CN109283791B - Negative colored photosensitive resin composition, optical filter, and liquid crystal display device - Google Patents
Negative colored photosensitive resin composition, optical filter, and liquid crystal display device Download PDFInfo
- Publication number
- CN109283791B CN109283791B CN201811227492.2A CN201811227492A CN109283791B CN 109283791 B CN109283791 B CN 109283791B CN 201811227492 A CN201811227492 A CN 201811227492A CN 109283791 B CN109283791 B CN 109283791B
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- China
- Prior art keywords
- alkali
- soluble resin
- colored photosensitive
- negative
- photosensitive resin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 230000003287 optical effect Effects 0.000 title claims abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 13
- -1 optical filter Substances 0.000 title description 18
- 229920005989 resin Polymers 0.000 claims abstract description 61
- 239000011347 resin Substances 0.000 claims abstract description 61
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 239000000049 pigment Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000007514 bases Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000005520 diaryliodonium group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- IHDKBHLTKNUCCW-UHFFFAOYSA-N 1,3-thiazole 1-oxide Chemical class O=S1C=CN=C1 IHDKBHLTKNUCCW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229960004599 sodium borate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 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
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Abstract
The present invention relates to a negative colored photosensitive resin composition, an optical filter, and a liquid crystal display device, which belong to the technical field of liquid crystal display. The negative-type colored photosensitive resin composition includes: a first alkali-soluble resin A, a second alkali-soluble resin B, a monomer C, a pigment liquid D, a photopolymerization initiator E, a photoacid generator F and a solvent G; the first alkali-soluble resin a has a repeating unit represented by the following chemical formula 1:
in the formula, R1、R2、R3Each independently is hydrogen or methyl, R4Is a linear or branched alkylene or alkyleneoxy radical of C1 to C5, R5Linear or branched alkylene or alkyleneoxy groups of C1-C5, a/(a + b + C) 10-50%, b/(a + b + C) 10-50%, C/(a + b + C) 10-50%; the second alkali-soluble resin B has a repeating unit represented by the following chemical formula 2:
in the formula, R6Is a linear or branched alkylene or alkoxy group of C1-C5, R7Is a linear or branched alkylene or alkoxy group of C1-C5, R8Is a linear or branched alkylene or alkoxy group of C1-C5, and n is an integer of 50-200.
Description
Technical Field
The present invention relates to a negative colored photosensitive resin composition, an optical filter, and a liquid crystal display device, which belong to the technical field of liquid crystal display.
Background
In the display field, a negative type colored photosensitive resin composition is required to be used for forming various photo-curing patterns such as a filter. Conventionally, an optical filter is prepared by uniformly coating a negative type colored photosensitive resin composition including red, green, and blue on a substrate of a black matrix pattern, then drying by heating, exposing and developing the uniformly coated film, and further post-baking by heating at a high temperature is required to form a pixel of each color, and the above processes are repeated for each color.
In order to provide better adhesion and chemical resistance to the optical filter, it has been necessary to perform a post-baking process at a high temperature to sufficiently cure the optical filter. In order to apply the optical filter to an OLED display or a flexible display which is not resistant to high temperature, it is required to develop a negative type colored photosensitive resin composition which can be sufficiently cured under a low-temperature post-baking condition and exhibits good adhesion and chemical resistance.
Negative-type colored photosensitive resin composition japanese patent No. 2937208 discloses a colored photosensitive resin composition including a thermal crosslinking agent such as a melamine resin or an epoxy resin to allow post-baking at a low temperature. However, when the colored photosensitive resin composition is post-baked at a temperature of less than 200 ℃, the degree of curing is still insufficient.
Disclosure of Invention
In view of the disadvantages of the prior art, the present invention provides a negative colored photosensitive resin composition, an optical filter, and a liquid crystal display device.
According to an aspect of the present invention, there is provided a negative-type colored photosensitive resin composition comprising: a first alkali-soluble resin A, a second alkali-soluble resin B, a monomer C, a pigment liquid D, a photopolymerization initiator E, a photoacid generator F and a solvent G;
the first alkali-soluble resin a has a repeating unit represented by the following chemical formula 1:
in the formula, R1、R2、R3Each independently of the other being hydrogen or methyl,
R4is a linear or branched alkylene or alkoxy group of C1-C5,
R5is a linear or branched alkylene or alkoxy group of C1-C5,
a/(a+b+c)＝10-50％、b/(a+b+c)＝10-50％、c/(a+b+c)＝10-50％。
the second alkali-soluble resin B has a repeating unit represented by the following chemical formula 2:
in the formula, R6Is a linear or branched alkylene or alkoxy group of C1-C5,
R7is a linear or branched alkylene or alkoxy group of C1-C5,
R8is a linear or branched alkylene or alkoxy group of C1-C5,
n is an integer of 50 to 200.
According to one embodiment of the invention, the first alkali-soluble resin a is contained in an amount of 0.1 to 8% by weight, relative to the total weight of the composition.
According to one embodiment of the present invention, the weight average molecular weight of the first alkali-soluble resin A is 5000-20000 and the acid value is 50-140KOH mg/g.
According to one embodiment of the present invention, in the first alkali-soluble resin A, R1、R2、R3Are each methyl, R4、R5Are all methylene groups.
According to one embodiment of the present invention, the weight average molecular weight of the second alkali-soluble resin B is 5000-.
According to one embodiment of the invention, the second alkali-soluble resin B is contained in an amount of 0.1 to 8% by weight, relative to the total weight of the composition.
According to one embodiment of the present invention, the weight ratio of the first alkali-soluble resin a to the second alkali-soluble resin B is (1:4) to (4: 1).
The negative-type colored photosensitive resin composition of the present invention contains both the first alkali-soluble resin a and the second alkali-soluble resin B, and can exhibit a better curing effect by allowing a plurality of reactions to proceed when both of them are contained due to the specific functional groups contained in each of them.
According to another aspect of the present invention, there is provided an optical filter including the negative-type colored photosensitive resin composition as described above.
According to still another aspect of the present invention, there is also provided a display device including the optical filter as described above.
The negative-type photosensitive resin composition according to the present invention can be cured at a low temperature of less than 100 ℃ and exhibits excellent adhesion and chemical resistance.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below.
The present invention provides a negative-type colored photosensitive resin characterized by comprising: the coating comprises a first alkali-soluble resin A, a second alkali-soluble resin B, a monomer C, a pigment liquid D, a photopolymerization initiator E, a photoacid generator F and a solvent G.
The first alkali-soluble resin a has a repeating unit represented by the following chemical formula 1:
in the formula, R1、R2、R3Each independently of the other being hydrogen or methyl,
R4is a linear or branched alkylene or alkoxy group of C1-C5,
R5is a linear or branched alkylene or alkoxy group of C1-C5,
a/(a+b+c)＝10-50％、b/(a+b+c)＝10-50％、c/(a+b+c)＝10-50％。
the weight average molecular weight of the first alkali-soluble resin A is 5000-20000, and the acid value is 50-140 KOHmg/g.
“R4Straight-chain or branched alkylene or alkoxy of C1 to C5 "means R4May be selected from: linear alkylene of C1 to C5, such as methylene, ethylene, propylene, butylene, pentylene; branched alkylene of C1 to C5, for exampleSuch as-CH (CH)3)2-、-CH(CH3)(CH2CH3)-、-CH(CH2CH3)2-、-CH(CH3)(CH2CH2CH3) -; linear alkoxy of C1 to C5, such as methoxy, ethoxy, propoxy, butoxy, pentoxy; C1-C5 branched alkoxy groups such as isopropoxy, 2-methylbutoxy, 3-methylbutoxy and the like.
When R is4In the case of C1-C5 alkoxy, the oxygen atom is attached to a quaternary carbon in the structure and the carbon atom is attached to a carboxyl moiety in the structure.
For example, when R is4In the case of methoxy, the structure corresponding to formula 1 is:
for R5～R8The same should be understood.
According to one embodiment of the present invention, in the first alkali-soluble resin A, R1、R2、R3Are each methyl, R4、R5Are all methylene groups.
The first alkali-soluble resin a may be contained in an amount of 0.1 to 8% by weight, relative to the total weight of the composition. For example, the amount may be 0.1 wt%, 0.2 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 5 wt%, 7 wt%, 8 wt%.
The second alkali-soluble resin B has a repeating unit represented by the following chemical formula 2:
in the formula, R6Is a linear or branched alkylene or alkoxy group of C1-C5,
R7is a linear or branched alkylene or alkoxy group of C1-C5,
R8is a linear or branched alkylene or alkoxy group of C1-C5,
n is an integer of 50 to 200.
The weight average molecular weight of the second alkali-soluble resin B was 5000-20000.
The negative-type colored photosensitive resin composition may contain the second alkali-soluble resin B in an amount of 0.1 to 8 wt% based on the total weight of the composition. For example, the amount may be 0.1 wt%, 0.2 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 5 wt%, 7 wt%, 8 wt%.
The weight ratio of the first alkali-soluble resin a to the second alkali-soluble resin B may be (1:4) to (4:1), and may be, for example, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, or the like.
When the weight difference between the first alkali-soluble resin A and the second alkali-soluble resin B is not large, the first alkali-soluble resin A and the second alkali-soluble resin B can be sufficiently reacted, and the better adhesive property and chemical resistance result is shown; when one of the two is excessively large, the excessive resin may not be completely reacted, thereby exhibiting poor adhesion and chemical resistance results.
Monomer C
The monomer C is not particularly limited as long as it is a polymerizable compound used in the art, and examples thereof include monofunctional monomers, difunctional monomers, and other polyfunctional monomers, and the kind thereof is not particularly limited, and the following compounds can be exemplified.
Specific examples of the monofunctional monomer include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Specific examples of the 2-functional monomer include 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol a, 3-methylpentanediol di (meth) acrylate, and the like. Specific examples of the other polyfunctional monomer include trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, and the like. Among them, a polyfunctional monomer having two or more functions is preferably used.
The content of the above-mentioned monomer C is not particularly limited, and may be in the range of 50 to 200 parts by weight, preferably 80 to 150 parts by weight, based on 100 parts by weight of the total weight of the first alkali-soluble resin a and the second alkali-soluble resin B.
Pigment liquid D
The pigment liquid contains more than one of pigment green G58, G59 and pigment yellow Y150, Y138 and Y139 of ENF. The amount of the pigment liquid added may be adjusted according to the requirement of chromaticity, and the content of the pigment powder may be 10 to 50 parts by weight, preferably 20 to 40 parts by weight, based on 100 parts by weight of the solid component in the negative-type colored photosensitive resin composition.
Photopolymerization initiator E
The photopolymerization initiator E of the present invention is not particularly limited in its specific kind as long as it can polymerize the monomer C. For example, at least one compound selected from acetophenone compounds, benzophenone compounds, triazine compounds, biimidazole compounds, thiazolone compounds, oxime ester compounds, and nitrooxime ester compounds may be used, and preferably, a nitrooxime ester compound may be used.
In order to improve the sensitivity of the negative-type colored photosensitive resin composition of the present invention, the photopolymerization initiator E may further contain a photopolymerization initiator aid. The negative-type colored photosensitive resin composition according to the present invention contains a photopolymerization initiation aid, and thus can further improve sensitivity and improve polymerization performance.
The photopolymerization initiation assistant may be at least one compound selected from the group consisting of carboxylic acid compounds and organic sulfur compounds having a thiol group.
The content of the photopolymerization initiator is not particularly limited, and for example, the photopolymerization initiator may be 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, based on 100 parts by weight of the solid content in the negative-type colored photosensitive resin composition.
Photoacid generator F
The specific kind of the photoacid generator F according to the present invention is not particularly limited as long as the oxetanyl group in the second alkali-soluble resin B can be opened. For example, at least one compound selected from aryldiazonium salt compounds, diaryliodonium salt compounds, triarylsulfonium salt compounds, and arylferrocenium salt compounds can be used, and diaryliodonium salt compounds and triarylsulfonium salt compounds are preferable.
The content of the photoacid generator is not particularly limited, and for example, the photoacid generator may be 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, based on 100 parts by weight of the solid content in the negative-type colored photosensitive resin composition.
Solvent G
The solvent G is not particularly limited as long as it can dissolve the above-mentioned components a to F, has an appropriate drying rate, and can form a uniform and smooth coating film after evaporation of the solvent.
As the solvent, esters such as alkylene glycol alkyl ether acetates, ketones, butanediol alkyl ether acetates, butanediol monoalkyl ethers, ethyl 3-ethoxypropionate, and methyl 3-methoxypropionate can be preferably used in consideration of coatability and drying property. More preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, methoxybutyl acetate, methoxybutanol, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like can be used.
Among the solvents exemplified above, in view of coatability and drying properties, organic solvents having a boiling point of 100 to 200 ℃ are preferred, and esters such as alkylene glycol alkyl ether acetates, ketones, ethyl 3-ethoxypropionate and methyl 3-methoxypropionate are more preferred, and propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate and methyl 3-methoxypropionate are more preferred. These solvents may be used either individually or as a mixture of two or more thereof.
The negative-type colored photosensitive resin composition contains 30 to 90 wt%, preferably 35 to 85 wt%, of the solvent G, based on the total weight of the composition. When the content of the solvent is within the above range, it is preferable because the coating property is good when the coating is performed by a coating apparatus such as a spin coater, a slit and spin coater, a slit coater (also referred to as "die coater", "curtain flow coater"), or an inkjet.
According to another aspect of the present invention, there is provided an optical filter including the negative-type colored photosensitive resin composition as described above.
The optical filter according to one embodiment of the present invention includes a colored layer formed by coating a negative-type colored photosensitive resin composition on a substrate, and then exposing and developing to form a pattern.
A method of forming a pattern using the negative-type colored photosensitive resin composition of the present invention is as follows.
First, the negative-type colored photosensitive resin composition of the present invention is coated on a substrate (typically, a glass substrate), and then heated and dried to remove volatile components such as a solvent, thereby forming a smooth film layer.
The coating process can be performed by various methods such as spin coating, casting, roll coating, slot and spin coating, and slot coating. After coating, volatile components such as a solvent are volatilized by heating and drying (prebaking) or by drying under reduced pressure and then heating. The heating is usually carried out at from 50 to 100 ℃ and preferably at from 70 to 85 ℃. The film layer after heating and drying generally has a thickness of 1 μm to 10 μm.
The coating film thus obtained is irradiated with ultraviolet rays through a mask for forming a desired pattern. In order to uniformly irradiate the entire exposure area with parallel light rays and properly align the mask with the substrate, a mask aligner or stepper is preferably used. The ultraviolet irradiation causes the irradiated portion to be cured. g-line (436nm), h-line, i-line (365nm) can be used as the ultraviolet ray. The illuminance of ultraviolet rays may be appropriately selected as necessary, and the present invention is not limited thereto.
The cured coating film is contacted with a developing solution to dissolve the non-exposed regions for development, thereby obtaining a desired pattern. The developing process may be performed by a solution addition, dipping, or spraying method without limitation. In addition, the substrate may be tilted at alternative angles during development. The developing solution is generally an aqueous solution containing an alkaline compound and a surfactant.
The basic compound may be an inorganic or organic basic compound. Examples of the inorganic basic compound may include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium borate, potassium borate, and ammonia.
In addition, examples of the organic basic compound may include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, and ethanolamine.
These inorganic and organic basic compounds may be used alone or in combination of two or more. The content of the alkaline compound may be 0.01 to 10 wt%, preferably 0.03 to 5 wt%, based on the total weight of the developing solution.
The surfactant in the developing solution may be at least one selected from the group consisting of nonionic, anionic and cationic surfactants. The surfactant may be contained in an amount of 0.01 to 10 wt%, preferably 0.05 to 8 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the developing solution.
After development, the film is washed and baked at less than 100 deg.C (preferably 100 deg.C) for 1 h.
As described above, the colored photosensitive resin composition is subjected to coating, drying, exposure for patterning, and development to produce pixels or black matrices corresponding to the respective colors of the coloring materials in the photosensitive resin composition, and such procedures are repeated according to the number of colors required for the filter, thereby obtaining the filter. The construction and preparation of the optical filter are known in the art, and thus a detailed description thereof is omitted herein.
According to another aspect of the present invention, there is provided a display device, such as a liquid crystal or OLED display apparatus, including the above-described optical filter.
The liquid crystal and OLED display device of the present invention has the above-described filter and includes other components known in the art. That is, any liquid crystal display device to which the filter of the present invention can be applied is included in the present invention. For example, there is a transmissive liquid crystal display device in which opposing electrode substrates having a Thin Film Transistor (TFT), a pixel electrode, and an alignment layer are made to face each other at a predetermined interval, and a liquid crystal material is introduced into the interval to form a liquid crystal layer. Mention may furthermore be made of OLED display devices which are coated with the filters according to the invention on top of the cathode.
The present invention is further illustrated by the following examples, comparative examples and experimental examples which should not be construed as limiting the scope of the present invention. It is apparent to those skilled in the art that these examples, comparative examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
Preparation example 1: preparation of alkali-soluble resin (first alkali-soluble resin A-1)
In a 500ml flask having a reflux condenser, a dropping device and a stirrer, nitrogen gas was introduced at 0.01L/min to form a nitrogen atmosphere, and 200g of propylene glycol monomethyl ether acetate was then added thereto. After the temperature is raised to 87 ℃, the monomers m (0.3mol), n (0.5mol) and p (0.6mol) are added and stirred uniformly, then 3.6g of azodiisobutyronitrile dissolved in 50g of propylene glycol monomethyl ether acetate is slowly dripped into the flask through a dropping funnel for 1h, and after dripping is finished, the mixture is stirred and reacted for 5 h.
After 5 hours of reaction, a solution prepared by dissolving 0.5g of p-methoxyphenol in 20g of propylene glycol monomethyl ether acetate was slowly dropped into the flask via a dropping funnel over 1 hour, and the reaction was carried out with stirring for 1 hour, thereby obtaining copolymer A-1 having a solid acid value of 75 mgKOH/g. The weight average molecular weight according to GPC measurement was 8000.
In the first alkali-soluble resin A-1, R1、R2、R3Are each methyl, R4、R5All are methylene groups, a is 21 mol%, b is 36 mol%, and c is 43 mol%.
The first alkali-soluble resin a of other structure can be prepared by the same method as in preparation example 1.
Preparation example 2: preparation of alkali-soluble resin (second alkali-soluble resin B-1)
In a 500ml flask having a reflux condenser, a dropping device and a stirrer, nitrogen gas was introduced at 0.01L/min to form a nitrogen atmosphere, and 200g of propylene glycol monomethyl ether acetate was then added thereto. After the temperature is raised to 87 ℃, the monomer q (1.2mol) is added, after uniform stirring, a solution prepared by dissolving 3.6g of azobisisobutyronitrile in 50g of propylene glycol methyl ether acetate is slowly dripped into the flask through a dropping funnel for 1 hour, and after dripping is finished, the mixture is stirred and reacts for 5 hours.
After 5 hours of reaction, a solution prepared by dissolving 0.5g of p-methoxyphenol in 20g of propylene glycol monomethyl ether acetate was slowly dropped into the flask via a dropping funnel over 1 hour, and the reaction was stirred for 1 hour to obtain copolymer B-1 having a weight average molecular weight of 7000 according to GPC measurement.
The second alkali-soluble resin B having other polymerization degree can be prepared by the same method as in preparation example 2.
Examples 1 to 6 and comparative examples 1 to 6: preparation of negative-type colored photosensitive resin composition
A negative-type colored photosensitive resin composition was prepared by mixing the ingredients in the proportions listed in table 1 below (unit: parts by weight).
[ Table 1]
A-1: resin obtained in production example 1
B-1: resin obtained in production example 2
The alkali soluble resins used in the comparative examples are all acrylic acid alkali soluble resins sold by Showa electrician, and SPDD-2, SPDD-36, SPDD-41, SPDD-51 and SPDD-52 are different types.
C-1: dipentaerythritol hexaacrylate (Saedoma)
D-1: G59/Y138 ═ 17/10, G59 is ES-29G (ENF), Y138 is ES-31Y (ENF)
E-1: oxime ester photopolymerization initiator OXE-02(BASF)
F-1: diaryl iodonium salt photoacid generator TR-PAG-201 (Changzhou powerful electronic new material)
Experimental example 1: evaluation of adhesion after development
Each of the photosensitive resin compositions obtained in examples and comparative examples was spin-coated on a 7cm by 7cm glass substrate, and then heated at 100 ℃ for 100 seconds using a hot plate. After cooling the substrate to room temperature, the exposure process was performed at an interval of 75 μm using an i-line exposure machine at an exposure dose of 60mJ (365 nm). The substrate on which the exposure process was completed was shower-developed in a developing aqueous solution containing 0.043% potassium hydroxide for 60s, and washed with water. Postbaking at 100 ℃ for 1h, followed by testing for adhesion with a hundred-grignard knife.
Evaluation criteria
Very good: the result of the Baigeli test is 5B-4B
Baige force test result is 4B-3B
The test result of the Baige force is 3B-2B
The result of the Baige testing is below 2B
Experimental example 2: evaluation of chemical resistance
The post-baked substrate was coated with an R-color photoresist as a glass substrate, and baked at 100 ℃ for 100 seconds, and then observed under an optical microscope, the smaller the surface shrinkage, the more excellent the post-baking chemical resistance.
Evaluation criteria
Very good: lower layer without shrinkage
Lower layer less shrinkage
Delta, more shrinkage of the lower layer
The lower layer falls off
[ Table 2]
As shown in table 2, the negative-type photosensitive resin compositions according to examples 1 to 4 of the present invention can simultaneously exhibit excellent adhesion and excellent chemical resistance even when cured at a low temperature of 100 ℃. On the other hand, when an alkali-soluble resin alone or a comparative resin was used, the post-baking adhesion and chemical resistance were poor.
The above embodiments are only used to describe the technical solutions of the present application in detail, but the above embodiments are only used to help understanding the method of the embodiments of the present invention, and should not be construed as limiting the embodiments of the present invention. Variations or substitutions that may be readily apparent to one skilled in the art are intended to be included within the scope of the embodiments of the present invention.
Claims (8)
1. A negative-type colored photosensitive resin composition, comprising: a first alkali-soluble resin A, a second alkali-soluble resin B, a monomer C, a pigment liquid D, a photopolymerization initiator E, a photoacid generator F and a solvent G;
the first alkali-soluble resin a has a repeating unit represented by the following chemical formula 1:
in the formula, R1、R2、R3Each independently of the other being hydrogen or methyl,
R4is a linear or branched alkylene or alkoxy group of C1-C5,
R5is a linear or branched alkylene or alkoxy group of C1-C5,
a/(a+b+c)＝10-50％、b/(a+b+c)＝10-50％、c/(a+b+c)＝10-50％；
the second alkali-soluble resin B has a repeating unit represented by the following chemical formula 2:
in the formula, R6Is a linear or branched alkylene or alkoxy group of C1-C5,
R7is a linear or branched alkylene or alkoxy group of C1-C5,
R8is a linear or branched alkylene or alkoxy group of C1-C5,
n is an integer of 50 to 200;
the weight ratio of the first alkali-soluble resin A to the second alkali-soluble resin B is 1:4 to 4: 1.
2. The negative-type colored photosensitive resin composition according to claim 1, wherein R in the first alkali-soluble resin A is R1、R2、R3Are each methyl, R4、R5Are all methylene groups.
3. The negative-type colored photosensitive resin composition according to claim 1, wherein the first alkali-soluble resin A has a weight average molecular weight of 5000-20000 and an acid value of 50-140KOH mg/g.
4. The negative-type colored photosensitive resin composition according to claim 1, wherein the first alkali-soluble resin A is contained in an amount of 0.1 to 8% by weight based on the total weight of the composition.
5. The negative-type colored photosensitive resin composition according to claim 1, wherein the weight average molecular weight of the second alkali-soluble resin B is 5000-20000.
6. The negative-type colored photosensitive resin composition according to claim 1, wherein the second alkali-soluble resin B is contained in an amount of 0.1 to 8% by weight based on the total weight of the composition.
7. An optical filter comprising the negative-type colored photosensitive resin composition according to any one of claims 1 to 6.
8. A display device comprising the filter according to claim 7.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000112121A (en) * | 1998-10-06 | 2000-04-21 | Fuji Photo Film Co Ltd | Photosensitive resin composition |
| CN1474961A (en) * | 2000-11-15 | 2004-02-11 | ���ƹɷ�����˾ | Positive type photosensitive epoxy resin composition and printed circuit board using same |
| JP2008224970A (en) * | 2007-03-12 | 2008-09-25 | Fujifilm Corp | Photosensitive resin composition, method for producing cured relief pattern using the same, and semiconductor device |
| TW201120014A (en) * | 2009-09-18 | 2011-06-16 | Fujifilm Corp | Colored curable composition, color filter, and method for producing color filter |
| CN103975274A (en) * | 2011-12-06 | 2014-08-06 | 株式会社钟化 | Black photosensitive resin composition and use of same |
| CN105425542A (en) * | 2014-09-12 | 2016-03-23 | 奇美实业股份有限公司 | Photosensitive resin composition for color filter and application thereof |
-
2018
- 2018-10-22 CN CN201811227492.2A patent/CN109283791B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000112121A (en) * | 1998-10-06 | 2000-04-21 | Fuji Photo Film Co Ltd | Photosensitive resin composition |
| CN1474961A (en) * | 2000-11-15 | 2004-02-11 | ���ƹɷ�����˾ | Positive type photosensitive epoxy resin composition and printed circuit board using same |
| JP2008224970A (en) * | 2007-03-12 | 2008-09-25 | Fujifilm Corp | Photosensitive resin composition, method for producing cured relief pattern using the same, and semiconductor device |
| TW201120014A (en) * | 2009-09-18 | 2011-06-16 | Fujifilm Corp | Colored curable composition, color filter, and method for producing color filter |
| CN103975274A (en) * | 2011-12-06 | 2014-08-06 | 株式会社钟化 | Black photosensitive resin composition and use of same |
| CN105425542A (en) * | 2014-09-12 | 2016-03-23 | 奇美实业股份有限公司 | Photosensitive resin composition for color filter and application thereof |
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