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CN102591148A - Colored photosensitive resin composition for touch panel, touch panel and display device - Google Patents

Colored photosensitive resin composition for touch panel, touch panel and display device Download PDF

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Publication number
CN102591148A
CN102591148A CN2012100053438A CN201210005343A CN102591148A CN 102591148 A CN102591148 A CN 102591148A CN 2012100053438 A CN2012100053438 A CN 2012100053438A CN 201210005343 A CN201210005343 A CN 201210005343A CN 102591148 A CN102591148 A CN 102591148A
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China
Prior art keywords
methyl
compound
acid
contact panel
photosensitive composition
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Granted
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CN2012100053438A
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CN102591148B (en
Inventor
铃木茂
山口尚人
塩田大
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Tokyo Ohka Kogyo Co Ltd
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Tokyo Ohka Kogyo Co Ltd
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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133512—Light shielding layers, e.g. black matrix
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • 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

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Epoxy Resins (AREA)
  • Position Input By Displaying (AREA)

Abstract

The invention provides a colored photosensitive resin composition, which possesses excellent chemical resistance and weather resistance, and is adaptive for touch panel, and the touch panel and display device applying the composition. The colored photosensitive resin composition provided in the utility model includes the components as following: (A) binder compound, (B) photopolymerizable monomer, (C) photopolymerization initiator and (D) colorant, wherein (A) binder compound includes epoxy compound, preferably, the compound indicated in the formular (A-1). In the formular, Ra1 indicates the organic compound with k active hydrogen groups wherein the active hydrogen group are removed, n1,..., nk indicates integer from 1 to 100, the summation is from 1 to 100, k indicates an integer from 1 to 100, and A indicates an oxygen cyclohexane skeleton with a substituent such as an epoxy group or an oxygen norbornene skeleton.

Description

The photosensitive composition and contact panel and the display device that are used for contact panel
Technical field
The present invention relates to a kind of photosensitive composition and contact panel and display device that is used for contact panel.
Background technology
At present, the input media as in the display device with LCD etc. uses contact panel widely.Wherein, owing to optics shows reasons such as bright and simple in structure, the contact panel of capacitive way receives the concern of industry.
The contact panel of capacitive way has: dielectric material, respectively in the dielectric material both sides with formed the 1st electric conductor of different pattern and the 2nd electric conductor.The 1st electric conductor and the 2nd electric conductor are via (active area) links to each other with external control circuit with the formed derivation distribution of exterior domain in the zone of action.According to the contact panel of this capacitive way, the position that electromagnetic change that is produced in the time of can be based on external conductor (being generally finger) contact or near contact panel or capacitance variations detect external conductor.
Patent documentation 1: Japanese Patent Laid is opened the 2010-198615 communique
Summary of the invention
Yet for can be with metal as the 1st electric conductor and the 2nd electric conductor in this contact panel, the someone proposes the 1st electric conductor and the 2nd electric conductor are hidden in the back (with reference to patent documentation 1) of black-face picture tube.In addition, lose the derivation distribution in order to make to look sideways from user one, also the someone attempts deriving the back that distribution is hidden in black-face picture tube.In this case, owing to after forming black-face picture tube, need carry out processing such as etching to metal film, so become key factor as its chemical resistance of material of black-face picture tube.
In addition, under situation, become key factor in the display device applications that will have contact panel as its against weather of material of black-face picture tube like the vehicle-mounted purposes of auto-navigation system.
But, the black-face picture tube of colored filter is being diverted under the situation of contact panel purposes with photosensitive composition, exist and do not reaching the problem that requires standard aspect chemical resistance or the against weather.
The present invention accomplishes in view of above-mentioned problem, its purpose be to provide chemical resistance and against weather excellent and be applicable to the contact panel purposes the photosensitive composition that is used for contact panel, have the contact panel of this formed solidified resin pattern of photosensitive composition that is used for contact panel and display device with this contact panel.
The inventor etc. have carried out wholwe-hearted research repeatedly for realizing above-mentioned purpose.The result finds, can solve above-mentioned problem through adding epoxy compound as the binder compound of photosensitive composition, thereby accomplish the present invention.Particularly, the present invention provides following content.
First embodiment of the present invention relates to a kind of photosensitive composition that is used for contact panel; It contains (A) binder compound, (B) photopolymerization monomer, (C) Photoepolymerizationinitiater initiater and (D) colorant, and above-mentioned (A) binder compound comprises epoxy compound.
Second embodiment of the present invention is the contact panel with the solidified resin pattern that uses the photosensitive composition that is used for contact panel in first embodiment and form.
The 3rd embodiment of the present invention is the display device with the contact panel in second embodiment.
According to the present invention, can provide chemical resistance and against weather excellent and be applicable to the contact panel purposes the photosensitive composition that is used for contact panel, have contact panel that uses this formed solidified resin pattern of photosensitive composition that is used for contact panel and display device with this contact panel.
Embodiment
" photosensitive composition that is used for contact panel "
The photosensitive composition (being designated hereinafter simply as " photosensitive composition ") that is used for contact panel of the present invention contains (A) binder compound, (B) photopolymerization monomer, (C) Photoepolymerizationinitiater initiater and (D) colorant.Below, each composition that is contained in the photosensitive composition is described.
(A) binder compound
Photosensitive composition of the present invention contains epoxy compound as (A) binder compound (below be also referred to as " (A) composition ").
As epoxy compound, not special the qualification can be used the existing known epoxy compound with cementing agent effect, but wherein from the represented epoxy compound of the preferred following formula of the viewpoint of chemical resistance and against weather (A-1).
[changing 1]
[in the formula, R A1Be to have the residue of removing the reactive hydrogen base in the organic compound of k reactive hydrogen base; N1, n2 ..., nk representes 0～100 integer respectively independently, its summation is 1～100; K representes 1～100 integer; A has oxygen cyclohexane (oxycyclohexane) skeleton of substituent B or oxygen ENB (oxynorbornene) skeleton with substituent B, by following formula (A-2) or (A-3) expression A.
[changing 2]
(in the formula, B is respectively independently by following formula (A-4), formula (A-5) or the represented group of formula (A-6);
[changing 3]
Wherein, in this epoxy compound, contain the represented group of above-mentioned formula (A-4) more than 1.R A2Expression alkyl, alkyl-carbonyl or aryl carbonyl)].
In the above-mentioned formula (A-1), R A1Be to have the residue of removing the reactive hydrogen base in the organic compound of reactive hydrogen base; Promptly have the organic compound of reactive hydrogen base as its precursor, can enumerate: alcohols, phenols, carboxylic acids, amine, thio-alcohol etc.
As above-mentioned alcohols, can be that monohydroxy alcohol also can be a polyvalent alcohol.Can enumerate particularly: aliphatic alcohols such as methyl alcohol, ethanol, propyl alcohol, butanols, amylalcohol, hexanol, octanol; Aromatic alcohols such as phenmethylol; Monoethylene glycol, diethylene glycol, triethylene glycol, polyglycol, propylene glycol, dipropylene glycol, 1; 3-butylene glycol, 1; 4-butylene glycol, pentanediol, 1,6-hexanediol, neopentyl glycol, hydroxy new pentane acid DOPCP (hydroxypivalic acid neopentylglycol ester), cyclohexanedimethanol, glycerine, polyvalent alcohols such as two glycerine, polyglycereol, trimethylolpropane, trimethylolethane, pentaerythrite, dipentaerythritol etc. that contract.
As above-mentioned phenols; Can enumerate: phenol, cresols, catechol, pyrogallol, p-dihydroxy-benzene, hydroquinone monomethyl ether, bisphenol-A, Bisphenol F, 4,4 '-dihydroxy benaophenonel, bisphenol S, phenolics, cresol novolac resin (cresol novolac resin) etc.
As above-mentioned carboxylic acids, can enumerate: the fatty acid of formic acid, acetate, propionic acid, butyric acid, vegetable and animals oils, fumaric acid, maleic acid, hexane diacid, dodecanedioic acid, trimellitic acid, Pyromellitic Acid, polyacrylic acid, phthalic acid, m-phthalic acid, terephthalic acid (TPA) etc.In addition, also can enumerate: lactic acid, citric acid, hydroxycaproic acid (oxycaproic acid) etc. have the compound of hydroxyl and carboxyl simultaneously.
As above-mentioned amine; Can enumerate: monomethyl amine, dimethylamine, monoethyl amine, diethylamine, propylamine, monobutylamine (MBA), dibutylamine, amylamine, hexylamine, cyclohexylamine, octylame, lauryl amine, 4,4 '-diaminodiphenyl-methane, IPD, toluene diamine, cyclohexanediamine, xylylene diamines, diethylene triamine, trien, monoethanolamine etc.
As above-mentioned thio-alcohol, can enumerate: mercapto classes such as methyl mercaptan, ethyl mercaptan, propanethiol, benzenethiol; The polyol ester of glycol dimercaptopropionate (ethylene glycol dimercaptopropionic acid ester), trimethylolpropane tris mercaptopropionic acid ester (trimethylolpropane trimercaptopropionic acid ester), pentaerythrite four mercaptopropionic acid esters mercaptopropionic acids such as (pentaerythritol tetramercaptopropionic acid ester) or mercaptopropionic acid etc.
In addition; As organic compound, also can enumerate: polyvinyl alcohol (PVA), polyvinyl acetate partial hydrolystate, starch, cellulose, cellulose acetate, cellulose acetate-butyrate, hydroxyethyl cellulose, acrylic polyol resin, styrene-propene alcohol copolymer resins, styrene-maleic acid copolymer resins, alkyd resin, polyester polyol resin, polyester carboxylic acid resin, polycaprolactone polyol resin, polypropylene polyvalent alcohol, polytetramethylene glycol (polytetramethylene glycol) etc. with reactive hydrogen base.
This has the organic compound of reactive hydrogen base, also can in its skeleton, have unsaturated double-bond.As concrete example, can enumerate: vinylcarbinol, acrylic acid, methacrylic acid, 3-cyclohexene methyl alcohol, tetrahydrophthalic acid etc.
The organic compound that more than has the reactive hydrogen base can use separately or combination use more than 2 kinds.
In the above-mentioned formula (A-1), n1, n2 ..., nk representes 0～100 integer respectively independently, its summation is 1～100.In addition, k representes 1～100 integer.
N1, n2 ..., nk is preferably 2～10 integer, more preferably 3～6 integer respectively independently.In addition, n1, n2 ..., nk summation be preferably 4～30, more preferably 4～20.Through above-mentioned summation is set at more than 4, can improves the cross-linking density after the curing, thereby can improve hardness.In addition, through above-mentioned summation is set at below 30, can improve the dissolubility in solvent, thereby can improve operability.
In the above-mentioned formula (A-1), A has the oxygen cyclohexane skeleton of substituent B or an oxygen ENB skeleton with substituent B, by above-mentioned formula (A-2) or (A-3) expression A.Preferably, by above-mentioned formula (A-2) expression A.In addition, k A can be respectively identical also can be different.
In the represented epoxy compound of above-mentioned formula (A-1), must contain the represented group of above-mentioned formula (A-4) more than 1, this group is The more the better.On the other hand, the represented group of above-mentioned formula (A-6) is few more good more.
The represented epoxy compound of above-mentioned formula (A-1); Can make through the following mode described in the japanese patent laid-open 7-119270 communique: the organic compound that will have the reactive hydrogen base is as initiating agent; With Peracetic acid or hydrogen peroxide etc.; Carry out epoxidation to making 4 vinyl cyclohexene-1-oxide or 5-vinyl two ring [2.2.1] hept-2-ene"-2-oxides and potpourri carry out the polyether resin that ring-opening polymerization obtained (that is, having the polyether resin that vinyl side chain and cyclohexane skeleton perhaps have vinyl side chain and ENB skeleton) with compound of 1 epoxy radicals.
As suitable commercially available article, can enumerate: the EHPE3150 (the summation average out to 15 of n1～nk) of ダ イ セ Le chemical industry society system.
In addition, as epoxy compound, also can use the alicyclic epoxy compound.
As the alicyclic epoxy compound, can enumerate: 3,4-epoxycyclohexyl methyl-3 '; 4 '-epoxycyclohexane carboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiral shell-3; The 4-epoxy radicals) cyclohexane-methyl-dioxs (2-(and 3,4-epoxycyclohexyl-5,5-spiro-3; 4-epoxy) cyclohexane-meta-dioxane), two (3,4-epoxycyclohexyl methyl) adipate (adipate), two (3,4-epoxy radicals-6-methyl cyclohexane ylmethyl) adipate, 3; 4-epoxy radicals-6-methylcyclohexyl-3 ', 4 '-epoxy radicals-6 '-methylcyclohexanecarboxylic acid ester, 6-caprolactone modification 3,4-epoxycyclohexyl methyl-3 '; 4 '-epoxycyclohexane carboxylate, trimethyl caprolactone modification 3,4-epoxycyclohexyl methyl-3 ' 4 '-epoxycyclohexane carboxylate, Beta-methyl-δ-Wu Neizhi modification 3,4-epoxycyclohexyl methyl-3 '; 4 '-epoxycyclohexane carboxylate, di-2-ethylhexylphosphine oxide (3; The 4-7-oxa-bicyclo[4.1.0), two of monoethylene glycol (3,4-epoxycyclohexyl methyl) ether, ethene two (3, the 4-epoxycyclohexane carboxylate), epoxy basic ring di-2-ethylhexyl hexahydrophthalates, epoxy basic ring di-2-ethylhexyl hexahydrophthalate etc.
As suitable commercially available article; Can enumerate: セ ロ キ サ イ De 2021, the 2021P, 2081,2083,2085 of ダ イ セ Le chemical industry society system; エ Port リ one De GT-300, GT-301, GT-302, GT-400,401,403 etc., or new daily use chemicals エ Port キ シ makes the サ Application ト one ト ST-3000, ST-4000, ST-5080, ST-5100 of society's system etc.
In addition, as epoxy compound, also can use: phenolic epoxy compound, bisphenol type epoxy compound, cresol-novolak type epoxy compound, biphenyl type epoxy compound etc.
As above-mentioned phenolic epoxy compound, preferred epoxide equivalent is 200～220 phenolic epoxy compound.As commercially available article, can enumerate: the エ ピ Network ロ Application N-660 of big Japanese イ Application キ society system, N-665, N-670, N-673, N-680, N-690, N-695, N-685-EXP, N-672-EXP, N-655-EXP-S, N-865, N-865-80M, YDCN-701, YDCN-702, YDCN-703, YDCN-704, YDCN-704L etc.
Commercially available article as above-mentioned bisphenol type epoxy compound; Can enumerate: the エ Port ト one ト YD-115 of the society of daily use chemicals エ Port キ シ manufacturing newly system, YD-118T, YD-127, YD-128, YD-134, YD-8125, YD-7011R, ZX-1059, YDF-8170, YDF-170 etc.; Or デ Na コ one Le EX-1101 of Na ガ セ ケ system テ Star Network ス society system, EX-1102, EX-1103 etc., or プ ラ Network セ Le GL-61 of ダ イ セ Le chemical industry society system, GL-62, G101, G102 etc.
Commercially available article as above-mentioned cresol-novolak type epoxy compound; Can enumerate: the エ Port ト one ト YDPN-638 of new daily use chemicals エ Port キ シ system society system, YDPN-701, YDPN-702, YDPN-703, YDPN-704 etc., or デ Na コ one Le-125 of Na ガ セ ケ system テ Star Network ス society system etc.
As above-mentioned biphenyl type epoxy compound, can enumerate: 3,5,3 ', 5 '-tetramethyl-4,4 '-diglycidyl biphenyl etc.
Preferably, photosensitive composition of the present invention except that containing above-mentioned epoxy compound, further contains other binder compound.As this other binder compound; Can enumerate: (methyl) acrylic acid, fumaric acid, maleic acid, monomethyl fumarate, monomethyl ester, (methyl) acrylic acid 2-hydroxyl ethyl ester, glycol monoethyl ether (methyl) acrylic ester, ethylene glycol monoethyl ether (methyl) acrylic ester, (methyl) acrylic acid glyceride, (methyl) acrylic amide, vinyl cyanide, methacrylonitrile, (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) isobutyl acrylate, (methyl) 2-EHA, (methyl) benzyl acrylate, ethylene glycol bisthioglycolate (methyl) acrylic ester, diethylene glycol diacrylate, triethylene glycol two (methyl) acrylic ester, TEG two (methyl) acrylic ester, butanediol dimethylacrylate, propylene glycol two (methyl) acrylic ester, trimethylolpropane tris (methyl) acrylic ester, tetra methylol propane four (methyl) acrylic ester, pentaerythrite three (methyl) acrylic ester, pentaerythrite four (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, dipentaerythritol six (methyl) acrylic ester, two (methyl) acrylic acid-1, the oligomer class of polymerization takes place in the own diester of 6-, cardo-epoxy diacrylate (cardo epoxy diacrylate) etc.; The polyester prepolyer that makes polyalcohols and monoacid or polyprotonic acid condensation gained reacts with (methyl) acrylic acid and polyester (methyl) acrylic ester that obtains; After polyvalent alcohol and the compound with 2 NCOs are reacted, again with the reaction of (methyl) acrylic acid, the polyurethane that is obtained (methyl) acrylic ester; Epoxy radicals (methyl) acrylate resin that epoxy resin such as bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, phenol or cresols novolac epoxy resin, solvable phenol aldehyde type epoxy resin, triphenol methylmethane type epoxy resin, poly carboxylic acid poly glycidyl ester, polyvalent alcohol poly glycidyl ester, aliphatics or cycloaliphatic epoxy resin, amine epoxy resin, dihydroxy benzenes type epoxy resin and (methyl) acrylic acid is reacted and obtain etc.In addition, can be fit to make the resin of multi-anhydride and epoxy (methyl) acrylate resin reaction formation.
In addition; As other binder compound, the resin that the following method of use that also can suit obtains, promptly; Make epoxy compound obtain reactant, further make the reaction of this reactant and multi-anhydride and the acquisition resin with the carboxylic acid compound reaction that contains unsaturated group.Wherein, consider the represented compound of preferred following formula (A-7) from the higher aspect of the curable of himself.
[changing 4]
Figure BDA0000129591940000071
In the above-mentioned formula (A-7), X representes with the represented group of following formula (A-8).
[changing 5]
Figure BDA0000129591940000072
In the above-mentioned formula (A-8), R A3Represent independently that respectively hydrogen atom, carbon number are 1～6 alkyl or halogen atom, R A4Represent hydrogen atom or methyl respectively independently, W representes singly-bound or the represented group of following formula (A-9).
[changing 6]
In addition, in the above-mentioned formula (A-7), Y representes from dicarboxylic anhydride, to remove anhydride group (residue CO-O-CO-).As dicarboxylic anhydride, can enumerate: maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrabydrophthalic anhydride, hexahydrophthalic anhydride, methyl inner methylidyne tetrahydric phthalic anhydride (methyl endomethylenetetrahydrophthalic anhydride), HET acid acid anhydride, methyl tetrahydrophthalic anhydride, glutaric anhydride etc.
In addition, in the above-mentioned formula (A-7), Z representes from the tetracarboxylic dianhydride, to remove the residue of 2 anhydride group.As the tetracarboxylic dianhydride, for example can enumerate: pyromellitic dianhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, diphenyl ether tetracarboxylic dianhydride etc.
In addition, in the above-mentioned formula (A-7), m representes 0～20 integer.
The acid value of the compound that above-mentioned formula (A-7) is represented in the resin solid composition, is preferably 10～150mgKOH/g, more preferably 70～110mgKOH/g.Through acid value is set at more than the 10mgKOH/g, can obtain development property fully.In addition,, sufficient curable can be obtained, superficiality can be improved through acid value is set at below the 150mgKOH/g.
In addition, the matter average molecular weight of the represented compound of above-mentioned formula (A-7) is preferably 1000～40000, more preferably 2000～30000.Through the matter average molecular weight is set at more than 1000, can improve thermotolerance and film strength.In addition, through the matter average molecular weight is set at below 40000, can obtain sufficient dissolubility to imaging liquid.
With respect to the solid constituent of photosensitive composition of the present invention, (A) content of composition is preferably 30～90 quality %, more preferably 50～70 quality %.In addition, with respect to (A) composition total amount, the ratio of epoxy compound is preferably 30～70 quality %, more preferably 40～60 quality %.Be set at more than the 30 quality % through ratio, can improve chemical resistance and against weather epoxy compound.In addition, be set at below the 70 quality %, can prevent the decline of susceptibility or development property through ratio with epoxy compound.
(B) photopolymerization monomer
As (B) photopolymerization monomer (below be also referred to as " (B) composition "), not special the qualification can not used known in the past monofunctional monomer or polyfunctional monomer.
As above-mentioned monofunctional monomer; Can enumerate: (methyl) acrylic amide, methylol (methyl) acrylic amide, methoxy (methyl) acrylic amide, ethoxyl methyl (methyl) acrylic amide, propoxyl group methyl (methyl) acrylic amide, butoxy methoxy (methyl) acrylic amide, N-methylol (methyl) acrylic amide, N-methylol (methyl) acrylic amide, (methyl) acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, butenoic acid, 2-acrylic amide-2-methyl propane sulfonic acid, tert-butyl group acrylic amide sulfonic acid (tert-butyl acrylamide sulfonic acid), (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) butyl acrylate, (methyl) 2-EHA, (methyl) cyclohexyl acrylate, (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) acrylic acid 2-hydroxypropyl acrylate, (methyl) acrylic acid 2-hydroxy butyl ester, (methyl) acrylic acid 2-phenoxy group-2-hydroxypropyl acrylate, 2-(methyl) acryloyl-oxy-2-hydroxypropyl phthalic ester, glycerine list (methyl) acrylic ester, (methyl) tetrahydrofurfuryl acrylate, dimethylamino (methyl) acrylic ester, (methyl) glycidyl acrylate, 2; 2; 2-trifluoroethyl (methyl) acrylic ester, 2; 2; 3, half (methyl) acrylic ester of 3-tetrafluoro propyl group (methyl) acrylic ester, phthalic acid derivatives etc.These monofunctional monomers can use separately or combination use more than 2 kinds.
On the other hand; As above-mentioned polyfunctional monomer; Can enumerate: ethylene glycol bisthioglycolate (methyl) acrylic ester, diethylene glycol two (methyl) acrylic ester, TEG two (methyl) acrylic ester, propylene glycol two (methyl) acrylic ester, polypropylene glycol two (methyl) acrylic ester, butylene glycol two (methyl) acrylic ester, neopentyl glycol two (methyl) acrylic ester, 1; 6-hexanediol two (methyl) acrylic ester (1; 6-hexane glycol di (meth) acrylate), trimethylolpropane tris (methyl) acrylic ester, two (methyl) acrylic acid glyceride, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, dipentaerythritol five acrylic ester, dipentaerythritol acrylate, pentaerythrite two (methyl) acrylic ester, pentaerythrite three (methyl) acrylic ester, pentaerythrite four (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, dipentaerythritol six (methyl) acrylic ester, 2; Two (4-(methyl) the acryloxy diethoxy phenyl) propane, 2 of 2-; Two (4-(methyl) the acryloxy polyethoxy phenyl) propane of 2-, 2-hydroxyl-3-(methyl) acryloxy propyl group (methyl) acrylic ester, ethylene glycol diglycidylether two (methyl) acrylic ester, diethylene glycol diglycidyl ether two (methyl) acrylic ester, o-phthalic acid diglycidyl ester two (methyl) acrylic ester, glycerol tri-acrylate, glycerine polyglycidyl ether gather polyfunctional monomer such as the condensation product of (methyl) acrylic ester, carbamate (methyl) acrylic ester (urethane (meth) acrylate) (that is benzal diisocyanate), trimethyl hexamethylene diisocyanate and hexamethylene diisocyanate etc. and (methyl) acrylic acid 2-hydroxyl ethyl ester three's reactant, di-2-ethylhexylphosphine oxide (methyl) acrylic amide, (methyl) acrylic amide methylene ether ((meth) acrylamidemethylene ether), polyvalent alcohol and N-methylol (methyl) acrylic amide or triacryl formal (triacrylformal) etc.These multiple functional radical monomers can use separately or combination use more than 2 kinds.
With respect to (A) composition, (B) content of composition is preferably 20～60 quality %, more preferably 30～50 quality %.Through being set in above-mentioned scope, can improve curable, can make pattern become to become easy.
(C) Photoepolymerizationinitiater initiater
As (C) Photoepolymerizationinitiater initiater (below be also referred to as " (C) composition "), not special the qualification can not used known in the past Photoepolymerizationinitiater initiater.As this Photoepolymerizationinitiater initiater; Can enumerate: acetophenone, 2; The 2-diethoxy acetophenone (2,2-diethoxyacetophenone), to dimethyl acetophenone, to acetophenones such as dimethylamino propiophenone, dichloroacetophenone, trichloroacetophenone, p-tert.-butyl acetophenones; Benzophenone, 2-chlorobenzophenone, p, benzophenones such as p '-two (dimethylamino) benzophenone; Styrax ethers such as benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether; Thioxanthene, 2-diuril ton, 2, sulphur compounds such as 4-diethyl thioxanthene, 2-methyl thioxanthene, 2-isopropyl thioxanthene; 2-EAQ, prestox anthraquinone, 1, and 2-benzo anthraquinone (1,2-benzanthraquinone), 2,3-diphenyl anthraquinone (2,3-diphenylanthraquinone) wait the anthraquinone class; Benzoyl peroxide, dicumyl peroxide organic peroxides such as (cumene peroxide); Mercaptan compounds such as 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole; 2-(Chloro-O-Phenyl)-4, imidazolium compoundss such as 5-two (m-methoxyphenyl) imidazole dimer; To triaizine compounds such as methoxyl triazines; 2; 4,6-three (trichloromethyl)-s-triazine, 2-methyl-4, two (the trichloromethyl)-s-triazine of 6-, 2-[2-(5-methylfuran-2-yl) ethylidine]-4; Two (the trichloromethyl)-s-triazine of 6-, 2-[2-(furans-2-yl) ethylidine]-4; Two (the trichloromethyl)-s-triazine of 6-, 2-[2-(4-diethylin-2-tolyl) ethylidine]-4, two (the trichloromethyl)-s-triazine of 6-, 2-[2-(3, the 4-dimethoxy phenyl) ethylidine]-4; Two (the trichloromethyl)-s-triazine of 6-, 2-(4-anisyl)-4; Two (the trichloromethyl)-s-triazine of 6-, 2-(4-ethoxybenzene vinyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-n-butoxy phenyl)-4, two (the trichloromethyl)-s-triazine etc. of 6-have the triaizine compounds of halomethyl; 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butane-amino ketones compounds such as 1-ketone; Ethyl ketone-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-1-oxime ester compounds such as (O-acetyl oximes) etc.
In these compounds, from the susceptibility of keeping photosensitive composition fully, the viewpoint that improves the rectilinear propagation of pattern, preferred oxime ester compound.As this oxime ester compound, the represented compound of preferred following formula (C-1).
[changing 7]
Figure BDA0000129591940000111
In the above-mentioned formula (C-1), R C1Expression-NO 2Perhaps-COR C5In addition, R C5Expression heterocyclic radical, condensed ring formula aromatic series base or aromatic series base, and can contain substituting group.R C2～R C4The organic group of representing monovalence respectively independently.
As R C5Represented heterocyclic radical can be enumerated: contain the above heterocyclic radical of 5 yuan of rings of a kind of atom in nitrogen-atoms, sulphur atom and the oxygen atom, the heterocyclic radical of preferred 5 yuan of rings or 6 yuan of rings at least.As heterocyclic radical, for example can enumerate: nitrogenous 5 yuan of cyclic groups such as pyrrole radicals, imidazole radicals, pyrazolyl; Nitrogenous 6 yuan of cyclic groups such as pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl; The nitrogenous sulfenyl that contains such as thiazolyl, isothiazolyl; The nitrogenous oxygen bases that contain such as oxazolyl 、 isoxazolyl; Thienyl, thiapyran base etc. contain sulfenyl; Furyl, pyranose etc. contain oxygen base etc.Wherein, the heterocyclic radical that preferably contains 1 nitrogen-atoms or sulphur atom.Also can contain condensed ring in this heterocycle.As the heterocyclic radical that contains condensed ring, for example can enumerate benzothienyl etc.
As R C5Represented condensed ring formula aromatic series base can be enumerated: naphthyl, anthryl, phenanthryl etc.In addition, as R C1Represented aromatic series base can be enumerated phenyl.
Also can have substituting group in heterocyclic radical, condensed ring formula aromatic series base or the aromatic series base.Particularly at R C5Under the situation for the aromatic series base, preferably has substituting group.As this substituting group, can enumerate :-NO 2,-CN ,-SO 2R C6,-COR C6,-NR C7R C8,-R C9,-OR C9,-O-R C10-O-R C11Deng.
R C6Represent alkyl respectively independently, these groups also can be replaced by halogen atom, also can be interrupted because of ehter bond, thioether bond, ester bond.R C6In the carbon number of alkyl be preferably 1～5, for example can enumerate: methyl, ethyl, propyl group, isopropyl, butyl, isobutyl etc.
R C7, R C8Represent hydrogen atom, alkyl or alkoxy respectively independently, these groups also can be replaced by halogen atom, and wherein the alkylene moiety of alkyl and alkoxy can be interrupted because of ehter bond, thioether bond or ester bond.In addition, R C7Also can with R C8In conjunction with and form ring texture.R C7, R C8In alkyl or the carbon number of alkoxy be preferably 1～5, for example can enumerate: methyl, ethyl, propyl group, isopropyl, butyl, isobutyl, methoxyl, ethoxy, propoxyl group etc.
As R C7Can with R C8In conjunction with formed ring texture, can enumerate heterocycle.As this heterocycle, can enumerate the above heterocycle of 5 yuan of rings that contains nitrogen-atoms at least, the heterocycle of preferred 5～7 yuan of rings.Also can contain condensed ring in this heterocycle.For example can enumerate as heterocycle: piperidine ring, morpholine ring, thiomorpholine ring etc.Wherein preferred morpholine ring.
R C9Represent that part or all of hydrogen atom can be by the substituted alkyl of halogen atom.R C9In the carbon number of alkyl be preferably 1～5, for example can enumerate: methyl, ethyl, propyl group, isopropyl, butyl, isobutyl etc.
R C10, R C11Represent alkyl respectively independently, these groups also can be replaced by halogen atom, also can be interrupted because of, ehter bond, thioether bond, ester bond.Preferred carbon number and its concrete example and above-mentioned R C6Explanation identical.
Wherein, as R C5, can for example preferably enumerate: pyrrole radicals, pyridine radicals, thienyl, thiapyran base, benzothienyl, naphthyl, have substituent phenyl.
In the above-mentioned formula (C-1), R C2The organic group of expression monovalence.As this organic group, preferred-R C12,-OR C12,-COR C12,-SR C12,-NR C12R C13Represented group.R C12, R C13Represent alkyl, thiazolinyl, aryl, aralkyl or heterocyclic radical respectively independently; These groups also can be replaced by halogen atom, alkyl or heterocyclic radical, and wherein the alkylene moiety of alkyl and aralkyl also can be interrupted because of unsaturated link, ehter bond, thioether bond, ester bond.In addition, also can R C12With R C13In conjunction with forming ring texture jointly with nitrogen-atoms again.
As R C12, R C13Represented alkyl, preferred carbon number is 1～20 alkyl, more preferably carbon number is 1～5 alkyl.As alkyl, for example can enumerate: the group of a straight chain shape such as methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, n-pentyl, isopentyl, sec-amyl, tertiary pentyl, n-hexyl, n-heptyl, n-octyl, iso-octyl, secondary octyl, uncle's octyl group, n-nonyl, different nonyl, positive decyl, isodecyl or a chain.In addition, also can have substituting group in this alkyl.As having substituent alkyl, for example can enumerate: methoxyethoxyethyl, ethoxy ethoxy ethyl, propoxyl group ethoxyethyl group, methoxy-propyl etc.
As R C12, R C13Represented thiazolinyl, preferred carbon number is 1～20 thiazolinyl, more preferably carbon number is 1～5 thiazolinyl.As thiazolinyl, for example can enumerate: the group of straight or brancheds such as vinyl (vinyl), allyl, butenyl group, ethylidine (ethenyl), propinyl.In addition, also can have substituting group in this thiazolinyl.As having substituent thiazolinyl, for example can enumerate 2-! benzoxazole-2-yl) ethylidine etc.
As R C12, R C13Represented aryl, preferred carbon number is 6～20 aryl, more preferably carbon number is 6～10 aryl.As aryl, for example can enumerate: phenyl, tolyl, xylyl, ethylbenzene base, naphthyl, anthryl, phenanthryl etc.
As R C12, R C13Represented aralkyl, preferred carbon number is 7～20 aralkyl, more preferably carbon number is 7～12 aralkyl.As aralkyl, for example can enumerate: benzyl, α-Jia Jibianji, α, α-Er Jiajibianji, phenethyl, styryl etc.
As R C12, R C13Represented heterocyclic radical can be enumerated: contain the above heterocyclic radical of 5 yuan of rings of a kind of atom in nitrogen-atoms, sulphur atom and the oxygen atom, the heterocyclic radical of preferred 5～7 yuan of rings at least.Also can contain condensed ring in this heterocyclic radical.As heterocyclic radical, for example can enumerate: pyrrole radicals, pyridine radicals, pyrimidine radicals, furyl, thienyl etc.
These R C12, R C13In, the alkylene moiety of alkyl and aralkyl also can be interrupted because of unsaturated link, ehter bond, thioether bond, ester bond.
In addition, as R C12With R C13In conjunction with formed ring texture, can enumerate heterocycle.As this heterocycle, can enumerate the above heterocycle of 5 yuan of rings that contains nitrogen-atoms at least, the heterocycle of preferred 5～7 yuan of rings.Also can contain condensed ring in this heterocycle.As heterocycle, for example can enumerate: piperidine ring, morpholine ring, thiomorpholine ring etc.
Wherein, as R C2, most preferable, ethyl, propyl group, phenyl.
In the above-mentioned formula (C-1), R C3The organic group of expression monovalence.As this organic group, preferred carbon number is 1～5 alkyl, can have substituent carbon number is the represented group of 6～12 aryl, following formula (C-2) or can has substituent heterocyclic radical.As substituting group, can enumerate and above-mentioned R C5The identical group of situation.As carbon number is 6～12 aryl, can enumerate: phenyl, naphthyl, anthryl, phenanthryl etc.
[changing 8]
-R c14-R c15?(C-2)
In the above-mentioned formula (C-2), R C14Expression also can be 1～5 alkylidene by the carbon number that oxygen atom interrupts.As this alkylidene, can enumerate: methylene, ethylidene, positive propylidene, isopropylidene, positive butylidene, isobutylene, sec-butylidene, positive pentylidene, isopentylidene, secondary pentylidene straight or branched group.In these groups, R C14Most preferably be isopropylidene.
In the above-mentioned formula (C-2), R C15Expression-NR C16R C17Represented any monovalent organic radical (R C16, R C17The organic group of representing monovalence respectively independently).In this organic group, consider from the dissolubility aspect that can improve Photoepolymerizationinitiater initiater, as long as R C15Structure be the represented structure of following formula (C-3), then preferred.
[changing 9]
In the above-mentioned formula (C-3), R C18, R C19Represent independently that respectively carbon number is 1～5 alkyl.As this alkyl, can enumerate: methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, n-pentyl, isopentyl, sec-amyl, tertiary pentyl etc.Wherein, R C18, R C19Most preferably be methyl.
As R C3Represented heterocyclic radical can be enumerated: contain the above heterocyclic radical of 5 yuan of rings of a kind of atom in nitrogen-atoms, sulphur atom and the oxygen atom, the heterocyclic radical of preferred 5 yuan of rings or 6 yuan of rings at least.As heterocyclic radical, for example can enumerate: 5 yuan of nitrogenous cyclic groups such as pyrrole radicals, imidazole radicals, pyrazolyl; 6 yuan of nitrogenous cyclic groups such as pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl; The nitrogenous sulfenyl that contains such as thiazolyl, isothiazolyl; The nitrogenous oxygen bases that contain such as oxazolyl 、 isoxazolyl; Thienyl, thiapyran base etc. contain sulfenyl; Furyl, pyranose etc. contain oxygen base etc.Wherein, the heterocyclic radical that preferably contains 1 nitrogen-atoms or sulphur atom.Also can contain condensed ring in this heterocycle.As the heterocyclic radical that contains condensed ring, for example can enumerate benzothienyl etc.
In addition, also can have substituting group in the heterocyclic radical.As substituting group, can enumerate and above-mentioned R C5The identical group of situation.
In the above-mentioned formula (C-1), R C4The organic group of expression monovalence.Wherein, preferred carbon number is 1～5 alkyl.As this alkyl, can enumerate: methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl, sec-butyl, the tert-butyl group, n-pentyl, isopentyl, sec-amyl, tertiary pentyl etc.Wherein, R C4Most preferably be methyl.
With respect to the solid constituent of photosensitive composition of the present invention, (C) content of composition is preferably 0.1～50 quality %, 1～45 quality % more preferably.Be set in the above-mentioned scope through content, can obtain sufficient thermotolerance and chemical resistance, can suppress to solidify simultaneously bad (C) composition.
(D) colorant
As (D) colorant (below be also referred to as " (D) composition "), not special the qualification can not used known in the past colorant.
As colorant, for example can enumerate: カ ラ one イ Application デ Star Network ス (C.I.; The distribution of THE SOCIETY OF DYERS AND COLOURISTS society) is classified into the compound of pigment (pigment) in, specifically can enumerates the colorant of enclosing following カ ラ one イ Application デ Star Network ス (C.I.) sequence number.
C.I. pigment yellow 1 (following because " C.I. pigment yellow " so be the identical sequence number of only putting down in writing); 3; 11; 12; 13; 14; 15; 16; 17; 20; 24; 31; 53; 55; 60; 61; 65; 71; 73; 74; 81; 83; 86; 93; 95; 97; 98; 99; 100; 101; 104; 106; 108; 109; 110; 113; 114; 116; 117; 119; 120; 125; 126; 127; 128; 129; 137; 138; 139; 147; 148; 150; 151; 152; 153; 154; 155; 156; 166; 167; 168; 175; 180; 185;
C.I. pigment orange 1 (following because " C.I. pigment orange " so be the identical sequence number of only putting down in writing), 5,13,14,16,17,24,34,36,38,40,43,46,49,51,55,59,61,63,64,71,73;
C.I. pigment violet 1 (following because " C.I. pigment violet " so be the identical sequence number of only putting down in writing), 19,23,29,30,32,36,37,38,39,40,50;
C.I. paratonere 1 (following because " C.I. paratonere " so be the identical sequence number of only putting down in writing); 2; 3; 4; 5; 6; 7; 8; 9; 10; 11; 12; 14; 15; 16; 17; 18; 19; 21; 22; 23; 30; 31; 32; 37; 38; 40; 41; 42; 48:1; 48:2; 48:3; 48:4; 49:1; 49:2; 50:1; 52:1; 53:1; 57; 57:1; 57:2; 58:2; 58:4; 60:1; 63:1; 63:2; 64:1; 81:1; 83; 88; 90:1; 97; 101; 102; 104; 105; 106; 108; 112; 113; 114; 122; 123; 144; 146; 149; 150; 151; 155; 166; 168; 170; 171; 172; 174; 175; 176; 177; 178; 179; 180; 185; 187; 188; 190; 192; 193; 194; 202; 206; 207; 208; 209; 215; 216; 217; 220; 223; 224; 226; 227; 228; 240; 242; 243; 245; 254; 255; 264; 265;
C.I. pigment blue 1 (following because " C.I. alizarol saphirol " so be the same sequence number of only putting down in writing), 2,15,15:3,15:4,15:6,16,22,60,64,66;
C.I. pigment Green 7, C.I. pigment green 36, C.I. naphthol green 37;
C.I. pigment brown 23, C.I. pigment brown 25, C.I. pigment brown 26, C.I. pigment brown 28;
C.I. pigment black 1, pigment black 7.
In addition, as colorant, preferably use black pigment.As black pigment; Can enumerate: metal oxide, composite oxides, metal sulfide, metal sulfate, metal alloy or the metal carbonate etc. of carbon black, titanium black (titan black), copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver, tin etc., organism or inorganics all can various pigment.In these black pigments, more preferably use carbon black with high light-proofness.
As carbon black, can use known carbon blacks such as channel black, furnace black, pyrolytic carbon black, lamp black carbon black, but preferably use channel black or furnace black.
With respect to the solid constituent of photosensitive composition of the present invention, (D) content of composition is preferably 5～70 quality %, and more preferably 25～55 quality % further are preferably 30～50 quality %.
(S) organic solvent
Preferably, photosensitive composition of the present invention contains the organic solvent that is useful on dilution.As this organic solvent, can enumerate: (gathering) alkylene glycol monoalkyl ethers classes such as glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol list positive propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol ethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol list positive propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, DPG list ether, DPG list positive propyl ether, DPG mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol list ether; (gathering) alkylene glycol monoalkyl ethers acetate esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate; Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran; Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone; Lactic acid alkyl ester classes such as 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester; 2-hydroxy-2-methyl ethyl propionate; 3-methoxypropionic acid methyl esters; 3-methoxy propyl acetoacetic ester; 3-ethoxy-propionic acid methyl esters; The 3-ethoxyl ethyl propionate; Ethoxy ethyl acetate; Hydroxyl ethyl acetate; 2-hydroxy-3-methyl methyl butyrate; 3-methyl-3-methoxyacetic acid butyl ester (3-methyl-3-methoxy butyl acetate); 3-methyl-3-methoxy propyl acid butyl ester (3-methyl-3-methoxy butyl propionate); Ethyl acetate; N-propyl acetate; Isopropyl acetate; N-butyl acetate; Isobutyl acetate; The formic acid n-pentyl ester; Isoamyl acetate; N-butyl propionate; Ethyl butyrate; The butyric acid n-propyl; Isopropyl isobutyrate; The positive butyl ester of butyric acid; Methyl pyruvate; Ethyl pyruvate; The pyruvic acid n-propyl; Methyl acetoacetate; Ethyl acetoacetate; Other ester classes such as 2-ethyl acetoacetate; Arene such as toluene, xylene; N-Methyl pyrrolidone, N, amide-types such as dinethylformamide, DMAC N,N etc.These organic solvents can use separately or combination use more than 2 kinds.
In these organic solvents; Propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, acetate 3-methoxyl butyl ester show excellent dissolubility to (A) composition, (B) composition, (C) composition; And can improve the dispersiveness of insoluble compositions such as black pigment, therefore preferred.
(S) content of composition preferably makes the solid component concentration of photosensitive composition of the present invention become the amount of 5～30 quality %.
< other compositions >
Photosensitive composition of the present invention can add adjuvant as required.As adjuvant, can enumerate: sensitizer, curing accelerator, crosslinking chemical, disperse additive, filling agent, adhesion promoter, anti-oxidant, ultraviolet light absorber, anti flocculant, thermal polymerization inhibitor, foam-breaking agent, surfactant etc.
< preparation method of photosensitive composition >
Photosensitive composition of the present invention can obtain through in stirring machine, all above-mentioned each compositions being mixed.In addition, become evenly in order to make resulting composition, available membrane filter filters.
" contact panel and display device "
Contact panel of the present invention has the formed solidified resin pattern of the photosensitive composition of the present invention of use.In addition, display device of the present invention has contact panel of the present invention.
In order on contact panel, to form solidified resin pattern; At first use contact transfer printing type apparatus for coating such as coating roller, reverse coating machine, bar coating machine or spinner (rotary apparatus for coating), the curtain formula non-contact type apparatus for coating such as coating machine that flow, photosensitive composition of the present invention is coated on the substrate.
Then, the photosensitive composition that is applied is carried out drying, formation is filmed.Do not limit for drying means is special, for example can adopt following any method: (1) utilizes hot plate under 80～120 ℃, preferred 90～100 ℃ temperature, to carry out 60～120 seconds dry methods; (2) at room temperature place the method for several hours～a couple of days; (3) in warm air heater or infrared heater, place tens of minutes～several hours to remove the method for desolvating.
Then, see through negative mask and carry out the part exposure to this irradiation ultraviolet radiation of filming, PRK isoreactivity energy line.The exposure of energy line is also different because of the composition of photosensitive composition, but is preferably for example 20～200mJ/cm 2About.
Then, utilize developer solution to develop, make filming after the exposure form the pattern of intended shape thus.Do not limit for developing method is special, can adopt infusion process, spray-on process etc.As developer solution, can enumerate: organic type of monoethanolamine, diethanolamine, triethanolamine etc., the perhaps WS of NaOH, potassium hydroxide, sodium carbonate, ammonia, quaternary ammonium salt etc.
Then, under 200～250 ℃ of left and right sides temperature, cure after the pattern after developing carried out.At this moment, preferably formation pattern is carried out blanket exposure.
Except forming the method for solidified resin pattern through part exposure and development in the above described manner, for example also can use ink-jet printer to form solidified resin pattern.In the case, photosensitive composition of the present invention is injected on the substrate forms the desired pattern shape, then through dry, make public and after cure and form solidified resin pattern.
The contact panel that will form solidified resin pattern according to conventional method in the above described manner is assembled in the display device, can make display device of the present invention thus.
[embodiment]
Below, embodiments of the invention are described, but scope of the present invention is not limited to these embodiment.Should explain that " portion ", " % " in below describing are respectively benchmark with the quality.
< synthetic example 1 >
At first; In 500ml four neck flasks, drop into bisphenol fluorene type epoxy resin (epoxide equivalent is 235) 235g, tetramethyl ammonium chloride 110mg, 2; 6-di-t-butyl-4-cresols 100mg and acrylic acid 72.0g, with 25ml/ minute speed to flask in be blown into air on one side 90～100 ℃ down heating fusions on one side.Then, under the state of solution maintenance gonorrhoea, slowly heat up, be heated to 120 ℃ it is fused fully.At this moment, the solution transparent thickness that becomes gradually continues to stir under this state., measure acid value therebetween, continue heated and stirred up to acid value less than 1.0mgKOH/g.Acid value reaches desired value needs 12 hours.Then, be cooled to room temperature, obtain water white transparency and be the represented bisphenol fluorene type epoxy acrylate of following formula (A-10) of solid, shaped.
[changing 10]
Figure BDA0000129591940000181
Then; In the above-mentioned bisphenol fluorene type epoxy acrylate 307.0g that obtains in this way, add acetate 3-methoxyl butyl ester 600g and make its dissolving; Be mixed into benzophenone tetracarboxylic dianhydride 80.5g and teabrom 1g then, slowly heat up, reacted 4 hours down at 110～115 ℃.After confirming that anhydride group disappears, be mixed into 1,2,3,6-tetrabydrophthalic anhydride 38.0g reacted 6 hours down at 90 ℃, obtained Resin A 1.Utilize infrared spectrum to confirm the disappearance of anhydride group.
This Resin A 1 is equivalent to the represented compound of above-mentioned formula (A-7).
< embodiment 1 >
Each composition shown in following is dissolved in the mixed solvent of acetate 3-methoxyl butyl ester/cyclohexanone/propylene glycol methyl ether acetate=60/20/20 (mass ratio); So that solid component concentration is 15 quality %; Mixed 2 hours with stirring machine; Using the aperture then is that the membrane filter of 5 μ m filters, the preparation photosensitive composition.
Binder compound
The Resin A 1 that obtains in the synthetic example 1 ... 95 parts
The multipolymer of styrene/methacrylic acid=80/20 (mass ratio) (Resin A 2, matter average molecular weight are 13000) ... 60 parts
" EHPE3150 " (ダ イ セ Le chemical industry society system; 2,1 of two (the methylol)-1-butanols of 2-, 2-epoxy radicals-4-(2-oxirane base) cyclohexane addition product; With reference to following formula (1)) ... 155 parts
Photopolymerization monomer
Dipentaerythritol acrylate (Japanese chemical drug society system) ... 175 parts
Photoepolymerizationinitiater initiater
" OXE-02 " (BASF society system;-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethyl ketone-1-(O-acetyl oxime)) ... 100 parts
Colorant
Carbon black (driving state pigment society system) ... 450 parts
[changing 11]
Figure BDA0000129591940000201
< embodiment 2～5 >
According to the composition that changes binder compound shown in the table 1, with respect to the binder compound total amount, the ratio of epoxy compound is 40%, 30%, 20%, 10%, in addition, adopts with embodiment 1 same mode to prepare photosensitive composition.Numeric representation mass parts in the table 1 should be described.
< embodiment 6 >
According to using represented " セ ロ キ サ イ De 2021P " (the ダ イ セ Le chemical industry society system) of following formula (2) to replace " EHPE3150 " shown in the table 1, in addition, adopt with embodiment 1 same mode to prepare photosensitive composition.
[changing 12]
Figure BDA0000129591940000202
< embodiment 7～10 >
According to the composition that changes binder compound shown in the table 1, with respect to the binder compound total amount, the ratio of epoxy compound is 40%, 30%, 20%, 10%, in addition, adopts with embodiment 6 same modes to prepare photosensitive composition.Numeric representation mass parts in the table 1 should be described.
< embodiment 11 >
According to using represented " セ ロ キ サ イ De 2081 " (the ダ イ セ Le chemical industry society system) of following formula (3) to replace " EHPE3150 " shown in the table 1, in addition, adopt with embodiment 1 same mode to prepare photosensitive composition.
[changing 13]
Figure BDA0000129591940000211
< embodiment 12～15 >
According to the composition that changes binder compound shown in the table 1, with respect to the binder compound total amount, the ratio of epoxy compound is 40%, 30%, 20%, 10%, in addition, adopts with embodiment 11 same modes to prepare photosensitive composition.Numeric representation mass parts in the table 1 should be described.
< embodiment 16 >
According to using represented " セ ロ キ サ イ De 2000 " (the ダ イ セ Le chemical industry society system) of following formula (4) to replace " EHPE3150 " shown in the table 2, in addition, adopt with embodiment 1 same mode to prepare photosensitive composition.
[changing 14]
Figure BDA0000129591940000212
< embodiment 17～20 >
According to the composition that changes binder compound shown in the table 2, with respect to the binder compound total amount, the ratio of epoxy compound is 40%, 30%, 20%, 10%, in addition, adopts with embodiment 16 same modes to prepare photosensitive composition.Numeric representation mass parts in the table 2 should be described.
< embodiment 21 >
According to using represented " セ ロ キ サ イ De 3000 " (the ダ イ セ Le chemical industry society system) of following formula (5) to replace " EHPE3150 " shown in the table 2, in addition, adopt with embodiment 1 same mode to prepare photosensitive composition.
[changing 15]
< embodiment 22～25 >
According to the composition that changes binder compound shown in the table 2, with respect to the binder compound total amount, the ratio of epoxy compound is 40%, 30%, 20%, 10%, in addition, adopts with embodiment 21 same modes to prepare photosensitive composition.Numeric representation mass parts in the table 2 should be described.
< comparative example 1 >
According to the composition of the binder compound of change shown in the table 2, and do not contain epoxy compound in the binder compound, in addition, adopt with embodiment 1 same mode to prepare photosensitive composition.Numeric representation mass parts in the table 2 should be described.
< evaluation >
[chemical-resistant evaluation]
Use rotary coating machine (TR25000: chemical industry society system is answered in Tokyo) that the photosensitive composition of preparation in embodiment 1～25, the comparative example 1 is coated glass substrate (Corning society system; E2K glass) on; Under 90 ℃, carrying out 120 seconds dryings, is filming of 1.8 μ m thereby form thickness.Then, aim at exposer (mirror projection aligner) (TME-150RTO: with mirror surface projection ト プ コ Application society system) to this irradiation ultraviolet radiation of filming (wavelength 365nm, exposure 50mJ).Then, in circulating baker, after carrying out 20 minutes under 230 ℃, cure, thereby obtain cured film.
The glass substrate that will be formed with this cured film is placed on 40 ℃ etching solution (H 3PO 4/ CH 3COOH/HNO 3/ H 2O=65/3/12/22) soaked 1 minute in, after the washing, dewater through air blast.In addition, the glass substrate that will be formed with cured film is placed in 60 ℃ the stripper (DMSO/ monoethanolamine=30/70) and soaked 1 minute, after the washing, dewaters through air blast.
Then, for the chemical resistance of evaluate cure film, and carry out the reticulate pattern test.Particularly; According to ISO2409 (ASTM D-3359); Interval with 2.0mm becomes 100 lattice (order) (respectively cutting 11 times on the direction in length and breadth) with the cured film crosscut, makes adhesive tape adhere to this crosscut position securely, peels off adhesive tape then apace; Whether the inspection cured film is peeled off, and estimates to a class 5 B6 grade with grade 0B.The result is like below table 1, shown in 2.
[evaluation of against weather]
Use prepared photosensitive composition in embodiment 1～25, the comparative example 1, according on glass substrate, forming cured film with above-mentioned [chemical-resistant evaluation] same mode.
Use weather-proof tester (Xenon X75: ス ガ testing machine society system) this cured film is implemented weathering test.Particularly, 1 dark test of 60 ℃ of temperature, humidity 100%RH, 1 exposure experiment that UV is arranged and 50 ℃ of temperature, humidity 100%RH, no UV irradiation as 1 circulation (8 hours), is carried out circulate for 25 times (200 hours).
Then, for the against weather of evaluate cure film, adopt with above-mentioned " chemical-resistant evaluation " same mode and carry out the reticulate pattern test.The result is like below table 1, shown in 2.
[table 1]
Figure BDA0000129591940000241
[table 2]
Figure BDA0000129591940000251
By knowing in the table 1,2; Contain under the situation of epoxy compound as the photosensitive composition of the embodiment 1～25 of binder compound in use; In reticulate pattern test after the chemical resistance test and these two tests of reticulate pattern test after the weathering test, the adhesiveness that display level 0B is above.Wherein, Be under 40～50% the situation in ratio with respect to binder compound total amount epoxy compound; The adhesiveness of display level 5B in the reticulate pattern test after the chemical resistance test, the adhesiveness in the reticulate pattern test after weathering test more than the display level 3B is particularly in using the embodiment 1,2 of EHPE3150 as epoxy compound; In reticulate pattern test after the chemical resistance test and these two tests of reticulate pattern test after the weathering test, the adhesiveness of display level 5B.
To this; Using under the situation about not containing as the photosensitive composition of the comparative example 1 of the epoxy compound of binder compound; The adhesiveness of display level 0B in the reticulate pattern test after weathering test; So but, therefore do not implement the reticulate pattern test after chemical resistance is tested because obviously relatively poor in etch processes or foliation processing, the filming of chemical resistance peeled off.

Claims (6)

1. photosensitive composition that is used for contact panel, it contains (A) binder compound, (B) photopolymerization monomer, (C) Photoepolymerizationinitiater initiater and (D) colorant, and said (A) binder compound comprises epoxy compound.
2. the photosensitive composition that is used for contact panel as claimed in claim 1, wherein, said epoxy compound is by the represented compound of following formula (A-1):
[changing 1]
Figure FDA0000129591930000011
In the formula, R A1Be to have the residue of having removed the reactive hydrogen base in the organic compound of k reactive hydrogen base; N1, n2 ..., nk representes 0～100 integer respectively independently, its summation is 1～100; K representes 1～100 integer; A has the oxygen cyclohexane skeleton of substituent B or the oxygen ENB skeleton with substituent B, by following formula (A-2) or (A-3) expression;
[changing 2]
Figure FDA0000129591930000012
In the formula, B is respectively independently by following formula (A-4), formula (A-5) or the represented group of formula (A-6);
[changing 3]
Figure FDA0000129591930000013
Wherein, contain the represented group of above-mentioned formula (A-4) more than 1 in this epoxy compound; R A2Expression alkyl, alkyl-carbonyl or aryl carbonyl.
3. the photosensitive composition that is used for contact panel as claimed in claim 1, wherein, with respect to the total amount of said (A) binder compound, the ratio of said epoxy compound is 40～60 quality %.
4. the photosensitive composition that is used for contact panel as claimed in claim 1, wherein, said (D) colorant is a black pigment.
5. contact panel, it has each described formed solidified resin pattern of photosensitive composition that is used for contact panel in the claim 1 to 4 of use.
6. display device, it has the described contact panel of claim 5.
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