CN104428322B - Photocurable composition and its cured article - Google Patents

Photocurable composition and its cured article Download PDF

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Publication number
CN104428322B
CN104428322B CN201480001826.8A CN201480001826A CN104428322B CN 104428322 B CN104428322 B CN 104428322B CN 201480001826 A CN201480001826 A CN 201480001826A CN 104428322 B CN104428322 B CN 104428322B
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photoepolymerizationinitiater initiater
photocurable composition
methyl
compound
quality
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CN104428322A (en
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吉田正人
乘越明男
近藤忍
松本茂
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Taiyo Holdings Co Ltd
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Taiyo Ink Mfg Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • 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
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions
    • H05K3/287—Photosensitive compositions

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Non-Metallic Protective Coatings For Printed Circuits (AREA)
  • Polymerisation Methods In General (AREA)
  • Paints Or Removers (AREA)

Abstract

The Photocurable composition that solidified nature excellence is provided and the cured article solidified.A kind of use in printed circuit board Photocurable composition; it contains at least one Photoepolymerizationinitiater initiater in the group being selected from and being made up of oxime ester system Photoepolymerizationinitiater initiater, alkyl phenones system Photoepolymerizationinitiater initiater, acylphosphine oxide system Photoepolymerizationinitiater initiater and luxuriant titanium system Photoepolymerizationinitiater initiater, and the Photoepolymerizationinitiater initiater shown in following general formula (I).(in formula (I), R represents the structure shown in following formula (II), l 1represent the integer of 2 ~ 4, m 1represent the integer of more than 1.)

Description

Photocurable composition and its cured article
Technical field
The present invention relates to Photocurable composition and its cured article.
Background technology
For containing Photoepolymerizationinitiater initiater as composition, and the Photocurable composition solidified by irradiation ultraviolet radiation isoreactivity energy-ray, be used in because having the advantages such as quick solidification is excellent coating, resin insulating barrier, solder resist, for the formation of electrode paste etc. widely (such as, patent documentation 1,2) in field.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2000-214584 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2001-075281 publication
Summary of the invention
the problem that invention will solve
In recent years, from the viewpoint such as productivity, operability, require the solidified nature improving Photocurable composition further.Such as, to reduce power consumption, operating cost etc. as object, replace current UV lamp and use LED-UV lamp to receive much concern as the curing of light source.But the light irradiated due to above-mentioned light source is long wavelength, and therefore curing performance is low, compared with during the UV lamp that use is current, cannot Photocurable composition be made fully to solidify.
Therefore, the Photocurable composition that the object of the present invention is to provide solidified nature excellence and the cured article solidified.
for the scheme of dealing with problems
The present inventor etc. conduct in-depth research in view of the above problems, found that: by using the specific Photoepolymerizationinitiater initiater of combination to solve the problem, thus complete the present invention.
Namely; the feature of use in printed circuit board Photocurable composition of the present invention is; it contains: be selected from by oxime ester system Photoepolymerizationinitiater initiater, alkyl phenones (alkylphenone) be Photoepolymerizationinitiater initiater, at least one Photoepolymerizationinitiater initiater in the group that forms of acylphosphine oxide system Photoepolymerizationinitiater initiater and luxuriant titanium system Photoepolymerizationinitiater initiater, and the Photoepolymerizationinitiater initiater shown in following general formula (I).
(in formula, R represents the structure shown in following formula (II), l 1represent the integer of 2 ~ 4, m 1represent the integer of more than 1.)
Use in printed circuit board Photocurable composition of the present invention is also preferably containing photosensitivity (methyl) acrylic compound.
Use in printed circuit board Photocurable composition of the present invention is also preferably containing organic binder bond.
The feature of cured article of the present invention is, aforementioned use in printed circuit board Photocurable composition solidification forms by it.
the effect of invention
According to the present invention, the Photocurable composition that solidified nature excellence can be provided and the cured article solidified.
Accompanying drawing explanation
Fig. 1 represents the figure of the weight loss on heating curve that the Photoepolymerizationinitiater initiater that reference example uses is obtained by differential thermal-thermogravimetric Simultaneously test (TG/DTA mensuration).Transverse axis represents temperature (Cel: centigradetemperature), and the longitudinal axis represents the reduction ratio (%) of thermogravimetric.
Embodiment
Below, Photocurable composition of the present invention is described in detail.
[Photoepolymerizationinitiater initiater]
Photocurable composition of the present invention contains at least one Photoepolymerizationinitiater initiater in the group being selected from and being made up of oxime ester system Photoepolymerizationinitiater initiater, alkyl phenones system Photoepolymerizationinitiater initiater, acylphosphine oxide system Photoepolymerizationinitiater initiater and luxuriant titanium system Photoepolymerizationinitiater initiater.
As oxime ester system Photoepolymerizationinitiater initiater, the N-1919 etc. that CGI-325, IRGACUREOXE01, IRGACUREOXE02, ADEKACORPORATION that the BASFJAPANLTD. that can enumerate commercially available product manufactures manufacture.
In addition, also can use in molecule the Photoepolymerizationinitiater initiater with two oxime ester bases aptly, the oxime ester compound with carbazole structure shown in following general formula (2) can be enumerated specifically.
(in formula (2), X represents hydrogen atom, the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, phenyl, phenyl is (by the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, amino, alkylamino or the dialkyl amido with the alkyl of carbon number 1 ~ 8 replace), naphthyl is (by the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, amino, alkylamino or the dialkyl amido with the alkyl of carbon number 1 ~ 8 replace), Y, Z represents hydrogen atom respectively, the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, halogen group, phenyl, phenyl is (by the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, amino, alkylamino or the dialkyl amido with the alkyl of carbon number 1 ~ 8 replace), naphthyl is (by the alkyl of carbon number 1 ~ 17, the alkoxyl group of carbon number 1 ~ 8, amino, alkylamino or the dialkyl amido with the alkyl of carbon number 1 ~ 8 replace), anthryl, pyridyl, benzofuryl, benzothienyl, Ar represents the alkylidene group of carbon number 1 ~ 10, vinylidene, phenylene, diphenylene, pyridylidene, naphthylidene, thiophene, anthrylene, sub-thienyl, furylidene, 2,5-pyrroles-two base, 4,4 '-toluylene-two base, 4,2 '-vinylbenzene-two base, n is the integer of 0 or 1)
Particularly, in above-mentioned formula, X, Y are respectively methyl or ethyl, and Z is methyl or phenyl, and n is 0, Ar is phenylene, the oxime ester system Photoepolymerizationinitiater initiater of naphthylidene, thiophene or sub-thienyl is preferred.
Oxime ester system Photoepolymerizationinitiater initiater can be used alone one, also can be used in combination of two or more.Use compounding amount during oxime ester system's Photoepolymerizationinitiater initiater to convert with solids component, in Photocurable composition, be preferably 0.1 ~ 25 quality %, be more preferably 5 ~ 15 quality %.If below 25 quality %, then film is formed well.In addition, if more than 0.1 quality %, then can obtain sufficient light solidified, and patternability is good.
As alkyl phenones system Photoepolymerizationinitiater initiater, can enumerate: the benzil dimethyl ketal system Photoepolymerizationinitiater initiaters such as 2,2-dimethoxy-1,2-diphenylethane-1-ketone; 1-hydroxy-cyclohexyl-phenyl-one, 2-hydroxy-2-methyl-1-phenyl-propan-1-ketone, 1-[4-(2-hydroxyl-oxethyl)-phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone, 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl] phenyl } the Alpha-hydroxy alkyl phenones system Photoepolymerizationinitiater initiater such as-2-methyl-propan-1-ketone; 2-methyl isophthalic acid-[4-(methylthio group) phenyl]-2-morpholinopropanone-1,2-benzyl-2-dimethylamino-1-(4-morphlinophenyl)-butane-1-ketone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl] the alpha-aminoacetophenone system Photoepolymerizationinitiater initiater such as-1-butanone, N, N-dimethylamino benzoylformaldoxime.As the commercially available product of benzil dimethyl ketal system Photoepolymerizationinitiater initiater, can enumerate: the IRGACURE651 etc. that BASFJAPANLTD. manufactures.As the commercially available product of Alpha-hydroxy alkyl phenones system Photoepolymerizationinitiater initiater, can enumerate: IRGACURE184, DAROCUR1173, IRGACURE2959, IRGACURE127 etc. that BASFJAPANLTD. manufactures.As the commercially available product of alpha-aminoacetophenone system Photoepolymerizationinitiater initiater, can enumerate: IRGACURE907, IRGACURE369, IRGACURE379 etc. that BASFJAPANLTD. manufactures.
As acylphosphine oxide system Photoepolymerizationinitiater initiater; can list: 2; 4; 6-trimethyl benzoyl diphenyl base phosphine oxide, two (2; 4,6-trimethylbenzoyl)-phenyl phosphine oxide, two (2,6-Dimethoxybenzoyl)-2; 4,4-trimethyl-pentyl phosphine oxide etc.As commercially available product, can enumerate: LucirinTPO, IRGACURE819 etc. that BASFJAPANLTD. manufactures.
As luxuriant titanium system Photoepolymerizationinitiater initiater, specifically, two (cyclopentadiene)-two-phenyl-titanium, two (cyclopentadiene)-two-chloro-titanium, two (cyclopentadiene)-bis-(2 can be listed, 3,4,5,6 pentafluorophenyl groups) titanium, two (cyclopentadiene)-bis-(the fluoro-3-of 2,6-bis-(pyrroles-1-base) phenyl) titanium etc.As commercially available product, can enumerate: the IRGACURE784 etc. that BASFJAPANLTD. manufactures.
For alkyl phenones system Photoepolymerizationinitiater initiater, acylphosphine oxide system Photoepolymerizationinitiater initiater and luxuriant titanium system Photoepolymerizationinitiater initiater, can be used alone one respectively, also can be used in combination of two or more.Use compounding amount during aforementioned each Photoepolymerizationinitiater initiater to convert with solids component, in Photocurable composition, be preferably 2 ~ 25 quality %, be more preferably 5 ~ 15 quality %.If below 25 quality %, then film is formed well.In addition, if more than 2 quality %, then can obtain sufficient light solidified, and patternability is good.
In addition, Photocurable composition of the present invention contains the Photoepolymerizationinitiater initiater shown in following general formula (I).
(in formula (I), R represents the structure shown in following formula (II), l 1represent the integer of 2 ~ 4, m 1represent the integer of more than 1.)
L in above-mentioned general formula (I) 1be preferably 2 or 4, m 1be preferably 1 ~ 5, be more preferably 1 ~ 3, be particularly preferably 1.
Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I) is at room temperature preferably liquid.Under this room temperature, liquid state to refer in 10 ~ 40 DEG C at arbitrary temperature, put in the developmental tube of internal diameter 30mm height to the sample of 55mm and developmental tube is placed in level time, be the state within 90 seconds from bottom to the part by 85mm.
5% weightless temperature of the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I) is preferably more than 260 DEG C.In addition, less than 500 DEG C are preferably as the upper limit.In this manual, 5% weightless temperature refers in the weight loss on heating curve obtained by differential thermal-thermogravimetric Simultaneously test (TG/DTA mensuration), and thermogravimetric reduces the temperature (condition determination: 10 DEG C/min) when 5%.
As the example of the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I), can enumerate: the diester etc. of Carboxvmethoxv thioxanthone and polytetramethylene glycol 250.
Record the chemical formula of the concrete example of the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I).Wherein, the present invention is not restricted because of following compound.
(in formula, n represents the integer of more than 1.)
As the example of the commercially available product of the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I), can enumerate: the OmnipolTX etc. that InternationalHeraldTribuneCorporation manufactures.
Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I) can be used alone one, also can be used in combination of two or more.The compounding amount of the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I) converts with solids component, is preferably 0.01 ~ 15 quality %, is more preferably 0.1 ~ 15 quality % in Photocurable composition.If below 15 quality %, then film is formed easily.In addition, if more than 0.01 quality %, then can obtain sufficient light solidified, and patternability is good.
(photosensitivity (methyl) acrylic compound)
Photocurable composition of the present invention is also preferably containing photosensitivity (methyl) acrylic compound.Photosensitivity (methyl) acrylic compound irradiates through active energy beam and after carrying out photocuring, makes above-mentioned insoluble or contribute to insoluble compound in alkaline aqueous solution containing carboxy resin.Photosensitivity (methyl) acrylic compound also can use as the thinner of Photocurable composition.
For the compound used as above-mentioned photosensitivity (methyl) acrylic compound, such as, can enumerate: known usual polyester (methyl) acrylate, polyethers (methyl) acrylate, carbamate (methyl) acrylate, carbonic ether (methyl) acrylate, epoxy (methyl) acrylate etc.Specifically, can enumerate: (methyl) acrylic acid hydroxy alkyl ester classes such as vinylformic acid 2-hydroxyl ethyl ester, vinylformic acid 2-hydroxypropyl acrylate, methacrylic acid 2-hydroxyl methyl esters; The diacrylate class of the glycol such as ethylene glycol, methoxyl group TEG, polyoxyethylene glycol, propylene glycol, Diethylene Glycol; The acrylic amides such as N,N-DMAA, N hydroxymethyl acrylamide, N, N-dimethylaminopropylacryl acid amides; The amino alkyl acrylates classes such as N, N-dimethyl amino ethyl acrylate, N, N-dimethylaminopropylacryl acid esters; The multicomponent methacrylate classes such as the polyvalent alcohols such as hexylene glycol, TriMethylolPropane(TMP), tetramethylolmethane, Dipentaerythritol, tris(2-hydroxy ethyl)isocyanurate or their ethylene oxide adduct, propylene oxide adduct or 6-caprolactone affixture; The multicomponent methacrylate classes such as the ethylene oxide adduct of phenoxy group acrylate, bisphenol a diacrylate and their phenols or propylene oxide adduct; The multicomponent methacrylate class of the glycidyl ethers such as glycerin diglycidyl ether, T 55, trihydroxymethylpropanyltri diglycidyl ether, triglycidyl group isocyanuric acid ester; Be not limited to above-claimed cpd, also can list the direct acroleic acid esterifications of polyvalent alcohol such as polyether glycol, polycarbonate diol, C-terminal polyhutadiene, polyester polyol or the esters of acrylic acid carrying out urethane acrylate via vulcabond and obtain and melamine acrylate and each methyl acrylic ester etc. corresponding with aforesaid propylene acid esters.
And then the hydroxyl reaction of the Epocryl that the polyfunctional epoxy resin such as vinylformic acid and cresol novolak type epoxy resin can also be used to react and then half carbamate compounds making the vulcabond such as hydroxy acrylate and isophorone diisocyanate such as pentaerythritol triacrylate be formed and this Epocryl and epoxy amino manthanoate acrylic compound obtained etc. are as photo-sensitive monomer.This Epoxy Acrylates resin can improve solidified nature and can not reduce tackiness (touch dry).
Especially in the present invention, for the multicomponent methacrylate classes such as the ethylene oxide adduct of the multicomponent methacrylate classes such as polyvalent alcohol or their ethylene oxide adduct, propylene oxide adduct or 6-caprolactone affixture, phenols or propylene oxide adduct and then the oligourethane class containing (methyl) acrylate, can use aptly from the viewpoint of low warpage properties, bendability.
Above-mentioned photosensitivity (methyl) acrylic compound can be used alone one, also can be used in combination of two or more.The compounding amount of above-mentioned photosensitivity (methyl) acrylic compound converts with solids component, is preferably 1 ~ 30 quality %, is more preferably 2 ~ 20 quality %, is particularly preferably 5 ~ 15 quality % in Photocurable composition.If below 30 quality %, then can not be clamminess in surface, and touch dry is good.In addition, if more than 1 quality %, then can obtain sufficient light solidified during exposure, and patternability is good.
(organic binder bond)
Photocurable composition of the present invention is also preferably containing organic binder resins.As organic binder resins, preferably use containing carboxy resin, Photocurable composition can be made to become the Photocurable composition of alkali-developable.Now, the Photocurable composition of excellent in resolution can be obtained.As containing the not special restriction of carboxy resin, use in the Photocurable composition of solder resist, interlayer insulating film known containing carboxy resin can be adopted.
In addition, from the view point of light solidified, resistance to developability, except carboxyl, also in preferred molecule, there is ethylenic unsaturated bond, but also can for do not have ethylenical unsaturated double bonds containing carboxy resin.When not there is ethylenic unsaturated bond containing carboxy resin, in order to make compositions table reveal light solidified, the compound (photoreactivity monomer) with more than 1 ethylenically unsaturated group can be combinationally used in molecule.As ethylenical unsaturated double bonds, be preferably derived from the double bond of vinylformic acid or methacrylic acid or their derivative.
As in above-mentioned molecule containing carboxyl and do not have in molecule ethylenic unsaturated bond containing carboxy resin, can enumerate,
(1) make the unsaturated carboxylic acid such as vinylformic acid, methacrylic acid and vinylbenzene, alpha-methyl styrene, (methyl) lower alkyl acrylate, iso-butylene etc. have unsaturated double-bond compound copolymerization and obtain containing carboxy resin,
(2) make to have the epoxy group(ing) of the compound of unsaturated double-bond and the multipolymer of (methyl) glycidyl acrylate, with 1 molecule in there is 1 carboxyl and not there is the organic acid of ethylenic unsaturated bond, such as carbonatoms is the alkyl carboxylic acid of 2 ~ 17, the reaction such as alkyl carboxylic acid containing aromatic series base, the secondary hydroxyl generated and saturated or unsaturated multi-anhydride react and obtain containing carboxy resin,
(3) make hydroxyl polymer-containing, such as ethylene series hydroxyl polymer-containing, acrylic polyol, rubber series polyvalent alcohol, polyvinyl acetal, styrene allyl alcohol system resin, cellulose family etc. react with saturated or unsaturated multi-anhydride and obtain containing carboxy resin,
(4) make the reaction product of the dicarboxylic acid such as diepoxides and oxalic acid, propanedioic acid, succinic acid, phthalic acid, m-phthalic acid such as bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, brominated bisphenol a type epoxy resin, bisphenol-A epoxy resin, united phenol-type epoxy resin, di-toluene phenol-type epoxy resin, with saturated or unsaturated multi-anhydride react and obtains contain carboxy resin and
(5) make the reaction product of two functional epoxide compound and the bisphenols such as dihydroxyphenyl propane, Bisphenol F, react with saturated or unsaturated multi-anhydride and obtains contain carboxy resin etc.
In addition, as have in previous molecular in carboxyl and molecule have ethylenic unsaturated bond containing carboxyl photosensitivity prepolymer, can enumerate:
(1) unsaturated monocarboxylics such as the multi-functional epoxy compound making at least to have in 1 molecules such as phenolic resin varnish type epoxy resin two epoxy group(ing) and (methyl) vinylformic acid reacts, the hydroxyl generated again or unsaturated multi-anhydride saturated with hexahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride etc. react and obtain contain carboxyl photosensitivity prepolymer,
(2) multi-functional epoxy compound at least in 1 molecules such as phenolic resin varnish type epoxy resin with two epoxy group(ing) is made, with unsaturated monocarboxylic and the nonyl phenols etc. such as (methyl) vinylformic acid 1 have in molecule with the alcoholic extract hydroxyl group of epoxy reaction beyond the compound of 1 reactive group, more preferably have in p-hydroxyphenylethanol etc. 1 molecule at least 1 alcoholic extract hydroxyl group and with the alcoholic extract hydroxyl group of epoxy reaction beyond the compound of 1 reactive group react after, with hexahydrophthalic anhydride, saturated or the unsaturated multi-anhydride reaction such as Tetra Hydro Phthalic Anhydride and obtain containing carboxyl photosensitivity prepolymer,
(3) make unsaturated carboxylic acid such as (methyl) vinylformic acid, toxilic acid etc. and (methyl) methyl acrylate etc. have the carboxyl of the multipolymer of the compound of ethylenical unsaturated double bonds a part, with 1 molecule such as (methyl) glycidyl acrylate in there is 1 epoxy group(ing) and ethylenical unsaturated double bonds compound react and obtain carboxylic photosensitivity prepolymer,
(4) make unsaturated carboxylic acid such as (methyl) vinylformic acid, toxilic acid etc. and (methyl) methyl acrylate etc. have the compound of ethylenical unsaturated double bonds multipolymer, with 1 molecule such as (methyl) glycidyl acrylate in there is 1 epoxy group(ing) and ethylenical unsaturated double bonds compound react, the hydroxyl generated and hexahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride etc. are saturated or unsaturated multi-anhydride reacts and obtains contain carboxyl photosensitivity prepolymer and
(5) make the unsaturated dicarboxylic acid anhydrides such as maleic anhydride and (methyl) methyl acrylate etc. have the compound of ethylenical unsaturated double bonds multipolymer, react with (methyl) acrylic acid hydroxy alkyl ester such as (methyl) vinylformic acid-2-hydroxyl ethyl ester and obtain contain carboxyl photosensitivity prepolymer etc.
In addition, the polyfunctional epoxy resin used in the synthesis of above-mentioned resin is when having structure of bisphenol A, Bisphenol F structure, biphenol structural, xenol novolac structure, di-cresylol structure, the compound particularly with xenyl novolac structure and its hydride, and the cured article of the Photocurable composition obtained because low warpage, resistance to bend(ing) are excellent preferably.
(methyl) acrylate being noted that herein is the term of general name acrylate, methacrylic ester and their mixture, is also same for other similar expression following.
In addition, the acid number of above-mentioned organic binder bond is preferably the scope of 20 ~ 200mgKOH/g, is more preferably the scope of 40 ~ 150mgKOH/g.When the acid number of organic binder bond is more than 20mgKOH/g, can obtain the adaptation of film, when forming Photocurable composition, alkali-developable is good.In addition, when acid number is below 200mgKOH/g, the dissolving in the exposure portion that developing solution can be suppressed to cause, line can not be made to become thinner than required, in addition, be dissolved by the developing stripping with can suppressing exposure portion and unexposed portion indistinction, therefore the description of normal corrosion-resisting pattern becomes easy.
The weight-average molecular weight of above-mentioned organic binder bond is different according to resin matrix, is in general preferably 2000 ~ 150000.If weight-average molecular weight is more than 2000, then non-adhesion behavior is excellent, and the wet fastness of the film after exposure is good, and can not produce film during development and reduce, resolving power is good.In addition, if weight-average molecular weight is less than 150000, then the material that developability is good, storage stability is also excellent is become.Be more preferably 5000 ~ 100000.
(other composition)
In Photocurable composition of the present invention, only otherwise damage effect of the present invention, can compounding known additive except mentioned component.As additive, can enumerate: thermal polymerization inhibitor, UV light absorber, silane coupling agent, softening agent, fire retardant, static inhibitor, protective agent, antibacterial/mould inhibitor, defoamer, flow agent, filler, thickening material, adaptation imparting agent, thixotropy conferring agents, tinting material, Photoepolymerizationinitiater initiater other than the above, light-initiated auxiliary agent, sensitizing agent etc.As solder resist, carry out being coated with at substrate surface, after drying, when carrying out photocuring, also can use solvent.In addition, when using as solder resist, the Thermocurable compositions such as the heat-curing resin of preferred compounding epoxy compounds etc.
(filler)
Photocurable composition of the present invention also can contain filler (inorganic filler).Filler is the cure shrinkage of the cured article in order to suppress Photocurable composition, and the characteristic such as adaptation, hardness is improved and uses.As filler, such as, can enumerate: barium sulfate, amorphous silica, fused silica, spheroidal silica, talcum, clay, magnesiumcarbonate, calcium carbonate, aluminum oxide, aluminium hydroxide, silicon nitride, aluminium nitride, boron nitride, Nuo Yibao tripoli (neuburgsiliceousearth) etc.
The median size (D50) of filler is preferably less than 1 μm, is more preferably less than 0.7 μm, more preferably less than 0.5 μm.When median size is more than 1 μm, Photocurable composition is had to be the worry of gonorrhoea, not preferred according to purposes.Median size (D50) can utilize laser diffraction/scattering method to measure.Be in above-mentioned scope by median size, specific refractory power will level off to resinous principle, and transmissivity improves.
(Thermocurable composition)
In Photocurable composition of the present invention, in order to give thermotolerance, preferably add Thermocurable composition.As the Thermocurable composition used in the present invention, can enumerate: the known usual heat-curing resin etc. such as blocked isocyanate compounds, aminoresin, maleimide compound, benzoxazine colophony, carbodiimide resin, cyclic carbonate compound, multi-functional epoxy compound, multifunctional oxetane compound, episulfide resin.In the middle of them, preferred Thermocurable composition is at least any one the Thermocurable composition had in 1 molecule in multiple cyclic ether group and cyclic thioether base (hreinafter referred to as ring-type (sulphur) ether).These commercially available kinds with the Thermocurable composition of ring-type (sulphur) ether are a lot, can give multifrequency nature according to its structure.
The Thermocurable composition in this molecule with multiple ring-type (sulphur) ether is the compound of any one or two kinds of groups had in molecule in the cyclic ether group of two or more 3,4 or 5 ring or cyclic thioether base, include, for example out: have the compound of multiple epoxy group(ing), i.e. multi-functional epoxy compound in molecule; There is in molecule the compound of multiple oxetanyl, i.e. multifunctional oxetane compound; There are in molecule the compound of multiple thioether group, i.e. episulfide resin etc.
Above-mentioned multi-functional epoxy compound be have in 1 molecule two or more epoxy group(ing) (oxyethane ring) multi-functional epoxy compound or make this multi-functional epoxy compound be polymerized the resin obtained.As above-mentioned multi-functional epoxy compound, can enumerate: epoxidized vegetable oil; Bisphenol A type epoxy resin; Hydroquinone type epoxy resin, bisphenol-type epoxy resin, thioether-type epoxy resin; Brominated epoxy resin; Phenolic resin varnish type epoxy resin; Xenol phenolic resin varnish type epoxy resin; Bisphenol f type epoxy resin; Bisphenol-A epoxy resin; Glycidyl amine type epoxy resin; Glycolylurea type epoxy resin; Alicyclic epoxy resin; Trihydroxybenzene methylmethane type (trihydroxyphenylmethane) epoxy resin; Di-toluene phenolic or united phenol-type epoxy resin or their mixture; Bisphenol-s epoxy resin; Bisphenol A novolac type epoxy resin; Four phenol (phenylol) ethane type epoxy resin; Hetero ring type epoxy resin; O-phthalic acid diglycidyl ester (Phthalicaciddiglycidylester) resin; Four glycidyl group xylenol ethane resin; Containing Naphthol-based Epoxy Resin; There is the epoxy resin of dicyclopentadiene skeleton; Glycidyl methacrylate copolymerization system epoxy resin; The copolymerization epoxy resin of N-cyclohexylmaleimide and glycidyl methacrylate; Epoxide modified polybutadiene rubber derivative, CTBN modified epoxy etc., but be not limited to these.These epoxy resin can be used alone and maybe can be used in combination of two or more.In them, particularly preferably bisphenol-type epoxy resin.
As aforementioned multifunctional oxetane compound, can list: two [(3-methyl-3-oxetanylmethoxy) methyl] ether, two [(3-ethyl-3-oxetanylmethoxy) methyl] ether, 1, two [(3-methyl-3-oxetanylmethoxy) methyl] benzene of 4-, 1, two [(3-ethyl-3-oxetanylmethoxy) methyl] benzene of 4-, vinylformic acid (3-methyl-3-oxetanyl) methyl esters, vinylformic acid (3-ethyl-3-oxetanyl) methyl esters, methacrylic acid (3-methyl-3-oxetanyl) methyl esters, methacrylic acid (3-ethyl-3-oxetanyl) methyl esters, the multifunctional trimethylene oxide classes such as their oligopolymer or multipolymer, and oxa-cyclobutanol and novolac resin, poly-(4-Vinyl phenol), cardo type bisphenols, calixarene kind, Resorcinol calixarene kind, or silsesquioxane etc. has the etherate etc. of the resin of hydroxyl.In addition, the multipolymer etc. of unsaturated monomer and (methyl) alkyl acrylate with trimethylene oxide ring can also be listed.
As the episulfide resin in above-mentioned molecule with multiple cyclic thioether base, such as, can enumerate: the YSLV-120TE etc. that the YL7000 (bisphenol A-type episulfide resin) that Mitsubishi chemical Co., Ltd manufactures, Toto Kasei KK manufacture.In addition, also can adopt same synthetic method that the Sauerstoffatom of the epoxy group(ing) of phenolic resin varnish type epoxy resin is replaced with the episulfide resin etc. of sulphur atom.
In addition, except above-mentioned Thermocurable composition, the Thermocurable compositions such as the aminoresin that Photocurable composition of the present invention can also use melamine derivative, benzoguanamine derivative such.As this Thermocurable composition, include, for example out melamine methylol compound, methylolbenzoguanamine compound, methylol glycoluril compound, hydroxymethyl urea compound, alkoxymethylated melamine compound, aikoxymethytated benzoguanamine compound, aikoxymethytated glycolurils compound, aikoxymethytated urea compounds etc.Being not particularly limited the kind of above-mentioned alkoxy methyl, such as, can be methoxymethyl, ethoxyl methyl, propoxy methyl, butoxymethyl etc.Be particularly preferably the melamine derivative of less than 0.2% to human body, environmentally friendly formalin concentration.Above-mentioned Thermocurable composition can be used alone one, also can combinationally use two or more.
(solvent)
Photocurable composition of the present invention also can contain the organic solvent of the viscosity for adjusting composition.As organic solvent, as long as Photoepolymerizationinitiater initiater of the present invention can be dissolved just can use known usual solvent.Such as can enumerate: toluene, dimethylbenzene, ethyl acetate, butylacetate, methyl alcohol, ethanol, Virahol, isopropylcarbinol, n-butyl alcohol, diacetone alcohol, ethylene glycol monobutyl ether, dihydroxypropane single-ether, propylene glycol methyl ether acetate, Terpineol 350, methyl ethyl ketone, Trivalin SF, carbitol acetate, diethylene glycol monobutyl ether, acetate of butyl carbitol etc.Solvent can be used alone one, also can be used in combination of two or more.
Such as, for Photocurable composition of the present invention, after utilizing following coating method to be coated on base material etc., irradiation ultraviolet radiation, preferably illumination wavelength are that 10 ~ 420nm, more preferably illumination wavelength are the ultraviolet of 250 ~ 420nm and can solidify.Even if Photocurable composition of the present invention irradiates the ultraviolet of 320 ~ 420nm long wavelength, solidified nature is also excellent.
As ultraviolet irradiation light source, can enumerate: low pressure mercury lamp, medium pressure mercury lamp, high voltage mercury lamp, ultrahigh pressure mercury lamp, xenon lamp or metal halide lamp, laser, UV-LED etc.
Coating process can apply the arbitrary method such as dip coating, flow coat method, rolling method, stick coating method, silk screen print method, curtain painting method, woodburytype, flexographic printing process.
Photocurable composition of the present invention is preferred for solder mask.The feature of solder mask is, is coated on substrate by the Photocurable composition of the invention described above, and makes it solidify to form.
Also arbitrary known method can be adopted about the coating of the Photocurable composition for solder mask, curing.Such as, following method can be utilized.
As required, solvent is utilized to carry out diluting to be adjusted to the viscosity being suitable for coating process, it is coated with the methods such as method, spraying method, rolling method is coated with by silk screen print method, curtain on the printed circuit board (PCB) being such as formed with circuit, at the temperature of about 60 ~ 100 DEG C, such as make organic solvent volatile dry contained in composition, thus the film that can cannot do not formed stickyly.Then, optionally expose by forming figuratum photomask according to pattern direct irradiation laser isoreactivity energy-ray or employing ultraviolet, thus make it solidify.If when Photocurable composition is alkali developable, is developed by dilute alkali aqueous solution in unexposed portion, can corrosion-resisting pattern be formed.And then, according to expectation, be heating and curing by making it after ultraviolet irradiation or finally solidify (this solidification), thus cured film (cured article) can be formed.
Photocurable composition of the present invention, except solder resist, can also be used for the purposes such as the conductive paste of the electrode formation in the interlayer insulating film of printed circuit board (PCB), Plasmia indicating panel, touch panel.In addition, Photocurable composition of the present invention is except the method for directly carrying out being coated with on base material with liquid state, also can use with the form of dry film, this dry film has and to be coated with in advance by Photocurable composition and the dry film layer formed on the films such as pet film.
[embodiment]
Below, by embodiment, comparative example, the present invention is described in detail further, but the present invention is not limited to these embodiments, comparative example.It should be noted that, when not having special declaration, " part " represents mass parts, and " % " represents quality %.
[reference example]
(mensuration of 5% weightless temperature of Photoepolymerizationinitiater initiater)
Use differential thermal-thermogravimetric Simultaneously test device (TG/DTA), by 5% weightless temperature of the OmnIpolTX that InternationalHeraldTribuneCorporation manufactures, with following condition, reduce by the weight that certain speed measures when heating up, obtain temperature when thermogravimetric reduces 5%.The weight loss on heating curve obtained is shown in Fig. 1.5% weightless temperature is 318 DEG C.
Working sample: Photoepolymerizationinitiater initiater (measuring this sample 10mg in sample disc).
Determining instrument: HitachiHigh-TechScienceCorporation manufactures TG/DTA6200.
Measurement range: 30 DEG C ~ 600 DEG C.
Heat-up rate: 10 DEG C/min.
[embodiment 1 ~ 5 and comparative example 1 ~ 4]
(preparation of Photocurable composition)
Carry out mixing with triple-roller mill to each composition that following table 1 is recorded, prepare Photocurable composition.The unit of the compounding amount in table is mass parts.It should be noted that, as the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I), use the Photoepolymerizationinitiater initiater of above-mentioned chemical formula No.1.
For the Photocurable composition obtained, carry out following evaluation.Evaluation result is shown in following table 2.
< solidified nature >
Utilize coating device to be coated on full copper base by the Photocurable composition of embodiment and comparative example, and utilize the light of LED light source illumination wavelength 395nm and 405nm.Confirm the tackiness of solidification Hou Tu film, evaluate according to following benchmark.
Zero: be not clamminess.
△: be clamminess a little.
×: be clamminess.
[table 1]
※ 1:M-350 (TOAGOSEICO., LTD. manufacture); TriMethylolPropane(TMP) EO modification (3 moles) triacrylate
※ 2:IRGACUREOXE01 (BASFJAPANLTD. manufacture); 1-[4-(thiophenyl)-2-(O-benzoyl oximes)]-1,2-acetyl caproyl
※ 3:IRGACURE907 (BASFJAPANLTD. manufacture); 2-methyl isophthalic acid-(4-methylthiophenyi)-2-morpholino propane-1-ketone
※ 4:LucirinTPO (BASFJAPANLTD. manufacture); 2,4,6-trimethylbenzoyl phenyl phosphinic acid ethyl ester
※ 5:IRGACURE784 (BASFJAPANLTD. manufacture); Two (η 5-2,4-cyclopentadiene-1-base)-bis-(the fluoro-3-of 2,6-bis-(1H-pyrroles-1-base)-phenyl) titanium
※ 6:IRGACURE127 (BASFJAPANLTD. manufacture); 2-hydroxyl-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl }-2-methyl-propan-1-ketone
※ 7:OMNIPOLTX (INTERNATIONALHERALDTRIBUNECORPORATION manufacture); The diester of Carboxvmethoxv thioxanthone and polytetramethylene glycol 250
※ 8:DETX-S (NipponKayakuCo., Ltd. manufacture); 2,4-diethyl thioxanthone
※ 9:ITX (NipponKayakuCo., Ltd. manufacture); ITX
Result is as shown in Table 1 known, and the Photocurable composition of the embodiment any person in oxime ester system, alkyl phenones system, acylphosphine oxide system and luxuriant titanium system Photoepolymerizationinitiater initiater and the Photoepolymerizationinitiater initiater shown in above-mentioned general formula (I) combined is excellent in solidified nature.
In addition, prepare compounding the present invention uses in light photo-sensitive monomer etc. is as principal constituent, the inkjet compositions that formed with low viscosity initiator respectively and the material that obtains and compounding DETX-S and the material that obtains, relatively known based on the printing of ink-jet, use time the former and can print no problemly, can spray nozzle clogging be there is in contrast, use during the latter and cause printing.
Cured article of the present invention is like this specially adapted to the field of the products formed requiring above-mentioned characteristic, the button of such as mobile phone, various housings etc.; Or the purposes etc. of UV products formed material, light chisel material, ink-jet material, 3D ink-jet printer material etc.

Claims (4)

1. a use in printed circuit board Photocurable composition, is characterized in that, it contains:
Be selected from least one Photoepolymerizationinitiater initiater in the group be made up of the luxuriant titanium system Photoepolymerizationinitiater initiater of the oxime ester system Photoepolymerizationinitiater initiater of 0.1 ~ 25 quality %, the alkyl phenones system Photoepolymerizationinitiater initiater of 2 ~ 25 quality %, the acylphosphine oxide system Photoepolymerizationinitiater initiater of 2 ~ 25 quality % and 2 ~ 25 quality %, and
The Photoepolymerizationinitiater initiater shown in following general formula (I) of 0.01 ~ 15 quality %,
In formula (I), R represents the structure shown in following formula (II), l 1represent the integer of 2 ~ 4, m 1represent the integer of more than 1,
2. use in printed circuit board Photocurable composition according to claim 1, is characterized in that, it is also containing photosensitivity (methyl) acrylic compound.
3. use in printed circuit board Photocurable composition according to claim 1, is characterized in that, it is also containing organic binder bond.
4. a cured article, is characterized in that, it is solidified by the use in printed circuit board Photocurable composition according to any one of claims 1 to 3.
CN201480001826.8A 2013-06-28 2014-06-17 Photocurable composition and its cured article Active CN104428322B (en)

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