TWI840555B - Colored hardening resin composition - Google Patents
Colored hardening resin composition Download PDFInfo
- Publication number
- TWI840555B TWI840555B TW109114427A TW109114427A TWI840555B TW I840555 B TWI840555 B TW I840555B TW 109114427 A TW109114427 A TW 109114427A TW 109114427 A TW109114427 A TW 109114427A TW I840555 B TWI840555 B TW I840555B
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- Prior art keywords
- group
- carbon atoms
- substituent
- alkyl group
- formula
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- 239000011342 resin composition Substances 0.000 title claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 235
- 229920005989 resin Polymers 0.000 claims abstract description 91
- 239000011347 resin Substances 0.000 claims abstract description 91
- 239000000470 constituent Substances 0.000 claims abstract description 69
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 39
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 25
- 239000003086 colorant Substances 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 343
- 125000000217 alkyl group Chemical group 0.000 claims description 273
- 125000001424 substituent group Chemical group 0.000 claims description 198
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 239000000049 pigment Substances 0.000 claims description 71
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007870 radical polymerization initiator Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 abstract description 38
- 238000000576 coating method Methods 0.000 abstract description 22
- 239000011248 coating agent Substances 0.000 abstract description 20
- 238000010438 heat treatment Methods 0.000 abstract description 9
- -1 propylphenyl Chemical group 0.000 description 174
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 155
- 239000000975 dye Substances 0.000 description 77
- 239000002904 solvent Substances 0.000 description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 50
- 239000000178 monomer Substances 0.000 description 47
- 239000006185 dispersion Substances 0.000 description 37
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000001054 red pigment Substances 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 9
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000011324 bead Substances 0.000 description 9
- 239000001055 blue pigment Substances 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 235000006708 antioxidants Nutrition 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 239000011572 manganese Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 7
- 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 7
- 238000001035 drying Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 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 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000000206 photolithography Methods 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 5
- 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 5
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 229940007550 benzyl acetate Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003759 ester based solvent Substances 0.000 description 4
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- JUHDUIDUEUEQND-UHFFFAOYSA-N methylium Chemical compound [CH3+] JUHDUIDUEUEQND-UHFFFAOYSA-N 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- 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 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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- 229910052701 rubidium Inorganic materials 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000007858 starting 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
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-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
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229910001432 tin ion Inorganic materials 0.000 description 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- JOHIXGUTSXXADV-UHFFFAOYSA-N undec-2-ene Chemical compound CCCCCCCCC=CC JOHIXGUTSXXADV-UHFFFAOYSA-N 0.000 description 1
- NVPYPLODXLUCNR-UHFFFAOYSA-N undec-3-ene Chemical compound [CH2]CCCCCCC=CCC NVPYPLODXLUCNR-UHFFFAOYSA-N 0.000 description 1
- BQGFQLZEZOPJFT-UHFFFAOYSA-N undec-4-ene Chemical compound [CH2]CCC=CCCCCCC BQGFQLZEZOPJFT-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- JXUKQCUPTNLTCS-UHFFFAOYSA-N vat green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Abstract
本發明提供一種可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少的著色硬化性樹脂組成物。一種著色硬化性樹脂組成物,其為包含著色劑(A)、樹脂(B)、聚合性化合物(C)以及聚合起始劑(D)的著色硬化性樹脂組成物,並且著色硬化性樹脂組成物進而包含酚系抗氧化劑(E),且樹脂(B)含有包含式(1b)所表示的構成單元(b1-1)的樹脂(B1)[下述式中的記號的定義如說明書中所記載般]。 The present invention provides a coloring curable resin composition that can suppress the reduction in thickness of a coloring pattern or a coloring coating film caused by heating (particularly post-baking). A coloring curable resin composition comprising a coloring agent (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), wherein the coloring curable resin composition further comprises a phenolic antioxidant (E), and the resin (B) comprises a resin (B1) comprising a constituent unit (b1-1) represented by formula (1b) [the symbols in the following formula are defined as described in the specification].
Description
本發明是有關於一種著色硬化性樹脂組成物。 The present invention relates to a colored curable resin composition.
著色硬化性樹脂組成物是於液晶顯示裝置、電致發光顯示裝置及電漿顯示器等顯示裝置中所使用的彩色濾光片的製造中使用,且開發有多種樹脂組成物。例如,專利文獻1中記載有一種彩色濾光片用樹脂組成物,其含有:溶劑、反應性稀釋劑、光聚合起始劑、著色劑、以及包含式(1)所表示的構成單元的共聚物。 Colored curable resin compositions are used in the manufacture of color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and a variety of resin compositions have been developed. For example, Patent Document 1 describes a resin composition for a color filter, which contains: a solvent, a reactive diluent, a photopolymerization initiator, a colorant, and a copolymer containing a constituent unit represented by formula (1).
[式(1)中的記號的定義如專利文獻1的記載般] [The definitions of symbols in formula (1) are as described in patent document 1]
[現有技術文獻] [Prior art literature]
[專利文獻] [Patent Literature]
[專利文獻1]WO 2018/110097 A1 [Patent Document 1] WO 2018/110097 A1
作為利用著色硬化性樹脂組成物形成彩色濾光片的方法,例如可列舉光微影法及使用噴墨設備的方法。於光微影法中,通常包括如下步驟:將著色硬化性樹脂組成物塗佈於基板上,藉由加熱乾燥(預烘烤)及/或減壓乾燥去除溶劑等揮發成分而形成組成物層,對該組成物層照射(曝光)光,使顯影液與曝光後的組成物層接觸而形成(顯影)著色圖案或著色塗膜。該顯影後,經常進行對著色圖案進行加熱的後烘烤。 As a method of forming a color filter using a colored curable resin composition, for example, photolithography and a method using an inkjet device can be cited. In the photolithography method, the following steps are generally included: the colored curable resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and/or reduced pressure drying to form a composition layer, and the composition layer is irradiated (exposed) with light, so that the developer contacts the exposed composition layer to form (develop) a colored pattern or a colored coating film. After the development, the colored pattern is often post-baked by heating.
於現有的著色硬化性樹脂組成物中,著色圖案或著色塗膜的厚度有時會因後烘烤而大幅減少。本發明是著眼於此種情況而成,其目的在於提供一種可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少的著色硬化性樹脂組成物。 In existing coloring curable resin compositions, the thickness of the coloring pattern or the coloring coating film is sometimes greatly reduced due to post-baking. The present invention is made with this in mind, and its purpose is to provide a coloring curable resin composition that can suppress the reduction in the thickness of the coloring pattern or the coloring coating film caused by heating (especially post-baking).
可達成所述目的的本發明為如下所述。 The present invention that can achieve the above-mentioned purpose is as follows.
[1]一種著色硬化性樹脂組成物,其為包含著色劑(A)、樹脂(B)、聚合性化合物(C)以及聚合起始劑(D)的著色硬化性樹脂組成物,並且著色硬化性樹脂組成物進而包含酚系抗氧化劑(E),且樹脂(B)含有包含式(1b)所表示的構成單元(b1-1)的樹 脂(B1)。 [1] A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D), wherein the colored curable resin composition further comprises a phenolic antioxidant (E), and the resin (B) comprises a resin (B1) comprising a constituent unit (b1-1) represented by formula (1b).
[式(1b)中,R1B表示氫原子或甲基,R2B~R4B分別獨立地表示氫原子、碳數1~6的烷基或碳數1~6的烷氧基,n表示1~10的整數,以及*表示鍵結位置,其中,R2B~R4B的至少一個為碳數1~6的烷氧基]。 [In formula (1b), R 1B represents a hydrogen atom or a methyl group, R 2B to R 4B each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, n represents an integer of 1 to 10, and * represents a bonding position, wherein at least one of R 2B to R 4B is an alkoxy group having 1 to 6 carbon atoms].
[2]如所述[1]所述的著色硬化性樹脂組成物,其中樹脂(B1)為包含構成單元(b1-1)、源自具有酸性基的聚合性不飽和化合物的構成單元(b1-2)及其他構成單元(b1-3)的共聚物,且將共聚物中的所有構成單元的合計設為100莫耳%時的構成單元(b1-1)的量為1莫耳%~50莫耳%。 [2] The colored curable resin composition as described in [1], wherein the resin (B1) is a copolymer comprising a constituent unit (b1-1), a constituent unit (b1-2) derived from a polymerizable unsaturated compound having an acidic group, and other constituent units (b1-3), and the amount of the constituent unit (b1-1) is 1 mol% to 50 mol% when the total of all the constituent units in the copolymer is taken as 100 mol%.
[3]如所述[1]或[2]所述的著色硬化性樹脂組成物,其中樹脂(B1)的重量平均分子量為1,000~50,000。 [3] The colored curable resin composition as described in [1] or [2], wherein the weight average molecular weight of the resin (B1) is 1,000 to 50,000.
[4]如所述[1]至[3]中任一項所述的著色硬化性樹脂組成物,其中樹脂(B1)的含量相對於聚合性化合物(C)100重量份 而為5重量份~400重量份。 [4] A colored curable resin composition as described in any one of [1] to [3], wherein the content of the resin (B1) is 5 parts by weight to 400 parts by weight relative to 100 parts by weight of the polymerizable compound (C).
[5]如所述[1]至[4]中任一項所述的著色硬化性樹脂組成物,其中酚系抗氧化劑(E)的含量相對於聚合性化合物(C)100重量份而為0.1重量份~25重量份。 [5] The colored curable resin composition as described in any one of [1] to [4], wherein the content of the phenolic antioxidant (E) is 0.1 parts by weight to 25 parts by weight relative to 100 parts by weight of the polymerizable compound (C).
[6]如所述[1]至[5]中任一項所述的著色硬化性樹脂組成物,其中著色劑(A)包含染料(A1)及顏料(A2)。 [6] The colored curable resin composition as described in any one of [1] to [5], wherein the coloring agent (A) comprises a dye (A1) and a pigment (A2).
[7]如所述[1]至[6]中任一項所述的著色硬化性樹脂組成物,其中聚合性化合物(C)為自由基聚合性化合物,且聚合起始劑(D)為光自由基聚合起始劑。 [7] The colored curable resin composition as described in any one of [1] to [6], wherein the polymerizable compound (C) is a radical polymerizable compound, and the polymerization initiator (D) is a photoradical polymerization initiator.
[8]如所述[1]至[7]中任一項所述的著色硬化性樹脂組成物,其中著色劑(A)包含選自由式(A3-1)所表示的化合物、以及式(A3-2)所表示的化合物所組成的群組中的至少一種化合物(A3)。 [8] The colored curable resin composition as described in any one of [1] to [7], wherein the coloring agent (A) comprises at least one compound (A3) selected from the group consisting of compounds represented by formula (A3-1) and compounds represented by formula (A3-2).
[式(A3-1)中,R41a及R42a分別獨立地表示氫原子、可
具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R41a與R42a鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環,R43a及R44a分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R43a與R44a鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環,R47a~R54a分別獨立地表示氫原子、鹵素原子、硝基、羥基、-SO3 -、-SO2-N--SO2-Rf、或可具有取代基的碳數1~8的烷基,Rf表示碳數1~12的氟烷基,環T1a表示可具有取代基的碳數6~14的芳香族烴環或可具有取代基的5員~10員的芳香族雜環,所述碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個,所述碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述碳數7~30的芳烷基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述碳數6~14的芳香族烴環可具有的取代基為選自由鹵素
原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述5員~10員的芳香族雜環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個,於所述碳數1~20的飽和烴基為碳數2~20的飽和烴基的情況下,所述飽和烴基中所含的-CH2-可經取代為-O-或-CO-,於所述碳數1~8的烷基為碳數2~8的烷基的情況下,所述烷基中所含的-CH2-可經取代為-O-或-CO-,r表示1以上的整數,Mr+表示氫離子、r價的金屬離子或N+(R55a)4,四個R55a可相同亦可不同,R55a表示氫原子、碳數1~20的飽和烴基或碳數7~10的芳烷基,k表示式(A3-1a)所表示的陰離子所具有的-SO3 -及-SO2-N--SO2-Rf的個數的合計,且為2以上的整數,[化4]
[式(A3-1a)中,環T1a、R41a~R44a及R47a~R54a分別與所述為相同含義] [In formula (A3-1a), ring T1a , R41a to R44a and R47a to R54a have the same meanings as described above]
於r為2以上的整數的情況下,式(A3-1a)所表示的多個陰離子可相同亦可不同,以及於k-1為2以上的整數的情況下,多個Mr+可相同亦可不同] When r is an integer greater than 2, the multiple anions represented by formula (A3-1a) may be the same or different, and when k-1 is an integer greater than 2, the multiple Mr + may be the same or different.]
[式(A3-2)中,R41b及R42b分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R41b與R42b鍵結並與該些所鍵結的氮原子一同形成3員~10員
的含氮雜環,R43b及R44b分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R43b與R44b鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環,R47b~R54b分別獨立地表示氫原子、鹵素原子、硝基、羥基、或可具有取代基的碳數1~8的烷基,環T1b表示可具有取代基的碳數6~14的芳香族烴環或可具有取代基的5員~10員的芳香族雜環,所述碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個,所述碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述碳數7~30的芳烷基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述碳數6~14的芳香族烴環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個,所述5員~10員的芳香族雜環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基
所組成的群組中的至少一個,所述碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個,於所述碳數1~20的飽和烴基為碳數2~20的飽和烴基的情況下,所述飽和烴基中所含的-CH2-可經取代為-O-或-CO-,於所述碳數1~8的烷基為碳數2~8的烷基的情況下,所述烷基中所含的-CH2-可經取代為-O-或-CO-,m表示1以上的整數,[Y]m-表示m價的陰離子,以及於m為2以上的整數的情況下,式(A3-2c)所表示的多個陽離子可相同亦可不同;
[式(A3-2c)中,環T1b、R41b~R44b及R47b~R54b分別與所述為相同含義]]。 [In formula (A3-2c), ring T 1b , R 41b to R 44b and R 47b to R 54b have the same meanings as described above]].
[9]如所述[8]所述的著色硬化性樹脂組成物,其中著色劑 (A)包含與化合物(A3)不同的染料(A1)。 [9] The colored curable resin composition as described in [8], wherein the coloring agent (A) contains a dye (A1) different from the compound (A3).
若使用本發明的著色硬化性樹脂組成物,則可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少。 If the colored curable resin composition of the present invention is used, the reduction in thickness of the colored pattern or colored coating film caused by heating (especially post-baking) can be suppressed.
本發明的著色硬化性樹脂組成物包含:著色劑(A)、樹脂(B)、聚合性化合物(C)、聚合起始劑(D)以及酚系抗氧化劑(E)。進而,樹脂(B)含有包含所述式(1b)所表示的構成單元(b1-1)的樹脂(B1)。以下,依次說明本發明的著色硬化性樹脂組成物的各成分。 The coloring curable resin composition of the present invention comprises: a coloring agent (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and a phenolic antioxidant (E). Furthermore, the resin (B) contains a resin (B1) comprising a constituent unit (b1-1) represented by the formula (1b). The components of the coloring curable resin composition of the present invention are described below in sequence.
只要並無特別說明,則本說明書中說明的各成分及用於製造各成分的原料均可使用僅一種,亦可併用兩種以上。 Unless otherwise specified, each component and the raw materials used to produce each component described in this manual may be used alone or in combination of two or more.
<著色劑(A)> <Colorant (A)>
著色劑(A)被分類為可溶於溶劑的染料(A1)、與不溶於溶劑的顏料(A2)。於本發明的一態樣中,著色劑(A)包含染料(A1)及顏料(A2)兩者。 Colorants (A) are classified into dyes (A1) soluble in solvents and pigments (A2) insoluble in solvents. In one embodiment of the present invention, colorants (A) include both dyes (A1) and pigments (A2).
染料(A1)較佳為包含選自由氧雜蒽染料、三芳基甲烷染料及香豆素染料所組成的群組中的至少一種染料。於使用選自 所述群組中的至少一種染料的情況下,其合計量相對於染料(A1)整體而較佳為1重量%以上且100重量%以下,更佳為2重量%以上且100重量%以下,進而佳為5重量%以上且100重量%以下。 The dye (A1) preferably includes at least one dye selected from the group consisting of oxanthracene dyes, triarylmethane dyes and coumarin dyes. When at least one dye selected from the group is used, the total amount thereof is preferably 1% by weight or more and 100% by weight or less, more preferably 2% by weight or more and 100% by weight or less, and further preferably 5% by weight or more and 100% by weight or less, relative to the whole dye (A1).
染料(A1)更佳為包含氧雜蒽染料。於使用氧雜蒽染料的情況下,其含量相對於染料(A1)整體而較佳為1重量%以上且100重量%以下,更佳為2重量%以上且100重量%以下,進而佳為5重量%以上且100重量%以下,最佳為100重量%。即,染料(A1)最佳為由氧雜蒽染料構成。 The dye (A1) preferably contains an oxyanthracene dye. When an oxyanthracene dye is used, its content is preferably 1% by weight or more and 100% by weight or less, more preferably 2% by weight or more and 100% by weight or less, further preferably 5% by weight or more and 100% by weight or less, and most preferably 100% by weight, relative to the whole dye (A1). That is, the dye (A1) is preferably composed of an oxyanthracene dye.
氧雜蒽染料為包含分子內具有氧雜蒽骨架的化合物的染料。作為氧雜蒽染料,例如可列舉:C.I.酸性紅(acid red)51(以下,省略C.I.酸性紅的記載而僅記載編號;其他染料亦同樣如此)、52、87、92、94、289、388;C.I.酸性紫(acid violet)9、30、102;C.I.鹼性紅(basic red)1(玫瑰紅(rhodamine)6G)、2、3、4、8;C.I.鹼性紅10、11;C.I.鹼性紫(basic violet)10(玫瑰紅B)、11;C.I.溶劑紅(solvent red)218;C.I.媒介紅(mordant red)27;C.I.活性紅(reactive red)36(孟加拉玫瑰紅(rose bengal)B);酸性玫瑰紅(sulforhodamine)G;日本專利特開2010-32999號公報中記載的氧雜蒽染料及日本專利第4492760號公報中記載的氧雜蒽染料等。作為氧雜蒽染料,較佳為溶解於有機溶劑的染料。 The oxanthracene dye is a dye including a compound having an oxanthracene skeleton in the molecule. Examples of oxyanthracene dyes include C.I. acid red 51 (hereinafter, C.I. acid red is omitted and only the number is recorded; the same applies to other dyes), 52, 87, 92, 94, 289, 388; C.I. acid violet 9, 30, 102; C.I. basic red 1 (rhodamine 6G), 2, 3, 4, 8; C.I. basic red 10, 11; C.I. basic violet 10 (rose red B), 11; C.I. solvent red 218; C.I. mordant red 27; C.I. reactive red 36 (rose Bengal) bengal) B); acid rose red (sulforhodamine) G; oxyanthracene dyes described in Japanese Patent Publication No. 2010-32999 and oxyanthracene dyes described in Japanese Patent Publication No. 4492760, etc. As oxyanthracene dyes, dyes that are soluble in organic solvents are preferred.
作為較佳的氧雜蒽染料,可列舉式(1a)所表示的化合物(以下,有時記載為「化合物(1a)」)。化合物(1a)亦可為其互變異構體。於使用化合物(1a)的情況下,其含量相對於氧雜 蒽染料整體而較佳為50重量%以上,更佳為70重量%以上,進而佳為90重量%以上。特佳為僅使用化合物(1a)作為氧雜蒽染料。 As a preferred oxyanthracene dye, a compound represented by formula (1a) (hereinafter, sometimes described as "compound (1a)") can be listed. Compound (1a) may also be a tautomer. When compound (1a) is used, its content is preferably 50% by weight or more, more preferably 70% by weight or more, and further preferably 90% by weight or more relative to the total oxyanthracene dye. It is particularly preferred to use only compound (1a) as the oxyanthracene dye.
[式(1a)中,R1~R4分別獨立地表示氫原子、可具有取代基的碳數1~20的一價飽和烴基、可具有取代基的碳數6~10的一價芳香族烴基或*-R12-Si(R13)3所表示的基(所述式中,*表示與氮原子的鍵結位置),所述飽和烴基中所含的-CH2-可經-O-、-CO-或-NR11-取代,R1及R2可一起形成包含氮原子的環,R3及R4可一起形成包含氮原子的環,R5表示-OH、-SO3 -、-SO3H、-SO3 -Z+、-CO2H、-CO2 -Z+、-CO2R8、-SO3R8或-SO2NR9R10,R6及R7分別獨立地表示氫原子或碳數1~6的烷基,m表示0~5的整數,於m為2以上時,多個R5可相同亦可不同,a表示0或1的整數, X表示鹵素原子,Z+表示N+(R11)4、Na+或K+,四個R11可相同亦可不同,R8表示可經鹵素原子取代的碳數1~20的一價飽和烴基,R9及R10分別獨立地表示氫原子或可具有取代基的碳數1~20的一價飽和烴基,所述飽和脂肪族烴基中所含的-CH2-可經-O-、-CO-、-NH-或-NR8-取代,R9及R10可彼此鍵結而形成包含氮原子的3員環~10員環的雜環,R11表示氫原子、碳數1~20的一價飽和烴基或碳數7~10的芳烷基,R12表示碳數1~10的烷二基,所述烷二基中所含的-CH2-可經-O-、-CO-、-NR8-、-OCO-、-COO-、-OCONH-、-CONH-或-NHCO-取代,以及R13表示氫原子、羥基、碳數1~4的烷基或碳數1~4的烷氧基,以及多個R13可分別相同亦可不同,其中,於在式(1a)中存在離子形態的-SO3 -的情況下,其數量為一個] [In the formula (1a), R 1 to R 4 each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a group represented by *-R 12 -Si(R 13 ) 3 (in the above formula, * represents a bonding position to a nitrogen atom), -CH 2 - contained in the above saturated hydrocarbon group may be substituted by -O-, -CO-, or -NR 11 -, R 1 and R 2 may form a ring containing a nitrogen atom together, R 3 and R 4 may form a ring containing a nitrogen atom together, and R 5 represents -OH, -SO 3 - , -SO 3 H, -SO 3 - Z + , -CO 2 H, -CO 2 - Z + , -CO 2 R 8 , -SO 3 R 8 , or -SO 2 NR 9 R 10 , R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 5's may be the same or different, a represents an integer of 0 or 1, X represents a halogen atom, Z + represents N + (R 11 ) 4 , Na + or K + , and four R 11's may be the same or different, R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may be substituted by a halogen atom, R 9 and R 10 each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - contained in the saturated aliphatic hydrocarbon group may be substituted by -O-, -CO-, -NH- or -NR 8 -, and R 9 and R R 10 may be bonded to each other to form a 3- to 10-membered heterocyclic ring including a nitrogen atom, R 11 represents a hydrogen atom, a monovalent saturated alkyl group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms, R 12 represents an alkanediyl group having 1 to 10 carbon atoms, wherein -CH 2 - contained in the alkanediyl group may be substituted by -O-, -CO-, -NR 8 -, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-, and R 13 represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and a plurality of R 13 may be the same or different, wherein, when -SO 3 - in ionic form is present in formula (1a), the number thereof is one]
作為R1~R4中的可具有取代基的碳數6~10的一價芳香族烴基,例如可列舉:苯基、甲苯基、二甲苯基、均三甲苯基、丙基苯基及丁基苯基等。 Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent in R 1 to R 4 include phenyl, tolyl, xylyl, mesityl, propylphenyl, and butylphenyl.
作為所述芳香族烴基可具有的取代基,可列舉:鹵素原子、-R8、-OH、-OR8、-SO3 -、-SO3H、-SO3 -Z+、-CO2H、-CO2R8、-SR8、-SO2R8、-SO3R8或-SO2NR9R10。該些中,較佳為-SO3 -、-SO3H、 -SO3 -Z+及-SO2NR9R10,更佳為-SO3 -Z+及-SO2NR9R10。作為該情況下的-SO3 -Z+,較佳為-SO3 -N+(R11)4。 Examples of the substituent which the aromatic hydrocarbon group may have include a halogen atom, -R 8 , -OH, -OR 8 , -SO 3 - , -SO 3 H, -SO 3 - Z + , -CO 2 H, -CO 2 R 8 , -SR 8 , -SO 2 R 8 , -SO 3 R 8 or -SO 2 NR 9 R 10 . Among these, -SO 3 - , -SO 3 H, -SO 3 - Z + and -SO 2 NR 9 R 10 are preferred, and -SO 3 - Z + and -SO 2 NR 9 R 10 are more preferred. In this case, -SO 3 - Z + is preferably -SO 3 - N + (R 11 ) 4 .
R1~R4及R8~R11中的碳數1~20的一價飽和烴基可為直鏈狀、分支鏈狀或環狀的任一種。作為其例子,可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十六烷基、二十烷基、異丙基、異丁基、異戊基、新戊基、2-乙基己基等碳數1~20的烷基;環丙基、環戊基、環己基、環庚基、環辛基、三環癸基等碳數3~20的脂環式飽和烴基。 The monovalent saturated alkyl group having 1 to 20 carbon atoms in R 1 to R 4 and R 8 to R 11 may be in any of a linear, branched or cyclic form. Examples thereof include: alkyl groups having 1 to 20 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl, and the like; and alicyclic saturated alkyl groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl, and the like.
作為R1~R4中的飽和烴基可具有的取代基,例如可列舉碳數6~10的芳香族烴基、鹵素原子及羧基。 Examples of the substituent that the saturated hydrocarbon group in R 1 to R 4 may have include an aromatic hydrocarbon group having 6 to 10 carbon atoms, a halogen atom, and a carboxyl group.
作為R9及R10中的飽和烴基可具有的取代基,例如可列舉羥基及鹵素原子。 Examples of the substituent that the saturated alkyl group in R9 and R10 may have include a hydroxyl group and a halogen atom.
作為R1及R2一起形成的環、以及R3及R4一起形成的環,例如可列舉以下環。 Examples of the ring formed by R1 and R2 together and the ring formed by R3 and R4 together include the following rings.
作為-OR8,例如可列舉:甲氧基、乙氧基、丙氧基、丁 氧基、戊氧基、己氧基、庚氧基、辛氧基、2-乙基己氧基及二十烷氧基等。 Examples of -OR 8 include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and eicosyloxy.
作為-CO2R8,例如可列舉:甲氧基羰基、乙氧基羰基、丙氧基羰基、第三丁氧基羰基、己氧基羰基及二十烷氧基羰基等。 Examples of -CO 2 R 8 include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxycarbonyl, hexyloxycarbonyl and eicosyloxycarbonyl.
作為-SR8,例如可列舉:甲巰基、乙巰基、丁巰基、己巰基、癸巰基及二十烷巰基等。 Examples of -SR 8 include methylbenzene, ethylbenzene, butylbenzene, hexylbenzene, decylbenzene and eicosylbenzene.
作為-SO2R8,例如可列舉:甲基磺醯基、乙基磺醯基、丁基磺醯基、己基磺醯基、癸基磺醯基及二十烷基磺醯基等。 Examples of -SO 2 R 8 include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an eicosylsulfonyl group.
作為-SO3R8,例如可列舉:甲氧基磺醯基、乙氧基磺醯基、丙氧基磺醯基、第三丁氧基磺醯基、己氧基磺醯基及二十烷氧基磺醯基等。 Examples of -SO 3 R 8 include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a t-butoxysulfonyl group, a hexyloxysulfonyl group, and an eicosyloxysulfonyl group.
作為-SO2NR9R10,例如可列舉以下基:胺磺醯基;N-甲基胺磺醯基、N-乙基胺磺醯基、N-丙基胺磺醯基、N-異丙基胺磺醯基、N-丁基胺磺醯基、N-異丁基胺磺醯基、N-第二丁基胺磺醯基、N-第三丁基胺磺醯基、N-戊基胺磺醯基、N-(1-乙基丙基)胺磺醯基、N-(1,1-二甲基丙基)胺磺醯基、N-(1,2-二甲基丙基)胺磺醯基、N-(2,2-二甲基丙基)胺磺醯基、N-(1-甲基丁基)胺磺醯基、N-(2-甲基丁基)胺磺醯基、N-(3-甲基丁基)胺磺醯基、N-環戊基胺磺醯基、N-己基胺磺醯基、N-(1,3-二甲基丁基)胺磺醯基、N-(3,3-二甲基丁基)胺磺醯基、N-庚基胺磺醯基、N-(1-甲基己基)胺磺醯基、N-(1,4-二甲基戊基)胺磺醯基、N-辛基胺磺醯基、N-(2- 乙基己基)胺磺醯基、N-(1,5-二甲基)己基胺磺醯基、N-(1,1,2,2-四甲基丁基)胺磺醯基等N-1取代胺磺醯基;N,N-二甲基胺磺醯基、N,N-乙基甲基胺磺醯基、N,N-二乙基胺磺醯基、N,N-丙基甲基胺磺醯基、N,N-異丙基甲基胺磺醯基、N,N-第三丁基甲基胺磺醯基、N,N-丁基乙基胺磺醯基、N,N-雙(1-甲基丙基)胺磺醯基、N,N-庚基甲基胺磺醯基等N,N-2取代胺磺醯基等。 As -SO 2 NR 9 R 10 , for example, the following groups can be cited: sulfonylamine; N-methylsulfonylamine, N-ethylsulfonylamine, N-propylsulfonylamine, N-isopropylsulfonylamine, N-butylsulfonylamine, N-isobutylsulfonylamine, N-sec-butylsulfonylamine, N-tert-butylsulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropyl)sulfonylamine, N-(1,1-dimethylpropyl)sulfonylamine, N-(1,2-dimethylpropyl)sulfonylamine, N-(2,2-dimethylpropyl)sulfonylamine, propyl) amine sulfonyl, N-(1-methylbutyl) amine sulfonyl, N-(2-methylbutyl) amine sulfonyl, N-(3-methylbutyl) amine sulfonyl, N-cyclopentyl amine sulfonyl, N-hexyl amine sulfonyl, N-(1,3-dimethylbutyl) amine sulfonyl, N-(3,3-dimethylbutyl) amine sulfonyl, N-heptyl amine sulfonyl, N-(1-methylhexyl) amine sulfonyl, N-(1,4-dimethylpentyl) amine sulfonyl, N-octyl amine sulfonyl, N-(2- The invention also includes N-1-substituted sulfonylamines such as N-(1,5-dimethyl)hexylsulfonylamine, N-(1,1,2,2-tetramethylbutyl)sulfonylamine; and N,N-2-substituted sulfonylamines such as N,N-dimethylsulfonylamine, N,N-ethylmethylsulfonylamine, N,N-diethylsulfonylamine, N,N-propylmethylsulfonylamine, N,N-isopropylmethylsulfonylamine, N,N-tert-butylmethylsulfonylamine, N,N-butylethylsulfonylamine, N,N-bis(1-methylpropyl)sulfonylamine, and N,N-heptylmethylsulfonylamine.
R5較佳為-CO2H、-CO2 -Z+、-CO2R8、-SO3 -、-SO3 -Z+、-SO3H或SO2NHR9,更佳為SO3 -、-SO3 -Z+、-SO3H或SO2NHR9。 R 5 is preferably -CO 2 H, -CO 2 - Z + , -CO 2 R 8 , -SO 3 - , -SO 3 - Z + , -SO 3 H or SO 2 NHR 9 , and more preferably SO 3 - , -SO 3 - Z + , -SO 3 H or SO 2 NHR 9 .
m較佳為1~4,更佳為1或2。 m is preferably 1 to 4, more preferably 1 or 2.
作為R6及R7中的碳數1~6的烷基,例如可列舉所述列舉的烷基中的碳數1~6的基。 Examples of the alkyl group having 1 to 6 carbon atoms in R6 and R7 include the alkyl groups having 1 to 6 carbon atoms listed above.
作為R11中的碳數7~10的芳烷基,例如可列舉:苄基、苯基乙基、苯基丁基等。 Examples of the aralkyl group having 7 to 10 carbon atoms in R 11 include benzyl, phenylethyl, and phenylbutyl.
作為R12中的碳數1~10的烷二基,例如可列舉:亞甲基、伸乙基、三亞甲基、四亞甲基、五亞甲基、六亞甲基、伸異丙基、伸異丁基、2-甲基三亞甲基、伸異戊基、伸異己基、伸異辛基、2-乙基伸己基等。該些中,較佳為碳數1~6的烷二基,更佳為碳數1~4的烷二基。 Examples of the alkanediyl group having 1 to 10 carbon atoms in R12 include methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, isopropylene, isobutylene, 2-methyltrimethylene, isopentylene, isohexylene, isooctylene, 2-ethylhexylene, etc. Among these, an alkanediyl group having 1 to 6 carbon atoms is preferred, and an alkanediyl group having 1 to 4 carbon atoms is more preferred.
作為R13中的碳數1~4的烷基,例如可列舉:甲基、乙基、丙基、丁基。 Examples of the alkyl group having 1 to 4 carbon atoms in R 13 include methyl, ethyl, propyl and butyl.
作為R13中的碳數1~4的烷氧基,例如可列舉:甲氧基、乙 氧基、丙氧基、第三丁氧基等。 Examples of the alkoxy group having 1 to 4 carbon atoms in R 13 include methoxy, ethoxy, propoxy, and tert-butoxy.
R13較佳為甲基、乙基、甲氧基、乙氧基,更佳為甲氧基或乙氧基。 R 13 is preferably methyl, ethyl, methoxy or ethoxy, more preferably methoxy or ethoxy.
作為鹵素原子,例如可列舉:氟原子、氯原子、溴原子及碘原子。 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.
Z+為N+(R11)4、Na+或K+,較佳為N+(R11)4。 Z + is N + (R 11 ) 4 , Na + or K + , preferably N + (R 11 ) 4 .
作為所述N+(R11)4,較佳為四個R11中的至少兩個為碳數5~20的一價飽和烴基。另外,四個R11的合計碳數較佳為20~80,更佳為20~60。於在化合物(1a)中存在N+(R11)4的情況下,若R11為該些基,則可由包含化合物(1a)的本發明的著色硬化性樹脂組成物形成異物少的彩色濾光片。 As the N + (R 11 ) 4 , at least two of the four R 11s are preferably monovalent saturated alkyl groups having 5 to 20 carbon atoms. The total carbon number of the four R 11s is preferably 20 to 80, more preferably 20 to 60. When N + (R 11 ) 4 is present in the compound (1a), if R 11 is any of these groups, a color filter having less foreign matter can be formed from the colored curable resin composition of the present invention containing the compound (1a).
作為化合物(1a),較佳為式(2a)所表示的化合物(以下,有時記載為「化合物(2a)」)。化合物(2a)亦可為其互變異構體。 As compound (1a), a compound represented by formula (2a) (hereinafter, sometimes described as "compound (2a)") is preferred. Compound (2a) may also be a tautomer thereof.
[式(2a)中,R21~R24分別獨立地表示氫原子、可具有 羧基的碳數1~20的一價飽和烴基、可具有取代基的碳數6~10的一價芳香族烴基或*-R12-Si(R13)3所表示的基(所述式中,*表示與氮原子的鍵結位置),R21及R22可一起形成包含氮原子的環,R23及R24可一起形成包含氮原子的環,R25表示-SO3 -、-SO3H、-SO3 -Z1+或-SO2NHR26,m表示0~5的整數,於m為2以上時,多個R25可相同亦可不同,a表示0或1的整數,X表示鹵素原子,R26表示碳數1~20的一價飽和烴基,Z1+表示N+(R27)4、Na+或K+,四個R27可相同亦可不同,以及R27表示碳數1~20的一價飽和烴基或苄基,其中,於在式(2a)中存在離子形態的-SO3 -的情況下,其數量為一個] [In the formula (2a), R 21 to R 24 each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a carboxyl group, a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a group represented by *-R 12 -Si(R 13 ) 3 (in the above formula, * represents a bonding position to a nitrogen atom), R 21 and R 22 may together form a ring containing a nitrogen atom, R 23 and R 24 may together form a ring containing a nitrogen atom, R 25 represents -SO 3 - , -SO 3 H, -SO 3 - Z1 + or -SO 2 NHR 26 , m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 25 may be the same or different, a represents an integer of 0 or 1, X represents a halogen atom, R wherein Z1 + represents N + ( R27 ) 4 , Na + or K + , the four R27s may be the same or different, and R27 represents a monovalent saturated alkyl group having 1 to 20 carbon atoms or a benzyl group, wherein when -SO3- in ionic form exists in formula (2a), the number thereof is one]
作為R21~R24中的碳數6~10的一價芳香族烴基,例如可列舉與作為所述R1~R4的芳香族烴基而列舉者相同的基。作為所述芳香族烴基可具有的取代基,例如可列舉:-SO3 -、-SO3H、-SO3 -Z1+、-SO3R26或-SO2NHR26。 Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R 21 to R 24 include the same groups as those listed as the aromatic hydrocarbon groups for R 1 to R 4. Examples of the substituent that the aromatic hydrocarbon group may have include -SO 3 - , -SO 3 H, -SO 3 - Z1 + , -SO 3 R 26 or -SO 2 NHR 26 .
R21~R24中的*-R12-Si(R13)3所表示的基的說明與所述相同。 The explanation of the group represented by *-R 12 -Si(R 13 ) 3 in R 21 to R 24 is the same as described above.
作為R21~R24的組合,較佳為R21及R23為氫原子、R22及R24為碳數6~10的一價芳香族烴基、所述芳香族烴基經-SO3 -、 -SO3H、-SO3 -Z1+、-SO3R26或-SO2NHR26取代者。進而佳的組合為R21及R23為氫原子、R22及R24為碳數6~10的一價芳香族烴基、所述芳香族烴基經-SO3 -Z1+或-SO2NHR26取代者。若R21~R24為該些基,則可由包含化合物(2a)的本發明的著色硬化性樹脂組成物形成耐熱性優異的彩色濾光片。 As a combination of R 21 to R 24 , it is preferred that R 21 and R 23 are hydrogen atoms, R 22 and R 24 are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the aromatic hydrocarbon groups are substituted by -SO 3 - , -SO 3 H, -SO 3 - Z1 + , -SO 3 R 26 , or -SO 2 NHR 26. A further preferred combination is that R 21 and R 23 are hydrogen atoms, R 22 and R 24 are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the aromatic hydrocarbon groups are substituted by -SO 3 - Z1 + or -SO 2 NHR 26. When R 21 to R 24 are these groups, a color filter having excellent heat resistance can be formed from the colored curable resin composition of the present invention containing compound (2a).
作為R21及R22一起形成的包含氮原子的環、以及R23及R24一起形成的包含氮原子的環,例如可列舉與R1及R2一起形成的環相同者。其中,較佳為脂肪族雜環。作為所述脂肪族雜環,例如可列舉下述環。 Examples of the ring containing a nitrogen atom formed by R 21 and R 22 together, and the ring containing a nitrogen atom formed by R 23 and R 24 together include the same rings as those formed by R 1 and R 2 together. Among them, an aliphatic heterocyclic ring is preferred. Examples of the aliphatic heterocyclic ring include the following rings.
作為R21~R24、R26及R27中的碳數1~20的一價飽和烴基,例如可列舉與R8~R11中作為飽和烴基而列舉者相同的基。 Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 21 to R 24 , R 26 and R 27 include the same groups as those exemplified as the saturated hydrocarbon group in R 8 to R 11 .
於R21~R24為可具有羧基的碳數1~20的一價飽和烴基的情況下,R21~R24較佳為分別獨立地為可具有羧基的甲基、可具有羧基的乙基、或可具有羧基的丙基。另外,作為-SO3R26及-SO2NHR26 中的R26,較佳為碳數3~20的分支鏈狀烷基,更佳為碳數6~12的分支鏈狀烷基,進而佳為2-乙基己基。若R26為該些基,則可由包含化合物(2a)的本發明的著色硬化性樹脂組成物形成異物的產生少的彩色濾光片。 When R 21 to R 24 are monovalent saturated alkyl groups having 1 to 20 carbon atoms which may have a carboxyl group, R 21 to R 24 are preferably independently methyl groups which may have a carboxyl group, ethyl groups which may have a carboxyl group, or propyl groups which may have a carboxyl group. In addition, R 26 in -SO 3 R 26 and -SO 2 NHR 26 is preferably a branched chain alkyl group having 3 to 20 carbon atoms, more preferably a branched chain alkyl group having 6 to 12 carbon atoms, and further preferably a 2-ethylhexyl group. When R 26 is any of these groups, a color filter having less generation of foreign substances can be formed from the colored curable resin composition of the present invention containing the compound (2a).
Z1+為N+(R27)4、Na+或K+,較佳為N+(R27)4。作為所述N+(R27)4,較佳為四個R27中的至少兩個為碳數5~20的一價飽和烴基。另外,四個R27的合計碳數較佳為20~80,更佳為20~60。於在化合物(2a)中存在N+(R27)4的情況下,若R27為該些基,則可由包含化合物(2a)的本發明的著色硬化性樹脂組成物形成異物的產生少的彩色濾光片。 Z1 + is N + ( R27 ) 4 , Na + or K + , preferably N + ( R27 ) 4 . As the N + ( R27 ) 4 , at least two of the four R27 are preferably monovalent saturated alkyl groups having 5 to 20 carbon atoms. The total carbon number of the four R27 is preferably 20 to 80, more preferably 20 to 60. When N + ( R27 ) 4 is present in compound (2a), if R27 is any of these groups, a color filter with less generation of foreign matter can be formed from the colored curable resin composition of the present invention containing compound (2a).
m較佳為1~4,更佳為1或2。 m is preferably 1 to 4, more preferably 1 or 2.
另外,作為化合物(1a),亦較佳為式(3a)所表示的化合物(以下,有時記載為「化合物(3a)」)。化合物(3a)亦可為其互變異構體。 In addition, as compound (1a), a compound represented by formula (3a) (hereinafter, sometimes described as "compound (3a)") is also preferred. Compound (3a) may also be a tautomer thereof.
[式(3a)中,R31及R32分別獨立地表示碳數1~10的一價飽和烴基、或*-R12-Si(R13)3所表示的基(所述式中,*表示與 氮原子的鍵結位置),所述飽和烴基可經碳數6~10的一價芳香族烴基、鹵素原子或羧基取代,所述飽和烴基中所含的-CH2-可經-O-、-CO-或-NR11-取代,所述芳香族烴基可經碳數1~3的烷氧基取代,R33及R34分別獨立地表示碳數1~4的烷基、碳數1~4的烷巰基或碳數1~4的烷基磺醯基,R31及R33可一起形成包含氮原子的環,R32及R34可一起形成包含氮原子的環,以及p及q分別獨立地表示0~5的整數,於p為2以上時,多個R33可相同亦可不同,於q為2以上時,多個R34可相同亦可不同,以及R11與所述為相同含義] [In the formula (3a), R 31 and R 32 each independently represent a monovalent saturated alkyl group having 1 to 10 carbon atoms, or a group represented by *-R 12 -Si(R 13 ) 3 (in the formula, * represents the bonding position to the nitrogen atom), the saturated alkyl group may be substituted by a monovalent aromatic alkyl group having 6 to 10 carbon atoms, a halogen atom or a carboxyl group, the -CH 2 - contained in the saturated alkyl group may be substituted by -O-, -CO- or -NR 11 -, the aromatic alkyl group may be substituted by an alkoxy group having 1 to 3 carbon atoms, R 33 and R 34 each independently represent an alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms or an alkylsulfonyl group having 1 to 4 carbon atoms, R 31 and R 33 may form a ring containing a nitrogen atom together, and R 32 and R R 34 may together form a ring containing a nitrogen atom, and p and q each independently represent an integer of 0 to 5, when p is 2 or more, a plurality of R 33 may be the same or different, when q is 2 or more, a plurality of R 34 may be the same or different, and R 11 has the same meaning as described above]
R31及R32中的碳數1~10的一價飽和烴基可為直鏈狀、分支鏈狀或環狀的任一種。作為其例子,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、異丙基、異丁基、異戊基、新戊基、2-乙基己基等碳數1~10的烷基;環丙基、環戊基、環己基、環庚基、環辛基等碳數3~10的脂環式飽和烴基。 The monovalent saturated alkyl group having 1 to 10 carbon atoms in R 31 and R 32 may be in a linear, branched or cyclic form. Examples thereof include alkyl groups having 1 to 10 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, isobutyl, isopentyl, neopentyl and 2-ethylhexyl; and alicyclic saturated alkyl groups having 3 to 10 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
R31及R32中的*-R12-Si(R13)3所表示的基的說明與所述相同。 The group represented by *-R 12 -Si(R 13 ) 3 in R 31 and R 32 is the same as described above.
作為R31及R32可以取代基的形式所具有的碳數6~10的一價芳香族烴基,例如可列舉苯基。 Examples of the monovalent aromatic alkyl group having 6 to 10 carbon atoms which may be substituted for R 31 and R 32 include phenyl.
作為芳香族烴基可以取代基的形式所具有的碳數1~3的烷 基,例如可列舉:甲基、乙基、丙基。 Examples of alkyl groups having 1 to 3 carbon atoms that may be present as substituents in aromatic hydrocarbon groups include methyl, ethyl, and propyl.
作為芳香族烴基可以取代基的形式所具有的碳數1~3的烷氧基,例如可列舉:甲氧基、乙氧基、丙氧基等。 Examples of alkoxy groups having 1 to 3 carbon atoms that may be present as substituents on aromatic hydrocarbon groups include methoxy, ethoxy, propoxy, etc.
R31及R32中的*-R12-Si(R13)3所表示的基的說明與所述相同。 The group represented by *-R 12 -Si(R 13 ) 3 in R 31 and R 32 is the same as described above.
R31及R32較佳為分別獨立地為可具有羧基的碳數1~3的一價飽和烴基。 R 31 and R 32 are preferably each independently a monovalent saturated hydrocarbon group having 1 to 3 carbon atoms which may have a carboxyl group.
作為R33及R34中的碳數1~4的烷基,例如可列舉:甲基、乙基、丙基、丁基、異丙基、異丁基、第二丁基、第三丁基等。 Examples of the alkyl group having 1 to 4 carbon atoms in R 33 and R 34 include methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, t-butyl and the like.
作為R33及R34中的碳數1~4的烷巰基,例如可列舉:甲巰基、乙巰基、丙巰基、丁巰基及異丙巰基等。 Examples of the alkyl group having 1 to 4 carbon atoms in R33 and R34 include methyl, ethyl, propyl, butyl and isopropyl groups.
作為R33及R34中的碳數1~4的烷基磺醯基,例如可列舉:甲基磺醯基、乙基磺醯基、丙基磺醯基、丁基磺醯基及異丙基磺醯基等。 Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R 33 and R 34 include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and isopropylsulfonyl.
R33及R34較佳為碳數1~4的烷基,更佳為甲基。 R 33 and R 34 are preferably alkyl groups having 1 to 4 carbon atoms, more preferably methyl groups.
p及q較佳為0~2的整數,更佳為0或1。 p and q are preferably integers between 0 and 2, and more preferably 0 or 1.
作為化合物(1a),例如可列舉式(1-1)~式(1-45)所表示的化合物。再者,下述式中的R40表示碳數1~20的一價飽和烴基,較佳為碳數6~12的分支鏈狀烷基,更佳為2-乙基己基。另外,下述式中的R26如上所述般表示碳數1~20的一價飽和烴基。 As compound (1a), for example, compounds represented by formula (1-1) to formula (1-45) can be listed. In the following formula, R40 represents a monovalent saturated alkyl group having 1 to 20 carbon atoms, preferably a branched chain alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group. In addition, R26 in the following formula represents a monovalent saturated alkyl group having 1 to 20 carbon atoms as described above.
[化12]
[化13]
[化14]
[化15]
[化17]
[化19]
作為氧雜蒽染料,較佳為C.I.酸性紅289的磺醯胺化物、C.I.酸性紅289的四級銨鹽、C.I.酸性紫102的磺醯胺化物或C.I.酸性紫102的四級銨鹽。作為此種化合物,例如可列舉式(1-1)~式(1-8)、式(1-11)或式(1-12)所表示的化合物。 As the oxyanthracene dye, preferably, it is a sulfonamide of C.I. Acid Red 289, a quaternary ammonium salt of C.I. Acid Red 289, a sulfonamide of C.I. Acid Violet 102, or a quaternary ammonium salt of C.I. Acid Violet 102. As such a compound, for example, compounds represented by formula (1-1) to formula (1-8), formula (1-11) or formula (1-12) can be cited.
另外,就於有機溶媒中的溶解性優異的方面而言,亦較佳為式(1-24)~式(1-33)、式(1-44)及式(1-45)的任一者所表示的化合物。 In addition, in terms of excellent solubility in organic solvents, compounds represented by any one of formula (1-24) to formula (1-33), formula (1-44) and formula (1-45) are also preferred.
氧雜蒽染料可使用市售的氧雜蒽染料(例如,中外化成公司製造的「中外亞米諾法斯特品庫(Chugai Aminol Fast Pink)R-H/C」,田岡化學工業公司製造的「羅丹明(Rhodamin)6G」)。另外,亦可將市售的氧雜蒽染料作為起始原料並參考公知技術(例如,日本專利特開2010-32999號公報)來合成。 Oxygenated anthracene dyes can be commercially available oxyanthracene dyes (e.g., "Chugai Aminol Fast Pink R-H/C" manufactured by Chugai Chemical Co., Ltd., "Rhodamin 6G" manufactured by Tagoka Chemical Industry Co., Ltd.). In addition, commercially available oxyanthracene dyes can be used as starting materials and synthesized with reference to known techniques (e.g., Japanese Patent Publication No. 2010-32999).
三芳基甲烷染料較佳為式(4a)所表示的化合物。 The triarylmethane dye is preferably a compound represented by formula (4a).
[式(4a)中,R1A~R8A分別獨立地表示氫原子、鹵素原子、硝基、羥基、或碳數1~20的飽和烴基,於所述飽和烴基的碳數為2~20的情況下,所述飽和烴基中所含的-CH2-可經-O-或-CO-取代,R9A~R12A分別獨立地表示氫原子、碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基,所述飽和烴基可被經取代或未經取代的胺基或鹵素原子取代,於所述飽和烴基的碳數為2~20的情況下,所述飽和烴基中所含的-CH2-可經-O-或-CO-取代,R9A及R10A亦可鍵結而與該些所鍵結的氮原子一同形成環,R11A及R12A亦可鍵結而與該些所鍵結的氮原子一同形成環,R13A表示可經取代的碳數6~20的芳香族烴基,[G]g-表示任意的g價的抗衡陰離子,以及 g表示0或任意的自然數,於g為2以上的自然數的情況下,式(4a)中的多個陽離子可分別相同亦可不同] [In formula (4a), R 1A to R 8A each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or a saturated alkyl group having 1 to 20 carbon atoms. When the saturated alkyl group has 2 to 20 carbon atoms, the -CH 2 - contained in the saturated alkyl group may be substituted by -O- or -CO-. R 9A to R 12A each independently represent a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms, an aromatic alkyl group having 6 to 20 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent. The saturated alkyl group may be substituted by a substituted or unsubstituted amino group or a halogen atom. When the saturated alkyl group has 2 to 20 carbon atoms, the -CH 2 - contained in the saturated alkyl group may be substituted by -O- or -CO-. - may be substituted by -O- or -CO-, R 9A and R 10A may also be bonded to form a ring together with the nitrogen atoms to which they are bonded, R 11A and R 12A may also be bonded to form a ring together with the nitrogen atoms to which they are bonded, R 13A represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted, [G] g- represents any g-valent counter anion, and g represents 0 or any natural number, and when g is a natural number greater than 2, the multiple cations in formula (4a) may be the same or different]
香豆素染料為包含分子內具有香豆素骨架的化合物的染料。作為香豆素染料,例如可列舉:C.I.酸性黃(acid yellow)227、250;C.I.分散黃(disperse yellow)82、184;C.I.溶劑橙(solvent orange)112;C.I.溶劑黃(solvent yellow)160、172;日本專利第1299948號公報中記載的香豆素染料等。較佳為溶解於有機溶劑的染料。 Coumarin dyes are dyes containing compounds with a coumarin skeleton in the molecule. Examples of coumarin dyes include: C.I. Acid Yellow 227, 250; C.I. Disperse Yellow 82, 184; C.I. Solvent Orange 112; C.I. Solvent Yellow 160, 172; coumarin dyes described in Japanese Patent No. 1299948, etc. Preferably, the dye is soluble in an organic solvent.
作為所述染料以外的染料,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)中所記載的染料、染色筆記(色染公司(shikisensha))中所記載的染料。另外,作為染料,例如可列舉:偶氮染料、花青染料、酞菁染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、偶氮甲鹼染料、方酸內鎓染料、吖啶染料、苯乙烯基染料、喹啉染料及硝基染料等。該些中,較佳為溶解於有機溶劑的染料。 As dyes other than the above dyes, for example, dyes listed in the Color Index (published by The Society of Dyers and Colourists) and dyes listed in the Dyeing Notes (Shikisensha) can be listed. In addition, as dyes, for example, azo dyes, cyanine dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azoformine dyes, squarylium dyes, acridine dyes, styryl dyes, quinoline dyes, and nitro dyes can be listed. Among these, dyes that are soluble in organic solvents are preferred.
作為染料的具體例,可列舉以下染料。 As specific examples of dyes, the following dyes can be listed.
(1)C.I.溶劑染料 (1) C.I. solvent dye
C.I.溶劑黃4、14、15、23、24、25、38、62、63、68、79、81、82、83、89、94、98、99、162;C.I.溶劑橙2、7、11、15、26、41、54、56、99;C.I.溶劑紅24、49、90、91、111、118、119、122、124、125、 127、130、132、143、145、146、150、151、155、160、168、169、172、175、181、207、222、227、230、245、247;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)14、18、35、36、45、58、59、59:1、63、68、69、78、79、83、94、97、98、100、101、102、104、105、111、112、122、128、132、136、139;C.I.溶劑綠(solvent green)1、3、5、28、29、32、33等。 C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; C.I. Solvent Violet C.I. violet) 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. solvent blue (solvent blue) 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. solvent green (solvent green) 1, 3, 5, 28, 29, 32, 33, etc.
(2)C.I.酸性染料 (2) C.I. Acid dyes
C.I.酸性黃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.酸性橙(acid orange)6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、149、162、169、173;C.I.酸性紅73、80、91、97、138、151、211、274;C.I.酸性綠(acid green)3、5、9、25、27、28、41;C.I.酸性紫34、120;C.I.酸性藍(acid blue)25、27、40、45、78、80、112等。 C.I. 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 Orange Orange) 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Acid Red 73, 80, 91, 97, 138, 151, 211, 274; C.I. Acid Green (acid green) 3, 5, 9, 25, 27, 28, 41; C.I. Acid Violet 34, 120; C.I. Acid Blue (acid blue) 25, 27, 40, 45, 78, 80, 112, etc.
(3)C.I.鹼性染料 (3) C.I. Alkaline dyes
C.I.鹼性綠(basic green)1等。 C.I. Basic green 1, etc.
(4)C.I.活性染料 (4) C.I. reactive dyes
C.I.活性黃(reactive yellow)2、76、116;C.I.活性橙(reactive orange)16等。 C.I. reactive yellow 2, 76, 116; C.I. reactive orange 16, etc.
(5)C.I.直接染料 (5) C.I. Direct dyes
C.I.直接黃(direct yellow)2、4、28、33、34、35、38、39、43、44、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、132、136、138、141;C.I.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.直接藍(direct blue)40等。 C.I. Direct yellow: 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; C.I. Direct orange: 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct blue: 40, etc.
(6)C.I.分散染料 (6) C.I. Disperse Dyes
C.I.分散黃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. Disperse Yellow 51, 54, 76; C.I. Disperse Violet 26, 27; C.I. Disperse Blue 1, 14, 56, 60, etc.
(7)C.I.媒介染料 (7) C.I. mordant dyes
C.I.媒介黃(mordant yellow)5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;C.I.媒介橙(mordant orange)3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48等。 C.I. mordant yellow: 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; 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, etc.
(8)C.I.還原染料 (8) C.I. reduced dyes
C.I.還原綠(vat green)1等。 C.I. Vat green 1, etc.
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(染色與印染工作者協會(The Society of Dyers and Colourists)出版)中記載的顏料。 The pigment (A2) is not particularly limited, and known pigments can be used, for example, pigments listed in the Dye Index (published by The Society of Dyers and Colourists).
作為顏料(A2),例如可列舉以下顏料: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、129、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、15:3、15:4、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。 As the pigment (A2), for example, the following pigments can be cited: yellow pigments such as 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, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214; orange pigments such as C.I. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; and red pigments such as C.I. pigment red. C.I. pigment blue (pigment blue) 15, 15:3, 15:4, 15:6, 60 and other blue pigments; C.I. pigment violet (pigment 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 (pigment black) 1, 7 and other black pigments, etc.
顏料(A2)較佳為紅色顏料或藍色顏料。 The pigment (A2) is preferably a red pigment or a blue pigment.
紅色顏料較佳為於580nm以下的波長區域中具有吸收,更佳為於480nm以上且560nm以下的波長區域中具有吸收。另外,所述紅色顏料較佳為透過610nm以上的波長區域的光的顏料。 The red pigment preferably has absorption in the wavelength region below 580nm, and more preferably has absorption in the wavelength region above 480nm and below 560nm. In addition, the red pigment is preferably a pigment that transmits light in the wavelength region above 610nm.
作為紅色顏料,可使用公知的顏料,例如可列舉染料索引(染色與印染工作者協會(The Society of Dyers and Colourists)出版)中所記載的顏料。 As the red pigment, known pigments can be used, for example, pigments listed in the Dye Index (published by The Society of Dyers and Colourists).
紅色顏料中,較佳為蒽醌顏料、偶氮顏料、喹吖啶酮顏料、苝顏料、二酮基吡咯並吡咯顏料,更佳為蒽醌顏料及二酮基吡咯並吡咯顏料。 Among red pigments, anthraquinone pigments, azo pigments, quinacridone pigments, perylene pigments, and diketopyrrolopyrrole pigments are preferred, and anthraquinone pigments and diketopyrrolopyrrole pigments are more preferred.
作為較佳的紅色顏料的具體例,可列舉:C.I.顏料紅9、97、105、122、123、144、149、166、168、176、177、179、180、192、202、208、209、215、216、224、242、254、255、264、265、266、268、269、273、及日本專利特開2013-014750中記載的式(P)所表示的化合物等。該些中,更佳為C.I.顏料紅177、208、242、254、269、及日本專利特開2013-014750中記載的式(P)所表示的化合物,進而佳為C.I.顏料紅177、254、及日本專利特開2013-014750中記載的式(P)所表示的化合物。 Specific examples of preferred red pigments include C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 202, 208, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, and compounds represented by formula (P) described in Japanese Patent Laid-Open No. 2013-014750. Among these, C.I. Pigment Red 177, 208, 242, 254, 269 and compounds represented by formula (P) described in Japanese Patent Laid-Open No. 2013-014750 are more preferred, and C.I. Pigment Red 177, 254 and compounds represented by formula (P) described in Japanese Patent Laid-Open No. 2013-014750 are further preferred.
藍色顏料較佳為於700nm以下的波長區域中具有吸收,更佳為於580nm以上且650nm以下的波長區域中具有吸收。另外,藍色顏料較佳為透過400nm以上的波長區域的光的顏料。 The blue pigment preferably has absorption in the wavelength region below 700nm, and more preferably has absorption in the wavelength region above 580nm and below 650nm. In addition, the blue pigment is preferably a pigment that transmits light in the wavelength region above 400nm.
藍色顏料較佳為酞菁顏料,更佳為銅酞菁顏料及/或鋅酞菁顏料,進而佳為鹵化銅酞菁顏料及/或鹵化鋅酞菁顏料,特佳為 鹵化銅酞菁顏料。 The blue pigment is preferably a phthalocyanine pigment, more preferably a copper phthalocyanine pigment and/or a zinc phthalocyanine pigment, further preferably a copper phthalocyanine halide pigment and/or a zinc phthalocyanine halide pigment, and particularly preferably a copper phthalocyanine halide pigment.
具體而言,較佳為C.I.顏料藍15、15:3、15:4、15:6、60,更佳為C.I.顏料藍15、15:3、15:4、15:6,特佳為C.I.顏料藍15:6。藉由使用所述藍色顏料,容易實現透過光譜的最佳化,彩色濾光片的耐光性及耐化學品性變良好。 Specifically, C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 are preferred, C.I. Pigment Blue 15, 15:3, 15:4, 15:6 are more preferred, and C.I. Pigment Blue 15:6 is particularly preferred. By using the above blue pigment, it is easy to optimize the transmitted spectrum, and the light resistance and chemical resistance of the color filter become good.
對於顏料,視需要可實施松香處理、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進行的對顏料表面的接枝處理、利用硫酸微粒化法等進行的微粒化處理、或者用於去除雜質的利用有機溶劑或水等進行的清洗處理、利用離子交換法等去除離子性雜質的處理等。顏料的粒徑較佳為均勻。 For the pigment, rosin treatment, surface treatment using pigment derivatives with acidic or alkaline groups, grafting treatment on the pigment surface using polymer compounds, micronization treatment using sulfuric acid micronization method, or cleaning treatment using organic solvents or water to remove impurities, or treatment to remove ionic impurities using ion exchange method, etc. can be performed as needed. The particle size of the pigment is preferably uniform.
藉由使用分散劑進行分散處理,可獲得顏料於溶液中均勻地分散的狀態的顏料分散液。 By using a dispersant for dispersion treatment, a pigment dispersion in which the pigment is evenly dispersed in the solution can be obtained.
作為分散劑,例如可列舉界面活性劑。界面活性劑可為陽離子界面活性劑、陰離子界面活性劑、非離子界面活性劑、兩性界面活性劑的任一種。作為界面活性劑,例如可列舉:聚酯系界面活性劑、多胺系界面活性劑、丙烯酸系界面活性劑等。作為分散劑的市售品,例如可列舉:KP(信越化學工業公司製造)、弗洛倫(Flowlen)(共榮社化學公司製造)、索努帕斯(Solsperse)(註冊商標)(捷力康(zeneca)公司製造)、艾夫卡(EFKA)(巴斯夫(BASF)公司製造)、阿吉斯帕(Ajisper)(註冊商標)(味之素精細科技(Ajinomoto Fine-Techno)公司製造)、迪斯帕畢克 (DISPERBYK)(註冊商標)(畢克化學(BYK-Chemie)公司製造)、畢克艾皮恩(BYKLPN)(畢克(BYK)公司製造)等。 As the dispersant, for example, a surfactant can be cited. The surfactant can be any of a cationic surfactant, an anionic surfactant, a nonionic surfactant, and an amphoteric surfactant. As the surfactant, for example, polyester-based surfactants, polyamine-based surfactants, acrylic-based surfactants, etc. can be cited. Examples of commercially available dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno), DISPERBYK (registered trademark) (manufactured by BYK-Chemie), BYKLPN (manufactured by BYK), etc.
於顏料分散液中包含分散劑的情況下,其含量相對於顏料(A2)100重量份而較佳為1重量份以上且500重量份以下,更佳為5重量份以上且300重量份以下。若分散劑的含量處於所述範圍內,則有可獲得均勻的分散狀態的顏料分散液的傾向。 When a dispersant is included in the pigment dispersion, its content is preferably 1 part by weight or more and 500 parts by weight or less, and more preferably 5 parts by weight or more and 300 parts by weight or less, relative to 100 parts by weight of the pigment (A2). If the content of the dispersant is within the above range, a uniformly dispersed pigment dispersion tends to be obtained.
相對於固體成分的總量,著色劑(A)的含量較佳為1重量%以上且60重量%以下,更佳為3重量%以上且55重量%以下,進而佳為5重量%以上且50重量%以下。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後的量。若著色劑(A)的含量處於所述範圍內,則可獲得顏色濃度充分的彩色濾光片。另外,若著色劑(A)的含量處於所述範圍內,則可使組成物中含有必要量的樹脂或聚合性化合物,因此可形成機械強度充分的彩色濾光片。固體成分的總量及相對於其的各成分的含量例如可利用液相層析法或氣相層析法等公知的分析手段進行測定。 The content of the colorant (A) relative to the total amount of solid components is preferably 1% by weight or more and 60% by weight or less, more preferably 3% by weight or more and 55% by weight or less, and even more preferably 5% by weight or more and 50% by weight or less. The so-called "total amount of solid components" in this specification refers to the amount after deducting the content of the solvent from the total amount of the colored curable resin composition. If the content of the colorant (A) is within the above range, a color filter with sufficient color concentration can be obtained. In addition, if the content of the colorant (A) is within the above range, the composition can contain a necessary amount of resin or polymerizable compound, thereby forming a color filter with sufficient mechanical strength. The total amount of solid components and the content of each component relative to it can be measured using known analytical methods such as liquid chromatography or gas chromatography.
於使用染料(A1)的情況下,其含量相對於固體成分的總量而較佳為0.5重量%以上,更佳為1重量%以上,且更佳為60重量%以下,進而佳為55重量%以下。若染料(A1)的含量處於所述範圍,則可獲得對於鹼性顯影液的顯影性良好的著色硬化性樹脂組成物。 When the dye (A1) is used, its content is preferably 0.5% by weight or more, more preferably 1% by weight or more, and more preferably 60% by weight or less, and further preferably 55% by weight or less relative to the total amount of the solid component. If the content of the dye (A1) is within the above range, a colored curable resin composition having good developability with an alkaline developer can be obtained.
於使用顏料(A2)的情況下,其含量相對於固體成分的 總量而較佳為1重量%以上,更佳為1.5重量%以上,且較佳為60重量%以下,更佳為55重量%以下,進而佳為50重量%以下。若顏料(A2)的含量處於所述範圍,則可獲得色度良好的彩色濾光片。 When the pigment (A2) is used, its content relative to the total amount of solid components is preferably 1% by weight or more, more preferably 1.5% by weight or more, and preferably 60% by weight or less, more preferably 55% by weight or less, and further preferably 50% by weight or less. If the content of the pigment (A2) is within the above range, a color filter with good chromaticity can be obtained.
於使用染料(A1)及顏料(A2)的情況下,染料(A1)與顏料(A2)的重量比(染料(A1):顏料(A2))較佳為1:99~99:1,更佳為1:99~95:5,特佳為5:95~90:10。 When dye (A1) and pigment (A2) are used, the weight ratio of dye (A1) to pigment (A2) (dye (A1): pigment (A2)) is preferably 1:99~99:1, more preferably 1:99~95:5, and particularly preferably 5:95~90:10.
於本發明的一態樣中,著色劑(A)包含選自由式(A3-1):
所表示的化合物(以下,有時記載為「化合物(A3-1)」)、以及式(A3-2):[化22]
所表示的化合物(以下,有時記載為「化合物(A3-2)」)所組成的群組中的至少一種化合物(A3)。 At least one compound (A3) in the group consisting of the compounds represented (hereinafter, sometimes described as "compound (A3-2)").
化合物(A3)(即,化合物(A3-1)及化合物(A3-2))根據其結構(例如,作為抗衡離子的(Mr+)k-1及[Y]m-的種類)而成為「可溶於溶劑的染料」或「不溶於溶劑的顏料」。即,化合物(A3)的範圍中包含作為染料的化合物及作為顏料的化合物兩者。 Compound (A3) (i.e., compound (A3-1) and compound (A3-2)) is a "solvent-soluble dye" or a "solvent-insoluble pigment" depending on its structure (e.g., the types of (M r+ ) k-1 and [Y] m- as counter ions). That is, the scope of compound (A3) includes both compounds that are dyes and compounds that are pigments.
首先,對化合物(A3)中的基等的定義進行說明。只要並無特別記載,化合物(A3)中的基等具有以下定義。 First, the definitions of the groups in compound (A3) are explained. Unless otherwise specified, the groups in compound (A3) have the following definitions.
作為鹵素原子,例如可列舉:氟原子、氯原子、溴原子、碘原子。 Examples of halogen atoms include fluorine atom, chlorine atom, bromine atom, and iodine atom.
飽和烴基可為直鏈狀、分支鏈狀及環狀的任一種。作為碳數1~20的飽和烴基,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、十二烷基、十六烷基、二十烷基、異丙基、異丁基、異戊基、新戊基、2-乙基己基等碳數1~20的烷基;環丙基、環戊基、環己基、環庚基、環辛基、三環癸基等碳數3~20的脂環式飽和烴基。 The saturated alkyl group may be any of a straight chain, a branched chain, and a ring. Examples of saturated alkyl groups having 1 to 20 carbon atoms include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl, and other alkyl groups having 1 to 20 carbon atoms; and alicyclic saturated alkyl groups having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl.
烷基可為直鏈狀及分支鏈狀的任一種。作為碳數1~10 的烷基的例子,可列舉所述碳數1~20的烷基的例示中碳數為1~10的基。其他碳數不同的烷基的例示亦相同。另外,關於烷基以外的基,碳數不同的基的例示亦相同。例如,作為碳數2~20的飽和烴基的例子,可列舉所述碳數1~20的飽和烴基的例示中碳數為2~20的基。 The alkyl group may be a straight chain or a branched chain. As examples of alkyl groups having 1 to 10 carbon atoms, the groups having 1 to 10 carbon atoms in the examples of alkyl groups having 1 to 20 carbon atoms can be cited. The examples of alkyl groups having different carbon atoms are the same. In addition, regarding groups other than alkyl groups, the examples of groups having different carbon atoms are the same. For example, as examples of saturated alkyl groups having 2 to 20 carbon atoms, the groups having 2 to 20 carbon atoms in the examples of saturated alkyl groups having 1 to 20 carbon atoms can be cited.
烷二基可為直鏈狀及分支鏈狀的任一種。作為碳數1~10的烷二基,例如可列舉:亞甲基、伸乙基、三亞甲基、四亞甲基、五亞甲基、六亞甲基、伸異丙基、伸異丁基、2-甲基三亞甲基、伸異戊基、伸異己基、伸異辛基、2-乙基伸己基等。 The alkanediyl group may be either a straight chain or a branched chain. Examples of alkanediyl groups having 1 to 10 carbon atoms include methylene, ethyl, trimethylene, tetramethylene, pentamethylene, hexamethylene, isopropyl, isobutyl, 2-methyltrimethylene, isopentyl, isohexyl, isooctyl, and 2-ethylhexyl.
氟烷基可為直鏈狀及分支鏈狀的任一種。作為碳數1~12的氟烷基,例如可列舉:單氟甲基、二氟甲基、全氟甲基、單氟乙基、二氟乙基、三氟乙基、四氟乙基、全氟乙基、單氟丙基、二氟丙基、三氟丙基、四氟丙基、五氟丙基、六氟丙基、全氟丙基、單氟丁基、二氟丁基、三氟丁基、四氟丁基、五氟丁基、六氟丁基、七氟丁基、八氟丁基、全氟丁基。 The fluoroalkyl group may be a straight chain or a branched chain. Examples of the fluoroalkyl group having 1 to 12 carbon atoms include monofluoromethyl, difluoromethyl, perfluoromethyl, monofluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, perfluoroethyl, monofluoropropyl, difluoropropyl, trifluoropropyl, tetrafluoropropyl, pentafluoropropyl, hexafluoropropyl, perfluoropropyl, monofluorobutyl, difluorobutyl, trifluorobutyl, tetrafluorobutyl, pentafluorobutyl, hexafluorobutyl, heptafluorobutyl, octafluorobutyl, and perfluorobutyl.
烷氧基可為直鏈狀及分支鏈狀的任一種。作為碳數1~6的烷氧基,例如可列舉:甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、異丙氧基、異丁氧基、異戊氧基、新戊氧基。 The alkoxy group may be either a straight chain or a branched chain. Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, isobutoxy, isopentyloxy, and neopentyloxy.
作為碳數6~14的芳香族烴基,例如可列舉:苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基。 Examples of aromatic hydrocarbon groups having 6 to 14 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, and 9-anthryl.
作為碳數7~30的芳烷基,例如可列舉:苄基、苯乙基、萘基甲基、3-苯基丙基。 Examples of aralkyl groups having 7 to 30 carbon atoms include benzyl, phenethyl, naphthylmethyl, and 3-phenylpropyl.
含氮雜環可為單環及縮合環的任一種。作為3員~10員的含氮雜環,例如可列舉:吡咯啶環、嗎啉環、哌啶環、哌嗪環。 The nitrogen-containing heterocyclic ring may be either a monocyclic ring or a condensed ring. Examples of nitrogen-containing heterocyclic rings having 3 to 10 members include: pyrrolidine ring, morpholine ring, piperidine ring, and piperazine ring.
芳香族烴環可為單環及縮合環的任一種。碳數6~14的芳香族烴環可為苯環、萘環、菲環及蒽環的任一種。 The aromatic hydrocarbon ring may be a single ring or a condensed ring. The aromatic hydrocarbon ring with 6 to 14 carbon atoms may be a benzene ring, a naphthalene ring, a phenanthrene ring, or an anthracene ring.
芳香族雜環可為單環及縮合環的任一種。作為5員~10員的芳香族雜環,例如可列舉:吡咯環、噁唑環、吡唑環、咪唑環、噻唑環、呋喃環、噻吩環、吡啶環、嘧啶環、噠嗪環、吡嗪環、吲哚環、苯並咪唑環、苯並噻唑環、喹啉環、苯並呋喃環等。 Aromatic heterocyclic rings may be either monocyclic or condensed rings. Examples of 5- to 10-membered aromatic heterocyclic rings include pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring, furan ring, thiophene ring, pyridine ring, pyrimidine ring, oxazine ring, pyrazine ring, indole ring, benzimidazole ring, benzothiazole ring, quinoline ring, benzofuran ring, etc.
其次,對式(A3-1)中的基等進行說明。 Next, the bases etc. in formula (A3-1) are explained.
式(A3-1)中的R41a及R42a分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R41a與R42a鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環。 R 41a and R 42a in formula (A3-1) each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 41a and R 42a are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded.
式(A3-1)中的碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The saturated alkyl group having 1 to 20 carbon atoms in formula (A3-1) may have a substituent which is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group, and an amino group.
於式(A3-1)中的碳數1~20的飽和烴基為碳數2~20的飽和烴基的情況下,所述飽和烴基中所含的-CH2-可經取代為-O-或-CO-。此處,所述-CH2-中並不包含與氮原子鍵結的-CH2-及作為所述飽和烴基的末端的甲基中的-CH2-。另外,所述飽和烴基中所 含的-CH2-CH2-不會經取代為-O-O-或-CO-CO-。 When the saturated alkyl group having 1 to 20 carbon atoms in formula (A3-1) is a saturated alkyl group having 2 to 20 carbon atoms, -CH2- contained in the saturated alkyl group may be substituted with -O- or -CO-. Here, the -CH2- does not include -CH2- bonded to a nitrogen atom and -CH2- in a methyl group at the end of the saturated alkyl group. In addition, -CH2 - CH2- contained in the saturated alkyl group may not be substituted with -OO- or -CO-CO-.
式(A3-1)中的碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic alkyl group having 6 to 14 carbon atoms in formula (A3-1) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(A3-1)中的碳數7~30的芳烷基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The aralkyl group having 7 to 30 carbon atoms in formula (A3-1) may have at least one substituent selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms which may have a substituent.
式(A3-1)中的Rf表示碳數1~12的氟烷基。 Rf in formula (A3-1) represents a fluoroalkyl group having 1 to 12 carbon atoms.
式(A3-1)中的碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The alkyl group having 1 to 8 carbon atoms in formula (A3-1) may have at least one substituent selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group, and an amino group.
於式(A3-1)中的碳數1~8的烷基為碳數2~8的烷基的情況下,所述烷基中所含的-CH2-可經取代為-O-或-CO-。此處,所述-CH2-中並不包含作為所述烷基的末端的甲基中的-CH2-。另外,所述烷基中所含的-CH2-CH2-不會經取代為-O-O-或-CO-CO-。 When the alkyl group having 1 to 8 carbon atoms in formula (A3-1) is an alkyl group having 2 to 8 carbon atoms, -CH2- contained in the alkyl group may be substituted with -O- or -CO-. Here, the -CH2- does not include -CH2- in the methyl group at the end of the alkyl group. In addition, the -CH2 - CH2- contained in the alkyl group may not be substituted with -OO- or -CO-CO-.
R41a較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 41a is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R42a較佳為可具有選自由碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,更佳為具有一個或兩個碳數1~8的烷基作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基、且可具有-SO3 -的苯基。 R 42a is preferably a phenyl group which may have at least one substituent selected from the group consisting of an alkyl group having 1 to 8 carbon atoms and -SO 3 - , more preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 8 carbon atoms as substituents, and further preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 4 carbon atoms as substituents.
式(A3-1)中的R43a及R44a分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14 的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R43a與R44a鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環。 R 43a and R 44a in formula (A3-1) each independently represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 43a and R 44a are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded.
R43a較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 43a is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R44a較佳為可具有選自由碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,更佳為具有一個或兩個碳數1~8的烷基作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基、且可具有-SO3 -的苯基。 R 44a is preferably a phenyl group which may have at least one substituent selected from the group consisting of an alkyl group having 1 to 8 carbon atoms and -SO 3 - , more preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 8 carbon atoms as substituents, and further preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 4 carbon atoms as substituents.
式(A3-1)中的R47a~R54a分別獨立地表示氫原子、鹵素原子、硝基、羥基、-SO3 -、-SO2-N--SO2-Rf、或可具有取代基的碳數1~8的烷基。R47a~R54a分別獨立地較佳為氫原子、碳數1~8的烷基或-SO3 -,更佳為氫原子或-SO3 -。 R 47a to R 54a in formula (A3-1) each independently represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , or an alkyl group having 1 to 8 carbon atoms which may have a substituent. R 47a to R 54a each independently represent preferably a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or -SO 3 - , and more preferably a hydrogen atom or -SO 3 - .
式(A3-1)中的環T1a表示可具有取代基的碳數6~14的芳香族烴環或可具有取代基的5員~10員的芳香族雜環。 Ring T1a in Formula (A3-1) represents an aromatic hydrocarbon ring having 6 to 14 carbon atoms which may have a substituent, or an aromatic heterocyclic ring having 5 to 10 members which may have a substituent.
式(A3-1)中的碳數6~14的芳香族烴環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic hydrocarbon ring having 6 to 14 carbon atoms in formula (A3-1) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(A3-1)中的5員~10員的芳香族雜環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The 5- to 10-membered aromatic heterocyclic ring in formula (A3-1) may have a substituent which is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms which may have a substituent.
環T1a較佳為式(1t)所表示的環。 The ring T 1a is preferably a ring represented by the formula (1t).
式(1t)中的R45a及R46a分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R45a與R46a鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環。 R 45a and R 46a in formula (1t) each independently represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 45a and R 46a are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded.
式(1t)中的碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The saturated alkyl group having 1 to 20 carbon atoms in formula (1t) may have a substituent which is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group, and an amino group.
式(1t)中的碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic alkyl group having 6 to 14 carbon atoms in formula (1t) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(1t)中的碳數7~30的芳烷基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、-SO3 -、-SO2-N--SO2-Rf、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The aralkyl group having 7 to 30 carbon atoms in formula (1t) may have at least one substituent selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, -SO 3 - , -SO 2 -N - -SO 2 -R f , and an alkyl group having 1 to 8 carbon atoms which may have a substituent.
式(1t)中的碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The alkyl group having 1 to 8 carbon atoms in formula (1t) may have at least one substituent selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group and an amino group.
R45a較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 45a is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R46a較佳為可具有選自由碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,更佳為具有一個或兩個碳數1~8的烷基作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基、且可具有-SO3 -的苯基。 R 46a is preferably a phenyl group which may have at least one substituent selected from the group consisting of an alkyl group having 1 to 8 carbon atoms and -SO 3 - , more preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 8 carbon atoms as substituents, and further preferably a phenyl group which may have -SO 3 - and may have one or two alkyl groups having 1 to 4 carbon atoms as substituents.
式(1t)中的R56a表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基。 R 56a in formula (1t) represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent.
R56a較佳為可具有選自由鹵素原子、碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,更佳為具有一個或兩個鹵素原子作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個氟原子作為取代基、且可具有-SO3 -的苯基。 R 56a is preferably a phenyl group which may have at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 8 carbon atoms and -SO 3 - , more preferably a phenyl group which may have -SO 3 - and further preferably a phenyl group which may have -SO 3 - and one or two fluorine atoms as substituents.
式(1t)中的L1a表示硫原子、氧原子或-NR57a-。R57a表示氫原子或碳數1~10的烷基。L1a較佳為硫原子。 In formula (1t), L 1a represents a sulfur atom, an oxygen atom or -NR 57a -. R 57a represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. L 1a is preferably a sulfur atom.
式(1t)中的*表示與碳陽離子的鍵結位置。換言之,式(1t)中的-*表示鍵結。其他式中的-*亦同樣地表示鍵結。 The * in formula (1t) indicates the bonding position with the carbon cation. In other words, -* in formula (1t) indicates bonding. -* in other formulas also indicates bonding in the same way.
式(A3-1)中的r表示1以上的整數。r較佳為2。於r為2以上的整數的情況下,式(A3-1a)所表示的多個陰離子可相同亦可不同。 In formula (A3-1), r represents an integer greater than 1. Preferably, r is 2. When r is an integer greater than 2, the multiple anions represented by formula (A3-1a) may be the same or different.
[化24]
[式(A3-1a)中,環T1a、R41a~R44a及R47a~R54a分別與所述為相同含義] [In formula (A3-1a), ring T1a , R41a to R44a and R47a to R54a have the same meanings as described above]
以下有時將式(A3-1a)所表示的陰離子記載為「陰離子(A3-1a)」。多個陰離子(A3-1a)較佳為相同。 In the following, the anion represented by formula (A3-1a) is sometimes described as "anion (A3-1a)". It is preferred that a plurality of anions (A3-1a) are the same.
式(A3-1)中的k表示陰離子(A3-1a)所具有的-SO3 -及-SO2-N--SO2-Rf的個數的合計,且為2以上的整數。k較佳為2。 In the formula (A3-1), k represents the total number of -SO 3 - and -SO 2 -N - -SO 2 -R f possessed by the anion (A3-1a), and is an integer greater than or equal to 2. Preferably, k is 2.
式(A3-1)中的Mr+表示氫離子、r價的金屬離子或N+(R55a)4,四個R55a可相同,亦可不同。R55a表示氫原子、碳數1~20的飽和烴基或碳數7~10的芳烷基。於式(A3-1)中的k-1為2以上的整數的情況下,多個Mr+可相同亦可不同。 Mr + in formula (A3-1) represents a hydrogen ion, an r-valent metal ion or N + ( R55a ) 4 , and four R55a may be the same or different. R55a represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. When k-1 in formula (A3-1) is an integer greater than 2, multiple Mr + may be the same or different.
Mr+較佳為r價的金屬離子。作為r價的金屬離子,例如可列舉:鋰離子、鈉離子、鉀離子等鹼金屬離子;鈹離子、鎂離子、鈣離子、鍶離子、鋇離子等鹼土類金屬離子;鈦離子、鋯離子、鉻離子、錳離子、鐵離子、鈷離子、鎳離子、銅離子等過渡金屬離子;鋅離子、鎘離子、鋁離子、銦離子、錫離子、鉛離子、鉍離子等典型金屬離子。 Mr + is preferably an r-valent metal ion. Examples of r-valent metal ions include alkaline metal ions such as lithium ion, sodium ion, potassium ion; alkaline earth metal ions such as palladium ion, magnesium ion, calcium ion, strontium ion, barium ion; transition metal ions such as titanium ion, zirconium ion, chromium ion, manganese ion, iron ion, cobalt ion, nickel ion, copper ion; and typical metal ions such as zinc ion, cadmium ion, aluminum ion, indium ion, tin ion, lead ion, and bismuth ion.
Mr+更佳為二價金屬離子,進而佳為鹼土類金屬離子,特佳為鋇離子(Ba2+)。 Mr + is more preferably a divalent metal ion, further preferably an alkali earth metal ion, and particularly preferably a barium ion (Ba2 + ).
作為化合物(A3-1),較佳為如下化合物(以下,有時記載為「化合物(A3-1')」),所述化合物中R41a及R43a分別獨立地為氫原子或碳數1~8的烷基,R42a及R44a分別獨立地為可具有選自由碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,R47a~R54a分別獨立地為氫原子、碳數1~8的烷基或-SO3 -,環T1a為所述式(1t)所表示的環[式(1t)中,R45a為氫原子或碳數1~8的烷基,R46a為可具有選自由碳數1~8的烷基及-SO3 -所組成的群組中的至少一個取代基的苯基,R56a為可具有選自由鹵素原子、碳數1~8的烷基及-SO3 -所組成的群組的至少一個取代基的苯基,L1a為硫原子,以及*表示與碳陽離子的鍵結位置],r為2,k表示陰離子(A3-1a)所具有的-SO3 -的個數的合計且為2,兩個陰離子(A3-1a)相同,以及Mr+為Ba2+。 The compound (A3-1) is preferably a compound (hereinafter sometimes described as "compound (A3-1')"), wherein R 41a and R 43a are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 42a and R 44a are each independently a phenyl group which may have at least one substituent selected from the group consisting of an alkyl group having 1 to 8 carbon atoms and -SO 3 - , R 47a to R 54a are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or -SO 3 - , and ring T 1a is a ring represented by the formula (1t) [in the formula (1t), R 45a is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 46a is a phenyl group which may have at least one substituent selected from the group consisting of an alkyl group having 1 to 8 carbon atoms and -SO 3 - , R 56a is a phenyl group which may have at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 8 carbon atoms, and -SO 3 - , L 1a is a sulfur atom, and * represents a bonding position with a carbon cation], r is 2, k represents the total number of -SO 3 - contained in the anion (A3-1a) and is 2, the two anions (A3-1a) are the same, and Mr + is Ba 2+ .
於化合物(A3-1')中,R41a及R43a更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基;R42a及R44a分別獨立地 更佳為具有一個或兩個碳數1~8的烷基作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基、且可具有-SO3 -的苯基;R47a~R54a更佳為氫原子或-SO3 -;R45a更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基,R46a更佳為具有一個或兩個碳數1~8的烷基作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基、且可具有-SO3 -的苯基;以及R56a更佳為具有一個或兩個鹵素原子作為取代基、且可具有-SO3 -的苯基,進而佳為具有一個或兩個氟原子作為取代基、且可具有-SO3 -的苯基。 In compound (A3-1'), R 41a and R 43a are more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms; R 42a and R 44a are each independently more preferably a phenyl group having one or two alkyl groups having 1 to 8 carbon atoms as substituents and optionally having -SO 3 - , and more preferably a phenyl group having one or two alkyl groups having 1 to 4 carbon atoms as substituents and optionally having -SO 3 - ; R 47a to R 54a are more preferably a hydrogen atom or -SO 3 - ; R 45a is more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms; R 46a is more preferably a phenyl group having one or two alkyl groups having 1 to 8 carbon atoms as substituents and optionally having -SO 3 -. -phenyl , further preferably phenyl having one or two alkyl groups of 1 to 4 carbon atoms as substituents and optionally having -SO 3 - ; and R 56a is more preferably phenyl having one or two halogen atoms as substituents and optionally having -SO 3 - , further preferably phenyl having one or two fluorine atoms as substituents and optionally having -SO 3 - .
化合物(A3-1)中,特佳為下述式(A3-1-1)所表示的化合物(以下,有時記載為「化合物(A3-1-1)」)。再者,下述式(A3-1-1)中,兩個「-SO3 -」的記載是指各陰離子具有-SO3 -作為取代基,且各陰離子中的-SO3 -的個數的合計為2(即,兩個陰離子中的-SO3 -的個數的合計為4)。 Among the compounds (A3-1), particularly preferred are compounds represented by the following formula (A3-1-1) (hereinafter, sometimes described as "compound (A3-1-1)"). In the following formula (A3-1-1), the description of two "-SO 3 - " means that each anion has -SO 3 - as a substituent, and the total number of -SO 3 - in each anion is 2 (that is, the total number of -SO 3 - in the two anions is 4).
化合物(A3-1)可依據公知的方法(例如,「有機化學期刊(Journal of Organic Chemistry)」((1994),vol.59,#11,pp.3232-3236)中記載的方法、日本專利特開2018-127596號公報中記載的方法)來製造。 Compound (A3-1) can be produced according to a known method (for example, the method described in "Journal of Organic Chemistry" ((1994), vol.59, #11, pp.3232-3236), and the method described in Japanese Patent Publication No. 2018-127596).
其次,對式(A3-2)中的基等進行說明。 Next, the bases etc. in formula (A3-2) are explained.
式(A3-2)中的R41b及R42b分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R41b與R42b鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環。 R 41b and R 42b in formula (A3-2) each independently represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 41b and R 42b are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded.
式(A3-2)中的碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The saturated alkyl group having 1 to 20 carbon atoms in formula (A3-2) may have a substituent which is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a formyl group, and an amino group.
於式(A3-2)中的碳數1~20的飽和烴基為碳數2~20的飽和烴基的情況下,所述飽和烴基中所含的-CH2-可經取代為-O-或-CO-。此處,所述-CH2-中並不包含與氮原子鍵結的-CH2-及作為所述飽和烴基的末端的甲基中的-CH2-。另外,所述飽和烴基中所含的-CH2-CH2-不會經取代為-O-O-或-CO-CO-。 When the saturated alkyl group having 1 to 20 carbon atoms in formula (A3-2) is a saturated alkyl group having 2 to 20 carbon atoms, -CH2- contained in the saturated alkyl group may be substituted with -O- or -CO-. Here, the -CH2- does not include -CH2- bonded to a nitrogen atom and -CH2- in a methyl group at the end of the saturated alkyl group. In addition, -CH2 - CH2- contained in the saturated alkyl group may not be substituted with -OO- or -CO-CO-.
式(A3-2)中的碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic alkyl group having 6 to 14 carbon atoms in formula (A3-2) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(A3-2)中的碳數7~30的芳烷基可具有的取代基為 選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aralkyl group having 7 to 30 carbon atoms in formula (A3-2) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(A3-2)中的碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The alkyl group with 1 to 8 carbon atoms in formula (A3-2) may have at least one substituent selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group and an amino group.
於式(A3-2)中的碳數1~8的烷基為碳數2~8的烷基的情況下,所述烷基中所含的-CH2-可經取代為-O-或-CO-。此處,所述-CH2-中並不包含作為所述烷基的末端的甲基中的-CH2-。另外,所述烷基中所含的-CH2-CH2-不會經取代為-O-O-或-CO-CO-。 When the alkyl group having 1 to 8 carbon atoms in formula (A3-2) is an alkyl group having 2 to 8 carbon atoms, -CH2- contained in the alkyl group may be substituted with -O- or -CO-. Here, the -CH2- does not include -CH2- in the methyl group at the end of the alkyl group. In addition, -CH2 - CH2- contained in the alkyl group may not be substituted with -OO- or -CO-CO-.
R41b較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 41b is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R42b較佳為可具有碳數1~8的烷基的苯基,更佳為可具有碳數1~4的烷基的苯基,進而佳為苯基。 R 42b is preferably a phenyl group which may have an alkyl group having 1 to 8 carbon atoms, more preferably a phenyl group which may have an alkyl group having 1 to 4 carbon atoms, and further preferably a phenyl group.
式(A3-2)中的R43b及R44b分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R43b與R44b鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮雜環。 R 43b and R 44b in formula (A3-2) each independently represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 43b and R 44b are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atoms to which they are bonded.
R43b較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 43b is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R44b較佳為可具有碳數1~8的烷基的苯基,更佳為可具有碳數1~4的烷基的苯基,進而佳為苯基。 R 44b is preferably a phenyl group which may have an alkyl group having 1 to 8 carbon atoms, more preferably a phenyl group which may have an alkyl group having 1 to 4 carbon atoms, and further preferably a phenyl group.
式(A3-2)中的R47b~R54b分別獨立地表示氫原子、鹵 素原子、硝基、羥基、或可具有取代基的碳數1~8的烷基。 In formula (A3-2), R 47b to R 54b each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms which may have a substituent.
R47b~R54b分別獨立地較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為氫原子。 R 47b to R 54b are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably a hydrogen atom.
式(A3-2)中的環T1b表示可具有取代基的碳數6~14的芳香族烴環或可具有取代基的5員~10員的芳香族雜環。 Ring T 1b in formula (A3-2) represents an aromatic hydrocarbon ring having 6 to 14 carbon atoms which may have a substituent, or an aromatic heterocyclic ring having 5 to 10 members which may have a substituent.
式(A3-2)中的碳數6~14的芳香族烴環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic hydrocarbon ring having 6 to 14 carbon atoms in formula (A3-2) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(A3-2)中的5員~10員的芳香族雜環可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基、及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The 5- to 10-membered aromatic heterocyclic ring in formula (A3-2) may have a substituent that is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
環T1b較佳為式(2t)所表示的環。 The ring T 1b is preferably a ring represented by the formula (2t).
式(2t)中的R45b及R46b分別獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基,或者R45b與R46b鍵結並與該些所鍵結的氮原子一同形成3員~10員的含氮 雜環。 R 45b and R 46b in formula (2t) each independently represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, or R 45b and R 46b are bonded to form a 3- to 10-membered nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded.
式(2t)中的碳數1~20的飽和烴基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The saturated alkyl group having 1 to 20 carbon atoms in formula (2t) may have a substituent which is at least one selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group and an amino group.
式(2t)中的碳數6~14的芳香族烴基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aromatic hydrocarbon group having 6 to 14 carbon atoms in formula (2t) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a methyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(2t)中的碳數7~30的芳烷基可具有的取代基為選自由鹵素原子、硝基、羥基、甲醯基及可具有取代基的碳數1~8的烷基所組成的群組中的至少一個。 The substituent that the aralkyl group having 7 to 30 carbon atoms in formula (2t) may have is at least one selected from the group consisting of a halogen atom, a nitro group, a hydroxyl group, a formyl group, and an alkyl group having 1 to 8 carbon atoms that may have a substituent.
式(2t)中的碳數1~8的烷基可具有的取代基為選自由鹵素原子、羥基、甲醯基及胺基所組成的群組中的至少一個。 The alkyl group having 1 to 8 carbon atoms in formula (2t) may have at least one substituent selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group and an amino group.
R45b較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基。 R 45b is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.
R46b較佳為可具有碳數1~8的烷基的苯基,更佳為具有一個或兩個碳數1~8的烷基作為取代基的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基的苯基。 R 46b is preferably a phenyl group which may have an alkyl group having 1 to 8 carbon atoms, more preferably a phenyl group having one or two alkyl groups having 1 to 8 carbon atoms as substituents, and further preferably a phenyl group having one or two alkyl groups having 1 to 4 carbon atoms as substituents.
式(2t)中的R56b表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~14的芳香族烴基、或可具有取代基的碳數7~30的芳烷基。 R 56b in formula (2t) represents a hydrogen atom, a saturated alkyl group having 1 to 20 carbon atoms which may have a substituent, an aromatic alkyl group having 6 to 14 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent.
R56b較佳為可具有選自由鹵素原子及碳數1~8的烷基所組成的群組中的至少一個取代基的苯基,更佳為具有一個或兩 個鹵素原子作為取代基的苯基,進而佳為具有一個或兩個氟原子作為取代基的苯基。 R 56b is preferably a phenyl group which may have at least one substituent selected from the group consisting of a halogen atom and an alkyl group having 1 to 8 carbon atoms, more preferably a phenyl group having one or two halogen atoms as substituents, and further preferably a phenyl group having one or two fluorine atoms as substituents.
式(2t)中的L1b表示硫原子、氧原子或-NR57b-。R57b表示氫原子或碳數1~10的烷基。L1b較佳為硫原子。 In formula (2t), L 1b represents a sulfur atom, an oxygen atom or -NR 57b -. R 57b represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. L 1b is preferably a sulfur atom.
式(2t)中的*表示與碳陽離子的鍵結位置。 The * in formula (2t) represents the bonding position with the carbon cation.
式(A3-2)中的m表示1以上的整數。m較佳為1~20的整數,更佳為2~14的整數,進而佳為2~8的整數,特佳為3。於m為2以上的整數的情況下,式(A3-2c)所表示的多個陽離子可相同亦可不用。 In formula (A3-2), m represents an integer greater than 1. m is preferably an integer of 1 to 20, more preferably an integer of 2 to 14, further preferably an integer of 2 to 8, and particularly preferably 3. When m is an integer greater than 2, the multiple cations represented by formula (A3-2c) may be the same or different.
[式(A3-2c)中,環T1b、R41b~R44b及R47b~R54b分別與所述為相同含義] [In formula (A3-2c), ring T1b , R41b to R44b and R47b to R54b have the same meanings as described above]
以下有時將式(A3-2c)所表示的陽離子記載為「陽離子(A3-2c)」。多個陽離子(A3-2c)較佳為相同。 Hereinafter, the cation represented by formula (A3-2c) may be referred to as "cation (A3-2c)". It is preferred that the plurality of cations (A3-2c) are the same.
式(A3-2)中的[Y]m-表示m價的陰離子。[Y]m-較佳為 含有鎢原子的多酸根陰離子,更佳為[PW12O40]3-、[P2W18O62]6-、[SiW12O40]4-、[P2W17O61]10-、[P2W15O56]12-、[H2P2W12O48]12-、[NaP5W30O110]14-、[SiW9O34]10-、[SiW10O36]8-、[SiW11O39]8-、[W6O19]2-、[W10O32]4-或[WO4]2-,進而佳為[PW12O40]3-。 [Y] m- in formula (A3-2) represents an m-valent anion. [Y] m- is preferably a polyanion containing a tungsten atom, more preferably [PW 12 O 40 ] 3- , [P 2 W 18 O 62 ] 6- , [SiW 12 O 40 ] 4- , [P 2 W 17 O 61 ] 10- , [P 2 W 15 O 56 ] 12- , [H 2 P 2 W 12 O 48 ] 12- , [NaP 5 W 30 O 110 ] 14- , [SiW 9 O 34 ] 10- , [SiW 10 O 36 ] 8- , [SiW 11 O 39 ] 8- , [W 6 O 19 ] 2- , [W 10 O 32 ] 4- or [WO 4 ] 2- , and preferably [PW 12 O 40 ] 3- .
作為化合物(A3-2),較佳為如下化合物(以下,有時記載為「化合物(A3-2')」),所述化合物中R41b、R43b及R47b~R54b分別獨立地為氫原子或碳數1~8的烷基,R42b及R44b分別獨立地為可具有碳數1~8的烷基的苯基,環T1b為式(2t)所表示的環[式(2t)中,R45b為氫原子或碳數1~8的烷基,R46b為可具有碳數1~8的烷基的苯基,R56b為可具有選自由鹵素原子及碳數1~8的烷基所組成的群組中的至少一個取代基的苯基,L1b為硫原子,以及*表示與碳陽離子的鍵結位置],m為3,三個陽離子(A3-2c)相同,以及[Y]m-為[PW12O40]3-。 The compound (A3-2) is preferably a compound (hereinafter sometimes described as "compound (A3-2')"), wherein R 41b , R 43b and R 47b to R 54b are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 42b and R 44b are each independently a phenyl group which may have an alkyl group having 1 to 8 carbon atoms, and ring T 1b is a ring represented by formula (2t) [in formula (2t), R 45b is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 46b is a phenyl group which may have an alkyl group having 1 to 8 carbon atoms, and R 56b is a phenyl group which may have at least one substituent selected from the group consisting of a halogen atom and an alkyl group having 1 to 8 carbon atoms, and L 1b is a sulfur atom, and * indicates a bonding position with a carbon cation], m is 3, the three cations (A3-2c) are the same, and [Y] m- is [PW 12 O 40 ] 3- .
於化合物(A3-2')中,R41b及R43b分別獨立地較佳為氫原子或碳數1~8的烷基,更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基;R42b及R44b分別獨立地更佳為可具有碳 數1~4的烷基的苯基,進而佳為苯基;R47b~R54b分別獨立地更佳為氫原子或碳數1~4的烷基,進而佳為氫原子;R45b更佳為氫原子或碳數1~4的烷基,進而佳為碳數1~4的烷基;R46b更佳為具有一個或兩個碳數1~8的烷基作為取代基的苯基,進而佳為具有一個或兩個碳數1~4的烷基作為取代基的苯基;以及R56b更佳為具有一個或兩個鹵素原子作為取代基的苯基,進而佳為具有一個或兩個氟原子作為取代基的苯基。 In compound (A3-2'), R 41b and R 43b are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and further preferably an alkyl group having 1 to 4 carbon atoms; R 42b and R 44b are each independently more preferably a phenyl group which may have an alkyl group having 1 to 4 carbon atoms, and further preferably a phenyl group; R 47b to R 54b are each independently more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and further preferably a hydrogen atom; R 45b is more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and further preferably an alkyl group having 1 to 4 carbon atoms; R 46b is more preferably a phenyl group having one or two alkyl groups having 1 to 8 carbon atoms as substituents, and further preferably a phenyl group having one or two alkyl groups having 1 to 4 carbon atoms as substituents; and R 56b is more preferably a phenyl group having one or two halogen atoms as substituents, and further preferably a phenyl group having one or two fluorine atoms as substituents.
於化合物(A3-2)中,特佳為下述式(A3-2-1)所表示的化合物(以下,有時記載為「化合物(A3-2-1)」)。 Among the compounds (A3-2), the compounds represented by the following formula (A3-2-1) are particularly preferred (hereinafter, sometimes described as "compound (A3-2-1)").
化合物(A3-2)可依據公知的方法(例如,日本專利特開2015-28121號公報中記載的方法)來製造。 Compound (A3-2) can be produced according to a known method (for example, the method described in Japanese Patent Publication No. 2015-28121).
化合物(A3)較佳為與不溶解其的溶劑混合而作為化合物(A3)的分散液來使用。於製造化合物(A3)的分散液時,較 佳為使用分散劑。作為分散劑,例如可列舉針對顏料分散液所敘述的分散劑。 The compound (A3) is preferably mixed with a solvent that does not dissolve it and used as a dispersion of the compound (A3). When preparing the dispersion of the compound (A3), it is preferred to use a dispersant. As the dispersant, for example, the dispersants described for the pigment dispersion can be cited.
於在化合物(A3)的分散液中包含分散劑的情況下,其含量相對於化合物(A3)100重量份而較佳為1重量份以上且500重量份以下,更佳為5重量份以上且300重量份以下。若分散劑的含量處於所述範圍內,則有可獲得均勻的分散狀態的顏料分散液的傾向。 When a dispersant is included in the dispersion of compound (A3), its content is preferably 1 part by weight or more and 500 parts by weight or less, and more preferably 5 parts by weight or more and 300 parts by weight or less, relative to 100 parts by weight of compound (A3). If the content of the dispersant is within the above range, a uniformly dispersed pigment dispersion tends to be obtained.
於使用化合物(A3)的情況下,其含量相對於固體成分的總量而較佳為1重量%以上,更佳為1.5重量%以上,且較佳為60重量%以下,更佳為55重量%以下,進而佳為50重量%以下。 When compound (A3) is used, its content is preferably 1% by weight or more, more preferably 1.5% by weight or more, and preferably 60% by weight or less, more preferably 55% by weight or less, and further preferably 50% by weight or less relative to the total amount of solid components.
於使用化合物(A3)的情況下,較佳為使用與化合物(A3)不同的染料(A1)。即,於本發明的一較佳態樣中,著色劑(A)包含與化合物(A3)不同的染料(A1)及化合物(A3)。該一態樣中的染料(A1)的種類及含量等的說明為如上所述。 When using compound (A3), it is preferred to use a dye (A1) different from compound (A3). That is, in a preferred embodiment of the present invention, the coloring agent (A) contains a dye (A1) different from compound (A3) and compound (A3). The type and content of the dye (A1) in this embodiment are as described above.
於使用染料(A1)及化合物(A3)的情況下,染料(A1)與化合物(A3)的重量比(染料(A1):化合物(A3))較佳為0.5:99.5~99:1,更佳為0.5:99.5~95:5,特佳為0.5:99.5~90:10。 When dye (A1) and compound (A3) are used, the weight ratio of dye (A1) to compound (A3) (dye (A1): compound (A3)) is preferably 0.5:99.5~99:1, more preferably 0.5:99.5~95:5, and particularly preferably 0.5:99.5~90:10.
<樹脂(B)> <Resin (B)>
本發明中使用的樹脂(B)含有包含式(1b)所表示的構成單元(b1-1)(以下,有時記載為「構成單元(b1-1)」)的樹脂(B1)。 The resin (B) used in the present invention contains a resin (B1) containing a constituent unit (b1-1) represented by formula (1b) (hereinafter, sometimes described as "constituent unit (b1-1)").
[化29]
[式(1b)中,R1B表示氫原子或甲基,R2B~R4B分別獨立地表示氫原子、碳數1~6的烷基或碳數1~6的烷氧基,n表示1~10的整數,以及*表示鍵結位置,其中,R2B~R4B的至少一個為碳數1~6的烷氧基] [In formula (1b), R 1B represents a hydrogen atom or a methyl group, R 2B to R 4B each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, n represents an integer of 1 to 10, and * represents a bonding position, wherein at least one of R 2B to R 4B is an alkoxy group having 1 to 6 carbon atoms]
樹脂(B1)中,構成單元(b1-1)可包含僅一種,亦可包含兩種以上。藉由使用樹脂(B1),可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少。 In the resin (B1), the constituent unit (b1-1) may include only one type or two or more types. By using the resin (B1), the reduction in thickness of the coloring pattern or the coloring coating film caused by heating (especially post-baking) can be suppressed.
作為R2B~R4B中的碳數1~6的烷基,例如可列舉:甲基、乙基、丙基、丁基、戊基、己基、異丙基、異丁基、異戊基、新戊基。 Examples of the alkyl group having 1 to 6 carbon atoms in R 2B to R 4B include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, isopentyl and neopentyl.
作為R2B~R4B中的碳數1~6的烷氧基,例如可列舉:甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、異丙氧基、異丁氧基、異戊氧基、新戊氧基。 Examples of the alkoxy group having 1 to 6 carbon atoms in R 2B to R 4B include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, isobutoxy, isopentyloxy and neopentyloxy.
R2B~R4B分別獨立地較佳為甲氧基、乙氧基或丙氧基,更佳為甲氧基或乙氧基。 R 2B to R 4B are each independently preferably methoxy, ethoxy or propoxy, more preferably methoxy or ethoxy.
n較佳為1~6的整數,更佳為1~3的整數。 n is preferably an integer between 1 and 6, and more preferably an integer between 1 and 3.
樹脂(B1)較佳為包含構成單元(b1-1)、源自具有酸性基的聚合性不飽和化合物的構成單元(b1-2)(以下,有時記載為「構成單元(b1-2)」)以及其他構成單元(b1-3)(以下,有時記載為「構成單元(b1-3)」)的共聚物。此處,所謂其他構成單元(b1-3),是指與構成單元(b1-1)及構成單元(b1-2)不同的構成單元。作為共聚物的樹脂(B1)中,構成單元(b1-1)、構成單元(b1-2)以及構成單元(b1-3)均可包含僅一種,亦可包含兩種以上。 The resin (B1) is preferably a copolymer comprising a constituent unit (b1-1), a constituent unit (b1-2) derived from a polymerizable unsaturated compound having an acidic group (hereinafter, sometimes described as "constituent unit (b1-2)"), and other constituent units (b1-3) (hereinafter, sometimes described as "constituent unit (b1-3)"). Here, the so-called other constituent unit (b1-3) refers to a constituent unit different from the constituent unit (b1-1) and the constituent unit (b1-2). In the resin (B1) as a copolymer, the constituent unit (b1-1), the constituent unit (b1-2), and the constituent unit (b1-3) may each contain only one kind or two or more kinds.
作為構成單元(b1-2)所具有的酸性基,例如可列舉:羧基、磷酸基(-O-P(=O)(OH)2)、磺基(-S(=O)2OH)。該些中,較佳為羧基。 Examples of the acidic group contained in the constituent unit (b1-2) include a carboxyl group, a phosphoric acid group (-OP(=O)(OH) 2 ), and a sulfonic acid group (-S(=O) 2 OH). Among these, a carboxyl group is preferred.
就耐溶劑性的觀點而言,將共聚物中的所有構成單元的合計設為100莫耳%時的構成單元(b1-1)的量較佳為1莫耳%~50莫耳%,更佳為5莫耳%~40莫耳%,進而佳為10莫耳%~30莫耳%。 From the viewpoint of solvent resistance, the amount of the constituent unit (b1-1) when the total of all constituent units in the copolymer is set to 100 mol% is preferably 1 mol% to 50 mol%, more preferably 5 mol% to 40 mol%, and even more preferably 10 mol% to 30 mol%.
就顯影性的觀點而言,將共聚物中的所有構成單元的合計設為100莫耳%時的構成單元(b1-2)的量較佳為10莫耳%~50莫耳%,更佳為15莫耳%~45莫耳%,進而佳為20莫耳%~40莫耳%。 From the viewpoint of developing properties, the amount of the constituent unit (b1-2) when the total of all constituent units in the copolymer is set to 100 mol% is preferably 10 mol% to 50 mol%, more preferably 15 mol% to 45 mol%, and even more preferably 20 mol% to 40 mol%.
就顯影性及耐溶劑性的觀點而言,將共聚物中的所有構成單元的合計設為100莫耳%時的構成單元(b1-3)的量較佳為1 莫耳%~89莫耳%,更佳為15莫耳%~80莫耳%,進而佳為30莫耳%~70莫耳%。 From the viewpoint of developing properties and solvent resistance, the amount of the constituent unit (b1-3) when the total of all constituent units in the copolymer is set to 100 mol% is preferably 1 mol% to 89 mol%, more preferably 15 mol% to 80 mol%, and even more preferably 30 mol% to 70 mol%.
就顯影性的觀點而言,樹脂(B1)的重量平均分子量(Mw)為1,000~50,000,較佳為2,000~40,000,更佳為3,000~30,000。所述重量平均分子量(Mw)是使用凝膠滲透層析法(Gel Permeation Chromatography,GPC)並藉由聚苯乙烯換算來算出的值。 From the perspective of developing properties, the weight average molecular weight (Mw) of the resin (B1) is 1,000 to 50,000, preferably 2,000 to 40,000, and more preferably 3,000 to 30,000. The weight average molecular weight (Mw) is a value calculated by gel permeation chromatography (GPC) and converted to polystyrene.
就耐熱分解性、耐熱黃變性及耐溶劑性的觀點而言,樹脂(B1)的矽烷基當量較佳為400~4,000,更佳為500~3,000。若樹脂(B1)的矽烷基當量為400以上,則對於進一步提高著色圖案或著色塗膜的耐熱分解性及耐熱黃變性而言有效。再者,樹脂(B1)的矽烷基當量為根據下述式子算出的值: 矽烷基當量=樹脂(B1)的重量平均分子量/每一分子中的矽烷基的平均個數。 From the viewpoint of thermal decomposition resistance, thermal yellowing resistance and solvent resistance, the silyl equivalent of resin (B1) is preferably 400 to 4,000, and more preferably 500 to 3,000. If the silyl equivalent of resin (B1) is 400 or more, it is effective for further improving the thermal decomposition resistance and thermal yellowing resistance of the colored pattern or colored coating. In addition, the silyl equivalent of resin (B1) is a value calculated according to the following formula: Silyl equivalent = weight average molecular weight of resin (B1) / average number of silyl groups in one molecule.
矽烷基當量可根據樹脂(B1)的製造中使用的單量體的投入量來算出。 The silyl equivalent can be calculated from the input amount of the monomer used in the production of the resin (B1).
於樹脂(B1)為包含構成單元(b1-2)的共聚物的情況下,就顯影性的觀點而言,樹脂(B1)的酸價較佳為20mgKOH/g~300mgKOH/g,更佳為30mgKOH/g~200mgKOH/g。再者,所謂樹脂(B1)的酸價,是依照日本工業標準(Japanese Industrial Standards,JIS)K6901 5.3並使用溴瑞香草酚藍(bromothymol blue)與酚紅的混合指示劑來測定的值,為作為中和樹脂(B1)1g所需的氫氧化鉀的量(mg)來算出的值,例如可藉由使用氫氧化鉀水溶液進行滴定來求出。 When the resin (B1) is a copolymer containing the constituent unit (b1-2), the acid value of the resin (B1) is preferably 20 mgKOH/g to 300 mgKOH/g, and more preferably 30 mgKOH/g to 200 mgKOH/g from the viewpoint of developing properties. The acid value of the resin (B1) is a value measured in accordance with Japanese Industrial Standards (JIS) K6901 5.3 using a mixed indicator of bromothymol blue and phenol red, and is a value calculated as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B1), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.
就於鹼顯影後形成無缺損及剝離的良好的圖案的觀點而言,相對於聚合性化合物(C)100重量份,樹脂(B1)的含量較佳為5重量份~400重量份,更佳為7.5重量份~375重量份,進而佳為10重量份~350重量份。 From the perspective of forming a good pattern without defects and peeling after alkali development, the content of the resin (B1) is preferably 5 to 400 parts by weight, more preferably 7.5 to 375 parts by weight, and further preferably 10 to 350 parts by weight, relative to 100 parts by weight of the polymerizable compound (C).
樹脂(B1)可藉由如下方式來製造:於溶劑的存在下,依照公知的自由基聚合方法僅使下述式(2b)所表示的化合物(m1-1)(以下,有時記載為「化合物(m1-1)」)、或使包含化合物(m1-1)及其他化合物的單體混合物進行共聚。 The resin (B1) can be produced by copolymerizing only the compound (m1-1) represented by the following formula (2b) (hereinafter, sometimes described as "compound (m1-1)") or a monomer mixture containing the compound (m1-1) and other compounds in the presence of a solvent according to a known free radical polymerization method.
[式(2b)中的記號的含義為如上所述] [The meanings of the symbols in formula (2b) are as described above]
作為共聚物的樹脂(B1)例如可藉由如下方式來製造:將化合物(m1-1)以及視需要的其他化合物溶解於溶劑中,製備溶液後,於該溶液中添加聚合起始劑,並在50℃~130℃下反應1 小時~20小時。 The copolymer resin (B1) can be produced, for example, by dissolving the compound (m1-1) and other compounds as needed in a solvent, preparing a solution, adding a polymerization initiator to the solution, and reacting at 50°C to 130°C for 1 hour to 20 hours.
作為包含構成單元(b1-1)、構成單元(b1-2)及構成單元(b1-3)的共聚物的樹脂(B1)可藉由如下方式來製造:於溶劑的存在下,依照公知的自由基聚合方法使包含化合物(m1-1)、具有酸性基的聚合性不飽和化合物(m1-2)(以下,有時記載為「化合物(m1-2)」)、以及其他聚合性不飽和化合物(m1-3)(以下,有時記載為「化合物(m1-3)」)的單體混合物進行共聚。此處,所謂其他聚合性不飽和化合物(m1-3),是指與化合物(m1-1)及化合物(m1-2)不同的聚合性不飽和化合物。另外,構成單元(b1-1)源自化合物(m1-1),構成單元(b1-2)源自化合物(m1-2),構成單元(b1-3)源自化合物(m1-3)。 The resin (B1) which is a copolymer comprising the constituent unit (b1-1), the constituent unit (b1-2) and the constituent unit (b1-3) can be produced by copolymerizing a monomer mixture comprising the compound (m1-1), a polymerizable unsaturated compound (m1-2) having an acidic group (hereinafter, sometimes described as "the compound (m1-2)") and other polymerizable unsaturated compounds (m1-3) (hereinafter, sometimes described as "the compound (m1-3)") in the presence of a solvent according to a known free radical polymerization method. Here, the other polymerizable unsaturated compound (m1-3) refers to a polymerizable unsaturated compound different from the compound (m1-1) and the compound (m1-2). In addition, the constituent unit (b1-1) is derived from the compound (m1-1), the constituent unit (b1-2) is derived from the compound (m1-2), and the constituent unit (b1-3) is derived from the compound (m1-3).
作為共聚物的樹脂(B1)例如可藉由如下方式來製造:將化合物(m1-1)、化合物(m1-2)及化合物(m1-3)溶解於溶劑中,製備溶液後,於該溶液中添加聚合起始劑,並在50℃~130℃下反應1小時~20小時。 The copolymer resin (B1) can be produced, for example, by dissolving compound (m1-1), compound (m1-2) and compound (m1-3) in a solvent, preparing a solution, adding a polymerization initiator to the solution, and reacting at 50°C to 130°C for 1 hour to 20 hours.
作為化合物(m1-1),例如可列舉:3-(甲基)丙烯醯基氧基丙基甲基二甲氧基矽烷、3-(甲基)丙烯醯基氧基丙基乙基二甲氧基矽烷、3-(甲基)丙烯醯基氧基丙基甲基二乙氧基矽烷、3-(甲基)丙烯醯基氧基丙基乙基二乙氧基矽烷、3-(甲基)丙烯醯基氧基丙基三甲氧基矽烷、3-(甲基)丙烯醯基氧基丙基三乙氧基矽烷等。該些中,就獲得的容易性及反應性的觀點而言,較佳為3-(甲基)丙烯醯基氧基丙基三甲氧基矽烷及3-(甲基)丙烯醯基氧基丙基三乙氧基 矽烷。此處,所謂「3-(甲基)丙烯醯基氧基丙基甲基二甲氧基矽烷」,是指選自3-丙烯醯基氧基丙基甲基二甲氧基矽烷及3-甲基丙烯醯基氧基丙基甲基二甲氧基矽烷中的至少一種。其他相同的記載亦為相同的含義。 Examples of compound (m1-1) include 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropylethyldimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropylethyldiethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, and 3-(meth)acryloxypropyltriethoxysilane. Among these, 3-(meth)acryloxypropyltrimethoxysilane and 3-(meth)acryloxypropyltriethoxysilane are preferred in terms of availability and reactivity. Here, "3-(meth)acryloxypropylmethyldimethoxysilane" refers to at least one selected from 3-acryloxypropylmethyldimethoxysilane and 3-methacryloxypropylmethyldimethoxysilane. Other identical descriptions have the same meaning.
作為化合物(m1-2)所具有的酸性基,例如可列舉:羧基、磷酸基(-O-P(=O)(OH)2)、磺基(-S(=O)2OH)。該些中,較佳為羧基。 Examples of the acidic group contained in compound (m1-2) include a carboxyl group, a phosphate group (—OP(═O)(OH) 2 ), and a sulfone group (—S(═O) 2 OH). Among these, a carboxyl group is preferred.
作為化合物(m1-2),例如可列舉:(甲基)丙烯酸、丁烯酸、肉桂酸、乙烯基磺酸、2-(甲基)丙烯醯基氧基乙基琥珀酸、2-丙烯醯基氧基乙基鄰苯二甲酸、2-(甲基)丙烯醯基氧基乙基六氫鄰苯二甲酸、2-(甲基)丙烯醯基氧基乙基酸式磷酸酯等。該些中,就獲得的容易性及反應性的觀點而言,較佳為(甲基)丙烯酸。 As compound (m1-2), for example, (meth)acrylic acid, crotonic acid, cinnamic acid, vinyl sulfonic acid, 2-(meth)acryloyloxyethyl succinic acid, 2-acryloyloxyethyl phthalic acid, 2-(meth)acryloyloxyethyl hexahydrophthalic acid, 2-(meth)acryloyloxyethyl acid phosphate, etc. Among them, (meth)acrylic acid is preferred from the viewpoint of ease of acquisition and reactivity.
作為化合物(m1-3),例如可列舉以下化合物:丁二烯;(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸戊酯、(甲基)丙烯酸新戊酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸異戊酯、(甲基)丙烯酸己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸月桂基酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸甲基環己酯、(甲基)丙烯酸乙基環己酯、1,4-環己烷二甲醇單(甲基)丙烯酸酯、(甲基)丙烯酸松香酯、(甲 基)丙烯酸降冰片基酯、(甲基)丙烯酸5-甲基降冰片基酯、(甲基)丙烯酸5-乙基降冰片基酯、(甲基)丙烯酸烯丙基酯、(甲基)丙烯酸四氫糠基酯、(甲基)丙烯酸1,1,1-三氟乙酯、(甲基)丙烯酸全氟乙酯、(甲基)丙烯酸全氟-丙酯、(甲基)丙烯酸全氟-異丙酯、(甲基)丙烯酸三苯基甲酯、(甲基)丙烯酸枯基酯、(甲基)丙烯酸3-(N,N-二甲基胺基)丙酯、丙三醇單(甲基)丙烯酸酯、丁三醇單(甲基)丙烯酸酯、戊三醇單(甲基)丙烯酸酯、(甲基)丙烯酸二環戊烯基酯、(甲基)丙烯酸二環戊烷基酯、(甲基)丙烯酸異冰片基酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸萘酯、(甲基)丙烯酸蒽酯、(甲基)丙烯酸2-(2-乙烯氧基乙氧基)乙酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸3,4-環氧環己基甲酯、(甲基)丙烯酸(3-乙基氧雜環丁烷-3-基)甲酯、(甲基)丙烯酸2-異氰酸基乙酯、(甲基)丙烯酸2-異氰酸基丙酯、(甲基)丙烯酸3-異氰酸基丙酯、(甲基)丙烯酸2-異氰酸基-1-甲基乙酯、(甲基)丙烯酸2-異氰酸基-1,1-二甲基乙酯、(甲基)丙烯酸4-異氰酸基環己酯、藉由使用封端劑將所述具有異氰酸基的(甲基)丙烯酸酯(例如,(甲基)丙烯酸2-異氰酸基乙酯)的異氰酸基封端化而獲得的具有封端異氰酸基的(甲基)丙烯酸酯、(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸N,N-二乙基胺基乙酯、(甲基)丙烯酸N-第三丁基胺基乙酯、(甲基)丙烯酸四甲基哌啶基酯、(甲基)丙烯酸六甲基哌啶基酯;(甲基)丙烯酸醯胺、(甲基)丙烯酸N,N-二甲基醯胺、(甲基)丙烯酸N,N-二乙基醯胺、(甲基)丙烯酸N,N-二丙基醯胺、(甲基) 丙烯酸N,N-二異丙基醯胺、(甲基)丙烯酸蒽基醯胺、N-異丙基(甲基)丙烯醯胺、(甲基)丙烯酸嗎啉、二丙酮(甲基)丙烯醯胺;降冰片烯(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、四環[4.4.0.12,5.17,10]十二碳-3-烯、8-甲基四環[4.4.0.12,5.17,10]十二碳-3-烯、8-乙基四環[4.4.0.12,5.17,10]十二碳-3-烯、二環戊二烯、三環[5.2.1.02,6]癸-8-烯、三環[5.2.1.02,6]癸-3-烯、三環[4.4.0.12,5]十一碳-3-烯、三環[6.2.1.01,8]十一碳-9-烯、三環[6.2.1.01,8]十一碳-4-烯、四環[4.4.0.12,5.17,10.01,6]十二碳-3-烯、8-甲基四環[4.4.0.12,5.17,10.01,6]十二碳-3-烯、8-亞乙基四環[4.4.0.12,5.17,12]十二碳-3-烯、8-亞乙基四環[4.4.0.12,5.17,10.01,6]十二碳-3-烯、五環[6.5.1.13,6.02,7.09,13]十五碳-4-烯、五環[7.4.0.12,5.19,12.08,13]十五碳-3-烯、5-降冰片烯-2,3-二羧酸酐、(甲基)丙烯酸醯苯胺、(甲基)丙烯醯基腈、丙烯醛、氯乙烯、偏二氯乙烯、氟乙烯、偏二氟乙烯、乙烯基吡啶、乙酸乙烯基酯、乙烯基甲苯;苯乙烯及其衍生物;檸康酸二乙酯、馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯;馬來酸酐、衣康酸酐、檸康酸酐。 As the compound (m1-3), for example, the following compounds can be cited: butadiene; methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, neopentyl (meth)acrylate, benzyl (meth)acrylate, isopentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, dodecyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, Ethyl cyclohexyl acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, rosin (meth)acrylate, norbornyl (meth)acrylate, 5-methylnorbornyl (meth)acrylate, 5-ethylnorbornyl (meth)acrylate, allyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 1,1,1-trifluoroethyl (meth)acrylate, perfluoroethyl (meth)acrylate, perfluoro-propyl (meth)acrylate, perfluoro-isopropyl (meth)acrylate, triphenylmethyl (meth)acrylate, cumyl (meth)acrylate, 3-(N,N-dimethylamino)propyl (meth)acrylate, glycerol mono(meth)acrylate, butanetriol mono(meth)acrylate, pentatriol mono(meth)acrylate Acrylate, dicyclopentenyl (meth)acrylate, dicyclopentyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, naphthyl (meth)acrylate, anthracene (meth)acrylate, 2-(2-vinyloxyethoxy)ethyl (meth)acrylate, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, (3-ethyloxycyclobutane-3-yl)methyl (meth)acrylate, 2-isocyanatoethyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanato-1-methylethyl (meth)acrylate, 2-isocyanato-1,1-diisocyanatopropyl (meth)acrylate ethyl (meth)acrylate, 4-isocyanatocyclohexyl (meth)acrylate, a (meth)acrylate having a blocked isocyanate group obtained by blocking the isocyanate group of the (meth)acrylate having an isocyanate group (e.g., 2-isocyanatoethyl (meth)acrylate) using a blocking agent, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N-tert-butylaminoethyl (meth)acrylate, tetramethylpiperidyl (meth)acrylate, hexamethylpiperidyl (meth)acrylate; (meth)acrylic acid amide, N,N-dimethyl (meth)acrylate amide, N,N-diethyl (meth)acrylate amide, N,N-dipropyl (meth)acrylate amide, (meth) N,N-diisopropyl acrylate, anthracenyl (meth)acrylate, N-isopropyl (meth)acrylamide, morpholine (meth)acrylate, diacetone (meth)acrylamide; norbornene (bicyclo[2.2.1]hept-2-ene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodec-3-ene, 8-methyltetracyclo[4.4.0.1 2,5 .1 7,10 ]dodec-3-ene, 8-ethyltetracyclo[4.4.0.1 2,5 .1 7,10 ] dodec-3-ene, dicyclopentadiene, tricyclo[5.2.1.0 2,6 ]dec-8-ene, tricyclo[5.2.1.0 2,6 ]dec-3-ene, tricyclo[4.4.0.1 2,5 ]undec-3-ene, tricyclo[6.2.1.0 1,8 ]undec-9-ene, tricyclo[6.2.1.0 1,8 ]undec-4-ene, tetracyclo[4.4.0.1 2,5 .1 7,10 .0 1,6 ]dodec-3-ene, 8-methyltetracyclo[4.4.0.1 2,5 .1 7,10 .0 1,6 ]dodec-3-ene, 8-ethylenetetracyclo[4.4.0.1 2,5 .1 7,12 ] dodec-3-ene, 8-ethylenetetracyclo[4.4.0.1 2,5 .1 7,10 .0 1,6 ] dodec-3-ene, pentacyclo[6.5.1.1 3,6 .0 2,7 .0 9,13 ] pentadeca-4-ene, pentacyclo[7.4.0.1 2,5 .1 9,12 .0 8,13 ] pentadeca-3-ene, 5-norbornene-2,3-dicarboxylic anhydride, (meth)acrylic anilide, (meth)acrylic nitrile, acrolein, vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride, vinylpyridine, vinyl acetate, vinyltoluene; styrene and its derivatives; diethyl citric acid, diethyl maleate, diethyl fumarate, diethyl itaconate; maleic anhydride, itaconic anhydride, citric anhydride.
就獲得的容易性及反應性的觀點而言,作為化合物(m1-3),較佳為(甲基)丙烯酸甲酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸二環戊烷基酯、(甲基)丙烯酸縮水 甘油酯、(甲基)丙烯酸(3-乙基氧雜環丁烷-3-基)甲酯、(甲基)丙烯酸N,N-二乙基胺基乙酯、(甲基)丙烯酸N,N-二甲基醯胺、(甲基)丙烯酸嗎啉、苯乙烯、乙烯基甲苯及降冰片烯,更佳為(甲基)丙烯酸甲酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸二環戊烷基酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸(3-乙基氧雜環丁烷-3-基)甲酯、苯乙烯及乙烯基甲苯。 From the viewpoint of ease of acquisition and reactivity, as compound (m1-3), methyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentyl (meth)acrylate, glyceryl (meth)acrylate, (3-ethyloxycyclobutane-3-yl)methyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylamide (meth)acrylate, benzoline (meth)acrylate, styrene, vinyltoluene and norbornene are preferred, and methyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentyl (meth)acrylate, glyceryl (meth)acrylate, (3-ethyloxycyclobutane-3-yl)methyl (meth)acrylate, styrene and vinyltoluene are more preferred.
就耐熱分解性及耐熱黃變性的觀點而言,作為化合物(m1-3),較佳為(甲基)丙烯酸烷基酯,更佳為(甲基)丙烯酸甲酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸二環戊烷基酯。 From the viewpoint of heat decomposition resistance and heat yellowing resistance, the compound (m1-3) is preferably an alkyl (meth)acrylate, and more preferably methyl (meth)acrylate, benzyl (meth)acrylate, or dicyclopentanyl (meth)acrylate.
就耐溶劑性的觀點而言,作為化合物(m1-3),較佳為具有與酸性基進行反應的官能基(例如,縮水甘油基、氧雜環丁基、異氰酸基、封端異氰酸基)的聚合性化合物,更佳為(甲基)丙烯酸縮水甘油酯、甲基丙烯酸(3-乙基氧雜環丁烷-3-基)甲酯。 From the viewpoint of solvent resistance, the compound (m1-3) is preferably a polymerizable compound having a functional group that reacts with an acidic group (e.g., glycidyl, cyclobutylene oxide, isocyanate, blocked isocyanate), and more preferably glycidyl (meth)acrylate or (3-ethylcyclobutylene oxide)methyl methacrylate.
作為所述異氰酸基的封端中使用的封端劑,例如可列舉以下封端劑:ε-己內醯胺、δ-戊內醯胺、γ-丁內醯胺、β-丙內醯胺等內醯胺系封端劑;甲醇、乙醇、丙醇、丁醇、乙二醇、甲基溶纖劑、丁基溶纖劑、甲基卡必醇、苄醇、苯基溶纖劑、糠醇、環己醇等醇系封端劑;苯酚、甲酚、二甲苯酚、乙基苯酚、鄰異丙基苯酚、對第三丁基苯酚等丁基苯酚、對第三辛基苯酚、壬基苯酚、二壬基苯酚、 苯乙烯化苯酚、氧基苯甲酸酯、瑞香酚、對萘酚、對硝基苯酚、對氯苯酚等酚系封端劑;丙二酸二甲酯、丙二酸二乙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙醯丙酮等活性亞甲基系封端劑;丁硫醇(butyl mercaptan)、苯硫酚(thiophenol)、第三-十二烷基硫醇等硫醇系封端劑;二苯基胺、苯基萘基胺、苯胺、咔唑等胺系封端劑;乙醯苯胺(acetanilide)、甲氧基乙醯苯胺(acetanisidide)、乙酸醯胺、苯甲醯胺等酸醯胺系封端劑;琥珀酸醯亞胺、馬來酸醯亞胺等酸醯亞胺系封端劑;咪唑、2-甲基咪唑、2-乙基咪唑等咪唑系封端劑;脲、硫脲、乙烯脲等脲系封端劑;N-苯基胺基甲酸苯基酯、2-噁唑啶酮等胺甲酸鹽系封端劑;乙烯亞胺、聚乙烯亞胺等亞胺系封端劑;甲醛肟、乙醛肟、丙酮肟、甲基乙基酮肟、甲基異丁基酮肟、環己酮肟等肟系封端劑;亞硫酸氫鈉、亞硫酸氫鉀等亞硫酸氫鹽系封端劑。 As the blocking agent used for blocking the isocyanate group, for example, the following blocking agents can be cited: ε-caprolactam, δ-valerolactamide, γ-butyrolactam, β-propiolactamide and other lactam-based blocking agents; methanol, ethanol, propanol, butanol, ethylene glycol, methyl solvent, butyl solvent, methyl carbitol, benzyl alcohol, phenyl solvent, furfuryl alcohol, cyclohexanol and other alcohol-based blocking agents; phenol, cresol, xylenol, ethylphenol, etc. Phenol-based end-capping agents such as butylphenol, o-isopropylphenol, tert-butylphenol, tert-octylphenol, nonylphenol, dinonylphenol, styrenated phenol, oxybenzoic acid esters, daphneol, p-naphthol, p-nitrophenol, p-chlorophenol, etc.; active methylene-based end-capping agents such as dimethyl malonate, diethyl malonate, methyl acetylacetate, ethyl acetylacetate, acetylacetone, etc.; butanethiol (butyl Mercaptan), thiophenol, tertiary-dodecyl mercaptan and other thiol-based capping agents; diphenylamine, phenylnaphthylamine, aniline, carbazole and other amine-based capping agents; acetanilide, acetanisidide, acetamide, benzamide and other acid amide-based capping agents; succinimide, maleic imide and other acid imide-based capping agents Agent; imidazole-based end-capping agents such as imidazole, 2-methylimidazole, and 2-ethylimidazole; urea-based end-capping agents such as urea, thiourea, and ethyleneurea; aminocarbamate-based end-capping agents such as N-phenylaminophenyl ester and 2-oxazolidinone; imine-based end-capping agents such as ethyleneimine and polyethyleneimine; oxime-based end-capping agents such as formaldehyde oxime, acetaldehyde oxime, acetone oxime, methyl ethyl ketone oxime, methyl isobutyl ketone oxime, and cyclohexanone oxime; bisulfite-based end-capping agents such as sodium bisulfite and potassium bisulfite.
為了將樹脂(B1)的重量分子量(Mw)及分子量分佈(Mw/Mn)控制為較佳的範圍內,以及為了抑制聚合時的凝膠化,所述聚合中使用的溶劑較佳為包含碳數3~10的含有羥基的溶劑。作為碳數3~10的含有羥基的溶劑,例如可列舉:丙基醇、丁基醇、戊基醇、己基醇、辛基醇、壬基醇、癸基醇、苄醇等單 醇類;乙二醇單甲醚、乙二醇單乙醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丙醚、二乙二醇單丁醚、三乙二醇單甲醚、三乙二醇單乙醚、丙二醇單甲醚、丙二醇單乙醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丙醚、二丙二醇單丁醚、三丙二醇單甲醚等(聚)烷二醇單烷基醚類。 In order to control the molecular weight (Mw) and molecular weight distribution (Mw/Mn) of the resin (B1) within a preferred range and to suppress gelation during polymerization, the solvent used in the polymerization is preferably a solvent containing a hydroxyl group having 3 to 10 carbon atoms. As solvents containing hydroxyl groups having 3 to 10 carbon atoms, for example, monoalcohols such as propyl alcohol, butyl alcohol, amyl alcohol, hexyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, and benzyl alcohol; (poly)alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, and tripropylene glycol monomethyl ether.
所述聚合中使用的溶劑亦可包含碳數3~10的含有羥基的溶劑以外的溶劑。作為所述溶劑,例如可列舉:乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯等(聚)烷二醇單烷基醚乙酸酯類;二乙二醇二甲醚、二乙二醇甲基乙基醚、二乙二醇二乙醚、四氫呋喃等醚類;甲基乙基酮、環己酮、2-庚酮、3-庚酮等酮類;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、乙氧基乙酸乙酯、羥基乙酸乙酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、乙酸乙酯、乙酸丁酯、乙酸丙酯、乙酸異丙酯、乙酸異丁酯、乙酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸乙酯、丁酸丙酯、丁酸異丙酯、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、2-氧代丁酸乙酯等酯類;甲苯、二甲苯等芳香族烴類;N-甲基吡咯啶酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等羧酸醯胺類等。該些中,就反應性的觀點而言,較佳為(聚)烷二醇單烷基醚乙酸酯類。 The solvent used in the polymerization may also contain solvents other than the solvent containing a hydroxyl group having 3 to 10 carbon atoms. Examples of the solvent include (poly)alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxylate, ethyl hydroxylate, 3-methyl- Esters such as 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, butyl acetate, propyl acetate, isopropyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate, butyl propionate, ethyl butyrate, propyl butyrate, isopropyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, ethyl 2-oxobutyrate; aromatic hydrocarbons such as toluene and xylene; carboxylic acid amides such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, etc. Among these, (poly)alkylene glycol monoalkyl ether acetates are preferred from the viewpoint of reactivity.
就控制樹脂(B1)的重量分子量及分子量分佈(Mw/Mn)的觀點而言,相對於所述聚合中使用的溶劑整體的碳數3~10的 含有羥基的溶劑的含量較佳為10重量%~100重量%,更佳為20重量%~100重量%。 From the viewpoint of controlling the weight molecular weight and molecular weight distribution (Mw/Mn) of the resin (B1), the content of the solvent containing a hydroxyl group having 3 to 10 carbon atoms relative to the total amount of the solvent used in the polymerization is preferably 10 wt% to 100 wt%, more preferably 20 wt% to 100 wt%.
所述聚合中的溶劑的使用量並無特別限定,相對於化合物(m1-1)、化合物(m1-2)及化合物(m1-3)的使用量的合計100重量份,較佳為30重量份~1,000重量份,更佳為50重量份~800重量份。 The amount of the solvent used in the polymerization is not particularly limited, but is preferably 30 to 1,000 parts by weight, and more preferably 50 to 800 parts by weight, relative to 100 parts by weight of the total amount of compound (m1-1), compound (m1-2) and compound (m1-3).
所述聚合中可使用的聚合起始劑並無特別限定,例如可列舉:2,2'-偶氮雙(異丁腈)、2,2'-偶氮雙(2,4-二甲基戊腈)、2,2'-偶氮雙(異丁酸)二甲酯、過氧化苯甲醯、第三丁基過氧化-2-乙基己酸酯等。聚合起始劑的使用量並無特別限定,相對於化合物(m1-1)、化合物(m1-2)及化合物(m1-3)的使用量的合計100重量份,較佳為0.5重量份~20重量份,更佳為1.0重量份~10重量份。 The polymerization initiator that can be used in the polymerization is not particularly limited, and examples thereof include: 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(isobutyric acid) dimethyl ester, benzoyl peroxide, tert-butyl peroxy-2-ethylhexanoate, etc. The amount of the polymerization initiator used is not particularly limited, and is preferably 0.5 to 20 parts by weight, and more preferably 1.0 to 10 parts by weight, relative to 100 parts by weight of the total amount of compound (m1-1), compound (m1-2), and compound (m1-3).
樹脂(B1)較佳為(甲基)丙烯酸、3-(甲基)丙烯醯基氧基丙基三甲氧基矽烷及(甲基)丙烯酸甲酯的共聚物。於使用化合物(A3)的情況下,樹脂(B1)較佳為(甲基)丙烯酸、3-(甲基)丙烯醯基氧基丙基三乙氧基矽烷及(甲基)丙烯酸二環戊烷基酯的共聚物。 The resin (B1) is preferably a copolymer of (meth)acrylic acid, 3-(meth)acryloxypropyltrimethoxysilane and methyl (meth)acrylate. When compound (A3) is used, the resin (B1) is preferably a copolymer of (meth)acrylic acid, 3-(meth)acryloxypropyltriethoxysilane and dicyclopentanyl (meth)acrylate.
樹脂(B)亦可含有與樹脂(B1)不同的樹脂(B2)。樹脂(B2)較佳為鹼可溶性樹脂,且較佳為包含如下構成單元的聚合物,所述構成單元源自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單量體(以下,有時記載為「單量體 (m2-1)」)。所述聚合物中,所述構成單元可包含僅一種,亦可包含兩種以上。 Resin (B) may also contain a resin (B2) different from resin (B1). Resin (B2) is preferably an alkali-soluble resin, and is preferably a polymer containing the following constituent units, wherein the constituent units are derived from at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter, sometimes described as "monomer (m2-1)"). In the polymer, the constituent units may include only one type or two or more types.
樹脂(B2)更佳為包含源自單量體(m2-1)的構成單元、及源自具有碳數2~4的環狀醚結構與乙烯性不飽和鍵的單量體(以下,有時記載為「單量體(m2-2)」)的構成單元的共聚物。所述共聚物亦可包含其他構成單元。作為其他構成單元,例如可列舉源自與單量體(m2-1)及單量體(m2-2)不同的單量體(以下,有時記載為「單量體(m2-3)」)的構成單元、具有乙烯性不飽和鍵的構成單元等。於共聚物中,所述構成單元均可包含僅一種,亦可包含兩種以上。 Resin (B2) is preferably a copolymer containing constituent units derived from monomer (m2-1) and constituent units derived from a monomer having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter, sometimes described as "monomer (m2-2)"). The copolymer may also contain other constituent units. As other constituent units, for example, constituent units derived from a monomer different from monomer (m2-1) and monomer (m2-2) (hereinafter, sometimes described as "monomer (m2-3)"), constituent units having an ethylenic unsaturated bond, etc. can be listed. In the copolymer, the constituent units may include only one kind or two or more kinds.
作為單量體(m2-1),例如可列舉以下單量體:丙烯酸、甲基丙烯酸、丁烯酸及鄰乙烯基苯甲酸、間乙烯基苯甲酸、對乙烯基苯甲酸等不飽和單羧酸;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及1,4-環己烯二羧酸等不飽和二羧酸;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-羧基甲基雙環[2.2.1]庚-2-烯及5-羧基乙基雙環[2.2.1]庚-2-烯等含有羧基的雙環不飽和化合物;將富馬酸及中康酸除外的所述不飽和二羧酸的酐等羧酸酐;琥珀酸單〔2-(甲基)丙烯醯基氧基乙基〕酯及鄰苯二甲酸單 〔2-(甲基)丙烯醯基氧基乙基〕酯等二價以上的多元羧酸的不飽和單〔(甲基)丙烯醯基氧基烷基〕酯類;α-(羥基甲基)丙烯酸等同一分子中含有羥基及羧基的不飽和丙烯酸酯類。 Examples of the monomer (m2-1) include the following monomers: unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, liraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6- Bicyclic unsaturated compounds containing carboxyl groups such as dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene; carboxylic anhydrides such as anhydrides of the unsaturated dicarboxylic acids mentioned above except fumaric acid and mesaconic acid; unsaturated mono[(meth)acryloxyalkyl] esters of polycarboxylic acids having a valence of more than two such as mono[2-(meth)acryloxyethyl] succinate and mono[2-(meth)acryloxyethyl] phthalate; unsaturated acrylic esters containing hydroxyl and carboxyl groups in the same molecule such as α-(hydroxymethyl)acrylic acid.
作為單量體(m2-1),就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、甲基丙烯酸及馬來酸酐。 As the monomer (m2-1), acrylic acid, methacrylic acid and maleic anhydride are preferred in terms of reactivity or solubility of the obtained resin in alkaline aqueous solution.
單量體(m2-2)是指具有碳數2~4的環狀醚結構與乙烯性不飽和鍵的聚合性化合物。單量體(m2-2)較佳為具有碳數2~4的環狀醚結構與(甲基)丙烯醯基氧基的單量體。作為碳數2~4的環狀醚結構,例如可列舉:氧雜環丙烷環、氧雜環丁烷環及四氫呋喃環。 The monomer (m2-2) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenic unsaturated bond. The monomer (m2-2) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group. Examples of the cyclic ether structure with 2 to 4 carbon atoms include: an oxycyclopropane ring, an oxycyclobutane ring, and a tetrahydrofuran ring.
作為單量體(m2-2),例如可列舉:具有氧雜環丙基與乙烯性不飽和鍵的單量體(以下,有時記載為「單量體(m2-2-1)」)、具有氧雜環丁基與乙烯性不飽和鍵的單量體(以下,有時記載為「單量體(m2-2-2)」)及具有四氫呋喃基與乙烯性不飽和鍵的單量體(以下,有時記載為「單量體(m2-2-3)」)等。 Examples of the monomer (m2-2) include a monomer having an oxocyclopropyl group and an ethylenic unsaturated bond (hereinafter, sometimes described as "monomer (m2-2-1)"), a monomer having an oxocyclobutyl group and an ethylenic unsaturated bond (hereinafter, sometimes described as "monomer (m2-2-2)"), and a monomer having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter, sometimes described as "monomer (m2-2-3)"), etc.
作為單量體(m2-2-1),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(以下,有時記載為「單量體(m2-2-1a)」)及具有脂環式不飽和烴經環氧化而成的結構的單量體(以下,有時記載為「單量體(m2-2-1b)」)。 作為單量體(m2-2-1a),較佳為具有縮水甘油基與乙烯性不飽和鍵的單量體。作為單量體(m2-2-1a),例如可列舉:(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、乙烯基苄基縮水甘油醚、α-甲基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)苯乙烯及2,4,6-三(縮水甘油基氧基甲基)苯乙烯等。 Examples of monomers (m2-2-1) include monomers having a structure formed by epoxidation of aliphatic unsaturated hydrocarbons in a straight chain or branched chain (hereinafter, sometimes described as "monomer (m2-2-1a)") and monomers having a structure formed by epoxidation of alicyclic unsaturated hydrocarbons (hereinafter, sometimes described as "monomer (m2-2-1b)"). As monomers (m2-2-1a), monomers having a glycerol group and an ethylenic unsaturated bond are preferred. Examples of the monomer (m2-2-1a) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α-methylvinylbenzyl 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-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5-tri(glycidyloxymethyl)styrene and 2,4,6-tri(glycidyloxymethyl)styrene, etc.
作為單量體(m2-2-1b),例如可列舉: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)(註冊商標)2000;大賽璐(Daicel)公司製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)(註冊商標)A400;大賽璐(Daicel)公司製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)(註冊商標)M100;大賽璐(Daicel)公司製造)、式(BI)所表示的化合物及式(BII)所表示的化合物等。 Examples of monomers (m2-2-1b) include vinylcyclohexene oxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel), compounds represented by formula (BI) and compounds represented by formula (BII), etc.
[化31]
[式(BI)及式(BII)中,Ra及Rb分別獨立地表示氫原子、或可經羥基取代的碳數1~4的烷基,Xa及Xb分別獨立地表示單鍵、*-Rc-、*-Rc-O-、*-Rc-S-或*-Rc-NH-,Rc表示碳數1~6的烷二基,以及*表示與O的鍵結位置] [In formula (BI) and formula (BII), Ra and Rb each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted with a hydroxyl group, Xa and Xb each independently represent a single bond, * -Rc- , *-Rc - O-, *-Rc - S- or *-Rc - NH-, Rc represents an alkanediyl group having 1 to 6 carbon atoms, and * represents a bonding position with O]
作為式(BI)所表示的化合物,例如可列舉式(I-1)~式(I-15)的任一者所表示的化合物等。其中,較佳為式(I-1)、式(I-3)、式(I-5)、式(I-7)、式(I-9)及式(I-11)~式(I-15)的任一者所表示的化合物,更佳為式(I-1)、式(I-7)、式(I-9)及式(I-15)的任一者所表示的化合物。 As the compound represented by formula (BI), for example, compounds represented by any one of formula (I-1) to formula (I-15) can be listed. Among them, compounds represented by any one of formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) and formula (I-11) to formula (I-15) are preferred, and compounds represented by any one of formula (I-1), formula (I-7), formula (I-9) and formula (I-15) are more preferred.
[化32]
作為式(BII)所表示的化合物,例如可列舉式(II-1)~式(II-15)的任一者所表示的化合物等。其中,較佳為式(II-1)、式(II-3)、式(II-5)、式(II-7)、式(II-9)及式(II-11)~式(II-15)的任一者所表示的化合物,更佳為式(II-1)、式(II-7)、式(II-9)及式(II-15)的任一者所表示的化合物。 As the compound represented by formula (BII), for example, there can be listed compounds represented by any one of formula (II-1) to formula (II-15). Among them, preferably, it is a compound represented by any one of formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) and formula (II-11) to formula (II-15), and more preferably, it is a compound represented by any one of formula (II-1), formula (II-7), formula (II-9) and formula (II-15).
[化33]
另外,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,亦可併用式(BI)所表示的化合物與式(BII)所表示的化合物。於併用該些的情況下,以式(BI)所表示的化合物及式(BII)所表示的化合物的莫耳比(式(BI)所表示的化合物:式(BII)所表示的化合物)計,較佳為5:95~95:5,更佳為10:90~90:10,進而佳為20:80~80:20。 In addition, the compound represented by formula (BI) and the compound represented by formula (BII) can be used separately or in combination. When used in combination, the molar ratio of the compound represented by formula (BI) and the compound represented by formula (BII) (compound represented by formula (BI) : compound represented by formula (BII)) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.
作為單量體(m2-3),例如可列舉以下單量體:(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)丙烯酸十二烷基酯、(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)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-9-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-9-基酯、(甲基)丙烯酸二環戊烷基氧基乙酯、(甲基)丙烯酸異冰片基酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸烯丙基酯、(甲基)丙烯酸炔丙基酯、(甲基)丙烯酸苯基酯、(甲基)丙烯酸萘基酯及(甲基)丙烯酸苄基酯等(甲基)丙烯酸酯;(甲基)丙烯酸2-羥基乙酯及(甲基)丙烯酸2-羥基丙酯等含有羥基的(甲基)丙烯酸酯;馬來酸二乙酯、富馬酸二乙酯及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-烯及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; N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-琥珀醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-琥珀醯亞胺基-4-馬來醯亞胺丁酸酯、N-琥珀醯亞胺基-6-馬來醯亞胺己酸酯、N-琥珀醯亞胺基-3-馬來醯亞胺丙酸酯及N-(9-吖啶基)馬來醯亞胺等二羰基醯亞胺衍生物;苯乙烯、α-甲基苯乙烯、乙烯基甲苯及對甲氧基苯乙烯等含有乙烯基的芳香族化合物;(甲基)丙烯腈等含有乙烯基的腈;氯乙烯及偏二氯乙烯等鹵化烴;(甲基)丙烯醯胺等含有乙烯基的醯胺;乙酸乙烯基酯等酯;1,3-丁二烯、異戊二烯及2,3-二甲基-1,3-丁二烯等二烯。 Examples of the monomer (m2-3) include the following monomers: methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] (meth)acrylates such as decen-9-yl ester, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; (meth)acrylates containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; diethyl maleate, fumaric acid Diethyl ester and diethyl itaconate; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1] Hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[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-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate and N-(9-acridinyl)maleimide and other dicarbonyl acyl groups. Amine derivatives; aromatic compounds containing vinyl groups such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; nitriles containing vinyl groups such as (meth)acrylonitrile; halides such as vinyl chloride and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene.
就反應性及耐熱性的方面而言,作為單量體(m2-3),較佳為:苯乙烯、乙烯基甲苯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-9-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-9-基酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、雙環[2.2.1]庚-2-烯及(甲基)丙烯酸苄基酯。 In terms of reactivity and heat resistance, the monomer (m2-3) is preferably styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and benzyl (meth)acrylate.
具有乙烯性不飽和鍵的構成單元較佳為具有(甲基)丙烯醯基的構成單元。具有此種構成單元的樹脂(B2)可藉由如下方式來獲得:對包含源自單量體(m2-1)的構成單元及源自單量體(m2-2)的構成單元的聚合物,加成具有可與所述構成單元所具 有的基進行反應的基以及乙烯性不飽和鍵的單量體。 The constituent unit having an ethylenic unsaturated bond is preferably a constituent unit having a (meth)acryl group. The resin (B2) having such a constituent unit can be obtained by adding a monomer having a group that can react with the group possessed by the constituent unit and an ethylenic unsaturated bond to a polymer comprising a constituent unit derived from a monomer (m2-1) and a constituent unit derived from a monomer (m2-2).
作為具有乙烯性不飽和鍵的構成單元,例如可列舉:藉由對(甲基)丙烯酸單元加成(甲基)丙烯酸縮水甘油酯而獲得的構成單元;藉由對馬來酸酐單元加成(甲基)丙烯酸2-羥基乙酯而獲得的構成單元;以及藉由對(甲基)丙烯酸縮水甘油酯單元加成(甲基)丙烯酸而獲得的構成單元;藉由對具有羥基的構成單元加成羧酸酐而獲得的構成單元等。 As constituent units having ethylenic unsaturated bonds, for example, there can be listed: constituent units obtained by adding glycidyl (meth)acrylate to a (meth)acrylate unit; constituent units obtained by adding 2-hydroxyethyl (meth)acrylate to a maleic anhydride unit; constituent units obtained by adding (meth)acrylic acid to glycidyl (meth)acrylate units; constituent units obtained by adding carboxylic anhydride to constituent units having a hydroxyl group, etc.
包含源自單量體(m2-1)的構成單元的聚合物例如可藉由如下方式來製造:於聚合起始劑的存在下,使構成聚合物的構成單元的單量體於溶劑中進行聚合。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。作為聚合起始劑,例如可列舉: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(苯甲醯基過氧化物等)。作為溶劑,若為溶解各單量體的溶劑,則並無特別限定,例如可列舉後述的溶劑(H)。再者,所獲得的聚合物可直接使用反應後的溶液,亦可使用濃縮或稀釋後的溶液,亦可使用藉由再沈澱等方法以固體(粉體)形式取出者。 A polymer containing constituent units derived from a monomer (m2-1) can be produced, for example, by polymerizing monomers constituting constituent units of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator and the solvent are not particularly limited, and those commonly used in this field can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or organic peroxides (benzoyl peroxide, etc.). As for the solvent, there is no particular limitation if it is a solvent that dissolves each monomer, and examples thereof include the solvent (H) described later. Furthermore, the obtained polymer can be used directly as a solution after the reaction, or as a concentrated or diluted solution, or can be taken out in a solid (powder) form by re-precipitation or other methods.
於包含源自單量體(m2-1)的構成單元的聚合物的製造中,作為單量體,亦可使用具有乙烯性不飽和鍵的羧酸酐。作為所述羧酸酐,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及5,6- 二羧基雙環[2.2.1]庚-2-烯酐等。 In the production of a polymer containing a constituent unit derived from the monomer (m2-1), a carboxylic anhydride having an ethylenic unsaturated bond may also be used as a monomer. Examples of the carboxylic anhydride include maleic anhydride, conic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6- dicarboxybicyclo[2.2.1]hept-2-ene anhydride.
作為樹脂(B2),例如可列舉:(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/乙烯基甲苯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/(甲基)丙烯酸2-乙基己酯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸三環[5.2.1.02,6]癸烯基酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、3-甲基-3-(甲基)丙烯醯基氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯共聚物、(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、苯乙烯/(甲基)丙烯酸共聚物以及日本專利特開平9-106071號公報、日本專利特開2004-29518號公報及日本專利特開2004-361455號公報中記載的樹脂等。 Examples of the resin (B2) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymers, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer , ] decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxycyclobutane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, and resins described in Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004-29518, and Japanese Patent Laid-Open No. 2004-361455.
於使用兩種以上的樹脂(B2)的組合的情況下,所述組合較佳為包含選自由(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共 聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/乙烯基甲苯共聚物、及(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/(甲基)丙烯酸2-乙基己酯共聚物所組成的群組中的至少一種。 When a combination of two or more resins (B2) is used, the combination preferably comprises at least one selected from the group consisting of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl(meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate/(meth)acrylic acid/2-ethylhexyl(meth)acrylate copolymer.
樹脂(B2)的重量平均分子量(Mw)較佳為3,000~100,000,更佳為5,000~50,000,進而佳為5,000~30,000。樹脂(B2)的分子量分佈(Mw/Mn)(即,重量平均分子量(Mw)及數量平均分子量(Mn)的比)較佳為1.1~6,更佳為1.2~4。此處,樹脂(B2)的重量平均分子量(Mw)及數量平均分子量(Mn)是使用凝膠滲透層析法(GPC)並藉由聚苯乙烯換算來算出的值。 The weight average molecular weight (Mw) of the resin (B2) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. The molecular weight distribution (Mw/Mn) of the resin (B2) (i.e., the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn)) is preferably 1.1 to 6, and more preferably 1.2 to 4. Here, the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin (B2) are values calculated by gel permeation chromatography (GPC) and converted to polystyrene.
樹脂(B2)的酸價(固體成分換算值)較佳為10mgKOH/g~300mgKOH/g,更佳為20mgKOH/g~250mgKOH/g,進而佳為20mgKOH/g~200mgKOH/g,進而更佳為20mgKOH/g~170mgKOH/g,進而尤佳為30mgKOH/g~170mgKOH/g,特佳為50mgKOH/g~150mgKOH/g,進而特佳為60mgKOH/g~140mgKOH/g,最佳為60mgKOH/g~135mgKOH/g。樹脂(B2)的酸價是作為中和樹脂(B2)1g所需的氫氧化鉀的量(mg)來算出的值,例如可藉由使用氫氧化鉀水溶液進行滴定來求出。 The acid value (solid content conversion value) of the resin (B2) is preferably 10 mgKOH/g to 300 mgKOH/g, more preferably 20 mgKOH/g to 250 mgKOH/g, further preferably 20 mgKOH/g to 200 mgKOH/g, further preferably 20 mgKOH/g to 170 mgKOH/g, further preferably 30 mgKOH/g to 170 mgKOH/g, particularly preferably 50 mgKOH/g to 150 mgKOH/g, further particularly preferably 60 mgKOH/g to 140 mgKOH/g, and most preferably 60 mgKOH/g to 135 mgKOH/g. The acid value of the resin (B2) is a value calculated as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B2), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.
於使用樹脂(B2)的情況下,其相對於著色劑(A)100重量份的含量較佳為1重量份~1,200重量份,更佳為5重量份~1,000重量份,進而佳為10重量份~800重量份。 When the resin (B2) is used, its content relative to 100 parts by weight of the colorant (A) is preferably 1 part by weight to 1,200 parts by weight, more preferably 5 parts by weight to 1,000 parts by weight, and even more preferably 10 parts by weight to 800 parts by weight.
於使用樹脂(B2)的情況下,其相對於固體成分的總量 的含量較佳為1重量%~50重量%,更佳為1重量%~45重量%,進而佳為1重量%~40重量%,最佳為1重量%~30重量%。 When resin (B2) is used, its content relative to the total amount of solid components is preferably 1% to 50% by weight, more preferably 1% to 45% by weight, further preferably 1% to 40% by weight, and most preferably 1% to 30% by weight.
<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/或酸而進行聚合的化合物。聚合性化合物(C)較佳為自由基聚合性化合物。作為自由基聚合性化合物,例如可列舉聚合性的具有乙烯性不飽和鍵的化合物等。自由基聚合性化合物較佳為(甲基)丙烯酸酯類。 The polymerizable compound (C) is a compound that can be polymerized by active free radicals and/or acids generated from the polymerization initiator (D). The polymerizable compound (C) is preferably a free radical polymerizable compound. Examples of free radical polymerizable compounds include polymerizable compounds having ethylenic unsaturated bonds. Free radical polymerizable compounds are preferably (meth)acrylates.
作為聚合性化合物(C),例如可列舉以下化合物:壬基苯基卡必醇丙烯酸酯、丙烯酸2-羥基-3-苯氧基丙酯、2-乙基己基卡必醇丙烯酸酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯啶酮等具有一個乙烯性不飽和鍵的化合物;1,6-己二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、雙酚A的雙(丙烯醯氧基乙基)醚及3-甲基戊二醇二(甲基)丙烯酸酯等具有兩個乙烯性不飽和鍵的化合物;三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三(2-(甲基)丙烯醯基氧基乙基)異氰脲酸酯等具有三個乙烯性不飽和鍵的化合物;季戊四醇四(甲基)丙烯酸酯、乙二醇改質季戊四醇四(甲基)丙烯酸酯、丙二醇改質季戊四醇四(甲基)丙烯酸酯、己內酯改質季戊四醇四(甲基)丙烯酸酯等具有四個乙烯性不飽和鍵的化合物; 二季戊四醇五(甲基)丙烯酸酯等具有五個乙烯性不飽和鍵的化合物;二季戊四醇六(甲基)丙烯酸酯、乙二醇改質二季戊四醇六(甲基)丙烯酸酯、丙二醇改質二季戊四醇六(甲基)丙烯酸酯、己內酯改質二季戊四醇六(甲基)丙烯酸酯等具有六個乙烯性不飽和鍵的化合物;三季戊四醇七(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、四季戊四醇九(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯等具有七個以上的乙烯性不飽和鍵的化合物。 Examples of the polymerizable compound (C) include compounds having one ethylenically unsaturated bond, such as nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinyl pyrrolidone; compounds having one ethylenically unsaturated bond, such as 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate. Compounds having two ethylenically unsaturated bonds, such as trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(2-(meth)acryloxyethyl) isocyanurate, etc.; compounds having three ethylenically unsaturated bonds, such as pentaerythritol tetra(meth)acrylate, triethylene glycol di(meth)acrylate, bisphenol A bis(acryloyloxyethyl) ether, and 3-methylpentanediol di(meth)acrylate; compounds having three ethylenically unsaturated bonds, such as trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and tris(2-(meth)acryloyloxyethyl) isocyanurate; Compounds with four ethylenic unsaturated bonds, such as ethylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, and caprolactone modified pentaerythritol tetra(meth)acrylate; Compounds with five ethylenic unsaturated bonds, such as dipentaerythritol penta(meth)acrylate; Compounds with six ethylenic unsaturated bonds, such as dipentaerythritol hexa(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate; Compounds with seven or more ethylenic unsaturated bonds, such as tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, four-season pentaerythritol nona(meth)acrylate, and four-season pentaerythritol deca(meth)acrylate.
聚合性化合物(C)較佳為具有三個以上的乙烯性不飽和鍵的聚合性化合物,更佳為具有五個或六個乙烯性不飽和鍵的聚合性化合物。具體而言,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。作為聚合性化合物(C)的市售品,例如可列舉:卡亞拉得(KAYARAD)(註冊商標)DPHA(日本化藥公司)、A-TMM-3LM-N(新中村化學工業公司)及A9550(新中村化學工業公司)等。 The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds, and more preferably a polymerizable compound having five or six ethylenic unsaturated bonds. Specifically, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred. Commercially available products of the polymerizable compound (C) include, for example: KAYARAD (registered trademark) DPHA (Nippon Kayaku Co., Ltd.), A-TMM-3LM-N (Shin-Nakamura Chemical Co., Ltd.), and A9550 (Shin-Nakamura Chemical Co., Ltd.).
聚合性化合物(C)的分子量較佳為150以上且2,900以下,更佳為250以上且1,500以下。再者,1,000以上的聚合性化合物(C)的分子量是使用凝膠滲透層析法(GPC)並藉由聚苯乙烯換算來算出的重量平均分子量(Mw)。 The molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less. The molecular weight of the polymerizable compound (C) of 1,000 or more is the weight average molecular weight (Mw) calculated by gel permeation chromatography (GPC) and converted to polystyrene.
相對於固體成分的總量,聚合性化合物(C)的含量較佳為7重量%~65重量%,更佳為13重量%~60重量%,進而佳 為17重量%~55重量%。若聚合性化合物(C)的含量處於所述範圍內,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高的傾向。 The content of the polymerizable compound (C) relative to the total amount of the solid component is preferably 7% to 65% by weight, more preferably 13% to 60% by weight, and further preferably 17% to 55% by weight. If the content of the polymerizable compound (C) is within the above range, the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter tend to be improved.
另外,樹脂(B)與聚合性化合物(C)的重量比(樹脂(B):聚合性化合物(C))較佳為20:80~80:20,更佳為35:65~80:20。 In addition, the weight ratio of resin (B) to polymerizable compound (C) (resin (B): polymerizable compound (C)) is preferably 20:80~80:20, and more preferably 35:65~80:20.
<聚合起始劑(D)> <Polymerization initiator (D)>
聚合起始劑(D)若為可藉由光或熱的作用而產生活性自由基、酸等並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。聚合起始劑(D)較佳為光自由基聚合起始劑。更佳為聚合性化合物(C)為自由基聚合性化合物,並且聚合起始劑(D)為光自由基聚合起始劑(即,本發明的著色硬化性樹脂組成物為光硬化性樹脂組成物)。 The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. and initiate polymerization by the action of light or heat, and a known polymerization initiator can be used. The polymerization initiator (D) is preferably a photoradical polymerization initiator. More preferably, the polymerizable compound (C) is a radical polymerizable compound, and the polymerization initiator (D) is a photoradical polymerization initiator (that is, the coloring curable resin composition of the present invention is a photocurable resin composition).
光自由基聚合起始劑較佳為選自由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,更佳為O-醯基肟化合物。 The photo-radical polymerization initiator is preferably at least one selected from the group consisting of O-acyl oxime compounds, phenyl alkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds and biimidazole compounds, and is more preferably an O-acyl oxime compound.
O-醯基肟化合物為具有式(d1)所表示的部分結構的化合物(下述式中,*表示鍵結位置)。 O-acyl oxime compounds are compounds having a partial structure represented by formula (d1) (in the following formula, * represents a bonding position).
[化34]
作為O-醯基肟化合物,例如可列舉:N-苯甲醯基氧基-1-(4-苯巰基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯巰基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯巰基苯基)-3-環戊基丙烷-1-酮-2-亞胺、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、N-乙醯基氧基-1-[4-(2-羥基乙基氧基)苯巰基苯基]丙烷-1-酮-2-亞胺等。亦可使用TR-PBG327(常州強力電子新材料公司製造)、豔佳固(Irgacure)(註冊商標)OXE01、豔佳固(Irgacure)(註冊商標)OXE02、豔佳固(Irgacure)(註冊商標)OXE03、豔佳固(Irgacure)(註冊商標)OXE04(以上,巴斯夫(BASF)公司製造)、N-1919(艾迪科(ADEKA)公司製造)等市售品。其中,O-醯基肟化合物較佳為選自由TR-PBG327(常州強力電子新材料公司製造)、豔佳固(Irgacure)(註冊商標)OXE01、豔佳固(Irgacure)(註冊商標)OXE02、豔佳固(Irgacure)(註冊商標)OXE03、 豔佳固(Irgacure)(註冊商標)OXE04(以上,巴斯夫(BASF)公司製造)、N-苯甲醯基氧基-1-(4-苯巰基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯巰基苯基)辛烷-1-酮-2-亞胺及N-苯甲醯基氧基-1-(4-苯巰基苯基)-3-環戊基丙烷-1-酮-2-亞胺所組成的群組中的至少一種,更佳為選自由TR-PBG327(常州強力電子新材料公司製造)、豔佳固(Irgacure)(註冊商標)OXE01、豔佳固(Irgacure)(註冊商標)OXE02、豔佳固(Irgacure)(註冊商標)OXE03、豔佳固(Irgacure)(註冊商標)OXE04(以上,巴斯夫(BASF)公司製造)及N-苯甲醯基氧基-1-(4-苯巰基苯基)辛烷-1-酮-2-亞胺所組成的群組中的至少一種。若使用該些O-醯基肟化合物,則有可獲得高亮度的彩色濾光片的傾向。 Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3- dimethyl-2,4-dioxolanecyclopentylmethyloxy)benzyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylphenyl]propane-1-one-2-imine, and the like. Commercially available products such as TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.), Irgacure (registered trademark) OXE01, Irgacure (registered trademark) OXE02, Irgacure (registered trademark) OXE03, Irgacure (registered trademark) OXE04 (all manufactured by BASF), and N-1919 (manufactured by ADEKA) may also be used. Among them, the O-acyl oxime compound is preferably selected from TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.), Irgacure (registered trademark) OXE01, Irgacure (registered trademark) OXE02, Irgacure (registered trademark) OXE03, Irgacure (registered trademark) OXE04 (all manufactured by BASF), N-benzoyloxy-1-(4-phenylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylphenyl)octane-1-one-2-imine and N-benzoyloxy- At least one of the group consisting of 1-(4-phenylphenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably at least one of the group consisting of TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.), Irgacure (registered trademark) OXE01, Irgacure (registered trademark) OXE02, Irgacure (registered trademark) OXE03, Irgacure (registered trademark) OXE04 (all manufactured by BASF) and N-benzoyloxy-1-(4-phenylphenyl)octane-1-one-2-imine. If these O-acyl oxime compounds are used, a color filter with high brightness tends to be obtained.
苯烷基酮化合物為具有式(d2)所表示的部分結構或式(d3)所表示的部分結構的化合物(下述式中,*表示鍵結位置)。該些部分結構中,苯環亦可具有取代基。 The phenyl alkyl ketone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3) (in the following formula, * represents a bonding position). In these partial structures, the benzene ring may also have a substituent.
作為具有式(d2)所表示的部分結構的化合物,例如可列舉:2-甲基-2-嗎啉基-1-(4-甲巰基苯基)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-酮等。亦可使用豔佳固(Irgacure)(註冊商標)369、豔佳固(Irgacure)(註冊商標)907、豔佳固(Irgacure)(註冊商標)379(以上,巴斯夫(BASF)公司製造)等市售品。 Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-oxo-1-(4-oxo-phenyl)propane-1-one, 2-dimethylamino-1-(4-oxo-phenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methyl phenyl)methyl]-1-[4-(4-oxo-phenyl)phenyl]butane-1-one. Commercially available products such as Irgacure (registered trademark) 369, Irgacure (registered trademark) 907, and Irgacure (registered trademark) 379 (all manufactured by BASF) can also be used.
作為具有式(d3)所表示的部分結構的化合物,例如可列舉: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。 Examples of compounds having a partial structure represented by formula (d3) include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-〔4-(2-hydroxyethoxy)phenyl〕propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, benzyl dimethyl ketal, etc.
就感度的方面而言,苯烷基酮化合物較佳為具有式(d2)所表示的部分結構的化合物。 In terms of sensitivity, the phenylalkyl ketone compound is preferably a compound having a partial structure represented by formula (d2).
作為三嗪化合物,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-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2 -(5-methylfuran-2-yl)vinyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(furan-2-yl)vinyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(4-diethylamino-2-methylphenyl)vinyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(3,4-dimethoxyphenyl)vinyl〕-1,3,5-triazine, etc.
作為醯基氧化膦化合物,例如可列舉2,4,6-三甲基苯甲醯基二苯基氧化膦等。亦可使用豔佳固(Irgacure)(註冊商標)819(巴斯夫(BASF)公司製造)等市售品。 As the acylphosphine oxide compound, for example, 2,4,6-trimethylbenzyldiphenylphosphine oxide can be listed. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.
作為聯咪唑化合物,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)、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)、4,4',5,5'-位的苯基由烷氧羰基(carboalkoxy)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。 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 (see, for example, Japanese Patent Laid-Open No. 6-75372 and Japanese Patent Laid-Open No. 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole , 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204), biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted by carboalkoxy groups (for example, see Japanese Patent Publication No. 7-10913), etc.
作為其他聚合起始劑(D),例如可列舉: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。該些較佳為與後述的聚合起始助劑(F)(尤其是胺類)組合使用。 As other polymerization initiators (D), for example, there can be listed: benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, and titaniumocene compounds. These are preferably used in combination with the polymerization initiator aid (F) (especially amines) described later.
作為酸產生劑,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、硝基苄基甲苯磺酸鹽類、安息香甲苯磺酸鹽類等。 Examples of acid generators include onium salts such as 4-hydroxyphenyl dimethyl zirconia p-toluenesulfonate, 4-hydroxyphenyl dimethyl zirconia hexafluoroanticorate, 4-acetoxyphenyl dimethyl zirconia p-toluenesulfonate, 4-acetoxyphenyl/methyl/benzyl zirconia hexafluoroanticorate, triphenyl zirconia p-toluenesulfonate, triphenyl zirconia hexafluoroanticorate, diphenyl iodine p-toluenesulfonate, diphenyl iodine hexafluoroanticorate, nitrobenzyl toluenesulfonates, and benzoin toluenesulfonates.
相對於樹脂(B)及聚合性化合物(C)的合計100重量份,聚合起始劑(D)的含量較佳為0.1重量份~30重量份,更佳為1重量份~20重量份。若聚合起始劑(D)的含量處於所述範圍內,則有本發明的著色硬化性樹脂組成物的感度提高而曝光時間縮短的傾向,因此彩色濾光片的生產性提高。 The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by weight, and more preferably 1 to 20 parts by weight, relative to 100 parts by weight of the total of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, the sensitivity of the colored curable resin composition of the present invention tends to be improved and the exposure time is shortened, thereby improving the productivity of the color filter.
<酚系抗氧化劑(E)> <Phenolic antioxidant (E)>
本發明的著色硬化性樹脂組成物的特徵之一在於包含酚系抗氧化劑(E)。藉由使用酚系抗氧化劑(E),可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少。另外,藉由使用酚系抗氧化劑(E),可提高著色圖案或著色塗膜的耐熱性。 One of the characteristics of the coloring curable resin composition of the present invention is that it contains a phenolic antioxidant (E). By using a phenolic antioxidant (E), the thickness reduction of the coloring pattern or the coloring coating film caused by heating (especially post-baking) can be suppressed. In addition, by using a phenolic antioxidant (E), the heat resistance of the coloring pattern or the coloring coating film can be improved.
本說明書中,所謂「酚系抗氧化劑」,是指具有酚性羥基的抗氧化劑。因此,於本說明書中,例如,包含酚性羥基及磷原子兩者的抗氧化劑是被分類為酚系抗氧化劑而非磷系抗氧化劑。另外,本說明書中的酚系抗氧化劑亦包含具有經保護的酚性羥基的抗氧化劑(以下,有時記載為「經保護的酚系抗氧化劑」)。 In this manual, the so-called "phenolic antioxidant" refers to an antioxidant having a phenolic hydroxyl group. Therefore, in this manual, for example, an antioxidant containing both a phenolic hydroxyl group and a phosphorus atom is classified as a phenolic antioxidant rather than a phosphorus antioxidant. In addition, the phenolic antioxidant in this manual also includes an antioxidant having a protected phenolic hydroxyl group (hereinafter, sometimes described as a "protected phenolic antioxidant").
作為酚系抗氧化劑,例如可列舉以下抗氧化劑: As phenolic antioxidants, for example, the following antioxidants can be listed:
(1)烷硫基甲基苯酚 (1) Alkylthiomethylphenol
2,4-二辛硫基甲基-6-第三丁基苯酚、2,4-二辛硫基甲基-6-甲基苯酚、2,4-二辛硫基甲基-6-乙基苯酚、2,6-二-十二烷硫基甲基-4-壬基苯酚。 2,4-Dioctylthiomethyl-6-tert-butylphenol, 2,4-Dioctylthiomethyl-6-methylphenol, 2,4-Dioctylthiomethyl-6-ethylphenol, 2,6-Di-dodecylthiomethyl-4-nonylphenol.
(2)生育酚類 (2) Tocopherols
α-生育酚、β-生育酚、γ-生育酚、δ-生育酚。 α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol.
(3)O-苄基衍生物、N-苄基衍生物及S-苄基衍生物 (3) O-benzyl derivatives, N-benzyl derivatives and S-benzyl derivatives
3,5,3',5'-四-第三丁基-4,4'-二羥基二苄基醚、十八烷基-4-羥基-3,5-二甲基苄基氫硫基乙酸酯、三(3,5-二-第三丁基-4-羥基苄基)胺、雙(4-第三丁基-3-羥基-2,6-二甲基苄基)二硫基對苯二甲酸酯、雙(3,5-二-第三丁基-4-羥基苄基)硫醚、異辛基-3,5-二-第三丁基-4-羥基苄基氫硫基乙酸酯。 3,5,3',5'-Tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl hydrothioacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) disulfide terephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl hydrothioacetate.
(4)羥基苄基化丙二酸酯衍生物 (4) Hydroxybenzylated malonate derivatives
二-十八烷基-2,2-雙(3,5-二-第三丁基-2-羥基苄基)丙二酸酯、二-十八烷基-2-(3-第三丁基-4-羥基-5-甲基苄基)丙二酸酯、二-十二烷基氫硫基乙基-2,2-雙(3,5-二-第三丁基-4-羥基苄基)丙二酸酯、雙[4-(1,1,3,3-四甲基丁基)苯基]-2,2-雙(3,5-二-第三丁基-4-羥基苄基)丙二酸酯。 Dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, di-dodecylthioethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
(5)芳香族羥基苄基衍生物 (5) Aromatic hydroxybenzyl derivatives
1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、1,4-雙(3,5-二-第三丁基-4-羥基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-第三丁基-4-羥基苄基)苯酚。 1,3,5-Trimethyl-2,4,6-tri(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tri(3,5-tert-butyl-4-hydroxybenzyl)phenol.
(6)三嗪衍生物 (6) Triazine derivatives
2,4-雙(正辛硫基)-6-(4-羥基-3,5-二-第三丁基苯胺基)-1,3,5-三嗪、2-正辛硫基-4,6-雙(4-羥基-3,5-二-第三丁基苯胺基)-1,3,5-三嗪、2-正辛硫基-4,6-雙(4-羥基-3,5-二-第三丁基苯氧基)-1,3,5-三 嗪、2,4,6-三(3,5-二-第三丁基-4-苯氧基)-1,3,5-三嗪、三(4-第三丁基-3-羥基-2,6-二甲基苄基)異氰脲酸酯、三(3,5-二-第三丁基-4-羥基苄基)異氰脲酸酯、2,4,6-三(3,5-二-第三丁基-4-羥基苯基乙基)-1,3,5-三嗪、2,4,6-三(3,5-二-第三丁基-4-羥基苯基丙基)-1,3,5-三嗪、三(3,5-二環己基-4-羥基苄基)異氰脲酸酯、三[2-(3',5'-二-第三丁基-4'-羥基肉桂醯基氧基)乙基]異氰脲酸酯。 2,4-Bis(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine, 2-n-octylthio-4,6-bis(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine, 2-n-octylthio-4,6-bis(4-hydroxy-3,5-di-tert-butylphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-phenoxy)-1,3,5-triazine, tris(4-tert-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate, tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylpropyl)-1,3,5-triazine, tris(3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate, tris[2-(3',5'-di-tert-butyl-4'-hydroxycinnamyloxy)ethyl] isocyanurate.
(7)苄基膦酸酯衍生物 (7) Benzylphosphonate derivatives
二甲基-3,5-二-第三丁基-4-羥基苄基膦酸酯、二乙基-3,5-二-第三丁基-4-羥基苄基膦酸酯、二-十八烷基-3,5-二-第三丁基-4-羥基苄基膦酸酯、二-十八烷基-5-第三丁基-4-羥基-3-甲基苄基膦酸酯、3,5-二-第三丁基-4-羥基苄基膦酸單酯的鈣鹽。 Dimethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, calcium salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonate.
(8)醯基胺基苯酚衍生物 (8) Acylaminophenol derivatives
4-羥基月桂酸醯苯胺、4-羥基硬脂酸醯苯胺、辛基-N-(3,5-二-第三丁基-4-羥基苯基)胺基甲酸酯。 4-Hydroxylauric acid anilide, 4-Hydroxystearic acid anilide, Octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.
(9)β-(3,5-二-第三丁基-4-羥基苯基)丙酸與以下的一元醇或多元醇的酯 (9) Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and the following monohydric or polyhydric alcohols
甲醇、乙醇、辛醇、十八烷醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺二醇、三乙二醇、季戊四醇、三(羥基乙基)異氰脲酸酯、N,N'-雙(羥基乙基)草醯胺、3-硫雜十一烷醇、3-硫雜十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜雙環[2,2,2]辛烷。 Methanol, ethanol, octanol, octadecyl alcohol, ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tri(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trihydroxymethylpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane.
(10)β-(5-第三丁基-4-羥基-3-甲基苯基)丙酸與以下的一元醇或多元醇的酯 (10) Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid and the following monohydric or polyhydric alcohols
甲醇、乙醇、辛醇、十八烷醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺二醇、三乙二醇、季戊四醇、三(羥基乙基)異氰脲酸酯、N,N'-雙(羥基乙基)草醯胺、3-硫雜十一烷醇、3-硫雜十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜雙環[2,2,2]辛烷。 Methanol, ethanol, octanol, octadecyl alcohol, ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tri(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trihydroxymethylpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane.
(11)β-(3,5-二環己基-4-羥基苯基)丙酸與以下的一元醇或多元醇的酯 (11) Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid and the following monohydric or polyhydric alcohols
甲醇、乙醇、辛醇、十八烷醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺二醇、三乙二醇、季戊四醇、三(羥基乙基)異氰脲酸酯、N,N'-雙(羥基乙基)草醯胺、3-硫雜十一烷醇、3-硫雜十五烷醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜雙環[2,2,2]辛烷。 Methanol, ethanol, octanol, octadecyl alcohol, ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tri(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trihydroxymethylpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane.
(12)3,5-二-第三丁基-4-羥基苯基乙酸與以下的一元醇或多元醇的酯 (12) Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid and the following monohydric alcohols or polyhydric alcohols
甲醇、乙醇、辛醇、十八烷醇、乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇、新戊二醇、二乙二醇、硫代乙二醇、螺二醇、三乙二醇、季戊四醇、三(羥基乙基)異氰脲酸酯、N,N'-雙(羥基乙基)草醯胺、3-硫雜十一烷醇、3-硫雜十五烷醇、三 甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷雜-2,6,7-三氧雜雙環[2,2,2]辛烷。 Methanol, ethanol, octanol, octadecyl alcohol, ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tri(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trihydroxymethylpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane.
(13)β-(3,5-二-第三丁基-4-羥基苯基)丙酸的醯胺 (13) Amide of β-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid
N,N'-雙[3-(3',5'-二-第三丁基-4'-羥基苯基)丙醯基]肼、N,N'-雙[3-(3',5'-二-第三丁基-4'-羥基苯基)丙醯基]六亞甲基二胺、N,N'-雙[3-(3',5'-二-第三丁基-4'-羥基苯基)丙醯基]三亞甲基二胺。 N,N'-Bis[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionyl]hydrazine, N,N'-bis[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionyl]hexamethylenediamine, N,N'-bis[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionyl]trimethylenediamine.
利用保護基對所述例示的酚系抗氧化劑的酚性羥基進行保護而成者亦可作為本發明中的酚系抗氧化劑來使用。作為保護基,例如可列舉:醚系保護基、縮醛系保護基、醯基系保護基、矽烷基醚系保護基。作為醚系保護基,例如可列舉甲基、苄基、對甲氧基苄基、第三丁基。作為縮醛系保護基,例如可列舉甲氧基甲基、2-四氫吡喃基、乙氧基乙基。作為醯基系保護基,可列舉乙醯基、三甲基乙醯基、苯甲醯基。作為矽烷基醚系保護基,例如可列舉三甲基矽烷基、三乙基矽烷基、第三丁基二甲基矽烷基、三異丙基矽烷基、第三丁基二苯基矽烷基。另外,作為保護基,亦可使用第三丁氧基羰基(Boc)基。作為酚性羥基的保護基,較佳為Boc基。 The phenolic antioxidants in the present invention may be formed by protecting the phenolic hydroxyl groups of the exemplified phenolic antioxidants with protecting groups. Examples of the protecting groups include ether protecting groups, acetal protecting groups, acyl protecting groups, and silyl ether protecting groups. Examples of ether protecting groups include methyl, benzyl, p-methoxybenzyl, and tert-butyl. Examples of acetal protecting groups include methoxymethyl, 2-tetrahydropyranyl, and ethoxyethyl. Examples of acyl protecting groups include acetyl, trimethylacetyl, and benzoyl. As silyl ether protecting groups, for example, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, triisopropylsilyl, and tert-butyldiphenylsilyl can be listed. In addition, tert-butyloxycarbonyl (Boc) can also be used as a protecting group. As a protecting group for phenolic hydroxyl groups, the Boc group is preferred.
酚系抗氧化劑可使用市售品。作為酚系抗氧化劑的市售品,例如可列舉:蘇米萊澤(Sumilizer)(註冊商標)GP(住友化學公司製造)、艾迪科斯塔波(Adekastab)(註冊商標)AO系列(艾迪科(ADEKA)公司製造)。作為經保護的酚系抗氧化劑的市售品,例如可列舉艾迪科亞科魯茲(Adeka arkls)(註冊商標) GPA-5001(艾迪科(ADEKA)公司製造)。 Commercially available phenolic antioxidants can be used. Examples of commercially available phenolic antioxidants include Sumilizer (registered trademark) GP (manufactured by Sumitomo Chemical Co., Ltd.) and Adekastab (registered trademark) AO series (manufactured by ADEKA Corporation). Examples of commercially available protected phenolic antioxidants include Adeka Arkls (registered trademark) GPA-5001 (manufactured by ADEKA Corporation).
就抑制由加熱引起的著色圖案或著色塗膜的厚度減少及於鹼顯影後獲得良好的著色圖案的觀點而言,相對於聚合性化合物(C)100重量份,酚系抗氧化劑(E)的含量較佳為0.1重量份~25重量份,更佳為0.2重量份~20重量份,進而佳為0.5重量份~20重量份,特佳為3重量份~10重量份。 From the viewpoint of suppressing the reduction of the coloring pattern or the thickness of the coloring film caused by heating and obtaining a good coloring pattern after alkali development, the content of the phenolic antioxidant (E) is preferably 0.1 to 25 parts by weight, more preferably 0.2 to 20 parts by weight, further preferably 0.5 to 20 parts by weight, and particularly preferably 3 to 10 parts by weight, relative to 100 parts by weight of the polymerizable compound (C).
<聚合起始助劑(F)> <Polymerization initiation aid (F)>
本發明的著色硬化性樹脂組成物亦可進而包含聚合起始助劑(F)。聚合起始助劑(F)為用於促進藉由聚合起始劑而開始聚合的聚合性化合物的聚合的化合物、或增感劑。作為聚合起始助劑(F),例如可列舉:胺化合物、烷氧基蒽化合物、硫雜蒽酮化合物及羧酸化合物等。 The colored curable resin composition of the present invention may further contain a polymerization initiator (F). The polymerization initiator (F) is a compound or a sensitizer used to promote the polymerization of a polymerizable compound that starts polymerization by the polymerization initiator. Examples of the polymerization initiator (F) include amine compounds, alkoxyanthracene compounds, thioxanthrone compounds, and carboxylic acid compounds.
作為胺化合物,例如可列舉:三乙醇胺、甲基二乙醇胺、三異丙醇胺、4-二甲基胺基苯甲酸甲酯、4-二甲基胺基苯甲酸乙酯、4-二甲基胺基苯甲酸異戊酯、苯甲酸2-二甲基胺基乙酯、4-二甲基胺基苯甲酸2-乙基己酯、N,N-二甲基對甲苯胺、4,4'-雙(二甲基胺基)二苯甲酮(通稱:米其勒酮(Michler's ketone))、4,4'-雙(二乙基胺基)二苯甲酮、4,4'-雙(乙基甲基胺基)二苯甲酮等。該些中,較佳為4,4'-雙(二乙基胺基)二苯甲酮。作為胺化合物,亦可使用EAB-F(保土谷化學工業公司製造)等市售品。 As amine compounds, for example, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc. Among them, 4,4'-bis(diethylamino)benzophenone is preferred. As amine compounds, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.
作為烷氧基蒽化合物,例如可列舉:9,10-二甲氧基蒽、2-乙基-9,10-二甲氧基蒽、9,10-二乙氧基蒽、2-乙基-9,10-二乙氧基 蒽、9,10-二丁氧基蒽、2-乙基-9,10-二丁氧基蒽等。 Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
作為硫雜蒽酮化合物,例如可列舉:2-異丙基硫雜蒽酮、4-異丙基硫雜蒽酮、2,4-二乙基硫雜蒽酮、2,4-二氯硫雜蒽酮、1-氯-4-丙氧基硫雜蒽酮等。 Examples of thioxanthrone compounds include 2-isopropylthioxanthrone, 4-isopropylthioxanthrone, 2,4-diethylthioxanthrone, 2,4-dichlorothioxanthrone, and 1-chloro-4-propoxythioxanthrone.
作為羧酸化合物,例如可列舉:苯巰基乙酸、甲基苯巰基乙酸、乙基苯巰基乙酸、甲基乙基苯巰基乙酸、二甲基苯巰基乙酸、甲氧基苯巰基乙酸、二甲氧基苯巰基乙酸、氯苯巰基乙酸、二氯苯巰基乙酸、N-苯基甘胺酸、苯氧基乙酸、萘基硫基乙酸、N-萘基甘胺酸、萘氧基乙酸等。 Examples of carboxylic acid compounds include: phenylacetic acid, methylphenylacetic acid, ethylphenylacetic acid, methylethylphenylacetic acid, dimethylphenylacetic acid, methoxyphenylacetic acid, dimethoxyphenylacetic acid, chlorophenylacetic acid, dichlorophenylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc.
聚合起始助劑(F)較佳為硫雜蒽酮化合物,更佳為2,4-二乙基硫雜蒽酮。 The polymerization initiation aid (F) is preferably a thioxanthrone compound, more preferably 2,4-diethylthioxanthrone.
於使用聚合起始助劑(F)的情況下,其相對於樹脂(B)及聚合性化合物(C)的合計100重量份的含量較佳為0.1重量份~30重量份,更佳為1重量份~20重量份。另外,於使用聚合起始助劑(F)的情況下,其相對於聚合起始劑(D)100重量份的含量較佳為5重量份~80重量份,更佳為10重量份~60重量份,進而佳為15重量份~55重量份。若聚合起始助劑(F)的量處於所述範圍內,則可以高感度形成著色圖案,有彩色濾光片的生產性提高的傾向。 When a polymerization initiator (F) is used, its content relative to 100 parts by weight of the total of the resin (B) and the polymerizable compound (C) is preferably 0.1 parts by weight to 30 parts by weight, and more preferably 1 part by weight to 20 parts by weight. In addition, when a polymerization initiator (F) is used, its content relative to 100 parts by weight of the polymerization initiator (D) is preferably 5 parts by weight to 80 parts by weight, more preferably 10 parts by weight to 60 parts by weight, and further preferably 15 parts by weight to 55 parts by weight. If the amount of the polymerization initiator (F) is within the above range, a colored pattern can be formed with high sensitivity, and the productivity of the color filter tends to be improved.
<硫醇化合物(thiol compound)(G)> <Thiol compound (G)>
本發明的著色硬化性樹脂組成物亦可進而包含硫醇化合物(G)。硫醇化合物(G)為具有巰基(-SH)的化合物。 The colored curable resin composition of the present invention may further contain a thiol compound (G). The thiol compound (G) is a compound having a styryl group (-SH).
作為具有一個巰基的化合物,例如可列舉:2-巰基噁唑、2-巰基噻唑、2-巰基苯並咪唑、2-巰基苯並噻唑、2-巰基苯並噁唑、2-巰基煙鹼酸、2-巰基吡啶、2-巰基吡啶-3-醇、2-巰基吡啶-N-氧化物、4-胺基-6-羥基-2-巰基嘧啶、4-胺基-2-巰基嘧啶、6-胺基-5-亞硝基-2-硫尿嘧啶、4,5-二胺基-6-羥基-2-巰基嘧啶、4,6-二胺基-2-巰基嘧啶、2,4-二胺基-6-巰基嘧啶、4,6-二羥基-2-巰基嘧啶、4,6-二甲基-2-巰基嘧啶、4-羥基-2-巰基-6-甲基嘧啶、4-羥基-2-巰基-6-丙基嘧啶、2-巰基-4-甲基嘧啶、2-巰基嘧啶、2-硫尿嘧啶、3,4,5,6-四氫嘧啶-2-硫醇、4,5-二苯基咪唑-2-硫醇、2-巰基咪唑、2-巰基-1-甲基咪唑、4-胺基-3-肼基-5-巰基-1,2,4-三唑、3-胺基-5-巰基-1,2,4-三唑、2-甲基-4H-1,2,4-三唑-3-硫醇、4-甲基-4H-1,2,4-三唑-3-硫醇、3-巰基-1H-1,2,4-三唑-3-硫醇、2-胺基-5-巰基-1,3,4-噻二唑、5-胺基-1,3,4-噻二唑-2-硫醇、2,5-二巰基-1,3,4-噻二唑、(呋喃-2-基)甲硫醇、2-巰基-5-噻唑啶酮、2-巰基噻唑啉、2-巰基-4(3H)-喹唑啉酮、1-苯基-1H-四唑-5-硫醇、2-喹啉硫醇、2-巰基-5-甲基苯並咪唑、2-巰基-5-硝基苯並咪唑、6-胺基-2-巰基苯並噻唑、5-氯-2-巰基苯並噻唑、6-乙氧基-2-巰基苯並噻唑、6-硝基-2-巰基苯並噻唑、2-巰基萘並咪唑、2-巰基萘並噁唑、3-巰基-1,2,4-三唑、4-胺基-6-巰基吡唑並[2,4-d]吡啶、2-胺基-6-嘌呤硫醇、6-巰基嘌呤、4-巰基-1H-吡唑並[2,4-d]嘧啶等。 Examples of the compound having one alkyl group include 2-alkyl oxazole, 2-alkyl thiazole, 2-alkyl benzimidazole, 2-alkyl benzothiazole, 2-alkyl benzoxazole, 2-alkyl nicotinic acid, 2-alkyl pyridine, 2-alkyl pyridine-3-ol, 2-alkyl pyridine-N-oxide, 4-amino-6-hydroxy-2-alkyl pyrimidine, 4-amino-2-alkyl pyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5-diamino-6-hydroxy-2-alkyl pyrimidine, 4,6-diamino-2-alkyl pyrimidine, 2,4-diamino- 6-Alkylopyrimidine, 4,6-dihydroxy-2-alkynylpyrimidine, 4,6-dimethyl-2-alkynylpyrimidine, 4-hydroxy-2-alkynyl-6-methylpyrimidine, 4-hydroxy-2-alkynyl-6-propylpyrimidine, 2-alkynyl-4-methylpyrimidine, 2-alkynylpyrimidine, 2-thiouracil, 3,4,5,6-tetrahydropyrimidine-2-thiol, 4,5-diphenylimidazole-2-thiol, 2-alkynylimidazole, 2-alkynyl-1-methylimidazole, 4-amino-3-hydrazino-5-alkynyl-1,2,4-triazole, 3-amino-5-alkynyl-1,2,4-triazole triazole, 2-methyl-4H-1,2,4-triazole-3-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, 3-butyl-1H-1,2,4-triazole-3-thiol, 2-amino-5-butyl-1,3,4-thiadiazole, 5-amino-1,3,4-thiadiazole-2-thiol, 2,5-dibutyl-1,3,4-thiadiazole, (furan-2-yl) methyl mercaptan, 2-butyl-5-thiazolidinone, 2-butylthiazoline, 2-butyl-4 (3H)-quinazolinone, 1-phenyl-1H-tetrazolyl-5-thiophene Alcohol, 2-quinolinethiol, 2-hydroxy-5-methylbenzimidazole, 2-hydroxy-5-nitrobenzimidazole, 6-amino-2-hydroxybenzothiazole, 5-chloro-2-hydroxybenzothiazole, 6-ethoxy-2-hydroxybenzothiazole, 6-nitro-2-hydroxybenzothiazole, 2-hydroxynaphthoimidazole, 2-hydroxynaphthooxazole, 3-hydroxy-1,2,4-triazole, 4-amino-6-hydroxypyrazolo[2,4-d]pyridine, 2-amino-6-purinethiol, 6-hydroxypurine, 4-hydroxy-1H-pyrazolo[2,4-d]pyrimidine, etc.
作為具有兩個以上的巰基的化合物,例如可列舉:己烷二硫醇、癸烷二硫醇、1,4-雙(甲巰基)苯、丁二醇雙(3-巰基丙酸 酯)、丁二醇雙(3-巰基乙酸酯)、乙二醇雙(3-巰基乙酸酯)、三羥甲基丙烷三(3-巰基乙酸酯)、丁二醇雙(3-巰基丙酸酯)、三羥甲基丙烷三(3-巰基丙酸酯)(別名「三羥甲基丙烷三(3-氫硫基丙酸酯)」)、三羥甲基丙烷三(3-巰基乙酸酯)、季戊四醇四(3-巰基丙酸酯)、季戊四醇四(3-巰基乙酸酯)、三羥基乙基三(3-巰基丙酸酯)、季戊四醇四(3-巰基丁酸酯)、1,4-雙(3-巰基丁基氧基)丁烷等。 Examples of compounds having two or more alkyl groups include hexanedithiol, decanedithiol, 1,4-di(methylalkyl)benzene, butanediol bis(3-alkylpropionate), butanediol bis(3-alkyl acetate), ethylene glycol bis(3-alkyl acetate), trihydroxymethylpropane tris(3-alkyl acetate), butanediol bis(3-alkyl propionate), trihydroxymethylpropane tris(3 -Benzyl propionate) (also known as "trihydroxymethylpropane tris (3-hydrogenthiopropionate)"), trihydroxymethylpropane tris (3-benzylacetate), pentaerythritol tetra (3-benzylacetate), pentaerythritol tetra (3-benzylacetate), trihydroxyethyl tris (3-benzylacetate), pentaerythritol tetra (3-benzylacetate), 1,4-bis (3-benzybutyloxy) butane, etc.
硫醇化合物(G)較佳為具有兩個以上的巰基的化合物,更佳為三羥甲基丙烷三(3-巰基丙酸酯)。 The thiol compound (G) is preferably a compound having two or more hydroxyl groups, and more preferably trihydroxymethylpropane tris(3-hydroxypropionate).
於使用硫醇化合物(G)的情況下,其含量相對於聚合性化合物(C)100重量份而較佳為0.5重量份~20重量份,更佳為1重量份~15重量份。若硫醇化合物(G)的含量處於該範圍內,則有感度變高、且顯影性變良好的傾向。 When a thiol compound (G) is used, its content is preferably 0.5 to 20 parts by weight, and more preferably 1 to 15 parts by weight, relative to 100 parts by weight of the polymerizable compound (C). If the content of the thiol compound (G) is within this range, the sensitivity tends to be higher and the developing property tends to be better.
<溶劑(H)> <Solvent (H)>
本發明的著色硬化性樹脂組成物亦可進而包含溶劑(H)。溶劑(H)並無特別限定,可使用本領域中通常所使用的溶劑。作為溶劑(H),例如可列舉:酯溶劑(分子內包含-COO-且不含-O-的溶劑)、醚溶劑(分子內包含-O-且不含-COO-的溶劑)、醚酯溶劑(分子內包含-COO-與-O-的溶劑)、酮溶劑(分子內包含-CO-且不含-COO-的溶劑)、醇溶劑(分子內包含OH且不含-O-、-CO-及-COO-的溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸等。再者,所述「-O-」的概念中不包含「-COO-」中的「-O-」,所述「-CO-」的概念中不包含「-COO-」中的「-CO-」。 The colored curable resin composition of the present invention may further contain a solvent (H). The solvent (H) is not particularly limited, and a solvent commonly used in the art may be used. Examples of the solvent (H) include: ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO-, and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like. Furthermore, the concept of "-O-" does not include the "-O-" in "-COO-", and the concept of "-CO-" does not include the "-CO-" in "-COO-".
作為酯溶劑,例如可列舉:乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、乙酸乙酯、乙酸正丁酯、乙酸異丁酯、甲酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、環己醇乙酸酯及γ-丁內酯等。 Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, cyclohexanol acetate, and γ-butyrolactone.
作為醚溶劑,例如可列舉: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, diethylene 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, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.
作為醚酯溶劑,例如可列舉: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、二乙二醇單丁醚乙酸酯及二丙二醇甲醚乙酸酯等。 As ether ester solvents, for example, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, etc.
作為酮溶劑,例如可列舉: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、二丙酮醇、環戊酮、環己酮及異佛爾酮等。 Examples of ketone solvents include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, diacetone alcohol, cyclopentanone, cyclohexanone and isophorone.
作為醇溶劑,例如可列舉:甲醇、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、丙二醇及甘油等。 Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.
作為芳香族烴溶劑,例如可列舉:苯、甲苯、二甲苯及均三甲苯等。 Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
作為醯胺溶劑,例如可列舉: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 amide solvents include: N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
作為溶劑(H),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(H),較佳為3-甲氧基-1-丁醇、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、二丙酮醇、4-羥基-4-甲基-2-戊酮及N,N-二甲基甲醯胺,更佳為3-甲氧基-1-丁醇、丙二醇單甲醚乙酸酯、丙二醇單甲醚、乳酸乙酯、二丙酮醇及3-乙氧基丙酸乙酯。 As the solvent (H), in terms of coating properties and drying properties, an organic solvent having a boiling point of 120°C or higher and 180°C or lower at 1 atm is preferred. As the solvent (H), 3-methoxy-1-butanol, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide are preferred, and 3-methoxy-1-butanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and ethyl 3-ethoxypropionate are more preferred.
於使用溶劑(H)的情況下,其含量相對於本發明的著色硬化性樹脂組成物整體而較佳為35重量%~95重量%,更佳為40重量%~92重量%。換言之,著色硬化性樹脂組成物的固體成分的總量較佳為5重量%~65重量%,更佳為8重量%~60重量%。若溶劑(H)的含量處於所述範圍內,則塗佈時的平坦性變良好,另外,於形成彩色濾光片時顏色濃度不會不足,因此有顯示 特性變良好的傾向。 When a solvent (H) is used, its content is preferably 35% to 95% by weight, and more preferably 40% to 92% by weight, relative to the entire coloring curable resin composition of the present invention. In other words, the total amount of solid components of the coloring curable resin composition is preferably 5% to 65% by weight, and more preferably 8% to 60% by weight. If the content of the solvent (H) is within the above range, the flatness during coating becomes good, and in addition, the color concentration will not be insufficient when forming a color filter, so there is a tendency for the display characteristics to become good.
<調平劑(I)> <Leveling agent (I)>
本發明的著色硬化性樹脂組成物亦可包含調平劑(I)。作為調平劑(I),例如可列舉矽酮系界面活性劑及氟系界面活性劑等。該些亦可於側鏈具有聚合性基。 The colored curable resin composition of the present invention may also contain a leveling agent (I). Examples of the leveling agent (I) include silicone-based surfactants and fluorine-based surfactants. These may also have polymerizable groups in the side chains.
作為矽酮系界面活性劑,例如可列舉分子內具有矽氧烷鍵的界面活性劑等。作為其市售品,例如可列舉: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)公司製造);KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業公司製造);TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF-4446、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 silicone-based surfactants include surfactants having siloxane bonds in the molecule. Examples of commercially available products include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (Toray Dow Corning) and Toray Silicone SH8400. Corning); KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.), etc.
矽酮系界面活性劑亦可具有氟原子。作為具有氟原子的矽酮系界面活性劑,例如可列舉: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)公司製造)等。 Silicone-based surfactants may also have fluorine atoms. Examples of silicone-based surfactants having fluorine atoms include Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation).
作為氟系界面活性劑,例如可列舉分子內具有氟碳鏈的界面活性劑等。作為其市售品,例如可列舉:佛羅德(Fluorad)(註冊商標)FC430、佛羅德(Fluorad)FC431(住友3M公司製造);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)公司製造);艾福拓(Eftop)(註冊商標)EF301、艾福拓(Eftop)EF303、艾福拓(Eftop)EF351、艾福拓(Eftop)EF352(三菱材料電子化成公司製造);沙福隆(Surflon)(註冊商標)S381、沙福隆(Surflon)S382、沙福隆(Surflon)SC101、沙福隆(Surflon)SC105(旭硝子公司製造)及E5844(大金精細化學(Daikin Fine Chemical)研究所(股)製造)等。 Examples of fluorine-based surfactants include surfactants having a fluorine-carbon chain in the molecule. Examples of commercially available products include: Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co.); Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac R40, Megafac R555, Megafac R60, Megafac R70, Megafac R80, Megafac R90, Megafac R100, Megafac R110, Megafac R111, Megafac R112, Megafac R113, Megafac R114, Megafac R115, Megafac R116, Megafac R117, Megafac R118, Megafac R119, Megafac R120, Megafac R121, Megafac R122, Megafac R123, Megafac R124, Megafac R125, Megafac R126, Megafac R127, Megafac R128, Megafac R129, Megafac R130, Megafac R131, Megafac R132, Megafac R133, Megafac R134, Megafac R135, Megafac R136, Megafac R137, Megafac R138, Megafac R139, Megafac R140, Megafac R141, Megafac R142 fac) RS-718-K (manufactured by DIC Corporation); Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.); Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Ltd.), etc.
於使用調平劑(I)的情況下,其含量相對於著色硬化性樹脂組成物整體而較佳為0.001重量%以上且0.2重量%以下,更佳為0.002重量%以上且0.1重量%以下,進而佳為0.01重量%以上且0.05重量%以下。再者,該含量中不包含顏料分散液的製造中使用的分散劑的含量。若調平劑(I)的含量處於所述範圍內,則可使彩色濾光片的平坦性良好。 When the leveling agent (I) is used, its content is preferably 0.001% by weight or more and 0.2% by weight or less, more preferably 0.002% by weight or more and 0.1% by weight or less, and further preferably 0.01% by weight or more and 0.05% by weight or less, relative to the entire coloring curable resin composition. Furthermore, this content does not include the content of the dispersant used in the manufacture of the pigment dispersion. If the content of the leveling agent (I) 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、鏈轉移劑等本技術領 域中公知的添加劑。 The colored curable resin composition of the present invention may also contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and other additives known in the art as needed.
<著色硬化性樹脂組成物的製造方法> <Method for producing a colored curable resin composition>
本發明的著色硬化性樹脂組成物例如可藉由如下方式來製備:將著色劑(A)、樹脂(B)(樹脂(B1)及視需要的樹脂(B2))、聚合性化合物(C)、聚合起始劑(D)及酚系抗氧化劑(E)、以及視需要的溶劑(H)、調平劑(I)、聚合起始助劑(F)、硫醇化合物(G)以及其他成分混合。 The colored curable resin composition of the present invention can be prepared, for example, by mixing a colorant (A), a resin (B) (resin (B1) and optionally a resin (B2)), a polymerizable compound (C), a polymerization initiator (D) and a phenolic antioxidant (E), and optionally a solvent (H), a leveling agent (I), a polymerization initiator aid (F), a thiol compound (G) and other components.
於使用顏料(A2)的情況下,較佳為將顏料(A2)預先與溶劑(H)的一部分或全部混合,並使用珠磨機等對顏料(A2)進行分散直至顏料(A2)的平均粒子徑為0.2μm以下左右,從而製備顏料分散液。此時,視需要可調配分散劑、樹脂(B)(尤其是樹脂(B2))的一部分或全部。藉由在如此獲得的顏料分散液中以成為規定濃度的方式混合剩餘的成分,可製備目標著色硬化性樹脂組成物。 When using the pigment (A2), it is preferred to mix the pigment (A2) with a part or all of the solvent (H) in advance, and disperse the pigment (A2) using a bead mill or the like until the average particle size of the pigment (A2) is about 0.2 μm or less, thereby preparing a pigment dispersion. At this time, a part or all of the dispersant and the resin (B) (especially the resin (B2)) may be prepared as needed. By mixing the remaining components in the thus obtained pigment dispersion in a manner to obtain a predetermined concentration, the target coloring curable resin composition may be prepared.
於使用染料(A1)的情況下,亦可使染料(A1)預先溶解於溶劑(H)的一部分或全部中,從而製備染料溶液。較佳為利用孔徑0.01μm~1μm左右的過濾器對該溶液進行過濾。另外,較佳為利用孔徑0.01μm~10μm左右的過濾器對混合所述成分而獲得的著色硬化性樹脂組成物進行過濾。 When the dye (A1) is used, the dye (A1) may be dissolved in part or all of the solvent (H) to prepare a dye solution. The solution is preferably filtered using a filter having a pore size of about 0.01 μm to 1 μm. In addition, the colored curable resin composition obtained by mixing the above components is preferably filtered using a filter having a pore size of about 0.01 μm to 10 μm.
<彩色濾光片及液晶顯示裝置的製造方法> <Color filter and liquid crystal display device manufacturing method>
作為利用本發明的著色硬化性樹脂組成物形成彩色濾光片的方法,例如可列舉光微影法及使用噴墨設備的方法。於光微影法 中,通常包括如下步驟:將著色硬化性樹脂組成物塗佈於基板上,藉由加熱乾燥(預烘烤)及/或減壓乾燥來去除溶劑等揮發成分而形成組成物層,介隔光罩對該組成物層照射(曝光)光,使顯影液與曝光後的組成物層接觸而形成(顯影)著色圖案。於該顯影後,經常進行對著色圖案進行加熱的後烘烤。於所述光微影法中,藉由在曝光時不使用光罩、及/或不進行顯影,可形成作為所述組成物層的硬化物的著色塗膜。可使用如此獲得的著色圖案及著色塗膜作為彩色濾光片。 As a method of forming a color filter using the colored curable resin composition of the present invention, for example, photolithography and a method using an inkjet device can be cited. In the photolithography method, the following steps are generally included: the colored curable resin composition is applied to a substrate, volatile components such as a solvent are removed by heat drying (pre-baking) and/or reduced pressure drying to form a composition layer, the composition layer is irradiated (exposed) with light through a photomask, and a developer is brought into contact with the exposed composition layer to form (develop) a colored pattern. After the development, a post-baking of heating the colored pattern is often performed. In the photolithography method, a colored coating film as a cured product of the composition layer can be formed by not using a photomask during exposure and/or not performing development. The colored pattern and colored coating thus obtained can be used as a color filter.
作為基板,例如可列舉:玻璃板、樹脂板、矽板等。亦可於所述基板上形成鋁、銀、銀/銅/鈀合金薄膜等。進而,亦可於所述基板上形成其他的彩色濾光片層、樹脂層、電晶體、電路等。 As the substrate, for example, glass plates, resin plates, silicon plates, etc. can be listed. Aluminum, silver, silver/copper/palladium alloy thin films, etc. can also be formed on the substrate. Furthermore, other color filter layers, resin layers, transistors, circuits, etc. can also be formed on the substrate.
要製作的彩色濾光片的厚度並無特別限定,可根據目標用途等適宜調整,例如為0.1μm~30μm,較佳為1μm~20μm,更佳為1μm~6μm。 The thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the target use, for example, 0.1μm~30μm, preferably 1μm~20μm, and more preferably 1μm~6μm.
利用光微影法進行的著色圖案(畫素)的形成可藉由公知或慣用的裝置或條件來進行。例如,可以如下方式形成著色圖案。 The formation of a colored pattern (pixel) using photolithography can be performed by known or conventional devices or conditions. For example, a colored pattern can be formed as follows.
首先,將著色硬化性樹脂組成物塗佈於基板上,藉由進行加熱乾燥(預烘烤)及/或減壓乾燥來去除溶劑等揮發成分,從而獲得平滑的組成物層。作為塗佈方法,例如可列舉:旋轉塗佈法、狹縫塗佈法、狹縫與旋轉塗佈法等。 First, a colored curable resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth composition layer. Examples of coating methods include spin coating, slit coating, slit and spin coating, etc.
其次,介隔用於形成目標著色圖案的光罩對組成物層照 射(曝光)光。為了可對曝光面整體均勻地照射平行光線、或進行光罩與形成有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。 Next, the component layer is irradiated (exposed) with light through a photomask for forming the target coloring pattern. In order to evenly irradiate the entire exposure surface with parallel light or to accurately align the photomask with the substrate on which the component layer is formed, it is preferred to use an exposure device such as a mask aligner and a stepper.
藉由使曝光後的組成物層與顯影液接觸,可於基板上形成(顯影)著色圖案。藉由顯影而將組成物層的未曝光部溶解於顯影液中並去除。作為顯影液,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。顯影方法可為覆液法、浸漬法及噴霧法等的任一種。進而,顯影時亦可使基板以任意角度傾斜。較佳為於顯影後進行水洗。 By bringing the exposed component layer into contact with a developer, a colored pattern can be formed (developed) on the substrate. The unexposed portion of the component layer is dissolved in the developer and removed by development. As a developer, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide, etc. is preferred. The developing method may be any of a coating method, an immersion method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. It is preferred to wash with water after development.
由本發明的著色硬化性樹脂組成物製造的彩色濾光片作為顯示裝置(例如,液晶顯示裝置、有機電致發光(electroluminescence,EL)裝置、電子紙等)及固體攝像元件中所使用的彩色濾光片有用。 The color filter produced from the colored curable resin composition of the present invention is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging devices.
[實施例] [Implementation example]
以下,列舉實施例來更具體地說明本發明,但本發明根本不受下述實施例的限制,亦能夠於可適合所述、下述的主旨的範圍內適當施加變更而實施,該些均包含於本發明的技術範圍內。再者,以下,只要無特別說明,則「份」是指「重量份」,厚度保持率以外的「%」是指「重量%」。 The following examples are given to more specifically illustrate the present invention, but the present invention is not limited to the following examples at all, and can be implemented with appropriate changes within the scope of the above and the following purposes, all of which are included in the technical scope of the present invention. In addition, below, unless otherwise specified, "parts" means "parts by weight", and "%" other than thickness retention rate means "% by weight".
以下,化合物的結構是由質量分析(LC;安捷倫(Agilent)製造的1200型、MASS;安捷倫(Agilent)製造的LC/MSD型)確認。 The structures of the compounds below were confirmed by mass spectrometry (LC; 1200 model manufactured by Agilent, MASS; LC/MSD model manufactured by Agilent).
製造例中所獲得的樹脂的重量平均分子量(Mw)及數量平均分子量(Mn)的測定是使用GPC並於以下條件下進行。 The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin obtained in the production example were measured using GPC under the following conditions.
裝置:K2479(島津製作所(股)製造) Device: K2479 (manufactured by Shimadzu Corporation)
管柱:SHIMADZU Shim-pack GPC-80M Column: SHIMADZU Shim-pack GPC-80M
管柱溫度:40℃ Column temperature: 40℃
溶媒:THF(四氫呋喃) Solvent: THF (tetrahydrofuran)
流速:1.0mL/min Flow rate: 1.0mL/min
檢測器:RI Detector: RI
校正用標準物質:TSK標準聚苯乙烯(TSK STANDARD POLYSTYRENE)F-40、F-4、F-228、A-2500、A-500(東曹(Tosoh)公司製造) Standard materials for calibration: TSK standard polystyrene F-40, F-4, F-228, A-2500, A-500 (manufactured by Tosoh Corporation)
將所述所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)設為分子量分佈。 The ratio of the obtained polystyrene-converted weight average molecular weight to the number average molecular weight (Mw/Mn) is defined as the molecular weight distribution.
<製造例1:樹脂(B1-1)的製造> <Manufacturing Example 1: Manufacture of Resin (B1-1)>
於包括攪拌裝置、滴加漏斗、冷凝器、溫度計以及氣體導入管的燒瓶中,放入3-甲氧基丁醇750.0g,一邊進行氮氣置換一邊進行攪拌,升溫至80℃。 Place 750.0 g of 3-methoxybutanol in a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, stir while replacing the atmosphere with nitrogen, and heat to 80°C.
其次,自滴加漏斗向所述燒瓶中滴加如下物質,所述物質是於包含甲基丙烯酸25.6g(0.30莫耳)、3-甲基丙烯醯基氧基丙基三甲氧基矽烷146.4g(0.50莫耳)及甲基丙烯酸甲酯49.2g(0.49莫耳)的單體混合物中添加2,2'-偶氮雙(2,4-二甲基戊腈)(聚合起始劑)28.8g而成。 Next, the following substance was added dropwise into the flask from the dropping funnel. The substance was prepared by adding 28.8 g of 2,2'-azobis(2,4-dimethylvaleronitrile) (polymerization initiator) to a monomer mixture containing 25.6 g (0.30 mol) of methacrylic acid, 146.4 g (0.50 mol) of 3-methacryloyloxypropyltrimethoxysilane, and 49.2 g (0.49 mol) of methyl methacrylate.
滴加結束後,於80℃下對混合物進行5小時攪拌並進行共聚反應,獲得樹脂(B1-1)(重量平均分子量(Mw):5,500,酸價:82mgKOH/g,矽烷基當量:500)。 After the addition was completed, the mixture was stirred at 80°C for 5 hours and copolymerized to obtain resin (B1-1) (weight average molecular weight (Mw): 5,500, acid value: 82 mgKOH/g, silane equivalent: 500).
<製造例2:樹脂(B1-2)的製造> <Manufacturing Example 2: Manufacture of Resin (B1-2)>
於包括攪拌裝置、滴加漏斗、冷凝器、溫度計以及氣體導入管的燒瓶中,放入丙二醇單甲醚750.0g,一邊進行氮氣置換一邊進行攪拌,升溫至80℃。 Place 750.0 g of propylene glycol monomethyl ether in a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, stir while replacing the atmosphere with nitrogen, and heat to 80°C.
其次,自滴加漏斗向所述燒瓶中滴加如下物質,所述物質是於包含甲基丙烯酸39.2g(0.46莫耳)、3-甲基丙烯醯基氧基丙基三乙氧基矽烷132.0g(0.46莫耳)及甲基丙烯酸二環戊烷基酯50.1g(0.23莫耳)的單體混合物中添加2,2'-偶氮雙(2,4-二甲基戊腈)(聚合起始劑)28.8g而成。 Next, the following substance was added dropwise into the flask from the dropping funnel. The substance was prepared by adding 28.8 g of 2,2'-azobis(2,4-dimethylvaleronitrile) (polymerization initiator) to a monomer mixture containing 39.2 g (0.46 mol) of methacrylic acid, 132.0 g (0.46 mol) of 3-methacryloyloxypropyltriethoxysilane and 50.1 g (0.23 mol) of dicyclopentyl methacrylate.
滴加結束後,於80℃下對混合物進行5小時攪拌並進行共聚反應,獲得樹脂(B1-2)(重量平均分子量(Mw):4,000,酸價:135mgKOH/g,矽烷基當量:550)。 After the addition was completed, the mixture was stirred at 80°C for 5 hours and copolymerized to obtain resin (B1-2) (weight average molecular weight (Mw): 4,000, acid value: 135 mgKOH/g, silane equivalent: 550).
<製造例3:樹脂(B2-1)的製造> <Production Example 3: Production of Resin (B2-1)>
於包括回流冷卻器、滴加漏斗及攪拌機的燒瓶內,置換為氮氣環境,放入丙二醇單甲醚乙酸酯280份,一邊進行攪拌一邊加熱至80℃。繼而,歷時5小時滴加丙烯酸38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(含有比以莫耳比計為1:1)289份、丙二醇單甲醚乙酸酯125份的混合溶液。另一方面,歷時6小時滴加使2,2- 偶氮雙(2,4-二甲基戊腈)33份溶解於丙二醇單甲醚乙酸酯235份中而成的溶液。滴加結束後,將混合物於80℃下保持4小時後,冷卻至室溫,獲得固體成分為35.1%、利用B型黏度計(23℃)測定的黏度為125mPa.s的共聚物(樹脂(B2-1))溶液。所獲得的共聚物的重量平均分子量(Mw)為9.2×103、分子量分佈(Mw/Mn)為2.08、酸價(固體成分換算值)為77mgKOH/g。樹脂(B2-1)具有以下構成單元(下述式中,*表示鍵結位置)。 In a flask equipped with a reflux cooler, a dropping funnel and a stirrer, a nitrogen atmosphere was replaced, 280 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 80°C while stirring. Subsequently, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in molar ratio), and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B2-1)) solution having a solid content of 35.1% and a viscosity of 125 mPa.s measured by a B-type viscometer (23°C). The weight average molecular weight (Mw) of the obtained copolymer was 9.2×10 3 , the molecular weight distribution (Mw/Mn) was 2.08, and the acid value (solid content conversion value) was 77 mgKOH/g. Resin (B2-1) has the following structural units (in the following formula, * indicates the bonding position).
<製造例4:紅色顏料的分散液的製造> <Production Example 4: Production of red pigment dispersion>
將以後述方式合成的紅色顏料50.6份、分散劑(畢克(BYK)公司製造的畢克艾皮恩(BYKLPN)-6919;丙二醇單甲醚乙酸酯60%溶液)10.1份、樹脂(B2-1)20.3份(以固體成分換算計)、丙二醇單甲醚64.5份及丙二醇單甲醚乙酸酯216.0份混合,加入0.4μm的氧化鋯珠粒600份,使用塗料調節器(paint conditioner)(LAU公司製造)將所獲得的混合物振盪1小時。其後,藉由過濾將氧化鋯珠粒去除,獲得紅色顏料的分散液。 50.6 parts of the red pigment synthesized in the following manner, 10.1 parts of a dispersant (BYKLPN-6919 manufactured by BYK; 60% solution of propylene glycol monomethyl ether acetate), 20.3 parts of a resin (B2-1) (calculated as solid content), 64.5 parts of propylene glycol monomethyl ether, and 216.0 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and the obtained mixture was vibrated for 1 hour using a paint conditioner (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to obtain a dispersion of the red pigment.
紅色顏料的分散液的製造中所使用的紅色顏料是以如下方式合成。 The red pigment used in the preparation of the red pigment dispersion is synthesized as follows.
使174g的第三戊基醇與金屬鈉22.2g於氮氣環境下、130℃下進行反應,合成第三戊基醇鈉。將其加熱至60℃,加入4-溴苯甲腈91.0g、琥珀酸二-第三戊基酯71.05g、及第三戊基醇108.9g,以所獲得的懸浮液的溫度為85℃以下的方式將懸浮液攪拌2小時。將該懸濁液於85℃下直接攪拌18小時以上,然後加入至冷卻為-10℃的甲醇200g與水1000g及硫酸49.21g的混合液中。懸浮液的添加結束後,將所獲得的混合物一邊保持為0℃一邊攪拌5小時,使反應結束,然後藉由過濾回收固態物質。利用甲醇及水對所回收的固態物質交替地進行清洗。該清洗是重覆進行至清洗中所使用的甲醇及水的著色消失且鹽的析出消失為止。利用80℃的真空乾燥機對清洗後的固態物質進行18小時乾燥,獲得紅色顏料。 174 g of tert-amyl alcohol and 22.2 g of metallic sodium were reacted at 130° C. in a nitrogen atmosphere to synthesize sodium tert-amyl alcohol. The mixture was heated to 60° C., 91.0 g of 4-bromobenzonitrile, 71.05 g of di-tert-amyl succinate, and 108.9 g of tert-amyl alcohol were added, and the suspension was stirred for 2 hours so that the temperature of the obtained suspension was 85° C. or less. The suspension was stirred at 85° C. for more than 18 hours, and then added to a mixture of 200 g of methanol, 1000 g of water, and 49.21 g of sulfuric acid cooled to -10° C. After the addition of the suspension is completed, the obtained mixture is stirred for 5 hours while being kept at 0°C to complete the reaction, and then the solid matter is recovered by filtration. The recovered solid matter is washed alternately with methanol and water. The washing is repeated until the coloring of the methanol and water used in the washing disappears and the precipitation of the salt disappears. The washed solid matter is dried in a vacuum dryer at 80°C for 18 hours to obtain a red pigment.
<製造例5:藍色顏料的分散液的製造> <Production Example 5: Production of a blue pigment dispersion>
將C.I.顏料藍15:6 19.2份、分散劑(畢克(BYK)公司製造的畢克艾皮恩(BYKLPN)-6919;丙二醇單甲醚乙酸酯60%溶液)6.7份、樹脂(B2-1)7.7份(以固體成分換算計)、乳酸乙酯14.6份及丙二醇單甲醚乙酸酯143.8份混合,加入0.4μm的氧化鋯珠粒600份,使用塗料調節器(LAU公司製造)將所獲得的混合物振盪1小時。其後,藉由過濾將氧化鋯珠粒去除,獲得藍色顏料的分散液。 19.2 parts of C.I. Pigment Blue 15:6, 6.7 parts of dispersant (BYKLPN-6919 manufactured by BYK; 60% solution of propylene glycol monomethyl ether acetate), 7.7 parts of resin (B2-1) (calculated as solid content), 14.6 parts of ethyl lactate and 143.8 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4μm zirconia beads were added, and the obtained mixture was vibrated for 1 hour using a paint conditioner (manufactured by LAU). Afterwards, the zirconia beads were removed by filtration to obtain a dispersion of blue pigment.
<製造例6:化合物(A3-1-1)的製造> <Production Example 6: Production of Compound (A3-1-1)>
藉由日本專利特開2018-127596號公報的實施例7中記載的方法來製造下述式(A3-1-1)所表示的化合物。 The compound represented by the following formula (A3-1-1) was prepared by the method described in Example 7 of Japanese Patent Publication No. 2018-127596.
<製造例7:化合物(A3-2-1)的製造> <Production Example 7: Production of Compound (A3-2-1)>
藉由日本專利特開2015-38201號公報的合成例19中記載的方法來製造下述式(A3-2-1)所表示的化合物。 The compound represented by the following formula (A3-2-1) was prepared by the method described in Synthesis Example 19 of Japanese Patent Publication No. 2015-38201.
<製造例8:化合物(A3-1-1)的分散液的製造> <Production Example 8: Production of a dispersion of compound (A3-1-1)>
將化合物(A3-1-1)7份、分散劑(畢克化學(BYK-Chemie)公司製造的迪斯帕畢克(DISPERBYK)(註冊商標)-2050;丙二醇單甲醚乙酸酯52%溶液)3份、樹脂(B2-1)(以固體成分換算計)3份、丙二醇單甲醚乙酸酯81份、二丙酮醇6份及0.2mm的氧化鋯珠粒300份混合,使用塗料調節器(LAU公司製造)將所獲得的混合物振盪3小時。其後,藉由過濾將氧化鋯珠粒去除,製造化合物(A3-1-1)的分散液。再者,化合物(A3-1-1)雖為溶解於二丙酮醇的染料,但為了提高與耐熱性及耐光性相關的化合物(A3-1-1)的可靠性,而使用丙二醇單甲醚乙酸酯來製造化合物(A3-1-1)的分散液,並使用該分散液。 7 parts of compound (A3-1-1), 3 parts of dispersant (DISPERBYK (registered trademark)-2050 manufactured by BYK-Chemie; 52% solution of propylene glycol monomethyl ether acetate), 3 parts of resin (B2-1) (calculated as solid content), 81 parts of propylene glycol monomethyl ether acetate, 6 parts of diacetone alcohol, and 300 parts of 0.2 mm zirconia beads were mixed, and the obtained mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to prepare a dispersion of compound (A3-1-1). Furthermore, although compound (A3-1-1) is a dye soluble in diacetone alcohol, in order to improve the reliability of compound (A3-1-1) related to heat resistance and light resistance, propylene glycol monomethyl ether acetate is used to prepare a dispersion of compound (A3-1-1), and the dispersion is used.
<製造例9:化合物(A3-2-1)的分散液的製造> <Production Example 9: Production of a dispersion of compound (A3-2-1)>
將化合物(A3-2-1)14份、分散劑(畢克(BYK)公司製造的畢克艾皮恩(BYKLPN)-6919;丙二醇單甲醚乙酸酯60%溶液)2份、樹脂(B2-1)(以固體成分換算計)6份、丙二醇單甲醚乙酸酯74份、二丙酮醇4份及0.2mm的氧化鋯珠粒300份混合,使用塗料調節器(LAU公司製造)將所獲得的混合物振盪3小時。其後,藉由過濾將氧化鋯珠粒去除,製造化合物(A3-2-1)的分散液。再者,化合物(A3-2-1)雖為溶解於二丙酮醇的染料,但為了提高與耐熱性及耐光性相關的化合物(A3-2-1)的可靠性,而使用丙二醇單甲醚乙酸酯來製造化合物(A3-2-1)的分散液, 並使用該分散液。 14 parts of compound (A3-2-1), 2 parts of dispersant (BYKLPN-6919 manufactured by BYK; 60% solution of propylene glycol monomethyl ether acetate), 6 parts of resin (B2-1) (calculated as solid content), 74 parts of propylene glycol monomethyl ether acetate, 4 parts of diacetone alcohol, and 300 parts of 0.2 mm zirconia beads were mixed, and the obtained mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to prepare a dispersion of compound (A3-2-1). Furthermore, although compound (A3-2-1) is a dye soluble in diacetone alcohol, in order to improve the reliability of compound (A3-2-1) related to heat resistance and light resistance, propylene glycol monomethyl ether acetate is used to prepare a dispersion of compound (A3-2-1), and the dispersion is used.
實施例1~實施例16及比較例1~比較例5 Example 1 to Example 16 and Comparative Example 1 to Comparative Example 5
(1)著色硬化性樹脂組成物的製造 (1) Production of coloring curable resin composition
以成為下述表1~表3所示的組成的方式混合各成分,獲得著色硬化性樹脂組成物。 The components are mixed in such a manner as to form the compositions shown in Tables 1 to 3 below to obtain a colored curable resin composition.
著色硬化性樹脂組成物的製造中所使用的各成分為如下所述。 The components used in the production of the colored curable resin composition are as follows.
<染料(A1)> <Dye (A1)>
(A1-1):藉由日本專利特開2016-27075的實施例1中記載的方法而獲得的下述式(A1-1)所表示的染料 (A1-1): A dye represented by the following formula (A1-1) obtained by the method described in Example 1 of Japanese Patent Laid-Open No. 2016-27075
(A1-2):藉由日本專利特開2017-226814的實施例2中記載的方法而獲得的下述式(A1-2)所表示的染料 (A1-2): A dye represented by the following formula (A1-2) obtained by the method described in Example 2 of Japanese Patent Laid-Open No. 2017-226814
(A1-3):藉由日本專利特開2016-176075的合成例2中記載的方法而獲得的下述式(A1-3)所表示的染料 (A1-3): A dye represented by the following formula (A1-3) obtained by the method described in Synthesis Example 2 of Japanese Patent Laid-Open No. 2016-176075
<顏料(A2)的分散液> <Dispersion of pigment (A2)>
紅色顏料的分散液:製造例4中所獲得的分散液 Red pigment dispersion: the dispersion obtained in Preparation Example 4
藍色顏料的分散液:製造例5中所獲得的分散液 Blue pigment dispersion: the dispersion obtained in Preparation Example 5
<化合物(A3)的分散液> <Dispersion of compound (A3)>
化合物(A3-1-1)的分散液:製造例8中所獲得的分散液 Dispersion of compound (A3-1-1): the dispersion obtained in Preparation Example 8
化合物(A3-2-1)的分散液:製造例9中所獲得的分散液 Dispersion of compound (A3-2-1): the dispersion obtained in Preparation Example 9
<樹脂(B)> <Resin (B)>
(B1-1):製造例1中所獲得的樹脂(B1-1) (B1-1): Resin (B1-1) obtained in Production Example 1
(B1-2):製造例2中所獲得的樹脂(B1-2) (B1-2): Resin (B1-2) obtained in Production Example 2
(B2-1):製造例3中所獲得的樹脂(B2-1)(於顏料(A2)的分散液的製造、化合物(A3)的分散液的製造、以及比較例4中使用) (B2-1): Resin (B2-1) obtained in Preparation Example 3 (used in the preparation of the dispersion of the pigment (A2), the preparation of the dispersion of the compound (A3), and Comparative Example 4)
<聚合性化合物(C)> <Polymerizable compound (C)>
(C-1):二季戊四醇六丙烯酸酯(日本化藥公司製造的「卡亞拉得(KAYARAD)(註冊商標)DPHA」) (C-1): Dipentaerythritol hexaacrylate ("KAYARAD (registered trademark) DPHA" manufactured by Nippon Kayaku Co., Ltd.)
<聚合起始劑(D)> <Polymerization initiator (D)>
(D-1):下述式(D-1)所表示的化合物(常州強力電子新材料公司製造的「TR-PBG327」) (D-1): The compound represented by the following formula (D-1) ("TR-PBG327" manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)
(D-2):巴斯夫(BASF)公司製造的「豔佳固(Irgacure)(註冊商標)907」 (D-2): "Irgacure (registered trademark) 907" manufactured by BASF
[化40]
<酚系抗氧化劑(E)> <Phenolic antioxidant (E)>
(E-1):6-[3-(3-第三丁基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-第三丁基二苯並[d,f][1.3.2]二氧雜磷雜庚英(住友化學公司製造的「蘇米萊澤(Sumilizer)(註冊商標)GP」) (E-1): 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1.3.2]dioxophosphine ("Sumilizer (registered trademark) GP" manufactured by Sumitomo Chemical Co., Ltd.)
(E-2):艾迪科(ADEKA)公司製造的「艾迪科亞科魯茲(Adeka arkls)(註冊商標)GPA-5001」 (E-2): "Adeka arkls (registered trademark) GPA-5001" manufactured by ADEKA Corporation
(E-3):艾迪科(ADEKA)公司製造的「艾迪科斯塔波(Adekastab)(註冊商標)AO-60」 (E-3): "Adekastab (registered trademark) AO-60" manufactured by ADEKA Corporation
<磷系抗氧化劑> <Phosphorus antioxidants>
TPP:三苯基亞磷酸酯(艾迪科(ADEKA)公司製造的「艾迪科斯塔波(Adekastab)(註冊商標)TPP」) TPP: Triphenylphosphite ("Adekastab (registered trademark) TPP" manufactured by ADEKA)
<聚合起始助劑(F)> <Polymerization initiation aid (F)>
(F-1):2,4-二乙基硫雜蒽酮(日本化藥公司製造的「卡亞固(KAYACURE)(註冊商標)DETX-S」) (F-1): 2,4-diethylthioxanthrone ("KAYACURE (registered trademark) DETX-S" manufactured by Nippon Kayaku Co., Ltd.)
<硫醇化合物(G)> <Thiol compound (G)>
(G-1):三羥甲基丙烷三(3-氫硫基丙酸酯)(SC有機化學公 司製造) (G-1): Trihydroxymethylpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemicals)
<溶劑(H)> <Solvent (H)>
(H-1):3-甲氧基-1-丁醇(東京化成工業公司製造,沸點158℃) (H-1): 3-methoxy-1-butanol (manufactured by Tokyo Chemical Industry Co., Ltd., boiling point 158°C)
(H-2):二丙酮醇(東京化成工業公司製造,沸點168℃) (H-2): Diacetone alcohol (produced by Tokyo Chemical Industry Co., Ltd., boiling point 168°C)
(H-3):丙二醇單甲醚乙酸酯(KH耐奧凱姆(KHneochem)公司製造,146℃) (H-3): Propylene glycol monomethyl ether acetate (manufactured by KHneochem, 146°C)
(H-4):丙二醇單甲醚(KH耐奧凱姆(KHneochem)公司製造,沸點121℃) (H-4): Propylene glycol monomethyl ether (manufactured by KHneochem, boiling point 121°C)
<調平劑(I)> <Leveling agent (I)>
(I-1):矽酮系界面活性劑(東麗道康寧(Toray Dow Corning)公司製造的「東麗矽酮(Toray Silicone)SH8400」) (I-1): Silicone-based surfactant ("Toray Silicone SH8400" manufactured by Toray Dow Corning)
(2)彩色濾光片(著色塗膜)的形成 (2) Formation of color filter (colored coating)
於2英吋見方的玻璃基板(益格(eagle)2000;康寧(Corning)公司製造)上,利用旋轉塗佈法塗佈著色硬化性樹脂組成物,然後在100℃下預烘烤3分鐘,形成組成物層。冷卻後,使用曝光機(TME-150RSK;托普康(Topcon)公司製造),於大氣環境下,以60mJ/cm2的曝光量(365nm基準)對組成物層進行光照射。光照射後,於烘箱中,在230℃下進行20分鐘後烘烤,藉此獲得著色塗膜。放置冷卻後,使用膜厚測定裝置(DEKTAK3;日本真空技術公司製造)對所獲得的著色塗膜的厚度進行測定,結果為3.0μm。 A colored curable resin composition was applied to a 2-inch square glass substrate (Eagle 2000; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a composition layer. After cooling, the composition layer was irradiated with light at an exposure dose of 60mJ/ cm2 (365nm reference) in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon). After light irradiation, post-baking was performed in an oven at 230°C for 20 minutes to obtain a colored coating film. After being left to cool, the thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.) and the result was 3.0 μm.
(3)厚度保持率的評價 (3) Evaluation of thickness retention rate
使用膜厚測定裝置(DEKTAK3;日本真空技術公司製造)對所形成的著色塗膜的後烘烤前後的厚度進行測定,並依照下述式子算出厚度保持率。 The thickness of the formed colored coating before and after post-baking was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.), and the thickness retention rate was calculated according to the following formula.
厚度保持率(%)=(後烘烤後的厚度/後烘烤前的厚度)×100 Thickness retention rate (%) = (thickness after post-baking/thickness before post-baking) × 100
將結果示於表1~表3中。 The results are shown in Tables 1 to 3.
[表2]
如根據表1~表3所示的結果而明確般,使用酚系抗氧化劑及樹脂(B1)(即,樹脂(B1-1)或樹脂(B1-2))的實施例1~實施例16的著色硬化性樹脂組成物與未使用抗氧化劑的比較例1、比較例3及比較例5、或者使用磷系抗氧化劑代替酚系抗氧化劑的比較例2、未使用樹脂(B1)的比較例4的著色硬化性樹脂組成物相比,可抑制由後烘烤引起的著色塗膜的厚度減少。 As is clear from the results shown in Tables 1 to 3, the coloring curable resin compositions of Examples 1 to 16 using a phenolic antioxidant and resin (B1) (i.e., resin (B1-1) or resin (B1-2)) can suppress the reduction in thickness of the coloring coating film caused by post-baking, compared with the coloring curable resin compositions of Comparative Examples 1, 3, and 5 that do not use an antioxidant, or Comparative Example 2 that uses a phosphorus antioxidant instead of a phenolic antioxidant, and Comparative Example 4 that does not use resin (B1).
[產業上的可利用性] [Industrial availability]
若使用本發明的著色硬化性樹脂組成物,則可抑制由加熱(尤其是後烘烤)引起的著色圖案或著色塗膜的厚度減少。由本發明的著色硬化性樹脂組成物製造的彩色濾光片作為顯示裝置(例如,液晶顯示裝置、有機EL裝置、電子紙等)以及固體攝像元件中所使用的彩色濾光片有用。 If the coloring curable resin composition of the present invention is used, the reduction in thickness of the coloring pattern or the coloring coating film caused by heating (especially post-baking) can be suppressed. The color filter produced from the coloring curable resin composition of the present invention is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements.
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