WO2023171553A1 - 樹脂組成物、硬化物、プリプレグ、金属箔張積層板、樹脂複合シート、プリント配線板、および、半導体装置 - Google Patents

樹脂組成物、硬化物、プリプレグ、金属箔張積層板、樹脂複合シート、プリント配線板、および、半導体装置 Download PDF

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WO2023171553A1
WO2023171553A1 PCT/JP2023/007985 JP2023007985W WO2023171553A1 WO 2023171553 A1 WO2023171553 A1 WO 2023171553A1 JP 2023007985 W JP2023007985 W JP 2023007985W WO 2023171553 A1 WO2023171553 A1 WO 2023171553A1
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formula
resin composition
compound
group
mass
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PCT/JP2023/007985
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English (en)
French (fr)
Japanese (ja)
Inventor
和弘 橋口
恵一 長谷部
俊介 平野
宇志 小林
祐司 中島
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三菱瓦斯化学株式会社
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Application filed by 三菱瓦斯化学株式会社 filed Critical 三菱瓦斯化学株式会社
Priority to JP2024506131A priority Critical patent/JPWO2023171553A1/ja
Priority to KR1020247033052A priority patent/KR20240157733A/ko
Priority to CN202380025888.1A priority patent/CN118843649A/zh
Publication of WO2023171553A1 publication Critical patent/WO2023171553A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • 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
    • 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 cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.
  • Patent Document 1 discloses maleimide resins shown below as maleimide resins suitable for electronic material applications. Further, Patent Document 1 shows that a curable resin composition blended with an epoxy resin or the like has excellent dielectric properties. Further, Patent Document 2 also describes the following compounds.
  • the present invention aims to solve the above problems, and provides a resin composition that maintains excellent low dielectric properties (Dk and/or Df) and has a low coefficient of thermal expansion (CTE), and
  • the purpose of the present invention is to provide cured products, prepregs, metal foil-clad laminates, resin composite sheets, printed wiring boards, and semiconductor devices.
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom
  • R mx each independently represents a methylene group, an ethylidene group, or , 2,2-propylidene group
  • R my is a group selected from the following group (A)
  • m represents an integer of 0 to 3
  • n is the average value of the number of repeats, 1 .00 ⁇ n ⁇ 20.00) (Group (A))
  • R y is each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent
  • ny is , each independently an integer from 0 to 3
  • * is the bonding position with R mx .
  • Ar represents an aromatic hydrocarbon linking group.
  • the content of the compound (M) represented by the formula (M) is 1 to 90 parts by mass when the resin solid content in the resin composition is 100 parts by mass. resin composition.
  • the content of the polymer (V) having the structural unit represented by the formula (V) is 1 to 90 parts by mass, The resin composition according to ⁇ 1> or ⁇ 2>.
  • n is 1.05 ⁇ n ⁇ 20.00, the resin composition according to any one of ⁇ 1> to ⁇ 3>. thing.
  • R z each independently represents a hydrocarbon group having 1 to 10 carbon atoms, m represents an integer of 0 to 3, n is the average value of the number of repeats, (Represents 1.00 ⁇ n ⁇ 20.00.)
  • ⁇ 7> Any one of ⁇ 1> to ⁇ 6>, wherein the weight average molecular weight of the polymer (V) having a structural unit represented by the formula (V) is 3,000 to 130,000.
  • ⁇ 8> Any one of ⁇ 1> to ⁇ 6>, wherein the weight average molecular weight of the polymer (V) having a structural unit represented by the formula (V) is 10,000 to 130,000.
  • thermosetting compounds selected from the group consisting of polyphenylene ether compounds containing two or more unsaturated double bonds.
  • Resin composition ⁇ 10> The resin according to ⁇ 9>, wherein the content of the other thermosetting compound (C) is 1 to 70 parts by mass when the resin solid content contained in the resin composition is 100 parts by mass.
  • any one of ⁇ 1> to ⁇ 10> which further includes a low molecular weight vinyl compound having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule.
  • the low molecular weight vinyl compound having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule is a (meth)acrylic acid ester compound, an aromatic vinyl compound, a saturated selected from the group consisting of fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides, ethylenically unsaturated dicarboxylic acid monoalkyl esters, and ethylenically unsaturated carboxylic acid amides.
  • ⁇ 13> The resin composition according to any one of ⁇ 1> to ⁇ 12>, further comprising a filler (D).
  • ⁇ 14> The resin composition according to ⁇ 13>, wherein the content of the filler (D) in the resin composition is 10 to 1600 parts by mass based on 100 parts by mass of resin solid content.
  • ⁇ 15> The resin composition according to any one of ⁇ 1> to ⁇ 14>, further comprising a thermoplastic elastomer.
  • n 1.05 ⁇ n ⁇ 20.00
  • the compound (M) represented by the formula (M) includes a compound represented by the formula (M-1),
  • the weight average molecular weight of the polymer (V) having the structural unit represented by the formula (V) is 3,000 to 130,000,
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, m represents an integer of 0 to 3, and n represents , is the average value of the number of repetitions, and represents 1.00 ⁇ n ⁇ 20.00.
  • ⁇ 17> Any one of ⁇ 1> to ⁇ 16>, wherein the weight average molecular weight of the polymer (V) having a structural unit represented by the formula (V) is 10,000 to 130,000.
  • the resin composition described. ⁇ 18> A cured product of the resin composition according to any one of ⁇ 1> to ⁇ 17>.
  • ⁇ 19> A prepreg formed from a base material and the resin composition according to any one of ⁇ 1> to ⁇ 17>.
  • a metal foil-clad laminate comprising at least one layer formed from the prepreg according to ⁇ 19> and metal foil disposed on one or both sides of the layer formed from the prepreg.
  • a resin composite sheet comprising a support and a layer formed from the resin composition according to any one of ⁇ 1> to ⁇ 17> disposed on the surface of the support.
  • a printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer is made of the resin composition according to any one of ⁇ 1> to ⁇ 17>.
  • a printed wiring board comprising at least one of a layer formed from a material and a layer formed from a prepreg according to ⁇ 19>.
  • a semiconductor device including the printed wiring board according to ⁇ 22>.
  • the present invention provides a resin composition that maintains excellent low dielectric properties (Dk and/or Df) and has a low coefficient of thermal expansion (CTE), as well as a cured product, prepreg, metal foil-clad laminate, resin composite sheet, It is now possible to provide printed wiring boards and semiconductor devices.
  • Dk and/or Df low dielectric properties
  • CTE coefficient of thermal expansion
  • this embodiment a mode for carrying out the present invention (hereinafter simply referred to as "this embodiment") will be described in detail.
  • the present embodiment below is an illustration for explaining the present invention, and the present invention is not limited only to this embodiment.
  • " ⁇ " is used to include the numerical values described before and after it as a lower limit value and an upper limit value.
  • various physical property values and characteristic values are assumed to be at 23° C. unless otherwise stated.
  • the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
  • alkyl group includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the relative dielectric constant refers to the ratio of the dielectric constant to the vacuum dielectric constant of a substance. Further, in this specification, the relative dielectric constant may be simply referred to as "permittivity.”
  • (meth)acrylic represents both or either acrylic and methacryl.
  • (Meta)allyl represents allyl and/or metaallyl. If the standards shown in this specification differ in measurement methods, etc. depending on the year, unless otherwise stated, the standards as of January 1, 2022 shall be used.
  • a maleimide group refers to a group represented by the following.
  • each A independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. * indicates a bonding position with another site.
  • both A are preferably hydrogen atoms.
  • the number of carbon atoms in the alkyl group is preferably 1 to 3 from the viewpoint of suitable curing.
  • the resin solid content refers to the components excluding the filler and the solvent, and refers to the compound (M) represented by the formula (M), the polymer (V ), as well as other thermosetting compounds (C) blended as necessary, and other resin additive components (additives such as flame retardants, etc.).
  • the resin composition of this embodiment is characterized by containing a compound (M) represented by formula (M) and a polymer (V) having a structural unit represented by formula (V).
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom
  • R mx each independently represents a methylene group, an ethylidene group, or , 2,2-propylidene group
  • R my is a group selected from the following group (A)
  • m represents an integer of 0 to 3
  • n is the average value of the number of repeats, 1 .00 ⁇ n ⁇ 20.00)
  • Group (A) Group (A)
  • R y is each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent
  • ny is , each independently an integer from 0 to 3, and * is the bonding position with R mx
  • R mx is a methylene group, an ethylidene group, or a 2,2-propylidene group, and two R mx are bonded to one benzene ring. It is presumed that this makes the structure more compact, so even if the crosslinking reaction progresses, it will not become rigid and will be more compatible with other resin components.
  • the resin composition of this embodiment contains a compound (M) represented by formula (M).
  • a compound (M) represented by formula (M) By including the compound (M) represented by formula (M), low dielectric properties (Dk and/or Df) of the resulting resin composition can be effectively achieved.
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom
  • R mx each independently represents a methylene group, an ethylidene group, or , 2,2-propylidene group
  • R my is a group selected from the following group (A)
  • m represents an integer of 0 to 3
  • n is the average value of the number of repeats, 1 .00 ⁇ n ⁇ 20.00) (Group (A))
  • R y is each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent
  • ny is , each independently an integer from 0 to 3
  • * is the bonding position with R mx .
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, and an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom. or a phenyl group which may be substituted with a halogen atom, such as a methyl group, an ethyl group, a propyl group (preferably an isopropyl group), or a butyl group (preferably an isopropyl group), which may be substituted with a halogen atom. is more preferably at least one selected from the group consisting of a sec-butyl group, a tert-butyl group, and a phenyl group.
  • the halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom or a chlorine atom.
  • R is preferably a hydrocarbon group having 1 to 10 carbon atoms that is not substituted with a halogen atom.
  • m represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.
  • R mx is each independently a methylene group, an ethylidene group, or a 2,2-propylidene group.
  • R mx By using a methylene group, ethylidene group, or 2,2-propylidene group as R mx , it has a lower dielectric property (Dk and/or Df) and a flexible structure compared to an aromatic ring. Therefore, even if the crosslinking reaction progresses, it is difficult to become rigid and it is presumed that it becomes compatible with other resin components.
  • Each R mx is preferably an ethylidene group or a 2,2-propylidene group, more preferably a 2,2-propylidene group.
  • R my is a group selected from group (A).
  • R y is each independently an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent, and a methyl group, It is preferably at least one selected from the group consisting of ethyl group, propyl group, methoxy group, ethoxy group, and phenyl group.
  • ny is each independently an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.
  • n is the average value of the number of repetitions, and represents 1.00 ⁇ n ⁇ 20.00.
  • n is preferably 1.05 or more (1.05 ⁇ n), more preferably 1.10 or more (1.10 ⁇ n), and 1.20 or more (1.20 ⁇ n). It is more preferably 1.25 or more (1.25 ⁇ n), even more preferably 1.30 or more (1.30 ⁇ n), and even more preferably 1.50 or more (1.25 ⁇ n). It is even more preferable that 50 ⁇ n).
  • the low dielectric properties (Dk and/or Df) of the compound (M) represented by the formula (M) tend to improve, and the resin composition using the same or the resulting cured product
  • the low dielectric properties (Dk and/or Df) of these materials also tend to improve.
  • n is preferably 10.00 or less (n ⁇ 10.00), more preferably 5.00 or less (n ⁇ 5.00), and 3.00 or less (n ⁇ 3.00). ), more preferably 2.75 or less (n ⁇ 2.75), even more preferably 2.50 or less (n ⁇ 2.50).
  • n is, for example, the number average molecular weight determined by gel permeation chromatography (GPC, detector: RI) of the compound (M) represented by formula (M), or the area of each separated peak. It can be calculated from the ratio.
  • the compound (M) represented by formula (M) preferably includes a compound represented by formula (M-1).
  • R each independently represents a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom
  • m represents an integer of 0 to 3
  • n represents , is the average value of the number of repetitions, and represents 1.00 ⁇ n ⁇ 20.00.
  • R, m, and n have the same meanings as R, m, and n in formula (M), respectively, and the preferred ranges are also the same.
  • the compound (M) represented by formula (M) more preferably includes a compound represented by formula (M-2).
  • R z each independently represents a hydrocarbon group having 1 to 10 carbon atoms
  • m represents an integer of 0 to 3
  • n is the average value of the number of repeats, 1.00 ⁇ n ⁇ 20.00
  • R z is a hydrocarbon group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms or a phenyl group, and a methyl group or ethyl group which may be substituted with a halogen atom. , a propyl group (preferably an isopropyl group), a butyl group (preferably a sec-butyl group, a tert-butyl group), and a phenyl group.
  • One of the two terminal maleimide groups and R mx (preferably a 2,2-propylidene group) closest to the maleimide group are located at the meta or ortho position with respect to the benzene ring, and the other maleimide group group
  • a compound (M- C) A compound (M- C).
  • the compound (MA) is mixed with the compound (MB) and the compound (MC), which have a high degree of freedom of rotation of the phenylene maleimide group moiety in the molecule.
  • the degree of freedom in the distribution of crosslinking reaction points in the resin composition during the curing reaction increases, and a cured resin product having a stronger network tends to be formed.
  • the heat resistance for example, glass transition temperature
  • low thermal expansion of the resulting cured product tend to be further improved.
  • the terminal maleimide group and R mx preferably 2,2-propylidene group
  • the compound is preferable that the compound is
  • the proportion of compound (MA) in compound (M) represented by formula (M) is preferably 90 area% or less, and 80 area% or less. It is more preferable that the amount is at most 70 area %, even more preferably 70 area % or less, and may be 50 area % or less, or 30 area % or less. When the content is below the upper limit, crystallinity decreases, so solvent solubility tends to improve. Further, the proportion of the compound (M-A) may be 0 area%, but is more preferably 2 area% or more, even more preferably 5 area% or more, and even more preferably 10 area% or more. You can.
  • the proportion of compound (MB) among compound (M) represented by formula (M) is preferably less than 60 area %, and less than 55 area %. It is preferable that there be. By setting it below the above-mentioned upper limit value, it tends to be possible to reduce the manufacturing cost of the compound (M) represented by the formula (M) and the amount of industrial waste. Further, the proportion of the compound (MB) is preferably at least 30 area %, more preferably at least 35 area %, even more preferably at least 40 area %.
  • the above ratio of compound (MB) preferably satisfies the above range when 1.00 ⁇ n ⁇ 5.00 in formula (M), and 1.00 ⁇ n ⁇ 3.00. In some cases, it is more preferable to satisfy the above range. Further, it is preferable that the above range is satisfied when the compound (MB) contains the following compound as a main component (for example, in a proportion of 30% by mass or more of the compound (M) represented by the formula (M)).
  • the proportion of compound (MC) in compound (M) represented by formula (M) is preferably less than 60 area%, and less than 50 area%. It is preferable that there be. Further, the proportion of the compound (MC) is preferably 15 area % or more, more preferably 25 area % or more. When the proportion of the compound (MC) is 15 area% or more, it has excellent low dielectric properties (Dk and/or Df), and when it is less than 60 area%, it has good curability and adhesion, and it can be used for substrates, etc. Defects during production can be effectively suppressed.
  • Dk and/or Df low dielectric properties
  • the above ratio of compound (MC) preferably satisfies the above range when 1.00 ⁇ n ⁇ 5.00 in formula (M), and 1.00 ⁇ n ⁇ 3.00. In some cases, it is more preferable to satisfy the above range. Further, it is preferable that the above range is satisfied when the compound (MC) contains the following compound as a main component (for example, in a proportion of 15% by mass or more of the compound represented by the formula (M)).
  • the compound (M-A) has a large influence on the problem of crystallinity and the problem of deterioration of electrical properties
  • the compound (M-B) in the compound (M) represented by the formula (M) is preferably 50 area% or more, and 60% by area or more based on the total amount of the compound (MA), the compound (MB), and the compound (MC). It is more preferably at least 70% by area, particularly preferably at least 70% by area.
  • the upper limit may be, for example, 100 area % or less, or even 99 area % or less.
  • it is preferable that the above range is satisfied when 1.00 ⁇ n ⁇ 5.00, and it is more preferable that the above range is satisfied when 1.00 ⁇ n ⁇ 3.00. .
  • the softening point of the compound (M) represented by formula (M) measured by a method according to JIS K-7234 is preferably 50°C or higher, more preferably 80°C or higher, and even more preferably 90°C or higher. °C or higher, particularly preferably 95°C or higher.
  • the softening point is preferably 150°C or lower, more preferably 140°C or lower, even more preferably 130°C or lower, even more preferably 120°C or lower, even if it is 110°C or lower or 100°C or lower. good.
  • the acid value of the compound (M) represented by formula (M) is preferably 30 mgKOH/g or less, more preferably 1 to 15 mgKOH/g.
  • the acid value is high, there are many molecules that are not converted into maleimide, and structures having carboxylic acid become excessive, which affects electrical properties and water resistance.
  • the weight average molecular weight (Mw) of the compound (M) represented by formula (M) is preferably 500 or more, and further may be 600 or more, or 700 or more. When the amount is equal to or more than the lower limit, the resulting cured product tends to have better low dielectric properties (Dk and/or Df) and low water absorption.
  • the upper limit of the weight average molecular weight (Mw) of the compound (M) represented by formula (M) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, and even more preferably 5,000 or less. It is more preferably below, even more preferably 3000 or less, even more preferably 1000 or less. By setting it below the above-mentioned upper limit, the heat resistance and handleability of the obtained cured product tend to be further improved.
  • the compound represented by formula (M) represented by formula (M) is composed of compound (MA), compound (MB), and compound Obtained as a mixture of (MC).
  • the content of the compound (M) represented by formula (M) is 1 to 90 parts by mass when the resin solid content in the resin composition is 100 parts by mass. is preferred.
  • the lower limit of the content of the compound (M) represented by formula (M) is more preferably 5 parts by mass or more, and 10 parts by mass or more, based on 100 parts by mass of resin solids in the resin composition. It is more preferable that the amount is 15 parts by mass or more, even more preferably 20 parts by mass or more, or 25 parts by mass or more.
  • the upper limit of the content of the compound (M) represented by formula (M) is more preferably 80 parts by mass or less, and 70 parts by mass based on 100 parts by mass of the resin solid content in the resin composition. It is more preferably at most 60 parts by mass, even more preferably at most 50 parts by mass, and may be at most 40 parts by mass.
  • the resin composition in this embodiment may contain only one type of compound (M) represented by formula (M), or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition of this embodiment includes a polymer (V) having a structural unit represented by formula (V).
  • a resin composition having excellent low dielectric properties low dielectric constant, low dielectric loss tangent
  • a cured resin product with a strong network is formed, so it has excellent low dielectric properties and a low coefficient of thermal expansion (low CTE). It is also assumed to be excellent.
  • Ar represents an aromatic hydrocarbon linking group.
  • the aromatic hydrocarbon linking group may be a group consisting only of an aromatic hydrocarbon that may have a substituent, or a group consisting of an aromatic hydrocarbon that may have a substituent and another linking group. It may be a group consisting of a combination of.
  • the aromatic hydrocarbon linking group is preferably a group consisting only of aromatic hydrocarbons that may have substituents.
  • the substituent that the aromatic hydrocarbon may have is a substituent Z (for example, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxy groups, amino groups, carboxy groups, halogen atoms, etc.). Further, it is preferable that the aromatic hydrocarbon has no substituent.
  • the aromatic hydrocarbon linking group is usually a divalent linking group.
  • aromatic hydrocarbon linking group examples include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a biphenyldiyl group, and a fluorenediyl group, which may have a substituent, Among these, a phenylene group which may have a substituent is preferred.
  • the above-mentioned substituent Z is exemplified as the substituent, but it is preferable that groups such as the above-mentioned phenylene group have no substituent.
  • the structural unit represented by formula (V) is the structural unit represented by the following formula (V1), the structural unit represented by the following formula (V2), and the structural unit represented by the following formula (V3). More preferably, at least one is included. Note that * in the following formula represents the bonding position. Further, hereinafter, the constituent units represented by formulas (V1) to (V3) may be collectively referred to as “constituent unit (a)."
  • L 1 is an aromatic hydrocarbon linking group (preferably 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 10 carbon atoms).
  • examples include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a biphenyldiyl group, and a fluorenediyl group, which may have a substituent.
  • a phenylene group is preferred.
  • the above-mentioned substituent Z is exemplified as the substituent, but it is preferable that groups such as the above-mentioned phenylene group have no substituent.
  • the compound forming the structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, divinylphenanthrene, etc. It will be done. Among them, divinylbenzene is particularly preferred. One type of these divinyl aromatic compounds may be used, or two or more types may be used as necessary.
  • the polymer (V) having a structural unit represented by formula (V) may be a homopolymer of the structural unit (a), but it may also be a copolymer with a structural unit derived from another monomer. It may be a combination.
  • the copolymerization ratio of the structural unit (a) is preferably 3 mol % or more, and 5 mol % or more. % or more, more preferably 10 mol% or more, and may be 15 mol% or more.
  • the upper limit is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, and 60 mol% or less. % or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, even more preferably 30 mol% or less, and furthermore, It may be 25 mol% or less, or 20 mol% or less.
  • the structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound) is exemplified.
  • the structural unit (b) derived from the monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).
  • L 2 is an aromatic hydrocarbon linking group, and a preferred example is the above-mentioned example of L 1 .
  • R V1 is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). When R V1 is a hydrocarbon group, the number of carbon atoms is preferably 1 to 6, more preferably 1 to 3.
  • R V1 and L 2 may have the above-mentioned substituent Z.
  • the polymer (V) having the structural unit represented by formula (V) is a copolymer containing the structural unit (b) derived from a monovinyl aromatic compound
  • examples of the monovinyl aromatic compound include styrene, Vinyl aromatic compounds such as vinylnaphthalene and vinylbiphenyl; o-methylstyrene, m-methylstyrene, p-methylstyrene, o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinyl Examples include nuclear alkyl-substituted vinyl aromatic compounds such as benzene, methylvinylbiphenyl, and ethylvinylbiphenyl.
  • the monovinyl aromatic compound exemplified here may have the above-mentioned substituent Z as appropriate. Further, these monovinyl aromatic compounds may be used alone or
  • the copolymerization ratio of the structural unit (b) shall be 10 mol% or more. is preferable, more preferably 15 mol% or more, furthermore 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, 75 mol%. It may be more than that.
  • the upper limit is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.
  • the polymer (V) having the structural unit represented by formula (V) may have other structural units other than the structural unit (a) and the structural unit (b).
  • Examples of other structural units include a structural unit (c) derived from a cycloolefin compound.
  • the cycloolefin compound include hydrocarbons having a double bond in the ring structure.
  • cycloolefin compounds such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene
  • compounds having a norbornene ring structure such as norbornene and dicyclopentadiene
  • cycloolefin compounds condensed with aromatic rings such as indene and acenaphthylene. etc.
  • norbornene compounds include those described in paragraphs 0037 to 0043 of JP-A-2018-39995, the contents of which are incorporated herein.
  • the cycloolefin compound illustrated here may further have the above-mentioned substituent Z.
  • the copolymerization ratio of the structural unit (c) shall be 10 mol% or more. is preferable, more preferably 20 mol% or more, and even more preferably 30 mol% or more.
  • the upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, even more preferably 70 mol% or less, may be 50 mol% or less, and may be 30 mol% or less. It may be the following.
  • the polymer (V) having the structural unit represented by formula (V) further incorporates a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as other polymerizable compound).
  • a different polymerizable compound hereinafter also referred to as other polymerizable compound.
  • other polymerizable compounds include compounds containing three vinyl groups. Specific examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, ethylene glycol diacrylate, butadiene, etc. may be mentioned.
  • the copolymerization ratio of the structural unit (d) derived from another polymerizable compound is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less. .
  • a polymer containing the structural unit (a) as essential and at least one of the structural units (b) to (d) is Illustrated. Furthermore, an embodiment in which the total of structural units (a) to (d) accounts for 95 mol% or more, and further 98 mol% or more of the total structural units is exemplified.
  • Another embodiment of the polymer (V) having a structural unit represented by formula (V) is a structural unit in which the structural unit (a) is essential, and among all the structural units excluding the terminal, the structural unit contains an aromatic ring. is preferably 90 mol% or more, more preferably 95 mol% or more, and may be 100 mol%.
  • one structural unit refers to the monomer used to produce the polymer (V) having the structural unit represented by formula (V) (for example, divinyl Aromatic compounds, monovinyl aromatic compounds, etc.) shall originate from one molecule.
  • the method for producing the polymer (V) having the structural unit represented by the formula (V) is not particularly limited and may be any conventional method.
  • a raw material containing a divinyl aromatic compound if necessary, a monovinyl aromatic compound compound, cycloolefin compound, etc.
  • a Lewis acid catalyst a metal fluoride such as boron trifluoride or a complex thereof can be used.
  • the molecular weight of the polymer (V) having a structural unit represented by formula (V) is preferably a number average molecular weight Mn of 300 or more, more preferably 500 or more, and 1,000 or more. More preferably, it is 1,500 or more.
  • the upper limit is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, and even more preferably 100,000 or less.
  • the molecular weight of the polymer (V) having a structural unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, in weight average molecular weight Mw, 10, More preferably, it is 000 or more.
  • the excellent low dielectric properties (Dk and/or Df) of the polymer (V) having the structural unit represented by formula (V), especially Df and the dielectric properties after moisture absorption, can be improved.
  • the upper limit is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less.
  • the monodispersity (Mw/Mn) expressed by the ratio of weight average molecular weight Mw to number average molecular weight Mn is preferably 100 or less, more preferably 50 or less, and even more preferably 20 or less. .
  • the lower limit is practically 1.1 or more, preferably 5 or more, more preferably 7 or more, and even more preferably 10 or more.
  • the above Mw and Mn are measured according to the description in the examples below.
  • the resin composition of the present embodiment contains two or more kinds of polymers (V) having structural units represented by formula (V), it is preferable that Mw, Mn, and Mw/Mn of the mixture satisfy the above ranges.
  • the equivalent weight of vinyl groups in the polymer (V) having the structural unit represented by formula (V) is 200 g/eq. or more, preferably 230g/eq. More preferably, it is 250 g/eq. It is more preferable that it is above. Further, the equivalent weight of the vinyl group is 1200 g/eq. It is preferably less than 1000g/eq. It is more preferable that it is less than 800g/eq. Below, 600g/eq. Below, 400g/eq. Below, 300g/eq. It may be the following. By setting it to the above lower limit or more, the storage stability of the resin composition tends to improve, and the fluidity of the resin composition tends to improve.
  • the content of the polymer (V) having a structural unit represented by formula (V) is 1 to 90 parts by mass when the resin solid content in the resin composition is 100 parts by mass.
  • the lower limit of the content of the polymer (V) having a structural unit represented by formula (V) is preferably 5 parts by mass or more when the resin solid content in the resin composition is 100 parts by mass. It is preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, may be 20 parts by mass or more, and may be 25 parts by mass or more.
  • the upper limit of the content of the polymer (V) having a structural unit represented by formula (V) is 80 parts by mass or less when the resin solid content in the resin composition is 100 parts by mass.
  • the amount is more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and may be 50 parts by mass or less, or 40 parts by mass or less.
  • the resin composition may contain only one type of polymer (V) having a structural unit represented by formula (V), or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
  • thermosetting compounds (C) contains a maleimide compound, an epoxy compound, a phenol compound, an oxetane resin, a benzoxazine compound, a compound (preferably) containing a (meth)allyl group other than the compound (M) represented by formula (M), It may further contain one or more other thermosetting compounds (C) selected from the group consisting of alkenyl nadiimide compounds) and polyphenylene ether compounds containing two or more carbon-carbon unsaturated double bonds. . By including such components, the desired performance required of the printed wiring board can be more effectively exhibited.
  • the resin composition of this embodiment may contain a maleimide compound other than the compound (M) represented by formula (M).
  • the resin composition of this embodiment has 2 or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2) per molecule.
  • the compound is not particularly limited as long as it has a maleimide group, and a wide variety of compounds commonly used in the field of printed wiring boards can be used.
  • maleimide compounds other than the compound (M) represented by formula (M) are preferably compounds represented by formulas (M2) to (M4) and formula (M6).
  • R 54 each independently represents a hydrogen atom or a methyl group, and n 4 represents an integer of 1 or more.
  • n 4 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1 or 2.
  • the compound represented by formula (M2) may be a mixture of compounds in which n 4 is different, and is preferably a mixture.
  • R 55 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and n 5 represents an integer of 1 to 10.
  • R 55 is preferably a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, or phenyl group; More preferably, it is a methyl group, and even more preferably a hydrogen atom.
  • n 5 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2.
  • the compound represented by formula (M3) may be a mixture of compounds having different n 5 values, and is preferably a mixture.
  • R 56 each independently represents a hydrogen atom, a methyl group, or an ethyl group
  • R 57 each independently represents a hydrogen atom or a methyl group.
  • the maleimide compound (M6) is a compound having a structural unit represented by formula (M6) and maleimide groups at both ends of the molecular chain.
  • R 61 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • R 62 is R 63 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. Represents a chain or branched alkyl group, or a straight or branched alkenyl group having 2 to 16 carbon atoms.
  • n independently represents an integer of 0 to 10.
  • Maleimide compounds other than the compound (M) represented by formula (M) may be produced by a known method, or commercially available products may be used.
  • Commercially available products include, for example, "BMI-2300” manufactured by Daiwa Kasei Kogyo Co., Ltd. as a compound represented by formula (M2), "MIR-3000” manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M3),
  • Examples of the compound represented by formula (M4) include "BMI-70” manufactured by K.I. Kasei Co., Ltd., and "MIZ-001” manufactured by Nippon Kayaku Co., Ltd. as the maleimide compound (M6).
  • maleimide compounds other than those mentioned above include compounds having two or more maleimide groups, specifically m-phenylenebismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl) ) Propane, 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenylsulfone bis Examples include maleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, prepolymers thereof, and prepolymers of these maleimides and amines.
  • the lower limit of its content should be 1 part by mass or more based on 100 parts by mass of resin solid content in the resin composition. It is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, and may be 25 parts by mass or more.
  • the content of the maleimide compound other than the compound (M) represented by formula (M) is 1 part by mass or more, the flame resistance of the obtained cured product tends to improve.
  • the upper limit of the content of maleimide compounds other than the compound (M) represented by formula (M) is preferably 70 parts by mass or less with respect to 100 parts by mass of resin solid content in the resin composition, It is more preferably 50 parts by mass or less, and may be 40 parts by mass or less.
  • the content of maleimide compounds other than the compound (M) represented by formula (M) is 70 parts by mass or less, the metal foil peel strength and low water absorption tend to improve.
  • the resin composition in this embodiment may contain only one type of maleimide compound other than the compound (M) represented by formula (M), or may contain two or more types of maleimide compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be made into the structure which does not contain substantially the maleimide compound other than the compound (M) represented by Formula (M).
  • “Substantially free” means that the content of maleimide compounds other than the compound (M) represented by formula (M) is less than 1 part by mass based on 100 parts by mass of resin solid content in the resin composition. Yes, it is preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass.
  • the resin composition of this embodiment may contain an epoxy compound.
  • An epoxy compound is a compound having one or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2) epoxy groups in one molecule. Alternatively, it is not particularly limited as long as it is a resin, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of epoxy compounds include bisphenol A epoxy resin, bisphenol E epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, phenol novolac epoxy resin, bisphenol A novolac epoxy resin, glycidyl ester epoxy resin, and aralkyl epoxy resin.
  • Novolac type epoxy resin biphenylaralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, multifunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolac type epoxy resin, phenol Aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, glycidyl amine, glycidyl ester, butadiene, etc.
  • Examples include compounds in which bonds are epoxidized and compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin. By using these, the moldability and adhesion of the resin composition are improved.
  • biphenylaralkyl epoxy resins, naphthylene ether epoxy resins, polyfunctional phenol epoxy resins, and naphthalene epoxy resins are preferred; More preferably, it is a type epoxy resin.
  • the resin composition of the present embodiment preferably contains an epoxy compound within a range that does not impair the effects of the present invention.
  • the content thereof is preferably 0.1 parts by mass or more, and 1 part by mass or more, based on 100 parts by mass of resin solids in the resin composition. It is more preferable that the amount is at least 2 parts by mass, and even more preferably 2 parts by mass or more.
  • the content of the epoxy compound is 0.1 part by mass or more, the metal foil peel strength and toughness of the obtained cured product tend to improve.
  • the upper limit of the content of the epoxy compound is preferably 50 parts by mass or less, and 30 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition.
  • the amount is more preferably at most 20 parts by mass, even more preferably at most 10 parts by mass, and may be at most 8 parts by mass, and may be at most 5 parts by mass.
  • the content of the epoxy compound is 50 parts by mass or less, the electrical properties of the obtained cured product tend to improve.
  • the resin composition in this embodiment may contain only one type of epoxy compound, or may contain two or more types of epoxy compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also have a structure that does not substantially contain an epoxy compound.
  • “Substantially free” means that the content of the epoxy compound is less than 0.1 parts by mass, preferably less than 0.01 parts by mass, based on 100 parts by mass of resin solids in the resin composition. , and even less than 0.001 part by mass.
  • the resin composition of this embodiment may contain a phenol compound.
  • the phenol compound has one or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2) phenolic hydroxyl groups in one molecule.
  • the phenol compound is not particularly limited, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the phenol compound include bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolak resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolac phenol.
  • Resin biphenylaralkyl type phenolic resin, cresol novolac type phenolic resin, polyfunctional phenolic resin, naphthol resin, naphthol novolak resin, polyfunctional naphthol resin, anthracene type phenolic resin, naphthalene skeleton modified novolak type phenolic resin, phenol aralkyl type phenolic resin,
  • Examples include naphthol aralkyl type phenol resin, dicyclopentadiene type phenol resin, biphenyl type phenol resin, alicyclic phenol resin, polyol type phenol resin, phosphorus-containing phenol resin, and hydroxyl group-containing silicone resin.
  • At least one selected from the group consisting of biphenyl aralkyl type phenol resin, naphthol aralkyl type phenol resin, phosphorus-containing phenol resin, and hydroxyl group-containing silicone resin is a seed.
  • the resin composition of the present embodiment preferably contains a phenol compound within a range that does not impair the effects of the present invention.
  • the content is preferably 0.1 part by mass or more, and 1 part by mass or more, based on 100 parts by mass of resin solids in the resin composition. It is more preferable that the amount is at least 2 parts by mass, and even more preferably 2 parts by mass or more. Further, the amount is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and 5 parts by mass or less. There may be.
  • the resin composition in this embodiment may contain only one type of phenol compound, or may contain two or more types of phenol compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also have a structure that does not substantially contain a phenol compound. “Substantially free” means that the content of the phenol compound is less than 0.1 parts by mass based on 100 parts by mass of resin solids in the resin composition.
  • the resin composition of this embodiment may contain oxetane resin.
  • the oxetane resin is particularly a compound having one or more oxetanyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2).
  • oxetanyl groups preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2.
  • oxetane resin examples include oxetane, alkyloxetane (for example, 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3,3-di(trifluoromethyl)oxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl-type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), OXT-121 (manufactured by Toagosei Co., Ltd.) ), etc.
  • alkyloxetane for example, 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethylox
  • the resin composition of this embodiment preferably contains an oxetane resin within a range that does not impair the effects of the present invention.
  • the content thereof is preferably 0.1 parts by mass or more, and 1 part by mass or more based on 100 parts by mass of resin solids in the resin composition. More preferably, the amount is 2 parts by mass or more.
  • the content of the oxetane resin is 0.1 parts by mass or more, the metal foil peel strength and toughness of the obtained cured product tend to improve.
  • the upper limit of the content of oxetane resin is preferably 50 parts by mass or less, and 30 parts by mass or less, based on 100 parts by mass of resin solid content in the resin composition. It is more preferably at most parts by mass, even more preferably at most 20 parts by mass, even more preferably at most 10 parts by mass, and may be at most 5 parts by mass.
  • the content of the oxetane resin is 50 parts by mass or less, the electrical properties of the resulting cured product tend to improve.
  • the resin composition in this embodiment may contain only one type of oxetane resin, or may contain two or more types of oxetane resin.
  • the resin composition in this embodiment can also be configured to substantially not contain oxetane resin.
  • substantially free means that the content of oxetane resin is less than 0.1 part by mass based on 100 parts by mass of resin solid content in the resin composition.
  • the resin composition of this embodiment may contain a benzoxazine compound.
  • the benzoxazine compound includes 2 or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2) dihydrobenzoxazines in one molecule. Any compound having a ring is not particularly limited, and a wide variety of compounds commonly used in the field of printed wiring boards can be used.
  • benzoxazine compounds include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.). (manufactured by), etc.
  • the resin composition of the present embodiment preferably contains a benzoxazine compound within a range that does not impair the effects of the present invention.
  • the content thereof is preferably 0.1 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of resin solids in the resin composition.
  • the resin composition in this embodiment may contain only one type of benzoxazine compound, or may contain two or more types of benzoxazine compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be configured to substantially not contain a benzoxazine compound. "Substantially free" means that the content of the benzoxazine compound is less than 0.1 part by mass based on 100 parts by mass of resin solid content in the resin composition.
  • the resin composition of this embodiment preferably contains a compound containing a (meth)allyl group, and more preferably contains a compound containing an allyl group.
  • the compound containing a (meth)allyl group is preferably a compound containing two or more (meth)allyl groups, and more preferably a compound containing two or more allyl groups.
  • the compound containing a (meth)allyl group preferably contains at least one selected from the group consisting of an allyl isocyanurate compound, an allyl group-substituted nadimide compound, an allyl compound having a glycoluril structure, and diallyl phthalate, It is more preferable to contain at least one selected from the group consisting of an allyl isocyanurate compound, an allyl group-substituted nadimide compound, and an allyl compound having a glycoluril structure, and more preferably an allyl group-substituted nadimide compound, and an alkenyl More preferred are nadimide compounds.
  • the resin composition of the present embodiment contains a compound containing a (meth)allyl group
  • its molecular weight is preferably 195 or more, more preferably 300 or more, and even more preferably 400 or more. , more preferably 500 or more.
  • the molecular weight of the compound containing a (meth)allyl group is also preferably 3,000 or less, more preferably 2,000 or less, even more preferably 1,000 or less, and even more preferably 800 or less.
  • the content thereof is preferably 1 part by mass or more, and 3 parts by mass or more, based on 100 parts by mass of resin solids in the resin composition. It is more preferably at least 5 parts by mass, even more preferably at least 5 parts by mass, and may be at least 10 parts by mass.
  • the upper limit of the content of the compound containing a (meth)allyl group is preferably 40 parts by mass or less, and preferably 30 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. More preferably, the amount is 20 parts by mass or less.
  • the resin composition of this embodiment may contain only one type of compound containing a (meth)allyl group, or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be configured to substantially not contain a compound containing a (meth)allyl group.
  • substantially free means that the content of the compound containing a (meth)allyl group is less than 0.1 part by mass based on 100 parts by mass of resin solid content in the resin composition.
  • allyl isocyanurate compound is not particularly defined as long as it has two or more allyl groups and an isocyanurate ring (nurate skeleton), but a compound represented by formula (TA) is preferable.
  • Formula (TA) (In formula (TA), RA represents a substituent).
  • R A represents a substituent, and a substituent having a formula weight of 15 to 500 is more preferable.
  • a first example of R A is an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms.
  • a resin composition capable of obtaining a cured product having excellent crosslinkability and high toughness by using an allyl compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. can be provided. Thereby, even if the resin composition does not include a base material such as glass cloth, it is possible to suppress cracking during etching treatment or the like.
  • the number of carbon atoms in the alkyl group and/or alkenyl group is preferably 3 or more, more preferably 8 or more, may be 12 or more, and is preferably 18 or less.
  • the resin composition has good resin flowability, and it is considered that the resin composition of the present embodiment has better circuit filling properties when producing a multilayer circuit board or the like.
  • R A is a group containing an allyl isocyanurate group.
  • the compound represented by formula (TA) is preferably a compound represented by formula (TA-1).
  • Formula (TA-1) (In formula (TA-1), R A2 is a divalent linking group.)
  • R A2 is preferably a divalent linking group having a formula weight of 54 to 250, and a divalent linking group having a formula weight of 54 to 250 and having carbon atoms at both ends. is more preferable, and an aliphatic hydrocarbon group having 2 to 20 carbon atoms is even more preferable (however, the aliphatic hydrocarbon group may contain an ether group, and may have a hydroxyl group). ). More specifically, R A2 is preferably a group represented by any of the following formulas (i) to (iii). (In the formulas (i) to (iii), p c1 represents the number of repeating units of the methylene group and is an integer from 2 to 18.
  • p c2 represents the number of repeating units of the oxyethylene group and is 0 or 1. .* is the binding site.)
  • the p c1 is preferably an integer of 2 to 10, more preferably an integer of 3 to 8, and still more preferably an integer of 3 to 5.
  • the p c2 may be 0 or 1, but is preferably 1.
  • R A2 is the first example.
  • alkenyl group having 2 to 22 carbon atoms include an allyl group and a decenyl group.
  • Specific examples of the compound represented by formula (TA) include triallylisocyanurate, 5-octyl-1,3-diallylisocyanurate, 5-dodecyl-1,3-diallylisocyanurate, 5-tetradecyl- 1,3-diallylisocyanurate, 5-hexadecyl-1,3-diallylisocyanurate, 5-octadecyl-1,3-diallylisocyanurate, 5-eicosyl-1,3-diallylisocyanurate, 5-docosyl-1, Examples include 3-diallylisocyanurate and 5-decenyl-1,3-diallylisocyanurate. These may be used alone or in combination of two or more, or may be used as a prepolymer.
  • the method for producing the compound represented by formula (TA) is not particularly limited, but for example, diallylisocyanurate and alkyl halide are mixed in an aprotic polar solvent such as N,N'-dimethylformamide, and sodium hydroxide is added. It can be obtained by reacting at a temperature of about 60°C to 150°C in the presence of a basic substance such as , potassium carbonate, or triethylamine.
  • TA commercially available compounds
  • Commercially available products include, but are not particularly limited to, L-DAIC manufactured by Shikoku Kasei Kogyo Co., Ltd., for example.
  • Examples of triallyl isocyanurate include TAIC manufactured by Mitsubishi Chemical Corporation.
  • Examples of the compound represented by formula (TA-1) include DD-1 manufactured by Shikoku Kasei Kogyo Co., Ltd.
  • the molecular weight of the allyl isocyanurate compound (preferably the compound represented by formula (TA)) is preferably 200 or more, more preferably 300 or more, even more preferably 400 or more, and even more preferably 500 or more. It is more preferable that By setting the molecular weight to the lower limit value or more, the resulting cured product tends to have improved low dielectric properties and heat resistance. Further, the molecular weight of the allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, More preferably, it is 800 or less. By controlling the molecular weight to be less than or equal to the upper limit value, the resulting cured product tends to have improved low thermal expansion properties.
  • the content thereof is preferably 1 part by mass or more, and 3 parts by mass or more based on 100 parts by mass of resin solids in the resin composition.
  • the amount is more preferably 5 parts by mass or more, and may be 10 parts by mass or more.
  • the upper limit of the content of the allyl isocyanurate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and 20 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. It is more preferably less than parts by mass.
  • the resin composition of this embodiment may contain only one type of allyl isocyanurate, or may contain two or more types of allyl isocyanurate. When two or more types are included, it is preferable that the total amount falls within the above range.
  • allyl-substituted nadimide compounds include compounds having one or more allyl-substituted nadimide groups in the molecule (preferably compounds having one or more alkenyl-substituted nadimide groups in the molecule (alkenylnadimide compounds) ), it is not particularly limited.
  • a specific example thereof is a compound represented by the following formula (AN).
  • R 1 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 2 represents an alkylene group having 1 to 6 carbon atoms
  • a phenylene group, a biphenylene group Represents a naphthylene group or a group represented by formula (AN-2) or (AN-3).
  • Formula (AN-3) (In formula (AN-3), R 4 each independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.)
  • AN a commercially available compound can also be used as the compound represented by formula (AN).
  • Commercially available compounds include, but are not particularly limited to, compounds represented by the formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)), compounds represented by the formula (AN-5), Examples include compounds such as BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.). These may be used alone or in combination of two or more.
  • the molecular weight of the allyl group-substituted nadimide compound (preferably the compound represented by formula (AN)) is preferably 400 or more, more preferably 500 or more, and may be 550 or more.
  • the molecular weight of the allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is also preferably 1,500 or less, more preferably 1,000 or less, even more preferably 800 or less, It may be 700 or less, or 600 or less.
  • the content thereof is 0 parts by mass based on 100 parts by mass of resin solid content in the resin composition. It is preferably at least .1 part by mass, more preferably at least 1 part by mass, and even more preferably at least 2 parts by mass. Further, the amount is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and 5 parts by mass or less. There may be.
  • an allyl group-substituted nadimide compound preferably a compound represented by formula (AN)
  • the content thereof is 0 parts by mass based on 100 parts by mass of resin solid content in the resin composition. It is preferably at least .1 part by mass, more preferably at least 1 part by mass, and even more preferably at least 2 parts by mass. Further, the amount is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass
  • the resin composition of the present embodiment may contain only one type of allyl group-substituted nadimide compound, or may contain two or more types of allyl group-substituted nadimide compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be configured to substantially not contain the allyl group-substituted nadimide compound. "Substantially free" means that the content of the allyl group-substituted nadimide compound is less than 0.1 part by mass based on 100 parts by mass of resin solid content in the resin composition.
  • each R is independently a hydrogen atom or a substituent, and at least two of R are groups containing an allyl group.
  • each R is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, and an alkenyl group having 2 to 5 carbon atoms.
  • it is an allyl group.
  • R is preferably a group containing three or four allyl groups, and more preferably a group containing four allyl groups.
  • a specific example of the compound represented by formula (GU) is 1,3,4,6-tetraallylglycoluril (a compound in which all R's are allyl groups in formula (GU)).
  • GUI a commercially available one can also be used.
  • Commercially available products include, but are not particularly limited to, TA-G manufactured by Shikoku Kasei Kogyo Co., Ltd., for example.
  • the molecular weight of the allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, even more preferably 250 or more, It may be 300 or more, or 400 or more.
  • the molecular weight of the allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, further preferably 800 or less. It is preferably 700 or less, or may be 600 or less.
  • the content thereof is based on 100 parts by mass of resin solid content in the resin composition. , is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may be 10 parts by mass or more.
  • the upper limit of the content of the allyl compound having a glycoluril structure is 40 parts by mass or less based on 100 parts by mass of the resin solid content in the resin composition.
  • the amount is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, and may be 20 parts by mass or less.
  • the resin composition of this embodiment may contain only one kind of allyl compound having a glycoluril structure, or may contain two or more kinds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition of this embodiment may contain a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds.
  • the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is preferably a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminal, and a (meth)acrylic group at the terminal, More preferably, it is a polyphenylene ether compound having two or more groups selected from the group consisting of a maleimide group and a vinylbenzyl group.
  • the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is exemplified by a compound having a phenylene ether skeleton represented by the following formula (X1).
  • R 24 , R 25 , R 26 , and R 27 may be the same or different, and represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.
  • the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds has the formula (X2): (In formula (X2), R 28 , R 29 , R 30 , R 34 , and R 35 may be the same or different and represent an alkyl group or a phenyl group having 6 or less carbon atoms.
  • R 31 , R 32 , and R 33 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • -A- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is a modified polyphenylene ether compound (hereinafter referred to as a "modified polyphenylene ether compound (g )" is preferable, and a modified polyphenylene ether compound having two or more groups selected from the group consisting of a (meth)acrylic group, a maleimide group, and a vinylbenzyl group at the terminal is more preferable.
  • a modified polyphenylene ether compound (g) it becomes possible to further reduce the dielectric loss tangent (Df) of the cured product of the resin composition, and to increase low water absorption and metal foil peel strength. .
  • Df dielectric loss tangent
  • These may be used alone or in combination of two or more.
  • Examples of the modified polyphenylene ether compound (g) include a compound represented by formula (OP-1).
  • X represents an aromatic group
  • -(Y-O)n 2 - represents a polyphenylene ether structure
  • R 1 , R 2 and R 3 are each independently, Represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group
  • n 1 represents an integer of 1 to 6
  • n 2 represents an integer of 1 to 100
  • n 3 represents an integer of 1 to 4.
  • the n 2 structural units (YO) and/or the n 3 structural units may be the same or different.
  • n 3 is preferably 2 or more, more preferably 2.
  • the modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2).
  • -(O-X-O)- is the formula (OP-3):
  • R 4 , R 5 , R 6 , R 10 , and R 11 may be the same or different and are an alkyl group or a phenyl group having 6 or less carbon atoms.
  • R 7 , R 8 and R 9 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • formula (OP-4) (In formula (OP-4), R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 may be the same or different, and each has a hydrogen atom and a carbon number of 6 or less. is an alkyl group or phenyl group.
  • -A- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • -(YO)- is the formula (OP-5):
  • R 20 and R 21 may be the same or different and are an alkyl group or a phenyl group having 6 or less carbon atoms.
  • R 22 and R 23 may be the same or different, It is preferably represented by a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • a and b represent an integer of 0 to 100, at least one of which is not 0, preferably an integer of 0 to 50, more preferably an integer of 1 to 30. preferable.
  • 2 or more -(YO)- may each independently be an array of one type of structure, or two or more types of structures may be a block or They may be arranged randomly.
  • -A- in formula (OP-4) is, for example, a methylene group, ethylidene group, 1-methylethylidene group, 1,1-propylidene group, 1,4-phenylenebis(1-methylethylidene) group, 1, Examples include, but are not limited to, divalent organic groups such as 3-phenylenebis(1-methylethylidene) group, cyclohexylidene group, phenylmethylene group, naphthylmethylene group, and 1-phenylethylidene group.
  • R 4 , R 5 , R 6 , R 10 , R 11 , R 20 and R 21 are alkyl groups having 3 or less carbon atoms
  • R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 22 and R 23 are hydrogen atoms or alkyl groups having 3 or less carbon atoms
  • polyphenylene ether Compounds are preferred, and in particular -(O-X-O)- represented by formula (OP-3) or formula (OP-4) is represented by formula (OP-9), formula (OP-10), and/or Formula (OP-11), and -(YO)- represented by formula (OP-5) is preferably formula (OP-12) or formula (OP-13).
  • -(Y-O)- of 2 or more each independently represents a structure in which two or more of formula (OP-12) and/or formula (OP-13) are arranged. Alternatively, it may have a structure in which formula (OP-12) and formula (OP-13) are arranged in blocks or randomly.
  • R 44 , R 45 , R 46 , and R 47 may be the same or different and are a hydrogen atom or a methyl group.
  • -B- is a straight line having 20 or less carbon atoms. It is a chain, branched, or cyclic divalent hydrocarbon group.
  • Specific examples of -B- include the same examples as -A- in formula (OP-4).
  • -B- is a straight chain, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • Specific examples of -B- include the same examples as -A- in formula (OP-4).
  • JP 2018-016709 for details of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, the description in JP 2018-016709 can be referred to, and the contents thereof are incorporated herein.
  • the number average molecular weight of a polyphenylene ether compound (preferably a modified polyphenylene ether compound (g)) containing two or more carbon-carbon unsaturated double bonds in terms of polystyrene determined by the GPC (gel permeation chromatography) method (details will be given in Examples below) (according to the method described in ) is preferably 500 or more and 3,000 or less.
  • the number average molecular weight is 500 or more, stickiness tends to be further suppressed when the resin composition of this embodiment is formed into a coating film.
  • the number average molecular weight is 3,000 or less, the solubility in a solvent tends to be further improved.
  • the weight average molecular weight of a polyphenylene ether compound (preferably a modified polyphenylene ether compound (g)) containing two or more carbon-carbon unsaturated double bonds (preferably a modified polyphenylene ether compound (g)) in terms of polystyrene by GPC (for details, follow the method described in the Examples below) ) is preferably 800 or more and 10,000 or less, more preferably 800 or more and 5,000 or less.
  • the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to become lower.
  • the solubility, low viscosity, and moldability of the resin composition in the solvent during production tend to be further improved.
  • the terminal carbon-carbon unsaturated double bond equivalent is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, and 400 to 2500 g. It is more preferable that By setting it above the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to become lower. By setting it below the above upper limit, the solubility, low viscosity, and moldability of the resin composition in a solvent tend to be further improved.
  • the lower limit of the content of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is , preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and 7 parts by mass, based on 100 parts by mass of resin solids in the resin composition. It is more preferable that the amount is above, and even more preferably that it is 10 parts by mass or more. When the amount is equal to or more than the lower limit, the resulting cured product tends to have improved low water absorption and low dielectric properties (Dk and/or Df).
  • the upper limit of the content of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is preferably 70 parts by mass or less, and 60 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. It is more preferably at most 50 parts by mass, even more preferably at most 40 parts by mass, even more preferably at most 35 parts by mass, and even more preferably at most 25 parts by mass. Even more preferably, the amount may be 20 parts by mass or less. When the amount is below the upper limit, the heat resistance and chemical resistance of the resulting cured product tend to be further improved.
  • the resin composition in this embodiment may contain only one type of polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be configured to substantially not contain a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds.
  • substantially free means that the content of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is less than 0.1 part by mass based on 100 parts by mass of resin solid content in the resin composition. It is preferably less than 0.01 part by mass, and may even be less than 0.001 part by mass.
  • the content (total amount) is preferably 1 part by mass or more, and 5 parts by mass based on 100 parts by mass of the resin solid content.
  • the amount is more preferably at least 10 parts by mass, even more preferably at least 10 parts by mass, even more preferably at least 20 parts by mass, and may be at least 30 parts by mass.
  • the upper limit of the content of the other thermosetting compound (C) is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, and 50 parts by mass or less, based on 100 parts by mass of the resin solid content. It is more preferably at most 45 parts by mass, even more preferably at most 40 parts by mass. By setting it below the above-mentioned upper limit, the low dielectric properties (Dk and/or Df) and low water absorption of the obtained cured product tend to be further improved.
  • the resin composition of this embodiment may contain only one type of other thermosetting compound (C), or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition of this embodiment contains a filler (D).
  • a filler (D) By including the filler (D), physical properties such as dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame resistance, low thermal expansion, etc. of the resin composition and its cured product can be further improved.
  • the filler (D) used in this embodiment has excellent low dielectric properties (Dk and/or Df).
  • the filler (D) used in this embodiment preferably has a dielectric constant (Dk) of 8.0 or less, and preferably 6.0 or less, at a frequency of 10 GHz measured according to the cavity resonator perturbation method. More preferably, it is 4.0 or less.
  • the lower limit of the relative permittivity is practically, for example, 2.0 or more.
  • the filler (D) used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, at a frequency of 10 GHz measured according to the cavity resonator perturbation method. preferable.
  • the lower limit value of the dielectric loss tangent is practically, for example, 0.0001 or more.
  • filler (D) used in this embodiment is not particularly limited, and those commonly used in the industry can be suitably used.
  • silicas such as natural silica, fused silica, synthetic silica, amorphous silica, Aerosil, and hollow silica, metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, and zirconium oxide.
  • complex oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, nitrides such as boron nitride, agglomerated boron nitride, silicon nitride, aluminum nitride, aluminum hydroxide, Heat-treated aluminum hydroxide products (aluminum hydroxide heat-treated to reduce some of the crystal water), metal hydroxides (including hydrates) such as boehmite and magnesium hydroxide, molybdenum oxide and molybdic acid Molybdenum compounds such as zinc, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, Inorganic fillers such as S-glass, M-glass G20, short glass fibers (including fine glass powders such as E glass,
  • organic fillers such as styrene-type, butadiene-type, acrylic-type rubber powders, core-shell type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders.
  • inorganic fillers are preferred and are selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. It is more preferable to include one or more types, and from the viewpoint of low dielectric properties (Dk and/or Df), it is more preferable to include one or more types selected from the group consisting of silica and aluminum hydroxide. It is further preferred that silica is included. By using these inorganic fillers, properties such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardance of the cured product of the resin composition are further improved.
  • the content of the filler (D) in the resin composition of the present embodiment can be appropriately set depending on the desired properties, and is not particularly limited, but the content is based on 100 parts by mass of the resin solid content in the resin composition. It is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 40 parts by mass or more, even more preferably 60 parts by mass or more, and even more preferably 80 parts by mass or more. is even more preferable. When the amount is equal to or more than the lower limit, the resulting cured product tends to have improved low thermal expansion and low dielectric loss tangent.
  • the upper limit of the content of the filler (D) is preferably 1,600 parts by mass or less, more preferably 1,000 parts by mass or less, and 500 parts by mass or less, based on 100 parts by mass of the resin solid content. It is more preferably at most 300 parts by mass, even more preferably at most 250 parts by mass, and may be at most 200 parts by mass, or even at most 120 parts by mass. By setting it below the above upper limit, the moldability of the resin composition tends to be further improved.
  • the content of the filler (D) is 1 to 95% by mass of the components excluding the solvent, and the content of the filler (D) is 30 to 80% by mass. Certain embodiments are preferred.
  • the resin composition of this embodiment may contain only one type of filler (D), or may contain two or more types of filler (D). When two or more types are included, it is preferable that the total amount falls within the above range.
  • a filler (D) when using a filler (D), especially an inorganic filler, it may further contain a silane coupling agent.
  • a silane coupling agent By including a silane coupling agent, the dispersibility of the filler (D) and the adhesive strength between the resin component and the filler (D) and the substrate described below tend to be further improved.
  • Silane coupling agents are not particularly limited, and include silane coupling agents that are generally used for surface treatment of inorganic materials, such as aminosilane compounds (for example, ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl) - ⁇ -aminopropyltrimethoxysilane, etc.), epoxysilane compounds (e.g., ⁇ -glycidoxypropyltrimethoxysilane, etc.), vinylsilane compounds (e.g., vinyltrimethoxysilane, etc.), styrylsilane compounds (e.g., p-styryltrimethoxysilane, etc.), acrylic silane compounds (e.g., ⁇ -acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ - (aminopropyltrimeth
  • the resin composition of the present embodiment is a low-molecular vinyl compound (hereinafter simply referred to as a "low-molecular vinyl compound”) having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule. ) may also be included.
  • a low molecular weight vinyl compound By blending a low molecular weight vinyl compound, the moisture absorption and heat resistance of the resulting cured product tends to be further improved.
  • the carbon-carbon unsaturated bonds constituting the organic group containing carbon-carbon unsaturated bonds do not include those included as part of an aromatic ring.
  • carbon-carbon unsaturated bonds contained as part of non-aromatic rings are meant to include carbon-carbon unsaturated bonds contained as part of non-aromatic rings.
  • An example of a carbon-carbon unsaturated bond included as part of the non-aromatic ring includes a cyclohexenyl group. It is also intended to include portions other than the terminals of linear or branched organic groups, ie, carbon-carbon unsaturated bonds (eg, vinylene groups) contained in the linear or branched chains.
  • the organic group containing a carbon-carbon unsaturated bond is more preferably one selected from the group consisting of a vinyl group, an allyl group, an acrylic group, and a methacrylic group, and even more preferably a vinyl group. .
  • the low-molecular-weight vinyl compound used in this embodiment is also preferably composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, oxygen atoms, nitrogen atoms, and silicon atoms; More preferably, it is composed only of atoms selected from the group consisting of atoms, oxygen atoms, and silicon atoms, and it is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, and oxygen atoms. It is even more preferable.
  • the low molecular weight vinyl compound used in this embodiment may or may not have a polar group. It is preferable that the low molecular weight vinyl compound used in this embodiment has no polar group. Examples of the polar group include an amino group, a carboxyl group, a hydroxy group, and a nitro group.
  • the molecular weight of the low molecular weight vinyl compound is preferably 70 or more, more preferably 80 or more, and even more preferably 90 or more.
  • the upper limit of the molecular weight of the low molecular vinyl compound is preferably 500 or less, more preferably 400 or less, even more preferably 300 or less, even more preferably 200 or less, and 150 or less. Good too.
  • the effect of increasing the reactivity with the polymer (V) having the structural unit represented by the formula (V) tends to be further improved.
  • the resin composition of the present embodiment contains two or more kinds of low-molecular-weight vinyl compounds, it is preferable that the average molecular weight value of the low-molecular-weight vinyl compounds is within the above range, and the molecular weight of each compound is within the above preferable range. is more preferable.
  • the low molecular weight vinyl compound preferably has a boiling point of 110°C or higher, more preferably 115°C or higher, and even more preferably 120°C or higher.
  • a boiling point of 110°C or higher is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower.
  • the amount By controlling the amount to be less than or equal to the upper limit, it is possible to make it difficult for residual solvent to remain in the cured product.
  • the resin composition of the present embodiment contains two or more types of low-molecular-weight vinyl compounds, it is sufficient if the average value of the boiling points falls within the above-mentioned range, but it is preferable that the boiling point of each compound falls within the above-mentioned preferred range.
  • low-molecular vinyl compounds examples include (meth)acrylic acid ester compounds, aromatic vinyl compounds (preferably styrene compounds), saturated fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, and ethylenically unsaturated carboxylic acids.
  • Anhydrides ethylenically unsaturated dicarboxylic acid monoalkyl esters, ethylenically unsaturated carboxylic acid amides, vinyl silane compounds (e.g., vinyltrialkoxysilanes, etc.), acrylic silane compounds (e.g., acrylic trialkoxysilanes, etc.), methacrylsilane compounds (for example, methacryltrialkoxysilane, etc.), styrylsilane compounds (for example, styryltrialkoxysilane, etc.), and the like.
  • vinyl silane compounds e.g., vinyltrialkoxysilanes, etc.
  • acrylic silane compounds e.g., acrylic trialkoxysilanes, etc.
  • methacrylsilane compounds for example, methacryltrialkoxysilane, etc.
  • styrylsilane compounds for example, styryltrialkoxysilane, etc.
  • the first forms of low-molecular vinyl compounds include (meth)acrylic acid ester compounds, aromatic vinyl compounds, saturated fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides, It is at least one selected from the group consisting of ethylenically unsaturated dicarboxylic acid monoalkyl esters and ethylenically unsaturated carboxylic acid amides.
  • the second form of the low molecular weight vinyl compound is selected from the group consisting of (meth)acrylic acid ester compounds, aromatic vinyl compounds, saturated fatty acid vinyl compounds, vinyl silane compounds, acrylic silane compounds, methacrylic silane compounds, and styryl silane compounds. It is at least one kind, and aromatic vinyl compounds and/or vinyl silane compounds are preferred. Specific examples of low molecular weight vinyl compounds include methylstyrene, ethylvinylbenzene, vinyltrimethoxysilane, and vinyltriethoxysilane.
  • the content of the low molecular weight vinyl compound is preferably 1 part by mass or more, more preferably 2 parts by mass or more, based on 100 parts by mass of the resin solid content. More preferably, the amount is 5 parts by mass or more.
  • the amount is equal to or more than the lower limit, the amount of unreacted functional groups in the obtained cured product tends to decrease, and the moisture absorption and heat resistance tends to improve.
  • the upper limit of the content of the low molecular weight vinyl compound is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and 10 parts by mass or less based on 100 parts by mass of the resin solid content.
  • the resin composition of this embodiment may contain only one type of low-molecular-weight vinyl compound, or may contain two or more types of low-molecular-weight vinyl compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the mass ratio of the polymer (V) having the structural unit represented by formula (V) and the low molecular weight vinyl compound is such that the mass ratio of the polymer (V) having the structural unit represented by formula (V) is It is preferably 0.025 or more, more preferably 0.05 or more, based on 1 of coalescence (V).
  • the amount is equal to or more than the lower limit, the amount of unreacted functional groups in the obtained cured product tends to decrease, and the moisture absorption and heat resistance tends to improve.
  • the upper limit of the mass ratio of the polymer (V) having the structural unit represented by the above formula (V) and the low molecular weight vinyl compound is 1 for the polymer (V) having the structural unit represented by the formula (V).
  • the low dielectric properties (Dk and/or Df) of the obtained cured product tend to be further improved.
  • ⁇ Oligomer having ethylenically unsaturated group It is also possible to use an oligomer having an ethylenically unsaturated group in the resin composition of this embodiment in order to enhance thermosetting properties and curability by active energy rays (for example, photocurability by ultraviolet rays). .
  • the oligomer having an ethylenically unsaturated group used in this embodiment is not particularly limited as long as it has one or more ethylenically unsaturated group in one molecule.
  • Examples include oligomers having an acryloyl group, etc., and oligomers having a vinyl group are preferred.
  • a compound that corresponds to an oligomer having an ethylenically unsaturated group and also corresponds to a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is referred to as a carbon-carbon unsaturated group.
  • the oligomer having an ethylenically unsaturated group is preferably a styrene oligomer.
  • the styrene oligomer according to the present embodiment is preferably formed by polymerizing at least one member selected from the group consisting of styrene, the above-mentioned styrene derivatives, and vinyltoluene.
  • the number average molecular weight of the styrene oligomer is preferably 178 or more, and preferably 1,600 or less. Further, the styrene oligomer is preferably a compound without a branched structure having an average number of aromatic rings of 2 to 14, a total amount of 2 to 14 aromatic rings of 50% by mass or more, and a boiling point of 300° C. or more.
  • styrene oligomer examples include styrene polymer, vinyltoluene polymer, ⁇ -methylstyrene polymer, vinyltoluene- ⁇ -methylstyrene polymer, styrene- ⁇ -styrene polymer, etc. .
  • styrene polymer commercially available products may be used, such as Picolastic A5 (manufactured by Eastman Chemical Company), Picolastic A-75 (manufactured by Eastman Chemical Company), Picotex 75 (manufactured by Eastman Chemical Company), Examples include FTR-8100 (manufactured by Mitsui Chemicals, Inc.) and FTR-8120 (manufactured by Mitsui Chemicals, Inc.). Furthermore, examples of the vinyltoluene- ⁇ -methylstyrene polymer include Picotex LC (manufactured by Eastman Chemical Company).
  • Crystallex 3070 manufactured by Eastman Chemical Company
  • Crystallex 3085 manufactured by Eastman Chemical Company
  • Crystallex 5140 manufactured by Eastman Chemical Company
  • FMR -0100 manufactured by Mitsui Chemicals, Inc.
  • FMR-0150 manufactured by Mitsui Chemicals, Inc.
  • examples of the styrene- ⁇ -styrene polymer include FTR-2120 (manufactured by Mitsui Chemicals, Inc.). These styrene oligomers may be used alone or in combination of two or more.
  • ⁇ -methylstyrene oligomer is preferable because it can be thermally cured well and is excellent in embedding of fine wiring, soldering heat resistance, low dielectric constant, and low dielectric loss tangent.
  • the content thereof is preferably 0.5 parts by mass or more based on 100 parts by mass of resin solids in the resin composition. , more preferably 1 part by mass or more, further preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and furthermore, may be 5 parts by mass or more.
  • the amount is equal to or more than the lower limit, the resulting cured product tends to have improved low dielectric properties.
  • the upper limit of the content of the oligomer having an ethylenically unsaturated group is preferably 30 parts by mass or less, and preferably 25 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition.
  • the content is more preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less.
  • the resin composition of the present embodiment may contain only one kind of oligomer having an ethylenically unsaturated group, or may contain two or more kinds of oligomers having an ethylenically unsaturated group. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition of this embodiment may contain a thermoplastic elastomer.
  • the thermoplastic elastomer in this embodiment is not particularly limited, and includes, for example, polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene. , styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof.
  • the number average molecular weight of the thermoplastic elastomer used in this embodiment is preferably 50,000 or more. By setting the number average molecular weight to 50,000 or more, the resulting cured product tends to have better low dielectric properties (Dk and/or Df).
  • the number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, and even more preferably 80,000 or more.
  • the upper limit of the number average molecular weight of the thermoplastic elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. By setting it below the upper limit, the solubility of the thermoplastic elastomer component in the resin composition tends to improve.
  • the resin composition of this embodiment contains two or more types of thermoplastic elastomers, it is preferable that the number average molecular weight of the mixture satisfies the above range.
  • thermoplastic elastomer is preferably a thermoplastic elastomer containing a styrene monomer unit and a conjugated diene monomer unit (hereinafter referred to as "thermoplastic elastomer (E)").
  • thermoplastic elastomer (E) a thermoplastic elastomer containing a styrene monomer unit and a conjugated diene monomer unit
  • the thermoplastic elastomer (E) contains styrene monomer units. By including the styrene monomer unit, the solubility of the thermoplastic elastomer (E) in the resin composition is improved.
  • Styrene monomers include styrene, ⁇ -methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, N,N-diethyl-p-aminoethylstyrene, etc.
  • styrene ⁇ -methylstyrene, and p-methylstyrene are preferred from the viewpoint of availability and productivity.
  • styrene is particularly preferred.
  • the content of styrene monomer units in the thermoplastic elastomer (E) is preferably in the range of 10 to 50% by mass, more preferably in the range of 13 to 45% by mass, and more preferably in the range of 15 to 40% by mass of the total monomer units. The range of is more preferable. If the content of styrene monomer units is 50% by mass or less, the adhesiveness and tackiness to the substrate etc. will be better.
  • thermoplastic elastomer (E) may contain only one type of styrene monomer unit, or may contain two or more types of styrene monomer units. When two or more types are included, it is preferable that the total amount is within the above range.
  • the description in International Publication No. 2017/126469 can be referred to, and the content thereof is incorporated herein. The same applies to the conjugated diene monomer unit, etc., which will be described later.
  • the thermoplastic elastomer (E) contains a conjugated diene monomer unit. By including the conjugated diene monomer unit, the solubility of the thermoplastic elastomer (E) in the resin composition is improved.
  • the conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds.
  • Conjugated diene monomers include, for example, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl- Examples include 1,3-pentadiene, 1,3-hexadiene, and farnesene, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred.
  • the thermoplastic elastomer (E) may contain only one type of conjugated diene monomer unit, or may contain two or more types.
  • thermoplastic elastomer (E) all or some of the conjugated diene bonds of the thermoplastic elastomer may be hydrogenated, or may not be hydrogenated.
  • the thermoplastic elastomer (E) may or may not contain other monomer units in addition to the styrene monomer unit and the conjugated diene monomer unit.
  • examples of other monomer units include aromatic vinyl compound units other than styrene monomer units.
  • the sum of styrene monomer units and conjugated diene monomer units is preferably 90% by mass or more, more preferably 95% by mass or more of the total monomer units. , more preferably 97% by mass or more, even more preferably 99% by mass or more.
  • thermoplastic elastomer (E) may contain only one type of styrene monomer unit and conjugated diene monomer unit, or may contain two or more types of each. When two or more types are included, it is preferable that the total amount falls within the above range.
  • thermoplastic elastomer (E) used in this embodiment may be a block polymer or a random polymer.
  • the thermoplastic elastomer (E) is an unhydrogenated elastomer.
  • Unhydrogenated elastomer refers to an elastomer in which the proportion of double bonds based on conjugated diene monomer units that are hydrogenated, that is, the hydrogenation rate (hydrogenation rate) is 20% or less. .
  • the hydrogenation rate is preferably 15% or less, more preferably 10% or less, even more preferably 5% or less.
  • thermoplastic elastomers (E) used in this embodiment include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd. and SEPTON (registered trademark) 2104 manufactured by Asahi Kasei Corporation. O. R. (registered trademark) S1606, S1613, S1609, S1605, manufactured by JSR Corporation, DYNARON (registered trademark) 9901P, TR2250, and the like.
  • the content thereof is preferably 1 part by mass or more based on 100 parts by mass of the resin solid content, It is more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and may be 15 parts by mass or more.
  • the upper limit of the content of the thermoplastic elastomer is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, and 35 parts by mass or less based on 100 parts by mass of the resin solid content.
  • the resin composition of this embodiment may contain only one type of thermoplastic elastomer, or may contain two or more types of thermoplastic elastomer. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition of this embodiment may contain a flame retardant.
  • the flame retardant include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, with phosphorus-based flame retardants being preferred.
  • Known flame retardants can be used, such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromo Halogen flame retardants such as toluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, chlorinated paraffin, red phosphorus, tricresyl phosphate, triphenyl phosphate , cresyl diphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl) phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl
  • Examples include flame retardants, silicone-based flame retardants such as silicone rubber, and silicone resin.
  • 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferred because it does not impair low dielectric properties (Dk and/or Df).
  • the content thereof is preferably 1 part by mass or more, and preferably 5 parts by mass or more, based on 100 parts by mass of resin solids in the resin composition. is more preferable, still more preferably 10 parts by mass or more, and may be 15 parts by mass or more. Further, the lower limit of the flame retardant content is preferably 30 parts by mass or less, more preferably 25 parts by mass or less.
  • One kind of flame retardant can be used alone or two or more kinds can be used in combination. When two or more types are used, the total amount falls within the above range.
  • the resin composition of this embodiment may contain an active ester compound within a range that does not impair the effects of the present invention.
  • the active ester compound is not particularly limited, and for example, the description in paragraphs 0064 to 0066 of International Publication No. 2021/172317 can be referred to, the contents of which are incorporated herein.
  • the resin composition of this embodiment contains an active ester compound, it is preferably 1 part by mass or more, and preferably 50 parts by mass or less, based on 100 parts by mass of resin solid content in the resin composition. .
  • the resin composition in this embodiment may contain only one type of active ester compound, or may contain two or more types of active ester compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
  • the resin composition in this embodiment can also be configured to substantially not contain an active ester compound. "Substantially free" means that the content of the active ester compound is less than 1 part by mass, preferably less than 0.1 part by mass, per 100 parts by mass of resin solids in the resin composition. More preferably, it is less than 0.01 part by mass.
  • the resin composition of this embodiment may contain a dispersant.
  • a dispersant those commonly used for paints can be suitably used, and the type thereof is not particularly limited.
  • a copolymer-based wetting and dispersing agent is used, and specific examples thereof include DISPERBYK®-110, 111, 161, 180, 2009, and 2152 manufactured by BYK Chemie Japan Co., Ltd. , 2155, BYK (registered trademark)-W996, W9010, W903, W940, etc.
  • the lower limit of its content is preferably 0.01 parts by mass or more, and 0.01 parts by mass or more, based on 100 parts by mass of resin solids in the resin composition. It is more preferably 1 part by mass or more, and may be 0.3 part by mass or more.
  • the upper limit of the content of the dispersant is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and 3 parts by mass based on 100 parts by mass of resin solids in the resin composition. The following may be sufficient.
  • One type of dispersant can be used alone or two or more types can be used in combination. When two or more types are used, the total amount falls within the above range.
  • the resin composition of this embodiment may further contain a curing accelerator.
  • the curing accelerator include, but are not limited to, imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di- tert-butyl-di-perphthalate, ⁇ , ⁇ '-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 2,5-dimethyl- Organic peroxides such as 2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitrile; N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine , 2-N-
  • the lower limit of its content is preferably 0.005 parts by mass or more with respect to 100 parts by mass of resin solids in the resin composition, and 0. It is more preferably .01 part by mass or more, and even more preferably 0.1 part by mass or more.
  • the upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and 2 parts by mass or less, based on 100 parts by mass of resin solids in the resin composition. It is more preferable that the amount is less than 1 part.
  • the curing accelerator can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.
  • the resin composition of this embodiment may contain a solvent, and preferably contains an organic solvent.
  • the resin composition of the present embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the various resin solid components described above are dissolved or compatible with the solvent.
  • the solvent is not particularly limited as long as it is a polar organic solvent or a non-polar organic solvent that can dissolve or be compatible with at least a portion, preferably all, of the various resin solids mentioned above.
  • Examples of the polar organic solvent include ketones, etc.
  • nonpolar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.).
  • solvent e.g., toluene, xylene, etc.
  • One kind of solvent can be used alone or two or more kinds can be used in combination. When two or more types are used, the total amount falls within the above range.
  • the resin composition of this embodiment may contain various polymeric compounds such as thermoplastic resins and oligomers thereof, and various additives in addition to the above-mentioned components.
  • Additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, optical brighteners, photosensitizers, dyes, pigments, thickeners, fluidity regulators, lubricants, antifoaming agents, leveling agents, and gloss. agents, polymerization inhibitors, etc. These additives can be used alone or in combination of two or more.
  • the resin composition of this embodiment is used as a cured product.
  • the resin composition of this embodiment is suitable as a low dielectric constant material and/or a low dielectric loss tangent material as a resin composition for electronic materials such as insulating layers of printed wiring boards, materials for semiconductor packages, etc. Can be used.
  • the resin composition of this embodiment can be suitably used as a material for prepreg, a metal foil-clad laminate using prepreg, a resin composite sheet, and a printed wiring board.
  • the resin composition of this embodiment preferably has a low dielectric constant (Dk) when molded into a cured plate with a thickness of 0.8 mm.
  • the dielectric constant (Dk) at a frequency of 10 GHz measured according to the cavity resonator perturbation method is preferably 2.60 or less, more preferably 2.50 or less.
  • the lower limit of the dielectric constant (Dk) is not particularly determined, for example, 0.01 or more is practical.
  • the resin composition of this embodiment has a low dielectric loss tangent (Df) when molded into a cured plate with a thickness of 0.8 mm.
  • the dielectric loss tangent (Df) at a frequency of 10 GHz measured according to the cavity resonator perturbation method is preferably less than 0.0026, more preferably less than 0.0023.
  • the lower limit value of the dielectric loss tangent (Df) is not particularly determined, for example, 0.0001 or more is practical.
  • Such low dielectric properties (Dk and/or Df) are mainly achieved by using a polymer (V) having a structural unit represented by formula (V). More specifically, the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured plate are measured by the method described in the Examples described below.
  • the cured product of the resin composition of the present embodiment preferably has a glass transition temperature (Tan ⁇ ) according to DMA (dynamic mechanical measurement) of 230°C or higher, more preferably 250°C or higher.
  • a glass transition temperature is achieved mainly by using a compound (M) represented by formula (M).
  • M represented by formula (M).
  • the practical upper limit of the glass transition temperature is, for example, 350° C. or lower. More specifically, the glass transition temperature (Tan ⁇ ) is measured by the method described in the Examples below.
  • the cured product of the resin composition of this embodiment preferably has a low coefficient of thermal expansion (CTE).
  • CTE coefficient of thermal expansion
  • the linear thermal expansion coefficient in the direction perpendicular to the plane measured by the TMA method specified in JlS C 6481 5.19 is 80 ppm/ It is preferably at most 70 ppm/°C, more preferably at most 70 ppm/°C.
  • 0 is ideal, but 0.001 ppm/°C or more is practical.
  • CTE is measured by the method described in Examples below.
  • the resin composition of this embodiment is used as a layered material (including film-like, sheet-like, etc.) such as prepreg, resin composite sheet, etc., which becomes an insulating layer of a printed wiring board.
  • the thickness is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more.
  • the upper limit of the thickness is preferably 200 ⁇ m or less, more preferably 180 ⁇ m or less.
  • the thickness of the above-mentioned layered material means the thickness including the glass cloth, for example, when the resin composition of the present embodiment is impregnated into a glass cloth or the like.
  • the material formed from the resin composition of this embodiment may be used for forming a pattern by exposure and development, or may be used for applications that are not exposed and developed. It is particularly suitable for applications that do not involve exposure and development.
  • the prepreg of this embodiment is formed from a base material (prepreg base material) and the resin composition of this embodiment.
  • the prepreg of the present embodiment can be produced by, for example, applying the resin composition of the present embodiment to a base material (for example, impregnating and/or coating it), and then heating it (for example, drying it at 120 to 220°C for 2 to 15 minutes). etc.) by semi-curing.
  • the amount of the resin composition adhered to the base material that is, the amount of the resin composition (including filler (D)) relative to the total amount of prepreg after semi-curing, is preferably in the range of 20 to 99% by mass, and 20% by mass. More preferably, the content is in the range of 80% by mass.
  • the base material is not particularly limited as long as it is a base material used for various printed wiring board materials.
  • the material of the base material include glass fiber (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, spherical glass, etc.) , inorganic fibers other than glass (eg, quartz, etc.), and organic fibers (eg, polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.).
  • the form of the base material is not particularly limited, and examples thereof include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, and the like. These base materials may be used alone or in combination of two or more.
  • the base material has a thickness of 200 ⁇ m or less, a mass of 250 g/ A glass woven fabric having a size of m 2 or less is preferable, and from the viewpoint of moisture absorption and heat resistance, a glass woven fabric surface-treated with a silane coupling agent such as epoxy silane or amino silane is preferable.
  • a silane coupling agent such as epoxy silane or amino silane is preferable.
  • a low dielectric glass cloth made of glass fibers exhibiting a low dielectric constant and a low dielectric loss tangent, such as L-glass, NE-glass, and Q-glass is more preferable.
  • Examples of the base material having a low dielectric constant include a base material having a dielectric constant of 5.0 or less (preferably 3.0 to 4.9).
  • Examples of the low dielectric loss tangent base material include base materials with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005).
  • the relative dielectric constant and dielectric loss tangent are values measured at 10 GHz using a perturbation method cavity resonator.
  • the metal foil-clad laminate of this embodiment includes at least one layer formed from the prepreg of this embodiment, and metal foil disposed on one or both sides of the layer formed from the prepreg.
  • a method for producing the metal foil-clad laminate of this embodiment for example, at least one prepreg of this embodiment is arranged (preferably two or more prepregs are stacked), metal foil is arranged on one or both sides of the prepreg, and laminated molding is performed.
  • One method is to do so. More specifically, it can be produced by arranging a metal foil such as copper or aluminum on one or both sides of a prepreg and laminating it.
  • the number of prepreg sheets is preferably 1 to 10 sheets, more preferably 2 to 10 sheets, and even more preferably 2 to 9 sheets.
  • the metal foil is not particularly limited as long as it is used as a material for printed wiring boards, and examples thereof include copper foils such as rolled copper foil and electrolytic copper foil.
  • the thickness of the metal foil (preferably copper foil) is not particularly limited, and may be about 1.5 to 70 ⁇ m. Further, when copper foil is used as the metal foil, it is preferable that the roughness Rz of the surface of the copper foil measured according to JIS B0601:2013 is adjusted to 0.2 to 4.0 ⁇ m.
  • the roughness Rz of the copper foil surface By setting the roughness Rz of the copper foil surface to 0.2 ⁇ m or more, the roughness of the copper foil surface becomes appropriate, and the copper foil peel strength tends to be further improved. On the other hand, by setting the roughness Rz of the copper foil surface to 4.0 ⁇ m or less, the roughness of the copper foil surface becomes appropriate, and the dielectric loss tangent characteristics of the obtained cured product tend to be further improved.
  • the roughness Rz of the copper foil surface is more preferably 0.5 ⁇ m or more, still more preferably 0.6 ⁇ m or more, particularly preferably 0.7 ⁇ m or more, and more preferably is 3.5 ⁇ m or less, more preferably 3.0 ⁇ m or less, particularly preferably 2.0 ⁇ m or less.
  • Examples of the lamination molding method include methods normally used when molding laminate boards for printed wiring boards and multilayer boards, and more specifically, multistage press machines, multistage vacuum press machines, continuous molding machines, autoclave molding machines, etc.
  • An example of this method is to perform lamination molding at a temperature of about 180 to 350° C., a heating time of about 100 to 300 minutes, and a surface pressure of about 20 to 100 kg/cm 2 .
  • a multilayer board can be obtained by laminating and molding a combination of the prepreg of this embodiment and a separately produced wiring board for an inner layer.
  • a copper foil of approximately 35 ⁇ m is placed on both sides of one sheet of prepreg according to the present embodiment, and after lamination is formed using the above-mentioned forming method, an inner layer circuit is formed, and this circuit is coated with black. After that, the inner layer circuit board and the prepreg of this embodiment are alternately placed one by one, and a copper foil is placed on the outermost layer, and the above conditions are met.
  • a multilayer board can be produced by lamination molding, preferably under vacuum.
  • the metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.
  • the resin composition for electronic materials obtained using the resin composition of this embodiment has a cured product with low dielectric properties (low dielectric constant, low dielectric constant, low
  • the cured product can have excellent properties such as dielectric loss tangent), moisture absorption and heat resistance, and heat resistance, desmear resistance, metal foil peel strength, crack resistance, appearance of cured product, and low thermal expansion.
  • the printed wiring board of the present embodiment is a printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, the insulating layer being formed from the resin composition of the present embodiment. and a layer formed from the prepreg of this embodiment.
  • a printed wiring board can be manufactured according to a conventional method, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board will be shown below. First, a metal foil-clad laminate such as the copper foil-clad laminate described above is prepared. Next, the surface of the metal foil-clad laminate is etched to form an inner layer circuit, thereby producing an inner layer substrate.
  • the surface of the inner layer circuit of this inner layer board is subjected to surface treatment to increase adhesive strength as necessary, and then the required number of sheets of prepreg described above are layered on the surface of the inner layer circuit, and then metal foil for the outer layer circuit is laminated on the outside. Then heat and press to form an integral mold.
  • a multilayer laminate is produced in which an insulating layer made of the base material and the cured resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit.
  • a plating metal film is formed on the wall of the hole to conduct the inner layer circuit and the metal foil for the outer layer circuit, and then the outer layer circuit is formed.
  • a printed wiring board is manufactured by performing an etching process on metal foil to form an outer layer circuit.
  • the printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer is made of the resin composition of the present embodiment described above and/or a cured product thereof.
  • the configuration includes That is, the prepreg of the present embodiment described above (for example, the prepreg formed from the base material and the resin composition of the present embodiment impregnated or applied thereto), the resin composition of the metal foil-clad laminate of the present embodiment described above The layer formed from the material becomes the insulating layer of this embodiment.
  • the present embodiment also relates to a semiconductor device including the printed wiring board. For details of the semiconductor device, the descriptions in paragraphs 0200 to 0202 of JP-A-2021-021027 can be referred to, and the contents thereof are incorporated into this specification.
  • the insulating layer formed of the cured product of the resin composition of the present embodiment has a reduced surface roughness after the insulating layer is subjected to roughening treatment.
  • the arithmetic mean roughness Ra of the surface of the insulating layer after the roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, particularly preferably 100 nm or less.
  • the lower limit of the arithmetic mean roughness Ra is not particularly limited, but may be, for example, 10 nm or more.
  • the arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode using a 50x lens.
  • the non-contact surface roughness meter used is WYKONT3300 manufactured by Beaco Instruments.
  • the resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment disposed on the surface of the support.
  • the resin composite sheet can be used as a build-up film or a dry film solder resist.
  • the method for producing the resin composite sheet is not particularly limited, but for example, the resin composite sheet may be produced by applying (coating) a solution in which the resin composition of the present embodiment described above is dissolved in a solvent to a support and drying it. There are several ways to obtain it.
  • Examples of the support used here include polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylenetetrafluoroethylene copolymer film, and release films in which a release agent is applied to the surface of these films.
  • Examples include organic film base materials such as polyimide film, conductive foils such as copper foil and aluminum foil, plate-like materials such as glass plates, SUS (Steel Use Stainless) plates, and FRP (Fiber-Reinforced Plastics). It is not particularly limited.
  • Examples of the coating method include a method in which a solution of the resin composition of the present embodiment dissolved in a solvent is coated onto the support using a bar coater, die coater, doctor blade, Baker applicator, etc. It will be done. Further, after drying, the support can be peeled off or etched from the resin composite sheet in which the support and the resin composition are laminated, thereby forming a single layer sheet. Note that the support can be used by supplying a solution in which the resin composition of the present embodiment described above is dissolved in a solvent into a mold having a sheet-like cavity and drying it to form it into a sheet. It is also possible to obtain a single layer sheet.
  • the drying conditions for removing the solvent are not particularly limited, but if the temperature is low, the solvent tends to remain in the resin composition, and if the temperature is high, Since curing of the resin composition progresses, the temperature is preferably 20° C. to 200° C. for 1 to 90 minutes.
  • the single layer sheet or the resin composite sheet can be used in an uncured state where the solvent is simply dried, or it can be used in a semi-cured (B-staged) state if necessary.
  • the thickness of the resin layer in the single-layer sheet or resin composite sheet of this embodiment can be adjusted by the concentration of the solution of the resin composition of this embodiment used for application (coating) and the coating thickness, and there are no particular limitations. However, in general, as the coating thickness increases, solvent tends to remain during drying, so 0.1 to 500 ⁇ m is preferable.
  • Liquid pump manufactured by Shimadzu Corporation, LC-20AD
  • differential refractive index detector manufactured by Shimadzu Corporation, RID-10A
  • GPC column manufactured by Showa Denko Corporation, GPC KF-801, 802, 803, 804
  • the experiment was carried out using tetrahydrofuran as the solvent, a flow rate of 1.0 mL/min, a column temperature of 40° C., and a calibration curve using monodisperse polystyrene.
  • the obtained polymer (va) having a structural unit represented by formula (V) had a number average molecular weight Mn of 2,060, a weight average molecular weight Mw of 30,700, and a monodispersity Mw/Mn of 14.9. there were.
  • the polymer (va) having the structural unit represented by formula (V) had resonance lines originating from each monomer unit used as a raw material. observed.
  • the proportion of each monomer unit (constituent unit derived from each raw material) in the polymer (va) having the structural unit represented by formula (V) is as follows. was calculated.
  • Resin "A” had a number average molecular weight in terms of polystyrene determined by GPC of 1,975, a weight average molecular weight in terms of polystyrene determined by GPC of 3,514, and a hydroxyl equivalent of 990.
  • the modified polyphenylene ether compound had a number average molecular weight in terms of polystyrene determined by GPC of 2,250, a weight average molecular weight in terms of polystyrene determined by GPC of 3,920, and a vinyl group equivalent of 1189 g/vinyl group.
  • ⁇ Measurement method and evaluation method> Relative permittivity (Dk) and dielectric loss tangent (Df) After removing the copper foils on both sides of the obtained cured plate by etching, it was downsized to 10 mm x 1 mm to obtain a sample for evaluation. The obtained evaluation sample was dried at 120° C. for 60 minutes, and then the relative dielectric constant (Dk) and dielectric loss tangent (Df) after drying at 10 GHz were measured using a perturbation method cavity resonator. The measurement temperature was 23°C. The perturbation method cavity resonator used was Agilent 8722ES manufactured by Agilent Technologies.
  • Dk Specific permittivity
  • B Over 2.50 and 2.60 or less
  • C 2.60 super dielectric loss tangent
  • Df A: Less than 0.0023
  • B 0.0023 or more and less than 0.0026 C: 0.0026 or more
  • the glass transition temperature was measured using a dynamic viscoelasticity measuring device on a sample that was downsized to 12.7 mm x 30 mm after removing the copper foil on both sides of the obtained cured plate by etching, and was determined according to JIS-K7244-4:1999 ( Plastics - Dynamic mechanical properties test method - Part 4: Tensile vibration - Non-resonance method), starting temperature 30°C, ending temperature 400°C, heating rate 5°C/min, measurement frequency 1Hz, under nitrogen atmosphere The dynamic viscoelasticity was measured, and the temperature at which the loss tangent (Tan ⁇ ) obtained at that time reached the maximum value was taken as the glass transition temperature.
  • the dynamic viscoelasticity measuring device used was EXSTAR6000 DMS6100 manufactured by Seiko Instruments Inc. It was evaluated as follows. A: 250°C or more B: 230°C or more and less than 250°C C: Less than 230°C
  • CTE Coefficient of linear Thermal Expansion
  • Example 1 the compound represented by formula (M-2) (manufactured by Nippon Kayaku Co., Ltd., "MIR-5000”) was mixed with the same amount of a maleimide compound having the structure shown below (manufactured by DIC Corporation, "NE-X-”). 9470S”), and the other procedures were the same.
  • Example 1 the compound represented by formula (M-2) (manufactured by Nippon Kayaku Co., Ltd., "MIR-5000”) was mixed with the same amount of a maleimide compound having the structure shown below (manufactured by Nippon Kayaku Co., Ltd., "MIR-5000"). 3000''), and the other procedures were carried out in the same manner.

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WO2024090410A1 (ja) * 2022-10-26 2024-05-02 三菱瓦斯化学株式会社 樹脂組成物、硬化物、プリプレグ、金属箔張積層板、樹脂複合シート、および、プリント配線板

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WO2022054867A1 (ja) * 2020-09-11 2022-03-17 パナソニックＩｐマネジメント株式会社 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
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JP7005821B1 (ja) 2020-03-11 2022-02-10 日本化薬株式会社 マレイミド樹脂およびその製造方法、マレイミド溶液、並びに、硬化性樹脂組成物およびその硬化物

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WO2021149733A1 (ja) * 2020-01-24 2021-07-29 三菱瓦斯化学株式会社 樹脂組成物、樹脂シート、プリプレグ及びプリント配線板
WO2022054867A1 (ja) * 2020-09-11 2022-03-17 パナソニックＩｐマネジメント株式会社 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
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WO2024090408A1 (ja) * 2022-10-26 2024-05-02 三菱瓦斯化学株式会社 樹脂組成物、硬化物、プリプレグ、金属箔張積層板、樹脂複合シート、および、プリント配線板
WO2024090410A1 (ja) * 2022-10-26 2024-05-02 三菱瓦斯化学株式会社 樹脂組成物、硬化物、プリプレグ、金属箔張積層板、樹脂複合シート、および、プリント配線板

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