CN114415469A - Photoresist composition and photoresist - Google Patents
Photoresist composition and photoresist Download PDFInfo
- Publication number
- CN114415469A CN114415469A CN202111680620.0A CN202111680620A CN114415469A CN 114415469 A CN114415469 A CN 114415469A CN 202111680620 A CN202111680620 A CN 202111680620A CN 114415469 A CN114415469 A CN 114415469A
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- CN
- China
- Prior art keywords
- acrylic resin
- parts
- photoresist
- photoresist composition
- fluorosilane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 79
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 113
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 113
- 239000000178 monomer Substances 0.000 claims abstract description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 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 13
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 8
- 239000000049 pigment Substances 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims abstract description 5
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 claims description 30
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical group CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 abstract description 20
- 239000000853 adhesive Substances 0.000 abstract description 16
- 230000001070 adhesive effect Effects 0.000 abstract description 16
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 238000000034 method Methods 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 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
- 230000000052 comparative effect Effects 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
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000243 solution 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
- 239000010408 film 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
- 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
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000126 substance Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 230000008569 process 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- 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
- FARWYUGFTNOIPS-UHFFFAOYSA-N [2-(trifluoromethyl)oxetan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1C(F)(F)F FARWYUGFTNOIPS-UHFFFAOYSA-N 0.000 description 1
- IDNJLJOPWXDNJW-UHFFFAOYSA-N [4-(trifluoromethyl)oxetan-2-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC(C(F)(F)F)O1 IDNJLJOPWXDNJW-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000009471 action Effects 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
- 239000007864 aqueous solution Substances 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
- 150000001875 compounds Chemical class 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
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 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
- 239000000463 material Substances 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
- 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
- 238000011160 research Methods 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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 a photoresist. The photoresist composition comprises, by weight, 25-35 parts of black dispersion pigment liquid, 3-6 parts of organic fluorine-silicon modified acrylic resin, 8-10 parts of acrylic resin, 3-5 parts of monomers, 1-2 parts of a photoinitiator, 2-6 parts of an auxiliary agent and 60-80 parts of a solvent; the monomer is an acrylic acid or methacrylic acid ester compound having 3 or more 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 with each other, 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 more than 4B grade, and the water contact angle is more than 85 degrees.
Description
Technical Field
The application relates to the field of liquid crystal display panels, in particular to a photoresist composition and a 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.
In the current market, the preparation of the photoresist is carried out by combining acrylic resin and a black pigment dispersion liquid. The acrylic resin is used as film-forming resin of the photoresist and participates in photocuring reaction and photolysis reaction at the same time, and finally patterned film-forming resin is obtained. When the photoresist is used, the conventional acrylic resin is matched with the black pigment dispersion liquid for use, and the obtained photoresist has the problems of low adhesive force, insufficient water repellency and the like. Therefore, it is required to improve the adhesion and water repellency of the photoresist by changing the formulation of the photoresist.
Disclosure of Invention
To improve the adhesion and water repellency of a photoresist, a photoresist composition and a photoresist prepared therefrom are provided. The photoresist prepared by the method has high adhesive force and high water repellency, and when the photoresist is coated on the optical filter, the resolution of the optical filter is not influenced.
According to a first aspect, the application provides a photoresist composition, which comprises, by weight, 25-35 parts of a black dispersion pigment liquid, 3-6 parts of an organic fluorine-silicon modified acrylic resin, 8-10 parts of an acrylic resin, 3-5 parts of a monomer, 1-2 parts of a photoinitiator, 2-6 parts of an auxiliary agent and 60-80 parts of a 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 usage amount of the organic fluorine-silicon modified acrylic resin is 4-5 parts, and the usage amount of the acrylic resin is 8-9 parts.
According to the photoresist composition, the organic fluorine-silicon modified acrylic resin and the acrylic resin are matched with each other, so that the adhesive force and the water repellency of the photoresist can be improved. Particularly, the dosage of the organic fluorine-silicon modified acrylic resin and the acrylic resin has certain influence on the adhesive force and the water repellency of the photoresist. When the organic fluorine silicon modified acrylic resin and the acrylic resin are compounded according to the proportion of (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 any one selected from pentaerythritol triacrylate, pentaerythritol tetraacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, trimethylolpropane triacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate.
The methacrylate compound may be any one selected from trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, sorbitol trimethacrylate, and 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 dispersed 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 ratio, and the photoresist has better adhesive force and water repellency. The resolution of the optical filter is below 5 μm, 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 may affect 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-trapping performance 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 the development is blurred, and even the optical filter cannot be developed, so that 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 a fluorine group and a silicon group are carried on a side chain of the acrylic resin. And mixing the organic fluorine-silicon modified acrylic resin with the acrylic resin to prepare the photoresist. The addition of fluorine groups and silicon groups on the side chain of the acrylic resin can improve the water repellency, adhesive force, chemical resistance and high temperature resistance of the photoresist.
The organofluorosilicone-modified acrylic resin may be obtained commercially, or may be obtained by a preparation method known in the art. Related researches report preparation methods of various organic fluorine-silicon modified acrylic resins. In some reports, fluorine groups are first grafted to the side chains of acrylic resins to form F-C bonds, and then silicon groups are grafted to form Si-C bonds. In other reports, a silicon group is grafted to a side chain of an acrylic resin to form an Si-C chemical bond, and then a fluorine group is grafted to form an F-C chemical bond.
The application provides a preparation method of organic fluorine-silicon modified acrylic resin. In the preparation method of the present application, the organofluorosilane-modified acrylic resin is obtained by modifying an acrylic resin with fluorosilane. In one embodiment of the present application, a method for preparing an organofluorosilane-modified acrylic resin includes preparing fluorosilane into fluorosilane oligomers, and reacting the fluorosilane oligomers with an acrylic resin according to 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, whereby the fluorine group and the silicon group are introduced into the organofluorosilane-modified acrylic resin, and such fluorine group and silicon group are not directly connected to C of the acrylic fragment but are connected to C of the fluorosilane fragment. And then, when the organic fluorine-silicon modified acrylic resin and the acrylic resin are mixed to prepare the photoresist, the fluorine group in the organic fluorine-silicon modified acrylic resin, the silicon group and-OH of the acrylic resin form bonding action again.
In one embodiment, the organofluorosilicone modified acrylic resin is obtained by:
s1: preparing fluorosilane into fluorosilane oligomer;
s2: reacting fluorosilane oligomer with acrylic resin according to the weight ratio of 1 (22-27) to obtain organic fluorine-silicon modified acrylic resin,
in one embodiment, the fluorosilane is 1H,1H,2H, 2H-perfluorooctyltriethoxysilane.
In a specific embodiment, the weight ratio of the fluorosilane oligomer to the acrylic resin is 1: 25.
In the process of preparing the organic fluorine-silicon modified acrylic resin, the dosage ratio of the fluorine-silicon alkyl oligomer to the acrylic resin is an index influencing the organic fluorine-silicon modified acrylic resin. When the weight ratio of the fluorosilane oligomer to the acrylic resin is beyond 1 (22-27), the adhesive force of the photoresist is changed slightly, and the water contact angle is gradually reduced, which indicates that the water repellency of the photoresist is gradually weakened. Illustratively, the weight ratio of the fluorosilane oligomer to the 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 and 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 carrying out reduced pressure distillation on the reaction mixture to remove the PMA solvent, thus obtaining the organic fluorine-silicon modified acrylic resin.
In the present application, the preparation method of the fluorosilane oligomer comprises the steps of: and putting fluorosilane in an ethanol water solution, adjusting the pH of the solution to 10-11 by using ammonia water for hydrolysis, and drying to obtain fluorosilane oligomer.
In one embodiment, the hydrolysis time is 4 to 6 hours;
in one embodiment, the temperature of the drying is 130-150 ℃, and the time of the drying is 1.8-2 h.
In the preparation method of the fluorosilane oligomer, the ammonia water functions to promote hydrolysis of fluorosilane.
In a specific embodiment, the hydrolysis time is 5h, the drying temperature is 130 ℃, the drying time is 2h, and the reaction time is 3.5 h.
In the present application, the acrylic resin may be obtained by a commercially available method. Commercially available acrylic resins are, for example: a Dianna (DIANAL) series (manufactured by Mitsubishi Ra yon co., Ltd.)), an ACRYDIC series (manufactured by DIC dean corporation), and the like.
In the present application, the acrylic resin may also be obtained by a preparation method in which an unsaturated acrylic monomer having a carboxyl group, an unsaturated acrylic monomer having an aromatic or heterocyclic group, and other acrylic monomers are reacted in a weight ratio of (1-3) to (2-4) to (3-5), thereby obtaining the acrylic resin.
Illustratively, the carboxyl group-containing unsaturated acrylic monomer may be any one selected from monocarboxylic acid monomers, dicarboxylic acid monomers, and mono (meth) acrylate monomers. The monocarboxylic acid monomer may be acrylic acid, methacrylic acid, crotonic acid, etc. The dicarboxylic acid monomer may be fumaric acid, mesaconic acid, itaconic acid, or an anhydride of a dicarboxylic acid. The mono (meth) acrylate monomer may be omega-carboxy polycaprolactone mono (meth) acrylate, or the like.
Illustratively, the unsaturated acrylic monomer having an aromatic or heterocyclic group may be selected from any one of (meth) acrylic acid aryl ester monomers, N-substituted maleimide compounds, styrene, α -methylstyrene, and vinyltoluene. The aryl (meth) acrylate monomer may be phenyl (meth) acrylate, benzyl (meth) acrylate, methylphenyl (meth) acrylate, or the like.
The N-substituted maleimide-based 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.
Illustratively, the other acrylic monomer may be selected from any one of alkyl (meth) acrylates, 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-trifluoromethyloxetane, 3- (methacryloyloxymethyl) -2-phenyloxetane, 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane. In addition, an unsaturated acrylic monomer having a polymerizable group can be used as the other acrylic monomer. The polymerizable group may be a (meth) allyl group, a (meth) acryloyl group, or the like.
In one embodiment herein, 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 is the same as the acrylic resin used in the preparation of the photoresist, and the source may be different. The acrylic resins used in the preparation of the organofluorosilicone modified acrylic resin and in the preparation of the photoresist are both prepared by the method for preparing the acrylic resin described herein; the acrylic resin as used in the preparation of the organofluorosilicone modified acrylic resin is prepared by the method for preparing an acrylic resin as described in the present application, and the acrylic resin used in the preparation of the photoresist is commercially available as: the Diana (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 described herein. And mixing the organic fluorine-silicon modified acrylic resin with acrylic resin, and adjusting the adding 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 more than 4B, and the water contact angle is more than 85 degrees.
In summary, the present application has the following beneficial effects:
1. according to the method, the organic fluorine-silicon modified acrylic resin and the acrylic resin are mutually cooperated to prepare the photoresist, and the obtained photoresist can ensure that the optical filter has better resolution ratio and 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 method is above level 4B, even above level 5B;
3. the water contact angle of the photoresist obtained by the method is more than 85 degrees, even more than 91 degrees;
4. the photoresist prepared by the method is applied to an 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 organic FluoroSilicone-modified acrylic resin
Preparation example 1
S1: placing 2g of 1H,1H,2H, 2H-perfluorooctyltriethoxysilane in 98g of ethanol aqueous solution, adjusting the pH of the obtained solution to 10 by using ammonia water, promoting 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: mixing 0.4g of fluorosilane oligomer with 10g of acrylic resin (weight ratio of fluorosilane oligomer to acrylic resin 1:25), followed by adding 100mL of PMA solvent to the resulting mixture; reacting for 3.5h under the condition that the temperature of the water bath is 90 ℃; and distilling the obtained reaction solution under reduced pressure to remove the PMA solvent, thus obtaining the organic fluorine-silicon modified acrylic resin.
The preparation method of the acrylic resin comprises the following steps: methacrylic acid, styrene, n-butyl methacrylate and azobisisobutyronitrile were mixed as monomers, 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 2h at 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 time of the polymerization reaction.
The differences between preparation examples 2 to 10 and preparation example 1 are shown in Table 1.
TABLE 1 parameters distinguishing preparations 2 to 10 from preparation 1
Examples
Example 1
In a yellow light laboratory, 3kg of organic fluorine-silicon modified acrylic resin, 30kg of black dispersed 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, wherein the weight ratio of PMA solvent to EDM solvent is 2: 3;
wherein the monomer is dipentaerythritol hexaacrylate;
wherein the organic fluorine-silicon modified acrylic resin is obtained after preparation of preparation example 1;
wherein the acrylic resin was obtained after the preparation of the acrylic resin according to preparation example 1, and the weight average molecular weight of the acrylic resin was 15000.
The differences between examples 2 to 12 and example 1 are shown in Table 2.
TABLE 2 dosage of each component in examples 1-12 (unit: kg)
Example 13
Example 13 differs from example 2 in that the monomer in example 13 is trimethylolethane trimethacrylate.
Example 14
Example 14 is different from example 2 in that the acrylic resin in example 14 was Daiana (DIANAL) BR113 (manufactured by Mitsubishi Ra yon co., Ltd.) and had a weight average molecular weight of 30000.
Comparative example
The differences between comparative examples 1 to 7 and example 2 are shown in Table 3.
TABLE 3 dosage of each component in comparative examples 1 to 7 (unit: kg)
Performance test
21 kinds of photoresists were prepared according to the schemes of examples 1 to 14 and comparative examples 1 to 7, and the 21 kinds of photoresists were respectively spin-coated on a blank glass of 7cm × 7cm, so that the thickness of the photoresist was 1.2 μm by controlling the rotation speed, and then dried at 100 ℃ for 3min to obtain a glass with a thin film. Exposing the glass with the film by using a mask plate with a 1-50 μm line/gap pattern with an exposure of 40mj/cm2And developing by using an alkaline developing solution, washing by using water to remove residual developing solution, and finally baking the developed glass in a 230 ℃ oven for 30min to obtain the color chip for testing.
And (3) testing the adhesive force: and detecting by adopting a Baige test method. Firstly, a check with a certain specification and size is evenly marked on a film layer of a color film for testing by using a check force knife, and then the adhesion degree of the film layer to a base material is evaluated by evaluating the integrity degree of the film layer in the check by using 3M adhesive tape for sticking and pulling (refer to GB 9286-1998).
And (3) water repellency detection: and testing and analyzing the surface water repellency of the color chip for testing by using a contact angle measuring instrument. And (3) using ultrapure water as a water contact angle test liquid drop, dripping 5 mu L of the liquid drop on the surface of the color piece for test in each test, selecting 5 different positions on the surface of each color piece for measurement, and taking the average value of 5 measurement values (GB/T30693-2014) as the final test result.
Resolution evaluation criteria: the minimum line remaining from the color patch pattern was confirmed by an optical microscope as an evaluation criterion of the resolution. Specific detection results are shown in table 4.
TABLE 4 test results
As can be seen from the combination of examples 1 to 14 and table 4, in examples 1 to 14, the photoresist prepared by the mutual matching of the organofluorosilicone modified acrylic resin and the acrylic resin can ensure that the optical filter has a better resolution, and can improve the self adhesion and water repellency. The adhesive force grade of the photoresist is more than 4B grade, and the contact angle is more than 85 degrees. In particular, the photoresist prepared from example 2 had an adhesion rating of 5B and a contact angle of 99 °.
It can be seen by combining examples 1 to 14 and comparative examples 1 to 5 with table 4 that, when no organofluorosilicone modified acrylic resin is added to the photoresist, the optical filter has better resolution, but the photoresist has lower adhesion level and smaller contact angle, which indicates that the adhesion and water repellency of the photoresist are poorer.
Combining examples 2, 8, 9, 10 and comparative examples 6, 7 with table 4, it can be seen that as the weight average molecular weight of the acrylic resin is gradually increased, the contact angle of the photoresist is increased and then decreased, indicating that the water repellency of the photoresist is increased and then decreased.
The photoresists of comparative examples 6 and 7 both have satisfactory adhesion levels and contact angles, but the optical filter cannot have good resolution when the weight average molecular weight of the acrylic resin is less than 7000 or more than 30000.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the 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 fluorine-silicon 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 acid compound or a methacrylic acid ester compound containing 3 or more ethylenically unsaturated groups,
wherein the weight average molecular weight of the acrylic resin is 7000-30000.
2. The photoresist composition of claim 1, wherein the amount of the organofluorosilicone modified acrylic resin is 4-5 parts, and the amount of the acrylic resin is 8-9 parts.
3. The photoresist composition of claim 1, wherein the photoresist composition comprises: 30 parts of black dispersed 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 weight average molecular weight of the acrylic resin is 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: reacting fluorosilane oligomer with acrylic resin according to the weight ratio of 1 (22-27) to obtain the organic fluorine-silicon modified acrylic resin.
6. The photoresist composition of claim 5, wherein the fluorosilane is 1H,1H,2H, 2H-perfluorooctyltriethoxysilane.
7. The photoresist composition of claim 5, wherein the weight ratio of the fluorosilane oligomer to the acrylic resin is 1: 25.
8. A photoresist prepared from the photoresist composition of any one of claims 1 to 7.
9. The photoresist of claim 8, wherein the photoresist has an adhesion rating above level 4B and a water contact angle above 85 °.
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