WO2021065211A1 - Composition de formation de film de revêtement, stratifié obtenu par revêtement de ladite composition de formation de film de revêtement, panneau tactile obtenu à l'aide dudit stratifié et procédé de formation de film de revêtement durci - Google Patents

Composition de formation de film de revêtement, stratifié obtenu par revêtement de ladite composition de formation de film de revêtement, panneau tactile obtenu à l'aide dudit stratifié et procédé de formation de film de revêtement durci Download PDF

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Publication number
WO2021065211A1
WO2021065211A1 PCT/JP2020/030574 JP2020030574W WO2021065211A1 WO 2021065211 A1 WO2021065211 A1 WO 2021065211A1 JP 2020030574 W JP2020030574 W JP 2020030574W WO 2021065211 A1 WO2021065211 A1 WO 2021065211A1
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Prior art keywords
film
silane compound
forming composition
coating film
general formula
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PCT/JP2020/030574
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English (en)
Japanese (ja)
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健嗣 小倉
圭祐 池堂
正 中野
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サカタインクス株式会社
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Priority to KR1020227006447A priority Critical patent/KR20220073731A/ko
Priority to CN202080066096.5A priority patent/CN114430767B/zh
Publication of WO2021065211A1 publication Critical patent/WO2021065211A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • 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
    • C08F290/14—Polymers provided for in subclass C08G
    • 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
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/148—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means

Definitions

  • the present invention relates to a film-forming composition, a laminate formed by applying the film-forming composition, a touch panel formed by using the laminate, and a method for forming a cured film.
  • the touch panel used in smartphones and tablet PCs detects the position and movement of the finger, etc. that touches the panel surface, and clicks the icon, etc. displayed at the corresponding position on the display, enlarges or reduces the screen, and scrolls. It is a device that enables such things.
  • two methods a resistive film method and a capacitance method, are widely used as means for detecting the position and movement of a finger or the like on the touch panel.
  • the voltage fluctuation between the electrodes caused by pressing the finger, and in the capacitance method, the change in capacitance that occurs when the finger approaches or comes into contact with the panel surface is an electric signal at the sensor part.
  • the sensor portion is composed of a combination of an electrode layer, an insulating layer, and the like.
  • the film-forming composition for forming the insulating layer includes a cured film in an exposed portion and an uncured film in an unexposed portion. And, contradictory performance is required. That is, when exposed to a developing solution, the cured film remains undissolved, while the uncured film is quickly dissolved and removed. Further, even if the cured film itself is not dissolved, if the chemical adsorption force (adhesion) between the film and the interface between the translucent substrate or the ITO electrode is weak, the film is easily peeled off due to erosion of the developing solution. Therefore, the adhesion of the interface is also required.
  • the film-forming composition examples include, for example, Patent Document 1 in a lithography resist underlayer film-forming composition containing a hydrolyzable organosilane, a hydrolyzate thereof, a hydrolyzed condensate thereof, or a mixture thereof as a silane compound.
  • Patent Document 1 in a lithography resist underlayer film-forming composition containing a hydrolyzable organosilane, a hydrolyzate thereof, a hydrolyzed condensate thereof, or a mixture thereof as a silane compound.
  • a composition for forming a underlayer film of a resist for lithography, wherein the silane compound contains a silane compound having an amide bond in its molecule and an organic group having a carboxylic acid moiety, a carboxylic acid ester moiety, or both of them is disclosed. There is.
  • the cured film when exposed to the above-mentioned developer, the cured film remains undissolved, while the uncured film dissolves rapidly. It is hard to say that it has sufficient properties such as being removed by shaving and adhesion to a translucent substrate or ITO electrode, and when a dilute alkaline solution is used as a developing solution, a film that has not been cured is formed. Since it is difficult to dissolve and remove it, there is a problem that the equipment that can be used is limited, and there is room for improvement.
  • the silane compound (A) containing the above and the silane compound (B) having a radically polymerizable unsaturated double bond are contained, and the blending amount of the silane compound (A) and the silane compound (B). It was found that all of the above problems can be solved by containing a specific siloxane polymer having a predetermined range of, a photopolymerizable compound having two or more radically polymerizable double bonds, a polymerization initiator and an organic solvent. , The present invention is completed.
  • siloxane polymer having the structure of the following general formula (A)
  • a photopolymerizable compound having two or more radically polymerizable unsaturated double bonds
  • a polymerization initiator and an organic solvent
  • the ratio of p to q is high.
  • a film-forming composition characterized by being 1: 0.8 to 2.4.
  • X has the structure of the following general formula (B)
  • p and q represent integers
  • Y is a radically polymerizable double bond.
  • silane compound (C) selected from the group of tetraalkoxysilane and bis (trialkoxysilyl) alkane, and / or alkyltri. It is preferable that the silane compound (D), which is at least one selected from the group of alkoxysilane, dialkyldialkoxysilane, cycloalkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane, is further contained.
  • the molar ratio of the silane compound (C) to the silane compound (D) [the silane compound (C): the silane compound (D)] is 1: 0.1 to It is preferably 10.
  • the material constituting the siloxane polymer further contains a silane compound having an epoxy group in the molecule.
  • the present invention is also a laminate characterized by having a cured film of the above-mentioned film-forming composition on a base material.
  • the present invention is also a touch panel characterized by using a laminated body.
  • the coating step of applying the film-forming composition the exposure step of irradiating the exposed portion with active energy rays to form a cured film, and the coating liquid of the unexposed portion with a developing solution. It is also a method for forming a cured film, which comprises a developing step of dissolving and removing.
  • the film-forming composition of the present invention When the film-forming composition of the present invention is used in a photolithography method, the cured film formed in the exposed portion is not easily dissolved or eroded by the developing solution, and further, a translucent substrate such as a touch panel or the like.
  • the uncured film in the unexposed area has excellent adhesion to ITO electrodes and metal electrodes, and can be easily dissolved in a dilute alkaline developer and quickly removed, so that insulation with an appropriate film thickness can be obtained. Since a sex film can be formed, it has high developability.
  • a "dilute alkali" means a pH in the range of 10.0 to 12.5.
  • the film-forming composition of the present invention contains a siloxane polymer having the structure of the following general formula (A), a photopolymerizable compound having two or more radically polymerizable unsaturated double bonds, a polymerization initiator and an organic solvent. , The ratio of p to q is 1: 0.8 to 2.4.
  • X has the structure of the following general formula (B)
  • p and q represent integers
  • Y is a radically polymerizable double bond. It is a monovalent substituent having, m represents an integer of 1 or more and 5 or less, and n represents an integer of 1 or more.
  • the monomer containing the structure X (hereinafter, also referred to as the silane compound (A)) contains an organic group having an amide bond and a carboxylic acid moiety in the molecule.
  • the inclusion of an organic group having an amide bond and a carboxylic acid moiety in the molecule means that the silane molecule has a combination of an amide bond and a carboxylic acid moiety (amic acid structure).
  • the silane compound (A) the hydrolyzable organosilane disclosed in International Publication No. 2011/105368 and a method for producing the same can be appropriately selected and used.
  • m represents an integer of 1 or more and 5 or less
  • n represents an integer of 1 or more.
  • a trialkoxysilane having a substituent having a primary amino group for example, 3-aminopropyltrimethoxysilane, 3 -Aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, and other dibasic acid anhydrides, such as succinic anhydride and maleine anhydride.
  • the silane compound (A) is preferably a reaction product obtained by reacting aminopropyltriethoxysilane with succinic anhydride, hexahydrophthalic anhydride or itaconic acid, and is preferably aminopropyltriethoxysilane.
  • the reaction product is obtained by reacting with succinic anhydride. Specifically, it has the following structure.
  • the Y-containing monomer (also referred to as silane compound (B)) has a monovalent substituent having a radically polymerizable double bond.
  • the silane compound (B) include 3- (meth) acryloyloxypropylmethyldimethoxysilane, 3- (meth) acryloyloxypropyltrimethoxysilane, 3- (meth) acryloyloxypropylethyldiethoxysilane, and 3-(.
  • 3- (meth) acryloyloxypropylsilane compounds such as meta) acryloyloxypropyltriethoxysilane and allylsilane compounds such as allyltrimethoxysilane and allyltriethoxysilane.
  • 3-methacryloyloxypropyltrimethoxysilane is preferable from the viewpoint of high hydrolysis reactivity and crosslink density.
  • the siloxane polymer has a ratio (p: q) of p and q in the general formula (A) of 1: 0.8 to 2.4.
  • the molar ratio of the silane compound (A) to the silane compound (B) is preferably 1: 0.8 to 2.4. If the ratio of p and q (p: q) is less than 1: 0.8, the adhesion between the cured film and the translucent base material or the ITO electrode cannot be sufficiently imparted, and 1: 2.4.
  • the solubility of the uncured film in the developer becomes insufficient.
  • the molar ratio of the silane compound (A) to the silane compound (B) is preferably 1: 1.0 to 2.0, more preferably 1: 1.5 to 1.8.
  • a silane compound (C) which is at least one selected from the group of tetraalkoxysilane and bis (trialkoxysilyl) alkane, and / or alkyltrialkoxysilane and dialkyldialkoxy. It is preferable that the silane compound (D), which is at least one selected from the group of silane, cycloalkyltrialkoxysilane, vinyltrialkoxysilane, and phenyltrialkoxysilane, is further contained.
  • the silane compound (C) can impart solubility to a developing solution of an uncured film, and the silane compound (D) imparts resistance to a developing solution or an etching solution to the cured film. Can be done.
  • the cured film can be suitably provided with adhesion to a translucent base material or an ITO electrode, and , Solubility of the uncured film in the developing solution can be imparted.
  • the properties of the above-mentioned silane-based compound (C) and the above-mentioned silane-based compound (D) are preferable by containing the above-mentioned silane-based compound (C) and the above-mentioned silane-based compound (D) in a molar ratio. Therefore, it is possible to more preferably impart the adhesion to the translucent base material and the ITO electrode to the cured film, and more preferably impart the solubility of the uncured film to the developer. Can be done.
  • the silane compound (C) is at least one selected from the group of tetraalkoxysilane and bis (trialkoxysilyl) alkane.
  • the tetraalkoxysilane include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, ethoxytrimethoxysilane, dimethoxydiethoxysilane, and methoxy. Examples thereof include triethoxysilane.
  • bis (trialkoxysilyl) alkane examples include bis (trimethoxysilyl) methane, bis (triethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, and 1,2-bis (triethoxysilyl) methane. ) Ethane and the like can be mentioned.
  • tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, bis (triethoxysilyl) methane, 1 , 2-Bis (triethoxysilyl) ethane is preferable, and tetramethoxysilane, tetraethoxysilane, and tetraisopropoxysilane are more preferable.
  • the silane compound (D) is at least one selected from the group of alkyltrialkoxysilanes, dialkyldialkoxysilanes, cycloalkyltrialkoxysilanes, vinyltrialkoxysilanes, and phenyltrialkoxysilanes.
  • an alkyltrialkoxysilane is preferable as a compound having a saturated hydrocarbon group
  • a phenyltrialkoxysilane is preferable as a compound having an unsaturated hydrocarbon group.
  • alkyltrialkoxysilane examples include methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltriisopropoxysilane, methyltri-n-butoxysilane, methyltriisobutoxysilane, and methyltri-sec-butoxysilane.
  • Methyltri-tert-butoxysilane Methyltri-tert-butoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-propoxysilane, ethyltriisopropoxysilane, ethyltri-n-butoxysilane, ethyltriisobutoxysilane, n-propyltrimethoxysilane , N-propyltriethoxysilane, n-propyltri-n-propoxysilane, n-propyltriisopropoxysilane, n-propyltri-n-butoxysilane, n-propyltriisobutoxysilane, n-propyltri-sec -Butoxysilane, n-propyltri-tert-butoxysilane, isopropyltrimethoxysilane, isopropy
  • dialkyldialkoxysilane examples include dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldiisopropoxysilane, dimethyldi-n-butoxysilane, dimethyldiisobutoxysilane, dimethyldi-sec-butoxysilane, and dimethyldisilane.
  • cycloalkyltrialkoxysilane examples include cyclopentyltrimethoxysilane, cyclopentyltriethoxysilane, cyclopentyl-n-propoxysilane, cyclopentyltriisopropoxysilane, cyclopentyltri-n-butoxysilane, cyclopentyltriisobutoxysilane, and cyclopentylly.
  • vinyltrialkoxysilane examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-propoxysilane, vinyltriisopropoxysilane, vinyltri-n-butoxysilane, vinyltriisobutoxysilane, and vinyltri-sec-butoxysilane. , Vinyl tri-tert-butoxysilane and the like.
  • phenyltrialkoxysilane examples include phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-propoxysilane, phenyltrisopropoxysilane, phenyltri-nn-butoxysilane, phenyltriisobutoxysilane, and phenyltri-. Examples thereof include sec-butoxysilane and phenyltri-tert-butoxysilane.
  • At least one selected from the group of methyltriethoxysilane, dimethyldimethoxysilane, cyclohexyltriethoxysilane, vinyltriethoxysilane, and phenyltriethoxysilane is preferable, and methyltriethoxysilane and phenyltriethoxysilane. Is more preferable.
  • the siloxane polymer preferably further contains a silane compound having an epoxy group in the molecule, if necessary.
  • Examples of the silane compound having an epoxy group in the molecule include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3-glycidoxypropyl.
  • Methyldiethoxysilane 2- (3,4-epylcyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 2- (3,4-epylcyclohexyl) ethylmethyldimethoxysilane, Examples thereof include 2- (3,4-epoxycyclohexyl) ethylmethyldiethoxysilane. Of these, 3-glycidoxypropyltrimethoxysilane is preferable from the viewpoint of crosslink density and high hydrolysis reactivity.
  • the siloxane polymer may contain other silane compounds.
  • examples of other silane-based compounds include silane-based compounds having a mercapto group, and examples thereof include mercaptoalkyltrialkoxy silanes such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, and 2-mercaptoethyltrimethoxysilane. Examples include silane compounds.
  • the molar ratio of the silane compound (A) to the silane compound (D) [the silane compound (A): the silane compound (D)] is a cured film, a translucent substrate, or an ITO electrode. From the viewpoint of the adhesion of the uncured film and the solubility of the uncured film in the developing solution, the ratio is preferably 1: 0.1 to 5.0.
  • the molar ratio [the silane compound (A): the silane compound (D)] is more preferably 1: 0.8 to 3.0, and 1: 1.0 to 2.5. Is even more preferable.
  • the molar ratio of the silane compound (C) to the silane compound (D) is the cured film, the translucent substrate, and the ITO electrode. From the viewpoint of the adhesion of the uncured film and the solubility of the uncured film in the developing solution, the ratio is preferably 1: 0.1 to 10.
  • the molar ratio [the silane compound (C): the silane compound (D)] is more preferably 1: 0.3 to 5, and further preferably 1: 0.5 to 2.5. preferable.
  • the molar ratio of the silane compound (A) to the silane compound having an epoxy group in the molecule is a cured film and transparent. From the viewpoint of preferably imparting adhesion to a light base material or an ITO electrode, it is preferably 1: 0.1 to 1.0, more preferably 1: 0.2 to 0.7, and 1: 0. It is more preferably .3 to 0.6. Further, the molar ratio of the silane compound (A) to the other silane compound [the silane compound (A): the other silane compound] is a cured film, a translucent base material, or an ITO electrode. From the viewpoint of preferably imparting the adhesiveness of the above, it is preferably 1: 0.1 to 1.0, more preferably 1: 0.2 to 0.7, and 1: 0.3 to 0.6. Is even more preferable.
  • a method for producing the siloxane polymer for example, after mixing the silane compound (A) and the silane compound (B) in an appropriate container, the silane compound (C) and the silane are used as necessary.
  • the system compound (D), the silane compound having an epoxy group in the molecule, and the other silane compounds are mixed, and water, a polymerization catalyst, and a reaction solvent are added as necessary to hydrolyze and condense. You can use the method of making it. After the condensation reaction, unnecessary by-products other than the siloxane polymer can be removed by a method such as extraction, dehydration, or solvent removal to obtain the siloxane polymer.
  • the amount of water is preferably such that the number of water molecules is the same as the number of all hydrolyzable substituents of the silane compound charged in the container. Since the main silane compound used in the present invention has 3 or 4 hydrolyzable substituents per molecule, when a large amount of such a silane compound is contained, water is simply used.
  • the polymerization catalyst for example, an acid catalyst such as acetic acid or hydrochloric acid, or a base catalyst such as ammonia, triethylamine, cyclohexylamine or tetramethylammonium hydroxide can be used.
  • the amount of the polymerization catalyst the number of molecules of the polymerization catalyst is 0.05 to 0.2 times the number of all molecules of the silane compound charged in the container (as a molar ratio, the silane compound).
  • the total amount of the compound: polymerization catalyst 1: 0.05 to 0.2) is preferable.
  • reaction solvent lower alcohols such as ethanol, n-propyl alcohol and isopropyl alcohol, ketone compounds such as acetone and methyl ethyl ketone, and ester compounds such as ethyl acetate and n-propyl acetate are preferable, and lower alcohols are more preferable.
  • Ethanol and isopropyl alcohol are more preferable from the viewpoint that an appropriate reaction temperature can be maintained and distillation is easy.
  • the reaction temperature is preferably 60 to 80 ° C., and the reaction time is preferably about 2 to 24 hours so that the reaction can proceed sufficiently.
  • the siloxane polymer preferably has a weight average molecular weight (Mw) of 1,000 to 10,000. If the weight average molecular weight (Mw) is less than 1000, the curability of the film-forming composition may decrease, and if the weight average molecular weight (Mw) exceeds 10,000, the film-forming composition may be deteriorated. Solubility may decrease.
  • the siloxane polymer has a weight average molecular weight (Mw) of more preferably 1500 to 8000, and even more preferably 2000 to 6000.
  • the siloxane polymer was dissolved to prepare a solution of 0.02% by mass, and a filter (GL Sciences, GL chromatodisc, aqueous 25A, pore size 0.2 ⁇ m) was prepared. After passing through, it can be measured under the following conditions using an allity (manufactured by Nippon Waters Co., Ltd.) composed of size exclusion chromatography and a refractive index detector.
  • Eluent THF Flow velocity: 1.0 ml / min Injection volume: 100 ⁇ l
  • the film-forming composition of the present invention contains a photopolymerizable compound having two or more radically polymerizable unsaturated double bonds.
  • Examples of the photopolymerizable compound having two or more radically polymerizable unsaturated double bonds include an ester compound of a divalent or higher hydroxyl group-containing compound and (meth) acrylic acid, for example, 1,3-butylene glycol di (meth).
  • compounds having a trifunctional or higher reactive functional group such as trimethylolpropane tri (meth) acrylate and glycerin tri (meth) acrylate, are used from the viewpoint of increasing the cross-linking density and imparting hardness to the excellent cured film.
  • the film-forming composition of the present invention contains a polymerization initiator.
  • a polymerization initiator it is preferable to use a photopolymerization initiator that can obtain a sufficient photocuring reaction when forming a cured film by the photolithography method described later.
  • a photopolymerization initiator include benzyl, benzoin, benzophenone, phenylquinone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 4,4'-bis (dimethylamino) benzophenone, and the like.
  • Organic solvent organic solvents such as alcohols, polyhydric alcohols and derivatives thereof, ketone-based organic solvents, and ester-based organic solvents can be used.
  • Examples of the alcohols include lower alcohols such as methanol, ethanol, n-propyl alcohol-n-, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol and sec-butyl alcohol.
  • polyhydric alcohols examples include ethylene glycol, propylene glycol, 1,2-butanediol, 1,3-butanediol, diethylene glycol, dipropylene glycol and the like.
  • ethylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, ethylene Glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol monoisopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol monoisobutyl ether, propylene glycol monophenyl ether , Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol monoisopropyl ether, diethylene glycol mono-n-butyl ether,
  • Glycol monoether acylates such as propylene glycol monoethyl ether acetate, dipropylene glycol mono-n-propyl ether acetate, dipropylene glycol monoisopropyl ether acetate, dipropylene glycol mono-n-butyl ether acetate, dipropylene glycol monoisobutyl ether acetatekind is mentioned.
  • ketone-based organic solvent examples include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl isopropyl ketone, methyl-n-butyl ketone, methyl isobutyl ketone, cyclohexanone and the like.
  • ester-based organic solvent examples include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, methyl lactate, and lactic acid.
  • Ethyl, lactate-n-propyl and the like can be mentioned.
  • the organic solvent can be used alone or in combination of two or more. From the viewpoint of solubility and coating suitability of the siloxane polymer, derivatives of polyhydric alcohols and ester-based organic solvents are preferable, and propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, and propylene glycol are preferable. More preferably, monoisopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol monoisobutyl ether, propylene glycol monomethyl ether acetate, acetic acid-n-propyl, and isopropyl acetate.
  • the film-forming composition of the present invention contains a chelating compound of a metal such as aluminum, zirconium, or titanium, a carbodiimide-based, an isocyanate-based, a crosslinkable functional group such as an epoxy group or a thiol group, as long as the effect of the present invention is not reduced.
  • Cross-linking agents silicone-based, fluorine-based surfactants, aromatic hydrocarbon-based, amino compound-based, nitro compound-based, quinones, xanthones and other photosensitizers, hydroquinone, methquinone, hindered amine-based, hindered Polymerization inhibitors such as phenolic compounds, dit-butylhydroquinone, 4-methoxyphenol, butylhydroxytoluene and nitrosoamine salts, fillers such as inorganic metal oxides and organic fine particles can be added.
  • the photopolymerizable compound having two or more radically polymerizable unsaturated double bonds is preferably contained in an amount of 10 to 50 parts by mass with respect to 100 parts by mass of the siloxane polymer.
  • the content of the photopolymerizable compound having two or more radically polymerizable unsaturated double bonds is less than 10 parts by mass with respect to 100 parts by mass of the siloxane polymer, the curable or translucent group of the cured film Adhesion to the material or ITO electrode may be insufficient, and if it exceeds 50 parts by mass with respect to 100 parts by mass of the siloxane polymer, the solubility of the uncured film in the developing solution will be insufficient. There is.
  • the polymerization initiator is contained in an amount of 0.5 to 40 parts by mass when the total amount of the siloxane polymer and the polymerizable monomer having two or more radically polymerizable unsaturated double bonds is 100 parts by mass. Is preferable. If the content of the polymerization initiator is less than 0.5 parts by mass, the photopolymerizability is lowered, and unreacted components may remain in the exposed part of the photolithography method, and if it exceeds 40 parts by mass. , The storage stability of the film-forming composition may decrease.
  • the polymerization initiator may be 1 to 20 parts by mass when the total amount of the siloxane polymer and the polymerizable monomer having two or more radically polymerizable unsaturated double bonds is 100 parts by mass. More preferred.
  • Manufacturing method of film-forming composition As a method for producing the film-forming composition of the present invention, an organic solvent is charged in an appropriate container, and for example, the siloxane polymer and the radically polymerizable unsaturated double bond are formed while stirring with a high-speed stirrer or the like. A method of charging and mixing the above-mentioned photopolymerizable compound, the above-mentioned polymerization initiator, and other materials such as, if necessary, can be used.
  • the method for producing the film-forming composition of the present invention is not limited to the above method, and the order of charging each material may be arbitrary.
  • the material in a solid state is soluble in an organic solvent, it may be dissolved in advance before preparation, and if it can be dispersed directly in the organic solvent or by using a dispersant or the like, it is possible. It may be dispersed in advance before the preparation.
  • Method of forming a cured film As a method of forming a cured film using the film-forming composition of the present invention, a coating step of applying the film-forming composition to a substrate, and irradiating an exposed portion with active energy rays to form a cured film. It is preferable to have an exposure step for processing and a development step for dissolving and removing the coating liquid in the unexposed portion with a developing solution. Such a method for forming a cured film is also an aspect of the present invention.
  • the coating method in the coating process, the active energy rays irradiating the exposed portion in the exposure step and the irradiation method thereof, and the developing solution for removing the coating liquid in the exposed portion are used in the conventional photolithography method.
  • the thing and the method can be appropriately selected and used.
  • the film-forming composition is diluted so that the concentration of the non-volatile component is 25%, coated with a spin coater, heated (prebaked) at 80 ° C. for 3 minutes, and then mask-aligned.
  • the test pattern is baked under an irradiation condition of 100 mJ / cm 2 and immersed in a developing solution for 1 minute, and then heated (post-baked) at 150 ° C. for 30 minutes to obtain a cured film.
  • the prebaking condition it is preferable to carry out the treatment at 80 to 100 ° C. for 1 to 3 minutes.
  • the irradiation conditions are preferably 20 to 120 mJ / cm 2.
  • the post-baking conditions it is preferable to carry out the treatment under the conditions of 120 to 180 ° C. and 30 to 60 minutes.
  • a glass base material used for a touch panel and a conventionally known plastic base material can be appropriately used, and a base material having a transparent electrode formed on the surface thereof may be used.
  • a transparent electrode is provided on the surface, it is preferable to form a cured film of the film-forming composition of the present invention on the surface on which the transparent electrode is formed.
  • a laminate characterized by having a cured film of the film-forming composition of the present invention on the base material is also an aspect of the present invention.
  • a touch panel characterized by using the laminate of the present invention is also an aspect of the present invention.
  • the material constituting the touch panel conventionally known materials can be appropriately used except that the laminate of the present invention is used.
  • silane compound (A) 20.00 g of aminopropyltriethoxysilane was placed in a 200 ml three-necked flask, 9.04 g of powdered succinic anhydride was placed while cooling in a water bath, and the mixture was stirred at room temperature for 20 minutes. Then, the obtained crude product was concentrated and used for the synthesis of a siloxane polymer described later.
  • Photopolymerizable compound having two or more radically polymerizable unsaturated double bonds Triacrylate (2-hydroxyethyl) isocyanuric acid triacrylate (denoted as THITA, manufactured by Tokyo Chemical Industry Co., Ltd.) Dipentaerythritol hexaacrylate (denoted as DPHA, manufactured by Tokyo Chemical Industry Co., Ltd.) Pentaerythritol tetraacrylate (denoted as PTA, manufactured by Tokyo Chemical Industry Co., Ltd.)
  • Dissolution rate is less than 400 nm / s ⁇ : Dissolution rate is 400 nm / s or more and less than 600 nm / s ⁇ : Dissolution rate is 600 nm / s or more and less than 1200 nm / s ⁇ : Dissolution rate is 1200 nm / s s or more
  • a film thickness measuring device (Alpha-Step IQ surface profiler) measures the film thickness (T1) of the exposed part of the part where the evaluation test piece is exposed to the developer and the film thickness (T2) of the exposed part of the part not exposed to the developer. It was measured using KLM-Tencor), and the film thickness ratio of the film-forming composition was evaluated using the following as evaluation criteria.
  • test pattern was baked under irradiation conditions of 100 mJ / cm 2 using a mask aligner (PLA-501FA, manufactured by Canon Inc.), and a part of the test pattern was developed. After immersing in a 2.38% aqueous solution of tetramethylammonium hydroxide used as a film for 1 minute, it is heated (post-baked) at 150 ° C. for 30 minutes, washed with water, dried, and the transparent electrode of each film-forming composition. A test piece for evaluating adhesion to the skin was prepared.
  • Table 2 shows the evaluation results of the solubility, erosion, film thickness ratio and adhesion of the film-forming compositions of Examples 1 to 8 and Comparative Examples 1 to 5.
  • Example 4 contains the silane compound (A) and the silane compound (B) in a predetermined molar ratio, and the silane compound (C) and the silane compound (D) in a predetermined molar ratio. , Solubility, erosion, film thickness ratio and adhesion were all extremely excellent.
  • the film-forming compositions of Comparative Examples 1 and 4 had poor solubility in the unexposed portion and were inferior in the evaluation of the film thickness ratio. Further, the film-forming compositions of Comparative Examples 2, 3 and 5 had poor erosion evaluation of the exposed portion and were inferior in the evaluation of the film thickness ratio. Further, the film-forming composition of Comparative Example 2 is slightly inferior in adhesion to the ITO laminated surface of the glass substrate, and the film-forming composition of Comparative Example 5 is inferior in adhesion to the ITO laminated surface of the glass substrate. Was there.
  • the cured film formed in the exposed portion is not easily dissolved or eroded by the developing solution, and further, a translucent substrate such as a touch panel or the like.
  • the uncured film in the unexposed area has excellent adhesion to ITO electrodes and metal electrodes, can be easily dissolved in a dilute alkaline developer and can be quickly removed, and has an insulating property of an appropriate film thickness. Since a film can be formed, it can be suitably used as an insulating film to be applied to a translucent substrate such as a touch panel.

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Abstract

La présente invention concerne une composition de formation de film de revêtement par laquelle un film de revêtement durci, qui est formé sur une partie exposée à la lumière lorsque la composition est utilisée dans un procédé de photolithographie, est peu susceptible de se dissoudre dans une solution de développement ou d'être corrodé par cette dernière, et présente une excellente adhérence à un substrat transparent, une électrode ITO ou une électrode métallique d'un panneau tactile ou similaire, moyennant quoi un film de revêtement qui n'a pas été durci sur une partie non exposée à la lumière peut être rapidement éliminé par dissolution facile dans une solution de développement alcaline diluée, et un film de revêtement isolant ayant une épaisseur appropriée peut être formé. La présente invention concerne une composition de formation de film de revêtement caractérisée en ce qu'elle contient un polymère siloxane ayant une structure représentée par la formule générale (A), un composé photopolymérisable ayant au moins deux doubles liaisons insaturées polymérisables par voie radicalaire, un initiateur de polymérisation et un solvant organique, le rapport p:q allant de 1:0,8 à 1:2,4. (Dans la formule générale (A), X a une structure représentée par la formule générale (B), et p et q représentent des nombres entiers. Dans la formule générale (B), Y est un groupe substituant monovalent ayant une double liaison polymérisable par voie radicalaire, m représente un nombre entier de 1 à 5 et n représente un nombre entier supérieur ou égal à 1.)
PCT/JP2020/030574 2019-09-30 2020-08-11 Composition de formation de film de revêtement, stratifié obtenu par revêtement de ladite composition de formation de film de revêtement, panneau tactile obtenu à l'aide dudit stratifié et procédé de formation de film de revêtement durci WO2021065211A1 (fr)

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CN202080066096.5A CN114430767B (zh) 2019-09-30 2020-08-11 皮膜形成用组合物、涂布该组合物的层叠体、使用该层叠体的触控面板及固化皮膜的形成方法

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WO2013031985A1 (fr) * 2011-08-31 2013-03-07 旭化成イーマテリアルズ株式会社 Composition de résine de silicone photosensible alcalino-soluble
WO2014046210A1 (fr) * 2012-09-24 2014-03-27 旭硝子株式会社 Produit de condensation par hydrolyse partielle et agent répulsif d'encre utilisant celui-ci
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