CN102998902A - Colored photosensitive resin composition - Google Patents
Colored photosensitive resin composition Download PDFInfo
- Publication number
- CN102998902A CN102998902A CN2012103470531A CN201210347053A CN102998902A CN 102998902 A CN102998902 A CN 102998902A CN 2012103470531 A CN2012103470531 A CN 2012103470531A CN 201210347053 A CN201210347053 A CN 201210347053A CN 102998902 A CN102998902 A CN 102998902A
- Authority
- CN
- China
- Prior art keywords
- methyl
- structural unit
- formula
- resin
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000011342 resin composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 239000011347 resin Substances 0.000 claims abstract description 95
- 229920005989 resin Polymers 0.000 claims abstract description 95
- 239000000049 pigment Substances 0.000 claims abstract description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 239000003086 colorant Substances 0.000 claims abstract description 23
- 239000001018 xanthene dye Substances 0.000 claims abstract description 23
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims abstract description 15
- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 95
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 54
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract 1
- -1 decyl ester Chemical class 0.000 description 132
- 239000002904 solvent Substances 0.000 description 49
- 238000000034 method Methods 0.000 description 48
- 239000000243 solution Substances 0.000 description 35
- 239000000975 dye Substances 0.000 description 33
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 22
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- 239000004094 surface-active agent Substances 0.000 description 21
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 19
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 12
- 239000000470 constituent Substances 0.000 description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012752 auxiliary agent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IWQPVKKGSBGBBS-UHFFFAOYSA-N [O]CC1CO1 Chemical compound [O]CC1CO1 IWQPVKKGSBGBBS-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229920006243 acrylic copolymer Polymers 0.000 description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 7
- 238000001259 photo etching Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- GWCJNVUIVCCXER-UHFFFAOYSA-N 2-(1-phenylprop-2-enoxymethyl)oxirane Chemical group C=1C=CC=CC=1C(C=C)OCC1CO1 GWCJNVUIVCCXER-UHFFFAOYSA-N 0.000 description 6
- 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 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229960003328 benzoyl peroxide Drugs 0.000 description 4
- 150000001721 carbon Chemical group 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
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-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
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000002921 oxetanes Chemical group 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000004646 sulfenyl group Chemical group S(*)* 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
- 229950004288 tosilate Drugs 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical class CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 3
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- REUQOSNMSWLNPD-UHFFFAOYSA-N [2-(diethylamino)phenyl]-phenylmethanone Chemical compound CCN(CC)C1=CC=CC=C1C(=O)C1=CC=CC=C1 REUQOSNMSWLNPD-UHFFFAOYSA-N 0.000 description 2
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical class CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical class COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical class CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- YNXCGLKMOXLBOD-UHFFFAOYSA-N oxolan-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CCCO1 YNXCGLKMOXLBOD-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical compound C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-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
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YEIGUXGHHKAURB-UHFFFAOYSA-N viridine Natural products O=C1C2=C3CCC(=O)C3=CC=C2C2(C)C(O)C(OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
Abstract
The invention provides a colored photosensitive resin composition comprising a colorant, resin, a polymerizable compound and a polymerization initiator. The colorant contains xanthene dye and pigments. The resin is a copolymer containing at least one structural unit selected from unsaturated carboxylic acid and unsaturated carboxylic acid anhydride groups, a structural unit derived from a monomer having a C2-C4 cyclic ether structure and ethylene unsaturated bonds, and a structural unit represented by the formula (X). In the formula (X), each Ra1 represents a hydrogen atom or a methyl group; each Ra2 represents an alkyl group of C2-C6; each p represents an integer of 0 to 5; when p is greater than 2, the plurality of Ra2 can be the same or different from each other.
Description
Technical field
The present invention relates to photosensitive composition.
Background technology
Photosensitive composition is used to make the color filter that uses in the display device such as display panels, electroluminescence panel and plasm display panel.As such photosensitive composition, known have a kind of photosensitive composition (JP2010-211198-A), and as resin, it contains methacrylic acid and acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] multipolymer of decyl ester.
When using photosensitive composition to form colored pattern, can use photoetching process, be photosensitive composition is coated substrate formation composition layer, be situated between and by photomask the said composition layer exposed, develops, obtain the method for pattern with this.Yet the photosensitive composition that proposes now when developing, exists a part of unexposed portion generation of the composition layer that is formed by this photosensitive composition to peel off, this stripping film is attached to the situation that becomes foreign matter on the colored pattern.
Summary of the invention
The present invention comprises following invention.
[1] contain the photosensitive composition of colorant, resin, polymerizable compound and polymerization initiator,
Colorant is the colorant that contains xanthene dye and pigment,
Resin is the multipolymer that contains following structural unit: derive from least a kind structural unit being selected among the group that unsaturated carboxylic acid and unsaturated carboxylic acid anhydrides consist of, derive from the monomer of cyclic ether structure with carbon number 2~4 and ethene unsaturated link structural unit, derive from the structural unit of the monomer shown in the formula (x).
[in the formula (x), R
A1Expression hydrogen atom or methyl.
R
A2The alkyl of expression carbon number 1~6.
P represents 0~5 integer.When p is 2 when above, a plurality of R
A2Can be identical or different.]
[2] [1] described photosensitive composition, the content that derives from the structural unit of monomer shown in the formula (x) be with respect to the structural unit total amount that consists of this multipolymer, more than 1 % by mole below 80 % by mole.
[3] [1] or [2] described photosensitive composition, the monomer shown in the formula (x) is vinyltoluene.
[4] by the formed color filter of the described photosensitive composition of any one of [1]~[3].
[5] display device that contains [4] described color filter.
According to photosensitive composition of the present invention, a part of unexposed portion that can suppress the composition layer that formed by this photosensitive composition produces when developing to be peeled off, and then reduces the foreign matter on the colored pattern.
Embodiment
Photosensitive composition of the present invention contains colorant (A), resin (B), polymerizable compound (C) and polymerization initiator (D),
Colorant (A) is the colorant that contains xanthene dye (A1) and pigment (A2),
Resin (B) is the resin that contains with the multipolymer of lower unit: derive from least a kind structural unit being selected among the group that unsaturated carboxylic acid and unsaturated carboxylic acid anhydrides consist of, derive from the monomer of cyclic ether structure with carbon number 2~4 and ethene unsaturated link structural unit, derive from the structural unit of the monomer shown in the formula (x).
[in the formula (x), R
A1Expression hydrogen atom or methyl.
R
A2The alkyl of expression carbon number 1~6.
P represents 0~5 integer.When p is 2 when above, a plurality of R
A2Can be identical or different.]
Preferred photosensitive composition of the present invention further contains solvent (E).
In addition, photosensitive composition of the present invention also can contain at least a kind among the group who is selected from polymerization initiation auxiliary agent (D1) and surfactant (F) formation as required.
<colorant (A) 〉
Colorant (A) contains xanthene dye (A1) and pigment (A2).Further, also can contain the dyestuff that is different from xanthene dye (A1) (below be also referred to as " dyestuff (A3) ").
Xanthene dye (A1) is the dyestuff that contains the compound that has the xanthene skeleton in the molecule.Xanthene dye (A1) can be enumerated, for example C.I. CI 45430 (record of following omission C.I. acid red, only record numbering.Other too.), 52,87,92,94,289,388, C.I. acid violet 9,30,102, C.I. alkali red 1:1 (rhodamine 6G), 2,3,4,8, C.I. alkali red 1:1 0 (rhodamine B), 11, C.I. alkaline purple 10,11,25, C.I. solvent red 218, C.I. mordant rouge 27, C.I. reactive red 36 (rose red b), sulphonyl rhodamine G, the described xanthene dye of Japanese Patent Laid-Open 2010-32999 communique and No. 4492760 described xanthene dye of communique of patent etc.Be preferably dissolved in the dyestuff of organic solvent.
Wherein, as xanthene dye (A1), preferably contain the dyestuff of compound shown in the formula (1a) (below be also referred to as " compound (1a) ").When using compound (1a), the content of the compound (1a) in the preferred xanthene dye (A1) is more than 50 quality %, more preferably more than the 70 quality %, further more than the preferred 90 quality %.Especially, as xanthene dye (A1), preferably only use compound (1a).
[in the formula (1a), R
1~R
4Represent independently of one another hydrogen atom ,-R
8The 1 valency aromatic hydrocarbyl that perhaps can have substituent carbon number 6~10.R
1And R
2Can be in key and form ring, R with the nitrogen-atoms of adjacency
3And R
4Can be in key and form ring with the nitrogen-atoms of adjacency.
R
5Expression-OH ,-SO
3 -,-SO
3H ,-SO
3 -Z
+,-CO
2H ,-CO
2 -Z
+,-CO
2R
8,-SO
3R
8Or-SO
2NR
9R
10
R
6And R
7The alkyl that represents independently of one another hydrogen atom or carbon number 1~6.
M represents 0~5 integer.When m is integer more than 2, a plurality of R
5Identical or different.
A represents 0 or 1 integer.
X represents halogen atom.
R
81 valency saturated hydrocarbyl of expression carbon number 1~20, the contained hydrogen atom of this saturated hydrocarbyl can be replaced by halogen atom.
Z
+Expression
+N (R
11)
4, Na
+Or K
+
R
9And R
10The 1 valency saturated hydrocarbyl that represents independently of one another hydrogen atom or carbon number 1~20, R
9And R
10Can be in key and form the heterocycle of 3~10 yuan of rings with the nitrogen-atoms of adjacency.
R
11Represent independently of one another 1 valency saturated hydrocarbyl of hydrogen atom, carbon number 1~20 or the aralkyl of carbon number 7~10.]
Represent R
1~R
41 valency aromatic hydrocarbyl of carbon number 6~10 can enumerate such as phenyl, tolyl, xylyl, sym-trimethyl benzene base, propyl phenyl and butylbenzene base etc.
For representing R
1~R
41 valency aromatic hydrocarbyl of carbon number 6~10, the hydrogen atom that contains in this aromatic hydrocarbyl can by halogen atom ,-R
8,-OH ,-OR
8,-SO
3 -,-SO
3H ,-SO
3 -Z
+,-CO
2H ,-CO
2R
8,-SR
8,-SO
3R
8Or-SO
2NR
9R
10Replace.Among these substituting groups, be preferably selected from-SO
3 -,-SO
3H ,-SO
3 -Z
+And-SO
2NR
9R
10Among the group who consists of at least a kind more preferably is selected from-SO
3 -Z
+And-SO
2NR
9R
10Among the group who consists of at least a kind.As this moment-SO
3 -Z
+, preferred-SO
3 -+N (R
11)
4Work as R
1~R
4During for these groups, the photosensitive composition that contains compound (1a) can form foreign matter and produce still less, and the more excellent color filter of thermotolerance.
R
1And R
2Can be in key and form ring, R with the nitrogen-atoms of adjacency
3And R
4Can be in key and form ring with the nitrogen-atoms of adjacency.The ring that contains this nitrogen-atoms can be enumerated, and is for example as follows.
Represent R
8~R
111 valency saturated hydrocarbyl of carbon number 1~20 can enumerate the straight chain shape alkyl of carbon numbers 1~20 such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, dodecyl, cetyl, eicosyl; The branched-chain alkyl of the carbon numbers 3~20 such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl; Reach the ester ring type saturated hydrocarbyl of the carbon numbers 3~20 such as cyclopropyl, cyclopentyl, cyclohexyl, suberyl, ring octyl group, three ring decyls.
-OR
8Can enumerate, for example methoxyl, ethoxy, propoxyl group, butoxy, amoxy, own oxygen base, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy and eicosane oxygen base.
-CO
2R
8Can enumerate, for example methoxycarbonyl, ethoxy carbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxy carbonyl and eicosane oxygen base carbonyl.
-SR
8Can enumerate, for example methyl mercapto, ethylmercapto group, butylthio, own sulfenyl, the last of the ten Heavenly stems sulfenyl and eicosane sulfenyl.
-SO
2R
8Can enumerate, for example methyl sulphonyl, ethylsulfonyl, butyl sulfonyl, hexyl sulfonyl, decyl sulfonyl and eicosyl sulfonyl.
-SO
3R
8Can enumerate, for example methoxyl sulfonyl, ethoxy sulfonyl, propoxyl group sulfonyl, tert-butoxy sulfonyl, own oxygen base sulfonyl and eicosane oxygen base sulfonyl.
-SO
2NR
9R
10Can enumerate, for example sulfamoyl;
N-methyl sulfamoyl, N-ethyl sulfamoyl, N-propyl group sulfamoyl, N-isopropyl sulfamoyl, N-butyl sulfamoyl, N-isobutyl sulfamoyl, N-sec-butyl sulfamoyl, N-tert-butyl group sulfamoyl, N-amyl group sulfamoyl, N-(1-ethyl propyl) sulfamoyl, N-(1, the 1-dimethyl propyl) sulfamoyl, N-(1, the 2-dimethyl propyl) sulfamoyl, N-(2, the 2-dimethyl propyl) sulfamoyl, N-(1-methyl butyl) sulfamoyl, N-(2-methyl butyl) sulfamoyl, N-(3-methyl butyl) sulfamoyl, N-cyclopentyl sulfamoyl, N-hexyl sulfamoyl, N-(1, the 3-dimethylbutyl) sulfamoyl, N-(3, the 3-dimethylbutyl) sulfamoyl, N-heptyl sulfamoyl, N-(1-methyl hexyl) sulfamoyl, N-(1,4-dimethyl amyl group) sulfamoyl, N-octyl group sulfamoyl, N-(2-ethylhexyl) sulfamoyl, N-(1, the 5-dimethyl) hexyl sulfamoyl, N-(1,1,2,2-tetramethyl butyl) N-1 such as sulfamoyl replaces sulfamoyl;
N; N-dimethylamino sulfonyl, N; N-ethyl-methyl sulfamoyl, N, N-diethyl amino sulfonyl, N, N-propyl group methyl sulfamoyl, N; N-isopropyl methyl sulfamoyl, N; N-tert-butyl group methyl sulfamoyl, N, N-butyl ethyl sulfamoyl, N, N-two (1-methyl-propyl) sulfamoyl, N; the N such as N-heptyl methyl sulfamoyl, N-2 replaces sulfamoyl etc.
In addition for representing R
9And R
101 valency saturated hydrocarbyl of carbon number 1~20, the hydrogen atom that contains in this saturated hydrocarbyl can be replaced by-OH or halogen atom, contain in this saturated hydrocarbyl-CH
2-can by-O-,-CO-,-NH-or-NR
8-replace.
R
9And R
10Can be in key and form the heterocycle of 3~10 yuan of rings with the nitrogen-atoms of adjacency.This heterocycle can be enumerated, and is for example as follows.
Represent R
6And R
7The alkyl of carbon number 1~6 can enumerate, more than cited straight chain shape alkyl and the alkyl of the carbon number 1~6 among the branched-chain alkyl.
Represent R
11The aralkyl of carbon number 7~10 can enumerate for example benzyl, phenethyl and benzene butyl.
Z
+For
+N (R
11)
4, Na
+Or K
+, preferred
+N (R
11)
4
Above-mentioned
+N (R
11)
4Preferred 4 R
11Among, have at least 2 to be 1 valency saturated hydrocarbyl of carbon number 5~20.In addition, 4 R
11Total carbon atom number be preferably 20~80, more preferably 20~60.Work as R
11During for these groups, the photosensitive composition that contains compound (1a) can form foreign matter color filter still less.
M is preferably 1~4, and more preferably 1 or 2.
As xanthene dye (A1), more preferably contain the dyestuff of compound shown in the formula (2a) (following also claim " compound (2a) ").When using compound (2a), more than the preferred 50 quality % of the content of the compound (2a) in the xanthene dye (A1), more preferably more than the 70 quality %, further more than the preferred 90 quality %.
[in the formula (2a), R
21~R
24Represent independently of one another hydrogen atom ,-R
26The 1 valency aromatic hydrocarbyl that perhaps can have substituent carbon number 6~10.R
21And R
22Can be in key and form ring, R with the nitrogen-atoms of adjacency
23And R
24Can be in key and form ring with the nitrogen-atoms of adjacency.
R
25Expression-SO
3 -,-SO
3H ,-SO
3 -Z1
+Or-SO
2NHR
26
Ml represents 0~5 integer.When ml is integer more than 2, a plurality of R
25Identical or different.
A1 represents 0 or 1 integer.
X1 represents halogen atom.
R
261 valency saturated hydrocarbyl of expression carbon number 1~20.
Z1
+Expression+N (R
27)
4, Na
+Or K
+
R
271 valency saturated hydrocarbyl or the benzyl that represents independently of one another carbon number 1~20.]
Represent R
21~R
241 valency aromatic hydrocarbyl of carbon number 6~10 can enumerate, with above-mentioned R
1~R
4The group that cited aromatic hydrocarbyl is identical.The hydrogen atom that contains in this aromatic hydrocarbyl can be by-SO
3 -,-SO
3H ,-SO
3 -Z1
+,-SO
3R
26Or-SO
2NHR
26Replace.
As R
21~R
24Combination, preferred R
21And R
23Hydrogen atom, R
22And R
241 valency aromatic hydrocarbyl of carbon number 6~10, the hydrogen atom quilt-SO that this aromatic hydrocarbyl is contained
3 -,-SO
3H ,-SO
3 -Z1
+,-SO
3R
26Or-SO
2NHR
26Replace.Further preferred combination is R
21And R
23Be hydrogen atom, R
22And R
24Be 1 valency aromatic hydrocarbyl of carbon number 6~10, the hydrogen atom quilt-SO that this aromatic hydrocarbyl is contained
3 -Z1
+Or-SO
2NHR
26Replace.
In addition, preferred R
21And R
22Be in key and form the aliphatics heterocycle with nitrogen-atoms, and R
23And R
24Be in key and form the aliphatics heterocycle with nitrogen-atoms.
Work as R
21~R
24During for these groups, the photosensitive composition that contains compound (2a) can form the more excellent color filter of thermotolerance.
Above-mentioned aliphatics heterocycle can be enumerated, and is for example as follows.
Represent R
26And R
271 valency saturated hydrocarbyl of carbon number 1~20 can enumerate, with R
8~R
11The group that cited saturated hydrocarbyl is identical.
Preferred R
21~R
24In-R
26Be hydrogen atom, methyl or ethyl independently of one another.In addition ,-SO
3R
26And-SO
2NHR
26In R
26The branched-chain alkyl of preferred carbon number 3~20, the more preferably branched-chain alkyl of carbon number 6~12, further preferred 2-ethylhexyl.Work as R
26During for these groups, the photosensitive composition that contains compound (2a) can form foreign matter generation color filter still less.
Z1
+Be
+N (R
27)
4, Na
+Or K
+, preferred
+N (R
27)
4
As above-mentioned
+N (R
27)
4, preferred 4 R
27Among have at least 2 to be 1 valency saturated hydrocarbyl of carbon number 5~20.In addition, 4 R
27Total carbon atom number preferred 20~80, more preferably 20~60.Contain R
27For can forming foreign matter, the photosensitive composition of the compound (2a) of these groups produces still less color filter.
Ml is preferred 1~4, and more preferably 1 or 2.
Compound (2a) can be enumerated, for example the compound shown in formula (1-1)~formula (1-24).In addition, in the formula, R
261 valency saturated hydrocarbyl of expression carbon number 1~20, the branched-chain alkyl of preferred carbon number 6~12, further preferred 2-ethylhexyl.Wherein, sulfonamide compounds, the quaternary ammonium salt of C.I. acid red 289, the sulfonamide compounds of C.I. acid violet 102 or the quaternary ammonium salt of C.I. acid violet 102 of preferred C.I. acid red 289.Such compound can be enumerated, for example the compound shown in formula (1-1)~formula (1-8), formula (1-11) and the formula (1-12).
In addition, xanthene dye (A1) more preferably contains the dyestuff of compound shown in the formula (3a) (below be also referred to as " compound (3a) ").When using compound (3a), more than the preferred 50 quality % of the content of the compound (3a) in the xanthene dye (A1), more preferably more than the 70 quality %, further more than the preferred 90 quality %.
[in the formula (3a), R
31And R
32The alkyl that represents independently of one another carbon number 1~4.
R
33And R
34Represent independently of one another the alkyl of carbon number 1~4, alkyl (hydrocarbon) sulfenyl of carbon number 1~4 or the alkyl sulphonyl of carbon number 1~4.
R
31And R
33Can be in key and form ring, R with nitrogen-atoms and the carbon atom of adjacency
32And R
34Can be in key and form ring with nitrogen-atoms and the carbon atom of adjacency.
P and q represent 0~5 integer independently of one another.When p is 2 when above, a plurality of R
33Can be identical or different, when q is 2 when above, a plurality of R
34Can be identical or different.]
Represent R
31, R
32, R
33And R
34The alkyl of carbon number 1~4 can enumerate methyl, ethyl, propyl group, butyl, isopropyl, isobutyl, sec-butyl, the tert-butyl group etc.
Represent R
33And R
34Alkyl (hydrocarbon) sulfenyl of carbon number 1~4 can enumerate methyl mercapto, ethylmercapto group, rosickyite base, butylthio, isopropyl sulfenyl etc.
Represent R
33And R
34The alkyl sulphonyl of carbon number 1~4 can enumerate methyl sulphonyl, ethylsulfonyl, sulfonyl propyl base, butyl sulfonyl, isopropyl sulfonyl etc.
Preferred R
31And R
32Be methyl and ethyl independently of one another.R
33And R
34Be preferably the alkyl of carbon number 1~4, more preferably methyl.
M and n are preferably 0~2 integer, and more preferably 0 or 1.
Compound (3a) can be enumerated, for example the compound shown in formula (1-25)~formula (1-31) separately.Wherein, based on the deliquescent point in organic solvent, the compound shown in the preferred formula (1-25).
Xanthene dye (A1) can use commercially available xanthene dye (for example, China and foreign countries change into " the Chugai A minol Fast Pink R-H/C " of (strain) system, " Rhodamin6G " of hilllock, field chemical industry (strain) system).In addition, also available commercially available xanthene dye synthesizes with reference to JP2010-32999-A as initial feed.
Pigment (A2) can be enumerated, and for example classifies as the compound of pigment in the Colour Index (Colour Index) (The Society of Dyers and Colourists publication).
Pigment can be enumerated, such as C.I. pigment yellow 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,125,128,137,138,139,147,148,150,153,154,166,173,194, the yellow uitramarines such as 214;
C.I. pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65,71, the orange pigment such as 73;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215,216,224,242,254,255,264, the red pigments such as 265;
C.I. pigment blue 15,15:3,15:4,15:6, the blue pigments such as 60; C.I. pigment violet 1,19,23,29,32,36, the violet pigments such as 38;
C.I. pigment Green 7,36, the viridine greens such as 58;
C.I. bistre 23, the brown pigments such as 25;
C.I. pigment black 1, the black pigments such as 7 etc.
These pigment can separately or mix more than 2 kinds and use.
As pigment, preferred C.I. pigment blue 15,15:3,15:4,15:6, the blue pigments such as 60 and C.I. pigment violet 1,19,23,29,32,36, the violet pigments such as 38, more preferably C.I. pigment blue 15: 3,15:6 and C.I. pigment Violet 23, further preferred C.I. pigment blue 15: 6.By containing above-mentioned pigment, see through spectrum and be easy to optimization, the photostability of color filter and chemical proofing are good.
Pigment (A2) can be as required; implement rosin and process, use the pigment derivative that imported acidic groups or basic group etc. to carry out surface treatment, by macromolecular compound etc. surface of pigments carried out grafting and process, carry out micronize by sulfuric acid micronize method etc. and process, perhaps implement to remove impurity, remove the processing of ionic impurity etc. by ion exchange process etc. by the cleaning treatment of organic solvent or water etc.
Pigment (A2) preferable particle size homogeneous.Carry out dispersion treatment by making it to contain pigment dispersing agent, can obtain pigment and be scattered in dispersible pigment dispersion in the solution with the homogeneous state.
Above-mentioned pigment dispersing agent can be enumerated, pigment dispersing agents such as kation system, negative ion system, nonionic system, both sexes, polyester system, polyamine system, acrylic acid series etc.These pigment dispersing agents can be used singly or two or more kinds in combination.Pigment dispersing agent can be enumerated with trade name, KP (SHIN-ETSU HANTOTAI's chemical industry (strain) system), Off ロ one レ Application (common prosperity society chemistry (strain) system), ソ Le ス パ one ス (ゼ ネ カ (strain) system), EFKA (CIBA society system), ア ジ ス パ one (monosodium glutamate Off ア イ Application テ Network ノ (strain) system), Disperbyk (PVC Star Network ヶ ミ one society's system) etc.
When using pigment dispersing agent, its use amount is preferably below the above 100 quality % of 1 quality % with respect to pigment (A2), more preferably below the above 50 quality % of 5 quality %.If the use amount of pigment dispersing agent in above-mentioned scope, then has the tendency of the dispersible pigment dispersion that obtains the homogeneous disperse state.
Dyestuff (A3) is not particularly limited, and can use known dyestuff, has enumerated such as solvent dye, acid dyes, direct dyes, mordant dye etc., preferably is dissolvable in water the dyestuff of organic solvent.
Dyestuff (A3) can be enumerated, and for example classifies as the compound of dyestuff in the Colour Index (The Society of Dyers and Colourists publication), or the known dyestuff of record in the dyeing handbook (look dyes society).In addition, can enumerate azo dyes, cyanine dye, triphenhlmethane dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dyestuff, quinoneimine dye, methine type dye, azo methine type dye, squaraine dye, acridine dye, styryl dye, coumarine dye, quinoline dye, nitro dye etc. according to chemical constitution.Wherein, preferred organic solvent-soluble dye.
Can enumerate particularly C.I. solvent yellow 4,14,15,23,24,38,62,63,68,82,94,98,99,117,162,163,167,189;
C.I. solvent red 45,49,111,125,130,143,145,146,150,151,155,168,169,172,175,181,207,222,227,230,245,247;
C.I. solvent orange 2,7,11,15,26,56,77,86;
C.I. solvent violet 11,13,14,26,31,36,37,38,45,47,48,51,59,60;
C.I. solvent blue 4,5,14,18,35,36,37,45,58,59,59:1,63,67,68,69,70,78,79,83,90,94,97,98,100,101,102,104,105,111,112,122,128,132,136,139;
C.I. the C.I. solvent dye such as solvent green 1,3,4,5,7,28,29,32,33,34,35,
C.I. Indian 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. azogeramine, 4,8,14,17,18,26,27,29,31,33,34,35,37,40,42,44,57,66,73,76,80,88,97,103,106,111,114,129,133,134,138,143,145,150,151,155,158,160,172,176,182,183,195,198,206,211,215,216,217,227,228,249,252,257,258,260,261,266,268,270,274,277,280,281,308,312,315,316,339,341,345,346,349,382,383,394,401,412,417,418,422,426;
C.I. acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,169,173;
C.I. acid violet 6B, 7,17,19,34;
C.I. Blue VRS, 7,9,15,18,22,23,25,27,29,40,41,42,43,45,51,59,60,62,70,72,74,78,80,82,83,86,87,90,92,93,100,102,103,104,112,113,117,120,126,127,129,130,131,138,142,147,150,151,154,158,161,166,167,168,170,171,184,187,192,199,210,229,234,236,242,243,256,259,267,285,296,315,324:1,335;
C.I. acid green 1,3,5,9,16,25,27,28,41,50,58,63,65,80,104,105,106, the C.I. acid dyess such as 109,
C.I. directly yellow 2,33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98,102,108,109,129,136,138,141;
C.I. directly red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177,179,181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250;
C.I. direct orange 26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107;
C.I. directly purple 47,52,54,59,60,65,66,79,80,81,82,84,89,90,93,95,96,103,104;
C.I. directly blue 1,2,6,8,15,22,25,40,41,57,71,76,78,80,81,84,85,86,90,93,94,95,97,98,99,100,101,106,107,108,109,113,114,115,117,119,120,137,149,150,153,155,156,158,159,160,161,162,163,164,165,166,167,168,170,171,172,173,188,189,190,192,193,194,195,196,198,199,200,201,202,203,207,209,210,212,213,214,222,225,226,228,229,236,237,238,242,243,244,245,246,247,248,249,250,251,252,256,257,259,260,268,274,275,293;
C.I. direct green 25,27,31,32,34,37,63,65,66,67,68,69,72,77,79, the C.I. direct dyess such as 82,
C.I. disperse yellow 51,54,76;
C.I. disperse violet 26,27;
C.I. disperse blue 1,14,56,60 etc. is disperseed dyestuff;
C.I. alkali blue 1,3,5,7,9,19,22,24,25,26,28,29,40,41,47,54,58,59,64,65,66,67,68;
C.I. Viride Nitens 1; Deng the C.I. basic-dyeable fibre
C.I. reactive yellow 2,76,116;
C.I. reactive orange 16; Deng the C.I. reactive dye
C.I. mordant yellow 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65;
C.I. mordant rouge 1,2,3,4,9,11,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,41,43,45,46,48,53,56,63,71,74,85,86,88,90,94,95;
C.I. mordant dyeing orange 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47,48;
C.I. mordant dyeing purple 1,2,4,5,7,14,22,24,30,31,32,37,40,41,44,45,47,48,53,58;
C.I. mordant dyeing indigo plant 1,2,3,7,8,9,12,13,15,16,19,20,21,22,26,30,31,39,40,41,43,44,49,53,61,74,77,83,84;
C.I. viridon 1,3,4,5,10,15,26,29,33,34,35,41,43, the C.I. mordant dyes such as 53
C.I. vat green 1 reducing dye such as C.I. such as grade etc.
These dyestuffs are suitably selected to get final product according to the spectrophotometric spectra of desired color filter.These dyestuffs can use separately or also use more than 2 kinds.
When colorant (A) contained dyestuff (A3), the content of dyestuff (A3) was with respect to the total amount of colorant (A), preferred 1~90 quality %, more preferably 1~50 quality %.
When colorant (A) is made of xanthene dye (A1) and pigment (A2), the content ratio of dyestuff (A1) and pigment (A2) is in quality criteria, preferred 1: 99~90: 10, more preferably 2: 98~70: 30, further preferred 2: 98~50: 50.By making it to contain such ratio, see through spectrum and be easy to optimization, the color filter of acquisition has the more excellent tendency of contrast, brightness, thermotolerance and chemical proofing.
The content of colorant (A) is with respect to the total amount of solid constituent, preferred 5~60 quality %, more preferably 8~50 quality %, further preferred 10~40 quality %.When the content of colorant (A) was in above-mentioned scope, the colour saturation when making color filter was abundant, and can contain in the composition must amount resin (B) or polymerizable compound (C), so can form the enough color filters of physical strength.
Herein, " total amount of solid constituent " in this instructions refers to the amount from the total amount of photosensitive composition behind the desolventizing content.The total amount of solid constituent and with respect to its content of each composition can be measured by known analysis means such as, liquid phase chromatography, vapor-phase chromatography.
<resin (B) 〉
Resin (B) contains multipolymer with following structural unit (below be also referred to as " multipolymer (B1) "): the structural unit that derives from least a kind of being selected among the group that unsaturated carboxylic acid and unsaturated carboxylic acid anhydrides consist of (below be also referred to as " (a) "), derive from the structural unit of the monomer (below be also referred to as " (b) ") of cyclic ether structure with carbon number 2~4 and ethene unsaturated link, derive from the structural unit of monomer shown in the formula (x) (below be also referred to as " (x) ").
[in the formula (x), R
A1Expression hydrogen atom or methyl.
R
A2The alkyl of expression carbon number 1~6.
P represents 0~5 integer.When p is 2 when above, a plurality of R
A2Can be identical or different.]
Based on the point of the polymerism of monomer, R
A1Be preferably hydrogen atom.
In the formula (x), represent R
A2The alkyl of carbon number 1~6 can enumerate methyl, ethyl, propyl group, butyl, amyl group, hexyl, isopropyl, isobutyl, isopentyl, neopentyl etc.
R
A2Be preferably the alkyl of carbon number 1~3, more preferably methyl.
The integer of p preferred 0~2, more preferably 1.
(x) can enumerate, such as styrene, adjacent vinyltoluene, a vinyltoluene, to vinyltoluene, α-methyl styrene, ethyl styrene etc.Wherein, preferred adjacent vinyltoluene, a vinyltoluene reach to vinyltoluene, more preferably to vinyltoluene.When (x) is vinyltoluene because the film that has been coated with photosensitive composition has the excellent dissolubility in organic solvent, so have for example can be suppressed at, the pipe arrangement of apparatus for coating inside or the tendency of separating out of the section that spues.
(a) can enumerate particularly, such as acrylic acid, methacrylic acid, butenoic acid, neighbour,, to unsaturated monocarboxylic acid classes such as vinyl benzoic acids;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-ethene phthalandione, 4-ethene phthalandione, 3,4,5,6-tetrahydrochysene phthalandione, 1,2,3, the unsaturated dicarboxylic acid classes such as 6-tetrahydrochysene phthalandione, dimethyl tetrahydro phthalandione, 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norborene-2,3-dicarboxylic acid, 5-carboxyl dicyclo [2.2.1]-2-heptene, 5,6-dicarboxyl dicyclo [2.2.1]-2-heptene, 5-carboxyl-5-methyl bicycle [2.2.1]-2-heptene, 5-carboxyl-5-ethyl dicyclo [2.2.1]-2-heptene, 5-carboxyl-6-methyl bicycle [2.2.1]-2-heptene, 5-carboxyl-6-ethyl dicyclo [2.2.1]-2-heptene etc. have the dicyclo unsaturated compound class of carboxyl;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-ethene anhydride phthalic acid, 4-ethene anhydride phthalic acid, 3,4,5,6-tetrahydrochysene anhydride phthalic acid, 1,2,3,6-tetrahydrochysene anhydride phthalic acid, dimethyl tetrahydro anhydride phthalic acid, 5,6-dicarboxyl dicyclo [the 2.2.1]-unsaturated dicarboxylic acid class acid anhydrides such as 2-heptene acid anhydrides (carbic anhydride);
Unsaturated list ((methyl) acryloyloxyalkyl) the ester class of the above polybasic carboxylic acids of divalent such as mono succinate (2-(methyl) acrylyl oxy-ethyl), phthalandione list (2-(methyl) acrylyl oxy-ethyl);
α-unsaturated esters of acrylic acid (hydroxymethyl) acrylic compounds, that in a part, contain hydroxyl and carboxyl etc.
Wherein, based on the point of copolyreaction or the deliquescent point in aqueous alkali, preferred acrylic acid, methacrylic acid and maleic anhydride etc.
In addition, in this instructions, " (methyl) acryloyl group " expression is selected from least a kind among the group that acryloyl group and methacryl consist of.The narration that " (methyl) acrylic acid " reaches " (methyl) acrylate " etc. also has same meaning.
(b) refer to have the polymerizable compound of the cyclic ether structure of carbon number 2~4 for example (for example, be selected among the group that oxirane ring, oxetanes ring and tetrahydrofuran ring consist of at least a kind) and ethene unsaturated link.(b) be preferably the monomer of cyclic ether with carbon number 2~4 and (methyl) acryloxy.
(b) can enumerate, such as the monomer (b1) with epoxy ethyl and ethene unsaturated link (below be also referred to as " (b1) "), have oxa-cyclobutyl and ethene unsaturated link monomer (b2) (below be also referred to as " (b2) "), have monomer (b3) (below be also referred to as " (b3) ") of tetrahydrofuran base and ethene unsaturated link etc.
(b1) can enumerate, for example have the monomer (b1-1) of the structure behind straight chain shape or the chain unsaturated fatty hydrocarbons epoxidation (below be also referred to as " (b1-1) "), have the monomer (b1-2) of the structure behind the unsaturated lipid ring type hydrocarbon epoxidation (below be also referred to as " (b1-2) ").
(b1-1) can enumerate, (methyl) glycidyl acrylate, (methyl) acrylic acid Beta-methyl ethylene oxidic ester, (methyl) propenoic acid beta-ethyl ethylene oxidic ester, the glycidyl vinyl ether, adjacent vinyl benzyl glycidyl ether, between the vinyl benzyl glycidyl ether, to the vinyl benzyl glycidyl ether, the adjacent vinyl benzyl glycidyl ether of Alpha-Methyl, vinyl benzyl glycidyl ether between Alpha-Methyl, Alpha-Methyl is to the vinyl benzyl glycidyl ether, 2,3-two (glycidyl oxygen ylmethyl) styrene, 2,4-two (glycidyl oxygen ylmethyl) styrene, 2,5-two (glycidyl oxygen ylmethyl) styrene, 2,6-two (glycidyl oxygen ylmethyl) styrene, 2,3,4-three (glycidyl oxygen ylmethyl) styrene, 2,3,5-three (glycidyl oxygen ylmethyl) styrene, 2,3,6-three (glycidyl oxygen ylmethyl) styrene, 3,4,5-three (glycidyl oxygen ylmethyl) styrene, 2,4,6-three (glycidyl oxygen ylmethyl) styrene etc.
(b1-2) can enumerate, an oxyethylene group cyclohexene, 1, (for example, セ ロ キ サ イ De 2000 for 2-epoxy-4-vinyl cyclohexane; ダ イ セ Le chemical industry (strain) system), (methyl) acrylic acid 3,4-epoxycyclohexyl methyl ester (for example, サ イ Network ロ マ one A400; ダ イ セ Le chemical industry (strain) system), (methyl) acrylic acid 3,4-epoxycyclohexyl methyl ester (for example, サ イ Network ロ マ one M100; ダ イ セ Le chemical industry (strain) system), the compound shown in the formula (I), the compound shown in the formula (II) etc.
[in formula (I) and the formula (II), R
B1And R
B2The alkyl of expression hydrogen atom or carbon number 1~4, the contained hydrogen atom of this alkyl can be replaced by hydroxyl.
X
B1And X
B2The expression singly-bound ,-R
B3-, *-R
B3-O-, *-R
B3-S-or *-R
B3-NH-.
R
B3The alkylidene of expression carbon number 1~6.
* represent the bonding position with O.]
The alkyl of carbon number 1~4 can be enumerated, methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group etc.
Alkyl after hydrogen atom is replaced by hydroxyl can be enumerated, methylol, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxyl-1-Methylethyl, 2-hydroxyl-1-Methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl etc.
As R
B1And R
B2, preferably enumerate hydrogen atom, methyl, methylol, 1-hydroxyethyl and 2-hydroxyethyl, more preferably hydrogen atom and methyl.
Alkylidene can be enumerated, methylene, ethylidene, 1,2-propylidene, 1,3-propylidene, Isosorbide-5-Nitrae-butylidene, 1,5-pentylidene, 1,6-hexylidene etc.
As X
B1And X
B2, preferably enumerate singly-bound, methylene, ethylidene, *-CH
2-O-and *-CH
2CH
2-O-, more preferably singly-bound, *-CH
2CH
2-O-(* represents the bonding position with O).
Compound shown in the formula (I) can be enumerated, formula (I-1)~formula (I-15) arbitrarily shown in compound etc.Wherein, preferred formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) and formula (I-11)~formula (I-15) arbitrarily shown in compound, more preferably formula (I-1), formula (I-7), formula (I-9) and formula (I-15) arbitrarily shown in compound.
Compound shown in the formula (II) can be enumerated, formula (II-1)~formula (II-15) arbitrarily shown in compound etc.Wherein, preferred formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) and formula (II-11)~formula (II-15) arbitrarily shown in compound, more preferably formula (II-1), formula (II-7), formula (II-9) and formula (II-15) arbitrarily shown in compound.
Compound shown in compound shown in the formula (I) and the formula (II) can be distinguished separately use, also can mix with arbitrary ratio and use.When mix using, the compound shown in the compound shown in the formula (I) and the formula (II) contain ratio in molar basis, preferred 5: 95~95: 5, more preferably 10: 90~90: 10, further preferred 20: 80~80: 20.
As the monomer (b2) with oxa-cyclobutyl and ethene unsaturated link, more preferably has the monomer of oxa-cyclobutyl and (methyl) acryloxy.(b2) can enumerate 3-methyl-3-methacryloxy methyl oxetanes, 3-methyl-3-acryloyl-oxy ylmethyl oxetanes, 3-ethyl-3-methacryloxy methyl oxetanes, 3-ethyl-3-acryloyl-oxy ylmethyl oxetanes, 3-methyl-3-methacryloxyethyl oxetanes, 3-methyl-3-acryloxy Ethyloxetane, 3-ethyl-3-methacryloxyethyl oxetanes, 3-ethyl-3-acryloxy Ethyloxetane etc.
As the monomer (b3) with tetrahydrofuran base and ethene unsaturated link, more preferably has the monomer of tetrahydrofuran base and (methyl) acryloxy.(b3) can enumerate particularly acrylic acid tetrahydro furfuryl ester (such as, PVC ス コ one ト V#150, Osaka organic chemistry industry (strain) system) and methacrylic acid tetrahydro furfuryl ester etc.
As (b), the point based on the reliability of the thermotolerance that can further improve the color filter of acquisition, chemical proofing etc. is preferably (b1).Further, based on the point of the excellent storage stability of photosensitive composition, more preferably (b1-2).
Further, multipolymer (B1) also can have derive from be different from (a), (b) and (x) and can with the structural unit of the monomer of their copolymerization (below be also referred to as " (c) ").
(c) can enumerate (methyl) esters of acrylic acids such as (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-butyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) allyl acrylate, (methyl) acrylic acid alkynes propyl ester;
(methyl) acrylic acid 2-hydroxyethyl ester, (methyl) acrylic acid 2-hydroxy-propyl ester etc. contain (methyl) esters of acrylic acid of hydroxyl;
The dicarboxylic diesters such as diethyl maleate, DEF, diethyl itaconate;
Dicyclo [2.2.1]-2-heptene, 5-methyl bicycle [2.2.1]-2-heptene, 5-ethyl dicyclo [2.2.1]-2-heptene, 5-hydroxyl dicyclo [2.2.1]-2-heptene, 5-hydroxymethyl dicyclo [2.2.1]-2-heptene, 5-(2 '-hydroxyethyl) dicyclo [2.2.1]-2-heptene, 5-methoxyl dicyclo [2.2.1]-2-heptene, 5-ethoxy dicyclo [2.2.1]-2-heptene, 5,6-dihydroxy dicyclo [2.2.1]-2-heptene, 5,6-two (hydroxymethyl) dicyclo [2.2.1]-2-heptene, 5,6-two (2 '-hydroxyethyl) dicyclo [2.2.1]-2-heptene, 5,6-dimethoxy dicyclo [2.2.1]-2-heptene, 5,6-diethoxy dicyclo [2.2.1]-2-heptene, 5-hydroxy-5-methyl base dicyclo [2.2.1]-2-heptene, 5-hydroxyl-5-ethyl dicyclo [2.2.1]-2-heptene, 5-hydroxymethyl-5-methyl bicycle [2.2.1]-2-heptene, 5-tert-butoxycarbonyl dicyclo [2.2.1]-2-heptene, 5-cyclohexyl oxygen base carbonyl dicyclo [2.2.1]-2-heptene, 5-phenyloxycarbonyl dicyclo [2.2.1]-2-heptene, 5,6-two (tert-butoxycarbonyl) dicyclo [2.2.1]-2-heptene, 5,6-two (cyclohexyl oxygen base carbonyl) dicyclo [the 2.2.1]-dicyclo unsaturated compound classes such as 2-heptene;
The dicarbapentaborane imide derivative classes such as N-phenylmaleimide, N-N-cyclohexylmaleimide, N-benzyl maleimide, N-succinimido-3-maleimide benzoic ether, N-succinimido-4-maleimide butyric ester, N-succinimido-6-maleimide capronate, N-succinimido-3-maleimide propionic ester and N-(9-acridinyl) maleimide;
To methoxy styrene, vinyl cyanide, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, Methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene etc.
Wherein, based on copolyreaction and stable on heating point, preferred N-phenylmaleimide, N-N-cyclohexylmaleimide, N-benzyl maleimide and dicyclo [2.2.1]-2-heptene.
When multipolymer (B1) be origin come from the structural unit of (x), when deriving from the structural unit of (a) and deriving from the multipolymer that the structural unit of (b) consists of, the structural unit in each source contain ratio with respect to the structural unit total amount that consists of this multipolymer, be preferably following value:
Derive from the structural unit of (x): 1~80 % by mole
Derive from the structural unit of (a): 2~45 % by mole
Derive from the structural unit of (b): 2~95 % by mole
More preferably
Derive from the structural unit of (x): 1~65 % by mole
Derive from the structural unit of (a): 5~40 % by mole
Derive from the structural unit of (b): 5~80 % by mole.
When the ratio of each structural unit is in above-mentioned scope, in the composition layer that is formed by photosensitive composition, because the unexposed portion can suppress to develop the time is peeled off, produce the tendency that becomes still less so have foreign matter.
When multipolymer (B1) be origin come from (x) structural unit, derive from the structural unit of (a), when deriving from the structural unit of (b) and deriving from the multipolymer that the structural unit of (c) consists of, the structural unit in each source contain ratio with respect to the structural unit total amount that consists of this multipolymer, be preferably following value:
Derive from the structural unit of (x): 1~80 % by mole
Derive from the structural unit of (a): 2~45 % by mole
Derive from the structural unit of (b): 2~95 % by mole
Derive from the structural unit of (c): 2~80 % by mole
More preferably
Derive from the structural unit of (x): 1~65 % by mole
Derive from the structural unit of (a): 5~40 % by mole
Derive from the structural unit of (b): 5~80 % by mole
Derive from the structural unit of (c): 2~65 % by mole.
When the ratio of each structural unit is in above-mentioned scope, in the composition layer that is formed by photosensitive composition, because the unexposed portion can suppress to develop the time is peeled off, produce the tendency that tails off so have foreign matter.
As multipolymer (B1), be preferably structural unit that origin comes from (x), derive from the structural unit of (a) and derive from the multipolymer that the structural unit of (b) consists of.
Multipolymer (B1) but the citing document put down in writing in the method for record and the document in reference example such as the document " experimental method of Polymer Synthesizing " (the grand row work publishing house in large Tianjin (strain) chemistry is with the distribution on March 1st, 1972 of the 1st edition the 1st brush of people) make.
Particularly, can enumerate (x), (a) of ormal weight, (b) and as required (c), polymerization initiator and solvent etc. is packed in the reaction vessel, by for example by the nitrogen replace oxygen, make the deoxidation environment, the method that when stirring, heats and be incubated.In addition, polymerization initiator as used herein and solvent etc. are not particularly limited, and can use normally used compound in this field.For example, as polymerization initiator, can enumerate azo-compound (2,2 '-azoisobutyronitrile, 2,2 '-azo two (2,4-methyl pentane nitrile) etc.) or organic peroxide (benzoyl peroxide etc.), as solvent, get final product so long as can dissolve each monomer, can enumerate solvent described later (E) as the solvent of photosensitive composition etc.
In addition, the multipolymer for obtaining can directly use reacted solution, also can use the solution after concentrated or the dilution, also can use the solid (powder) by method taking-ups such as precipitations again.Especially, the solvent during as its polymerization by using solvent described later (E), can directly use reacted solution, and then simplifies manufacturing process.
The polystyrene conversion weight-average molecular weight of multipolymer (B1) is preferred 3,000~100,000, and more preferably 5,000~50,000, further preferred 5,000~30,000.When molecular weight was in above-mentioned scope, the hardness with color filter improved, residual film ratio is high, the favorable solubility for developer solution of unexposed portion, the tendency that the exploring degree is further enhanced.
The molecular weight distribution of multipolymer (B1) [weight-average molecular weight (Mw)/number-average molecular weight (Mn)] is preferred 1.1~6, and more preferably 1.2~4.
Preferred 50~the 170mg-KOH/g of acid number of multipolymer (B1), more preferably 60~150mg-KOH/g, further preferred 70~135mg-KOH/g.Acid number herein be as in and the amount (mg) of the required potassium hydroxide of 1g resin measure and value, can try to achieve by for example carrying out titration with potassium hydroxide aqueous solution.
Resin (B) also can contain the resin that is different from multipolymer (B1) (below be also referred to as " resin (B2) ").Resin (B2) is though be not particularly limited the preferred bases soluble resin.Resin (B2) can be enumerated, following resin [K1]~[K6] etc.
Resin [K1]: (a) with (b) multipolymer;
Resin [K2]: (a), (b) and (c) multipolymer;
Resin [K3]: (a) with can and be different from (a) and the multipolymer of (b) monomer (below be also referred to as " (c ') ") with (a) copolymerization;
Resin [K4]: (a) with the multipolymer of (c ') again with (b) reaction resin;
Resin [K5]: (b) with the multipolymer of (c ') again with (a) reaction resin;
Resin [K6]: (b) with the multipolymer of (c ') again with (a) reaction, further with the carboxylic acid anhydrides reaction resin.
Herein, (c ') can enumerate above-mentioned (x) and (c) in illustrative monomer.
In the resin [K1], the ratio of the structural unit in each source is preferably with respect to all structural units that consist of resin [K1]
Derive from the structural unit of (a): 2~60 % by mole
Derive from the structural unit of (b): 40~98 % by mole
More preferably
Derive from the structural unit of (a): 10~50 % by mole
Derive from the structural unit of (b): 50~90 % by mole.
When the ratio of the structural unit of resin [K1] is in above-mentioned scope, has the tendency of solvent resistance excellence of colored pattern of storage stability, the development when forming colored pattern and the acquisition of photosensitive composition.
Resin [K1] can be made by the method identical with the method for for example putting down in writing as the manufacture method of multipolymer (B1).
In the resin [K2], the ratio of the structural unit in each source is preferably in all structural units that consist of resin [K2]
Derive from the structural unit of (a): 2~45 % by mole
Derive from the structural unit of (b): 2~95 % by mole
Derive from the structural unit of (c): 1~65 % by mole
More preferably
Derive from the structural unit of (a): 5~40 % by mole
Derive from the structural unit of (b): 5~80 % by mole
Derive from the structural unit of (c): 5~60 % by mole.
When the ratio of the structural unit of resin [K2] is in above-mentioned scope, has the tendency of solvent resistance, thermotolerance and physical strength excellence of colored pattern of storage stability, the development when forming colored pattern and the acquisition of photosensitive composition.
Resin [K2] can be made by the method identical with the method for for example putting down in writing as the manufacture method of multipolymer (B1).
In the resin [K3], the ratio of the structural unit in each source is preferably in all structural units that consist of resin [K3]
Derive from the structural unit of (a): 2~60 % by mole
Derive from the structural unit of (c '): 40~98 % by mole
More preferably
Derive from the structural unit of (a): 10~50 % by mole
Derive from the structural unit of (c '): 50~90 % by mole.
Resin [K3] can be made by the method identical with the method for for example putting down in writing as the manufacture method of multipolymer (B1).
Resin [K4] can be by obtaining the multipolymer of (a) and (c '), and the cyclic ether of the carbon number 2~4 that (b) have is made with the carboxylic acid and/or the carboxylic acid anhydrides addition that (a) have.
At first, by the multipolymer of the method manufacturing (a) identical with the method for putting down in writing as the manufacture method of multipolymer (B1) with (c ').At this moment, preferably the cited ratio of the ratio of the structural unit in each source and resin [K3] is identical.
Then, make the part reaction of cyclic ether and the carboxylic acid that derives from (a) in the above-mentioned multipolymer and/or the carboxylic acid anhydrides of the carbon number 2~4 that (b) have.
After the multipolymer of making (a) and (c '), and then environmental gas in the flask is replaced into air by nitrogen, the catalysts (such as three (dimethylaminomethyl) phenol etc.) of (b), carboxylic acid or carboxylic acid anhydrides and cyclic ether and polymerization inhibitor (such as p-dihydroxy-benzene etc.) etc. are joined in the flask, by for example 60~130 ℃ of lower reactions 1~10 hour, can make resin [K4].
(b) use amount is with respect to 100 moles (a), and preferred 5~80 moles, more preferably 10~75 moles.By in this scope, has the tendency that the balance of solvent resistance, thermotolerance, physical strength and sensitivity of colored pattern of storage stability, the development when forming colored pattern and the acquisition of photosensitive composition improves.Reactive high, unreacted (b) based on cyclic ether are difficult for remaining point, employed (b) preferred (b1) in the resin [K4], further preferred (b1-1).
The use amount of above-mentioned catalysts is with respect to total amount 100 mass parts of (a), (b) and (c '), preferred 0.001~5 mass parts.The use amount of above-mentioned polymerization inhibitor is with respect to total amount 100 mass parts of (a), (b) and (c '), preferred 0.001~5 mass parts.
The reaction conditionss such as loading method, temperature of reaction and time can be considered the thermal value that manufacturing equipment or polymerization produce etc., suitably adjust.In addition, same polymerizing condition can be considered the thermal value of manufacturing equipment or polymerization generation etc., suitably adjusts loading method or temperature of reaction.
As the phase one of making resin [K5], can take the method identical with the manufacture method of multipolymer (B1), obtain the multipolymer of (b) and (c ').The same, the multipolymer of acquisition can directly use reacted solution, also can use the solution after concentrated or the dilution, also can use the solid (powder) by method taking-ups such as precipitations again.
Derive from the ratio of the structural unit of (b) and (c '), with respect to the total mole number of all structural units that consist of above-mentioned multipolymer, preferably in following scope.
Derive from the structural unit of (b): 5~95 % by mole
Derive from the structural unit of (c '): 5~95 % by mole
More preferably
Derive from the structural unit of (b): 10~90 % by mole
Derive from the structural unit of (c '): 10~90 % by mole.
Further, under the condition identical with the manufacture method of resin [K4], by carboxylic acid or the carboxylic acid anhydrides that (a) had, the cyclic ether reaction that derives from (b) with the multipolymer of (b) and (c ') has can obtain resin [K5] thus.
With the use amount of (a) of above-mentioned copolymer reaction, with respect to (b) 100 moles, preferred 5~80 moles.Reactive high, unreacted (b) based on cyclic ether are difficult for remaining point, employed (b) preferred (b1) in the resin [K5], further preferred (b1-1).
Resin [K6] is the resin that resin [K5] further gets with the carboxylic acid anhydrides reaction.Make carboxylic acid anhydrides with the hydroxyl reaction that produces via the reaction of cyclic ether and carboxylic acid or carboxylic acid anhydrides.
Carboxylic acid anhydrides can be enumerated, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-ethene anhydride phthalic acid, 4-ethene anhydride phthalic acid, 3,4,5,6-tetrahydrochysene anhydride phthalic acid, 1,2,3,6-tetrahydrochysene anhydride phthalic acid, dimethyl tetrahydro anhydride phthalic acid, 5,6-dicarboxyl dicyclo [2.2.1]-2-heptene acid anhydrides (carbic anhydride) etc.The use amount of carboxylic acid anhydrides is with respect to 1 mole of the use amount of (a), preferred 0.5~1 mole.
As resin (B2), can enumerate particularly (methyl) acrylic acid 3,4-epoxycyclohexyl methyl ester/(methyl) acrylic copolymer, acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] decyl ester/resins [K1] such as (methyl) acrylic copolymer; (methyl) glycidyl acrylate/(methyl) benzyl acrylate/(methyl) acrylic copolymer, acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] decyl ester/(methyl) acrylic acid/N-N-cyclohexylmaleimide multipolymer, 3-methyl-3-(methyl) acryloyl-oxy ylmethyl oxetanes/(methyl) acrylic acid/resins [K2] such as N-N-cyclohexylmaleimide multipolymer; (methyl) benzyl acrylate/(methyl) acrylic copolymer, the styrene/resins [K3] such as (methyl) acrylic copolymer; (methyl) benzyl acrylate/(methyl) acrylic copolymer and (methyl) glycidyl acrylate addition and resin, (methyl) acrylic acid three encircles decyl ester/styrene/(methyl) acrylic copolymers with (methyl) glycidyl acrylate addition and the resin that gets, (methyl) acrylic acid three encircles decyl ester/(methyl) benzyl acrylate/(methyl) acrylic copolymers with (methyl) glycidyl acrylate addition and the resins such as resin [K4] that get; The multipolymer of (methyl) acrylic acid three ring decyl ester/(methyl) glycidyl acrylates with the reaction of (methyl) acrylic acid the multipolymer of resin, (methyl) acrylic acid three ring decyl ester/styrene/(methyl) glycidyl acrylates with the reaction of (methyl) acrylic acid the resins such as resin [K5]; The multipolymer of (methyl) acrylic acid three ring decyl ester/(methyl) glycidyl acrylates with the reaction of (methyl) acrylic acid resin further with the reaction of tetrahydrochysene anhydride phthalic acid resins such as resin [K6] etc.
These resins can use separately or also use more than 2 kinds.
Wherein, resin (B2) is preferably resin [K1], resin [K2] and resin [K3].
The polystyrene conversion weight-average molecular weight of resin (B2) is preferred 3,000~100,000, and more preferably 5,000~50,000, further preferred 5,000~30,000.When molecular weight is in above-mentioned scope, the tendency that the hardness with color filter improves, residual film ratio is high, the favorable solubility for developer solution of unexposed portion, exploring degree improve.
The molecular weight distribution of resin (B2) [weight-average molecular weight (Mw)/number-average molecular weight (Mn)] is preferred 1.1~6, and more preferably 1.2~4.
Preferred 50~the 170mg-KOH/g of acid number of resin (B2), more preferably 60~150, further preferred 70~135mg-KOH/g.
Resin (B) can only be multipolymer (B1), but when containing resin (B2), and its content is with respect to the total amount of resin (B), preferred 1~95 quality %, more preferably 5~90 quality %.
The content of resin (B) is with respect to the total amount of solid constituent, preferred 7~65 quality %, more preferably 13~60 quality %, further preferred 17~55 quality %.When the content of resin (B2) is in above-mentioned scope, have the exploring degree of colored pattern and the tendency that residual film ratio improves.
<polymerizable compound (C) 〉
Polymerizable compound (C) is can be by living radical and/or the sour compound that carries out polymerization that is produced by heat or polymerization initiator (D), such as enumerating compound with polymerism ethene unsaturated link etc., preferred (methyl) acrylate compounds.
Wherein, polymerizable compound (C) is preferably the polymerizable compound with 3 above ethene unsaturated links.Such polymerizable compound can be enumerated, for example trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, dipentaerythritol six (methyl) acrylate, tripentaerythritol eight (methyl) acrylate, tripentaerythritol seven (methyl) acrylate, the four seasons penta tetrol ten (methyl) acrylate, the four seasons penta tetrol nine (methyl) acrylate, three (2-(methyl) acrylyl oxy-ethyl) isocyanuric acid ester, glycol-modified pentaerythrite four (methyl) acrylate, glycol-modified dipentaerythritol six (methyl) acrylate, propylene glycol modified pentaerythrite four (methyl) acrylate, propylene glycol modified dipentaerythritol six (methyl) acrylate, caprolactone modification pentaerythrite four (methyl) acrylate, caprolactone modification dipentaerythritol six (methyl) acrylate etc.Optical polymerism compound (C) can be used singly or two or more kinds in combination.
Wherein, preferred dipentaerythritol five (methyl) acrylate and dipentaerythritol six (methyl) acrylate.
The weight-average molecular weight of polymerizable compound (C) is preferred more than 150 below 2,900, and more preferably 250~1, below 500.
The content of polymerizable compound (C) is with respect to the total amount of solid constituent, preferred 7~65 quality %, more preferably 13~60 quality %, further preferred 17~55 quality %.When the content of polymerizable compound (C) is in above-mentioned scope, have the residual film ratio of colored pattern and the tendency that chemical proofing improves.
<polymerization initiator (D) 〉
Polymerization initiator (D) produces living radical, acid etc. so long as can pass through the effect of light or heat, and the compound that polymerization is begun namely is not particularly limited, and can use known polymerization initiator.
Polymerization initiator (D) is preferably at least a kind the polymerization initiator that contains among the group who is selected from benzene alkyl ketone compound, triaizine compounds, acylphosphine oxide compound, O-acyl group oxime compound and double imidazole compound formation, more preferably contains the polymerization initiator of O-acyl group oxime compound.
O-acyl group oxime compound is the compound with part-structure shown in the formula (d1).Below, * represents bonding position.
O-acyl group oxime compound can be enumerated; N-benzoyloxy-1-(4-thiophenyl phenyl)-1-butanone-2-imines for example; N-benzoyloxy-1-(4-thiophenyl phenyl)-1-octanone-2-imines; N-benzoyloxy-1-(4-thiophenyl phenyl)-3-cyclopentyl-1-acetone-2-imines; N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethane-1-imines; N-acetoxyl group-1-[9-ethyl-6-{2-methyl-4-(3; 3-dimethyl-2,4-dioxane n-pentyl methyl oxygen base) benzoyl }-9H-carbazole-3-yl] ethane-1-imines; N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-3-cyclopentyl propane-1-imines; N-benzoyloxy-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-3-cyclopentyl-1-acetone-2-imines etc.Can use the commercially available products such as イ Le ガ キ ュ ア (registered trademark) OXE01, OXE02 (above, BASF society system), N-1919 (ADEKA society system).
Benzene alkyl ketone compound is the compound with the part-structure shown in the part-structure shown in the formula (d2) or the formula (d3).In these part-structures, phenyl ring can have substituting group.
Compound with the part-structure shown in the formula (d2) can be enumerated, such as 2-methyl-2-morpholino-1-(4-methyl mercapto phenyl)-1-acetone, 2-dimethylamino-1-(4-morpholinyl phenyl)-2-benzyl-1-butanone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl]-the 1-butanone etc.Can use the commercially available products such as イ Le ガ キ ュ ア (registered trademark) 369,907 and 379 (more than, BASF society system).
Compound with the part-structure shown in the formula (d3) can be enumerated, for example 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-hydroxy-2-methyl-1-(4-(2-hydroxyl-oxethyl) phenyl)-1-acetone, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenyl the phenyl)-oligomer of 1-acetone, α, α-diethoxy acetophenone, benzyl dimethyl ketal etc.
Based on the point of sensitivity, benzene alkyl ketone compound is preferably the compound of the part-structure shown in (d2) that has formula.
Triaizine compounds can be enumerated, for example 2,4-two (trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazines, 2,4-two (trichloromethyl)-6-(4-methoxyl naphthyl)-1,3,5-triazine, 2,4-two (trichloromethyl)-6-piperonyl-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(4-methoxyl-styrene)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(2-(5-methylfuran-2-yl) vinyl)-1,3,5-triazines, 2,4-two (trichloromethyl)-6-(2-(furans-2-yl) vinyl)-1,3,5-triazine, 2,4-two (trichloromethyl)-6-(2-(diethylamino-2-aminomethyl phenyl) vinyl)-1,3, the 5-triazine, 2,4-two (trichloromethyl)-6-(2-(3,4-Dimethoxyphenyl) vinyl)-1,3,5-triazine etc.
The acylphosphine oxide compound can be enumerated, TMDPO etc.Can use the commercially available products such as イ Le ガ キ ュ ア 819 (チ バ ジ ャ パ Application society system).
Double imidazole compound can be enumerated, for example 2,2 '-two (2-chlorphenyls)-4; 4 '; 5,5 '-tetraphenyl double imidazole; 2,2 '-two (2; the 3-dichlorophenyl)-4; 4 ', 5,5 '-tetraphenyl double imidazole is (for example with reference to JPH06-75372-A; JPH06-75373-A etc.); 2; 2 '-two (2-chlorphenyls)-4; 4 ', 5,5 '-tetraphenyl double imidazole; 2; 2 '-two (2-chlorphenyls)-4; the two imidazoles of 4 ', 5,5 '-four (alkoxyl phenyls); 2; 2 '-two (2-chlorphenyls)-4; the two imidazoles of 4 ', 5,5 '-four (dialkoxy phenyl); 2; 2 '-two (2-chlorphenyls)-4; the two imidazoles of 4 ', 5,5 '-four (tri-alkoxy phenyls) are (for example with reference to JPS48-38403-B; JPS62-174204-A etc.); 4; the imidazolium compounds that the phenyl alkoxy carbonic acyl radical of 4 ' 5,5 '-position replaces (such as reference JPH07-10913-A etc.) etc.
Further polymerization initiator (D) can be enumerated the benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethylether, benzoin isopropyl ether, benzoin isobutyl ether; Benzophenone, o-benzoyl yl benzoic acid methyl esters, 4-phenyl benzophenone, 4-benzoyl-4 '-methyldiphenyl base sulfide, 3,3 ', 4,4 '-four (t-butylperoxy carbonyl) benzophenone, 2, the benzophenone cpds such as 4,6-tri-methyl benzophenone; The naphtoquinone compounds such as 9,10-phenanthrenequione, 2-EAQ, camphorquinone; 10-butyl-2-chloro-acridine ketone, dibenzoyl, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.Preferred these are used in combination with polymerization described later initiation auxiliary agent (D1) (particularly amine).
Acid agent can be enumerated, salts such as 4-hydroxy phenyl dimethyl sulfonium tosilate, 4-hydroxy phenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, diphenyl iodine tosilate, diphenyl iodine hexafluoro antimonate, or nitrobenzyl toluenesulfonic acid salt, benzoin toluenesulfonic acid salt etc.
The content of polymerization initiator (D) is with respect to total amount 100 mass parts of resin (B) and polymerizable compound (C), preferred 0.1~30 mass parts, more preferably 1~20 mass parts.When the content of polymerization initiator (D) is in above-mentioned scope, owing to have the tendency that high-sensitivity, time shutter shorten, and then throughput rate is improved.
When containing polymerization initiator (D), can further contain polymerization and cause auxiliary agent (D1).It is for the compound of promotion by the polymerization of the optical polymerism compound of polymerization initiator initiated polymerization, perhaps sensitizer that polymerization causes auxiliary agent (D1).
Polymerization causes auxiliary agent (D1) can enumerate amines, alkoxy anthracene compound, thioxanthones compound and carboxylic acid compound etc.
Amines can be enumerated, triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylaminobenzoic acid methyl esters, EDMAB, 4-dimethylaminobenzoic acid isopentyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, N, the N-dimethyl-p-toluidine, 4,4 '-two (dimethylamino) benzophenone (common name Michler's keton), 4,4 '-two (diethylamino) benzophenone, 4,4 '-two (ethylmethylamino) benzophenone etc., wherein, preferred 4,4 '-two (diethylamino) benzophenone.Can use the commercially available products such as EAB-F (hodogaya chemical industry (strain) system).
The alkoxy anthracene compound can be enumerated, 9,10-dimethoxy anthracene, EDMO, 9,10-diethoxy anthracene, 2-ethyl-9,10-diethoxy anthracene, 9,10-dibutoxy anthracene, 2-ethyl-9,10-dibutoxy anthracene etc.
The thioxanthones compound can be enumerated, ITX, ITX, 2,4-diethyl thioxanthone, 2,4-two clopenthixal ketones, 1-chloro-4-propoxyl group thioxanthones etc.
Carboxylic acid compound can be enumerated, thiophenyl acetic acid, methylbenzene ethyl thioglycollic acid, ethylbenzene ethyl thioglycollic acid, ethyl methyl benzene ethyl thioglycollic acid, dimethyl benzene ethyl thioglycollic acid, methoxybenzene ethyl thioglycollic acid, dimethoxy benzene ethyl thioglycollic acid, chlorobenzene ethyl thioglycollic acid, dichloro-benzenes ethyl thioglycollic acid, N-phenylglycine, phenoxyacetic acid, naphthyl thioacetic acid, N-naphthyl glycocoll, naphthoxy acetic acid etc.
Polymerization causes auxiliary agent (D1) and can be used singly or two or more kinds in combination.
When using these polymerizations to cause auxiliary agent (D1), its use amount is with respect to total amount 100 mass parts of resin (B) and polymerizable compound (C), preferred 0.1~30 mass parts, more preferably 1~20 mass parts.The amount that causes auxiliary agent (D1) when polymerization can further form colored pattern with high sensitivity in this scope the time, have the tendency that the throughput rate of color filter improves.
<solvent (E) 〉
Solvent (E) is not particularly limited, and can use normally used solvent in this field.Such as can from ester solvent (molecule contains-COO-, do not contain-O-solvent), ether solvents (molecule contains-O-, do not contain-COO-solvent), ether-ether solvent (molecule contains-COO-and-solvent of O-), choice for use the ketone solvent (molecule contains-CO-, do not contain-COO-solvent), alcoholic solvent, aromatic hydrocarbon solvents, amide solvent, dimethyl sulfoxide (DMSO) etc.
Ester solvent can be enumerated, methyl lactate, ethyl lactate, butyl lactate, 2-hydroxyl isobutyl alkanoic acid methyl esters, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl isobutyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, Propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, adnoral acetate, gamma-butyrolacton etc.
Ether solvents can be enumerated, the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, the glycol monomethyl propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, the diethylene glycol single-butyl ether, propylene glycol monomethyl ether, propylene glycol list ethylether, propylene glycol list propyl ether, the propylene glycol single-butyl ether, 3-methoxyl-n-butyl alcohol, 3-methoxyl-3-methyl butanol, tetrahydrofuran, oxinane, Isosorbide-5-Nitrae-dioxan, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, the diethylene glycol dipropyl ether, the diethylene glycol dibutyl ethers, anisole, phenetol and methyl anisole etc.
The ether-ether solvent can be enumerated, methoxy menthyl acetate, the methoxyacetic acid ethyl ester, the methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, the 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, the 2-methoxy methyl propionate, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, the 2-ethoxyl ethyl propionate, 2-methoxyl-2 Methylpropionic acid methyl esters, 2-ethoxy-2 Methylpropionic acid ethyl ester, 3-methoxyl butylacetic acid ester, 3-methyl-3-methoxyl butylacetic acid ester, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, propylene glycol list propyl ether acetic acid esters, the DPGME acetic acid esters, the ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, TC acetic acid esters and diethylene glycol single-butyl ether acetic acid esters etc.
Ketone solvent can be enumerated, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-HEPTANONE, 3-heptanone, 4-heptanone, 4-methyl-2 pentanone, cyclopentanone, cyclohexanone and isophorone etc.
Alcoholic solvent can be enumerated, methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerine etc.
Aromatic hydrocarbon solvents can be enumerated, benzene,toluene,xylene, mesitylene etc.
Amide solvent can be enumerated, DMF, DMA, 1-METHYLPYRROLIDONE etc.
These solvents can be used singly or two or more kinds in combination.
Among the above-mentioned solvent, based on the point of coating, drying property, the boiling point under the preferred 1atm (standard atmospheric pressure) is at the organic solvent below 180 ℃ more than 120 ℃.The preferred propylene glycol monomethyl ether of solvent (E), ethyl lactate, propylene glycol monomethyl ether, 3-ethoxyl ethyl propionate, glycol monomethyl methyl ether, diethylene glycol monomethyl ether, TC and 4-hydroxy-4-methyl-2-pentanone, more preferably propylene glycol monomethyl ether, propylene glycol monomethyl ether, ethyl lactate and 3-ethoxyl ethyl propionate.
The content of solvent (E) is with respect to the total amount of photosensitive composition, preferred 70~95 quality %, more preferably 75~92 quality %.In other words, preferred 5~30 quality % of the solid constituent of photosensitive composition, more preferably 8~25 quality %.When the content of solvent (E) was in above-mentioned scope, it is good that the flatness when having coating becomes, and colour saturation fully makes display characteristic become good tendency when forming color filter in addition.
<surfactant (F) 〉
Surfactant (F) can be enumerated, and silicone-based surfactant, fluorine are surfactant and the silicone-based surfactant with fluorine atom etc.They can have polymerizable group at side chain.
The silicone-based surfactant can be enumerated, and has the surfactant of siloxane bond etc. in the molecule.Can enumerate particularly ト one レ シ リ コ one Application DC3PA, same SH7PA, same DC11PA, same SH21PA, same SH28PA, same SH29PA, same SH30PA, same SH8400 (trade name: eastern レ ダ ゥ コ one ニ Application グ (strain) system), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (SHIN-ETSU HANTOTAI's chemical industry (strain) system), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (モ メ Application テ イ Block パ Off オ one マ Application ス マ テ リ ア Le ズ ジ ャ パ Application contract commercial firm system) etc.
Above-mentioned fluorine is that surfactant can be enumerated, and has the surfactant of fluoro carbochain etc. in the molecule.Can enumerate particularly Off ロ ラ one De (registered trademark) FC430, same FC431 (Sumitomo 3M (strain) system), メ ガ Off ア Star Network (registered trademark) F142D, same F171, same F172, same F173, same F177, same F183, same F554, same R30, same RS-718-K (DIC (strain) system), エ Off ト Star プ (registered trademark) EF301, same EF303, same EF351, same EF352 (the マ テ リ ア of Mitsubishi Le electronics changes into (strain) system), サ one Off ロ Application (registered trademark) S381, same S382, same SC101, same SC105 (Asahi Glass (strain) system), E5844 ((strain) ダ イ キ Application Off ア イ Application ヶ ミ カ Le institute system) etc.
Above-mentioned silicone-based surfactant with fluorine atom can be enumerated, and has the surfactant of siloxane bond and fluoro carbochain etc. in the molecule.Can enumerate particularly メ ガ Off ア ッ Network (registered trademark) R08, same BL20, same F475, same F477, same F443 (DIC (strain) system) etc.
These surfactants can be used in combination separately or more than 2 kinds.
The content of surfactant (F) is with respect to the total amount of photosensitive composition, below the above 0.2 quality % of preferred 0.001 quality %, below the above 0.1 quality % of preferred 0.002 quality %, more preferably below the above 0.05 quality % of 0.01 quality %.In addition, this content does not comprise the content of above-mentioned pigment dispersing agent.When the content of surfactant (F) is in above-mentioned scope, can make the flatness of color filter become good.
<other composition 〉
Photosensitive composition of the present invention also can contain known adjuvant in these technical fields such as filling agent, other macromolecular compound, adhesion promotor, antioxidant, light stabilizer, chain-transferring agent as required.
The manufacture method of<photosensitive composition 〉
Photosensitive composition of the present invention can be by for example, resin (B), polymerizable compound (C) and polymerization initiator (D) and the polymerization used as required caused auxiliary agent (D1), surfactant (F) and other composition mix to prepare with solvent (E).
When containing pigment (A2), preferably in advance pigment (A2) is mixed with solvent (E), use ball mill etc. makes it to disperse, until the averaged particles of pigment directly becomes the following degree of 0.2 μ m.At this moment, as required, can mix above-mentioned pigment dispersing agent, the resin (B) of part or all.In the dispersible pigment dispersion that obtains, with polymerization initiator (D), remaining solvent (E), surfactant (F) and other composition etc. that the concentration of regulation is mixed xanthene dye (A1), remaining resin (B) and polymerizable compound (C) and used as required, can prepare the target photosensitive composition thus.
Xanthene dye (A1) and the dyestuff (A3) when containing dyestuff (A3) can be dissolved in respectively in the solvent (E) in advance.Preferably the filtrator of this solution with aperture 0.01~1 μ m degree filtered.
Mixed photosensitive composition preferably filters with the filtrator of aperture 0.01~10 μ m degree.
The manufacture method of<color filter 〉
As the method for being made the colored pattern of color filter by photosensitive composition of the present invention, can enumerate photoetching process, ink-jet method, print process etc.Preferred photoetching process wherein.Photoetching process is that above-mentioned photosensitive composition is coated substrate, forms composition layer by drying, the method that is situated between and by photomask the said composition layer is exposed, develops.In the photoetching process, by the time not using photomask in exposure, and/or do not develop, can form painted the filming of solidfied material of above-mentioned composition layer.
The thickness of making color filter is not particularly limited, and can suitably adjust according to purpose or purposes etc. 0.1~30 μ m for example, preferred 0.1~20 μ m, further preferred 0.5~6 μ m.
Substrate can use the glass plates such as soda-lime glass of quartz glass, borosilicate glass, aluminosilicate glass, surface coating silicon dioxide, perhaps the resin plates such as polycarbonate, polymethylmethacrylate, polyethylene terephthalate, silicon, the substrate after aforesaid substrate forms aluminium, silver, silver/copper/palldium alloy film etc.Can form other color-filter layer, resin bed, transistor, circuit etc. on these substrates.
Forming each color pixel by photoetching process can carry out under known or habitual device and condition.For example can be performed as follows making.
At first, photosensitive composition is coated on the substrate, made it dry by volatile ingredients such as heat drying (preliminary drying) and/or drying under reduced pressure desolventizings, obtain level and smooth composition layer.
Coating process can be enumerated, spin-coating method, slot coated method, Xia Feng ﹠amp; Method of spin coating etc.
Preferred 30~120 ℃ of temperature when carrying out heat drying, more preferably 50~110 ℃.In addition, preferred 10 seconds~60 minutes of heat time heating time, more preferably 30 seconds~30 minutes.
When carrying out drying under reduced pressure, preferably under the pressure of 50~150Pa, carry out under 20~25 ℃ the temperature range.
The thickness of composition layer is not particularly limited, and can suitably adjust according to the material that uses, purposes etc.For example so that the colored pattern or the painted thickness of filming that obtain are that 0.1~20 μ m, preferred 0.5~6 μ m form composition layer.
Then, composition layer Jie is exposed so that it forms the target colored pattern by photomask.Pattern on this photomask is not particularly limited, and can use pattern according to the target purposes.
The used light source that exposes preferably produces the light source of the light of 250~450nm wavelength.For example can use by the end of the light filter of this wavelength region may light to not enough 350nm and end, also can use the bandpass filter of selecting this wavelength region may that near near near the light the 436nm, the 408nm, the 365nm is carried out selectivity and take out.Can enumerate particularly mercury lamp, light emitting diode, metal-halide lamp, Halogen lamp LED etc.
Owing to can shine equably parallel rays to plane of exposure integral body, or make photomask and the correct contraposition of composition layer, so preferably use the exposure devices such as mask alignment device, step-by-step exposure machine.
Develop by composition layer after the exposure is contacted with developer solution, can form colored pattern at substrate.By developing, can make the unexposed portion of composition layer be dissolved in developer solution in order to remove.The aqueous solution of the alkali compounds such as developer solution preference such as potassium hydroxide, sodium bicarbonate, sodium carbonate, Tetramethylammonium hydroxide.Concentration in the aqueous solution of these alkali compounds, preferred 0.01~10 quality %, more preferably 0.03~5 quality %.Further, developer solution also can contain surfactant.
Developing method can use in paddling process, infusion process and the spray-on process etc. arbitrarily.Further, during development, substrate can be with arbitrarily angled inclination.
Preferably wash after the development.
Further, preferably the colored pattern that obtains is carried out rear baking.Preferred 150~250 ℃ of rear baking temperature, more preferably 160~235 ℃.Preferred 0.5~10 minute of rear baking time, more preferably 1~5 minute.
The colored pattern and painted the filming that as above obtain can be used as color filter.
According to photosensitive composition of the present invention, can make the color filter of especially brightness excellence.This color filter is useful as the color filter that is used for display device (such as liquid crystal indicator, organic El device etc.), Electronic Paper, solid-state imager etc.
Embodiment
Then enumerate embodiment, the present invention is further specifically described.In the example, the % of expression content or use amount and part are if without special record, be quality criteria.
Synthesis example 1
In the flask that possesses condenser pipe and stirring apparatus, (the trade name Chugai Aminol Fast Pink R of the potpourri of compound shown in compound shown in the throw-in type (A1-1a) and the formula (A1-1b); China and foreign countries change into system) 8.9 parts of 15 parts, 150 parts of chloroforms and DMFs, stir when maintaining below 20 ℃ 10.9 parts of dropping thionyl chlorides.After drip finishing, be warming up to 50 ℃, keep making it to react 5 hours under synthermal, be cooled to thereafter 20 ℃.Cooled reaction solution when stirring is kept below 20 ℃, is dripped the mixed liquor of 22.1 parts of 12.5 parts of 2 ethyl hexylamines and triethylamines.Thereafter, synthermal lower stirring made it reaction in 5 hours.After then the reaction mixture that obtains being heated up in a steamer desolventizing with rotary evaporator, add a small amount of methyl alcohol vigorous stirring.This potpourri is added in the mixed liquor of 375 parts of ion exchange waters while stirring, crystal is separated out.The crystal that filtration is separated out carefully cleans with ion exchange water, in 60 ℃ of lower drying under reduced pressure, obtains dyestuff (A1-1) (potpourri of the compound shown in formula (A1-1-1)~formula (A2-2-8)) 11.3 parts.
Synthesis example 2
Mix the compound shown in 40.5 parts of formulas (A1-2a) and 64.4 parts of 2-aminotoluene (East capital and change into (strain) system), further add 263 parts of N-methylpyridones (Northeast chemistry (strain) system), in 120 ℃ of lower stirrings 8 hours.After the reactant liquor that obtains is cooled to room temperature, add in the mixed liquor of 1200 parts of entry, 75 parts of 35% hydrochloric acid, after stirring 1 hour under the room temperature, crystallize out.After the crystal of separating out obtained as the suction strainer residue, after 50 parts of tetrahydrofurans, 200 parts of cleanings of water, 60 ℃ of 1 evenings of drying under reduced pressure, 49 parts of the compounds shown in the acquisition formula (A1-2b).Productive rate is 89%.
Then, 130.7 parts of 20.1 parts of compounds shown in hybrid (A1-2b), 28.7 parts of iodoethane (Tokyo changes into (strain) system) and 25.4 parts in sal tartari, 1-METHYLPYRROLIDONEs (Northeast chemistry (strain) system), 80 ℃ of lower stirrings 4 hours under the shading condition.The reactant liquor that obtains is cooled to after the room temperature concentrated, add in 460 parts of the entry 10~15 ℃ lower stir 1 hour after, crystallize out.After the crystal that produces obtained as the suction strainer residue, after 500 parts of 20% methanol-waters, 1000 parts of cleanings of ion exchange water, 60 ℃ of 1 evenings of drying under reduced pressure, 20.6 parts of the compounds shown in the acquisition formula (A1-2).Productive rate is 93%.
The evaluation of the compound shown in the formula (A1-2)
(mass spectrophotometry) ionization mode=ESI+:m/z=[M+H]
+603.3
Exact Mass (accurate mass): 602.2
Synthesis example 3
With 40.5 parts of compounds shown in the formula (A1-3a) and 2,60.5 parts of 6-xylidins (Tokyo changes into (strain) system) mix under the shading condition, 150 ℃ of lower stirrings 8 hours in 200 parts of N-methylpyridones.After the reactant liquor that obtains is cooled to room temperature, add in the mixed liquor of 1200 parts in water, 75 parts of 35% hydrochloric acid, stir after 1 hour crystallize out under the room temperature.After the crystal of separating out obtained as the suction strainer residue, after 100 parts of cleanings of methyl alcohol, 60 ℃ of 1 evenings of drying under reduced pressure, 49 parts of the compounds shown in the acquisition formula (A1-3b).Productive rate is 85%.
Then, 24.2 parts in 28.8 parts of compounds shown in the formula (A1-3b) and 21.6 parts of 1-N-Propyl Bromides and sal tartari is joined in 144 parts of the N-methylpyridones 90 ℃ of lower stirrings 4 hours.The reactant liquor that obtains is cooled to after the room temperature concentrated, adds in 560 parts in the water, 10~15 ℃ lower stir 1 hour after, crystallize out.After the crystal that produces obtained as the suction strainer residue, after 1000 parts of cleanings of ion exchange water, 60 ℃ of 1 evenings of drying under reduced pressure, 30.0 parts of the compounds shown in the acquisition formula (A1-3).Productive rate is 91%.
The evaluation of the compound shown in the formula (A1-3)
(mass spectrophotometry) ionization mode=ESI+:m/z=[M+H]
+659.3
Exact?Mass:658.3
Synthesis example 4
Divide with 0.02L/ in the flask that possesses stirring machine, thermometer, reflux condenser and tap funnel to pass into nitrogen and make the nitrogen environment atmosphere, add propylene glycol monomethyl ether 257 mass parts, in the time of stirring, be heated to 70 ℃.Then, with methacrylic acid 68 mass parts, 83 parts of vinyltoluenes, acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] decyl ester (compound shown in the compound shown in the formula (I-1) and the formula (II-1) mixes with mol ratio at 50: 50) 227 mass parts are dissolved in propylene glycol monomethyl ether 140 mass parts, be mixed with solution, use tap funnel to last 4 hours and in 70 ℃ flask, drip this solution to being incubated.
On the other hand, with polymerization initiator 2,2 '-azo two (2,4-methyl pentane nitrile), 30 mass parts are dissolved in the solution in propylene glycol monomethyl ether 225 mass parts, last 4 hours with another tap funnel and drip in flask.After the dropping of polymerization initiator solution finishes, remain on 70 ℃ lower 4 hours, be cooled to thereafter room temperature, obtaining weight-average molecular weight (Mw) is 8.1 * 10
3, solid constituent 37.8 quality %, solid constituent acid number 106mg-KOH/g resin B 1 solution.Resin B 1 has following structural unit.
Synthesis example 5
Divide with 0.02L/ in the flask that possesses stirring machine, thermometer, reflux condenser and tap funnel to pass into nitrogen and make the nitrogen environment atmosphere, add propylene glycol monomethyl ether 257 mass parts, be heated to 70 ℃ in the time of stirring.Then, with acrylic acid 57 mass parts, 83 parts of vinyltoluenes, acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] decyl ester (compound shown in the compound shown in the formula (I-1) and the formula (II-1) mixes with mol ratio at 50: 50) 238 mass parts are dissolved in propylene glycol monomethyl ether 140 mass parts, be mixed with solution, use tap funnel to last 4 hours and in 70 ℃ flask, drip this solution to being incubated.On the other hand, with polymerization initiator 2,2 '-azo two (2,4-methyl pentane nitrile), 30 mass parts are dissolved in the solution that obtains after propylene glycol monomethyl ether 225 mass parts, last 4 hours with another tap funnel and drip in flask.After the dropping of polymerization initiator solution finishes, remain on 70 ℃ lower 4 hours, be cooled to thereafter room temperature, obtaining weight-average molecular weight Mw is 1.04 * 10
4, solid constituent 37.4 quality %, solid constituent acid number 112mg-KOH/g resin B 2 solution.Resin B 2 has following structural unit.
Synthesis example 6
Divide with 0.02L/ in the flask that possesses reflux condenser, tap funnel and stirring machine to pass into nitrogen and make the nitrogen environment atmosphere, add 220 parts of ethyl lactates, be heated to 70 ℃ in the time of stirring.Then, with 84 parts of methacrylic acids and acrylic acid 3,4-epoxy three ring [5.2.1.0
2.6] 336 parts of decyl ester (compound shown in the compound shown in the formula (I-1) and the formula (II-1) mixes with mol ratio at 50: 50), be dissolved in 140 parts of the ethyl lactates, be mixed with solution, use tap funnel to last 4 hours and in 70 ℃ flask, drip this solution to being incubated.On the other hand, with polymerization initiator 2,30 parts of 2 '-azos two (2,4-methyl pentane nitrile) are dissolved in solution in 95 parts of the ethyl lactates and last 4 hours with another tap funnel and drip in flask.After the dropping of polymerization initiator solution finishes, remain on 70 ℃ lower 4 hours, be cooled to thereafter room temperature, obtaining weight-average molecular weight Mw is 8.0 * 10
3, molecular weight distribution is 2.5, solid constituent is 48%, the solution acid number is resin B 3 solution of 50mg-KOH/g (acid number that solid constituent converts is 104mgKOH/g).Resin B 3 has following structural unit.
For the weight-average molecular weight (Mw) of the resin that obtains in the synthesis example and the mensuration of number-average molecular weight (Mn), use the GPC method to carry out according to following condition.
Device: K2479 ((strain) Shimadzu Seisakusho Ltd. system)
Chromatographic column: SHIMADZU Shim-pack GPC-80M
Chromatogram column temperature: 40 ℃
Solvent: THF (tetrahydrofuran)
Flow velocity: 1.0mL/min
Detecting device: RI
Proofread and correct and use standard substance: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (eastern ソ one (strain) system)
With the ratio (Mw/Mn) of the polystyrene conversion weight-average molecular weight of above-mentioned acquisition and number-average molecular weight as molecular weight distribution.
Embodiment 1,2 and comparative example 1
(preparation of dispersible pigment dispersion 1)
Mix following composition, after the use ball mill fully disperses pigment, obtain dispersible pigment dispersion 1.
Colorant (A): C.I. pigment blue 15: 10.1 parts of 6 (pigment)
6.5 parts of acrylic acid series pigment dispersing agents
Solvent (E): 59 parts of propylene glycol monomethyl ether
Solvent (E): 25 parts of ethyl lactates
(preparation of dispersible pigment dispersion 2)
Mix following composition, after the use ball mill fully disperses pigment, obtain dispersible pigment dispersion 2.
Colorant (A): C.I. pigment blue 15: 20 parts of 6 (pigment)
5 parts of acrylic acid series pigment dispersing agents
Solvent (E): 142 parts of propylene glycol monomethyl ether
(preparation of photosensitive composition)
Mixture table 1 described composition obtains photosensitive composition.
[table 1]
In addition, each composition that shows in the table 1 is as follows.
Colorant (A): (A1-1): dyestuff (A1-1)
Colorant (A): (A2-1): dispersible pigment dispersion 1
Colorant (A): (A2-2): dispersible pigment dispersion 2
Resin (B): (B-1): resin B 1 solution
Resin (B): (B-2): resin B 2 solution
Resin (B): (B-3): resin B 3 solution
Polymerizable compound (C): (C-1): dipentaerythritol acrylate (KAYARAD (registered trademark) DPHA: Japanese chemical drug (strain) system)
Polymerization initiator (D): (D-1): N-benzoyloxy-1-(4-thiophenyl phenyl)-1-octanone-2-imines (イ Le ガ キ ュ ア (registered trademark) OXE 01; BASF society system; O-acyl group oxime compound)
Polymerization initiator (D): (D-2): 2-methyl-2-morpholino-1-(4-methyl mercapto phenyl)-1-acetone (イ Le ガ キ ュ ア (registered trademark) 907; BASF society system; Benzene alkyl ketone compound)
Polymerization causes auxiliary agent (D1): (D1-1): 2,4-diethyl thioxanthone (KAYACURE (registered trademark)
DETX; Japan's chemical drug (strain) system; The thioxanthones compound)
Solvent (E): (E-1): propylene glycol monomethyl ether
Solvent (E): (E-2): ethyl lactate
Solvent (E): (E-3): propylene glycol monomethyl ether
Surfactant (F): (F-1): polyether modified silicone oil (ト one レ シ リ コ one Application SH8400: eastern レ ダ ゥ コ one ニ Application グ (strain) system)
(dissolubility evaluation)
At 2 inches square glass substrates (イ one グ Le XG; コ one ニ Application グ society system) on, behind spin-coating method coating coloring photosensitive combination, uses pressure Reduction Dryer (VCD; マ イ Network ロ テ ッ Network (strain) system) with 50Pa drying under reduced pressure 2 seconds.With dried film impregnated under 23 ℃ that to contain nonionic be surfactant 0.12% with the water system developer solution of sodium carbonate 2% in 20 seconds, wash.With microscope (250 times of multiplying powers; VF-7510; (strain) キ one エ Application ス system) observe substrate after the washing, be zero when finding on the substrate after the washing foreign matter to be arranged, when finding to have foreign matter on the substrate after the washing for *, remember in table 3.If can confirm there is not foreign matter on the substrate according to this test, then can say when on substrate, forming colored pattern by photoetching process, can not find foreign matter at substrate and colored pattern yet.
(making of colored pattern)
At 2 inches square glass substrates (イ one グ Le XG; コ one ニ Application グ society system) on, behind spin-coating method coating coloring photosensitive combination, in 100 ℃ of lower preliminary dryings 3 minutes.After the cooling, make the 100 μ m that are spaced apart between the substrate that is coated with this photosensitive composition and the figuratum quartz glass of tool photomask processed, use exposure machine (TME-150RSK; ト プ コ Application (strain) system), under atmospheric atmosphere gas, with 150mJ/cm
2Exposure (365nm benchmark) carry out irradiation.As photomask, use to have formed the live width of 100 μ m and the photomask of line intermittent pattern (Line and Space Pattern).Behind the irradiation, with above-mentioned film under 24 ℃, to be immersed in contain in the water system developer solution that nonionic is surfactant 0.12% and sodium carbonate 2% 60 seconds and develop, after the washing, in baking oven, carry out 30 minutes rear baking under 230 ℃, obtain colored pattern.
(determining film thickness)
For the colored pattern that obtains, use determining film thickness device (DEKTAK3: Japanese vacuum technique (strain) system)) to measure thickness.The results are shown in Table 2.
(chromaticity evaluation)
For the colored pattern on the glass substrate that obtains, use color measurement instrument (OSP-SP-200; オ リ Application パ ス (strain) system) measures light splitting (spectrum), xy chromaticity coordinates (x, y) and brightness Y in the XYZ colour system of the color matching function mensuration CIE of use illuminant-C.The results are shown in Table 2.
[table 2]
Embodiment 3,4
(preparation of photosensitive composition)
Mixture table 3 described compositions obtain photosensitive composition.In addition, carry out the evaluation identical with embodiment 1.The results are shown in Table 4.
[table 3]
[table 4]
Confirm the photosensitive composition of embodiment, in the time of can suppressing colored pattern and form, peeling off of developing and cause, do not find foreign matter on the substrate after colored pattern forms.Thus, by being used as color filter by the colored pattern that photosensitive composition of the present invention obtains, can make display device with high productivity.
According to photosensitive composition of the present invention, a part of unexposed portion that can suppress the composition layer that formed by this photosensitive composition produces when developing to be peeled off, and then reduces the foreign matter on the colored pattern.
Claims (5)
1. photosensitive composition, it contains colorant, resin, polymerizable compound and polymerization initiator,
Colorant is the colorant that contains xanthene dye and pigment,
Resin is the multipolymer that contains following structural unit: derive from least a kind structural unit being selected among the group that unsaturated carboxylic acid and unsaturated carboxylic acid anhydrides consist of, derive from the monomer of cyclic ether structure with carbon number 2~4 and ethene unsaturated link structural unit, derive from the structural unit of the monomer shown in the formula (x)
In the formula (x), R
A1Expression hydrogen atom or methyl,
R
A2The alkyl of expression carbon number 1~6,
P represents 0~5 integer, when p is 2 when above, and a plurality of R
A2Identical or different.
2. photosensitive composition according to claim 1 derives from the content of the structural unit of monomer shown in the formula (x) with respect to the structural unit total amount that consists of multipolymer, more than 1 % by mole below 80 % by mole.
3. photosensitive composition according to claim 1 and 2, the monomer shown in the formula (x) is vinyltoluene.
4. a color filter is formed by the described photosensitive composition of any one of claim 1~3.
5. a display device contains color filter claimed in claim 4.
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CN102914943A (en) * | 2011-08-04 | 2013-02-06 | 住友化学株式会社 | Colored curable resin composition |
CN112631074A (en) * | 2013-09-24 | 2021-04-09 | 罗门哈斯电子材料韩国有限公司 | Negative photosensitive resin composition and insulating film using the same |
CN112980213A (en) * | 2019-12-17 | 2021-06-18 | 保土谷化学工业株式会社 | Xanthene dye, coloring composition containing the dye, coloring agent for color filter, and method for producing the dye |
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JP6592257B2 (en) * | 2015-03-12 | 2019-10-16 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Colored curable resin composition |
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KR20130028686A (en) | 2013-03-19 |
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