, 이소프로판올 170.0부로 희석했다. 이어서, 희석한 반응 용액을 포화 식염수 300.0부 내에 부은 후, 톨루엔 100부를 첨가하여 30분 교반했다. 이어서 교반을 정지하고, 30분 정치한 바, 유기층과 수층으로 분리되었다. 수층을 분액 조작으로 폐기한 후, 유기층을 포화 식염수 300부로 세정했다. 유기층에 적당량의 황산 나트륨을 첨가하여 30분 교반한 후, 여과하여 건조된 유기층을 얻었다. 얻어진 유기층을 이배퍼레이터로 용매 증류 제거하여, 청자색 고체를 얻었다. 얻어진 청자색 고체를 칼럼 크로마토그래피로 정제했다. 정제한 청자색 고체를 감압하 60로 건조하여, 식(A-II-4)으로 나타나는 화합물을 18.3부 얻었다. 수율 100%.The following reaction was carried out in a nitrogen atmosphere. 8.1 parts of the compound represented by the formula (B-I-3), 10.0 parts of the compound represented by the formula (C-I-3) and 20.0 parts of toluene were charged into a flask equipped with a stirrer, And the mixture was stirred at 95 to 100 for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170.0 parts of isopropanol. Subsequently, the diluted reaction solution was poured into 300.0 parts of saturated saline, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Subsequently, stirring was stopped, and the mixture was allowed to stand for 30 minutes, and the organic layer and the aqueous layer were separated. After the aqueous layer was discarded by separating operation, the organic layer was washed with 300 parts of saturated saline. An appropriate amount of sodium sulfate was added to the organic layer, and the mixture was stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was subjected to solvent distillation with an equalizer to obtain a bluish green solid. The resulting violet solid was purified by column chromatography. The purified purple-violet solid was dried under reduced pressure to 60 to obtain 18.3 parts of a compound represented by the formula (A-II-4). Yield 100%.
<화학식 47>≪ EMI ID =
식(A-II-4)으로서 나타나는 화합물의 동정Identification of the compound represented by the formula (A-II-4)
(질량 분석) 이온화 모드=ESI+:m/z=733.3[M-Cl]+ (Mass analysis) Ionization mode = ESI +: m / z = 733.3 [M-Cl] +
Exact Mass:768.3Exact Mass: 768.3
식(A-II-4)으로 나타나는 화합물을 실시예 1과 동일하게 술폰화하면, 식(A-I-4)으로 나타나는 화합물이 얻어진다.When the compound represented by the formula (A-II-4) is sulfonated in the same manner as in Example 1, a compound represented by the formula (A-I-4) is obtained.
<화학식 48>(48)
식(A-I-4)에 있어서, "-SO3 -"및"-SO3H"는, 6개의 페닐환 중 적어도 1개에 있어서의 탄소 원자와 각각 결합하고 있는 것을 나타낸다.In the formula (A-I-4), "-SO 3 - " and "-SO 3 H" each represent a bond with carbon atoms in at least one of the six phenyl rings.
본 발명의 화합물은, 흡광도가 높다. 액정 표시 부품을 제조하기 위한 착색 경화성 수지 조성물이 본 발명의 화합물을 포함하는 경우, 사용량이 적어도 된다.The compounds of the present invention have high absorbance. When the colored curable resin composition for producing a liquid crystal display component contains the compound of the present invention, the usage amount is small.
Claims (4)
[식(A-I) 중,
R1a, R2a, R3a, R4a, R5a, R6a, R7a 및 R8a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, SO3 -기 또는 SO3M기를 나타낸다.
R9a 및 R10a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 치환되어 있어도 되는 방향족 탄화수소기, 또는 치환되어 있어도 되는 아르알킬기를 나타낸다.
R11a~R20a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 할로겐 원자, SO3 -기 또는 SO3M기를 나타낸다.
상기 R1a~R20a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.
R45a 및 R46a는, 각각 독립적으로, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.
R55a는, 수소 원자, 탄소수 1~10의 알킬기, 혹은 치환되어 있어도 되는 방향족 탄화수소기를 나타낸다.
상기 R45a, R46a, 및 R55a에 있어서, 상기 알킬기는, 구성하는 메틸렌기간에 산소 원자가 삽입되어 있어도 된다.
M은, 수소 이온, 금속 이온 또는 암모늄 이온을 나타낸다.
단, R1a~R20a, R45a, R46a 및 R55a는, 적어도(1) 및 (2) 중 어느 1개의 요건과, (4)의 요건을 만족한다.
(1) R1a~R8a 및 R11a~R20a중 적어도 1개는, SO3 -기 또는 SO3M기이다.
(2) R9a, R10a, R45a, R46a 및 R55a중 적어도 1개는, 치환기로서 SO3 -기 또는 SO3M기를 갖는 방향족 탄화수소기이다.
(4) 식(A-I)으로 나타나는 화합물이 갖는 SO3 -기의 수는 1이고, SO3M기의 수는 0~6이다.]
A compound represented by the formula (A-I).
[In the formula (A-I)
Each of R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a SO 3 - group or a SO 3 M group.
R 9a and R 10a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an optionally substituted aromatic hydrocarbon group, or an optionally substituted aralkyl group.
R 11a to R 20a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a SO 3 - group or a SO 3 M group.
In the above-mentioned R 1a to R 20a , the alkyl group may have an oxygen atom inserted in the methylene period constituting the alkyl group.
R 45a and R 46a each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group.
R 55a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon group.
In R 45a , R 46a and R 55a , the alkyl group may have oxygen atoms inserted into the constituent methylene period.
M represents a hydrogen ion, a metal ion or an ammonium ion.
Provided that R 1a to R 20a , R 45a , R 46a and R 55a satisfy at least one of the requirements of (1) and (2) and the requirement of (4).
(1) At least one of R 1a to R 8a and R 11a to R 20a is an SO 3 - group or a SO 3 M group.
(2) At least one of R 9a , R 10a , R 45a , R 46a and R 55a is an aromatic hydrocarbon group having a SO 3 - group or a SO 3 M group as a substituent.
(4) The number of SO 3 - groups in the compound represented by the formula (A-I) is 1 and the number of SO 3 M groups is 0 to 6.]
A colored curable resin composition comprising a compound represented by formula (A-I) according to claim 1.
A color filter formed using the colored curable resin composition according to claim 2.
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