CN114415469B - Photoresist composition and photoresist - Google Patents
Photoresist composition and photoresist Download PDFInfo
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- CN114415469B CN114415469B CN202111680620.0A CN202111680620A CN114415469B CN 114415469 B CN114415469 B CN 114415469B CN 202111680620 A CN202111680620 A CN 202111680620A CN 114415469 B CN114415469 B CN 114415469B
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- acrylic resin
- parts
- photoresist
- photoresist composition
- fluorosilane
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 80
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 113
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 113
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 18
- -1 methacrylic acid ester compound Chemical class 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- 239000000049 pigment Substances 0.000 claims abstract description 8
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 claims description 30
- 229940089951 perfluorooctyl triethoxysilane Drugs 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 abstract description 21
- 239000000853 adhesive Substances 0.000 abstract description 17
- 230000001070 adhesive effect Effects 0.000 abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000126 substance Substances 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
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- 229910018540 Si C Inorganic materials 0.000 description 2
- SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- HOSJNFCDDCLEBM-UHFFFAOYSA-N (2-phenyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1C1=CC=CC=C1 HOSJNFCDDCLEBM-UHFFFAOYSA-N 0.000 description 1
- RSHKWPIEJYAPCL-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CC)COC1 RSHKWPIEJYAPCL-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- CNDOSNMFHUSKGN-UHFFFAOYSA-N 1-(2-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC=C1N1C(=O)C=CC1=O CNDOSNMFHUSKGN-UHFFFAOYSA-N 0.000 description 1
- LJDGDRYFCIHDPX-UHFFFAOYSA-N 1-(2-methoxyphenyl)pyrrole-2,5-dione Chemical compound COC1=CC=CC=C1N1C(=O)C=CC1=O LJDGDRYFCIHDPX-UHFFFAOYSA-N 0.000 description 1
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
- YWODHBPFOGXUFX-UHFFFAOYSA-N 1-(3-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC(N2C(C=CC2=O)=O)=C1 YWODHBPFOGXUFX-UHFFFAOYSA-N 0.000 description 1
- UNCUTNPWBZKJHD-UHFFFAOYSA-N 1-(3-methoxyphenyl)pyrrole-2,5-dione Chemical compound COC1=CC=CC(N2C(C=CC2=O)=O)=C1 UNCUTNPWBZKJHD-UHFFFAOYSA-N 0.000 description 1
- PRZFFHNZHXGTRC-UHFFFAOYSA-N 1-(3-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=CC2=O)=O)=C1 PRZFFHNZHXGTRC-UHFFFAOYSA-N 0.000 description 1
- BLLFPKZTBLMEFG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(O)=CC=C1N1C(=O)C=CC1=O BLLFPKZTBLMEFG-UHFFFAOYSA-N 0.000 description 1
- XAHCEMQKWSQGLQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=CC1=O XAHCEMQKWSQGLQ-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000290143 Pyrus x bretschneideri Species 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- JBWNOQLQXKAODW-UHFFFAOYSA-N [4-(trifluoromethoxy)oxetan-2-yl]methyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCC1OC(C1)OC(F)(F)F JBWNOQLQXKAODW-UHFFFAOYSA-N 0.000 description 1
- BSYQEPMUPCBSBK-UHFFFAOYSA-N [F].[SiH4] Chemical compound [F].[SiH4] BSYQEPMUPCBSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KRGGVEDZUSPSAC-UHFFFAOYSA-N oxetan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCO1 KRGGVEDZUSPSAC-UHFFFAOYSA-N 0.000 description 1
- AMUUFLNQHMIHRP-UHFFFAOYSA-N oxetan-3-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1 AMUUFLNQHMIHRP-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
- G03F7/075—Silicon-containing compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Optical Filters (AREA)
Abstract
The application relates to the field of liquid crystal display panels, and particularly discloses a photoresist composition and photoresist. The photoresist composition comprises, by weight, 25-35 parts of black dispersion pigment liquid, 3-6 parts of organic fluorosilicone modified acrylic resin, 8-10 parts of acrylic resin, 3-5 parts of monomer, 1-2 parts of photoinitiator, 2-6 parts of auxiliary agent and 60-80 parts of solvent; the monomer is an acrylic acid or methacrylic acid ester compound containing more than 3 ethylenically unsaturated groups, and the weight average molecular weight of the acrylic resin is 7000-30000. According to the application, the organic fluorine-silicon modified acrylic resin and the acrylic resin are matched, so that the adhesive force and the water repellency of the photoresist are improved on the basis of ensuring that the optical filter has better resolution, the adhesive force grade of the obtained photoresist is above 4B, and the water contact angle is above 85 degrees.
Description
Technical Field
The application relates to the field of liquid crystal display panels, in particular to a photoresist composition and photoresist.
Background
The photoresist is a core material for preparing the optical filter, the cost of the photoresist accounts for 6% -8% of the cost of the optical filter, and the quality of the photoresist directly influences the performance of the optical filter.
At present, the preparation of photoresist is carried out by combining acrylic resin with black pigment dispersion liquid in the market. The acrylic resin is used as a film forming resin of the photoresist and participates in the photo-curing reaction and the photo-decomposition reaction at the same time, and finally the patterned film forming resin is obtained. In the use process of the photoresist, when the conventional acrylic resin is matched with black pigment dispersion liquid, the obtained photoresist has the problems of low adhesive force, insufficient water repellency and the like. Therefore, there is a need to improve the adhesion and water repellency of the photoresist by changing the formulation of the photoresist.
Disclosure of Invention
In order to improve the adhesion and water repellency of photoresist, the present application provides a photoresist composition and photoresist prepared therefrom. The photoresist prepared by the application has high adhesive force and high water repellency, and the resolution of the optical filter is not affected when the photoresist is coated on the optical filter.
In a first aspect, the application provides a photoresist composition, which comprises, by weight, 25-35 parts of black dispersion pigment liquid, 3-6 parts of organic fluorosilicone modified acrylic resin, 8-10 parts of acrylic resin, 3-5 parts of monomer, 1-2 parts of photoinitiator, 2-6 parts of auxiliary agent and 60-80 parts of solvent, wherein the monomer is an acrylic compound or a methacrylate compound containing more than 3 ethylenically unsaturated groups, and the weight average molecular weight of the acrylic resin is 7000-30000.
Preferably, the organic fluorine silicon modified acrylic resin is used in an amount of 4-5 parts and the acrylic resin is used in an amount of 8-9 parts.
The photoresist composition of the application can improve the adhesive force and the water repellency of the photoresist by matching the organic fluorine-silicon modified acrylic resin with the acrylic resin. In particular, the amount of the organofluorosilicone modified acrylic resin and the acrylic resin used has a certain influence on the adhesion and water repellency of the photoresist. When the organic fluorine silicon modified acrylic resin and the acrylic resin are compounded according to (3-6 parts by weight)/(8-10 parts by weight), the adhesive force of the photoresist can be improved to be more than 4B, and the water contact angle is more than 85 degrees.
In the present application, the monomer means an acrylic compound or a methacrylic compound having 3 or more ethylenically unsaturated groups. The acrylic compound having 3 or more ethylenically unsaturated groups may be selected from any one of pentaerythritol triacrylate, pentaerythritol tetraacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, trimethylolpropane triacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate.
The methacrylate compound may be selected from any one of trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethylacrylate, sorbitol trimethacrylate, sorbitol tetramethacrylate.
In the present application, the auxiliary agent may be a mixture of a silane coupling agent and a surfactant.
In the present application, the solvent may be a mixture of propylene glycol methyl ether acetate (PMA solvent) and ethylene glycol dimethyl ether (EDM solvent).
In a specific embodiment, the photoresist composition of the present application comprises: 30 parts of black dispersion pigment liquid, 5 parts of organic fluorine silicon modified acrylic resin, 9 parts of acrylic resin, 4 parts of monomer, 1.3 parts of photoinitiator, 4 parts of auxiliary agent and 70 parts of solvent. The photoresist prepared by the technical scheme is applied to the optical filter, so that the optical filter has better resolution, and the photoresist has better adhesive force and water repellency. The resolution of the optical filter is below 5 mu m, the adhesive force of the photoresist is above 4B, and the water contact angle is above 85 degrees.
Preferably, the weight average molecular weight of the acrylic resin is 15000.
In the present application, the weight average molecular weight of the acrylic resin affects the adhesion and water repellency of the photoresist. When the weight average molecular weight of the acrylic resin is higher than 30000 or lower than 7000, the adhesion and water-gathering property of the photoresist can meet the requirements, but after the photoresist is coated on the optical filter, the resolution of the optical filter is too high, so that development is blurred, even the optical filter cannot be developed, and thus the weight average molecular weight of the acrylic resin needs to be controlled. Illustratively, the weight average molecular weight of the acrylic resin may be 7000, 10000, 15000, 20000, 25000, or 30000.
In the present application, the organofluorosilicone-modified acrylic resin means that the acrylic resin has a fluorine group and a silicon group in a side chain thereof. And mixing the organic fluorine-silicon modified acrylic resin with the acrylic resin to prepare the photoresist. The fluorine group and the silicon group are added on the side chain of the acrylic resin, so that the water repellency, the adhesive force, the chemical resistance and the high temperature resistance of the photoresist can be improved.
The organofluorosilicone modified acrylic resin may be obtained commercially or by methods known in the art. Related studies report various methods for preparing organofluorosilicone modified acrylic resins. In some reports, fluorine groups are first attached to the side chains of the acrylic resin to form F-C chemical bonds, followed by silicon groups to form Si-C chemical bonds. In other reports, a silicon group is first attached to the side chain of an acrylic resin to form a Si-C chemical bond, and then a fluorine group is attached to form an F-C chemical bond.
The application provides a preparation method of organic fluorine silicon modified acrylic resin. In the production method of the present application, the organofluorosilicone-modified acrylic resin is obtained by modifying an acrylic resin with fluorosilane. In one embodiment of the present application, a method for preparing an organofluorosilicone modified acrylic resin includes preparing fluorosilane into fluorosilane oligomer and then reacting the fluorosilane oligomer with the acrylic resin in a predetermined ratio. In the reaction of the fluorosilane oligomer with the acrylic resin, not only polymerization reaction occurs, but also van der Waals force formed by the fluorine group of the fluorosilane oligomer, the silicon group and-OH of the acrylic resin exists, and thus, the fluorine group and the silicon group are introduced into the organofluorosilicone-modified acrylic resin, and such fluorine group and silicon group are not directly connected to C of the acrylic fragment but connected to C of the fluorosilane fragment. And then mixing the organic fluorine-silicon modified acrylic resin with acrylic resin to prepare photoresist, wherein fluorine groups and silicon groups in the organic fluorine-silicon modified acrylic resin and-OH of the acrylic resin form bonding effect again.
In a specific embodiment, the organofluorosilicone-modified acrylic resin is obtained by:
s1: preparing fluorosilane into fluorosilane oligomer;
s2: the fluorosilane oligomer and acrylic resin react according to the weight ratio of (22-27) to obtain the organic fluorosilicone modified acrylic resin,
In a specific embodiment, the fluorosilane is 1H, 2H-perfluorooctyl triethoxysilane.
In a specific embodiment, the weight ratio of fluorosilane oligomer to acrylic resin is 1:25.
In the preparation process of the organic fluorine silicon modified acrylic resin, the dosage ratio of the fluorine silane oligomer to the acrylic resin is an index for influencing the organic fluorine silicon modified acrylic resin. When the weight ratio of the fluorosilane oligomer to the acrylic resin is other than 1 (22-27), the adhesive force of the photoresist is less changed, the water contact angle is gradually reduced, which means that the water repellency of the photoresist is gradually weakened. Illustratively, the weight ratio of fluorosilane oligomer to acrylic resin may be 1:22,1:23,1:24,1:25,1:26, or 1:27.
In one embodiment of the present application, the method for preparing the organofluorosilicone modified acrylic resin comprises the steps of: mixing the fluorosilane oligomer with acrylic resin to obtain a mixture of the fluorosilane oligomer and the acrylic resin, adding a PMA solvent into the mixture, reacting for 3.5-6.0h at the temperature of 70-90 ℃, and then distilling the reaction mixture under reduced pressure to remove the PMA solvent to obtain the organic fluorosilicone modified acrylic resin.
In the present application, the preparation method of the fluorosilane oligomer includes the steps of: and (3) placing the fluorosilane in an ethanol water solution, regulating the pH of the solution to 10-11 by using ammonia water to hydrolyze, and drying to obtain the fluorosilane oligomer.
In one embodiment, the time of hydrolysis is from 4 to 6 hours;
in one embodiment, the drying is at a temperature of 130 to 150 ℃ and the drying is for a time of 1.8 to 2 hours.
In the preparation method of the fluorosilane oligomer, the ammonia water has the function of promoting the hydrolysis of the fluorosilane.
In a specific embodiment, the hydrolysis time is 5 hours, the drying temperature is 130 ℃, the drying time is 2 hours, and the reaction time is 3.5 hours.
In the present application, the acrylic resin may be obtained by a commercially available method. The acrylic resins obtained commercially are, for example: the Daianana (DIANAL) series (manufactured by mitsubishi yang polymer materials limited (Mitsubishi Ra yon co., ltd.)), ACRYDIC series (manufactured by DIC dieseng), and the like.
In the present application, the acrylic resin can also be obtained by a production method in which an unsaturated acrylic monomer containing a carboxyl group, an unsaturated acrylic monomer containing an aromatic or heterocyclic group, and other acrylic monomers are reacted in a ratio of (1-3): 2-4): 3-5 by weight, thereby obtaining an acrylic resin.
Illustratively, the carboxyl group-containing unsaturated acrylic monomer may be selected from any one of monocarboxylic acid-based monomers, dicarboxylic acid-based monomers, and mono (meth) acrylate-based monomers. Wherein the monocarboxylic acid monomer can be acrylic acid, methacrylic acid, crotonic acid, etc. The dicarboxylic acid monomer may be fumaric acid, mesaconic acid, itaconic acid, an anhydride of dicarboxylic acid, or the like. The mono (meth) acrylate monomer may be ω -carboxy polycaprolactone mono (meth) acrylate or the like.
The unsaturated acrylic monomer containing an aromatic or heterocyclic group may be exemplified by any one selected from the group consisting of aryl (meth) acrylate monomers, N-substituted maleimide compounds, styrene, α -methylstyrene, vinyl toluene. The aryl (meth) acrylate monomer may be phenyl (meth) acrylate, benzyl (meth) acrylate, toluene (meth) acrylate, or the like.
The N-substituted maleimide compound may be N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m-methylphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, N-p-methoxyphenylmaleimide, or the like.
The other acrylic monomer may be illustratively selected from any one of alkyl (meth) acrylate, unsaturated oxetane compounds.
The alkyl (meth) acrylate may be methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, or the like.
The unsaturated oxetane compound may be 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) -3-ethyloxetane, 3- (methacryloyloxymethyl) -2-trifluoromethyloxy oxetane, 3- (methacryloyloxymethyl) -2-phenyloxetane, 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxy oxetane. In addition, an unsaturated acrylic monomer having a polymerizable group may be used as the other acrylic monomer. The polymerizable group may be a (meth) allyl group, a (meth) acryl group, or the like.
In one embodiment of the present application, the monomers used to prepare the acrylic resin may be n-butyl methacrylate, styrene, and methacrylic acid, wherein the weight ratio of methacrylic acid, styrene, and n-butyl methacrylate is (1-3): 2-4): 3-5.
In the present application, the acrylic resin used in the preparation of the organofluorosilicone-modified acrylic resin may be the same as or different from the acrylic resin used in the preparation of the photoresist. The acrylic resin used for preparing the photoresist by neutralization of the organic fluorine silicon modified acrylic resin is prepared by the preparation method of the acrylic resin; the acrylic resin used in the preparation of the organosilicon modified acrylic resin is prepared by the preparation method of the acrylic resin in the application, and the acrylic resin used in the preparation of the photoresist is obtained by the commercial use such as: the Daianana (DIANAL) series.
In the present application, the photoinitiator may be selected from one or more of benzophenone and triethanolamine.
In a specific embodiment, the photoinitiator is a mixture of benzophenone and triethanolamine in a weight ratio of benzophenone to triethanolamine of 1:1.
In a second aspect, the present application provides a photoresist prepared from the photoresist composition of the present application. And mixing the organic fluorine silicon modified acrylic resin with the acrylic resin, and adjusting the addition amount of the organic fluorine silicon modified acrylic resin and the acrylic resin to obtain the photoresist. The adhesive force grade of the photoresist is above 4B, and the water contact angle is above 85 degrees.
In summary, the application has the following beneficial effects:
1. According to the application, the photoresist is prepared by adopting the mutual synergy of the organic fluorine-silicon modified acrylic resin and the acrylic resin, and the obtained photoresist not only can ensure that the optical filter has better resolution ratio, but also has higher adhesive force and water repellency to the optical filter in the use process;
2. the adhesive force of the photoresist obtained by the application is above 4B level, even above 5B level;
3. The water contact angle of the photoresist obtained by the application is more than 85 degrees, even more than 91 degrees;
4. The photoresist prepared by the application is applied to the optical filter, and the resolution of the optical filter is kept below 5 mu m.
Detailed Description
The present application will be described in further detail with reference to examples.
Raw materials
The components used in the present application are all commercially available.
Preparation example of organosilicon modified acrylic resin
Preparation example 1
S1: placing 2g of 1H, 2H-perfluoro octyl triethoxysilane into 98g of ethanol water solution, regulating the pH value of the obtained solution to 10 by using ammonia water to promote the hydrolysis of fluorosilane, and drying to obtain fluorosilane oligomer, wherein the hydrolysis time is 5 hours, the drying temperature is 130 ℃, and the drying time is 2 hours;
S2: 0.4g of fluorosilane oligomer was mixed with 10g of acrylic resin (the weight ratio of fluorosilane oligomer to acrylic resin was 1:25), and then 100mL of PMA solvent was added to the resultant mixture; reacting for 3.5h at the water bath temperature of 90 ℃; and (3) distilling the obtained reaction solution under reduced pressure to remove the PMA solvent, thus obtaining the organic fluorosilicone modified acrylic resin.
The preparation method of the acrylic resin comprises the following steps: as monomers, methacrylic acid, styrene, n-butyl methacrylate and azobisisobutyronitrile were mixed, wherein the weight ratio of methacrylic acid, styrene, n-butyl methacrylate and azobisisobutyronitrile was 1.5:3:4:1.5. Carrying out polymerization reaction for 2 hours at the temperature of 85 ℃ to obtain acrylic resin; the weight average molecular weight of the acrylic resin was 15000. The weight average molecular weight of the acrylic resin is adjusted by controlling the polymerization time.
The differences between preparation examples 2 to 10 and preparation example 1 are shown in Table 1.
TABLE 1 parameters for the distinction between PREPARATIVE EXAMPLES 2-10 and PREPARATIVE EXAMPLE 1
Examples
Example 1
Under a yellow light laboratory, 3kg of organic fluorine-silicon modified acrylic resin, 30kg of black dispersion pigment liquid, 9kg of acrylic resin, 4kg of monomer, 4kg of auxiliary agent, 70kg of solvent and 1.3kg of photoinitiator are mixed and stirred for 3 hours to obtain the black photoresist.
Wherein the photoinitiator is a mixture of benzophenone and triethanolamine, and the weight ratio of the benzophenone to the triethanolamine is 1:1;
Wherein the auxiliary agent is a mixture of a silane coupling agent and a surfactant, and the weight ratio of the silane coupling agent to the surfactant is 3:2;
wherein the solvent is a mixture of PMA solvent and EDM solvent, and the weight ratio of the PMA solvent to the EDM solvent is 2:3;
wherein the monomer is dipentaerythritol hexaacrylate;
wherein the organic fluorine silicon modified acrylic resin is obtained after being prepared by a preparation example 1;
Wherein the acrylic resin was obtained after the preparation of the acrylic resin described in preparation example 1, and the weight average molecular weight of the acrylic resin was 15000.
The differences between examples 2-12 and example 1 are shown in Table 2.
TABLE 2 dosage form (unit: kg) of the components in examples 1 to 12
Example 13
Example 13 differs from example 2 in that the monomer in example 13 is trimethylolethane trimethacrylate.
Example 14
Example 14 differs from example 2 in that the acrylic resin in example 14 was Daianan (DIANAL) BR113 (manufactured by mitsubishi yang polymer materials limited (Mitsubishi Ra yon co., ltd.)) and the weight average molecular weight was 30000.
Comparative example
The differences between comparative examples 1 to 7 and example 2 are shown in Table 3.
TABLE 3 dosage form (unit: kg) of each component in comparative examples 1 to 7
Performance test
21 Kinds of photoresists were prepared according to the schemes of examples 1 to 14 and comparative examples 1 to 7, the 21 kinds of photoresists were spin-coated on a blank glass of 7cm×7cm, and the thickness of the photoresists was 1.2 μm by controlling the rotation speed, and then baked at 100 ℃ for 3min to obtain a glass with a thin film. And exposing the glass with the film by using a mask plate with a line/gap pattern of 1-50 mu m, wherein the exposure amount is 40mj/cm 2, developing by using an alkaline developing solution, washing to remove residual developing solution, and finally baking the developed glass in a baking oven at 230 ℃ for 30min to obtain the color chip for testing.
Adhesion test: the detection is carried out by using a hundred-cell test method. Firstly, uniformly drawing a square lattice with a certain specification size on a film layer of a color chip for testing by using a Bai-li knife, and then, sticking and pulling by using a 3M adhesive tape, and evaluating the adhesion degree of the film layer to a substrate by evaluating the integrity degree of the film layer in the square lattice (refer to GB 9286-1998).
And (3) water repellency detection: and testing and analyzing the water repellency performance of the surface of the color chip for testing by using a contact angle measuring instrument. And 5 mu L of liquid drops are dripped on the surface of the color chip for test when the ultra-pure water is used as the water contact angle test liquid drops, 5 different positions are selected on the surface of each color chip for test for measurement, and the final test result is the average value of 5 times of measured values (GB/T30693-2014).
Resolution evaluation criteria: the minimum line remaining in the patch pattern was confirmed as an evaluation criterion for resolution using an optical microscope. The specific detection results are shown in Table 4.
TABLE 4 detection results
As can be seen from the combination of examples 1 to 14 and table 4, examples 1 to 14 were prepared into photoresists by the mutual cooperation of the organofluorosilicone modified acrylic resin and the acrylic resin, and the photoresists can ensure that the optical filter has better resolution and can improve the adhesive force and the water repellency of the optical filter. The adhesive force grade of the photoresist is above 4B grade, and the contact angle is above 85 degrees. In particular, the photoresist prepared in example 2 has an adhesion rating of 5B and a contact angle of 99 °.
It can be seen from the combination of examples 1 to 14 and comparative examples 1 to 5 and the combination of table 4 that when the organofluorosilicone-modified acrylic resin was not added to the photoresist, although the optical filter was ensured to have a good resolution, the adhesive force rating of the photoresist was low, the contact angle was small, indicating that the adhesive force and water repellency of the photoresist were poor.
As can be seen from the combination of examples 2, 8, 9, 10 and comparative examples 6, 7 and the combination of table 4, as the weight average molecular weight of the acrylic resin increases, the contact angle of the photoresist increases and decreases, indicating that the water repellency of the photoresist increases and decreases.
The photoresists of comparative examples 6 and 7 were satisfactory in both adhesion and contact angle, but when the weight average molecular weight of the acrylic resin was less than 7000 or more than 30000, the optical filter could not be ensured to have a good resolution.
The present embodiment is only for explanation of the present application and is not to be construed as limiting the present application, and modifications to the present embodiment, which may not creatively contribute to the present application as required by those skilled in the art after reading the present specification, are all protected by patent laws within the scope of claims of the present application.
Claims (9)
1. A photoresist composition is characterized by comprising, by weight, 25-35 parts of black dispersion pigment liquid, 3-6 parts of organic fluorosilicone modified acrylic resin, 8-10 parts of acrylic resin, 3-5 parts of monomer, 1-2 parts of photoinitiator, 2-6 parts of auxiliary agent and 60-80 parts of solvent,
Wherein the monomer refers to an acrylic compound or a methacrylic compound containing 3 or more ethylenically unsaturated groups,
Wherein the weight average molecular weight of the acrylic resin is 7000 to 30000.
2. The photoresist composition according to claim 1, wherein the organofluorosilicone modified acrylic resin is used in an amount of 4 to 5 parts and the acrylic resin is used in an amount of 8 to 9 parts.
3. The photoresist composition of claim 1, wherein the photoresist composition comprises: 30 parts of black dispersion pigment liquid, 5 parts of organic fluorine silicon modified acrylic resin, 9 parts of acrylic resin, 4 parts of monomer, 1.3 parts of photoinitiator, 4 parts of auxiliary agent and 70 parts of solvent.
4. The photoresist composition of claim 1, wherein the acrylic resin has a weight average molecular weight of 15000.
5. The photoresist composition according to any one of claims 1 to 4, wherein the organofluorosilicone modified acrylic resin is obtained by:
s1: preparing fluorosilane into fluorosilane oligomer;
S2: and (3) reacting the fluorosilane oligomer with acrylic resin according to the weight ratio of (22-27) to obtain the organic fluorosilicone modified acrylic resin.
6. The photoresist composition of claim 5, wherein the fluorosilane is 1h,2 h-perfluorooctyltriethoxysilane.
7. The photoresist composition of claim 5, wherein the weight ratio of fluorosilane oligomer to acrylic resin is 1:25.
8. A photoresist prepared from the photoresist composition of any one of claims 1 to 7.
9. The photoresist according to claim 8, wherein the adhesion rating of the photoresist is above 4B and the water contact angle is above 85 °.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6775390A (en) * | 1989-12-04 | 1991-06-06 | Nippon Paint Co., Ltd. | A method for forming a photoresist with a cover coat |
| KR20020042097A (en) * | 2000-11-30 | 2002-06-05 | 박종섭 | Selective photo resist and method for forming photo resist pattern and semiconductor device using the same |
| JP2004107447A (en) * | 2002-09-17 | 2004-04-08 | Kanegafuchi Chem Ind Co Ltd | Pressure-sensitive adhesive composition, pressure-sensitive adhesive tape or sheet using the adhesive composition and hot-melt type acrylic pressure-sensitive adhesive |
| WO2008021291A2 (en) * | 2006-08-14 | 2008-02-21 | E. I. Du Pont De Nemours And Company | Fluorinated polymers for use in immersion lithography |
| KR20090004054A (en) * | 2007-07-06 | 2009-01-12 | 주식회사 엘지화학 | Photosensitive resin composition for black matrix |
| CN104865794A (en) * | 2014-02-20 | 2015-08-26 | 上海飞凯光电材料股份有限公司 | Photoresist |
| CN105785716A (en) * | 2014-12-26 | 2016-07-20 | 上海飞凯光电材料股份有限公司 | Photoresist |
| CN109810638A (en) * | 2019-01-25 | 2019-05-28 | 苏州凡赛特材料科技有限公司 | A kind of low-refraction optics pressure sensitive adhesive and its preparation method and application |
| CN112745453A (en) * | 2020-12-30 | 2021-05-04 | 西安瑞联新材料股份有限公司 | Fluorine-containing acrylic resin and preparation method and application thereof |
-
2021
- 2021-12-30 CN CN202111680620.0A patent/CN114415469B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6775390A (en) * | 1989-12-04 | 1991-06-06 | Nippon Paint Co., Ltd. | A method for forming a photoresist with a cover coat |
| KR20020042097A (en) * | 2000-11-30 | 2002-06-05 | 박종섭 | Selective photo resist and method for forming photo resist pattern and semiconductor device using the same |
| JP2004107447A (en) * | 2002-09-17 | 2004-04-08 | Kanegafuchi Chem Ind Co Ltd | Pressure-sensitive adhesive composition, pressure-sensitive adhesive tape or sheet using the adhesive composition and hot-melt type acrylic pressure-sensitive adhesive |
| WO2008021291A2 (en) * | 2006-08-14 | 2008-02-21 | E. I. Du Pont De Nemours And Company | Fluorinated polymers for use in immersion lithography |
| KR20090004054A (en) * | 2007-07-06 | 2009-01-12 | 주식회사 엘지화학 | Photosensitive resin composition for black matrix |
| CN104865794A (en) * | 2014-02-20 | 2015-08-26 | 上海飞凯光电材料股份有限公司 | Photoresist |
| CN105785716A (en) * | 2014-12-26 | 2016-07-20 | 上海飞凯光电材料股份有限公司 | Photoresist |
| CN109810638A (en) * | 2019-01-25 | 2019-05-28 | 苏州凡赛特材料科技有限公司 | A kind of low-refraction optics pressure sensitive adhesive and its preparation method and application |
| CN112745453A (en) * | 2020-12-30 | 2021-05-04 | 西安瑞联新材料股份有限公司 | Fluorine-containing acrylic resin and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 光致抗蚀干膜用水溶性丙烯酸树脂的优化合成;邓秉明;叶代勇;;热固性树脂;20110130(01);第25-30页 * |
| 新型光敏封装胶的研制;郑永军;粘接;20040810(04);第14-16页 * |
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