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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/062—Polyethers
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
  • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
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  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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  • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F212/02—Monomers containing only one unsaturated aliphatic radical
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  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/52—Amides or imides
  • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
  • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
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  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
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  • C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block polymers
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  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/065—Polyamides; Polyesteramides; Polyimides
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  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
  • C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
  • C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
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  • C08F4/00—Polymerisation catalysts
  • C08F4/28—Oxygen or compounds releasing free oxygen
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  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
  • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/006—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to block copolymers containing at least one sequence of polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
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  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/04—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to rubbers
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  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
• • 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
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
  • H05K1/0313—Organic insulating material
• • 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
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
  • H05K1/0313—Organic insulating material
  • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B2457/00—Electrical equipment
  • B32B2457/08—PCBs, i.e. printed circuit boards
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  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
  • C08J2351/04—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to rubbers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
  • C08J2351/08—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J2301/00—Additional features of adhesives in the form of films or foils
  • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
  • C09J2301/414—Additional features of adhesives in the form of films or foils characterized by the presence of essential components presence of a copolymer
• • 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
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
  • H05K1/0313—Organic insulating material
  • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
  • H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics

Definitions

• the present invention relates to a thermosetting resin composition having excellent heat resistance, water resistance, and dielectric properties, and a cured product thereof.
• Patent Document 1 describes an adhesive composition using a polymer of N,N-[4,4'-bis( ⁇ , ⁇ -dimethylbenzyl)diphenyl]acrylamide as a coating agent with excellent adhesiveness and adhesion. It is stated that this will happen.
• Patent Document 2 discloses that a polymer of N,N-bis(4-(1,1,3,3-tetramethylbutyl)phenyl)acrylamide is an adhesive composition with excellent adhesion and adhesion. Are listed.
• An object of the present invention is to provide a thermosetting resin composition that has a low dielectric constant, a low dielectric loss tangent, a high glass transition point, and excellent water resistance, and a cured product thereof.
• X 1 and X 2 are each independently a C1 to C20 alkyl group, a C1 to C20 alkoxy group, a C3 to C6 cyclic alkyl group, a C3 to C6 cyclic alkoxy group, a benzyl group, or an ⁇ , ⁇ -dimethylbenzyl group; , n1 and n2 are each independently 0 or 1, Z 1 and Z 2 are each independently a single bond or a C1 to C3 alkylene group, X 3 and X 4 are each independently an organic group or a halogeno group, m1 and m2 are each independently an integer of 0 to 4, Y is a polymerizable functional group.
• SBS Styrene-butadiene-styrene block copolymer
• Z 3 is a C6 to C12 arylene group
• R 2 to R 4 are each independently a hydrogen atom or a C1 to C6 alkyl group
• R 5 to R 7 are each A thermosetting resin composition containing a polymer having a repeating unit represented by (independently a hydrogen atom or a C1-C6 alkyl group).
• thermosetting resin composition according to claim 1 further comprising (C) a radical polymerization initiator.
• the compound represented by formula (I) is a compound represented by formula (II).
• X 5 and X 6 are each independently a C1 to C20 alkyl group, a C1 to C20 alkoxy group, a C3 to C6 cyclic alkyl group, a C3 to C6 cyclic alkoxy group, a benzyl group, or an ⁇ , ⁇ -dimethylbenzyl group;
• R 1 is a hydrogen atom or a methyl group.
• thermosetting resin composition according to any one of (1) to (3) obtained by curing the thermosetting resin composition according to any one of (1) to (3).
• An adhesive film comprising a resin composition layer containing the thermosetting resin composition according to any one of (1) to (3) on a support film.
• thermosetting resin composition characterized in that it has a resin composition layer containing the thermosetting resin composition according to any one of (1) to (3) on the metal foil.
• a laminate with metal foil comprising a layer of a cured product of the thermosetting resin composition according to any one of (1) to (3), and metal foil.
• thermosetting resin composition of the present invention has a high glass transition point, a low dielectric constant and a low dielectric loss tangent, and exhibits excellent water resistance.
• thermosetting resin composition of the present invention contains at least one compound represented by formula (A) (I).
• X 1 and X 2 are each independently a C1 to C20 alkyl group, a C1 to C20 alkoxy group, a C3 to C6 cyclic alkyl group, a C3 to C6 cyclic alkoxy group, a benzyl group, or ⁇ , ⁇ -dimethylbenzyl group.
• the C1-C20 alkyl group in X 1 and X 2 includes a C1-20 straight chain alkyl group or a C3-20 branched alkyl group.
• Examples of C1-20 straight chain alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group.
• n-decyl group n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-hexadecyl group, n-octadecyl group, n-eicosyl group and the like.
• C3-20 branched alkyl groups include isopropyl group, sec-butyl group, isobutyl group, tert-butyl group, neopentyl group, isopentyl group, sec-pentyl group, 1-ethylpropyl group, tert-pentyl group, isohexyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 1,1,2,2-tetramethylpropyl group, 1,1,3-trimethylbutyl group, 1-ethylpentyl group , 1,1,3,3-tetramethylbutyl group, 2,2,3,3-tetramethylbutyl group, 1,2,4-trimethylpentyl group, 2,4,4-trimethylpentyl group, 2,2 , 4-trimethylpentyl group, 1-ethyl-4-methylpentyl group, 3-ethyl-3-methylpentyl group, 3-e
• the C1-C20 alkoxy group in X 1 and X 2 includes a C1-20 straight chain alkoxy group or a C3-20 branched alkoxy group.
• C1-20 straight chain alkoxy groups methoxy group, ethoxy group, n-propyloxy group, n-butyloxy group, n-pentyloxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group , n-decyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, n-octadecyloxy group, n-eicosyloxy group and the like.
• C3-20 branched alkoxy groups include isopropyloxy group, sec-butyloxy group, isobutyloxy group, tert-butyloxy group, neopentyloxy group, isopentyloxy group, sec-pentyloxy group, 1-ethylpropyloxy group , tert-pentyloxy group, isohexyloxy group, 3-methylpentyloxy group, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group, 1,1,2,2-tetramethylpropyloxy group , 1,1,3-trimethylbutyloxy group, 1-ethylpentyloxy group, 1,1,3,3-tetramethylbutyloxy group, 2,2,3,3-tetramethylbutyloxy group, 1,2 , 4-trimethylpentyloxy group, 2,4,4-trimethylpentyloxy group, 2,2,4-trimethylpentyloxy group, 1-ethyl-4-methyl
• Examples of the C3 to C6 cyclic alkyl group in X 1 and X 2 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
• Examples of the C3 to C6 cyclic alkoxy group in X 1 and X 2 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.
• n1 and n2 are each independently 0 or 1. It is preferable that n1 and n2 are 1.
• Z 1 and Z 2 are each independently a single bond or a C1 to C3 alkylene group.
• Examples of the C1 to C3 alkylene group in Z 1 and Z 2 include a methylene group, an ethylene group, a propane-1,3-diyl group, and the like. It is preferable that Z 1 and Z 2 are single bonds.
• X 3 and X 4 are each independently an organic group or a halogeno group.
• the organic groups in X 3 and X 4 are not particularly limited as long as they are chemically permissible and have the effects of the present invention. Examples of organic groups include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group.
• C1-6 alkyl groups such as phenyl group, C6-10 aryl group such as naphthyl group, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i -butoxy group, C1-6 alkoxy group such as t-butoxy group, chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, per Examples include C1-6 haloalkyl groups such as fluoro-n-pentyl groups. Examples of the halogeno group for X 3 and X 4 include a fluoro group, a chloro group, a bromo group, and an iodo group.
• n1 and m2 each independently represent an integer of 0 to 4. It is preferable that m1 and m2 are 0.
• Y represents a polymerizable functional group.
• polymerizable functional groups include polymerizable carbon-carbon groups such as vinyl group, allyl group, acryloyl group, methacryloyl group, vinyloxycarbonyl group, prop-1-en-2-yloxycarbonyl group, and allyloxycarbonyl group. Examples include groups having a double bond.
• Y is preferably an acryloyl group or a methacryloyl group.
• the compound represented by formula (I) is preferably a compound represented by formula (II).
• X 5 and X 6 are each independently a C1 to C20 alkyl group, a C1 to C20 alkoxy group, a C3 to C6 cyclic alkyl group, a C3 to C6 cyclic alkoxy group, a benzyl group, or ⁇ , ⁇ -dimethylbenzyl group.
• the C1-C20 alkyl group, C1-C20 alkoxy group, C3-C6 cyclic alkyl group, and C3-C6 cyclic alkoxy group in X 5 and X 6 can be the same as those exemplified in X 1 and X 2 .
• R 1 is a hydrogen atom or a methyl group.
• X 5 and X 6 are preferably a C1 to C20 alkyl group, a benzyl group, or an ⁇ , ⁇ -dimethylbenzyl group, and more preferably a C3 to C20 branched alkyl group or an ⁇ , ⁇ -dimethylbenzyl group.
• a tert-butyl group, a 1,1,3,3-tetramethylbutyl group, or an ⁇ , ⁇ -dimethylbenzyl group is more preferable.
• the method for producing the compound represented by formula (I) used in the present invention is not particularly limited, and it can be obtained using a known chemical reaction.
• the compound represented by formula (I) can be produced by the method described in WO2018/070079 pamphlet, WO2020/071456 pamphlet, WO2021/201207 pamphlet, and WO2021/201208 pamphlet.
• thermosetting resin composition of the present invention contains at least one of the following (B-1) to (B-5).
• B-1) Maleimide compound having one or more maleimide groups
• B-2) Polyphenylene ether compound
• the molar ratio of 1,2 bond structure and 1,4 bond structure is 80:20 to 100:0.
• SBS Styrene-butadiene-styrene block copolymer
• Z 3 represents a C6 to C12 arylene group
• R 2 to R 4 each independently represents a hydrogen atom or a C1 to C6 alkyl group
• R 5 to R 7 each independently represent a hydrogen atom or a C1 to C6 alkyl group.
• Maleimide compounds having one or more maleimide groups used in the present invention include N-phenylmaleimide, N-hydroxyphenylmaleimide, bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy) )-phenyl ⁇ propane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(3,5-diethyl-4-maleimidophenyl) ) Methane, polytetramethylene oxide-bis(4-maleimidobenzoate), 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, compound represented by the following formula (IV), the following formula (VI) Examples include compounds represented by the above, prepolymers of these maleimide compounds, and prepolymers of maleimide compounds and amine compounds. These may
• R 8 and R 9 each independently represent a halogeno group, a C1-C6 alkyl group, a hydroxyl group, a C1-C6 alkoxy group, a formyl group, a carboxyl group, a C1-C6 alkoxycarbonyl group, a C6-C10 aryl group, an amino group , represents a C1 to C6 alkyl group-substituted amino group, cyano group, or nitro group, a1 and a2 each independently represent an integer from 0 to 4; when a1 is 2 or more, R 8 may be the same or different; when a2 is 2 or more, R 9 may be the same or different from each other; often, m3 and m4 each independently represent an integer from 1 to 10, R 10 and R 11 are each independently a C1 to C6 alkyl group or a C6 to C10 aryl group, a3 represents an integer from 0 to 3, and when a3 is 2 or
• halogeno group for R 8 and R 9 examples include a fluoro group, a chloro group, a bromo group, an iodo group, and the like.
• the C1 to C6 alkyl group in R 8 and R 9 may be linear or branched.
• C1 to C6 alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t -butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
• Examples of the C1 to C6 alkoxy group in R 8 and R 9 include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group, etc. can be mentioned.
• Examples of the C1 to C6 alkoxycarbonyl group in R 8 and R 9 include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group, etc. I can do it.
• Examples of the C6 to C10 aryl group in R 8 and R 9 include a phenyl group and a naphthyl group.
• the C1 to C6 alkyl group-substituted amino group in R 8 and R 9 may be either mono-substituted or di-substituted.
• Examples of the C1 to C6 alkyl group-substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a methylethylamino group, and the like.
• a1 and a2 are 0.
• n3 and m4 are preferably 1 to 6, more preferably 1 to 3, still more preferably 1 to 2, and particularly preferably 1.
• a3 and a4 are 0.
• n3 is preferably 1 to 50, more preferably 1 to 20, and even more preferably 1 to 5.
• n4 represents an integer of 1 to 100. n4 is preferably from 1 to 50, more preferably from 1 to 20, even more preferably from 1 to 5.
• R 12 and R 13 each independently represent a hydrogen atom or a C1 to C6 alkyl group
• n5 represents an integer of 1 to 10
• X 7 and X 8 each independently represents a C1 to C6 alkyl group
• a5 and a6 each independently represent an integer of 0 to 2
• X 7 may be the same or different from each other
• a6 is 2 or more
• X 8 may be the same or different.
• Examples of the C1 to C6 alkyl group for R 12 and R 13 include the same ones as exemplified for R 8 and R 9 .
• R 12 and R 13 are preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom.
• n5 is preferably an integer of 1 to 7, more preferably an integer of 1 to 3, and even more preferably 1.
• X 7 and X 8 are a methyl group or an ethyl group.
• the compound represented by formula (VI) is preferably 4,4'-diphenylmethane bismaleimide or bis(3-ethyl-5-methyl-4-maleimidophenyl)methane.
• the maleimide compound used in the present invention is preferably a compound represented by formula (IV) or a compound represented by formula (VI), and a compound represented by formula (V) or a compound represented by formula (VI). More preferably, it is a compound represented by:
• MIR-3000 manufactured by Nippon Kayaku Co., Ltd.
• MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.
• BMI manufactured by K.I. Kasei Co., Ltd.
• BMI-70 manufactured by K.I. Kasei Co., Ltd.
• BMI-80 manufactured by K.I. Kasei Co., Ltd.
• the polyphenylene ether compound used in the present invention is not particularly limited as long as it is a polymer having a repeating unit represented by the following formula (VII).
• R 14 to R 17 are each independently a hydrogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, a C1 to C6 alkylcarbonyl group, or a C2 to C6 alkenyl group. Indicates a carbonyl group.
• Examples of the C1 to C6 alkyl group for R 14 to R 17 include the same ones as exemplified for R 8 and R 9 .
• Examples of the C2-C6 alkenyl group in R 14 to R 17 include a vinyl group and an allyl group.
• Examples of the C2 to C6 alkynyl group in R 14 to R 17 include ethynyl and 2-propynyl.
• Examples of the C1 to C6 alkylcarbonyl group in R 14 to R 17 include an acetyl group.
• Examples of the C2-C6 alkenylcarbonyl group in R 14 to R 17 include an acryloyl group and a methacryloyl group.
• R 14 to R 17 are preferably a hydrogen atom, a C1 to C6 alkyl group, or a C2 to C6 alkenyl group, more preferably a hydrogen atom, a methyl group, or an allyl group; It is more preferable that
• the polyphenylene ether compound used in the present invention may have its terminal modified.
• the terminal-modified polyphenylene ether compound include polyphenylene ether compounds whose terminals are modified with a hydroxyl group and polyphenylene ether compounds modified with a substituent having a carbon-carbon unsaturated double bond.
• the polyphenylene ether compound used in the present invention is preferably a polyphenylene ether compound modified with a substituent having a carbon-carbon unsaturated double bond at the end.
• Examples of the substituent having a carbon-carbon unsaturated double bond include a group represented by formula (VIII), an acryloyl group, and a methacryloyl group.
• * indicates a bonding position
• p indicates an integer of 0 to 10
• Z 4 indicates a C6 to C12 arylene group
• R 18 to R 20 each independently represent a hydrogen atom. , or a C1-C6 alkyl group.
• Examples of the C6 to C12 arylene group in Z 4 include a phenylene group.
• Examples of the C1 to C6 alkyl group in R 18 to R 20 include the same ones as exemplified in R 8 and R 9 .
• polyphenylene ether compound modified with a substituent having a carbon-carbon unsaturated double bond at the end include compounds represented by formula (IX) or formula (X).
• X 9 and X 10 each independently represent a group represented by formula (VIII), an acryloyl group or a methacryloyl group, and S1 and S2 each independently represent a group of 0 to 20. Indicates an integer.
• the group represented by formula (VIII) in X 9 and X 10 is as described above.
• X 11 and X 12 each independently represent a group represented by formula (VIII), an acryloyl group or a methacryloyl group, and S3 and S4 each independently represent a group of 0 to 20. It represents an integer, and Y 1 represents a C1 to C6 alkylene group or a single bond.
• the group represented by formula (VIII) in X 11 and X 12 is as described above. Examples of the C1 to C6 alkylene group in Y 1 include a methylene group, an ethylene group, a methylmethylene group, a dimethylmethylene group, and the like.
• the number average molecular weight (Mn) of the polyphenylene ether compound used is not particularly limited, but examples include 1,000 to 7,000, 1,000 to 5,000, and 1,000 to 3,000.
• the number average molecular weight (Mn) is a value obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
• the intrinsic viscosity of the polyphenylene ether compound used in the present invention can be 0.03 to 0.12 dl/g, 0.04 to 0.11 dl/g, 0.06 to 0.095 dl/g, etc.
• Intrinsic viscosity is the intrinsic viscosity measured in methylene chloride at 25°C. More specifically, it is a value measured using a viscometer using a 0.18 g/45 ml methylene chloride solution (liquid temperature: 25° C.).
• polyphenylene ether compound used in the present invention known ones or commercially available products can be used.
• commercially available products include SA90 (manufactured by SABIC), SA9000 (manufactured by SABIC), and OPE-2st (manufactured by Mitsubishi Gas Chemical Company).
• SA90 manufactured by SABIC
• SA9000 manufactured by SABIC
• OPE-2st manufactured by Mitsubishi Gas Chemical Company.
• synthesizing it can be synthesized by the method described in WO2014/203511 etc. or a method analogous thereto.
• the polybutadiene used in the present invention has only a 1,2-bond structure represented by formula (1), or a 1,2-bond structure represented by formula (1) and a 1,4-bond structure represented by formula (2). Consists of structure.
• the proportion of the 1,2-bond structure represented by formula (1) and the 1,4-bond structure represented by formula (2) contained in polybutadiene is not particularly limited, the proportion of the formula (I The molar ratio of the 1,2 bond structure and the 1,4 bond structure represented by ) is preferably 80:20 to 100:0.
• the molecular weight of the polybutadiene used is not particularly limited, but a weight average molecular weight (Mw) of 500 to 10,000, 500 to 8,000, 500 to 6,000, or 500 to 5,000 can be selected.
• the weight average molecular weight (Mw) is a value obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
• the polybutadiene may be a polybutadiene whose main chain and terminals are modified, or a polybutadiene whose main chain and terminals are not modified. Among them, from the viewpoint of obtaining a cured product having high insulation properties, it is preferable to use polybutadiene whose main chain and terminals are not modified.
• the polybutadiene commercially available products can be used.
• polybutadiene Commercially available polybutadiene includes NISSO-PB B-1000 (manufactured by Nippon Soda Co., Ltd.), NISSO-PB B-2000 (manufactured by Nippon Soda Co., Ltd.), and NISSO-PB B-3000 (manufactured by Nippon Soda Co., Ltd.). ), etc. These polybutadienes can be used alone or in combination of two or more.
• the styrene block in the styrene-butadiene-styrene block copolymer (SBS) used in the thermosetting resin composition of the present invention is a block obtained by polymerizing styrene
• the butadiene block is a block obtained by polymerizing butadiene.
• the butadiene block consists of only a 1,2-bond structure represented by formula (1), or a 1,2-bond structure represented by formula (1) and a 1,4-bond structure represented by formula (2). Become.
• the 1,2 bond structure represented by formula (1) and the 1,4 bond represented by formula (2) contained in the styrene-butadiene-styrene block copolymer used in the thermosetting resin of the present invention The molar ratio of the structures is between 80:20 and 100:0.
• the weight ratio of styrene block and butadiene block in the styrene-butadiene-styrene block copolymer is not particularly limited, but may be 10:90 to 80:20, 10:90 to 70:30, 10:90 to 60:40, Examples include 20:80 to 80:20, 30:70 to 80:20, and 40:60 to 80:20.
• the weight average molecular weight (Mw) of the styrene-butadiene-styrene block copolymer is not particularly limited, but examples include 2,000 to 100,000, 2,000 to 80,000, and 2,000 to 60,000. I can do it.
• the molecular weight distribution (Mw/Mn) of the styrene-butadiene-styrene block copolymer is not particularly limited, but examples include 1.00 to 3.00 and 1.00 to 2.00.
• the weight average molecular weight (Mw) and molecular weight distribution (Mw/Mn) are measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
• the measurement conditions were a mobile phase of THF (tetrahydrofuran), a mobile phase flow rate of 1 mL/min, a column temperature of 40° C., a sample injection amount of 40 ⁇ L, and a sample concentration of 2% by weight.
• the method for producing the styrene-butadiene-styrene block copolymer used is not particularly limited. For example, it can be produced by the methods described in JP-A-6-192502, JP-A-2000-514122, JP-A-2007-302901, WO2021/024679, and similar methods.
• thermosetting resin composition of the present invention may contain, as component (B), a polymer having a repeating unit represented by formula (III) in the molecule.
• Z 3 is a C6 to C12 arylene group
• R 2 to R 7 are each independently a hydrogen atom or a C1 to C6 alkyl group.
• C6-C12 arylene group for Z 3 the same ones as exemplified for Z 4 can be mentioned.
• Examples of the C1 to C6 alkyl group for R 2 to R 7 include the same ones as exemplified for R 8 and R 9 .
• formula (III) examples include formula (III-1).
• the polymer having a repeating unit represented by the formula (III) in the molecule may be a polymer further having a repeating unit represented by the following formula (3) in the molecule. Furthermore, it may have a repeating unit other than the repeating unit represented by formula (III) and the repeating unit represented by formula (3). That is, the polymer having a repeating unit represented by formula (III) in the molecule of component (B-5) includes the following polymers.
• the copolymer may be a random copolymer or a block copolymer.
• R 21 to R 23 each independently represent a hydrogen atom or a C1 to C6 alkyl group
• Ar 1 represents a C1 to C6 alkyl group-substituted or unsubstituted C6 to C12 aryl group. show.
• Examples of the C1 to C6 alkyl group in R 21 to R 23 include the same ones as exemplified in R 8 and R 9 .
• Examples of the C6 to C12 aryl group in Ar 1 include phenyl group, naphthyl group, and biphenyl group.
• the C1-C6 alkyl group which is a substituent on Ar 1 the same ones as exemplified for R 8 and R 9 can be mentioned.
• formula (3) examples include formula (3-1) and formula (3-2).
• polymers having repeating units represented by formula (III) in the molecule include repeating units represented by formula (III-1) in the molecule, and polymers having repeating units represented by formula (3-1). and a repeating unit represented by formula (3-2).
• This polymer may be a block copolymer or a random copolymer.
• the weight average molecular weight of the polymer having a repeating unit represented by formula (III) in the molecule is preferably 1,200 to 40,000, more preferably 1,200 to 35,000. Furthermore, if the weight average molecular weight is too high, moldability etc. tend to decrease. Therefore, when the weight average molecular weight of the resin composition is within the above range, it will have excellent heat resistance and moldability. Note that the weight average molecular weight here may be one measured by general molecular weight measurement, and specifically, a value measured using gel permeation chromatography (GPC), etc. can be mentioned.
• GPC gel permeation chromatography
• a polymer having a repeating unit represented by formula (III) in the molecule when the total of repeating units in the polymer having a repeating unit represented by formula (III) in the molecule is 100 mol%, the above-mentioned
• the molar content of the repeating unit represented by formula (III) is preferably 2 to 95 mol%, more preferably 8 to 81 mol%.
• a polymer having a repeating unit represented by formula (III) in the molecule has a repeating unit represented by formula (III) above and a repeating unit represented by the following formula (3) in the molecule.
• the molar content of the repeating unit represented by the formula (III) is preferably 2 to 95 mol%, more preferably 8 to 81 mol%, and The molar content of the repeating unit represented by is preferably 5 to 98 mol%, more preferably 19 to 92 mol%.
• thermosetting resin composition of the present invention can further contain (C) a radical polymerization initiator.
• Radical polymerization initiators used in the thermosetting resin composition of the present invention include azo initiators, peroxide initiators, and the like.
• azo-based initiators include azobisisobutyronitrile, 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis ⁇ 2-methyl-N-[1,1- bis(hydroxymethyl)ethyl]propionamide ⁇ , 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis[2-(hydroxymethyl)propionitrile ], 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobisisobutyrate dimethyl, 2,2 '-Azobis[2-(2-imidazolin-2-yl)propane], 2,2'-azobis ⁇ 2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide ⁇
• azobisisobutyrate dimethyl 2,2 '-Azobis[2-(2-imi
• Peroxide-based initiators include benzoyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, ⁇ , ⁇ '-di(t-butylperoxy)diisopropylbenzene.
• 2,3-dimethyl-2,3-diphenylbutane can also be used as a radical polymerization initiator (or polymerization catalyst).
• the radical polymerization initiator used for curing the resin composition of the present invention is not limited to these examples.
• the radical polymerization initiator used in the thermosetting resin composition of the present invention is preferably a peroxide-based polymerization initiator.
• thermosetting resin composition of the present invention may contain other components as necessary within a range that does not impair the effects of the present invention.
• Other components include organic solvents, crosslinking agents, thermoplastic resins, inorganic fillers, organic fillers, flame retardants, and other additives.
• organic solvents examples include amide-based, ether-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ketone-based, organic halogen compound-based, and the like.
• Amide-based organic solvents include N,N-dimethylformamide (DMF) and N,N-dimethylacetamide
• ether-based organic solvents include diethyl ether, dipropyl ether, dibutyl ether, diamyl ether, and tetrahydrofuran
• ester-based organic solvents examples include ethyl acetate, propyl acetate, butyl acetate, amyl acetate, heptyl acetate, ethyl butyrate, isoamyl isovalerate, and propylene glycol methyl ether acetate
• examples of aliphatic hydrocarbon organic solvents include normal hexane, Normal heptane, cyclohexane
• crosslinking agents examples include polyfunctional vinyl compounds such as divinylbenzene, divinylnaphthalene, and divinylbiphenyl; vinylbenzyl ether compounds synthesized from the reaction of phenol and vinylbenzyl chloride; styrene monomer; synthesized from the reaction of phenol and allyl chloride. Allyl ether compounds; trialkenyl isocyanurates such as triallyl isocyanurate (TAIC (registered trademark)) and triallyl cyanurate (TAC); (meth)acrylate compounds (methacrylate compounds and acrylate compounds) such as trimethylolpropane; acenaphthylene Examples include compounds having a skeleton. Heat resistance can be improved by using these crosslinking agents. Only one type of crosslinking agent may be used, or two or more types may be used.
• Examples of the compound having an acenaphthylene skeleton include acenaphthylene; hydroxyacenaphthylene compounds such as 3-hydroxyacenaphthylene, 4-hydroxyacenaphthylene, 5-hydroxyacenaphthylene, and 5,6-dihydroxyacenaphthylene; 3- Methylacenaphthylene, 3-ethylacenaphthylene, 3-propylacenaphthylene, 4-methylacenaphthylene, 4-ethylacenaphthylene, 4-propylacenaphthylene, 5-methylacenaphthylene, 5-ethyl Alkylacenaphthylene compounds such as acenaphthylene, 5-propylacenaphthylene, 3,8-dimethylacenaphthylene, 5,6-dimethylacenaphthylene, 3-methoxyacenap
• Alkoxyacenaphthylene compounds such as 3-chloroacenaphthylene, 3-bromoacenaphthylene, 4-chloroacenaphthylene, 4-bromoacenaphthylene, 5-chloroacenaphthylene, 5-bromoacenaphthylene, etc. and acenaphthylene compounds.
• thermoplastic resins include polyacrylate resin, polymethacrylate resin, polystyrene resin, polyphenylene ether resin, polyetherimide resin, polyether sulfone resin, polyphenylene sulfide resin, polycyclopentadiene resin, polycycloolefin resin, polycyclo Olefin copolymer resin, polyarylate resin, polyether resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyimide resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polycarbonate resin, polyether Ether ketone resin, polyester resin, liquid crystal polyester resin, fluororesin, etc., and known thermoplastic elastomers, such as styrene-ethylene-propylene copolymer, styrene-ethylene-butylene copolymer, styrene-butadiene copolymer, st
• the material of the inorganic filler is not particularly limited, but examples include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, and water.
• silica is particularly suitable. Further, as the silica, spherical silica is preferable.
• One type of inorganic filler may be used alone, or two or more types may be used in combination.
• Inorganic fillers include aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, organosilazane compounds, titanate coupling agents, vinylsilane coupling agents, and methacryloxysilane. It is preferable that the surface treatment agent be treated with one or more surface treatment agents such as a type coupling agent, an acryloxysilane type coupling agent, and a styrylsilane type coupling agent.
• organic filler examples include rubber particles, fluororesin particles (fluoropolymer particles), polyamide fine particles, silicone particles, and the like.
• the rubber particles commercially available products may be used, such as "EXL-2655” manufactured by Dow Chemical Japan Co., Ltd. and “AC3816N” manufactured by Aica Kogyo Co., Ltd., and the like.
• fluororesin particles include polytetrafluoroethylene (PTFE), perfluoroalkoxyalkane (PFA), perfluoroethylene propene copolymer (FEP), ethylene/tetrafluoroethylene copolymer (ETFE), and tetrafluoroethylene copolymer (ETFE).
• TFE/PDD fluoroethylene-perfluorodioxole copolymer
• PVDF polyvinylidene fluoride
• PCTFE polychlorotrifluoroethylene
• ECTFE ethylene-chlorotrifluoroethylene copolymer
• PVF polyvinyl fluoride
• fluororesin particles fluoropolymer particles
• fluororesin particles fluoropolymer particles
• Specific examples of commercially available PTFE particles, which are fluoropolymer particles include "Luburon (registered trademark) L-2" manufactured by Daikin Industries, Ltd., “Luburon L-5" manufactured by Daikin Industries, Ltd., and “Luburon L-5" manufactured by Daikin Industries, Ltd.
• the surface treatment may contain surface-treated particles.
• Examples of the surface treatment include surface treatment with a surface treatment agent.
• the surface treatment agent is not particularly limited.
• the surface treatment agent includes surfactants such as nonionic surfactants, amphoteric surfactants, cationic surfactants, and anionic surfactants, as well as inorganic fine particles. From the viewpoint of affinity, it is preferable to use a fluorine-based surfactant as the surface treatment agent.
• fluorine-based surfactants include “Surflon (registered trademark) S-243” (perfluoroalkyl ethylene oxide adduct) manufactured by AGC Seimi Chemical Co., Ltd. and “Megafac (registered trademark)” manufactured by DIC Corporation.
• the flame retardant is not particularly limited, but any known flame retardant can be used. Specifically, in fields where halogen-based flame retardants such as brominated flame retardants are used, for example, ethylene dipentabromobenzene, ethylene bistetrabromoimide, decabromodiphenyl oxide, and tetradecabromo with a melting point of 300°C or higher are used. Diphenoxybenzene is preferred. It is thought that by using a halogen-based flame retardant, desorption of halogen at high temperatures can be suppressed, and a decrease in heat resistance can be suppressed.
• halogen-based flame retardants such as brominated flame retardants
• ethylene dipentabromobenzene ethylene bistetrabromoimide
• decabromodiphenyl oxide tetradecabromo with a melting point of 300°C or higher are used.
• Diphenoxybenzene is preferred. It is thought that by using a halogen-based flame retardant, de
• phosphorus-based flame retardants such as phosphate ester-based flame retardants, phosphazene-based flame retardants, and phosphinate-based flame retardants can be mentioned.
• a specific example of the phosphoric acid ester flame retardant includes a condensed phosphoric acid ester of dixylenyl phosphate.
• a specific example of the phosphazene flame retardant is phenoxyphosphazene.
• phosphinate-based flame retardants include phosphinate metal salts of dialkyl phosphinate aluminum salts.
• Each of the exemplified flame retardants may be used alone, or two or more types may be used in combination.
• additives include, for example, antifoaming agents such as silicone antifoaming agents and acrylic acid ester antifoaming agents, organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds, leveling agents, and silane coupling agents.
• adhesion aids such as tackifiers, tackifiers such as tackifiers, heat stabilizers, antistatic agents, storage stabilizers such as BHT, antioxidants, light stabilizers, ultraviolet absorbers, dyes and pigments, lubricants, wet dispersions. agents, heavy metal deactivators, ion trapping agents, emulsifiers, water dispersion stabilizers, mold release agents, waxes, rheology control agents, surfactants and the like.
• thermosetting resin composition ⁇ Composition ratio of thermosetting resin composition>
• the content of component (C) in the thermosetting resin composition of the present invention is not particularly limited, but is 0.1 to 10% by mass based on the combined amount of components (A) and (B). %.
• thermosetting resin composition of the present invention is applicable to solder resists, underfill materials, die bonding materials, semiconductor sealing materials, hole filling resins, parts embedding resins, insulating materials for printed wiring boards, etc. where resin compositions are required. Can be used in a wide range of applications.
• the thermosetting resin composition of the present invention is preferably a resin composition for an insulating layer of a printed wiring board. Examples of the printed wiring board include a single-sided printed circuit board, a double-sided printed circuit board, a multilayer printed circuit board, a flexible printed circuit board, and a build-up circuit board.
• the resin composition of the present invention can also be applied to sheet-like laminated materials described below. Although the resin composition of the present invention can be applied in the form of a varnish to a printed wiring board to form an insulating layer, it is generally used industrially to form an insulating layer in the form of a sheet-like laminate material.
• the cured product obtained by curing the thermosetting resin composition of the present invention can be used as a molded product, a laminate, a cast product, an adhesive, a coating film, or a film.
• a cured product of a semiconductor encapsulating material is a cast product or a molded product, and methods for obtaining a cured product for such uses include casting a curable resin composition, or using a transfer molding machine, an injection molding machine, etc.
• a cured product can be obtained by molding using the resin and further heating at 80 to 300°C for 0.5 to 10 hours.
• thermosetting resin composition of the present invention is used for the purpose of impregnating a base material (fibrous base material) for forming a prepreg, or for the purpose of using it as a circuit board material for forming a circuit board. It can be prepared into a varnish form to make a resin varnish.
• This resin varnish is suitable for circuit boards and can be used as a varnish for circuit board materials. Note that specific uses of the circuit board material here include printed wiring boards, printed circuit boards, flexible printed wiring boards, build-up wiring boards, and the like.
• a resin varnish is prepared, for example, as follows. Each component is introduced into an organic solvent and dissolved. At this time, heating may be performed if necessary. Thereafter, if necessary, components that do not dissolve in organic solvents such as inorganic fillers are added and dispersed using a ball mill, bead mill, planetary mixer, roll mill, etc. to form a varnish-like curable resin composition. is prepared.
• thermosetting resin composition of the present invention can be used for sheet-like laminated materials.
• sheet-like laminated materials include prepregs, adhesive films, and metal foils coated with thermosetting resin compositions, which will be described later.
• the prepreg of the present invention is characterized in that a base material is impregnated with the thermosetting resin composition of the present invention.
• the base material include fibrous base materials such as glass cloth, aramid cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, polyester nonwoven fabric, pulp paper, and linter paper.
• the thickness of the base material is not particularly limited, but is preferably 20 to 800 ⁇ m, more preferably 20 to 300 ⁇ m.
• the prepreg of the present invention can be manufactured by a known method. For example, a method may be mentioned in which a base material is impregnated with the resin varnish of the present invention and then dried.
• a prepreg in a semi-cured state (B stage) can be obtained by heating the base material impregnated with the resin varnish under desired heating conditions, for example, 80 to 170°C for 1 to 10 minutes to remove the solvent. .
• the adhesive film of the present invention is characterized by having a resin composition layer containing the resin composition of the present invention on a support film.
• the adhesive film of the present invention can be manufactured by a known method.
• the resin varnish of the present invention can be manufactured by applying the resin varnish to a support film using a dicoder or the like, and then drying the organic solvent by heating or blowing hot air to form a resin composition layer. can.
• Drying conditions are not particularly limited, but drying is performed such that the content of organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although it varies depending on the amount of organic solvent in the varnish and the boiling point of the organic solvent, for example, by drying a varnish containing 30 to 60% by mass of an organic solvent at 50 to 150°C for about 3 to 10 minutes, a thermosetting resin composition can be obtained. A resin composition layer containing the following can be formed.
• the thickness of the resin composition layer formed in the adhesive film is not particularly limited, but is preferably 5 to 200 ⁇ m. From the viewpoint of thinning the film, the thickness is more preferably 15 to 80 ⁇ m.
• Supporting films include polyolefin films such as polyethylene, polypropylene, and polyvinyl chloride; polyester films such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate; polycarbonate films; polyimide films, etc. Examples include various plastic films. Also, release paper, metal foil such as copper foil, aluminum foil, etc. may be used. Among these, from the viewpoint of versatility, plastic films are preferred, and polyethylene terephthalate films are more preferred.
• the support and the protective film described below may be subjected to surface treatments such as mud treatment and corona treatment. Further, a mold release treatment may be performed using a mold release agent such as a silicone resin mold release agent, an alkyd resin mold release agent, or a fluororesin mold release agent.
• the thickness of the support film is not particularly limited, but is preferably 10 to 150 ⁇ m, more preferably 25 to 50 ⁇ m.
• a protective film similar to the support can be further laminated on the surface of the thermosetting resin composition layer that is not in close contact with the support.
• the thickness of the protective film is not particularly limited, but is, for example, 1 to 40 ⁇ m.
• the metal foil with a thermosetting resin composition of the present invention is characterized by having a resin composition layer containing the thermosetting resin composition of the present invention on the metal foil.
• the metal foil used here include copper foil, aluminum foil, and the like.
• the thickness is not particularly limited, but is preferably in the range of 3 to 200 ⁇ m, more preferably in the range of 5 to 105 ⁇ m.
• the method for producing the metal foil coated with the thermosetting resin composition of the present invention is not particularly limited. Examples include a method of uniformly dissolving or dispersing the material, applying it to metal foil, and then drying it. Application can be repeated multiple times if necessary, and in this case, application can be repeated using multiple solutions with different compositions and concentrations to finally adjust to the desired resin composition and resin amount. It is possible.
• the thickness of the resin composition layer formed in the thermosetting resin composition coated metal foil of the present invention is not particularly limited, but is preferably 5 to 200 ⁇ m.
• the metal foil coated with a thermosetting resin composition of the present invention may include a release film on the surface of the layer of the thermosetting resin composition to which the metal foil is not in close contact.
• a resin film whose main component is polyolefin such as polyethylene or polypropylene; polyester such as polyethylene terephthalate or polyethylene naphthalate; polyimide; or polycarbonate can be used.
• a silicone resin mold release agent or the like may be applied to these surfaces to adjust the peel strength.
• the thickness of the release film is preferably 1 to 300 ⁇ m, more preferably 5 to 200 ⁇ m, even more preferably 10 to 150 ⁇ m, even more preferably 20 to 120 ⁇ m.
• the surface of the release film that comes into contact with the resin sheet may be subjected to matte treatment, corona treatment, or antistatic treatment.
• the laminate with metal foil of the present invention includes a layer of the thermosetting resin of the present invention and metal foil.
• the metal foil used here include copper foil, aluminum foil, and the like.
• the thickness is not particularly limited, but is in the range of 3 to 200 ⁇ m, more preferably 5 to 105 ⁇ m.
• the method for producing the metal foil-coated laminate of the present invention is not particularly limited; A method of adhering each layer under pressure and simultaneously curing with heat can be mentioned.
• the thermosetting resin layer of the present invention and the metal foil are laminated in any layer configuration.
• Metal foil can be used both as a surface layer and as an intermediate layer. In addition to the above, it is also possible to repeat lamination and curing multiple times to form a multilayer structure.
• An adhesive can also be used for adhesion to the metal foil.
• adhesives include epoxy, acrylic, phenol, and cyanoacrylate adhesives, but are not particularly limited thereto.
• the resin composition of the present invention can also be used as an adhesive. The above lamination molding and curing can be performed under the same conditions as those for manufacturing the insulator for printed wiring boards of the present invention.
• thermosetting resin composition of the present invention can be processed into a molded material, sheet or film, and has properties such as low dielectric constant, low water absorption, and high heat resistance in fields such as the electrical industry, space and aircraft industry, and automobiles. It can be used for low dielectric materials, insulating materials, heat-resistant materials, structural materials, etc. that satisfy the characteristics. In particular, it can be used as a single-sided, double-sided, multilayer printed circuit board, flexible printed circuit board, build-up circuit board, etc. Furthermore, semiconductor-related materials or optical materials, as well as paints, photosensitive materials, adhesives, sewage treatment agents, heavy metal collectors, ion exchange resins, antistatic agents, antioxidants, antifogging agents, and rust preventive agents.
• anti-dye agents fungicides, insect repellents, medical materials, flocculants, surfactants, lubricants, solid fuel binders, conductive treatment agents, resin modifiers, asphalt modifier plasticizers, sintering binders, etc. can be applied.
• thermosetting resin composition of the present invention has a low dielectric constant and a low dielectric loss tangent, a high glass transition point, and exhibits excellent water resistance. Therefore, in the electrical/electronic industry, space/aircraft industry, etc., molding defects such as warping are being used as dielectric materials, insulating materials, heat-resistant materials, structural materials, etc. in response to the strong demand for smaller and thinner products in recent years. It is possible to provide a cured molded product without any phenomena. Examples of the present invention will be shown below, but the technical scope of the present invention is not limited to these Examples.
• the polymerization solution was separated and washed once with a 3% acetic acid aqueous solution and twice with pure water, and then added dropwise to methanol with stirring, followed by stirring for 2 hours after the dropwise addition.
• Examples 1 to 38 Comparative Examples 1 to 11
• Each reagent having the composition (parts by mass) shown in Tables 1 to 12 was added to toluene and mixed so that the solid content concentration was 50% by mass. Thereafter, the obtained liquid toluene was removed using an evaporator to obtain a powdered resin composition.
• the resin composition was cured by hot pressing at 200° C. for 90 minutes.
• the physical properties of the obtained cured product were measured for the following items, and the results are shown in Table 1.
• ⁇ Glass transition temperature (Tg)/TMA> Glass transition temperature (Tg) was evaluated by TMA method in accordance with IPC TM650.
• thermomechanical analysis (TMA) device (Discovery TMA450 EM manufactured by TA Instruments Japan Co., Ltd.) in the range of 0 to 200°C.
• TMA thermomechanical analysis
• Tg/DMA> Dynamic mechanical analysis (DMA) was performed, and the temperature at which tan ⁇ reached the maximum value when the temperature was raised from room temperature to 270° C. at a heating rate of 5° C./min was defined as Tg.
• the device used was RAS-G2 manufactured by TA Instruments Co., Ltd.
• ⁇ Dielectric loss tangent after water absorption treatment> The cured product used in the measurement of the dielectric loss tangent before the water absorption treatment was immersed in water at room temperature for 24 hours in accordance with JIS K7209. After the water absorption treatment, the moisture on the cured product was thoroughly wiped off with a dry, clean cloth. The dielectric loss tangent (dielectric loss tangent after water absorption) of the cured product subjected to water absorption treatment was measured in the same manner as the measurement of the dielectric loss tangent before the water absorption treatment.

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• 2023
  • 2023-03-27 KR KR1020247029929A patent/KR20240164888A/ko active Pending
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