[go: up one dir, main page]

WO2015002071A1 - Composition de résine photosensible - Google Patents

Composition de résine photosensible Download PDF

Info

Publication number
WO2015002071A1
WO2015002071A1 PCT/JP2014/067067 JP2014067067W WO2015002071A1 WO 2015002071 A1 WO2015002071 A1 WO 2015002071A1 JP 2014067067 W JP2014067067 W JP 2014067067W WO 2015002071 A1 WO2015002071 A1 WO 2015002071A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
photosensitive resin
mass
composition according
epoxy resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2014/067067
Other languages
English (en)
Japanese (ja)
Inventor
正応 依田
中村　茂雄
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to JP2015525178A priority Critical patent/JPWO2015002071A1/ja
Priority to CN202011041126.5A priority patent/CN112147844B/zh
Priority to CN201480036156.3A priority patent/CN105308506B/zh
Priority to KR1020167003029A priority patent/KR102228718B1/ko
Publication of WO2015002071A1 publication Critical patent/WO2015002071A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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
    • H05K3/46—Manufacturing multilayer circuits
    • H05K3/4644—Manufacturing multilayer circuits by building the multilayer layer by layer, i.e. build-up multilayer circuits
    • H05K3/4673—Application methods or materials of intermediate insulating layers not specially adapted to any one of the previous methods of adding a circuit layer
    • H05K3/4676—Single layer compositions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
    • 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
    • H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
    • H05K2203/05—Patterning and lithography; Masks; Details of resist
    • H05K2203/0502—Patterning and lithography
    • H05K2203/0514—Photodevelopable thick film, e.g. conductive or insulating paste
    • 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
    • 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
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/34—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by soldering
    • H05K3/3452—Solder masks

Definitions

  • the present invention relates to a photosensitive resin composition.
  • it is related with the photosensitive resin composition suitable for using for the interlayer insulation layer of a multilayer printed wiring board.
  • Patent Document 1 discloses a photosensitive resin composition for MEMS comprising a specific photocationic polymerization initiator and a specific epoxy resin, but its use is limited to MEMS use. Insulation reliability is insufficient, so that sufficient performance as a build-up layer of a multilayer printed wiring board could not be exhibited.
  • Patent Document 2 discloses a photosensitive resin composition for a protective film of a printed wiring board for a semiconductor package. However, the insulation reliability is not sufficient, and its use is limited to a protective film, which is also a multilayer. A sufficient performance as a build-up layer of a printed wiring board could not be exhibited.
  • an object of the present invention is to provide a resin composition that has photosensitivity, excellent insulation reliability, and suitable physical properties for a build-up layer (interlayer insulating layer) of a multilayer printed wiring board.
  • the inventors include (A) an epoxy resin, (B) one or more curing agents selected from the group consisting of an active ester curing agent, a cyanate ester curing agent and a benzoxazine curing agent, and (C) (meta). It has been found that the above problems can be solved by using a photosensitive resin composition containing a compound having an acrylate structure, and the present invention has been completed.
  • the present invention includes the following contents.
  • the photosensitive resin composition containing this.
  • Composition Composition.
  • the photosensitive resin composition of the present invention can provide a buildup layer with excellent dielectric properties and low power consumption, and can provide a buildup layer with excellent water resistance and heat resistance. it can.
  • the photosensitive resin composition of the present invention comprises (A) an epoxy resin, (B) an active ester curing agent, one or more curing agents selected from the group consisting of a cyanate ester curing agent and a benzoxazine curing agent, and (C ) A compound having a (meth) acrylate structure.
  • a component is an epoxy resin.
  • epoxy resin For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol epoxy Resin, naphthol novolac epoxy resin, phenol novolac type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, cresol Novolac type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin having butadiene structure, alicyclic epoxy resin, heterocyclic type Examples include epoxy resins, spiro ring-containing epoxy resins, cyclohexanedimethanol type epoxy resins, naphthylene ether type epoxy resins, and trimethylol type epoxy resins.
  • An epoxy resin may be used individually by 1 type,
  • the epoxy resin preferably contains an epoxy resin having two or more epoxy groups in one molecule.
  • the nonvolatile component of the epoxy resin is 100% by mass, at least 50% by mass or more is preferably an epoxy resin having two or more epoxy groups in one molecule.
  • liquid epoxy resin an epoxy resin that is liquid at a temperature of 20 ° C.
  • solid epoxy resin an epoxy resin that is a solid at a temperature of 20 ° C.
  • liquid epoxy resin bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, or naphthalene type epoxy resin are preferable, and bisphenol A type epoxy resin, bisphenol F type epoxy resin, or naphthalene type epoxy resin are preferable. More preferred. Specific examples of the liquid epoxy resin include “HP4032”, “HP4032D”, “EXA4032SS”, “HP4032SS” (naphthalene type epoxy resin) manufactured by DIC Corporation, and “jER828EL” (bisphenol A) manufactured by Mitsubishi Chemical Corporation.
  • Type epoxy resin "jER807” (bisphenol F type epoxy resin), “jER152” (phenol novolac type epoxy resin), “ZX1059” (bisphenol A type epoxy resin and bisphenol F type epoxy) manufactured by Nippon Steel Chemical Co., Ltd. Resin mixture).
  • the liquid epoxy resin “HP4032SS” (naphthalene type epoxy resin) and “ZX1059” (mixed product of bisphenol A type epoxy resin and bisphenol F type epoxy resin) are particularly preferable.
  • a liquid epoxy resin may be used individually by 1 type, or may use 2 or more types together.
  • solid epoxy resins examples include tetrafunctional naphthalene type epoxy resins, cresol novolac type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol epoxy resins, naphthol novolac epoxy resins, biphenyl type epoxy resins, and naphthylene ether type epoxy resins.
  • a tetrafunctional naphthalene type epoxy resin, a biphenyl type epoxy resin, or a naphthylene ether type epoxy resin is more preferable, and a biphenyl type epoxy resin is more preferable.
  • solid epoxy resin examples include “HP-4700”, “HP-4710” (tetrafunctional naphthalene type epoxy resin), “N-690” (cresol novolac type epoxy resin) manufactured by DIC Corporation, “ N-695 ”(cresol novolac type epoxy resin),“ HP7200 ”,“ HP7200H ”,“ HP7200K-65I ”(dicyclopentadiene type epoxy resin),“ EXA7311 ”,“ EXA7311-G3 ”,“ HP6000 ”(naphthylene) Ether type epoxy resin), “EPPN-502H” (trisphenol epoxy resin), “NC7000L” (naphthol novolak epoxy resin), “NC3000H”, “NC3000”, “NC3000L”, “NC3100” manufactured by Nippon Kayaku Co., Ltd.
  • YX4000HK (bixylenol type epoxy resin), “NC3000L” (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., and “HP7200H” (dicyclopentadiene type epoxy resin) manufactured by DIC Corporation are preferable.
  • a solid epoxy resin may be used individually by 1 type, or may use 2 or more types together.
  • the quantitative ratio thereof is in the range of 1: 0.1 to 1: 4 by mass ratio. preferable.
  • the amount ratio of the liquid epoxy resin and the solid epoxy resin in such a range, i) suitable adhesiveness is obtained when used in the form of an adhesive film, and ii) when used in the form of an adhesive film. Sufficient flexibility is obtained, handling properties are improved, and iii) an insulating layer having sufficient breaking strength can be obtained.
  • the quantitative ratio of liquid epoxy resin to solid epoxy resin is 1: 0.3 to 1: 3.5 in terms of mass ratio.
  • the range of 1: 0.6 to 1: 3 is more preferable, and the range of 1: 0.8 to 1: 2.5 is particularly preferable.
  • the content of the epoxy resin is preferably 3% by mass to 50% by mass, more preferably 5% by mass to 45% by mass, and more preferably 7% by mass to 35% by mass, assuming that the nonvolatile component in the photosensitive resin composition is 100% by mass. % By mass is more preferable, and 8% by mass to 20% by mass is particularly preferable.
  • the epoxy equivalent of the epoxy resin is preferably 50 to 3000, more preferably 80 to 2000, and still more preferably 110 to 1000. By being in this range, the cured product has a sufficient cross-linking density, resulting in an insulating layer having excellent heat resistance.
  • the epoxy equivalent can be measured according to JIS K7236, and is the mass of a resin containing 1 equivalent of an epoxy group.
  • the component (B) is one or more curing agents selected from the group consisting of an active ester curing agent, a cyanate ester curing agent, and a benzoxazine curing agent.
  • the active ester curing agent used in the photosensitive resin composition of the present invention can improve heat resistance, dielectric properties, and water resistance when cured, and is particularly excellent in dielectric properties and water resistance.
  • curing agent The compound which has two or more active ester groups in 1 molecule is preferable.
  • the active ester curing agent there are generally compounds having two or more ester groups with high reaction activity in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds. Preferably used.
  • the active ester curing agent is obtained from a reaction product obtained by condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound.
  • An active ester compound is preferred, an active ester compound obtained from a carboxylic acid compound and a hydroxy compound is more preferred, and an active ester compound obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is still more preferred.
  • An aromatic compound having two or more active ester groups in one molecule obtained from a reaction product obtained by reacting a carboxylic acid compound with an aromatic compound having a phenolic hydroxyl group is even more preferable.
  • the active ester curing agent is an aromatic compound obtained from a reaction product obtained by reacting a compound having at least two or more carboxylic acids in one molecule with an aromatic compound having a phenolic hydroxyl group, and Particularly preferred are aromatic compounds having two or more active ester groups in one molecule of the aromatic compound.
  • the active ester compound may be linear or hyperbranched.
  • the compatibility with the resin composition can be increased, and if it is a compound having an aromatic ring, it is heat resistant. Sexuality can be increased.
  • the active ester curing agent may be used alone or in combination of two or more.
  • carboxylic acid compounds examples include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.
  • succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, and isophthalic acid and terephthalic acid are more preferred from the viewpoint of improving heat resistance when cured.
  • the thiocarboxylic acid compound examples include thioacetic acid and thiobenzoic acid.
  • phenol compound or naphthol compound examples include hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, phenolphthaline, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o -Cresol, m-cresol, p-cresol, catechol, ⁇ -naphthol, ⁇ -naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetra Hydroxybenzophenone, Phloroglucin, Benzenetriol, Dicyclopentadiene type diphenol compound (Polycyclopentadiene type diphenol compound), Pheno For example, arnovolac.
  • phenol novolak dicyclopentadiene type diphenol compound (polycyclopentadiene type diphenol compound), phenol novolak are more preferable, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2, -Dihydroxynaphthalene, dicyclopentadiene type diphenol compound (polycyclopentadiene type diphenol compound), and phenol novolac are more preferable.
  • Dicyclopentadiene-type diphenol compounds are particularly preferred, and dicyclopentadiene-type diphenol compounds (polycyclopentadiene-type diphenol compounds) are particularly preferred.
  • Specific examples of the thiol compound include benzenedithiol and triazinedithiol.
  • the active ester curing agent containing a dicyclopentadiene type diphenol condensation structure includes a compound represented by the following formula (1).
  • two Rs are each independently a phenyl group or a naphthyl group.
  • k represents 0 or 1;
  • n is 0.05 to 2.5 on the average of the repeating units.
  • R is preferably a naphthyl group.
  • k is preferably 0.
  • N is preferably 0.25 to 1.5.
  • an active ester compound disclosed in Japanese Patent Application Laid-Open No. 2004-277460 may be used, or a commercially available active ester curing agent may be used.
  • commercially available active ester curing agents include, specifically, an active ester curing agent containing a dicyclopentadiene type diphenol condensation structure, an active ester curing agent containing a naphthalene structure, and an activity containing an acetylated product of phenol novolac.
  • ester hardeners Preferred are ester hardeners, active ester hardeners containing phenol novolac benzoylates, especially active ester hardeners containing naphthalene structures, dicyclopentadiene diphenol compounds (polycyclopentadiene diphenol compounds).
  • An active ester curing agent is more preferred.
  • the active ester curing agent containing a dicyclopentadiene type diphenol compound (polycyclopentadiene type diphenol compound) structure include EXB9451, EXB9460, EXB9460S, and HPC8000-65T (manufactured by DIC Corporation).
  • Examples of the active ester curing agent containing a naphthalene structure include EXB9416-70BK (manufactured by DIC Corporation).
  • Examples of the active ester curing agent containing an acetylated product of phenol novolak include DC808 (Mitsubishi Chemical Corporation).
  • Examples of the active ester curing agent containing a benzoylated product of phenol novolak include YLH1026 (manufactured by Mitsubishi Chemical Corporation).
  • HPC8000-65T an active ester curing agent containing a dicyclopentadiene-type diphenol compound (polycyclopentadiene-type diphenol compound) structure
  • DIC Corporation is preferable.
  • the cyanate ester curing agent used in the photosensitive resin composition of the present invention can improve heat resistance, dielectric properties, and water resistance when cured, and is particularly excellent in heat resistance.
  • the cyanate ester-based curing agent is not particularly limited.
  • novolak type phenol novolac type, alkylphenol novolak type, etc.
  • dicyclopentadiene type cyanate ester-based curing agent bisphenol type (bisphenol A type) , Bisphenol F type, bisphenol S type, etc.) cyanate ester-based curing agents, and prepolymers in which these are partially triazines.
  • the weight average molecular weight of the cyanate ester curing agent is not particularly limited, but is preferably 500 to 4500, more preferably 600 to 3000.
  • Specific examples of the cyanate ester curing agent include, for example, bisphenol A dicyanate, polyphenol cyanate (oligo (3-methylene-1,5-phenylene cyanate)), and 4,4′-methylenebis (2,6-dimethylphenyl cyanate).
  • Resin phenol novolac, Resole novolac, polyfunctional cyanate resin derived from dicyclopentadiene structure-containing phenol resin, these cyanate resins and partially triazine of prepolymer. These may be used alone or in combination of two or more.
  • cyanate ester resins include phenol novolac type polyfunctional cyanate ester resin (Lonza Japan Co., Ltd., PT30S), and a prepolymer in which a part or all of bisphenol A dicyanate is triazine and becomes a trimer ( Lonza Japan Co., Ltd., BA230S75), dicyclopentadiene structure-containing cyanate ester resin (Lonza Japan Co., Ltd., DT-4000, DT-7000) and the like.
  • phenol novolac type polyfunctional cyanate ester resin Lionza Japan Co., Ltd., PT30S
  • a prepolymer in which a part or all of bisphenol A dicyanate is triazine and becomes a trimer Lonza Japan Co., Ltd., BA230S75
  • dicyclopentadiene structure-containing cyanate ester resin Lionza Japan Co., Ltd., DT-4000, DT-7000
  • PT30S phenol novolak type polyfunctional cyanate ester resin
  • BA230S75 prepolymer in which a part or all of bisphenol A dicyanate is triazine-modified into a trimer manufactured by Lonza Japan Co., Ltd. are preferable. .
  • the benzoxazine curing agent used in the photosensitive resin composition of the present invention can improve heat resistance, dielectric properties, and water resistance when used as a cured product.
  • the benzoxazine curing agent is not particularly limited, but specific examples include Fa type benzoxazine, Pd type benzoxazine (manufactured by Shikoku Kasei Co., Ltd.), and HFB2006M (manufactured by Showa Polymer Co., Ltd.).
  • Pd-type benzoxazine (manufactured by Shikoku Kasei Co., Ltd.) is preferable.
  • the active ester curing agent, the cyanate ester curing agent, and the benzoxazine curing agent may be used singly or in combination of two or more.
  • an active ester curing agent is preferable because the dielectric loss tangent and water absorption can be reduced.
  • the content of the component (B) is preferably 1 to 30% by mass, more preferably 3 to 25% by mass, based on 100% by mass of the nonvolatile component of the photosensitive resin composition, and 5 to 20% by mass. % Is more preferable.
  • the component (C) is a compound having a (meth) acrylate structure.
  • Examples of the compound having a (meth) acrylate structure include, but are not limited to, hydroxyalkyl acrylates such as 2-hydroxyethyl acrylate and 2-hydroxybutyl acrylate, ethylene glycol, methoxytetraethylene glycol, polyethylene glycol, and propylene glycol.
  • Mono- or diacrylates of glycols such as N, N-dimethylacrylamide, acrylamides such as N-methylolacrylamide, aminoalkyl acrylates such as N, N-dimethylaminoethyl acrylate, trimethylolpropane, pentaerythritol, dipenta Polyhydric alcohols such as erythritol or their adducts of ethylene oxide, propylene oxide or ⁇ -caprolactone Polyhydric acrylates, phenols such as phenoxy acrylate, phenoxyethyl acrylate, acrylates such as ethylene oxide or propylene oxide adducts thereof, epoxy acrylates derived from glycidyl ether such as trimethylolpropane triglycidyl ether, melamine acrylates And / or methacrylates corresponding to the above acrylates.
  • glycols such as N, N-dimethylacrylamide, acrylamides such as N-
  • polyvalent acrylates or polyvalent methacrylates are preferable.
  • the trivalent acrylates or methacrylates include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, and trimethylolpropane.
  • EO-added tri (meth) acrylate glycerin PO-added tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, tetrafurfuryl alcohol oligo (meth) acrylate, ethyl carbitol oligo (meth) acrylate, 1,4-butanediol Oligo (meth) acrylate, 1,6-hexanediol oligo (meth) acrylate, trimethylolpropane oligo (meth) acrylate, pentaerythritol oligo (meth) acrylate Rate, tetramethylol methane tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, N, N, N ′, N′-tetrakis ( ⁇ -hydroxyethyl) ethyldiamine (meth)
  • tri (2- (meth) acryloyloxyethyl) phosphate tri (2- (meth) acryloyloxypropyl) phosphate, tri (3- (meth) acryloyloxypropyl) Phosphate, tri (3- (meth) acryloyl-2-hydroxyloxypropyl) phosphate, di (3- (meth) acryloyl-2-hydroxyloxypropyl) (2- (meth) acryloyloxyethyl) phosphate, (3- ( Meta) Acu Mention may be made of phosphoric acid triester (meth) acrylates such as liloyl-2-hydroxyloxypropyl) di (2- (meth) acryloyloxyethyl) phosphate.
  • a component has an epoxy group from the point which improves the crosslinking
  • Particularly preferred are “acrylate compounds having a cresol novolac structure and an epoxy group” synthesized according to Synthesis Example 1, and “methacrylate compounds having a bixylenol structure, a biscresol fluorene structure and an epoxy group” synthesized according to Synthesis Example 2. These (meth) acrylate compounds may be used alone or in combination of two or more.
  • Component (C) preferably contains a polymer having a (meth) acrylate structure having a weight average molecular weight of 500 to 100,000, more preferably 700 to 70,000, still more preferably 1,000 to 50,000, from the viewpoint of improving resolution. And particularly preferably from 1500 to 35000.
  • the weight average molecular weight in this invention is measured by the gel permeation chromatography (GPC) method (polystyrene conversion).
  • GPC gel permeation chromatography
  • the weight average molecular weight by the GPC method is LC-9A / RID-6A manufactured by Shimadzu Corporation as a measuring device, and Shodex K-800P / K-804L / K manufactured by Showa Denko KK as a column.
  • -804L can be measured using chloroform or the like as a mobile phase at a column temperature of 40 ° C. and calculated using a standard polystyrene calibration curve.
  • the insulation reliability of the photosensitive resin composition of the present invention is preferred. It can have a carboxyl group to the extent that it does not inhibit the sex.
  • the acid value of the component (C) is preferably 20 mgKOH / g or less, more preferably 10 mgKOH / g or less, further preferably 5 mgKOH / g or less, still more preferably 3 mgKOH / g or less, and particularly preferably 1 mgKOH / g or less.
  • the content of the component (C) is preferably 1 to 25% by mass, more preferably 5 to 15% by mass when the nonvolatile component of the photosensitive resin composition is 100% by mass.
  • the following components can be further blended into the photosensitive resin composition of the present invention.
  • the resin composition of the present invention by further containing (D) a photopolymerization initiator, the resin composition can be efficiently photocured to obtain a cured product.
  • the photopolymerization initiator is not particularly limited.
  • 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone 2- (dimethylamino) -2-[(4 -Methylphenyl) methyl]-[4- (4-morpholinyl) phenyl] -1-butanone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, benzophenone, methylbenzophenone O-benzoylbenzoic acid, benzoyl ethyl ether, 2,2-diethoxyacetophenone, 2,4-diethylthioxanthone, diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, ethyl- (2,4,6- Trimethylbenzoyl) phenylphosphinate, 4,4′-bis (diethylamino) benzophenone, 1- Hydroxy-cyclohexyl-phenyl
  • acylphosphine oxide photopolymerization initiators such as bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (manufactured by BASF Japan Ltd., IC819), 1,2-octanedione, 1- [4 Oxime ester photopolymerization initiators such as-(phenylthio)-, 2- (O-benzoyloxime)] (manufactured by BASF Japan Ltd., OXE-01) are preferred because of their high sensitivity. Any one photopolymerization initiator may be used alone, or two or more photopolymerization initiators may be used in combination.
  • the blending amount of the photopolymerization initiator is when the nonvolatile component in the photosensitive resin composition is 100% by mass from the viewpoint of sufficiently curing the photosensitive resin composition and improving the insulation reliability.
  • the content is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and still more preferably 0.3% by mass or more.
  • the blending amount of the photopolymerization initiator is 2% by mass when the nonvolatile component in the photosensitive resin composition is 100% by mass from the viewpoint of preventing a decrease in dimensional stability due to excessive sensitivity.
  • the content is preferably set to 1% by mass or less, more preferably 1% by mass or less, and further preferably 0.5% by mass or less.
  • the thermal expansion coefficient of the photosensitive resin composition of the present invention can be lowered by further containing (E) an inorganic filler.
  • an inorganic filler for example, silica, alumina, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum borate, titanium Barium acid, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, calcium zirconate, etc., among these, amorphous silica, fused silica, hollow silica, crystalline silica, Silica such as synthetic silica is particularly suitable.
  • silica As the silica, spherical silica is preferable. You may use these 1 type or in combination of 2 or more types. Examples of preferable spherical fused silica that is commercially available include “SOC2” and “SOC1” manufactured by Admatechs Corporation.
  • the average particle diameter of the inorganic filler is preferably 1 ⁇ m or less, more preferably 0.8 ⁇ m or less, and more preferably 0.6 ⁇ m or less from the viewpoint of improvement in insulation reliability and improvement in photocurability. More preferably, it is 0.4 ⁇ m or less.
  • the average particle diameter of the (E) inorganic filler is preferably 0.01 ⁇ m or more, and more preferably 0.05 ⁇ m or more.
  • Inorganic fillers include silane coupling agents (epoxysilane coupling agents, aminosilane coupling agents, mercaptosilane coupling agents, etc.) and titanate coupling agents to improve moisture resistance and dispersibility. Those that have been surface treated with a surface treating agent such as a silazane compound are preferred. You may use these 1 type or in combination of 2 or more types.
  • epoxysilane coupling agent examples include glycidoxypropyltrimethoxysilane, glycidoxypropyltriethoxysilane, glycidoxypropylmethyldiethoxysilane, glycidylbutyltrimethoxysilane, (3,4-epoxycyclohexyl)
  • aminosilane coupling agents include aminopropylmethoxysilane, aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-2 (aminoethyl) amino.
  • Examples of the mercaptosilane coupling agent include mercaptopropyltrimethoxysilane and mercaptopropyltriethoxysilane. You may use these 1 type or in combination of 2 or more types.
  • Examples of commercially available coupling agents include “KBM403” (3-glycidoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., and “KBM803” (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd.
  • KBE903 (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd.
  • KBM573 N-phenyl-3-aminopropyltrimethoxysilane manufactured by Shin-Etsu Chemical Co., Ltd., and the like.
  • titanate coupling agents include butyl titanate dimer, titanium octylene glycolate, diisopropoxy titanium bis (triethanolaminate), dihydroxy titanium bis lactate, dihydroxy bis (ammonium lactate) titanium, bis (dioctyl pyrophosphate) ethylene Titanate, bis (dioctylpyrophosphate) oxyacetate titanate, tri-n-butoxytitanium monostearate, tetra-n-butyl titanate, tetra (2-ethylhexyl) titanate, tetraisopropylbis (dioctylphosphite) titanate, tetraoctylbis (Ditridecyl phosphite) titanate, tetra (2,2-diallyloxymethyl-1-butyl) bis (ditridecyl) Sphite titanate, isopropyl trioctanoyl titanate, isopropyl trioc
  • silazane compound examples include hexamethyldisilazane, 1,3-divinyl-1,1,3,3-tetramethyldisilazane, octamethyltrisilazane, hexa (t-butyl) disilazane, hexabutyldisilazane, hexa Octyldisilazane, 1,3-diethyltetramethyldisilazane, 1,3-di-n-octyltetramethyldisilazane, 1,3-diphenyltetramethyldisilazane, 1,3-dimethyltetraphenyldisilazane, 1, 3-diethyltetramethyldisilazane, 1,1,3,3-tetraphenyl-1,3-dimethyldisilazane, 1,3-dipropyltetramethyldisilazane, hexamethylcyclotrisilazane
  • an inorganic filler surface-treated with a silazane compound from the viewpoint of improving the dispersibility of the photosensitive resin composition. And after surface-treating with a silazane compound, the further dispersibility improvement can be aimed at by surface-treating with a silane coupling agent.
  • the amount of the silazane compound used for the surface treatment is preferably 0.001% by mass to 0.3% by mass, and 0.005% by mass to 0.2% by mass with respect to 100% by mass of the inorganic filler. It is more preferable.
  • Examples of the spherical fused silica surface-treated with hexamethyldisilazane include “SC2050” manufactured by Admatechs Co., Ltd.
  • the amount of the silane coupling agent used for the surface treatment is preferably 0.1% by mass to 6% by mass, and preferably 0.2% by mass to 4% by mass with respect to 100% by mass of the inorganic filler. Is more preferable, and 0.3 to 3% by mass is still more preferable.
  • the average particle diameter of the inorganic filler can be measured by a laser diffraction / scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be created on a volume basis by a laser diffraction particle size distribution measuring device, and the median diameter can be measured as the average particle diameter.
  • an inorganic filler dispersed in water by ultrasonic waves can be preferably used.
  • LA-500, LA-750 manufactured by Horiba, Ltd. or the like can be used as a laser diffraction / scattering particle size distribution measuring apparatus.
  • blending an inorganic filler is 100 mass% of non-volatile components in the photosensitive resin composition from a viewpoint of reducing the linear thermal expansion coefficient of hardened
  • the content in the case of blending the (E) inorganic filler is 100% by mass of the non-volatile component in the photosensitive resin composition from the viewpoint of preventing deterioration of alkali developability and improving photocurability. In this case, it is preferably 85% by mass or less, more preferably 75% by mass or less, and further preferably 65% by mass or less.
  • ⁇ (F) Curing accelerator> In the photosensitive resin composition of this invention, the heat resistance of a hardened
  • (F) hardening accelerator Although it does not specifically limit as a hardening accelerator, for example, an amine hardening accelerator, a guanidine hardening accelerator, an imidazole hardening accelerator, a phosphonium hardening accelerator, a metal hardening accelerator etc. are mentioned. These may be used alone or in combination of two or more.
  • the amine curing accelerator is not particularly limited, and examples thereof include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6, -tris (dimethylamino). And amine compounds such as methyl) phenol and 1,8-diazabicyclo (5.4.0) -undecene. You may use these 1 type or in combination of 2 or more types.
  • the guanidine-based curing accelerator is not particularly limited, and examples thereof include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolyl) guanidine, Dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1,5,7-tria Zabicyclo [4.4.0] dec-5-ene, 1-methyl biguanide, 1-ethyl biguanide, 1-n-butyl biguanide, 1-n-octadecyl biguanide, 1,1-dimethyl biguanide, 1,1- Diethyl biguanide, 1-cyclohexyl biguanide, 1-allyl biguanide 1-phenyl biguanide, 1- (o-
  • the imidazole curing accelerator is not particularly limited.
  • the phosphonium curing accelerator is not particularly limited.
  • the photosensitive resin composition of the present invention it is preferable to use an amine-based curing accelerator or an imidazole-based curing accelerator as the curing accelerator (excluding the metal-based curing accelerator), among which 4-dimethylaminopyridine, It is particularly preferred to use 2-phenyl-4-methylimidazole.
  • the content of the curing accelerator (excluding the metal-based curing accelerator) is preferably in the range of 0.005% by mass to 1% by mass when the nonvolatile component in the photosensitive resin composition is 100% by mass. The range of 0.01% by mass to 0.08% by mass is more preferable. If it is less than 0.005% by mass, curing tends to be slow and a long curing time is required, and if it exceeds 1% by mass, the storage stability of the resin composition tends to decrease.
  • the metal curing accelerator is not particularly limited, and examples thereof include an organometallic complex or an organometallic salt of a metal such as cobalt, copper, zinc, iron, nickel, manganese, and tin.
  • organometallic complex include organic cobalt complexes such as cobalt (II) acetylacetonate and cobalt (III) acetylacetonate, organic copper complexes such as copper (II) acetylacetonate, and zinc (II) acetylacetonate.
  • Organic zinc complexes such as iron (III) acetylacetonate, organic nickel complexes such as nickel (II) acetylacetonate, and organic manganese complexes such as manganese (II) acetylacetonate.
  • organic metal salt include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate. These may be used alone or in combination of two or more.
  • an organic cobalt complex is preferably used as the metal curing accelerator, and cobalt (III) acetylacetonate is particularly preferably used.
  • the content of the metal-based curing accelerator is preferably such that the metal content based on the metal-based curing catalyst is in the range of 25 ppm to 500 ppm when the total solid content of the photosensitive resin composition is 100% by mass. More preferably, it is in the range of ⁇ 200 ppm.
  • the photosensitive resin composition of the present invention can further reduce the stress of the cured product by containing an organic filler (G), and can prevent the occurrence of cracks when the cured product is formed.
  • organic filler (G) include rubber particles, polyamide fine particles, and silicone particles. In the present invention, it is preferable to use rubber particles.
  • the rubber particles may be any rubber particles as long as they are fine particles of a resin that has been chemically cross-linked to a resin exhibiting rubber elasticity and is insoluble and infusible in an organic solvent.
  • Specific examples of the rubber particles include XER-91 (manufactured by Nippon Synthetic Rubber Co., Ltd.), Staphyloid AC3355, AC3816, AC3816N, AC3832, AC4030, AC3364, IM101 (manufactured by Gantz Chemical Co., Ltd.).
  • EXL2655, EXL2602 (manufactured by Kureha Chemical Industry Co., Ltd.) and the like can be mentioned, and AC3816N (manufactured by Ganz Kasei Co., Ltd.) is preferable.
  • the polyamide fine particles may be any polyamide fine particles as long as they are fine particles of 50 ⁇ m or less of a resin having an amide bond, and examples thereof include aliphatic polyamides such as nylon, aromatic polyamides such as Kevlar, and polyamideimide. Specific examples of the polyamide fine particles include VESTOSINT 2070 (manufactured by Daicel Huls Co., Ltd.) and SP500 (manufactured by Toray Industries, Inc.).
  • the average particle diameter of the organic filler is preferably in the range of 0.005 ⁇ m to 1 ⁇ m, and more preferably in the range of 0.2 ⁇ m to 0.6 ⁇ m.
  • the average particle diameter of the organic filler can be measured using a dynamic light scattering method.
  • the average particle size of the organic filler is determined by, for example, dispersing the organic filler uniformly in an appropriate organic solvent using ultrasonic waves or the like, and using a concentrated particle size analyzer (FPAR-1000; manufactured by Otsuka Electronics Co., Ltd.). It can be measured by creating a particle size distribution of the organic filler on a mass basis and setting its median diameter as the average particle size.
  • blending an organic filler is 0.1 mass when the solid content of the photosensitive resin composition shall be 100 mass% from a viewpoint of an improvement of heat resistance and a laser workability. % To 6% by mass is preferable, and 0.5% to 4% by mass is more preferable.
  • the photosensitive resin composition of the present invention comprises (H) photosensitizer, N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine Tertiary amines such as triethanolamine may be added, and photosensitizers such as pyrarizones, anthracenes, coumarins, xanthones, thioxanthones may be added.
  • thioxanthones are preferably used as photosensitizers, and 2,4-diethylthioxanthone is more preferably used. Any one of these photosensitizers may be used alone, or two or more thereof may be used in combination.
  • the photosensitive resin composition of the present invention can adjust the varnish viscosity by further containing (I) an organic solvent.
  • organic solvent include ketones such as ethyl methyl ketone and cyclohexanone, aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene, methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, and propylene glycol.
  • Glycol ethers such as monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol diethyl ether, triethylene glycol monoethyl ether, esters such as ethyl acetate, butyl acetate, butyl cellosolve acetate, carbitol acetate, octane, decane, etc.
  • Examples include petroleum hydrocarbons such as aliphatic hydrocarbons, petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, and solvent naphtha. Among them, solvent naphtha and methyl ethyl Tonnes is preferred. These are used singly or in combination of two or more. Content in the case of using an organic solvent can be suitably adjusted from a viewpoint of the applicability
  • additives examples include fine particles such as melamine and organic bentonite, coloring agents such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black and naphthalene black, hydroquinone Polymerization inhibitors such as phenothiazine, methyl hydroquinone, hydroquinone monomethyl ether, catechol and pyrogallol, thickeners such as benton and montmorillonite, silicone, fluorine and vinyl resin defoamers, brominated epoxy compounds, acid-modified bromine Add various additives such as flame retardants such as fluorinated epoxy compounds, antimony compounds, phosphorus compounds, aromatic condensed phosphate esters, halogen-containing condensed phosphate esters, thermosetting resins such as phenolic curing agents, etc. Can.
  • coloring agents such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide,
  • the photosensitive resin composition of the present invention is appropriately mixed with the above (A) to (C) (and optionally (D) to (J)), and if necessary, a three-roll, ball mill, bead mill, It can be produced as a resin varnish by kneading or stirring with a kneading means such as a sand mill or a stirring means such as a super mixer or a planetary mixer.
  • the use of the photosensitive resin composition of the present invention is not particularly limited, but a photosensitive film, a photosensitive film with a support, an insulating resin sheet such as a prepreg, a circuit board (for laminated board use, multilayer printed wiring board use, etc.), It can be used in a wide range of applications where a resin composition is required, such as solder resist, underfill material, die bonding material, semiconductor sealing material, hole filling resin, and component filling resin. Especially, it is suitable as a resin composition for insulating layers of a multilayer printed wiring board (multilayer printed wiring board using a cured product of a photosensitive resin composition as an insulating layer), particularly an interlayer insulating layer resin composition (photosensitive resin). A multilayer printed wiring board having a cured product of the composition as an interlayer insulating layer) and a resin composition for plating formation (a multilayer printed wiring board in which plating is formed on the cured product of the photosensitive resin composition). Can do.
  • the photosensitive resin composition of this invention can apply
  • the photosensitive film previously formed on the support body can also be laminated
  • the photosensitive film of the present invention can be laminated on various supporting substrates. Examples of the support substrate mainly include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, and a thermosetting polyphenylene ether substrate.
  • the photosensitive resin composition of the present invention can be suitably used in the form of a photosensitive film with a support in which a resin composition layer is formed on a support. That is, the photosensitive film with a support has a layer of the photosensitive resin composition formed on the support.
  • the support include a polyethylene terephthalate film, a polyethylene naphthalate film, a polypropylene film, a polyethylene film, a polyvinyl alcohol film, and a triacetyl acetate film, and a polyethylene terephthalate film is particularly preferable.
  • supports include, for example, product names “Alphan MA-410” and “E-200C” manufactured by Oji Paper Co., Ltd., polypropylene films manufactured by Shin-Etsu Film Co., Ltd., and product names “PS” manufactured by Teijin Limited. Polyethylene terephthalate film such as PS series such as “-25” can be mentioned, but it is not limited thereto.
  • these supports are preferably coated with a release agent such as a silicone coating agent on the surface.
  • the thickness of the support is preferably in the range of 5 ⁇ m to 50 ⁇ m, and more preferably in the range of 10 ⁇ m to 25 ⁇ m.
  • the support tends to be broken when the support is peeled off before development.
  • the thickness exceeds 50 ⁇ m, the support is exposed from above. The resolution tends to decrease.
  • a low fisheye support is preferred.
  • the fish eye means that a material is melted, kneaded, extruded, biaxially stretched, a film is produced by a casting method, etc., and foreign materials, undissolved materials, oxidized deterioration products, etc. of the material are taken into the film. It is a thing.
  • the support is preferably excellent in transparency.
  • the support preferably has a turbidity (haze standardized by JIS-K6714) as an index of transparency of 0.1 to 5.
  • the resin composition layer may be protected with a protective film.
  • the protective film By protecting the resin composition layer side of the photosensitive film with a support with a protective film, it is possible to prevent adhesion or scratches of dust or the like on the surface of the resin composition layer.
  • a film made of the same material as that of the support can be used.
  • the thickness of the protective film is not particularly limited, but is preferably in the range of 1 ⁇ m to 40 ⁇ m, more preferably in the range of 5 ⁇ m to 30 ⁇ m, and still more preferably in the range of 10 ⁇ m to 30 ⁇ m. If the thickness is less than 1 ⁇ m, the handleability of the protective film tends to be reduced, and if it exceeds 40 ⁇ m, the cost tends to be inferior.
  • the protective film preferably has a smaller adhesive force between the resin composition layer and the protective film than the adhesive force between the resin composition layer and the support.
  • the photosensitive film with a support of the present invention is prepared by, for example, preparing a resin varnish obtained by dissolving the photosensitive resin composition of the present invention in an organic solvent according to a method known to those skilled in the art, and applying this resin varnish on the support. And it can manufacture by drying an organic solvent by heating or hot air spraying, etc., and forming a resin composition layer. Specifically, first, after completely removing bubbles in the photosensitive resin composition by a vacuum defoaming method or the like, the photosensitive resin composition is applied onto a support, and a solvent is removed by a hot air furnace or a far infrared furnace.
  • the photosensitive film with a support can be produced by removing and drying, and then laminating a protective film on the resin composition layer obtained as necessary.
  • the specific drying conditions vary depending on the curability of the resin composition and the amount of the organic solvent in the resin varnish. However, in the case of a resin varnish containing 30% by mass to 60% by mass of the organic solvent, the drying condition is 3 ° C. It can be dried for 13 to 13 minutes.
  • the amount of the remaining organic solvent in the resin composition layer is preferably 5% by mass or less with respect to the total amount of the resin composition layer from the viewpoint of preventing diffusion of the organic solvent in the subsequent step. More preferably. Those skilled in the art can appropriately set suitable drying conditions by simple experiments.
  • the thickness of the resin composition layer is preferably in the range of 5 ⁇ m to 500 ⁇ m from the viewpoint of improving the handleability and preventing the sensitivity and resolution inside the resin composition layer from being lowered.
  • the range of 15 ⁇ m to 150 ⁇ m is more preferable, the range of 20 ⁇ m to 100 ⁇ m is still more preferable, and the range of 20 ⁇ m to 60 ⁇ m is even more preferable.
  • a coating method of the photosensitive resin composition for example, gravure coating method, micro gravure coating method, reverse coating method, kiss reverse coating method, die coating method, slot die method, lip coating method, comma coating method, blade coating method, Examples thereof include a roll coating method, a knife coating method, a curtain coating method, a chamber gravure coating method, a slot orifice method, a spray coating method, and a dip coating method.
  • the photosensitive resin composition may be applied in several times, may be applied once, or may be applied by combining a plurality of different methods.
  • the die coating method is preferable because it is excellent in uniform coatability. Further, in order to avoid contamination by foreign matters, it is preferable to carry out the coating process in an environment with little foreign matter generation such as a clean room.
  • a photosensitive resin composition is directly applied on a circuit board in a resin varnish state, and an organic solvent is dried to form a photosensitive film on the circuit board.
  • the circuit board include a glass epoxy board, a metal board, a polyester board, a polyimide board, a BT resin board, a thermosetting polyphenylene ether board, and the like.
  • the circuit board refers to a board on which a conductor layer (circuit) patterned on one or both sides of the board is formed.
  • a substrate having a conductor layer (circuit) in which one or both surfaces of the outermost layer of the multilayer printed wiring board are patterned is also here. It is included in the circuit board.
  • the surface of the conductor layer may be previously roughened by blackening, copper etching, or the like.
  • full-screen printing by screen printing is generally used, but any other means may be used as long as it can be uniformly applied.
  • spray coating method hot melt coating method, bar coating method, applicator method, blade coating method, knife coating method, air knife coating method, curtain flow coating method, roll coating method, gravure coating method, offset printing method, dip coating method , Brushing and other normal application methods can be used.
  • drying is performed in a hot air furnace or a far infrared furnace as necessary. The drying conditions are preferably 80 to 120 ° C. for 3 to 13 minutes. In this way, a photosensitive film is formed on the circuit board.
  • the resin composition layer side is laminated on the single side
  • the laminating process when the photosensitive film with a support has a protective film, the protective film is removed, and then the photosensitive film and the circuit board are preheated as necessary, and the resin composition layer is pressed. And crimping to the circuit board while heating.
  • a method of laminating on a circuit board under reduced pressure by a vacuum laminating method is suitably used.
  • the conditions for the laminating step are not particularly limited.
  • the pressure bonding temperature (laminating temperature) is preferably 70 ° C. to 140 ° C.
  • the pressure bonding pressure is preferably 1 kgf / cm 2 to 11 kgf / cm 2 (9. 8 ⁇ 10 4 N / m 2 to 107.9 ⁇ 10 4 N / m 2 )
  • the pressure bonding time is preferably 5 seconds to 300 seconds
  • the air pressure is 20 mmHg (26.7 hPa) or less.
  • the laminating step may be a batch type or a continuous type using a roll.
  • the vacuum laminating method can be performed using a commercially available vacuum laminator.
  • vacuum laminators include, for example, a vacuum applicator manufactured by Nichigo-Morton Co., Ltd., a vacuum pressurizing laminator manufactured by Meiki Seisakusho Co., Ltd., a roll dry coater manufactured by Hitachi Industries, Ltd., and Hitachi AIC Co., Ltd. ) Made vacuum laminator and the like. In this way, a photosensitive film is formed on the circuit board.
  • a predetermined part of the resin composition layer is then irradiated with actinic rays through a mask pattern, and a resin composition layer of an irradiated part
  • An exposure process for photocuring is performed.
  • the actinic rays include ultraviolet rays, visible rays, electron beams, and X-rays, and ultraviolet rays are particularly preferable.
  • the irradiation amount of ultraviolet rays is about 10 mJ / cm 2 to 1000 mJ / cm 2 .
  • the exposure method includes a contact exposure method in which a mask pattern is brought into close contact with a printed wiring board, and a non-contact exposure method in which exposure is carried out using parallel light rays without being brought into close contact, either of which may be used.
  • a contact exposure method in which a mask pattern is brought into close contact with a printed wiring board
  • a non-contact exposure method in which exposure is carried out using parallel light rays without being brought into close contact, either of which may be used.
  • you may expose from a support body and may expose after a support body peels.
  • a safe and stable developer having good operability such as an alkaline aqueous solution, an aqueous developer, an organic solvent, etc. is used. Is preferred. Further, as a developing method, a known method such as spraying, rocking dipping, brushing, scraping or the like is appropriately employed.
  • organic solvent used as the developer examples include acetone, ethyl acetate, alkoxyethanol having an alkoxy group having 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol. Monobutyl ether.
  • the concentration of such an organic solvent is preferably 2% by mass to 90% by mass with respect to the total amount of the developer. Moreover, the temperature of such an organic solvent can be adjusted according to developability. Furthermore, such organic solvents can be used alone or in combination of two or more. Examples of the organic solvent developer used alone include 1,1,1-trichloroethane, N-methylpyrrolidone, N, N-dimethylformamide, cyclohexanone, methyl isobutyl ketone, ⁇ -butyrolactone, propylene glycol 1-monomethyl ether 2 -Acetate (PGMEA), among which PGMEA is preferred in the present invention.
  • PGMEA propylene glycol 1-monomethyl ether 2 -Acetate
  • development methods include a dip method, a battle method, a spray method, a high-pressure spray method, brushing, and slapping, and the high-pressure spray method is suitable for improving the resolution.
  • the spray pressure when the spray method is employed is preferably 0.05 MPa to 0.3 MPa.
  • a post-bake step is performed to form an insulating layer (cured product).
  • the post-bake process include an ultraviolet irradiation process using a high-pressure mercury lamp and a heating process using a clean oven. Case of ultraviolet irradiation can adjust its dose optionally, the irradiation can be carried out, for example 0.05J / cm 2 ⁇ 10J / cm 2 of about dose.
  • the heating conditions may be appropriately selected according to the type and content of the resin component in the resin composition, but are preferably 150 ° C. to 220 ° C. for 20 minutes to 180 minutes, more preferably 160 ° C. It is selected in the range of 30 minutes to 120 minutes at 200 ° C.
  • a conductor layer is formed on the insulating layer by dry plating or wet plating.
  • a known method such as a vapor deposition method, a sputtering method, or an ion plating method can be used.
  • a metal film can be formed on the insulating layer by placing the support in a vacuum vessel and evaporating the metal by heating.
  • the sputtering method for example, the support is placed in a vacuum vessel, an inert gas such as argon is introduced, a direct current voltage is applied, the ionized inert gas is made to collide with the target metal, and the struck metal is used.
  • a metal film can be formed on the insulating layer.
  • the surface of the formed insulating layer is subjected to a swelling treatment with a swelling solution, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing solution in this order to form an uneven anchor.
  • the swelling treatment with the swelling liquid is performed by immersing the insulating layer in the swelling liquid at 50 to 80 ° C. for 5 to 20 minutes.
  • the swelling liquid include an alkaline solution, and examples of the alkaline solution include a sodium hydroxide solution and a potassium hydroxide solution.
  • Examples of commercially available swelling liquids include Swelling Dip Securigans P (Swelling Dip Securiganth P), Swelling Dip Securigans SBU (Swelling Dip Securiganth SBU) manufactured by Atotech Japan Co., Ltd. be able to.
  • the roughening treatment with an oxidizing agent is performed by immersing the insulating layer in an oxidizing agent solution at 60 to 80 ° C. for 10 to 30 minutes.
  • Examples of the oxidizing agent include alkaline permanganate solution in which potassium permanganate and sodium permanganate are dissolved in an aqueous solution of sodium hydroxide, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid and the like. it can.
  • the concentration of permanganate in the alkaline permanganate solution is preferably 5% by weight to 10% by weight.
  • examples of commercially available oxidizing agents include alkaline permanganate solutions such as Concentrate Compact CP and Dosing Solution Securigans P manufactured by Atotech Japan Co., Ltd.
  • the neutralization treatment with the neutralizing solution is performed by immersing in a neutralizing solution at 30 to 50 ° C. for 3 to 10 minutes.
  • an acidic aqueous solution is preferable, and as a commercially available product, Reduction Solution / Secligant P manufactured by Atotech Japan Co., Ltd. may be mentioned.
  • a conductor layer is formed by combining electroless plating and electrolytic plating.
  • a plating resist having a pattern opposite to that of the conductor layer can be formed, and the conductor layer can be formed only by electroless plating.
  • a subsequent pattern formation method for example, a subtractive method or a semi-additive method known to those skilled in the art can be used.
  • a semiconductor device can be manufactured by using the multilayer printed wiring board of the present invention.
  • a semiconductor device can be manufactured by mounting a semiconductor chip in a conductive portion of the multilayer printed wiring board of the present invention.
  • the “conduction location” is a “location where an electrical signal is transmitted in a multilayer printed wiring board”, and the location may be a surface or an embedded location.
  • the semiconductor chip is not particularly limited as long as it is an electric circuit element made of a semiconductor.
  • the semiconductor chip mounting method for manufacturing the semiconductor device of the present invention is not particularly limited as long as the semiconductor chip functions effectively, but specifically, a wire bonding mounting method, a flip chip mounting method, and no bumps.
  • Examples include a mounting method using a build-up layer (BBUL), a mounting method using an anisotropic conductive film (ACF), and a mounting method using a non-conductive film (NCF).
  • the photosensitive resin composition of the present invention can provide a resin composition having excellent physical properties and suitable for a buildup layer of a multilayer printed wiring board while having photosensitivity. Further, it is possible to provide a cured product which is excellent in dielectric properties, water resistance and heat resistance and suitable for development with an organic solvent. Hereinafter, these characteristics will be described in detail.
  • the dielectric loss tangent of the cured product of the photosensitive resin composition of the present invention can be measured by ⁇ Measurement of dielectric characteristics> described later. Specifically, the dielectric loss tangent can be measured by a cavity resonance perturbation method at a frequency of 5.8 GHz and a measurement temperature of 23 ° C. From the viewpoints of preventing heat generation at high frequencies, reducing signal delay and signal noise, the dielectric loss tangent is preferably 0.05 or less, more preferably 0.04 or less, and further preferably 0.03 or less. Preferably, it is 0.02 or less, and further preferably 0.013 or less. On the other hand, the lower limit value of the dielectric loss tangent is not particularly limited, but is 0.005 or more.
  • the water resistance (water absorption) of the cured product of the photosensitive resin composition of the present invention can be measured by a measurement method described in ⁇ Measurement of water resistance> described later.
  • the water absorption is preferably 3% or less, more preferably 2% or less, and more preferably 1% or less from the viewpoint of preventing generation of voids during printed wiring board production and improving insulation reliability. More preferably, it is still more preferably 0.8% or less.
  • the lower limit of the water absorption rate is not particularly limited, but is 0.01% or more, 0.1% or more, 0.2% or more, and the like.
  • the heat resistance of the cured product of the photosensitive resin composition of the present invention can be measured by a measurement method described in ⁇ Evaluation of heat resistance> described later.
  • a glass transition point in terms of preventing deterioration of the cured product when a thermal history is given to the cured product.
  • the glass transition point is preferably 110 ° C. or higher.
  • the upper limit of the glass transition point is not particularly limited, but is preferably 300 ° C. or lower.
  • a thermal expansion coefficient may be employed as a heat resistance index.
  • the coefficient of thermal expansion is preferably 10 to 30 ppm / ° C.
  • Part means part by mass.
  • the pressure bonding conditions were 20 seconds after evacuation, and a pressure bonding temperature of 80 ° C., a pressure bonding pressure of 0.2 MPa, and a pressure time of 20 seconds.
  • the laminate is allowed to stand at room temperature for 1 hour or longer, and a 100 mJ / cm 2 ultraviolet ray is used on the support of the laminate using a pattern forming apparatus so that a round hole having a diameter of 80 mm can be formed using a round hole pattern. The exposure was performed. After standing at room temperature for 30 minutes, the support was peeled off from the laminate.
  • the entire surface of the resin composition layer on the laminated plate was developed by being immersed in PGMEA (propylene glycol 1-monomethyl ether 2-acetate) at 30 ° C.
  • PGMEA propylene glycol 1-monomethyl ether 2-acetate
  • a 1 mass% sodium carbonate aqueous solution at 30 ° C. was applied as a developing solution over the entire surface of the resin composition layer on the laminated plate at a spray pressure of 0.15 MPa for a minimum developing time (minimum for developing an unexposed portion). Spray development for 1.5 times the time. After spray development, ultraviolet irradiation of 1 J / cm 2 was performed, followed by heat treatment at 190 ° C. for 60 minutes, and an insulating layer having an opening with a diameter of 80 mm was formed on the laminate.
  • the pressure bonding conditions were 20 seconds after evacuation, and a pressure bonding temperature of 80 ° C., a pressure bonding pressure of 0.2 MPa, and a pressure time of 20 seconds.
  • the laminate was allowed to stand at room temperature for 1 hour or longer, and exposed to ultraviolet light of 100 mJ / cm 2 from the support of the laminate.
  • the cured product for evaluation was cut into a length of 80 mm and a width of 2 mm, and used as an evaluation sample 1.
  • the dielectric loss tangent of this evaluation sample 1 was measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23 ° C. by a cavity resonance perturbation method using an HP 8362B apparatus manufactured by Agilent Technologies (AGILENT TECHNOLOGIES). Measurement was performed on two evaluation samples 1, and an average value was calculated.
  • thermomechanical analysis was performed by a tensile load method using a thermomechanical analyzer TMA-SS6100 (manufactured by Seiko Instruments Inc.). After the evaluation sample 3 was mounted on the apparatus, the measurement was continuously performed twice under the measurement conditions of a load of 1 G and a heating rate of 5 ° C./min. The glass transition temperature (° C.) was calculated from the point at which the slope of the dimensional change signal in the second measurement changed. As the thermal expansion coefficient, an average linear thermal expansion coefficient (ppm / ° C.) from 25 ° C. to 150 ° C. in the second measurement was calculated.
  • ⁇ Synthesis Example 2 Synthesis of methacrylate compound having bixylenol structure, biscresol fluorene structure and epoxy group>
  • a reaction vessel 190 g of bixylenol type epoxy resin (Mitsubishi Chemical Corporation YX4000, epoxy equivalent 185), 14 g of bisphenolacetophenone (phenolic hydroxyl group equivalent 145), biscresol fluorene (manufactured by JFE Chemical Co., Ltd., phenolic hydroxyl group equivalent) 190) 170 g and cyclohexanone 150 g were added and dissolved by stirring.
  • bixylenol type epoxy resin Mitsubishi Chemical Corporation YX4000, epoxy equivalent 185
  • bisphenolacetophenone phenolic hydroxyl group equivalent 145
  • biscresol fluorene manufactured by JFE Chemical Co., Ltd., phenolic hydroxyl group equivalent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Ceramic Engineering (AREA)
  • Materials For Photolithography (AREA)
  • Production Of Multi-Layered Print Wiring Board (AREA)
  • Non-Metallic Protective Coatings For Printed Circuits (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne une composition de résine photosensible qui présente une excellente fiabilité en termes d'isolation, qui a des propriétés physiques convenant à une couche à accumulation (couche d'isolation intercouche) d'un tableau de connexions imprimé multicouche, et qui fait également preuve de photosensibilité. Cette composition de résine photosensible contient : (A) une résine époxy, (B) un ou plusieurs agents de traitement choisis dans le groupe constitué par agents de traitement à l'ester actif, agents de traitement à l'ester de cyanate et agents de traitement à la benzoxazine, et (C) un composé ayant une structure (méth)acrylate.
PCT/JP2014/067067 2013-07-04 2014-06-26 Composition de résine photosensible Ceased WO2015002071A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2015525178A JPWO2015002071A1 (ja) 2013-07-04 2014-06-26 感光性樹脂組成物
CN202011041126.5A CN112147844B (zh) 2013-07-04 2014-06-26 感光性树脂组合物
CN201480036156.3A CN105308506B (zh) 2013-07-04 2014-06-26 感光性树脂组合物
KR1020167003029A KR102228718B1 (ko) 2013-07-04 2014-06-26 감광성 수지 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013141033 2013-07-04
JP2013-141033 2013-07-04

Publications (1)

Publication Number Publication Date
WO2015002071A1 true WO2015002071A1 (fr) 2015-01-08

Family

ID=52143649

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/067067 Ceased WO2015002071A1 (fr) 2013-07-04 2014-06-26 Composition de résine photosensible

Country Status (5)

Country Link
JP (4) JPWO2015002071A1 (fr)
KR (1) KR102228718B1 (fr)
CN (2) CN105308506B (fr)
TW (1) TWI687479B (fr)
WO (1) WO2015002071A1 (fr)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015106141A (ja) * 2013-12-03 2015-06-08 日立化成株式会社 感光性樹脂組成物、及び感光性エレメント
JP2016146394A (ja) * 2015-02-06 2016-08-12 太陽インキ製造株式会社 硬化性樹脂組成物、ドライフィルム、プリント配線板およびその製造方法
WO2017044381A1 (fr) * 2015-09-09 2017-03-16 Carbon3D, Inc. Résines époxydes à polymérisation duale pour une fabrication additive
US9676963B2 (en) 2014-06-23 2017-06-13 Carbon, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening
JP2017201350A (ja) * 2016-05-02 2017-11-09 日立化成株式会社 感光性導電フィルム、導電パターンの形成方法及び導電パターン基板の製造方法
KR20180103819A (ko) 2016-01-20 2018-09-19 미츠비시 가스 가가쿠 가부시키가이샤 수지 조성물, 지지체가 부착된 수지 시트, 다층 프린트 배선판 및 반도체 장치
US10316213B1 (en) 2017-05-01 2019-06-11 Formlabs, Inc. Dual-cure resins and related methods
JP2019158949A (ja) * 2018-03-08 2019-09-19 住友ベークライト株式会社 感光性樹脂組成物および電子装置
WO2019189220A1 (fr) * 2018-03-30 2019-10-03 太陽インキ製造株式会社 Film sec, produit durci et carte imprimée
JP2019183071A (ja) * 2018-04-16 2019-10-24 味の素株式会社 樹脂組成物
JP2019183070A (ja) * 2018-04-16 2019-10-24 味の素株式会社 樹脂組成物
KR20190120705A (ko) * 2018-04-16 2019-10-24 아지노모토 가부시키가이샤 수지 조성물
JP2019206624A (ja) * 2018-05-28 2019-12-05 味の素株式会社 樹脂組成物
JP2019218483A (ja) * 2018-06-20 2019-12-26 三菱ケミカル株式会社 トウプリプレグ、積層体、及び繊維強化複合材料
JP2020023678A (ja) * 2018-07-27 2020-02-13 日本化薬株式会社 電子部品用封止剤
WO2020040092A1 (fr) * 2018-08-20 2020-02-27 Jsr株式会社 Procédé pour former un motif, et composition sensible au rayonnement
CN110955115A (zh) * 2018-09-27 2020-04-03 味之素株式会社 树脂组合物、感光性膜、带支承体的感光性膜、印刷布线板和半导体装置
KR20200070275A (ko) * 2017-10-27 2020-06-17 제이엑스티지 에네루기 가부시키가이샤 경화 수지용 조성물, 상기 조성물의 경화물, 상기 조성물 및 상기 경화물의 제조방법, 및 반도체 장치
JP2020105523A (ja) * 2020-02-21 2020-07-09 味の素株式会社 樹脂組成物
JPWO2020218457A1 (fr) * 2019-04-26 2020-10-29
JP2021028699A (ja) * 2019-08-09 2021-02-25 味の素株式会社 感光性樹脂組成物、感光性樹脂組成物の硬化物、樹脂シート、プリント配線板及び半導体装置
JP2021107535A (ja) * 2019-12-27 2021-07-29 キヤノン株式会社 光硬化性組成物
US20210355364A1 (en) * 2019-02-01 2021-11-18 Fujifilm Corporation Composition for forming thermally conductive material, and thermally conductive material
JP2022024857A (ja) * 2020-07-28 2022-02-09 昭和電工マテリアルズ株式会社 感光性樹脂組成物、感光性樹脂フィルム、多層プリント配線板及び半導体パッケージ、並びに多層プリント配線板の製造方法
CN114253070A (zh) * 2020-09-25 2022-03-29 株式会社田村制作所 感光性树脂组合物、固化物和电子电路基板
WO2022181431A1 (fr) * 2021-02-26 2022-09-01 富士フイルム株式会社 Composition photosensible, film de transfert, procédé de formation de motif, procédé de production pour câblage de circuit et procédé de production pour panneau tactile
JPWO2023153103A1 (fr) * 2022-02-09 2023-08-17
JP2023183727A (ja) * 2022-06-16 2023-12-28 味の素株式会社 樹脂組成物
WO2024024881A1 (fr) * 2022-07-29 2024-02-01 株式会社スリーボンド Composition de résine époxydique
US12421426B2 (en) 2019-01-23 2025-09-23 Fujifilm Corporation Composition, thermally conductive sheet, and device with thermally conductive layer
US12441833B2 (en) 2018-12-10 2025-10-14 Eneos Corporation Composition for curable resin, cured product of said composition, production method for said composition and said cured product, and semiconductor device

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7046477B2 (ja) * 2016-07-01 2022-04-04 味の素株式会社 樹脂組成物
JP6776749B2 (ja) * 2016-09-12 2020-10-28 味の素株式会社 樹脂組成物
CN108024453B (zh) * 2016-10-31 2020-10-23 宏启胜精密电子(秦皇岛)有限公司 镂空电路板及其制作方法
TWI808064B (zh) * 2016-11-30 2023-07-11 美商Ｉｃｌ－Ｉｐ美國股份有限公司 熱固性樹脂之活性酯硬化劑、含彼之阻燃組成物及由彼製成的物品
CN108117634B (zh) * 2016-11-30 2019-08-27 广东生益科技股份有限公司 一种热固性树脂组合物
JP6354884B1 (ja) * 2017-03-13 2018-07-11 横浜ゴム株式会社 シアネートエステル樹脂組成物およびプリプレグ
JP6950536B2 (ja) * 2018-01-09 2021-10-13 味の素株式会社 樹脂組成物
CN110564099B (zh) * 2018-06-05 2021-09-14 汕头市夸克智能科技有限公司 一种线路板基材3d打印树脂及其制备方法
CN114270261A (zh) * 2019-08-14 2022-04-01 昭和电工材料株式会社 感光性树脂组合物、感光性树脂膜、多层印刷配线板和半导体封装体、以及多层印刷配线板的制造方法
TWI776557B (zh) * 2021-06-21 2022-09-01 昱鐳光電科技股份有限公司 活性聚酯、固化性樹脂組成物及樹脂固化物
JPWO2023021900A1 (fr) * 2021-08-20 2023-02-23
JPWO2023238732A1 (fr) * 2022-06-06 2023-12-14
KR20240066073A (ko) * 2022-11-07 2024-05-14 주식회사 엘지화학 수지 조성물 및 이를 포함하는 인쇄회로기판
CN116330791B (zh) * 2023-03-28 2025-12-05 杭州福斯特电子材料有限公司 层叠体、机械加强层叠体和其制备方法、含有其的感光元器件的制备方法
CN119684529B (zh) * 2024-12-18 2026-01-02 苏州闪铸三维科技有限公司 一种3d打印耐热性树脂及其制备方法和应用

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56141321A (en) * 1980-04-08 1981-11-05 Mitsubishi Gas Chem Co Inc Photosetting resin composition
JPH10142797A (ja) * 1996-11-11 1998-05-29 Mitsubishi Gas Chem Co Inc 耐熱性光選択熱硬化塗料
JP2001330951A (ja) * 2000-05-22 2001-11-30 San Nopco Ltd 感光性樹脂組成物およびその硬化物
JP2002357896A (ja) * 2001-06-01 2002-12-13 Mitsubishi Gas Chem Co Inc レジスト樹脂組成物
JP2004189976A (ja) * 2002-12-13 2004-07-08 Mitsubishi Gas Chem Co Inc 感光性樹脂組成物およびその硬化物
JP2006028498A (ja) * 2004-06-18 2006-02-02 Sanyo Chem Ind Ltd 硬化性組成物
JP2006343384A (ja) * 2005-06-07 2006-12-21 Sumitomo Bakelite Co Ltd 感光性樹脂組成物およびソルダーレジスト
JP2007003807A (ja) * 2005-06-23 2007-01-11 Sumitomo Bakelite Co Ltd 感光性樹脂組成物および該組成物を用いたソルダーレジスト
JP2009010057A (ja) * 2007-06-27 2009-01-15 Toray Ind Inc 電子素子の実装方法
WO2010026927A1 (fr) * 2008-09-04 2010-03-11 日立化成工業株式会社 Composition de résine photosensible pour film protecteur de carte de circuit imprimé pour ensemble semiconducteur
JP2011089038A (ja) * 2009-10-22 2011-05-06 Ajinomoto Co Inc 樹脂組成物

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005244150A (ja) * 2004-01-28 2005-09-08 Ajinomoto Co Inc 樹脂組成物、それを用いた接着フィルム及び多層プリント配線板
JP4587865B2 (ja) * 2004-04-22 2010-11-24 昭和電工株式会社 感光性樹脂組成物及びその硬化物並びにそれらを使用するプリント配線基板の製造方法
JP5072101B2 (ja) 2008-04-25 2012-11-14 日本化薬株式会社 Ｍｅｍｓ用感光性樹脂組成物及びその硬化物
JP2010026927A (ja) 2008-07-23 2010-02-04 Sony Corp 表示画面生成装置、表示画面生成方法およびプログラム
JP5412936B2 (ja) * 2009-04-23 2014-02-12 味の素株式会社 プリント配線板の製造方法
JP5515394B2 (ja) * 2009-04-30 2014-06-11 株式会社ピーアイ技術研究所 感光性変性ポリイミド樹脂組成物及びその用途
JP5633381B2 (ja) * 2011-01-17 2014-12-03 Jsr株式会社 感放射線性樹脂組成物、硬化膜及び硬化膜の形成方法
JP2012211943A (ja) * 2011-03-30 2012-11-01 Fujifilm Corp 感光性組成物、並びに、感光性フィルム、永久パターン、永久パターン形成方法、及びプリント基板

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56141321A (en) * 1980-04-08 1981-11-05 Mitsubishi Gas Chem Co Inc Photosetting resin composition
JPH10142797A (ja) * 1996-11-11 1998-05-29 Mitsubishi Gas Chem Co Inc 耐熱性光選択熱硬化塗料
JP2001330951A (ja) * 2000-05-22 2001-11-30 San Nopco Ltd 感光性樹脂組成物およびその硬化物
JP2002357896A (ja) * 2001-06-01 2002-12-13 Mitsubishi Gas Chem Co Inc レジスト樹脂組成物
JP2004189976A (ja) * 2002-12-13 2004-07-08 Mitsubishi Gas Chem Co Inc 感光性樹脂組成物およびその硬化物
JP2006028498A (ja) * 2004-06-18 2006-02-02 Sanyo Chem Ind Ltd 硬化性組成物
JP2006343384A (ja) * 2005-06-07 2006-12-21 Sumitomo Bakelite Co Ltd 感光性樹脂組成物およびソルダーレジスト
JP2007003807A (ja) * 2005-06-23 2007-01-11 Sumitomo Bakelite Co Ltd 感光性樹脂組成物および該組成物を用いたソルダーレジスト
JP2009010057A (ja) * 2007-06-27 2009-01-15 Toray Ind Inc 電子素子の実装方法
WO2010026927A1 (fr) * 2008-09-04 2010-03-11 日立化成工業株式会社 Composition de résine photosensible pour film protecteur de carte de circuit imprimé pour ensemble semiconducteur
JP2011089038A (ja) * 2009-10-22 2011-05-06 Ajinomoto Co Inc 樹脂組成物

Cited By (75)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015106141A (ja) * 2013-12-03 2015-06-08 日立化成株式会社 感光性樹脂組成物、及び感光性エレメント
US11358342B2 (en) 2014-06-23 2022-06-14 Carbon, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening
US10647879B2 (en) 2014-06-23 2020-05-12 Carbon, Inc. Methods for producing a dental mold, dental implant or dental aligner from materials having multiple mechanisms of hardening
US9676963B2 (en) 2014-06-23 2017-06-13 Carbon, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening
US10968307B2 (en) 2014-06-23 2021-04-06 Carbon, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening
US9982164B2 (en) 2014-06-23 2018-05-29 Carbon, Inc. Polyurea resins having multiple mechanisms of hardening for use in producing three-dimensional objects
US10899868B2 (en) 2014-06-23 2021-01-26 Carbon, Inc. Methods for producing footwear with materials having multiple mechanisms of hardening
US11299579B2 (en) 2014-06-23 2022-04-12 Carbon, Inc. Water cure methods for producing three-dimensional objects from materials having multiple mechanisms of hardening
US11312084B2 (en) 2014-06-23 2022-04-26 Carbon, Inc. Methods for producing helmet inserts with materials having multiple mechanisms of hardening
US10155882B2 (en) 2014-06-23 2018-12-18 Carbon, Inc. Methods of producing EPOXY three-dimensional objects from materials having multiple mechanisms of hardening
US10240066B2 (en) 2014-06-23 2019-03-26 Carbon, Inc. Methods of producing polyurea three-dimensional objects from materials having multiple mechanisms of hardening
US11850803B2 (en) 2014-06-23 2023-12-26 Carbon, Inc. Methods for producing three-dimensional objects with apparatus having feed channels
US10647880B2 (en) 2014-06-23 2020-05-12 Carbon, Inc. Methods of producing polyurethane three-dimensional objects from materials having multiple mechanisms of hardening
US11440266B2 (en) 2014-06-23 2022-09-13 Carbon, Inc. Methods of producing epoxy three-dimensional objects from materials having multiple mechanisms of hardening
US11707893B2 (en) 2014-06-23 2023-07-25 Carbon, Inc. Methods for producing three-dimensional objects with apparatus having feed channels
US12179435B2 (en) 2014-06-23 2024-12-31 Carbon, Inc. Methods of producing three-dimensional objects with apparatus having feed channels
US12172382B2 (en) 2014-06-23 2024-12-24 Carbon, Inc. Methods for producing three-dimensional objects
JP2016146394A (ja) * 2015-02-06 2016-08-12 太陽インキ製造株式会社 硬化性樹脂組成物、ドライフィルム、プリント配線板およびその製造方法
JP2018528107A (ja) * 2015-09-09 2018-09-27 カーボン，インコーポレイテッド 積層造形用エポキシ二重硬化樹脂
US11814472B2 (en) 2015-09-09 2023-11-14 Carbon, Inc. Epoxy dual cure resins for additive manufacturing
CN108291011A (zh) * 2015-09-09 2018-07-17 卡本有限公司 用于增材制造的环氧双重固化树脂
US10975193B2 (en) 2015-09-09 2021-04-13 Carbon, Inc. Epoxy dual cure resins for additive manufacturing
WO2017044381A1 (fr) * 2015-09-09 2017-03-16 Carbon3D, Inc. Résines époxydes à polymérisation duale pour une fabrication additive
CN108291011B (zh) * 2015-09-09 2021-03-02 卡本有限公司 用于增材制造的环氧双重固化树脂
KR20180103819A (ko) 2016-01-20 2018-09-19 미츠비시 가스 가가쿠 가부시키가이샤 수지 조성물, 지지체가 부착된 수지 시트, 다층 프린트 배선판 및 반도체 장치
JP2017201350A (ja) * 2016-05-02 2017-11-09 日立化成株式会社 感光性導電フィルム、導電パターンの形成方法及び導電パターン基板の製造方法
US10793745B2 (en) 2017-05-01 2020-10-06 Formlabs, Inc. Dual-cure resins and related methods
US10316213B1 (en) 2017-05-01 2019-06-11 Formlabs, Inc. Dual-cure resins and related methods
KR20200070275A (ko) * 2017-10-27 2020-06-17 제이엑스티지 에네루기 가부시키가이샤 경화 수지용 조성물, 상기 조성물의 경화물, 상기 조성물 및 상기 경화물의 제조방법, 및 반도체 장치
KR102427036B1 (ko) 2017-10-27 2022-08-01 에네오스 가부시키가이샤 경화 수지용 조성물, 상기 조성물의 경화물, 상기 조성물 및 상기 경화물의 제조방법, 및 반도체 장치
US11897998B2 (en) 2017-10-27 2024-02-13 Eneos Corporation Composition for curable resin, cured product of said composition, production method for said composition and said cured product, and semiconductor device
JP2019158949A (ja) * 2018-03-08 2019-09-19 住友ベークライト株式会社 感光性樹脂組成物および電子装置
WO2019189220A1 (fr) * 2018-03-30 2019-10-03 太陽インキ製造株式会社 Film sec, produit durci et carte imprimée
JP2019179223A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 ドライフィルム、硬化物およびプリント配線板
KR20190120705A (ko) * 2018-04-16 2019-10-24 아지노모토 가부시키가이샤 수지 조성물
KR20190120704A (ko) * 2018-04-16 2019-10-24 아지노모토 가부시키가이샤 수지 조성물
KR102749619B1 (ko) * 2018-04-16 2025-01-03 아지노모토 가부시키가이샤 수지 조성물
JP2019183071A (ja) * 2018-04-16 2019-10-24 味の素株式会社 樹脂組成物
JP2019183070A (ja) * 2018-04-16 2019-10-24 味の素株式会社 樹脂組成物
JP2021185228A (ja) * 2018-04-16 2021-12-09 味の素株式会社 樹脂組成物
KR102742383B1 (ko) * 2018-04-16 2024-12-16 아지노모토 가부시키가이샤 수지 조성물
KR102736536B1 (ko) * 2018-04-16 2024-12-03 아지노모토 가부시키가이샤 수지 조성물
TWI863905B (zh) * 2018-04-16 2024-12-01 日商味之素股份有限公司 樹脂組成物
JP7287418B2 (ja) 2018-04-16 2023-06-06 味の素株式会社 樹脂組成物
KR20190120711A (ko) * 2018-04-16 2019-10-24 아지노모토 가부시키가이샤 수지 조성물
JP2019206624A (ja) * 2018-05-28 2019-12-05 味の素株式会社 樹脂組成物
JP2019218483A (ja) * 2018-06-20 2019-12-26 三菱ケミカル株式会社 トウプリプレグ、積層体、及び繊維強化複合材料
JP2022191471A (ja) * 2018-06-20 2022-12-27 三菱ケミカル株式会社 複合材料およびその製造方法、成形品並びに中間基材
JP2020023678A (ja) * 2018-07-27 2020-02-13 日本化薬株式会社 電子部品用封止剤
JP7266484B2 (ja) 2018-07-27 2023-04-28 日本化薬株式会社 電子部品用封止剤
WO2020040092A1 (fr) * 2018-08-20 2020-02-27 Jsr株式会社 Procédé pour former un motif, et composition sensible au rayonnement
CN110955115A (zh) * 2018-09-27 2020-04-03 味之素株式会社 树脂组合物、感光性膜、带支承体的感光性膜、印刷布线板和半导体装置
US12441833B2 (en) 2018-12-10 2025-10-14 Eneos Corporation Composition for curable resin, cured product of said composition, production method for said composition and said cured product, and semiconductor device
US12421426B2 (en) 2019-01-23 2025-09-23 Fujifilm Corporation Composition, thermally conductive sheet, and device with thermally conductive layer
US12391859B2 (en) * 2019-02-01 2025-08-19 Fujifilm Corporation Composition for forming thermally conductive material, and thermally conductive material
US20210355364A1 (en) * 2019-02-01 2021-11-18 Fujifilm Corporation Composition for forming thermally conductive material, and thermally conductive material
JP7569784B2 (ja) 2019-04-26 2024-10-18 株式会社Ｅｎｅｏｓマテリアル 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置
US12258472B2 (en) 2019-04-26 2025-03-25 Eneos Corporation Composition for curable resins, cured product of said composition, production method for said composition and said cured product, and semiconductor device
WO2020218457A1 (fr) * 2019-04-26 2020-10-29 Ｊｘｔｇエネルギー株式会社 Composition de résine durcissable, produit durci de composition de résine durcissable, procédé de production pour composition de résine durcissable et produit durci de composition de résine durcissable, et dispositif à semi-conducteur
JPWO2020218457A1 (fr) * 2019-04-26 2020-10-29
JP7363182B2 (ja) 2019-08-09 2023-10-18 味の素株式会社 感光性樹脂組成物、感光性樹脂組成物の硬化物、樹脂シート、プリント配線板及び半導体装置
JP2021028699A (ja) * 2019-08-09 2021-02-25 味の素株式会社 感光性樹脂組成物、感光性樹脂組成物の硬化物、樹脂シート、プリント配線板及び半導体装置
JP2021107535A (ja) * 2019-12-27 2021-07-29 キヤノン株式会社 光硬化性組成物
US12030992B2 (en) 2019-12-27 2024-07-09 Canon Kabushiki Kaisha Photocurable composition
JP7237915B2 (ja) 2019-12-27 2023-03-13 キヤノン株式会社 光硬化性組成物
JP2020105523A (ja) * 2020-02-21 2020-07-09 味の素株式会社 樹脂組成物
JP7067576B2 (ja) 2020-02-21 2022-05-16 味の素株式会社 樹脂組成物
JP2022024857A (ja) * 2020-07-28 2022-02-09 昭和電工マテリアルズ株式会社 感光性樹脂組成物、感光性樹脂フィルム、多層プリント配線板及び半導体パッケージ、並びに多層プリント配線板の製造方法
JP7654944B2 (ja) 2020-07-28 2025-04-02 株式会社レゾナック 感光性樹脂組成物、感光性樹脂フィルム、多層プリント配線板及び半導体パッケージ、並びに多層プリント配線板の製造方法
CN114253070A (zh) * 2020-09-25 2022-03-29 株式会社田村制作所 感光性树脂组合物、固化物和电子电路基板
WO2022181431A1 (fr) * 2021-02-26 2022-09-01 富士フイルム株式会社 Composition photosensible, film de transfert, procédé de formation de motif, procédé de production pour câblage de circuit et procédé de production pour panneau tactile
JPWO2023153103A1 (fr) * 2022-02-09 2023-08-17
JP2023183727A (ja) * 2022-06-16 2023-12-28 味の素株式会社 樹脂組成物
JP7694470B2 (ja) 2022-06-16 2025-06-18 味の素株式会社 樹脂組成物
WO2024024881A1 (fr) * 2022-07-29 2024-02-01 株式会社スリーボンド Composition de résine époxydique

Also Published As

Publication number Publication date
CN112147844A (zh) 2020-12-29
KR20160030231A (ko) 2016-03-16
TWI687479B (zh) 2020-03-11
JP7099491B2 (ja) 2022-07-12
JPWO2015002071A1 (ja) 2017-02-23
JP2022107613A (ja) 2022-07-22
KR102228718B1 (ko) 2021-03-18
CN105308506A (zh) 2016-02-03
JP6711425B2 (ja) 2020-06-17
TW201516087A (zh) 2015-05-01
JP7334820B2 (ja) 2023-08-29
CN112147844B (zh) 2025-01-28
CN105308506B (zh) 2020-10-27
JP2020154325A (ja) 2020-09-24
JP2019056940A (ja) 2019-04-11

Similar Documents

Publication Publication Date Title
JP7334820B2 (ja) 感光性樹脂組成物、支持体付き感光性フィルム、多層プリント配線板及び半導体装置
JP6094271B2 (ja) 感光性樹脂組成物
JP7345429B2 (ja) 感光性樹脂組成物、感光性フィルム、多層プリント配線板、半導体装置、及び、多層プリント配線板の製造方法
JP6372108B2 (ja) 配線板及びその製造方法
US8912279B2 (en) Resin composition
JP7306343B2 (ja) 感光性樹脂組成物
WO2013061688A1 (fr) Composition de résine
CN116731471A (zh) 树脂组合物
JP2023118726A (ja) 感光性樹脂組成物
JP2021039202A (ja) 感光性樹脂組成物
JP7281263B2 (ja) 樹脂組成物、感光性フィルム、支持体付き感光性フィルム、プリント配線板及び半導体装置
JP2022119819A (ja) 感光性樹脂組成物
JP7363182B2 (ja) 感光性樹脂組成物、感光性樹脂組成物の硬化物、樹脂シート、プリント配線板及び半導体装置
JP6677203B2 (ja) 感光性樹脂組成物、感光性フィルム、支持体付き感光性フィルム、プリント配線板及び半導体装置
JP2022118633A (ja) 感光性樹脂組成物
JP6606823B2 (ja) 層間絶縁用樹脂組成物、支持体付き感光性フィルム、プリント配線板、半導体装置、及びプリント配線板の製造方法
JP7322988B2 (ja) 樹脂組成物、感光性フィルム、支持体付き感光性フィルム、プリント配線板及び半導体装置
JP2025140321A (ja) 樹脂組成物、樹脂シート及びその製造方法、回路基板及びその製造方法、並びに半導体装置
JP2025140502A (ja) 樹脂シート、回路基板及びその製造方法、並びに、半導体装置
JP2025140322A (ja) 樹脂組成物、樹脂シート及びその製造方法、回路基板及びその製造方法、並びに半導体装置

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201480036156.3

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14819309

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2015525178

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20167003029

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 14819309

Country of ref document: EP

Kind code of ref document: A1