WO2023090351A1 - 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ - Google Patents

樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ Download PDF

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WO2023090351A1
WO2023090351A1 PCT/JP2022/042516 JP2022042516W WO2023090351A1 WO 2023090351 A1 WO2023090351 A1 WO 2023090351A1 JP 2022042516 W JP2022042516 W JP 2022042516W WO 2023090351 A1 WO2023090351 A1 WO 2023090351A1
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group
resin composition
resin
carbon atoms
maleimide
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English (en)
French (fr)
Japanese (ja)
Inventor
諒 下川
俊希 藤井
真 柳田
圭芸 日▲高▼
幸雄 中村
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Resonac Corp
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Resonac Corp
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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate

Definitions

  • the present embodiment relates to resin compositions, prepregs, laminates, resin films, printed wiring boards, and semiconductor packages.
  • Patent Document 1 the object is to provide a curable resin composition that can be applied to the insulating layer of a printed wiring board, and the resulting cured product has a low relative dielectric constant and dielectric loss tangent and is excellent in heat resistance.
  • a curable resin composition containing a naphthol novolac type epoxy resin and a polyphenylene ether resin is disclosed.
  • the insulating layer is treated with an aqueous solution of an oxidizing agent for the purpose of removing residual components after drilling the insulating layer or roughening the surface for improving the adhesion between the insulating layer and the conductor layer.
  • Desmear processing is performed by According to the studies of the present inventors, when an insulating layer formed from a resin composition containing a thermosetting resin and polyphenylene ether is subjected to desmear treatment, a particle having a diameter exceeding about 0.5 ⁇ m is formed on the surface of the insulating layer. It has been found that pitting may occur.
  • the present embodiment provides a resin composition capable of forming a cured product in which the occurrence of depressions on the surface after desmear treatment is suppressed, a prepreg, a laminate, a resin film using the resin composition,
  • An object of the present invention is to provide a printed wiring board and a semiconductor package.
  • the present embodiment relates to the following [1] to [13].
  • [1] (A) one or more selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives of the maleimide resins; (B) a polyphenylene ether resin having a functional group containing an ethylenically unsaturated bond; (C) a styrene-based elastomer having a weight average molecular weight (Mw) of more than 10,000 and less than 100,000; (D) an organic peroxide; A resin composition containing [2] The resin composition according to [1] above, wherein the component (B) has a functional group containing an ethylenically unsaturated bond at its end.
  • a printed wiring board comprising a cured product of the resin composition according to any one of [1] to [8] above.
  • a resin composition capable of forming a cured product in which the occurrence of depressions on the surface after desmearing is suppressed, a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package using the resin composition can be provided.
  • a numerical range indicated using “to” indicates a range including the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the notation of a numerical range “X to Y” means a numerical range that is greater than or equal to X and less than or equal to Y.
  • the description "X or more” in this specification means X and a numerical value exceeding X.
  • the description “Y or less” in this specification means Y and a numerical value less than Y.
  • the lower and upper limits of any numerical range recited herein are optionally combined with the lower or upper limits of other numerical ranges, respectively. In the numerical ranges described herein, the lower or upper limit of the numerical range may be replaced with the values shown in the examples.
  • each component and material exemplified in this specification may be used singly or in combination of two or more unless otherwise specified.
  • the content of each component in the resin composition refers to the content of the plurality of substances present in the resin composition when there are multiple substances corresponding to each component in the resin composition, unless otherwise specified. means the total amount of
  • solid content means components other than the solvent, including those that are liquid at room temperature, starch syrup, and wax.
  • room temperature means 25°C.
  • (Meth)acryloyl as used herein means “acryloyl” and the corresponding “methacryloyl”.
  • the weight average molecular weight (Mw) in this specification means a value measured by gel permeation chromatography (GPC; Gel Permeation Chromatography) in terms of polystyrene. Specifically, the weight average molecular weight (Mw) in this specification can be measured by the method described in Examples.
  • the resin composition of this embodiment is (A) one or more selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives of the maleimide resins; (B) a polyphenylene ether resin having a functional group containing an ethylenically unsaturated bond; (C) a styrene-based elastomer having a weight average molecular weight (Mw) of more than 10,000 and less than 100,000; (D) an organic peroxide; It is a resin composition containing
  • maleimide resin having one or more N-substituted maleimide groups and derivatives of the maleimide resin
  • (A) maleimide resin or "(A) component ”
  • (B) the polyphenylene ether-based resin having a functional group containing an ethylenically unsaturated bond may be simply referred to as "(B) polyphenylene ether-based resin” or "(B) component".
  • (C) a styrene-based elastomer having a weight average molecular weight (Mw) of more than 10,000 and less than 100,000 may be simply referred to as "(C) styrene-based elastomer” or "(C) component”.
  • (D) organic peroxide may be called "(D)component.”
  • the reason why the resin composition of the present embodiment can form a cured product in which the occurrence of depressions on the surface after desmear treatment is suppressed is presumed as follows.
  • a conventional polyphenylene ether is blended with (A) a maleimide resin
  • the compatibility between the two decreases as the curing of the maleimide resin (A) progresses due to the difference in polarity between the two, and the cured product lacks homogeneity. It is presumed that there was an insufficient area and this was the cause of the depression.
  • the resin composition of the present embodiment uses, as the component (B), a polyphenylene ether-based resin having a functional group containing an ethylenically unsaturated bond that is reactive with the maleimide-based resin (A), Furthermore, it also contains (D) an organic peroxide. Therefore, (B) the polyphenylene ether-based resin is mixed with (A) the maleimide-based resin using (D) an organic peroxide as a polymerization initiator before the compatibility decreases with the progress of curing of the (A) maleimide-based resin. It is considered that the reaction becomes easier and the homogeneity of the cured product is improved.
  • the resin composition of the present embodiment further contains a styrene-based elastomer having a weight average molecular weight (Mw) of more than 10,000 and less than 100,000 as component (C).
  • component (C) has an excellent balance of physical properties such as dielectric properties, heat resistance and Young's modulus.
  • the component (C) has a weight average molecular weight (Mw) of more than 10,000, so that the fluidity of the resin composition during heating is moderately suppressed, resulting in excellent moldability and a weight average molecular weight (Mw) of When Mw) is less than 100,000, compatibility with other resins tends to be excellent.
  • the (C) styrene-based elastomer also loses compatibility with the (A) maleimide-based resin as the curing of the (A) maleimide-based resin progresses.
  • the (C) styrene-based elastomer since the (C) styrene-based elastomer has excellent affinity with the (B) polyphenylene ether-based resin, the (B) polyphenylene ether-based resin tends to be homogeneously present in the resin composition of the present embodiment.
  • (C) It is thought that the compatibility of the styrene-based elastomer became less likely to decrease.
  • the resin composition of the present embodiment suppresses the formation of depressions on the surface of the cured product after desmearing, and thus the cured product is preferably a resin composition that undergoes desmearing. It is more preferable that the cured product is a resin composition for a printed wiring board which is subjected to desmear treatment.
  • the resin composition of the present embodiment will be described below in order.
  • the maleimide resin is one or more selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives of the maleimide resins.
  • the maleimide-based resin may be used singly or in combination of two or more.
  • maleimide resin having one or more N-substituted maleimide groups may be referred to as "maleimide resin (AX)” or “(AX) component”.
  • a maleimide resin derivative having one or more N-substituted maleimide groups is sometimes referred to as a “maleimide resin derivative (AY)” or “(AY) component”.
  • the maleimide resin (AX) is not particularly limited as long as it has one or more N-substituted maleimide groups.
  • the maleimide resin (AX) is preferably an aromatic maleimide resin having two or more N-substituted maleimide groups from the viewpoint of conductor adhesion and heat resistance, and an aromatic bismaleimide having two N-substituted maleimide groups. Resin is more preferred.
  • aromatic maleimide resin means a compound having an N-substituted maleimide group directly bonded to an aromatic ring.
  • aromatic bismaleimide resin as used herein means a compound having two N-substituted maleimide groups directly bonded to an aromatic ring.
  • aromatic polymaleimide resin as used herein means a compound having 3 or more N-substituted maleimide groups directly bonded to an aromatic ring.
  • aliphatic maleimide resin as used herein means a compound having an N-substituted maleimide group directly bonded to an aliphatic hydrocarbon.
  • maleimide resin (AX) a maleimide resin represented by the following general formula (A1-1) [hereinafter referred to as "maleimide resin (A1)"] is preferable.
  • X a11 is a divalent organic group.
  • X a11 in general formula (A1-1) above is a divalent organic group.
  • the divalent organic group represented by X a11 in the general formula (A1-1) includes, for example, a divalent group represented by the following general formula (A1-2), and a divalent group represented by the following general formula (A1-3).
  • a divalent group represented by is mentioned.
  • R a11 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom.
  • n a11 is an integer of 0 to 4. * represents a bonding site.
  • Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R a11 in the general formula (A1-2) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and isobutyl t-butyl group, n-pentyl group and other alkyl groups having 1 to 5 carbon atoms; alkenyl groups having 2 to 5 carbon atoms and alkynyl groups having 2 to 5 carbon atoms.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group.
  • Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
  • n a11 in the general formula (A1-2) is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, still more preferably 0, from the viewpoint of availability. When n a11 is an integer of 2 or more, the plurality of R a11 may be the same or different.
  • R a12 and R a13 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom;
  • X a12 is an alkylene group having 1 to 5 carbon atoms;
  • n a12 and n a13 are an alkylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond, or a divalent group represented by the following general formula (A1-3-1). , each independently an integer from 0 to 4. * represents a binding site.)
  • Examples of aliphatic hydrocarbon groups having 1 to 5 carbon atoms represented by R a12 and R a13 in general formula (A1-3) include methyl group, ethyl group, n-propyl group, isopropyl group and n-butyl. alkyl groups having 1 to 5 carbon atoms such as isobutyl group, t-butyl group and n-pentyl group; alkenyl groups having 2 to 5 carbon atoms and alkynyl groups having 2 to 5 carbon atoms.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group or an ethyl group.
  • Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
  • Examples of the alkylene group having 1 to 5 carbon atoms represented by X a12 in the general formula (A1-3) include methylene group, 1,2-dimethylene group, 1,3-trimethylene group and 1,4-tetramethylene group, 1,5-pentamethylene group, and the like.
  • the alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and still more preferably a methylene group.
  • the alkylidene group having 2 to 5 carbon atoms represented by X a12 in the general formula (A1-3) includes, for example, an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group and an isopentylidene group. etc.
  • an alkylidene group having 2 to 4 carbon atoms is preferred, an alkylidene group having 2 or 3 carbon atoms is more preferred, and an isopropylidene group is even more preferred.
  • n a12 and n a13 in general formula (A1-3) are each independently an integer of 0 to 4.
  • n a12 or n a13 is an integer of 2 or more
  • the plurality of R a12s or the plurality of R a13s may be the same or different.
  • the divalent group represented by general formula (A1-3-1) represented by X a12 in general formula (A1-3) is as follows.
  • R a14 and R a15 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom;
  • X a13 is an alkylene group having 1 to 5 carbon atoms; an alkylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond,
  • n a14 and n a15 are each independently an integer of 0 to 4. * represents a bonding site.
  • Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R a14 and R a15 in the general formula (A1-3-1) include methyl group, ethyl group, n-propyl group, isopropyl group, n C1-5 alkyl groups such as -butyl group, isobutyl group, t-butyl group and n-pentyl group; C2-5 alkenyl groups and C2-5 alkynyl groups.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group.
  • Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
  • alkylene group having 1 to 5 carbon atoms represented by X a13 in the general formula (A1-3-1) examples include methylene group, 1,2-dimethylene group, 1,3-trimethylene group, 1,4- A tetramethylene group, a 1,5-pentamethylene group and the like can be mentioned.
  • the alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and still more preferably a methylene group.
  • Examples of the alkylidene group having 2 to 5 carbon atoms represented by X a13 in the general formula (A1-3-1) include ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentyl A lidene group and the like can be mentioned.
  • an alkylidene group having 2 to 4 carbon atoms is preferred, an alkylidene group having 2 or 3 carbon atoms is more preferred, and an isopropylidene group is even more preferred.
  • X a13 in the general formula (A1-3-1) is preferably an alkylidene group having 2 to 5 carbon atoms, more preferably an alkylidene group having 2 to 4 carbon atoms, and further an isopropylidene group. preferable.
  • n a14 and n a15 in the general formula (A1-3-1) are each independently an integer of 0 to 4, and from the viewpoint of availability, both are preferably integers of 0 to 2, and more It is preferably 0 or 1, more preferably 0.
  • n a14 or n a15 is an integer of 2 or more, the plurality of R a14s or the plurality of R a15s may be the same or different.
  • an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, and an alkylidene group having 2 to 5 carbon atoms, represented by the general formula (A1-3-1) is preferred, an alkylene group having 1 to 5 carbon atoms is more preferred, and a methylene group is even more preferred.
  • n a16 is an integer of 0 to 10. * represents a binding site.
  • n a16 in general formula (A1-4) is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and still more preferably an integer of 0 to 3, from the viewpoint of availability.
  • n a17 is a number from 0 to 5. * represents a binding site.
  • R a16 and R a17 are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
  • n a18 is an integer of 1 to 8. * represents a bonding site.
  • Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R a16 and R a17 in the general formula (A1-6) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and n-butyl. alkyl groups having 1 to 5 carbon atoms such as isobutyl group, t-butyl group and n-pentyl group; alkenyl groups having 2 to 5 carbon atoms and alkynyl groups having 2 to 5 carbon atoms.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • n a18 in general formula (A1-6) is an integer of 1 to 8, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and still more preferably 1.
  • n a18 is an integer of 2 or more, the plurality of R a16 or the plurality of R a17 may be the same or different.
  • maleimide resins (A1) include aromatic bismaleimide resins, aromatic polymaleimide resins, and aliphatic maleimide resins.
  • Specific examples of the maleimide resin (A1) include N,N'-ethylenebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'- [1,3-(2-methylphenylene)]bismaleimide, N,N'-[1,3-(4-methylphenylene)]bismaleimide, N,N'-(1,4-phenylene)bismaleimide, Bis(4-maleimidophenyl)methane, bis(3-methyl-4-maleimidophenyl)methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, bis(4-maleimide phenyl)ether, bis(4-maleimidophenyl)sulfone
  • maleimide resin derivative (AY) As the maleimide resin derivative (AY), an aminomaleimide resin having a structural unit derived from the maleimide resin (AX) and a structural unit derived from a diamine compound [hereinafter referred to as "aminomaleimide resin (A2)" or “(A2) component ” may be called. ] is preferable.
  • aminomaleimide resin (A2) has structural units derived from the maleimide resin (AX) and structural units derived from the diamine compound.
  • the structural unit derived from the maleimide resin (AX) for example, among the N-substituted maleimide groups possessed by the maleimide resin (AX), at least one N-substituted maleimide group undergoes a Michael addition reaction with an amino group possessed by the diamine compound.
  • a structural unit consisting of The structural unit derived from the maleimide resin (AX) contained in the aminomaleimide resin (A2) may be of one type alone or of two or more types.
  • the content of structural units derived from the maleimide resin (AX) in the aminomaleimide resin (A2) is not particularly limited, but is preferably 5 to 95% by mass, more preferably 30 to 93% by mass, and still more preferably 60 to 90%. % by mass.
  • the content of the structural unit derived from the maleimide resin (AX) in the aminomaleimide resin (A2) is within the above range, the dielectric properties and the handleability of the resin film tend to be better.
  • the structural unit derived from the diamine compound for example, one or both of the two amino groups of the diamine compound undergo a Michael addition reaction with an N-substituted maleimide group of the maleimide resin (AX).
  • AX N-substituted maleimide group of the maleimide resin
  • the structural unit derived from the diamine compound contained in the aminomaleimide resin (A2) may be of one type alone or of two or more types.
  • the amino group of the diamine compound is preferably a primary amino group.
  • Examples of the structural unit derived from the diamine compound having two primary amino groups include a group represented by the following general formula (A2-1), a group represented by the following general formula (A2-2), and the like. be done.
  • X a21 is a divalent organic group, and * represents a binding site.
  • X a21 in general formulas (A2-1) and (A2-2) above is a divalent organic group and corresponds to a divalent group obtained by removing two primary amino groups from a diamine compound. do.
  • X a21 in general formulas (A2-1) and (A2-2) above is preferably a divalent group represented by general formula (A2-3) below.
  • R a21 and R a22 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a hydroxyl group or a halogen atom. an alkylene group having up to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a fluorenylene group, a single bond, or the following general formula (A2-3-1) or the following It is a divalent group represented by the general formula (A2-3-2), n a21 and n a22 are each independently an integer of 0 to 4. * represents a binding site.)
  • R a23 and R a24 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom;
  • X a23 is an alkylene group having 1 to 5 carbon atoms; an alkylidene group, a m-phenylenediisopropylidene group, a p-phenylenediisopropylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond,
  • n a23 and n a24 are each independently , an integer from 0 to 4. * represents a binding site.
  • R a25 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom;
  • X a24 and X a25 each independently represent an alkylene group having 1 to 5 carbon atoms; is an alkylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond,
  • n a25 is an integer of 0 to 4. * represents a bonding site.
  • 1 to 5 aliphatic hydrocarbon groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group and the like. to 5 alkyl groups; alkenyl groups having 2 to 5 carbon atoms; and alkynyl groups having 2 to 5 carbon atoms.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group or an ethyl group.
  • Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine atoms.
  • X a22 in the general formula (A2-3), X a23 in the general formula (A2-3-1), and X a24 and X a25 in the general formula (A2-3-2) have 1 carbon atoms.
  • the alkylene group of 1 to 5 include methylene group, 1,2-dimethylene group, 1,3-trimethylene group, 1,4-tetramethylene group, 1,5-pentamethylene group and the like.
  • the alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and still more preferably a methylene group.
  • alkylidene groups of 2 to 5 include ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group and the like.
  • the alkylidene group having 2 to 5 carbon atoms is preferably an alkylidene group having 2 to 4 carbon atoms, more preferably an alkylidene group having 2 or 3 carbon atoms, and still more preferably an isopropylidene group.
  • n a21 and n a22 in the general formula (A2-3) are each independently an integer of 0 to 4, and from the viewpoint of availability, both are preferably integers of 0 to 3, more preferably It is an integer from 0 to 2, more preferably 0 or 2.
  • n a21 or n a22 is an integer of 2 or more, the plurality of R a21s or the plurality of R a22s may be the same or different.
  • n a23 and n a24 in the general formula (A2-3-1) are each independently an integer of 0 to 4, and from the viewpoint of availability, both are preferably integers of 0 to 2, and more It is preferably 0 or 1, more preferably 0.
  • n a23 or n a24 is an integer of 2 or more, the plurality of R a23s or the plurality of R a24s may be the same or different.
  • n a25 in the general formula (A2-3-2) is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, more preferably 0 from the viewpoint of availability is.
  • n a25 is an integer of 2 or more, a plurality of R a25 may be the same or different.
  • X a21 in general formulas (A2-1) and (A2-2) above may be a divalent group containing a structural unit represented by general formula (A2-4) below. Alternatively, it may be a divalent group represented by the following general formula (A2-5).
  • R a26 and R a27 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, a phenyl group or a substituted phenyl group. * represents a bonding site.
  • R a26 and R a27 are the same as those in the above general formula (A2-4), R a28 and R a29 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, a phenyl group or a substituted phenyl group, X a26 and X a27 each independently represent a divalent organic group, and n a26 is an integer of 2 to 100. * represents a binding site.
  • Examples of aliphatic hydrocarbon groups having 1 to 5 carbon atoms represented by R a26 to R a29 in general formulas (A2-4) and (A2-5) include methyl group, ethyl group, n-propyl group, C1-5 alkyl groups such as isopropyl group, n-butyl group, isobutyl group, t-butyl group and n-pentyl group; C2-5 alkenyl groups, C2-5 alkynyl groups, etc. mentioned.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched.
  • the aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group.
  • Substituents possessed by the phenyl groups in the substituted phenyl groups represented by R a26 to R a29 include the aforementioned aliphatic hydrocarbon groups having 1 to 5 carbon atoms.
  • Examples of the divalent organic group represented by X a26 and X a27 include an alkylene group, an alkenylene group, an alkynylene group, an arylene group, —O—, and a divalent linking group in which these are combined.
  • Examples of the alkylene group include alkylene groups having 1 to 10 carbon atoms such as a methylene group, ethylene group and propylene group.
  • Examples of the alkenylene group include alkenylene groups having 2 to 10 carbon atoms.
  • Examples of the alkynylene group include alkynylene groups having 2 to 10 carbon atoms.
  • Examples of the arylene group include arylene groups having 6 to 20 carbon atoms such as phenylene group and naphthylene group.
  • Xa26 and Xa27 are preferably an alkylene group or an arylene group, more preferably an alkylene group.
  • n a26 is an integer of 2-100, preferably an integer of 2-50, more preferably an integer of 3-40, and still more preferably an integer of 5-30.
  • n a26 is an integer of 2 or more
  • the plurality of R a26 or the plurality of R a27 may be the same or different.
  • the content of the structural unit derived from the diamine compound in the aminomaleimide resin (A2) is not particularly limited, but is preferably 5 to 95% by mass, more preferably 7 to 70% by mass, and still more preferably 10 to 40% by mass. be.
  • the content of the structural unit derived from the diamine compound in the aminomaleimide resin (A2) is within the above range, dielectric properties, heat resistance, flame retardancy and glass transition temperature tend to be better.
  • diamine compounds examples include 4,4′-diaminodiphenylmethane, 3,3′-dimethyl-4,4′-diaminodiphenylmethane, 3,3′-diethyl-4,4′-diaminodiphenylmethane, 4,4′- Diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ketone, 4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'- Diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3'-dimethyl- 5,5'-diethyl-4,4'-diaminodipheny
  • diamine compounds are 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4, 3,3'-dimethyl-4, 4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 4,4'-[1,3-phenylene Bis(1-methylethylidene)]bisaniline and 4,4′-[1,4-phenylenebis(1-methylethylidene)]bisaniline are preferred, and 3,3′-diethyl-4,4′-diaminodiphenylmethane is more preferred. preferable.
  • a silicone compound having two primary amino groups is preferable.
  • the silicone compound having two primary amino groups a silicone compound having primary amino groups at both terminals is preferable.
  • the primary amino group equivalent weight of the silicone compound having two primary amino groups is not particularly limited, but is preferably 300 to 2,000 g/mol, more preferably 400 to 1,500 g/mol, and still more preferably 500 g/mol. ⁇ 1,000 g/mol.
  • the ratio (Ta2/Ta1) is not particularly limited, it is preferably from 0.05 to 10, more preferably from 1 to 8, and still more preferably from 3 to 3, from the viewpoint of dielectric properties, heat resistance, flame retardancy and glass transition temperature.
  • the group derived from the —NH 2 group of the diamine compound includes —NH 2 itself. Further, the group derived from the N-substituted maleimide group of the maleimide resin (AX) includes the N-substituted maleimide group itself.
  • the weight average molecular weight (Mw) of the aminomaleimide resin (A2) is not particularly limited, but is preferably 400 to 10,000, more preferably 1,000 to 5,000, still more preferably 1,000 to 5,000, from the viewpoint of handleability and moldability. is 1,500 to 4,000, particularly preferably 2,000 to 3,000.
  • the aminomaleimide resin (A2) can be produced, for example, by reacting the maleimide resin (AX) with a diamine compound in an organic solvent. By reacting the maleimide resin (AX) with the diamine compound, an aminomaleimide resin (A2) is obtained through the Michael addition reaction between the maleimide resin (AX) and the diamine compound.
  • a reaction catalyst may be used as necessary.
  • the reaction temperature of the Michael addition reaction is preferably 50 to 160° C., more preferably 60 to 150° C., and still more preferably 70 to 140° C., from the viewpoint of workability such as reaction rate and suppression of gelation of the product during the reaction. °C.
  • the reaction time of the Michael addition reaction is preferably 0.5 to 10 hours, more preferably 1 to 8 hours, still more preferably 2 to 6 hours, from the viewpoint of productivity and sufficient progress of the reaction.
  • these reaction conditions are not particularly limited and can be appropriately adjusted depending on the type of raw material used.
  • the content of (A) the maleimide-based resin is not particularly limited, but is preferably 20 ⁇ 95% by mass, more preferably 50 to 90% by mass, still more preferably 70 to 85% by mass.
  • the content of the maleimide-based resin is at least the above lower limit, heat resistance, moldability, workability, and conductor adhesion tend to be better. Further, when the content of (A) the maleimide resin is equal to or less than the above upper limit, the dielectric properties tend to be more favorable.
  • the term "resin component” means a resin and a compound that forms a resin through a curing reaction.
  • resin component means a resin and a compound that forms a resin through a curing reaction.
  • (A) maleimide-based resin, (B) polyphenylene ether-based resin, (C) styrene-based elastomer, and (D) organic peroxide correspond to resin components.
  • the resin composition of the present embodiment contains, as optional components, a resin or a compound that forms a resin by a curing reaction in addition to the above components, these optional components are also included in the resin component.
  • the optional component corresponding to the resin component include (F) a curing accelerator other than the organic peroxide, which will be described later.
  • the (E) inorganic filler is not included in the resin component.
  • the total content of the resin components in the resin composition of the present embodiment is not particularly limited, but from the viewpoint of low thermal expansion, heat resistance, flame retardancy and conductor adhesion, the solid content of the resin composition of the present embodiment It is preferably 10 to 70% by mass, more preferably 20 to 60% by mass, and still more preferably 30 to 50% by mass relative to the total amount (100% by mass).
  • the polyphenylene ether-based resin is not particularly limited as long as it is a resin having a functional group containing a polyphenylene ether chain and an ethylenically unsaturated bond.
  • the resin composition of the present embodiment tends to easily obtain excellent dielectric properties by containing (B) a polyphenylene ether-based resin.
  • the polyphenylene ether-based resin may be used alone or in combination of two or more.
  • the polyphenylene ether-based resin has a phenylene ether bond, and preferably has a structural unit represented by the following general formula (B-1).
  • R b1 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom.
  • n b1 is an integer of 0 to 4.
  • Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R b1 in the general formula (B-1) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and isobutyl group, t-butyl group, n-pentyl group and the like.
  • the aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group.
  • n b1 is an integer of 0 to 4, preferably 1 or 2, more preferably 2;
  • the substitution position of R b1 is preferably the ortho position on the benzene ring with respect to the substitution position of the oxygen atom.
  • n b1 is an integer of 2 or more, a plurality of R b1 may be the same or different.
  • the structural unit represented by the above general formula (B-1) is preferably a structural unit represented by the following general formula (B-1').
  • the polyphenylene ether-based resin has a functional group containing an ethylenically unsaturated bond [hereinafter sometimes referred to as an "ethylenically unsaturated bond-containing group” from the viewpoint of suppressing the generation of depressions after desmear treatment. ].
  • ethylenically unsaturated bond means a carbon-carbon double bond capable of an addition reaction, and does not include a double bond of an aromatic ring.
  • Ethylenically unsaturated bond-containing groups include, for example, vinyl group, allyl group, 1-methylallyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, styryl group, maleimide group, the following general formula (B-2 ) and the like.
  • R b2 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms represented by R b2 may be a straight-chain alkyl group, a branched-chain alkyl group or a cyclic alkyl group, preferably a straight-chain alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, still more preferably 1-3, and particularly preferably 1.
  • alkyl group examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, pentadecyl group, hexadecyl group and heptadecyl group. Among them, a methyl group is preferred.
  • the group represented by the above general formula (B-2) in which R b2 is a hydrogen atom corresponds to an acryloyl group
  • the group represented by the above general formula (B-2) in which R b2 is a methyl group corresponds to a methacryloyl group.
  • the ethylenically unsaturated bond-containing group possessed by the polyphenylene ether-based resin is preferably a group represented by the general formula (B-2) from the viewpoint of dielectric properties, and (meth) An acryloyl group is more preferred, and a methacryloyl group is even more preferred.
  • the number of ethylenically unsaturated bond-containing groups that the polyphenylene ether-based resin has in one molecule is not particularly limited, but is preferably 1 to 5, more preferably 2 to 3, and still more preferably 2. be.
  • the number of ethylenically unsaturated bond-containing groups is at least the above lower limit, heat resistance tends to be better.
  • the number of ethylenically unsaturated bond-containing groups is equal to or less than the above upper limit, it tends to be easier to suppress the occurrence of depressions after the desmear treatment.
  • the polyphenylene ether-based resin preferably has ethylenically unsaturated bond-containing groups at its terminals, more preferably at both terminals.
  • the polyphenylene ether-based resin may have an ethylenically unsaturated bond-containing group in addition to the terminal, but preferably has an ethylenically unsaturated bond-containing group only at the terminal.
  • Polyphenylene ether-based resin is preferably a compound represented by the following general formula (B-3) from the viewpoint of dielectric properties.
  • R b1 and n b1 are as described in the general formula (B-1) above.
  • R b3 and R b4 each independently represent an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen
  • n b2 and n b3 are each independently an integer of 0 to 4.
  • n b4 and n b5 are each independently an integer of 0 to 20, and the sum of n b4 and n b5 is , an integer of 1 to 30.
  • X b1 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond.
  • Yb1 and Yb2 are each independently the above ethylenically unsaturated bond-containing group.
  • n b2 and n b3 are integers from 0 to 4, preferably integers from 0 to 3, more preferably 2 or 3.
  • nb2 or nb3 is an integer of 2 or more
  • the plurality of Rb3 's or the plurality of Rb4 's may be the same or different.
  • nb4 and nb5 are integers of 0-20, preferably integers of 1-20, more preferably integers of 2-15, and even more preferably integers of 3-10.
  • nb4 or nb5 is an integer of 2 or more
  • the plurality of nb1 may be the same or different.
  • the sum of n b4 and n b5 is an integer of 1-30, preferably an integer of 2-25, more preferably an integer of 5-20, and still more preferably an integer of 7-15.
  • Examples of the alkylene group having 1 to 5 carbon atoms represented by X b1 in the general formula (B-3) include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group and a 1,4-tetramethylene group. group, 1,5-pentamethylene group, and the like.
  • Examples of the alkylidene group having 2 to 5 carbon atoms represented by X b1 include ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group and the like.
  • an isopropylidene group is preferable from the viewpoint of dielectric properties.
  • Preferred embodiments of the ethylenically unsaturated bond-containing groups represented by Yb1 and Yb2 are as described above.
  • the compound represented by the general formula (B-3) is preferably a compound represented by the following general formula (B-4).
  • n b4 and n b5 are as described in the general formula (B-3) above.
  • R b5 and R b6 are each independently a hydrogen atom or a methyl group.
  • X b2 is methylene. group or isopropylidene group.
  • the weight average molecular weight (Mw) of the polyphenylene ether resin is not particularly limited, but is preferably 500 to 7,000, more preferably 800 to 5,000, still more preferably 1,000 to 3,000, especially It is preferably 1,200 to 2,500.
  • the weight average molecular weight (Mw) of the polyphenylene ether-based resin is at least the above lower limit, there is a tendency to easily obtain a cured product having excellent dielectric properties of the polyphenylene ether and excellent heat resistance. Further, when the weight average molecular weight (Mw) of the (B) polyphenylene ether resin is equal to or less than the above upper limit, moldability tends to be more favorable.
  • the method for synthesizing the polyphenylene ether-based resin is not particularly limited, and a known method for synthesizing and modifying a polyphenylene ether can be applied.
  • the content of (B) the polyphenylene ether-based resin in the resin composition of the present embodiment is not particularly limited, but is preferably 1 to 30% by mass, more preferably 5 to 25% by mass, still more preferably 10 to 20% by mass.
  • the content of the polyphenylene ether-based resin is at least the above lower limit, the dielectric properties tend to be more favorable.
  • the content of the (B) polyphenylene ether-based resin is equal to or less than the above upper limit, heat resistance, moldability, and workability tend to be improved.
  • the styrene elastomer is not particularly limited as long as it has a weight average molecular weight (Mw) of more than 10,000 and less than 100,000.
  • Mw weight average molecular weight
  • the resin composition of the present embodiment tends to easily obtain excellent dielectric properties by containing (C) the styrene-based elastomer.
  • elastomer as used herein means a polymer having a glass transition temperature of 25°C or less as measured by differential scanning calorimetry according to JIS K 6240:2011.
  • Styrene-based elastomers may be used singly or in combination of two or more.
  • (C) As the styrene-based elastomer, one having a structural unit derived from a styrene-based compound represented by the following general formula (C-1) is preferable.
  • R c1 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R c2 is an alkyl group having 1 to 5 carbon atoms
  • n c1 is an integer of 0 to 5.
  • alkyl groups having 1 to 5 carbon atoms represented by R c1 and R c2 in the general formula (C-1) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group and isobutyl group, t-butyl group, n-pentyl group and the like.
  • the alkyl group having 1 to 5 carbon atoms may be linear or branched. Among these, an alkyl group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 or 2 carbon atoms is more preferred, and a methyl group is even more preferred.
  • n c1 in the general formula (C-1) is an integer of 0 to 5, preferably an integer of 0 to 2, more preferably 0 or 1, still more preferably 0.
  • the styrene-based elastomer may contain structural units other than structural units derived from styrene-based compounds.
  • structural units other than structural units derived from styrene compounds that may be contained in the styrene elastomer (C) include structural units derived from butadiene, structural units derived from isoprene, structural units derived from maleic acid, and structural units derived from maleic anhydride. Structural units and the like can be mentioned.
  • the butadiene-derived structural unit and the isoprene-derived structural unit may be hydrogenated. When hydrogenated, structural units derived from butadiene become structural units in which ethylene units and butylene units are mixed, and structural units derived from isoprene become structural units in which ethylene units and propylene units are mixed.
  • Examples of (C) styrene elastomers include hydrogenated styrene-butadiene-styrene block copolymers, hydrogenated styrene-isoprene-styrene block copolymers, and styrene-maleic anhydride copolymers. be done. Hydrogenated products of styrene-butadiene-styrene block copolymers are SEBS obtained by completely hydrogenating the carbon-carbon double bonds in the butadiene block, and SBBS obtained by partially hydrogenating a heavy bond can be mentioned.
  • complete hydrogenation in SEBS usually means that the hydrogenation rate of the entire carbon-carbon double bond is 90% or more, may be 95% or more, or may be 99% or more. It may be 100%.
  • the partial hydrogenation rate in SBBS is, for example, 60 to 85% with respect to the entire carbon-carbon double bond.
  • a hydrogenated styrene-isoprene-styrene block copolymer is obtained as SEPS by hydrogenating the polyisoprene portion.
  • SEBS and SEPS are preferred, and SEBS is more preferred, from the viewpoint of dielectric properties, conductor adhesion, heat resistance, glass transition temperature and low thermal expansion.
  • the content of structural units derived from styrene compounds is not particularly limited, but is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, and still more preferably 30 to 60% by mass.
  • the melt flow rate (MFR) of the styrene elastomer is not particularly limited, but is preferably 0.1 to 20 g/10 min, more preferably 1 to 10 g/10 min, more preferably 3 to 7 g/10 min.
  • Examples of commercially available styrene-based elastomers include SEBS, Tuftec (registered trademark) H series and M series manufactured by Asahi Kasei Corporation, Septon (registered trademark) series manufactured by Kuraray Co., Ltd., and Kraton Polymer Japan Co., Ltd. Kraton (registered trademark) G polymer series manufactured by the company and the like can be mentioned.
  • the weight average molecular weight (Mw) of the styrene-based elastomer is more than 10,000 and less than 100,000, preferably 15,000 to 98,000, more preferably 30,000 to 95,000, even more preferably is 50,000 to 93,000, more preferably 70,000 to 92,000, particularly preferably 80,000 to 90,000.
  • Mw weight average molecular weight
  • the weight average molecular weight (Mw) of the styrene-based elastomer (C) is at least the above lower limit, the fluidity of the resin composition during heating is moderately suppressed, so that moldability tends to be excellent.
  • compatibility with other resins tends to be excellent.
  • the content of (C) the styrene-based elastomer in the resin composition of the present embodiment is not particularly limited, but is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and even more preferably 5 to 10% by mass.
  • the content of the styrene-based elastomer is at least the above lower limit, dielectric properties and flexibility tend to be better.
  • the content of (C) the styrene-based elastomer is equal to or less than the above upper limit, heat resistance and flame retardancy tend to be better.
  • Organic peroxide is not particularly limited as long as it is an organic compound containing a peroxide bond (--O--O--).
  • Organic peroxides may be used singly or in combination of two or more.
  • the one-hour half-life temperature of the organic peroxide is not particularly limited, but is preferably 100 to 200°C, more preferably 120 to 170°C, and still more preferably 130 to 150°C.
  • the 1-hour half-life temperature of the organic peroxide is at least the above lower limit, the progress of unintended reactions during storage tends to be suppressed.
  • the content of (D) the organic peroxide is equal to or less than the above upper limit, the occurrence of depressions after the desmear treatment tends to be more easily suppressed.
  • the 1-hour half-life temperature of the organic peroxide is obtained by decomposing the (D) organic peroxide in the solvent under a plurality of temperature conditions, determining the decomposition rate constants at each temperature, and calculating these decomposition rate constants. It can be calculated by Arrhenius plotting.
  • the 1-hour half-life temperature in the present embodiment is the 1-hour half-life temperature measured under the condition that the concentration of (D) organic peroxide is 0.1 mol/L in benzene.
  • Organic peroxides include, for example, 1,1-di(t-butylperoxy)cyclohexane, 2,2-di(t-butylperoxy)butane, 2,2-di(4,4- di-t-butylperoxycyclohexyl)propane, peroxyketals such as 1,1-di(t-amylperoxy)cyclohexane; hydroperoxides such as cumene hydroperoxide and t-butyl hydroperoxide; t - Alkyl peroxides such as butyl peroxyacetate and t-amyl peroxy isononanoate; t-butyl cumyl peroxide, di-t-butyl peroxide, dicumyl peroxide, di-t-hexyl peroxide, 1 , 3-bis(2-t-butylperoxyisopropyl)benzene and other dialkyl peroxides; t-butylperoxyacetate
  • the content of (D) organic peroxide in the resin composition of the present embodiment is not particularly limited, but is preferably is 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and still more preferably 0.5 to 2 parts by mass.
  • (D) When the content of the organic peroxide is at least the above lower limit, the occurrence of depressions after desmear treatment tends to be more easily suppressed. Further, when the content of (D) the organic peroxide is equal to or less than the above upper limit, the reaction rate becomes moderate, and the homogeneity of the cured product tends to be easily improved.
  • Inorganic fillers include, for example, silica, alumina, titanium oxide, mica, beryllia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, silicon aluminum oxide, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay, talc, aluminum borate, silicon carbide and the like.
  • silica, alumina, mica, and talc are preferred, and silica and alumina are more preferred, from the viewpoint of low thermal expansion, heat resistance, and flame retardancy.
  • Silica includes, for example, precipitated silica produced by a wet method and having a high moisture content, and dry-process silica produced by a dry method and containing almost no bound water.
  • dry process silica include crushed silica, fumed silica, fused silica, etc., depending on the production method.
  • the average particle size of the (E) inorganic filler is not particularly limited, but from the viewpoint of dispersibility and fine wiring properties of the (E) inorganic filler, it is preferably 0.01 to 20 ⁇ m, more preferably 0.1 to 10 ⁇ m. , more preferably 0.2 to 1 ⁇ m, particularly preferably 0.3 to 0.8 ⁇ m.
  • the average particle size of the inorganic filler (E) is the total volume of the particles as 100%, and when the cumulative frequency distribution curve by the particle size is obtained, the particle size of the point corresponding to 50% of the volume. That is.
  • the average particle size of the inorganic filler can be measured, for example, with a particle size distribution analyzer using a laser diffraction scattering method.
  • the shape of the inorganic filler includes, for example, a spherical shape, a crushed shape, etc., and a spherical shape is preferred.
  • ((E) content of inorganic filler When the resin composition of the present embodiment contains (E) an inorganic filler, the content is not particularly limited, but is preferably 30 to 90 with respect to the total solid content (100% by mass) of the resin composition. % by mass, more preferably 40 to 80% by mass, and even more preferably 50 to 70% by mass.
  • the content of the inorganic filler is at least the above lower limit, low thermal expansion, heat resistance and flame retardancy tend to be more favorable.
  • the content of (E) the inorganic filler is equal to or less than the above upper limit, moldability and conductor adhesiveness tend to be more favorable.
  • the resin composition of the present embodiment preferably further contains (F) a curing accelerator other than the organic peroxide.
  • (F) Curing accelerators other than organic peroxides may be used alone or in combination of two or more.
  • Curing accelerators other than organic peroxides include, for example, amine-based curing accelerators, imidazole-based curing accelerators, phosphorus-based curing accelerators, organic metal salts, and acidic catalysts.
  • imidazole-based curing accelerators are not classified as amine-based curing accelerators.
  • amine curing accelerators include amine compounds having primary to tertiary amines such as triethylamine, pyridine, tributylamine and dicyandiamide; quaternary ammonium compounds.
  • imidazole-based curing accelerators examples include imidazole compounds such as methylimidazole, phenylimidazole and 2-undecylimidazole; isocyanate masked imidazoles such as addition reaction products of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole; mentioned.
  • phosphorus curing accelerators include tertiary phosphines such as triphenylphosphine; quaternary phosphonium compounds such as tri-n-butylphosphine addition reaction product of p-benzoquinone.
  • Organic metal salts include, for example, carboxylates of manganese, cobalt, zinc and the like.
  • acidic catalysts examples include p-toluenesulfonic acid and the like.
  • acidic catalysts examples include p-toluenesulfonic acid and the like.
  • amine-based curing accelerators examples include amine-based curing accelerators, imidazole-based curing accelerators, and phosphorus-based curing accelerators are preferable.
  • Class phosphonium compounds are more preferred, and it is even more preferred to use them in combination.
  • the content thereof is preferably 0.01 to 10 parts per 100 parts by mass of the maleimide resin (A). parts by mass, more preferably 0.1 to 7 parts by mass, and even more preferably 1 to 5 parts by mass.
  • the content of the curing accelerator (F) other than the organic peroxide is at least the above lower limit, a sufficient curing acceleration effect tends to be obtained.
  • the content of (F) the curing accelerator other than the organic peroxide is equal to or less than the above upper limit, the storage stability tends to be more favorable.
  • the resin composition of the present embodiment may further contain a resin material other than the above components, a flame retardant, an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a coloring agent, a lubricant, and a silane. It may contain one or more optional components selected from the group consisting of coupling agents, organic solvents and additives other than these. Each of the above optional components may be used alone or in combination of two or more. The content of the above optional components in the resin composition of the present embodiment is not particularly limited, and may be used as necessary within a range that does not impair the effects of the present embodiment. Moreover, the resin composition of the present embodiment may not contain any of the above optional components depending on the desired performance.
  • the resin composition of this embodiment can be produced by mixing the components described above.
  • each component When mixing each component, each component may be dissolved or dispersed while stirring.
  • Conditions such as the order of mixing raw materials, mixing temperature, and mixing time are not particularly limited, and may be arbitrarily set according to the type of raw materials.
  • the relative dielectric constant (Dk) at 10 GHz of the cured product of the resin composition of the present embodiment is not particularly limited, but from the viewpoint of low transmission loss, it is preferably 3.8 or less, more preferably 3.6 or less, and further Preferably it is 3.4 or less.
  • the dielectric constant (Dk) of the cured product is preferably as small as possible, and the lower limit thereof is not particularly limited. It may be 4 or more, or 2.6 or more.
  • the conditions for obtaining a cured product from the resin composition of the present embodiment can be the conditions described in Examples.
  • the dielectric loss tangent (Df) at 10 GHz of the cured product of the resin composition of the present embodiment is not particularly limited, but from the viewpoint of low transmission loss, it is preferably 0.0040 or less, more preferably 0.0035 or less, and further preferably is 0.0030 or less.
  • the dielectric loss tangent (Df) of the cured product is preferably as small as possible, and the lower limit thereof is not particularly limited. or more, or 0.0020 or more.
  • the relative permittivity (Dk) and dielectric loss tangent (Df) are values based on the cavity resonator perturbation method, more specifically, values measured by the method described in Examples.
  • the conditions for obtaining a cured product from the resin composition of the present embodiment can be the conditions described in Examples.
  • the prepreg of the present embodiment is a prepreg containing the resin composition of the present embodiment or a semi-cured material of the resin composition. That is, the prepreg of this embodiment is a prepreg formed using the resin composition of this embodiment.
  • the prepreg of the present embodiment preferably contains a B-staged resin composition obtained by converting the resin composition of the present embodiment into a B-stage, and a sheet-like fiber base material.
  • the prepreg of the present embodiment is preferably obtained by impregnating or coating a sheet-like fiber base material with the resin composition of the present embodiment, followed by B-stage.
  • B-staging is to bring the material into a B-stage state defined in JIS K 6900:1994, and is also called semi-curing.
  • sheet-like fiber base material contained in the prepreg of the present embodiment for example, known sheet-like fiber base materials used for various laminates for electrical insulating materials can be used.
  • materials for the sheet-like fiber substrate include inorganic fibers such as E-glass, D-glass, S-glass and Q-glass; organic fibers such as polyimide, polyester and tetrafluoroethylene; and mixtures thereof.
  • These sheet-like fiber base materials have shapes such as woven fabrics, non-woven fabrics, robinks, chopped strand mats, surfacing mats, and the like.
  • the prepreg of the present embodiment can be produced, for example, by impregnating or applying the resin composition of the present embodiment to a sheet-like fiber base material, and then B-stages the resin composition by heating and drying.
  • the temperature and time of heat drying are not particularly limited, but from the viewpoint of productivity and moderate B-stage of the resin composition of the present embodiment, for example, 50 to 200 ° C., 1 to 30 minutes. .
  • the concentration of solids derived from the resin composition in the prepreg of the present embodiment is not particularly limited. More preferably 25 to 80 mass %, still more preferably 30 to 75 mass %.
  • the resin film of the present embodiment is a resin film containing the resin composition of the present embodiment or a semi-cured product of the resin composition. That is, the resin film of this embodiment is a resin film formed using the resin composition of this embodiment.
  • the resin film of the present embodiment is a film made from the resin composition of the present embodiment or a B-staged resin composition obtained by converting the resin composition of the present embodiment into a B-stage.
  • the resin film of the present embodiment can be produced, for example, by applying the resin composition of the present embodiment containing an organic solvent, ie, a resin varnish, to a support, followed by heating and drying. Examples of the support include plastic films, metal foils, release papers and the like.
  • the temperature and time of heat drying are not particularly limited, but from the viewpoint of productivity and moderate B-stage of the resin composition of the present embodiment, it can be 50 to 200 ° C. and 1 to 30 minutes.
  • the resin film of the present embodiment is preferably used for forming an insulating layer when manufacturing a printed wiring board.
  • the laminated board of this embodiment is a laminated board having a cured product of the prepreg of this embodiment. That is, the laminate of this embodiment is a laminate formed using the prepreg of this embodiment.
  • the laminate of the present embodiment preferably contains the cured prepreg of the present embodiment and metal foil.
  • a laminate having metal foil is sometimes referred to as a metal-clad laminate.
  • the metal of the metal foil is not particularly limited, and examples thereof include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing one or more of these metal elements. are mentioned.
  • the laminate of the present embodiment can be produced, for example, by placing a metal foil on one side or both sides of the prepreg of the present embodiment, followed by heating and pressure molding. Normally, the laminate of the present embodiment is obtained by curing the B-staged prepreg by this heat and pressure molding. In the heat and pressure molding, only one prepreg may be used, or two or more prepregs may be laminated.
  • heat-press molding for example, a multi-stage press, a multi-stage vacuum press, continuous molding, an autoclave molding machine, etc. can be used.
  • the conditions for the heat and pressure molding are not particularly limited, but can be, for example, a temperature of 100 to 300° C., a time of 10 to 300 minutes, and a pressure of 1.5 to 5 MPa.
  • the printed wiring board of this embodiment is a printed wiring board having a cured product of the resin composition of this embodiment.
  • the printed wiring board of the present embodiment is, for example, a printed wiring board formed using one or more selected from the group consisting of the prepreg of the present embodiment, the resin film of the present embodiment, and the laminate of the present embodiment. be.
  • the printed wiring board of the present embodiment includes at least a cured product of the resin composition of the present embodiment and a conductor circuit layer, a cured product of the prepreg of the present embodiment, and a cured product of the resin film of the present embodiment.
  • the method for manufacturing the printed wiring board of the present embodiment preferably includes a step of subjecting the insulating material containing the cured product of the resin composition of the present embodiment to desmear treatment.
  • a desmearing method a known method can be applied.
  • the printed wiring board of the present embodiment can be manufactured by forming a conductive circuit on the insulating material subjected to the desmear treatment by a known method.
  • a multilayer printed wiring board can also be manufactured by applying a multilayer adhesion process, if necessary.
  • the conductor circuit can be formed by appropriately performing, for example, drilling, metal plating, etching of metal foil, or the like.
  • the semiconductor package of this embodiment is a semiconductor package having the printed wiring board of this embodiment. That is, the semiconductor package of this embodiment is a semiconductor package formed using the printed wiring board of this embodiment.
  • the semiconductor package of this embodiment can be manufactured, for example, by mounting a semiconductor chip, a memory, etc. on the printed wiring board of this embodiment by a known method.
  • the weight average molecular weight (Mw) was measured by the following method. Conversion was performed from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). Calibration curve, standard polystyrene: TSK standard POLYSTYRENE (Type; A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40) [manufactured by Tosoh Corporation, product name] and approximated by a cubic equation. GPC measurement conditions are shown below.
  • Examples 1 and 2 Comparative Example 1 (Manufacture of resin composition)
  • Each component shown in Table 1 was blended according to the formulation shown in Table 1, and stirred and mixed with 58 parts by mass of toluene and 10 parts by mass of methyl isobutyl ketone at room temperature (25 ° C.) to obtain a solid content concentration of 55 to 65.
  • a mass % resin composition was produced.
  • the unit of the compounding amount of each component is parts by mass, and in the case of a solution, it means parts by mass in terms of solid content.
  • a double-sided copper-clad laminate (thickness: 0.23 mm) was manufactured by placing in contact with the prepreg and heat-pressing molding under the conditions of a temperature of 230° C., a pressure of 3.0 MPa, and a time of 90 minutes.
  • the copper foil was removed from the double-sided copper-clad laminate obtained in each example by immersing it in a copper etching solution to obtain a cured prepreg.
  • the test piece was desmeared by performing the following (1) to (4) in order.
  • (1) After being immersed in a swelling liquid (manufactured by Atotech Japan Co., Ltd., trade name "Swelling Dip Securigant P", an aqueous solution of glycol ethers and sodium hydroxide) at 70°C for 5 minutes, it was washed with water.
  • An ion milling device (manufactured by Hitachi High-Technologies Co., Ltd., trade name: E-3500) was applied to the test piece after the desmear treatment with an acceleration voltage of 6 kV, a discharge voltage of 4 kV, and an Ar gas flow rate of 1.80 cm 3 /min. , a processing width of 500 ⁇ m, and a processing time of 6 hours. Then, using a scanning electron microscope (SEM) (manufactured by Hitachi High-Technologies Co., Ltd., trade name: SV-4700), the above test was performed under the conditions of secondary electron mode, acceleration voltage of 20 kV, and observation magnification of 5,000 times. A cross-section of the piece was observed.
  • SEM scanning electron microscope
  • the test piece has a composite layer consisting of a glass cloth and a cured product of the resin composition, and a cured resin consisting only of a cured product of the resin composition on both sides of the composite layer. It was confirmed that it has a material layer.
  • the test pieces having dents dents were observed on the surface of the cured resin layer, that is, on the surface of the cured resin layer that was in contact with the copper foil before removal.
  • FIG. 1 shows a schematic cross-sectional view of a test piece 10 for explaining a method of calculating the existence ratio (%) of depressions in the test piece after desmear treatment.
  • an area S1 surrounded by a dotted line is an area when it is assumed that the test piece 10 does not have a depression.
  • a region S2 is a region of the depression 3 with a size exceeding 0.5 ⁇ m.
  • the size of the recess 3 here means the length of a straight line connecting both ends of the recess represented by D in the enlarged view of FIG.
  • the existence ratio (%) of depressions was calculated as the ratio of the total area of the region S2 to the area of the region S1 (S2 ⁇ 100/S1).
  • a specimen was prepared by etching the copper foil of the double-sided copper-clad laminate obtained in each example into a straight line with a width of 3 mm.
  • the formed straight line-shaped copper foil is attached to a small desktop tester (manufactured by Shimadzu Corporation, trade name "EZ-TEST"), and the copper foil is pulled by peeling it off in a 90 ° direction at room temperature (25 ° C.).
  • the peel strength was measured.
  • the pulling speed for peeling off the copper foil was 50 mm/min.
  • the outer layer copper foil of the double-sided copper-clad laminate obtained in each example was removed by immersion in a copper etching solution (10% by mass ammonium persulfate solution, manufactured by Mitsubishi Gas Chemical Co., Ltd.) to a length of 60 mm and a width of 2 mm. A cut piece was used as a test piece. Using the test piece, the dielectric constant (Dk) and dielectric loss tangent (Df) were measured by the cavity resonator perturbation method.
  • a cavity resonator is "CP129” (10 GHz band resonator) manufactured by Kanto Denshi Applied Development Co., Ltd., and a measurement program is "CPMA-V2". each used. The measurement was performed under conditions of a frequency of 10 GHz and a measurement temperature of 25°C.
  • SEBS maleic anhydride-modified hydrogenated styrene elastomer (SEBS), acid value 10 mgCH3ONa /g, styrene content 45% by mass, weight average molecular weight (Mw) 86,000
  • the resin composition of the present embodiment can form a cured product in which the occurrence of depressions on the surface after desmear treatment is suppressed, prepregs, laminates, printed wiring boards, and semiconductors obtained using the resin composition Packages and the like are particularly suitable for electronic component applications that handle high-frequency signals.

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WO2025126952A1 (ja) * 2023-12-12 2025-06-19 株式会社レゾナック 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
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