CN101652712A - Coloured composition and use the color filter of this coloured composition - Google Patents
Coloured composition and use the color filter of this coloured composition Download PDFInfo
- Publication number
- CN101652712A CN101652712A CN200880011567A CN200880011567A CN101652712A CN 101652712 A CN101652712 A CN 101652712A CN 200880011567 A CN200880011567 A CN 200880011567A CN 200880011567 A CN200880011567 A CN 200880011567A CN 101652712 A CN101652712 A CN 101652712A
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- coloured composition
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- acid
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- 239000000203 mixture Substances 0.000 title claims abstract description 106
- 239000000049 pigment Substances 0.000 claims abstract description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 239000000758 substrate Substances 0.000 claims abstract description 21
- 239000002270 dispersing agent Substances 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000003892 spreading Methods 0.000 claims description 14
- 230000007480 spreading Effects 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- -1 acetophenone compound Chemical class 0.000 description 47
- 239000002904 solvent Substances 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 25
- 239000006185 dispersion Substances 0.000 description 23
- 238000000576 coating method Methods 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 230000035945 sensitivity Effects 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- 239000001054 red pigment Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- 229920000178 Acrylic resin Polymers 0.000 description 10
- 239000004925 Acrylic resin Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000012860 organic pigment Substances 0.000 description 10
- 239000003513 alkali Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000005457 optimization Methods 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 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 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
- 241001597008 Nomeidae Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000001055 blue pigment Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 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 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical group CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical group CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
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- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- 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 2
- 238000005859 coupling reaction Methods 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
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- 229940124543 ultraviolet light absorber Drugs 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OZBIETPCMMGBGS-UHFFFAOYSA-N 1,1-dimethyl-2-propylhydrazine Chemical compound CCCNN(C)C OZBIETPCMMGBGS-UHFFFAOYSA-N 0.000 description 1
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
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- 229960005235 piperonyl butoxide Drugs 0.000 description 1
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- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- 239000005060 rubber Substances 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical group CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical compound [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 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
-
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
-
- 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
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
Abstract
Coloured composition of the present invention contains compound (A), pigment (B), pigment dispersing agent (C), the Photoepolymerizationinitiater initiater (D) with ethylenic unsaturated double-bond and comprises the organic solvent (E) of the above organic solvent (S) of 25 weight %, and the solubleness of water in organic solvent (S) surpasses 7.0 weight %.General assembly (TW) with coloured composition is a benchmark, and the water percentage of coloured composition is 0.3～2.0 weight %.Color filter of the present invention possesses the colored pixels that is formed by described coloured composition on substrate.
Description
Technical field
The present invention relates to be fit to be formed for liquid crystal display cells or solid-state imager (CCD, CMOS etc.) color filter rendered image coloured composition, and use the color filter of this coloured composition.
Background technology
The colored pixels that is configured for the color filter of color liquid crystal display arrangement or colour pick-up tube element etc. forms as described below.On glass substrate etc., be coated with photosensitive coloring composition (painted anticorrosive additive material), after drying is removed remaining solvent, be situated between, with shine active energy beam near exposure (ultraviolet source exposure) etc. by the photomask that is used to form pixel.When painted anticorrosive additive material was minus, illuminated portion solidified, and when painted anticorrosive additive material was eurymeric, the alkali solubility of illuminated portion improved.Then, the non-illuminated portion (situation of minus) or the illuminated portion (situation of eurymeric) of anticorrosive additive material are removed with developers such as aqueous slkalis.Other color pixel are carried out above-mentioned 1 color pixel repeatedly form technology, make color filter thus.
In recent years, color liquid crystal display arrangement as lcd tv or auto navigation with and the one-piece type notebook of liquid crystal indicator formed bigger market, the desktop computer of also energy-conservation as having utilized, space-efficient feature is popularized with display and televisor.In addition, along with market is normally popularized, the requirement that improves the Color reproduction characteristic is more and more higher.
In order to improve the Color reproduction characteristic of color filter, must improve the content of colorant in photosensitive coloring composition or the thickness of increase coloured composition.But, when increasing the content of colorant, produce problems such as sensitivity reduction, development and exploring degree variation.In addition, when increasing thickness, exposure light no show film bottom produces problems such as the rectilinearity of colored pixels or cross sectional shape be bad.
Improve colorant concentration even the spy of Japan opens to disclose in the flat 2003-156842 communique, also can obtain the photosensitive composition of colored pattern with low exposure.Said composition contains colorant, binder polymer, Photoepolymerizationinitiater initiater and solvent.Photoepolymerizationinitiater initiater contains acetophenone compound and triaizine compounds, and Photoepolymerizationinitiater initiater contains amines.
Summary of the invention
The object of the present invention is to provide and be suitable for making the sensitivity of color filter and the coloured composition that developing powder improves, has stable viscosity.
According to the present invention, a kind of coloured composition is provided, it contains: have compound (A), pigment (B), pigment dispersing agent (C), the Photoepolymerizationinitiater initiater (D) of ethylenic unsaturated double-bond and comprise the organic solvent (E) of the above organic solvent (S) of 25 weight %, the solubleness of water in organic solvent (S) surpasses 7.0 weight %; General assembly (TW) with coloured composition is a benchmark, and the water percentage of this coloured composition is 0.3～2.0 weight %.
In addition, according to the present invention, provide a kind of color filter, it possesses the colored pixels that is formed by coloured composition of the present invention on substrate.
Embodiment
At first, describe coloured composition of the present invention in detail.
Coloured composition of the present invention contains: have compound (A), pigment (B), pigment dispersing agent (C), the Photoepolymerizationinitiater initiater (D) of ethylenic unsaturated double-bond and comprise the organic solvent (E) of the above organic solvent (S) of 25 weight %, the solubleness of water in organic solvent (S) surpasses 7.0 weight %.And, be benchmark with the general assembly (TW) of coloured composition, the water percentage of coloured composition is 0.3～2.0 weight %.
＜water percentage 〉
The water percentage of coloured composition of the present invention can be measured by known methods such as karl Fischer methods.So-called karl Fischer method be shown in following formula (1), use with water optionally and the karl Fischer reagent of reaction quantitatively (by iodine, sulphuric dioxide, alkali, and alcohol (ROH) equal solvent constitute) measure the method for water percentage.As this method, coulometric titration and volumetric precipitation method are arranged, can use any method.
Formula (1):
I
2+ SO
2+ 3 alkali+ROH+H
2O → 2 alkali HI+ alkali HSO
4R
When being benchmark (100 weight %) with the general assembly (TW) of coloured composition, the water percentage of coloured composition of the present invention before just will coating substrate is 0.3～2.0 weight %, is preferably 0.3～1.5 weight %, more preferably 0.6～1.5 weight %.
The coloured composition that water percentage surpasses 2.0 weight % through the time ground thickening, cause being coated with bad when being coated on the substrate.In addition, water percentage can't fully improve sensitivity or developing powder less than the coloured composition of 0.3 weight %.
Amount of moisture in the coloured composition can be by coloured composition modulation the time, wittingly water is added in the coloured composition during keeping after the modulation and controls, perhaps also can be controlled at the water percentage of sneaking between circulating process, described circulating process is to remain in the coloured composition that is coated with on the cup and reclaim the operation that is coated with once more being coated with in the operation that by method of spin coating coloured composition is coated on the glass substrate.
＜have a compound (A) of ethylenic unsaturated double-bond 〉
Compound with ethylenic unsaturated double-bond is the compound that solidifies by active energy beam irradiation, contains monomer, oligomer and active energy ray-curable resin, can separately or mix that above-claimed cpd uses more than 2 kinds.
As above-mentioned monomer, oligomer, can use (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) acrylic acid 2-hydroxy methacrylate, (methyl) acrylic acid 2-hydroxy propyl ester, (methyl) cyclohexyl acrylate, (methyl) propenoic acid beta-carboxyl ethyl ester, polyglycol two (methyl) acrylate, 1,6-hexanediol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, tripropylene glycol two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, 1,6-hexanediol diglycidyl ether two (methyl) acrylate, bisphenol-A diglycidyl ether two (methyl) acrylate, neopentyl glycol diglycidyl ether two (methyl) acrylate, dipentaerythritol six (methyl) acrylate, (methyl) acrylic acid three ring decyl ester, (methyl) acrylate of methylolation melamine, epoxy radicals (methyl) acrylate, various acrylate such as urethane acrylate and methacrylate, (methyl) acrylic acid, styrene, vinyl-acetic ester, the hydroxyethyl vinyl ether, the ethylene glycol bisthioglycolate vinyl ether, the pentaerythrite trivinyl ether, (methyl) acrylamide, N-hydroxymethyl (methyl) acrylamide, the N-vinyl formamide, vinyl cyanide etc.
As the active energy ray-curable resin; can use wire macromolecule with hydroxyl, carboxyl, amino isoreactivity substituted radical and (methyl) acyclic compound with isocyanate group, aldehyde radical, epoxy radicals isoreactivity substituted radical or cinnamic acid reaction, photocrosslinking reaction groups such as (methyl) acryloyl group, styryl be imported this wire macromolecule and the resin that obtains.In addition, can use the wire macromolecule that styrene-maleic anhydride copolymer or alpha-olefin-maleic anhydride co-polymer etc. are contained acid anhydrides to carry out the resin that half esterization obtains by (methyl) acyclic compound that (methyl) acrylic acid hydroxyalkyl acrylate etc. has hydroxyl.
The content of the compound with ethylenic unsaturated double-bond in the coloured composition of the present invention is 50～2000 weight portions with respect to 100 weight portion pigment optimizations, more preferably 100～1000 weight portions.
＜pigment (B) 〉
As pigment, can use commercially available organic pigment usually, according to the tone of the colored pixels that forms, can and use dyestuff, natural pigment, inorganic pigment.As organic pigment, preferably use color emissivity height and thermotolerance, the particularly high pigment of heat-resisting decomposability.Organic pigments etc. can separately or mix more than 2 kinds and use.In addition, organic pigment can be the pigment by the salt mill is handled, the molten miniaturizations such as (acid pasting) of acid obtains.Below, number the concrete example that expression can be used for the organic pigment of coloured composition of the present invention with color index (C.I.).
When using coloured composition of the present invention to form red pixel, can use C.I. paratonere 7,9,14,41,48:1,48:2,48:3,48:4,81:1,81:2,81:3,122,123,146,149,168,177,178,179,184,185,187,192,200,202,208,210,216,220,223,224,226,240,254,255,264, red pigments such as 272.Can and use yellow uitramarine, orange pigment in red colored composition.
When using coloured composition of the present invention to form green pixel, can use C.I. pigment Green 7,10,36, viridine greens such as 37.Can and use yellow uitramarine in green coloring composition.
When using coloured composition of the present invention to form blue pixel, can use C.I. pigment blue 15,15:1,15:2,15:3,15:4,15:6,16,64, blue pigments such as 80.Can and use violet pigment in blue colored composition.
When using coloured composition of the present invention to form yellow pixel, can use C.I. pigment yellow 1,2,3,4,5,6,10,12,13,14,15,16,17,18,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,126,127,128,129,138,139,147,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,198,199,213,214 yellow uitramarines such as grade.
When using coloured composition of the present invention to form the purple pixel, can use C.I. pigment violet 1,19,23,27,29,30,32,37,40,42, pigment such as 50.
When using coloured composition of the present invention to form magenta pixel, can use C.I. paratonere 7,14,41,48:1,48:2,48:3,48:4,81:1,81:2,81:3,146,177,178,184,185,187,200,202,208,210,246,254,255,264,270, pigment such as 272.Can and use yellow uitramarine in the magenta coloured composition.
When using coloured composition of the present invention to form cyan pixel, can use the C.I. pigment blue 15: 1,15:2,15:3,15:4,15:6,16, pigment such as 80.
When using coloured composition of the present invention to form orange pixel, can use C.I. pigment orange 36,43,51,55,59,61,71, pigment such as 73.
In addition, can use inorganic pigments such as metal oxide, cadmium sulfide, lime carbonate, barium carbonate, barium sulphate, clay, talcum, chrome yellow such as titania, oxidation iron, antimony pentaoxide, zinc paste, silicon dioxide.
And then, also can use black pigment.As black pigment, can use that carbon black, titanium are black, nigrosine, anthraquinone be that black pigment, perylene is a black pigment, particularly, can use C.I. pigment black 1,6,7,12,20,31,32 etc., but, preferably use carbon black from the size of price, light-proofness.Carbon black can carry out surface treatment with resin etc.
＜pigment dispersing agent (C) 〉
As pigment dispersing agent, can use to have alkalescence or acid substituent pigment derivative, anthraquinone derivative, acridone derivatives, pyrrolotriazine derivatives or resin type spreading agent.Wherein, the preferred use has alkalescence or acid substituent pigment derivative or resin type spreading agent, even use the difficult pigment that disperses, also can make the coloured composition of dispersiveness, flowability, excellent storage stability.Below, detailed description has alkalescence or acid substituent pigment derivative and resin type spreading agent.
(i) have alkalescence or acid substituent pigment derivative
Have alkalescence or acid substituent pigment derivative and be the compound that in organic pigment, imports alkalescence or acid substituting group and obtain.As the organic pigment that constitutes pigment derivative, can enumerate for example diketopyrrolopyrrolecocrystals series pigments, azo, bisdiazo, azo pigments such as polyazo, phthualocyanine pigment, the diamido DIANTHRAQUINONE, anthrapyrimidine, flavanthrone, anthracene is formed anthrone (anthanthrone), indanthrone, pyranthrone, anthraquione pigmentss such as violanthrone, quinacridone pigment dioxazine series pigments, purple cyclic ketones (Perinone) perylene pigment, the thioindigo series pigments, the isoindoline series pigments, isoindolinone pigment, quinophthalones (quinophthalone) series pigments, intellectual circle's series pigments, metal complex series pigments etc.
Alkali subtituent is at least one substituting group that is selected from by in the group of following formula (2), (3), (4) and (5) expression.
Formula (2):
Formula (3):
Formula (4)
Formula (5):
In formula (2)～(5), symbol has following implication.
X represents-SO
2-,-CO-,-CH
2NHCOCH
2-,-CH
2-or Direct Bonding;
V represents 1～10 integer;
R
8, R
9Represent independently respectively alkyl, alkenyl, can substituted phenyl, perhaps R
8With R
9What form that one, expression can further contain nitrogen, oxygen or sulphur atom can substituted heterocycle residue.Alkyl has 1～36 carbon atom usually, and alkenyl has 2～36 carbon atoms usually.If the example of exemplified by alkyl groups can be enumerated for example branched alkyls such as straight chained alkyls such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, nonyl, decyl, isopentyl, 2-ethylhexyl, 1-heptyl decyl, 1-hexyl nonyl.If exemplify the example of alkenyl, then can be allyl derivs such as 1-allyl ethyl, 1-butyl allyl.Substituting group on the phenyl comprises abovementioned alkyl, alkenyl etc.;
R
10Expression alkyl, alkenyl or can substituted phenyl.Herein, alkyl has 1～36 carbon atom usually, and alkenyl has 2～36 carbon atoms usually.If the example of exemplified by alkyl groups for example can be branched alkyls such as straight chained alkyls such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, nonyl, decyl, isopentyl, 2-ethylhexyl, 1-heptyl decyl, 1-hexyl nonyl.If exemplify the example of alkenyl, then can be allyl derivs such as 1-allyl ethyl, 1-butyl allyl.Substituting group on the phenyl comprises abovementioned alkyl, alkenyl etc.;
R
11, R
12, R
13, R
14Represent hydrogen atom, alkyl, alkenyl or can substituted phenyl respectively independently.Herein, alkyl has 1～36 carbon atom usually, and alkenyl has 2～36 carbon atoms usually.If the example of exemplified by alkyl groups for example can be branched alkyls such as straight chained alkyls such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, nonyl, decyl, isopentyl, 2-ethylhexyl, 1-heptyl decyl, 1-hexyl nonyl.If exemplify the example of alkenyl, then can be allyl derivs such as 1-allyl ethyl, 1-butyl allyl.Substituting group on the phenyl comprises abovementioned alkyl, alkenyl etc.;
Y represents-NR
15-Z-NR
16-or Direct Bonding;
R
15, R
16Represent hydrogen atom, alkyl, alkenyl or can substituted phenyl respectively independently.Herein, alkyl has 1～36 carbon atom usually, and alkenyl has 2～36 carbon atoms usually.If the example of exemplified by alkyl groups for example can be branched alkyls such as straight chained alkyls such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, nonyl, decyl, isopentyl, 2-ethylhexyl, 1-heptyl decyl, 1-hexyl nonyl.If exemplify the example of alkenyl, then can be allyl deriv such as 1-allyl ethyl, 1-butyl allyl for example.Substituting group on the phenyl comprises abovementioned alkyl, alkenyl etc.;
Z represents alkylidene, alkylene group or can substituted phenylene.Herein, alkylidene and alkylene group have 1～36 carbon atom usually.When enumerating above-mentioned example, can enumerate for example methylene, ethylidene, propylidene, trimethylene, butylidene, tetramethylene, pentamethylene, hexa-methylene, heptamethylene, eight methylene, nine methylene, decamethylene, 11 methylene, ten dimethylenes, ten trimethylenes, ten tetramethylenes, ten pentamethylenes, ten hexa-methylenes.Substituting group on the phenylene comprises abovementioned alkyl, alkylidene etc.;
R represents the substituting group of following formula (6) expression or the substituting group of following formula (7) expression;
Q represents the substituting group of hydroxyl, alkoxy, following formula (6) expression or the substituting group of following formula (7) expression.Herein, alkoxy has 1～36 carbon atom usually.
Formula (6):
Formula (7):
In formula (6) and (7), R
8～R
14And v is as top definition.
Pigment derivative with alkali subtituent can be synthetic by various route of synthesis.For example, after in pigment, importing the substituting group shown in following formula (8)～formula (11), make the substituent amine component, for example N that form formula (2)～formula (5) expression with this substitution reaction, N-dimethylamino propylamine, N methyl piperazine, diethylamine or 4-[4-hydroxyl-6-[3-(dibutylamino) propyl group amino]-1,3,5-triazine-2-base is amino] reaction such as aniline obtains.
Formula (8)-SO
2Cl
Formula (9)-COCl
Formula (10)-CH
2NHCOCH
2Cl
Formula (11)-CH
2Cl
When the substituting group of formula (8)～(11) expression and the reaction of above-mentioned amine component, can mix the part generation hydrolysis of general formula (8)～(11), the material that chlorine is substituted by hydroxyl.At this moment, the substituting group of formula (8), formula (9) expression forms sulfonic group, carboxylic acid group respectively, but all groups can be the state of free acid, also can for the salt of 1～3 valency metal or above-mentioned monoamine.
In addition, when organic pigment was azo pigment, the substituting group that formula (2)～formula (5) is represented imported in diazonium composition or the coupling composition in advance, carries out coupling reaction then, also can make the azo pigment derivant with alkali subtituent thus.
As the substituent example of acidity, can enumerate sulfonic group, terephthalic acid (TPA) monoamides methyl etc.Can make effect of sulfuric acid import sulfonic group, organic pigment can be carried out carry out amino methylization with primary amine behind the chloromethylation, carry out monoamidesization with terephthalic acid (TPA) then and import terephthalic acid (TPA) monoamides methyl in organic pigment.
Pigment derivative can separately or be mixed more than 2 kinds and used.
The amount with alkalescence or acid substituent pigment derivative in the coloured composition of the present invention is 1～50 weight portion with respect to 100 weight portion pigment optimizations, and more preferably 3～30 weight portions most preferably are 5～25 weight portions.With respect to the content of the pigment derivative of 100 weight portion pigment during less than 1 weight portion, dispersed sometimes variation, when surpassing 50 weight portions, thermotolerance, photostability variation sometimes.
(ii) resin type spreading agent
The resin type spreading agent comprises pigment compatibility position with the character that is adsorbed on the pigment and the position that has compatibility with compound with ethylenic unsaturated double-bond and solvent, and performance is adsorbed on the pigment and makes the effect of pigment stable dispersion in compound with ethylenic unsaturated double-bond and solvent.As the resin type spreading agent, can enumerate for example polyurethane, polycarboxylates such as polyacrylate, the unsaturated polyester acid amides, poly carboxylic acid, poly carboxylic acid (part) amine salt, the poly carboxylic acid ammonium salt, the poly carboxylic acid alkylamine salt, polysiloxane, the long-chain polyaminoamide phosphate, the polycarboxylate of hydroxyl or their modifier, oiliness spreading agents such as the acid amides that poly-(rudimentary alkylene imines) and the pet reaction with free carboxy form or its salt, (methyl) acrylic acid-styrol copolymer, (methyl) acrylic acid-(methyl) acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol (PVA), water soluble resin or water-soluble high-molecular compounds such as polyvinyl pyrrolidone, polyester system, modified polyacrylate system, the ethylene oxide/propylene oxide additive compound, phosphate systems etc., above-mentioned spreading agent can separately or mix more than 2 kinds and uses.
The content of the resin type spreading agent in the coloured composition of the present invention is 0.1～100 weight portion with respect to 100 weight portion pigment optimizations, and more preferably 0.5～75 weight portion most preferably is 1.0～50 weight portions.
＜Photoepolymerizationinitiater initiater (D))
As Photoepolymerizationinitiater initiater, can use 4-phenoxy group dichloroacetophenone, the 4-tert-butyl group-dichloroacetophenone, diethoxy acetophenone, 1-(4-isopropyl phenyl)-2-hydroxy-2-methyl propane-1-ketone, 1-hydroxycyclohexylphenylketone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-butane-acetophenone based compounds such as 1-ketone; Benzoin based compounds such as benzoin, benzoin methyl ether, benzoin ethylether, benzoin isopropyl ether, benzyl dimethyl ketal; Benzophenone, benzoylbenzoic acid, benzoylbenzoic acid methyl esters, 4-phenyl benzophenone, dihydroxy benaophenonel, propylene acidylate benzophenone, 4-benzoyl-4 '-dimethyl diphenyl sulfide, 3,3 ', benzophenone based compounds such as 4,4 '-four (tert-butyl hydroperoxide carbonyl) benzophenone; Thioxanthones, 2-clopenthixal ketone, 2-methyl thioxanthones, isopropyl thioxanthone, 2,4-diisopropyl thioxanthones, 2, thioxanthones based compounds such as 4-diethyl thioxanthone; 2,4,6-three chloro-s-triazine, 2-phenyl-4, two (the trichloromethyl)-s-triazine of 6-, 2-(p-methoxyphenyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(p-methylphenyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-piperonyl-4, two (the trichloromethyl)-s-triazine of 6-, 2, two (the trichloromethyl)-6-styryl-s-triazine of 4-, 2-(naphthalene-1-yl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-methoxyl-naphthalene-1-yl)-4, two (the trichloromethyl)-s-triazine of 6-, 2,4-trichloromethyl-(piperonyl)-6-triazine, 2, the 4-trichloromethyl (4 '-methoxyl-styrene)-triazine based compounds such as 6-triazine; 1,2-acetyl caproyl, 1-[4-(phenyl sulfenyl) phenyl], oxime ester based compound such as-2-(O-benzoyl oxime), O-(acetyl group)-N-(1-phenyl-2-oxygen-2-(4 '-methoxyl-naphthyl) ethylidene) hydramine; Two (2,4, the 6-trimethylbenzoyl) phenyl phosphine oxide, 2,4, phosphine based compounds such as 6-trimethylbenzoyl diphenyl phosphine oxide; 9, quinoline based compounds such as 10-phenanthrenequione, camphorquinone, EAQ; Borate based compound, carbazole based compound, imidazole compound, two luxuriant titanium sub-group compounds etc.Above-mentioned Photoepolymerizationinitiater initiater can be used alone, and perhaps can mix more than 2 kinds and use.The content of Photoepolymerizationinitiater initiater is 5～200 weight portions with respect to 100 weight portion pigment optimizations, more preferably 10～150 weight portions.
＜solvent (E) 〉
The scope of organic solvent in the coloured composition of the present invention (E) more than 25 weight % of total solvent weight contains organic solvent (S), and the solubleness of water in this organic solvent (S) surpasses 7.0 weight %.Solvent (E) also can only be surpassed solvent (S) formation of 7.0 weight % by the solubleness of water.
Below, the solubleness of specifically enumerating water surpasses the organic solvent (S) of 7.0 weight %.The solubleness of expression water in solvent in the bracket in the illustration does not have the situation of special record to represent the solubleness infinity of water in solvent.Glyceryl triacetate (7 weight %), cyclohexanone (9.5 weight %), cyclohexanol (11 weight %), isobutyl alcohol (15 weight %), ethylene glycol mono hexyl ether (18.8 weight %), normal butyl alcohol (20 weight %), 3 third glycol single-butyl ethers, 3 third glycol monomethyl ether, dipropylene glycol list ethylether, the dipropylene glycol single-butyl ether, dipropylene glycol list propyl ether, the dipropylene glycol monomethyl ether, diethylene glycol monoethyl ether acetate, the diglycol monotertiary butyl ether, diglycol monotertiary butyl ether acetic acid esters, the diglycol monotertiary methyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, the diglycol monotertiary isopropyl ether, the ethylene glycol monomethyl ether acetate, the glycol monomethyl methyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether, the glycol monomethyl isopropyl ether, gamma-butyrolacton, N, dinethylformamide, 1, the 3-butanediol, 1, the 3-butylene glycol, 1, the 4-dioxane, the 2-methyl isophthalic acid, ammediol, the 3-methyl isophthalic acid, the 3-butylene glycol, 3-methoxyl-3-methyl isophthalic acid-butanols etc.
For solvent (S) in addition the solvent of water solubility above 7.0 weight %, consideration coating, security, the dissolubility when reaching use aftermentioned transparent resin are selected.Solvent (S) organic solvent in addition that surpasses 7.0 weight % as water solubility, for example can enumerate 1,2, the 3-trichloropropane, 1,3-butylene glycol diacetate esters, the 2-heptanone, 3,5,5-trimethyl-2-cyclohexene-1-ketone, 3,3, the 5-trimethylcyclohexanone, the 3-ethoxyl ethyl propionate, 3-methoxyl-3-methyl butyl acetic acid esters, the 3-methoxybutanol, 3-methoxyl butylacetic acid ester, the 4-heptanone, m-xylene, between diethylbenzene, m-dichlorobenzene, N, the N-dimethyl acetamide, n-butylbenzene, the n-pro-pyl acetic acid esters, N-Methyl pyrrolidone, o-xylene, ortho-chlorotolu'ene, adjacent diethylbenzene, o-dichlorobenzene, parachlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butyl benzene, different Buddhist ketone, the ethylene glycol bisthioglycolate ethylether, the ethylene glycol bisthioglycolate butyl ether, ethylene glycol monomethyl ether acetate, the glycol monomethyl tertbutyl ether, the ethylene glycol monobutyl ether acetic acid esters, the glycol monomethyl propyl ether, diisobutyl ketone, adnoral acetate, the dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetic acid esters, the dipropylene glycol single-butyl ether, diacetone alcohol, propylene-glycol diacetate, propylene glycol phenyl ether, propylene glycol list ethylether, propylene glycol list ethylether acetic acid esters, the propylene glycol single-butyl ether, propylene glycol list propyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether, the propylene glycol monomethyl ether propionic ester, phenmethylol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid esters etc. can use or mix the above-mentioned solvent of use separately.
Organic solvent (E) can use the amount of 800～4000 weight portions with respect to 100 weight portion pigment.
＜other adjuvants 〉
Coloured composition of the present invention can cooperate various adjuvants as required, for example surfactants such as filling agent, nonionic system, kation system, negative ion system, driving fit promoter, antioxidant, ultraviolet light absorber, anti-polycoagulant, the transparent resin that does not have the ethylenic unsaturated double-bond, sensitizer, the multi-functional thiol who plays a role as chain-transferring agent, hot polymerization inhibitor etc.
As filling agent, can enumerate glass, aluminium oxide etc.
As driving fit promoter, can enumerate vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, the 3-aminopropyltriethoxywerene werene, the 3-glycidoxypropyltrime,hoxysilane, 3-glycidoxy propyl group methyl dimethoxysilane, 2-(3,4-epoxy radicals cyclohexyl) ethyl trimethoxy silane, the 3-chloropropylmethyldimethoxysilane, the 3-r-chloropropyl trimethoxyl silane, the 3-methacryloxypropyl trimethoxy silane, 3-sulfydryl propyl trimethoxy silicane etc.
As antioxidant, can enumerate 2,2-thiobis (4-methyl-6-tert butyl phenol), 2,6 di t butyl phenol etc.
As ultraviolet light absorber, can enumerate 2-(the 3-tert-butyl group-5-methyl-2-hydroxy phenyl)-5-chlorobenzotriazole, alkoxy benzophenone etc.
As anti-polycoagulant, can enumerate sodium polyacrylate etc.
Above-mentioned adjuvant uses 0.05～20 weight portion, more preferably uses the amount of 0.1～10 weight portion with respect to 100 weight portion pigment optimizations.
The transparent resin that does not have the ethylenic unsaturated double-bond be in the long zone of the all-wave of visible region 400～700nm transmissivity be preferably more than 80%, the more preferably resin more than 95%, transparent resin comprises thermoplastic resin, thermoset resin.
As thermoplastic resin, for example can enumerating, butyral resin, styrene-maleic acid copolymer, haloflex, chlorinated polypropylene, Polyvinylchloride, vinyl chloride-vinyl-acetic ester multipolymer, polyvinyl acetate base ester, polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether, polyurethane series resin, vibrin, acrylic resin, alkyd resin, polystyrene resin, polyamide, rubber are that resin, thermoprene are resin, cellulose family, tygon (HDPE, LDPE), polybutadiene, polyimide resin etc.In addition, as thermoset resin, can enumerate for example epoxy resin, benzoguanamine resin, Abietyl modified maleic acid resin, Abietyl modified fumaric resin, melamine resin, urea resin, phenolics etc.The transparent resin that does not have the ethylenic unsaturated double-bond is 50～2000 weight portions with respect to 100 weight portion pigment optimizations, more preferably 100～1000 weight portions.
As sensitizer, can enumerate triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylaminobenzoic acid methyl esters, 4-dimethylaminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid isopentyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, N, N-dimethyl-p-toluidine, 4,4 '-two (dimethylamino) benzophenone, 4,4 '-two (diethylamino) benzophenone, 4,4 '-amine compounds such as two (ethylmethylamino) benzophenone.Above-mentioned sensitizer can use a kind or mix more than 2 kinds and use.The content of sensitizer is preferably 0.1～60 weight portion with respect to 100 weight portion Photoepolymerizationinitiater initiaters.
The multi-functional thiol is that the compound with 2 above mercaptos gets final product, for example can enumerate ethanthiol, the last of the ten Heavenly stems two mercaptan, 1, the two thiopropionates of 4-butylene glycol, 1, the two thioglycolic acid esters of 4-butylene glycol, ethylene glycol bis thioglycolic acid ester, the ethylene glycol bis thiopropionate, trimethylolpropane tris thioglycolic acid ester, the trimethylolpropane tris thiopropionate, trimethylolpropane tris (3-sulfydryl butyric ester), pentaerythrite tetrathio ethyl glycolate, pentaerythrite tetrathio propionic ester, tri-thiol propionic acid three (2-hydroxyethyl) isocyanuric acid ester, 1,4-dimethyl sulfydryl benzene, 2,4,6-tri-thiol-s-triazine, 2-(N, the N-dibutylamino)-4,6-dimercapto-s-triazine etc.Above-mentioned multi-functional thiol can use a kind or mix more than 2 kinds and use.Multi-functional thiol's content is 0.05～100 weight portion with respect to 100 weight portion pigment optimizations, more preferably 0.1～60 weight portion.
As hot polymerization inhibitor, quinhydrones, p methoxy phenol, di-t-butyl-paracresol, 1,2,3,-thrihydroxy-benzene, tert-butyl catechol, benzoquinones, 4,4 '-sulphur two (3 methy 6 tert butyl phenols), 2,2 '-di-2-ethylhexylphosphine oxide (4-methyl-6-tert butyl phenol), 2-mercaptobenzimidazole etc. are useful.The content of hot polymerization inhibitor is 0.01～10 weight portion with respect to 100 weight portion pigment optimizations.
Coloured composition of the present invention can be made according to as described below: will have the compound (A), pigment (B), pigment dispersing agent (C), organic solvent (E) of ethylenic unsaturated double-bond, and as required and mixing such as transparent resin that does not have the ethylenic unsaturated double-bond that adds and various adjuvants, disperse with horizontal sand mill, vertical grinding machine, ring-like ball mill, masher etc., add Photoepolymerizationinitiater initiater (D).Coloured composition of the present invention disperses after can mixing repertoire, but also can at first only pigment and pigment dispersing agent be dispersed in the solvent, adds other compositions then and disperses once more to modulate.
Below, color filter of the present invention is described.
Color filter of the present invention can be made according to as described below: by coating processes such as rotary coating, curtain coating coating, roller coat, coloured composition of the present invention is coated on the substrate, and drying is situated between by the mask pattern irradiation ultraviolet radiation of regulation, use developing liquid developing, form colored pixels.As employed ultraviolet ray this moment, preferred especially g ray, h ray, i ray etc.
As substrate, can enumerate soda-lime glass, PYREX (registered trademark) glass, quartz glass that for example is used for liquid crystal display cells etc. and the substrate that obtains at above-mentioned adhesion nesa coating on glass; Be used for photoelectricity conversion elements substrate, for example silicon substrate of imaging apparatus etc. etc.; Complementary burning film semiconductor (CMOS) etc.Aforesaid substrate forms the black-tape (black stripe) that each pixel is isolated sometimes.In addition, on aforesaid substrate, as required,, undercoat can be set in order to improve with the driving fit of the layer on top, to prevent material diffusion or make the substrate surface planarization.
As developer solution, so long as dissolving ultraviolet ray not the coloured composition of irradiation portion but the composition that do not dissolve the coloured composition of ultraviolet irradiation portion get final product, can use any developer solution.Particularly, can use various organic solvents or alkaline aqueous solution.As above-mentioned organic solvent, can enumerate above-mentioned solvent contained in the coloured composition of the present invention.
In addition, as above-mentioned alkaline aqueous solution, can use following alkaline aqueous solution, this alkaline aqueous solution be with 0.001～10 weight %, be preferably the concentration of 0.01～1 weight % will be for example NaOH, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammoniacal liquor, ethamine, diethylamine, dimethylethanolamine, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, choline, pyrroles, piperidines, 1,8-diazabicyclo-alkali compounds such as (5.4.0)-7-hendecene dissolving obtains.In addition, when using the developer solution that constitutes by above-mentioned alkaline aqueous solution, wash with water after developing usually.
Color filter of the present invention can be used for solid-state imagers such as liquid crystal display cells or CCD.
Below, based on embodiment the present invention is described, but the present invention is not limited thereto.In addition, in embodiment and the comparative example, " part " expression " weight portion ".In addition, in the ratio of the water solubility in the organic solvent general assembly (TW) above the solvent (S) of 7.0 weight %, the general assembly (TW) of organic solvent is the total weight that comprises whole organic solvents of solvent contained in pigment dispersion of all kinds and the acrylic resin soln.
At first, the Production Example of the acrylic resin soln that is used for embodiment and comparative example and the Production Example of pigment dispersion are described.
The modulation of＜acrylic resin soln 〉
In reaction vessel, add 650 parts of cyclohexanone, nitrogen injection limit in container, limit is heated to 100 ℃, under uniform temp,, carry out polyreaction with the potpourri that splashed into 70.0 parts of styrene, 70.0 parts of methacrylic acids, 75.0 parts of methyl methacrylates, 75.0 parts of butyl methacrylates and 10.0 parts of azobis isobutyronitriles in 1 hour.
After splashing into,, add that 2.0 parts of azobis isobutyronitriles are dissolved in 50 parts of cyclohexanone and the solution that obtains,, obtain weight-average molecular weight and be about 40000 acrylic resin soln further 100 ℃ of following sustained responses 1 hour further 100 ℃ of down reactions after 3 hours.
After being cooled to room temperature, gather about 2g resin solution, 180 ℃ of following heat dryings 20 minutes, measure nonvolatile component, based on this measured value, formerly add cyclohexanone according to the mode that makes nonvolatile component reach 30 weight % in the He Cheng resin solution, the modulation acrylic resin soln.
The Production Example of＜yellow pigment dispersion 〉
(a) the salt mill is handled
With 250g yellow uitramarine (C.I. pigment yellow 13 9; BASF AG's system " Paliotol YellowD1819 "), 700g sodium chloride, 107g maleic acid resin (waste river chemical company's system " マ Le キ one De No.3002 ", acid number: 100mgKOH/g) and 160g polyglycol (Tokyo changes into corporate system) drop in 1 gallon of kneader of stainless steel (aboveground making institute society system) mixing 3 hours.Then, this potpourri is dropped in about 3 intensification water, and the limit is heated to after about 80 ℃ of limits made slurry in 1 hour with the high-speed mixer stir about, and sodium chloride and solvent are removed in its filtration, washing, with dry about 24 hours of 60 ℃ hot-air ovens, obtain " the salt mill is handled P.Y.139 pigment ".
(b) modulation of pigment dispersion
After the potpourri of following composition evenly mixed, use the zirconium pearl of diameter as 0.5mm, disperse 10 hours with Ai Geer grinding machine (Eiger mill) after, filter the making yellow pigment dispersion with the filtrator of 1.0 μ m.
The salt mill is handled 10.0 parts of P.Y.139 pigment
1.0 parts of resin type spreading agents (Japanese Lubrizol corporate system " ソ Le ス パ one ズ 20000 ")
30.0 parts of acrylic resin solns
59.0 parts of propylene glycol monomethyl ether
The Production Example of＜red pigment dispersion α 〉
After the potpourri of following composition evenly mixed, use the zirconium pearl of diameter as 0.5mm, disperse 10 hours with the Ai Geer grinding machine after, filter with the filtrator of 1.0 μ m, modulate red pigment dispersion α.
Red pigment (C.I. paratonere 254; Ciba Specialty Chemicals corporate system " CromophtalRed B-CF ") 10.0 part
1.0 parts of resin type spreading agents (Japanese Lubrizol corporate system " ソ Le ス パ one ズ 20000 ")
30.0 parts of acrylic resin solns
59.0 parts of propylene glycol monomethyl ether
The Production Example of＜red pigment dispersion β 〉
Remove yellow uitramarine is replaced with red pigment (C.I. paratonere 177; Toyo Ink manufacturing company system " Lionol red 2B FG3300 ") in addition, use the method modulation " salt mill handle P.R.177 pigment " identical with the processing of above-mentioned salt mill.
Except that red pigment being replaced with " the salt mill is handled P.R.177 pigment ", use the method modulation red pigment dispersion β identical with the Production Example of red pigment dispersion α.
The Production Example of＜viridine green dispersion α 〉
Remove red pigment is replaced with viridine green (C.I. pigment green 36; Toyo Ink manufacturing company system " Lionol green 6Y-501 ") in addition, use the method identical to make viridine green dispersion α with the manufacture method of red pigment dispersion α.
The Production Example of＜viridine green dispersion β 〉
Remove red pigment is replaced with viridine green (C.I. pigment Green 7; Big Japanese ink chemical company system " Off ア ス ト ゲ Application グ リ one Application S ") in addition, use the method identical to make viridine green dispersion β with the manufacture method of red pigment dispersion α.
The Production Example of＜blue pigment dispersion 〉
The potpourri of following composition is evenly mixed, uses the zirconium pearl of diameter as 0.5mm, disperse 10 hours with sand mill after.Filtrator with 1.0 μ m filters, and makes blue pigment dispersion.
Blue pigment (C.I. pigment blue 15: 6; BASF system " ヘ リ オ ゲ Application Block Le one L-6700F ") 9.0 part
1.0 parts in following copper phthalocyanine derivant
2.0 parts of phosphate series pigments spreading agents (BYK chemical company system " BYK111 ")
27.0 parts of acrylic resin solns
61.0 parts of propylene glycol monomethyl ether
The copper phthalocyanine derivant:
Cu-pc: copper phthalocyanine residue
The Production Example of＜violet pigment dispersion 〉
The potpourri of following composition is evenly mixed, use the zirconium pearl of diameter, after 10 hours,, make the violet pigment dispersion with the filtrator filtration of 1.0 μ m with the sand mill dispersion as 0.5mm.
Violet pigment (C.I. pigment Violet 23)
(9.0 parts of Toyo Ink manufacturing company systems " リ オ ノ one ゲ Application バ イ オ レ ッ ト R6200 "
1.0 parts in following triazine dioxin pigment derivant
2.0 parts of resin type spreading agents (Japanese Lubrizol corporate system " ソ Le ス パ one ズ 24000GR ")
27.0 parts of acrylic resin solns
61.0 parts of propylene glycol monomethyl ether
The triazine dioxin pigment derivant:
The composed as follows of above-mentioned pigment dispersion stated shown in the table 1.
Embodiment 1～9 and comparative example 1～6
Potpourri with the described composition of following table 2 mixes respectively, make it evenly after, the filtrator filtration with 0.6 μ m obtains each coloured composition (resist).In addition, the ratio (weight %) that solvent (S) accounts for total solvent in each coloured composition is recorded in table 2 in the lump with the color of coloured composition.
For each coloured composition of gained, measure water percentage according to following method, and estimate the stability of sensitivity, developing powder, coating, viscosity respectively.The results are shown in table 3.
＜measurement of water-content coefficient method 〉
Use karl Fischer titration apparatus (the capacity titration formula determination of moisture device KF-06 type of Mitsubishi Chemical Ind's system) to measure amount of moisture (mg), calculate water percentage (%) by following formula.
Water percentage (%)=(amount of moisture (mg)/mensuration sample size (mg)) * 100
＜sensitivity evaluation 〉
Using coloured composition that spinner obtains embodiment 1～9 and comparative example 1～6 is that the mode rotary coating of 1.2 μ m is on glass substrate, 120 ℃ of following prebake conditions 120 seconds according to making dry film thickness.Then, after this substrate at room temperature cooled off, use extra-high-pressure mercury vapour lamp, carry out ultraviolet exposure by photomask.Then, this substrate carried out spray development with 23 ℃ aqueous sodium carbonate after, use the ion-exchange water washing, carry out air-dryly, in the cleaning baking oven,, on substrate, form banded colored pixels in 230 ℃ of back bakings 30 minutes down.
Use according to the picture size of photomask the pattern of the colored pixels that forms is carried out the sensitivity that accurately machined minimum irradiation exposure is estimated coloured composition.Opinion rating is as follows.
Zero: less than 100mJ/cm
2
△: more than 100 and less than 150mJ/cm
2
*: 150mJ/cm
2More than
＜developing powder evaluation 〉
Use spinner with the coloured composition that obtains in embodiment 1～9 and the comparative example 1～6 according to make dry film thickness be the mode rotary coating of 1.0 μ m on glass substrate, 70 ℃ dry 20 minutes down.
In above-mentioned filming, splash into 2 weight % potassium hydroxide aqueous solution 2ml, measure the time till the dissolving of filming disappears, estimate the developing powder of coloured composition.Opinion rating is as follows.
Zero: less than 10 seconds
△: more than 10 seconds and less than 15 seconds
*: more than 15 seconds
＜coating evaluation 〉
Use coloured composition rotary coating that spinner obtains embodiment 1～9 and comparative example 1～6 on glass substrate, visual inspection is coated with membrane stage, estimates the coating of coloured composition.Opinion rating is as follows.
Zero: form uniform film
△: a small amount of crawling is arranged, but can be coated with
*: there is crawling maybe can't be coated with
The estimation of stability of＜viscosity 〉
25 ℃ measure down the firm making of the coloured compositions that embodiment 1～9 and comparative example 1～6 obtain with 20rpm after with E type viscosity meter (eastern machine industry corporate system " ELD type viscosity meter ") viscosity (initial stage viscosity) and make the viscosity of back after preserving for 1 week under 40 ℃ the environment (through the time viscosity), calculate the viscosity variation.Opinion rating is as described below.
Zero: viscosity changes less than 0.5mPas
△: viscosity is changed to more than the 0.5mPas, less than 1.5mPas
*: viscosity is changed to more than the 1.5mPas
Table 3
| Water percentage | Sensitivity is estimated | Developing powder is estimated | Coating is estimated | Initial stage viscosity | Through the time viscosity | Viscosity changes | |
| Embodiment 1 | ??0.3 | ??○ | ??○ | ??○ | ??6.3 | ??6.3 | ??○ |
| Embodiment 2 | ??1.5 | ??○ | ??○ | ??○ | ??6.4 | ??7.3 | ??△ |
| Embodiment 3 | ??0.8 | ??○ | ??○ | ??○ | ??6.3 | ??6.5 | ??○ |
| Embodiment 4 | ??0.5 | ??○ | ??○ | ??○ | ??7.2 | ??7.3 | ??○ |
| Embodiment 5 | ??1.5 | ??○ | ??○ | ??○ | ??7.4 | ??8.5 | ??△ |
| Embodiment 6 | ??0.7 | ??○ | ??○ | ??○ | ??7.3 | ??7.5 | ??○ |
| Embodiment 7 | ??0.4 | ??○ | ??○ | ??○ | ??5.9 | ??6.0 | ??○ |
| Embodiment 8 | ??1.3 | ??○ | ??○ | ??○ | ??6.0 | ??7.1 | ??△ |
| Embodiment 9 | ??1.8 | ??○ | ??○ | ??○ | ??6.1 | ??7.4 | ??△ |
| Comparative example 1 | ??0.1 | ??× | ??× | ??○ | ??6.3 | ??6.3 | ??○ |
| Comparative example 2 | ??2.3 | ??○ | ??○ | ??△ | ??6.4 | ??8.1 | ??× |
| Comparative example 3 | ??0.1 | ??× | ??× | ??○ | ??7.2 | ??7.2 | ??○ |
| Comparative example 4 | ??2.1 | ??○ | ??○ | ??△ | ??7.5 | ??9.2 | ??× |
| Comparative example 5 | ??0.2 | ??× | ??△ | ??○ | ??5.8 | ??5.8 | ??○ |
| Comparative example 6 | ??2.7 | ??○ | ??○ | ??× | ??6.2 | ??12.5 | ??× |
In the coloured composition of embodiment 1,4, the result is having good stability of developing powder, coating, viscosity, but because water percentage is lower than i.e. 0.6～1.5 weight % of preferred scope of the present invention, so sensitivity reduces slightly as a result.
The coloured composition of embodiment 2,5,7,8 is because water percentage is i.e. 0.6～1.5 weight % of the preferred scope of the present invention, so that the result is the stability of sensitivity, developing powder, coating, viscosity is all good.
In the coloured composition of embodiment 3,6,9, the result is that sensitivity, developing powder, coating are good, but because water percentage exceeds i.e. 0.6～1.5 weight % of the preferred scope of the present invention, so viscosity stability has reduction slightly as a result.
The coloured composition of comparative example 1,3 is because water percentage is 0.1 weight %, so the result is that sensitivity is low, developing powder is slow.
The coloured composition of comparative example 2,4 is because water percentage surpasses 2.0 weight %, so coating is poor slightly as a result, viscosity stability is poor.
The coloured composition of comparative example 5 is because water percentage is 0.2 weight %, so sensitivity is low, developing powder is slow slightly.
The coloured composition of comparative example 6 is because water percentage is 2.7 weight %, and is more, so the result is that coating is poor, viscosity stability is poor.
Clear and definite by above result, the ratio of solvent (S) in solvent that water solubility surpasses 7.0 weight % is in the coloured composition more than the 25 weight %, water percentage is that the coloured composition of the coloured composition of the present invention of 0.3～2.0 weight % and the scope that water percentage is not 0.3～2.0 weight % compares, and sensitivity, developing powder, coating, viscosity stability improve.
As above detailed description, coloured composition of the present invention is owing to contain suitable quantity of water, so have high sensitivity, developing powder is fast.In addition, coloured composition of the present invention is because the scope more than 25 weight % of total solvent weight contains the solvent (S) that water solubility surpasses 7.0 weight %, so although contain water, viscosity is also stable.
Claims (4)
1, a kind of coloured composition, it contains compound (A), pigment (B), pigment dispersing agent (C), Photoepolymerizationinitiater initiater (D) and the organic solvent (E) with ethylenic unsaturated double-bond, this organic solvent (E) comprises the above organic solvent (S) of 25 weight %, and the solubleness of water in this organic solvent (S) surpasses 7.0 weight %; General assembly (TW) with coloured composition is a benchmark, and the water percentage of this coloured composition is 0.3～2.0 weight %.
2, coloured composition according to claim 1, wherein, the water percentage of described coloured composition is 0.6～1.5 weight %.
3, coloured composition according to claim 1, wherein, pigment dispersing agent (C) comprises and has alkalescence or acid substituent pigment derivative or resin type spreading agent.
4, a kind of color filter is characterized in that, possesses the colored pixels that is formed by the described coloured composition of claim 1 on substrate.
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| JP2007106742A JP5142579B2 (en) | 2007-04-16 | 2007-04-16 | Coloring composition and color filter using the same |
| JP106742/2007 | 2007-04-16 | ||
| PCT/JP2008/057188 WO2008129965A1 (en) | 2007-04-16 | 2008-04-11 | Colored composition and color filter therefrom |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102253599A (en) * | 2010-04-21 | 2011-11-23 | 东洋油墨Sc控股株式会社 | Red-colored composition for color filter, and color filter |
| CN103176357A (en) * | 2011-10-12 | 2013-06-26 | 东洋油墨Sc控股株式会社 | Coloring composition used for color filter and color filter |
| CN108369377A (en) * | 2015-12-08 | 2018-08-03 | 富士胶片株式会社 | Radiation sensitive resin composition, cured film, pattern forming method, solid-state imager and image display device |
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| JP5083520B2 (en) * | 2007-07-17 | 2012-11-28 | Ｊｓｒ株式会社 | Radiation sensitive resin composition, liquid crystal display spacer and liquid crystal display element |
| JP5254650B2 (en) * | 2008-03-28 | 2013-08-07 | 富士フイルム株式会社 | Photosensitive resin composition, light-shielding color filter, method for producing the same, and solid-state imaging device |
| JP4873101B2 (en) * | 2010-04-21 | 2012-02-08 | 東洋インキＳｃホールディングス株式会社 | Coloring composition for color filter, and color filter |
| JP5741141B2 (en) * | 2010-08-27 | 2015-07-01 | 東洋インキＳｃホールディングス株式会社 | Black resin composition and black matrix |
| JP5664171B2 (en) * | 2010-11-25 | 2015-02-04 | 凸版印刷株式会社 | Resist adjusting method and resist adjusting apparatus |
| JP5301596B2 (en) * | 2011-03-11 | 2013-09-25 | 富士フイルム株式会社 | Blue photosensitive composition, color filter, method for producing color filter, liquid crystal display device, and organic EL display device |
| JP6054824B2 (en) | 2013-08-01 | 2016-12-27 | 富士フイルム株式会社 | Coloring composition, cured film, color filter, method for producing color filter, solid-state imaging device, and image display device |
| JP6147133B2 (en) | 2013-08-01 | 2017-06-14 | 富士フイルム株式会社 | Coloring composition, cured film, color filter, method for producing color filter, solid-state imaging device, and image display device |
| JP6147134B2 (en) | 2013-08-01 | 2017-06-14 | 富士フイルム株式会社 | Coloring composition, cured film, color filter, method for producing color filter, solid-state imaging device, and image display device |
| JP6852474B2 (en) * | 2017-03-10 | 2021-03-31 | 東洋インキＳｃホールディングス株式会社 | A method for manufacturing a coloring composition for a color filter, a color filter for a solid-state image sensor, and a solid-state image sensor. |
| JP7263856B2 (en) * | 2019-03-14 | 2023-04-25 | 東洋インキＳｃホールディングス株式会社 | Photosensitive coloring composition, and color filter and liquid crystal display device using the same |
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| JPH10146806A (en) * | 1996-11-19 | 1998-06-02 | Showa Highpolymer Co Ltd | Wood treating composition |
| JP2003156842A (en) * | 2001-11-22 | 2003-05-30 | Sumitomo Chem Co Ltd | Colored photosensitive resin composition |
| JP2003295427A (en) * | 2002-03-29 | 2003-10-15 | Fuji Photo Film Co Ltd | Colored photosensitive resin composition and color filter using the same and method for producing the same |
| JP2006343648A (en) * | 2005-06-10 | 2006-12-21 | Mitsubishi Chemicals Corp | Color material dispersion liquid for color filter, curable resin composition for color filter, method for producing the same, color filter, and liquid crystal display device |
| JP5292708B2 (en) * | 2006-03-10 | 2013-09-18 | 三菱化学株式会社 | Curable composition, color filter, and liquid crystal display device |
| WO2007105649A1 (en) * | 2006-03-10 | 2007-09-20 | Mitsubishi Chemical Corporation | Curable composition, color filters, and liquid crystal displays |
| JP2007256684A (en) * | 2006-03-23 | 2007-10-04 | Fujifilm Corp | Photosensitive composition and material for forming light shielding film for display device |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102253599A (en) * | 2010-04-21 | 2011-11-23 | 东洋油墨Sc控股株式会社 | Red-colored composition for color filter, and color filter |
| CN103176357A (en) * | 2011-10-12 | 2013-06-26 | 东洋油墨Sc控股株式会社 | Coloring composition used for color filter and color filter |
| CN103176357B (en) * | 2011-10-12 | 2016-06-01 | 东洋油墨Sc控股株式会社 | Color composition for color filter and colour filter |
| CN108369377A (en) * | 2015-12-08 | 2018-08-03 | 富士胶片株式会社 | Radiation sensitive resin composition, cured film, pattern forming method, solid-state imager and image display device |
| US10921708B2 (en) | 2015-12-08 | 2021-02-16 | Fujifilm Corporation | Radiation-sensitive resin composition, cured film, pattern forming method, solid-state imaging device, and image display device |
| CN108369377B (en) * | 2015-12-08 | 2022-05-17 | 富士胶片株式会社 | Radiation-sensitive resin composition, cured film, pattern forming method, solid-state imaging element, and image display device |
| CN114706272A (en) * | 2015-12-08 | 2022-07-05 | 富士胶片株式会社 | Radiation-sensitive resin composition, cured film, pattern forming method, solid-state imaging element, and image display device |
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| KR20100014779A (en) | 2010-02-11 |
| CN101652712B (en) | 2012-09-05 |
| TWI443455B (en) | 2014-07-01 |
| JP2008268242A (en) | 2008-11-06 |
| JP5142579B2 (en) | 2013-02-13 |
| WO2008129965A1 (en) | 2008-10-30 |
| KR101431499B1 (en) | 2014-08-20 |
| TW200905385A (en) | 2009-02-01 |
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