TWI813835B - Colored curable resin composition, color filter and display device - Google Patents
Colored curable resin composition, color filter and display device Download PDFInfo
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- TWI813835B TWI813835B TW108146737A TW108146737A TWI813835B TW I813835 B TWI813835 B TW I813835B TW 108146737 A TW108146737 A TW 108146737A TW 108146737 A TW108146737 A TW 108146737A TW I813835 B TWI813835 B TW I813835B
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- resin
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- carbon atoms
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- 239000011342 resin composition Substances 0.000 title claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 229920005989 resin Polymers 0.000 claims abstract description 114
- 239000011347 resin Substances 0.000 claims abstract description 114
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- 239000003086 colorant Substances 0.000 claims abstract description 26
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 229920001577 copolymer Polymers 0.000 claims description 36
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 150000004292 cyclic ethers Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- -1 dibutyl Chemical group 0.000 description 61
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 52
- 239000002904 solvent Substances 0.000 description 52
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 44
- 239000000049 pigment Substances 0.000 description 41
- 150000002430 hydrocarbons Chemical group 0.000 description 33
- 239000000975 dye Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002835 absorbance Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229920001296 polysiloxane Polymers 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- GHBQLFWTMLRYKN-UHFFFAOYSA-N 9-prop-2-enylcarbazole Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3C2=C1 GHBQLFWTMLRYKN-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000011161 development Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- 238000000206 photolithography Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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 3
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 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 2
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-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
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-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
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- XQEOHFQIDHWQFK-UHFFFAOYSA-N 2-phenylmethoxyimino-1-(4-phenylsulfanylphenyl)octan-1-one Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(CCCCCC)=NOCC1=CC=CC=C1 XQEOHFQIDHWQFK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DOWVFPAIJRADGF-UHFFFAOYSA-N 4-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=CC2=C1C(=O)OC2=O DOWVFPAIJRADGF-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 2
- OHMDZMAJDUVGHO-UHFFFAOYSA-N 5-ethenyl-2-benzofuran-1,3-dione Chemical compound C=CC1=CC=C2C(=O)OC(=O)C2=C1 OHMDZMAJDUVGHO-UHFFFAOYSA-N 0.000 description 2
- INOIOAWTVPHTCJ-UHFFFAOYSA-N 6-acetamido-4-hydroxy-3-[[4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2-sulfonic acid Chemical compound CC(=O)NC1=CC=C2C=C(C(N=NC3=CC=C(C=C3)S(=O)(=O)CCOS(O)(=O)=O)=C(O)C2=C1)S(O)(=O)=O INOIOAWTVPHTCJ-UHFFFAOYSA-N 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
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- 230000003595 spectral effect Effects 0.000 description 1
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- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 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
- 239000010409 thin film Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-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
- 239000000984 vat dye Substances 0.000 description 1
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- 239000001018 xanthene dye Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
- C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F26/12—N-Vinyl-carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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
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- G—PHYSICS
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- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
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- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
本發明提供一種可形成耐熱性優異的彩色濾光片的著色硬化性樹脂組成物。一種著色硬化性樹脂組成物,其特徵在於包含著色劑、樹脂、聚合性化合物、以及聚合起始劑,且著色劑為含有方酸內鎓鹽染料的著色劑,樹脂為包含如下結構單元的樹脂,該結構單元含有可具有取代基的咔唑環。 The present invention provides a colored curable resin composition capable of forming a color filter excellent in heat resistance. A colored curable resin composition, characterized in that it contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, and the colorant is a colorant containing a squarylium dye, and the resin is a resin containing the following structural units , this structural unit contains a carbazole ring which may have a substituent.
Description
本發明是有關於一種著色硬化性樹脂組成物、彩色濾光片及顯示裝置。 The present invention relates to a colored curable resin composition, a color filter and a display device.
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)。 Display devices such as liquid crystal display devices, electroluminescence (electroluminescence) display devices, and plasma displays, or charge coupled device (CCD) or complementary metal-oxide semiconductor (Complementary Metal-Oxide-Semiconductor Transistor, CMOS) sensors Color filters used in solid-state imaging devices such as PTFE are made of colored resin compositions. As a coloring agent used in such a colored resin composition, squarylium dye is known (Patent Document 1, Patent Document 2, etc.).
[專利文獻1] 日本專利特開2015-086379號公報 [Patent Document 1] Japanese Patent Application Publication No. 2015-086379
[專利文獻2] 日本專利特開2015-086380號公報 [Patent Document 2] Japanese Patent Application Publication No. 2015-086380
但是,由先前已知的使用方酸內鎓鹽染料的著色硬化性樹脂 組成物所形成的彩色濾光片有時無法充分滿足耐熱性(較佳為耐熱性與吸光度保持率、或耐熱性與明度)。因此,本發明的課題在於提供一種可形成耐熱性(較佳為耐熱性與吸光度保持率、或耐熱性與明度)優異的彩色濾光片的著色硬化性樹脂組成物。 However, the previously known colored curable resin using squarylium dye The color filter formed of the composition may not fully satisfy the heat resistance (preferably heat resistance and absorbance retention, or heat resistance and brightness). Therefore, an object of the present invention is to provide a colored curable resin composition capable of forming a color filter excellent in heat resistance (preferably heat resistance and absorbance retention, or heat resistance and brightness).
本發明的主旨如下所述。 The gist of the present invention is as follows.
[1]一種著色硬化性樹脂組成物,其特徵在於包含著色劑、樹脂、聚合性化合物、以及聚合起始劑,且著色劑為含有方酸內鎓鹽染料的著色劑,樹脂為包含如下結構單元的樹脂,該結構單元含有可具有取代基的咔唑環。 [1] A colored curable resin composition, characterized in that it contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, and the colorant is a colorant containing a squarylium dye, and the resin has the following structure Resin of a unit, the structural unit contains a carbazole ring which may have a substituent.
[2]如[1]所述的著色硬化性樹脂組成物,其中方酸內鎓鹽染料為式(I)所表示的化合物。 [2] The colored curable resin composition according to [1], wherein the squarylium dye is a compound represented by formula (I).
[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。 [In formula (I), R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group.
R5~R8分別獨立地表示氫原子或羥基。 R 5 to R 8 each independently represent a hydrogen atom or a hydroxyl group.
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。 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). Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group.
Ar1及Ar2分別獨立地表示可具有取代基的碳數1~20的一價飽和烴基或下式(i)所表示的基團。] 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 the following formula (i). ]
[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] [In formula (i), R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and m represents an integer of 0 to 5 . Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. When m is 2 or more, each of the plurality of R 12 may be the same or different. *Indicates bond with nitrogen atom]
[3]如[1]或[2]所述的著色硬化性樹脂組成物,其中聚合起始 劑為O-醯基肟化合物。 [3] The colored curable resin composition according to [1] or [2], wherein polymerization is initiated The agent is O-acyl oxime compound.
[4]一種彩色濾光片,其是由如[1]至[3]中任一項所述的著色硬化性樹脂組成物形成。 [4] A color filter formed from the colored curable resin composition according to any one of [1] to [3].
[5]一種顯示裝置,包含如[4]所述的彩色濾光片。 [5] A display device including the color filter according to [4].
根據本發明的著色硬化性樹脂組成物,可提供一種耐熱性(較佳為耐熱性與吸光度保持率、或耐熱性與明度)優異的彩色濾光片。 According to the colored curable resin composition of the present invention, a color filter excellent in heat resistance (preferably heat resistance and absorbance retention, or heat resistance and brightness) can be provided.
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))。 The colored curable resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)), a resin (hereinafter, may be referred to as resin (B)), and a polymerizable compound (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as It is a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).
著色劑(A)含有方酸內鎓鹽染料。 The coloring agent (A) contains squarylium dye.
樹脂(B)包含如下結構單元,該結構單元含有可具有取代基的咔唑環。 Resin (B) contains a structural unit containing a carbazole ring which may have a substituent.
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))。 The colored curable resin composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as solvent (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))。 The colored curable resin composition of the present invention may also contain a leveling agent (hereinafter, may be referred to as a leveling agent (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。 In this specification, the compounds exemplified as each component can be used alone or in combination of multiple types unless otherwise specified.
<著色劑(A)> <Color(A)>
著色劑(A)中所含的方酸內鎓鹽染料例如可例示日本專利特開2013-76926號公報中記載的化合物等。 Examples of the squarylium dye contained in the colorant (A) include compounds described in Japanese Patent Application Laid-Open No. 2013-76926.
方酸內鎓鹽染料較佳為式(I)所表示的化合物(以下,有時稱為化合物(I))。 The squarylium dye is preferably a compound represented by formula (I) (hereinafter, may be referred to as compound (I)).
以下,對化合物(I)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。 Hereinafter, compound (I) will be described in detail, and it is assumed that compound (I) also includes compounds obtained by rotating the resonance structure of formula (I) or each group in formula (I) around the bond axis of a single bond.
[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。 [In formula (I), R 1 to R 4 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group.
R5~R8分別獨立地表示氫原子或羥基。 R 5 to R 8 each independently represent a hydrogen atom or a hydroxyl group.
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。 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). Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group.
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。] 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). ]
[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] [In formula (i), R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, and m represents an integer of 0 to 5 . Oxygen atoms or sulfur atoms may also be inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group. When m is 2 or more, each of the plurality of R 12 may be the same or different. *Indicates bond with nitrogen atom]
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 the 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的脂環式烷基。 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, Straight-chain alkyl groups with 1 to 20 carbon atoms such as pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl and eicosyl; isopropyl, isobutyl, Branched chain alkyl groups with 3 to 20 carbon atoms such as dibutyl, tert-butyl, isopentyl, neopentyl and 2-ethylhexyl; cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, Alicyclic alkyl groups with 3 to 20 carbon atoms such as cyclooctyl, tricyclodecyl and adamantyl.
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;-NRaRb(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 for these saturated hydrocarbon groups include: halogen atoms such as fluorine atoms, chlorine atoms, and iodine; hydroxyl groups; carboxyl groups; -NR a R b (R a and R b are each independently a hydrogen atom or a carbon number of 1 to 20 alkyl group); nitro group; alkoxycarbonyl groups having 1 to 10 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group; etc. Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms with a substituent include A group represented by the following formula. In the following formula, * represents a bond.
該些飽和烴基中所含的氫原子或甲基亦可取代為鹵素原子、羥基或者經1個或2個碳數1~8的烷基取代的胺基,作為 該基團,例如可列舉下述式所表示的基團。此處,作為經1個或2個碳數1~8的烷基取代的胺基,可列舉:甲基胺基、乙基胺基、正丙基胺基、正丁基胺基、正戊基胺基、二甲基胺基、二乙基胺基、二丁基胺基、甲基乙基胺基等。下述式中,*表示結合鍵。 The hydrogen atoms or methyl groups contained in these saturated hydrocarbon groups can also be substituted with halogen atoms, hydroxyl groups or amine groups substituted by 1 or 2 alkyl groups with 1 to 8 carbon atoms, as Examples of this group include groups represented by the following formula. Here, examples of the amino group substituted by one or two alkyl groups having 1 to 8 carbon atoms include: methylamino group, ethylamino group, n-propylamino group, n-butylamino group, n-pentylamine group methylamine group, dimethylamino group, diethylamine group, dibutylamino group, methylethylamino group, etc. In the following formula, * represents a bond.
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 the group having an oxygen atom or a sulfur atom inserted between the carbon atoms constituting the saturated hydrocarbon group include groups represented by the following formulas. In the following formula, * represents a bond.
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;-NRcRd(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 substituents for 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 R d are each independently a hydrogen atom or a carbon number of 1 to 20 alkyl group); nitro group; alkoxy groups with 1 to 10 carbon atoms such as methoxy and ethoxy groups; alkoxy carbonyl groups with 1 to 10 carbon atoms such as methoxycarbonyl and ethoxycarbonyl groups; 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2-乙基己基。 R 9 and R 10 are preferably an alkyl group having 3 to 14 carbon atoms which may have a substituent and a group represented by the formula (i), and more preferably a straight chain chain having 3 to 6 carbon atoms which may have a substituent. alkyl group, a linear or branched chain alkyl group having 7 to 14 carbon atoms that may have a substituent (such as octyl, nonyl, decyl, dodecyl, 2-ethylhexyl, etc.), and the formula The group represented by (i) is more preferably 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。 The saturated hydrocarbon group of 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.
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。 The unsaturated hydrocarbon group of R 12 is preferably an alkenyl group having 2 to 4 carbon atoms, more preferably a vinyl group or an allyl group.
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。 When m is 2 or more, it is preferred 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 that a part of R 12 is a saturated hydrocarbon group and a part of R 12 is an unsaturated hydrocarbon group.
m較佳為1~5,更佳為1~3。 m is preferably 1 to 5, more preferably 1 to 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。 Examples of the group represented by formula (i) include the following groups. *Indicates the bond with nitrogen atom.
[化7]
式(I)中,當將
所表示的基團設為X1,將[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。 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). *Indicates the bond with the carbon atom.
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)。 Examples of compound (I) include compound (AII-1) to compound (AII-27) shown in Table 1.
[表1]
就原料獲取性的觀點而言,更佳為化合物(AII-10)~化合物(AII-18)。 From the viewpoint of raw material availability, compound (AII-10) to compound (AII-18) are more preferred.
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 formula (I) can be produced by reacting the compound represented by formula (pt1), the compound represented by formula (pt2), and the compound represented by formula (pt3). In this reaction, the usage amount of the compound represented by formula (pt3) is preferably 0.05 mole or more and 0.8 mole per mole of the total of the compound represented by formula (pt1) and the compound represented by formula (pt2). mole or less, more preferably 0.1 mole or more and 0.6 mole or less.
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 respectively represent the same meanings 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, isopropyl alcohol and butanol; and nitrohydrocarbon solvents such as nitrobenzene. ; Ketone solvents such as methyl isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidinone; etc. These can also be used in combination. Among them, a mixed solvent of butanol and toluene is preferred. The usage amount of the organic solvent 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 in total of the compound represented by formula (pt1) and the compound represented by formula (pt2) And less than 150 parts by mass.
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。 Method for extracting compound (I) as the target compound from the reaction mixture The method is not particularly limited, and various known methods can be used. For example, a method of cooling and filtering the precipitated crystals after completion of the reaction can be cited. The filtered crystals are preferably washed with water and then dried. In addition, if necessary, it can be further purified 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 the formula (IV-2) with the compound represented by the formula (IV-3) to produce the compound represented by the formula (IV-4), the compound represented by the formula (IV-4) and the compound represented by the formula The compound represented by formula (pt1) can be produced by reacting the compound represented by (IV-5).
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 Formula (IV-2) to Formula (IV-5), R 1 , R 2 , R 5 , R 6 , R 9 and Ar 1 respectively have the same meanings 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。 Examples of a method for producing a compound represented by formula (IV-4) from a compound represented by formula (IV-2) and a compound represented by formula (IV-3) include various known methods. A method, such as the method described in 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 formula (pt1) from the compound represented by formula (IV-4) and the compound represented by formula (IV-5), various known methods can be cited, for example, Journal of Polymer Science Part A: The method described in 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 using the same method as described above.
著色劑(A)除方酸內鎓鹽染料以外,亦可包含與方酸內鎓鹽染料不同的著色劑,該與方酸內鎓鹽染料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,與方酸內鎓鹽染料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。 In addition to the squarium dye, the coloring agent (A) may also contain a coloring agent different from the squarium dye. The coloring agent different from the squarium dye may be a dye (hereinafter, sometimes referred to as It is any one of the dye (A1)) and the pigment (hereinafter, sometimes referred to as the pigment (A2)), and the coloring agent different from the squarylium dye may also include these dyes (A1) and the pigment (A2) ) one or both.
染料(A1)只要不包含方酸內鎓鹽染料,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 squarylium dye, and known dyes can be used. Examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Examples of dyes include compounds classified as having hues other than pigments in the Color Index (published by The Society of Dyers and Colourists), or dyeing notes (color index). Well-known dyes described in Shikisensha Co., Ltd. In addition, based on the chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, and methine dyes. Base dye, azomethine dye, acridine Dydine dyes, styrene-based dyes, coumarin dyes, quinoline dyes and nitro dyes, etc. 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。 Specifically, C.I. Solvent Yellow 4 (hereinafter, description of C.I. Solvent Yellow will be omitted and only the number will be described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; C.I. Solvent Red (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 (Solvent Orange) 2, 7, 11, 15, 26, 56, 77, 86; C.I. Solvent Violet (Solvent Violet) 11, 13 , 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue (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 (Solvent Green) 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. Solvent dye, C.I. Acid Yellow (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. 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; C.I. Acid Blue (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. Acid Green (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, etc. C.I. acid dyes, C.I. Direct Yellow (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. 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 (Direct Orange) 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct Violet (Direct Violet) 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. Direct Blue (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 (Direct Green) 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. C.I. direct dye, C.I. disperse yellow (Disperse Yellow) 51, 54, 76; C.I. Disperse Violet (Disperse Violet) 26, 27; C.I. Disperse Blue (Disperse Blue) 1, 14, 56, 60, etc. C.I. Disperse dye, C.I. Basic Red (Basic Red) 1, 10; C.I. 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 (Basic Violet) 2; C.I. Basic Red (Basic Red) 9; C.I. Basic Green (Basic Green) 1, etc. C.I. Basic dyes, C.I. Reactive Yellow (Reactive Yellow) 2, 76, 116; C.I. Reactive Orange (Reactive Orange) 16; C.I. Reactive Red (Reactive Red) 36, etc. C.I. Reactive dyes, C.I. Mordant Yellow (Mordant Yellow) 5, 8 ,10,16,20,26,30,31,33,42,43,45,56,61,62,65; C.I. 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. 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. 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. Mordant Blue (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 and other C.I. mordant dyes, C.I. Vat Green (Vat Green) 1 and other C.I. vat dyes, etc.
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。 These dyes may be appropriately selected based on the desired spectral spectrum of the 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。 The pigment (A2) is not particularly limited, and known pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be used. ) pigment.
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。 Examples of pigments include: C.I. 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 (Pigment Orange) 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. Pigment Red (Pigment Red) 9, 97, 105, 122, 123, 144, 149, 166, 168, 176 , 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments; C.I. Pigment Blue (Pigment Blue) 15: 6, 60 and other blue pigments; C.I. Pigment Violet (Pigment Purple) Violet) 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green (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 and other 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。 If necessary, the pigment may be subjected to rosin treatment, surface treatment using a pigment derivative introducing an acidic group or a basic group, grafting treatment on the pigment surface using a polymer compound, etc., or micronization using a sulfuric acid micronization method, etc. treatment, or cleaning treatment using an organic solvent or water to remove impurities, removal treatment of ionic impurities using an ion exchange method, etc.
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。 The pigment preferably has a uniform particle size. By containing a pigment dispersant and performing a dispersion treatment, a pigment dispersion in which 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。 Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic and other surfactants. These pigment dispersants may be used alone, or two or more types may be used in combination. Examples of pigment dispersants by trade name include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyeisha Chemical Co., Ltd.), Solsperse (Zeneca (Zeneca) Zeneca Co., Ltd.), EFKA (manufactured by CIBA Co., Ltd.), Ajisper (manufactured by Ajinomoto Fine-Techno Co., Ltd.), DI Disperbyk (manufactured by BYK-chemie), etc.
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。 When a pigment dispersant is used, the usage amount of the pigment dispersant is preferably 1 mass % or more and 100 mass % or less, and more preferably 5 mass % or more and 50 mass % with respect to the total amount of pigment (A2). %the following. When the usage amount of the pigment dispersant is within the above range, a pigment dispersion liquid in a uniformly dispersed state tends to be obtained.
於著色劑(A)除化合物(I)以外亦包含染料(A1)及/或顏料(A2)的情況下,相對於著色劑(A)的總量,化合物(I)的含有率較佳為1質量%以上且90質量%以下,更佳為1質量%以上且60質量%以下,進而佳為3質量%以上且40質量%以下。 When the colorant (A) includes the dye (A1) and/or the pigment (A2) in addition to the compound (I), the content rate of the compound (I) relative to the total amount of the colorant (A) is preferably: 1 mass % or more and 90 mass % or less, more preferably 1 mass % or more and 60 mass % or less, still more preferably 3 mass % or more and 40 mass % or less.
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 rate of the colorant (A) in the colored curable resin composition is preferably 0.1 mass% or more and 70 mass% or less, more preferably 0.5 mass% or more and 60 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 rate of the colorant (A) is within the above range, the color density when the color filter is made is sufficient, and the necessary amount of the resin (B) can be included in the composition. or a polymerizable compound (C), 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 excluding the content of the solvent from the total amount of the colored curable resin composition. The total amount of solid content and the content of each component relative thereto can be measured, for example, by a known analysis method such as liquid chromatography or gas chromatography.
<樹脂(B)> <Resin(B)>
樹脂(B)含有包含如下結構單元的樹脂,該結構單元含有可具有取代基的咔唑環。 Resin (B) contains a resin containing a structural unit containing a carbazole ring which may have a substituent.
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。 In addition, in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acrylyl" and "(meth)acrylate" also have the same meaning.
藉由本發明的著色硬化性樹脂組成物含有所述樹脂,從而彩色濾光片的耐熱性提升。 When the colored curable resin composition of the present invention contains the resin, the heat resistance of the color filter is improved.
含有可具有取代基的咔唑環的結構單元亦可源自含有可具有取代基的咔唑環的不飽和化合物。源自該不飽和化合物的結構單元只要包含於使用該不飽和化合物作為單量體而獲得的共聚物中即可。或者,亦可藉由使含有可具有取代基的咔唑環的化合物與其他結構單元反應而獲得。 The structural unit containing a carbazole ring which may have a substituent may also be derived from an unsaturated compound containing a carbazole ring which may have a substituent. The structural unit derived from the unsaturated compound only needs to be contained in the copolymer obtained using the unsaturated compound as a monomer. Alternatively, it can also be obtained by reacting a compound containing a carbazole ring which may have a substituent with other structural units.
包含含有可具有取代基的咔唑環的結構單元的不飽和化合物較佳為式(III)所表示的化合物。 The unsaturated compound containing a structural unit containing a carbazole ring which may have a substituent is preferably a compound represented by formula (III).
[化13]
式(III)中,R1a表示氫原子、甲基、或羥基甲基。 In formula (III), R 1a represents a hydrogen atom, a methyl group, or a hydroxymethyl group.
R2a~R9a相互獨立地表示氫原子、鹵素原子、碳數1~20的飽和烴基或碳數6~20的芳基,該飽和烴基中所含的氫原子亦可經烷氧基或芳基取代。 R 2a ~ R 9a independently represent a hydrogen atom, a halogen atom, a saturated hydrocarbon group with 1 to 20 carbon atoms, or an aryl group with 6 to 20 carbon atoms. The hydrogen atom contained in the saturated hydrocarbon group can also be represented by an alkoxy group or an aromatic group. base substitution.
Xa表示單鍵、碳數1以上的烷二基、或者直鏈狀或分支鏈狀的下述式(V)所表示的基團。 X a represents a single bond, an alkylenediyl group having 1 or more carbon atoms, or a linear or branched chain group represented by the following formula (V).
(式(V)中,所述la表示0以上的整數。ma表示1以上的整數) (In formula (V), la represents an integer greater than 0. ma represents an integer greater than 1)
R2a~R9a所表示的碳數1~20的飽和烴基可列舉: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的脂環式烷基。 The saturated hydrocarbon groups with 1 to 20 carbon atoms represented by R 2a to R 9a include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl Linear alkyl groups with 1 to 20 carbon atoms such as hexadecyl and eicosyl; isopropyl, isobutyl, second butyl, third butyl, isopentyl, neopentyl and 2- Branched chain alkyl groups with 3 to 20 carbon atoms such as ethylhexyl; cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecanyl and adamantyl groups with 3 to 20 carbon atoms Alicyclic alkyl.
R2a~R9a所表示的碳數6~20的芳基可列舉:苯基、甲苯基、二甲苯基、萘基等。 Examples of the aryl group having 6 to 20 carbon atoms represented by R 2a to R 9a include phenyl, tolyl, xylyl, naphthyl, and the like.
R2a~R9a所表示的烷氧基例如碳數為1~10,可列舉:甲氧基、乙氧基、丙氧基、丁氧基、戊基氧基、己基氧基、庚基氧基等。 The alkoxy group represented by R 2a to R 9a has, for example, a carbon number of 1 to 10, and includes: methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy Key et al.
作為Xa所表示的碳數1以上的烷二基,可列舉:亞甲基、伸乙基、丙烷-1,3-二基、丙烷-1,2-二基、丙烷-1,1-二基等。 Examples of the alkylenediyl group having 1 or more carbon atoms represented by Erji et al.
作為式(III)所表示的化合物,可列舉:N-乙烯基咔唑、N-烯丙基咔唑、N-(甲基)丙烯醯基咔唑、(甲基)丙烯酸2-(9-咔唑基)乙酯、(甲基)丙烯酸2-(9-咔唑基)乙氧基乙酯、(甲基)丙烯酸2-(9-咔唑基)-2-甲基乙酯、(甲基)丙烯酸2-(9-咔唑基)-1-甲基乙酯等。其中,較佳為N-乙烯基咔唑、N-烯丙基咔唑、(甲基)丙烯酸2-(9-咔唑基)乙酯。 Examples of the compound represented by formula (III) include: N-vinylcarbazole, N-allylcarbazole, N-(meth)acrylcarbazole, (meth)acrylic acid 2-(9- Carbazolyl)ethyl ester, (meth)acrylic acid 2-(9-carbazolyl)ethoxyethyl ester, (meth)acrylic acid 2-(9-carbazolyl)-2-methylethyl ester, ( 2-(9-carbazolyl)-1-methylethyl methacrylate, etc. Among them, N-vinylcarbazole, N-allylcarbazole, and 2-(9-carbazolyl)ethyl (meth)acrylate are preferred.
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。 Resin (B) is preferably an alkali-soluble resin. Examples of the resin (B) showing alkali solubility include the following resins [K1] to resins [K6] and the like.
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、以及源自不飽和化合物(z)(以下,有時稱為「(z)」)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,所述不飽和化合物(z)含有可具有取代基的咔唑環;樹脂[K2]:包含源自(a)的結構單元、源自(b)的結構單元、源自(z)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(z)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(z)的結構單元的共聚物;樹脂[K4]:包含源自(a)的結構單元、源自(z)的結構單元、以及源自(c)的結構單元的共聚物;樹脂[K5]:包含源自(a)的結構單元、對源自(b)的結構單元加成(a)而成的結構單元、以及源自(z)的結構單元的共聚物;樹脂[K6]:包含源自(a)的結構單元、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(z)的結構單元的共聚物。 Resin [K1]: Contains a structural unit derived from the monomer (a) (hereinafter, sometimes referred to as "(a)"), a structural unit derived from the monomer (b) (hereinafter, sometimes referred to as "(b)" ”), and a copolymer of structural units derived from the unsaturated compound (z) (hereinafter, sometimes referred to as “(z)”), wherein the monomer (a) is selected from the group consisting of unsaturated carboxylic acid and at least one of the group consisting of unsaturated carboxylic acid anhydrides, the monomer (b) has a cyclic ether structure with a carbon number of 2 to 4 and an ethylenically unsaturated bond, and the unsaturated compound (z) contains Carbazole ring which may have a substituent; Resin [K2]: contains a structural unit derived from (a), a structural unit derived from (b), a structural unit derived from (z), and a structural unit derived from (a) Copolymer of the structural unit of the copolymerized monomer (c) (which is different from (a), (b) and (z)) (hereinafter, sometimes referred to as "(c)"); resin [K3]: Copolymer containing a structural unit derived from (a) and a structural unit derived from (z); Resin [K4]: containing a structural unit derived from (a), a structural unit derived from (z), and a structural unit derived from (z) Copolymer of structural units derived from c); Resin [K5]: Contains a structural unit derived from (a), a structural unit derived from (b) added to a structural unit derived from (b), and a structural unit derived from (z) Copolymer of structural units; Resin [K6]: Contains a structural unit derived from (a), a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a source Copolymer of structural units from (z).
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) is preferably such that the carboxyl group or carboxylic acid anhydride of (a) remains in an unreacted state. In addition, in the resin [K1] and the resin [K2], it is preferable that the structural unit derived from (b) is that the cyclic ether structure having 2 to 4 carbon atoms in (b) remains 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酐類;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。 Specific examples of (a) include: acrylic acid, methacrylic acid Acid, crotonic acid, o-vinyl benzoic acid, m-vinyl benzoic acid, p-vinyl benzoic acid and other unsaturated monocarboxylic acids; maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3 -Vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic 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, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1] Unsaturated dicarboxylic anhydrides such as hept-2-ene anhydride; succinic acid mono[2-(meth)acryloxyethyl] ester, phthalic acid mono[2-(meth)acryloxyethyl] Unsaturated mono[(meth)acryloxyalkyl]esters of divalent or higher polycarboxylic acids such as ethyl]ester; containing hydroxyl groups in the same molecule such as α-(hydroxymethyl)acrylic acid and carboxyl unsaturated acrylates, etc.
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。 Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution. wait.
(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。 (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.
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)」)。 Examples of (b) include monomers (b1) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as “(b1)”), monomers having an oxetanyl group and an ethylenically unsaturated bond. The monomer (b2) with an ethylenically unsaturated bond (hereinafter, may be referred to as "(b2)"), and the monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter, may be referred to as "(b2)") (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, may be referred to as "(b1-1)" )"), a monomer (b1-2) (hereinafter, sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized.
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 (glycidylmeth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, and glycidylvinyl Ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-methylene Benzyl glycidyl ether, α-methyl-p-vinyl benzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl) styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyl)styrene Oxymethyl) Styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene Glyceryloxymethyl)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) (manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4 (meth)acrylic acid - Epoxy cyclohexyl 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.
[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。 [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. The hydrogen atom contained in the alkyl group may also be substituted by a hydroxyl group.
Xe及Xf表示單鍵、*-Rg-、*-Rg-O-、*-Rg-S-或*-Rg-NH-。 X e and X f represent single bonds, *-R g -, *-R g -O-, *-R g -S- or *-R g -NH-.
Rg表示碳數1~6的烷二基。 R g represents an alkanediyl group having 1 to 6 carbon atoms.
*表示與O的結合鍵] *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。 Examples of the alkyl group having 1 to 4 carbon atoms include: methyl, ethyl, n-propyl, Isopropyl, n-butyl, second butyl, third butyl, etc.
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。 Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxyl group 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.
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。 Re and R f are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably are a hydrogen atom and a methyl group.
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。 Examples of the alkylenediyl include: methylene, ethylidene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5 -diyl, hexane-1,6-diyl, etc.
作為Xe及Xf,較佳為可列舉:單鍵、亞甲基、伸乙基、*-CH2-O-及*-CH2CH2-O-,更佳為可列舉:單鍵、*-CH2CH2-O-(*表示與O的結合鍵)。 As X e and _ , *-CH 2 CH 2 -O- (* represents 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(BI-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。 Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to formula (BI-15). Among them, preferred are formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) or formula (BI-11) to 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]
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。 Examples of the compound represented by formula (BII) include compounds represented by any one of formula (BII-1) to formula (BII-15). Among them, formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) to 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]
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 individually, or two or more types may be used in combination. When a compound represented by formula (BI) and a compound represented by formula (BII) are used together, the content ratio of these [compound represented by formula (BI): compound represented by formula (BII)] is expressed in moles The preferred benchmark is 5:95~95:5, and the more preferred range is 20:80~80:20.
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 preferred. Examples of (b2) include: 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-Ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-acryloxy Methyl oxetane, 3-methyl-3-methacryloxyethyl oxetane, 3-methyl-3-propenyloxyethyl oxetane, 3-ethyl-3-methacryloxyethyloxetane, 3-ethyl-3-propenyloxyethyloxetane, etc.
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。 (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloxy group. 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 preferred in terms of further improving reliability such as heat resistance and chemical resistance of the obtained color filter. Furthermore, in terms of excellent storage stability of the colored curable resin composition, (b1-2) is more preferred.
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: (meth)acrylic acid methyl ester, (meth)ethyl acrylate, (meth)acrylic acid n-butyl ester, (meth)acrylic acid second butyl ester, (meth)acrylic acid third butyl ester Butyl ester, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclo(meth)acrylate Pentyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decan-8-yl (meth)acrylate (this technology In the field, it is called "dicyclopentyl (meth)acrylate" as a common name. In addition, it is sometimes called "tricyclodecyl (meth)acrylate"), (meth)acrylic acid tricyclo[ 5.2.1.0 2,6 ]Decene-8-yl ester (commonly known as "(meth)acrylic acid dicyclopentenyl ester" in this technical field), (meth)acrylic acid dicyclopentane Oxyethyl ester, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate , (meth)acrylates such as naphthyl (meth)acrylate, benzyl (meth)acrylate, etc.; hydroxyl-containing esters such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc. (Meth)acrylates; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; 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 [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-di(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- Alkene, 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-tert-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(tert-butyl Bicyclic unsaturated compounds such as oxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; styrene, α -Methyl styrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, toluene Acrylamide, vinyl acetate, 1,3-butadiene, isoprene, 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%~45莫耳%源自(b)的結構單元:2莫耳%~90莫耳%源自(z)的結構單元:1莫耳%~90莫耳%,更佳為源自(a)的結構單元:5莫耳%~40莫耳%源自(b)的結構單元:5莫耳%~80莫耳%源自(z)的結構單元:5莫耳%~80莫耳%。 In resin [K1], the ratio of the structural units derived from each to the constituting resin Among all the structural units of [K1], preferred are structural units derived from (a): 2 mol% to 45 mol% of structural units derived from (b): 2 mol% to 90 mol% derived from ( Structural units of z): 1 mol% to 90 mol%, more preferably structural units derived from (a): 5 mol% to 40 mol% Structural units derived from (b): 5 mol% ~80 mol% Structural units derived from (z): 5 mol% ~ 80 mol%.
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度保持率。 If the ratio of the structural units of the resin [K1] is within the above range, the absorbance 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 the resin [K1], for example, the method described in the document "Experimental Methods of Polymer Synthesis" (Otsu Takayuki's Chemical Doujin Publishing House Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the methods in this document can be referred to Made with reference to documented references.
具體而言,可列舉如下方法:將(a)、(b)及(z)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 (z), a polymerization initiator, a solvent, etc. into a reaction vessel, and replacing oxygen with nitrogen, for example. Create a deoxygenated environment and perform heating and heat preservation while stirring. In addition, the polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in this field can be used. For example, examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or organic polymers. The oxide (benzoyl peroxide, etc.) may be used as a solvent as long as it dissolves each monomer, and examples thereof include solvents for the colored curable resin composition of the present invention. agent (E) and solvents described below.
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 used directly as a reacted solution, as a concentrated or diluted solution, or as a solid (powder) taken out by reprecipitation or other methods. In particular, by using the solvent contained in the colored curable resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be directly used for the preparation of the colored curable resin composition of the present invention, so it can be 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%~45莫耳%源自(b)的結構單元:2莫耳%~90莫耳%源自(z)的結構單元:1莫耳%~90莫耳%源自(c)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%~40莫耳%源自(b)的結構單元:5莫耳%~80莫耳%源自(z)的結構單元:5莫耳%~80莫耳%源自(c)的結構單元:5莫耳%~50莫耳%。 In the resin [K2], the ratio of the structural units derived from each of the structural units derived from (a) among all the structural units constituting the resin [K2] is preferably: 2 mol % to 45 mol % derived from Structural units from (b): 2 mol % ~ 90 mol % Structural units derived from (z): 1 mol % ~ 90 mol % Structural units derived from (c): 1 mol % ~ 65 mol %, more preferably, the structural unit derived from (a): 5 mol % ~ 40 mol % of the structural unit derived from (b): 5 mol % ~ 80 mol % of the structural unit derived from (z) : 5 mol% to 80 mol% of the structural unit derived from (c): 5 mol% to 50 mol%.
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度保持率。 If the ratio of the structural units of the resin [K2] is within the above range, the absorbance retention rate of the color filter obtained from the colored 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 described as the manufacturing method of the resin [K1], for example. The method is manufactured in the same way.
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(z)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%~50莫耳%源自(z)的結構單元:50莫耳%~90莫耳%。 In the resin [K3], the ratio of the structural units derived from each of the structural units derived from (a) among all the structural units constituting the resin [K3] is preferably: 2 mol % to 60 mol % derived from Structural units from (z): 40 mol% to 98 mol%, more preferably structural units derived from (a): 10 mol% to 50 mol% Structural units derived from (z): 50 mol% %~90mol%.
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。 The resin [K3] can be produced in the same manner as the method described as the production 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[K4]的全部結構單元中較佳為源自(a)的結構單元:2莫耳%~45莫耳%源自(z)的結構單元:1莫耳%~90莫耳%源自(c)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%~40莫耳%源自(z)的結構單元:5莫耳%~80莫耳%源自(c)的結構單元:5莫耳%~50莫耳%。 In the resin [K4], the ratio of the structural units derived from each of the structural units derived from (a) among all the structural units constituting the resin [K4] is preferably: 2 mol% to 45 mol% derived from Structural units from (z): 1 mol % to 90 mol % Structural units derived from (c): 1 mol % to 65 mol %, more preferably structural units derived from (a): 5 mol % %~40 mol% Structural units derived from (z): 5 mol%~80 mol% Structural units derived from (c): 5 mol%~50 mol%.
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。 The resin [K4] can be produced in the same manner as the method described as the production 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(a)與(b)與(z)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。 Regarding the resin [K5], as the first stage, the same process as the resin [K1] was The copolymers of (a), (b) and (z) are obtained in the same manner as the manufacturing method. In the same manner as described above, the obtained copolymer may be used directly as a reacted solution, a concentrated or diluted solution, or a copolymer obtained in the form of a solid (powder) by reprecipitation or the like.
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(a)、(b)及(z)的結構單元的比率分別較佳為源自(a)的結構單元:2莫耳%~45莫耳%源自(b)的結構單元:2莫耳%~90莫耳%源自(z)的結構單元:1莫耳%~90莫耳%,更佳為源自(a)的結構單元:5莫耳%~40莫耳%源自(b)的結構單元:5莫耳%~80莫耳%源自(z)的結構單元:5莫耳%~80莫耳%。 The ratio of the structural units derived from (a), (b) and (z) relative to the total molar number of all structural units constituting the copolymer is preferably: structural unit derived from (a): 2 moles. %~45 mol% of the structural units derived from (b): 2~90 mol% of the structural units derived from (z): 1%~90 mol% of the structural units derived from (z), preferably from ( Structural units from a): 5 mol%~40 mol% Structural units derived from (b): 5 mol%~80 mol% Structural units derived from (z): 5 mol%~80 mol %.
繼而,使燒瓶內成為空氣環境,將(a)與(b)與(z)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(a)與(b)與(z)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]。 Then, the inside of the flask is brought into an air environment, and the reaction catalyst (for example, tris(dimethyl (Aminomethyl)phenol, etc.) and polymerization inhibitors (such as hydroquinone, etc.) are put into the flask, and reacted at 60°C to 130°C for 1 hour to 10 hours, so that (a) and (b) ) reacts with the cyclic ether derived from (b) contained in the copolymer of (z) and the carboxylic acid or carboxylic acid anhydride contained in (a) to obtain resin [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)。 The amount of (a) used to react with the copolymer is preferably 5 moles to 80 moles relative to 100 moles of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, the (b) used in the resin [K5] is preferably (b1).
相對於(a)、(b)及(z)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(z)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。 The usage amount of the reaction catalyst is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (z). The usage amount of the polymerization inhibitor is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (z).
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。 Reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted taking into consideration the production equipment or the heat generated by polymerization. In addition, similarly to the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted by taking into consideration the production equipment, the amount of heat generated by the polymerization, and the like.
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。 Resin [K6] is a resin obtained by further reacting carboxylic acid anhydride and resin [K5]. A carboxylic acid anhydride is reacted with a hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride.
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。相對於藉由所述環狀醚與羧酸或羧酸酐的反應而產生的羥基的使用量1莫耳,羧酸酐的使用量較佳為0.5莫耳~1莫耳。 Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, and 3,4,5,6-tetrahydrophthalic 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 mole to 1 mole relative to 1 mole of usage amount of hydroxyl group generated by the reaction of the cyclic ether and carboxylic acid or carboxylic anhydride.
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-乙烯基咔唑共聚物、(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸/N-烯丙基咔唑共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-乙烯基咔唑共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-烯丙基咔 唑共聚物等樹脂[K1];(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-乙烯基咔唑共聚物、(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-烯丙基咔唑共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸/N-乙烯基咔唑共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸/N-烯丙基咔唑共聚物、丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-乙烯基咔唑/(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-烯丙基咔唑/(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-乙烯基咔唑共聚物、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-烯丙基咔唑共聚物等樹脂[K2];N-乙烯基咔唑/(甲基)丙烯酸共聚物、N-烯丙基咔唑/(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-乙烯基咔唑共聚物、(甲基)丙烯酸苄酯/(甲基)丙烯酸/N-烯丙基咔唑共聚物、苯乙烯/(甲基)丙烯酸/N-乙烯基咔唑共聚物、苯乙烯/(甲基)丙烯酸/N-烯丙基咔唑共聚物、(甲基)丙烯酸/N-乙烯基咔唑/(甲基)丙烯酸2-羥基乙酯共聚物、(甲基)丙烯酸/N-烯丙基咔唑/(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-乙烯基咔唑/(甲基)丙烯酸/(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-烯丙 基咔唑/(甲基)丙烯酸/(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-乙烯基咔唑/(甲基)丙烯酸/(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-烯丙基咔唑/(甲基)丙烯酸/(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。 Specific examples of the resin (B) include: (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester/(meth)acrylic acid/N-vinylcarbazole copolymer, (meth)acrylic acid 3 ,4-epoxycyclohexylmethyl ester/(meth)acrylic acid/N-allylcarbazole copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(methyl) Resins such as acrylic acid/N-vinylcarbazole copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylic acid/(meth)acrylic acid/N-allylcarbazole copolymer [K1 ]; Glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid/N-vinylcarbazole copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate /(meth)acrylic acid/N-allylcarbazole copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid/N-vinylcarbazole copolymer, (meth)acrylic acid shrinkage Glyceride/styrene/(meth)acrylic acid/N-allylcarbazole copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(meth)acrylic acid/N- Vinyl carbazole/(meth)acrylic acid 2-hydroxyethyl ester copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl ester/(meth)acrylic acid/N-allylcarbo Azole/2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene/N- Vinylcarbazole copolymer, 3-methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene/N-allylcarbazole copolymer, etc. Resin [K2]; N-vinylcarbazole/(meth)acrylic acid copolymer, N-allylcarbazole/(meth)acrylic acid copolymer and other resins [K3]; Benzyl (meth)acrylate/( Meth)acrylic acid/N-vinylcarbazole copolymer, benzyl (meth)acrylate/(meth)acrylic acid/N-allylcarbazole copolymer, styrene/(meth)acrylic acid/N-ethylene carbazole copolymer, styrene/(meth)acrylic acid/N-allylcarbazole copolymer, (meth)acrylic acid/N-vinylcarbazole/(meth)acrylic acid 2-hydroxyethyl ester copolymer , (meth)acrylic acid/N-allylcarbazole/(meth)acrylic acid 2-hydroxyethyl copolymer and other resins [K4]; make (meth)acrylic acid and N-vinylcarbazole/(meth)acrylic acid ) Resin obtained by reacting a copolymer of acrylic acid/glycidyl (meth)acrylate, copolymerization of (meth)acrylic acid and N-allylcarbazole/(meth)acrylic acid/glycidyl (meth)acrylate Resins such as resins obtained by the reaction [K5]; resins obtained by reacting (meth)acrylic acid with a copolymer of N-vinylcarbazole/(meth)acrylic acid/glycidyl (meth)acrylate The resin obtained by further reacting with tetrahydrophthalic anhydride is reacted with a copolymer of (meth)acrylic acid and N-allylcarbazole/(meth)acrylic acid/glycidyl (meth)acrylate. The resin obtained by this reaction is further reacted with tetrahydrophthalic anhydride, such as resin [K6] and the like.
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]。 Among them, as the resin (B), resin [K1] to resin [K4] are preferred, and resin [K1] and resin [K2] are more preferred.
相對於樹脂(B)的固體成分總量,選自由樹脂[K1]~樹脂[K4]所組成的群組中的一種以上(較佳為樹脂[K1]及樹脂[K2]中的一者或兩者,更佳為樹脂[K1])的含有率較佳為80質量%~100質量%,更佳為100質量%。 Relative to the total solid content of resin (B), one or more types selected from the group consisting of resin [K1] to resin [K4] (preferably one of resin [K1] and resin [K2] or Of both, the content rate of resin [K1]) is preferably 80 mass% to 100 mass%, and more preferably 100 mass%.
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 polystyrene-reduced weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, further preferably 5,000 to 30,000. If the molecular weight is within the above range, the hardness of the color filter is increased, the residual film rate is high, the solubility of the unexposed portion to the developer is good, and the resolution of the color pattern is improved.
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 dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.
樹脂(B)的酸價以固體成分換算計較佳為20mg-KOH/g 以上,更佳為30mg-KOH/g以上,進而佳為40mg-KOH/g以上,較佳為200mg-KOH/g以下,更佳為180mg-KOH/g以下,進而佳為150mg-KOH/g以下。此處,酸價是作為中和樹脂(B)1g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 resin (B) is preferably 20 mg-KOH/g in terms of solid content. Above, more preferably 30 mg-KOH/g or more, further preferably 40 mg-KOH/g or more, more preferably 200 mg-KOH/g or less, more preferably 180 mg-KOH/g or less, still more preferably 150 mg-KOH/g the following. Here, the acid value is a value measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined by titration using a potassium hydroxide aqueous solution, for example.
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 rate of resin (B) is preferably 7% to 80% by mass, more preferably 13% to 75% by mass, and even more preferably 17% to 65% by mass relative to the total amount of solid content. When the content rate 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 be improved.
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。 The content of the resin (B) is preferably not less than 10 parts by mass and not more than 95 parts by mass, more preferably not less than 20 parts by mass and not more than 90 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). or less, and more preferably not less than 30 parts by mass and not more than 85 parts by mass. If the content of the resin (B) is within the above range, the absorbance retention rate of the obtained color filter will be further improved.
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。 In addition, the content of the resin (B) is also 55 to 95 parts by mass, preferably 60 to 90 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Less than 1 serving is appropriate. If the content of the resin (B) is within the above range, the absorbance retention rate of the obtained color filter is significantly improved.
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 the 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, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Under the following conditions, the absorbance retention and brightness of the obtained color filter are improved.
<聚合性化合物(C)> <Polymerizable compound (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。 The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D). Examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and preferably (meth)acrylate compounds.
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。 Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Esters, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol ten(meth)acrylate, tetrapentaerythritol nona(meth)acrylate Ester, tris(2-(meth)acryloxyethyl)isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(methyl) 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 (meth)acrylate.
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, 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) is preferably 1% to 65% by mass, more preferably 5% to 60% by mass, and even more preferably 10% to 55% by mass relative to the total amount of solid content. When the content rate of the polymerizable compound (C) is within the above range, the residual film rate during formation of the colored pattern and the chemical resistance of the color filter tend to improve.
<聚合起始劑(D)> <Polymerization initiator (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。 The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of polymerization initiators that generate active radicals include O-acyl oxime compounds, phenylalkyl 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-acyl oxime compound include: N-benzoyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, N-benzyloxy Cyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3 -Cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. O-acyl oxime compound with diphenyl sulfide skeleton; N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3- base]ethane-1-imine, N-ethyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxy Heterocyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6- (2-Methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl- 6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine and other O-carbazole skeleton oxime compounds ; 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyl oxime and other O-acyl groups with fluorene skeleton Oxime compounds; etc. You can also use Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA), DFI-091 (Daito Chemix) ) Co., Ltd.) and other commercially available Taste. Among them, the O-acyl oxime compound is preferably selected from the group consisting of N-benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-acetyloxy Oxy-1-(4-phenylmercaptophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-{2- Methyl-4-(3,3-dimethyl-2,4-dioxolylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1- In the group consisting of imine and 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyl oxime At least one. If these O-acyl oxime compounds are used, a high-brightness color filter tends to be obtained.
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。 Examples of the phenylalkyl ketone compound include: 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]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane- 1-ketone oligomers, α,α-diethoxyacetophenone, benzyldimethyl ketal, etc. Commercially available products such as Irgacure (registered trademark) 369, 907, and 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。 Examples of the triazine compound include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis( Trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5- Triazine, 2,4-bis(trichloromethyl)-6-(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- base)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-dimethyl Oxyphenyl)vinyl]-1,3,5-triazine, etc.
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。 Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) 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。 Examples of the biimidazole compound include: 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 Application Laid-Open No. 6-75372, Japanese Patent Application 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 2 , 2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. Publication No. 62-174204, etc.), biimidazole compounds in which the phenyl groups at the 4, 4', 5, 5'-positions are substituted with alkoxycarbonyl groups (see, for example, Japanese Patent Publication No. 7-10913, etc.), 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 acid-generating polymerization initiator include 4-hydroxyphenyldimethylsulfonate p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonate hexafluoroantimonate, and 4-acetyloxybenzene. Dimethylsulfonyl p-toluenesulfonate, 4-acetyloxyphenyl. methyl. Benzylsonium hexafluoroantimonate, triphenylsonium p-toluenesulfonate, triphenylsonium hexafluoroantimonate, diphenylphosphonium p-toluenesulfonate, diphenylphosphonium hexafluoroantimonate, etc. Salts, or nitrobenzyl toluene sulfonate, benzoin toluene sulfonate, 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, examples of the polymerization initiator (D) include: benzoin, benzoin Benzoin compounds such as methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- 4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc. Benzophenone compounds; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, phenylglyoxylate methyl ester, 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, phenylalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds. The polymerization initiator is more preferably a polymerization initiator containing an O-acyl oxime 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 to 30 parts by mass, more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). . When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time is shortened. Therefore, the productivity of the color filter is improved.
<溶劑(E)> <Solvent (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。 The solvent (E) is not particularly limited, and solvents commonly used in this field can be used. For example, ester solvents (solvents that contain -COO- but not -O- in the molecule), ether solvents (solvents that contain -O- but do not contain -COO- in the molecule), ether ester solvents (solvents that do not contain -COO- in the molecule), Solvents that contain -COO- and -O-), ketone solvents (solvents that contain -CO- and do not contain -COO- in the molecule), alcohol solvents (solvents that contain OH in the molecule and do not contain -O-, -CO - and -COO- solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl styrene.
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 the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , Butyl propionate, Isopropyl butyrate, Ethyl butyrate, Butyl butyrate, Methyl pyruvate, Ethyl pyruvate, Propyl pyruvate, Methyl acetate acetate, Ethyl acetate acetate, Ring 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, 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 ether Dibutyl glycol, anisole, phenylethyl 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 the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethoxyethyl acetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, 2-methoxypropylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol mono 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 acetate Acid esters, etc.
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 the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.
作為芳香族烴溶劑,可列舉:苯、甲苯、二甲苯及均三甲苯等。 Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, and the like.
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1atm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、乳酸乙酯及3-乙氧基丙酸乙酯。 Among the solvents, an organic solvent having a boiling point at 1 atm of 120° C. or more and 180° C. or less is preferred in terms of coating properties and drying properties. As the solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethyl ether are preferred. Glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 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 rate of the solvent (E) is preferably 70 mass% to 95 mass%, more preferably 75 mass% to 92 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. When the content rate of the solvent (E) is within the above range, the flatness during coating tends to be improved, and the color density is not insufficient when forming a color filter, so the display characteristics tend to be improved.
<調平劑(F)> <Leveling agent (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。 Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, silicone surfactants having fluorine atoms, and the like. These may have a polymerizable group in a side chain.
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。 Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) , KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Japanese Momentive Performance Materials) 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 surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), 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 Co., Ltd.), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), 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 siloxane bond and a fluorocarbon chain in the molecule. Specifically, examples include: Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (DIC). ) (shares, manufacturing), etc.
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。 The content rate 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, relative to the total amount of the colored curable resin composition, 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> <Other ingredients>
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。 The colored curable resin composition of the present invention may optionally contain additives known in the technical field such as polymerization starting aids, fillers, other polymer compounds, adhesion accelerators, light stabilizers, and chain transfer agents.
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。 Examples of the adhesion accelerator include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, and 3-glycidyloxy Propyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxy Cyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3 -Mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N- 2-(Aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyl Trimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane wait.
<著色硬化性樹脂組成物的製造方法> <Production method of colored curable resin composition>
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。 The colored curable resin composition of the present invention can be prepared by, for example, using a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and an optional solvent (E), Leveling agent (F) and other ingredients are mixed and prepared.
<彩色濾光片的製造方法> <Manufacturing method of color filter>
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。 Examples of methods for producing a colored pattern from the colored curable resin composition of the present invention include photolithography, inkjet, and printing. Among them, photolithography is preferred. The photolithography method is a method of applying 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 light mask. In the photolithography method, by not using a photomask during exposure and/or not performing development, a colored coating film that is a cured product of the colored composition layer can be formed. The colored pattern or colored coating film thus formed is the color filter of the present invention.
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0.1μm~30μm、較佳為0.1μm~20μm、進而佳為0.5μm~6μm。 The film thickness of the color filter to be produced is not particularly limited and can be determined according to the purpose or use. It is appropriately adjusted according to the purpose, for example, 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and even 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, and soda-lime glass with a silica-coated surface can be used; or polycarbonate, polymethyl methacrylate, poly(methylmethacrylate), etc. 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 the 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。 The formation of pixels of various colors based on the photolithography method can be performed by well-known or conventional devices or conditions. For example, it can be produced as follows.
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。 First, the colored curable resin composition is applied to a substrate, and is heated and dried (prebaked) and/or dried under reduced pressure to remove volatile components such as solvents and dry them, thereby obtaining a smooth colored composition. layer.
作為塗佈方法,可列舉:旋塗法、狹縫塗佈法、狹縫及旋塗法等。 Examples of coating methods include spin coating, slit coating, slit and spin coating, and the like.
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。 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, more preferably 30 seconds to 30 minutes.
於進行減壓乾燥的情況下,較佳為於50Pa~150Pa的壓力下,於20℃~25℃的溫度範圍內進行。 When drying under reduced pressure is performed, it is preferably carried out under a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C.
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 film thickness of the coloring composition layer is not particularly limited and may be 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。 Then, the coloring composition layer blocks the light used to form the target coloring pattern. Covered and exposed. The pattern on this photomask is not particularly limited, and a pattern corresponding to the intended use can be used.
作為曝光中使用的光源,較佳為產生250nm~450nm的波長的光的光源。例如,亦可對於未滿350nm的光,使用截止該波長範圍的濾光片進行截止,或者對於436nm附近、408nm附近、365nm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。 As a light source used for exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, you can also use a filter that cuts off the wavelength range of less than 350 nm, or you can use a band pass filter that cuts out the light in those wavelength ranges around 436 nm, 408 nm, and 365 nm. filter) for selective removal. Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.
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。 In order to uniformly irradiate the entire exposure surface with parallel light or to accurately align the mask 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。 The exposed colored composition layer is brought into contact with a developer and developed, thereby forming a colored pattern on the substrate. By development, the unexposed portion of the colored composition layer is dissolved in the developer and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 mass% to 10 mass%, more preferably 0.03 mass% to 5 mass%. Furthermore, the developer may contain a surfactant.
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。 The development method may be any one of liquid coating method, dipping method, spray method, etc. Furthermore, the substrate can be tilted to any angle during development.
顯影後,較佳為進行水洗。 After development, it is preferred 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。 Furthermore, it is preferable to post-bake the obtained colored pattern. post bake The temperature is preferably 150°C~250°C, and more preferably 160°C~235°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes.
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。 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.
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。 In the following synthesis examples, the compound was identified by Nuclear Magnetic Resonance (NMR) (JNM-EX-270; (manufactured by JEOL Ltd.)).
(著色劑合成例1) (Coloring agent synthesis example 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。 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 Co., Ltd.) 44.0 parts mixed. The resulting mixture was stirred at 90°C for 8 hours. After the reaction, 50 parts of 10% baking soda water was added, and then 100 parts of ethyl acetate was added, and the water layer was discarded. After repeating the washing operation 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]
式(a-1)所表示的化合物的1H-NMR(270MHz、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)-d6) δ 0.85 of the compound represented by formula (a-1) (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 formula (a-1) thus obtained, 2.2 parts of 3-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.015 part of palladium acetate, and sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) Co., Ltd.), 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. To the obtained mixture were added 30 parts of ethyl acetate and 100 parts of water, and the aqueous layer was discarded. After repeating the washing operation with water twice, the solvent was distilled off. The residue was purified using silica gel chromatography (chloroform/hexane=1/1), and the obtained oil was dried under reduced pressure at 60°C for 24 hours to obtain the following formula (a-2) 1.9 parts of the compound represented.
[化19]
式(a-2)所表示的化合物的1H-NMR(270MHz、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 (270MHz, δ value (ppm, TMS standard), 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)
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 above-obtained formula (a-2), 0.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.), 1 -Mix 90.0 parts of butanol and 60.0 parts of toluene. The resulting mixture was stirred at 125° C. for 3 hours while removing the generated water using a Dean-Stark tube. After the reaction, the solvent was distilled off, 15 parts of acetic acid was added, and then added dropwise to 100 parts of 18% saline, 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 the compound represented by formula (AII-10).
[化20]
式(AII-10)所表示的化合物的1H-NMR(270MHz、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 (270MHz, δ value (ppm, TMS standard), 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)
(樹脂合成例1) (Resin synthesis example 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,放入丙二醇單甲醚乙酸酯324份,一面攪拌一面加熱至85℃。繼而,使用滴加泵花4小時向該燒瓶內滴加甲基丙烯酸60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30份(混合比例為1:1)、9-乙烯基咔唑210份、丙二醇單甲醚乙酸酯190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)31份溶解於丙二醇單甲醚乙酸酯155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163mPa.s、固體成分為31.8%的共聚物(樹脂(B-1))溶液。 An appropriate amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere. 324 parts of propylene glycol monomethyl ether acetate was added and heated to 85°C while stirring. Then, 60 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4 acrylic acid were added dropwise into the flask over 4 hours using a dropping pump. - 30 parts of a mixture of epoxy tricyclic [5.2.1.0 2,6 ] decane-9-yl ester (mixing ratio is 1:1), 210 parts of 9-vinylcarbazole, 190 parts of propylene glycol monomethyl ether acetate portions of mixed solution. On the other hand, 31 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in propylene glycol monomethyl ether was added dropwise into the flask over 5 hours using another dropping pump. A mixed solution containing 155 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 B-type viscosity (23°C) of 163mPa. s. A copolymer (resin (B-1)) solution with a solid content of 31.8%.
所得到的樹脂(B-1)的重量平均分子量(Mw)為7900,分散度(Mw/Mn)為1.99,固體成分換算的酸價為107mg-KOH/g。樹脂(B-1)具有下述結構單元。 The weight average molecular weight (Mw) of the obtained resin (B-1) was 7900, the dispersion degree (Mw/Mn) was 1.99, and the acid value in terms of solid content was 107 mg-KOH/g. Resin (B-1) has the following structural units.
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。 The polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by gel permeation chromatography (GPC) using the following conditions.
裝置:HLC-8120GPC(東曹(Tosoh)(股)製造) Device: HLC-8120GPC (manufactured by Tosoh Corporation)
管柱:TSK-GELG2000HXL Column: TSK-GELG2000HXL
管柱溫度:40℃ Tube string temperature: 40℃
溶劑:四氫呋喃(tetrahydrofuran,THF) Solvent: tetrahydrofuran (THF)
流速:1.0mL/min Flow rate: 1.0mL/min
被檢液固體成分濃度:0.001質量%~0.01質量% Solid content concentration of the liquid to be tested: 0.001 mass%~0.01 mass%
注入量:50μL Injection volume: 50μL
檢測器:折射率(refractive index,RI) Detector: 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) Calibration standard materials: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)
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 ratio (Mw/Mn) of the obtained weight average molecular weight in terms of polystyrene and the number average molecular weight was defined as the degree of dispersion.
(樹脂合成例2) (Resin synthesis example 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,放入丙二醇單甲醚乙酸酯100份,一面攪拌一面加熱至85℃。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-2))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53mg-KOH/g。樹脂(B-2)具有下述結構單元。 An appropriate amount of nitrogen was circulated in a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere. 100 parts of propylene glycol monomethyl ether acetate was added and heated to 85°C while stirring. Next, 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3 acrylic acid were added dropwise into the flask over about 5 hours using a dropping pump. , a solution of 171 parts of a mixture of 4-epoxy tricyclic [5.2.1.0 2,6 ] decane-9-yl ester (mixing ratio 1:1) dissolved in 40 parts of propylene glycol monomethyl ether acetate. . On the other hand, 26 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) dissolved in propylene glycol monomethyl was added dropwise into the flask over about 5 hours using another dropping pump. A solution containing 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-2)) with a solid content of 43.5%. The weight average molecular weight of the obtained resin (B-2) was 8000, the dispersion degree was 1.98, and the acid value in terms of solid content was 53 mg-KOH/g. Resin (B-2) has the following structural units.
[化22]
[實施例1~實施例3、比較例1] [Example 1 to Example 3, Comparative Example 1]
[著色硬化性樹脂組成物的製備] [Preparation of colored curable resin composition]
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。 Each component was mixed so as to have the composition shown in Table 2, and a colored curable resin composition was obtained.
表2中,各成分表示以下的化合物。 In Table 2, each component represents the following compound.
著色劑(A-1):式(AII-10)所表示的化合物 Colorant (A-1): compound represented by formula (AII-10)
樹脂(B-1):樹脂(B-1)(固體成分換算) Resin (B-1): Resin (B-1) (solid content conversion)
樹脂(B-2):樹脂(B-2)(固體成分換算) Resin (B-2): Resin (B-2) (solid content conversion)
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) Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
聚合起始劑(D-1):N-1919(艾迪科(ADEKA)公司製造;O-醯基肟化合物) Polymerization initiator (D-1): N-1919 (manufactured by ADEKA; O-acyl oxime compound)
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) Polymerization initiator (D-2): DFI-091 (manufactured by Daito Chemix; O-acyl oxime compound)
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) Polymerization initiator (D-3): N-benzyloxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine (Irgacure (registered) Trademark) OXE-01; manufactured by BASF; O-acyl oxime compound)
溶劑(E-1):4-羥基-4-甲基-2-戊酮 Solvent (E-1): 4-hydroxy-4-methyl-2-pentanone
溶劑(E-2):丙二醇單甲醚乙酸酯 Solvent (E-2): Propylene glycol monomethyl ether acetate
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」) Leveling agent (F-1): Polyether modified silicone oil ("Toray Silicone SH8400" manufactured by Toray Dow Corning Co., Ltd.)
<著色塗膜的製作> <Preparation of colored coating>
於5cm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2.0μm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100mJ/cm2的曝光量(365nm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。 The colored curable resin composition was applied on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Corporation) by spin coating so that the film thickness after baking would be 2.0 μm. Pre-bake at 100°C for 3 minutes to form a colored composition layer. After leaving it to cool, an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used to irradiate the colored composition layer with light at an exposure dose of 100 mJ/cm 2 (based on 365 nm) in an atmospheric environment. Thereafter, post-baking was performed at 230° C. for 30 minutes in an oven to obtain a colored coating film.
1.耐熱性(△Eab*) 1. Heat resistance (△Eab*)
於預烘烤後及後烘烤後進行色度的測定,根據該測定值並利用日本工業標準(Japanese Industrial Standards,JIS)Z 8730:2009(7.色差的計算方法)中記載的方法來計算色差△Eab*,將結果示於表3中。△Eab*越小,意味著顏色變化越小。 Measure the color after pre-baking and post-baking, and calculate based on the measured value using the method described in Japanese Industrial Standards (JIS) Z 8730: 2009 (7. Calculation method of color difference) Color difference ΔEab*, the results are shown in Table 3. The smaller △Eab* means the smaller the color change.
2.極大吸光度保持率 2. Maximum absorbance retention rate
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4中。 The maximum absorbance was determined from the spectra measured after prebaking and postbaking, and the retention rate of the maximum absorbance was calculated according to the following formula. The results are shown in Table 4.
吸光度保持率(△Abs.Max)=後烘烤後的極大吸光度/預烘烤後的極大吸光度 Absorbance retention rate (△Abs.Max) = maximum absorbance after post-baking/maximum absorbance after pre-baking
吸光度保持率越高,意味著成膜步驟中的適應性越高。 The higher the absorbance retention rate, the higher the adaptability in the film-forming step.
3.明度 3.Brightness
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光源的特性函數求出國際照明學會(Commission Internationale de I'Eclairage,CIE)的XYZ表色系中的xy色度座標(x,y)與刺激值Y,將結果示於表5中。Y的值越大,表示明度越高。 About the colored curable resin set of Example 1, Example 3, and Comparative Example 1 The chromaticity of the colored coating film formed on the finished product was calculated based on the spectrum measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.) and the characteristic function of the C light source. Table 5 shows the results of the xy chromaticity coordinates (x, y) and stimulus value Y in the XYZ color system of the Commission Internationale de I'Eclairage (CIE). The larger the value of Y, the higher the brightness.
根據本發明的著色硬化性樹脂組成物,可形成耐熱性優異的彩色濾光片。 According to the colored curable resin composition of the present invention, a color filter excellent in heat resistance can be formed.
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