WO2021010431A1 - 樹脂組成物、プリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板、及び配線板 - Google Patents

樹脂組成物、プリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板、及び配線板 Download PDF

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Publication number
WO2021010431A1
WO2021010431A1 PCT/JP2020/027599 JP2020027599W WO2021010431A1 WO 2021010431 A1 WO2021010431 A1 WO 2021010431A1 JP 2020027599 W JP2020027599 W JP 2020027599W WO 2021010431 A1 WO2021010431 A1 WO 2021010431A1
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Prior art keywords
resin composition
group
compound
resin
polyphenylene ether
Prior art date
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Ceased
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PCT/JP2020/027599
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English (en)
French (fr)
Japanese (ja)
Inventor
宏典 齋藤
誼群 王
博晴 井上
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Panasonic Intellectual Property Management Co Ltd
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Panasonic Intellectual Property Management Co Ltd
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Priority to JP2021533093A priority Critical patent/JP7519587B2/ja
Priority to CN202080051204.1A priority patent/CN114207021B/zh
Priority to US17/626,881 priority patent/US12098257B2/en
Priority to KR1020227004909A priority patent/KR102931421B1/ko
Publication of WO2021010431A1 publication Critical patent/WO2021010431A1/ja
Anticipated expiration legal-status Critical
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    • 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
    • C08J2315/00—Characterised by the use of rubber derivatives
    • 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
    • C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • 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
    • C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/08—Epoxidised polymerised polyenes
    • 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
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2371/12—Polyphenylene oxides
    • 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
    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • 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
    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2453/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • 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
    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2463/08—Epoxidised polymerised polyenes
    • 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
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2471/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2471/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0326—Organic insulating material consisting of one material containing O
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics

Definitions

  • the present invention relates to a resin composition, a prepreg, a film with a resin, a metal foil with a resin, a metal-clad laminate, and a wiring board.
  • the wiring board used for various electronic devices is required to be a wiring board compatible with high frequencies, for example, a millimeter-wave radar board for in-vehicle use.
  • the substrate material for forming the insulating layer of the wiring board used in various electronic devices is required to have a low dielectric constant and a low dielectric loss tangent in order to increase the signal transmission speed and reduce the loss during signal transmission. ..
  • Polyphenylene ether has excellent low dielectric properties such as low dielectric constant and low dielectric loss tangent, and has excellent low dielectric constant and low dielectric loss tangent even in the high frequency band (high frequency region) from MHz band to GHz band. It is known that Therefore, polyphenylene ether is being studied for use as, for example, a molding material for high frequencies. More specifically, it is preferably used as a substrate material for forming an insulating layer of a wiring board provided in an electronic device using a high frequency band.
  • a resin composition containing an elastomer such as a hydrogenated styrene-butadiene-styrene copolymer may be used in order to improve the impact resistance of the insulating layer.
  • an elastomer such as a hydrogenated styrene-butadiene-styrene copolymer
  • the resin composition containing such an elastomer include the resin composition described in Patent Document 1.
  • Patent Document 1 describes a curable resin composition containing a predetermined vinyl compound having a polyphenylene ether skeleton and a high molecular weight substance having a weight average molecular weight of 10,000 or more as an essential component, such as a styrene-based thermoplastic elastomer. There is. According to Patent Document 1, it is disclosed that when a curable film is formed, it has no tackiness, has a low dielectric constant, has a low dielectric loss tangent, and can provide a cured product having excellent heat resistance.
  • the metal-clad laminate and the metal foil with resin used when manufacturing a wiring board or the like include not only an insulating layer but also a metal foil on the insulating layer. Further, the wiring board is provided with wiring not only on the insulating layer but also on the insulating layer. Examples of the wiring include wiring derived from a metal foil provided on the metal-clad laminate and the like.
  • the wiring board With the thinning of the wiring board, the miniaturization of the wiring is required, and the thickness of the wiring becomes thin. Therefore, it is further required that the wiring board does not peel off the wiring from the insulating layer. Therefore, the wiring board is required to have high adhesiveness between the wiring and the insulating layer, and the metal-clad laminate and the metal foil with resin are required to have high adhesiveness between the metal foil and the insulating layer. .. Therefore, it is required that a cured product having high adhesiveness to the metal foil can be obtained as the substrate material for forming the insulating layer of the wiring board.
  • the insulating layer provided on the wiring board has a low dielectric constant. The rate is required more.
  • One aspect of the present invention is a polybutadiene compound having an epoxy group in the molecule, and a polyphenylene ether compound having at least one of a group represented by the following formula (1) and a group represented by the following formula (2) in the molecule. It is a resin composition characterized by containing a styrene-based block copolymer and a curing agent.
  • p represents 0 to 10
  • Z represents an arylene group
  • R 1 to R 3 each independently represent a hydrogen atom or an alkyl group.
  • R 4 represents a hydrogen atom or an alkyl group.
  • FIG. 1 is a schematic cross-sectional view showing an example of a prepreg according to an embodiment of the present invention.
  • FIG. 2 is a schematic cross-sectional view showing an example of a metal-clad laminate according to an embodiment of the present invention.
  • FIG. 3 is a schematic cross-sectional view showing an example of a wiring board according to an embodiment of the present invention.
  • FIG. 4 is a schematic cross-sectional view showing an example of a metal leaf with a resin according to an embodiment of the present invention.
  • FIG. 5 is a schematic cross-sectional view showing an example of a resin-coated film according to an embodiment of the present invention.
  • the resin composition according to the present embodiment has at least one of a polybutadiene compound having an epoxy group in the molecule, a group represented by the following formula (1) and a group represented by the following formula (2) in the molecule. It contains a polyphenylene ether compound, a styrene-based block copolymer, and a curing agent.
  • p represents 0 to 10
  • Z represents an arylene group
  • R 1 to R 3 each independently represent a hydrogen atom or an alkyl group.
  • R 4 represents a hydrogen atom or an alkyl group.
  • the resin composition is obtained by curing the polyphenylene ether compound together with the curing agent, so that even if the polybutadiene compound and the styrene-based block copolymer are contained, the polyphenylene ether has excellent low dielectric properties. It is considered that a cured product that maintains the above can be obtained. Further, since the resin composition contains a polybutadiene compound having an epoxy group in the molecule together with the styrene-based block copolymer, a cured product having high adhesiveness to the metal foil can be obtained.
  • the resin composition is a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Further, for example, when a metal-clad laminate is manufactured using the resin composition, a metal-clad laminate having an insulating layer having low dielectric properties and high adhesiveness to a metal foil can be obtained. Further, when the wiring board is manufactured, a wiring board having an insulating layer having low dielectric properties and high adhesiveness to the wiring can be obtained. Such a wiring board can be obtained by subjecting the metal foil to fine circuit processing, for example, a semi-additive method (SAP: Semi Adaptive Process), a modified semi-additive method (MSAP: Modified Semi Adaptive Process), or the like.
  • SAP Semi Adaptive Process
  • MSAP Modified Semi Adaptive Process
  • wiring such as metal foil-derived wiring is difficult to peel off from the insulating layer.
  • a low-roughness and thin metal foil is used.
  • the wiring such as the wiring derived from the metal leaf tends to be easily peeled off from the insulating layer, but when the resin composition according to the present embodiment is used, even in such a case, the metal Wiring such as foil-derived wiring is difficult to peel off from the insulating layer.
  • the polybutadiene compound is not particularly limited as long as it is a polybutadiene compound having an epoxy group in the molecule.
  • the polybutadiene compound include epoxidized polybutadiene, that is, a compound in which an epoxy group is introduced into the molecule by epoxidizing at least a part of carbon-carbon double bonds contained in the polybutadiene, and polybutadiene. Examples thereof include compounds in which both ends are glycidyl etherified.
  • one oxygen atom is added to the carbon-carbon double bond contained in polybutadiene (non-epoxidized polybutadiene) by an epoxidizing agent to form a three-membered ring epoxy group. And so on.
  • a compound in which both ends of polybutadiene are glycidyl etherified can be obtained by adding epichlorohydrin to polybutadiene having hydroxyl groups at both ends.
  • the polybutadiene (non-epoxy polybutadiene) has a carbon-carbon double bond configuration of any of cis-1,4, trans-1,4, cis-1,2, and trans-1,2. You may. Moreover, these ratios are not particularly limited.
  • the epoxidizing agent is not particularly limited as long as it can epoxidize the carbon-carbon double bond contained in polybutadiene.
  • examples of the epoxidizing agent include peracetic acids such as peracetic acid, performic acid, perbenzoic acid, trifluoroperacetic acid, and perpropionic acid, and organic hydroperoxides such as t-butyl hydroperoxide and cumene hydroperoxide. And hydrogen peroxide and the like.
  • the polybutadiene compound preferably has an oxylan oxygen concentration of 1 to 10% by mass, and more preferably 5 to 9% by mass. If the concentration of the oxylan oxygen is too low, the effect of adding the polybutadiene compound and the effect of enhancing the adhesiveness of the cured product of the resin composition to the metal leaf tend not to be sufficiently obtained. Further, if the concentration of the oxylan oxygen is too high, the number of the epoxy groups tends to be too large, and the low dielectric property tends to be deteriorated. By using the polybutadiene compound in which the concentration of oxylane oxygen is within the above range, when cured, a resin composition having low dielectric properties and high adhesiveness to a metal foil can be obtained.
  • the concentration of oxylan oxygen is an index of the content of epoxy groups contained in the polybutadiene compound, and can be measured by, for example, the hydrogen bromide-glacial acetic acid solution method or the like.
  • the polyphenylene ether compound is not particularly limited as long as it is a polyphenylene ether compound having at least one of the group represented by the formula (1) and the group represented by the formula (2) in the molecule.
  • Specific examples of the polyphenylene ether compound include a polyphenylene ether compound having at least one of a group represented by the formula (1) and a group represented by the formula (2) at the molecular end. More specific examples of the polyphenylene ether compound include a modified polyphenylene ether compound terminally modified by at least one of the group represented by the formula (1) and the group represented by the formula (2). ..
  • p represents 0 to 10.
  • Z represents an arylene group.
  • R 1 to R 3 are independent of each other. That is, R 1 to R 3 may be the same group or different groups, respectively. Further, R 1 to R 3 represent a hydrogen atom or an alkyl group.
  • This allylene group is not particularly limited.
  • the arylene group include a monocyclic aromatic group such as a phenylene group and a polycyclic aromatic group in which the aromatic is not a monocyclic ring but a polycyclic aromatic group such as a naphthalene ring.
  • the arylene group also includes a derivative in which the hydrogen atom bonded to the aromatic ring is replaced with a functional group such as an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. ..
  • the alkyl group is not particularly limited, and for example, an alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 10 carbon atoms is more preferable. Specific examples thereof include a methyl group, an ethyl group, a propyl group, a hexyl group, a decyl group and the like.
  • R 4 represents a hydrogen atom or an alkyl group.
  • the alkyl group is not particularly limited, and for example, an alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 10 carbon atoms is more preferable. Specific examples thereof include a methyl group, an ethyl group, a propyl group, a hexyl group, a decyl group and the like.
  • Preferred specific examples of the group represented by the formula (1) include a vinylbenzyl group (ethenylbenzyl group) represented by the following formula (3), a vinylphenyl group and the like.
  • Examples of the vinylbenzyl group include an o-ethenylbenzyl group, a p-ethenylbenzyl group and an m-ethenylbenzyl group.
  • Examples of the group represented by the formula (2) include an acryloyl group and a methacryloyl group.
  • the polyphenylene ether compound has at least one of the group represented by the formula (1) and the group represented by the formula (2) in the molecule, and has one kind of these groups. It may have two or more kinds.
  • the polyphenylene ether compound may have, for example, any of an o-ethenylbenzyl group, a p-ethenylbenzyl group and an m-ethenylbenzyl group, and has two or three of these. It may be.
  • the polyphenylene ether compound has a polyphenylene ether chain in the molecule, and for example, it is preferable that the polyphenylene ether compound has a repeating unit represented by the following formula (4) in the molecule.
  • t represents 1 to 50.
  • R 5 to R 8 are independent of each other. That is, R 5 to R 8 may be the same group or different groups, respectively.
  • R 5 to R 8 represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. Of these, a hydrogen atom and an alkyl group are preferable.
  • R 5 to R 8 Specific examples of the functional groups listed in R 5 to R 8 include the following.
  • the alkyl group is not particularly limited, but for example, an alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 10 carbon atoms is more preferable. Specific examples thereof include a methyl group, an ethyl group, a propyl group, a hexyl group, a decyl group and the like.
  • the alkenyl group is not particularly limited, but for example, an alkenyl group having 2 to 18 carbon atoms is preferable, and an alkenyl group having 2 to 10 carbon atoms is more preferable. Specific examples thereof include a vinyl group, an allyl group, a 3-butenyl group and the like.
  • the alkynyl group is not particularly limited, but for example, an alkynyl group having 2 to 18 carbon atoms is preferable, and an alkynyl group having 2 to 10 carbon atoms is more preferable. Specific examples thereof include an ethynyl group and a propa-2-in-1-yl group (propargyl group).
  • the alkylcarbonyl group is not particularly limited as long as it is a carbonyl group substituted with an alkyl group, but for example, an alkylcarbonyl group having 2 to 18 carbon atoms is preferable, and an alkylcarbonyl group having 2 to 10 carbon atoms is more preferable. Specific examples thereof include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a hexanoyl group, an octanoyl group, a cyclohexylcarbonyl group and the like.
  • the alkenylcarbonyl group is not particularly limited as long as it is a carbonyl group substituted with an alkenyl group, but for example, an alkenylcarbonyl group having 3 to 18 carbon atoms is preferable, and an alkenylcarbonyl group having 3 to 10 carbon atoms is more preferable. Specific examples thereof include an acryloyl group, a methacryloyl group, and a crotonoyl group.
  • the alkynylcarbonyl group is not particularly limited as long as it is a carbonyl group substituted with an alkynyl group, but for example, an alkynylcarbonyl group having 3 to 18 carbon atoms is preferable, and an alkynylcarbonyl group having 3 to 10 carbon atoms is more preferable. Specifically, for example, a propioloyl group and the like can be mentioned.
  • the weight average molecular weight (Mw) of the polyphenylene ether compound is not particularly limited. Specifically, it is preferably 500 to 5000, more preferably 800 to 4000, and even more preferably 1000 to 3000.
  • the weight average molecular weight may be measured by a general molecular weight measuring method, and specific examples thereof include values measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • t is a numerical value such that the weight average molecular weight of the polyphenylene ether compound is within such a range. It is preferable to have. Specifically, t is preferably 1 to 50.
  • the polyphenylene ether compound When the weight average molecular weight of the polyphenylene ether compound is within such a range, the polyphenylene ether has excellent low-dielectric properties, and not only the heat resistance of the cured product is excellent, but also the moldability is excellent. Become. This is considered to be due to the following. When the weight average molecular weight of ordinary polyphenylene ether is within such a range, the heat resistance of the cured product tends to decrease because the molecular weight is relatively low. In this respect, since the polyphenylene ether compound according to the present embodiment has at least one of the group represented by the formula (1) and the group represented by the formula (2) in the molecule, the heat resistance of the cured product is high. It is considered that a sufficiently high product can be obtained.
  • the weight average molecular weight of the polyphenylene ether compound is within such a range, it is considered to be excellent in moldability because it has a relatively low molecular weight. Therefore, it is considered that such a polyphenylene ether compound is not only excellent in heat resistance of the cured product but also excellent in moldability.
  • the average number (number of terminal functional groups) of at least one (substituent) of the group represented by the formula (1) and the group represented by the formula (2) per molecule of the polyphenylene ether compound. ) Is not particularly limited. Specifically, the number of terminal functional groups is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.5 to 3. If the number of terminal functional groups is too small, it tends to be difficult to obtain a cured product having sufficient heat resistance. Further, if the number of terminal functional groups is too large, the reactivity becomes too high, and there is a possibility that problems such as a decrease in the storage stability of the resin composition and a decrease in the fluidity of the resin composition may occur. .. That is, when such a polyphenylene ether compound is used, molding defects such as voids generated during multi-layer molding occur due to insufficient fluidity, etc., and it is difficult to obtain a highly reliable printed wiring board. There was a risk of problems.
  • the number of terminal functional groups of the polyphenylene ether compound includes a numerical value representing the average value of the substituents per molecule of all the polyphenylene ether compounds present in 1 mol of the polyphenylene ether compound.
  • the number of terminal functional groups is determined, for example, by measuring the number of hydroxyl groups remaining in the obtained polyphenylene ether compound and calculating the amount of decrease from the number of hydroxyl groups of the polyphenylene ether before having the substituent (before modification). , Can be measured.
  • the decrease from the number of hydroxyl groups of the polyphenylene ether before this modification is the number of terminal functional groups.
  • the method for measuring the number of hydroxyl groups remaining in the polyphenylene ether compound is to add a quaternary ammonium salt (tetraethylammonium hydroxide) that associates with the hydroxyl groups to the solution of the polyphenylene ether compound and measure the UV absorbance of the mixed solution. Can be obtained by.
  • a quaternary ammonium salt tetraethylammonium hydroxide
  • the intrinsic viscosity of the polyphenylene ether compound is not particularly limited. Specifically, it is preferably 0.03 to 0.12 dl / g, more preferably 0.04 to 0.11 dl / g, and further preferably 0.06 to 0.095 dl / g. preferable. If this intrinsic viscosity is too low, the molecular weight tends to be low, and it tends to be difficult to obtain low dielectric constants such as low dielectric constant and low dielectric loss tangent. Further, if the intrinsic viscosity is too high, the viscosity is high, sufficient fluidity cannot be obtained, and the moldability of the cured product tends to decrease. Therefore, if the intrinsic viscosity of the polyphenylene ether compound is within the above range, excellent heat resistance and moldability of the cured product can be realized.
  • the intrinsic viscosity here is the intrinsic viscosity measured in methylene chloride at 25 ° C., more specifically, for example, a 0.18 g / 45 ml methylene chloride solution (liquid temperature 25 ° C.) is used in a viscometer. It is a value measured in. Examples of this viscometer include AVS500 Visco System manufactured by Schott.
  • polyphenylene ether compound examples include a polyphenylene ether compound represented by the following formula (5), a polyphenylene ether compound represented by the following formula (6), and the like. Further, as the polyphenylene ether compound, these polyphenylene ether compounds may be used alone, or these two types of polyphenylene ether compounds may be used in combination.
  • R 9 to R 16 and R 17 to R 24 are independently hydrogen atoms, alkyl groups, alkenyl groups, alkynyl groups, formyl groups, alkylcarbonyl groups, and alkenylcarbonyls. Indicates a group or an alkynylcarbonyl group.
  • X 1 and X 2 independently represent a group represented by the above formula (1) or a group represented by the above formula (2).
  • a and B represent repeating units represented by the following formulas (7) and (8), respectively.
  • Y represents a linear, branched, or cyclic hydrocarbon having 20 or less carbon atoms.
  • R 25 to R 28 and R 29 to R 32 independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group.
  • the polyphenylene ether compound represented by the formula (5) and the polyphenylene ether compound represented by the formula (6) are not particularly limited as long as they satisfy the above constitution.
  • R 9 to R 16 and R 17 to R 24 are independent of each other as described above. That is, R 9 to R 16 and R 17 to R 24 may be the same group or different groups, respectively.
  • R 9 to R 16 and R 17 to R 24 represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. Of these, a hydrogen atom and an alkyl group are preferable.
  • m and n preferably represent 0 to 20, respectively, as described above. Further, it is preferable that m and n represent numerical values in which the total value of m and n is 1 to 30. Therefore, it is more preferable that m indicates 0 to 20, n indicates 0 to 20, and the total of m and n indicates 1 to 30. Further, R 25 to R 28 and R 29 to R 32 are independent of each other. That is, R 25 to R 28 and R 29 to R 32 may be the same group or different groups, respectively.
  • R 25 to R 28 and R 29 to R 32 represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. Of these, a hydrogen atom and an alkyl group are preferable.
  • R 9 to R 32 are the same as R 5 to R 8 in the above formula (4).
  • Y is a linear, branched, or cyclic hydrocarbon having 20 or less carbon atoms, as described above.
  • Examples of Y include groups represented by the following formula (9).
  • R 33 and R 34 each independently represent a hydrogen atom or an alkyl group.
  • the alkyl group include a methyl group and the like.
  • the group represented by the formula (9) include a methylene group, a methylmethylene group, a dimethylmethylene group and the like, and among these, a dimethylmethylene group is preferable.
  • X 1 and X 2 are independently a group represented by the above formula (1) or a group represented by the above formula (2).
  • X 1 and X 2 may be the same group or different groups. May be.
  • polyphenylene ether compound represented by the formula (5) for example, a polyphenylene ether compound represented by the following formula (10) and the like can be mentioned.
  • polyphenylene ether compound represented by the formula (6) include, for example, a polyphenylene ether compound represented by the following formula (11), a polyphenylene ether compound represented by the following formula (12), and the like. Can be mentioned.
  • m and n are the same as m and n in the above formula (7) and the above formula (8).
  • the formula (10) and the formula (11), R 1 ⁇ R 3, p and Z are the same as R 1 ⁇ R 3, p and Z in the formula (1).
  • Y is the same as Y in the above formula (6).
  • R 4 is the same as R 1 in the above formula (2).
  • the method for synthesizing the polyphenylene ether compound used in the present embodiment is as long as the polyphenylene ether compound having at least one of the group represented by the formula (1) and the group represented by the formula (2) in the molecule can be synthesized.
  • the polyphenylene ether compound having at least one of the group represented by the formula (1) and the group represented by the formula (2) in the molecule can be synthesized.
  • a method for synthesizing a modified polyphenylene ether compound terminal-modified by at least one of the group represented by the formula (1) and the group represented by the formula (2) will be described. Specifically, as this method, a compound in which a halogen atom is bonded to at least one of a group represented by the formula (1) and a group represented by the formula (2) is reacted with polyphenylene ether.
  • the method and the like can be mentioned.
  • halogen atom examples include a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom, and among these, a chlorine atom is preferable. More specifically, as a compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) is bonded to a halogen atom, o-chloromethylstyrene, p- Examples thereof include chloromethylstyrene and m-chloromethylstyrene.
  • the compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) is bonded to a halogen atom may be used alone or in combination of two or more. You may. For example, o-chloromethylstyrene, p-chloromethylstyrene, and m-chloromethylstyrene may be used alone, or two or a combination of three may be used.
  • the polyphenylene ether as a raw material is not particularly limited as long as it can finally synthesize a predetermined modified polyphenylene ether compound.
  • the bifunctional phenol is a phenol compound having two phenolic hydroxyl groups in the molecule, and examples thereof include tetramethylbisphenol A and the like.
  • the trifunctional phenol is a phenol compound having three phenolic hydroxyl groups in the molecule.
  • Examples of the method for synthesizing the modified polyphenylene ether compound include the methods described above. Specifically, the above-mentioned polyphenylene ether and a compound in which at least one of the group represented by the above formula (1) and the group represented by the above formula (2) and a halogen atom are bonded are used as a solvent. Dissolve and stir. By doing so, the polyphenylene ether reacts with a compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) is bonded to a halogen atom, and the present embodiment The modified polyphenylene ether compound used in the above is obtained.
  • the alkali metal hydroxide functions as a dehydrohalogenating agent, specifically, a dehydrochloric acid agent. That is, the alkali metal hydroxide is a compound in which the phenol group of the polyphenylene ether, at least one of the group represented by the formula (1) and the group represented by the formula (2), and a halogen atom are bonded. By desorbing hydrogen halide from the group, at least the group represented by the above formula (1) and the group represented by the above formula (2) are replaced with the hydrogen atom of the phenol group of the polyphenylene ether. One is thought to bind to the oxygen atom of the phenol group.
  • the alkali metal hydroxide is not particularly limited as long as it can act as a dehalogenating agent, and examples thereof include sodium hydroxide. Further, the alkali metal hydroxide is usually used in the state of an aqueous solution, and specifically, it is used as an aqueous solution of sodium hydroxide.
  • Reaction conditions such as reaction time and reaction temperature also differ depending on the compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) is bonded to a halogen atom, and the like.
  • the condition is not particularly limited as long as the reaction as described above proceeds favorably.
  • the reaction temperature is preferably room temperature to 100 ° C., more preferably 30 to 100 ° C.
  • the reaction time is preferably 0.5 to 20 hours, more preferably 0.5 to 10 hours.
  • the solvent used in the reaction can dissolve polyphenylene ether and a compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) and a halogen atom are bonded. , Especially as long as it does not inhibit the reaction between the polyphenylene ether and the compound in which at least one of the group represented by the formula (1) and the group represented by the formula (2) is bonded to a halogen atom. Not limited. Specific examples thereof include toluene and the like.
  • the above reaction is carried out in the presence of not only the alkali metal hydroxide but also the phase transfer catalyst. That is, the above reaction is preferably carried out in the presence of an alkali metal hydroxide and a phase transfer catalyst. By doing so, it is considered that the above reaction proceeds more preferably. This is considered to be due to the following.
  • the phase transfer catalyst has a function of taking in alkali metal hydroxide and is soluble in both a polar solvent phase such as water and a non-polar solvent phase such as an organic solvent, and is soluble between these phases. It is considered that it is a catalyst capable of moving.
  • aqueous sodium hydroxide solution when an aqueous sodium hydroxide solution is used as the alkali metal hydroxide and an organic solvent such as toluene, which is incompatible with water, is used as the solvent, the aqueous sodium hydroxide solution is subjected to the reaction. It is considered that the solvent and the aqueous sodium hydroxide solution are separated even when the solution is added dropwise to the solvent, and the sodium hydroxide is unlikely to be transferred to the solvent. In that case, it is considered that the sodium hydroxide aqueous solution added as the alkali metal hydroxide is less likely to contribute to the reaction promotion.
  • an organic solvent such as toluene, which is incompatible with water
  • the reaction when the reaction is carried out in the presence of the alkali metal hydroxide and the phase transfer catalyst, the alkali metal hydroxide is transferred to the solvent in a state of being incorporated into the phase transfer catalyst, and the sodium hydroxide aqueous solution reacts. It is thought that it will be easier to contribute to promotion. Therefore, it is considered that the above reaction proceeds more preferably when the reaction is carried out in the presence of an alkali metal hydroxide and a phase transfer catalyst.
  • phase transfer catalyst is not particularly limited, and examples thereof include quaternary ammonium salts such as tetra-n-butylammonium bromide.
  • the resin composition used in the present embodiment preferably contains the modified polyphenylene ether compound obtained as described above as the polyphenylene ether compound.
  • the styrene-based block copolymer may be a styrene-based block copolymer that can be used as a resin contained in a resin composition or the like used for forming an insulating layer provided on a metal-clad laminate, a wiring board, or the like.
  • a resin composition or the like used for forming an insulating layer provided on a metal-clad laminate, a wiring board, or the like.
  • styrene-based block copolymer examples include methylstyrene (ethylene / butylene) methylstyrene copolymer, methylstyrene (ethylene-ethylene / propylene) methylstyrene copolymer, styreneisoprene copolymer, and styreneisoprenestyrene.
  • Polymer Polymer, styrene (ethylene / butylene) styrene copolymer, styrene (ethylene-ethylene / propylene) styrene copolymer, styrene butadiene styrene copolymer, styrene (butadiene / butylene) styrene copolymer, and styrene isobutylene styrene Examples thereof include copolymers, and these may be hydrogenated products.
  • the styrene-based block copolymers include styrene-butadiene-styrene copolymers, styrene (ethylene / butylene) styrene copolymers, methylstyrene (ethylene / butylene) methylstyrene copolymers, and hydrogenated products thereof. preferable. Further, the styrene-based block copolymer may be used alone or in combination of two or more.
  • a resin composition that becomes a cured product having high adhesiveness to a metal foil can be obtained when cured.
  • the styrene-based block copolymer preferably has a weight average molecular weight of 10,000 to 300,000, more preferably 50,000 to 250,000, and even more preferably 60,000 to 200,000. If the molecular weight of the styrene-based block copolymer is too low, the glass transition temperature of the cured product tends to decrease, and the heat resistance of the cured product tends to decrease. Further, if the molecular weight of the styrene-based block copolymer is too high, the viscosity of the varnish of the resin composition and the melt viscosity at the time of heat molding may become too high.
  • the weight average molecular weight of the styrene-based block copolymer is within the above range, the glass transition temperature and heat resistance are superior, and the adhesiveness between the metal foil and the insulating layer is lowered by heating and moisture absorption. It can be suppressed.
  • the curing agent is a curing agent capable of reacting with the polyphenylene ether compound to cure the resin composition containing the polyphenylene ether compound. Further, the curing agent is not particularly limited as long as it is a curing agent capable of curing the resin composition containing the polyphenylene ether compound.
  • the curing agent include styrene, styrene derivatives, compounds having an acryloyl group in the molecule, compounds having a methacryloyl group in the molecule, compounds having a vinyl group in the molecule, compounds having an allyl group in the molecule, and molecules. Examples thereof include a compound having an acenaftylene structure, a compound having a maleimide group in the molecule, and an isocyanurate compound having an isocyanurate group in the molecule.
  • styrene derivative examples include bromostyrene and dibromostyrene.
  • the compound having an acryloyl group in the molecule is an acrylate compound.
  • the acrylate compound include a monofunctional acrylate compound having one acryloyl group in the molecule and a polyfunctional acrylate compound having two or more acryloyl groups in the molecule.
  • the monofunctional acrylate compound include methyl acrylate, ethyl acrylate, propyl acrylate, and butyl acrylate.
  • Examples of the polyfunctional acrylate compound include diacrylate compounds such as tricyclodecanedimethanol diacrylate.
  • the compound having a methacryloyl group in the molecule is a methacrylate compound.
  • the methacrylate compound include a monofunctional methacrylate compound having one methacryloyl group in the molecule and a polyfunctional methacrylate compound having two or more methacryloyl groups in the molecule.
  • the monofunctional methacrylate compound include methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate and the like.
  • the polyfunctional methacrylate compound include a dimethacrylate compound such as tricyclodecanedimethanol dimethacrylate and a trimethacrylate compound such as trimethylolpropane trimethacrylate.
  • the compound having a vinyl group in the molecule is a vinyl compound.
  • the vinyl compound include a monofunctional vinyl compound (monovinyl compound) having one vinyl group in the molecule and a polyfunctional vinyl compound having two or more vinyl groups in the molecule.
  • the polyfunctional vinyl compound include divinylbenzene and polybutadiene.
  • the compound having an allyl group in the molecule is an allyl compound.
  • the allyl compound include a monofunctional allyl compound having one allyl group in the molecule and a polyfunctional allyl compound having two or more allyl groups in the molecule.
  • the polyfunctional allyl compound include triallyl isocyanurate compounds such as triallyl isocyanurate (TAIC), diallyl bisphenol compounds, and diallyl phthalate (DAP).
  • the compound having an acenaphthylene structure in the molecule is an acenaphthylene compound.
  • the acenaphthylene compound include acenaphthylene, alkylacenaphthylenes, halogenated acenaphthylenes, and phenylacenaphthylenes.
  • the alkyl acenaphthylenes include 1-methylacenaftylene, 3-methylacenaftylene, 4-methylacenaftylene, 5-methylacenaftylene, 1-ethylacenaftylene, and 3-ethylacena.
  • Examples thereof include phthalene, 4-ethylacenaftylene, 5-ethylacenaftylene and the like.
  • Examples of the halogenated asenaftylenes include 1-chloroacenaftylene, 3-chloroacenaftylene, 4-chloroacenaftylene, 5-chloroacenaftylene, 1-bromoacenaftylene, and 3-bromoacenafti. Lene, 4-bromoacenaftylene, 5-bromoacenaftylene and the like can be mentioned.
  • phenylacenaftylenes examples include 1-phenylacenaftylene, 3-phenylacenaftylene, 4-phenylacenaftylene, 5-phenylacenaftylene and the like.
  • the acenaphthylene compound may be a monofunctional acenaphthylene compound having one acenaphthylene structure in the molecule as described above, or a polyfunctional acenaphthylene compound having two or more acenaphthylene structures in the molecule. ..
  • the compound having a maleimide group in the molecule is a maleimide compound.
  • the maleimide compound include a monofunctional maleimide compound having one maleimide group in the molecule, a polyfunctional maleimide compound having two or more maleimide groups in the molecule, and a modified maleimide compound.
  • the modified maleimide compound include a modified maleimide compound in which a part of the molecule is modified with an amine compound, a modified maleimide compound in which a part of the molecule is modified with a silicone compound, and a part of the molecule of an amine compound. And modified maleimide compounds modified with silicone compounds.
  • the compound having an isocyanurate group in the molecule is an isocyanurate compound.
  • the isocyanurate compound include compounds having an alkenyl group in the molecule (alkenyl isocyanurate compound), and examples thereof include trialkenyl isocyanurate compounds such as triallyl isocyanurate (TAIC).
  • the curing agent preferably contains, for example, an allyl compound having an allyl group in the molecule.
  • an allyl compound having an allyl group in the molecule is preferable, and triallyl isocyanurate (TAIC) is more preferable.
  • the curing agent may be used alone or in combination of two or more.
  • the weight average molecular weight of the curing agent is not particularly limited, and is, for example, preferably 100 to 5000, more preferably 100 to 4000, and even more preferably 100 to 3000. If the weight average molecular weight of the curing agent is too low, the curing agent may easily volatilize from the compounding component system of the resin composition. Further, if the weight average molecular weight of the curing agent is too high, the viscosity of the varnish of the resin composition and the melt viscosity at the time of heat molding may become too high. Therefore, when the weight average molecular weight of the curing agent is within such a range, a resin composition having more excellent heat resistance of the cured product can be obtained.
  • the resin composition containing the polyphenylene ether compound can be suitably cured by the reaction with the polyphenylene ether compound.
  • the weight average molecular weight may be measured by a general molecular weight measuring method, and specific examples thereof include values measured by gel permeation chromatography (GPC).
  • the average number of functional groups of the curing agent that contributes to the reaction with the polyphenylene ether compound per molecule of the curing agent (number of functional groups) varies depending on the weight average molecular weight of the curing agent, and is, for example, 1 to 20.
  • the number is preferably 2, and more preferably 2 to 18. If the number of functional groups is too small, it tends to be difficult to obtain a cured product having sufficient heat resistance. On the other hand, if the number of functional groups is too large, the reactivity becomes too high, and there is a possibility that problems such as a decrease in the storage stability of the resin composition and a decrease in the fluidity of the resin composition may occur.
  • the content of the polybutadiene compound is preferably 5 to 40 parts by mass, preferably 5 to 25 parts by mass, based on 100 parts by mass of the total of the polybutadiene compound, the polyphenylene ether compound, and the curing agent. preferable.
  • the content of the polybutadiene compound is preferably 3 to 20 parts by mass with respect to a total of 100 parts by mass of the polybutadiene compound, the polyphenylene ether compound, the styrene block copolymer, and the curing agent. It is preferably 5 to 17.5 parts by mass.
  • the content of the polyphenylene ether compound may be 10 to 70 parts by mass with respect to 100 parts by mass in total of the polybutadiene compound, the polyphenylene ether compound, the styrene block copolymer, and the curing agent. It is preferably 20 to 50 parts by mass.
  • the content of the styrene-based block copolymer is 5 to 60 parts by mass with respect to 100 parts by mass of the total of the polybutadiene compound, the polyphenylene ether compound, the styrene-based block copolymer, and the curing agent. It is preferably 10 to 50 parts by mass.
  • the content of the curing agent is preferably 3 to 30 parts by mass with respect to 100 parts by mass in total of the polybutadiene compound, the polyphenylene ether compound, the styrene-based block copolymer, and the curing agent. It is preferably 5 to 20 parts by mass.
  • the contents of the polybutadiene compound, the polyphenylene ether compound, the styrene-based block copolymer, and the curing agent are within the above ranges, when cured, the metal foil maintains excellent low dielectric properties. A resin composition that becomes a cured product having higher adhesiveness to and from can be obtained.
  • the resin composition according to the present embodiment contains components other than the polybutadiene compound, the polyphenylene ether compound, the styrene block copolymer, and the curing agent, if necessary, as long as the effects of the present invention are not impaired. Other components) may be contained. Other components contained in the resin composition according to the present embodiment include, for example, a silane coupling agent, a flame retardant, an initiator, a curing accelerator, an antifoaming agent, an antioxidant, a polymerization inhibitor, and a polymerization retarder. , Dispersants, leveling agents, heat stabilizers, antistatic agents, UV absorbers, dyes and pigments, lubricants, fillers and other additives may be further included. In addition to the polyphenylene ether compound, the resin composition may contain a thermosetting resin such as an epoxy resin, an unsaturated polyester resin, and a thermosetting polyimide resin.
  • a thermosetting resin such as an epoxy resin, an unsaturated polyester resin, and a thermo
  • the resin composition according to the present embodiment may contain a flame retardant.
  • a flame retardant By containing a flame retardant, the flame retardancy of the cured product of the resin composition can be enhanced.
  • the flame retardant is not particularly limited. Specifically, in the field of using halogen-based flame retardants such as brominated flame retardants, for example, ethylenedipentabromobenzene, ethylenebistetrabromoimide, decabromodiphenyloxide, and tetradecabromo having a melting point of 300 ° C. or higher are used. Diphenoxybenzene is preferred.
  • a halogen-based flame retardant By using a halogen-based flame retardant, it is considered that desorption of halogen at high temperature can be suppressed and deterioration of heat resistance can be suppressed. Further, in the field where halogen-free is required, a phosphoric acid ester flame retardant, a phosphazene flame retardant, a bisdiphenylphosphine oxide flame retardant, and a phosphinate flame retardant can be mentioned. Specific examples of the phosphoric acid ester flame retardant include condensed phosphoric acid ester of dixylenyl phosphate. Specific examples of the phosphazene-based flame retardant include phenoxyphosphazene.
  • the bisdiphenylphosphine oxide-based flame retardant include xylylene bisdiphenylphosphine oxide.
  • Specific examples of the phosphinate-based flame retardant include a phosphinic acid metal salt of a dialkylphosphinic acid aluminum salt.
  • each of the illustrated flame retardants may be used alone, or two or more kinds may be used in combination.
  • the resin composition according to the present embodiment may contain a silane coupling agent.
  • the silane coupling agent may be contained in the resin composition, or may be contained as a silane coupling agent which has been surface-treated in advance in the inorganic filler contained in the resin composition.
  • the silane coupling agent is preferably contained as a silane coupling agent that has been surface-treated in the inorganic filler in advance, and is contained as a silane coupling agent that has been surface-treated in the inorganic filler in this way.
  • the resin composition also contains a silane coupling agent.
  • the prepreg may be contained as a silane coupling agent that has been surface-treated on the fibrous base material in advance.
  • silane coupling agent examples include a silane coupling agent having at least one functional group selected from the group consisting of a vinyl group, a styryl group, a methacryloyl group, an acryloyl group, and a phenylamino group. That is, this silane coupling agent has at least one of a vinyl group, a styryl group, a methacryloyl group, an acryloyl group, and a phenylamino group as a reactive functional group, and further contains a methoxy group, an ethoxy group, and the like. Examples thereof include compounds having a hydrolyzable group.
  • silane coupling agent having a vinyl group examples include vinyltriethoxysilane and vinyltrimethoxysilane.
  • silane coupling agent having a styryl group examples include p-styryltrimethoxysilane and p-styryltriethoxysilane.
  • silane coupling agent examples include those having a methacryloyl group, such as 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-methacryloxypropylmethyl.
  • Examples thereof include diethoxysilane and 3-methacryloxypropyl ethyldiethoxysilane.
  • Examples of the silane coupling agent having an acryloyl group include 3-acryloxypropyltrimethoxysilane and 3-acryloxypropyltriethoxysilane.
  • Examples of the silane coupling agent having a phenylamino group include N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane.
  • the resin composition according to the present embodiment may contain an initiator (reaction initiator). Even if the resin composition does not contain a reaction initiator, the curing reaction can proceed. However, depending on the process conditions, it may be difficult to raise the temperature until curing progresses, so a reaction initiator may be added.
  • the reaction initiator is not particularly limited as long as it can accelerate the curing reaction between the polyphenylene ether compound and the curing agent. Specifically, for example, ⁇ , ⁇ '-bis (t-butylperoxy-m-isopropyl) benzene, 2,5-dimethyl-2,5-di (t-butylperoxy) -3-hexine, excess.
  • Benzoyl Oxide 3,3', 5,5'-Tetramethyl-1,4-diphenoquinone, Chloranyl, 2,4,6-Tri-t-Butylphenoxyl, t-Butylperoxyisopropyl Monocarbonate, Azobisisobuty
  • oxidizing agents such as benzene.
  • a carboxylic acid metal salt or the like can be used in combination. By doing so, the curing reaction can be further promoted.
  • ⁇ , ⁇ '-bis (t-butylperoxy-m-isopropyl) benzene is preferably used.
  • ⁇ ⁇ '-bis (t-butylperoxy-m-isopropyl) benzene has a relatively high reaction start temperature, it suppresses the promotion of the curing reaction when curing is not necessary, such as during prepreg drying. It is possible to suppress a decrease in the storage stability of the resin composition. Further, since ⁇ , ⁇ '-bis (t-butylperoxy-m-isopropyl) benzene has low volatility, it does not volatilize during prepreg drying or storage, and has good stability.
  • the reaction initiator may be used alone or in combination of two or more.
  • the resin composition according to the present embodiment may contain a curing accelerator.
  • the curing accelerator is not particularly limited as long as it can accelerate the curing reaction of the resin composition.
  • Specific examples of the curing accelerator include imidazoles and derivatives thereof, organic phosphorus compounds, amines such as secondary amines and tertiary amines, quaternary ammonium salts, and organic boron compounds. And metal soap and the like.
  • Examples of the imidazoles include 2-ethyl-4-methylimidazole, 2-methylimidazole, 2-phenyl-4-methylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole and the like.
  • organophosphorus compound examples include triphenylphosphine, diphenylphosphine, phenylphosphine, tributylphosphine, and trimethylphosphine.
  • organophosphorus compound examples include triphenylphosphine, diphenylphosphine, phenylphosphine, tributylphosphine, and trimethylphosphine.
  • amines examples include dimethylbenzylamine, triethylenediamine, triethanolamine, 1,8-diazabicyclo (5,4,0) undecene-7 (DBU) and the like.
  • DBU 1,8-diazabicyclo
  • quaternary ammonium salt examples include tetrabutylammonium bromide and the like.
  • the organic boron-based compound examples include tetraphenylborone salts such as 2-ethyl-4-methylimidazole and tetraphenylborate, and tetra-substituted phosphonium and tetra-substituted borates such as tetraphenylphosphonium and ethyltriphenylborate.
  • the metal soap refers to a fatty acid metal salt, and may be a linear fatty acid metal salt or a cyclic fatty acid metal salt. Specific examples of the metal soap include a linear aliphatic metal salt having 6 to 10 carbon atoms and a cyclic aliphatic metal salt.
  • linear fatty acids such as stearic acid, lauric acid, ricinoleic acid, and octyl acid
  • cyclic fatty acids such as naphthenic acid, lithium, magnesium, calcium, barium, copper, zinc, and the like.
  • aliphatic metal salts composed of the above metals.
  • zinc octylate and the like can be mentioned.
  • the curing accelerator may be used alone or in combination of two or more.
  • the resin composition according to the present embodiment may contain a filler such as an inorganic filler.
  • a filler such as an inorganic filler.
  • the filler include those added to enhance the heat resistance and flame retardancy of the cured product of the resin composition, and the filler is not particularly limited. Further, by containing a filler, heat resistance, flame retardancy and the like can be further improved.
  • Specific examples of the filler include silica such as spherical silica, metal oxides such as alumina and titanium oxide, and mica, metal hydroxides such as aluminum hydroxide and magnesium hydroxide, talc, aluminum borate, and sulfuric acid. Examples include barium and calcium carbonate.
  • filler silica, mica, and talc are preferable, and spherical silica is more preferable.
  • one type of filler may be used alone, or two or more types may be used in combination.
  • the filler it may be used as it is, or a filler surface-treated with the silane coupling agent may be used.
  • the content (filler content) thereof is preferably 20 to 270% by mass, more preferably 30 to 250% by mass, based on the resin composition.
  • the method for producing the resin composition is not particularly limited, and examples thereof include a method of mixing the polybutadiene compound, the polyphenylene ether compound, and the curing agent so as to have a predetermined content. Specifically, when a varnish-like composition containing an organic solvent is obtained, a method described later and the like can be mentioned.
  • a prepreg, a metal-clad laminate, a wiring board, a metal foil with a resin, and a film with a resin can be obtained as follows.
  • FIG. 1 is a schematic cross-sectional view showing an example of a prepreg 1 according to an embodiment of the present invention.
  • the prepreg 1 includes the resin composition or the semi-cured product 2 of the resin composition, and the fibrous base material 3.
  • the prepreg 1 includes the resin composition or the semi-cured product 2 of the resin composition, and the fibrous base material 3 existing in the resin composition or the semi-cured product 2 of the resin composition.
  • the semi-cured product is a state in which the resin composition is partially cured to the extent that it can be further cured. That is, the semi-cured product is a semi-cured resin composition (B-staged). For example, when the resin composition is heated, the viscosity gradually decreases first, then curing starts, and then curing starts and the viscosity gradually increases. In such a case, the semi-curing state includes a state between the time when the viscosity starts to increase and the time before it is completely cured.
  • the prepreg obtained by using the resin composition according to the present embodiment may include a semi-cured product of the resin composition as described above, or the resin composition which has not been cured. It may be provided with itself. That is, it may be a prepreg comprising a semi-cured product of the resin composition (the resin composition of the B stage) and a fibrous base material, or the resin composition before curing (the resin composition of the A stage). It may be a prepreg including a thing) and a fibrous base material. Further, the resin composition or the semi-cured product of the resin composition may be a dried or heat-dried resin composition.
  • the resin composition 2 When producing a prepreg, the resin composition 2 is often prepared and used in the form of a varnish in order to impregnate the fibrous base material 3 which is a base material for forming the prepreg. That is, the resin composition 2 is usually a resin varnish prepared in the form of a varnish.
  • a varnish-like resin composition (resin varnish) is prepared, for example, as follows.
  • each component that can be dissolved in an organic solvent is put into an organic solvent and dissolved. At this time, heating may be performed if necessary. Then, if necessary, a component that is insoluble in an organic solvent is added and dispersed using a ball mill, a bead mill, a planetary mixer, a roll mill, or the like until a predetermined dispersion state is obtained, thereby forming a varnish-like resin.
  • the composition is prepared.
  • the organic solvent used here is not particularly limited as long as it dissolves the polybutadiene compound, the polyphenylene ether compound, the curing agent and the like and does not inhibit the curing reaction. Specific examples thereof include toluene and methyl ethyl ketone (MEK).
  • the method for producing the prepreg is not particularly limited as long as the prepreg can be produced. Specifically, when producing a prepreg, the resin composition used in the present embodiment described above is often prepared in the form of a varnish as described above and used as a resin varnish.
  • the fibrous base material include glass cloth, aramid cloth, polyester cloth, glass non-woven fabric, aramid non-woven fabric, polyester non-woven fabric, pulp paper, and linter paper.
  • a glass cloth is used, a laminated plate having excellent mechanical strength can be obtained, and a flattened glass cloth is particularly preferable.
  • Specific examples of the flattening process include a method in which a glass cloth is continuously pressed with a press roll at an appropriate pressure to flatten the yarn.
  • the thickness of the generally used fibrous base material is, for example, 0.01 mm or more and 0.3 mm or less.
  • the method for producing the prepreg is not particularly limited as long as the prepreg can be produced.
  • the resin composition according to the present embodiment described above is often prepared in the form of a varnish as described above and used as a resin varnish.
  • Examples of the method for producing the prepreg 1 include a method in which the fibrous base material 3 is impregnated with the resin composition 2, for example, the resin composition 2 prepared in the form of a varnish, and then dried.
  • the resin composition 2 is impregnated into the fibrous base material 3 by dipping, coating or the like. It is also possible to repeat impregnation a plurality of times as needed. Further, at this time, by repeating impregnation using a plurality of resin compositions having different compositions and concentrations, it is possible to finally adjust the desired composition and impregnation amount.
  • the fibrous base material 3 impregnated with the resin composition (resin varnish) 2 is heated under desired heating conditions, for example, 80 ° C. or higher and 180 ° C. or lower for 1 minute or more and 10 minutes or less.
  • desired heating conditions for example, 80 ° C. or higher and 180 ° C. or lower for 1 minute or more and 10 minutes or less.
  • prepreg 1 before curing (A stage) or in a semi-cured state (B stage) is obtained.
  • the organic solvent can be volatilized from the resin varnish to reduce or remove the organic solvent.
  • the resin composition according to the present embodiment is a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Therefore, the prepreg including the resin composition or the semi-cured product of the resin composition is a prepreg that has low dielectric properties and high adhesiveness to the metal foil. Then, this prepreg can suitably manufacture a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring.
  • FIG. 2 is a schematic cross-sectional view showing an example of the metal-clad laminate 11 according to the embodiment of the present invention.
  • the metal-clad laminate 11 is composed of an insulating layer 12 containing a cured product of the prepreg 1 shown in FIG. 1 and a metal foil 13 laminated together with the insulating layer 12. That is, the metal-clad laminate 11 has an insulating layer 12 containing a cured product of the resin composition, and a metal foil 13 provided on the insulating layer 12. Further, the insulating layer 12 may be made of a cured product of the resin composition or may be made of a cured product of the prepreg. Further, the thickness of the metal foil 13 varies depending on the performance and the like required for the finally obtained wiring board, and is not particularly limited.
  • the thickness of the metal foil 13 can be appropriately set according to a desired purpose, and is preferably 0.2 to 70 ⁇ m, for example.
  • Examples of the metal foil 13 include a copper foil and an aluminum foil.
  • the metal foil 13 is a copper foil with a carrier provided with a release layer and a carrier for improving handleability. May be good.
  • the method for manufacturing the metal-clad laminate 11 is not particularly limited as long as the metal-clad laminate 11 can be manufactured. Specifically, a method of manufacturing the metal-clad laminate 11 using the prepreg 1 can be mentioned. In this method, one or a plurality of prepregs 1 are laminated, metal foils 13 such as copper foils are laminated on both upper and lower sides or one side thereof, and the metal foils 13 and the prepregs 1 are heat-press molded and integrated. By doing so, a method of producing a laminated plate 11 covered with double-sided metal leaf or single-sided metal leaf can be mentioned. That is, the metal-clad laminate 11 is obtained by laminating a metal foil 13 on a prepreg 1 and heat-pressing molding.
  • the heating and pressurizing conditions can be appropriately set depending on the thickness of the metal-clad laminate 11 to be manufactured, the type of the composition of the prepreg 1, and the like.
  • the temperature can be 170 to 230 ° C.
  • the pressure can be 2 to 5 MPa
  • the time can be 60 to 150 minutes.
  • the metal-clad laminate may be manufactured without using a prepreg. For example, a method of applying a varnish-like resin composition on a metal foil, forming a layer containing the resin composition on the metal foil, and then heating and pressurizing the metal foil can be mentioned.
  • the thickness of the metal foil is preferably 0.2 to 35 ⁇ m, more preferably 1 to 18 ⁇ m. Even if the metal foil is so thin, when the metal-clad laminate is manufactured using the resin composition according to the present embodiment, the obtained metal-clad laminate contains insulation containing a cured product of the resin composition. The adhesiveness between the layer and the metal foil was sufficiently high.
  • the resin composition according to the present embodiment is a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Therefore, the metal-clad laminate provided with an insulating layer containing a cured product of this resin composition is a metal-clad laminate having an insulating layer having low dielectric properties and high adhesiveness to a metal foil. Then, this metal-clad laminate can suitably manufacture a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring such as wiring derived from metal foil.
  • FIG. 3 is a schematic cross-sectional view showing an example of the wiring board 21 according to the embodiment of the present invention.
  • the wiring board 21 As shown in FIG. 3, the wiring board 21 according to the present embodiment is laminated with the insulating layer 12 used by curing the prepreg 1 shown in FIG. 1 and the insulating layer 12, and the metal foil 13 is partially removed. It is composed of the wiring 14 formed in the above. That is, the wiring board 21 has an insulating layer 12 containing a cured product of the resin composition, and a wiring 14 provided on the insulating layer 12. Further, the insulating layer 12 may be made of a cured product of the resin composition or may be made of a cured product of the prepreg.
  • the method for manufacturing the wiring board 21 is not particularly limited as long as the wiring board 21 can be manufactured. Specifically, a method of manufacturing the wiring board 21 using the prepreg 1 and the like can be mentioned. As this method, for example, wiring is provided as a circuit on the surface of the insulating layer 12 by forming wiring by etching the metal foil 13 on the surface of the metal-clad laminate 11 produced as described above. Examples thereof include a method of manufacturing the wiring board 21. That is, the wiring board 21 is obtained by forming a circuit by partially removing the metal foil 13 on the surface of the metal-clad laminate 11.
  • examples of the method for forming a circuit include a semi-additive method (SAP: Semi Adaptive Process) and a modified semi-additive method (MSAP: Modified Semi Adaptive Process).
  • the wiring board 21 has an insulating layer 12 having a high glass transition temperature, excellent flame retardancy, low water absorption, and sufficiently suppressing an increase in dielectric constant and dielectric loss tangent due to water absorption even after water absorption. ..
  • Such a wiring board is a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring.
  • FIG. 4 is a schematic cross-sectional view showing an example of the resin-attached metal leaf 31 according to the present embodiment.
  • the resin-attached metal foil 31 includes a resin layer 32 containing the resin composition or a semi-cured product of the resin composition, and the metal foil 13.
  • the resin-attached metal foil 31 has the metal foil 13 on the surface of the resin layer 32. That is, the resin-attached metal foil 31 includes the resin layer 32 and the metal foil 13 laminated together with the resin layer 32. Further, the metal leaf 31 with resin may be provided with another layer between the resin layer 32 and the metal leaf 13.
  • the resin layer 32 may include the semi-cured product of the resin composition as described above, or may contain the uncured resin composition. .. That is, the resin-attached metal foil 31 may include a resin layer containing a semi-cured product of the resin composition (the resin composition of the B stage) and a metal foil, or the resin before curing. It may be a metal foil with a resin including a resin layer containing the composition (the resin composition of the A stage) and the metal foil. Further, the resin layer may contain the resin composition or a semi-cured product of the resin composition, and may or may not contain a fibrous base material. Further, the resin composition or the semi-cured product of the resin composition may be a dried or heat-dried resin composition. Further, as the fibrous base material, the same one as that of the prepreg fibrous base material can be used.
  • the metal foil used for the metal-clad laminate can be used without limitation.
  • the metal foil include copper foil and aluminum foil.
  • the resin-attached metal foil 31 and the resin-attached film 41 may be provided with a cover fill or the like, if necessary.
  • a cover fill or the like By providing the cover film, it is possible to prevent foreign matter from being mixed.
  • the cover film is not particularly limited, and examples thereof include a polyolefin film, a polyester film, a polymethylpentene film, and a film formed by providing a release agent layer on these films.
  • the method for producing the resin-attached metal leaf 31 is not particularly limited as long as the resin-attached metal leaf 31 can be produced.
  • Examples of the method for producing the resin-attached metal foil 31 include a method in which the varnish-like resin composition (resin varnish) is applied onto the metal foil 13 and heated.
  • the varnish-like resin composition is applied onto the metal foil 13 by using, for example, a bar coater.
  • the applied resin composition is heated under the conditions of, for example, 40 ° C. or higher and 180 ° C. or lower, and 0.1 minutes or longer and 10 minutes or shorter.
  • the heated resin composition is formed on the metal foil 13 as an uncured resin layer 32. By the heating, the organic solvent can be volatilized from the resin varnish to reduce or remove the organic solvent.
  • the resin composition according to the present embodiment is a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Therefore, the resin-attached metal foil provided with the resin composition or the resin layer containing the semi-cured product of the resin composition has a resin layer having low dielectric properties and high adhesiveness to the metal foil. It is a metal leaf with a resin.
  • the resin-attached metal foil can be used when a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring is preferably manufactured. For example, a multi-layered wiring board can be manufactured by laminating on the wiring board. As a wiring board obtained by using such a metal foil with a resin, a wiring board having an insulating layer having low dielectric properties and high adhesiveness to the metal foil can be obtained.
  • FIG. 5 is a schematic cross-sectional view showing an example of the resin-attached film 41 according to the present embodiment.
  • the resin-attached film 41 includes a resin layer 42 containing the resin composition or a semi-cured product of the resin composition, and a support film 43.
  • the resin-attached film 41 includes the resin layer 42 and a support film 43 laminated together with the resin layer 42. Further, the resin-attached film 41 may be provided with another layer between the resin layer 42 and the support film 43.
  • the resin layer 42 may include the semi-cured product of the resin composition as described above, or may contain the resin composition that has not been cured. .. That is, the resin-attached film 41 may include a resin layer containing a semi-cured product of the resin composition (the resin composition of the B stage) and a support film, or the resin composition before curing. It may be a film with a resin including a resin layer containing a substance (the resin composition of the A stage) and a support film. Further, the resin layer may contain the resin composition or a semi-cured product of the resin composition, and may or may not contain a fibrous base material. Further, the resin composition or the semi-cured product of the resin composition may be a dried or heat-dried resin composition. Further, as the fibrous base material, the same one as that of the prepreg fibrous base material can be used.
  • the support film used for the resin-attached film can be used without limitation.
  • the support film include electrically insulating properties such as polyester film, polyethylene terephthalate (PET) film, polyimide film, polyparavanic acid film, polyether ether ketone film, polyphenylene sulfide film, polyamide film, polycarbonate film, and polyarylate film. Examples include films.
  • the resin-attached film 41 may be provided with a cover film or the like, if necessary. By providing the cover film, it is possible to prevent foreign matter from being mixed.
  • the cover film is not particularly limited, and examples thereof include a polyolefin film, a polyester film, and a polymethylpentene film.
  • the support film and cover film may be subjected to surface treatment such as matte treatment, corona treatment, mold release treatment, and roughening treatment, if necessary.
  • the method for producing the resin-containing film 41 is not particularly limited as long as the resin-containing film 41 can be produced.
  • Examples of the method for producing the resin-attached film 41 include a method in which the varnish-like resin composition (resin varnish) is applied onto the support film 43 and heated.
  • the varnish-like resin composition is applied onto the support film 43, for example, by using a bar coater.
  • the applied resin composition is heated under the conditions of, for example, 40 ° C. or higher and 180 ° C. or lower, and 0.1 minutes or longer and 10 minutes or shorter.
  • the heated resin composition is formed on the support film 43 as an uncured resin layer 42. By the heating, the organic solvent can be volatilized from the resin varnish to reduce or remove the organic solvent.
  • the resin composition according to the present embodiment is a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Therefore, the resin-coated film including the resin composition or the resin layer containing the semi-cured product of the resin composition has a resin layer having low dielectric properties and high adhesiveness to the metal foil. It is a film with resin.
  • the resin-coated film can be used when a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring is preferably manufactured.
  • a multilayer wiring board can be manufactured by laminating on a wiring board and then peeling off the support film, or by peeling off the support film and then laminating on the wiring board.
  • a wiring board having an insulating layer having low dielectric properties and high adhesiveness to wiring can be obtained.
  • One aspect of the present invention is a polybutadiene compound having an epoxy group in the molecule, and a polyphenylene ether compound having at least one of a group represented by the following formula (1) and a group represented by the following formula (2) in the molecule. It is a resin composition characterized by containing a styrene-based block copolymer and a curing agent.
  • p represents 0 to 10
  • Z represents an arylene group
  • R 1 to R 3 each independently represent a hydrogen atom or an alkyl group.
  • R 4 represents a hydrogen atom or an alkyl group.
  • the resin composition is obtained by curing the polyphenylene ether compound together with the curing agent, so that even if the polybutadiene compound and the styrene-based block copolymer are contained, the polyphenylene ether has excellent low dielectric properties. It is considered that a cured product that maintains the above can be obtained. Further, since the resin composition contains a polybutadiene compound having an epoxy group in the molecule together with the styrene-based block copolymer, a cured product having high adhesiveness to the metal foil can be obtained. From these facts, it is considered that the resin composition can obtain a cured product having low dielectric properties and high adhesiveness to the metal foil.
  • the content of the polybutadiene compound is preferably 5 to 40 parts by mass with respect to 100 parts by mass in total of the polybutadiene compound, the polyphenylene ether compound, and the curing agent.
  • a resin composition when cured, a resin composition can be obtained which is a cured product having higher adhesiveness to the metal foil while maintaining excellent low dielectric properties.
  • the content of the polybutadiene compound is 3 to 20 mass by mass with respect to 100 parts by mass of the total of the polybutadiene compound, the polyphenylene ether compound, the styrene block copolymer, and the curing agent. It is preferably a part.
  • a resin composition when cured, a resin composition can be obtained which is a cured product having higher adhesiveness to the metal foil while maintaining excellent low dielectric properties.
  • the curing agent contains an allyl compound.
  • a resin composition in which a cured product having low dielectric properties and high adhesiveness to a metal foil can be preferably obtained. It is considered that this is because the allyl compound can suitably cure the polyphenylene ether compound together with the polybutadiene compound and the styrene-based block copolymer.
  • the allyl compound contains an allyl isocyanurate compound having two or more allyl groups in the molecule.
  • a resin composition in which a cured product having low dielectric properties and high adhesiveness to a metal foil can be preferably obtained. It is considered that this is because the allyl isocyanurate compound can suitably cure the polyphenylene ether compound together with the polybutadiene compound and the styrene-based block copolymer.
  • the polybutadiene compound preferably has a concentration of oxylan oxygen of 1 to 10% by mass.
  • a resin composition when cured, a resin composition can be obtained which is a cured product having higher adhesiveness to the metal foil while maintaining excellent low dielectric properties. It is considered that this is because the effect of improving the adhesiveness of the cured product to the metal foil by containing the polybutadiene compound can be more preferably exhibited.
  • the styrene-based block copolymer is a methylstyrene (ethylene / butylene) methylstyrene copolymer, a methylstyrene (ethylene-ethylene / propylene) methylstyrene copolymer, or a styreneisoprene copolymer.
  • Styrene isoprene styrene copolymer styrene (ethylene / butylene) styrene copolymer, styrene (ethylene-ethylene / propylene) styrene copolymer, styrene butadiene styrene copolymer, styrene (butadiene / butylene) styrene copolymer, It is preferable to contain at least one selected from the group consisting of styrene isobutylene styrene copolymers and hydrogenated products thereof.
  • a resin composition when cured, a resin composition can be obtained which is a cured product having higher adhesiveness to the metal foil while maintaining excellent low dielectric properties. It is considered that this is because the inclusion of the styrene-based block copolymer can suppress the deterioration of the adhesiveness of the cured product to the metal foil.
  • the polyphenylene ether compound contains a polyphenylene ether compound having a group represented by the formula (2) in the molecule.
  • Another aspect of the present invention is a prepreg comprising the resin composition or a semi-cured product of the resin composition and a fibrous base material.
  • Another aspect of the present invention is a resin-coated film including a resin layer containing the resin composition or a semi-cured product of the resin composition, and a support film.
  • another aspect of the present invention is a metal foil with a resin including a resin layer containing the resin composition or a semi-cured product of the resin composition, and a metal foil.
  • Another aspect of the present invention is a metal-clad laminate provided with an insulating layer containing a cured product of the resin composition or a cured product of the prepreg, and a metal foil.
  • Another aspect of the present invention is a wiring board provided with an insulating layer containing a cured product of the resin composition or a cured product of the prepreg, and wiring.
  • a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Further, according to the present invention, there are provided a prepreg, a film with a resin, a metal foil with a resin, a metal-clad laminate, and a wiring board obtained by using the resin composition.
  • Epoxy group-containing polybutadiene Epoxy group-containing polybutadiene 1: Polybutadiene compound having an epoxy group in the molecule (JP-100 manufactured by Nippon Soda Co., Ltd., oxylan concentration: 7.7% by mass)
  • Epoxy group-containing polybutadiene 2 Polybutadiene compound having an epoxy group in the molecule (PB3600 manufactured by Daicel Co., Ltd., oxylan concentration: 8.2% by mass)
  • Epoxy group-containing polybutadiene 3 Polybutadiene compound having an epoxy group in the molecule (Ricon 657 manufactured by Cray Valley, oxylan concentration: 6.7% by mass)
  • PPE Modified PPE1: A polyphenylene ether compound having a methacryloyl group at the terminal (modified polyphenylene ether in which the terminal hydroxyl group of the polyphenylene ether is modified with a methacryloyl group, represented by the above formula (12), and Y
  • Modified PPE2 A polyphenylene ether compound having a vinylbenzyl group (ethenylbenzyl group) at the terminal (modified polyphenylene ether obtained by reacting polyphenylene ether with chloromethylstyrene).
  • polyphenylene ether (SA90 manufactured by SABIC Innovative Plastics, 2 terminal hydroxyl groups, weight average molecular weight Mw1700).
  • SA90 manufactured by SABIC Innovative Plastics, 2 terminal hydroxyl groups, weight average molecular weight Mw1700.
  • the mixture was stirred until polyphenylene ether, chloromethylstyrene, and tetra-n-butylammonium bromide were dissolved in toluene. At that time, it was gradually heated and finally heated until the liquid temperature reached 75 ° C. Then, an aqueous sodium hydroxide solution (20 g of sodium hydroxide / 20 g of water) was added dropwise to the solution over 20 minutes as an alkali metal hydroxide. Then, the mixture was further stirred at 75 ° C. for 4 hours. Next, after neutralizing the contents of the flask with 10% by mass of hydrochloric acid, a large amount of methanol was added.
  • the obtained solid was analyzed by 1 H-NMR (400 MHz, CDCl 3 , TMS). As a result of NMR measurement, a peak derived from a vinylbenzyl group (ethenylbenzyl group) was confirmed at 5 to 7 ppm. As a result, it was confirmed that the obtained solid was a modified polyphenylene ether having a vinylbenzyl group (ethenylbenzyl group) as the substituent at the molecular terminal in the molecule. Specifically, it was confirmed that the polyphenylene ether was ethenylbenzylated.
  • the obtained modified polyphenylene ether compound is represented by the above formula (11), Y is represented by a dimethylmethylene group (represented by formula (9), and R 33 and R 34 in the formula (9) are methyl groups. ), and, Z is a phenylene group, R 1 ⁇ R 3 is a hydrogen atom, p is a modified polyphenylene ether compound is 1.
  • TEAH tetraethylammonium hydroxide
  • Residual OH amount ( ⁇ mol / g) [(25 ⁇ Abs) / ( ⁇ ⁇ OPL ⁇ X)] ⁇ 10 6
  • ⁇ represents the extinction coefficient and is 4700 L / mol ⁇ cm.
  • the OPL is the cell optical path length, which is 1 cm.
  • the intrinsic viscosity (IV) of the modified polyphenylene ether was measured in methylene chloride at 25 ° C. Specifically, the intrinsic viscosity (IV) of the modified polyphenylene ether is measured by using a 0.18 g / 45 ml methylene chloride solution (liquid temperature 25 ° C.) of the modified polyphenylene ether with a viscometer (AVS500 Visco System manufactured by Schott). It was measured. As a result, the intrinsic viscosity (IV) of the modified polyphenylene ether was 0.086 dl / g.
  • Mw weight average molecular weight
  • each component other than the filler was added to toluene with the composition (parts by mass) shown in Table 1 so that the solid content concentration was 50% by mass, and mixed. The mixture was stirred for 60 minutes. Then, a filler was added to the obtained liquid, and the filler was dispersed by a bead mill. By doing so, a varnish-like resin composition (varnish) was obtained.
  • an evaluation substrate (cured product of metal foil with resin) was obtained as follows.
  • the obtained varnish is applied to a metal foil (copper foil, 3EC-VLP manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 12 ⁇ m) so as to have a thickness of 50 ⁇ m, and heated at 120 ° C. for 3 minutes to form a resin. Obtained a metal leaf. Then, two of the obtained metal foils with resin were laminated so that the resin layers were in contact with each other. Using this as a pressure-pressed body, the resin layer of the metal leaf with resin was cured by heating and pressurizing for 2 hours under the conditions of vacuum at 200 ° C. and pressure of 4 MPa. This was used as an evaluation substrate (cured product of metal foil with resin). The thickness of the resin layer (thickness other than the metal foil) on the evaluation substrate was 100 ⁇ m.
  • the evaluation substrate (cured product of metal foil with resin) prepared as described above was evaluated by the method shown below.
  • the relative permittivity and dielectric loss tangent of the laminated plate from which the copper foil of the evaluation substrate (cured product of the metal foil with resin) was removed at 10 GHz was measured by the cavity resonator perturbation method. Specifically, a network analyzer (N5230A manufactured by Agilent Technologies, Inc.) was used to measure the relative permittivity and dielectric loss tangent of the laminated board from which the copper foil of the evaluation substrate was removed at 10 GHz.
  • the copper foil was peeled off from the evaluation substrate (cured product of the metal foil with resin), and the peel strength (copper foil peel strength) at that time was measured in accordance with JIS C 6481. Specifically, the copper foil was pulled from the evaluation substrate and peeled off at a speed of 50 mm / min by a testing machine, and the peel strength (N / mm) at that time was measured.
  • Tg Glass transition temperature
  • the resin composition containing the polyphenylene ether compound and the cured product contains a polybutadiene compound having an epoxy group in the molecule and a styrene-based block copolymer (Examples 1 to 7).
  • the dielectric property was low and the copper foil peel strength was high.
  • the copper foil peel strength could not be increased.
  • the concentration of oxylan oxygen is 8.2% by mass.
  • the epoxy group-containing polybutadiene 2 is used (Example 5) or the epoxy group-containing polybutadiene 3 having an oxygen concentration of 6.7% by mass is used (Example 6).
  • the dielectric properties were low and the copper foil peel strength was high. From this, it can be seen that the concentration of oxylan oxygen in the polybutadiene compound having an epoxy group in the molecule is preferably 1 to 10% by mass.
  • the glass transition temperature was higher than that of Example 7 which was the same as Example 2 except that TMPT was used. From this, it can be seen that the curing agent preferably contains an allyl compound such as an allyl isocyanurate compound having two or more allyl groups in the molecule.
  • an allyl compound such as an allyl isocyanurate compound having two or more allyl groups in the molecule.
  • a resin composition capable of obtaining a cured product having low dielectric properties and high adhesiveness to a metal foil. Further, according to the present invention, there are provided a prepreg, a film with a resin, a metal foil with a resin, a metal-clad laminate, and a wiring board obtained by using the resin composition.

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PCT/JP2020/027599 2019-07-17 2020-07-16 樹脂組成物、プリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板、及び配線板 Ceased WO2021010431A1 (ja)

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CN202080051204.1A CN114207021B (zh) 2019-07-17 2020-07-16 树脂组合物、预浸料、带树脂的膜、带树脂的金属箔、覆金属箔层压板以及布线板
US17/626,881 US12098257B2 (en) 2019-07-17 2020-07-16 Resin composition, prepreg, film with resin, metal foil with resin, metal-clad laminate, and wiring board
KR1020227004909A KR102931421B1 (ko) 2019-07-17 2020-07-16 수지 조성물, 프리프레그, 수지 부가 필름, 수지 부가 금속박, 금속 클래드 적층판, 및 배선판

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JP2024516137A (ja) * 2021-04-20 2024-04-12 エスエイチピーピー グローバル テクノロジーズ べスローテン フェンノートシャップ フェニレンエーテルオリゴマーおよびフェニレンエーテルオリゴマーを含む硬化可能な熱硬化性組成物
JPWO2024185371A1 (https=) * 2023-03-06 2024-09-12
WO2025070328A1 (ja) * 2023-09-29 2025-04-03 パナソニックＩｐマネジメント株式会社 樹脂付き金属箔、金属張積層板、及び配線板
WO2026062844A1 (ja) * 2024-09-19 2026-03-26 株式会社レゾナック 樹脂組成物、シート状材料、プリント配線板、及び半導体装置
TWI923863B (zh) 2021-11-19 2026-05-01 日商松下知識產權經營股份有限公司 樹脂組成物、附樹脂之薄膜、附樹脂之金屬箔、覆金屬積層板及印刷配線板

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