CN103969948A - Black Photosensitive Composition Used For Touch Control Panel And Touch Control Panel - Google Patents
Black Photosensitive Composition Used For Touch Control Panel And Touch Control Panel Download PDFInfo
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- CN103969948A CN103969948A CN201410040163.2A CN201410040163A CN103969948A CN 103969948 A CN103969948 A CN 103969948A CN 201410040163 A CN201410040163 A CN 201410040163A CN 103969948 A CN103969948 A CN 103969948A
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- 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
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- 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
-
- 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
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- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Position Input By Displaying (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The invention provides a black photosensitive composition used for a touch control panel and the touch control panel employing the composition. The black photosensitive composition contains: (A) alkali soluable resin obtained through reacting (a) dicarboxylic acid, tricarboxylic acid or anhydride thereof and (b) tetracarboxylic acid or dianhydride thereof at a mole ratio from 0.1 to 10 and epoxy compound provided with two glycidyl ether groups derivated from bisphenols with reaction of monocarboxylic acid with unsaturated groups; (B) polymerizable monomer provided with at least one alkene unsaturated bond; (C) compound provided with epoxy groups; (D) polymerization initiator; (E) shading material. Relative to 100 parts of (A) by weight, (B) is 10 to 60 parts by weight, (C) is 10 to 80 parts by weight. Relative to 100 parts by weight relative to (A) and (B), (D) is 2 to 40 parts by weight. (E) counts for 40 to 60% by mass in solid component.
Description
Technical field
The present invention relates to chemical proofing excellence, can form desirable pattern, there is the contact panel black-colored photosensitive resin composition of high light-proofness.Particularly, relate to the contact panel of contact panel black-colored photosensitive resin composition and use said composition.
Background technology
The colored filter of liquid crystal indicator is conventionally by forming successively the method manufacture of the pixel of red, green, blue with the multicolour pattern of striated or zyklopisch etc. on the transparency carrier such as glass, the plastic plate surface being formed with the black film for separating each pixel.This black film works to prevent the contrast that causes because of the light leak between pixel and the reduction of excitation, the main black-colored photosensitive resin composition that contains the light screening materials such as carbon black, oxynitriding titanium, titanium be black, alkali-developable that uses.
At present, as the data input means in the display device such as liquid crystal display, contact panel is used widely, and wherein, electrostatic capacity type contact panel is in practical application.In the picture of electrostatic capacity type contact panel, there is the zyklopisch electrode pattern that is formed as two layers with transparent conductive materials such as ITO.Two layers of electrode pattern are presented at respectively x direction of principal axis and the shape being connected on y direction of principal axis, are situated between and are connected with outside control circuit by taking-up distributions such as metals.During with finger touch picture, on electrode pattern in its vicinity, static capacity changes, and control circuit detects this variation with coordinate information, thereby can identify the position (for example can referring to patent documentation 1) of finger.
Use in substrate at this contact panel, the black film same with colored filter is also used to hiding of shading, distribution etc., but according to the formation of substrate, need to after formation black film, form electrode, metal wiring etc., so, require black film to there are the thermotolerance to the temperature in these manufacturing procedures, the high resistance to chemicals medicine to the chemicals using etc. in manufacturing procedure.For example, the in the situation that of forming metal wiring after black film forms, form the treating fluids such as middle use alkalescence or acidic etching liquid, alkaline anticorrosive additive stripping liquid controlling at pattern, especially in the situation that using strong basicity treating fluid, due to film in the compatibility of contained alkali soluble resin, there will be film to dissolve and the problem peeled off maybe cannot be guaranteed sufficient adhering problem.Increase the ratio of the light screening materials such as carbon black, oxynitriding titanium, titanium be black for this reason, can reduce the ratio of the alkali soluble resin in black film, thus, chemical proofing improves, but photo-curable, pattern form and can significantly decline, be difficult to take into account the problem such as developing property and sufficient chemical proofing thereby produce.
In order to address this is that, also someone proposes black-colored photosensitive resin composition for contact panel (can referring to patent documentation 2,3), but still cannot take into account chemical proofing and pattern form can, expect to develop more high performance material.
Patent documentation:
Patent documentation 1: TOHKEMY 2011-186717 communique
Patent documentation 2: TOHKEMY 2012-145699 communique
Patent documentation 3:WO2012/133148 Publication
Summary of the invention
Therefore, the present invention aims to provide and can solve above-mentioned each problem of the prior art, has the contact panel black-colored photosensitive resin composition of sufficient chemical proofing and developing property excellence and uses the contact panel of this resin combination.
In order to address the above problem, present inventor conducts in-depth research, found that, by the compound with epoxy radicals is coexisted in the black-colored photosensitive resin composition that contains alkali soluble resin, photopolymerizable monomer (photopolymerization monomer), Photoepolymerizationinitiater initiater, light screening material etc., can obtain improving chemical proofing and pattern forms the contact panel black-colored photosensitive resin composition that can also can not reduce., main contents of the present invention are as follows.
(1) the present invention is a kind of contact panel black-colored photosensitive resin composition, it is characterized in that, contain: (A) alkali soluble resin, it is by making (a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides and (b) tetrabasic carboxylic acid or its dianhydride react and obtain with the reactant of the monocarboxylic acid that contains unsaturated group in the mol ratio of 0.1～10 scope and the epoxy compound with 2 glycidyl ethers being derived by bisphenols with (a)/(b); (B) there is the photopolymerizable monomer of at least one alkene unsaturated link; (C) there is the compound of epoxy radicals; (D) Photoepolymerizationinitiater initiater; (E) light screening material, with respect to (A) 100 mass parts, (B) is 10～60 mass parts, (C) be 10～80 mass parts, and with respect to (A) and 100 mass parts of total amount (B), be (D) 2～40 mass parts, and (E) account for 40～60 quality % in solid constituent.
(2) contact panel of the present invention is also (C) to have at least 3 epoxy radicals by the feature of black-colored photosensitive resin composition.
(3) the present invention or a kind of solidfied material, it is cured and obtains again after using above-mentioned black-colored photosensitive resin composition Jie to be formed by photoetching process.
(4) the present invention or a kind of contact panel with above-mentioned solidfied material.
The present invention is described in detail below.
Contact panel of the present invention is alkali soluble resin with (A) in black-colored photosensitive resin composition, and it is by making (a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides and (b) tetrabasic carboxylic acid or its dianhydride react and obtain with the reactant of the monocarboxylic acid that contains unsaturated group with (a)/(b) mol ratio in 0.1～10 scope and the epoxy compound with 2 glycidyl ethers that derived by bisphenols.
As the bisphenols of raw material that forms (A), can list two (4-hydroxy phenyl) ketone, two (4-hydroxyl-3,5-3,5-dimethylphenyl) ketone, two (4-hydroxyl-3,5-dichlorophenyl) ketone, two (4-hydroxy phenyl) sulfone, two (4-hydroxyl-3,5-3,5-dimethylphenyl) sulfone, two (4-hydroxyl-3,5-dichlorophenyl) sulfone, two (4-hydroxy phenyl) HFC-236fa, two (4-hydroxyl-3,5-3,5-dimethylphenyl) HFC-236fa, two (4-hydroxyl-3,5-dichlorophenyl) HFC-236fa, two (4-hydroxy phenyl) dimethylsilane, two (4-hydroxyl-3,5-3,5-dimethylphenyl) dimethylsilane, two (4-hydroxyl-3,5-dichlorophenyl) dimethylsilane, two (4-hydroxy phenyl) methane, two (4-hydroxyl-3,5-dichlorophenyl) methane, two (4-hydroxyl-3,5-dibromo phenyl) methane, two (4-hydroxy phenyl) propane of 2,2-, two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) propane of 2,2-, two (4-hydroxyl-3, the 5-dichlorophenyl) propane of 2,2-, two (the 4-hydroxy-3-methyl phenyl) propane of 2,2-, two (4-hydroxyl-3-chlorphenyl) propane of 2,2-, two (4-hydroxy phenyl) ether, two (4-hydroxyl-3,5-3,5-dimethylphenyl) ether, two (4-hydroxyl-3,5-dichlorophenyl) ether, two (4-hydroxy phenyl) fluorenes of 9,9-, two (the 4-hydroxy-3-methyl phenyl) fluorenes of 9,9-, two (4-hydroxyl-3-chlorphenyl) fluorenes of 9,9-, two (4-hydroxyl-3-bromophenyl) fluorenes of 9,9-, two (4-hydroxyl-3-fluorophenyl) fluorenes of 9,9-, two (4-hydroxyl-3, the 5-3,5-dimethylphenyl) fluorenes of 9,9-, two (4-hydroxyl-3, the 5-dichlorophenyl) fluorenes of 9,9-, two (4-hydroxyl-3, the 5-dibromo phenyl) fluorenes of 9,9-, 4,4'-xenol, 3,3 '-xenol etc. and their derivant.Wherein, the bisphenols that has 9,9-fluorenyl especially can utilize well.
Then, above-mentioned bisphenols is reacted with chloropropylene oxide, obtain having the epoxy compound of 2 glycidyl ethers.Due to the oligomerization with 2-glycidyl ether compound conventionally in the time carrying out this reaction, thereby can obtain the epoxy compound of following general formula (I).
(changing 1)
In the formula of general formula (I), R
1, R
2, R
3and R
4represent independently respectively alkyl, halogen atom or the phenyl of hydrogen atom, carbon number 1～5, represent-CO-of A ,-SO
2-,-C (CF
3)
2-,-Si (CH
3)
2-,-CH
2-,-C (CH
3)
2-,-O-, 9,9-fluorenyl or directly key.I is 0～10 integer.Preferably R
1, R
2, R
3, R
4for hydrogen atom, preferably A is 9,9-fluorenyl.In addition, the normally multiple values of I are mixed in together, though thereby mean value be that 0～10(is not limited to integer), the mean value of I is preferably 0～3.If the value of I exceedes higher limit, in the time that use forms black-colored photosensitive resin composition with the synthetic alkali soluble resin of this epoxy compound, the viscosity of composition is excessive, there will be coating cannot carry out smoothly or can not fully give the situation of alkali-soluble, the non-constant of alkali-developable.
Then, make that the two reacts with the compound of general formula (I) as the acrylic or methacrylic acid of the monocarboxylic acid that contains unsaturated group or they, obtain having the reactant of hydroxyl, make again (a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides and (b) tetrabasic carboxylic acid or its dianhydride, so that (a)/(b) mol ratio in 0.1～10 scope is reacted with above-mentioned reactant, obtain the alkali soluble resin with epoxy (methyl) acrylate acid addition product structure that following general formula (II) represents.
(changing 2)
(in formula, R
1, R
2, R
3and R
4represent independently respectively alkyl, halogen atom or the phenyl of hydrogen atom, carbon number 1～5, R
5represent hydrogen atom or methyl, represent-CO-of A ,-SO
2-,-C (CF
3)
2-,-Si (CH
3)
2-,-CH
2-,-C (CH
3)
2-,-O-, 9,9-fluorenyl or directly key, X represents 4 yuan of carboxylic acid residues, Y
1and Y
2represent independently respectively hydrogen atom or-OC-Z-(COOH)
m(wherein, Z represents 2 yuan or 3 yuan of carboxylic acid residues, and m represents 1～2 number), n represents 1～20 integer.）
Because this epoxy (methyl) acrylate acid addition product (II) is for having the alkali soluble resin of alkene unsaturated double-bond and carboxyl concurrently, therefore, (A) as contact panel of the present invention with black-colored photosensitive resin composition, can give excellent photo-curable, good developability, pattern-forming characteristic, obtain good contact panel black film pattern.
As (a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides that use in epoxy (methyl) the acrylate acid addition product that is general formula (II) at (A) of the present invention, use chain hydrocarbon dicarboxylic acid, tricarboxylic acids or its acid anhydrides, ester ring type dicarboxylic acid, tricarboxylic acids or its acid anhydrides, aromatic dicarboxylic acid, tricarboxylic acids or its acid anhydrides.Here; as chain hydrocarbon dicarboxylic acid, tricarboxylic acids or its acid anhydrides; for example having the compounds such as succinic acid, acetyl group succinic acid, maleic acid, hexane diacid, itaconic acid, azelaic acid, citramalic acid, malonic acid, glutaric acid, citric acid, tartrate, ketoglutaric acid, heptandioic acid, decanedioic acid, suberic acid, diglycolic acid, can also be to have imported any substituent dicarboxylic acid, tricarboxylic acids or its acid anhydrides.In addition, as ester ring type dicarboxylic acid, tricarboxylic acids or its acid anhydrides, for example having the compounds such as cyclobutane dicarboxylic acid, cyclopentane dicarboxylic acid, hexahydrophthalic acid, tetrahydrophthalic acid, norbornane dicarboxylic acid, can also be to have imported any substituent dicarboxylic acid or tricarboxylic acids or its acid anhydrides.In addition, as aromatic dicarboxylic acid or tricarboxylic acids or its acid anhydrides, for example, having the compounds such as phthalic acid, m-phthalic acid, trimellitic acid, can also be to have imported any substituent dicarboxylic acid, tricarboxylic acids or its acid anhydrides.
In addition, as (b) tetrabasic carboxylic acid or its dianhydride that use in epoxy (methyl) the acrylate acid addition product that is general formula (II) at (A) of the present invention, use chain hydrocarbon tetrabasic carboxylic acid or its dianhydride, ester ring type tetrabasic carboxylic acid or its dianhydride or aromatic polycarboxylic acid or its dianhydride.Here, as chain hydrocarbon tetrabasic carboxylic acid or its dianhydride, for example, having BTCA, pentane tetrabasic carboxylic acid, hexane tetrabasic carboxylic acid etc., can also be to have imported substituent tetrabasic carboxylic acid or its dianhydride.In addition, as ester ring type tetrabasic carboxylic acid or its dianhydride, for example, having cyclo-butane tetrabasic carboxylic acid, cyclopentane tetrabasic carboxylic acid, cyclohexane tetrabasic carboxylic acid, cycloheptane tetrabasic carboxylic acid, norbornane tetrabasic carboxylic acid etc., can also be to have imported substituent tetrabasic carboxylic acid or its dianhydride.In addition, as aromatic tetracarboxylic acid or its dianhydride, for example, can be Pyromellitic Acid, benzophenone tetrabasic carboxylic acid, biphenyltetracarboxyacid acid, Biphenyl Ether tetrabasic carboxylic acid or its dianhydride, can also be to have imported substituent tetrabasic carboxylic acid or its dianhydride.
(a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides using in epoxy (methyl) acrylate that (A) of the present invention is general formula (II) acid addition product and (b) mol ratio (a) of tetrabasic carboxylic acid or its dianhydride/(b) in 0.1～10 scope, preferably in 0.2～3.0 scope.If mol ratio (a)/(b) depart from above-mentioned scope, can not get the suitableeest molecular weight, for using the black-colored photosensitive resin composition of (A), alkali-developable, thermotolerance, solvent resistance, pattern form etc. can be deteriorated, thereby unsuitable.In addition, have that mol ratio (a)/(b) is less, alkali dissolubility is larger, also larger tendency of molecular weight.
The weight-average molecular weight (Mw) of epoxy (methyl) the acrylate acid addition product that in addition, (A) of the present invention is general formula (II) is preferably between 2000～10000, especially preferably between 3000～7000.If weight-average molecular weight (Mw) is less than 2000, in the time using the development of black-colored photosensitive resin composition of (A), cannot maintain the adhesiveness of pattern, pattern can occur and peel off, and in the time that weight-average molecular weight (Mw) exceedes 10000, the residual film of develop residue and unexposed portion is easily residual.In addition, the acid value of preferred (A) is in the scope of 30～200mgKOH/g.If this value is less than 30mgKOH/g, use the alkali of the black-colored photosensitive resin composition of (A) to develop and can not carry out smoothly, or need the special development conditions such as highly basic, and in the time that this value exceedes 200mgKOH/g, alkaline developer is too fast to the infiltration of the black-colored photosensitive resin composition of use (A), can peel off development, thereby all be not suitable for.
Epoxy (methyl) the acrylate acid addition product of the general formula (II) using in the present invention can be manufactured by above-mentioned operation, by the method for record in known method such as No. 8-278629 report of Japanese kokai publication hei or TOHKEMY 2008-9401 communique etc.First, the method of reacting with the epoxy compound of general formula (I) as the monocarboxylic acid that makes to contain unsaturated group, for example have and will add in solvent with the equimolar monocarboxylic acid that contains unsaturated group of epoxy radicals of epoxy compound, at catalyzer (benzyltriethylammoinium chloride, 2,6-diisobutyl phenol etc.) existence under, limit is blown into air limit and at 90～120 DEG C, heats, stirs the method for reacting.Then, as the method that makes acid anhydrides with the hydroxyl reaction of the epoxy acrylic ester compounds for above-mentioned resultant of reaction, have the ormal weight of epoxy acrylic ester compounds and dianhydride and an acid anhydride is added in solvent, under the existence of catalyzer (tetraethylammonium bromide, triphenylphosphine etc.), heating at 90～130 DEG C, stirring, the method for reacting.
At least there is the photopolymerizable monomer of 1 alkene unsaturated link as contact panel of the present invention with (B) in black-colored photosensitive resin composition, for example, can enumerate (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) acrylic acid 2-hydroxypropyl acrylate, (methyl) 2-EHA etc. has (methyl) esters of acrylic acid of hydroxyl, ethylene glycol bisthioglycolate (methyl) acrylate, diethylene glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, TEG two (methyl) acrylate, tetramethylene glycol two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, trimethylolethane trimethacrylate (methyl) acrylate, pentaerythrite two (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol four (methyl) acrylate, glycerine (methyl) acrylate, D-sorbite five (methyl) acrylate, dipentaerythritol five (methyl) acrylate or dipentaerythritol six (methyl) acrylate, D-sorbite six (methyl) acrylate, alkylene oxide modification six (methyl) acrylate of phosphonitrile, (methyl) esters of acrylic acids such as caprolactone modification dipentaerythritol six (methyl) acrylate, can use one kind or two or more in these.This photopolymerizable monomer with at least 1 alkene unsaturated link is preferably used the compound that has more than 3 optical polymerism group, the molecule of the alkali soluble resin that contains unsaturated group can be cross-linked with each other.In addition, the photopolymerizable monomer that (B) has at least 1 alkene unsaturated link does not have free carboxy.
There is the compound of epoxy radicals as contact panel of the present invention with (C) in black-colored photosensitive resin composition, for example, can enumerate bisphenol type epoxy compound, Bisphenol F type epoxy compound, bisphenol fluorene type epoxy compound, phenol phenolic varnish type epoxy compound, cresols phenolic varnish type epoxy compound, the glycidol ether of polyvalent alcohol, the ethylene oxidic ester of polybasic carboxylic acid, contain the polymkeric substance of (methyl) glycidyl acrylate as polymerized unit, the alicyclic epoxy compound that is representative with 3,4-7-oxa-bicyclo[4.1.0 carboxylic acid (3 ', 4 '-epoxycyclohexyl) methyl esters, there is multi-functional epoxy compound's (HP7200 series that for example DIC company produces) of bicyclopentadiene skeleton, 1 of two (the methylol)-n-butyl alcohols of 2,2-, 2-epoxy radicals-4-(2-epoxy ethyl) cyclohexane addition product (for example Daicel company product " EHPE3150 "), epoxidized polybutadiene (for example Japanese Cao Da company's product " NISSO-PBJP-100 "), there is the epoxy compound of silicone skeleton etc.As these compositions, preferably epoxide equivalent is the compound that 100～300g/eq and number-average molecular weight are 100～5000.More preferably use the epoxy compound in 1 molecule with more than 3 epoxy radicals.In addition, (C) can only use the compound of a kind, also can multiple kinds be used in combination.
As (D) Photoepolymerizationinitiater initiater in black-colored photosensitive resin composition for contact panel of the present invention, for example, can enumerate acetophenone, 2,2-diethoxy acetophenone, to dimethyl acetophenone, to dimethylamino propiophenone, dichloroacetophenone, trichloroacetophenone, the acetophenones such as p-tert.-butyl acetophenone, benzophenone, 2-chlorobenzophenone, p, p '-benzophenones such as bis-dimethylamino benzophenone, benzyl, styrax, benzoin methyl ether, benzoin isopropyl ether, the styrax ethers such as benzoin isobutyl ether, 2-(Chloro-O-Phenyl)-4, the two imidazoles of 5-phenyl, 2-(Chloro-O-Phenyl)-4, the two imidazoles of 5-bis-(m-methoxyphenyl), the adjacent fluorophenyl of 2-()-4, the two imidazoles of 5-diphenyl, 2-(o-methoxyphenyl)-4, the two imidazoles of 5-diphenyl, two imidazole compound classes such as the two imidazoles of 2,4,5-triaryl, 2-trichloromethyl-5-styryl-1,3,4-oxadiazole, 2-trichloromethyl-5-(is to cyano styrene base)-1,3,4-oxadiazole, 2-trichloromethyl-5-(is to methoxyl-styrene)-1,3, the halomethyl diazole compounds classes such as 4-oxadiazole, 2,4,6-tri-(trichloromethyl)-1,3,5-triazines, 2-methyl-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-phenyl-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(4-chlorphenyl)-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(4-methoxyphenyl)-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(4-methoxyl naphthyl)-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(4-methoxyl-styrene)-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(3,4,5-trimethoxy styryl)-4, two (the trichloromethyl)-1,3,5-triazines of 6-, 2-(4-methyl thio phenyl vinyl)-4, two (trichloromethyl)-halomethyl-S-triazine based compound classes such as 1,3,5-triazines of 6-, 1-(4-(thiophenyl) phenyl)-1,2-octane diketone 2-(O-benzoyl oxime), 1-(4-phenyl sulfur phenenyl) butane-1,2-diketone-2-oxime-O-benzoic ether, 1-(4-methyl thio phenyl) butane-1,2-diketone-2-oxime-O-acetic acid esters, 1-(4-methyl thio phenyl) the O-acyl group oxime compound class such as butane-1-ketoxime-O-acetic acid esters, benzyl dimethyl ketal, thioxanthones, CTX, 2,4-diethyl thioxanthone, 2-methyl thioxanthones, the sulphur compounds such as ITX, 2-EAQ, prestox anthraquinone, 1,2-benzo anthraquinone, the Anthraquinones such as 2,3-diphenyl anthraquinone, azoisobutyronitrile, benzoyl peroxide, the organic peroxides such as cumene peroxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, the sulphur compounds such as 2-mercaptobenzothiazole, triethanolamine, the tertiary amines such as triethylamine, etc.Wherein, the angle of the highly sensitive black-colored photosensitive resin composition that is easy to get is calmly considered, is preferably used O-acyl group oxime compound class.In addition, these Photoepolymerizationinitiater initiaters also can use two or more.It should be noted that, in the present invention, said Photoepolymerizationinitiater initiater one word is that the implication that comprises sensitizer is used.
As (E) light screening material in black-colored photosensitive resin composition for contact panel of the present invention, can not be subject to particular restriction and use black organic pigment, colour mixture organic pigment or inorganic series pigments etc.As black organic pigment, for example can be being that perylene is black, Hua Jing is black, nigrosine etc.As colour mixture organic pigment, can be to mix at least two or more pigment being selected from red, blue, green, purple, yellow, cyanic colours, carmetta etc., the organic pigment that has carried out plan black.As inorganic series pigments, can be that carbon black, chromium oxide, iron oxide, titanium are black, oxynitriding titanium, titanium nitride etc.These light screening materials can use separately a kind, also can suitably select two or more to use, but from light-proofness, surface smoothness, dispersion stabilization, consider especially preferably carbon black with the good angle of the compatibility of resin.
In black-colored photosensitive resin composition of the present invention, except above-mentioned (A)～(E), preferably use solvent adjustment viscosity.As solvent, can be for example methyl alcohol, ethanol, n-propanol, isopropyl alcohol, ethylene glycol, the alcohols such as propylene glycol, α-or the terpene such as β-terpilenol, acetone, methyl ethyl ketone, cyclohexanone, the ketones such as METHYLPYRROLIDONE, toluene, dimethylbenzene, the aromatic hydrocarbons such as tetramethylbenzene, cellosolve, methyl cellosolve, ethyl cellosolve, carbitol, methyl carbitol, ethyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dihydroxypropane single-ether, dipropylene glycol monomethyl ether, DPE, triethylene glycol monomethyl ether, the glycol ethers such as Triethylene glycol ethyl ether, ethyl acetate, butyl acetate, cellosolve acetic acid esters, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetic acid esters, ethyl carbitol acetic acid esters, acetate of butyl carbitol, propylene glycol methyl ether acetate, the acetate esters such as propylene glycol monoethyl ether acetate, etc., use these solvents, by dissolving, mix, can form uniform molten liquid composition.
In addition,, in black-colored photosensitive resin composition of the present invention, can add as required the adjuvants such as curing accelerator, thermal polymerization inhibitor, plastifier, packing material, solvent, levelling agent, defoamer, coupling agent, surfactant.As thermal polymerization inhibitor, can enumerate quinhydrones, hydroquinone monomethyl ether, pyrogallol, tert-butyl catechol, phenothiazine etc., as plastifier, can enumerate dibutyl phthalate, dioctyl phthalate, tricresyl phosphate etc., as packing material, glass fibre, silica, mica, alumina etc. can be enumerated, as defoamer and levelling agent, silicone-based, fluorine system, acrylic acid series compound can be enumerated.In addition, as surfactant, can enumerate fluorine is surfactant, silicone-based surfactant etc., as silane coupling agent, can enumerate 3-(glycidoxypropyl) propyl trimethoxy silicane, 3-isocyanate group propyl-triethoxysilicane, 3-urea groups propyl-triethoxysilicane etc.
About the preferred composition of each composition of (A) in black-colored photosensitive resin composition～(E), with respect to (A) 100 mass parts, (B) be 10～60 mass parts, (C) be 10～80 mass parts, in addition, (D) with respect to (A) and 100 mass parts of total amount (B), be 2～40 mass parts.More preferably, with respect to (A) 100 mass parts, (B) being 30～50 mass parts, is (C) 20～70 mass parts, in addition,, with respect to (A) and 100 mass parts of total amount (B), is (D) 3～30 mass parts.In solid constituent (comprising the monomer component that forms solid constituent because of photocuring reaction), (E) account for 40～60 quality % of solid constituent.
Contact panel of the present invention contains above-mentioned (A)～(E) as principal ingredient with black-colored photosensitive resin composition.For photosensitive polymer combination solution, in the solid constituent (forming the monomer component of solid constituent after comprising photocuring) except after desolventizing, (A)～(E) become subtotaling containing more than 70 quality %, preferably containing more than 80 quality %, more preferably containing more than 90 quality %.The amount of solvent changes depending on target viscosities, but preferred in the scope of 60～90 quality % in photosensitive polymer combination solution.
Contact panel black film of the present invention uses black-colored photosensitive resin composition for contact panel of the present invention, utilize photoetching process and form.Its manufacturing process can adopt with the following method: first, by photosensitive polymer combination solution coat to substrate surface, then make solvent seasoning (prebake conditions), afterwards, on the film of gained thus, put photomask, irradiation ultraviolet radiation solidifies exposure portion, make the stripping of unexposed portion with aqueous alkali again, develop, form pattern, then carry out rear baking as rear curing.Here as the substrate of photosensitive resin coating composition solution, use glass, hyaline membrane (such as polycarbonate, polyethylene terephthalate, polyethersulfone etc.) etc..
As by photosensitive polymer combination solution coat to the method on substrate, except known solution dipping method, spray-on process, can also adopt any methods such as the method that uses roll coater, mould to be coated with machine, slit coater, rotary coating machine.Be coated with into after desirable thickness by these methods, except desolventizing (prebake conditions), forming film.Prebake conditions is by carrying out with the heating such as baking box, hot plate.Heating-up temperature when prebake conditions and heat time can suitably be selected according to used solvent, for example, at the temperature of 60～110 DEG C, toast 1～3 minute.
The exposure exposure machine carrying out after prebake conditions carries out, and is exposed by photomask by being situated between, and only makes the photosensitive polymer combination sensitization with pattern corresponding part.Exposure machine and exposure irradiation condition thereof can suitably be selected, and use the light sources such as ultrahigh pressure mercury lamp, high-pressure sodium lamp, metal halide lamp, far ultraviolet lamp to expose, and make the photosensitive polymer combination photocuring in film.
The photosensitive polymer combination that alkali after exposure develops to remove unexposed portion is that object is carried out, and by this development, forms desirable pattern.As the developer solution that is applicable to this alkali development, can be for example aqueous solution, the aqueous solution of alkali-metal oxyhydroxide etc. of the carbonate of alkaline metal, alkaline-earth metal, but the weak alkaline aqueous solution that uses the carbonate such as sodium carbonate, sal tartari that contains 0.03～1 % by weight is especially good while development at the temperature of 23～27 DEG C, can use commercially available developing machine, supersonic wave cleaning machine etc. to form accurate fine image.
After developing by this method, under the temperature of 200～240 DEG C, the condition of 20～60 minutes, heat-treat (baking afterwards).The object of carrying out this rear baking is to improve the adhesiveness between the figuratum black film of etching and substrate etc.This rear baking is the same with prebake conditions, by carrying out with the heating such as baking oven, hot plate.The figuratum black film of etching of the present invention forms through utilizing above photolithographic each operation.
Contact panel of the present invention can form pattern by photoetching with black-colored photosensitive resin composition, and developing property is especially excellent, and the black film of formation also has ability and be exposed for the sufficient chemical proofing etc. of the manufacturing procedure such as circuit formation of making contact panel.
Embodiment
Below by embodiment, the present invention will be described in more detail, but the present invention is not limited to these embodiment.
Embodiment
(modulation of black-colored photosensitive resin composition)
Allocate by the composition shown in table 1, modulate the black-colored photosensitive resin composition of embodiment 1～15 and comparative example 1.The each composition using in allotment is as follows:
(A) alkali soluble resin: the propylene glycol methyl ether acetate solution (resin solid constituent concentration 56.5%, Zhu Jin chemical company of Nippon Steel product, trade name V259ME) with the epoxy acrylate acid addition product of fluorene skeleton
(B) photopolymerizable monomer: the potpourri of dipentaerythritol acrylate and dipentaerythritol five acrylate (Japanese chemical drug company product, trade name DPHA)
(C) epoxy compound:
(C)-1: bisphenol A type epoxy resin (the product J ER828 of Mitsubishi Chemical Ind, the average functional group number 2.0 in epoxide equivalent 190,1 molecules)
(C)-2:3,4-7-oxa-bicyclo[4.1.0 carboxylic acid (3 ', 4 '-epoxycyclohexyl) methyl esters (the products C elloxide2021P of Daicel company, the average functional group number 2.0 in epoxide equivalent 135,1 molecules)
(C)-3: multi-functional epoxy compound's (the product HP7200L of DIC company, average functional group number 2.2 in epoxide equivalent 247,1 molecules) with bicyclopentadiene skeleton
(C)-4: multi-functional epoxy compound's (the product HP7200H of DIC company, average functional group number 3.0 in epoxide equivalent 276,1 molecules) with bicyclopentadiene skeleton
(C)-5: phenol novolak type epoxy resin (the product J ER154 of Mitsubishi Chemical Ind, the average functional group number 3.0 in epoxide equivalent 178,1 molecules)
(D) Photoepolymerizationinitiater initiater: 1-(9-ethyl-6-(2-methyl benzoyl) carbazole-3 base) ethyl ketone=O-acetyl group oxime (BASF AG's product, trade name Irgacure OXEO2)
(E) light screening material: the carbon black dispersion of the propylene glycol methyl ether acetate solvent of carbon black concentration 25 % by weight, dispersion resin (using alkali soluble resin (A)) 8 % by weight, macromolecule dispersing agent 2 % by weight
(F) solvent:
(F)-1: propylene glycol methyl ether acetate
(F)-2: cyclohexanone
(F)-3: ethoxyl ethyl propionate
(G) surfactant
(H) silane coupling agent (1% cyclohexanone solution)
Table 1
Table 1-1
Table 1-2
(evaluation of black-colored photosensitive resin composition: developability)
The black-colored photosensitive resin composition solution of embodiment 1～15 and comparative example 1 is applied to rotary coating machine on the glass plate of the thick 1.2mm that cleaning by degreasing crosses, be dried, after forming the dry film thickness of 1.2 μ m, photomask in attaching, the illumination under the high voltage mercury lamp radiation wavelength 365nm of use 500W is 10mW/cm
210 seconds of ultraviolet ray.After exposure, under 23 DEG C, 60 seconds, the condition of pressure 0.1MPa, develop with 0.4% aqueous sodium carbonate, remove the unexposed portion of film, afterwards, use air drier to be heating and curing at 230 DEG C and process 30 minutes.
The state of the black film patterned surfaces forming by visual judgement, with the formation of microscopic examination fine rule, measures the minimum pattern width that reaches predetermined pattern size.
Surface state
Zero: surface is glossy, has no deteriorated
△: tarnish, find that surface has deteriorated
×: surface is seriously coarse, finds deteriorated
(evaluation of black-colored photosensitive resin composition: chemical proofing)
The black-colored photosensitive resin composition solution of embodiment 1～15 and comparative example 1 is applied to rotary coating machine on the glass plate of the thick 1.2mm that cleaning by degreasing crosses, be dried, after forming the dry film thickness of 1.2 μ m, do not use photomask, on whole of black film formation use glass plate, the illumination under the high voltage mercury lamp radiation wavelength 365nm of use 500W is 10mW/cm
210 seconds of ultraviolet ray.After exposure, under 23 DEG C, 60 seconds, the condition of pressure 0.1MPa, carry out developer solution processing with 0.4% aqueous sodium carbonate.Afterwards, using air drier to be heating and curing at 230 DEG C processes 30 minutes.
Gained sample is impregnated in the solution that remains on 80 DEG C being made up of the mixed liquor of 2-ethylaminoethanol 30 mass parts, glycol ether 70 mass parts, after 10 minutes, pulls out, with pure water cleaning, dry, make the impregnated sample of chemicals.
Residual film ratio
To determining thickness through the impregnated sample of chemicals with surfaceness instrumentation, calculate residual film ratio.
Thickness after residual film ratio (%)=dipping (μ m)/thickness (μ m) × 100 before dipping
Adhesiveness
Cut carrying out cross on the impregnated film of chemicals, make film be at least 100 gos grid-like, then, carry out disbonded test with cellophane tape, by the state of visual valuation grid.
Zero: have no at all and peel off
△: find to peel off on a small quantity
×: film is peeled off substantially
The evaluation result of black-colored photosensitive resin of the present invention is shown in table 2.
Table 2
Table 2-1
Table 2-2
From the result of embodiment 1～15 and comparative example 1, by adding (C) epoxy compound, except having maintained the characteristic of fine pattern that can form 7 μ m, use the strong basicity chemicals using in manufacturing procedure to process, the film loss amount of black film is also few, is also maintained with the adhesiveness of glass substrate.Particularly in use 1 molecule, have in the embodiment 10～15 of epoxy resin of 3 functional groups, in adhesiveness test, have no grid completely and peel off, especially effective.
The chemical proofing excellence of black photosensitive composition of the present invention, thereby can before using the manufacturing procedure of strong basicity stripper etc., be pre-formed black film.And, can carry out pattern formation by photoetching, thereby have advantages of and can form with existing photo-mask process, and because mode that can film forms the slimming that can contribute to structure, be applicable to the formation of the black film of contact panel in making.
Claims (5)
1. contact panel black-colored photosensitive resin composition, contain: (A) alkali soluble resin, it is by making (a) dicarboxylic acid, tricarboxylic acids or its acid anhydrides and (b) tetrabasic carboxylic acid or its dianhydride react and obtain with the reactant of the monocarboxylic acid that contains unsaturated group with (a)/(b) mol ratio in 0.1～10 scope and the epoxy compound with 2 glycidyl ethers that derived by bisphenols; (B) there is the photopolymerizable monomer of at least 1 alkene unsaturated link; (C) there is the compound of epoxy radicals; (D) Photoepolymerizationinitiater initiater; (E) light screening material; Wherein, with respect to (A) 100 mass parts, (B) be 10～60 mass parts, (C) be 10～80 mass parts, and with respect to (A) and 100 mass parts of total amount (B), (D) be 2～40 mass parts, and (E) accounts for 40～60 quality % in solid constituent.
2. contact panel black-colored photosensitive resin composition according to claim 1, is characterized in that, described (C) has at least 3 epoxy radicals in 1 molecule.
3. solidfied material, it is heating and curing and obtains again after requiring black-colored photosensitive resin composition described in 1 or 2 to be situated between to be formed by photoetching process by right to use.
4. contact panel, it has solidfied material claimed in claim 3.
5. display device, it has contact panel claimed in claim 4.
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| JP2013013000A JP6139894B2 (en) | 2013-01-28 | 2013-01-28 | Black photosensitive composition for touch panel and touch panel |
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| CN105467761A (en) * | 2014-09-30 | 2016-04-06 | 新日铁住金化学株式会社 | Photosensitive resin composition used for touch screen, and hardening film thereof, and touch screen with hardening film |
| CN105938297A (en) * | 2015-03-04 | 2016-09-14 | 太阳油墨制造株式会社 | Etching resisting composition and dry film |
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| JP6607682B2 (en) * | 2015-03-05 | 2019-11-20 | 日鉄ケミカル＆マテリアル株式会社 | Black resin composition for light-shielding film, substrate with light-shielding film having light-shielding film obtained by curing said composition, and color filter and touch panel having said substrate with light-shielding film |
| JP2017156590A (en) * | 2016-03-02 | 2017-09-07 | 太陽インキ製造株式会社 | Photosensitive resin composition, dry film, cured product and printed wiring board prepared therewith |
| JP6886782B2 (en) * | 2016-06-30 | 2021-06-16 | 東京応化工業株式会社 | A photosensitive resin composition, a cured film, a bank for partitioning a light emitting layer in an organic EL element, a substrate for an organic EL element, an organic EL element, a method for producing a cured film, a method for producing a bank, and a method for producing an organic EL element. |
| JP6872302B2 (en) * | 2017-03-24 | 2021-05-19 | 株式会社タムラ製作所 | Black photosensitive resin composition |
| JP6797265B2 (en) * | 2019-10-21 | 2020-12-09 | 日鉄ケミカル＆マテリアル株式会社 | A black resin composition for a light-shielding film, a substrate with a light-shielding film having a light-shielding film obtained by curing the composition, and a color filter and a touch panel having the substrate with the light-shielding film. |
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| TWI607281B (en) | 2017-12-01 |
| CN103969948B (en) | 2019-10-01 |
| KR20140097008A (en) | 2014-08-06 |
| KR102180655B1 (en) | 2020-11-19 |
| JP6139894B2 (en) | 2017-05-31 |
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