TW202039699A - Colored curable resin composition - Google Patents
Colored curable resin composition Download PDFInfo
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- TW202039699A TW202039699A TW108146742A TW108146742A TW202039699A TW 202039699 A TW202039699 A TW 202039699A TW 108146742 A TW108146742 A TW 108146742A TW 108146742 A TW108146742 A TW 108146742A TW 202039699 A TW202039699 A TW 202039699A
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- meth
- resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 239000011347 resin Substances 0.000 claims abstract description 124
- 229920005989 resin Polymers 0.000 claims abstract description 124
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 37
- 239000003086 colorant Substances 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- -1 N-substituted maleimide Chemical class 0.000 abstract description 84
- 230000014759 maintenance of location Effects 0.000 abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- 239000002904 solvent Substances 0.000 description 58
- 229920001577 copolymer Polymers 0.000 description 48
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 40
- 150000002430 hydrocarbons Chemical group 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000049 pigment Substances 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- 239000000126 substance Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 23
- 239000000975 dye Substances 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229920001296 polysiloxane Polymers 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 16
- 238000002835 absorbance Methods 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 150000004292 cyclic ethers Chemical group 0.000 description 8
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 7
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 7
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229920006026 co-polymeric resin Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 4
- VDBSRPBXFACZJJ-UHFFFAOYSA-N 4-oxatetracyclo[6.2.1.02,7.03,5]undecan-9-yl prop-2-enoate Chemical compound C12CC3OC3C2C2CC(OC(=O)C=C)C1C2 VDBSRPBXFACZJJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 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 4
- 238000011161 development Methods 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 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 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 125000000623 heterocyclic 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 3
- CGILRHVKKLYKNE-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(C)COC1 CGILRHVKKLYKNE-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- FVNIMHIOIXPIQT-UHFFFAOYSA-N 2-methoxybutane Chemical compound CCC(C)OC FVNIMHIOIXPIQT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- WERQPPCVTFSKSO-UHFFFAOYSA-N 3a,7a-dimethyl-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1CC=CC2(C)C(=O)OC(=O)C21C WERQPPCVTFSKSO-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- JXUKQCUPTNLTCS-UHFFFAOYSA-N vat green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
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- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C08F22/40—Imides, e.g. cyclic imides
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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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
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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Abstract
Description
本發明是有關於一種著色硬化性樹脂組成物。The present invention relates to a colored curable resin composition.
液晶顯示裝置、電致發光(electroluminescence)顯示裝置及電漿顯示器等顯示裝置或電荷耦合器件(Charge Coupled Device,CCD)或互補金屬氧化物半導體(Complementary Metal-Oxide-Semiconductor Transistor,CMOS)感測器等固體攝像元件中使用的彩色濾光片是由著色樹脂組成物製造。作為此種著色樹脂組成物中所使用的著色劑,已知有方酸內鎓鹽染料(squarylium dye)(專利文獻1、專利文獻2等)。 [現有技術文獻] [專利文獻]Display devices such as liquid crystal display devices, electroluminescence (electroluminescence) display devices, and plasma displays, or charge coupled devices (CCD) or complementary metal oxide semiconductor (Complementary Metal-Oxide-Semiconductor Transistor, CMOS) sensors The color filters used in solid-state imaging devices are made of colored resin compositions. As a coloring agent used in such a coloring resin composition, a squarelium dye (squarylium dye) is known (Patent Document 1, Patent Document 2, etc.). [Prior Art Literature] [Patent Literature]
[專利文獻1]日本專利特開2015-86379號公報 [專利文獻2]日本專利特開2015-86380號公報[Patent Document 1] Japanese Patent Laid-Open No. 2015-86379 [Patent Document 2] Japanese Patent Laid-Open No. 2015-86380
[發明所欲解決之課題] 但是,由先前已知的使用方酸內鎓鹽染料作為著色劑的所述著色硬化性樹脂組成物所形成的彩色濾光片有時無法充分滿足吸光度保持率。因此,本發明的課題在於提供一種可形成吸光度保持率優異的彩色濾光片的著色硬化性樹脂組成物。 [解決課題之手段][The problem to be solved by the invention] However, the color filter formed of the previously known colored curable resin composition using a squarylium dye as a colorant sometimes fails to sufficiently satisfy the absorbance retention rate. Therefore, the subject of the present invention is to provide a colored curable resin composition capable of forming a color filter excellent in absorbance retention. [Means to solve the problem]
本發明的主旨如下所述。 [1] 一種著色硬化性樹脂組成物,包含著色劑、樹脂、聚合性化合物、以及聚合起始劑,且 所述著色劑為含有式(I)所表示的方酸內鎓鹽染料的著色劑, 所述樹脂為包含源自N-取代馬來醯亞胺的結構單元的樹脂。 [化1] [式(I)中, R1 ~R4 分別獨立地表示氫原子、鹵素原子、羥基或可具有取代基的碳數1~20的一價飽和烴基。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子。 R5 ~R8 分別獨立地表示氫原子或羥基。 Ar1 及Ar2 分別獨立地表示可具有取代基的碳數1~20的一價飽和烴基或式(i)所表示的基團。 [化2] [式(i)中, R12 表示可具有取代基的碳數1~20的一價飽和烴基或可具有取代基的碳數2~20的一價不飽和烴基,m表示0~5的整數。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子。m為2以上時,多個R12 分別可相同亦可不同。*表示與氮原子的結合鍵] R9 及R10 分別獨立地表示可具有取代基的碳數1~20的一價飽和烴基或式(i)所表示的基團。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子] [2] 一種彩色濾光片,其是由如[1]所述的著色硬化性樹脂組成物形成。 [3] 一種顯示裝置,包含如[2]所述的彩色濾光片。 [發明的效果]The gist of the present invention is as follows. [1] A coloring and curable resin composition comprising a coloring agent, a resin, a polymerizable compound, and a polymerization initiator, and the coloring agent is a coloring agent containing a squarylium dye represented by formula (I) , The resin is a resin containing a structural unit derived from N-substituted maleimide. [化1] [In formula (I), R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, or an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbons. An oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. R 5 to R 8 each independently represent a hydrogen atom or a hydroxyl group. Ar 1 and Ar 2 each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or a group represented by formula (i). [化2] [In formula (i), R 12 represents an optionally substituted monovalent saturated hydrocarbon group of 1 to 20 carbons or an optionally substituted monovalent unsaturated hydrocarbon group of 2 to 20 carbons, and m represents an integer of 0 to 5 . An oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. When m is 2 or more, a plurality of R 12 may be the same or different. *Represents a bond to a nitrogen atom] R 9 and R 10 each independently represent an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by formula (i). An oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group] [2] A color filter formed of the colored curable resin composition as described in [1]. [3] A display device including the color filter as described in [2]. [Effects of the invention]
根據本發明的著色硬化性樹脂組成物,可提供一種吸光度保持率優異的彩色濾光片。According to the colored curable resin composition of the present invention, it is possible to provide a color filter excellent in absorbance retention.
本發明的著色硬化性樹脂組成物包含:著色劑(以下,有時稱為著色劑(A))、樹脂(以下,有時稱為樹脂(B))、聚合性化合物(以下,有時稱為聚合性化合物(C))、以及聚合起始劑(以下,有時稱為聚合起始劑(D))。 著色劑含有式(I)所表示的方酸內鎓鹽染料(以下,有時稱為化合物(I))。 樹脂包含源自N-取代馬來醯亞胺的結構單元。 本發明的著色硬化性樹脂組成物較佳為更包含溶劑(以下,有時稱為溶劑(E))。 本發明的著色硬化性樹脂組成物亦可包含調平劑(以下,有時稱為調平劑(F))。 於本說明書中,作為各成分而例示的化合物只要無特別說明,則可單獨使用,或組合使用多種。The colored curable resin composition of the present invention includes a colorant (hereinafter, sometimes referred to as colorant (A)), resin (hereinafter, sometimes referred to as resin (B)), and a polymerizable compound (hereinafter, sometimes referred to as It is a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). The colorant contains a squarylium dye represented by formula (I) (hereinafter, sometimes referred to as compound (I)). The resin contains structural units derived from N-substituted maleimines. The colored curable resin composition of the present invention preferably further contains a solvent (hereinafter, sometimes referred to as solvent (E)). The colored curable resin composition of the present invention may also contain a leveling agent (hereinafter, it may be referred to as a leveling agent (F)). In this specification, the compound exemplified as each component can be used alone or in combination of multiple types unless otherwise specified.
<著色劑(A)> 著色劑(A)含有化合物(I)。以下,使用式(I)對本發明進行詳細敘述,設為化合物(I)中亦包含使式(I)的共振結構、或式(I)中的各基團繞單鍵的鍵軸旋轉所得的化合物。<Colorant (A)> The colorant (A) contains the compound (I). Hereinafter, the present invention will be described in detail using the formula (I), assuming that the compound (I) also includes the resonance structure of the formula (I) or the resultant rotation of each group in the formula (I) around the bond axis of the single bond Compound.
[化3] [化3]
[式(I)中, R1 ~R4 分別獨立地表示氫原子、鹵素原子、羥基或可具有取代基的碳數1~20的一價飽和烴基。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子。 R5 ~R8 分別獨立地表示氫原子或羥基。 Ar1 及Ar2 分別獨立地表示可具有取代基的碳數1~20的一價飽和烴基或式(i)所表示的基團,較佳為表示式(i)所表示的基團。 [化4] [式(i)中, R12 表示可具有取代基的碳數1~20的一價飽和烴基或可具有取代基的碳數2~20的一價不飽和烴基,m表示0~5的整數。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子。m為2以上時,多個R12 分別可相同亦可不同。*表示與氮原子的結合鍵] R9 及R10 分別獨立地表示可具有取代基的碳數1~20的一價飽和烴基或式(i)所表示的基團。於構成該一價飽和烴基的碳原子之間亦可插入有氧原子或硫原子][In formula (I), R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, or an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbons. An oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. R 5 to R 8 each independently represent a hydrogen atom or a hydroxyl group. Ar 1 and Ar 2 each independently represent an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by formula (i), and preferably represent a group represented by formula (i). [化4] [In formula (i), R 12 represents an optionally substituted monovalent saturated hydrocarbon group of 1 to 20 carbons or an optionally substituted monovalent unsaturated hydrocarbon group of 2 to 20 carbons, and m represents an integer of 0 to 5 . An oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. When m is 2 or more, a plurality of R 12 may be the same or different. *Represents a bond to a nitrogen atom] R 9 and R 10 each independently represent an optionally substituted monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by formula (i). An oxygen atom or sulfur atom may be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group]
式(I)中,作為R1 ~R4 中的鹵素原子,可列舉:氟原子、氯原子、溴原子或碘原子。In formula (I), examples of the halogen atom in R 1 to R 4 include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
作為R1 ~R4 、R9 、R10 、R12 、Ar1 及Ar2 中的碳數1~20的一價飽和烴基,例如可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二基、十六基及二十基等碳數1~20的直鏈狀烷基;異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基及2-乙基己基等碳數3~20的分支鏈狀烷基;環丙基、環戊基、環己基、環庚基、環辛基、三環癸基及金剛烷基等碳數3~20的脂環式飽和烴基。Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 1 to R 4 , R 9 , R 10 , R 12 , Ar 1 and Ar 2 include methyl, ethyl, propyl, butyl, Pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl and other linear alkyl groups with 1 to 20 carbon atoms; isopropyl, isobutyl, and Dibutyl, tert-butyl, isopentyl, neopentyl and 2-ethylhexyl and other branched chain alkyl groups with 3 to 20 carbon atoms; cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, Cyclooctyl, tricyclodecyl, adamantyl and other alicyclic saturated hydrocarbon groups with 3 to 20 carbon atoms.
作為該些飽和烴基的取代基,可列舉:氟原子、氯原子、碘等鹵素原子;羥基;羧基;-NRa Rb (Ra 及Rb 分別獨立地為氫原子或碳數1~20的烷基);硝基;甲氧基羰基、乙氧基羰基等碳數1~10的烷氧基羰基;等,作為具有取代基的碳數1~20的一價飽和烴基,例如可列舉下述式所表示的基團。下述式中,*表示結合鍵。Examples of substituents of these saturated hydrocarbon groups include halogen atoms such as fluorine atom, chlorine atom, and iodine; hydroxyl group; carboxyl group; -NR a R b (R a and R b are each independently a hydrogen atom or a carbon number of 1-20的alkyl); nitro; alkoxycarbonyl having 1 to 10 carbons such as methoxycarbonyl and ethoxycarbonyl; etc., as a substituted monovalent saturated hydrocarbon group having 1 to 20 carbons, for example, A group represented by the following formula. In the following formula, * represents a bond.
[化5] [化5]
作為於構成該些飽和烴基的碳原子之間插入有氧原子或硫原子的基團,例如可列舉下述式所表示的基團。下述式中,*表示結合鍵。Examples of groups in which an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting these saturated hydrocarbon groups include groups represented by the following formulas. In the following formula, * represents a bond.
[化6] [化6]
作為R12 中的碳數2~20的一價不飽和烴基,例如可列舉:乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基。Examples of the monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms in R 12 include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, and nonenyl. , Decenyl.
作為該不飽和烴基的取代基,可列舉:氟原子、氯原子、碘等鹵素原子;羥基;羧基;-NRc Rd (Rc 及Rd 分別獨立地為氫原子或碳數1~20的烷基);硝基;甲氧基、乙氧基等碳數1~10的烷氧基;甲氧基羰基、乙氧基羰基等碳數1~10的烷氧基羰基;等。Examples of the substituent of the unsaturated hydrocarbon group include halogen atoms such as fluorine atom, chlorine atom, and iodine; hydroxyl group; carboxyl group; -NR c R d (R c and Rd are each independently a hydrogen atom or a carbon number of 1-20的alkyl); nitro; alkoxy, ethoxy and other alkoxy groups having 1 to 10 carbons; methoxycarbonyl, ethoxycarbonyl, and other alkoxycarbonyl groups having 1 to 10 carbons; etc.
作為R1 ~R4 ,較佳為氫原子、羥基及碳數1~4的烷基,更佳為氫原子、羥基及甲基,進而佳為氫原子。R 1 to R 4 are preferably a hydrogen atom, a hydroxyl group, and an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a hydroxyl group, and a methyl group, and still more preferably a hydrogen atom.
R5 ~R8 較佳為至少一個為羥基。更佳為:R5 及R6 的至少一者為羥基,R7 及R8 的至少一者為羥基。Preferably, at least one of R 5 to R 8 is a hydroxyl group. More preferably, at least one of R 5 and R 6 is a hydroxyl group, and at least one of R 7 and R 8 is a hydroxyl group.
作為R9 及R10 ,較佳為可具有取代基的碳數3~14的烷基及式(i)所表示的基團,更佳為可具有取代基的碳數3~6的直鏈狀烷基、可具有取代基的碳數7~14的直鏈狀或分支鏈狀的烷基(例如辛基、壬基、癸基、十二基、2-乙基己基等)、及式(i)所表示的基團,進而佳為末端具有羥基的碳數3~5的直鏈狀烷基、末端具有羧基的碳數3~5的直鏈狀烷基、及2-乙基己基。As R 9 and R 10 , an optionally substituted alkyl group having 3 to 14 carbon atoms and a group represented by formula (i) are preferred, and an optionally substituted straight chain carbon number of 3 to 6 is more preferred Alkyl groups, linear or branched alkyl groups having 7 to 14 carbon atoms that may have substituents (for example, octyl, nonyl, decyl, dodecyl, 2-ethylhexyl, etc.), and the formula The group represented by (i) is more preferably a linear alkyl group having 3 to 5 carbon atoms having a hydroxyl group at the terminal, a linear alkyl group having 3 to 5 carbon atoms having a carboxyl group at the terminal, and 2-ethylhexyl .
作為R12 的飽和烴基,較佳為碳數1~4的烷基,更佳為甲基、乙基、異丙基。 作為R12 的不飽和烴基,較佳為碳數2~4的烯基,更佳為乙烯基、烯丙基。 於m為2以上的情況下,較佳為至少一個R12 為飽和烴基。於m為2以上的情況下,更佳的是全部R12 為飽和烴基的形態;或者一部分R12 為飽和烴基、一部分R12 為不飽和烴基的形態。The saturated hydrocarbon group for R 12 is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group, an ethyl group, or an isopropyl group. The unsaturated hydrocarbon group for R 12 is preferably an alkenyl group having 2 to 4 carbon atoms, and more preferably a vinyl group or an allyl group. When m is 2 or more, it is preferable that at least one R 12 is a saturated hydrocarbon group. When m is 2 or more, it is more preferable that all R 12 are saturated hydrocarbon groups; or some R 12 are saturated hydrocarbon groups and some R 12 are unsaturated hydrocarbon groups.
m較佳為1~5,更佳為1~3。 作為式(i)所表示的基團,例如可列舉如下基團。*表示與氮原子的結合鍵。m is preferably 1-5, more preferably 1-3. As a group represented by formula (i), the following groups are mentioned, for example. * Indicates the bond with the nitrogen atom.
[化7] [化7]
式(I)中,當將In formula (I), when
[化8] 所表示的基團設為X1 ,將[化8] The represented group is set to X 1 , and
[化9] 所表示的基團設為X2 時,作為X1 及X2 所表示的基團,例如可列舉式(A2-1)~式(A2-9)所表示的基團。*表示與碳原子的結合鍵。[化9] When the represented group is X 2 , examples of the groups represented by X 1 and X 2 include groups represented by formula (A2-1) to formula (A2-9). * Represents the bond with the carbon atom.
[化10] [化10]
作為化合物(I),例如可列舉表1所示的化合物(AII-1)~化合物(AII-27)。As the compound (I), for example, the compound (AII-1) to the compound (AII-27) shown in Table 1 are mentioned.
[表1] [Table 1]
更佳為化合物(AII-10)~化合物(AII-18)。More preferred are compound (AII-10) to compound (AII-18).
式(I)所表示的化合物可藉由使式(pt1)所表示的化合物與式(pt2)所表示的化合物與式(pt3)所表示的化合物反應而製造。於本反應中,相對於式(pt1)所表示的化合物及式(pt2)所表示的化合物的合計1莫耳,式(pt3)所表示的化合物的使用量較佳為0.05莫耳以上且0.8莫耳以下,更佳為0.1莫耳以上且0.6莫耳以下。The compound represented by the formula (I) can be produced by reacting the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3). In this reaction, the amount of the compound represented by the formula (pt3) is preferably 0.05 mol or more and 0.8 mol relative to the total of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) 1 mol Molar or less, more preferably 0.1 mol or more and 0.6 mol or less.
[化11] [化11]
式中,R1 ~R10 、Ar1 及Ar2 分別表示與所述為相同的含義。In the formula, R 1 to R 10 , Ar 1 and Ar 2 each have the same meaning as described above.
反應溫度較佳為30℃~180℃,更佳為80℃~140℃。反應時間較佳為1小時~12小時,更佳為3小時~8小時。The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.
就產率的方面而言,反應較佳為於有機溶劑中進行。作為有機溶劑,可列舉:甲苯、二甲苯等烴溶劑;氯苯、二氯苯、氯仿等鹵化烴溶劑;甲醇、乙醇、異丙醇、丁醇等醇溶劑;硝基苯等硝基烴溶劑;甲基異丁基酮等酮溶劑;1-甲基-2-吡咯啶酮等醯胺溶劑;等,亦可將該些混合使用。其中,較佳為丁醇及甲苯的混合溶劑。相對於式(pt1)所表示的化合物及式(pt2)所表示的化合物的合計1質量份,有機溶劑的使用量較佳為10質量份以上且200質量份以下,更佳為30質量份以上且150質量份以下。In terms of yield, the reaction is preferably carried out in an organic solvent. Examples of organic solvents 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; nitro hydrocarbon solvents such as nitrobenzene Ketone solvents such as methyl isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidone; etc., these can also be mixed and used. Among them, a mixed solvent of butanol and toluene is preferred. The amount of the organic solvent used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 30 parts by mass or more, relative to 1 part by mass of the compound represented by formula (pt1) and the compound represented by formula (pt2) in total And 150 parts by mass or less.
自反應混合物取出作為目標化合物的化合物(I)的方法並無特別限定,可使用公知的各種方法。例如可列舉:反應結束後進行冷卻並濾取所析出的結晶的方法。所濾取的結晶較佳為利用水等進行清洗,繼而加以乾燥。另外,視需要亦可藉由再結晶等公知的方法進一步進行精製。The method for taking out the compound (I) as the target compound from the reaction mixture is not particularly limited, and various known methods can be used. For example, the method of cooling after completion|finish of reaction, and filtering the precipitated crystal|crystallization is mentioned. The filtered crystals are preferably washed with water or the like, and then dried. In addition, if necessary, it can be further refined by a known method such as recrystallization.
使式(IV-2)所表示的化合物與式(IV-3)所表示的化合物反應而製造式(IV-4)所表示的化合物後,使式(IV-4)所表示的化合物與式(IV-5)所表示的化合物反應,藉此可製造式(pt1)所表示的化合物。After reacting the compound represented by formula (IV-2) with the compound represented by formula (IV-3) to produce the compound represented by formula (IV-4), the compound represented by formula (IV-4) is reacted with By reacting the compound represented by (IV-5), the compound represented by formula (pt1) can be produced.
[化12] [化12]
式(IV-2)~式(IV-5)中,R1 、R2 、R5 、R6 、R9 及Ar1 分別表示與所述為相同的含義。In formulas (IV-2) to (IV-5), R 1 , R 2 , R 5 , R 6 , R 9 and Ar 1 each have the same meaning as described above.
作為由式(IV-2)所表示的化合物與式(IV-3)所表示的化合物製造式(IV-4)所表示的化合物的方法,可列舉公知的各種方法,例如歐洲有機化學雜誌(Eur. J. Org. Chem.)2012, 3105-3111.中記載的方法。As a method for producing the compound represented by the formula (IV-4) from the compound represented by the formula (IV-2) and the compound represented by the formula (IV-3), various known methods can be cited, for example, the European Journal of Organic Chemistry ( Eur. J. Org. Chem.) 2012, 3105-3111.
作為由式(IV-4)所表示的化合物與式(IV-5)所表示的化合物製造式(pt1)所表示的化合物的方法,可列舉公知的各種方法,例如聚合物科學雜誌 A部分:聚合物化學(J. Polymer Science Part A:Polymer Chemistry)2012, 50, 3788-3796中記載的方法。As a method for producing the compound represented by the formula (pt1) from the compound represented by the formula (IV-4) and the compound represented by the formula (IV-5), various well-known methods can be cited, for example, part A of the Journal of Polymer Science: Polymer Chemistry (J. Polymer Science Part A: Polymer Chemistry) 2012, 50, 3788-3796.
可使用與所述相同的方法製造式(pt2)所表示的化合物。The compound represented by formula (pt2) can be produced by the same method as described above.
著色劑(A)除化合物(I)以外,亦可包含與化合物(I)不同的著色劑,該與化合物(I)不同的著色劑可為染料(以下,有時稱為染料(A1))及顏料(以下,有時稱為顏料(A2))中的任一者,與化合物(I)不同的著色劑亦可包含該些染料(A1)及顏料(A2)中的一者或兩者。The coloring agent (A) may include a coloring agent different from the compound (I) in addition to the compound (I), and the coloring agent different from the compound (I) may be a dye (hereinafter, sometimes referred to as dye (A1)) And pigment (hereinafter, sometimes referred to as pigment (A2)), and a coloring agent different from compound (I) may include one or both of these dyes (A1) and pigments (A2) .
染料(A1)只要不包含化合物(I),則無特別限定,可使用公知的染料,可列舉:溶劑染料、酸性染料、直接染料、媒染染料等。作為染料,例如可列舉染料索引(Color Index)(染色與印染工作者協會(The Society of Dyers and Colourists)出版)中被分類為除顏料(pigment)以外具有色相者的化合物、或染色筆記(色染(Shikisensha)公司)中記載的公知的染料。另外,根據化學結構,可列舉:偶氮染料、花青染料、三苯基甲烷染料、呫噸染料(xanthene dye)、酞菁染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、次甲基偶氮染料(azomethine dye)、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料及硝基染料等。該些中,較佳為有機溶劑可溶性染料。The dye (A1) is not particularly limited as long as it does not contain the compound (I), and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as having a hue in addition to pigments in the Color Index (published by The Society of Dyers and Colourists), or dyeing notes (color Known dyes described in Shikisensha (Shikisensha). In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine Based dyes, azomethine dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes and nitro dyes. Among these, organic solvent-soluble dyes are preferred.
具體而言,可列舉:C.I.溶劑黃(Solvent Yellow)4(以下,省略C.I.溶劑黃的記載而僅記載編號)、14、15、23、24、38、62、63、68、82、94、98、99、117、162、163、167、189; C.I.溶劑紅(Solvent Red)45、49、111、125、130、143、145、146、150、151、155、168、169、172、175、181、207、218、222、227、230、245、247; C.I.溶劑橙(Solvent Orange)2、7、11、15、26、56、77、86; C.I.溶劑紫(Solvent Violet)11、13、14、26、31、36、37、38、45、47、48、51、59、60; C.I.溶劑藍(Solvent Blue)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; C.I.溶劑綠(Solvent Green)1、3、4、5、7、28、29、32、33、34、35等C.I.溶劑染料, C.I.酸性黃(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.酸性紅(Acid Red)1、4、8、14、17、18、26、27、29、31、33、34、35、37、40、42、44、50、51、52、57、66、73、76、80、87、88、91、92、94、95、97、98、103、106、111、114、129、133、134、138、143、145、150、151、155、158、160、172、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.酸性橙(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.酸性紫(Acid Violet)6B、7、9、15、16、17、19、21、23、24、25、30、34、38、49、72、102; C.I.酸性藍(Acid Blue)1、3、5、7、9、11、13、15、17、18、22、23、24、25、26、27、29、34、38、40、41、42、43、45、48、51、54、59、60、62、70、72、74、75、78、80、82、83、86、87、88、90、90:1、91、92、93、93:1、96、99、100、102、103、104、108、109、110、112、113、117、119、120、123、126、127、129、130、131、138、140、142、143、147、150、151、154、158、161、166、167、168、170、171、175、182、183、184、187、192、199、203、204、205、210、213、229、234、236、242、243、256、259、267、269、278、280、285、290、296、315、324:1、335、340; C.I.酸性綠(Acid Green)1、3、5、6、7、8、9、11、13、14、15、16、22、25、27、28、41、50、50:1、58、63、65、80、104、105、106、109等C.I.酸性染料, C.I.直接黃(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.直接紅(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.直接橙(Direct Orange)26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107; C.I.直接紫(Direct Violet)47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104; C.I.直接藍(Direct Blue)1、2、3、6、8、15、22、25、28、29、40、41、42、47、52、55、57、71、76、77、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.直接綠(Direct Green)25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82等C.I.直接染料, C.I.分散黃(Disperse Yellow)51、54、76; C.I.分散紫(Disperse Violet)26、27; C.I.分散藍(Disperse Blue)1、14、56、60等C.I.分散染料, C.I.鹼性紅(Basic Red)1、10; C.I.鹼性藍(Basic Blue)1、3、5、7、9、19、21、22、24、25、26、28、29、40、41、45、47、54、58、59、60、64、65、66、67、68、81、83、88、89; C.I.鹼性紫(Basic Violet)2; C.I.鹼性紅(Basic Red)9; C.I.鹼性綠(Basic Green)1等C.I.鹼性染料, C.I.活性黃(Reactive Yellow)2、76、116; C.I.活性橙(Reactive Orange)16; C.I.活性紅(Reactive Red)36等C.I.活性染料, C.I.媒染黃(Mordant Yellow)5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65; C.I.媒染紅(Mordant Red)1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、27、29、30、32、33、36、37、38、39、41、42、43、45、46、48、52、53、56、62、63、71、74、76、78、85、86、88、90、94、95; C.I.媒染橙(Mordant 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.媒染紫(Mordant Violet)1、1:1、2、3、4、5、6、7、8、10、11、14、15、16、17、18、19、21、22、23、24、27、28、30、31、32、33、36、37、39、40、41、44、45、47、48、49、53、58; C.I.媒染藍(Mordant Blue)1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83、84; C.I.媒染綠(Mordant Green)1、3、4、5、10、13、15、19、21、23、26、29、31、33、34、35、41、43、53等C.I.媒染染料, C.I.還原綠(Vat Green)1等C.I.還原染料等。 該些染料只要根據所期望的彩色濾光片的分光光譜來適當選擇即可。Specifically, examples include: CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted and only the numbers are described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245 , 247; C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; 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 , 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other C.I. solvent dyes, 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 ; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66 , 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158 , 160, 172, 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. Acid Orange (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. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1,3,5,7,9,11,13,15,17,18,22,23,24,25,26,27,29,34,38,40,41,42 , 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93 , 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142 ,143,147,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,210,213,229 , 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340; CI Acid Green 1,3,5,6,7,8,9,11,13,14,15,16,22,25,27,28,41,50,50:1,58,63 , 65, 80, 104, 105, 106, 109 and other CI acid dyes, 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; 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. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 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. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other C.I. direct dyes, C.I. Disperse Yellow 51, 54, 76; C.I. Disperse Violet 26, 27; C.I. Disperse Blue (Disperse Blue) 1, 14, 56, 60 and other C.I. Disperse dyes, C.I. Basic Red 1, 10; CI Basic Blue (Basic Blue) 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C.I. Basic Violet 2; C.I. Basic Red 9; C.I. Basic Green 1 and other C.I. Basic dyes, C.I. Reactive Yellow 2, 76, 116; C.I. Reactive Orange 16; C.I. Reactive Red 36 and other C.I. Reactive dyes, C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36 , 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48 ; CI Mordant Violet 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24 , 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40 , 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. C.I. Mordant Dyes, C.I. Vat Green 1, etc. C.I. Vat dyes, etc. These dyes may be appropriately selected according to the spectroscopic spectrum of the desired color filter.
作為顏料(A2),並無特別限定,可使用公知的顏料,例如可列舉染料索引(Color Index)(染色與印染工作者協會(The Society of Dyers and Colourists)出版)中被分類為顏料(pigment)的顏料。 作為顏料,例如可列舉:C.I.顏料黃(Pigment Yellow)1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、194、214等黃色顏料; C.I.顏料橙(Pigment Orange)13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色的顏料; C.I.顏料紅(Pigment Red)9、97、105、122、123、144、149、166、168、176、177、180、192、209、215、216、224、242、254、255、264、265等紅色顏料; C.I.顏料藍(Pigment Blue)15:6、60等藍色顏料; C.I.顏料紫(Pigment Violet)1、19、23、29、32、36、38等紫色顏料; C.I.顏料綠(Pigment Green)7、36、58等綠色顏料; C.I.顏料棕(Pigment Brown)23、25等棕色顏料; C.I.顏料黑(Pigment Black)1、7等黑色顏料等。The pigment (A2) is not particularly limited, and well-known pigments can be used. For example, the Color Index (published by The Society of Dyers and Colourists) is classified as pigment (pigment). ) Paint. Examples of pigments include CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 Red pigment C.I. Pigment Blue 15: 6, 60 and other blue pigments; C.I. Purple pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38; C.I. Pigment Green 7, 36, 58 and other green pigments; C.I. Pigment Brown (Pigment Brown) 23, 25 and other brown pigments; C.I. Pigment Black 1, 7 black pigments, etc.
顏料視需要亦可實施松香處理、使用導入有酸性基或鹼性基的顏料衍生物等的表面處理、利用高分子化合物等的對顏料表面的接枝處理、利用硫酸微粒化法等的微粒化處理、或者用以將雜質去除的利用有機溶劑或水等的清洗處理、離子性雜質的利用離子交換法等的去除處理等。 顏料較佳為粒徑均勻。藉由含有顏料分散劑並進行分散處理,可獲得顏料於溶液中均勻分散的狀態的顏料分散液。If necessary, the pigment can be subjected to rosin treatment, surface treatment using pigment derivatives introduced with acidic or basic groups, grafting treatment to the surface of the pigment using polymer compounds, etc., and microparticulation by sulfuric acid microparticulation method, etc. Treatment or cleaning treatment using organic solvents or water to remove impurities, removal treatment of ionic impurities using ion exchange methods, etc. The pigment preferably has a uniform particle size. By containing the pigment dispersant and performing the dispersion treatment, a pigment dispersion in a state where the pigment is uniformly dispersed in the solution can be obtained.
作為所述顏料分散劑,例如可列舉:陽離子系、陰離子系、非離子系、兩性、聚酯系、多胺系、丙烯酸系等的界面活性劑。該些顏料分散劑可單獨使用,亦可組合使用兩種以上。作為顏料分散劑,以商品名可列舉:KP(信越化學工業(股)製造)、佛羅倫(Flowlen)(共榮社化學(股)製造)、索努帕斯(Solsperse)(捷利康(Zeneca)(股)製造)、埃夫卡(EFKA)(汽巴(CIBA)公司製造)、阿吉斯帕(Ajisper)(味之素精密技術(Ajinomoto Fine-Techno)(股)製造)、迪斯帕畢克(Disperbyk)(畢克化學(BYK-chemie)公司製造)等。 於使用顏料分散劑的情況下,相對於顏料(A2)的總量,所述顏料分散劑的使用量較佳為1質量%以上且100質量%以下,更佳為5質量%以上且50質量%以下。若顏料分散劑的使用量處於所述範圍,則有可獲得均勻分散狀態的顏料分散液的傾向。Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic, and other surfactants. These pigment dispersants may be used alone or in combination of two or more. As a pigment dispersant, trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), and Solsperse (by Zelikon ( Zeneca (share), EFKA (CIBA), Ajisper (Ajinomoto Fine-Techno (share)), Di Disperbyk (manufactured by BYK-chemie), etc. In the case of using a pigment dispersant, relative to the total amount of the pigment (A2), the usage amount of the pigment dispersant is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 50% by mass %the following. If the amount of the pigment dispersant used is in the above range, there is a tendency that a pigment dispersion in a uniformly dispersed state can be obtained.
相對於固體成分的總量,著色硬化性樹脂組成物中的著色劑(A)的含有率較佳為0.1質量%以上且70質量%以下,更佳為0.5質量%以上且60質量%以下,進而佳為1質量%以上且50質量%以下。若著色劑(A)的含有率為所述範圍內,則製成彩色濾光片時的色濃度充分,且可於組成物中含有必要量的樹脂(B)或聚合性化合物(C),因此可形成機械強度充分的圖案。The content of the coloring agent (A) in the colored curable resin composition is preferably 0.1% by mass or more and 70% by mass or less, and more preferably 0.5% by mass or more and 60% by mass or less, relative to the total solid content, More preferably, it is 1 mass% or more and 50 mass% or less. If the content of the coloring agent (A) is within the above range, the color density when the color filter is made is sufficient, and the necessary amount of resin (B) or polymerizable compound (C) can be contained in the composition, Therefore, a pattern with sufficient mechanical strength can be formed.
此處,所謂本說明書中的「固體成分的總量」,是指自著色硬化性樹脂組成物的總量中去除溶劑的含量之後的量。固體成分的總量以及相對於其的各成分的含量例如可藉由液相層析法或氣相層析法等公知的分析手段進行測定。Here, the "total amount of solid content" in this specification refers to the amount after removing the solvent content from the total amount of the colored curable resin composition. The total amount of solid content and the content of each component relative to it can be measured, for example, by known analysis means such as liquid chromatography or gas chromatography.
於著色劑(A)的總量中,化合物(I)的含有率較佳為1質量%以上,更佳為3質量%以上,亦可為100質量%,可為90質量%以下,亦可為60質量%以下,亦可為40質量%以下。In the total amount of the colorant (A), the content of the compound (I) is preferably 1% by mass or more, more preferably 3% by mass or more, may be 100% by mass, may be 90% by mass or less, or It is 60% by mass or less, and may be 40% by mass or less.
<樹脂(B)> 樹脂含有包含源自N-取代馬來醯亞胺的結構單元的樹脂。<Resin (B)> The resin contains a resin containing structural units derived from N-substituted maleimines.
藉由本發明的著色硬化性樹脂組成物含有所述樹脂,從而彩色濾光片的吸光度保持率提升。When the colored curable resin composition of the present invention contains the resin, the absorbance retention rate of the color filter is improved.
源自N-取代馬來醯亞胺的結構單元較佳為下述式(Bm)所表示的結構單元。The structural unit derived from N-substituted maleimines is preferably a structural unit represented by the following formula (Bm).
[化13] [化13]
[式(Bm)中,R13 表示可具有取代基的碳數1~15的一價飽和烴基、可具有取代基的碳數6~20的一價芳香族烴基、或可具有取代基的碳數3~20的一價雜環基][In formula (Bm), R 13 represents a monovalent saturated hydrocarbon group with 1 to 15 carbons that may have a substituent, a monovalent aromatic hydrocarbon group with 6 to 20 carbons that may have a substituent, or a substituted carbon A monovalent heterocyclic group of 3 to 20]
作為碳數1~15的一價飽和烴基,例如可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二基、十六基及二十基等碳數1~15的直鏈狀烷基;異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基及2-乙基己基等碳數3~15的分支鏈狀烷基;環丙基、環戊基、環己基、環庚基、環辛基、三環癸基及金剛烷基等碳數3~15的脂環式飽和烴基。Examples of monovalent saturated hydrocarbon groups having 1 to 15 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and decyl groups. Hexyl and eicosyl and other linear alkyl groups with 1 to 15 carbons; isopropyl, isobutyl, second butyl, tertiary butyl, isopentyl, neopentyl and 2-ethylhexyl Branched chain alkyl with 3 to 15 carbons; alicyclic with 3 to 15 carbons such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl and adamantyl Saturated hydrocarbon group.
作為該飽和烴基的取代基,可列舉:氟原子、氯原子、碘等鹵素原子;羥基;羧基;-NRh Ri (Rh 及Ri 分別獨立地為氫原子或碳數1~20的烷基);硝基;甲氧基、乙氧基等碳數1~10的烷氧基;苯基、萘基、蒽基、菲基、聯苯基等碳數6~15的芳香族烴基;甲氧基羰基、乙氧基羰基等碳數1~10的烷氧基羰基;下述式(m-1)所表示的基團等。Examples of the substituent of the saturated hydrocarbon group include halogen atoms such as fluorine atom, chlorine atom, and iodine; hydroxyl group; carboxyl group; -NR h R i (R h and R i are each independently a hydrogen atom or one having 1 to 20 carbon atoms) Alkyl); Nitro; Alkoxy with 1 to 10 carbons such as methoxy and ethoxy; Aromatic hydrocarbon with 6 to 15 carbons such as phenyl, naphthyl, anthryl, phenanthryl, and biphenyl ; C1-C10 alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl; groups represented by the following formula (m-1) and the like.
[化14] [化14]
[式(m-1)中,*表示結合鍵][In the formula (m-1), * represents the bond]
作為碳數6~20的一價芳香族烴基,可列舉:苯基、萘基、蒽基、菲基、聯苯基、三聯苯基等。As a C6-C20 monovalent aromatic hydrocarbon group, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, etc. are mentioned.
作為該芳香族烴基的取代基,可列舉:羥基;羧基;氟原子、氯原子、碘原子、溴原子等鹵素原子;甲氧基、乙氧基等碳數1~6的烷氧基;胺磺醯基;甲基磺醯基等碳數1~6的烷基磺醯基;甲氧基羰基、乙氧基羰基等碳數1~6的烷氧基羰基;式(m-1)所表示的基團等。Examples of the substituent of the aromatic hydrocarbon group include: a hydroxyl group; a carboxyl group; halogen atoms such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; Sulfonyl; methylsulfonyl and other alkylsulfonyl groups with 1 to 6 carbons; methoxycarbonyl, ethoxycarbonyl and other alkoxycarbonyl groups with 1 to 6 carbons; represented by formula (m-1) Expressed groups and so on.
R13 為具有取代基的碳數1~6的一價飽和烴基,於該飽和烴基為烷基且取代基為碳數6~15的芳香族烴基的情況下,R13 表示碳數7~21的芳烷基。 作為碳數7~21的一價芳烷基,可列舉:苄基、苯乙基、苯基丙基、萘基甲基及萘基乙基等。R 13 is a substituted monovalent saturated hydrocarbon group having 1 to 6 carbons, and when the saturated hydrocarbon group is an alkyl group and the substituent is an aromatic hydrocarbon group having 6 to 15 carbons, R 13 represents a carbon number of 7 to 21的arylalkyl. Examples of the monovalent aralkyl group having 7 to 21 carbon atoms include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl.
作為該芳烷基的取代基,可列舉與作為芳香族烴基的取代基而說明的基團相同者。Examples of the substituent of the aralkyl group include the same groups as those explained as the substituent of the aromatic hydrocarbon group.
作為碳數3~20的一價雜環基,可列舉:噻吩基、苯並[b]噻吩基、萘並[2,3-b]噻吩基、噻蒽基(thianthrenyl group)、呋喃基(furyl group)、吡喃基、異苯並呋喃基、苯並哌喃基(chromenyl group)、呫噸基(xanthenyl group)、啡噁噻基(phenoxathiinyl group)、2H-吡咯基、吡咯基、咪唑基、吡唑基、吡啶基、吡嗪基、嘧啶基、噠嗪基、吲嗪基、異吲哚基、3H-吲哚基、吲哚基、1H-吲唑基、嘌呤基、4H-喹嗪基、異喹啉基、喹啉基、酞嗪基、萘啶基、喹噁啉基(quinoxalinyl group)、喹唑啉基、噌啉基、喋啶基、4aH-咔唑基、咔唑基、β-咔啉基、啡啶基、吖啶基、啶基(perimidinyl group)、啡啉基(phenanthrolinyl group)、啡嗪基、啡呻嗪基(phenarsazinyl group)、異噻唑基、啡噻嗪基、異噁唑基、呋呫基(furazanyl group)、啡噁嗪基、異基(isochromanyl group)、基(chromanyl group)、吡咯啶基、吡咯啉基、咪唑啶基、咪唑啉基、吡唑啶基、吡唑啉基、哌啶基、哌嗪基、吲哚啉基、異吲哚啉基、啶基(quinuclidinyl group)、嗎啉基、噻噸酮基(thioxantholyl group)等。Examples of monovalent heterocyclic groups having 3 to 20 carbon atoms include thienyl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thianthrenyl group, and furyl ( furyl group, pyranyl, isobenzofuranyl, chromenyl group, xanthenyl group, phenoxathiinyl group, 2H-pyrrolyl, pyrrolyl, imidazole Group, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazinyl, isoindolyl, 3H-indolyl, indolyl, 1H-indazolyl, purinyl, 4H- Quinazinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl group, quinoxalinyl group, quinoxalinyl group, pterridinyl, 4aH-carbazolyl, carbohydrate Azolyl, β-carbolinyl, phenanthridinyl, acridinyl, Perimidinyl group, phenanthrolinyl group, phenanthrolinyl group, phenarsazinyl group, isothiazolyl, phenothiazinyl, isoxazolyl, furazinyl group, Phenoxazinyl, iso 基 (isochromanyl group), Chromanyl group, pyrrolidinyl, pyrrolinyl, imidazolinyl, imidazolinyl, pyrazolinyl, pyrazolinyl, piperidinyl, piperazinyl, indolinyl, isoindolinyl , Quinuclidinyl group, morpholinyl group, thioxantholyl group, etc.
作為該雜環基的取代基,可列舉與作為芳香族烴基的取代基而說明的基團相同者。As the substituent of this heterocyclic group, the same thing as demonstrated as a substituent of an aromatic hydrocarbon group is mentioned.
作為R13 ,較佳為碳數3~8的脂環式飽和烴基、碳數6~10的一價芳香族烴基或碳數7~11的一價芳烷基。R 13 is preferably an alicyclic saturated hydrocarbon group having 3 to 8 carbons, a monovalent aromatic hydrocarbon group having 6 to 10 carbons, or a monovalent aralkyl group having 7 to 11 carbons.
作為源自N-取代馬來醯亞胺的結構單元,可例示源自N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-琥珀醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-琥珀醯亞胺基-4-馬來醯亞胺丁酸酯、N-琥珀醯亞胺基-6-馬來醯亞胺己酸酯、N-琥珀醯亞胺基-3-馬來醯亞胺丙酸酯、N-(9-吖啶基)馬來醯亞胺等的結構單元,其中,較佳為源自N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺的結構單元。As the structural unit derived from N-substituted maleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N -Succinimidyl-3-maleiminobenzoate, N-succinimidyl-4-maleimidin butyrate, N-succinimidyl-6-male Structural units such as acetimidate caproate, N-succinimidyl-3-maleimidate propionate, N-(9-acridinyl)maleimines, etc., of which, preferred are It is a structural unit derived from N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide.
樹脂(B)較佳為鹼可溶性樹脂。作為顯示出鹼可溶性的樹脂(B),可列舉以下的樹脂[K1]~樹脂[K6]等。The resin (B) is preferably an alkali-soluble resin. As the resin (B) exhibiting alkali solubility, the following resin [K1] to resin [K6] and the like can be cited.
樹脂[K1]:包含源自單量體(a)(以下,有時稱為「(a)」)的結構單元、源自單量體(b)(以下,有時稱為「(b)」)的結構單元、以及源自N-取代馬來醯亞胺(m)(以下,有時稱為「(m)」)的結構單元的共聚物,其中,所述單量體(a)為選自由不飽和羧酸及不飽和羧酸酐所組成的群組中的至少一種,所述單量體(b)具有碳數2~4的環狀醚結構與乙烯性不飽和鍵; 樹脂[K2]:包含源自(a)的結構單元、源自(b)的結構單元、源自(m)的結構單元、以及源自可與(a)共聚的單量體(c)(其中,與(a)、(b)及(m)不同)(以下,有時稱為「(c)」)的結構單元的共聚物; 樹脂[K3]:包含源自(a)的結構單元與源自(m)的結構單元的共聚物; 樹脂[K4]:包含源自(a)的結構單元、源自(m)的結構單元、以及源自(c)的結構單元的共聚物; 樹脂[K5]:包含對源自(b)的結構單元加成(a)而成的結構單元、以及源自(m)的結構單元的共聚物; 樹脂[K6]:包含對源自(b)的結構單元加成(a)並進一步加成羧酸酐而成的結構單元、以及源自(m)的結構單元的共聚物。Resin [K1]: Contains structural units derived from monomer (a) (hereinafter, sometimes referred to as "(a)"), and derived from monomer (b) (hereinafter, sometimes referred to as "(b)) ") and a copolymer of structural units derived from N-substituted maleimide (m) (hereinafter, sometimes referred to as "(m)"), wherein the monomer (a) Is at least one selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride, and the monomer (b) has a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: Contains a structural unit derived from (a), a structural unit derived from (b), a structural unit derived from (m), and a monomer (c) which can be copolymerized with (a) ( Among them, different from (a), (b) and (m)) (hereinafter, sometimes referred to as "(c)") a copolymer of structural units; Resin [K3]: a copolymer containing a structural unit derived from (a) and a structural unit derived from (m); Resin [K4]: a copolymer containing a structural unit derived from (a), a structural unit derived from (m), and a structural unit derived from (c); Resin [K5]: a copolymer containing a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (m); Resin [K6]: A copolymer containing a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride, and a structural unit derived from (m).
所述源自(a)的結構單元較佳為(a)所具有的羧基或羧酸酐以未反應的狀態殘留。另外,於樹脂[K1]、樹脂[K2]中,所述源自(b)的結構單元較佳為(b)所具有的碳數2~4的環狀醚結構以未反應的狀態殘留。The structural unit derived from (a) preferably has the carboxyl group or carboxylic anhydride of (a) remaining in an unreacted state. In addition, in resin [K1] and resin [K2], the structural unit derived from (b) is preferably the cyclic ether structure having 2 to 4 carbons in (b) remaining in an unreacted state.
作為(a),具體而言,例如可列舉:丙烯酸、甲基丙烯酸、巴豆酸、鄰乙烯基苯甲酸、間乙烯基苯甲酸、對乙烯基苯甲酸等不飽和單羧酸類; 馬來酸、富馬酸、檸康酸、中康酸、衣康酸、3-乙烯基鄰苯二甲酸、4-乙烯基鄰苯二甲酸、3,4,5,6-四氫鄰苯二甲酸、1,2,3,6-四氫鄰苯二甲酸、二甲基四氫鄰苯二甲酸、1,4-環己烯二羧酸等不飽和二羧酸類; 甲基-5-降冰片烯-2,3-二羧酸、5-羧基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚-2-烯、5-羧基-5-甲基雙環[2.2.1]庚-2-烯、5-羧基-5-乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-乙基雙環[2.2.1]庚-2-烯等含有羧基的雙環不飽和化合物類; 馬來酸酐、檸康酸酐、衣康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐等不飽和二羧酸類酐; 琥珀酸單[2-(甲基)丙烯醯基氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯基氧基乙基]酯等二元以上的多元羧酸的不飽和單[(甲基)丙烯醯基氧基烷基]酯類; 如α-(羥基甲基)丙烯酸般的於同一分子中含有羥基及羧基的不飽和丙烯酸酯類等。 該些中,就共聚反應性的方面或所獲得的樹脂於鹼性水溶液中的溶解性的方面而言,較佳為丙烯酸、甲基丙烯酸、馬來酸酐等。Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-vinyl benzoic acid, m-vinyl benzoic acid, and p-vinyl benzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid Unsaturated dicarboxylic acids such as dicarboxylic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[ 2.2.1]Hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1, Unsaturated dicarboxylic acid anhydrides such as 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride ; Succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester, etc. Unsaturated mono[(meth)acryloxyalkyl] esters; Unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule like α-(hydroxymeth)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable in terms of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution.
(b)是指例如具有碳數2~4的環狀醚結構(例如,選自由氧雜環丙烷環、氧雜環丁烷環及四氫呋喃環所組成的群組中的至少一種)與乙烯性不飽和鍵的聚合性化合物。(b)較佳為具有碳數2~4的環狀醚與(甲基)丙烯醯基氧基的單量體。 再者,於本說明書中,所謂「(甲基)丙烯酸」,表示選自由丙烯酸及甲基丙烯酸所組成的群組中的至少一種。「(甲基)丙烯醯基」及「(甲基)丙烯酸酯」等的表述亦具有相同的含義。(B) refers to, for example, a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxetane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenic Polymeric compounds with unsaturated bonds. (B) Preferably, it is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group. Furthermore, in this specification, the term "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.
作為(b),例如可列舉:具有氧雜環丙烷基與乙烯性不飽和鍵的單量體(b1)(以下,有時稱為「(b1)」)、具有氧雜環丁烷基與乙烯性不飽和鍵的單量體(b2)(以下,有時稱為「(b2)」)、具有四氫呋喃基與乙烯性不飽和鍵的單量體(b3)(以下,有時稱為「(b3)」)。As (b), for example, a monomer having an oxetanyl group and an ethylenically unsaturated bond (b1) (hereinafter, sometimes referred to as "(b1)"), an oxetanyl group and Monomer of ethylenically unsaturated bond (b2) (hereinafter, sometimes referred to as "(b2)"), monomer (b3) with tetrahydrofuran group and ethylenically unsaturated bond (hereinafter, sometimes referred to as " (B3)”).
作為(b1),例如可列舉具有直鏈狀或分支鏈狀的脂肪族不飽和烴經環氧化而成的結構的單量體(b1-1)(以下,有時稱為「(b1-1)」)、具有脂環式不飽和烴經環氧化而成的結構的單量體(b1-2)(以下,有時稱為「(b1-2)」)。As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "(b1-1) )”), a monomer (b1-2) having a structure formed by epoxidation of alicyclic unsaturated hydrocarbon (hereinafter, sometimes referred to as “(b1-2)”).
作為(b1-1),可列舉:(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸β-甲基縮水甘油酯、(甲基)丙烯酸β-乙基縮水甘油酯、縮水甘油基乙烯基醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚、α-甲基-鄰乙烯基苄基縮水甘油醚、α-甲基-間乙烯基苄基縮水甘油醚、α-甲基-對乙烯基苄基縮水甘油醚、2,3-雙(縮水甘油基氧基甲基)苯乙烯、2,4-雙(縮水甘油基氧基甲基)苯乙烯、2,5-雙(縮水甘油基氧基甲基)苯乙烯、2,6-雙(縮水甘油基氧基甲基)苯乙烯、2,3,4-三(縮水甘油基氧基甲基)苯乙烯、2,3,5-三(縮水甘油基氧基甲基)苯乙烯、2,3,6-三(縮水甘油基氧基甲基)苯乙烯、3,4,5-三(縮水甘油基氧基甲基)苯乙烯、2,4,6-三(縮水甘油基氧基甲基)苯乙烯等。Examples of (b1-1) include: glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, and glycidyl vinyl Ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-ethylene Benzyl benzyl glycidyl ether, α-methyl-p-vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl) Base)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyl) Oxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4, 5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.
作為(b1-2),可列舉:乙烯基環己烯單氧化物、1,2-環氧-4-乙烯基環己烷(例如,賽羅西德(Celloxide)2000;大賽璐(Daicel)(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)A400;大賽璐(Daicel)(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)M100;大賽璐(Daicel)(股)製造)、式(BI)所表示的化合物及式(BII)所表示的化合物等。Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; Daicel) (Stock) Manufacturing), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; Daicel (Stock) Manufacturing), (meth)acrylic acid 3,4 -Epoxycyclohexyl methyl ester (for example, Cyclomer M100; manufactured by Daicel Co., Ltd.), a compound represented by formula (BI), a compound represented by formula (BII), and the like.
[化15] [化15]
[式(BI)及式(BII)中,Re 及Rf 表示氫原子、或碳數1~4的烷基,該烷基中所含的氫原子亦可經羥基取代。 Xe 及Xf 表示單鍵、*-Rg -、*-Rg -O-、*-Rg -S-或*-Rg -NH-。 Rg 表示碳數1~6的烷二基。 *表示與O的結合鍵][In formula (BI) and formula (BII), R e and R f represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X e and X f represents a single bond, * - R g -, * - R g -O -, * - R g -S- or * -R g -NH-. R g represents an alkanediyl group having 1 to 6 carbon atoms. *Indicates the bond with O]
作為碳數1~4的烷基,可列舉:甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基等。 作為氫原子經羥基取代的烷基,可列舉:羥基甲基、1-羥基乙基、2-羥基乙基、1-羥基丙基、2-羥基丙基、3-羥基丙基、1-羥基-1-甲基乙基、2-羥基-1-甲基乙基、1-羥基丁基、2-羥基丁基、3-羥基丁基、4-羥基丁基等。 作為Re 及Rf ,較佳為可列舉:氫原子、甲基、羥基甲基、1-羥基乙基、2-羥基乙基,更佳為可列舉:氫原子、甲基。Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, second butyl group, and tertiary butyl group. Examples of alkyl groups in which hydrogen atoms are substituted with hydroxy groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, and 1-hydroxy -1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc. As R e and R f , preferably, a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are mentioned, and more preferably, a hydrogen atom and a methyl group are mentioned.
作為烷二基,可列舉:亞甲基、伸乙基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基等。 作為Xe 及Xf ,較佳為可列舉:單鍵、亞甲基、伸乙基、*-CH2 -O-及*-CH2 CH2 -O-,更佳為可列舉:單鍵、*-CH2 CH2 -O-(*表示與O的結合鍵)。Examples of alkanediyl groups include: methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5 -Diyl, hexane-1,6-diyl, etc. X e and X f preferably include single bond, methylene group, ethylene group, *-CH 2 -O- and *-CH 2 CH 2 -O-, and more preferably include: single bond , *-CH 2 CH 2 -O- (* indicates the bond with O).
作為式(BI)所表示的化合物,可列舉式(BI-1)~式(BI-15)中的任一者所表示的化合物等。其中,較佳為式(BI-1)、式(BI-3)、式(BII-5)、式(BI-7)、式(BI-9)或式(BI-11)~式(BI-15)所表示的化合物,更佳為式(BI-1)、式(BI-7)、式(BI-9)或式(BI-15)所表示的化合物。As a compound represented by Formula (BI), the compound etc. which are represented by any one of Formula (BI-1)-Formula (BI-15) are mentioned. Among them, the formula (BI-1), the formula (BI-3), the formula (BII-5), the formula (BI-7), the formula (BI-9) or the formula (BI-11) to the formula (BI The compound represented by -15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15).
[化16] [化16]
作為式(BII)所表示的化合物,可列舉式(BII-1)~式(BII-15)中的任一者所表示的化合物等。其中,較佳為式(BII-1)、式(BII-3)、式(BII-5)、式(BII-7)、式(BII-9)或式(BII-11)~式(BII-15)所表示的化合物,更佳為式(BII-1)、式(BII-7)、式(BII-9)或式(BII-15)所表示的化合物。As a compound represented by Formula (BII), the compound etc. which are represented by any one of Formula (BII-1)-Formula (BII-15) etc. are mentioned. Among them, the formula (BII-1), the formula (BII-3), the formula (BII-5), the formula (BII-7), the formula (BII-9) or the formula (BII-11) to the formula (BII The compound represented by -15) is more preferably a compound represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15).
[化17] [化17]
式(BI)所表示的化合物及式(BII)所表示的化合物可分別單獨使用,亦可併用兩種以上。於併用式(BI)所表示的化合物及式(BII)所表示的化合物的情況下,該些的含有比率[式(BI)所表示的化合物:式(BII)所表示的化合物]以莫耳基準計較佳為5:95~95:5,更佳為20:80~80:20。The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, respectively, or two or more of them may be used in combination. When the compound represented by the formula (BI) and the compound represented by the formula (BII) are used in combination, the content ratio of these [the compound represented by the formula (BI): the compound represented by the formula (BII)] is in moles The reference meter is preferably 5:95 to 95:5, more preferably 20:80 to 80:20.
作為(b2),更佳為具有氧雜環丁烷基與(甲基)丙烯醯基氧基的單量體。作為(b2),可列舉:3-甲基-3-甲基丙烯醯基氧基甲基氧雜環丁烷、3-甲基-3-丙烯醯基氧基甲基氧雜環丁烷、3-乙基-3-甲基丙烯醯基氧基甲基氧雜環丁烷、3-乙基-3-丙烯醯基氧基甲基氧雜環丁烷、3-甲基-3-甲基丙烯醯基氧基乙基氧雜環丁烷、3-甲基-3-丙烯醯基氧基乙基氧雜環丁烷、3-乙基-3-甲基丙烯醯基氧基乙基氧雜環丁烷、3-乙基-3-丙烯醯基氧基乙基氧雜環丁烷等。As (b2), a monomer having an oxetanyl group and a (meth)acryloxy group is more preferable. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-methacryloyloxymethyloxetane, 3-Ethyl-3-methylpropenyloxymethyloxetane, 3-ethyl-3-propenyloxymethyloxetane, 3-methyl-3-methyl Allyloxyethyl oxetane, 3-methyl-3-propenyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl Oxetane, 3-ethyl-3-propenyloxyethyloxetane and the like.
作為(b3),更佳為具有四氫呋喃基與(甲基)丙烯醯基氧基的單量體。作為(b3),具體而言,可列舉:丙烯酸四氫糠基酯(例如,比斯克(Viscoat)V#150,大阪有機化學工業(股)製造)、甲基丙烯酸四氫糠基酯等。As (b3), a monomer having a tetrahydrofuran group and a (meth)acryloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
作為(b),就可進一步提高所獲得的彩色濾光片的耐熱性、耐化學品性等可靠性的方面而言,較佳為(b1)。進而,就著色硬化性樹脂組成物的保存穩定性優異的方面而言,更佳為(b1-2)。As (b), (b1) is preferable from the point which can further improve the reliability, such as heat resistance and chemical resistance of the color filter obtained. Furthermore, in terms of excellent storage stability of the colored curable resin composition, (b1-2) is more preferable.
作為(c),可列舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二基酯、(甲基)丙烯酸月桂基酯、(甲基)丙烯酸硬脂基酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.02,6 ]癸烷-8-基酯(該技術領域中,作為慣用名而稱為「(甲基)丙烯酸二環戊烷基酯」。另外,有時稱為「(甲基)丙烯酸三環癸酯」)、(甲基)丙烯酸三環[5.2.1.02,6 ]癸烯-8-基酯(該技術領域中,作為慣用名而稱為「(甲基)丙烯酸二環戊烯基酯」)、(甲基)丙烯酸二環戊烷基氧基乙酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸炔丙酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸萘酯、(甲基)丙烯酸苄酯等(甲基)丙烯酸酯類; (甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯等含羥基的(甲基)丙烯酸酯類; 馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯等二羧酸二酯; 雙環[2.2.1]庚-2-烯、5-甲基雙環[2.2.1]庚-2-烯、5-乙基雙環[2.2.1]庚-2-烯、5-羥基雙環[2.2.1]庚-2-烯、5-羥基甲基雙環[2.2.1]庚-2-烯、5-(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5-甲氧基雙環[2.2.1]庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯、5,6-二羥基雙環[2.2.1]庚-2-烯、5,6-二(羥基甲基)雙環[2.2.1]庚-2-烯、5,6-二(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5,6-二甲氧基雙環[2.2.1]庚-2-烯、5,6-二乙氧基雙環[2.2.1]庚-2-烯、5-羥基-5-甲基雙環[2.2.1]庚-2-烯、5-羥基-5-乙基雙環[2.2.1]庚-2-烯、5-羥基甲基-5-甲基雙環[2.2.1]庚-2-烯、5-第三丁氧基羰基雙環[2.2.1]庚-2-烯、5-環己基氧基羰基雙環[2.2.1]庚-2-烯、5-苯氧基羰基雙環[2.2.1]庚-2-烯、5,6-雙(第三丁氧基羰基)雙環[2.2.1]庚-2-烯、5,6-雙(環己基氧基羰基)雙環[2.2.1]庚-2-烯等雙環不飽和化合物類; 苯乙烯、α-甲基苯乙烯、間甲基苯乙烯、對甲基苯乙烯、乙烯基甲苯、對甲氧基苯乙烯、丙烯腈、甲基丙烯腈、氯乙烯、偏二氯乙烯、丙烯醯胺、甲基丙烯醯胺、乙酸乙烯酯、1,3-丁二烯、異戊二烯、2,3-二甲基-1,3-丁二烯等。Examples of (c) include: methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second butyl (meth)acrylate, and third (meth)acrylate Butyl ester, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, (meth)acrylate ring Amyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate (the technology In the field, it is called "dicyclopentyl (meth)acrylate" as a common name. In addition, it is sometimes called "tricyclodecyl (meth)acrylate"), tricyclo (meth)acrylate [ 5.2.1.0 2,6 ]decene-8-yl ester (in this technical field, it is called "dicyclopentenyl (meth)acrylate" as a common name), dicyclopentane (meth)acrylate Ethyloxyethyl, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate , Naphthyl (meth)acrylate, benzyl (meth)acrylate and other (meth)acrylates; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate and other hydroxy-containing (Meth) acrylates; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconic acid, etc.; bicyclo[2.2.1]hept-2-ene, 5-methyl Bicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo [2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[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-bis(hydroxymethyl)bicyclo[2.2.1 ]Hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2- Ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethyl Bicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tertiary butoxycarbonylbicyclo[2.2.1]hept- 2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tertiary but Oxycarbonyl) bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; styrene, α -Methyl styrene, m-methyl styrene, p-methyl styrene, vinyl methyl Benzene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene Ene, 2,3-dimethyl-1,3-butadiene, etc.
樹脂[K1]中,源自每一者的結構單元的比率於構成樹脂[K1]的全部結構單元中較佳為 源自(a)的結構單元:2莫耳%~55莫耳% 源自(b)的結構單元:2莫耳%~85莫耳% 源自(m)的結構單元:1莫耳%~65莫耳%, 更佳為 源自(a)的結構單元:5莫耳%~50莫耳% 源自(b)的結構單元:5莫耳%~70莫耳% 源自(m)的結構單元:5莫耳%~60莫耳%。 若樹脂[K1]的結構單元的比率處於所述範圍,則可更進一步提升由著色硬化性樹脂組成物所獲得的彩色濾光片的吸光保持率。In the resin [K1], the ratio of the structural unit derived from each to all the structural units constituting the resin [K1] is preferably Structural unit derived from (a): 2mol%~55mol% Structural unit derived from (b): 2 mol%~85 mol% Structural unit derived from (m): 1 mol%~65 mol%, Better Structural unit derived from (a): 5 mol%~50 mol% Structural unit derived from (b): 5 mol%~70 mol% Structural unit derived from (m): 5 mol% to 60 mol%. If the ratio of the structural unit of the resin [K1] is in the above range, the light absorption retention rate of the color filter obtained from the colored curable resin composition can be further improved.
樹脂[K1]例如可參考文獻「高分子合成的實驗法」(大津隆行著 化學同人出版社(股) 第1版第1次印刷 1972年3月1日發行)中記載的方法以及該文獻中記載的引用文獻而製造。For resin [K1], for example, refer to the method described in the document "Experimental Method of Polymer Synthesis" (Otsu Takayuki Chemical Dojin Publishing Co., Ltd., 1st edition, first printing, issued on March 1, 1972) and the document Manufactured by the cited literature.
具體而言,可列舉如下方法:將(a)、(b)及(m)的規定量、聚合起始劑、以及溶劑等放入至反應容器中,例如利用氮氣對氧氣進行置換,藉此製成脫氧環境,一面攪拌一面進行加熱及保溫。再者,此處所使用的聚合起始劑及溶劑等並無特別限定,可使用該領域中通常所使用者。例如,作為聚合起始劑,可列舉偶氮化合物(2,2'-偶氮雙異丁腈、2,2'-偶氮雙(2,4-二甲基戊腈)等)或有機過氧化物(過氧化苯甲醯等),作為溶劑,只要為溶解各單體者即可,可列舉作為本發明的著色硬化性樹脂組成物的溶劑(E)而後述的溶劑等。Specifically, the following method can be cited: putting predetermined amounts of (a), (b), and (m), a polymerization initiator, a solvent, etc., into a reaction vessel, for example, replacing oxygen with nitrogen, thereby Create a deoxygenated environment, and heat and keep warm while stirring. In addition, the polymerization initiator, solvent, etc. used here are not particularly limited, and those generally used in this field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or organic The oxides (benzyl peroxide, etc.) may be solvents as long as they dissolve each monomer, and examples include solvents (E) described later as the solvent (E) of the colored curable resin composition of the present invention.
再者,所得到的共聚物可直接使用反應後的溶液,亦可使用經濃縮或稀釋的溶液,亦可使用藉由再沈澱等方法而以固體(粉體)的形式取出者。尤其是,藉由使用本發明的著色硬化性樹脂組成物中所含的溶劑作為該聚合時的溶劑,可將反應後的溶液直接用於本發明的著色硬化性樹脂組成物的製備,因此可使本發明的著色硬化性樹脂組成物的製造步驟簡化。In addition, the obtained copolymer may be directly used as a solution after the reaction, a concentrated or diluted solution may also be used, or a solid (powder) obtained by a method such as reprecipitation may be used. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during the polymerization, the reacted solution can be directly used for the preparation of the colored curable resin composition of the present invention. The manufacturing steps of the colored curable resin composition of the present invention are simplified.
樹脂[K2]中,源自每一者的結構單元的比率於構成樹脂[K2]的全部結構單元中較佳為 源自(a)的結構單元:2莫耳%~55莫耳% 源自(b)的結構單元:2莫耳%~85莫耳% 源自(m)的結構單元:1莫耳%~65莫耳% 源自(c)的結構單元:1莫耳%~50莫耳%, 更佳為 源自(a)的結構單元:5莫耳%~50莫耳% 源自(b)的結構單元:5莫耳%~70莫耳% 源自(m)的結構單元:5莫耳%~60莫耳% 源自(c)的結構單元:2莫耳%~40莫耳%。 若樹脂[K2]的結構單元的比率處於所述範圍,則可更進一步提升由著色硬化性樹脂組成物所獲得的彩色濾光片的吸光保持率。In the resin [K2], the ratio of the structural units derived from each to all the structural units constituting the resin [K2] is preferably Structural unit derived from (a): 2mol%~55mol% Structural unit derived from (b): 2 mol%~85 mol% Structural unit derived from (m): 1 mol%~65 mol% The structural unit derived from (c): 1 mol%~50 mol%, Better Structural unit derived from (a): 5 mol%~50 mol% Structural unit derived from (b): 5 mol%~70 mol% Structural unit derived from (m): 5 mol%~60 mol% Structural unit derived from (c): 2 mol%-40 mol%. If the ratio of the structural unit of the resin [K2] is in the above range, the light absorption retention rate of the color filter obtained from the coloring curable resin composition can be further improved.
樹脂[K2]例如能夠以與作為樹脂[K1]的製造方法而記載的方法相同的方式進行製造。The resin [K2] can be manufactured in the same manner as the method described as the manufacturing method of the resin [K1], for example.
樹脂[K3]中,源自每一者的結構單元的比率於構成樹脂[K3]的全部結構單元中較佳為 源自(a)的結構單元:2莫耳%~60莫耳% 源自(m)的結構單元:40莫耳%~98莫耳%, 更佳為 源自(a)的結構單元:10莫耳%~55莫耳% 源自(m)的結構單元:45莫耳%~90莫耳%。 樹脂[K3]例如能夠以與作為樹脂[K1]的製造方法而記載的方法相同的方式進行製造。In the resin [K3], the ratio of the structural units derived from each to all the structural units constituting the resin [K3] is preferably Structural unit derived from (a): 2 mol%~60 mol% Structural unit derived from (m): 40 mol%~98 mol%, Better Structural unit derived from (a): 10 mol%~55 mol% Structural unit derived from (m): 45 mol% to 90 mol%. The resin [K3] can be manufactured in the same manner as the method described as the manufacturing method of the resin [K1], for example.
樹脂[K4]中,源自每一者的結構單元的比率於構成樹脂[K1]的全部結構單元中較佳為 源自(a)的結構單元:2莫耳%~55莫耳% 源自(m)的結構單元:1莫耳%~65莫耳% 源自(c)的結構單元:1莫耳%~50莫耳%, 更佳為 源自(a)的結構單元:5莫耳%~50莫耳% 源自(m)的結構單元:5莫耳%~60莫耳% 源自(c)的結構單元:2莫耳%~40莫耳%。 樹脂[K4]例如能夠以與作為樹脂[K1]的製造方法而記載的方法相同的方式進行製造。In the resin [K4], the ratio of the structural unit derived from each to all the structural units constituting the resin [K1] is preferably Structural unit derived from (a): 2mol%~55mol% Structural unit derived from (m): 1 mol%~65 mol% The structural unit derived from (c): 1 mol%~50 mol%, Better Structural unit derived from (a): 5 mol%~50 mol% Structural unit derived from (m): 5 mol%~60 mol% Structural unit derived from (c): 2 mol%-40 mol%. The resin [K4] can be manufactured in the same manner as the method described as the manufacturing method of the resin [K1], for example.
關於樹脂[K5],作為第一階段,以與所述樹脂[K1]的製造方法相同的方式獲得(b)與(m)的共聚物。與所述同樣地,所得到的共聚物可直接使用反應後的溶液,亦可使用經濃縮或稀釋的溶液,亦可使用藉由再沈澱等方法而以固體(粉體)的形式取出者。 相對於構成所述共聚物的全部結構單元的合計莫耳數,源自(b)及(m)的結構單元的比率分別較佳為 源自(b)的結構單元:5莫耳%~95莫耳% 源自(m)的結構單元:5莫耳%~95莫耳%, 更佳為 源自(b)的結構單元:10莫耳%~90莫耳% 源自(m)的結構單元:10莫耳%~90莫耳%。Regarding the resin [K5], as the first stage, a copolymer of (b) and (m) is obtained in the same manner as the production method of the resin [K1]. In the same manner as described above, the obtained copolymer may be directly used as a solution after the reaction, a concentrated or diluted solution may be used, or a solid (powder) obtained by a method such as reprecipitation may be used. The ratios of the structural units derived from (b) and (m) to the total molar number of all structural units constituting the copolymer are preferably Structural unit derived from (b): 5 mol%~95 mol% Structural unit derived from (m): 5 mol%~95 mol%, Better Structural unit derived from (b): 10 mol%~90 mol% Structural unit derived from (m): 10 mol% to 90 mol%.
繼而,使燒瓶內成為空氣環境,將(b)與(m)的共聚物、(a)、羧酸或羧酸酐與環狀醚的反應觸媒(例如,三(二甲基胺基甲基)苯酚等)及聚合抑制劑(例如,對苯二酚等)等放入至燒瓶內,例如於60℃~130℃下反應1小時~10小時,使(b)與(m)的共聚物所具有的源自(b)的環狀醚和(a)所具有的羧酸或羧酸酐反應,藉此可獲得樹脂[K5]。 相對於(b)100莫耳,與所述共聚物進行反應的(a)的使用量較佳為5莫耳~80莫耳。就環狀醚的反應性高、難以殘存未反應的(b)而言,作為樹脂[K5]中使用的(b),較佳為(b1)。 相對於(a)、(b)及(m)的合計量100質量份,所述反應觸媒的使用量較佳為0.001質量份~5質量份。相對於(a)、(b)及(m)的合計量100質量份,所述聚合抑制劑的使用量較佳為0.001質量份~5質量份。 裝入方法、反應溫度及時間等反應條件可考慮製造設備或聚合所帶來的發熱量等而適當調整。再者,可與聚合條件同樣地,考慮製造設備或聚合所帶來的發熱量等而適當調整裝入方法或反應溫度。Then, the inside of the flask is made into an air environment, and the copolymer of (b) and (m), (a), carboxylic acid or carboxylic anhydride and the reaction catalyst of cyclic ether (for example, tris(dimethylaminomethyl) ) Phenol, etc.) and polymerization inhibitors (for example, hydroquinone, etc.) are put into the flask, for example, react at 60°C to 130°C for 1 hour to 10 hours to make the copolymer of (b) and (m) Resin [K5] is obtained by reacting the cyclic ether derived from (b) and the carboxylic acid or carboxylic anhydride that (a) has. The amount of (a) used to react with the copolymer is preferably 5 mol to 80 mol relative to (b) 100 mol. As for the (b) which has high reactivity of the cyclic ether and is unlikely to remain unreacted, (b) used for the resin [K5] is preferably (b1). The amount of the reaction catalyst used is preferably 0.001 parts by mass to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (m). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (m). The reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of manufacturing equipment or heat generation due to polymerization. In addition, in the same manner as the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of manufacturing equipment or heat generation due to polymerization.
樹脂[K6]是進一步使羧酸酐與樹脂[K5]反應而獲得的樹脂。使羧酸酐和藉由環狀醚與羧酸或羧酸酐的反應而產生的羥基進行反應。 作為羧酸酐,可列舉:馬來酸酐、檸康酸酐、衣康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐等。相對於(a)的使用量1莫耳,羧酸酐的使用量較佳為0.5莫耳~1莫耳。Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic acid anhydride is reacted with the hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride. Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydroophthalic anhydride, Phthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride Wait. The usage amount of carboxylic anhydride is preferably 0.5 mol to 1 mol relative to 1 mol of the usage amount of (a).
作為樹脂(B),具體而言,可列舉:(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚物等樹脂[K1]; (甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-苯基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸酯/(甲基)丙烯酸/N-苄基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、3-甲基-3-(甲基)丙烯醯基氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯/N-苯基馬來醯亞胺共聚物、3-甲基-3-(甲基)丙烯醯基氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯/N-環己基馬來醯亞胺共聚物、3-甲基-3-(甲基)丙烯醯基氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯/N-苄基馬來醯亞胺共聚物等樹脂[K2]; N-苯基馬來醯亞胺/(甲基)丙烯酸共聚物、N-環己基馬來醯亞胺/(甲基)丙烯酸共聚物、N-苄基馬來醯亞胺/(甲基)丙烯酸共聚物等樹脂[K3]; (甲基)丙烯酸苄酯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚、苯乙烯/(甲基)丙烯酸/N-苯基馬來醯亞胺共聚物、苯乙烯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、苯乙烯/(甲基)丙烯酸/N-苄基馬來醯亞胺共聚、(甲基)丙烯酸/N-苯基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、(甲基)丙烯酸/N-苄基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物等樹脂[K4]; 使(甲基)丙烯酸與N-苯基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應所得的樹脂、使(甲基)丙烯酸與N-環己基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應所得的樹脂、使(甲基)丙烯酸與N-苄基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應所得的樹脂等樹脂[K5]; 使(甲基)丙烯酸與N-苯基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應並使該反應所得的樹脂進一步與四氫鄰苯二甲酸酐反應而得到的樹脂、使(甲基)丙烯酸與N-環己基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應並使該反應所得的樹脂進一步與四氫鄰苯二甲酸酐反應而得到的樹脂、使(甲基)丙烯酸與N-苄基馬來醯亞胺/(甲基)丙烯酸縮水甘油酯的共聚物反應並使該反應所得的樹脂進一步與四氫鄰苯二甲酸酐反應而得到的樹脂等樹脂[K6]等。 其中,作為樹脂(B),較佳為樹脂[K1]~樹脂[K4],更佳為樹脂[K1]及樹脂[K2]。As the resin (B), specifically, 3,4-epoxycyclohexyl methyl (meth)acrylate/(meth)acrylic acid/N-phenylmaleimide copolymer, (methyl) ) 3,4-epoxycyclohexyl methyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxycyclohexyl methyl (meth)acrylate/(methyl) )Acrylic acid/N-benzylmaleimide copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(meth)acrylic acid/N-phenylmaleimide Copolymer, acrylic 3,4-epoxy tricyclic [5.2.1.0 2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, acrylic 3,4-epoxy tricyclic [5.2.1.0 2,6 ] Decyl ester/(meth)acrylic acid/N-benzylmaleimide copolymer and other resins [K1]; (meth)glycidyl acrylate/(meth)acrylic acid benzyl ester /(Meth)acrylic acid/N-phenylmaleimide copolymer, glycidyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide Amine copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid/N-benzylmaleimide copolymer, glycidyl (meth)acrylate/styrene/ (Meth) acrylic acid/N-phenylmaleimide copolymer, (meth)acrylic acid glycidyl ester/styrene/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, (formaldehyde) Base) glycidyl acrylate/styrene/(meth)acrylic acid/N-benzylmaleimide copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(methyl) )Acrylic acid/N-phenylmaleimide/(meth)acrylic acid 2-hydroxyethyl copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(methyl) Acrylic acid/N-cyclohexylmaleimide/(meth)acrylic acid 2-hydroxyethyl copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(meth)acrylic acid /N-benzylmaleimide/(meth)acrylic acid 2-hydroxyethyl copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(formaldehyde) Base) acrylic acid/styrene/N-phenylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/benzene Ethylene/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene/N-benzyl Resins such as maleimide copolymer [K2]; N-phenylmaleimide/(meth)acrylic acid copolymer, N-cyclohexylmaleimide/(meth)acrylic acid copolymer, N-benzyl maleimide/(meth)acrylic acid copolymer and other resins [K3]; (meth) benzyl acrylate/(meth)acrylic acid/N-phenylmaleimide copolymer, ( Benzyl meth)acrylate Ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, benzyl (meth)acrylate/(meth)acrylic acid/N-benzylmaleimide copolymer, styrene/(formaldehyde) Base) acrylic acid/N-phenylmaleimide copolymer, styrene/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, styrene/(meth)acrylic acid/N-benzyl Copolymerization of maleimide, (meth)acrylic acid/N-phenylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, (meth)acrylic acid/N-cyclohexylmaleimide Amine/(meth)acrylic acid 2-hydroxyethyl copolymer, (meth)acrylic acid/N-benzyl maleimide/(meth)acrylic acid 2-hydroxyethyl copolymer and other resins [K4]; (Meth)acrylic acid and N-phenylmaleimide/(meth)acrylic acid glycidyl ester copolymer resin obtained by reacting (meth)acrylic acid and N-cyclohexylmaleimide/( Resins obtained by reacting a copolymer of glycidyl meth)acrylate, resins obtained by reacting a copolymer of (meth)acrylic acid and N-benzyl maleimide/glycidyl (meth)acrylate, etc. [ K5]; The copolymer of (meth)acrylic acid and N-phenylmaleimide/glycidyl (meth)acrylate is reacted and the resin obtained by the reaction is further reacted with tetrahydrophthalic anhydride Resin obtained, reacting (meth)acrylic acid with a copolymer of N-cyclohexylmaleimide/glycidyl (meth)acrylate and further reacting the resin obtained by the reaction with tetrahydrophthalic anhydride The resulting resin is reacted with a copolymer of (meth)acrylic acid and N-benzylmaleimide/glycidyl (meth)acrylate, and the resin obtained by the reaction is further reacted with tetrahydrophthalic anhydride Resin [K6] etc., such as resin obtained by reaction. Among them, as the resin (B), resin [K1] to resin [K4] are preferred, and resin [K1] and resin [K2] are more preferred.
樹脂(B)的聚苯乙烯換算的重量平均分子量較佳為3,000~100,000,更佳為5,000~50,000,進而佳為5,000~30,000。若分子量處於所述範圍內,則有如下傾向:彩色濾光片的硬度提升,殘膜率高,未曝光部對顯影液的溶解性良好,且著色圖案的解析度提升。The weight average molecular weight in terms of polystyrene of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. If the molecular weight is within the above range, there is a tendency that the hardness of the color filter increases, the residual film rate is high, the solubility of the unexposed part to the developing solution is good, and the resolution of the colored pattern increases.
樹脂(B)的分散度[重量平均分子量(Mw)/數量平均分子量(Mn)]較佳為1.1~6,更佳為1.2~4。The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.
樹脂(B)的酸價以固體成分換算計較佳為70 mg-KOH/g以上,更佳為90 mg-KOH/g以上,進而佳為110 mg-KOH/g以上,較佳為220 mg-KOH/g以下,更佳為210 mg-KOH/g以下,進而佳為200 mg-KOH/g以下。此處,酸價是作為中和樹脂(B)1 g所需要的氫氧化鉀的量(mg)而測定的值,例如可藉由使用氫氧化鉀水溶液進行滴定而求出。The acid value of the resin (B) in terms of solid content is preferably 70 mg-KOH/g or more, more preferably 90 mg-KOH/g or more, still more preferably 110 mg-KOH/g or more, and more preferably 220 mg-KOH/g KOH/g or less, more preferably 210 mg-KOH/g or less, and still more preferably 200 mg-KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and it can be determined, for example, by titration using an aqueous potassium hydroxide solution.
相對於固體成分的總量,樹脂(B)的含有率較佳為7質量%~80質量%,更佳為13質量%~75質量%,進而佳為17質量%~65質量%。若樹脂(B)的含有率處於所述範圍內,則有可形成著色圖案,另外著色圖案的解析度及殘膜率提升的傾向。The content of the resin (B) relative to the total solid content is preferably 7 mass% to 80 mass%, more preferably 13 mass% to 75 mass%, and still more preferably 17 mass% to 65% by mass. If the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to increase.
相對於樹脂(B)及聚合性化合物(C)的合計量100質量份,樹脂(B)的含量較佳為10質量份以上且95質量份以下,更佳為20質量份以上且90質量份以下,進而佳為30質量份以上且85質量份以下。若樹脂(B)的含量處於所述範圍內,則所得到的彩色濾光片的吸光度保持率進一步提升。 另外,相對於樹脂(B)及聚合性化合物(C)的合計量100質量份,樹脂(B)的含量亦以55質量份以上且95質量份以下、較佳為60質量份以上且90質量份以下為宜。若樹脂(B)的含量處於所述範圍,則所得到的彩色濾光片的吸光度保持率顯著提升。 在相對於樹脂(B)及聚合性化合物(C)的合計量100質量份而樹脂(B)的含量例如為10質量份以上且60質量份以下、較佳為20質量份以上且55質量份以下的情況下,所得到的彩色濾光片的吸光度保持率與明度提升。The content of resin (B) is preferably 10 parts by mass or more and 95 parts by mass or less, and more preferably 20 parts by mass or more and 90 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) Below, it is more preferable that it is 30 mass parts or more and 85 mass parts or less. If the content of the resin (B) is within the above-mentioned range, the absorbance retention rate of the obtained color filter is further improved. In addition, relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C), the content of resin (B) is also 55 parts by mass or more and 95 parts by mass or less, preferably 60 parts by mass or more and 90 parts by mass The following is appropriate. If the content of the resin (B) is in the above range, the absorbance retention rate of the obtained color filter is significantly improved. The content of resin (B) is, for example, 10 parts by mass or more and 60 parts by mass or less, preferably 20 parts by mass or more and 55 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) In the following cases, the absorbance retention and brightness of the obtained color filter are improved.
<聚合性化合物(C)> 聚合性化合物(C)為可藉由自聚合起始劑(D)產生的活性自由基及/或酸而聚合的化合物,例如可列舉具有聚合性的乙烯性不飽和鍵的化合物,較佳為(甲基)丙烯酸酯化合物。<Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by living radicals and/or an acid generated from the polymerization initiator (D). For example, a compound having a polymerizable ethylenic unsaturated bond can be mentioned, preferably (Meth)acrylate compound.
其中,聚合性化合物(C)較佳為具有3個以上的乙烯性不飽和鍵的聚合性化合物。作為此種聚合性化合物,例如可列舉:三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯、四季戊四醇九(甲基)丙烯酸酯、三(2-(甲基)丙烯醯基氧基乙基)異氰脲酸酯、乙二醇改質季戊四醇四(甲基)丙烯酸酯、乙二醇改質二季戊四醇六(甲基)丙烯酸酯、丙二醇改質季戊四醇四(甲基)丙烯酸酯、丙二醇改質二季戊四醇六(甲基)丙烯酸酯、己內酯改質季戊四醇四(甲基)丙烯酸酯、己內酯改質二季戊四醇六(甲基)丙烯酸酯。 其中,較佳為二季戊四醇五(甲基)丙烯酸酯及二季戊四醇六(甲基)丙烯酸酯。Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate Esters, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, pentaerythritol deca(meth)acrylate, pentaerythritol nona(meth)acrylate Ester, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth) Acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, caprolactone modified dipentaerythritol hexa (Meth)acrylate. Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred.
相對於固體成分的總量,聚合性化合物(C)的含有率較佳為1質量%~65質量%,更佳為5質量%~60質量%,進而佳為10質量%~55質量%。若聚合性化合物(C)的含有率處於所述範圍內,則有著色圖案形成時的殘膜率及彩色濾光片的耐化學品性提升的傾向。The content rate of the polymerizable compound (C) relative to the total solid content is preferably 1% by mass to 65% by mass, more preferably 5% by mass to 60% by mass, and still more preferably 10% by mass to 55% by mass. If the content rate of the polymerizable compound (C) is within the above-mentioned range, the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter tend to improve.
<聚合起始劑(D)> 聚合起始劑(D)只要為可藉由光或熱的作用而產生活性自由基、酸等而使聚合開始的化合物,則並無特別限定,可使用公知的聚合起始劑。作為產生活性自由基的聚合起始劑,例如可列舉:O-醯基肟化合物、苯烷基酮化合物、三嗪化合物、醯基氧化膦化合物及聯咪唑化合物。<Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate a living radical, acid, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator that generates living radicals include O-acyl oxime compounds, phenalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds.
作為所述O-醯基肟化合物,例如可列舉:N-苯甲醯基氧基-1-(4-苯基巰基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯基巰基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯基巰基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯基氧基-1-(4-苯基巰基苯基)-3-環己基丙烷-1-酮-2-亞胺等具有二苯基硫醚骨架的O-醯基肟化合物;N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-{2-甲基-4-(3,3-二甲基-2,4-二氧雜環戊烷基甲基氧基)苯甲醯基}-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-亞胺、N-苯甲醯基氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-酮-2-亞胺等具有咔唑骨架的O-醯基肟化合物;1-[7-(2-甲基苯甲醯基)-9,9-二丙基-9H-芴-2-基]乙酮 O-乙醯基肟等具有芴骨架的O-醯基肟化合物;等。亦可使用豔佳固(Irgacure)(註冊商標)OXE01、OXE02(以上,巴斯夫(BASF)公司製造)、N-1919(艾迪科(ADEKA)公司製造)、DFI-091(大東化學(Daito Chemix)股份有限公司製造)等市售品。其中,O-醯基肟化合物較佳為選自由N-苯甲醯基氧基-1-(4-苯基巰基苯基)辛烷-1-酮-2-亞胺、N-乙醯基氧基-1-(4-苯基巰基苯基)-3-環己基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-[9-乙基-6-{2-甲基-4-(3,3-二甲基-2,4-二氧雜環戊烷基甲基氧基)苯甲醯基}-9H-咔唑-3-基]乙烷-1-亞胺及1-[7-(2-甲基苯甲醯基)-9,9-二丙基-9H-芴-2-基]乙酮 O-乙醯基肟所組成的群組中的至少一種。若為該些O-醯基肟化合物,則有可獲得高明度的彩色濾光片的傾向。Examples of the O-acetoxime compound include N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine Benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzyloxy-1-(4-phenylmercaptophenyl)-3 -Cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. O-acetoxy oxime compound with diphenyl sulfide skeleton; N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazole-3- Yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxide Cyclopentylmethyloxy)benzyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6- (2-Methylbenzyl)-9H-carbazol-3-yl)-3-cyclopentylpropane-1-imine, N-benzyloxy-1-[9-ethyl- 6-(2-Methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine and other O-acyloxime compounds with carbazole skeleton ; 1-[7-(2-methylbenzyl)-9,9-dipropyl-9H-fluoren-2-yl] ethyl ketone O-acetoxyoxime, etc. O-acetyl group with fluorene skeleton Oxime compound; etc. Irgacure (registered trademark) OXE01, OXE02 (above, made by BASF), N-1919 (made by ADEKA), DFI-091 (Daito Chemix) can also be used ) Manufactured by a company limited by shares) and other commercial products. Among them, the O-acetoxime compound is preferably selected from N-benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-acetoxy Oxy-1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-{2- Methyl-4-(3,3-dimethyl-2,4-dioxolanemethyloxy)benzyl}-9H-carbazol-3-yl)ethane-1- Imine and 1-[7-(2-methylbenzyl)-9,9-dipropyl-9H-fluoren-2-yl] ethyl ketone O-acetyloxime in the group consisting of At least one. In the case of these O-acetoxime compounds, there is a tendency to obtain a color filter with high brightness.
作為所述苯烷基酮化合物,例如可列舉:2-甲基-2-嗎啉基-1-(4-甲基巰基苯基)丙烷-1-酮、2-二甲基胺基-1-(4-嗎啉基苯基)-2-苄基丁烷-1-酮、2-(二甲基胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-嗎啉基)苯基]丁烷-1-酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、2-羥基-2-甲基-1-[4-(2-羥基乙氧基)苯基]丙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-(4-異丙烯基苯基)丙烷-1-酮的寡聚物、α,α-二乙氧基苯乙酮、苄基二甲基縮酮等。亦可使用豔佳固(Irgacure)(註冊商標)369、907、379(以上,巴斯夫(BASF)公司製造)等市售品。As the phenalkyl ketone compound, for example, 2-methyl-2-morpholinyl-1-(4-methylmercaptophenyl)propan-1-one, 2-dimethylamino-1 -(4-morpholinylphenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[ 4-(4-morpholinyl)phenyl]butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[ 4-(2-hydroxyethoxy)phenyl)propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane- 1-ketone oligomer, α,α-diethoxy acetophenone, benzyl dimethyl ketal, etc. Commercial products such as Irgacure (registered trademark) 369, 907, 379 (above, manufactured by BASF) can also be used.
作為所述三嗪化合物,例如可列舉:2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三嗪等。As the triazine compound, for example, 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-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6 -[2-(5-Methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2- Yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl ]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5- Triazine and so on.
作為所述醯基氧化膦化合物,可列舉:2,4,6-三甲基苯甲醯基二苯基氧化膦等。亦可使用豔佳固(Irgacure)(註冊商標)819(巴斯夫(BASF)公司製造)等市售品。As said acylphosphine oxide compound, 2,4,6-trimethylbenzyl diphenyl phosphine oxide etc. are mentioned. Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.
作為所述聯咪唑化合物,例如可列舉:2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(2,3-二氯苯基)-4,4',5,5'-四苯基聯咪唑(例如參照日本專利特開平6-75372號公報、日本專利特開平6-75373號公報等)、2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(二烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(三烷氧基苯基)聯咪唑(例如參照日本專利特公昭48-38403號公報、日本專利特開昭62-174204號公報等)、4,4',5,5'-位的苯基經烷氧羰基取代的聯咪唑化合物(例如參照日本專利特開平7-10913號公報等)等。As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2, 3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2, 2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5 '-Tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2 ,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Kokai 62-174204, etc.), a biimidazole compound in which the phenyl group at the 4,4',5,5'-position is substituted with an alkoxycarbonyl group (for example, refer to Japanese Patent Laid-Open No. 7-10913 etc.).
作為產生酸的聚合起始劑,例如可列舉:4-羥基苯基二甲基鋶對甲苯磺酸鹽、4-羥基苯基二甲基鋶六氟銻酸鹽、4-乙醯氧基苯基二甲基鋶對甲苯磺酸鹽、4-乙醯氧基苯基·甲基·苄基鋶六氟銻酸鹽、三苯基鋶對甲苯磺酸鹽、三苯基鋶六氟銻酸鹽、二苯基錪對甲苯磺酸鹽、二苯基錪六氟銻酸鹽等鎓鹽類、或硝基苄基甲苯磺酸鹽類、安息香甲苯磺酸鹽類等。Examples of the polymerization initiator that generates acid include: 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, and 4-acetoxybenzene Dimethyl sulfonate p-toluene sulfonate, 4-acetoxyphenyl·methyl·benzyl sulfonate hexafluoroantimonate, triphenyl sulfonate p-toluenesulfonate, triphenyl sulfonium hexafluoroantimonate Salts, onium salts such as diphenyl iodonium p-toluenesulfonate, diphenyl iodonium hexafluoroantimonate, or nitrobenzyl toluenesulfonate, benzoin toluenesulfonate, etc.
進而,作為聚合起始劑(D),可列舉:安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香異丁醚等安息香化合物;二苯甲酮、鄰苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4'-甲基二苯基硫醚、3,3',4,4'-四(第三丁基過氧化羰基)二苯甲酮、2,4,6-三甲基二苯甲酮等二苯甲酮化合物;9,10-菲醌、2-乙基蒽醌、樟腦醌等醌化合物;10-丁基-2-氯吖啶酮、苯偶醯、苯基乙醛酸甲酯、二茂鈦化合物等。Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like; benzophenone, methyl benzoin benzoate , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)diphenyl Benzophenone compounds such as methyl ketone and 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone; 10-butyl-2- Chloracridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc.
作為聚合起始劑(D),較佳為包含選自由O-醯基肟化合物、苯烷基酮化合物、三嗪化合物、醯基氧化膦化合物及聯咪唑化合物所組成的群組中的至少一種的聚合起始劑,更佳為包含O-醯基肟化合物的聚合起始劑。The polymerization initiator (D) preferably contains at least one selected from the group consisting of O-acyl oxime compounds, phenalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds The polymerization initiator is more preferably a polymerization initiator containing an O-acetoxime compound.
相對於樹脂(B)及聚合性化合物(C)的合計量100質量份,聚合起始劑(D)的含量較佳為0.1質量份~30質量份,更佳為1質量份~20質量份。若聚合起始劑(D)的含量處於所述範圍內,則有發生高感度化而曝光時間縮短的傾向,因此,彩色濾光片的生產性提升。The content of the polymerization initiator (D) is preferably 0.1 parts by mass to 30 parts by mass, more preferably 1 part by mass to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and polymerizable compound (C) . If the content of the polymerization initiator (D) is within the above-mentioned range, there is a tendency for high sensitivity to occur and shorten the exposure time, and therefore, the productivity of the color filter improves.
<溶劑(E)> 溶劑(E)並無特別限定,可使用該領域中通常所使用的溶劑。例如可列舉:酯溶劑(於分子內包含-COO-且不包含-O-的溶劑)、醚溶劑(於分子內包含-O-且不包含-COO-的溶劑)、醚酯溶劑(於分子內包含-COO-與-O-的溶劑)、酮溶劑(於分子內包含-CO-且不包含-COO-的溶劑)、醇溶劑(於分子內包含OH且不包含-O-、-CO-及-COO-的溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸。<Solvent (E)> The solvent (E) is not particularly limited, and solvents generally used in this field can be used. Examples include: ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents Solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (containing OH but not -O-, -CO in the molecule) -And -COO- solvent), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfide.
作為酯溶劑,可列舉:乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、乙酸乙酯、乙酸正丁酯、乙酸異丁酯、甲酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、環己醇乙酸酯及γ-丁內酯等。Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, and isoamyl acetate , Butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, cyclic Hexanol acetate and γ-butyrolactone, etc.
作為醚溶劑,可列舉:乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、3-甲氧基-1-丁醇、3-甲氧基-3-甲基丁醇、四氫呋喃、四氫吡喃、1,4-二噁烷、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙基醚、二乙二醇二丙醚、二乙二醇二丁醚、苯甲醚、苯乙醚及甲基苯甲醚等。Examples of ether solvents 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, and Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, Tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethyl Dibutyl glycol ether, anisole, phenethyl ether and methyl anisole, etc.
作為醚酯溶劑,可列舉:甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單乙醚乙酸酯及二乙二醇單丁醚乙酸酯等。Examples of ether ester solvents include: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-methoxypropionic acid Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, 2-methoxypropyl propionate, 2-ethoxy methyl propionate, 2-ethoxy ethyl propionate, 2-methoxy-2-methyl propionate, 2- Ethoxy-2-methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol mono Ethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether ethyl Acid esters and so on.
作為酮溶劑,可列舉:4-羥基-4-甲基-2-戊酮、丙酮、2-丁酮、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊酮、環戊酮、環己酮及異佛爾酮等。Examples of the ketone solvent include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2- Pentanone, cyclopentanone, cyclohexanone and isophorone, etc.
作為醇溶劑,可列舉:甲醇、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、丙二醇及甘油等。Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
作為芳香族烴溶劑,可列舉:苯、甲苯、二甲苯及均三甲苯等。As an aromatic hydrocarbon solvent, benzene, toluene, xylene, mesitylene, etc. are mentioned.
作為醯胺溶劑,可列舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺及N-甲基吡咯啶酮等。Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.
所述溶劑中,就塗佈性、乾燥性的方面而言,較佳為1 atm下的沸點為120℃以上且180℃以下的有機溶劑。作為溶劑,較佳為丙二醇單甲醚乙酸酯、乳酸乙酯、丙二醇單甲醚、3-乙氧基丙酸乙酯、乙二醇單甲醚、二乙二醇單甲醚、二乙二醇單乙醚、4-羥基-4-甲基-2-戊酮及N,N-二甲基甲醯胺,更佳為丙二醇單甲醚乙酸酯、丙二醇單甲醚、4-羥基-4-甲基-2-戊酮、乳酸乙酯及3-乙氧基丙酸乙酯。Among the solvents, in terms of coatability and drying properties, an organic solvent having a boiling point of 120°C or more and 180°C or less at 1 atm is preferred. The solvent is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy ethyl propionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethyl Glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy- 4-methyl-2-pentanone, ethyl lactate and ethyl 3-ethoxypropionate.
相對於本發明的著色硬化性樹脂組成物的總量,溶劑(E)的含有率較佳為70質量%~95質量%,更佳為75質量%~92質量%。換言之,著色硬化性樹脂組成物的固體成分的總含有率較佳為5質量%~30質量%,更佳為8質量%~25質量%。若溶劑(E)的含有率處於所述範圍內,則有如下傾向:塗佈時的平坦性變良好,另外於形成彩色濾光片時色濃度不會不足,因而顯示特性變良好。The content of the solvent (E) is preferably 70% by mass to 95% by mass, and more preferably 75% by mass to 92% by mass, relative to the total amount of the colored curable resin composition of the present invention. In other words, the total solid content of the colored curable resin composition is preferably 5% by mass to 30% by mass, more preferably 8% by mass to 25% by mass. If the content of the solvent (E) is within the above-mentioned range, there is a tendency that flatness during coating becomes better, and the color density is not insufficient when forming a color filter, and thus display characteristics become better.
<調平劑(F)> 作為調平劑(F),可列舉:矽酮系界面活性劑、氟系界面活性劑及具有氟原子的矽酮系界面活性劑等。該些亦可於側鏈具有聚合性基。 作為矽酮系界面活性劑,可列舉分子內具有矽氧烷鍵的界面活性劑等。具體而言,可列舉:東麗矽酮(Toray Silicone)DC3PA、東麗矽酮(Toray Silicone)SH7PA、東麗矽酮(Toray Silicone)DC11PA、東麗矽酮(Toray Silicone)SH21PA、東麗矽酮(Toray Silicone)SH28PA、東麗矽酮(Toray Silicone)SH29PA、東麗矽酮(Toray Silicone)SH30PA、東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(股)製造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452及TSF4460(日本邁圖高新材料(Momentive Performance Materials Japan)有限責任公司製造)等。<Leveling agent (F)> As the leveling agent (F), silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having fluorine atoms, and the like can be cited. These may have a polymerizable group in the side chain. Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule, and the like. Specifically, they include: Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone Ketone (Toray Silicone) SH28PA, Toray Silicone (Toray Silicone) SH29PA, Toray Silicone (Toray Silicone) SH30PA, Toray Silicone (Toray Silicone) SH8400 (manufactured by Toray Dow Corning (stock)) , 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) Co., Ltd.), etc.
作為所述氟系界面活性劑,可列舉分子內具有氟碳鏈的界面活性劑等。具體而言,可列舉:弗拉德(Fluorad)(註冊商標)FC430、弗拉德(Fluorad)FC431(住友3M(股)製造)、美佳法(Megafac)(註冊商標)F142D、美佳法(Megafac)F171、美佳法(Megafac)F172、美佳法(Megafac)F173、美佳法(Megafac)F177、美佳法(Megafac)F183、美佳法(Megafac)F554、美佳法(Megafac)R30、美佳法(Megafac)RS-718-K(迪愛生(DIC)(股)製造)、艾福拓(Eftop)(註冊商標)EF301、艾福拓(Eftop)EF303、艾福拓(Eftop)EF351、艾福拓(Eftop)EF352(三菱材料電子化成(股)製造)、沙福隆(Surflon)(註冊商標)S381、沙福隆(Surflon)S382、沙福隆(Surflon)SC101、沙福隆(Surflon)SC105(旭硝子(股)製造)及E5844(大金精細化學品研究所(股)製造)等。Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule, and the like. Specifically, it can include: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M (stock)), Megafac (registered trademark) F142D, Megafac ) F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC (shares)), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop ) EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (Asahi Glass (Stock) Manufacturing) and E5844 (Daikin Fine Chemicals Research Institute (Stock) Manufacturing), etc.
作為所述具有氟原子的矽酮系界面活性劑,可列舉分子內具有矽氧烷鍵及氟碳鏈的界面活性劑等。具體而言,可列舉:美佳法(Megafac)(註冊商標)R08、美佳法(Megafac)BL20、美佳法(Megafac)F475、美佳法(Megafac)F477及美佳法(Megafac)F443(迪愛生(DIC)(股)製造)等。Examples of the silicone-based surfactant having a fluorine atom include surfactants having a silicone bond and a fluorocarbon chain in the molecule. Specifically, it can include: Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (DIC ) (Stock) Manufacturing) and so on.
相對於著色硬化性樹脂組成物的總量,調平劑(F)的含有率較佳為0.001質量%以上且0.2質量%以下,更佳為0.002質量%以上且0.2質量%以下,進而佳為0.005質量%以上且0.2質量%以下。再者,該含有率中並不包含所述分散劑的含有率。若調平劑(F)的含有率處於所述範圍內,則可使彩色濾光片的平坦性變良好。Relative to the total amount of the colored curable resin composition, the content of the leveling agent (F) is preferably 0.001 mass% or more and 0.2 mass% or less, more preferably 0.002 mass% or more and 0.2 mass% or less, and still more preferably 0.005 mass% or more and 0.2 mass% or less. In addition, this content rate does not include the content rate of the said dispersing agent. If the content rate of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
<其他成分> 本發明的著色硬化性樹脂組成物視需要亦可包含聚合起始助劑、填充劑、其他高分子化合物、密接促進劑、光穩定劑、鏈轉移劑等該技術領域中公知的添加劑。 作為密接促進劑,可列舉:乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、3-縮水甘油基氧基丙基三甲氧基矽烷、3-縮水甘油基氧基丙基甲基二甲氧基矽烷、3-縮水甘油基氧基丙基甲基二乙氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯基氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷、3-異氰酸基丙基三乙氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二乙氧基矽烷、N-2-(胺基乙基)-3-胺基丙基三甲氧基矽烷、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、N-苯基-3-胺基丙基三甲氧基矽烷及N-苯基-3-胺基丙基三乙氧基矽烷等。<Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as polymerization initiation aids, fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, and the like as necessary. Examples of adhesion promoters include vinyl trimethoxysilane, vinyl triethoxy silane, vinyl tris(2-methoxyethoxy) silane, and 3-glycidyloxypropyl trimethoxy. Silane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl Trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethyl Oxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl) Ethyl)-3-aminopropylmethyl diethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane , 3-Aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.
<著色硬化性樹脂組成物的製造方法> 本發明的著色硬化性樹脂組成物例如可藉由將著色劑(A)、樹脂(B)、聚合性化合物(C)、及聚合起始劑(D)以及視需要使用的溶劑(E)、調平劑(F)及其他成分混合而製備。<Method for manufacturing colored curable resin composition> The colored curable resin composition of the present invention can be obtained by, for example, combining the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and optionally the solvent (E), The leveling agent (F) and other ingredients are mixed and prepared.
<彩色濾光片的製造方法> 作為由本發明的著色硬化性樹脂組成物製造著色圖案的方法,可列舉:光微影法、噴墨法、印刷法等。其中,較佳為光微影法。光微影法是將所述著色硬化性樹脂組成物塗佈於基板上,使其乾燥而形成著色組成物層,並介隔光罩對該著色組成物層進行曝光、顯影的方法。於光微影法中,藉由在曝光時不使用光罩、及/或不進行顯影,可形成作為所述著色組成物層的硬化物的著色塗膜。如此形成的著色圖案或著色塗膜為本發明的彩色濾光片。 所製作的彩色濾光片的膜厚並無特別限定,可根據目的或用途等而適當調整,例如為0.1 μm~30 μm、較佳為0.1 μm~20 μm、進而佳為0.5 μm~6 μm。<Method of manufacturing color filter> As a method of manufacturing a colored pattern from the colored curable resin composition of the present invention, a photolithography method, an inkjet method, a printing method, etc. can be cited. Among them, the photolithography method is preferred. The photolithography method is a method of coating the colored curable resin composition on a substrate, drying it to form a colored composition layer, and exposing and developing the colored composition layer through a photomask. In the photolithography method, by not using a photomask during exposure and/or not performing development, a colored coating film can be formed as a cured product of the colored composition layer. The colored pattern or colored coating film thus formed is the color filter of the present invention. The thickness of the color filter produced is not particularly limited, and can be appropriately adjusted according to the purpose or application. For example, it is 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and more preferably 0.5 μm to 6 μm. .
作為基板,可使用石英玻璃、硼矽酸玻璃、氧化鋁矽酸鹽玻璃、對表面進行了二氧化矽塗佈的鈉鈣玻璃等玻璃板;或聚碳酸酯、聚甲基丙烯酸甲酯、聚對苯二甲酸乙二酯等樹脂板;矽;於所述基板上形成有鋁、銀、銀/銅/鈀合金薄膜等者。亦可於該些基板上形成有其他的彩色濾光片層、樹脂層、電晶體、電路等。As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass coated with silica; or polycarbonate, polymethylmethacrylate, polycarbonate, etc. can be used. Resin plates such as ethylene terephthalate; silicon; aluminum, silver, silver/copper/palladium alloy thin films, etc. formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may also be formed on these substrates.
基於光微影法的各色畫素的形成可藉由公知或慣用的裝置或條件而進行。例如,可如下述般製作。 首先,將著色硬化性樹脂組成物塗佈於基板上,進行加熱乾燥(預烘烤)及/或減壓乾燥,藉此將溶劑等揮發成分去除而使其乾燥,從而獲得平滑的著色組成物層。 作為塗佈方法,可列舉:旋塗法、狹縫塗佈法、狹縫及旋塗法等。 進行加熱乾燥時的溫度較佳為30℃~120℃,更佳為50℃~110℃。另外,作為加熱時間,較佳為10秒~60分鐘,更佳為30秒~30分鐘。 於進行減壓乾燥的情況下,較佳為於50 Pa~150 Pa的壓力下,於20℃~25℃的溫度範圍內進行。 著色組成物層的膜厚並無特別限定,只要根據目標彩色濾光片的膜厚適當選擇即可。The formation of pixels of each color based on the photolithography method can be performed by known or customary devices or conditions. For example, it can be produced as follows. First, the colored curable resin composition is coated on the substrate, and then heated and dried (pre-baking) and/or reduced pressure drying to remove volatile components such as the solvent and dry it to obtain a smooth colored composition Floor. Examples of the coating method include spin coating, slit coating, slit and spin coating, and the like. The temperature during heat drying is preferably 30°C to 120°C, more preferably 50°C to 110°C. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. In the case of drying under reduced pressure, it is preferably carried out under a pressure of 50 Pa to 150 Pa and in a temperature range of 20°C to 25°C. The film thickness of the colored composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.
繼而,著色組成物層是介隔用於形成目標著色圖案的光罩而經曝光。該光罩上的圖案並無特別限定,可使用與目標用途相對應的圖案。 作為曝光中使用的光源,較佳為產生250 nm~450 nm的波長的光的光源。例如,亦可對於未滿350 nm的光,使用截止該波長範圍的濾光片進行截止,或者對於436 nm附近、408 nm附近、365 nm附近的光,使用取出該些波長範圍的帶通濾波器(band pass filter)進行選擇性取出。具體而言,可列舉:水銀燈、發光二極體、金屬鹵化物燈、鹵素燈等。 為了可對曝光面整體均勻地照射平行光線、或者進行光罩與形成有著色組成物層的基板的準確的對位,較佳為使用遮罩對準器(mask aligner)及步進機(stepper)等曝光裝置。Then, the colored composition layer is exposed through a photomask for forming a target colored pattern. The pattern on the mask is not particularly limited, and a pattern corresponding to the target application can be used. As the light source used for exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, for light less than 350 nm, use a filter that cuts off the wavelength range, or for light near 436 nm, 408 nm, and 365 nm, use bandpass filters that extract these wavelength ranges. (Band pass filter) for selective removal. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. can be mentioned. In order to uniformly irradiate the entire exposure surface with parallel light, or perform accurate alignment of the photomask and the substrate on which the colored composition layer is formed, it is preferable to use a mask aligner and a stepper. ) And other exposure devices.
藉由使曝光後的著色組成物層與顯影液接觸並進行顯影,從而於基板上形成著色圖案。藉由顯影,著色組成物層的未曝光部溶解於顯影液中而被去除。作為顯影液,例如較佳為氫氧化鉀、碳酸氫鈉、碳酸鈉、氫氧化四甲基銨等鹼性化合物的水溶液。該些鹼性化合物於水溶液中的濃度較佳為0.01質量%~10質量%,更佳為0.03質量%~5質量%。進而,顯影液亦可包含界面活性劑。 顯影方法可為覆液法、浸漬法及噴霧法等中的任一種。進而,亦可於顯影時將基板傾斜為任意角度。 顯影後,較佳為進行水洗。The coloring composition layer after exposure is brought into contact with a developing solution and developed to form a coloring pattern on the substrate. By developing, the unexposed part of the colored composition layer is dissolved in the developing solution and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide is preferred. The concentration of these basic compounds in the aqueous solution is preferably 0.01% by mass to 10% by mass, more preferably 0.03% by mass to 5% by mass. Furthermore, the developer may contain a surfactant. The development method may be any of a liquid coating method, a dipping method, and a spray method. Furthermore, the substrate may be inclined to an arbitrary angle during development. After development, it is preferable to wash with water.
進而,較佳為對所獲得的著色圖案進行後烘烤。後烘烤溫度較佳為150℃~250℃,更佳為160℃~235℃。後烘烤時間較佳為1分鐘~120分鐘,更佳為10分鐘~60分鐘。 [實施例]Furthermore, it is preferable to post-bak the obtained colored pattern. The post-baking temperature is preferably 150°C to 250°C, more preferably 160°C to 235°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes. [Example]
以下,藉由實施例來更詳細地說明本發明,但本發明並不受該些實施例的限定。例中,表示含量或使用量的%及份只要無特別說明則為質量基準。 於以下的合成例中,化合物是藉由核磁共振(Nuclear Magnetic Resonance,NMR)(JNM-EX-270;(日本電子(股)製造))而鑑定。Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited by these examples. In the examples,% and parts indicating content or usage amount are based on mass unless otherwise specified. In the following synthesis example, the compound was identified by Nuclear Magnetic Resonance (NMR) (JNM-EX-270; (manufactured by JEOL Ltd.)).
(著色劑合成例1) 將2,4-二甲基苯胺(東京化成工業(股)製造)10.0份、2-乙基溴化己烷(東京化成工業(股)製造)17.0份、以及溴化四丁基銨(和光化學工業(股)製造)44.0份混合。將所得到的混合物於90℃下攪拌8小時。反應結束後,加入50份的10%小蘇打水後,加入乙酸乙酯100份,將水層廢棄。重覆進行2次利用水、10%鹽酸洗滌的操作後,將溶劑蒸餾去除。將所得到的油於60℃下減壓乾燥24小時,得到下述式(a-1)所表示的化合物9.3份。(Colorant synthesis example 1) 10.0 parts of 2,4-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 17.0 parts of 2-ethylhexane bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and tetrabutylammonium bromide (Wako Chemical Industry (Stock) Manufacturing) 44.0 parts mixed. The resulting mixture was stirred at 90°C for 8 hours. After the reaction was completed, 50 parts of 10% baking soda water was added, and 100 parts of ethyl acetate was added, and the water layer was discarded. After repeated washing with water and 10% hydrochloric acid twice, the solvent was distilled off. The obtained oil was dried under reduced pressure at 60°C for 24 hours to obtain 9.3 parts of a compound represented by the following formula (a-1).
[化18] [化18]
式(a-1)所表示的化合物的1 H-NMR(270 MHz、δ值(ppm、四甲基矽烷(tetramethylsilane,TMS)基準)、二甲基亞碸(dimethylsulfoxide,DMSO)-d6 ) δ 0.85(m, 6H), 1.23-1.42(br, 8H), 1.59(br, 1H), 2.04(s, 3H), 2.12(s, 3H), 2.91(d, 2H), 4.37(br, 1H), 6.38(d, 1H), 6.75(s, 1H), 6.77(d, 1H) 1 H-NMR (270 MHz, δ value (ppm, tetramethylsilane (TMS) standard), dimethylsulfoxide (DMSO)-d 6 of the compound represented by formula (a-1) δ 0.85(m, 6H), 1.23-1.42(br, 8H), 1.59(br, 1H), 2.04(s, 3H), 2.12(s, 3H), 2.91(d, 2H), 4.37(br, 1H) ), 6.38(d, 1H), 6.75(s, 1H), 6.77(d, 1H)
將所述得到的式(a-1)所表示的化合物3.0份、3-溴苯酚(東京化成工業(股)製造)2.2份、乙酸鈀0.015份、第三丁氧基鈉(東京化成工業(股)製造)3.2份、三-第三丁基膦(東京化成工業(股)製造)0.055份、以及甲苯25.6份混合,並於100℃下攪拌15小時。向所得到的混合物中加入乙酸乙酯30份、水100份,將水層廢棄。重覆進行2次利用水洗滌的操作後,將溶劑蒸餾去除。利用矽膠層析法(silica gel chromatography)(氯仿/己烷=1/1)對殘渣進行精製,將所得到的油於60℃下減壓乾燥24小時,得到下述式(a-2)所表示的化合物1.9份。3.0 parts of the compound represented by the formula (a-1), 2.2 parts of 3-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.015 parts of palladium acetate, and sodium tertiary butoxide (Tokyo Chemical Industry Co., Ltd.) Co., Ltd.) 3.2 parts, 0.055 parts of tri-tert-butylphosphine (manufactured by Tokyo Chemical Industry Co., Ltd.), and 25.6 parts of toluene were mixed and stirred at 100°C for 15 hours. 30 parts of ethyl acetate and 100 parts of water were added to the obtained mixture, and the water layer was discarded. After the operation of washing with water was repeated twice, the solvent was distilled off. The residue was purified by silica gel chromatography (chloroform/hexane=1/1), and the resulting oil was dried under reduced pressure at 60°C for 24 hours to obtain the following formula (a-2) 1.9 parts of the indicated compound.
[化19] [化19]
式(a-2)所表示的化合物的1 H-NMR(270 MHz、δ值(ppm、TMS基準)、DMSO-d6 ) δ 0.85(m, 6H), 1.23-1.42(br, 8H), 1.55(br, 1H), 1.94(s, 3H), 2.27(s, 3H), 2.90(d, 2H), 6.37(d, 1H), 6.75(s, 1H), 6.76(d, 1H), 6.92-7.14(m, 4H), 8.93(s, 1H) 1 H-NMR (270 MHz, δ value (ppm, TMS standard), DMSO-d 6 ) of the compound represented by formula (a-2) δ 0.85(m, 6H), 1.23-1.42(br, 8H), 1.55(br, 1H), 1.94(s, 3H), 2.27(s, 3H), 2.90(d, 2H), 6.37(d, 1H), 6.75(s, 1H), 6.76(d, 1H), 6.92 -7.14(m, 4H), 8.93(s, 1H)
將所述得到的式(a-2)所表示的化合物4.4份、3,4-二羥基-3-環丁烯-1,2-二酮(東京化成工業(股)製造)0.8份、1-丁醇90.0份、以及甲苯60.0份混合。一面使用迪恩-斯達克(Dean-Stark)管將所生成的水去除,一面於125℃下將所得到的混合物攪拌3小時。反應結束後,將溶劑蒸餾去除,加入15份乙酸後,滴加至18%食鹽水100份中,濾取所析出的固體。利用己烷對所濾取的固體進行清洗。將所得到的固體於60℃下減壓乾燥24小時,得到式(AII-10)所表示的化合物4.9份。4.4 parts of the compound represented by the formula (a-2) obtained above, 0.8 part of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.), 1 -90.0 parts of butanol and 60.0 parts of toluene are mixed. While using a Dean-Stark tube to remove the generated water, the resulting mixture was stirred at 125°C for 3 hours. After the reaction, the solvent was distilled off, 15 parts of acetic acid were added, and then added dropwise to 100 parts of 18% brine, and the precipitated solid was filtered. The filtered solid was washed with hexane. The obtained solid was dried under reduced pressure at 60° C. for 24 hours to obtain 4.9 parts of a compound represented by formula (AII-10).
[化20] [化20]
式(AII-10)所表示的化合物的1 H-NMR(270 MHz、δ值(ppm、TMS基準)、DMSO-d6 ) δ 0.87(m, 12H), 1.21-1.57(m, 16H), 1.72(br, 2H), 2.05(s, 6H), 2.36(s, 6H), 3.37(br, 2H), 3.78(br, 2H), 6.00(br, 4H), 6.97-7.12(m, 6H), 7.77-7.95(m, 2H), 11.35(s, 1H), 12.06(s, 1H) 1 H-NMR (270 MHz, δ value (ppm, TMS standard), DMSO-d 6 ) of the compound represented by formula (AII-10) δ 0.87(m, 12H), 1.21-1.57(m, 16H), 1.72(br, 2H), 2.05(s, 6H), 2.36(s, 6H), 3.37(br, 2H), 3.78(br, 2H), 6.00(br, 4H), 6.97-7.12(m, 6H) , 7.77-7.95(m, 2H), 11.35(s, 1H), 12.06(s, 1H)
以下,化合物的結構是藉由質量分析(液相層析(liquid chromatography,LC);安捷倫(Agilent)製造的1200型、MASS;安捷倫(Agilent)製造的LC/MSD型)進行確認。Hereinafter, the structure of the compound is confirmed by mass analysis (liquid chromatography (LC); 1200 type and MASS manufactured by Agilent; LC/MSD type manufactured by Agilent).
(著色劑合成例2) 將間溴苯酚(東京化成工業(股)製造)50份及咪唑(東京化成工業(股)製造)30份溶解於二氯甲烷(關東化學(股)製造)500份中並冷卻為0℃後,滴加第三丁基二甲基氯矽烷(東京化成工業(股)製造)48份。滴加結束後,升溫至23℃並攪拌16小時。反應結束後,加入水並萃取有機層,對溶劑進行濃縮後,利用矽膠管柱層析法進行分離精製,得到74份式(a-3)所表示的化合物。(Colorant synthesis example 2) 50 parts of m-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 30 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) are dissolved in 500 parts of methylene chloride (manufactured by Kanto Chemical Co., Ltd.) and cooled to 0°C , Add 48 parts of tertiary butyl dimethyl chlorosilane (manufactured by Tokyo Chemical Industry Co., Ltd.). After the dropwise addition, the temperature was raised to 23°C and stirred for 16 hours. After the reaction, water was added to extract the organic layer, and the solvent was concentrated, and then separated and purified by silica gel column chromatography to obtain 74 parts of the compound represented by formula (a-3).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 287.0 精確質量(Exact Mass):+286.0Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 287.0 Exact Mass: +286.0
[化21] [化21]
將2,4-二甲基苯胺(東京化成工業(股)製造)15份、式(a-3)所表示的化合物35份、氫氧化鉀(和光純藥工業(股)製造)14份、溴化四丁基銨(東京化成工業(股)製造)2份以及雙(三-第三丁基膦)鈀(0)(奧德里奇(Aldrich)(股)製造)0.6份溶解於甲苯(關東化學(股)製造)250份及水15份中,加熱為90℃並攪拌30分鐘。反應結束後,萃取有機層並濃縮,利用矽膠管柱層析法進行分離精製,得到14份式(a-4)所表示的化合物。15 parts of 2,4-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 35 parts of compound represented by formula (a-3), 14 parts of potassium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.), 2 parts of tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 0.6 part of bis(tri-tertiarybutylphosphine) palladium (0) (manufactured by Aldrich (stock)) dissolved in toluene ( In 250 parts of Kanto Chemical Co., Ltd. and 15 parts of water, heat to 90°C and stir for 30 minutes. After the reaction, the organic layer was extracted and concentrated, and then separated and purified by silica gel column chromatography to obtain 14 parts of the compound represented by formula (a-4).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 328.3 精確質量(Exact Mass):+327.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 328.3 Exact Mass: +327.2
[化22] [化22]
將式(a-4)所表示的化合物14份及4-氯-4-氧代丁酸甲酯(東京化成工業(股)製造)10份溶解於甲苯(關東化學(股)製造)255份中,升溫至90℃並攪拌1小時。反應結束後,加入水並萃取有機層,對溶劑進行濃縮後,利用矽膠層析法對溶劑進行分離精製,得到15份式(a-5)所表示的化合物。14 parts of the compound represented by the formula (a-4) and 10 parts of methyl 4-chloro-4-oxobutanoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 255 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) In the middle, the temperature was raised to 90°C and stirred for 1 hour. After the reaction, water was added to extract the organic layer, and the solvent was concentrated, and then the solvent was separated and purified by silica gel chromatography to obtain 15 parts of the compound represented by formula (a-5).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 442.3 精確質量(Exact Mass):+441.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 442.3 Exact Mass: +441.2
[化23] [化23]
將式(a-5)所表示的化合物15份溶解於四氫呋喃(關東化學(股)製造)150份中,冷卻為0℃後,滴加氟化四-正丁基銨1M四氫呋喃溶液(東京化成工業(股)製造)15份。滴加結束後,升溫至23℃並攪拌2小時。反應結束後,對溶劑進行濃縮,並利用矽膠管柱層析法進行分離精製,得到12份式(a-6)所表示的化合物。15 parts of the compound represented by formula (a-5) was dissolved in 150 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.), and after cooling to 0°C, a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (Tokyo Kasei Industrial (Stock) Manufacturing) 15 copies. After the dropwise addition, the temperature was raised to 23°C and stirred for 2 hours. After the reaction, the solvent was concentrated, and the silica gel column chromatography was used for separation and purification to obtain 12 parts of the compound represented by the formula (a-6).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 328.2 精確質量(Exact Mass):+327.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 328.2 Exact Mass: +327.2
[化24] [化24]
將式(a-6)所表示的化合物12份溶解於四氫呋喃(關東化學(股)製造)240份中並冷卻為0℃後,滴加硼烷-1M四氫呋喃溶液(關東化學(股)製造)180份。滴加結束後攪拌30分鐘,加入水之後,對四氫呋喃進行濃縮,利用乙酸乙酯來萃取有機層。對溶劑進行濃縮後,利用矽膠管柱層析法進行分離精製,得到6份式(a-7)所表示的化合物。After dissolving 12 parts of the compound represented by formula (a-6) in 240 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.) and cooling to 0°C, borane-1M tetrahydrofuran solution (manufactured by Kanto Chemical Co., Ltd.) was added dropwise. 180 copies. After the dropwise addition, the mixture was stirred for 30 minutes, and after adding water, the tetrahydrofuran was concentrated, and the organic layer was extracted with ethyl acetate. After concentrating the solvent, it was separated and purified by silica gel column chromatography to obtain 6 parts of the compound represented by formula (a-7).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 314.2 精確質量(Exact Mass):+313.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 314.2 Exact Mass: +313.2
[化25] [化25]
將式(a-7)所表示的化合物6份及氫氧化鋰一水合物(和光純藥工業(股))0.2份溶解於甲醇(關東化學(股)製造)20份、四氫呋喃(關東化學(股)製造)20份、水10份中,於23℃下攪拌1小時。反應結束後,對有機溶劑進行濃縮,利用乙酸乙酯來萃取有機層,並利用矽膠管柱層析法進行分離精製,得到4份式(a-8)所表示的化合物。6 parts of the compound represented by formula (a-7) and 0.2 part of lithium hydroxide monohydrate (Wako Pure Chemical Industries, Ltd.) were dissolved in 20 parts of methanol (manufactured by Kanto Chemical Co., Ltd.), and tetrahydrofuran (Kanto Chemical Co., Ltd.) (Stock) Manufacturing) 20 parts and 10 parts of water are stirred at 23°C for 1 hour. After the reaction, the organic solvent was concentrated, the organic layer was extracted with ethyl acetate, and the silica gel column chromatography was used for separation and purification to obtain 4 parts of the compound represented by formula (a-8).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 300.2 精確質量(Exact Mass):+299.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 300.2 Exact Mass: +299.2
[化26] [化26]
將式(a-8)所表示的化合物4份及3,4-二羥基-3-環丁烯-1,2-二酮(和光純藥工業(股)製造)0.8份溶解於甲苯(關東化學(股)製造)40份、正丁醇(關東化學(股)製造)10份中,升溫至140℃並攪拌2小時。對溶劑進行濃縮後,利用矽膠管柱層析法進行分離精製,得到1.6份式(AII-17)所表示的化合物。4 parts of the compound represented by formula (a-8) and 0.8 part of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in toluene (Kanto) In 40 parts of Chemical Co., Ltd. and 10 parts of n-butanol (manufactured by Kanto Chemical Co., Ltd.), the temperature was raised to 140°C and stirred for 2 hours. After concentrating the solvent, it was separated and purified by silica gel column chromatography to obtain 1.6 parts of the compound represented by formula (AII-17).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 677.3 精確質量(Exact Mass):+676.3Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 677.3 Exact Mass: +676.3
[化27] [化27]
(著色劑合成例3) 將3-溴苯甲醚(東京化成工業(股)製造)50份溶解於2,4,6-三甲基苯胺(東京化成工業(股)製造)36.1份與甲苯(關東化學(股)製造)434份中,並於該溶液中混合氫氧化鉀(關東化學(股)製造)30份、水25份、溴化四丁基銨(東京化成工業(股)製造)2份、雙(三-第三丁基膦)鈀(0)(東京化成工業(股)製造)1.4份。升溫至90℃並攪拌5小時後,藉由萃取而獲得有機層,將溶劑蒸餾去除而得到52.1份粗產物。利用管柱層析法對所得到的粗產物進行分離精製,得到50.2份式(a-9)所表示的化合物。(Colorant synthesis example 3) 50 parts of 3-bromoanisole (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 36.1 parts of 2,4,6-trimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and toluene (manufactured by Kanto Chemical Co., Ltd.) ) 434 parts, and mix 30 parts of potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.), 25 parts of water, 2 parts of tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and double (three -Tertiary butyl phosphine) palladium (0) (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.4 parts. After heating up to 90°C and stirring for 5 hours, an organic layer was obtained by extraction, and the solvent was distilled off to obtain 52.1 parts of a crude product. The obtained crude product was separated and purified by column chromatography to obtain 50.2 parts of the compound represented by formula (a-9).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 242.3 精確質量(Exact Mass):+241.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 242.3 Exact Mass: +241.2
[化28] [化28]
將式(a-9)所表示的化合物33份、4-氯-4-氧代丁酸甲酯(東京化成工業(股)製造)26.8份及甲苯(關東化學(股)製造)286份混合,一面於100℃下攪拌16小時一面加熱。反應結束後將溶劑蒸餾去除,利用管柱層析法對所得到的粗產物進行分離精製,得到30.7份式(a-10)所表示的化合物。33 parts of the compound represented by the formula (a-9), 26.8 parts of methyl 4-chloro-4-oxobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 286 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) , While stirring at 100°C for 16 hours while heating. After the completion of the reaction, the solvent was distilled off, and the obtained crude product was separated and purified by column chromatography to obtain 30.7 parts of the compound represented by the formula (a-10).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 356.2 精確質量(Exact Mass):+355.2 [化29] Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 356.2 Exact Mass: +355.2 [化29]
將式(a-10)所表示的化合物10份溶解於二氯甲烷(methylene chloride)(關東化學(股)製造)95份中,一面攪拌一面冷卻至0℃。一面攪拌一面滴加投入三溴化硼(富士膠片和光純藥(股)製造)28.2份。滴加結束後,緩緩升溫,於10℃下攪拌4小時。反應結束後將溶劑減壓蒸餾去除,實施水-有機溶劑萃取操作,將溶劑蒸餾去除,得到9.1份的粗產物。於其中含有48%的式(a-11)所表示的化合物、36%的式(a-12)所表示的化合物。10 parts of the compound represented by formula (a-10) was dissolved in 95 parts of methylene chloride (manufactured by Kanto Chemical Co., Ltd.) and cooled to 0°C while stirring. While stirring, 28.2 parts of boron tribromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added dropwise. After the dropwise addition, the temperature was gradually increased and stirred at 10°C for 4 hours. After the reaction, the solvent was distilled off under reduced pressure, water-organic solvent extraction was performed, and the solvent was distilled off to obtain 9.1 parts of a crude product. It contains 48% of the compound represented by formula (a-11) and 36% of the compound represented by formula (a-12).
[化30] 鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 342.2 精確質量(Exact Mass):+341.2 [化31] 鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 328.1 精確質量(Exact Mass):+327.2[化30] Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 342.2 Exact Mass: +341.2 [化31] Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 328.1 Exact Mass: +327.2
一面將使亞硫醯氯(東京化成工業(股)製造)13.2份溶解於72份的甲醇(關東化學(股)製造)中而成的溶液冷卻至0℃並攪拌,一面投入所述得到的含有式(a-11)所表示的化合物與式(a-12)所表示的化合物的粗產物9.1份。升溫至室溫並使其反應16小時。將溶劑減壓蒸餾去除,得到含有式(a-11)所表示的化合物的8.3份粗產物。利用矽膠管柱層析法對所得到的粗產物進行精製,得到7.4份式(a-11)所表示的化合物。While a solution of 13.2 parts of sulfite chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) dissolved in 72 parts of methanol (manufactured by Kanto Chemical Co., Ltd.) was cooled to 0°C and stirred, the obtained 9.1 parts of crude products containing the compound represented by formula (a-11) and the compound represented by formula (a-12). The temperature was raised to room temperature and allowed to react for 16 hours. The solvent was distilled off under reduced pressure to obtain 8.3 parts of crude products containing the compound represented by formula (a-11). The obtained crude product was purified by silica gel column chromatography to obtain 7.4 parts of the compound represented by formula (a-11).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 342.2 精確質量(Exact Mass):+341.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 342.2 Exact Mass: +341.2
將式(a-11)所表示的化合物2份、硼烷1M四氫呋喃溶液(關東化學(股)製造)26.3份、四氫呋喃(關東化學(股)製造)18份於0℃下混合,升溫至10℃並攪拌5小時。反應結束後,加入水並淬滅(quench),利用有機溶劑進行萃取。利用矽膠管柱層析法對將溶劑蒸餾去除而得到的粗產物進行精製,得到1.64份式(a-13)所表示的化合物。2 parts of the compound represented by formula (a-11), 26.3 parts of borane 1M tetrahydrofuran solution (manufactured by Kanto Chemical Co., Ltd.), and 18 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.) were mixed at 0°C and heated to 10 ℃ and stir for 5 hours. After the reaction is over, water is added and quenched, and extraction is performed with an organic solvent. The crude product obtained by distilling off the solvent was purified by silica gel column chromatography to obtain 1.64 parts of the compound represented by the formula (a-13).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 300.2 精確質量(Exact Mass):+299.2Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 300.2 Exact Mass: +299.2
[化32] [化32]
使式(a-13)所表示的化合物2.5份及3,4-二羥基-3-環丁烯-1,2-二酮(富士膠片和光純藥(股)製造)0.55份溶解於甲苯(關東化學(股)製造)50份、正丁醇(關東化學(股)製造)50份中,一面於110℃下攪拌6小時一面加熱。反應結束後,利用矽膠管柱層析法對將溶劑蒸餾去除而得到的粗產物進行分離精製,得到2.7份式(AII-18)所表示的化合物。2.5 parts of the compound represented by formula (a-13) and 0.55 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were dissolved in toluene ( 50 parts of Kanto Chemical (manufactured by Kanto Chemical Co., Ltd.) and 50 parts of n-butanol (manufactured by Kanto Chemical Co., Ltd.) were heated while stirring at 110°C for 6 hours. After the reaction, the crude product obtained by distilling off the solvent was separated and purified by silica gel column chromatography to obtain 2.7 parts of the compound represented by the formula (AII-18).
鑑定:(質量分析)離子化模式=ESI+:m/z=[M+H]+ 677.4 精確質量(Exact Mass):+676.4Identification: (mass analysis) ionization mode=ESI+: m/z=[M+H] + 677.4 Exact Mass: +676.4
[化33] [化33]
(樹脂合成例1) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入3-甲氧基丁醇223份、及3-甲氧基丁基乙酸酯110份,一面攪拌一面加熱至70℃。繼而,使用滴加泵花5小時向該燒瓶內滴加丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)180份、丙烯酸54份、N-環己基馬來醯亞胺67份、以及3-甲氧基丁醇180份的混合溶液。 另一方面,使用另一個滴加泵花5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)6份溶解於3-甲氧基丁基乙酸酯150份中而成的混合溶液。於聚合起始劑的滴加結束後,以該溫度保持3小時後,冷卻至室溫,得到B型黏度(23℃)為130 mPa·s、固體成分為30.9%的共聚物(樹脂(B-1))的溶液。所生成的共聚物的重量平均分子量(Mw)為8800,固體成分換算的酸價為137 mg-KOH/g,分散度為1.76。樹脂(B-1)具有下述結構單元。(Resin Synthesis Example 1) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer. The atmosphere was replaced with a nitrogen atmosphere, and 223 parts of 3-methoxybutanol and 3-methoxybutyl ethyl were put in 110 parts of acid ester, heating to 70°C while stirring. Then, 3,4-epoxytricyclic acrylic acid [5.2.1.0 2,6 ]decane-8-yl ester and 3,4-epoxytricyclic acrylic acid [ 5.2.1.0 2,6 ]decane-9-yl ester mixture (mixing ratio is 1:1) 180 parts, 54 parts of acrylic acid, 67 parts of N-cyclohexylmaleimide, and 3-methoxybutane A mixed solution of 180 parts of alcohol. On the other hand, 6 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in 3-methoxy by using another dripping pump for 5 hours. A mixed solution of 150 parts of butyl acetate. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained for 3 hours, and then cooled to room temperature to obtain a copolymer (resin (B) with a viscosity (23°C) of 130 mPa·s and a solid content of 30.9% -1)) solution. The weight average molecular weight (Mw) of the resulting copolymer was 8,800, the acid value in terms of solid content was 137 mg-KOH/g, and the degree of dispersion was 1.76. The resin (B-1) has the following structural unit.
[化34] [化34]
樹脂的聚苯乙烯換算的重量平均分子量(Mw)及數量平均分子量(Mn)的測定是藉由凝膠滲透層析法(Gel Permeation Chromatography,GPC)並利用以下條件進行。 裝置:HLC-8120GPC(東曹(Tosoh)(股)製造) 管柱:TSK-GELG2000HXL 管柱溫度:40℃ 溶劑:四氫呋喃(tetrahydrofuran,THF) 流速:1.0 mL/min 被檢液固體成分濃度:0.001質量%~0.01質量% 注入量:50 μL 檢測器:折射率(refractive index,RI) 校正用標準物質:TSK標準聚苯乙烯 F-40、F-4、F-288、A-2500、A-500(東曹(Tosoh)(股)製造) 將所述獲得的聚苯乙烯換算的重量平均分子量及數量平均分子量的比(Mw/Mn)設為分散度。The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in terms of polystyrene of the resin was performed by Gel Permeation Chromatography (GPC) under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh (stock)) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran (tetrahydrofuran, THF) Flow rate: 1.0 mL/min Solid content concentration of the tested liquid: 0.001% by mass to 0.01% by mass Injection volume: 50 μL Detector: Refractive index (RI) Standard material for calibration: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh (stock)) The ratio (Mw/Mn) of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained as described above is defined as the degree of dispersion.
(樹脂合成例2) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入3-甲氧基丁醇185份、及丙二醇單甲醚乙酸酯216份,一面攪拌一面加熱至70℃。繼而,使用滴加泵花5小時向該燒瓶內滴加丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)149份、丙烯酸45份、N-環己基馬來醯亞胺56份、以及3-甲氧基丁醇158份的混合溶液。 另一方面,使用另一個滴加泵花5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)8份溶解於丙二醇單甲醚乙酸酯183份中而成的混合溶液。於聚合起始劑的滴加結束後,以該溫度保持4小時後,冷卻至室溫,得到B型黏度(23℃)為22 mPa·s、固體成分為26.1%的共聚物(樹脂(B-2))的溶液。所生成的共聚物的重量平均分子量(Mw)為8900,固體成分換算的酸價為143 mg-KOH/g,分散度為1.92。樹脂(B-2)具有與樹脂(B-1)相同的結構單元。(Resin Synthesis Example 2) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 185 parts of 3-methoxybutanol and 216 of propylene glycol monomethyl ether acetate were put in Serving, heat to 70°C while stirring. Then, 3,4-epoxytricyclo [5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo [ 5.2.1.0 2,6 ]decane-9-yl ester mixture (mixing ratio is 1:1) 149 parts, acrylic acid 45 parts, N-cyclohexyl maleimide 56 parts, and 3-methoxybutane A mixed solution of 158 parts of alcohol. On the other hand, 8 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethyl ether by using another dripping pump for 5 hours. A mixed solution of 183 parts of acetate. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained for 4 hours, and then cooled to room temperature. A type B viscosity (23°C) of 22 mPa·s and a solid content of 26.1% copolymer (resin (B -2)) solution. The weight average molecular weight (Mw) of the produced copolymer was 8900, the acid value in terms of solid content was 143 mg-KOH/g, and the degree of dispersion was 1.92. Resin (B-2) has the same structural unit as resin (B-1).
(樹脂合成例3) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入丙二醇單甲醚乙酸酯248份,一面攪拌一面加熱至80℃。繼而,使用滴加泵花5小時向該燒瓶內滴加丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)52份、丙烯酸42份、N-環己基馬來醯亞胺141份、以及丙二醇單甲醚乙酸酯352份的混合溶液。 另一方面,使用另一個滴加泵花5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)20份溶解於丙二醇單甲醚乙酸酯145份中而成的混合溶液。於聚合起始劑的滴加結束後,以該溫度保持3小時後,冷卻至室溫,得到B型黏度(23℃)為18 mPa·s、固體成分為25.7%的共聚物(樹脂(B-3))的溶液。所生成的共聚物的重量平均分子量(Mw)為8000,固體成分換算的酸價為119 mg-KOH/g,分散度為2.09。樹脂(B-3)具有與樹脂(B-1)相同的結構單元。(Resin Synthesis Example 3) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 248 parts of propylene glycol monomethyl ether acetate was put in and heated to 80°C while stirring. Then, 3,4-epoxytricyclo [5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo [ 5.2.1.0 The mixture of 2,6 ]decane-9-yl ester (mixing ratio is 1:1) 52 parts, 42 parts acrylic acid, 141 parts N-cyclohexyl maleimide, and propylene glycol monomethyl ether acetic acid A mixed solution of 352 parts of esters. On the other hand, 20 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethyl ether by using another dripping pump for 5 hours. A mixed solution of 145 parts of acetate. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained at this temperature for 3 hours, and then cooled to room temperature to obtain a copolymer (resin (B) with a B-type viscosity (23°C) of 18 mPa·s and a solid content of 25.7% -3)) solution. The weight average molecular weight (Mw) of the produced copolymer was 8000, the acid value in terms of solid content was 119 mg-KOH/g, and the dispersion degree was 2.09. Resin (B-3) has the same structural unit as resin (B-1).
(樹脂合成例4) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入丙二醇單甲醚乙酸酯191份、及丙二醇單甲醚79份,一面攪拌一面加熱至80℃。繼而,使用滴加泵花5小時向該燒瓶內滴加丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)112份、丙烯酸80份、N-環己基馬來醯亞胺128份、以及丙二醇單甲醚258份的混合溶液。 另一方面,使用另一個滴加泵花5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)7份溶解於丙二醇單甲醚乙酸酯145份中而成的混合溶液。於聚合起始劑的滴加結束後,以該溫度保持3小時後,冷卻至室溫,得到B型黏度(23℃)為75 mPa·s、固體成分為34.7%的共聚物(樹脂(B-4))的溶液。所生成的共聚物的重量平均分子量(Mw)為8800,固體成分換算的酸價為181 mg-KOH/g,分散度為2.20。樹脂(B-4)具有與樹脂(B-1)相同的結構單元。(Resin Synthesis Example 4) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 191 parts of propylene glycol monomethyl ether acetate and 79 parts of propylene glycol monomethyl ether were put in one side Heat to 80°C while stirring. Then, 3,4-epoxytricyclo [5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo [ 5.2.1.0 2,6 ]Decane-9-yl ester mixture (mixing ratio is 1:1) 112 parts, acrylic acid 80 parts, N-cyclohexyl maleimide 128 parts, and propylene glycol monomethyl ether 258 parts The mixed solution. On the other hand, another dripping pump was used to drop 7 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) into the flask for 5 hours to dissolve in propylene glycol monomethyl ether A mixed solution of 145 parts of acetate. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained for 3 hours and then cooled to room temperature to obtain a type B viscosity (23°C) of 75 mPa·s and a copolymer of 34.7% solid content (resin (B -4)) solution. The weight average molecular weight (Mw) of the resulting copolymer was 8,800, the acid value in terms of solid content was 181 mg-KOH/g, and the degree of dispersion was 2.20. Resin (B-4) has the same structural unit as resin (B-1).
(樹脂合成例5) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入二乙二醇甲基乙基醚149份、及丙二醇單甲醚110份,一面攪拌一面加熱至70℃。繼而,使用滴加泵花5小時向該燒瓶內滴加丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)45份、丙烯酸75份、N-環己基馬來醯亞胺180份、以及二乙二醇甲醚309份的混合溶液。 另一方面,使用另一個滴加泵花5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)5份溶解於丙二醇單甲醚127份中而成的混合溶液。於聚合起始劑的滴加結束後,以該溫度保持4小時後,冷卻至室溫,得到B型黏度(23℃)為66 mPa·s、固體成分為34.5%的共聚物(樹脂(B-5))的溶液。所生成的共聚物的重量平均分子量(Mw)為9000,固體成分換算的酸價為183 mg-KOH/g,分散度為2.06。樹脂(B-5)具有與樹脂(B-1)相同的結構單元。(Resin Synthesis Example 5) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 149 parts of diethylene glycol methyl ethyl ether and 110 parts of propylene glycol monomethyl ether were placed , While stirring, heat to 70°C. Then, 3,4-epoxytricyclo [5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo [ 5.2.1.0 2,6 ] Decane-9-yl ester mixture (mixing ratio is 1:1) 45 parts, acrylic acid 75 parts, N-cyclohexyl maleimide 180 parts, and diethylene glycol methyl ether 309 parts of mixed solution. On the other hand, 5 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethyl ether by using another dripping pump for 5 hours. A mixed solution in 127 parts. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained for 4 hours and then cooled to room temperature to obtain a type B viscosity (23°C) of 66 mPa·s and a copolymer of 34.5% solid content (resin (B -5)) solution. The weight average molecular weight (Mw) of the resulting copolymer was 9000, the acid value in terms of solid content was 183 mg-KOH/g, and the degree of dispersion was 2.06. Resin (B-5) has the same structural unit as resin (B-1).
(樹脂合成例6) 於具備回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入丙二醇單甲醚乙酸酯100份,一面攪拌一面加熱至85℃為止。繼而,使用滴加泵花約5小時向該燒瓶內滴加將甲基丙烯酸19份、丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6 ]癸烷-9-基酯的混合物(混合比例為1:1)171份溶解於丙二醇單甲醚乙酸酯40份中而成的溶液。 另一方面,使用另一個滴加泵花約5小時向燒瓶內滴加將聚合起始劑2,2'-偶氮雙(2,4-二甲基戊腈)26份溶解於丙二醇單甲醚乙酸酯120份中而成的溶液。於聚合起始劑的滴加結束後,以該溫度保持約3小時後,冷卻至室溫,得到固體成分為43.5%的共聚物(樹脂(B-6))的溶液。所得到的樹脂(B-2)的重量平均分子量為8000,分散度為1.98,固體成分換算的酸價為53 mg-KOH/g。樹脂(B-6)具有下述結構單元。(Resin Synthesis Example 6) A suitable amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 100 parts of propylene glycol monomethyl ether acetate were put in and heated to 85°C while stirring. Then, 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylic acid and 3 acrylic acid were dropped into the flask for about 5 hours using a dropping pump. A solution of 171 parts of a mixture of ,4-epoxytricyclo[5.2.1.0 2,6 ] decane-9-yl ester (mixing ratio is 1:1) dissolved in 40 parts of propylene glycol monomethyl ether acetate . On the other hand, 26 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethyl by using another dripping pump for about 5 hours. A solution of 120 parts of ether acetate. After the dropwise addition of the polymerization initiator was completed, the temperature was maintained for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer (resin (B-6)) having a solid content of 43.5%. The weight average molecular weight of the obtained resin (B-2) was 8000, the degree of dispersion was 1.98, and the acid value in terms of solid content was 53 mg-KOH/g. The resin (B-6) has the following structural unit.
[化35] [化35]
[實施例1~實施例9、比較例1] [著色硬化性樹脂組成物的製備] 以成為表2所示的組成的方式將各成分混合,獲得著色硬化性樹脂組成物。[Example 1 to Example 9, Comparative Example 1] [Preparation of colored curable resin composition] Each component was mixed so that it might become the composition shown in Table 2, and the colored curable resin composition was obtained.
[表2]
表2中,各成分表示以下的化合物。 著色劑(A-1):式(AII-10)所表示的化合物 著色劑(A-2):式(AII-17)所表示的化合物 著色劑(A-3):式(AII-18)所表示的化合物 樹脂(B-1):樹脂(B-1)(固體成分換算) 樹脂(B-2):樹脂(B-2)(固體成分換算) 樹脂(B-3):樹脂(B-3)(固體成分換算) 樹脂(B-4):樹脂(B-4)(固體成分換算) 樹脂(B-5):樹脂(B-5)(固體成分換算) 樹脂(B-6):樹脂(B-6)(固體成分換算) 聚合性化合物(C-1):二季戊四醇六丙烯酸酯(卡亞拉得(KAYARAD)(註冊商標)DPHA;日本化藥(股)製造) 聚合起始劑(D-1):N-1919(艾迪科(ADEKA)公司製造;O-醯基肟化合物) 聚合起始劑(D-2):DFI-091(大東化學(Daito Chemix)公司製造;O-醯基肟化合物) 聚合起始劑(D-3):N-苯甲醯基氧基-1-(4-苯基巰基苯基)辛烷-1-酮-2-亞胺(豔佳固(Irgacure)(註冊商標)OXE-01;巴斯夫(BASF)公司製造;O-醯基肟化合物) 溶劑(E-1):4-羥基-4-甲基-2-戊酮 溶劑(E-2):丙二醇單甲醚乙酸酯 溶劑(E-3):3-甲氧基丁基乙酸酯 溶劑(E-4):3-甲氧基-1-丁醇 溶劑(E-5):二乙二醇甲基乙基醚 溶劑(E-6):丙二醇單甲醚 調平劑(F-1):聚醚改質矽油(東麗道康寧(Toray Dow Corning)(股)製造的「東麗矽酮(Toray Silicone)SH8400」)In Table 2, each component represents the following compound. Coloring agent (A-1): compound represented by formula (AII-10) Coloring agent (A-2): compound represented by formula (AII-17) Coloring agent (A-3): compound represented by formula (AII-18) Resin (B-1): Resin (B-1) (in terms of solid content) Resin (B-2): Resin (B-2) (calculated in solid content) Resin (B-3): Resin (B-3) (calculated in solid content) Resin (B-4): Resin (B-4) (calculated as solid content) Resin (B-5): Resin (B-5) (calculated in solid content) Resin (B-6): Resin (B-6) (calculated in solid content) Polymerizable compound (C-1): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D-1): N-1919 (manufactured by ADEKA; O-acetoxime compound) Polymerization initiator (D-2): DFI-091 (manufactured by Daito Chemix; O-acetoxy oxime compound) Polymerization initiator (D-3): N-benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine (Irgacure) (registered Trademark) OXE-01; BASF (BASF) company manufacture; O-acetoxime compound) Solvent (E-1): 4-hydroxy-4-methyl-2-pentanone Solvent (E-2): propylene glycol monomethyl ether acetate Solvent (E-3): 3-methoxybutyl acetate Solvent (E-4): 3-methoxy-1-butanol Solvent (E-5): Diethylene glycol methyl ethyl ether Solvent (E-6): propylene glycol monomethyl ether Leveling agent (F-1): Polyether modified silicone oil ("Toray Silicone SH8400" manufactured by Toray Dow Corning (stock))
[著色塗膜的製作] 於5 cm見方的玻璃基板(益格(Eagle)2000;康寧(Corning)公司製造)上,以後烘烤後的膜厚成為2.0 μm的方式藉由旋塗法塗佈著色硬化性樹脂組成物,之後於100℃下預烘烤3分鐘,形成著色組成物層。放置冷卻後,使用曝光機(TME-150RSK;拓普康(Topcon)(股)製造)於大氣環境下以100 mJ/cm2 的曝光量(365 nm基準)對著色組成物層進行光照射。其後,於烘箱中以230℃進行30分鐘後烘烤,獲得著色塗膜。[Production of colored coating film] On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning), the film thickness after baking becomes 2.0 μm by spin coating The colored curable resin composition is then prebaked at 100°C for 3 minutes to form a colored composition layer. After being left to cool, an exposure machine (TME-150RSK; manufactured by Topcon (stock)) was used to irradiate the colored composition layer with light at an exposure amount of 100 mJ/cm 2 (365 nm standard) in an atmospheric environment. Thereafter, post-baking was performed in an oven at 230°C for 30 minutes to obtain a colored coating film.
[步驟性評價] 1. 吸光度保持率 根據於預烘烤後及後烘烤後所測定的分光而求出極大吸光度,按照下述式來計算極大吸光度的保持率。將結果示於表3中。 吸光度保持率(ΔAbs.Max)=後烘烤後的極大吸光度/預烘烤後的極大吸光度 吸光度保持率越高,意味著成膜步驟中的適應性越高。[Step Evaluation] 1. Absorbance retention rate The maximum absorbance was obtained from the spectra measured after the pre-baking and after the post-baking, and the retention of the maximum absorbance was calculated according to the following formula. The results are shown in Table 3. Absorbance retention rate (ΔAbs.Max) = maximum absorbance after post-baking/maximum absorbance after pre-baking The higher the absorbance retention rate, the higher the adaptability in the film forming step.
[表3]
2. 色度 關於由實施例1、實施例3、及比較例1的著色硬化性樹脂組成物所形成的著色塗膜的色度,根據使用測色機(OSP-SP-200;奧林巴斯(Olympus)(股)製造)所測定的分光、以及C光源的特性函數,作為國際照明學會(Commission Internationale de I'Eclairage,CIE)的XYZ表色系中的xy色度座標(x,y)與Y而求出,將結果示於表4中。Y的值越大,表示明度越高。2. Chroma Regarding the chromaticity of the colored coating film formed from the colored curable resin composition of Example 1, Example 3, and Comparative Example 1, according to the use of a color measuring machine (OSP-SP-200; Olympus (Olympus) (Stock) Manufacturing) The measured spectroscopy and the characteristic function of the C light source are used as the xy chromaticity coordinates (x, y) and Y in the XYZ color system of the Commission Internationale de I'Eclairage (CIE) It was calculated, and the results are shown in Table 4. The larger the value of Y, the higher the brightness.
[表4]
根據本發明的著色樹脂組成物,可形成吸光度保持率優異的彩色濾光片。According to the colored resin composition of the present invention, a color filter excellent in absorbance retention can be formed.
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JP2019021919A JP7203626B2 (en) | 2019-02-08 | 2019-02-08 | Colored curable resin composition |
JP2019-021919 | 2019-02-08 |
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JP (1) | JP7203626B2 (en) |
KR (1) | KR20210124315A (en) |
CN (1) | CN113286828B (en) |
TW (1) | TWI816003B (en) |
WO (1) | WO2020162009A1 (en) |
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JP6149353B2 (en) * | 2011-07-08 | 2017-06-21 | 住友化学株式会社 | Colored photosensitive resin composition |
US9350676B2 (en) | 2012-12-11 | 2016-05-24 | Qualcomm Incorporated | Method and apparatus for classifying flows for compression |
JP5869536B2 (en) | 2013-08-08 | 2016-02-24 | Kyb株式会社 | Manufacturing data management method for casting products |
CN104513510B (en) * | 2013-09-26 | 2018-07-06 | 东友精细化工有限公司 | Colored curable resin composition |
JP6662615B2 (en) * | 2014-11-25 | 2020-03-11 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound |
JP6625409B2 (en) * | 2014-11-25 | 2019-12-25 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Colored curable composition, coating film, color filter, and display device |
JP6498929B2 (en) * | 2014-12-22 | 2019-04-10 | 住友化学株式会社 | Colored curable resin composition |
JP6592257B2 (en) * | 2015-03-12 | 2019-10-16 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Colored curable resin composition |
JP6971021B2 (en) * | 2016-11-16 | 2021-11-24 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Color curable resin composition, color filter, and display device |
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- 2019-02-08 JP JP2019021919A patent/JP7203626B2/en active Active
- 2019-12-03 WO PCT/JP2019/047175 patent/WO2020162009A1/en active Application Filing
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TWI816003B (en) | 2023-09-21 |
JP2020128496A (en) | 2020-08-27 |
KR20210124315A (en) | 2021-10-14 |
JP7203626B2 (en) | 2023-01-13 |
CN113286828B (en) | 2023-04-28 |
CN113286828A (en) | 2021-08-20 |
WO2020162009A1 (en) | 2020-08-13 |
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