CN115210647A - Positive photosensitive resin composition - Google Patents
Positive photosensitive resin composition Download PDFInfo
- Publication number
- CN115210647A CN115210647A CN202180018213.5A CN202180018213A CN115210647A CN 115210647 A CN115210647 A CN 115210647A CN 202180018213 A CN202180018213 A CN 202180018213A CN 115210647 A CN115210647 A CN 115210647A
- Authority
- CN
- China
- Prior art keywords
- positive photosensitive
- resin composition
- photosensitive resin
- compound
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 26
- 239000005871 repellent Substances 0.000 claims abstract description 25
- 230000002378 acidificating effect Effects 0.000 claims abstract description 24
- 230000002940 repellent Effects 0.000 claims abstract description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 11
- -1 acrylic compound Chemical class 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- 239000005011 phenolic resin Substances 0.000 claims description 7
- 238000005192 partition Methods 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 abstract description 2
- 238000011156 evaluation Methods 0.000 description 23
- 125000000524 functional group Chemical group 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method 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
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- HOEPBGSXAFUSIH-UHFFFAOYSA-N (2-isocyanato-1-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound O=C=NC(C)C(OC(=O)C=C)OC(=O)C=C HOEPBGSXAFUSIH-UHFFFAOYSA-N 0.000 description 1
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- NCCTVAJNFXYWTM-UHFFFAOYSA-N 2-tert-butylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=CC(=O)C=CC1=O NCCTVAJNFXYWTM-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- BNWKXMCELVEAPW-UHFFFAOYSA-N chembl3305990 Chemical compound O=C1C(=[N+]=[N-])C=CC2=C1C=CC=C2S(=O)(=O)O BNWKXMCELVEAPW-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a positive photosensitive resin composition comprising an alkali-soluble resin (A), a photosensitizer (B), a crosslinking agent (C) and an ink repellent (D), wherein the crosslinking agent (C) contains a compound having at least 1 or more selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric group as an acidic group, the proportion of the compound having the acidic group is in the range of 5 to 35% by mass relative to the total of (A) + (B) + (C) + (D), and the ink repellent (D) contains at least one of an acrylic compound having a F atom and a silicone compound having a F atom.
Description
Technical Field
The present invention relates to a positive photosensitive resin composition.
Background
Positive photosensitive resin compositions are used for the production of color filters, partition walls for pixel portions of organic EL devices, and microlenses (for example, patent documents 1 and 2).
Documents of the prior art
Patent document
Patent document 1: international publication No. 2013/133392
Patent document 2: japanese patent laid-open publication No. 2012-102314
Disclosure of Invention
In recent years, the required performance of products has been increasing, and the performance of conventional positive photosensitive resin compositions has been insufficient.
Under such circumstances, a positive photosensitive resin composition having excellent coatability, liquid repellency, and solvent resistance has been demanded.
The present invention includes the following aspects.
1. A positive photosensitive resin composition comprising an alkali-soluble resin (A), a sensitizer (B), a crosslinking agent (C), and an ink-repellent agent (D),
the crosslinking agent (C) contains a compound having at least 1 kind selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric group as an acidic group,
the proportion of the compound having an acidic group is in the range of 5 to 35% by mass relative to the total amount of (A) + (B) + (C) + (D), and the ink repellent (D) contains at least one of an acrylic compound having an F atom and an organosilicon compound having an F atom.
2. The positive photosensitive resin composition according to claim 1, wherein the photosensitizer (B) contains a quinonediazide compound.
3. The positive photosensitive resin composition according to 1 or 2, wherein the alkali-soluble resin (a) has a mass average molecular weight in a range of 500 to 10000.
4. The positive photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) is a phenolic resin.
5. The positive photosensitive resin composition according to claim 4, wherein the phenol resin is an o-cresol resin.
6. The positive photosensitive resin composition according to any one of claims 1 to 5, wherein the acidic group is a carboxyl group.
7. The positive photosensitive resin composition according to claim 6, wherein the crosslinking agent (C) contains a compound having 1 to 3 carboxyl groups in 1 molecule.
8. The positive photosensitive resin composition according to any one of claims 1 to 7, wherein a proportion of the compound having the acidic group in the crosslinking agent (C) is 30% or more by mass.
9. The positive photosensitive resin composition according to any one of claims 1 to 8, further comprising a solvent (E), wherein the proportion of the compound having a boiling point of 170 ℃ or higher in the solvent is in the range of 10 to 70% by mass.
10. A cured product obtained by curing the positive photosensitive resin composition described in any one of 1 to 9.
11. An optical element comprising the cured product of 10 as a partition wall.
The present invention can provide a positive photosensitive resin composition having excellent coatability, liquid repellency, and solvent resistance.
Detailed Description
The positive photosensitive resin composition of the present invention will be described below.
[ Positive photosensitive resin composition ]
The positive photosensitive resin composition of the present invention is composed of a combination of essential components and optional components. The essential component is required to be contained in the positive photosensitive resin composition and provides a main function of performance. Any component may be used as required.
Unless otherwise specified, the term "mass" means "mass%. However, in the present specification, the proportion on the mass basis (percentage, parts, etc.) is the same as the proportion on the weight basis (percentage, parts, etc.). Numerical ranges include ranges that are rounded. In addition, the numerical range "X to Y" means "X to Y inclusive".
[ essential Components ]
Examples of the essential components include an alkali-soluble resin (a), a sensitizer (B), a crosslinking agent (C), and an ink repellent (D).
< alkali soluble resin (A) >)
The alkali-soluble resin (a) is a resin that is dissolved in an alkali used in a developing step, and is a resin that becomes a main component of a partition wall used in a pixel portion or the like.
As the alkali-soluble resin (a) used in the present invention, a known resin used in a positive photosensitive resin composition can be used.
As a specific example, alkali-soluble resins described in japanese patent No. 6177495, japanese patent No. 5447384, japanese patent No. 4770985, japanese patent No. 4600477, japanese patent No. 5444749, and international publication No. 2019/156000 can be exemplified as the alkali-soluble resin (a), but the alkali-soluble resin (a) is not limited to these.
Specific examples of the preferable alkali-soluble resin (a) are described below, but the alkali-soluble resin (a) is not limited to these.
As the alkali-soluble resin (a), a phenol resin is preferable. When a phenolic resin is used, the curability of the obtained positive photosensitive resin composition is improved, and the occurrence of outgas is reduced. In addition, as the phenol resin, o-cresol resin is particularly preferable because the molecular weight of the resin can be controlled to be small.
The mass average molecular weight of the alkali-soluble resin (A) is preferably in the range of 500 to 10000, more preferably 1000 to 5000, and particularly preferably 1000 to 3000, for excellent residue removability.
The mass average molecular weight (Mw) in the present specification represents a mass average molecular weight in terms of standard polystyrene as measured by Gel Permeation Chromatography (GPC) with tetrahydrofuran as a mobile phase.
The amount of the alkali-soluble resin (A) to be used is preferably in the range of 40 to 80% by mass, more preferably 50 to 75% by mass, and particularly preferably 55 to 72% by mass based on the total amount of (A) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be effectively exhibited.
< photosensitizer (B) >
The sensitizer (B) is a compound which reacts with light upon exposure to change the solubility of the positive photosensitive resin composition in an alkaline solution.
Examples of the sensitizer (B) used in the present invention include known sensitizers used for positive photosensitive resin compositions.
As the photosensitizer (B), a compound having a quinonediazide group (hereinafter also referred to as a quinonediazide compound) is preferable because of its excellent photosensitivity.
The amount of the photosensitizer (B) to be used is preferably in the range of 10 to 35% by mass, more preferably 15 to 30% by mass, and particularly preferably 17 to 22% by mass, based on the total amount of (A) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be effectively exhibited.
< crosslinking agent (C) >
The crosslinking agent (C) is a compound contributing to curability of the positive photosensitive resin composition, and has 2 or more photocurable functional groups. The photocurable functional group is preferably the same kind of functional group as the photocurable functional group of the alkali-soluble resin (a). Specifically, an ethylenic double bond is preferable as the photocurable functional group.
The number of the photocurable functional groups of the crosslinking agent (C) is 2 or more, preferably 3 or more, more preferably 4 or more, and particularly preferably 5 or more per 1 molecule. The larger the number of the photocurable functional groups, the higher the curability of the coating film surface, and the higher the reliability of the cured product such as solvent resistance and outgassing.
The crosslinking agent (C) used in the present invention contains a compound having at least 1 kind selected from a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric group as an acidic group (hereinafter, also referred to as a compound having an acidic group), and preferably contains a compound having a carboxyl group. The number of the acid groups of the compound having an acid group is 1 or more, preferably 1 to 3, and particularly preferably 1 in 1 molecule.
The compound having the acidic group has such a structure, and the effects of the present invention can be effectively exhibited. In addition, the crosslinking agent is uniformly dispersed in the cured film, and the permeability of the developer can be improved.
The mass average molecular weight of the compound having an acidic group is preferably 100 to 1500, more preferably 300 to 1000, and particularly preferably 400 to 800, from the viewpoint of permeation of the developer and diffusion in the liquid.
Specific examples of the compound having the above-mentioned acidic group are given below, but the compound having an acidic group is not limited to these.
The compound having an acidic group is preferably a compound in which an acidic group is introduced into an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a hydroxyl compound having a (meth) acryloyl group, such as an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, an ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid, and the like, and 2 or more unsaturated bonds (ethylenic double bonds) remain.
In addition, from the viewpoint of the introduction ratio of the ethylenic double bond, the compound having an acidic group is preferably a compound having an isocyanurate skeleton, a trimethylolpropane skeleton, a phthalic acid skeleton, a pentaerythritol skeleton, a dipentaerythritol skeleton, or a tripentaerythritol skeleton.
More preferred specific examples thereof include compounds having a dipentaerythritol skeleton. Particularly preferred is a compound in which 5 hydroxyl groups of dipentaerythritol are substituted with (meth) acryloyloxy groups, and the remaining 1 hydroxyl group is ester-bonded to, for example, succinic acid to introduce an acidic group. In particular, these compounds have 2 or more, preferably 3 or more, more preferably 4 or more, and particularly preferably 5 or more photocurable functional groups in 1 molecule, preferably an ethylenic double bond, more preferably an acrylate, and further have an acidic group, and thus can achieve both the effects of solvent resistance, coatability, and reduction of development residues at a high level.
The acid value of the crosslinking agent (C) is preferably not less than 10mgKOH/g, more preferably not less than 20mgKOH/g, and still more preferably not less than 50 mgKOH/g. The acid value is preferably 200mgKOH/g or less, more preferably 150mgKOH/g or less, and still more preferably 100mgKOH/g or less. The acid value is preferably from 10 to 200mgKOH/g, more preferably from 20 to 150mgKOH/g, and particularly preferably from 50 to 100mgKOH/g. If the acid value of the crosslinking agent (C) is not less than the lower limit, good solubility in a developer can be obtained in the positive photosensitive resin composition.
The crosslinking agent (C) may be used alone or in combination with other crosslinking agents, wherein the crosslinking agent (C) is 1 compound having the above-mentioned acidic group.
The proportion of the compound having an acidic group in the crosslinking agent (C) is preferably 30% or more, more preferably 50% or more, and particularly preferably 60% or more by mass ratio.
The amount of the compound having an acidic group is 5 to 35% by mass relative to the total amount of (A) + (B) + (C) + (D). The amount of the above-mentioned compound is preferably 6% or more, more preferably 8% or more. The amount used is preferably 25% or less, more preferably 20% or less. The amount used is preferably 6 to 25%, particularly preferably 8 to 20%. When the amount is within this range, the effects of the present invention can be effectively exhibited. More specifically, when the amount of the compound having an acidic group used is not less than the lower limit, excellent solvent resistance and coatability can be easily achieved at the same time. When the amount is less than the upper limit, the liquid repellency is easily improved.
The proportion of the crosslinking agent (C) is preferably 8% or more, more preferably 10% or more, further preferably 12% or more, and particularly preferably 14% or more, by mass relative to the alkali-soluble resin (a). The above proportion is preferably 40% or less, more preferably 35% or less, further preferably 30% or less, and particularly preferably 26% or less. The above proportion is preferably 8 to 40%, more preferably 10 to 35%, particularly preferably 12 to 30%, most preferably 14 to 26%. When the ratio of the crosslinking agent (C) to the alkali-soluble resin (a) is in this range, the developer solubility and the pattern shape are well balanced.
< ink repellent (D) >
The ink repellent (D) imparts an ink repellent function to the partition walls made of the positive photosensitive resin composition of the present invention. Therefore, the ink repellent (D) of the present invention has F atoms, and has moderate hydrophobicity and hydrophilicity.
The ink-repellent agent (D) having F atoms can be selected from ink-repellent agents used in general positive photosensitive resin compositions as long as it has F atoms.
Specific preferred examples thereof include copolymers of acrylic acid and resins having a silicone skeleton. When the ink-repellent agent (D) contains at least one of an acrylic compound having a F atom and an organosilicon compound having a F atom, the liquid-repellent property and the development residue reduction effect are excellent.
More preferred specific examples include the ink-repellent agents described below.
Ink-repellent agents described in Japanese patent No. 4609587, japanese patent No. 4905563, japanese patent No. 5152332, japanese patent No. 5173543, japanese patent No. 5466375, japanese patent No. 5338258, international publication No. 2013/024764, international publication No. 2013/133392, japanese patent No. 5516484, international publication No. 2016/088757, and International publication No. 2019/156000.
Among them, the ink repellent (D) preferably has a component crosslinkable by light or heat. Specific examples of the above-mentioned component include a component having a specific functional group. Examples of the functional group include a (meth) acryloyl group, an epoxy group, a glycidyl group, and a thiol group.
The ink repellent (D) preferably has a compatibility-improving component in order to improve the stability of the ink repellent in the composition. Specific examples of the compatibility-improving component include a component having a specific functional group. Examples of the functional group include an alkyl group, a phenyl group, a phenylamino group, and a hydroxyphenyl group.
The amount of the ink repellent (D) used is preferably in the range of 0.1 to 2.0% by mass, particularly preferably 0.5 to 1.0% by mass, based on the total amount of (a) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be effectively exhibited.
[ optional Components ]
< solvent (E) >
The positive photosensitive resin composition of the present invention may contain a solvent (E).
By containing the solvent (E), the positive photosensitive resin composition is excellent in coatability, adhesion to a substrate, and stability.
As the solvent (E), a known solvent used for a positive photosensitive resin composition can be used. Specific examples thereof include alcohols, ethers, aromatics and hydrocarbons, but the solvent (E) is not limited thereto.
In order to improve the uniformity of the coating film of the positive photosensitive resin composition and to achieve excellent layer separation, the proportion of the compound having a boiling point of 170 ℃ or higher in the solvent (E) is preferably in the range of 10 to 70% by mass, more preferably in the range of 20 to 60% by mass, and particularly preferably in the range of 30 to 50% by mass. When the proportion of the compound having a boiling point of 170 ℃ or higher is in this range, the liquid repellency of the surface of the cured product of the present invention can be more effectively exhibited.
The solvent (E) is preferably in the range of 60 to 90% by mass, particularly preferably in the range of 75 to 85% by mass in the positive photosensitive resin composition.
< other ingredients >
The positive photosensitive resin composition of the present invention may contain known components added as a positive photosensitive resin composition, such as a thermosetting agent, a thermosetting accelerator, a coloring agent, a silane coupling agent, fine particles, a thickener, a plasticizer, an antifoaming agent, a leveling agent, an anti-shrinking agent, and an ultraviolet absorber, as necessary, within a range not to impair the effects of the present invention. More specifically, the components described in paragraphs 0080 to 0095 of Japanese patent No. 6098635 and the like can be added.
[ method for producing Positive photosensitive resin composition ]
The positive photosensitive resin composition is prepared by mixing an alkali-soluble resin (a), a sensitizer (B), a crosslinking agent (C), and an ink-repellent agent (D), and a solvent and other components as necessary until uniform.
The positive photosensitive resin composition of the present invention is suitable for use in optical devices such as organic EL devices, microlenses, color filters, and organic TFT arrays, but the use is not limited thereto. For example, a cured product obtained by curing the positive photosensitive resin composition of the present invention can be suitably used for the above-mentioned applications.
As an example, a method for manufacturing an organic EL element is shown.
A transparent electrode such as tin-doped indium oxide (ITO) is formed on a transparent substrate such as glass by a sputtering method or the like, and the transparent electrode is etched into a desired pattern as necessary. Next, partition walls (cured products) were formed using the positive photosensitive resin composition of the present invention, and after a dot-oleophilic ink treatment was performed, a solution of a hole transport material and a light emitting material was applied to the dots in this order using an ink jet method, and dried to form a hole transport layer and a light emitting layer. Thereafter, an electrode of aluminum or the like is formed by a vapor deposition method or the like, thereby obtaining a pixel of an organic EL element.
Examples
The present invention is specifically described with reference to examples and comparative examples, but the embodiments may be modified as appropriate as long as the effects of the present invention are obtained. Examples 1 to 11 are examples, and examples 12 to 14 are comparative examples.
< measurement Condition and evaluation Condition >
[ sample for evaluation ]
A cured film was formed on an ITO substrate using the positive photosensitive resin composition described in table 1, and a sample for evaluation was prepared. As evaluation samples, 3 kinds of evaluation samples 1 to 3 were prepared. Solvent resistance was evaluated using evaluation sample 1. The liquid repellency was evaluated using sample 2 for evaluation. The coating properties were evaluated using sample 3 for evaluation.
[ sample 1 for evaluation ]
An ITO substrate (ITO product having a resistance value of 10. Omega./sq or less, manufactured by Kabushiki Kaisha, size 7.5 cm. Times.7.5 cm. Times.0.7 mm) was subjected to ultrasonic cleaning in ethanol (30 minutes). Then, ultraviolet/ozone cleaning was performed for 5 minutes (apparatus: PL7-200Sen Engineering Co., ltd.).
The cleaned substrate surface was spin-coated (rotation speed 610rpm,10 seconds) with a positive photosensitive resin composition using a spinner (IH-DX 2, mikasa corporation). Then, the mixture was dried on a hot plate at 100 ℃ for 2 minutes to form a film having a thickness of 1.3. Mu.m. The surface of the obtained film was exposed to light under the following conditions.
< Condition >
[ photomask ]: a light shielding part having a repeating 18 line pattern in a range of 20mm × 20mm
Shape of light shielding portion: 1, 2,3,4, 5,6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 30, 40, 50 μm × 1000 μm
Pattern interval: 50 μm
[ Lamp]: exposure Power (exposure output) 25mW/cm in USH-255BY365nm, manufactured BY Ushio Motor Co., ltd 2
[ conditions of irradiation]: cut off light below 330nm at a rate of 25mW/cm with a gap of 50 μm 2 The irradiation was carried out for 8 seconds.
The exposed ITO substrate was immersed in a tetramethylammonium hydroxide aqueous solution (0.4 mass%) for 40 seconds and developed. Thereafter, washing with water and drying were performed.
The dried substrate was heated on a hot plate (220 ℃ C., 60 minutes) to prepare an ITO substrate having a cured film with a specific pattern formed thereon (sample 1 for evaluation).
[ sample 2 for evaluation ]
Except for the step of exposure, an evaluation sample 2 was prepared in the same manner as in the evaluation sample 1.
[ sample 3 for evaluation ]
Sample 3 for evaluation was produced by the same method as sample 1 for evaluation except that the photomask used was changed.
[ photomask ]: the opening was formed in a pattern of 20mm × 20mm in the following manner.
Shape of opening part: 100 μm × 200 μm
Pattern spacing: 20 μm
[ coatability ]
For sample 3 for evaluation, 20pl of a 1wt% triphenyldiamine solution in cyclohexylbenzene was dropped using an IJ apparatus (manufactured by LaboJET 500Micro jet) into an arbitrary opening 100 μm × 200 μm in a region of 20mm × 20mm corresponding to the photomask to remove the inside of the film by development. Diffusion of the triphenyldiamine dried product inside the spot after drying was confirmed. The evaluation was carried out according to the following criteria.
Good: the spot was completely covered with a dry mass of triphenyldiamine.
Not: the spot had a portion not covered with the dry matter of triphenyldiamine.
The product is qualified.
[ liquid repellency ]
The contact angle with respect to PGMEA (propylene glycol monomethyl ether acetate) was measured by the θ/2 method for sample 2 for evaluation. The evaluation was carried out according to the following criteria.
Good: the contact angle exceeds 45 deg..
Can be as follows: the contact angle is 30 DEG or more and 45 DEG or less.
Not: the contact angle is less than 30 deg..
Good, can be qualified.
[ solvent resistance ]
To the cured film of sample 1 for evaluation, 2.5. Mu.l of PGMEA was dropped and left for 60 seconds. Thereafter, the PGMEA was wiped with a wiping cloth (manufactured by Bemcot M-3II Asahi chemical Co., ltd.), and the presence or absence of a dissolution mark on the upper surface of the film was confirmed by visual observation, and evaluated according to the following criteria.
Good: no dissolution mark.
Can be as follows: the surface had a slight trace of rounding.
Not: there were dissolution marks.
Good, can be qualified.
[ examples and comparative examples ]
The raw materials were stirred (about 30 minutes) at the ratio described in table 1 until uniform, to prepare a positive photosensitive resin composition. Samples 1, 2, and 3 for evaluation were prepared from the positive photosensitive resin composition, and evaluated.
The evaluation results are shown in table 1. Note that the blank column in the table indicates that the column is not included.
[ Table 1]
< description of abbreviations >
[ alkali-soluble resin (A) ]
A1: o-cresol novolac resin (Mw: 1740)
A2: o-cresol novolac resin (Mw: 2470)
[ photosensitizer (B) ]
B1: (mono-to tetra-) esters of 2,3, 4' -tetrahydroxybenzophenone with 6-diazo-5, 6-dihydro-5-oxo-naphthalene-1-sulfonic acid
[ crosslinking agent (C) ]
C1: polyacid-modified acrylic oligomer (mixture of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and succinate ester of dipentaerythritol pentaacrylate (acid value 92mgKOH/g, molecular weight 612))
C2:2, 2-Triacryloyloxymethylethyl phthalic acid (acid value 87mgKOH/g, molecular weight 446)
C3: mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate
[ ink-repellent agent (D) ]
D1: the substance synthesized in the following manner was used.
(Synthesis method)
2-butanone (415.1 g) and CH were added 2 ＝C(CH 3 )COOCH 2 CH 2 (CF 2 ) 6 F (81.0 g), methacrylic acid (18.0 g), 2-hydroxyethyl methacrylate (81.0 g), 2' -azobis (2, 4-dimethylvaleronitrile) (5.0 g) and n-dodecyl mercaptan (4.7 g) were polymerized at 50 ℃ for 24 hours under stirring in a nitrogen atmosphere. Further, the mixture was heated at 70 ℃ for 5 hours to deactivate the polymerization initiator, thereby obtaining a copolymer solution. Number average of copolymerThe molecular weight is 5540 and the mass average molecular weight is 13200.
Next, 130.0g of the above-mentioned copolymer solution, 1- (bisacryloxymethyl) ethyl isocyanate (33.5 g), dibutyltin dilaurate (0.13 g) and tert-butyl-p-benzoquinone (1.5 g) were polymerized at 40 ℃ for 24 hours while stirring.
The polymer was purified using hexane, followed by drying, to obtain 65.6g of an ink repellent (D1).
D2: the substance synthesized in the following manner was used.
(Synthesis method)
F (CF) 2 ) 6 CH 2 CH 2 Si(OCH 3 ) 3 (0.38g)、Si(OC 2 H 5 ) 4 (0.63g)、CH 2 ＝CHCOO(CH 2 ) 3 Si(OCH 3 ) 3 (0.71 g) and PGME propylene glycol monomethyl ether (7.44 g) were mixed until homogeneous.
To the mixed solution, 0.85g of a 1% aqueous hydrochloric acid solution was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at 40 ℃ for 5 hours to effect a reaction, and the reaction mixture was used as an ink repellent (D2).
[ solvent (E) ]
E-1: diethylene glycol ethyl methyl ether (boiling point 176 ℃ C.)
E-2: propylene glycol monomethyl ether acetate (boiling point 146 ℃ C.)
E-3: propylene glycol monomethyl ether (boiling point 120 ℃ C.)
While the present invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof. This application is based on Japanese patent application No. 3/4/2020 (Japanese patent application No. 2020-037171), the contents of which are incorporated herein by reference.
Claims (11)
1. A positive photosensitive resin composition comprising an alkali-soluble resin (A), a photosensitizer (B), a crosslinking agent (C), and an ink-repellent agent (D),
the crosslinking agent (C) contains a compound having 1 or more kinds of acid groups selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric acid group,
the proportion of the compound having the acidic group is in the range of 5 to 35% by mass relative to the total amount of (A) + (B) + (C) + (D), and the ink repellent (D) contains at least one of an acrylic compound having a F atom and an organosilicon compound having a F atom.
2. The positive photosensitive resin composition according to claim 1, wherein the sensitizer (B) contains a quinonediazide compound.
3. The positive photosensitive resin composition according to claim 1 or 2, wherein the alkali-soluble resin (a) has a mass average molecular weight in the range of 500 to 10000.
4. The positive photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) is a phenolic resin.
5. The positive photosensitive resin composition according to claim 4, wherein the phenol resin is an o-cresol resin.
6. The positive photosensitive resin composition according to any one of claims 1 to 5, wherein the acidic group is a carboxyl group.
7. The positive photosensitive resin composition according to claim 6, wherein the crosslinking agent (C) contains a compound having 1 to 3 carboxyl groups in 1 molecule.
8. The positive photosensitive resin composition according to any one of claims 1 to 7, wherein the proportion of the compound having the acidic group in the crosslinking agent (C) is 30% or more by mass ratio.
9. The positive photosensitive resin composition according to any one of claims 1 to 8, further comprising a solvent (E), wherein the proportion of a compound having a boiling point of 170 ℃ or higher in the solvent is in the range of 10 to 70% by mass.
10. A cured product obtained by curing the positive photosensitive resin composition according to any one of claims 1 to 9.
11. An optical element comprising the cured product of claim 10 as partition walls.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020037171 | 2020-03-04 | ||
| JP2020-037171 | 2020-03-04 | ||
| PCT/JP2021/007783 WO2021177251A1 (en) | 2020-03-04 | 2021-03-01 | Positive-type photosensitive resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115210647A true CN115210647A (en) | 2022-10-18 |
Family
ID=77614284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180018213.5A Withdrawn CN115210647A (en) | 2020-03-04 | 2021-03-01 | Positive photosensitive resin composition |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2021177251A1 (en) |
| KR (1) | KR20220150301A (en) |
| CN (1) | CN115210647A (en) |
| TW (1) | TW202141187A (en) |
| WO (1) | WO2021177251A1 (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5786475B2 (en) | 2010-10-13 | 2015-09-30 | Jnc株式会社 | Photocurable composition |
| WO2013133392A1 (en) | 2012-03-09 | 2013-09-12 | 旭硝子株式会社 | Positive photosensitive resin composition, partition wall and optical element |
| JP2014041264A (en) * | 2012-08-22 | 2014-03-06 | Sumitomo Bakelite Co Ltd | Photosensitive resin composition, cured film, protective film, insulator film, and semiconductor device and display body device using the same |
| JP2016166951A (en) * | 2015-03-09 | 2016-09-15 | Jnc株式会社 | Photosensitive composition |
| KR102611589B1 (en) * | 2016-12-22 | 2023-12-07 | 에이지씨 가부시키가이샤 | Negative photosensitive resin composition |
| TWI683182B (en) * | 2017-04-07 | 2020-01-21 | 日商昭和電工股份有限公司 | Photosensitive resin composition and method for manufacturing radiation lithography structure |
| KR20210073517A (en) * | 2018-10-12 | 2021-06-18 | 도레이 카부시키가이샤 | A photosensitive resin composition, a cured film, and the display device using this cured film |
-
2021
- 2021-03-01 JP JP2022504365A patent/JPWO2021177251A1/ja not_active Withdrawn
- 2021-03-01 CN CN202180018213.5A patent/CN115210647A/en not_active Withdrawn
- 2021-03-01 KR KR1020227030027A patent/KR20220150301A/en unknown
- 2021-03-01 WO PCT/JP2021/007783 patent/WO2021177251A1/en active Application Filing
- 2021-03-04 TW TW110107714A patent/TW202141187A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW202141187A (en) | 2021-11-01 |
| JPWO2021177251A1 (en) | 2021-09-10 |
| KR20220150301A (en) | 2022-11-10 |
| WO2021177251A1 (en) | 2021-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI734756B (en) | Positive tone photosensitive resin composition, curable film and display device | |
| TW200905264A (en) | Curable resin composition, protective film, and method for forming protective film | |
| KR20060049045A (en) | Silsesquioxane-containing compound and method for preparing the same | |
| JP4915500B2 (en) | Thermosetting resin composition, method for forming color filter protective film, and color filter protective film | |
| KR101986763B1 (en) | Negative-type photosensitive resin composition having high thermal stability and high resolution, and hardened overcoat layer prepared therefrom | |
| CN103890128A (en) | Method for manufacturing ink-repellent agent, negative-type photosensitive resin composition, partition wall, and optical device | |
| CN107203096B (en) | Negative photosensitive resin composition and photocured pattern made therefrom | |
| JP5514566B2 (en) | Photosensitive resin composition | |
| KR20130113635A (en) | Photosensitive resin composition comprising organopolysiloxane | |
| TW201928523A (en) | Negative photosensitive resin composition | |
| JP5653173B2 (en) | Photosensitive resin composition | |
| CN107817652B (en) | Photosensitive resin composition and photocured pattern produced therefrom | |
| JP2019510992A (en) | Low temperature curable negative photosensitive composition | |
| CN115210647A (en) | Positive photosensitive resin composition | |
| CN115151865A (en) | Positive photosensitive resin composition | |
| CN110419000B (en) | Photosensitive silicone resin composition, cured film, and member for touch panel | |
| CN115279815A (en) | (meth) acrylate resin, active energy ray-curable (meth) acrylate resin composition, resist underlayer film, and method for producing (meth) acrylate resin | |
| CN115244462A (en) | Positive photosensitive resin composition | |
| TW201335284A (en) | Curable resin composition comprising organopolysiloxane | |
| TWI827824B (en) | Positive photosensitive resin composition, cured film manufacturing method, cured film, optical element and electronic material | |
| KR101580854B1 (en) | Curable resin composition set for forming resin cured film protective film and process for forming protective film | |
| CN115176201A (en) | Positive photosensitive resin composition | |
| KR101963593B1 (en) | Photosensitive resin comopsition and photocurable pattern forming by the same | |
| KR20230169934A (en) | Photosensitive resin composition | |
| KR20180001751A (en) | Photosensitive resin composition and photo-cured pattern prepared from the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20221018 |