WO2022176883A1 - 表面調整剤、感光性樹脂組成物、硬化物及びディスプレイ - Google Patents
表面調整剤、感光性樹脂組成物、硬化物及びディスプレイ Download PDFInfo
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- WO2022176883A1 WO2022176883A1 PCT/JP2022/006086 JP2022006086W WO2022176883A1 WO 2022176883 A1 WO2022176883 A1 WO 2022176883A1 JP 2022006086 W JP2022006086 W JP 2022006086W WO 2022176883 A1 WO2022176883 A1 WO 2022176883A1
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- WIPO (PCT)
- Prior art keywords
- group
- fluorine
- resin composition
- photosensitive resin
- fluororesin
- Prior art date
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- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 176
- 239000011737 fluorine Substances 0.000 claims abstract description 149
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- 238000005192 partition Methods 0.000 claims abstract description 29
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- 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
- 239000003921 oil Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-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
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
- C08F20/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- 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
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/122—Pixel-defining structures or layers, e.g. banks
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
Definitions
- the present disclosure relates to surface conditioners, photosensitive resin compositions, cured products, and displays.
- An inkjet method is known as a method for forming an organic layer having a function such as light emission when manufacturing display elements such as an organic EL display, a micro LED display, and a quantum dot display.
- There are several methods for the inkjet method Specifically, a method of solidifying ink dropped from a nozzle into concave portions of a pattern film having unevenness formed on a substrate, or a method of solidifying a lyophilic portion, which is a portion that is wet with ink, and the ink.
- an ink droplet is dropped onto a pattern film in which a lyophobic portion, which is a portion that repels , is formed on a substrate in advance, and the ink adheres only to the lyophilic portion.
- two main methods can be employed to produce such a pattern film having unevenness.
- One is a photolithography method in which the surface of a photosensitive resist film coated on a substrate is exposed in a pattern to form an exposed portion and an unexposed portion, and one of the portions is dissolved and removed with a developer.
- the other is an imprint method using printing technology.
- the convex portions of the formed pattern film having unevenness are called banks (partition walls), and the banks function as barriers to prevent the inks from mixing when ink is dropped into the concave portions of the pattern film.
- this barrier it is required that the substrate surface of the concave portion of the pattern film is exposed, the substrate surface is lyophilic to the ink, and the upper surface of the bank is lyophobic to the ink. .
- a fluorine-containing resin is used as an ink-repellent agent. Liquid repellency is improved by using a fluorine-containing resin.
- a resist composition containing a fluorine-containing resin has a monomer unit formed from a monomer represented by the following formula and has a fluorine atom content of 7 to 35% by mass.
- Patent Document 2 as an ink repellent agent containing a polymer unit containing a fluorine atom, an alkyl group having 20 or less carbon atoms in which at least one of the hydrogen atoms is substituted with a fluorine atom (wherein the above alkyl group does not contain etheric oxygen and a polymer unit (b2) having an ethylenic double bond, having a fluorine content of 5 to 25% by mass and a number average molecular weight of 500
- an ink repellent agent characterized in that it is not less than 10,000 and less than 10,000.
- a resist composition containing a fluorine-containing resin has a monomer unit formed from a monomer represented by the following formula, has an ethylenic double bond, and has a fluorine atom content of
- E photoradical initiator
- F alkali-soluble resin having an acidic group and two or more ethylenic double bonds in one molecule.
- CH2 C(R)COOXR f1 (In the formula, R and R f1 are the same as above.)
- Patent Document 4 as a negative photosensitive resin composition containing an ink repellent agent having a fluorine atom, a photocurable alkali-soluble resin or alkali-soluble monomer (A) and a photoradical polymerization initiator (B ), a photoacid generator (C), an acid curing agent (D), and an ink repellent agent (E) having a fluorine atom, wherein the ink repellent agent (
- a negative photosensitive resin composition is disclosed, wherein the fluorine atom content in E) is 1 to 40% by mass, and the ink repellent agent (E) has an ethylenic double bond.
- the fluorine-containing resins and ink-repellent agents disclosed in Patent Documents 1 to 4 are resins having excellent liquid-repellent properties, and are also suitable as partition wall materials. On the other hand, it has been found that these resins still have room for improvement in surface roughness after curing.
- An object of the present disclosure is to improve the surface roughness of a fluorine-containing resin suitable for use as a partition wall material.
- the inventors of the present invention conducted intensive studies. As a result, the inventors have found that the above problems can be solved by using a fluorine-containing resin having a specific group as a surface conditioner, and have completed the present disclosure.
- the surface conditioner of the present disclosure contains a fluororesin (A) having a structure represented by general formula (1) below.
- each Ra independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched chain having 3 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, or a fluorine atom. , Any number of hydrogen atoms in the above alkyl group are substituted with fluorine atoms.
- the photosensitive resin composition of the present disclosure contains the above surface conditioner, a fluororesin (B) having a crosslinked site, a solvent, and a photopolymerization initiator.
- the cured product of the present disclosure is characterized by curing a photosensitive resin composition.
- a photosensitive resin composition of the present disclosure By using the photosensitive resin composition of the present disclosure, a cured product and partition walls with improved surface roughness can be produced.
- a display of the present disclosure includes a light-emitting element including partition walls obtained by curing the photosensitive resin composition, and a light-emitting layer or wavelength conversion layer disposed in a region partitioned by the partition walls.
- the display of the present disclosure includes a light-emitting element in which the ink is patterned with high precision by including the partition walls obtained from the photosensitive resin composition.
- the surface conditioning method for a molded article of the present disclosure uses the fluororesin (A) having the structure represented by the above general formula (1).
- the use of the present disclosure is the use of the fluororesin (A) having the structure represented by the above general formula (1) for conditioning the surface of molded articles.
- the present disclosure will now be described in detail.
- the present disclosure is not limited to the following embodiments, and can be implemented as appropriate based on the ordinary knowledge of those skilled in the art within the scope of the present disclosure.
- (Surface conditioner) ⁇ Fluorine-containing resin (A)>
- the surface conditioner of the present disclosure contains a fluororesin (A) having a structure represented by general formula (1) below.
- each Ra independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched chain having 3 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, or a fluorine atom; Any number of hydrogen atoms in the above alkyl group are substituted with fluorine atoms.
- linear alkyl groups having 1 to 6 carbon atoms include trifluoromethyl group, difluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, heptafluoropropyl group, 3,3, 3-trifluoropropyl group, nonafluorobutyl group and the like.
- the branched alkyl group having 3 to 6 carbon atoms includes heptafluoroisopropyl group, hexafluoroisopropyl group, nonafluoroisobutyl group, nonafluoro-tert-butyl group and the like.
- Examples of cyclic alkyl groups having 3 to 6 carbon atoms include pentafluorocyclopropyl groups.
- Ra is preferably a linear alkyl group having 1 to 6 carbon atoms, more preferably a trifluoromethyl group.
- the structure represented by formula (1) examples include a difluoromethanol group, a tetrafluoroethanol group, a hexafluoroisopropanol group, a trifluoropropanol group and the like, with the hexafluoroisopropanol group being preferred.
- the structure represented by general formula (1) is preferably not directly bonded to an aromatic ring.
- the structure represented by general formula (1) is preferably directly bonded to a linear, branched or cyclic alkylene group.
- the fluororesin (A) can be obtained by polymerizing a monomer having a structure represented by general formula (1).
- monomers having a structure represented by general formula (1) include 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate, 4- (1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propanyl)styrene (4-HFA-ST), 3,5-bis(1,1,1,3,3,3 -hexafluoro-2-hydroxy-2-propanyl)styrene (3,5-HFA-ST), 2,4-bis(1,1,1,3,3,3-hexafluoro-2-hydroxy-2- propanyl)cyclohexyl methacrylate, 3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propanyl)cyclohexyl methacrylate, 2,4,6-tris(1,1,1 ,3,3,3-hexafluoro-2-hydroxy-2-
- the fluororesin (A) is a homopolymer obtained by polymerizing only one of these monomers, or any two or more of these monomers.
- a heteropolymer obtained by copolymerization is preferred. This is because it is easy to polymerize and has excellent performance as a surface conditioner.
- the fluororesin (A) may contain structural units derived from monomers other than the monomer having the structure represented by formula (1).
- Such other monomers include, for example, monomers used for synthesizing the fluororesin (B) having a crosslinked site, which will be described later.
- Other monomers can be used singly or in combination of two or more. Specific examples of other monomers include hexafluoroisopropyl methacrylate and butyl methacrylate.
- the fluororesin (A) contains structural units derived from the other monomers, the content thereof is preferably 50 mol % or less in the fluororesin (A). If the constituent units derived from other monomers exceed 50 mol %, the surface conditioning effect of the fluororesin (A) may not be sufficiently obtained. More preferably, it is 30 mol % or less.
- the molar ratio of structural units derived from each monomer in the fluororesin (A) can be determined from NMR (nuclear magnetic resonance spectroscopy) measurements.
- the fluorine-containing resin (A) functions as a surface conditioner, it preferably does not have a crosslinked site.
- the content of the structure represented by the general formula (1) is 50 mol% or more and 300 mol, based on 100 mol% of the total amount of repeating units constituting the fluororesin (A). % or less. If the content of the structure represented by formula (1) is less than 50 mol %, the effect of the fluororesin (A) as a surface conditioner may not be sufficiently obtained. If it exceeds 300 mol %, it is not preferable because the synthesis takes time and the manufacturing cost increases. It is more preferably 100 mol % or more and 200 mol % or less.
- the fluororesin (A) preferably has a weight average molecular weight of 1,000 or more and 50,000 or less. If the weight-average molecular weight of the fluororesin (A) is outside the above range, the surface roughness of the resin film and partition walls may not be sufficiently improved. More preferably 5,000 or more and 40,000 or less, still more preferably 5,000 or more and 30,000 or less.
- the degree of dispersion of the fluororesin (A) is preferably 1.01 to 5.00, more preferably 1.10 to 4.00, and 1 0.30 to 3.00 is particularly preferred.
- the weight average molecular weight and dispersity of the fluororesin (A) are values obtained by high-speed gel permeation chromatography using polystyrene as a standard substance.
- the fluorine-containing resin (A) can be synthesized, for example, by a method of dissolving a monomer in a solvent, adding a polymerization initiator, and heating and reacting if necessary.
- a chain transfer agent is preferably present in the reaction as necessary.
- the monomer, solvent, polymerization initiator and chain transfer agent may be added in their entirety at the start of the reaction or may be added continuously.
- the solvent in the above synthesis method is not particularly limited, and examples include ketones, alcohols, polyhydric alcohols and their derivatives, ethers, esters, aromatic solvents, fluorine-based solvents, and the like. These may be used alone or in combination of two or more.
- ketones include acetone, methyl ethyl ketone (MEK), cyclopentanone, cyclohexanone, methyl isoamyl ketone, 2-heptylcyclopentanone, methyl isobutyl ketone, methyl isopentyl ketone, and 2-heptanone.
- MEK methyl ethyl ketone
- cyclopentanone cyclohexanone
- methyl isoamyl ketone 2-heptylcyclopentanone
- 2-heptylcyclopentanone methyl isobutyl ketone
- 2-heptanone 2-heptanone
- alcohols include isopropanol, butanol, isobutanol, n-pentanol, isopentanol, tert-pentanol, 4-methyl-2-pentanol, 3-methyl-3-pentanol, 2, 3-dimethyl-2-pentanol, n-hexanol, n-heptanol, 2-heptanol, n-octanol, n-decanol, s-amyl alcohol, t-amyl alcohol, isoamyl alcohol, 2-ethyl-1-butanol, Lauryl alcohol, hexyldecanol, oleyl alcohol and the like can be mentioned.
- polyhydric alcohols and derivatives thereof include ethylene glycol, ethylene glycol monoacetate, ethylene glycol dimethyl ether, diethylene glycol, diethylene glycol dimethyl ether, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, propylene glycol monomethyl ether (PGME ), propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate (PGMEA), monomethyl ether of dipropylene glycol or dipropylene glycol monoacetate, monoethyl ether, monopropyl ether, mono Butyl ether, monophenyl ether and the like can be mentioned.
- ethers include diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, and anisole.
- esters include methyl lactate, ethyl lactate (EL), methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methyl methoxypropionate, ethyl ethoxypropionate, ⁇ -butyrolactone, and the like.
- aromatic solvents include xylene and toluene.
- fluorine-based solvents examples include freon, substitute freon, perfluoro compounds, hexafluoroisopropyl alcohol, and the like.
- polymerization initiators include known organic peroxides, inorganic peroxides, azo compounds, and the like.
- Organic peroxides and inorganic peroxides can also be used as redox catalysts in combination with reducing agents.
- Chain transfer agents include mercaptans such as n-butyl mercaptan, n-dodecyl mercaptan, t-butyl mercaptan, ethyl thioglycolate, 2-ethylhexyl thioglycolate, and 2-mercaptoethanol; chloroform, carbon tetrachloride, tetraodor Halogenated alkyls such as carbon dioxide and the like can be mentioned.
- the content of the fluororesin (A) in the surface conditioner of the present disclosure is not particularly limited, but is preferably 0.001 to 99.99% by mass, more preferably 0.01 to 99.9% by mass.
- the fluorine-containing resin (A) in the surface conditioner of the present disclosure may be used alone or in combination of two or more.
- the surface conditioner of the present disclosure may contain solvents and additives other than the fluororesin (A). Solvents that can be contained in the surface conditioner of the present disclosure include, for example, PGMEA and butyl acetate.
- the surface conditioner of the present disclosure contains the fluororesin (A) having the structure represented by general formula (1), it can be suitably used as a surface conditioner for various resins.
- the surface conditioner of the present disclosure by introducing the surface conditioner of the present disclosure into a resin composition and using it, it is possible to produce molded articles such as resin films and partition walls (banks) with improved surface roughness.
- the type of resin in the resin composition is not particularly limited, and examples thereof include olefin resins, epoxy resins, (meth)acrylic resins, urethane resins, fluorine resins, and the like, or a combination of two or more thereof.
- the surface conditioner of the present disclosure can be particularly suitably used in compositions containing two or more resins with different fluorine contents.
- the surface conditioner of the present disclosure can be used more specifically as an antifoaming agent, a leveling agent, an anti-popping agent, and the like.
- the surface conditioner of the present disclosure also acts as a surfactant, it can also be used as a surfactant.
- the photosensitive resin composition of the present disclosure contains the above surface conditioner, a fluororesin (B) having a crosslinked site, a solvent, and a photopolymerization initiator.
- a resin film or a partition with improved surface roughness.
- the terms "bank” and “partition wall” are synonymous, and unless otherwise noted, they mean convex portions of a pattern film having concavo-convex portions in the inkjet method.
- Examples of the surface control agent in the photosensitive resin composition of the present disclosure include those containing the fluororesin (A) described above.
- the content of the fluorine-containing resin (A) is 0.01% by mass or more and 4.0% by mass or less with respect to the total solid content of the photosensitive resin composition. preferable. Outside the above range, the surface roughness of the resin film and partition walls may not be sufficiently improved. It is more preferably 0.1% by mass or more and 2.5% by mass or less, and still more preferably 0.2% by mass or more and 2.5% by mass or less.
- the fluorine-containing resin (B) having a cross-linking site has a repeating unit composed of a hydrocarbon having a fluorine atom, and a photopolymerizable group is added to the side chain of the polymer as a cross-linking site.
- the cross-linking site of the "fluorine-containing resin (B) having a cross-linking site” means a site capable of undergoing a polymerization reaction with another monomer.
- the "fluorinated resin (B) having a crosslinked site” is also referred to as "fluorinated resin (B)".
- the fluororesin (B) may have a structure represented by the following chemical formula (2), or have a structure represented by the following formula (3): good too.
- Rb each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched chain having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms or a fluorine atom, Any number of hydrogen atoms in the alkyl group are substituted with fluorine atoms, and R 2 is a hydrogen atom, a linear chain having 1 to 6 carbon atoms, a branched chain having 3 to 6 carbon atoms, or a chain having 3 to 6 carbon atoms. represents a cyclic alkyl group of 6.
- Rb each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched chain having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms or a fluorine atom, Any number of hydrogen atoms in the alkyl group are substituted with fluorine atoms, R 1 represents a hydrogen atom, a fluorine atom or a methyl group, R 2 represents a hydrogen atom, a straight chain having 1 to 6 carbon atoms, , represents a branched chain having 3 to 6 carbon atoms or a cyclic alkyl group having 3 to 6 carbon atoms.
- R 1 is preferably a hydrogen atom or a methyl group.
- R 2 include a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 1-methylpropyl group, 2-methylpropyl group, tert-butyl group, n- pentyl group, isopentyl group, 1,1-dimethylpropyl group, 1-methylbutyl group, 1,1-dimethylbutyl group, n-hexyl group, cyclopentyl group, cyclohexyl group and the like, hydrogen atom, methyl group, An ethyl group, an n-propyl group and an isopropyl group are preferred, and a hydrogen atom and a methyl group are more preferred.
- Rb in formula (2) or formula (3) is a fluorine atom, a trifluoromethyl group, a difluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, an n-heptafluoropropyl group.
- the content of the repeating unit represented by formula (3) in the fluororesin (B) is 5 mol% or more and 70 mol% or less with respect to 100 mol% of all repeating units constituting the fluororesin (B). is preferable, 10 mol % or more and 50 mol % or less is more preferable, and 10 mol % or more and 30 mol % or less is particularly preferable.
- the content of the repeating unit of formula (3) is more than 70 mol %, the fluororesin (B) tends to be difficult to dissolve in the solvent. On the other hand, when the content of the repeating unit of formula (3) is less than 5 mol %, the resistance to UV ozone treatment or oxygen plasma treatment tends to decrease.
- the fluorine-containing resin (B) has a repeating unit represented by formula (3), it is one of preferred embodiments because it has resistance to UV ozone treatment or oxygen plasma treatment.
- the fluorine-containing resin (B) may contain a structure represented by the following formula (4).
- R 3 and R 4 each independently represent a hydrogen atom or a methyl group.
- the divalent linking group A 1 is a linear alkylene group having 1 to 10 carbon atoms, for example, methylene group, ethylene group, propylene group, n-butylene group, n-pentylene group, n-hexalene group , n-heptalene group, n-octalene group, n-nonalene group and n-decalene group.
- the divalent linking group A 1 is a branched alkylene group having 3 to 10 carbon atoms, for example, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, isopentalene group, isohexalene group, etc. can be mentioned.
- the divalent linking group A 1 is a cyclic alkylene group having 3 to 10 carbon atoms, for example, disubstituted cyclopropane, disubstituted cyclobutane, disubstituted cyclopentane, disubstituted cyclohexane, disubstituted Examples include cycloheptane, disubstituted cyclooctane, disubstituted cyclodecane, and disubstituted 4-tert-butylcyclohexane.
- examples of the hydroxyl-substituted alkylene groups include a hydroxyethylene group, a 1-hydroxy-n-propylene group, and a 2-hydroxy-n-propylene group.
- the divalent linking group A 1 is a methylene group, ethylene group, propylene group, n-butylene group, isobutylene group, sec-butylene group, cyclohexyl group, 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 —), 2-hydroxy-n-butylene group, hydroxy-sec-butylene group (—CH(CH 2 OH)CH 2 CH 2 —) are preferred, ethylene group, propylene group , 2-hydroxy-n-propylene group and hydroxy-isopropylene group (--CH(CH 2 OH)CH 2 --) are more preferable, and ethylene group and 2-hydroxy-n-propylene group are particularly preferable.
- Y 1 represents a divalent linking group and represents —O— or —NH—, more preferably —O—.
- n represents an integer of 1 to 3, and n is preferably 1.
- the substitution positions on the aromatic ring independently represent ortho-position, meta-position and para-position, preferably para-position.
- Preferred examples of the repeating unit represented by formula (4) include the following structures.
- the substitution position of the aromatic ring is exemplified by the para position, the substitution position may independently be the ortho position or the meta position.
- the content of the repeating unit represented by formula (4) in the fluororesin (B) is 5 mol% or more and 70 mol% or less with respect to 100 mol% of all repeating units constituting the fluororesin (B). is preferable, 10 mol % or more and 50 mol % or less is more preferable, and 10 mol % or more and 30 mol % or less is particularly preferable.
- the fluororesin (B) tends to be difficult to dissolve in the solvent.
- the content of the repeating unit of formula (4) is less than 5 mol %, the resistance to UV ozone treatment or oxygen plasma treatment tends to decrease.
- the fluororesin (B) of the present disclosure is a copolymer containing a repeating unit represented by the above formula (3) and a repeating unit represented by the above formula (4); It may be a mixture (blend) of a repeating unit represented by and another copolymer containing a repeating unit represented by the above formula (4).
- the fluorine-containing resin (B) may contain a structure represented by the following formula (5).
- R 5 and R 6 each independently represent a hydrogen atom or a methyl group.
- the fluororesin (B) of the present disclosure has more excellent liquid repellency against ink after UV ozone treatment or oxygen plasma treatment, so This is one of preferred embodiments.
- a 2 and A 3 each independently represent a divalent linking group, which is linear with 1 to 10 carbon atoms, branched with 3 to 10 carbon atoms, or 3 to 10 carbon atoms. represents a cyclic alkylene group, and any number of hydrogen atoms in the alkylene group may be substituted with a hydroxyl group or —O—C( ⁇ O)—CH 3 .
- the divalent linking groups A 2 and A 3 are each independently a linear alkylene group having 1 to 10 carbon atoms, for example, a methylene group, an ethylene group, a propylene group, an n-butylene group, an n- Examples include pentylene group, n-hexalene group, n-heptalene group, n-octalene group, n-nonalene group and n-decalene group.
- each of the divalent linking groups A 2 and A 3 is independently a branched alkylene group having 3 to 10 carbon atoms
- examples thereof include an isopropylene group, an isobutylene group, a sec-butylene group and a tert-butylene group. , an isopentalene group, an isohexalene group, and the like.
- divalent linking groups A 2 and A 3 are each independently a cyclic alkylene group having 3 to 10 carbon atoms, for example, disubstituted cyclopropane, disubstituted cyclobutane, disubstituted cyclopentane, 2 Examples include substituted cyclohexane, disubstituted cycloheptane, disubstituted cyclooctane, disubstituted cyclodecane, and disubstituted 4-tert-butylcyclohexane.
- the hydroxyl group-substituted alkylene groups include, for example, 1-hydroxyethylene group (—CH(OH)CH 2 —), 2-hydroxyethylene group (—CH 2 CH(OH)—), 1-hydroxy-n-propylene group, 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 —), 1- hydroxy-n-butylene group, 2-hydroxy-n-butylene group, hydroxy-sec-butylene group (--CH(CH 2 OH)CH 2 CH 2 --), hydroxy-isobutylene group (--CH 2 CH(CH 2 OH )CH 2 —), hydroxy-tert-butylene group (—C(CH 2 OH)(CH 3 )CH 2 —), and the like.
- the divalent linking groups A 2 and A 3 are each independently a methylene group, ethylene group, propylene group, n-butylene group, isobutylene group, sec-butylene group, cyclohexyl group, 1-hydroxyethylene group (- CH(OH)CH 2 —), 2-hydroxyethylene group (—CH 2 CH(OH)—), 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 — ), 2-hydroxy-n-butylene group and hydroxy-sec-butylene group (--CH(CH 2 OH)CH 2 CH 2 --) are preferred, and ethylene group, propylene group and 1-hydroxyethylene group (--CH(OH )CH 2 —), 2-hydroxyethylene group (—CH 2 CH(OH)—), 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 —) are more An ethylene group, a 1-hydroxyethylene group (-----
- Y 2 and Y 3 each represent a divalent linking group, each independently representing -O- or -NH-, and more preferably -O-.
- n represents an integer of 1 to 3, and n is preferably 1.
- r represents 0 or 1.
- Preferred examples of the repeating unit represented by formula (5) include the following structures.
- the content of the repeating unit represented by formula (5) in the fluororesin (B) is 5 mol% or more and 70 mol% or less with respect to 100 mol% of all repeating units constituting the fluororesin (B). is preferable, 10 mol % or more and 50 mol % or less is more preferable, and 10 mol % or more and 30 mol % or less is particularly preferable.
- the fluororesin (B) tends to be difficult to dissolve in the solvent.
- the content of the repeating unit of formula (5) is less than 5 mol %, the adhesiveness of the resin film or bank obtained from the fluororesin (B) to the substrate tends to decrease.
- the fluorine-containing resin (B) is a copolymer containing a repeating unit represented by the above formula (3) and a repeating unit represented by the above formula (5), and a repeating unit represented by the above formula (3). It may be a mixture (blend) with another type of copolymer containing the repeating unit represented by the above formula (5).
- the fluororesin of the present disclosure is a fluororesin containing a repeating unit in which W 2 in formula (5) is —O—C( ⁇ O)—NH—, and W 2 in formula (5) is —C
- the fluorine-containing resin (B) may contain a structure represented by the following formula (6).
- R7 represents a hydrogen atom or a methyl group.
- R 8 represents a linear alkyl group having 1 to 15 carbon atoms, a branched chain having 3 to 15 carbon atoms or a cyclic alkyl group having 3 to 15 carbon atoms, and any number in the alkyl group is substituted with a fluorine atom, and the fluorine content in the repeating unit is 30% by mass or more.
- R 8 is a linear alkyl group, specifically, it is a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group or C 10-14 Any number of hydrogen atoms in the linear alkyl group of are substituted with fluorine atoms.
- R 8 is a linear alkyl group
- the repeating unit represented by formula (6) above is preferably a repeating unit represented by formula (6-1) below.
- R 9 has the same definition as R 7 in formula (6).
- X is a hydrogen atom or a fluorine atom.
- p is an integer of 1-4.
- q is an integer from 1 to 14; Particularly preferably, p is an integer of 1 to 2, q is an integer of 2 to 8, and X is a fluorine atom.
- Preferred examples of the repeating unit represented by formula (6) include the following structures.
- the content of the repeating unit represented by formula (6) is preferably 5 mol% or more and 70 mol% or less, more preferably 10 mol% or more and 50 mol%, based on 100 mol% of all repeating units constituting the fluororesin (B). mol % or less is more preferable, and 10 mol % or more and 30 mol % or less is particularly preferable.
- the fluororesin (B) tends to be difficult to dissolve in the solvent.
- the repeating unit represented by formula (6) is a repeating unit that imparts liquid repellency to ink after UV ozone treatment or oxygen plasma treatment. Therefore, when it is desired to pursue high liquid repellency to ink, it is preferable that the fluororesin (B) of the present disclosure contains a repeating unit represented by formula (6).
- the fluorine-containing resin (B) may contain a structure represented by the following formula (7).
- R 10 represents a hydrogen atom or a methyl group.
- R 11 is a straight chain having 1 to 15 carbon atoms, a branched chain having 3 to 15 carbon atoms, represents a cyclic alkyl group having 3 to 15 carbon atoms, any number of hydrogen atoms in the alkyl group is substituted with fluorine atoms, and the fluorine content in R 11 is 30% by mass or more
- m represents an integer of 0 to 3.
- Preferred examples of the repeating unit represented by formula (7) include the following structures.
- the content of the repeating unit represented by the formula (7) is preferably 5 mol% or more and 70 mol% or less, more preferably 10 mol% or more and 50 mol%, based on 100 mol% of all repeating units constituting the fluororesin (B). mol % or less is more preferable, and 20 mol % or more and 40 mol % or less is particularly preferable.
- the fluororesin (B) tends to be difficult to dissolve in the solvent.
- the repeating unit represented by formula (7) has solubility in an alkaline developer. Therefore, when it is desired to impart alkali developability to the fluororesin film obtained from the fluororesin (B), the fluororesin (B) of the present disclosure is added with the formula ( It preferably contains a repeating unit represented by 7).
- the fluorine-containing resin (B) may contain a structure represented by the following formula (8).
- R 13 represents a hydrogen atom or a methyl group.
- a 4 represents a divalent linking group, and represents a straight chain having 1 to 10 carbon atoms, a branched chain having 3 to 10 carbon atoms or a cyclic alkylene group having 3 to 10 carbon atoms. , any number of hydrogen atoms in the alkylene group may be substituted with a hydroxyl group or —O—C( ⁇ O)—CH 3 .
- the divalent linking group A 4 is a linear alkylene group having 1 to 10 carbon atoms, for example, methylene group, ethylene group, propylene group, n-butylene group, n-pentylene group, n-hexalene group , n-heptalene group, n-octalene group, n-nonalene group and n-decalene group.
- the divalent linking group A4 is a branched alkylene group having 3 to 10 carbon atoms, for example, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, isopentalene group, isohexalene group, etc. can be mentioned.
- divalent linking group A 4 is a cyclic alkylene group having 3 to 10 carbon atoms
- disubstituted cyclopropane disubstituted cyclobutane
- disubstituted cyclopentane disubstituted cyclohexane
- disubstituted Examples include cycloheptane, disubstituted cyclooctane, disubstituted cyclodecane, and disubstituted 4-tert-butylcyclohexane.
- the hydroxyl group-substituted alkylene groups include, for example, 1-hydroxyethylene group (—CH(OH)CH 2 —), 2-hydroxyethylene group (—CH 2 CH(OH)—), 1-hydroxy-n-propylene group, 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 —), 1- hydroxy-n-butylene group, 2-hydroxy-n-butylene group, hydroxy-sec-butylene group (--CH(CH 2 OH)CH 2 CH 2 --), hydroxy-isobutylene group (--CH 2 CH(CH 2 OH )CH 2 —), hydroxy-tert-butylene group (—C(CH 2 OH)(CH 3 )CH 2 —), and the like.
- the divalent linking group A4 is a methylene group, ethylene group, propylene group, n-butylene group, isobutylene group, sec-butylene group, cyclohexyl group, 1 -hydroxyethylene group (-CH(OH)CH2- ), 2-hydroxyethylene group (—CH 2 CH(OH)—), 2-hydroxy-n-propylene group, hydroxy-isopropylene group (—CH(CH 2 OH)CH 2 —), 2-hydroxy-n -butylene group, hydroxy-sec-butylene group (-CH(CH 2 OH)CH 2 CH 2 -) are preferred, ethylene group, propylene group, 1-hydroxyethylene group (-CH(OH)CH 2 -), 2 -Hydroxyethylene group (-CH 2 CH(OH)-), 2-hydroxy-n-propylene group, hydroxy-isopropylene group (-CH(CH 2 OH)CH 2 -) is more preferable, ethylene group, 1- A hydroxyethylene group (-CH(OH
- Y 4 represents a divalent linking group and represents —O— or —NH—, more preferably —O—.
- r represents 0 or 1.
- E1 represents a hydroxyl group, a carboxyl group or an oxirane group.
- E 1 is an oxirane group
- examples include an ethylene oxide group, a 1,2-propylene oxide group, a 1,3-propylene oxide group and the like. Among them, an ethylene oxide group is preferred.
- s represents 0 or 1.
- (-Y 4 -A 4 -) represents a single bond.
- r is 0 and s is 0 , the structure is such that E1 is bound to the main chain of the repeating unit.
- Preferred examples of the repeating unit represented by formula (8) include the following structures.
- the repeating unit represented by the formula (8) imparts solubility of the fluororesin (B) to an alkaline developer. Therefore, when it is desired to impart alkali developability to the film obtained from the fluororesin (B), the fluororesin (B) of the present disclosure is added with formula (8) when E 1 is a hydroxyl group or a carboxyl group. It is preferable to include a repeating unit represented by
- the fluorine-containing resin (B) having a cross-linking site is obtained, for example, by polymerizing a monomer to obtain a fluorine-containing resin precursor having a repeating unit having a structure represented by the above formulas (3), (6) to (8), and then By reacting a fluorine-containing resin precursor with a photopolymerizable group derivative, a photopolymerizable group is introduced into the side chain of the polymer to form a repeating unit having the structure represented by the above formulas (4) and (5).
- the photopolymerizable group to be introduced into the fluorine-containing resin precursor is preferably an acrylic group, a methacrylic group, a vinyl group, or an allyl group, and more preferably an acrylic group.
- examples of the photopolymerizable group derivative include acrylic acid derivatives such as isocyanate monomers having an acrylic group and epoxy monomers having an acrylic group.
- Isocyanate monomers having an acrylic group include, for example, 2-isocyanatoethyl methacrylate, 2-isocyanatoethyl acrylate, 2-(2-methacryloyloxyethyloxy)ethyl isocyanate, 1,1-(bisacryloyloxymethyl) and ethyl isocyanate. 2-isocyanatoethyl acrylate is preferred.
- Examples of epoxy monomers having an acrylic group include glycidyl acrylate, 4-hydroxybutyl acrylate glycidyl ether (4HBAGE, manufactured by Mitsubishi Chemical Corporation), and the like.
- a photopolymerizable group is introduced into the fluororesin precursor by an addition reaction between the hydroxyl group of the fluororesin precursor and the photopolymerizable group derivative.
- the proportion of the photopolymerizable group in the fluororesin (B) is preferably 10 mol % or more and 70 mol % or less in the fluororesin (B). If the proportion of the photopolymerizable group is less than 10 mol %, the strength of the resin film and the partition walls tends to decrease. If the proportion of the photopolymerizable group exceeds 70 mol %, it may become difficult to form a resin film by coating. It is more preferably 15 mol % to 60 mol %.
- the molecular weight of the fluorine-containing resin (B) is a weight average molecular weight measured by high-performance gel permeation chromatography (GPC) using polystyrene as a standard substance, preferably 1,000 or more, 1 ,000,000 or less, more preferably 2,000 or more and 500,000 or less, and particularly preferably 3,000 or more and 100,000 or less. If the molecular weight is less than 1,000, the strength of the formed resin film or bank tends to decrease. can be.
- GPC high-performance gel permeation chromatography
- the dispersion degree (Mw/Mn) of the fluororesin (B) is preferably 1.01 to 5.00, more preferably 1.01 to 4.00, and particularly preferably 1.01 to 3.00.
- the fluorine-containing resin (B) may be a random copolymer, an alternating copolymer, a block copolymer, or a graft copolymer. .
- a random copolymer is preferable from the viewpoint of dispersing each characteristic appropriately rather than locally.
- the fluorine content of the fluorine-containing resin (B) is desirably 20 to 50% by mass, more desirably 25 to 40% by mass. If the fluorine content is within this range, it will easily dissolve in the solvent.
- the fluorine-containing resin (B) contains fluorine atoms, a resin film or bank having excellent liquid repellency can be obtained.
- the "fluorine content of the fluororesin (B)” refers to the molar ratio of the monomers constituting the fluororesin (B) measured by NMR (nuclear magnetic resonance spectroscopy). It means a value calculated from the molecular weight of the monomer constituting (B) and the content of fluorine contained in the monomer.
- the fluorine content when the fluorine-containing resin (B) is a resin obtained by polymerizing 1,1-bistrifluoromethylbutadiene, 4-hydroxystyrene and 2-(perfluorohexyl)ethyl methacrylate will be explained.
- the ratio of each composition is calculated by NMR measurement of the fluorine-containing resin (B) (molar ratio).
- Mw molecular weight of the monomer of each composition of the fluorine-containing resin
- the weight ratio (wt%) of each composition is calculated from the total value.
- the molecular weight of 1,1-bistrifluoromethylbutadiene is 190
- the molecular weight of 4-hydroxystyrene is 120
- the molecular weight of 2-(perfluorohexyl)ethyl methacrylate is 432.
- the fluorine-containing resin (B) can be used alone or in combination of two or more.
- the proportion of the fluorine-containing resin (B) in the total solid content of the photosensitive resin composition of the present disclosure is preferably 0.1 to 40% by mass, more preferably 1 to 30% by mass. Within this range, the water and oil repellency of the resin film and the adhesion to the substrate are improved.
- the solvent is not particularly limited as long as the fluororesin (B) is soluble. is mentioned. Preferred are methyl ethyl ketone, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), cyclohexanone, ethyl lactate, butyl acetate and ⁇ -butyrolactone.
- the amount of the solvent in the photosensitive resin composition of the present disclosure is the concentration of the fluorine-containing resin (B) (however, if the photosensitive resin composition contains an alkali-soluble resin (D) described later, the alkali-soluble resin (D ) is preferably in the range of 50 parts by mass or more and 2,000 parts by mass or less with respect to 100 parts by mass of the combined concentration). It is more preferably 100 parts by mass or more and 1,000 parts by mass or less.
- the photopolymerization initiator is not particularly limited as long as it polymerizes a monomer having a polymerizable double bond with high energy rays such as electromagnetic waves and electron beams. It is possible to use a known photopolymerization initiator. As a photopolymerization initiator, a photoradical initiator or a photoacid initiator can be used, and these may be used alone, or a photoradical initiator and a photoacid initiator may be used in combination. You may mix and use the above photo radical initiators or photo-acid initiators. Moreover, by using an additive together with the photopolymerization initiator, it is possible to carry out living polymerization in some cases, and known additives can be used.
- an intramolecular cleavage type that generates radicals by cleaving the bonds in the molecule by absorption of electromagnetic waves or electron beams, and hydrogen donors such as tertiary amines and ethers are used in combination. It can be classified into a hydrogen abstraction type that generates radicals by Photoradical initiators other than the types listed above can also be used.
- photoradical initiators include benzophenone-based, acetophenone-based, diketone-based, acylphosphine oxide-based, quinone-based, and acyloin-based initiators.
- benzophenones include benzophenone, 4-hydroxybenzophenone, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid, 4,4′-bis(dimethylamino)benzophenone, and 4,4′-bis(diethylamino)benzophenone. etc. Among them, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid and 4,4'-bis(diethylamino)benzophenone are preferred.
- acetophenones include acetophenone, 2-(4-toluenesulfonyloxy)-2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2′-dimethoxy-2-phenylacetophenone, p-methoxyacetophenone, 2 -methyl-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and the like. Among them, p-dimethylaminoacetophenone and p-methoxyacetophenone are preferred.
- diketones include 4,4'-dimethoxybenzyl, methyl benzoylformate, and 9,10-phenanthrenequinone. Among them, 4,4'-dimethoxybenzyl and methyl benzoylformate are preferred.
- acylphosphine oxides include bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
- quinones examples include anthraquinone, 2-ethylanthraquinone, camphorquinone, 1,4-naphthoquinone, and the like. Among them, camphorquinone and 1,4-naphthoquinone are preferred.
- acyloin-based compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether. Among them, benzoin and benzoin methyl ether are preferred.
- Benzophenone-based, acetophenone-based, and diketone-based photoradical initiators are preferred, and benzophenone-based initiators are more preferred.
- the product names manufactured by BSA are preferred.
- Irgacure 127, Irgacure 184, Irgacure 369, Irgacure 651, Irgacure 819, Irgacure 907, Irgacure 2959, Irgacure OXE-01, Darocure are preferred.
- Irgacure 651 and Irgacure 369 are more preferable.
- Photoacid initiators are specifically aromatic sulfonic acids, aromatic iodonium, aromatic diazonium, aromatic ammonium, thianthrenium, thioxanthonium, (2,4-cyclopentadien-1-yl)(1- Onium consisting of a pair of at least one cation selected from the group consisting of iron and at least one anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, and pentafluorophenylborate is salt.
- bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluorophosphate bis[4-(diphenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate, and diphenyliodonium hexafluorophosphate are particularly preferred.
- photoacid generators include, for example, San-Apro product names: CPI-100P, CPI-110P, CPI-101A, CPI-200K, CPI-210S, Dow Chemical Japan Co., Ltd. product names: Cyracure photocuring initiator UVI-6990, Cyracure photocuring initiator UVI-6992, Cyracure photocuring initiator UVI-6976, product names manufactured by ADEKA Co., Ltd.: Adeka Optomer SP-150, Adeka Optomer SP-152, Adeka Optomer SP-170, Adeka Optomer SP-172, Adeka Optomer SP-300, product names manufactured by Nippon Soda Co., Ltd.: CI-5102, CI-2855, product names manufactured by Sanshin Chemical Industry Co., Ltd.: San-Aid SI -60L, San-Aid SI-80L, San-Aid SI-100L, San-Aid SI-110L, San-Aid SI-180
- the content of the photopolymerization initiator in the photosensitive resin composition of the present disclosure is the fluorine-containing resin (B) (however, if the photosensitive resin composition contains an alkali-soluble resin (D) described later, the alkali-soluble resin It is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less per 100 parts by mass of (D) combined. If the content of the photopolymerization initiator is less than 0.1 parts by mass, the crosslinking effect tends to be insufficient, and if it exceeds 30 parts by mass, the resolution and sensitivity tend to decrease.
- the photosensitive resin composition of the present disclosure preferably further contains an ethylenically unsaturated compound (C) and/or an alkali-soluble resin (D).
- ⁇ Ethylenically unsaturated compound (C)> When the photosensitive resin composition of the present disclosure contains the ethylenically unsaturated compound (C), the curing of the photosensitive resin composition by light irradiation is accelerated, enabling curing in a shorter time.
- ethylenically unsaturated compound (C) examples include polyfunctional acrylates (for example, product names manufactured by Shin-Nakamura Chemical Co., Ltd.: A-TMM-3, A-TMM-3L, A-TMM-3LM-N , A-TMPT, AD-TMP), polyethylene glycol diacrylate (e.g., product names manufactured by Shin-Nakamura Chemical Co., Ltd.: A-200, A-400, A-600), urethane acrylate (e.g., Shin-Nakamura Chemical Industry Product names manufactured by Co., Ltd.: UA-122P, UA-4HA, UA-6HA, UA-6LPA, UA-11003H, UA-53H, UA-4200, UA-200PA, UA-33H, UA-7100, UA-7200 ), pentaerythritol tetraacrylate, and the like.
- polyfunctional acrylates for example, product names manufactured by Shin-Nakamura Chemical Co.
- Preferred polyfunctional acrylate compounds are exemplified below.
- the content of the ethylenically unsaturated compound (C) is the concentration of the fluorine-containing resin (B) (however, when the photosensitive resin composition contains an alkali-soluble resin (D) described later, the alkali-soluble resin (D) is preferably 10 parts by mass or more and 300 parts by mass or less, more preferably 50 parts by mass or more and 200 parts by mass or less. If the content of the ethylenically unsaturated compound (C) is less than 10 parts by mass, the crosslinking effect tends to be insufficient, and if it exceeds 300 parts by mass, the resolution and sensitivity tend to decrease.
- Alkali-soluble resin (D) When the photosensitive resin composition of the present disclosure contains the alkali-soluble resin (D), the shape of the bank obtained from the photosensitive resin composition of the present disclosure can be improved.
- the alkali-soluble resin (D) an alkali-soluble novolac resin can be mentioned.
- Alkali-soluble novolac resins can be obtained by condensing phenols and aldehydes in the presence of an acidic catalyst.
- phenols include phenol, o-cresol, m-cresol, p-cresol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol and 3,4-dimethylphenol. , 3,5-dimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, resorcinol, 2-methylresorcinol, 4-ethylresorcinol, hydroquinone, methylhydroquinone, catechol, 4-methyl-catechol , pyrogallol, phloroglucinol, thymol, isothymol and the like. These phenols may be used alone or in combination of two or more.
- aldehydes include formaldehyde, trioxane, paraformaldehyde, benzaldehyde, acetaldehyde, propylaldehyde, phenylacetaldehyde, ⁇ -phenylpropylaldehyde, ⁇ -phenylpropylaldehyde, o-hydroxybenzaldehyde, m-hydroxybenzaldehyde, p- Examples include hydroxybenzaldehyde, o-methylbenzaldehyde, m-methylbenzaldehyde, p-methylbenzaldehyde, nitrobenzaldehyde, furfural, glyoxal, glutaraldehyde, terephthalaldehyde, and isophthalaldehyde.
- acid catalysts include hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, phosphorous acid, formic acid, oxalic acid, acetic acid, methanesulfonic acid, diethylsulfonic acid, and p-toluenesulfonic acid. These acid catalysts may be used alone or in combination of two or more.
- alkali-soluble resin (D) examples include acid-modified epoxy acrylates.
- acid-modified epoxy acrylates examples include product names manufactured by Nippon Kayaku Co., Ltd.: CCR-1218H, CCR-1159H, CCR-1222H, CCR-1291H, CCR-1235, PCR-1050, TCR-1335H, UXE -3024, ZAR-1035, ZAR-2001H, ZAR2051H, ZFR-1185 and ZCR-1569H and the like can be used.
- the weight average molecular weight of the alkali-soluble resin (D) component is preferably 1,000 to 50,000 from the viewpoint of developability and resolution of the photosensitive resin composition.
- the content of the alkali-soluble resin (D) in the photosensitive resin composition of the present disclosure is preferably 500 parts by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the fluorine-containing resin (B), and more preferably. is 1,000 parts by mass or more and 7,000 parts by mass or less. If the content of the alkali-soluble resin (D) exceeds 10,000 parts by mass, the fluororesin of the present disclosure tends to have insufficient liquid repellency against ink after UV ozone treatment or oxygen plasma treatment. .
- the photosensitive resin composition of the present disclosure further includes at least one selected from the group consisting of photoradical sensitizers (E), chain transfer agents (F), ultraviolet absorbers (G) and polymerization inhibitors (H). is preferably included.
- the photoradical sensitizer (E) is preferably a compound that absorbs light or radiation and becomes an excited state.
- the photoradical sensitizer (E) is in an excited state, and upon contact with the photopolymerization initiator, causes electron transfer, energy transfer, heat generation, or the like, thereby decomposing the photopolymerization initiator to generate an acid. becomes easier.
- the photoradical sensitizer (E) may have an absorption wavelength in the region of 350 nm to 450 nm, and includes polynuclear aromatics, xanthenes, xanthones, cyanines, merocyanines, thiazines, acridines, acridones, Mention may be made of anthraquinones, squariums, styryls, base styryls or coumarins.
- polynuclear aromatics examples include pyrene, perylene, triphenylene, anthracene, 9,10-dibutoxyanthracene, 9,10-diethoxyanthracene, 3,7-dimethoxyanthracene, and 9,10-dipropyloxyanthracene. be able to.
- xanthenes include fluorescein, eosin, erythrosine, rhodamine B, and rose bengal.
- xanthones include xanthone, thioxanthone, dimethylthioxanthone, diethylthioxanthone, and isopropylthioxanthone.
- Examples of cyanines include thiacarbocyanine and oxacarbocyanine.
- Examples of merocyanines include merocyanine and carbomerocyanine.
- Examples of thiazines include thionin, methylene blue, and toluidine blue.
- Examples of acridines include acridine orange, chloroflavin, and acriflavin.
- Examples of acridones include acridone and 10-butyl-2-chloroacridone.
- Anthraquinones can be exemplified as anthraquinones.
- Squarium can be exemplified as the squarium.
- Examples of base styryl compounds include 2-[2-[4-(dimethylamino)phenyl]ethenyl]benzoxazole.
- Coumarins include 7-diethylamino 4-methylcoumarin, 7-hydroxy 4-methylcoumarin, or 2,3,6,7-tetrahydro-9-methyl-1H,5H,11H[l]benzopyrano[6,7, 8-ij]quinolizin-11-nones can be exemplified.
- These radical photosensitizers (E) may be used alone or in combination of two or more.
- the photoradical sensitizer (E) used in the photosensitive resin composition of the present disclosure is preferably polynuclear aromatics, acridones, styryls, base styryls, They are coumarins or xanthones, and xanthones are particularly preferred. Among the xanthones, diethylthioxanthone and isopropylthioxanthone are preferred.
- the content of the photoradical sensitizer (E) is preferably 0.1 parts by mass to 8 parts by mass, more preferably 1 part by mass to 4 parts by mass with respect to 100 parts by mass of the fluorine-containing resin (B). be.
- a chain transfer agent (F) is preferably used in the photosensitive resin composition of the present disclosure, if necessary.
- Examples of the chain transfer agent (F) include the same compounds that can be used in the synthesis of the fluorine-containing resin (A) described above.
- the photosensitive resin composition of the present disclosure preferably uses an ultraviolet absorber (G) as necessary, and examples of the ultraviolet absorber (G) include salicylic acid-based, benzophenone-based, triazole-based, and the like.
- the content of the ultraviolet absorber (G) is preferably 0.5 to 5% by mass, more preferably 1 to 3% by mass in the photosensitive resin composition.
- the polymerization inhibitor (H) used in the photosensitive resin composition of the present disclosure is not particularly limited, but o-cresol, m-cresol, p-cresol, 6-t-butyl-2,4-xylenol, 2, 6-di-t-butyl-p-cresol, hydroquinone, catechol, 4-t-butylpyrocatechol, 2,5-bistetramethylbutylhydroquinone, 2,5-di-t-butylhydroquinone, p-methoxyphenol, 1,2,4-trihydroxybenzene, 1,2-benzoquinone, 1,3-benzoquinone, 1,4-benzoquinone, leucoquinizarin, phenothiazine, 2-methoxyphenothiazine, tetraethylthiuram disulfide, 1,1-diphenyl-2-picri Ruhydrazyl or 1,1-diphenyl-2-pic
- polymerization inhibitors include N,N'-di-2-naphthyl-p-phenylenediamine (trade name, Nonflex F) manufactured by Seiko Chemical Co., Ltd., N,N-diphenyl-p- Phenylenediamine (trade name, Nonflex H), 4,4′-bis(a,a-dimethylbenzyl)diphenylamine (trade name, Nonflex DCD), 2,2′-methylene-bis(4-methyl-6- tert-butylphenol) (trade name, Nonflex MBP), N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine (trade name, Ozonon 35) or ammonium manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
- Examples include N-nitrosophenylhydroxyamine (trade name, Q-1300) or N-nitrosophenylhydroxyamine aluminum salt (trade name, Q-1301).
- the content of the polymerization inhibitor (H) in the total solid content of the photosensitive resin composition of the present disclosure is preferably 0.001 to 20% by mass, more preferably 0.005 to 10% by mass, and 0.01 to 5 % by weight is particularly preferred. When the content is within the above range, the development residue of the photosensitive resin composition is reduced, and the pattern linearity is good.
- the photosensitive resin composition of the present disclosure may contain other additives as necessary.
- Other additives include various additives such as dissolution inhibitors, plasticizers, stabilizers, colorants, thickeners, adhesion agents, and antioxidants. These other additives may be known ones.
- the cured product of the present disclosure is characterized by curing a photosensitive resin composition.
- the photosensitive resin composition of the present disclosure is formed into a film by a known method and exposed to light to obtain a "resin film" which is a film composed of a cured product of a composition containing the fluororesin (B) as the main component. be able to.
- the specific method of film formation and exposure is the same as the method of forming partition walls, which will be described later.
- the surface roughness of the resin film obtained from the photosensitive resin composition of the present disclosure is improved by containing the above-described surface conditioner.
- the cured product of the present disclosure is preferably used as partition walls, and particularly preferably used as partition walls for organic EL displays, quantum dot displays, and the like.
- the method of forming the partition may include (1) a film forming step, (2) an exposure step, and (3) a developing step. Each step will be described below.
- the photosensitive resin composition of the present disclosure is applied to a substrate and then heated to form a fluorine-containing resin film from the photosensitive resin composition.
- the heating conditions are not particularly limited, but preferably 80 to 100° C. for 60 to 200 seconds. Thereby, the solvent and the like contained in the photosensitive resin composition can be removed.
- a silicon wafer, metal, glass, ITO substrate, or the like can be used as the substrate.
- an organic or inorganic film may be provided in advance on the substrate.
- the substrate may be washed in advance.
- ultrapure water, acetone, alcohol (methanol, ethanol, isopropyl alcohol) or the like can be used for cleaning.
- a known method such as spin coating can be used as a method for applying the photosensitive resin composition of the present disclosure to the substrate.
- the high-energy ray is preferably at least one selected from the group consisting of ultraviolet rays, gamma rays, X-rays and ⁇ -rays.
- the exposure dose of high-energy rays is preferably 1 mJ/cm 2 or more and 200 mJ/cm 2 or less, more preferably 10 mJ/cm 2 or more and 100 mJ/cm 2 or less.
- the fluorine-containing resin film after the exposure step is developed with an alkaline aqueous solution to form a fluorine-containing resin pattern film. That is, a fluorine-containing resin pattern film is formed by dissolving either the exposed portion of the fluorine-containing resin film or the unexposed portion of the film in an alkaline aqueous solution.
- TMAH tetramethylammonium hydroxide
- TBAH tetrabutylammonium hydroxide
- concentration is preferably 0.1% by mass or more and 5% by mass or less, more preferably 2% by mass or more and 3% by mass or less.
- a known method can be used as a developing method, and examples thereof include a dip method, a puddle method, and a spray method.
- the development time (time during which the developer contacts the fluorine-containing resin film) is preferably 10 seconds or more and 3 minutes or less, more preferably 30 seconds or more and 2 minutes or less.
- the cleaning method and cleaning time are preferably 10 seconds or more and 3 minutes or less, more preferably 30 seconds or more and 2 minutes or less.
- the partitions thus manufactured can be used as banks for displays.
- the display of the present disclosure comprises a partition wall obtained by curing the photosensitive resin composition of the present disclosure, and a light-emitting element comprising a light-emitting layer or a wavelength conversion layer arranged in a region partitioned by the partition wall.
- a light-emitting element comprising a light-emitting layer or a wavelength conversion layer arranged in a region partitioned by the partition wall.
- Characterized by Examples of displays include organic EL displays and quantum dot displays.
- the surface conditioning method for a molded article of the present disclosure is characterized by using the fluororesin (A) having the structure represented by the general formula (1).
- the fluororesin (A) the same ones as those described above for the surface conditioner and the photosensitive resin composition can be used.
- the method of the present disclosure can condition the surface of molded articles of various resins. Surface conditioning of molded products is to suppress the occurrence of various coating film defects such as bubbles, brush marks, orange peel, repelling, craters, pinholes, and floating spots that occur during resin molding and coating film preparation. be. By suppressing the occurrence of these coating film defects, for example, surface roughness can be improved.
- the type of resin used as the material for the molded article is not particularly limited, and examples thereof include olefin resins, epoxy resins, (meth)acrylic resins, urethane resins, fluorine resins, and the like, or combinations thereof.
- the method of the present disclosure can be used particularly well when molding a composition containing two or more resins with different fluorine contents.
- a photosensitive resin composition is particularly preferred.
- the fluororesin (A) can be used by mixing with the resin composition. Preferred aspects and blending amounts of the fluorine-containing resin (A) are the same as those in the photosensitive resin composition described above.
- the fluorine-containing resin (A) acts as a defoaming agent, a leveling agent, a surface conditioner such as an anti-popping agent, and a surfactant.
- the present disclosure also includes the use of the fluororesin (A) having the structure represented by the general formula (1) for conditioning the surface of molded articles.
- HEMA 2-hydroxyethyl methacrylate
- MEK methyl ethyl ketone
- AIBN 2,2'-azobis(2-methylbutyronitrile) (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as AIBN) ) was added, and after deaeration with stirring, the inside of the flask was replaced with nitrogen gas, the internal temperature was raised to 79° C., and the reaction was allowed to proceed overnight.
- AIBN 2,2'-azobis(2-methylbutyronitrile)
- Synthesis Example 2 Synthesis of fluororesin B-2 having a cross-linking site
- Synthesis of fluororesin precursor 2 In a 300 ml glass flask equipped with a stirrer, 13.01 g (0.1 mol) of HEMA and 2-(perfluorohexyl)ethyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as MA-C6F) were added at room temperature.
- Example 2 [Synthesis of fluororesin A-2] A fluorine-containing resin A-2 was obtained with a yield of 68% in the same procedure as the synthesis of the fluorine-containing resin A-1, except that the internal temperature was raised to 85°C.
- Example 3 [Synthesis of fluororesin A-3] A fluororesin A-3 was produced with a yield of 87% in the same procedure as the synthesis of fluororesin A-1, except that 0.16 g (0.001 mol) of AIBN (manufactured by Tokyo Chemical Industry Co., Ltd.) was used. Obtained.
- Example 4 [Synthesis of fluororesin A-4] Using 3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propanyl)cyclohexyl methacrylate (manufactured by Central Glass Co., Ltd.) instead of MA-BTHB-OH A fluorine-containing resin A-4 was obtained with a yield of 84% in the same procedure as the synthesis of the fluorine-containing resin A-1, except for the above.
- Example 5 [Synthesis of fluororesin A-5]
- MA-BTHB-OH 1,3-bis (1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propanyl) isopropyl methacrylate (manufactured by Central Glass Co., Ltd., hereinafter referred to as MA- BTHB-HFA) was used to obtain a fluororesin A-5 with a yield of 82% in the same procedure as for the synthesis of the fluororesin A-1.
- Example 6 [Synthesis of fluororesin A-6] At room temperature (about 20° C.) in a 300 ml glass flask equipped with a stirrer, 13.86 g (0.3 mol) of MA-BTHB-HFA, 2.36 g (0.1 mol) of HFIP-M, and 32 g of MEK were collected, 0.25 g (0.002 mol) of AIBN (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added, and after degassing with stirring, the inside of the flask was replaced with nitrogen gas, and the internal temperature was raised to 79° C. and reacted overnight.
- AIBN manufactured by Tokyo Kasei Kogyo Co., Ltd.
- Example 7 Synthesis of fluororesin A-7
- a fluorine-containing resin A-7 was obtained with a yield of 81% in the same procedure as the synthesis of the fluorine-containing resin A-6, except that butyl methacrylate (Tokyo Kasei Kogyo Reagent) was used instead of HFIP-M. .
- Example 8 Fluorine-containing resin A was prepared in the same manner as in the synthesis of fluororesin A-6, except that MA-BTHB-HFA was changed to 4.62 g (0.1 mol) and HFIP-M was changed to 7.08 g (0.3 mol). -8 was obtained in 79% yield.
- Fluorine-containing resin A was prepared in the same manner as in the synthesis of fluororesin A-6, except that MA-BTHB-HFA was changed to 9.24 g (0.2 mol) and HFIP-M was changed to 4.72 g (0.2 mol). -9 was obtained in 82% yield.
- Example 10 [Synthesis of fluororesin A-10] At room temperature (about 20° C.) in a 300 ml glass flask equipped with a stirrer, 14.62 g (0.1 mol) of MA-BTHB-HFA, 2.36 g (0.1 mol) of HFIP-M, and 1.5 g (0.1 mol) of butyl methacrylate were added. 42 g (0.1 mol) and 36 g of MEK were collected, 0.25 g (0.002 mol) of AIBN (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and after degassing while stirring, the inside of the flask was replaced with nitrogen gas, The inner temperature was raised to 79° C. and the mixture was reacted overnight.
- AIBN manufactured by Tokyo Chemical Industry Co., Ltd.
- Comparative example 1 Synthesis of comparative fluorine-containing resin A-1
- HFIP-M manufactured by Central Glass Co., Ltd.
- MA-BTHB-OH MA-BTHB-OH
- Comparative example 2 [Synthesis of comparative fluorine-containing resin A-2] At room temperature (about 20 ° C.) in a 100 ml glass flask equipped with a stirrer, 16.6 g (0.07 mol) of HFIP-M (manufactured by Central Glass Co., Ltd.) and 4.0 g (0.07 mol) of HEMA (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.03 mol), 20 g of MEK was collected, 0.17 g (0.001 mol) of AIBN (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and after degassing while stirring, the inside of the flask was replaced with nitrogen gas, and the internal temperature was The temperature was raised to 80° C.
- Example 11 [Preparation of photosensitive resin composition 1-1] To the photosensitive resin composition 1 prepared above, the fluororesin A-1 obtained in "2. Synthesis of a fluororesin for a surface conditioner” (mass %) of and after dissolution, the resulting solution was filtered through a 0.2 ⁇ m membrane filter to prepare a photosensitive resin composition 1-1.
- Example 12 Preparation of photosensitive resin composition 1-2
- a photosensitive resin composition 1-2 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-2 was used instead of the fluorine-containing resin A-1.
- Example 13 Preparation of photosensitive resin composition 1-3
- a photosensitive resin composition 1-3 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-3 was used instead of the fluorine-containing resin A-1.
- Example 14 Preparation of photosensitive resin composition 1-4
- a photosensitive resin composition 1-4 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-4 was used instead of the fluorine-containing resin A-1.
- Example 15 [Preparation of photosensitive resin composition 1-5] A photosensitive resin composition 1-5 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-5 was used instead of the fluorine-containing resin A-1.
- Example 16 Preparation of photosensitive resin composition 1-6
- a photosensitive resin composition 1-6 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-6 was used instead of the fluorine-containing resin A-1.
- Example 17 [Preparation of photosensitive resin composition 1-7] A photosensitive resin composition 1-7 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-7 was used instead of the fluorine-containing resin A-1.
- Example 18 [Preparation of photosensitive resin composition 1-8] A photosensitive resin composition 1-8 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-8 was used instead of the fluorine-containing resin A-1.
- Example 19 [Preparation of photosensitive resin composition 1-9] A photosensitive resin composition 1-9 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-9 was used instead of the fluorine-containing resin A-1.
- Example 20 [Preparation of photosensitive resin composition 1-10] A photosensitive resin composition 1-10 was prepared in the same manner as the photosensitive resin composition 1-1, except that the fluorine-containing resin A-10 was used instead of the fluorine-containing resin A-1.
- Comparative example 4 [Preparation of Comparative Photosensitive Resin Composition 1-1] A comparative photosensitive resin composition 1-1 was prepared in the same manner as the photosensitive resin composition 1-1, except that the comparative fluororesin A-1 was used instead of the fluororesin A-1. .
- Comparative example 5 [Preparation of Comparative Photosensitive Resin Composition 1-2] A comparative photosensitive resin composition 1-2 was prepared in the same manner as the photosensitive resin composition 1-1, except that the comparative fluororesin A-2 was used instead of the fluororesin A-1. .
- Comparative example 6 [Preparation of photosensitive resin composition 2] 0.5 parts by mass of the produced fluorine-containing resin B-2 having a cross-linking site, 0.5 parts by mass of Irgacure 369 as a polymerization initiator, 50 parts by mass of pentaerythritol tetraacrylate as a cross-linking agent, and ZAR2051H as an alkali-soluble resin.
- a photosensitive resin composition 2 was prepared by mixing 50 parts by mass, 160 parts by mass of PGMEA and 70 parts by mass of PGME as solvents, and filtering the resulting solution through a 0.2 ⁇ m membrane filter.
- Example 21 [Preparation of photosensitive resin composition 2-1] The fluororesin A-1 obtained in "2. Synthesis of fluororesin for surface conditioner” was added to the photosensitive resin composition 2 prepared above, and the total solid content of the photosensitive resin composition 2 was A photosensitive resin composition 2-1 was prepared by adding and dissolving the proportion (% by mass) and filtering the resulting solution through a 0.2 ⁇ m membrane filter.
- Example 22 [Preparation of photosensitive resin composition 2-2] A photosensitive resin composition 2-2 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-2 was used instead of the fluorine-containing resin A-1.
- Example 23 [Preparation of photosensitive resin composition 2-3] A photosensitive resin composition 2-3 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-3 was used instead of the fluorine-containing resin A-1.
- Example 24 [Preparation of photosensitive resin composition 2-4] A photosensitive resin composition 2-4 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-4 was used instead of the fluorine-containing resin A-1.
- Example 25 [Preparation of photosensitive resin composition 2-5] A photosensitive resin composition 2-5 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluororesin A-5 was used instead of the fluororesin A-1.
- Example 26 [Preparation of photosensitive resin composition 2-6] A photosensitive resin composition 2-6 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-6 was used instead of the fluorine-containing resin A-1.
- Example 27 [Preparation of photosensitive resin composition 2-7] A photosensitive resin composition 2-7 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-7 was used instead of the fluorine-containing resin A-1.
- Example 28 [Preparation of photosensitive resin composition 2-8] A photosensitive resin composition 2-8 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-8 was used instead of the fluorine-containing resin A-1.
- Example 29 [Preparation of photosensitive resin composition 2-9] A photosensitive resin composition 2-9 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluororesin A-9 was used instead of the fluororesin A-1.
- Example 30 [Preparation of photosensitive resin composition 2-10] A photosensitive resin composition 2-10 was prepared in the same manner as the photosensitive resin composition 2-1, except that the fluorine-containing resin A-10 was used instead of the fluorine-containing resin A-1.
- Comparative example 7 [Preparation of Comparative Photosensitive Resin Composition 2-1] A comparative photosensitive resin composition 2-1 was prepared in the same manner as the photosensitive resin composition 2-1, except that the comparative fluororesin A-1 was used instead of the fluororesin A-1. .
- Comparative example 8 Preparation of comparative photosensitive resin composition 2-2
- a comparative photosensitive resin composition 2-2 was prepared in the same manner as the photosensitive resin composition 2-1, except that the comparative fluororesin A-2 was used instead of the fluororesin A-1. .
- a fluorine-containing resin film and a comparative fluorine-containing resin film having a thickness of 2 ⁇ m were formed.
- the obtained resin film was irradiated with i-line (wavelength: 365 nm) for exposure.
- the obtained resin film after exposure was heated at 230° C. for 60 minutes, and after cooling the entire surface of the substrate, it was observed with a laser microscope (manufactured by Keyence Corporation, VX-1100) with an objective lens of 150 times.
- the surface roughness was evaluated by measuring 10 points within a 1 mm square and calculating the arithmetic average roughness.
- the resin film obtained using the photosensitive resin composition of Comparative Example had a surface roughness of 90 nm or more. All of the resin films had a surface roughness of 10 to 60 nm, which was clearly superior to the comparative examples.
- Preparation of a photosensitive resin composition" and the comparative photosensitive resin composition 1- 1 to 1-2 and 2-1 to 2-2 were applied onto the obtained substrate after UV ozone treatment using a spin coater at a rotation speed of 1,000 rpm, and heated on a hot plate at 100 ° C. for 150 seconds.
- a fluorine-containing resin film and a comparative fluorine-containing resin film having a film thickness of 2 ⁇ m were formed.
- a mask aligner manufactured by Suss Microtech Co., Ltd.
- the obtained resin film was exposed to i-rays (wavelength: 365 nm) through a mask having a line and space of 5 ⁇ m.
- the obtained resin film after exposure was evaluated for developer solubility, bank performance (sensitivity and resolution), and measured for contact angle.
- TMAH tetramethylammonium hydroxide
- both the bank of the example and the bank of the comparative example are negative resists in which only the unexposed areas are dissolved in the developer solubility evaluation, and the bank performance evaluation shows the same level of sensitivity. 5 ⁇ m lines and spaces of the mask were transferred with good resolution, and the resolution was “excellent” with no line edge roughness. The liquid repellency of anisole in the exposed area also showed a sufficient value. In other words, these evaluations revealed that the surface conditioners of the examples and the surface conditioners of the comparative examples had little effect on the bank.
- the surface roughness of the exposed portion was about 100 nm or more, but in the bank of the example, the surface roughness was 10 to 70 nm, which is significantly higher than that of the comparative example. It turned out to be excellent.
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Abstract
Description
CH2=C(R)COOXRf1
(式中、Rは、水素原子、メチル基又はトリフルオロメチル基、Xは炭素数1~6の2価のフッ素原子を含まない有機基を示し、Rf1は、炭素数4~6のパーフルオロアルキル基を示す。)
CH2=C(R)COOXRf1
(式中、R及びRf1は上記に同じ。)
本開示では、隔壁材として用いるのに好適な含フッ素樹脂の表面粗さを改善することを課題とする。
本開示の表面調整剤は、下記一般式(1)で表される構造を有する含フッ素樹脂(A)を含む。
本開示の表面調整剤を感光性樹脂組成物に導入して用いることにより、表面粗さが改善された隔壁を作製することができる。
本開示の感光性樹脂組成物を用いることにより、表面粗さが改善された隔壁を作製することができる。
本開示の感光性樹脂組成物を用いることにより、表面粗さが改善された硬化物及び隔壁を作製することができる。
本開示のディスプレイは、上記感光性樹脂組成物より得られる隔壁を備えることにより、インクが高精度でパターニングされている発光素子を含むディスプレイとなる。
(表面調整剤)
<含フッ素樹脂(A)>
本開示の表面調整剤は、下記一般式(1)で表される構造を有する含フッ素樹脂(A)を含む。
炭素数1~6の直鎖状のアルキル基としては、トリフルオロメチル基、ジフルオロメチル基、ペンタフルオロエチル基、2,2,2-トリフルオロエチル基、へプタフルオロプロピル基、3,3,3-トリフルオロプロピル基、ノナフルオロブチル基等が挙げられる。炭素数3~6の分岐鎖状のアルキル基としては、へプタフルオロイソプロピル基、ヘキサフルオロイソプロピル基、ノナフルオロイソブチル基、ノナフルオロ-tert-ブチル基等が挙げられる。炭素数3~6の環状のアルキル基としては、ペンタフルオロシクロプロピル基等が挙げられる。Raとして好ましくは炭素数1~6の直鎖状アルキル基であり、より好ましくはトリフルオロメチル基である。
一般式(1)で表される構造の具体例としては、ジフルオロメタノール基、テトラフルオロエタノール基、ヘキサフルオロイソプロパノール基、トリフルオロプロパノール基等が挙げられ、ヘキサフルオロイソプロパノール基が好ましい。
含フッ素樹脂(A)において、一般式(1)で表される構造は、芳香環に直接結合していないことが好ましい。一般式(1)で表される構造は、直鎖状、分岐鎖状又は環状のアルキレン基に直接結合していることが好ましい。
一般式(1)で表される構造を有する単量体としては、例えばメタクリル酸-5,5,5-トリフルオロ-4-ヒドロキシ-4-(トリフルオロメチル)ペンタン-2-イル、4-(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)スチレン(4-HFA-ST)、3,5-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)スチレン(3,5-HFA-ST)、2,4-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)シクロヘキシルメタクリレート、3,5-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)シクロヘキシルメタクリレート、2,4,6-トリス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)シクロヘキシルメタクリレート、1,3-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)イソプロピルメタクリレート等が挙げられる。これらの単量体は、1種又は2種以上用いることができる。好ましくはメタクリル酸-5,5,5-トリフルオロ-4-ヒドロキシ-4-(トリフルオロメチル)ペンタン-2-イル、3,5-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)シクロヘキシルメタクリレート、1,3-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)イソプロピルメタクリレートである。
一態様として、含フッ素樹脂(A)は、これらの単量体のいずれか1種のみを重合して得られるホモポリマーであるか、又は、これらの単量体の任意の2種以上のみを共重合して得られるヘテロポリマーであることが好ましい。重合が容易であり、表面調整剤としての性能も優れているからである。
含フッ素樹脂(A)における各単量体に由来する構成単位のモル比は、NMR(核磁気共鳴分光法)の測定値から決定することができる。
本開示において、含フッ素樹脂(A)は表面調整剤として機能するため、架橋部位を有しないことが好ましい。
含フッ素樹脂(A)の分散度(重量平均分子量Mwと数平均分子量Mnの比;Mw/Mn)は、1.01~5.00が好ましく、1.10~4.00がより好ましく、1.30~3.00が特に好ましい。
本開示において、含フッ素樹脂(A)の重量平均分子量と分散度は、ポリスチレンを標準物質とした高速ゲルパーミエーションクロマトグラフィで得られる値である。
アルコール類としては、具体的に、イソプロパノール、ブタノール、イソブタノール、n-ペンタノール、イソペンタノール、tert-ペンタノール、4-メチル-2-ペンタノール、3-メチル-3-ペンタノール、2,3-ジメチル-2-ペンタノール、n-ヘキサノール、n-ヘプタノール、2-ヘプタノール、n-オクタノール、n-デカノール、s-アミルアルコール、t-アミルアルコール、イソアミルアルコール、2-エチル-1-ブタノール、ラウリルアルコール、ヘキシルデカノール、オレイルアルコール等を挙げることができる。
エステル類としては、具体的に、乳酸メチル、乳酸エチル(EL)、酢酸メチル、酢酸エチル、酢酸ブチル、ピルビン酸メチル、ピルビン酸エチル、メトキシプロピオン酸メチル、エトキシプロピオン酸エチル、γ-ブチロラクトンなどを挙げることができる。
芳香族系溶媒としては、キシレン、トルエンなどを挙げることができる。
本開示の表面調整剤は、より具体的には消泡剤、レベリング剤、ワキ防止剤などとして用いることができる。また本開示の表面調整剤は界面活性剤としての作用も有するので、界面活性剤として用いることも可能である。
本開示の感光性樹脂組成物は、上記表面調整剤と、架橋部位を有する含フッ素樹脂(B)と、溶媒と、光重合開始剤と、を含む。上記表面調整剤を含む感光性樹脂組成物を用いることにより、表面粗さが改善された樹脂膜や隔壁を作製することができる。
なお本明細書において、「バンク」と「隔壁」とは同義語であり、別途注釈のない限り、インクジェット法における凹凸を有するパターン膜の凸部を意味する。
本開示の感光性樹脂組成物における表面調整剤としては、上述した含フッ素樹脂(A)を含むものが挙げられる。
本開示の感光性樹脂組成物において、含フッ素樹脂(A)の含有量は、感光性樹脂組成物の全固形分に対して0.01質量%以上、4.0質量%以下であることが好ましい。上記範囲外であると、樹脂膜や隔壁の表面粗さが充分改善されない場合がある。より好ましくは0.1質量%以上、2.5質量%以下、さらに好ましくは0.2質量%以上、2.5質量%以下である。
本開示の感光性樹脂組成物において、架橋部位を有する含フッ素樹脂(B)は、フッ素原子を有する炭化水素からなる繰り返し単位を有し、架橋部位として重合体の側鎖に光重合性基を有する。本開示において、「架橋部位を有する含フッ素樹脂(B)」の架橋部位は、他のモノマーと重合反応可能な部位を意味する。
以下では「架橋部位を有する含フッ素樹脂(B)」を「含フッ素樹脂(B)」とも記載する。
また、式(2)又は式(3)中のRbは、フッ素原子、トリフルオロメチル基、ジフルオロメチル基、ペンタフルオロエチル基、2,2,2-トリフルオロエチル基、n-ヘプタフルオロプロピル基、2,2,3,3,3-ペンタフルオロプロピル基、3,3,3-トリフルオロプロピル基、ヘキサフルオロイソプロピル基、ヘプタフルオロイソプロピル基、n-ノナフルオロブチル基、イソノナフルオロブチル基、tert-ノナフルオロブチル基が好ましく、フッ素原子、トリフルオロメチル基、ジフルオロメチル基、ペンタフルオロエチル基、2,2,2-トリフルオロエチル基、n-ヘプタフルオロプロピル基、2,2,3,3,3-ペンタフルオロプロピル基、3,3,3-トリフルオロプロピル基、ヘキサフルオロイソプロピル基がより好ましく、フッ素原子、ジフルオロメチル基、トリフルオロメチル基が特に好ましい。
芳香環の置換位置はそれぞれ独立に、オルト位、メタ位、パラ位を表し、パラ位であることが好ましい。
E1がオキシラン基であるとき、例えば、エチレンオキシド基、1,2-プロピレンオキシド基、1,3-プロピレンオキシド基などを挙げることができる。中でも、エチレンオキシド基であることが好ましい。
含フッ素樹脂前駆体に導入する光重合性基としては、アクリル基、メタクリル基、ビニル基、アリル基が好ましく、アクリル基がより好ましい。
光重合性基としてアクリル基を導入する場合、光重合性基誘導体としては、例えばアクリル基を有するイソシアネートモノマー、アクリル基を有するエポキシモノマー等のアクリル酸誘導体が挙げられる。
アクリル基を有するイソシアネートモノマーとしては、例えば、2-イソシアナトエチルメタクリレート、2-イソシアナトエチルアクリラート、2-(2-メタクリロイルオキシエチルオキシ)エチルイソシアナート、1,1-(ビスアクリロイルオキシメチル)エチルイソシアネート等が挙げられる。好ましくは2-イソシアナトエチルアクリラートである。
アクリル基を有するエポキシモノマーとしては、例えば、アクリル酸グリシジル、4-ヒドロキシブチルアクリレートグリシジルエーテル(4HBAGE、三菱ケミカル株式会社製)等が挙げられる。
含フッ素樹脂(B)における光重合性基の割合は、含フッ素樹脂(B)中、10モル%以上、70モル%以下であることが好ましい。光重合性基の割合が10モル%未満であると、樹脂膜や隔壁の強度が低下する傾向がある。光重合性基の割合が70モル%を超えると、塗布による樹脂膜の形成が困難になることがある。より好ましくは15モル%~60モル%である。
<態様1>
次の式(3)で表される繰り返し単位、式(5)で表される繰り返し単位、式(6-1)で表される繰り返し単位及び式(7)で表される繰り返し単位を含む含フッ素樹脂(B)
式(3):R1及びR2は水素原子、Rbはそれぞれ独立に、フッ素原子、ジフルオロメチル基又はトリフルオロメチル基
式(5):R5及びR6はそれぞれ独立に、水素原子又はメチル基、W2は-O-C(=O)-NH-、-C(=O)-O-C(=O)-NH-又は-C(=O)-NH-、A2、A3はそれぞれ独立に、エチレン基、Y2及びY3は-O-、nは1、rは1
式(6-1):R9はメチル基、pは2の整数、qは4~8の整数、Xはフッ素原子
式(7):R10は水素原子、Bは水酸基又はカルボキシル基、mは1
次の式(5)で表される繰り返し単位、式(6)で表される繰り返し単位、式(6-1)で表される繰り返し単位及び式(8)で表される繰り返し単位を含む含フッ素樹脂(B)
式(5):R5及びR6はそれぞれ独立に、水素原子又はメチル基、W2は-O-C(=O)-NH-、-C(=O)-O-C(=O)-NH-又は-C(=O)-NH-、A2、A3はそれぞれ独立に、エチレン基、Y2及びY3は-O-、nは1、rは1
式(6):R7はメチル基、R8は炭素数3~15の分岐鎖状のパーフルオロアルキル基
式(6-1):R9はメチル基、pは2の整数、qは4~8の整数、Xはフッ素原子
式(8):R13はメチル基、A4はエチレン基、Y4は-O-、rは1、sは0又は1、E1は水酸基又はカルボキシル基
フッ素含有率がこの範囲内であれば、溶媒に溶解し易い。含フッ素樹脂(B)がフッ素原子を含むことで、撥液性に優れる樹脂膜又はバンクを得ることができる。
ここで一例として、含フッ素樹脂(B)が、1,1-ビストリフルオロメチルブタジエン、4-ヒドロキシスチレン及び2-(パーフルオロヘキシル)エチルメタクリレートを重合してなる樹脂である場合のフッ素の含有量の測定方法を説明する。
(i)まず、含フッ素樹脂(B)をNMR測定することにより、各組成の割合を算出する(モル割合)。
(ii)含フッ素樹脂(B)の各組成のモノマーの分子量(Mw)と、モル割合を掛け、得られた値を足し合わせ、合計値を求める。その合計値から各組成の重量割合(wt%)を算出する。
なお、1,1-ビストリフルオロメチルブタジエンの分子量は190であり、4-ヒドロキシスチレンの分子量は120であり、2-(パーフルオロヘキシル)エチルメタクリレートの分子量は432である。
(iii)次に、フッ素を含有する組成において、モノマー中のフッ素含有量を計算する。
(iv)各成分における「モノマー中のフッ素含有量÷モノマー分子量(Mw)×重量割合(wt%)」の値を算出し、得られた数値を合算する。
(v)「上記(iv)で得られた数値」/「上記(ii)で得られた合計値」を算出し、含フッ素樹脂(B)のフッ素含有率を算出する。
本開示の感光性樹脂組成物の全固形分における含フッ素樹脂(B)の割合は、0.1~40質量%が好ましく、1~30質量%がより好ましい。当該範囲であると樹脂膜の撥水撥油性や基材密着性が良好となる。
本開示の感光性樹脂組成物において、溶媒は含フッ素樹脂(B)が可溶であれば特に制限されず、例えば上記含フッ素樹脂(A)の合成で使用することができる溶媒と同じもの等が挙げられる。好ましくは、メチルエチルケトン、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノメチルエーテル(PGME)、シクロヘキサノン、乳酸エチル、酢酸ブチル、γ-ブチロラクトンである。
本開示の感光性樹脂組成物において、光重合開始剤は、電磁波や電子線等の高エネルギー線により、重合性二重結合を有する単量体を重合させるものであれば特に限定されるものではなく、公知の光重合開始剤を用いることができる。
光重合開始剤として、光ラジカル開始剤又は光酸開始剤を用いることができ、これらは単独で用いてもよいし、光ラジカル開始剤及び光酸開始剤を併用してもよいし、2種以上の光ラジカル開始剤又は光酸開始剤を混合して用いてもよい。また、光重合開始剤と併せて添加剤を使用することにより、場合によってリビング重合を行うことも可能であり、当該添加剤は公知のものを使用することができる。
中でも、ビス[4-(ジフェニルスルホニオ)フェニル]スルフィドビスヘキサフルオロホスフェート、ビス[4-(ジフェニルスルホニオ)フェニル]スルフィドテトラキス(ペンタフルオロフェニル)ボレート、ジフェニルヨードニウムヘキサフルオロホスフェートが特に好ましい。
<エチレン性不飽和化合物(C)>
本開示の感光性樹脂組成物がエチレン性不飽和化合物(C)を含むと、光照射による感光性樹脂組成物の硬化が促進され、より短時間での硬化が可能となる。
エチレン性不飽和化合物(C)の具体例としては、多官能アクリレート(例えば、新中村化学工業株式会社製の製品名:A-TMM-3、A-TMM-3L、A-TMM-3LM-N、A-TMPT、AD-TMP)、ポリエチレングリコールジアクリレート(例えば、新中村化学工業株式会社製の製品名:A-200、A-400、A-600)、ウレタンアクリレート(例えば、新中村化学工業株式会社製の製品名:UA-122P、UA-4HA、UA-6HA、UA-6LPA、UA-11003H、UA-53H、UA-4200、UA-200PA、UA-33H、UA-7100、UA-7200)、ペンタエリスリトールテトラアクリレートなどが挙げられる。
エチレン性不飽和化合物(C)の含有量が10質量部よりも少ないと架橋効果が十分得られない傾向があり、300質量部を超えると解像性や感度が低下する傾向がある。
本開示の感光性樹脂組成物がアルカリ可溶性樹脂(D)を含むと、本開示の感光性樹脂組成物から得られるバンクの形状を良好にすることができる。
アルカリ可溶性樹脂(D)としては、アルカリ溶解性ノボラック樹脂を挙げることができる。
アルカリ溶解性ノボラック樹脂は、フェノール類とアルデヒド類とを酸性触媒存在下で縮合して得ることができる。
酸触媒としては、具体的に、塩酸、硝酸、硫酸、リン酸、亜リン酸、ギ酸、シュウ酸、酢酸、メタンスルホン酸、ジエチル硫酸、p-トルエンスルホン酸などを例示することができる。これら酸触媒は単独で使用してもよいし、2種類以上を組み合わせて使用してもよい。
本開示の感光性樹脂組成物が光ラジカル増感剤(E)を含むと、本開示の感光性樹脂組成物の露光感度をより向上させることができる。光ラジカル増感剤(E)は、光線又は放射線を吸収して励起状態となる化合物であることが好ましい。光ラジカル増感剤(E)は励起状態となることで、光重合開始剤と接触した際、電子移動、エネルギー移動又は発熱等を生じ、これにより、光重合開始剤は分解し酸を生成し易くなる。光ラジカル増感剤(E)は、350nm~450nmの領域に吸収波長を有すればよく、多核芳香族類、キサンテン類、キサントン類、シアニン類、メロシアニン類、チアジン類、アクリジン類、アクリドン類、アントラキノン類、スクアリウム類、スチリル類、ベーススチリル類、又はクマリン類を挙げることができる。
キサントン類としては、キサントン、チオキサントン、ジメチルチオキサントン、ジエチルチオキサントン、又はイソプロピルチオキサントンを例示することができる。
メロシアニン類としては、メロシアニン、カルボメロシアニンを例示することができる。
チアジン類としては、チオニン、メチレンブルー、トルイジンブルーを例示することができる。
アクリドン類としては、アクリドン、10-ブチル-2-クロロアクリドンを例示することができる。
スクアリウム類としては、スクアリウムを例示することができる。
ベーススチリル類としては、2-[2-[4-(ジメチルアミノ)フェニル]エテニル]ベンゾオキサゾールを例示することができる。
これら光ラジカル増感剤(E)は、単独、又は2種類以上を組み合わせて用いてもよい。
本開示の感光性樹脂組成物は、必要に応じて連鎖移動剤(F)を用いることが好ましい。
連鎖移動剤(F)としては、上述の含フッ素樹脂(A)の合成に用い得るものと同じ化合物等を挙げることができる。
本開示の感光性樹脂組成物は、必要に応じて紫外線吸収剤(G)を用いることが好ましく、紫外線吸収剤(G)としてはサリチル酸系、ベンゾフェノン系、トリアゾール系等を挙げることができる。
紫外線吸収剤(G)の含有量は、感光性樹脂組成物中に好ましくは0.5~5質量%であり、より好ましくは1~3質量%である。
本開示の感光性樹脂組成物に使用する重合禁止剤(H)としては特に限定されないが、o-クレゾール、m-クレゾール、p-クレゾール、6-t-ブチル-2,4-キシレノール、2,6-ジ-t-ブチル-p-クレゾール、ヒドロキノン、カテコール、4-t-ブチルピロカテコール、2,5-ビステトラメチルブチルヒドロキノン、2,5-ジ-t-ブチルヒドロキノン、p-メトキシフェノール、1,2,4-トリヒドロキシベンゼン、1,2-ベンゾキノン、1,3-ベンゾキノン、1,4-ベンゾキノン、ロイコキニザリン、フェノチアジン、2-メトキシフェノチアジン、テトラエチルチウラムジスルフィド、1,1-ジフェニル-2-ピクリルヒドラジル又は1,1-ジフェニル-2-ピクリルヒドラジンを例示することができる。
本開示の感光性樹脂組成物により得られる樹脂膜は、上記の表面調整剤を含むことにより、表面粗さが改善されている。本開示の硬化物は、隔壁として用いることが好ましく、有機ELディスプレイや量子ドットディスプレイ等の隔壁として用いることが特に好ましい。
当該隔壁を形成する方法は、(1)成膜工程と、(2)露光工程と、(3)現像工程とを含んでいてもよい。
各工程について以下に説明する。
まず、上記本開示の感光性樹脂組成物を、基板に塗布した後、加熱することにより上記感光性樹脂組成物を含フッ素樹脂膜とする。
加熱の条件は特に限定されないが、80~100℃、60~200秒であることが好ましい。
これにより、感光性樹脂組成物に含まれる溶媒等を除去することができる。
また、基板上には予め有機系あるいは無機系の膜が設けられていてもよい。例えば、反射防止膜、多層レジストの下層があってもよく、それにパターンが形成されていてもよい。また、基板を予め洗浄してもよい。例えば、超純水、アセトン、アルコール(メタノール、エタノール、イソプロピルアルコール)などを用いて洗浄することができる。
次に、所望のフォトマスクを露光装置にセットし、高エネルギー線を、該フォトマスクを介して上記含フッ素樹脂膜に露光する。
高エネルギー線は、紫外線、ガンマ線、X線、及びα線からなる群から選択される少なくとも1種であることが好ましい。
次に、露光工程後の含フッ素樹脂膜をアルカリ水溶液で現像して含フッ素樹脂パターン膜とする。
すなわち、含フッ素樹脂膜露光部又は膜未露光部のいずれかをアルカリ水溶液に溶解させることにより、含フッ素樹脂パターン膜とする。
アルカリ水溶液がテトラメチルアンモニウムヒドロキシド(TMAH)水溶液である場合、その濃度は、0.1質量%以上5質量%以下であることが好ましく、2質量%以上3質量%以下であることがより好ましい。
ディスプレイとしては、有機ELディスプレイや、量子ドットディスプレイ等が挙げられる。
含フッ素樹脂(A)は、上述の表面調整剤及び感光性樹脂組成物について説明したものと同じものを用いることができる。
本開示の方法では、様々な樹脂の成形品の表面を調整することができる。成形品の表面調整とは、樹脂の成形時や塗膜作製時に発生する泡、刷毛目、オレンジピール、ハジキ、クレーター、ピンホール、浮きまだら等の種々の塗膜欠陥の発生を抑制することである。これらの塗膜欠陥の発生を抑制することにより、例えば表面粗さを改善することができる。
成形品の材料である樹脂の種類は特に限定されず、例えばオレフィン系樹脂、エポキシ樹脂、(メタ)アクリル樹脂、ウレタン樹脂、フッ素樹脂等の1種又は2種以上を組み合わせたものが挙げられる。本開示の方法は、フッ素含有量が異なる2種以上の樹脂を含有する組成物で成形品を作製するときに特に好適に用いることができる。組成物としては、感光性樹脂組成物が特に好ましい。
本開示の方法において、含フッ素樹脂(A)は、樹脂組成物に混合して用いることができる。含フッ素樹脂(A)の好ましい態様や配合量は、上述の感光性樹脂組成物における態様及び配合量と同様である。
含フッ素樹脂(A)は、消泡剤、レベリング剤、ワキ防止剤等の表面調整剤、界面活性剤として作用する。
重合体における各繰り返し単位のモル比は、1H-NMR、19F-NMR又は13C-NMRの測定値から決定した。
重合体の重量平均分子量Mwと分子量分散度(重量平均分子量Mwと数平均分子量Mnの比;Mw/Mn)は、高速ゲルパーミエーションクロマトグラフィ(以下、GPCということがある。東ソー株式会社製、形式HLC-8320GPC)を使用し、ALPHA-MカラムとALPHA-2500カラム(ともに東ソー株式会社製)を1本ずつ直列に繋ぎ、ポリスチレンを標準物質とし、展開溶媒としてテトラヒドロフラン(THF)を用いて測定した。検出器には、屈折率差測定検出器を用いた。
合成例1 架橋部位を有する含フッ素樹脂B-1の合成
[含フッ素樹脂前駆体1の合成]
攪拌機付き300mlガラス製フラスコ内に室温(約20℃)で、1,1-ビス(トリフルオロメチル)-1,3-ブタジエン(セントラル硝子株式会社製。以下、BTFBEと表記する)を4.3g(0.02mol)、4-アセトキシスチレン(東京化成工業株式会社製。以下、p-AcO-Stと表記する)を2.7g(0.02mol)、2-(パーフルオロブチル)エチルメタクリレート(東京化成工業株式会社製。以下、MA-C4Fと表記する)を21.4g(0.07mol)、メタクリル酸2-ヒドロキシエチル(東京化成工業株式会社製。以下、HEMAと表記する)を6.1g(0.05mol)、メチルエチルケトン(以下、MEKと表記する)を36.9g採取し、2,2’-アゾビス(2-メチルブチロニトリル)(東京化成工業株式会社製。以下、AIBNと表記する)を2.46g(0.02mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、内温79℃に昇温し終夜反応させた。反応系にn-ヘプタン250gを滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度45℃下にて減圧乾燥を行い、白色固体として含フッ素樹脂前駆体1を30.4g、収率88%で得た。
含フッ素樹脂前駆体1の各繰り返し単位の組成比は、mol比で表して、BTFBEによる繰り返し単位:p-AcO-Stによる繰り返し単位:MA-C4Fによる繰り返し単位:HEMAによる繰り返し単位=15:11:43:31であった。
Mw=7,201、Mw/Mn=1.4
攪拌機付き100mlガラス製フラスコ内に、含フッ素樹脂前駆体1を10g(水酸基当量0.01mol)、トリエチルアミンを0.07g(水酸基当量0.0007mol)、PGMEAを20g採取し、カレンズ-AOI(2-イソシアナトエチルアクリラート、昭和電工株式会社製)を1.51g(水酸基当量0.01mol)加え、45℃で4時間反応させた。反応終了後の反応液を濃縮後、n-ヘプタン100gを加え、沈殿を析出させた。この沈殿を濾別し、40℃にて減圧乾燥を行い、白色固体として架橋部位を有する含フッ素樹脂B-1を収率75%で得た。
架橋部位を有する含フッ素樹脂B-1において、カレンズ-AOI由来のアクリル酸誘導体導入量(反応率)及び残水酸基量(未反応率)は、mol比で表して96:4であった。また、架橋部位と反応しない各繰り返し単位(BTFBEによる繰り返し単位、p-AcO-Stによる繰り返し単位、MA-C4Fによる繰り返し単位)の組成比は、用いた含フッ素樹脂前駆体1から変化がない(架橋部位導入前と同じ)ことを確認した。
[含フッ素樹脂前駆体2の合成]
攪拌機付き300mlガラス製フラスコ内に、室温で、HEMAを13.01g(0.1mol)、2-(パーフルオロヘキシル)エチルメタクリレート(東京化成工業株式会社製。以下、MA-C6Fと表記する)を43.2g(0.1mol)、メタクリル酸ヘキサフルオロイソプロピル(セントラル硝子株式会社製。以下、HFIP-Mと表記する)を23.6g(0.1mol)、メタクリル酸(東京化成工業株式会社製。以下MAAと表記する。)を8.66g(0.1mol)、MEKを88g採取し、AIBNを1.6g(0.010mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、80℃に昇温した後6時間反応させた。反応終了後の反応液を、n-ヘプタン500gに滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度60℃下にて減圧乾燥を行い、白色固体として含フッ素樹脂前駆体2を60g、収率68%で得た。
含フッ素樹脂前駆体2の各繰り返し単位の組成比は、mol比で表して、HEMAによる繰り返し単位:MA-C6Fによる繰り返し単位:HFIP-Mによる繰り返し単位:MAAによる繰り返し単位=24:26:24:26であった。
Mw=10,700、Mw/Mn=1.5
含フッ素樹脂前駆体1の替わりに含フッ素樹脂前駆体2を用いたこと以外は、架橋部位を有する含フッ素樹脂B-1の合成と同様の手順で、架橋部位を有する含フッ素樹脂B-2を収率90%で得た。
架橋部位を有する含フッ素樹脂B-2において、カレンズ-AOI由来のアクリル酸誘導体導入量(反応率)及び残水酸基量(未反応率)は、mol比で表わして96:4であった。また、架橋部位と反応しない各繰り返し単位(MA-C6Fによる繰り返し単位、HFIP-Mによる繰り返し単位)の組成比は、用いた含フッ素樹脂前駆体2から変化がない(架橋基導入前と同じ)ことを確認した。
実施例1
[含フッ素樹脂A-1の合成]
攪拌機付き100mlガラス製フラスコ内に室温(約20℃)で、メタクリル酸-5,5,5-トリフルオロ-4-ヒドロキシ-4-(トリフルオロメチル)ペンタン-2-イル(セントラル硝子株式会社製。以下、MA-BTHB-OHと表記する)を11.8g(0.04mol)、MEKを24g採取し、AIBN(東京化成工業株式会社製)を0.65g(0.004mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、内温79℃に昇温し6時間反応させた。反応系にn-ヘプタン200gを滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度45℃下にて減圧乾燥を行い、白色固体として含フッ素樹脂A-1を8.47g、収率72%で得た。
Mw=13,370、Mw/Mn=1.9
[含フッ素樹脂A-2の合成]
内温を85℃に昇温した以外は、含フッ素樹脂A-1の合成と同様の手順で、含フッ素樹脂A-2を収率68%で得た。
Mw=8770、Mw/Mn=1.6
[含フッ素樹脂A-3の合成]
AIBN(東京化成工業株式会社製)を0.16g(0.001mol)用いたこと以外は、含フッ素樹脂A-1の合成と同様の手順で、含フッ素樹脂A-3を収率87%で得た。
Mw=38,400、Mw/Mn=2.3
[含フッ素樹脂A-4の合成]
MA-BTHB-OHの替わりに3,5-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)シクロヘキシルメタクリレート(セントラル硝子株式会社製)を用いたこと以外は、含フッ素樹脂A-1の合成と同様の手順で、含フッ素樹脂A-4を収率84%で得た。
Mw=14,800、Mw/Mn=1.9
[含フッ素樹脂A-5の合成]
MA-BTHB-OHの替わりに1,3-ビス(1,1,1,3,3,3-ヘキサフルオロ-2-ヒドロキシ-2-プロパニル)イソプロピルメタクリレート(セントラル硝子株式会社製、以下、MA-BTHB-HFAと表記する)を用いたこと以外は、含フッ素樹脂A-1の合成と同様の手順で、含フッ素樹脂A-5を収率82%で得た。
Mw=11,800、Mw/Mn=1.5
[含フッ素樹脂A-6の合成]
攪拌機付き300mlガラス製フラスコ内に室温(約20℃)で、MA-BTHB-HFAを13.86g(0.3mol)、HFIP-Mを2.36g(0.1mol)、MEKを32g採取し、AIBN(東京化成工業株式会社製)を0.25g(0.002mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、内温79℃に昇温し終夜反応させた。反応系にn-ヘプタン200gを滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度50℃下にて減圧乾燥を行い、白色固体として含フッ素樹脂A-6を13g、収率80%で得た。
含フッ素樹脂A-6の各繰り返し単位の組成比は、mol比で表して、MA-BTHB-HFAによる繰り返し単位:HFIP-Mによる繰り返し単位=75:25であった。
Mw=12,300、Mw/Mn=1.6
[含フッ素樹脂A-7の合成]
HFIP-Mの替わりにメタクリル酸ブチル(東京化成工業試薬)を用いたこと以外は、含フッ素樹脂A-6の合成と同様の手順で、含フッ素樹脂A-7を収率81%で得た。
含フッ素樹脂A-7の各繰り返し単位の組成比は、mol比で表して、MA-BTHB-HFAによる繰り返し単位:メタクリル酸ブチルによる繰り返し単位=75:25であった。
Mw=11,300、Mw/Mn=1.5
[含フッ素樹脂A-8の合成]
MA-BTHB-HFAを4.62g(0.1mol)、HFIP-Mを7.08g(0.3mol)と変更した以外は含フッ素樹脂A-6の合成と同様の手順で、含フッ素樹脂A-8を収率79%で得た。
含フッ素樹脂A-8の各繰り返し単位の組成比は、mol比で表して、MA-BTHB-HFAによる繰り返し単位:HFIP-Mによる繰り返し単位=25:75であった。
Mw=13,000、Mw/Mn=1.7
[含フッ素樹脂A-9の合成]
MA-BTHB-HFAを9.24g(0.2mol)、HFIP-Mを4.72g(0.2mol)と変更した以外は含フッ素樹脂A-6の合成と同様の手順で、含フッ素樹脂A-9を収率82%で得た。
含フッ素樹脂A-9の各繰り返し単位の組成比は、mol比で表して、MA-BTHB-HFAによる繰り返し単位:HFIP-Mによる繰り返し単位=50:50であった。
Mw=12,500、Mw/Mn=1.6
[含フッ素樹脂A-10の合成]
攪拌機付き300mlガラス製フラスコ内に室温(約20℃)で、MA-BTHB-HFAを14.62g(0.1mol)、HFIP-Mを2.36g(0.1mol)、メタクリル酸ブチルを1.42g(0.1mol)、MEKを36g採取し、AIBN(東京化成工業株式会社製)を0.25g(0.002mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、内温79℃に昇温し終夜反応させた。反応系にn-ヘプタン200gを滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度50℃下にて減圧乾燥を行い、白色固体として含フッ素樹脂A-10を14g、収率76%で得た。
含フッ素樹脂A-10の各繰り返し単位の組成比は、mol比で表して、MA-BTHB-HFAによる繰り返し単位:HFIP-Mによる繰り返し単位:メタクリル酸ブチルによる繰り返し単位=1:1:1であった。
Mw=13,800、Mw/Mn=1.8
[比較含フッ素樹脂A-1の合成]
MA-BTHB-OHの替わりにHFIP-M(セントラル硝子株式会社製)を用いたこと以外は、含フッ素樹脂A-1の合成と同様の手順で、比較含フッ素樹脂A-1を収率81%で得た。
Mw=12,123、Mw/Mn=1.8
[比較含フッ素樹脂A-2の合成]
攪拌機付き100mlガラス製フラスコ内に室温(約20℃)で、HFIP-M(セントラル硝子株式会社製)を16.6g(0.07mol)、HEMA(東京化成工業株式会社製)を4.0g(0.03mol)、MEKを20g採取し、AIBN(東京化成工業株式会社製)を0.17g(0.001mol)加え、攪拌しつつ脱気した後に、フラスコ内を窒素ガスで置換し、内温80℃に昇温し終夜で反応させた。反応系にn-ヘプタン160gを滴下したところ、白色の沈殿を得た。この沈殿を濾別し、温度45℃下にて減圧乾燥を行い、白色固体として比較含フッ素樹脂A-2を17.0g、収率83%で得た。
比較含フッ素樹脂A-2の各繰り返し単位の組成比は、mol比で表わして、HFIP-Mによる繰り返し単位:HEMAによる繰り返し単位=70:30であった。
Mw=14,289、Mw/Mn=1.7
比較例3
[感光性樹脂組成物1の調製]
製造した架橋部位を有する含フッ素樹脂B-1を0.5質量部、重合開始剤としてイルガキュア369(2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタン-1-オン、ビーエーエスエフ株式会社製品)を0.5質量部、架橋剤としてペンタエリスリトールテトラアクリレート(東京化成工業株式会社製品)を50質量部、アルカリ可溶性樹脂としてZAR2051H(ビスフェノールA型エポキシアクリレート、日本化薬株式会社製品)を50質量部、溶媒としてプロピレングリコールモノメチルエーテルアセテート(PGMEA)を160質量部とプロピレングリコールモノメチルエーテル(PGME)を70質量部配合し、得られた溶液を0.2μmのメンブランフィルターで濾過することにより、感光性樹脂組成物1を調製した。
[感光性樹脂組成物1-1の調製]
上記で調製した感光性樹脂組成物1に「2.表面調整剤用含フッ素樹脂の合成」で得られた含フッ素樹脂A-1を感光性樹脂組成物1の全固形分に対して表1の割合(質量%)で添加し溶解後、得られた溶液を0.2μmのメンブランフィルターで濾過することにより、感光性樹脂組成物1-1を調製した。
[感光性樹脂組成物1-2の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-2を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-2を調製した。
[感光性樹脂組成物1-3の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-3を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-3を調製した。
[感光性樹脂組成物1-4の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-4を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-4を調製した。
[感光性樹脂組成物1-5の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-5を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-5を調製した。
[感光性樹脂組成物1-6の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-6を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-6を調製した。
[感光性樹脂組成物1-7の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-7を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-7を調製した。
[感光性樹脂組成物1-8の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-8を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-8を調製した。
[感光性樹脂組成物1-9の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-9を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-9を調製した。
[感光性樹脂組成物1-10の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-10を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で感光性樹脂組成物1-10を調製した。
[比較感光性樹脂組成物1-1の調製]
含フッ素樹脂A-1の替わりに比較含フッ素樹脂A-1を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で比較感光性樹脂組成物1-1を調製した。
[比較感光性樹脂組成物1-2の調製]
含フッ素樹脂A-1の替わりに比較含フッ素樹脂A-2を用いたこと以外は、感光性樹脂組成物1-1の調製と同様の手順で比較感光性樹脂組成物1-2を調製した。
[感光性樹脂組成物2の調製]
製造した架橋部位を有する含フッ素樹脂B-2を0.5質量部、重合開始剤としてイルガキュア369を0.5質量部、架橋剤としてペンタエリスリトールテトラアクリレートを50質量部、アルカリ可溶性樹脂としてZAR2051Hを50質量部、溶媒としてPGMEAを160質量部とPGMEを70質量部配合し、得られた溶液を0.2μmのメンブランフィルターで濾過することにより、感光性樹脂組成物2を調製した。
[感光性樹脂組成物2-1の調製]
上記で調製した感光性樹脂組成物2に「2.表面調整剤用含フッ素樹脂の合成」で得られた含フッ素樹脂A-1を感光性樹脂組成物2全固形分に対して表1の割合(質量%)で添加し溶解後、得られた溶液を0.2μmのメンブランフィルターで濾過することにより、感光性樹脂組成物2-1を調製した。
[感光性樹脂組成物2-2の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-2を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-2を調製した。
[感光性樹脂組成物2-3の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-3を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-3を調製した。
[感光性樹脂組成物2-4の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-4を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-4を調製した。
[感光性樹脂組成物2-5の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-5を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-5を調製した。
[感光性樹脂組成物2-6の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-6を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-6を調製した。
[感光性樹脂組成物2-7の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-7を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-7を調製した。
[感光性樹脂組成物2-8の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-8を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-8を調製した。
[感光性樹脂組成物2-9の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-9を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-9を調製した。
[感光性樹脂組成物2-10の調製]
含フッ素樹脂A-1の替わりに含フッ素樹脂A-10を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で感光性樹脂組成物2-10を調製した。
[比較感光性樹脂組成物2-1の調製]
含フッ素樹脂A-1の替わりに比較含フッ素樹脂A-1を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で比較感光性樹脂組成物2-1を調製した。
[比較感光性樹脂組成物2-2の調製]
含フッ素樹脂A-1の替わりに比較含フッ素樹脂A-2を用いたこと以外は、感光性樹脂組成物2-1の調製と同様の手順で比較感光性樹脂組成物2-2を調製した。
「3.感光性樹脂組成物の調製」で得られた感光性樹脂組成物1、1-1~1-10、2、2-1~2-10、及び比較感光性樹脂組成物1-1~1-2、2-1~2-2を用いて、樹脂膜を作製し、表面粗さを評価及び比較した。結果を表1に示す。
10cm四方の無アルカリ基板を超純水、次いでアセトンにより洗浄後、UVオゾン処理装置(セン特殊光源株式会社製、型番、PL17-110)を用い、当該基板に対するUVオゾン処理を5分間行った。次いで、「3.感光性樹脂組成物の調製」で得られた感光性樹脂組成物1、1-1~1-10、2、2-1~2-10及び比較感光性樹脂組成物1-1~1-2、2-1~2-2を用いて、得られたUVオゾン処理後の基板上にスピンコータを用い回転数1,000rpmで塗布し、ホットプレート上で100℃、150秒間、加熱し、膜厚2μmの含フッ素樹脂膜及び比較含フッ素樹脂膜を形成した。得られた樹脂膜にi線(波長365nm)を照射し、露光を行った。
得られた露光後の樹脂膜に対して、230℃で60分間、加熱を行った後、当該基板全面を冷却後、レーザー顕微鏡(キーエンス社製、VX-1100)にて、対物レンズ150倍で1mm四方内の10点を測定して算術平均粗さを算出し、表面粗さを評価した。
「3.感光性樹脂組成物の調製」で得られた感光性樹脂組成物1、1-1~1-10、2、2-1~2-10及び比較感光性樹脂組成物1-1~1-2、2-1~2-2を用いて、バンクを形成し、バンク性能を評価及び比較した。本開示のバンクの結果及び比較バンクの結果を表2及び表3に示す。
[バンクの形成]
10cm四方のITO基板を超純水、次いでアセトンにより洗浄後、前述のUVオゾン処理装置を用い、当該基板に対するUVオゾン処理を5分間行った。次いで、「3.感光性樹脂組成物の調製」で得られた感光性樹脂組成物1、1-1~1-10、2、2-1~2-10及び比較感光性樹脂組成物1-1~1-2、2-1~2-2を用いて、得られたUVオゾン処理後の基板上にスピンコータを用い回転数1,000rpmで塗布し、ホットプレート上で100℃、150秒間加熱し、膜厚2μmの含フッ素樹脂膜及び比較含フッ素樹脂膜を形成した。マスクアライナ(ズース・マイクロテック株式会社製品)を用いて、ラインアンドスペースが5μmのマスクを介し、得られた樹脂膜にi線(波長365nm)を照射し、露光を行った。
得られた露光後の樹脂膜に対して現像液溶解性、バンク性能の評価(感度、解像度)、及び接触角の測定を行った。
ITO基板上の露光後の樹脂膜を、アルカリ現像液に室温で80秒間浸漬し、アルカリ現像液に対する溶解性を評価した。アルカリ現像液には、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液(以下、TMAHということがある)を用いた。バンクの溶解性は、浸漬後のバンクの膜厚を接触式膜厚計で測定することによって評価した。バンクが完全に溶解している場合を「可溶」、バンクが未溶解で残っている場合を「不溶」とした。
上記ラインアンドスペースのパターンであるバンクを形成する際の最適露光量Eop(mJ/cm2)を求め、感度の指標とした。
また、得られたバンクパターンを顕微鏡で観察し解像度を評価した。ラインエッジラフネスが確認できないものを「優」、僅かに確認されるものを「良」、顕著であるものを「不可」とした。
上記工程により得られたバンクを有する基板を、230℃で60分間、加熱工程後において、バンク表面のアニソール接触角を測定した。
レーザー顕微鏡にてバンクの表面粗さを評価した。レーザー顕微鏡はキーエンス社製VX-1100を用いて、樹脂膜の表面粗さの評価と同様に行った。
Claims (15)
- 前記含フッ素樹脂(A)中の一般式(1)で表される構造の含有量が、前記含フッ素樹脂(A)を構成する繰り返し単位の合計量を100モル%として、50モル%以上、300モル%以下である請求項1に記載の表面調整剤。
- 前記含フッ素樹脂(A)の重量平均分子量が、5,000以上、40,000以下である請求項1又は2に記載の表面調整剤。
- 前記一般式(1)中のRaがトリフルオロメチル基である請求項1~3のいずれか1項に記載の表面調整剤。
- 請求項1~4のいずれか1項に記載の表面調整剤と、架橋部位を有する含フッ素樹脂(B)と、溶媒と、光重合開始剤と、を含む感光性樹脂組成物。
- 前記含フッ素樹脂(A)の含有量が全固形分に対して0.1質量%以上、2.5質量%以下である、請求項5に記載の感光性樹脂組成物。
- さらにエチレン性不飽和化合物(C)及び/又はアルカリ可溶性樹脂(D)を含む、請求項5又は6に記載の感光性樹脂組成物。
- さらに光ラジカル増感剤(E)、連鎖移動剤(F)、紫外線吸収剤(G)及び重合禁止剤(H)からなる群から選択される少なくとも1種を含む、請求項5~7のいずれか1項に記載の感光性樹脂組成物。
- 隔壁の形成に用いられる請求項5~8のいずれか1項に記載の感光性樹脂組成物。
- 請求項5~9のいずれか1項に記載の感光性樹脂組成物を硬化させたことを特徴とする硬化物。
- 隔壁である、請求項10に記載の硬化物。
- 請求項5~9のいずれか1項に記載の感光性樹脂組成物を硬化させて得られる隔壁と、前記隔壁により区画される領域に配置される発光層又は波長変換層とを備える発光素子を含むディスプレイ。
- 有機ELディスプレイ又は量子ドットディスプレイである請求項12に記載のディスプレイ。
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JP2005099157A (ja) * | 2003-09-22 | 2005-04-14 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
JP2017016115A (ja) * | 2015-06-30 | 2017-01-19 | 信越化学工業株式会社 | レジスト組成物及びパターン形成方法 |
JP2018044034A (ja) * | 2016-09-12 | 2018-03-22 | セントラル硝子株式会社 | 含フッ素単量体およびその含フッ素重合体、それを用いたレジストおよびパターン形成方法 |
JP2019038764A (ja) * | 2017-08-24 | 2019-03-14 | 信越化学工業株式会社 | スルホニウム化合物、レジスト組成物及びパターン形成方法 |
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CA997000A (en) | 1969-12-29 | 1976-09-14 | Allen L. Limberg | Multiplex decoding system |
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JP2005099157A (ja) * | 2003-09-22 | 2005-04-14 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
JP2017016115A (ja) * | 2015-06-30 | 2017-01-19 | 信越化学工業株式会社 | レジスト組成物及びパターン形成方法 |
JP2018044034A (ja) * | 2016-09-12 | 2018-03-22 | セントラル硝子株式会社 | 含フッ素単量体およびその含フッ素重合体、それを用いたレジストおよびパターン形成方法 |
JP2019038764A (ja) * | 2017-08-24 | 2019-03-14 | 信越化学工業株式会社 | スルホニウム化合物、レジスト組成物及びパターン形成方法 |
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