WO2023048024A1 - Composition de résine, préimprégné, carte stratifiée revêtue d'une feuille métallique, feuille composite de résine, carte de circuit imprimé et dispositif semi-conducteur - Google Patents

Composition de résine, préimprégné, carte stratifiée revêtue d'une feuille métallique, feuille composite de résine, carte de circuit imprimé et dispositif semi-conducteur Download PDF

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WO2023048024A1
WO2023048024A1 PCT/JP2022/034258 JP2022034258W WO2023048024A1 WO 2023048024 A1 WO2023048024 A1 WO 2023048024A1 JP 2022034258 W JP2022034258 W JP 2022034258W WO 2023048024 A1 WO2023048024 A1 WO 2023048024A1
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group
mass
formula
resin composition
thermoplastic elastomer
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PCT/JP2022/034258
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English (en)
Japanese (ja)
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悠仁 鎌田
克哉 山本
恵一 長谷部
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三菱瓦斯化学株式会社
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Priority to JP2023549494A priority Critical patent/JPWO2023048024A1/ja
Priority to CN202280064918.5A priority patent/CN118019807A/zh
Priority to KR1020247012994A priority patent/KR20240065287A/ko
Publication of WO2023048024A1 publication Critical patent/WO2023048024A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/126—Polyphenylene oxides modified by chemical after-treatment
    • 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
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • C08G65/485—Polyphenylene oxides
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/295—Organic, e.g. plastic containing a filler
    • 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

Definitions

  • the present invention relates to resin compositions, prepregs, metal foil-clad laminates, resin composite sheets, printed wiring boards, and semiconductor devices.
  • Patent Document 1 discloses a maleimide compound (A), a cyanate ester compound (B), a polyphenylene ether compound (C) represented by a predetermined formula and having a number average molecular weight of 1,000 to 7,000, and a block copolymer having a styrene skeleton.
  • a resin composition containing a polymer (D) is disclosed.
  • Patent Document 2 discloses a resin composition containing a polyfunctional vinyl aromatic polymer (A) and a thermosetting compound (B) and containing no radical polymerization initiator.
  • An object of the present invention is to solve the above-mentioned problems, and a novel resin composition having excellent moisture absorption and heat resistance while maintaining an excellent low dielectric loss tangent, as well as a prepreg and a metal foil clad laminate , a resin composite sheet, a printed wiring board, and a semiconductor device.
  • thermoplastic elastomer (A) contains styrene monomer units and conjugated diene monomer units, and has a number average molecular weight of 50,000 or more.
  • thermoplastic elastomer (B) contains styrene monomer units and conjugated diene monomer units, and has a number average molecular weight of 50,000 or more. a partially hydrogenated and/or fully unsaturated thermoplastic elastomer, Resin composition. ⁇ 2> The total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition is 1 to 40 parts by mass with respect to 100 parts by mass of the resin solid content, ⁇ 1 > The resin composition according to .
  • thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group.
  • the compatible thermosetting resin (C) consists of a polymer having a structural unit represented by formula (V) and a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end.
  • Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.
  • the maleimide compound is a compound represented by the formula (M0), a compound represented by the formula (M1), a compound represented by the formula (M2), a compound represented by the formula (M3), a compound represented by the formula (M0), a compound represented by the formula (M0), a compound represented by the formula (M1), a compound represented by the formula (M2), a compound represented by the formula (M3), a compound represented by the formula (M0), a compound represented by the formula (M1), a compound represented by the formula (M2), a compound represented by the formula (M3), a compound represented by the formula (M5).
  • each R 51 independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group; each R 52 independently represents a hydrogen atom or a methyl group; n 1 represents an integer of 1 or more.
  • R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group.
  • R M5 and R M6 each independently represent a hydrogen atom or an alkyl group.
  • Ar M represents a divalent aromatic group, A is a 4- to 6-membered alicyclic group, R M7 and R M8 are each independently an alkyl group, mx is 1 or 2; and lx is 0 or 1.
  • R M9 and R M10 each independently represent a hydrogen atom or an alkyl group
  • R M11 , R M12 , R M13 and R M14 each independently represent a hydrogen atom or Representing an organic group
  • R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, represents an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group or a mercapto group
  • px represents an integer of 0 to 3
  • nx represents an integer of 1 to 20.
  • each R 54 independently represents a hydrogen atom or a methyl group
  • n 4 represents an integer of 1 or more.
  • each R 55 independently represents a hydrogen atom, an alkyl group
  • R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group.
  • R M5 and R M6 each independently represent a hydrogen atom or an alkyl group.
  • Ar M represents a divalent aromatic group, A is a 4- to 6-membered alicyclic group, R M7 and R M8 are each independently an alkyl group, mx is 1 or 2; and lx is 0 or 1.
  • R M9 and R M10 each independently represent a hydrogen atom or an alkyl group
  • R M11 , R M12 , R M13 and R M14 each independently represent a hydrogen atom or Representing an organic group
  • R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, represents an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group or a mercapto group
  • px represents an integer of 0 to 3
  • nx represents an integer of 1 to 20.
  • each R 55 independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group
  • n 5 represents an integer of 1 or more and 10 or less.
  • the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition is 1 to 40 parts by mass with respect to 100 parts by mass of the resin solid content,
  • the mass ratio of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition is 1:1 to 10
  • the compatible thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group
  • the compatible thermosetting resin (C) is selected from the group consisting of a polymer having a structural unit represented by formula (V) and a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end. including one or more (In formula (V), Ar represents an aromatic hydrocarbon linking group.
  • the content of the compatible thermosetting resin (C) is 10 to 90 parts by mass with respect to 100 parts by mass of the resin solid content, Furthermore, containing one or more other resins (D) selected from the group consisting of cyanate ester compounds, maleimide compounds, and epoxy compounds,
  • the maleimide compound includes one or more selected from the group consisting of a compound represented by formula (M1), a compound represented by formula (M3), and a compound represented by formula (M5),
  • a flame retardant (E) contains a phosphorus-based flame retardant
  • the filler (F) is one or more selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate.
  • the content of the filler (F) is 10 to 300 parts by mass with respect to 100 parts by mass of the resin solid content
  • R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group.
  • R M5 and R M6 each independently represent a hydrogen atom or an alkyl group.
  • Ar M represents a divalent aromatic group
  • A is a 4- to 6-membered alicyclic group
  • R M7 and R M8 are each independently an alkyl group
  • mx is 1 or 2
  • lx is 0 or 1.
  • R M9 and R M10 each independently represent a hydrogen atom or an alkyl group
  • R M11 , R M12 , R M13 and R M14 each independently represent a hydrogen atom or Representing an organic group
  • R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, represents an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group or a mercapto group
  • px represents an integer of 0 to 3
  • a metal foil-clad laminate comprising at least one layer formed from the prepreg according to ⁇ 17> and a metal foil disposed on one side or both sides of the layer formed from the prepreg.
  • a resin composite sheet comprising a support and a layer formed from the resin composition according to any one of ⁇ 1> to ⁇ 16> disposed on the surface of the support.
  • a printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer comprises the resin composition according to any one of ⁇ 1> to ⁇ 16>.
  • a printed wiring board comprising at least one of a layer formed from a material and a layer formed from the prepreg according to ⁇ 17>.
  • a semiconductor device including the printed wiring board according to ⁇ 20>.
  • the present invention provides a novel resin composition having excellent moisture absorption and heat resistance while maintaining an excellent low dielectric loss tangent, as well as a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. became possible.
  • an "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the dielectric constant indicates the ratio of the dielectric constant of a substance to the vacuum dielectric constant.
  • the relative dielectric constant may be simply referred to as "permittivity”.
  • (meth)acryl represents both or either acryl and methacryl. If the standards shown in this specification differ from year to year in terms of measurement methods, etc., the standards as of January 1, 2021 shall be used unless otherwise specified.
  • the resin solid content refers to components excluding fillers and solvents, and includes thermoplastic elastomer (A), thermoplastic elastomer (B), thermoplastic elastomer (A) and thermoplastic elastomer (B).
  • thermoplastic elastomer A thermoplastic elastomer compatible with both (C), and other resins (D) that are blended as necessary, silane coupling agents, and other resin additive components (additives such as flame retardants, etc.)
  • the purpose is to include
  • the resin composition of the present embodiment comprises a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin compatible with both the thermoplastic elastomer (A) and the thermoplastic elastomer (B).
  • thermoplastic elastomer (A) contains styrene monomer units and conjugated diene monomer units and has a number average molecular weight of 50,000 or more
  • the thermoplastic elastomer is a thermoplastic elastomer in which all of the conjugated diene bonds of the plastic elastomer are hydrogenated
  • thermoplastic elastomer (B) contains styrene monomer units and conjugated diene monomer units, and has a number average molecular weight of 50.
  • thermoplastic elastomer in which some of the conjugated diene bonds of the thermoplastic elastomer are hydrogenated and/or all of the conjugated diene bonds are unsaturated bonds.
  • thermoplastic elastomer (A) it is presumed that a resin composition having excellent dielectric properties can be obtained. It is presumed that this is due to the fact that the conjugated diene bonds are hydrogenated to lower the polarity of the elastomer.
  • thermoplastic elastomer (B) has a large number average molecular weight of 50,000 or more and is a highly polar resin. It is presumed that the compatibility with the thermosetting resin (C) compatible with is excellent, and the moisture absorption heat resistance of the resin composition is improved.
  • thermoplastic elastomer (A) The resin composition of this embodiment contains a thermoplastic elastomer (A).
  • the thermoplastic elastomer (A) is a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more, wherein all of the conjugated diene bonds of the thermoplastic elastomer is a hydrogenated thermoplastic elastomer (in this specification, it may be referred to as "hydrogenated styrene thermoplastic elastomer").
  • hydroplastic elastomer (A) By including the thermoplastic elastomer (A), the effects of excellent low dielectric loss tangent, crack resistance, and low thermal expansion are achieved.
  • thermoplastic elastomer (A) in this embodiment contains styrene monomer units. By including a styrene monomer unit, it tends to have excellent compatibility with the thermosetting resin (C).
  • Styrene monomers include styrene, ⁇ -methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, N,N-diethyl-p-aminoethylstyrene and the like.
  • styrene, ⁇ -methylstyrene and p-methylstyrene are preferred from the viewpoint of availability and productivity.
  • styrene is particularly preferred.
  • the content of styrene monomer units is preferably in the range of 10 to 50% by mass, more preferably in the range of 13 to 45% by mass, and even more preferably in the range of 15 to 40% by mass based on the total monomer units. If the content of styrene monomer units is 50% by mass or less, the adhesiveness and adhesiveness to substrates and the like will be better.
  • thermoplastic elastomer (A) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more kinds are included, the total amount is preferably within the above range.
  • the method for measuring the content of styrene monomer units in the thermoplastic elastomer (A) of the present embodiment can be referred to the description of WO 2017/126469, the content of which is incorporated herein. The same applies to the conjugated diene monomer units and the like, which will be described later.
  • the thermoplastic elastomer (A) in this embodiment contains conjugated diene monomer units. By containing the conjugated diene monomer unit, it tends to be excellent in low dielectric loss tangent property, crack resistance, and low thermal expansion property.
  • the conjugated diene monomer is not particularly limited as long as it is a diolefin having a pair of conjugated double bonds.
  • Conjugated diene monomers are, for example, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl- 1,3-pentadiene, 1,3-hexadiene, and farnesene are included, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred.
  • the thermoplastic elastomer (A) may contain only one type of conjugated diene monomer unit, or may contain two or more types.
  • the mass ratio of the styrene polymer unit and the conjugated diene monomer unit is in the range of 5/95 to 40/60, it is possible to suppress the increase in adhesion, maintain high adhesive strength, and improve the easy peelability of the adhesive surfaces. get better.
  • thermoplastic elastomer (A) used in this embodiment all of the conjugated diene bonds of the thermoplastic elastomer are hydrogenated.
  • all hydrogenated means that the double bonds based on the conjugated diene monomer units in the thermoplastic elastomer (A) are substantially hydrogenated, and the hydrogenation rate (hydrogenation rate) is 100%, as well as 80% or more.
  • the degree of hydrogenation in the thermoplastic elastomer (A) used in the present embodiment is preferably 85% or higher, more preferably 90% or higher, even more preferably 95% or higher.
  • the thermoplastic elastomer (A) used in the present embodiment may or may not contain other monomer units in addition to the styrene monomer units and the conjugated diene monomer units.
  • examples of other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers.
  • the total amount of styrene monomer units and conjugated diene monomer units is preferably 90% by mass or more of the total monomer units, and 95% by mass or more. It is more preferable that the content is 97% by mass or more.
  • thermoplastic elastomer (A) may contain only one kind of styrene monomer units and conjugated diene monomer units, or may contain two or more kinds thereof. When two or more types are included, the total amount is preferably within the above range.
  • the number average molecular weight of the thermoplastic elastomer (A) used in this embodiment is 50,000 or more. By making it 50,000 or more, it tends to be excellent in crack resistance.
  • the number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, still more preferably 80,000 or more, even more preferably 90,000 or more, and 100 ,000 or greater, and even more preferably 150,000 or greater.
  • the upper limit of the number average molecular weight of the thermoplastic elastomer (A) is preferably 400,000 or less, more preferably 350,000 or less, even more preferably 300,000 or less.
  • the amount is equal to or less than the upper limit, the compatibility with the thermoplastic elastomer (B) and the thermosetting resin (C) tends to be further improved.
  • the resin composition of the present embodiment contains two or more thermoplastic elastomers (A), the number average molecular weight of the mixture thereof preferably satisfies the above range.
  • thermoplastic elastomer (A) used in this embodiment may be a block polymer or a random polymer.
  • examples of the composition of the thermoplastic elastomer (A) used in this embodiment include SEBS (styrene-ethylene/butylene-styrene copolymer) and SEPS (styrene-ethylene/propylene-styrene copolymer).
  • thermoplastic elastomer (A) used in this embodiment examples include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., S.E.M. O. E. (registered trademark) S1606, S1613, S1605, manufactured by JSR Corporation, DYNARON (registered trademark) 9901P, and the like.
  • the content of the thermoplastic elastomer (A) in the resin composition of the present embodiment is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, relative to 100 parts by mass of the resin solid content. , more preferably 2 parts by mass or more, still more preferably 3 parts by mass or more, and even more preferably 4 parts by mass or more.
  • the content is at least the above lower limit, the low dielectric loss tangent property, crack resistance, and low thermal expansion property tend to be further improved.
  • the upper limit of the content of the thermoplastic elastomer (A) is preferably 20 parts by mass or less, more preferably 18 parts by mass or less, and 15 parts by mass with respect to 100 parts by mass of the resin solid content.
  • the resin composition of the present embodiment may contain only one type of thermoplastic elastomer (A), or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of this embodiment contains a thermoplastic elastomer (B).
  • the thermoplastic elastomer (B) is a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more. It is a partially hydrogenated and/or fully unsaturated thermoplastic elastomer.
  • the compatibility with the thermoplastic elastomer (A) is improved, and the moisture absorption and heat resistance is excellent.
  • thermoplastic elastomer (B) in this embodiment contains styrene monomer units. By including a styrene monomer unit, it tends to have excellent compatibility with the thermosetting resin (C).
  • Styrene monomers include styrene, ⁇ -methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, N,N-diethyl-p-aminoethylstyrene and the like.
  • styrene, ⁇ -methylstyrene, and p-methylstyrene are preferred from the viewpoint of availability and productivity.
  • styrene is particularly preferred.
  • the content of styrene monomer units is preferably in the range of 10 to 50% by mass, more preferably in the range of 13 to 45% by mass, even more preferably in the range of 15 to 40% by mass, based on the total monomer units. If the content of styrene monomer units is 50% by mass or less, the adhesiveness and adhesiveness to substrates and the like will be better.
  • thermoplastic elastomer (B) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more kinds are included, the total amount is preferably within the above range.
  • the method for measuring the content of styrene monomer units in the thermoplastic elastomer (B) of the present embodiment can be referred to the description of WO 2017/126469, the content of which is incorporated herein. The same applies to the conjugated diene monomer unit and the like, which will be described later.
  • the thermoplastic elastomer (B) in this embodiment contains conjugated diene monomer units. By containing the conjugated diene monomer unit, it tends to be excellent in low dielectric loss tangent property, crack resistance, and low thermal expansion property.
  • the conjugated diene monomer is not particularly limited as long as it is a diolefin having a pair of conjugated double bonds.
  • Conjugated diene monomers are, for example, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl- 1,3-pentadiene, 1,3-hexadiene, and farnesene are included, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred.
  • the thermoplastic elastomer (B) may contain only one type of conjugated diene monomer unit, or may contain two or more types.
  • the mass ratio of the styrene polymer unit and the conjugated diene monomer unit is in the range of 5/95 to 40/60, it is possible to suppress the increase in adhesion, maintain high adhesive strength, and improve the easy peelability of the adhesive surfaces. get better.
  • the conjugated diene bonds of the thermoplastic elastomer are not hydrogenated or only partially hydrogenated.
  • “only partially hydrogenated” means that some of the double bonds based on the conjugated diene monomer units in the thermoplastic elastomer (B) are hydrogenated. It means that the (hydrogenation rate) is less than 80%.
  • the hydrogenation rate of the thermoplastic elastomer (B) used in the present embodiment is more preferably 60% or less, more preferably 40% or less, even more preferably 20% or less, even more preferably 10% or less, and 5% or less. Even more preferred.
  • the thermoplastic elastomer (B) used in the present embodiment may or may not contain other monomer units in addition to the styrene monomer units and the conjugated diene monomer units.
  • examples of other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers.
  • the total amount of styrene monomer units and conjugated diene monomer units is preferably 90% by mass or more of the total monomer units, and 95% by mass or more. It is more preferably 97% by mass or more, and even more preferably 99% by mass or more.
  • thermoplastic elastomer (B) may contain only one kind of styrene monomer units and conjugated diene monomer units, or may contain two or more kinds thereof. When two or more types are included, the total amount is preferably within the above range.
  • the number average molecular weight of the thermoplastic elastomer (B) used in this embodiment is 50,000 or more. When it is 50,000 or more, crack resistance and compatibility with the thermoplastic elastomer (A) tend to be more excellent.
  • the number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, still more preferably 80,000 or more, even more preferably 100,000 or more, and 120 ,000 or greater, and even more preferably 150,000 or greater.
  • the upper limit of the number average molecular weight of the thermoplastic elastomer (B) is preferably 400,000 or less, more preferably 350,000 or less, even more preferably 300,000 or less.
  • thermosetting resin (C) tends to be further improved by making it equal to or less than the upper limit.
  • the resin composition of the present embodiment contains two or more thermoplastic elastomers (B), the number average molecular weight of the mixture thereof preferably satisfies the above range.
  • thermoplastic elastomer (B) used in this embodiment may be a block polymer or a random polymer.
  • examples of the composition of the thermoplastic elastomer (B) used in this embodiment include SBS (styrene-butadiene-styrene copolymer).
  • thermoplastic elastomer (B) used in this embodiment include TR2250 manufactured by JSR Corporation, S.T. O. E. (registered trademark) S1609 and the like are exemplified.
  • the content of the thermoplastic elastomer (B) in the resin composition of the present embodiment is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, relative to 100 parts by mass of the resin solid content. , more preferably 2 parts by mass or more, still more preferably 3 parts by mass or more, and even more preferably 4 parts by mass or more.
  • the content is at least the above lower limit, the low dielectric loss tangent property, crack resistance, and low thermal expansion property tend to be further improved.
  • the upper limit of the content of the thermoplastic elastomer (B) is preferably 20 parts by mass or less, more preferably 18 parts by mass or less, and 15 parts by mass with respect to 100 parts by mass of the resin solid content.
  • the resin composition of the present embodiment may contain only one type of thermoplastic elastomer (B), or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the mass ratio of thermoplastic elastomer (A) to thermoplastic elastomer (B) is preferably 1:1-10.
  • the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is preferably 1:1 to 9, more preferably 1:1 to 8, and 1:1 to 7. is more preferred, and 1:1 to 5 is even more preferred.
  • the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition of the present embodiment is preferably 1 to 40 parts by mass per 100 parts by mass of the resin solid content.
  • the total amount is more preferably 3 parts by mass or more, more preferably 5 parts by mass or more, even more preferably 7 parts by mass or more, and 10 parts by mass with respect to 100 parts by mass of the resin solid content. Part or more is even more preferable.
  • the total amount is more preferably 35 parts by mass or less, further preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less with respect to 100 parts by mass of the resin solid content, It is more preferably 20 parts by mass or less.
  • thermosetting resin (C) compatible with both the thermoplastic elastomer (A) and the thermoplastic elastomer (B).
  • a compatible thermosetting resin (C) hereinafter also referred to as “compatible thermosetting resin (C)” or “thermosetting resin (C)” in this specification
  • a low dielectric The effect of improving properties and moisture absorption heat resistance is achieved.
  • compatible means that the thermoplastic elastomer (A), the thermoplastic elastomer (B), and the thermosetting resin (C) are sufficiently mixed and allowed to stand, and then coarse separation does not occur. This means that it can be observed, usually by visual inspection.
  • the compatible thermosetting resin (C) is preferably a thermosetting resin containing an aromatic ring and a vinyl group. By using such a resin, it tends to be compatible with the styrene monomer units contained in the thermoplastic elastomer (A) and the thermoplastic elastomer (B), and the compatibility tends to be further improved.
  • the compatible thermosetting resin (C) has a number average molecular weight Mn of preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more. , 500 or more.
  • the upper limit is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, even more preferably 100,000 or less. When two or more thermosetting resins (C) are included, the number average molecular weight of the mixture is preferably within the above range.
  • the compatible thermosetting resin (C) is a polymer having a structural unit represented by the formula (V), and a polyphenylene ether having a carbon-carbon unsaturated double bond at the end It preferably contains one or more selected from the group consisting of compounds. By using such a resin, the effects of the present invention are exhibited more effectively.
  • Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.
  • the compatible thermosetting resin (C) may also contain structural units derived from maleic anhydride. Details of such resins can be referred to in International Publication No. 2017/209108, the content of which is incorporated herein. Furthermore, the compatible thermosetting resin (C) may contain structural units derived from a compound having an acid group and an acid anhydride group.
  • the content of the compatible thermosetting resin (C) is preferably 10 to 90 parts by mass when the resin solid content in the resin composition is 100 parts by mass. .
  • the lower limit of the content of the compatible thermosetting resin (C) is preferably 15 parts by mass or more, preferably 20 parts by mass or more, when the resin solid content in the resin composition is 100 parts by mass. more preferably 25 parts by mass or more.
  • the upper limit of the content of the compatible thermosetting resin (C) is preferably 80 parts by mass or less, and 60 parts by mass when the resin solid content in the resin composition is 100 parts by mass. or less, more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less. By making it equal to or less than the upper limit, the metal foil peel strength of the resulting cured product can be effectively increased.
  • the compatible thermosetting resin (C) may be contained in the resin composition either alone or in combination of two or more. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of the present embodiment preferably contains a polymer having a structural unit represented by formula (V).
  • a resin composition having excellent low dielectric properties low dielectric constant, low dielectric loss tangent
  • Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.
  • the aromatic hydrocarbon linking group may be a group consisting only of an optionally substituted aromatic hydrocarbon, or may be a group consisting of an optionally substituted aromatic hydrocarbon and another linking group.
  • the aromatic hydrocarbon may be a group consisting of a combination of groups, and is preferably a group consisting only of an optionally substituted aromatic hydrocarbon.
  • the substituent that the aromatic hydrocarbon may have is a substituent Z (e.g., an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, an amino group, a carboxy group, a halogen atom, etc.).
  • the aromatic hydrocarbon preferably has no substituents.
  • the aromatic hydrocarbon linking group is generally a divalent linking group.
  • the aromatic hydrocarbon linking group specifically includes a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a biphenyldiyl group, and a fluorenediyl group, which may have a substituent.
  • a phenylene group optionally having a substituent is preferable.
  • the substituent is exemplified by the above-described substituent Z, but the above-described groups such as the phenylene group preferably have no substituent.
  • the structural unit represented by the formula (V) includes a structural unit represented by the following formula (V1), a structural unit represented by the following formula (V2), and a structural unit represented by the following formula (V3). More preferably, at least one is included. In addition, * in the following formula represents a binding position. Further, hereinafter, the structural units represented by formulas (V1) to (V3) may be collectively referred to as "structural unit (a)".
  • L 1 is an aromatic hydrocarbon linking group (preferably 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 10 carbon atoms).
  • Specific examples include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a biphenyldiyl group, and a fluorenediyl group, which may have a substituent.
  • a phenylene group having a low molecular weight is preferred.
  • the substituent is exemplified by the above-described substituent Z, but the above-described groups such as the phenylene group preferably have no substituent.
  • the compound forming the structural unit (a) is preferably a divinyl aromatic compound, and examples thereof include divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene. be done. Among them, divinylbenzene is particularly preferred. One type of these divinyl aromatic compounds may be used, or two or more types may be used as necessary.
  • the polymer having the structural unit represented by formula (V) may be a homopolymer of the structural unit (a), or may be a copolymer with a structural unit derived from another monomer.
  • the copolymerization ratio of the structural unit (a) is preferably 5 mol% or more, and preferably 10 mol% or more. more preferably 15 mol % or more.
  • the upper limit is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, and 60 mol%. % or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, even more preferably 30 mol% or less, and 25 mol% or less. It may be below.
  • structural units derived from other monomers include structural units (b) derived from aromatic compounds having one vinyl group (monovinyl aromatic compounds).
  • the structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).
  • L 2 is an aromatic hydrocarbon linking group, and preferred specific examples thereof include the above examples of L 1 .
  • R V1 is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). When R V1 is a hydrocarbon group, it preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. R V1 and L 2 may have the substituent Z described above.
  • the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (b) derived from a monovinyl aromatic compound
  • examples of the monovinyl aromatic compound include styrene and vinylnaphthalene.
  • vinyl aromatic compounds such as vinylbiphenyl; o-methylstyrene, m-methylstyrene, p-methylstyrene, o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, Examples thereof include nuclear alkyl-substituted vinyl aromatic compounds such as methylvinylbiphenyl and ethylvinylbiphenyl.
  • the monovinyl aromatic compounds exemplified here may optionally have the substituent Z described above. Moreover, one of these monovinyl aromatic compounds may be used, or two or more thereof may be used.
  • the copolymerization ratio of the structural unit (b) is preferably 10 mol% or more, It is more preferably 15 mol% or more, and further 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, 75 mol% or more.
  • the upper limit is preferably 98 mol % or less, more preferably 90 mol % or less, and even more preferably 85 mol % or less.
  • the polymer having the structural unit represented by formula (V) may have structural units other than the structural unit (a) and the structural unit (b).
  • Examples of other structural units include structural units (c) derived from cycloolefin compounds.
  • Cycloolefin compounds include hydrocarbons having a double bond in the ring structure.
  • monocyclic cyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene
  • compounds having a norbornene ring structure such as norbornene and dicyclopentadiene
  • cycloolefin compounds in which aromatic rings are condensed such as indene and acenaphthylene etc.
  • norbornene compounds examples include those described in paragraphs 0037 to 0043 of JP-A-2018-39995, the contents of which are incorporated herein.
  • the cycloolefin compounds exemplified here may further have the substituent Z described above.
  • the copolymerization ratio of the structural unit (c) is preferably 10 mol% or more, It is more preferably 20 mol % or more, and even more preferably 30 mol % or more.
  • the upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, even more preferably 70 mol% or less, may be 50 mol% or less, or 30 mol%. It may be below.
  • a polymer having a structural unit represented by formula (V) may further incorporate a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as another polymerizable compound).
  • Other polymerizable compounds (monomers) include, for example, compounds containing three vinyl groups. Specific examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, ethylene glycol diacrylate, butadiene and the like can be used.
  • the copolymerization ratio of structural units (d) derived from other polymerizable compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less. .
  • a polymer having a structural unit represented by formula (V) a polymer essentially containing the structural unit (a) and containing at least one of the structural units (b) to (d) is exemplified. . Furthermore, an embodiment is exemplified in which the total of structural units (a) to (d) accounts for 95 mol% or more, further 98 mol% or more of all structural units.
  • the structural unit (a) is essential, and 90 mol of structural units containing an aromatic ring are included in all structural units excluding terminals. % or more, more preferably 95 mol % or more, and may be 100 mol %.
  • one structural unit is a monomer used for producing a polymer having a structural unit represented by formula (V) (for example, a divinyl aromatic compound , monovinyl aromatic compounds, etc.).
  • the method for producing a polymer having a structural unit represented by formula (V) is not particularly limited and may be a conventional method.
  • a raw material containing a divinyl aromatic compound if necessary, a coexistence of an olefin compound, etc.
  • a metal fluoride such as boron trifluoride or a complex thereof can be used as the Lewis acid catalyst.
  • the structure of the chain end of the polymer having the structural unit represented by the formula (V) is not particularly limited, but the group derived from the divinyl aromatic compound may have the structure of the following formula (E1). mentioned.
  • the molecular weight of the polymer having the structural unit represented by the formula (V), in terms of number average molecular weight Mn, is preferably 300 or more, more preferably 500 or more, and further preferably 1,000 or more. It is preferably 1,500 or more, and more preferably 1,500 or more.
  • the upper limit of the number average molecular weight Mn is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, and further preferably 100,000 or less. preferable.
  • the weight-average molecular weight Mw of the polymer having the structural unit represented by formula (V) is preferably 1,000 or more, more preferably 2,000 or more, and 3,000 or more.
  • the excellent low dielectric properties of the polymer having the structural unit represented by the formula (V), especially Df and dielectric properties after moisture absorption, are effectively applied to the cured product of the resin composition.
  • the upper limit of the weight average molecular weight Mw is preferably 160,000 or less, more preferably 150,000 or less, even more preferably 140,000 or less, and even more preferably 130,000 or less. .
  • the thickness is equal to or less than the above upper limit, there is a tendency that poor embedding is less likely to occur when the prepreg or resin sheet is laminated on the circuit board.
  • the monodispersity (Mw/Mn) represented by the ratio of the weight average molecular weight Mw to the number average molecular weight Mn is preferably 100 or less, more preferably 50 or less, and even more preferably 20 or less. . It is practical that the lower limit of the monodispersity is 1.1 or more, and even if it is 10 or more, the required performance is satisfied.
  • the above Mw and Mn are measured according to the description of Examples described later.
  • the resin composition of the present embodiment contains two or more polymers having structural units represented by formula (V)
  • the Mw, Mn and Mw/Mn of the mixture preferably satisfy the above ranges.
  • the vinyl group equivalent weight of the polymer having the structural unit represented by formula (V) is 200 g/eq. 230 g/eq. more preferably 250 g/eq. It is more preferable that it is above. Moreover, the equivalent weight of the vinyl group is 1200 g/eq. It is preferably less than or equal to 1000 g/eq. It is more preferably less than or equal to 800 g/eq. 600 g/eq. 400 g/eq. 300 g/eq. It may be below. When the amount is at least the above lower limit, the storage stability of the resin composition tends to improve, and the fluidity of the resin composition tends to improve.
  • the cured product of the polymer having the structural unit represented by the formula (V) used in the present embodiment has excellent dielectric properties.
  • the cured polymer having the structural unit represented by the formula (V) used in this embodiment has a dielectric constant (Dk) of 2.80 or less at 10 GHz measured according to the cavity resonator perturbation method. is preferably 2.60 or less, more preferably 2.50 or less, and even more preferably 2.40 or less.
  • the lower limit of the dielectric constant is practically 1.80 or more, for example.
  • the cured product of the polymer having the structural unit represented by the formula (V) used in the present embodiment has a dielectric loss tangent (Df) at 10 GHz measured according to the cavity resonator perturbation method, which is 0.0030 or less. It is preferably 0.0020 or less, more preferably 0.0010 or less. Moreover, the lower limit value of the dielectric loss tangent is practically 0.0001 or more, for example.
  • the dielectric loss tangent (Df) is measured according to the method described in Examples below.
  • the dielectric constant (Dk) is also measured according to the method for measuring Df in Examples.
  • the resin composition of the present embodiment contains a polymer having a structural unit represented by formula (V), when the resin solid content in the resin composition is 100 parts by mass, it is represented by formula (V) It is preferable that the content of the polymer having the structural unit is 5 to 50 parts by mass.
  • the lower limit of the content of the polymer having the structural unit represented by formula (V) is preferably 10 parts by mass or more, preferably 15 parts by mass, when the resin solid content in the resin composition is 100 parts by mass. It is more preferably 20 parts by mass or more, or 25 parts by mass or more.
  • the upper limit of the content of the polymer having the structural unit represented by formula (V) is preferably 45 parts by mass or less when the resin solid content in the resin composition is 100 parts by mass. It is more preferably 40 parts by mass or less, and even more preferably 35 parts by mass or less. Moreover, the metal foil peel strength of the obtained hardened
  • the polymer having the structural unit represented by formula (V) may be contained in the resin composition either singly or in combination of two or more. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of the present embodiment may contain a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminal.
  • the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is preferably a polyphenylene ether compound having a group selected from the group consisting of a (meth)acrylic group, a maleimide group and a vinylbenzyl group at the terminal.
  • the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is preferably a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminal.
  • polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the end include compounds having a phenylene ether skeleton represented by the following formula (X1).
  • R 24 , R 25 , R 26 and R 27 may be the same or different and represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom or a hydrogen atom. )
  • a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end has the formula (X2): (In Formula (X2), R 28 , R 29 , R 30 , R 34 and R 35 may be the same or different and represent an alkyl group having 6 or less carbon atoms or a phenyl group.
  • R 31 and R 32 , and R33 which may be the same or different, are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and/or the formula (X3):
  • R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 and R 43 may be the same or different, hydrogen atom, alkyl having 6 or less carbon atoms or a phenyl group, and -A- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.).
  • a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end is a modified polyphenylene ether compound (hereinafter referred to as "modified polyphenylene ether compound (g )”), and more preferably a modified polyphenylene ether compound having two or more groups selected from the group consisting of a (meth)acrylic group, a maleimide group, and a vinylbenzyl group at the end.
  • modified polyphenylene ether compound (g) By employing such a modified polyphenylene ether compound (g), it becomes possible to further reduce the dielectric loss tangent (Df) of the cured product of the resin composition. These may be used singly or in combination of two or more.
  • Modified polyphenylene ether compounds include compounds represented by formula (OP-1).
  • X represents an aromatic group
  • -(YO)n 2 - represents a polyphenylene ether structure
  • R 1 , R 2 and R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl group
  • n1 represents an integer of 1 to 6
  • n2 represents an integer of 1 to 100
  • n3 represents an integer of 1 to 4.
  • n 2 and/or n 3 is an integer of 2 or more
  • n 2 structural units (YO) and/or n 3 structural units may be the same or different.
  • n3 is preferably 2 or more, more preferably 2.
  • the modified polyphenylene ether compound (g) in the present embodiment is preferably a compound represented by formula (OP-2). where -(O-X-O)- is the formula (OP-3): (In formula (OP-3), R 4 , R 5 , R 6 , R 10 and R 11 may be the same or different and are an alkyl group having 6 or less carbon atoms or a phenyl group.
  • R 7 , R 8 and R 9 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and/or formula (OP-4): (In formula (OP-4), R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 may be the same or different, hydrogen atom, carbon number 6 or less is an alkyl group or a phenyl group, and -A- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.).
  • -(Y-O)- is the formula (OP-5):
  • R 20 and R 21 may be the same or different and are an alkyl group having 6 or less carbon atoms or a phenyl group.
  • R 22 and R 23 may be the same or different, a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group).
  • a and b represent an integer of 0 to 100, at least one of which is not 0, preferably an integer of 0 to 50, more preferably an integer of 1 to 30 preferable.
  • 2 or more -(Y-O)- may each independently be an arrangement of one structure, and two or more structures may be block or They may be arranged randomly.
  • -A- in formula (OP-4) includes, for example, a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, 1, Divalent organic groups such as 3-phenylenebis(1-methylethylidene) group, cyclohexylidene group, phenylmethylene group, naphthymethylene group, 1-phenylethylidene group, etc., but are not limited thereto. .
  • R 4 , R 5 , R 6 , R 10 , R 11 , R 20 and R 21 are alkyl groups having 3 or less carbon atoms
  • R 7 and R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 22 and R 23 are hydrogen atoms or alkyl groups having 3 or less carbon atoms.
  • —(O—X—O)— represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and/or —(Y—O)— represented by formula (OP-11) and represented by formula (OP-5) is preferably formula (OP-12) or formula (OP-13).
  • a and / or b is an integer of 2 or more
  • 2 or more -(YO)- are each independently a structure in which 2 or more of formula (OP-12) and / or formula (OP-13) are arranged or a structure in which the formulas (OP-12) and (OP-13) are arranged in blocks or randomly.
  • R 44 , R 45 , R 46 and R 47 may be the same or different and are a hydrogen atom or a methyl group.
  • -B- is a straight chain having 20 or less carbon atoms. A chain, branched or cyclic divalent hydrocarbon group.
  • Specific examples of -B- are the same as the specific examples of -A- in formula (OP-4).
  • -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • Specific examples of -B- are the same as the specific examples of -A- in formula (OP-4).
  • a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its end may be produced by a known method, or a commercially available product may be used.
  • Commercially available products include, for example, "SA9000” manufactured by SABIC Innovative Plastics Co., Ltd. as a modified polyphenylene ether compound having a methacryl group at the end.
  • modified polyphenylene ether compounds having a terminal vinylbenzyl group include "OPE-2St1200” and "OPE-2st2200” manufactured by Mitsubishi Gas Chemical.
  • a polyphenylene ether compound having a terminal hydroxyl group such as "SA90" manufactured by SABIC Innovative Plastics was modified into a vinylbenzyl group using vinylbenzyl chloride or the like. You can also use things.
  • Polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end preferably, modified polyphenylene ether compound (g)) by GPC (gel permeation chromatography) method polystyrene equivalent number average molecular weight (details will be described later Examples according to the method described in ) is preferably 500 or more and 3,000 or less.
  • the number average molecular weight is 500 or more, stickiness tends to be further suppressed when the resin composition of the present embodiment is formed into a coating film.
  • the number average molecular weight is 3,000 or less, the solubility in solvents tends to be further improved.
  • the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end is preferably 800 or more and 10,000 or less, more preferably 800 or more and 5,000 or less.
  • the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower, and by setting it to the above upper limit or less, the varnish or the like described later can be reduced.
  • the solubility, low viscosity, and moldability of the resin composition in a solvent during production are further improved.
  • the terminal carbon-carbon unsaturated double bond equivalent is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, and 400 to 2500 g. is more preferable.
  • the content is at least the lower limit, the cured product of the resin composition tends to have a lower dielectric constant (Dk) and dielectric loss tangent (Df).
  • Dk dielectric constant
  • Df dielectric loss tangent
  • the lower limit of the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is , With respect to 100 parts by mass of the resin solid content in the resin composition, it is preferably 1 part by mass or more, more preferably 3 parts by mass or more, further preferably 5 parts by mass or more, 7 parts by mass It is more preferable that it is above.
  • the content is at least the above lower limit, the resulting cured product tends to have improved low water absorption and low dielectric properties (Dk and/or Df).
  • the upper limit of the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end is preferably 70 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, and may be 30 parts by mass or less, or 25 parts by mass or less.
  • the resin composition in the present embodiment may contain only one type of polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of the present embodiment may further contain another resin (D).
  • the other resin (D) preferably contains at least one selected from the group consisting of maleimide compounds, cyanate ester compounds, epoxy compounds, phenol compounds, alkenyl-substituted nadimide compounds, oxetane resins, and benzoxazine compounds. , cyanate compounds, maleimide compounds, and other resins (D) selected from the group consisting of epoxy compounds.
  • Such other resin (D) is not necessarily an essential component for achieving the effects of the present invention, but by blending these components, various physical properties can be imparted to the resin composition or cured product. , the dielectric properties, moisture absorption and heat resistance of the resin composition or cured product can be further improved.
  • These other resins (D) may be used alone or in combination of two or more.
  • the resin composition of the present embodiment may contain a cyanate ester compound.
  • the cyanate ester compound has 1 or more cyanate groups (cyanato groups) per molecule (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, more preferably 2 or 3, still more preferably is not particularly limited as long as it is a compound containing 2), and a wide range of compounds commonly used in the field of printed wiring boards can be used.
  • the cyanate ester compound is preferably a compound in which a cyanate group is directly bonded to an aromatic skeleton (aromatic ring).
  • cyanate ester compounds include phenol novolak-type cyanate ester compounds, naphthol aralkyl-type cyanate ester compounds (naphthol aralkyl-type cyanates), naphthylene ether-type cyanate ester compounds, biphenyl aralkyl-type cyanate ester compounds, and xylene resins.
  • type cyanate ester compound trisphenolmethane type cyanate ester compound, adamantane skeleton type cyanate ester compound, bisphenol M type cyanate ester compound, bisphenol A type cyanate ester compound, and diallylbisphenol A type cyanate ester compound At least one selected from the group is included.
  • phenol novolac type cyanate ester compounds from the viewpoint of further improving the low water absorption of the resulting cured product, phenol novolac type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds, naphthylene ether type cyanate ester compounds, xylene resin type cyanic acid It is preferably at least one selected from the group consisting of an ester compound, a bisphenol M-type cyanate compound, a bisphenol A-type cyanate compound, and a diallyl bisphenol A-type cyanate compound, and a naphthol aralkyl-type cyanate ester. Compounds are more preferred. These cyanate ester compounds may be prepared by known methods, or commercially available products may be used.
  • a cyanate ester compound having a naphthol aralkyl skeleton, a naphthylene ether skeleton, a xylene skeleton, a trisphenolmethane skeleton, or an adamantane skeleton has a relatively large number of functional group equivalents, and the number of unreacted cyanate ester groups is small. Therefore, a cured product of a resin composition using these tends to be even more excellent in low water absorption. Also, mainly due to having an aromatic skeleton or adamantane skeleton, the plating adhesion tends to be further improved.
  • the resin composition of the present embodiment preferably contains a cyanate ester compound within a range that does not impair the effects of the present invention.
  • the lower limit of the content is preferably 0.1 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. , more preferably 2 parts by mass or more, and may be 5 parts by mass or more.
  • the content of the cyanate ester compound is 0.1 part by mass or more, the heat resistance, combustion resistance, chemical resistance, low dielectric constant, low dielectric loss tangent, and insulation properties of the obtained cured product are improved. There is a tendency.
  • the upper limit of the content of the cyanate ester compound is 70 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. Preferably, it is 50 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less.
  • the resin composition in the present embodiment may contain only one type of cyanate ester compound, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of this embodiment may contain a maleimide compound.
  • the resin composition of the present embodiment has 1 or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, still more preferably 2 or 3, still more preferably 2) per molecule.
  • the compound is not particularly limited as long as it has a maleimide group, and a wide range of compounds commonly used in the field of printed wiring boards can be used.
  • the maleimide compound is a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), It preferably contains one or more selected from the group consisting of a compound represented by formula (M4) and a compound represented by formula (M5), and a compound represented by formula (M0), a compound represented by formula (M1 ), a compound represented by formula (M3), a compound represented by formula (M4), and one or more selected from the group consisting of a compound represented by formula (M5) More preferably, it contains one or more selected from the group consisting of a compound represented by formula (M1), a compound represented by formula (M3), and a compound represented by formula (M5).
  • the maleimide compounds contains a compound represented by formula (M1) and/or a compound represented by formula (M3).
  • M1 a compound represented by formula (M1)
  • M3 a compound represented by formula (M3).
  • each R 51 independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group; each R 52 independently represents a hydrogen atom or a methyl group; n 1 represents an integer of 1 or more.
  • each R 51 is independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group; It is preferably one selected, more preferably a hydrogen atom and/or a methyl group, and even more preferably a hydrogen atom.
  • R 52 is preferably a methyl group.
  • n 1 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.
  • each R 8 independently represents a hydrogen atom, a methyl group or an ethyl group, preferably a methyl group.
  • the compound represented by formula (M0) may be a single compound or a mixture of two or more compounds.
  • mixtures include mixtures of compounds with different n 1 , mixtures of compounds with different types of substituents for R 51 and/or R 52 , and the bonding positions of the maleimide group and the oxygen atom to the benzene ring (meta-position, para-position, mixtures of compounds with different ortho positions) and mixtures of compounds in which two or more of the above different points are combined.
  • R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group.
  • R M5 and R M6 each independently represent a hydrogen atom or an alkyl group.
  • Ar M represents a divalent aromatic group
  • A is a 4- to 6-membered alicyclic group
  • R M7 and R M8 are each independently an alkyl group
  • mx is 1 or 2
  • lx is 0 or 1.
  • R M9 and R M10 each independently represent a hydrogen atom or an alkyl group
  • R M11 , R M12 , R M13 and R M14 each independently represent a hydrogen atom or Representing an organic group
  • R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, represents an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group or a mercapto group
  • px represents an integer of 0 to 3
  • nx represents an integer of 1 to 20.
  • R M1 , R M2 , R M3 and R M4 in the formula each independently represent a hydrogen atom or an organic group.
  • the organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group. Among them, a methyl group is particularly preferred.
  • R M1 and R M3 are each independently preferably an alkyl group, and R M2 and R M4 are preferably hydrogen atoms.
  • RM5 and RM6 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group.
  • the alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and especially a methyl group.
  • Ar 1 M represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthenediyl group or an anthracenediyl group, more preferably a phenylene group, still more preferably an m-phenylene group.
  • Ar M may have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, Ethyl group, propyl group and butyl group are more preferred, and methyl group is particularly preferred.
  • Ar M is unsubstituted.
  • A is a 4- to 6-membered alicyclic group, more preferably a 5-membered alicyclic group (preferably a group forming an indane ring in combination with a benzene ring).
  • R 1 M7 and R 1 M8 are each independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group.
  • mx is 1 or 2, preferably 2;
  • lx is 0 or 1, preferably 1;
  • R M9 and R M10 each independently represent a hydrogen atom or an alkyl group, more preferably an alkyl group.
  • the alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and especially a methyl group.
  • R M11 , R M12 , R M13 and R M14 each independently represent a hydrogen atom or an organic group.
  • the organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group.
  • R M12 and R M13 are each independently preferably an alkyl group, and R M11 and R M14 are preferably hydrogen atoms.
  • R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aryl group having 1 to 10 carbon atoms.
  • aryloxy group, arylthio group having 1 to 10 carbon atoms, halogen atom, hydroxyl group or mercapto group, alkyl group having 1 to 4 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, or 6 to 10 carbon atoms is preferably an aryl group of px represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and still more preferably 0.
  • nx represents an integer of 1-20.
  • nx may be an integer of 10 or less.
  • the resin composition of the present embodiment may contain only one compound represented by the formula (M1) and having at least different nx values, or may contain two or more compounds. .
  • the average value of nx (average number of repeating units) n in the compound represented by formula (M1) in the resin composition has a low melting point (low softening point) and a low melt viscosity, It is preferably 0.92 or more, more preferably 0.95 or more, still more preferably 1.0 or more, and 1.1 or more for excellent handling properties. More preferred. Also, n is preferably 10.0 or less, more preferably 8.0 or less, still more preferably 7.0 or less, and even more preferably 6.0 or less. It may be 0 or less. The same applies to formula (M1-1) and the like, which will be described later.
  • the compound represented by formula (M1) is preferably a compound represented by formula (M1-1) below.
  • R M21 , R M22 , R M23 and R M24 each independently represent a hydrogen atom or an organic group
  • R M25 and R M26 each independently represent a hydrogen atom or an alkyl
  • R M27 , R M28 , R M29 and R M30 each independently represent a hydrogen atom or an organic group
  • R M31 and R M32 each independently represent a hydrogen atom or an alkyl group
  • R M33 , RM34 , RM35 and RM36 each independently represent a hydrogen atom or an organic group
  • RM37 , RM38 and RM39 each independently represent a hydrogen atom or an alkyl group
  • nx is represents an integer of 1 or more and 20 or less.
  • R M21 , R M22 , R M23 , and R M24 in the formula each independently represent a hydrogen atom or an organic group.
  • the organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group. More preferred, and a methyl group is particularly preferred.
  • R M21 and R M23 are preferably alkyl groups, and R M22 and R M24 are preferably hydrogen atoms.
  • RM25 and RM26 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group.
  • the alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and especially a methyl group.
  • R M27 , R M28 , R M29 and R M30 each independently represent a hydrogen atom or an organic group, preferably a hydrogen atom.
  • the organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group. More preferred, and a methyl group is particularly preferred.
  • R M31 and R M32 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group.
  • the alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and especially a methyl group.
  • R M33 , R M34 , R M35 and R M36 each independently represent a hydrogen atom or an organic group.
  • the organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group.
  • R M33 and R M36 are preferably hydrogen atoms, and R M34 and R M35 are preferably alkyl groups.
  • R M37 , R M38 and R M39 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group.
  • the alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and especially a methyl group.
  • nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.
  • the compound represented by formula (M1-1) is preferably a compound represented by formula (M1-2) below.
  • R M21 , R M22 , R M23 and R M24 each independently represent a hydrogen atom or an organic group
  • R M25 and R M26 each independently represent a hydrogen atom or an alkyl
  • R M27 , R M28 , R M29 and R M30 each independently represent a hydrogen atom or an organic group
  • R M31 and R M32 each independently represent a hydrogen atom or an alkyl group
  • R M33 , RM34 , RM35 and RM36 each independently represent a hydrogen atom or an organic group
  • RM37 , RM38 and RM39 each independently represent a hydrogen atom or an alkyl group
  • nx is represents an integer of 1 or more and 20 or less.
  • R M21 , R M22 , R M23 , R M24 , R M25 , R M26 , R M27 , R M28 , R M29 , R M30 , R M31 , R M32 , R M33 , R M34 , R M35 , R M36 , R M37 , R M38 , R M39 and nx are respectively R M21 , R M22 , R M23 , R M24 , R M25 , R M26 , R M27 , R M27 , R M26 , R M27 in formula (M1-1) RM28 , RM29 , RM30 , RM31 , RM32 , RM33 , RM34 , RM35 , RM36 , RM37 , RM38 , RM39 , and nx, and the preferred ranges are also the same .
  • the compound represented by formula (M1-1) is preferably a compound represented by formula (M1-3) below, more preferably a compound represented by formula (M1-4) below.
  • nx represents an integer of 1 or more and 20 or less.
  • nx may be an integer of 10 or less.
  • nx represents an integer of 1 or more and 20 or less.
  • nx may be an integer of 10 or less.
  • the molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. When the content is at least the above lower limit, the resulting cured product tends to be further improved in low dielectric properties and low water absorption. Further, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, further preferably 7,000 or less, and even more preferably 5,000 or less, It is more preferably 4000 or less. By adjusting the amount to the above upper limit or less, the heat resistance and handleability of the resulting cured product tend to be further improved.
  • each R 54 independently represents a hydrogen atom or a methyl group, and n 4 represents an integer of 1 or more.
  • n4 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, more preferably 1 or 2, and may be 1.
  • the compound represented by formula (M2) may be a mixture of compounds with different n4 , and is preferably a mixture. Also, as described in the section of the compound represented by formula (M0), it may be a mixture of compounds in which other moieties are different.
  • each R 55 independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group, and n 5 represents an integer of 1 or more and 10 or less.
  • R 55 each independently represents a group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group; It is preferably one more selected, more preferably a hydrogen atom and/or a methyl group, and even more preferably a hydrogen atom.
  • n5 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2.
  • the compound represented by formula (M3) may be a mixture of compounds with different n5 , and is preferably a mixture. Also, as described in the section of the compound represented by formula (M0), it may be a mixture of compounds in which other moieties are different.
  • each R 56 independently represents a hydrogen atom, a methyl group or an ethyl group, and each R 57 independently represents a hydrogen atom or a methyl group.
  • Each R 56 is preferably a methyl group or an ethyl group independently, more preferably a methyl group and an ethyl group in each of the two benzene rings, and R 57 is preferably a methyl group.
  • R 58 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group; R 59 each independently represents a hydrogen atom or a methyl group; n 6 represents an integer of 1 or more.
  • R 58 each independently represents a group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group; It is preferably one more selected, more preferably a hydrogen atom and/or a methyl group, and even more preferably a hydrogen atom.
  • R 59 is preferably a methyl group.
  • n6 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, more preferably 1 or 2, and may be 1.
  • the compound represented by formula (M5) may be a mixture of compounds with different n6 , and is preferably a mixture. Also, as described in the section of the compound represented by formula (M0), it may be a mixture of compounds in which other moieties are different.
  • the maleimide compound may be produced by a known method, or a commercially available product may be used.
  • Commercially available products include, for example, "BMI-80” manufactured by K-I Kasei Co., Ltd. as the compound represented by the formula (M0), and “NE-X-9470S” manufactured by DIC as the compound represented by the formula (M1). ”, “BMI-2300” manufactured by Daiwa Kasei Kogyo Co., Ltd. as a compound represented by formula (M2), “MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd.
  • formula (M3) formula (M4)
  • Examples of the compound represented by M4) include “BMI-70” manufactured by KI Kasei Co., Ltd., and “MIR-5000” manufactured by Nippon Kayaku Co., Ltd., as a compound represented by formula (M5).
  • maleimide compounds other than the above include N-phenylmaleimide, phenylmethanemaleimide oligomer, m-phenylenebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2 ,2,4-trimethyl)hexane, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimide phenoxy)benzene, prepolymers thereof, prepolymers of these maleimides and amines, and the like.
  • the lower limit of the content is preferably 1 part by mass or more and 5 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. More preferably, it is 10 parts by mass or more, and may be 20 parts by mass or more.
  • the upper limit of the content of the maleimide compound is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, and 50 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferably 40 parts by mass or less.
  • the resin composition in the present embodiment may contain only one type of maleimide compound, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of this embodiment may contain an epoxy compound.
  • the epoxy compound is a compound having one or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, still more preferably 2 or 3, still more preferably 2) epoxy groups in one molecule.
  • it is a resin, it is not particularly limited, and a wide range of compounds commonly used in the field of printed wiring boards can be used.
  • Epoxy compounds include, for example, bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, bisphenol A novolak type epoxy resin, glycidyl ester type epoxy resin, aralkyl Novolak type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolak type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolak type epoxy resin, phenol Aralkyl-type epoxy resin, naphthol-aralkyl-type epoxy resin, dicyclopentadiene-type epoxy resin, biphenyl-type epoxy resin, alicyclic epoxy resin, polyol-type epoxy resin, phosphorus-containing epoxy resin, glycidylamine, glycidyl ester, butadiene, etc.
  • the resin composition of the present embodiment preferably contains an epoxy compound within a range that does not impair the effects of the present invention.
  • the content thereof is preferably 0.1 parts by mass or more, and 1 part by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferable that the amount is 2 parts by mass or more.
  • the content of the epoxy compound is 0.1 parts by mass or more, the metal foil peel strength and toughness tend to be improved.
  • the upper limit of the content of the epoxy compound is preferably 50 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition, and is preferably 30 parts by mass.
  • the resin composition in the present embodiment may contain only one type of epoxy compound, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range. In addition, the resin composition in the present embodiment can also be configured so as not to substantially contain an epoxy compound.
  • Substantially free means that the content of the epoxy compound is less than 1 part by mass, preferably less than 0.1 part by mass, with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferably less than 0.01 part by mass.
  • the total amount of the other resin (D) when the other resin (D) is included, the total content is preferably 5 parts by mass or more, and 10 parts by mass or more, relative to 100 parts by mass of the resin solid content. is more preferably 20 parts by mass or more, and even more preferably 30 parts by mass or more. By making it more than the said lower limit, there exists a tendency for a glass transition temperature and heat resistance to improve more.
  • the upper limit of the total content of the other resin (D) is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, and 50 parts by mass with respect to 100 parts by mass of the resin solid content. It is more preferably 40 parts by mass or less. When the content is equal to or less than the upper limit, the low dielectric loss tangent property tends to be further improved.
  • the resin composition of the present embodiment may contain a flame retardant (E).
  • flame retardants (E) include phosphorus flame retardants, halogen flame retardants, inorganic flame retardants and silicone flame retardants, with phosphorus flame retardants being preferred.
  • Known flame retardants (E) can be used, for example, brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate.
  • pentabromotoluene tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, halogenated flame retardants such as chlorinated paraffin, red phosphorus, tricresyl phosphate, triphenyl phosphate, cresyl diphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl) phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), 10-(2 ,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, phosphorus-based flame retardants such as aluminum hydroxide, magnesium hydroxide, partial boehmite, boehmite, zinc borate,
  • the content thereof is preferably 1 part by mass or more, and 5 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. is more preferable.
  • the lower limit of the content of the flame retardant is preferably 25 parts by mass or less, more preferably 20 parts by mass or less.
  • a flame retardant (E) can be used individually by 1 type or in combination of 2 or more types. When using two or more kinds, the total amount is within the above range.
  • the resin composition of the present embodiment preferably contains a filler (F).
  • a filler (F) By including the filler (F), physical properties such as dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame resistance, and low thermal expansion of the resin composition and its cured product can be further improved.
  • the filler (F) used in the present embodiment preferably has excellent low dielectric properties.
  • the filler (F) used in the present embodiment preferably has a dielectric constant (Dk) of 8.0 or less, more preferably 6.0 or less, measured according to the cavity resonator perturbation method. It is more preferably 4.0 or less.
  • the lower limit of the dielectric constant is practically 2.0 or more, for example.
  • the dielectric loss tangent (Df) of the filler (F) used in the present embodiment measured according to the cavity resonator perturbation method, is preferably 0.05 or less, more preferably 0.01 or less. Moreover, the lower limit value of the dielectric loss tangent is practically 0.0001 or more, for example.
  • the type of the filler (F) used in this embodiment is not particularly limited, and those generally used in the industry can be suitably used. Specifically, silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, and hollow silica, and metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, and zirconium oxide.
  • complex oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, nitrides such as boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, aluminum hydroxide, Aluminum hydroxide heat-treated product (aluminum hydroxide heat-treated to reduce some of the water of crystallization), boehmite, metal hydroxides such as magnesium hydroxide (including hydrates), molybdenum oxide and molybdic acid Molybdenum compounds such as zinc, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, Inorganic fillers such as S-glass, M-glass G20, glass short fibers (including fine glass powders such as E-glass,
  • the filler (F) preferably contains an inorganic filler such as silica, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and titanium. It is more preferable to contain one or more selected from the group consisting of calcium oxide, and from the viewpoint of low dielectric properties, it is more preferable to contain one or more selected from the group consisting of silica and aluminum hydroxide. More preferably, it contains silica.
  • properties such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability and flame retardancy of the cured product of the resin composition are further improved.
  • the content of the filler (F) in the resin composition of the present embodiment can be appropriately set according to the desired properties, and is not particularly limited. It is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, still more preferably 40 parts by mass or more, even more preferably 60 parts by mass or more, and 80 parts by mass or more. is even more preferred. By making it more than the said lower limit, there exists a tendency for the low thermal expansion property and the low dielectric tangent property to improve more.
  • the upper limit of the content of the filler is preferably 300 parts by mass or less, more preferably 250 parts by mass or less, and 200 parts by mass or less with respect to 100 parts by mass of the resin solid content.
  • the content of the filler (F) is 30% by mass to 80% by mass of the components excluding the solvent.
  • the resin composition of the present embodiment may contain only one filler (F), or may contain two or more fillers (F). When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of the present embodiment may further contain a silane coupling agent when using a filler (F), particularly an inorganic filler.
  • a silane coupling agent when using a filler (F), particularly an inorganic filler.
  • Inclusion of the silane coupling agent tends to further improve the dispersibility of the filler (F) and the adhesive strength between the resin component, the filler (F), and the substrate described later.
  • the silane coupling agent is not particularly limited, and includes silane coupling agents generally used for surface treatment of inorganic substances, aminosilane compounds (eg, ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl) - ⁇ -aminopropyltrimethoxysilane, etc.), epoxysilane compounds (eg, ⁇ -glycidoxypropyltrimethoxysilane, etc.), vinylsilane compounds (eg, vinyltrimethoxysilane, etc.), styrylsilane compounds (eg, styryltrimethoxysilane, etc.), acrylsilane compounds (eg, ⁇ -acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (eg, N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyl) trimethoxysilane hydrochloride, etc.),
  • a silane coupling agent is used individually by 1 type or in combination of 2 or more types.
  • the silane coupling agent at least one selected from the group consisting of vinylsilane-based compounds, acrylsilane-based compounds, and styrylsilane-based compounds is used, and as the compatible thermosetting resin (C), aromatic
  • a thermosetting resin containing a ring and a vinyl group particularly, a polymer having a structural unit represented by formula (V)
  • a resin having excellent moisture absorption and heat resistance while maintaining excellent dielectric properties is obtained.
  • the content of the silane coupling agent is not particularly limited, but may be 0.1 to 5.0 parts by mass with respect to 100 parts by mass of the resin solid content.
  • a monomer or oligomer having an ethylenically unsaturated group can be used in combination in order to enhance thermosetting and curability with active energy rays (for example, photocurability with ultraviolet rays).
  • active energy rays for example, photocurability with ultraviolet rays.
  • the oligomer or monomer having an ethylenically unsaturated group used in the present embodiment is not particularly limited as long as it is an oligomer or monomer having one or more ethylenically unsaturated groups in one molecule.
  • (meth)acryloyl groups, vinyl groups, and the like are examples of (meth)acryloyl groups, vinyl groups, and the like.
  • a compound corresponding to a monomer or oligomer having an ethylenically unsaturated group and a compound corresponding to a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is A polyphenylene ether compound having a carbon-carbon unsaturated double bond is used.
  • the monomer having an ethylenically unsaturated group includes a compound (F1) (compound (F1 )).
  • compound (F1) compound (compound (F1 )
  • the ethylenically unsaturated bond of the compound (F1) reacts with the compatible thermosetting resin (C) to improve the moisture absorption and heat resistance of the obtained cured product.
  • the ethylenically unsaturated bond constituting the organic group containing the ethylenically unsaturated bond does not include those included as part of the aromatic ring.
  • Examples of ethylenically unsaturated bonds contained as part of non-aromatic rings include cyclohexenyl groups in the molecule. It is also meant to include the portion other than the end of the linear or branched organic group, that is, the ethylenically unsaturated bond contained in the linear or branched chain.
  • the organic group containing an ethylenically unsaturated bond is more preferably one selected from the group consisting of a vinyl group, an allyl group, an acrylic group, and a methacrylic group, and more preferably a vinyl group.
  • a compound that corresponds to a monomer or oligomer having an ethylenically unsaturated group and that also corresponds to a silane coupling agent is a silane coupling agent.
  • the compound (F1) used in this embodiment is also preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms and silicon atoms, and from carbon atoms, hydrogen atoms and oxygen atoms More preferably, it is composed only of selected atoms.
  • the compound (F1) used in this embodiment may or may not have a polar group.
  • the compound (F1) used in this embodiment preferably does not have a polar group.
  • Polar groups are exemplified by amino groups, carboxyl groups, hydroxy groups and nitro groups.
  • the molecular weight of compound (F1) is preferably 70 or more, more preferably 80 or more, even more preferably 90 or more.
  • the upper limit of the molecular weight of the compound (F1) is preferably 500 or less, more preferably 400 or less, still more preferably 300 or less, even more preferably 200 or less, and 150 or less. may By making it equal to or less than the upper limit, the effect of increasing the reactivity with the compatible thermosetting resin (C) tends to be further improved.
  • the average molecular weight value of the compound (F1) is preferably included in the above range, and the molecular weight of each compound is included in the preferred range. is more preferred.
  • the boiling point of compound (F1) is preferably 110° C. or higher, more preferably 115° C. or higher, even more preferably 120° C. or higher.
  • the boiling point of the compound (F1) is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower.
  • Examples of the compound (F1) include (meth)acrylate compounds, aromatic vinyl compounds (preferably styrene compounds), saturated fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, and ethylenically unsaturated carboxylic acids.
  • Anhydrides, ethylenically unsaturated dicarboxylic acid monoalkyl esters, ethylenically unsaturated carboxylic acid amides, etc. are exemplified, and selected from the group consisting of (meth)acrylic acid ester compounds, aromatic vinyl compounds, and saturated fatty acid vinyl compounds. is preferably at least one of the aromatic vinyl compounds, and more preferably an aromatic vinyl compound.
  • Specific examples of the compound (F1) include methylstyrene and ethylvinylbenzene.
  • the resin composition according to this embodiment also preferably contains a styrene oligomer (F2) in order to improve low dielectric constant and low dielectric loss tangent.
  • the styrene oligomer (F2) according to the present embodiment is obtained by polymerizing at least one selected from the group consisting of styrene, the above styrene derivative, and vinyltoluene, and has a number average molecular weight of 178 to 1600 and an average aromatic ring. 2 to 14 aromatic rings, the total amount of 2 to 14 aromatic rings is 50% by mass or more, and the boiling point is 300° C. or higher and does not have a branched structure.
  • styrene oligomer (F2) used in the present embodiment examples include styrene polymer, vinyltoluene polymer, ⁇ -methylstyrene polymer, vinyltoluene- ⁇ -methylstyrene polymer, styrene- ⁇ -styrene polymer, and the like. are mentioned.
  • styrene polymer commercially available products may be used. Examples include FTR-8100 (manufactured by Mitsui Chemicals, Inc.) and FTR-8120 (manufactured by Mitsui Chemicals, Inc.).
  • Examples of the vinyltoluene- ⁇ -methylstyrene polymer include Picotex LC (manufactured by Eastman Chemical Co.).
  • Examples of ⁇ -methylstyrene polymers include Crystalex 3070 (manufactured by Eastman Chemical Co.), Crystalex 3085 (manufactured by Eastman Chemical Co.), Crystalex (3100), Crystalex 5140 (manufactured by Eastman Chemical Co.) and FMR. -0100 (manufactured by Mitsui Chemicals, Inc.) and FMR-0150 (manufactured by Mitsui Chemicals, Inc.).
  • the styrene- ⁇ -styrene polymer includes FTR-2120 (manufactured by Mitsui Chemicals, Inc.). These styrene oligomers may be used alone or in combination of two or more. In the resin composition of the present embodiment, an ⁇ -methylstyrene oligomer is preferable because it is well heat-cured, and is excellent in fine wiring embedding properties, solder heat resistance, low dielectric constant, and low dielectric loss tangent.
  • thermosetting resin (C) a thermosetting resin containing an aromatic ring and a vinyl group (particularly, the formula (V)
  • the content is preferably 0.5 parts by mass or more with respect to 100 parts by mass of the resin solid content, and 1 mass It is more preferably 2 parts by mass or more, even more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and may be 5 parts by mass or more.
  • the upper limit of the content of the monomer or oligomer having the ethylenically unsaturated group is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, relative to 100 parts by mass of the resin solid content.
  • the resin composition of the present embodiment may contain only one type of monomer or oligomer having an ethylenically unsaturated group, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition of this embodiment may contain an active ester compound.
  • the active ester compound is not particularly limited. 2) includes compounds having an active ester group.
  • the active ester compound may be a linear or branched or cyclic compound.
  • an active ester compound obtained by reacting a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxy compound and/or a thiol compound is preferable from the viewpoint of further improving the heat resistance of the resulting cured product.
  • An active ester compound obtained by reacting a carboxylic acid compound with one or more compounds selected from the group consisting of a phenol compound, a naphthol compound, and a thiol compound is more preferred, and has a carboxylic acid compound and a phenolic hydroxyl group.
  • An aromatic compound obtained by reacting with an aromatic compound and having two or more active ester groups in one molecule is more preferable, and a compound having two or more carboxylic acids in one molecule and a phenolic hydroxyl group.
  • An aromatic compound obtained by reacting with an aromatic compound and having two or more active ester groups in one molecule is particularly preferred.
  • Examples of the carboxylic acid compound include one or more selected from the group consisting of benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.
  • benzoic acid acetic acid
  • succinic acid maleic acid, itaconic acid
  • phthalic acid isophthalic acid
  • terephthalic acid pyromellitic acid.
  • one or more selected from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, isophthalic acid and One or more selected from the group consisting of terephthalic acid is more preferable.
  • the above thiocarboxylic acid compound includes one or more selected from thioacetic acid and thiobenzoic acid.
  • the phenolic compound or naphthol compound include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalin, 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, tetrahydroxybenzophenone, phloroglucine, One or more selected from the group consisting of benzenetriol, dicyclopentadienyldiphenol, and phenol novolak, and from the viewpoint of further improving the heat resistance and
  • the thiol compound includes one or more selected from the group consisting of benzenedithiol and triazinedithiol.
  • the active ester compound is preferably a compound having two or more carboxylic acids in one molecule and containing an aliphatic chain. From the viewpoint of improvement, compounds having an aromatic ring are preferable. More specific active ester compounds include active ester compounds described in JP-A-2004-277460.
  • a commercial product may be used for the active ester compound, or it may be prepared by a known method.
  • Commercially available products include compounds containing a dicyclopentadienyldiphenol structure (e.g., EXB9451, EXB9460, EXB9460S, HPC-8000-65T (all manufactured by DIC), etc.), acetylated phenol novolaks (e.g., DC808 ( Mitsubishi Chemical Corp.)), and benzoyl compounds of phenol novolak (e.g., YLH1026, YLH1030, YLH1048 (all manufactured by Mitsubishi Chemical Corp.)).
  • EXB9460S is preferable from the viewpoint of further improving the low thermal expansion property of the material).
  • An active ester compound can be prepared by a known method, for example, by condensation reaction between a carboxylic acid compound and a hydroxy compound.
  • Specific examples include (a) a carboxylic acid compound or its halide, (b) a hydroxy compound, and (c) an aromatic monohydroxy compound, per mol of the carboxy group or acid halide group of (a), (b) 0.05 to 0.75 mol of the phenolic hydroxyl group of (c) and 0.25 to 0.95 mol of (c).
  • the active ester compound is preferably contained within a range that does not impair the effects of the present invention.
  • the resin composition of the present embodiment contains an active ester compound, it is preferably 1 part by mass or more and preferably 90 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition.
  • the resin composition in the present embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the resin composition in the present embodiment may be configured so as not to substantially contain an active ester compound.
  • Substantially free means that the content of the active ester compound is less than 1 part by mass, preferably less than 0.1 part by mass, with respect to 100 parts by mass of the resin solid content in the resin composition. More preferably, it is less than 0.01 part by mass.
  • the resin composition of this embodiment may contain a dispersant.
  • a dispersant those generally used for paints can be suitably used, and the type thereof is not particularly limited.
  • the dispersant is preferably a copolymer-based wetting and dispersing agent, and specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, and 2152 manufactured by BYK-Chemie Japan Co., Ltd. , 2155, BYK®-W996, W9010, W903, W940 and the like.
  • the lower limit of the content is preferably 0.01 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferably 1 part by mass or more, and may be 0.3 parts by mass or more.
  • the upper limit of the content of the dispersant is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and 3 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition. Part or less is more preferable.
  • a dispersing agent can be used individually by 1 type or in combination of 2 or more types. When using two or more kinds, the total amount is within the above range.
  • the resin composition of this embodiment may further contain a curing accelerator.
  • the curing accelerator is not particularly limited, but for example, 2-ethyl-4-methylimidazole, imidazoles such as triphenylimidazole; benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di- tert-butyl-di-per-phthalate, ⁇ , ⁇ '-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 2,5-dimethyl- organic peroxides such as 2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitrile (e.g.
  • the present embodiment it is also possible to adopt a configuration that does not substantially contain a polymerization initiator such as an organic peroxide or an azo compound. “Substantially free” means that the content of the polymerization initiator is less than 0.1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.
  • the lower limit of the content is preferably 0.005 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. It is more preferably 0.01 part by mass or more, and even more preferably 0.1 part by mass or more.
  • the upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, with respect to 100 parts by mass of the resin solid content in the resin composition. Part or less is more preferable.
  • a hardening accelerator can be used individually by 1 type or in combination of 2 or more types. When using two or more kinds, the total amount is within the above range.
  • the resin composition of the present embodiment may contain a solvent, and preferably contains an organic solvent.
  • a solvent is contained, the resin composition of the present embodiment is in a form (solution or varnish) in which at least part, preferably all of the various resin solids described above are dissolved or compatible with the solvent.
  • the solvent is not particularly limited as long as it is a polar organic solvent or a non-polar organic solvent capable of dissolving or dissolving at least a part, preferably all, of the various resin solids described above. Examples of polar organic solvents include ketones.
  • nonpolar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.).
  • a solvent can be used individually by 1 type or in combination of 2 or more types. When using two or more kinds, the total amount is within the above range.
  • the resin composition of the present embodiment may contain thermoplastic resins, various polymer compounds such as oligomers thereof, and various additives.
  • Additives include UV absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow control agents, lubricants, antifoaming agents, leveling agents, gloss agents, polymerization inhibitors, and the like. These additives can be used singly or in combination of two or more.
  • the resin composition of this embodiment is used as a cured product.
  • the resin composition of the present embodiment is a low dielectric constant material and/or a low dielectric loss tangent material, and is suitable as a resin composition for electronic materials such as an insulating layer of a printed wiring board and a semiconductor package material. can be used.
  • the resin composition of the present embodiment can be suitably used as a material for prepregs, metal foil-clad laminates using prepregs, resin composite sheets, and printed wiring boards.
  • the resin composition of the present embodiment is used as a layered (film-like, sheet-like, etc.) material such as prepreg, resin composite sheet, etc., which becomes an insulating layer of a printed wiring board.
  • the thickness is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more.
  • the upper limit of the thickness is preferably 200 ⁇ m or less, more preferably 180 ⁇ m or less.
  • the thickness of the layered material means the thickness including the glass cloth, for example, when the resin composition of the present embodiment is impregnated into the glass cloth or the like.
  • the material formed from the resin composition of the present embodiment may be used for applications in which a pattern is formed by exposure and development, or may be used in applications without exposure and development. In particular, it is suitable for applications that do not require exposure and development.
  • the prepreg of this embodiment is formed from a base material (prepreg base material) and the resin composition of this embodiment.
  • the prepreg of the present embodiment can be produced, for example, by applying (for example, impregnating and/or coating) the resin composition of the present embodiment to a substrate and then heating (for example, drying at 120 to 220° C. for 2 to 15 minutes. etc.).
  • the amount of the resin composition adhered to the substrate that is, the amount of the resin composition (including the filler (F)) relative to the total amount of the prepreg after semi-curing is preferably in the range of 20 to 99% by mass. It is more preferably in the range of ⁇ 80% by mass.
  • the base material is not particularly limited as long as it is a base material used for various printed wiring board materials.
  • materials for the base material include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, spherical glass, etc.). , inorganic fibers other than glass (eg, quartz), and organic fibers (eg, polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.).
  • the form of the substrate is not particularly limited, and includes woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, and the like. These substrates may be used alone or in combination of two or more.
  • a woven fabric subjected to super-spreading treatment and stuffing treatment is preferable.
  • a glass woven fabric having a thickness of m 2 or less is preferable, and from the viewpoint of moisture absorption and heat resistance, a glass woven fabric surface-treated with a silane coupling agent such as epoxysilane or aminosilane is preferable.
  • a low dielectric glass cloth made of glass fibers exhibiting a low dielectric constant and a low dielectric loss tangent, such as L-glass, NE-glass, and Q-glass is more preferable.
  • Examples of low dielectric constant substrates include substrates having a dielectric constant of 5.0 or less (preferably 3.0 to 4.9).
  • low dielectric loss tangent substrates include substrates having a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005).
  • the dielectric constant and dielectric loss tangent are values measured at 10 GHz using a perturbation method cavity resonator.
  • the metal foil-clad laminate of this embodiment includes at least one layer formed from the prepreg of this embodiment, and a metal foil disposed on one side or both sides of the layer formed from the prepreg.
  • a method for producing the metal foil-clad laminate of the present embodiment for example, at least one sheet of the prepreg of the present embodiment is arranged (preferably two or more sheets are stacked), a metal foil is arranged on one or both sides thereof, and lamination molding is performed. method. More specifically, the prepreg can be produced by arranging a metal foil such as copper or aluminum on one side or both sides of the prepreg and laminating the prepreg.
  • the number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9.
  • the metal foil is not particularly limited as long as it is used as a material for printed wiring boards, and examples thereof include copper foil such as rolled copper foil and electrolytic copper foil.
  • the thickness of the metal foil (preferably copper foil) is not particularly limited, and may be about 1.5 to 70 ⁇ m.
  • Examples of the molding method include methods commonly used for molding laminates and multilayer boards for printed wiring boards, and more specifically, using a multi-stage press machine, a multi-stage vacuum press machine, a continuous molding machine, an autoclave molding machine, and the like.
  • a multilayer board can also be obtained by combining the prepreg of the present embodiment and a wiring board for an inner layer, which is separately prepared, and performing lamination molding.
  • a method for manufacturing a multilayer board for example, copper foil of about 35 ⁇ m is placed on both sides of one prepreg of the present embodiment, laminated by the above molding method, an inner layer circuit is formed, and black is applied to this circuit.
  • the inner layer circuit board and the prepreg of the present embodiment are alternately arranged one by one, and copper foil is arranged on the outermost layer to satisfy the above conditions.
  • a multi-layer board can be produced by lamination molding, preferably under vacuum.
  • the metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.
  • the metal foil-clad laminate of the present embodiment preferably has a low dielectric loss tangent (Df) measured using a laminate from which the metal foil has been removed by etching.
  • the dielectric loss tangent (Df) at 10 GHz measured according to the cavity resonator perturbation method is preferably 0.0040 or less, more preferably 0.0030 or less, and 0.0025 or less. More preferably, it is even more preferably less than 0.0025.
  • the lower limit of the dielectric loss tangent (Df) is not particularly defined, for example, 0.0001 or more is practical. The measurement of the dielectric loss tangent follows the description of the examples described later.
  • the metal foil-clad laminate of the present embodiment preferably has a low coefficient of thermal expansion (CTE) measured using a laminate from which the metal foil has been removed by etching.
  • CTE is preferably 10 ppm/° C. or less.
  • 0 is ideal, but 0.001 ppm/°C or more is practical.
  • the measurement of CTE follows description of the Example mentioned later.
  • the resin composition for electronic materials obtained by using the resin composition of the present embodiment has a cured product having dielectric properties (low dielectric loss tangent), moisture absorption, In addition to heat resistance, it can have excellent properties such as crack resistance, appearance of the cured product, and low thermal expansion.
  • the printed wiring board of the present embodiment is a printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer is formed from the resin composition of the present embodiment. It includes at least one of a layer and a layer formed from the prepreg of this embodiment.
  • Such a printed wiring board can be manufactured according to a conventional method, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is shown below. First, a metal foil-clad laminate such as the copper foil-clad laminate described above is prepared. Next, the surface of the metal foil-clad laminate is etched to form an inner layer circuit, thereby producing an inner layer substrate.
  • the surface of the inner layer circuit of this inner layer substrate is subjected to a surface treatment to increase the adhesive strength as necessary, and then the required number of prepregs described above are laminated on the surface of the inner layer circuit, and a metal foil for the outer layer circuit is laminated on the outer side. Then, heat and pressurize to integrally mold. In this manner, a multi-layer laminate is produced in which an insulating layer composed of the substrate and the cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, after drilling holes for through holes and via holes in this multi-layer laminate, a plated metal film is formed on the walls of the holes for conducting the inner layer circuit and the metal foil for the outer layer circuit, and further the outer layer circuit. A printed wiring board is manufactured by etching the metal foil for the purpose to form an outer layer circuit.
  • the printed wiring board obtained in the above production example has an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer is the resin composition of the present embodiment and / or a cured product thereof.
  • the configuration includes That is, the prepreg of the present embodiment described above (for example, a prepreg formed from a base material and the resin composition of the present embodiment impregnated or applied thereto), and the resin composition of the metal foil clad laminate of the present embodiment described above. A layer formed from a material serves as an insulating layer in this embodiment.
  • the present embodiment also relates to a semiconductor device including the printed wiring board. Details of the semiconductor device can be referred to in paragraphs 0200 to 0202 of Japanese Patent Application Laid-Open No. 2021-021027, and the contents thereof are incorporated into this specification.
  • the resin composite sheet of the present embodiment includes a support and a layer formed from the resin composition of the present embodiment arranged on the surface of the support.
  • the resin composite sheet can be used as a build-up film or dry film solder resist.
  • the method for producing the resin composite sheet is not particularly limited, but for example, a solution obtained by dissolving the resin composition of the present embodiment in a solvent is applied (coated) to a support and dried to form a resin composite sheet. method to obtain.
  • Examples of the support used here include polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylenetetrafluoroethylene copolymer film, and a release film obtained by applying a release agent to the surface of these films, Organic film substrates such as polyimide films, conductor foils such as copper foils and aluminum foils, glass plates, SUS (Steel Use Stainless) plates, FRP (Fiber-Reinforced Plastics) and other plate-like substrates. It is not particularly limited.
  • Examples of the coating method include a method in which a solution obtained by dissolving the resin composition of the present embodiment in a solvent is applied onto a support using a bar coater, a die coater, a doctor blade, a baker applicator, or the like. be done. Also, after drying, a single-layer sheet can be obtained by peeling or etching the support from the resin composite sheet in which the support and the resin composition are laminated. It should be noted that a solution obtained by dissolving the resin composition of the present embodiment in a solvent is supplied into a mold having a sheet-like cavity and dried to form a sheet, thereby using a support. It is also possible to obtain a single layer sheet without
  • the drying conditions for removing the solvent are not particularly limited. A temperature of 20° C. to 200° C. and a time of 1 to 90 minutes are preferable because the curing of the resin composition proceeds. Further, the single-layer sheet or resin composite sheet can be used in an uncured state by simply drying the solvent, or can be used in a semi-cured (B-staged) state as necessary. Furthermore, the thickness of the resin layer in the single-layer sheet or resin composite sheet of the present embodiment can be adjusted by the concentration of the solution of the resin composition of the present embodiment used for coating (coating) and the thickness of the coating. However, the thickness is preferably 0.1 to 500 ⁇ m, because the solvent tends to remain during drying when the coating thickness is thick.
  • Resin "A” had a polystyrene-equivalent number-average molecular weight of 1975, a polystyrene-equivalent weight-average molecular weight of 3514, and a hydroxyl equivalent of 990 by GPC.
  • the resulting solution was concentrated by an evaporator and added dropwise to methanol for solidification, and the solid was collected by filtration and vacuum dried to obtain 450.1 g of a modified polyphenylene ether compound.
  • the modified polyphenylene ether compound had a polystyrene-equivalent number average molecular weight by GPC method of 2250, a polystyrene-equivalent weight average molecular weight by GPC method of 3920, and a vinyl group equivalent of 1189 g/vinyl group.
  • Solution 1 was added dropwise over 1.5 hours to 300 g of a 0.93 mol chloroform solution of cyanogen chloride charged in the reactor, and the mixture was stirred for 30 minutes after completion of the dropwise addition. Thereafter, a mixed solution of 0.1 mol of triethylamine and 30 g of chloroform was added dropwise into the reactor and stirred for 30 minutes to complete the reaction. After the by-produced triethylamine hydrochloride was filtered off from the reaction solution, the resulting filtrate was washed with 500 mL of 0.1N hydrochloric acid, and then washed with 500 mL of water four times. After drying this with sodium sulfate, it was evaporated at 75° C.
  • the resulting polymer (va) having a structural unit represented by formula (V) had a number average molecular weight Mn of 2,060, a weight average molecular weight Mw of 30,700, and a monodispersity Mw/Mn of 14.9. there were.
  • the polymer (va) having the structural unit represented by the formula (V) has resonance lines derived from each monomer unit used as a raw material. observed.
  • the ratio of each monomer unit (structural unit derived from each raw material) in the polymer (va) having the structural unit represented by formula (V) is as follows.
  • Structural unit derived from divinylbenzene 20.9 mol% (24.3% by mass)
  • Structural unit derived from ethylvinylbenzene 9.1 mol% (10.7% by mass)
  • Structural unit derived from styrene 70.0 mol% (65.0% by mass)
  • the structural unit having a residual vinyl group derived from divinylbenzene was 16.7 mol % (18.5 mass %).
  • Weight average molecular weight (Mw) and number average molecular weight (Mn) were measured by gel permeation chromatography (GPC) method.
  • a liquid feed pump (manufactured by Shimadzu Corporation, LC-20AD), a differential refractive index detector (manufactured by Shimadzu Corporation, RID-10A), and a GPC column (manufactured by Showa Denko Corporation, GPC KF-801, 802, 803, 804).
  • tetrahydrofuran as a solvent, a flow rate of 1.0 mL/min, a column temperature of 40° C., and a calibration curve using monodisperse polystyrene.
  • Example 1 30 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 1, a maleimide compound (manufactured by Nippon Kayaku Co., Ltd., MIR-3000-70MT, corresponding to the compound represented by formula (M3)) 30 parts by mass, the above synthesis 5 parts by mass of the naphthol aralkyl cyanate compound (SNCN) obtained in Example 2, 5 parts by mass of ⁇ -methylstyrene oligomer (KA3085 (trade name), weight average molecular weight: 664, manufactured by Eastman Chemical Co.), phosphorus flame retardant (PX-200, Daihachi Chemical Co., Ltd.) 15 parts by mass, hydrogenated styrene thermoplastic elastomer (SEBS, SEPTON2104, Mn83000, manufactured by Kuraray Co., Ltd.) 7.5 parts by mass, non-hydrogenated styrene heat 7.5 parts by mass of plastic elastomer (SBS, TR2250, Mn
  • This varnish is impregnated on a 0.1 mm thick NE glass woven fabric (2013 S101S manufactured by Nitto Boseki Co., Ltd.), dried by heating at 165 ° C. for 5 minutes, and a prepreg with a resin composition content of 60% by mass. (thickness 0.1 mm) was obtained.
  • the properties of the NE glass woven fabric used are as follows.
  • IPC applicable variety 2013 Density (book/25mm) Vertical: 46 Density (book/25mm) Horizontal: 44.1 Thickness (mm): 0.070 Mass (g/m 2 ): 80.7
  • 12 ⁇ m thick electrolytic copper foil 3EC-M3-VLP, manufactured by Mitsui Kinzoku Mining Co., Ltd.
  • the pressure was 30 kgf/cm 2 and the temperature was 220° C. at 120° C.
  • Vacuum pressing was performed for a minute to obtain a copper foil-clad laminate having an insulating layer thickness of 0.1 mm or 0.8 mm as a metal foil-clad laminate.
  • the physical properties (dielectric loss tangent (Df), moisture absorption heat resistance, crack resistance, post-curing appearance, coefficient of thermal expansion (CTE)) of the obtained copper foil-clad laminate were evaluated according to the methods described later.
  • a test piece (30 mm ⁇ 150 mm ⁇ 0.8 mm) was prepared by removing the copper foil from the obtained copper foil clad laminate by etching, and the dielectric loss tangent (Df) at 10 GHz was measured using a perturbation method cavity resonator. bottom. The measurement temperature was 23°C.
  • the perturbation method cavity resonator used was Agilent 8722ES, a product of Agilent Technologies. It was evaluated as follows. A: Less than 0.0025 B: 0.0025 or more
  • a test piece (50 mm x 50 mm x 0.5 mm) was prepared by removing all the copper foil on one side of the obtained copper foil clad laminate by etching, and removing the copper foil on half of the other side by etching. 8 mm) were produced. Using a pressure cooker tester, this test piece was allowed to stand in the presence of saturated steam at 121° C. and 2 atm for 3 hours, and then immersed in a solder bath at 260° C. for 30 seconds to observe the presence or absence of delamination. As the pressure cooker tester, PC-3 type manufactured by Hirayama Seisakusho Co., Ltd. was used. A: No abnormality B: With peeling
  • ⁇ Crack resistance (MIT test)> For the obtained copper foil clad laminate, a test piece (15 mm ⁇ 130 mm ⁇ 0.1 mm) was prepared by forming a wiring pattern with a wiring width of 1 mm on the copper foil according to JIS C5016: 1994, and the conductor pattern of the test piece was prepared. Attach an insulated wire to the terminal of the test piece, fix the upper end of the test piece to the plunger, set a load of 1 kgf on the lower end, and then bend in both directions at an angle of 135 ° and a speed of 175 cpm while energized. was started, and the number of reciprocating flexures up to disconnection was measured. It was evaluated as follows. S: 81 times or more A: 71 times or more and 80 times or less B: 40 times or more and 70 times or less C: 39 times or less
  • the copper foil of the obtained copper foil clad laminate was removed by etching to obtain a test piece (330 mm ⁇ 330 mm ⁇ 0.1 mm) for observing the appearance after curing.
  • the surface was observed to confirm the state of separation between the thermoplastic elastomer (A) and/or the thermoplastic elastomer (B) and the thermosetting resin (C), and the presence or absence of appearance abnormality was evaluated according to the following evaluation criteria. It was evaluated as follows. The evaluation was made by five experts and majority decision was taken. A: No abnormality B: Defective appearance
  • CTE Coefficient of linear thermal expansion
  • a TMA method thermo-mechanical analysis: Thermo -Mechanical Analysis
  • the coefficient of thermal expansion of the test piece was measured to obtain the value.
  • the temperature was changed from 30° C. to 340° C. per minute with a thermomechanical analyzer (manufactured by TA Instruments).
  • the temperature was raised at 10°C, and the linear thermal expansion coefficient (CTE(X)) (unit: ppm/°C) in the surface direction was measured from 30°C to 300°C.
  • the measurement direction was the longitudinal direction (Warp) of the glass cloth of the laminate.
  • ppm is the volume ratio.
  • Other details conform to JIS C 6481 5.19 above. It was evaluated as follows. A: 10 ppm/°C or less
  • Example 2 In Example 1, the hydrogenated styrene thermoplastic elastomer (SEPTON2104) was changed to the same amount of hydrogenated styrene thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Corporation). and others did likewise.
  • SEBS hydrogenated styrene thermoplastic elastomer
  • S.O.E. registered trademark
  • Example 3 In Example 2, the same amount of partially hydrogenated styrene thermoplastic elastomer (SBBS, S.O.E. (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Corp.) were blended, and other operations were carried out in the same manner.
  • SBBS partially hydrogenated styrene thermoplastic elastomer
  • Example 4 In Example 3, the amount of the modified polyphenylene ether compound obtained in Synthesis Example 1 was changed to 15 parts by mass, and 15 parts by mass of the polymer (va) obtained in Synthesis Example 3 was blended, Others did likewise.
  • Example 5 In Example 4, the blending amount of the hydrogenated styrene thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Corporation) was changed to 2 parts by mass. The procedure was the same except that the blending amount of the styrene-based thermoplastic elastomer (SBBS, S.O.E. (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Corp.) was changed to 13 parts by mass.
  • SEBS hydrogenated styrene thermoplastic elastomer
  • SBBS styrene-based thermoplastic elastomer
  • Example 1 Comparative example 1 In Example 1, the hydrogenated styrene thermoplastic elastomer (SEPTON2104) and the non-hydrogenated styrene thermoplastic elastomer (TR2250) were not blended, and the maleimide compound (MIR-3000-70MT) was blended in an amount of 45 parts by mass. and the others did the same.
  • SEPTON2104 hydrogenated styrene thermoplastic elastomer
  • TR2250 non-hydrogenated styrene thermoplastic elastomer
  • MIR-3000-70MT maleimide compound
  • Comparative example 2 In Example 1, the hydrogenated styrene thermoplastic elastomer (SEPTON2104) and the non-hydrogenated styrene thermoplastic elastomer (TR2250) were not blended, and 15 parts by mass of the hydrogenated styrene thermoplastic elastomer (S1605) was blended. , others did as well.
  • Comparative example 3 In Example 1, instead of the non-hydrogenated styrene thermoplastic elastomer (TR2250), the same amount of hydrogenated styrene thermoplastic elastomer (S1605) was blended, and the rest was carried out in the same manner.
  • TR2250 non-hydrogenated styrene thermoplastic elastomer
  • S1605 hydrogenated styrene thermoplastic elastomer
  • Comparative example 4 In Example 1, the modified polyphenylene ether compound obtained in Synthesis Example 1 was not blended, and the blending amount of the maleimide compound (MIR-3000-70MT) was changed to 60 parts by mass.
  • Comparative example 5 In Comparative Example 4, the same amount of hydrogenated styrene thermoplastic elastomer (S1605) was blended instead of the hydrogenated styrene thermoplastic elastomer (SEPTON2104), and the rest was carried out in the same manner.
  • S1605 hydrogenated styrene thermoplastic elastomer
  • SEPTON2104 hydrogenated styrene thermoplastic elastomer

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Abstract

L'invention se réfère à une nouvelle composition de résine qui présente une excellente résistance à la chaleur après absorption d'humidité tout en maintenant une excellente tangente de faible perte diélectrique, ainsi qu'à un préimprégné, à une carte stratifiée revêtue d'une feuille métallique, à une feuille composite de résine, à une carte de circuit imprimé et à un dispositif semi-conducteur. La composition de résine comprend un élastomère thermoplastique (A), un élastomère thermoplastique (B) et une résine thermodurcissable (C) qui est compatible avec (A) et (B). L'élastomère thermoplastique (A) est un élastomère thermoplastique comprenant une unité monomère de styrène et une unité monomère de diène conjugué, et dont le poids moléculaire moyen en nombre est d'au moins 50 000, toutes les liaisons diène conjuguées de l'élastomère thermoplastique étant hydrogénées. L'élastomère thermoplastique (B) est un élastomère thermoplastique comprenant une unité monomère de styrène et une unité monomère de diène conjugué, et dont le poids moléculaire moyen en nombre est d'au moins 50 000, une partie des liaisons diène conjuguées de l'élastomère thermoplastique étant hydrogénées et/ou toutes étant des liaisons insaturées.
PCT/JP2022/034258 2021-09-27 2022-09-13 Composition de résine, préimprégné, carte stratifiée revêtue d'une feuille métallique, feuille composite de résine, carte de circuit imprimé et dispositif semi-conducteur WO2023048024A1 (fr)

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JP2023549494A JPWO2023048024A1 (fr) 2021-09-27 2022-09-13
CN202280064918.5A CN118019807A (zh) 2021-09-27 2022-09-13 树脂组合物、预浸料、覆金属箔层叠板、树脂复合片、印刷电路板及半导体装置
KR1020247012994A KR20240065287A (ko) 2021-09-27 2022-09-13 수지 조성물, 프리프레그, 금속박 피복 적층판, 수지 복합 시트, 프린트 배선판, 및 반도체 장치

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0790173A (ja) * 1993-09-21 1995-04-04 Mitsubishi Gas Chem Co Inc 樹脂組成物
JPH1180535A (ja) * 1997-09-04 1999-03-26 Sumitomo Chem Co Ltd 熱可塑性樹脂組成物
JP2000143891A (ja) * 1998-09-09 2000-05-26 Asahi Chem Ind Co Ltd 熱可塑性樹脂組成物
WO2015159912A1 (fr) * 2014-04-16 2015-10-22 旭化成ケミカルズ株式会社 Composition élastomère thermoplastique, bouchon pour récipient médical et récipient médical

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3805316A4 (fr) 2018-06-01 2022-04-06 Mitsubishi Gas Chemical Company, Inc. Composition de résine, préimprégné, stratifié revêtu d'une feuille métallique, feuille de résine et carte imprimée
JP7409369B2 (ja) 2019-02-28 2024-01-09 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、金属箔張積層板、樹脂複合シート、および、プリント配線板

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0790173A (ja) * 1993-09-21 1995-04-04 Mitsubishi Gas Chem Co Inc 樹脂組成物
JPH1180535A (ja) * 1997-09-04 1999-03-26 Sumitomo Chem Co Ltd 熱可塑性樹脂組成物
JP2000143891A (ja) * 1998-09-09 2000-05-26 Asahi Chem Ind Co Ltd 熱可塑性樹脂組成物
WO2015159912A1 (fr) * 2014-04-16 2015-10-22 旭化成ケミカルズ株式会社 Composition élastomère thermoplastique, bouchon pour récipient médical et récipient médical

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CN118019807A (zh) 2024-05-10

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