JPWO2008032675A1 - Black photosensitive resin composition, method for forming black matrix, method for producing color filter, and color filter - Google Patents
Black photosensitive resin composition, method for forming black matrix, method for producing color filter, and color filter Download PDFInfo
- Publication number
- JPWO2008032675A1 JPWO2008032675A1 JP2008534329A JP2008534329A JPWO2008032675A1 JP WO2008032675 A1 JPWO2008032675 A1 JP WO2008032675A1 JP 2008534329 A JP2008534329 A JP 2008534329A JP 2008534329 A JP2008534329 A JP 2008534329A JP WO2008032675 A1 JPWO2008032675 A1 JP WO2008032675A1
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- JP
- Japan
- Prior art keywords
- black
- resin composition
- photosensitive resin
- meth
- group
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 61
- 239000011159 matrix material Substances 0.000 title claims description 72
- 238000000034 method Methods 0.000 title claims description 51
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000000049 pigment Substances 0.000 claims abstract description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 37
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 37
- 239000011230 binding agent Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 68
- 239000000178 monomer Substances 0.000 description 52
- -1 acryl Chemical group 0.000 description 35
- 239000003960 organic solvent Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 230000003287 optical effect Effects 0.000 description 19
- 239000000758 substrate Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000010030 laminating Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000036211 photosensitivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000005357 flat glass Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- TXZNVWGSLKSTDH-XCADPSHZSA-N (1Z,3Z,5Z)-cyclodeca-1,3,5-triene Chemical class C1CC\C=C/C=C\C=C/C1 TXZNVWGSLKSTDH-XCADPSHZSA-N 0.000 description 1
- GCIHZDWTJCGMDK-UHFFFAOYSA-N (2-methylphenyl) prop-2-enoate Chemical compound CC1=CC=CC=C1OC(=O)C=C GCIHZDWTJCGMDK-UHFFFAOYSA-N 0.000 description 1
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DVFAVJDEPNXAME-UHFFFAOYSA-N 1,4-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(C)=CC=C2C DVFAVJDEPNXAME-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KPYPNTLKDIYIKB-UHFFFAOYSA-N 2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2 KPYPNTLKDIYIKB-UHFFFAOYSA-N 0.000 description 1
- GSKOWRJEBKQTKZ-UHFFFAOYSA-N 2,6-dihydroxy-2,6-dimethylheptan-4-one Chemical compound CC(C)(O)CC(=O)CC(C)(C)O GSKOWRJEBKQTKZ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- NSWNXQGJAPQOID-UHFFFAOYSA-N 2-(2-chlorophenyl)-4,5-diphenyl-1h-imidazole Chemical class ClC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 NSWNXQGJAPQOID-UHFFFAOYSA-N 0.000 description 1
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- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/28—Interference filters
- G02B5/281—Interference filters designed for the infrared light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
-
- 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
- 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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
-
- 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
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
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- 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
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- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- Physics & Mathematics (AREA)
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
Abstract
バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料を含有する黒色感光性樹脂組成物であって、バインダーポリマーが、下記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂を含む黒色感光性樹脂組成物。A black photosensitive resin composition comprising a binder polymer, a photopolymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a black pigment, wherein the binder polymer has the following general formulas (I), (II) and The black photosensitive resin composition containing the acrylic resin which has a repeating unit represented by (III).
Description
本発明は、黒色感光性樹脂組成物、ブラックマトリクスの形成方法、カラーフィルタの製造方法及びカラーフィルタに関する。 The present invention relates to a black photosensitive resin composition, a black matrix forming method, a color filter manufacturing method, and a color filter.
従来、液晶表示デバイス、センサー及び色分解デバイス等にカラーフィルタが使用されている。これらカラーフィルタは、コントラスト向上、色純度の低下を防ぐ目的で各色画素の境界をブラックマトリクスで遮光している。 Conventionally, color filters are used in liquid crystal display devices, sensors, color separation devices, and the like. In these color filters, the boundary of each color pixel is shielded by a black matrix for the purpose of improving the contrast and preventing the decrease in color purity.
通常、ブラックマトリクスは、クロム、ニッケル、アルミニウム等の金属膜を蒸着、スパッタリング等の真空成膜によりガラス基板上に成膜し、次いで、フォトリソグラフィー技術によりマトリクス状に金属膜のパターンを施すことで形成される。具体的には、上記金属膜上に感光性レジストを塗布し、フォトマスクを介して紫外線を照射した後、未露光部を除去してレジストパターンを形成し、エッチング処理により金属膜にパターンを施し、レジストを剥離することによりブラックマトリクスを形成している。 Normally, a black matrix is formed by depositing a metal film such as chromium, nickel, or aluminum on a glass substrate by vacuum film formation such as vapor deposition or sputtering, and then applying a pattern of the metal film in a matrix form by photolithography technology. It is formed. Specifically, after applying a photosensitive resist on the metal film and irradiating ultraviolet rays through a photomask, a resist pattern is formed by removing an unexposed portion, and a pattern is applied to the metal film by an etching process. The black matrix is formed by removing the resist.
しかしながら、金属膜を用いると、ブラックマトリクスの形成に長時間を要するため生産コストが高くなりやすい。また、カラーフィルタを廃棄処理する際、そのカラーフィルタがクロムからなるブラックマトリクスを備えると、その処分方法が大きな問題となる。 However, when a metal film is used, the production cost is likely to increase because it takes a long time to form the black matrix. Further, when the color filter is disposed of, if the color filter includes a black matrix made of chromium, the disposal method becomes a big problem.
そこで、感光性樹脂に黒色顔料を加えた黒色感光性樹脂組成物を用いたブラックマトリクスの形成が検討されている(例えば、特許文献1参照)。
しかしながら、従来の黒色感光性樹脂組成物を用いフォトリソグラフィー技術でブラックマトリクスを形成する場合、光学濃度(OD値)を高くすることや、ブラックマトリクスの細線化が難しい等の問題がある。さらに、黒色顔料としてカーボンブラックを使用した場合、ブラックマトリクスの電気抵抗値が小さくなる傾向がある。 However, when a black matrix is formed by a photolithography technique using a conventional black photosensitive resin composition, there are problems such as an increase in optical density (OD value) and difficulty in thinning the black matrix. Furthermore, when carbon black is used as the black pigment, the electric resistance value of the black matrix tends to be small.
そこで本発明は、上記事情に鑑みてなされたものであり、ブラックマトリクスとしての光学濃度及び電気抵抗値を十分に満足すると共に、解像度が十分に高い黒色感光性樹脂組成物及びこれを用いたブラックマトリクスの形成方法、カラーフィルタの製造方法並びにカラーフィルタを提供することを目的とする。 Therefore, the present invention has been made in view of the above circumstances, and a black photosensitive resin composition having a sufficiently high resolution and a black photosensitive resin composition sufficiently satisfying an optical density and an electric resistance value as a black matrix. It is an object to provide a matrix forming method, a color filter manufacturing method, and a color filter.
上記目的を達成するために、本発明は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料を含有し、バインダーポリマーが、下記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂を含む黒色感光性樹脂組成物を提供する。
ここで、R1、R2、R4及びR5はそれぞれ独立に水素原子又はメチル基を示し、R3は下記式(i)、(ii)又は(iii)で表されるジシクロ環又はトリシクロ環を有する1価の基を示し、X1は単結合、炭素数1〜10のアルキレン基又は炭素数1〜10のオキシアルキレン基を示し、Yは単結合又は2価の有機基を示す。
本発明の黒色感光性樹脂組成物は、上記構成を備えることで、ブラックマトリクスとしての光学濃度及び電気抵抗値を十分に満足すると共に、解像度を十分に高くすることができる。 By providing the black photosensitive resin composition of the present invention with the above-described configuration, the optical density and electrical resistance value as a black matrix can be sufficiently satisfied, and the resolution can be sufficiently increased.
本発明者らは、特定の理論に拘束されるものではないが、このようなカルボキシル基を有するアクリル樹脂を含むことで、本発明の黒色感光性樹脂組成物は、光感度が高く、アルカリ現像性に優れるものとなり、現像時のバリの発生を低減し解像度を十分に向上できると推察している。 Although the present inventors are not bound by a specific theory, by including such an acrylic resin having a carboxyl group, the black photosensitive resin composition of the present invention has high photosensitivity and alkali development. It is presumed that the resolution is sufficiently improved by reducing the occurrence of burrs during development.
本発明の黒色感光性樹脂組成物において、黒色顔料がチタンブラックを含むことが好ましい。このような黒色感光性樹脂組成物から形成されるブラックマトリクスは光学濃度及び電気抵抗をより一層高くすることができ、遮光性に優れるものとなる。 In the black photosensitive resin composition of the present invention, the black pigment preferably contains titanium black. The black matrix formed from such a black photosensitive resin composition can further increase the optical density and electrical resistance, and has excellent light shielding properties.
上記アクリル樹脂は、前記一般式(I)、(II)及び(III)で表される繰り返し単位並びに下記一般式(IV)で表される繰り返し単位を有するアクリル樹脂であることが好ましい。
ここで、R6は水素原子又はメチル基を示し、X2は単結合又は2価の有機基を示し、Zはヒドロキシル基又は置換基を有していてもよい炭素数1〜10のアルキル基を示し、hは0〜5の整数を示す。hが2以上の場合、複数のZは互いに同一でも異なっていてもよい。Zは水素原子又は1価の有機基を示す。これにより、黒色感光性樹脂組成物は、解像度に優れるのみでなく、密着性にも優れるものとなる。Here, R 6 represents a hydrogen atom or a methyl group, X 2 represents a single bond or a divalent organic group, Z represents an alkyl group having 1 to 10 carbon atoms which may have a hydroxyl group or a substituent. H represents an integer of 0-5. When h is 2 or more, the plurality of Z may be the same as or different from each other. Z represents a hydrogen atom or a monovalent organic group. Thereby, the black photosensitive resin composition is excellent not only in resolution but also in adhesion.
また、上記一般式(III)において、Yが下記一般式(vi)で表される2価の基であることが好ましい。
これにより、本発明の黒色感光性樹脂組成物は、解像度がより一層向上する。 Thereby, the resolution of the black photosensitive resin composition of the present invention is further improved.
本発明は、上記黒色感光性樹脂組成物からなるブラックマトリクス形成用感光液を提供する。このような感光液は取り扱い性に優れ、ブラックマトリクスを形成するために用いることができる。 The present invention provides a black matrix forming photosensitive solution comprising the above black photosensitive resin composition. Such a photosensitive solution is excellent in handleability and can be used to form a black matrix.
また、本発明は、上述した黒色感光性樹脂組成物からなる感光層に活性光線を照射した後、感光層の一部を除去してブラックマトリクスを形成させるブラックマトリクスの形成方法を提供する。 The present invention also provides a black matrix forming method in which a photosensitive layer comprising the above-described black photosensitive resin composition is irradiated with actinic rays and then a part of the photosensitive layer is removed to form a black matrix.
この形成方法によると、解像度が十分に高く、光学濃度及び電気抵抗値を十分に満足し遮光性に優れるブラックマトリクスを形成することができる。 According to this forming method, it is possible to form a black matrix having a sufficiently high resolution, sufficiently satisfying the optical density and electric resistance value, and excellent in light shielding properties.
さらに、本発明は、上記ブラックマトリクスの形成方法によりブラックマトリクスを形成する工程を備えるカラーフィルタの製造方法及び上記製造方法で得られるカラーフィルタを提供する。 Furthermore, this invention provides the manufacturing method of a color filter provided with the process of forming a black matrix by the formation method of the said black matrix, and the color filter obtained by the said manufacturing method.
上記製造方法によれば、従来よりもカラーフィルタの作製工程を簡略化することができる。さらに、このようなカラーフィルタは、上記黒色感光性樹脂組成物を用いて形成されたブラックマトリクスを備えるため、ブラックマトリクスの遮光性が十分に高く、カラーフィルタのコントラストを十分に向上できる。 According to the manufacturing method, the color filter manufacturing process can be simplified as compared with the conventional method. Furthermore, since such a color filter includes a black matrix formed using the black photosensitive resin composition, the black matrix has a sufficiently high light-shielding property and can sufficiently improve the contrast of the color filter.
本発明によれば、ブラックマトリクスとしての光学濃度及び電気抵抗値を十分に満足すると共に、解像度が十分に高い黒色感光性樹脂組成物及びこれを用いたブラックマトリクスの形成方法、カラーフィルタの製造方法並びにカラーフィルタを提供することができる。 According to the present invention, a black photosensitive resin composition sufficiently satisfying optical density and electric resistance value as a black matrix and having a sufficiently high resolution, a method for forming a black matrix using the same, and a method for producing a color filter In addition, a color filter can be provided.
以下、必要に応じて図面を参照しつつ、本発明の好適な実施形態について詳細に説明する。また、本明細書における「(メタ)アクリレート」とは、「アクリレート」及びそれに対応する「メタクリレート」を意味する。同様に「(メタ)アクリル」とは、「アクリル」及びそれに対応する「メタクリル」を意味し、「(メタ)アクリロイル」とは「アクリロイル」及びそれに対応する「メタクリロイル」を意味する。 Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the drawings as necessary. In addition, “(meth) acrylate” in the present specification means “acrylate” and “methacrylate” corresponding thereto. Similarly, “(meth) acryl” means “acryl” and “methacryl” corresponding thereto, and “(meth) acryloyl” means “acryloyl” and corresponding “methacryloyl”.
(黒色感光性樹脂組成物)
本発明の黒色感光性樹脂組成物は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料を含有する。(Black photosensitive resin composition)
The black photosensitive resin composition of the present invention contains a binder polymer, a photopolymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a black pigment.
黒色感光性樹脂組成物の解像度を十分に向上させる観点から、バインダーポリマーは、上記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂を含む。 From the viewpoint of sufficiently improving the resolution of the black photosensitive resin composition, the binder polymer contains an acrylic resin having a repeating unit represented by the general formulas (I), (II), and (III).
一般式(I)において、R1は水素原子又はメチル基を示す。In the general formula (I), R 1 represents a hydrogen atom or a methyl group.
一般式(II)において、R2は水素原子又はメチル基を示し、R3は上記式(i)、(ii)又は(iii)で表されるジシクロ環又はトリシクロ環を有する1価の基を示す。また、X1は単結合、炭素数1〜10のアルキレン基又は炭素数1〜10のオキシアルキレン基を示し、炭素数1〜5のアルキレン基又は炭素数1〜5のオキシアルキレン基を示すことが好ましい。In the general formula (II), R 2 represents a hydrogen atom or a methyl group, and R 3 represents a monovalent group having a dicyclo ring or a tricyclo ring represented by the above formula (i), (ii) or (iii). Show. X 1 represents a single bond, an alkylene group having 1 to 10 carbon atoms or an oxyalkylene group having 1 to 10 carbon atoms, and represents an alkylene group having 1 to 5 carbon atoms or an oxyalkylene group having 1 to 5 carbon atoms. Is preferred.
一般式(III)において、R4及びR5はそれぞれ独立に水素原子又はメチル基を示す。また、Yは単結合又は2価の有機基を示し、炭素数1〜10のオキシアルキレン基であることが好ましく、炭素数が2以上の場合、主鎖炭素原子間に酸素原子及び/又はウレタン結合を有してもよく、ヒドロキシル基で置換されていてもよい。解像度をより一層向上させる観点から、Yが上記一般式(iv)で表される2価の基であることがより好ましい。式(iv)中、m及びnはそれぞれ独立に1〜20の整数を示し、1〜5の整数を示すことが好ましい。In the general formula (III), R 4 and R 5 each independently represent a hydrogen atom or a methyl group. Y represents a single bond or a divalent organic group, and is preferably an oxyalkylene group having 1 to 10 carbon atoms. When the number of carbon atoms is 2 or more, oxygen atoms and / or urethanes between main chain carbon atoms It may have a bond and may be substituted with a hydroxyl group. From the viewpoint of further improving the resolution, Y is more preferably a divalent group represented by the above general formula (iv). In formula (iv), m and n each independently represent an integer of 1 to 20, preferably an integer of 1 to 5.
上記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の合成法は特に限定されないが、例えば、下記に示す方法A、B又はCにより得ることができる。 Although the synthesis method of the acrylic resin which has a repeating unit represented by the said general formula (I), (II) and (III) is not specifically limited, For example, it can obtain by the method A, B, or C shown below.
(方法A)
一般式(I)で表される繰り返し単位を形成するための(メタ)アクリル化合物(以下、「モノマーa」という)、一般式(II)で表される繰り返し単位を形成するための(メタ)アクリル化合物(以下、「モノマーb」という)及び一般式(III)で表される繰り返し単位を形成するためのジ(メタ)アクリル化合物(以下、「モノマーc」という)を共重合する。(Method A)
(Meth) acrylic compound (hereinafter referred to as “monomer a”) for forming the repeating unit represented by the general formula (I), (meth) for forming the repeating unit represented by the general formula (II) An acrylic compound (hereinafter referred to as “monomer b”) and a di (meth) acrylic compound (hereinafter referred to as “monomer c”) for forming a repeating unit represented by the general formula (III) are copolymerized.
(方法B)
上記モノマーa、上記モノマーb及び下記一般式(V)で表されるヒドロキシル基を有する(メタ)アクリル化合物(以下、「モノマーd」という)を共重合し、ポリマー主骨格を構築する。次いで、モノマーdと同モル数の下記一般式(VI)で表されるイソシアネート基を有する(メタ)アクリル化合物(以下、「モノマーe」という)とポリマー主骨格のヒドロキシル基とを反応させ、上記一般式(III)で表される繰り返し単位を形成する。(Method B)
The monomer a, the monomer b, and a (meth) acryl compound having a hydroxyl group represented by the following general formula (V) (hereinafter referred to as “monomer d”) are copolymerized to construct a polymer main skeleton. Subsequently, the (meth) acrylic compound (hereinafter referred to as “monomer e”) having the same number of moles as the monomer d and the isocyanate group represented by the following general formula (VI) is reacted with the hydroxyl group of the polymer main skeleton, and A repeating unit represented by the general formula (III) is formed.
(方法C)
上記モノマーa、上記モノマーb及び下記一般式(VII)で表されるエポキシ基を有する(メタ)アクリル化合物(以下、「モノマーf」という)を共重合し、ポリマー主骨格を構築する。次いで、モノマーfと同モル数の(メタ)アクリル酸とポリマー主骨格のエポキシ基と反応させ、上記一般式(III)で表される繰り返し単位を形成する。(Method C)
The monomer a, the monomer b, and a (meth) acrylic compound (hereinafter referred to as “monomer f”) having an epoxy group represented by the following general formula (VII) are copolymerized to construct a polymer main skeleton. Next, the same number of moles of (meth) acrylic acid as the monomer f and the epoxy group of the polymer main skeleton are reacted to form the repeating unit represented by the general formula (III).
しかしながら、これら方法A、B及びCのうち、方法B又はCによって上述のアクリル樹脂を合成することが好ましい。これにより、重合反応の制御が一層容易となり、得られるポリマーのゲル化をより有効に制御することができる。 However, among these methods A, B and C, it is preferable to synthesize the above-mentioned acrylic resin by method B or C. Thereby, control of a polymerization reaction becomes still easier and the gelation of the polymer obtained can be controlled more effectively.
モノマーaとしては、(メタ)アクリル酸が挙げられる。モノマーaの含有割合は、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の合成に用いられるモノマー総量を基準として、5〜50質量%であることが好ましく、10〜45質量%であることがより好ましく、10〜30質量%であることが更に好ましい。モノマーaの含有割合が5質量%未満では、アルカリ現像性が低下し、精細な画素パターンを得られ難くなる。モノマーaの含有割合が50質量%を超えると、黒色感光性樹脂組成物の粘度が高くなり取り扱い難くなると共に、アルカリ現像時にブラックマトリクスが剥離しやすくなる。 Examples of the monomer a include (meth) acrylic acid. The content ratio of the monomer a is 5 to 50% by mass based on the total amount of monomers used for the synthesis of the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III). Preferably, it is 10-45 mass%, More preferably, it is 10-30 mass%. When the content ratio of the monomer a is less than 5% by mass, the alkali developability is lowered and it becomes difficult to obtain a fine pixel pattern. When the content ratio of the monomer a exceeds 50 mass%, the viscosity of the black photosensitive resin composition becomes high and handling becomes difficult, and the black matrix is easily peeled off during alkali development.
モノマーbとしては、例えば、上記式(i)、(ii)又は(iii)で表されるジシクロ環又はトリシクロ環を有する(メタ)アクリル酸エステルが挙げられる。このモノマーは、ジシクロ環又はトリシクロ環の一方のみを有してもよく、両方を有していてもよい。具体的には、ジシクロペンテニル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デシル基を有する(メタ)アクリル酸エステルが挙げられる。特に、トリシクロ[5.2.1.02,6]デシル(メタ)アクリレート等のトリシクロ[5.2.1.02,6]デシル基を有する(メタ)アクリル酸エステル、又はトリシクロ[5.2.1.02,6]デシル基を有する(メタ)アクリル酸エステル樹脂が有効である。これらのモノマーは、1種を単独で又は2種以上を組み合わせて用いることができる。Examples of the monomer b include (meth) acrylic acid esters having a dicyclo ring or a tricyclo ring represented by the above formula (i), (ii), or (iii). This monomer may have only one of a dicyclo ring or a tricyclo ring, or may have both. Specific examples include dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and (meth) acrylic acid ester having a tricyclo [5.2.1.0 2,6 ] decyl group. In particular, tricyclo [5.2.1.0 2, 6] decyl (meth) acrylate tricyclo [5.2.1.0 2, 6] (meth) acrylic acid ester having a decyl group, etc., or tricyclo [5, .2.1.0 2,6 ] (meth) acrylic acid ester resin having a decyl group is effective. These monomers can be used alone or in combination of two or more.
モノマーbの含有割合は、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の合成に用いられるモノマー総量を基準として、3〜70質量%であることが好ましく、5〜60質量%であることがより好ましく、40〜60質量%であることが更に好ましい。モノマーbの含有割合が3質量%未満では、バインダーポリマーの透明性が低下し、光感度が低下する傾向がある。モノマーbの含有割合が70質量%を超えると、黒色感光性樹脂組成物の粘度が高くなり取り扱い難くなる。 The content ratio of the monomer b is 3 to 70% by mass based on the total amount of monomers used for the synthesis of the acrylic resin having the repeating units represented by the general formulas (I), (II), and (III). Preferably, it is 5-60 mass%, More preferably, it is 40-60 mass%. When the content ratio of the monomer b is less than 3% by mass, the transparency of the binder polymer is lowered and the photosensitivity tends to be lowered. When the content rate of the monomer b exceeds 70 mass%, the viscosity of the black photosensitive resin composition becomes high and handling becomes difficult.
モノマーcとしては、例えば、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート等のジ(メタ)アクリレート化合物が挙げられる。 Examples of the monomer c include diethylene methacrylate di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and the like. A (meth) acrylate compound is mentioned.
方法Bで用いられるモノマーdとしては、ヒドロキシル基を有する(メタ)アクリル化合物であれば特に限定されず、例えば、2−ヒドロキシエチル(メタ)アクリレート、3−ヒドロキシプロピル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレートを挙げることができる。また、モノマーeとしては、イソシアネート基を有する(メタ)アクリル化合物であれば、特に限定されず、例えば、2−イソシアネートエチル(メタ)アクリレートを挙げることができる。 The monomer d used in Method B is not particularly limited as long as it is a (meth) acrylic compound having a hydroxyl group. For example, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxy Mention may be made of butyl (meth) acrylate. The monomer e is not particularly limited as long as it is a (meth) acrylic compound having an isocyanate group, and examples thereof include 2-isocyanatoethyl (meth) acrylate.
方法Cで用いられるモノマーfとしては、エポキシ基を有する(メタ)アクリル化合物であれば特に限定されず、例えば、グリシジル(メタ)アクリレートを挙げることができる。モノマーc、モノマーd及び/又はモノマーfの含有割合は、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の合成に用いられるモノマー総量を基準として、5〜50質量%であることが好ましく、10〜45質量%であることがより好ましく、10〜30質量%であることが更に好ましい。5質量%未満では、パターン形成時間が遅くなり、本発明の効果を奏し難くなり、50質量%を超えると、黒色感光性樹脂組成物の粘度が高くなり、さらに、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の溶解性が低下する傾向にある。モノマーeの含有割合は、モノマーd1モルに対して、0.8〜1モルであることが好ましい。 The monomer f used in Method C is not particularly limited as long as it is a (meth) acrylic compound having an epoxy group, and examples thereof include glycidyl (meth) acrylate. The content ratio of the monomer c, the monomer d and / or the monomer f is 5 based on the total amount of monomers used for the synthesis of the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III). It is preferable that it is -50 mass%, It is more preferable that it is 10-45 mass%, It is still more preferable that it is 10-30 mass%. If it is less than 5% by mass, the pattern formation time is delayed, and it is difficult to achieve the effects of the present invention. If it exceeds 50% by mass, the viscosity of the black photosensitive resin composition increases, and the general formula (I), ( The solubility of the acrylic resin having the repeating units represented by II) and (III) tends to be lowered. It is preferable that the content rate of the monomer e is 0.8-1 mol with respect to 1 mol of monomers d.
密着性を向上させる観点から、バインダーポリマーは、上記一般式(I)、(II)及び(III)で表される繰り返し単位並びに上記一般式(IV)で表される繰り返し単位を有するアクリル樹脂を含むことが好ましい。 From the viewpoint of improving the adhesion, the binder polymer is an acrylic resin having a repeating unit represented by the general formulas (I), (II) and (III) and a repeating unit represented by the general formula (IV). It is preferable to include.
一般式(I)、(II)、(III)及び(IV)で表される繰り返し単位を有するアクリル樹脂の合成法は特に限定されないが、上記一般式(IV)で表される繰り返し単位を形成するための(メタ)アクリル化合物(以下、「モノマーg」という)を更に共重合することにより得られる。合成方法は、上記方法A、B及びCに準じて行なうことができる。 The method for synthesizing the acrylic resin having the repeating units represented by the general formulas (I), (II), (III) and (IV) is not particularly limited, but forms the repeating units represented by the general formula (IV). (Meth) acrylic compound (hereinafter referred to as “monomer g”) for further copolymerization. The synthesis method can be performed according to the above methods A, B and C.
モノマーgとしては、例えば、ベンジル(メタ)アクリレート、ノニルフェノキシポリエチレングリコール(メタ)アクリレート、α−(メタ)アクリロイル−ω−トリルオキシポリオキシエチレン、2−tert−ブチル−6−(3−tert−ブチル−2−ヒドロキシ−5−メチルベンジル)−4−メチルフェニル=アクリラート、2−tert−ブチル−6−〔1−(3−tert−ブチル−2−ヒドロキシ−5−メチルフェニル)エチル−4−メチルフェニル=アクリラートが挙げられる。これらのモノマーは1種を単独で又は2種以上を組み合わせて用いることができる。モノマー(g)の含有割合は、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の合成に用いられるモノマ成分総量を基準として、5〜50質量%であることが好ましく、10〜45質量%であることがより好ましく、10〜30質量%であることが更に好ましい。モノマーgの含有割合が5質量%未満では、形成するブラックマトリクスの解像度が低くなる傾向がある。モノマーgの含有割合が50質量%を超えると、形成するブラックマトリクスの密着性が低下する傾向がある。 Examples of the monomer g include benzyl (meth) acrylate, nonylphenoxypolyethylene glycol (meth) acrylate, α- (meth) acryloyl-ω-tolyloxypolyoxyethylene, 2-tert-butyl-6- (3-tert- Butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 2-tert-butyl-6- [1- (3-tert-butyl-2-hydroxy-5-methylphenyl) ethyl-4- Mention may be made of methylphenyl acrylate. These monomers can be used alone or in combination of two or more. The content ratio of the monomer (g) is 5 to 50% by mass based on the total amount of monomer components used in the synthesis of the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III). It is preferably 10 to 45% by mass, more preferably 10 to 30% by mass. When the content ratio of the monomer g is less than 5% by mass, the resolution of the black matrix to be formed tends to be low. When the content ratio of the monomer g exceeds 50% by mass, the adhesion of the black matrix to be formed tends to be lowered.
また、上記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂は、必要に応じて、上述したモノマーa、b、c、d、f又はgに加えて、その他の(メタ)アクリル化合物をモノマー成分として共重合してもよい。その他の(メタ)アクリル化合物としては、例えば、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸シクロヘキシル等の(メタ)アクリル酸アルキルエステル又は(メタ)アクリル酸シクロアルキルエステルが挙げられる。これらのモノマーは、1種を単独で又は2種以上を組み合わせて用いることができる。 In addition, the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III) may be added to the above-described monomers a, b, c, d, f or g as necessary. Other (meth) acrylic compounds may be copolymerized as monomer components. Other (meth) acrylic compounds include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ( Examples include (meth) acrylic acid alkyl esters such as methacrylic cyclohexyl or (meth) acrylic acid cycloalkyl esters. These monomers can be used alone or in combination of two or more.
さらに、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂は、必要に応じて、上記(メタ)アクリル酸に加えて、その他のカルボキシル基を有する重合性化合物をモノマー成分として共重合してもよい。このような重合性化合物としては、イタコン酸、マレイン酸、フマル酸、クロトン酸、シトラコン酸、メサコン酸又はα−クロロアクリル酸が挙げられる。 Furthermore, the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III) may be polymerized having other carboxyl groups in addition to the (meth) acrylic acid, if necessary. A compound may be copolymerized as a monomer component. Examples of such a polymerizable compound include itaconic acid, maleic acid, fumaric acid, crotonic acid, citraconic acid, mesaconic acid, and α-chloroacrylic acid.
なお、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂は、それぞれの繰り返し単位のランダム共重合体、ブロック共重合体又は交互共重合体のいずれであってもよい。 The acrylic resin having the repeating units represented by the general formulas (I), (II) and (III) is any of a random copolymer, a block copolymer or an alternating copolymer of each repeating unit. May be.
一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の重量平均分子量は、3000〜200000が好ましく、3000〜100000がより好ましく、5000〜50000が更に好ましく、10000〜40000が特に好ましい。重量平均分子量が3000未満では、耐アルカリ性が低下する傾向があり、重量平均分子量が200000を超えると、黒色感光性樹脂組成物の粘度が高くなるため、特に黒色感光性樹脂組成物をスピンコートする際の塗布性が低下する傾向がある。 3000-200000 are preferable, as for the weight average molecular weight of the acrylic resin which has a repeating unit represented by general formula (I), (II) and (III), 3000-100000 are more preferable, 5000-50000 are still more preferable, and 10,000. ˜40000 is particularly preferred. When the weight average molecular weight is less than 3000, the alkali resistance tends to decrease. When the weight average molecular weight exceeds 200000, the viscosity of the black photosensitive resin composition is increased, and thus the black photosensitive resin composition is particularly spin-coated. The applicability at the time tends to be reduced.
なお、本明細書における重量平均分子量は、ゲルパーミネーションクロマトグラフィー(GPC)分析により下記条件に従って測定し、標準ポリスチレンの検量線を使用して換算することにより求められる。
(GPC条件)
使用機器:日立L−6000型((株)日立製作所製、商品名)
検出器:L−3300RI((株)日立製作所製、商品名)
カラム:ゲルパックGL−R420+ゲルパックGL−R430+ゲルパックGL−R440(計3本)(日立化成工業(株)製、商品名)
溶離液:テトラヒドロフラン
測定温度:40℃
流量:1.75mL/minIn addition, the weight average molecular weight in this specification is calculated | required by measuring according to the following conditions by gel permeation chromatography (GPC) analysis, and converting using a standard polystyrene calibration curve.
(GPC conditions)
Equipment used: Hitachi L-6000 type (manufactured by Hitachi, Ltd., trade name)
Detector: L-3300RI (trade name, manufactured by Hitachi, Ltd.)
Column: Gel pack GL-R420 + Gel pack GL-R430 + Gel pack GL-R440 (3 in total) (trade name, manufactured by Hitachi Chemical Co., Ltd.)
Eluent: Tetrahydrofuran Measurement temperature: 40 ° C
Flow rate: 1.75 mL / min
また、バインダーポリマーは上記アクリル樹脂に加えて、他のアクリル樹脂、スチレン樹脂、エポキシ樹脂、ポリアミド樹脂、アミドエポキシ樹脂、アルキド樹脂、フェノール樹脂、エポキシ(メタ)アクリレート樹脂等の1種以上の樹脂を含むことができる。 In addition to the above acrylic resin, the binder polymer is made of one or more resins such as other acrylic resins, styrene resins, epoxy resins, polyamide resins, amide epoxy resins, alkyd resins, phenol resins, epoxy (meth) acrylate resins and the like. Can be included.
一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の含有割合は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料の総量に対して、5〜50質量%であることが好ましく、10〜30質量%であることがより好ましく、10〜20質量%であることが更に好ましい。一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の含有割合が5質量%未満では現像時に形成されたブラックマトリクスが剥離しやすくなる。一方、一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂の含有割合が50%を超えると黒色感光性樹脂組成物の粘度が高くなるため、特に、黒色感光性樹脂組成物をスピンコートする際の塗布性が低下する傾向がある。 The content ratio of the acrylic resin having the repeating units represented by the general formulas (I), (II), and (III) includes a binder polymer, a photopolymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a black pigment. It is preferable that it is 5-50 mass% with respect to the total amount of, It is more preferable that it is 10-30 mass%, It is still more preferable that it is 10-20 mass%. When the content ratio of the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III) is less than 5% by mass, the black matrix formed at the time of development is easily peeled off. On the other hand, when the content ratio of the acrylic resin having the repeating units represented by the general formulas (I), (II) and (III) exceeds 50%, the viscosity of the black photosensitive resin composition increases. There exists a tendency for the applicability | paintability at the time of spin-coating the photosensitive resin composition to fall.
エチレン性不飽和結合を有する光重合性化合物としては、例えば、メチル(メタ)アクリレート、ベンジル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、ブトキシトリエチレングリコール(メタ)アクリレート、エピクロルヒドリン(以下、「ECH」と表記する)変性ブチル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、エチレンオキシド(以下、「EO」と表記する)変性ジシクロペンテニル(メタ)アクリレート、N,N−ジメチルアミノエチル(メタ)アクリレート、エチルジエチレングリコール(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、グリセロール(メタ)アクリレート、ヘプタデカフロロデシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、カプロラクトン変性−2−ヒドロキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、メトキシジプロピレングリコール(メタ)アクリレート、メトキシ化シクロデカトリエン(メタ)アクリレート、フェノキシヘキサエチレングリコール(メタ)アクリレート、EO変性リン酸(メタ)アクリレート、カプロラクトン変性テトラヒドロフルフリル(メタ)アクリレート、EO変性ビスフェノールAジ(メタ)アクリレート、ECH変性ビスフェノールAジ(メタ)アクリレート、ビスフェノールAジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,3−ブチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、グリセロールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、EO変性リン酸ジ(メタ)アクリレート、ECH変性フタル酸ジ(メタ)アクリレート、ポリエチレングリコール400ジ(メタ)アクリレート、ポリプロピレングリコール400ジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ECH変性1,6−ヘキサンジオールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、EO変性リン酸トリ(メタ)アクリレート、EO変性トリメチロールプロパントリ(メタ)アクリレート、プロピレンオキシド(以下、「PO」と表記する)変性トリメチロールプロパントリ(メタ)アクリレート、トリス((メタ)アクリロキシエチル)イソシアヌレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレートが挙げられる。これらの化合物は、1種を単独で又は2種以上を組み合わせて用いることができる。 Examples of the photopolymerizable compound having an ethylenically unsaturated bond include methyl (meth) acrylate, benzyl (meth) acrylate, butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate, epichlorohydrin (hereinafter referred to as “ECH”). Modified butyl (meth) acrylate, dicyclopentanyl (meth) acrylate, ethylene oxide (hereinafter referred to as “EO”) modified dicyclopentenyl (meth) acrylate, N, N-dimethylaminoethyl (meta) ) Acrylate, ethyldiethylene glycol (meth) acrylate, 2-ethylhexyl (meth) acrylate, glycerol (meth) acrylate, heptadecafluorodecyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate Caprolactone-modified-2-hydroxyethyl (meth) acrylate, isobornyl (meth) acrylate, methoxydipropylene glycol (meth) acrylate, methoxylated cyclodecatriene (meth) acrylate, phenoxyhexaethylene glycol (meth) acrylate, EO modified Phosphoric acid (meth) acrylate, caprolactone modified tetrahydrofurfuryl (meth) acrylate, EO modified bisphenol A di (meth) acrylate, ECH modified bisphenol A di (meth) acrylate, bisphenol A di (meth) acrylate, 1,4-butane Diol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, glycerol di (meth) acrylate , Neopentyl glycol di (meth) acrylate, EO-modified phosphoric acid di (meth) acrylate, ECH-modified phthalic acid di (meth) acrylate, polyethylene glycol 400 di (meth) acrylate, polypropylene glycol 400 di (meth) acrylate, tetra Ethylene glycol di (meth) acrylate, ECH modified 1,6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, EO modified tri (meth) acrylate phosphate, EO Modified trimethylolpropane tri (meth) acrylate, propylene oxide (hereinafter referred to as “PO”) modified trimethylolpropane tri (meth) acrylate, tris ((meth) acryloxyethyl) Examples include isocyanurate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and dipentaerythritol penta (meth) acrylate. These compounds can be used individually by 1 type or in combination of 2 or more types.
エチレン性不飽和結合を有する光重合性化合物の含有割合は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料の総量に対して、2〜15質量%であることが好ましく、5〜10質量%であることがより好ましく、5〜8質量%であることが更に好ましい。 The content ratio of the photopolymerizable compound having an ethylenically unsaturated bond is 2 to 15% by mass with respect to the total amount of the binder polymer, the photopolymerizable compound having an ethylenically unsaturated bond, the photopolymerization initiator, and the black pigment. It is preferably 5 to 10% by mass, more preferably 5 to 8% by mass.
また、現像後の解像度を向上できる観点から、エチレン性不飽和結合を有する光重合性化合物に対するバインダーポリマーの質量比(以下、「ポリマー/モノマー比」ということもある。)は、2〜5であることが好ましく、2.5〜3.5であることがより好ましく、2.8〜3.4であることが更に好ましい。 In addition, from the viewpoint of improving the resolution after development, the mass ratio of the binder polymer to the photopolymerizable compound having an ethylenically unsaturated bond (hereinafter sometimes referred to as “polymer / monomer ratio”) is 2 to 5. Preferably, it is 2.5 to 3.5, more preferably 2.8 to 3.4.
光重合開始剤としては、例えば、ベンゾフェノン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン,N,N’−テトラエチル−4,4’−ジアミノベンゾフェノン、4−メトキシ−4’−ジメチルアミノベンゾフェノン、ベンジル、2,2−ジエトキシアセトフェノン、ベンゾイン、ベンゾインメチルエーテル、ベンゾインイソブチルエーテル、ベンジルジメチルケタール、α−ヒドロキシイソブチルフェノン、2−ベンジル−2−ジメチルアミノ−4’−モルフォリノブチロフェノン、チオキサントン、2−クロロチオキサントン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノ−1−プロパノン、t−ブチルアントラキノン、1−クロロアントラキノン、2,3−ジクロロアントラキノン、3−クロル−2−メチルアントラキノン、2−エチルアントラキノン、1,4−ナフトキノン、9,10−フェナントラキノン、1,2−ベンゾアントラキノン、1,4−ジメチルアントラキノン、2−フェニルアントラキノン、2−メルカプトベンゾイミダゾール、2−(o−クロロフェニル)−4,5−ジフェニルイミダゾール二量体が挙げられる。これらの光重合開始剤は、1種を単独で又は2種以上を組み合わせて使用される。 Examples of the photopolymerization initiator include benzophenone, 4,4′-bis (diethylamino) benzophenone, N, N′-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, benzyl, 2,2-diethoxyacetophenone, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzyldimethyl ketal, α-hydroxyisobutylphenone, 2-benzyl-2-dimethylamino-4′-morpholinobutyrophenone, thioxanthone, 2-chlorothioxanthone 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propanone, t-butylanthraquinone, 1-chloroanthraquinone, 2,3 Dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 1,2-benzoanthraquinone, 1,4-dimethylanthraquinone, 2-phenylanthraquinone 2-mercaptobenzimidazole and 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer. These photoinitiators are used individually by 1 type or in combination of 2 or more types.
光重合開始剤の含有割合は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料の総量に対して、2〜30質量%であることが好ましく、5〜15質量%であることがより好ましく、5〜10質量%であることが更に好ましい。光重合開始剤の含有割合が2質量%未満では、黒色感光性樹脂組成物の光感度が低くなる傾向があり、30質量%を越えると黒色感光性樹脂組成物からなる感光層の密着性が低下する傾向がある。 The content of the photopolymerization initiator is preferably 2 to 30% by mass with respect to the total amount of the binder polymer, the photopolymerizable compound having an ethylenically unsaturated bond, the photopolymerization initiator, and the black pigment, More preferably, it is 15 mass%, and it is still more preferable that it is 5-10 mass%. When the content of the photopolymerization initiator is less than 2% by mass, the photosensitivity of the black photosensitive resin composition tends to be low, and when it exceeds 30% by mass, the adhesion of the photosensitive layer made of the black photosensitive resin composition is low. There is a tendency to decrease.
黒色顔料としては,無機顔料及び有機顔料のいずれでもよく、1種を単独で又は2種以上の顔料を混合したものを用いてもよい。無機顔料としては、例えば、カーボンブラック、黒鉛、鉄黒、チタンカーボン、チタンブラック、二酸価マンガン、銅クロムマンガン酸化物を挙げることができる。着色力を向上する観点から、カーボンブラック又はチタンブラックが好ましい。さらに、光学濃度及び電気抵抗値を大きくできる観点から、チタンブラックがより好ましい。また、表面を樹脂等で被覆したカーボンブラック又はチタンブラックを使用することもできる。 As a black pigment, either an inorganic pigment or an organic pigment may be used, and one pigment may be used alone or a mixture of two or more pigments may be used. Examples of the inorganic pigment include carbon black, graphite, iron black, titanium carbon, titanium black, manganese diacid value, and copper chromium manganese oxide. From the viewpoint of improving coloring power, carbon black or titanium black is preferable. Furthermore, titanium black is more preferable from the viewpoint of increasing the optical density and the electrical resistance value. Carbon black or titanium black whose surface is coated with a resin or the like can also be used.
黒色顔料の含有割合は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料の総量に対して、20〜80質量%であることが好ましく、30〜70質量%であることがより好ましく、50〜70質量%であることが更に好ましい。黒色顔料の含有割合が20質量%未満では光学濃度が低くなる傾向にあり、80質量%を超えると光感度が低下する傾向にある。 The content ratio of the black pigment is preferably 20 to 80% by mass, and preferably 30 to 70% by mass with respect to the total amount of the binder polymer, the photopolymerizable compound having an ethylenically unsaturated bond, the photopolymerization initiator, and the black pigment. % Is more preferable, and 50 to 70% by mass is even more preferable. If the black pigment content is less than 20% by mass, the optical density tends to be low, and if it exceeds 80% by mass, the photosensitivity tends to decrease.
黒色顔料の種類及び含有割合は、ブラックマトリクスの光学濃度が2〜5になるように調整されることが好ましい。さらに、遮光性の観点から、光学濃度が3〜5になるように調整されることがより好ましい。ブラックマトリクスの光学濃度が2未満では遮光性が低下する傾向にあり、5を超えると黒色感光性樹脂組成物の現像性及び密着性が低下し、現像時に形成したブラックマトリクスが剥離しやすくなる。ここで、光学濃度は、例えば、デンシトメータ「PDA−65」(コニカ社製、商品名)で測定することができる。 The kind and content ratio of the black pigment are preferably adjusted so that the optical density of the black matrix is 2 to 5. Furthermore, it is more preferable that the optical density is adjusted to 3 to 5 from the viewpoint of light shielding properties. If the optical density of the black matrix is less than 2, the light-shielding property tends to be lowered. If the optical density exceeds 5, the developability and adhesion of the black photosensitive resin composition are lowered, and the black matrix formed during development is easily peeled off. Here, the optical density can be measured by, for example, a densitometer “PDA-65” (trade name, manufactured by Konica Corporation).
黒色感光性樹脂組成物の取り扱い性及び黒色顔料の分散性の観点から、黒色感光性樹脂組成物は、有機溶剤を含有することが好ましい。有機溶剤としては、例えば、ケトン化合物、アルキレングリコールエーテル化合物、アルコール化合物、芳香族化合物などが挙げられる。具体的には、ケトン化合物として、アセトン、メチルエチルケトン、シクロヘキサノン等が挙げられる。アルキレングリコールエーテル化合物として、メチルセロソルブ、エチルセロソルブ、ブチルセロソルブ、メチルセロソルブアセテート、エチルセロソルブアセテート、ブチルセロソルブアセテート、エチレングリコールモノプロピルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールジメチルエーテル、ジエチレングリコールエチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテルアセテート、ジエチレングリコールメチルエーテルアセテート、ジエチレングリコールエチルエーテルアセテート、ジエチレングリコールプロピルエーテルアセテート、ジエチレングリコールイソプロピルエーテルアセテート、ジエチレングリコールブチルエーテルアセテート、ジエチレングリコール−t−ブチルエーテルアセテート、トリエチレングリコールメチルエーテルアセテート、トリエチレングリコールエチルエーテルアセテート、トリエチレングリコールプロピルエーテルアセテート、トリエチレングリコールイソプロピルエーテルアセテート、トリエチレングリコールブチルエーテルアセテート、トリエチレングリコール−t−ブチルエーテルアセテート等が挙げられる。アルコール化合物として、メチルアルコール、エチルアルコール、イソプロピルアルコール、n−ブチルアルコール、3−メチル−3−メトキシブタノール等が挙げられる。芳香族化合物として、ベンゼン、トルエン、キシレンが挙げられる。その他として、N−メチル−2−ピロリドン、N−ヒドロキシメチル−2−ピロリドン等3−メチル−3−メトキシブチルアセテート、酢酸エチル、テトラヒドロフラン、ジオキサン等の有機溶剤が挙げられる。これらの有機溶剤は1種を単独で又は2種以上を組み合わせて用いることができる。 From the viewpoint of the handleability of the black photosensitive resin composition and the dispersibility of the black pigment, the black photosensitive resin composition preferably contains an organic solvent. Examples of the organic solvent include ketone compounds, alkylene glycol ether compounds, alcohol compounds, and aromatic compounds. Specific examples of the ketone compound include acetone, methyl ethyl ketone, and cyclohexanone. As alkylene glycol ether compounds, methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, diethylene glycol diethyl ether, propylene Glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate , Diethylene glycol propyl ether acetate, diethylene glycol isopropyl ether acetate, diethylene glycol butyl ether acetate, diethylene glycol-t-butyl ether acetate, triethylene glycol methyl ether acetate, triethylene glycol ethyl ether acetate, triethylene glycol propyl ether acetate, triethylene glycol isopropyl ether Examples include acetate, triethylene glycol butyl ether acetate, and triethylene glycol tert-butyl ether acetate. Examples of the alcohol compound include methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, 3-methyl-3-methoxybutanol and the like. Examples of aromatic compounds include benzene, toluene, and xylene. Other examples include organic solvents such as 3-methyl-3-methoxybutyl acetate such as N-methyl-2-pyrrolidone and N-hydroxymethyl-2-pyrrolidone, ethyl acetate, tetrahydrofuran and dioxane. These organic solvents can be used alone or in combination of two or more.
有機溶剤は、本発明に係る黒色感光性樹脂組成物中の全固形分が5〜50質量%になるように用いられることが好ましい。全固形分が50質量%を超えると粘度が高くなり、塗布性が悪くなる傾向がある。全固形分が5質量%未満では粘度が低くなり、塗布性が悪くなる傾向がある。 The organic solvent is preferably used so that the total solid content in the black photosensitive resin composition according to the present invention is 5 to 50% by mass. If the total solid content exceeds 50% by mass, the viscosity tends to be high and the applicability tends to be poor. If the total solid content is less than 5% by mass, the viscosity tends to be low and the applicability tends to be poor.
本発明の黒色感光性樹脂組成物は、暗反応を抑制するための熱重合禁止剤(ハイドロキノン、ハイドロキノンモノメチルエーテル、ピロガロール、t−ブチルカテコール等)、基板との密着性を向上させるためのチタネートカップリング剤(ビニル基、エポキシ基、アミノ基、メルカプト基等を有したシランカップリング剤やイソプロピルトリメタクリロイルチタネート、ジイソプロピルイソステアロイル−4−アミノベンゾイルチタネート等)、膜の平滑性を向上させるための界面活性剤(フッ素系、シリコン系、炭化水素系等)、紫外線吸収剤又は酸化防止剤等の各種添加剤を適宜使用することができる。 The black photosensitive resin composition of the present invention comprises a thermal polymerization inhibitor (hydroquinone, hydroquinone monomethyl ether, pyrogallol, t-butylcatechol, etc.) for suppressing a dark reaction, and a titanate cup for improving adhesion to a substrate. Ring agent (silane coupling agent having vinyl group, epoxy group, amino group, mercapto group, isopropyl trimethacryloyl titanate, diisopropylisostearoyl-4-aminobenzoyl titanate, etc.), interface for improving the smoothness of the film Various additives such as activators (fluorine-based, silicon-based, hydrocarbon-based, etc.), ultraviolet absorbers or antioxidants can be used as appropriate.
黒色感光性樹脂組成物は、バインダーポリマー、エチレン性不飽和結合を有する光重合性化合物、光重合開始剤及び黒色顔料を有機溶剤中で混合/分散する分散工程により調整することができる。 The black photosensitive resin composition can be prepared by a dispersion process in which a binder polymer, a photopolymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a black pigment are mixed / dispersed in an organic solvent.
分散方法としては、超音波分散機、3本ロール、ボールミル、サンドミル、ビーズミル、ホモジナイザー、ニーダー等の分散/混練装置を用いる公知の方法が挙げられる。 Examples of the dispersion method include known methods using a dispersion / kneading apparatus such as an ultrasonic disperser, three rolls, a ball mill, a sand mill, a bead mill, a homogenizer, and a kneader.
分散工程において、まず、バインダーポリマー、黒色顔料及び有機溶剤を上述の装置を用い混合/分散し、黒色顔料をバインダーポリマー溶液中に均一に分散させることが好ましい。 In the dispersing step, it is preferable that the binder polymer, the black pigment and the organic solvent are first mixed / dispersed using the above-described apparatus to uniformly disperse the black pigment in the binder polymer solution.
エチレン性不飽和結合を有する光重合性化合物及び光重合開始剤は、バインダーポリマーと一緒に黒色顔料分散時に添加してもよく、黒色顔料が分散した後に添加してもよい。 The photopolymerizable compound having an ethylenically unsaturated bond and the photopolymerization initiator may be added together with the binder polymer when the black pigment is dispersed, or may be added after the black pigment is dispersed.
バインダーポリマーは、その全量を黒色顔料と共に混合してもよく、その一部を黒色顔料と共に混合し、残りを黒色顔料が分散した後に添加してもよい。ただし、黒色顔料分散時のバインダーポリマーの添加量は、黒色顔料100質量部に対し、20質量部以上であることが好ましい。バインダーポリマーの添加量が20質量部未満では、黒色顔料の分散安定性が低下する傾向がある。 The whole amount of the binder polymer may be mixed with the black pigment, a part thereof may be mixed with the black pigment, and the rest may be added after the black pigment is dispersed. However, the amount of the binder polymer added when dispersing the black pigment is preferably 20 parts by mass or more with respect to 100 parts by mass of the black pigment. If the addition amount of the binder polymer is less than 20 parts by mass, the dispersion stability of the black pigment tends to be lowered.
同様に、有機溶剤も黒色顔料分散時にその全量を添加してもよく、有機溶剤の一部を黒色顔料分散時に添加し、残りを黒色顔料が分散した後に添加してもよい。ただし、黒色顔料分散時に添加する有機溶剤の添加割合は、分散時の黒色顔料及びバインダーポリマー100質量部に対して、少なくとも100質量部であることが好ましい。この有機溶剤の添加割合が100質量部未満では分散時の粘度が高くなるため、特にボールミル、サンドミル、ビーズミルで分散する場合、黒色顔料を分散し難くなる。 Similarly, the organic solvent may be added in its entirety when the black pigment is dispersed, or a part of the organic solvent may be added when the black pigment is dispersed, and the rest may be added after the black pigment is dispersed. However, the addition ratio of the organic solvent added at the time of dispersing the black pigment is preferably at least 100 parts by mass with respect to 100 parts by mass of the black pigment and the binder polymer at the time of dispersion. When the addition ratio of the organic solvent is less than 100 parts by mass, the viscosity at the time of dispersion becomes high. Therefore, particularly when dispersed by a ball mill, sand mill, or bead mill, it is difficult to disperse the black pigment.
上記黒色顔料の分散時に、分散剤を添加してもよい。分散剤としては、例えば、ポリカルボン酸型高分子活性剤、ポリスルホン型高分子活性剤等のアニオン系顔料分散剤;ポリオキシエチレン・ポリプロピレンブロックポリマー等の顔料分散剤;アントラキノン系、ペリレン系、フタロシアニン系、キナクリドン系等の有機顔料にカルボキシル基、スルホ基、スルホン酸塩基、カルボン酸アミド基、スルホン酸アミド基、ヒドロキシル基等の官能基を有する有機顔料の誘導体を添加することができる。これにより、黒色顔料の分散性及び分散安定性が向上する。分散剤の添加割合は、黒色顔料100質量部に対して50質量部以下で用いることが好ましい。 You may add a dispersing agent at the time of dispersion | distribution of the said black pigment. Examples of the dispersant include anionic pigment dispersants such as polycarboxylic acid type polymer activator and polysulfone type polymer activator; pigment dispersants such as polyoxyethylene / polypropylene block polymer; anthraquinone type, perylene type, phthalocyanine Organic pigment derivatives having a functional group such as a carboxyl group, a sulfo group, a sulfonate group, a carboxylic acid amide group, a sulfonic acid amide group, and a hydroxyl group can be added to organic pigments such as those based on quinacridone. Thereby, the dispersibility and dispersion stability of the black pigment are improved. The addition ratio of the dispersant is preferably 50 parts by mass or less with respect to 100 parts by mass of the black pigment.
(ブラックマトリクスの形成方法)
本発明のブラックマトリクスの形成方法は、上述した黒色感光性樹脂組成物からなる感光層に活性光線を照射した後、感光層の一部を除去してブラックマトリクスを得るものである。(Black matrix formation method)
In the method for forming a black matrix of the present invention, the photosensitive layer comprising the above-described black photosensitive resin composition is irradiated with actinic rays, and then a part of the photosensitive layer is removed to obtain a black matrix.
より具体的に説明すると、このブラックマトリクスの形成方法は、黒色感光性樹脂組成物からなる感光層を基板上に積層する積層工程と、積層された感光層の所定部分に活性光線を照射する露光工程と、活性光線を照射した感光層を現像してブラックマトリクスを形成する現像工程を備えることが好ましい。 More specifically, this black matrix forming method includes a laminating step of laminating a photosensitive layer made of a black photosensitive resin composition on a substrate, and exposure in which a predetermined portion of the laminated photosensitive layer is irradiated with actinic rays. It is preferable to include a step and a developing step of developing the photosensitive layer irradiated with actinic rays to form a black matrix.
積層工程では、黒色感光性樹脂組成物を直接基板上に塗布又は印刷することによって感光層を形成する。あるいは、黒色感光性樹脂組成物を一旦、別の支持体上に塗布又は印刷して感光層を形成した後、その感光層を基板上に転写して、基板上に感光層を積層する。 In the laminating step, the photosensitive layer is formed by coating or printing the black photosensitive resin composition directly on the substrate. Alternatively, the black photosensitive resin composition is once applied or printed on another support to form a photosensitive layer, and then the photosensitive layer is transferred onto the substrate, and the photosensitive layer is laminated on the substrate.
黒色感光性樹脂組成物が流動性を有する場合、黒色感光性樹脂組成物をそのまま感光層を形成するために用いることができる。しかしながら、取り扱い性の観点から、黒色感光性樹脂組成物に有機溶剤を添加して低粘度化させて感光液として用いることが好ましい。この場合、黒色感光性樹脂組成物が有機溶媒を含有する場合であっても、有機溶剤を更に添加して、所定の粘度に調整してから使用することも可能である。添加する有機溶剤としては、上述した有機溶剤と同様のものを用いることができる。 When the black photosensitive resin composition has fluidity, the black photosensitive resin composition can be used as it is to form a photosensitive layer. However, from the viewpoint of handleability, it is preferable to add an organic solvent to the black photosensitive resin composition to lower the viscosity and use it as a photosensitive solution. In this case, even when the black photosensitive resin composition contains an organic solvent, it can be used after further adding an organic solvent to adjust the viscosity to a predetermined level. As the organic solvent to be added, the same organic solvents as described above can be used.
黒色感光性樹脂組成物を塗布する方法としては、例えば、ドクターブレードコーティング法、ダイコーティング法、ロールコーティング法、コンマコーティング法、スピンコーティング法、スプレーコーティング法、ホエラーコーティング法、ディップコーティング法、カーテンーコーティング法、ワイヤーバーコーティング法、グラビアコーティング法、エアナイフコーティング法が挙げられる。また、黒色感光性樹脂組成物が有機溶剤を含む場合、有機溶剤の除去は、例えば、加熱により行うことができる。その場合の加熱温度は50〜130℃であると好ましく、加熱時間は1〜30分間であると好ましい。 Examples of methods for applying the black photosensitive resin composition include a doctor blade coating method, a die coating method, a roll coating method, a comma coating method, a spin coating method, a spray coating method, a whaler coating method, a dip coating method, a car coating method, and the like. Examples include ten coating, wire bar coating, gravure coating, and air knife coating. Moreover, when a black photosensitive resin composition contains the organic solvent, the removal of the organic solvent can be performed by heating, for example. In that case, the heating temperature is preferably 50 to 130 ° C., and the heating time is preferably 1 to 30 minutes.
また、塗布によって感光層を形成する他に、オフセット印刷法、グラビア印刷法、スクリーン印刷法、インクジェット印刷法等の印刷法により感光層を形成することもできる。 In addition to forming the photosensitive layer by coating, the photosensitive layer can also be formed by a printing method such as an offset printing method, a gravure printing method, a screen printing method, or an ink jet printing method.
支持体上に感光層を形成した後の基板上への感光層の積層方法としては、基板上に感光層面を重ねて感光層を加熱しながら基板に圧着することにより積層する方法が挙げられる。また、密着性及び追従性を向上させる観点から、減圧下で積層することが好ましい。なお、支持体は、基板に感光層を転写してから剥離することが好ましい。 As a method of laminating the photosensitive layer on the substrate after forming the photosensitive layer on the support, a method of laminating by laminating the photosensitive layer surface on the substrate and pressing the photosensitive layer on the substrate while heating is mentioned. Moreover, it is preferable to laminate | stack under reduced pressure from a viewpoint of improving adhesiveness and followable | trackability. The support is preferably peeled off after the photosensitive layer is transferred to the substrate.
感光層の厚さは、用途によって適宜設定することができ、例えば、0.1〜10μmであることが好ましく、0.2〜5μmであることがより好ましい。感光層の厚さが0.1μm未満であると、所望の厚さに塗布し難くなる傾向にあり、一方、10μmを超えると、ブラックマトリクスの密着性及び解像度が低下する傾向がある。 The thickness of the photosensitive layer can be appropriately set depending on the application, and is preferably 0.1 to 10 μm, and more preferably 0.2 to 5 μm, for example. If the thickness of the photosensitive layer is less than 0.1 μm, it tends to be difficult to apply to a desired thickness, while if it exceeds 10 μm, the adhesion and resolution of the black matrix tend to be reduced.
支持体としては、例えば、ポリエチレンフィルム、ポリプロピレンフィルム、アクリル樹脂フィルム、ポリエステルフィルムを用いることができる。 As the support, for example, a polyethylene film, a polypropylene film, an acrylic resin film, or a polyester film can be used.
基板は、用途により適宜選択され、例えば、白板ガラス、青板ガラス、シリカコート青板ガラス等の透明ガラス板;ポリエステル樹脂、ポリカーボネート樹脂、アクリル樹脂、塩化ビニル樹脂等の合成樹脂製シート、フィルム又は板;アルミニウム板、銅板、ニッケル板、ステンレス板等の金属板;その他セラミック板;光電変換素子を有する半導体基板が挙げられる。 A board | substrate is suitably selected according to a use, for example, transparent glass plates, such as white plate glass, blue plate glass, and silica coat blue plate glass; Sheets, films, or plates made of synthetic resin such as polyester resin, polycarbonate resin, acrylic resin, and vinyl chloride resin; Metal plates such as aluminum plates, copper plates, nickel plates, stainless steel plates, etc .; other ceramic plates; semiconductor substrates having photoelectric conversion elements.
露光工程では、基材上の感光層の所定部分に活性光線を照射し、照射部分を硬化させて露光部を形成する。所定部分に活性光線を照射する方法としては、アートワークと呼ばれるネガ又はポジマスクパターンを通して活性光線を画像状に照射し、露光部を光硬化する方法が挙げられる。この際、感光層上に支持体が存在する場合、支持体が透明なら、そのまま、活性光線を照射することができ、支持体が活性光線に対して遮光性を示すなら、支持体を除去した後に、活性光線を感光層に照射する。一方、感光層を基板上に直接形成した場合には、そのまま、活性光線を照射することができる。また、感光層表面にポリビニルアルコール等の酸素遮断膜を0.5〜30μmの厚みで形成した後、その上から活性光線を照射することもできる。 In the exposure step, a predetermined portion of the photosensitive layer on the substrate is irradiated with actinic rays, and the irradiated portion is cured to form an exposed portion. Examples of the method of irradiating a predetermined portion with actinic rays include a method of irradiating actinic rays in an image form through a negative or positive mask pattern called an artwork and photocuring the exposed portion. At this time, when a support is present on the photosensitive layer, if the support is transparent, it can be irradiated with actinic rays as it is, and if the support shows a light-shielding property against actinic rays, the support is removed. Later, the photosensitive layer is irradiated with actinic rays. On the other hand, when the photosensitive layer is directly formed on the substrate, it can be irradiated with actinic rays as it is. Moreover, after forming oxygen barrier film, such as polyvinyl alcohol by the thickness of 0.5-30 micrometers, on the surface of a photosensitive layer, actinic light can also be irradiated from it.
活性光線の光源としては、従来公知の光源、例えば、カーボンアーク灯、水銀蒸気アーク灯、超高圧水銀灯、高圧水銀灯、キセノンランプ、メタルハライドランプ、蛍光ランプ、タングステンランプ、可視光レーザーが用いられる。 As the active light source, conventionally known light sources such as carbon arc lamps, mercury vapor arc lamps, ultrahigh pressure mercury lamps, high pressure mercury lamps, xenon lamps, metal halide lamps, fluorescent lamps, tungsten lamps, and visible light lasers are used.
上述のようにマスクパターンを介して行うマスク露光法以外に、レーザー直接描画露光法及びDLP露光法等の直接描画露光法により感光層の所定部分に活性光線を照射して露光部を光硬化せしめることができる。 In addition to the mask exposure method performed through the mask pattern as described above, the exposed portion is irradiated with actinic rays by a direct drawing exposure method such as a laser direct drawing exposure method and a DLP exposure method, and the exposed portion is photocured. be able to.
現像工程においては、現像液を直接感光層に吹き付けるか、あるいは現像液に感光層を浸漬することによって、感光層の未露光部を除去する。現像液としては、アルカリ性水溶液、水系現像液及び有機溶剤を用いることができる。これらのうち、アルカリ性水溶液が、安全かつ安定であり、操作性が良好であることから特に好ましい。 In the development step, the unexposed portion of the photosensitive layer is removed by spraying the developer directly on the photosensitive layer or immersing the photosensitive layer in the developer. As the developer, an alkaline aqueous solution, an aqueous developer and an organic solvent can be used. Of these, alkaline aqueous solutions are particularly preferred because they are safe and stable and have good operability.
アルカリ性水溶液の現像液における塩基としては、例えば、リチウム、ナトリウム又はカリウムの水酸化物等の水酸化アルカリ;リチウム、ナトリウム、カリウム若しくはアンモニウムの炭酸塩又は重炭酸塩等の炭酸アルカリ;リン酸カリウム、リン酸ナトリウム等のアルカリ金属リン酸塩;ピロリン酸ナトリウム、ピロリン酸カリウム等のアルカリ金属ピロリン酸塩が挙げられる。また、アルカリ性水溶液の現像液としては、0.1〜5質量%炭酸ナトリウムの希薄溶液、0.1〜5質量%炭酸カリウムの希薄溶液、0.1〜5質量%水酸化ナトリウムの希薄溶液、0.1〜5質量%四ホウ酸ナトリウムの希薄溶液等を用いることがより好ましい。さらに、アルカリ性水溶液のpHは、9〜11の範囲とすることが好ましく、その温度は、感光層の現像性に合わせて調整することができる。また、アルカリ性水溶液中には、表面活性剤、消泡剤、現像を促進させるための少量の有機溶剤等を添加してもよい。 Examples of the base in the alkaline aqueous developer include alkali hydroxides such as lithium, sodium or potassium hydroxide; alkali carbonates such as lithium, sodium, potassium or ammonium carbonate or bicarbonate; potassium phosphate, Examples thereof include alkali metal phosphates such as sodium phosphate; alkali metal pyrophosphates such as sodium pyrophosphate and potassium pyrophosphate. Examples of the alkaline aqueous developer include a dilute solution of 0.1 to 5% by mass sodium carbonate, a dilute solution of 0.1 to 5% by mass potassium carbonate, a dilute solution of 0.1 to 5% by mass sodium hydroxide, It is more preferable to use a dilute solution of 0.1 to 5% by mass sodium tetraborate. Furthermore, the pH of the alkaline aqueous solution is preferably in the range of 9 to 11, and the temperature can be adjusted according to the developability of the photosensitive layer. In the alkaline aqueous solution, a surfactant, an antifoaming agent, a small amount of an organic solvent for promoting development, and the like may be added.
水系現像液としては、水又はアルカリ水溶液と1種以上の有機溶剤とからなるものが挙げられる。ここで、アルカリ水溶液の塩基としては、上記の塩基以外に、例えば、ホウ砂やメタケイ酸ナトリウム、水酸化テトラメチルアンモニウム、エタノールアミン、エチレンジアミン、ジエチレントリアミン、2−アミノ−2−ヒドロキシメチル−1,3−プロパンジオール、1,3−ジアミノプロパノール−2、モルホリンが挙げられる。有機溶剤としては、例えば、三アセトンアルコール、アセトン、酢酸エチル、炭素数1〜4のアルコキシ基をもつアルコキシエタノール、エチルアルコール、イソプロピルアルコール、ブチルアルコール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル及びジエチレングリコールモノブチルエーテルが挙げられる。これらは、1種を単独で又は2種類以上を組み合わせて使用される。 Examples of the aqueous developer include those composed of water or an alkaline aqueous solution and one or more organic solvents. Here, as the base of the alkaline aqueous solution, in addition to the above bases, for example, borax, sodium metasilicate, tetramethylammonium hydroxide, ethanolamine, ethylenediamine, diethylenetriamine, 2-amino-2-hydroxymethyl-1,3 -Propanediol, 1,3-diaminopropanol-2, morpholine. Examples of the organic solvent include triacetone alcohol, acetone, ethyl acetate, alkoxyethanol having an alkoxy group having 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monobutyl ether. Is mentioned. These are used individually by 1 type or in combination of 2 or more types.
水系現像液は、有機溶剤の濃度を2〜90質量%とすることが好ましく、その温度は、感光層の現像性に合わせて調整することができる。さらに、水系現像液のpHは、ブラックマトリクスの現像が十分にできる範囲でできるだけ小さくすることが好ましい。具体的には、水系現像液のpHは、pH8〜12とすることが好ましく、pH9〜10とすることがより好ましい。また、水系現像液中には、界面活性剤、消泡剤等を少量添加してもよい。 The aqueous developer preferably has an organic solvent concentration of 2 to 90% by mass, and the temperature can be adjusted according to the developability of the photosensitive layer. Furthermore, the pH of the aqueous developer is preferably as low as possible within a range where the black matrix can be sufficiently developed. Specifically, the pH of the aqueous developer is preferably 8 to 12, and more preferably 9 to 10. A small amount of a surfactant, an antifoaming agent or the like may be added to the aqueous developer.
有機溶剤系現像液としては、例えば、1,1,1−トリクロロエタン、N−メチルピロリドン、N,N−ジメチルホルムアミド、シクロヘキサノン、メチルイソブチルケトン、γ−ブチロラクトン等が挙げられる。これらの有機溶剤は、引火防止のため、1〜20質量%の範囲で水を添加することが好ましい。 Examples of the organic solvent developer include 1,1,1-trichloroethane, N-methylpyrrolidone, N, N-dimethylformamide, cyclohexanone, methyl isobutyl ketone, and γ-butyrolactone. These organic solvents preferably add water in the range of 1 to 20% by mass in order to prevent ignition.
こうして、画像に対応した所望のパターンを有するブラックマトリクスを基板上に形成することができる。現像後、形成したブラックマトリクスをより強固に硬化させるため、後加熱(ポストベーク)を行うことが好ましい。この場合、加熱温度は60〜280℃が好ましく、加熱時間は1〜60分間が好ましい。 Thus, a black matrix having a desired pattern corresponding to the image can be formed on the substrate. After development, it is preferable to perform post-heating (post-bake) in order to harden the formed black matrix more firmly. In this case, the heating temperature is preferably 60 to 280 ° C., and the heating time is preferably 1 to 60 minutes.
(カラーフィルタの製造方法及びカラーフィルタ)
本発明のカラーフィルタの製造方法は、上述のブラックマトリクスの形成方法によりブラックマトリクスを形成する工程を備える。このカラーフィルタの製造方法において、ブラックマトリクスを形成する工程を上記工程とする以外は、公知と同様の方法によって、カラーフィルタを製造すればよい。こうして、本発明に係るカラーフィルタが得られる。このようなカラーフィルタは、ブラックマトリクスの遮光性が高いため、コントラストを十分に向上できる。(Color filter manufacturing method and color filter)
The color filter manufacturing method of the present invention includes a step of forming a black matrix by the above-described black matrix forming method. In this color filter manufacturing method, the color filter may be manufactured by a method similar to a known method except that the step of forming the black matrix is the above step. Thus, the color filter according to the present invention is obtained. Such a color filter can sufficiently improve the contrast because the black matrix has a high light shielding property.
以上、本発明の好適な実施形態について説明したが、本発明はこれに制限されるものではない。 As mentioned above, although preferred embodiment of this invention was described, this invention is not restrict | limited to this.
以下に、本発明を実施例に基づいて具体的に説明するが、本発明はこれに限定されるものではない。 Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited thereto.
(1)アクリル樹脂の合成
(合成例1)
1Lの四つ口フラスコにプロピレングリコールモノメチルエーテルアセテート210gを入れ、窒素をバブリングしながら液温を120℃に保ち、溶液aとした。次いで、1Lビーカーにジシクロペンタニルアクリレート170g、2−ヒドロキシエチルメタクリレート50g及びメタクリル酸30gを入れ、窒素をバブリングしながら溶解させ、溶解後、2,2’−アゾビスイソブチロニトリル3gを加え、溶液bとした。次に、溶液bを120℃に保たれている溶液aへ2時間かけて滴下し、滴下終了後、120℃で2時間反応を行った。(1) Synthesis of acrylic resin (Synthesis Example 1)
Into a 1 L four-necked flask, 210 g of propylene glycol monomethyl ether acetate was added, and the liquid temperature was kept at 120 ° C. while bubbling nitrogen to obtain a solution a. Next, 170 g of dicyclopentanyl acrylate, 50 g of 2-hydroxyethyl methacrylate and 30 g of methacrylic acid were put into a 1 L beaker, dissolved while bubbling nitrogen, and after dissolution, 3 g of 2,2′-azobisisobutyronitrile was added. Solution b was obtained. Next, the solution b was dripped at the solution a currently hold | maintained at 120 degreeC over 2 hours, and reaction was performed at 120 degreeC after completion | finish of dripping for 2 hours.
上記120℃での反応中、反応溶液へ2,2’−アゾビスイソブチロニトリル0.3gをプロピレングリコールモノメチルエーテルアセテート70gに溶解した溶液を数回に分けて添加した。次いで、140℃まで反応溶液の液温を上昇させ、140℃で1時間保持した後、自然冷却した。その後、ジブチルスズジラウリレート0.1g、2−イソシアネートエチルアクリレート50g及びメチルハイドロキノン0.5gを反応溶液に加えた。更に、75℃で2時間撹拌し、乳酸メチル120gで希釈してアクリル樹脂Aの溶液を得た。アクリル樹脂Aの重量平均分子量は、30000であった。 During the reaction at 120 ° C., a solution prepared by dissolving 0.3 g of 2,2′-azobisisobutyronitrile in 70 g of propylene glycol monomethyl ether acetate was added to the reaction solution in several portions. Subsequently, the liquid temperature of the reaction solution was raised to 140 ° C., held at 140 ° C. for 1 hour, and then naturally cooled. Thereafter, 0.1 g of dibutyltin dilaurate, 50 g of 2-isocyanatoethyl acrylate and 0.5 g of methylhydroquinone were added to the reaction solution. Further, the mixture was stirred at 75 ° C. for 2 hours and diluted with 120 g of methyl lactate to obtain an acrylic resin A solution. The weight average molecular weight of the acrylic resin A was 30000.
(合成例2)
ジシクロペンタニルアクリレート170g、2−ヒドロキシエチルメタクリレート50g及びメタクリル酸30gに代えて、ジシクロペンタニルアクリレート140g、ベンジルメタクリレート30g、2−ヒドロキシエチルメタクリレート50g及びメタクリル酸30gを用い溶液bを調整した以外は、合成例1と同様の操作を行い、アクリル樹脂Bの溶液を得た。アクリル樹脂Bの重量平均分子量は、30000であった。(Synthesis Example 2)
The solution b was adjusted using 170 g of dicyclopentanyl acrylate, 50 g of 2-hydroxyethyl methacrylate and 30 g of methacrylic acid, and using 140 g of dicyclopentanyl acrylate, 30 g of benzyl methacrylate, 50 g of 2-hydroxyethyl methacrylate and 30 g of methacrylic acid. Performed the same operation as the synthesis example 1, and obtained the solution of the acrylic resin B. The weight average molecular weight of the acrylic resin B was 30000.
(合成例3)
1Lの四つ口フラスコにビスフェノールF/クレゾールノボラック共重合型エポキシ樹脂(東都化成社製、商品名「YDPF−1000」)280g、アクリル酸55g、メチルハイドロキノン0.5g及びカルビトールアセテート120gを混合し、90℃で撹拌して混合物を溶解した。次いで、上記混合物の溶解液を60℃まで冷却し、トリフェニルホスフィン1gを加え、100℃で酸価が1mgKOH/gになるまで反応を行った。そこへ、テトラヒドロ無水フタル酸110g及びカルビトールアセテート60gを加え、80℃で約6時間反応後冷却し、アクリル樹脂Cの溶液を得た。(Synthesis Example 3)
Into a 1 L four-necked flask, 280 g of bisphenol F / cresol novolak copolymerized epoxy resin (product name “YDPF-1000” manufactured by Tohto Kasei Co., Ltd.), 55 g of acrylic acid, 0.5 g of methylhydroquinone and 120 g of carbitol acetate are mixed. And stirred at 90 ° C. to dissolve the mixture. Subsequently, the solution of the above mixture was cooled to 60 ° C., 1 g of triphenylphosphine was added, and the reaction was performed at 100 ° C. until the acid value became 1 mgKOH / g. Thereto were added 110 g of tetrahydrophthalic anhydride and 60 g of carbitol acetate, and the mixture was reacted at 80 ° C. for about 6 hours and then cooled to obtain an acrylic resin C solution.
(2)黒色感光性樹脂組成物の調整
下記表1に示す各成分を同表に示す量(g)で配合し、ホモジナイザー(PRIMIX社製、商品名「ROBOMICS」)で1時間撹拌混合して、実施例及び比較例の黒色感光性樹脂組成物をそれぞれ調製した。(2) Preparation of black photosensitive resin composition Each component shown in Table 1 below is blended in the amount (g) shown in the same table, and stirred and mixed for 1 hour with a homogenizer (manufactured by PRIMIX, trade name “ROBOMICS”). The black photosensitive resin compositions of Examples and Comparative Examples were respectively prepared.
(3)ブラックマトリクスの形成
実施例及び比較例で得られた黒色感光性樹脂組成物をそれぞれガラス基板(コーニング社製、商品名「1737」)上にスピンコートし、90℃で3分間乾燥を行い、膜厚1.25μmの感光層を形成した。上記感光層に所定パターンを有するフォトマスクを介し超高圧水銀灯によりに100mJ/cm2の露光を行った。次いで、0.5質量%の炭酸カリウム水溶液で現像後、230℃で30分間熱硬化し、膜厚1.0μmのパターンを有するブラックマトリクスを形成した。(3) Formation of Black Matrix Each of the black photosensitive resin compositions obtained in Examples and Comparative Examples was spin-coated on a glass substrate (product name “1737” manufactured by Corning) and dried at 90 ° C. for 3 minutes. Then, a photosensitive layer having a thickness of 1.25 μm was formed. The photosensitive layer was exposed to 100 mJ / cm 2 with a super high pressure mercury lamp through a photomask having a predetermined pattern. Subsequently, after developing with a 0.5 mass% potassium carbonate aqueous solution, it was thermally cured at 230 ° C. for 30 minutes to form a black matrix having a film thickness of 1.0 μm.
(4)ブラックマトリクスの評価
上記ブラックマトリクスの光学濃度、電気抵抗、解像度及び密着性を下記の方法で評価した。結果を表2に示す。(4) Evaluation of black matrix The optical density, electrical resistance, resolution and adhesion of the black matrix were evaluated by the following methods. The results are shown in Table 2.
<光学濃度>
デンシトメータ(コニカ社製、商品名「PDA−65」)を用い、上述のようにして形成したブラックマトリクスの光学濃度(OD値)を測定した。<Optical density>
Using a densitometer (trade name “PDA-65” manufactured by Konica Corporation), the optical density (OD value) of the black matrix formed as described above was measured.
<電気抵抗>
ガラス基板に代えてHAST試験用櫛型銅配線板を用いた以外は上記と同様の操作を行い、ブラックマトリクスを形成した。次に、絶縁抵抗測定器(アドバンテスト社製、商品名「TR8601」)を用い電圧10Vを印加し、形成したブラックマトリクスの電気抵抗値(Ω)を測定した。<Electrical resistance>
A black matrix was formed in the same manner as described above except that a HAST test comb copper wiring board was used instead of the glass substrate. Next, a voltage of 10 V was applied using an insulation resistance measuring instrument (trade name “TR8601” manufactured by Advantest Corporation), and the electric resistance value (Ω) of the formed black matrix was measured.
<解像度>
解像度評価用ネガとしてライン幅とスペース幅が合計100μmとなるパターンを有する石英ネガマスクを用い、上記の「(3)ブラックマトリクスの形成」と同様の操作を行い、ブラックマトリクスを形成した。露光後の現像によって形成されたブラックマトリクスにおいて、未露光部がきれいに除去された部分におけるライン幅(パターン幅)のうち最も小さい値(単位:μm)を解像度の指標とした。解像度の評価は数値が小さいほど良好な値である。<Resolution>
A quartz negative mask having a pattern with a total line width and space width of 100 μm was used as a resolution evaluation negative, and the same operation as in “(3) Formation of black matrix” was performed to form a black matrix. In the black matrix formed by the development after exposure, the smallest value (unit: μm) among the line widths (pattern widths) in the portions where the unexposed portions were removed cleanly was used as an index of resolution. The smaller the numerical value, the better the resolution evaluation.
また、形成したブラックマトリクスのパターンエッジ部を走査電子顕微鏡(SEM)で観察し、バリの出現度合いを1〜5段階で評価した。バリの出現度合いは、パターンエッジ部からパターン外周に向って成長したバリの幅で評価した。図1は、ブラックマトリクスのパターンエッジ部の形状を比較したSEM写真である。評価=5ではバリが認められないのに対し、評価=1では顕著にバリが発生し、パターンエッジ部からのバリの幅が大きいことが認められる。このように、バリの発生が認められない場合の評価を「5」、発生したバリの幅が図1の評価「1」に示す幅以上である場合を総じて評価「1」とした。また、バリの発生が認められ、かつバリの幅が図1の評価「1」に示すものの1/3倍未満である場合を評価「4」、1/3倍以上2/3倍未満である場合を評価「3」、2/3倍以上1倍未満である場合を評価「2」とした。 Moreover, the pattern edge part of the formed black matrix was observed with the scanning electron microscope (SEM), and the appearance degree of the burr | flash was evaluated in 1-5 steps. The appearance degree of burrs was evaluated by the width of burrs grown from the pattern edge portion toward the outer periphery of the pattern. FIG. 1 is an SEM photograph comparing the shapes of pattern edges of a black matrix. When evaluation = 5, no burrs are observed, but when evaluation = 1, burrs are remarkably generated and it is recognized that the width of burrs from the pattern edge portion is large. Thus, the evaluation when the occurrence of burrs was not recognized was “5”, and the case where the width of the generated burrs was equal to or larger than the width indicated by the evaluation “1” in FIG. In addition, when the occurrence of burrs is recognized and the width of the burrs is less than 1/3 times that shown in the evaluation “1” of FIG. 1, the evaluation is “4”, which is 1/3 times or more and less than 2/3 times The case was evaluated as “3”, and the case of 2/3 times or more and less than 1 time was evaluated as “2”.
<密着性>
感光層を超高圧水銀灯によりに100mJ/cm2の露光を行なった後、0.5質量%炭酸カリウム水溶液を0.1274MPa(1.3kgf/cm2)の圧力でスプレー噴霧し、形成したライン幅18μmのブラックマトリクスのパターンが剥離し流れだす時間(秒)を測定した。この時間が長いほど密着性に優れる。<Adhesion>
The photosensitive layer was exposed to 100 mJ / cm 2 with an ultra-high pressure mercury lamp and then sprayed with a 0.5 mass% potassium carbonate aqueous solution at a pressure of 0.1274 MPa (1.3 kgf / cm 2 ) to form a line width formed. The time (seconds) required for the 18 μm black matrix pattern to peel off and flow was measured. The longer this time, the better the adhesion.
実施例1〜3で得られた黒色感光性樹脂組成物を用いることで、従来パターン形成ができなかった光学濃度4以上でも、解像度が高く5μmまで細線化したラインバリの少ないブラックマトリクスを形成できることがわかる。 By using the black photosensitive resin composition obtained in Examples 1 to 3, it is possible to form a black matrix with a small line burr that has a high resolution and is thinned to 5 μm even at an optical density of 4 or higher, which has not been able to form a pattern conventionally. I understand.
また、実施例1〜4で得られた黒色感光性樹脂組成物から形成されたブラックマトリクスは、光学濃度4以上でありながら解像度に優れ、かつ電気抵抗値が十分に高い。さらに、実施例1〜5で得られた黒色感光性樹脂組成物から形成されたブラックマトリクスは、密着性に十分に優れている。 Moreover, the black matrix formed from the black photosensitive resin composition obtained in Examples 1 to 4 has an optical density of 4 or more, has excellent resolution, and has a sufficiently high electrical resistance value. Furthermore, the black matrix formed from the black photosensitive resin composition obtained in Examples 1 to 5 is sufficiently excellent in adhesion.
実施例1及び2の結果から、上記一般式(IV)で表される繰り返し単位を有するアクリル樹脂を用いることにより、密着性がより一層向上することがわかる。 From the results of Examples 1 and 2, it can be seen that the adhesion is further improved by using the acrylic resin having the repeating unit represented by the general formula (IV).
また、ポリマー/モノマー比を変更した実施例2〜4を比較すると、ポリマー/モノマー比が2.5未満である2.1と小さい実施例3では、ラインバリが出現しやすくなる。一方、ポリマー/モノマー比が3.5を超える4.85と大きい実施例4では、形成したブラックマトリクスが流れ易くなる傾向がある。これらの結果から、実施例2のようにポリマー/モノマー比が特に2.5〜3.5であると、バリをより一層低減し、密着性を更に向上することがわかる。 Further, when Examples 2 to 4 in which the polymer / monomer ratio is changed are compared, in Example 3 where the polymer / monomer ratio is less than 2.5 and 2.1 is small, line burrs are likely to appear. On the other hand, in Example 4 where the polymer / monomer ratio is as large as 4.85 exceeding 3.5, the formed black matrix tends to flow easily. From these results, it can be seen that when the polymer / monomer ratio is particularly 2.5 to 3.5 as in Example 2, the burrs are further reduced and the adhesion is further improved.
本発明によれば、ブラックマトリクスとしての光学濃度及び電気抵抗値を十分に満足すると共に、解像度が十分に高い黒色感光性樹脂組成物及びこれを用いたブラックマトリクスの形成方法、カラーフィルタの製造方法並びにカラーフィルタを提供することができる。 According to the present invention, a black photosensitive resin composition sufficiently satisfying optical density and electric resistance value as a black matrix and having a sufficiently high resolution, a method for forming a black matrix using the same, and a method for producing a color filter In addition, a color filter can be provided.
Claims (8)
前記バインダーポリマーが、下記一般式(I)、(II)及び(III)で表される繰り返し単位を有するアクリル樹脂を含む、黒色感光性樹脂組成物。
The black photosensitive resin composition in which the said binder polymer contains the acrylic resin which has a repeating unit represented by the following general formula (I), (II) and (III).
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JP5441352B2 (en) * | 2008-04-25 | 2014-03-12 | 富士フイルム株式会社 | Polymerizable composition, light-shielding color filter, and solid-state imaging device |
KR101441998B1 (en) * | 2008-04-25 | 2014-09-18 | 후지필름 가부시키가이샤 | Polymerizable composition, light shielding color filter, black curable composition, light shielding color filter for solid-state imaging device, method of manufacturing the same, and solid-state imaging device |
KR101121038B1 (en) * | 2008-07-01 | 2012-03-15 | 주식회사 엘지화학 | Photoresist resin composition containing a number of photo-initiators, transparent thin film layer and liquid crystal display using the same |
JP2010122381A (en) * | 2008-11-18 | 2010-06-03 | Hitachi Chem Co Ltd | Black photosensitive resin composition, method for producing black matrix, method for producing color filter, and color filter |
KR101084262B1 (en) | 2009-12-15 | 2011-11-16 | 삼성모바일디스플레이주식회사 | LCD panel and manufacturing method thereof |
JP5456552B2 (en) * | 2010-04-19 | 2014-04-02 | 東レコーテックス株式会社 | Polymer with both low hygroscopicity and alkaline water solubility |
TWI420244B (en) * | 2011-04-08 | 2013-12-21 | Chi Mei Corp | Photosensitive resin composition, and color filter and liquid crystal display device made by using the composition |
JP5456183B2 (en) * | 2013-01-11 | 2014-03-26 | 富士フイルム株式会社 | Black curable composition, light-shielding color filter for solid-state imaging device, method for producing the same, and solid-state imaging device. |
JP5456184B2 (en) * | 2013-01-15 | 2014-03-26 | 富士フイルム株式会社 | Black curable composition, light-shielding color filter for solid-state image sensor, antireflection film for solid-state image sensor, method for producing light-shielding color filter for solid-state image sensor, and solid-state image sensor |
SG11201802613SA (en) | 2015-09-30 | 2018-04-27 | Toray Industries | Negative type coloring photosensitive resin composition, cured film, element, and display device |
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