JP2022119326A - heterocyclic compound - Google Patents

Abstract

To provide a novel heterocyclic compound, and a production method of the same.SOLUTION: A heterocyclic compound represented by the following general formula (1) is provided, where, in the formula (1), R2 is a univalent hydrocarbon group, or a hydrogen atom, R3 is a hydrogen atom, a methyl group, or an ethyl group, X is a triazole structure, or a tetrazole structure represented by the following formulae (2), Y is a sulfur atom, or an NH group, and, in the general formula (2), R1 is a univalent hydrocarbon group, or a hydrogen atom.SELECTED DRAWING: Figure 1

Description

TECHNICAL FIELD The present invention relates to a heterocyclic compound, a method for producing the same, and the like.

Heterocyclic compounds are cyclic compounds containing at least two different elements in the ring. Known rings include, for example, three-, four-, five-, six-, seven-, eight-, nine-, and fused rings, all of which are saturated or unsaturated. good. Heteroatoms in the ring are known to include, for example, carbon (C) atoms in combination with at least one heteroatom, and heteroatoms include, for example, boron (B) atoms, nitrogen (N) atoms, , an oxygen (O) atom, a phosphorus (P) atom, a sulfur (S) atom, and the like.

Heterocyclic compounds are used in various fields such as chemical synthesis, heterocyclic chemistry, nucleic acids and drugs derived therefrom, biological resources, biofuels, dyes, optical materials, electronic materials, and transmission lines. Among them, in the formation of a metal-clad laminate that can be used for high-frequency transmission and fifth-generation (5G) communication systems, a heterocyclic ring containing a nitrogen atom is used as an adhesion aid to improve the adhesion between a member and a metal surface. compounds are of interest.

For example, Patent Document 1 discloses a curable resin composition containing a triazole cyclic compound having a 1,2,3-triazole ring or a 1,2,4-triazole ring in order to increase the adhesion between a cured product and a conductor layer. It is described to be contained in things.

For example, Patent Literature 2 describes imidazole-based, thiazole-based, and triazole-based adhesion imparting agents as additives.

WO2016/088358 Japanese Patent Application Laid-Open No. 2001-298275

The triazole compound described in Patent Document 1 does not have a polymerizable group and is poor in polycondensation property with the target member. In addition, since the curable resin composition described in Patent Document 1 enhances the adhesion between the cured product and the conductor layer by the combination of the epoxy compound, the triazole compound, and the tertiary amine, the adhesion due to the triazole compound alone Not focused on improvement.

Moreover, the adhesion-imparting agent described in Patent Document 2 does not disclose a specific structure or embodiment of the imidazole compound having a polymerizable group.

Furthermore, the heterocyclic compounds containing nitrogen atoms described in Patent Documents 1 and 2 improve the adhesion between a member and a metal surface, adhesion, lamination, etc., and prevent corrosion of the metal surface. There is still room for improvement in compatibility with protection.

Accordingly, an object of the present invention is to provide a novel heterocyclic compound, a method for producing the same, and to improve adhesion between a member and a metal surface and to protect the metal surface from corrosion.

｛式中、Ｒ^２は、１価の炭化水素基、又は水素原子であり、Ｒ^３は、水素原子、メチル基、又はエチル基であり、Ｘは、下記一般式（２）：

（式中、Ｒ^１は、１価の炭化水素基、又は水素原子である）で表されるトリアゾール構造又はテトラゾール構造であり、そしてＹは、硫黄原子、又はＮＨ基である｝
で表される複素環化合物。
［２］
（Ａ）項目１に記載の複素環化合物；
（Ｂ）エチレン性不飽和基を有する樹脂；
（Ｃ）重合開始剤；及び
（Ｄ）溶剤；
を含むことを特徴とする樹脂組成物。
［３］
前記（Ｂ）エチレン性不飽和基を有する樹脂が、ポリフェニレンエーテル、ポリスチレン、脂環式構造を有する樹脂、ポリベンゾオキサゾール前駆体樹脂、ポリイミド前駆体樹脂、及びフェノール樹脂からなる群から選ばれる少なくとも１種の樹脂である、項目２に記載の樹脂組成物。
［４］
前記（Ｃ）重合開始剤が、オキシムエステル、及びパーオキサイドからなる群から選ばれる少なくとも１種である、項目２又は３に記載の樹脂組成物。
［５］
項目２～４のいずれか１項に記載の樹脂組成物と支持体または基材とを備える積層体。
［６］
下記の特性：
（ｉ）ピール強度≧0.4Ｎ；
（ｉｉ）Df2 - Df1 ≦ 0.001；
｛式中、Df2は、前記（Ａ）成分を含む前記樹脂組成物の硬化物の誘電正接を示し、そしてDf1は、前記樹脂組成物から前記（Ａ）成分を除いた樹脂組成物の硬化物の誘電正接を示す）を満たす、項目５に記載の積層体。
［７］
項目５又は６に記載の積層体を備えるプリント配線板。
［８］
項目７に記載のプリント配線板を備える高速通信用モジュール。 The above problems can be solved by the following examples of technical means.
[1]
The following general formula (1):

{Wherein, R ² is a monovalent hydrocarbon group or a hydrogen atom, R ³ is a hydrogen atom, a methyl group, or an ethyl group, and X is the following general formula (2):

(wherein R ¹ is a monovalent hydrocarbon group or a hydrogen atom), and Y is a sulfur atom or an NH group}
A heterocyclic compound represented by
[2]
(A) the heterocyclic compound according to item 1;
(B) a resin having an ethylenically unsaturated group;
(C) a polymerization initiator; and (D) a solvent;
A resin composition comprising:
[3]
The (B) resin having an ethylenically unsaturated group is at least one selected from the group consisting of polyphenylene ether, polystyrene, a resin having an alicyclic structure, a polybenzoxazole precursor resin, a polyimide precursor resin, and a phenolic resin. 3. The resin composition according to item 2, which is a seed resin.
[4]
The resin composition according to item 2 or 3, wherein the (C) polymerization initiator is at least one selected from the group consisting of oxime esters and peroxides.
[5]
A laminate comprising the resin composition according to any one of items 2 to 4 and a support or substrate.
[6]
The following characteristics:
(i) peel strength ≥ 0.4N;
(ii) Df2 - Df1 ≤ 0.001;
{In the formula, Df2 represents the dielectric loss tangent of the cured product of the resin composition containing the component (A), and Df1 represents the cured product of the resin composition excluding the component (A) from the resin composition. The laminate according to item 5, which satisfies the dielectric loss tangent of ).
[7]
A printed wiring board comprising the laminate according to item 5 or 6.
[8]
A high-speed communication module comprising the printed wiring board according to item 7.

INDUSTRIAL APPLICABILITY According to the present invention, novel heterocyclic compounds and methods for producing the same are provided, and various chemical reactions, polymerization reactions, syntheses or formulations can be carried out using the novel heterocyclic compounds as starting materials or intermediates. For example, it can be used as an adhesion aid in adhesion, adhesion, lamination, etc. between a member and a metal surface, or can protect the metal surface from corrosion or rust and improve adhesion.

1 is a ¹ H-NMR chart of a heterocyclic compound according to one embodiment of the present invention. 1 is a GPC chart of a heterocyclic compound according to one embodiment of the present invention. 1 is a ¹ H-NMR chart of a heterocyclic compound according to another embodiment of the present invention. 1 is a ¹ H-NMR chart of a heterocyclic compound according to still another embodiment of the present invention.

｛式中、Ｒ²は、１価の炭化水素基、又は水素原子であり、Ｒ³は、水素原子、メチル基、又はエチル基であり、Ｘは、下記一般式（２）：

（式中、Ｒ¹は、１価の炭化水素基、又は水素原子である。）で表されるトリアゾール構造又はテトラゾール構造であり、そしてＹは、硫黄原子、又はＮＨ基である｝
で表される。 <Heterocyclic compound>
The heterocyclic compound according to this embodiment has the following general formula (1):

{In the formula, R ² is a monovalent hydrocarbon group or a hydrogen atom, R ³ is a hydrogen atom, a methyl group, or an ethyl group, and X is the following general formula (2):

(Wherein, R ¹ is a monovalent hydrocarbon group or a hydrogen atom.) is a triazole structure or a tetrazole structure, and Y is a sulfur atom or an NH group}
is represented by

The heterocyclic compound represented by the general formula (1) forms a complex with a metal by a triazole structure or a tetrazole structure represented by the general formula (2), an acryloyl group for a resin having an ethylenically unsaturated group, a methacryloyl group, or By controlling the polarity through the chemical bonding of the ethacryloyl group and the —OR ² modification of the linking portion, there is a tendency to achieve both adhesion between the metal surface and the adherend and corrosion resistance of the metal. This tendency is remarkable when the metal surface is made of copper (Cu) and the Cu surface is a low roughness surface, an ultra-low roughness surface, or a non-roughened surface.

In general formula (1), R ² is a monovalent hydrocarbon group or a hydrogen atom. A monovalent hydrocarbon group as the R ² group may have from 1 to 33 carbon atoms, may be substituted or unsubstituted, may be saturated or unsaturated, may be linear or cyclic, and/or may be aliphatic or aromatic. In the case of chain, it may be linear or branched, and in the case of substitution, the substituent may be a monovalent aliphatic or aromatic group having 1 to 10 carbon atoms, such as , methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n- Decyl group; vinyl, allyl, propenyl, 3-butenyl, 2-butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, and hexynyl groups; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; phenyl, aryl, and benzyl groups, and the like.

Specific examples of monovalent hydrocarbon groups as R ² groups may be substituted or unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms or substituted or unsubstituted aromatic groups having 6 to 24 carbon atoms. .

The substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms as the R ² group preferably has 1 to 10, 1 to 15 or 4 to 12 carbon atoms in the case of a chain, and alicyclic C3-18 or 3-20 is preferred, and specific examples of substituted or unsubstituted aliphatic hydrocarbon groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl , t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups; straight or branched chain alkyl groups; vinyl, allyl, propenyl, 3- Unsaturated aliphatic hydrocarbon groups such as butenyl, 2-butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, and hexynyl groups; and cyclopropyl, cyclobutyl cycloalkyl groups such as , cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

Specific examples of substituted or unsubstituted aromatic groups having 6 to 24 carbon atoms as R ² groups include phenyl, aryl, benzyl, naphthyl, anthryl and phenanthryl groups.

In general formula (1), R ² is preferably a hydrogen (H) atom from the viewpoint of preventing deterioration of the dielectric properties of the metal-clad laminate due to deposits on the metal surface. When —OR ² is —OH in general formula (1), the linking portion between the triazole structure or tetrazole structure and the acryloyl group, methacryloyl group or ethacryloyl group is —OH modified, whereby the adherend Even if the heterocyclic compound represented by the general formula (1) is contained in the resin composition for forming, the increase in the Df (dielectric loss tangent) value of the adherend can be suppressed.

In general formula (1), R ³ is a hydrogen atom, a methyl group, or an ethyl group, and from the viewpoint of availability of synthetic raw materials for the heterocyclic compound represented by general formula (1), or is preferably a methyl group, and from the viewpoint of protecting the metal surface from corrosion or rust and improving adhesion to the adherend, it is preferably a methyl group, and the bulkiness of the resulting heterocyclic compound From the viewpoint of, it is preferably an ethyl group.

In the general formula (1), Y is a sulfur (S) atom or an NH group, and -S- or - NH- is formed.

In the general formula (1), the presence of the linking portion Y consists of a triazole structure or a tetrazole structure capable of forming a complex with copper (Cu) and an acryloyl group, methacryloyl group or ethacryloyl group capable of chemically bonding to the constituent resin of the adherend. To suppress an increase in the Df (dielectric loss tangent) value of the adherend while improving the adhesion strength between the adherend containing the molecule and the metal surface by coexisting the group and the —OR ² modified portion in one molecule. enable

（式中、Ｒ¹は、１価の炭化水素基、又は水素原子である）
で表される置換若しくは非置換の１，２，４－トリアゾール骨格を有する１価の基、又は下記式（２Ａ－２）：

で表される３－アミノ－１，２，４－トリアゾール由来の１価の基であり、そしてテトラゾール構造の場合には、下記式（２Ｚ）：

で表されるテトラゾール由来の１価の基である。 In general formula (1), X is a triazole structure or tetrazole structure represented by general formula (2), and in the case of a triazole structure, the following formula (2A-1):

(Wherein, R ¹ is a monovalent hydrocarbon group or a hydrogen atom)
A monovalent group having a substituted or unsubstituted 1,2,4-triazole skeleton represented by or the following formula (2A-2):

is a monovalent group derived from 3-amino-1,2,4-triazole represented by and in the case of a tetrazole structure, the following formula (2Z):

is a monovalent group derived from tetrazole represented by

In the 1,2,4-triazole ring represented by formula (2A-1), the positional relationship between the linking portion to Y in general formula (1) and R ¹ is 3-position and 5-position, or vice versa. is.

In formula (2A-1), R ¹ is a monovalent hydrocarbon group or a hydrogen (H) atom, and when R ¹ =H, the monovalent The group is an unsubstituted 1,2,4-triazole group and can be linked to Y in general formula (1) at the 3-position in the 1,2,4-triazole ring.

The monovalent hydrocarbon group as the R ¹ group may have from 1 to 33 carbon atoms, may be substituted or unsubstituted, may be saturated or unsaturated, may be linear or cyclic, and/or may be aliphatic or aromatic. In the case of chain, it may be linear or branched, and in the case of substitution, the substituent may be a monovalent aliphatic or aromatic group having 1 to 10 carbon atoms, such as , methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n- Decyl group; vinyl, allyl, propenyl, 3-butenyl, 2-butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, and hexynyl groups; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; phenyl, aryl, and benzyl groups, and the like.

Specific examples of monovalent hydrocarbon groups as R ¹ groups may be substituted or unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms or substituted or unsubstituted aromatic groups having 6 to 24 carbon atoms. .

The substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms as the R ¹ group preferably has 1 to 10, 1 to 15 or 4 to 12 carbon atoms in the case of a chain, and alicyclic C3-18 or 3-20 is preferred, and specific examples of substituted or unsubstituted aliphatic hydrocarbon groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl , t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups; straight or branched chain alkyl groups; vinyl, allyl, propenyl, 3- Unsaturated aliphatic hydrocarbon groups such as butenyl, 2-butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, octenyl, nonenyl, decenyl, ethynyl, propynyl, butynyl, pentynyl, and hexynyl groups; and cyclopropyl, cyclobutyl cycloalkyl groups such as , cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

Specific examples of the substituted or unsubstituted aromatic group having 6 to 24 carbon atoms as the R ¹ group include phenyl, aryl, benzyl, naphthyl, anthryl and phenanthryl groups.

The monovalent group represented by the formula (2A-2) is substituted with an amino group at the 3-position in the 1,2,4-triazole ring, and at the 5-position, Y in the general formula (1) can be concatenated with

The monovalent group represented by formula (2Z) can be linked to Y in general formula (1) at the 5-position in the tetrazole ring.

The molecular weight of the heterocyclic compound represented by general formula (1) is determined depending on the selection of X, Y, R ¹ , R ² or R ³ , for example 200-1,030, 200-830, 200-630. , 200-530, 200-430, 200-380, or 200-330.

Regarding the heterocyclic compound represented by the general formula (1), a preferable combination of X, Y, R ² and R ³ from the viewpoint of protection of the metal surface from corrosion or rust and improvement of adhesion to the adherend. is shown below:
heterocyclic compound I {X = monovalent group represented by formula (2A-1), Y = S, R ² = H, R ³ = methyl group};
Heterocyclic compound II {X = monovalent group represented by formula (2A-2), Y = S, R ² = H, R ³ = methyl group}; and heterocyclic compound III {X = formula (2Z) Y=NH, R ² =H, R ³ =methyl group}.

｛式中、Ｒ¹は、式（２）及び（２Ａ－１）について定義されたとおりである｝
で表される。 Specifically, the heterocyclic compound I has the following general formula (I):

{wherein R ¹ is as defined for formulas (2) and (2A-1)}
is represented by

で表される化合物であることが好ましい。 The heterocyclic compound I has the following formula (I-1):

It is preferably a compound represented by.

で表される。 The heterocyclic compound II is specifically represented by the following formula (II):

is represented by

で表される。 Heterocyclic compound III is specifically represented by the following formula (III):

is represented by

The heterocyclic compounds I to III can be contained in the resin composition independently or in any combination, thereby suppressing deterioration of the dielectric properties of the cured product of the resin composition, It is possible to improve the adhesion to the metal surface of the metal clad laminate and prevent metal corrosion or rust of the metal clad laminate.

<Method for producing heterocyclic compound>
The method for producing a heterocyclic compound according to the present embodiment includes, for example, an epoxide cleavage reaction, an epoxide addition reaction, an oxirane ring-opening reaction, an amine-epoxide reaction, a thiol-epoxide reaction, and an epoxy-based compound. It can include (partial) crosslinking reaction or curing reaction, reaction promotion of epoxide by imidazoles or tetrazoles, reaction promotion of thiols and epoxide by tertiary amine, reaction promotion by other catalytic actions, and the like. These can be used alone or in combination.

Specifically, glycidyl acrylate (GA), glycidyl methacrylate (GMA), glycidyl ethacrylate (GEA), or any combination thereof (hereinafter collectively referred to as "glycidyl (alkyl) acrylate compound") and , the following formula:
X—SH {wherein X is as defined in formula (1) above}; and/or X—NH ₂ {wherein X is as defined in formula (1) above }
The heterocyclic compound represented by the general formula (1) can be obtained by reacting the compound represented by the above.

As the glycidyl (alkyl) acrylate compound, GA, GMA, GEA or any combination thereof can be selected depending on the given R ³ in general formula (1). GA or GMA is preferable from the viewpoint of raw material availability, GMA is preferable from the viewpoint of protecting the metal surface from corrosion or rust and improving adhesion to the adherend, and the bulkiness of the reaction product is preferable. GEA is preferred from.

For the reaction of a glycidyl (alkyl) acrylate compound with a compound represented by the formula X-SH and/or X-NH ₂ , it is preferred to use an organic solvent as a reaction solvent, for example ketones such as acetone. alcohols such as methanol and ethanol; and glycol-based solvents such as glycol ether, propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate.

Regarding the reaction conditions, the reaction temperature may be normal temperature or room temperature, for example, within the range of 15°C to 40°C or 20°C to 35°C, and the reaction time may be 3 hours to 120 hours, 4 hours to 118°C. hours, 4 hours to 50 hours, or 6 hours to 25 hours, and the reaction atmosphere is preferably under draft drying or vacuum drying.

After completion of the reaction, from the viewpoint of improving the yield of the product or identifying the product, for example, filtration, evaporation to dryness, vacuum drying, standing, decantation, precipitation, redissolution, reprecipitation, gel permeation chromatography The product can be fractionated by lithography (GPC), nuclear magnetic resonance (NMR) measurement, etc. alone or in combination.

A reaction of a glycidyl (alkyl) acrylate compound with a compound represented by the formula X-SH and/or X- _NH2 yields a heterocyclic compound in which ^R2 is a hydrogen (H) atom in general formula (1). tend to be easily stolen.

When obtaining a heterocyclic compound in which R ² is a monovalent hydrocarbon in the general formula (1), (i) in the above reaction, R ² OH (provided that R ² is a monovalent hydrocarbon) ^{( ii} ) a method of intervening a nucleophilic agent such as After converting the —OH group of the heterocyclic compound where R ² =H in (1) to a metal alkoxide such as sodium alkoxide (—O ⁻ Na ⁺ ) using a base such as sodium hydride or sodium hydroxide, , a reaction with a halogen compound such as an alkyl halide, or a reaction with a halogen compound such as an alkyl halide in the presence of a tertiary amine such as triethylamine, to form an —OR ² group (where R ² is a monovalent hydrocarbon There can be employed a method of forming a

In the reaction between the glycidyl (alkyl) acrylate compound and the compound represented by the formula X-SH or X- _NH2 , the molar ratio of the two (glycidyl (alkyl) acrylate compound: represented by the formula X-SH or X- _NH2 compound) is preferably 1:1.0 to 1.3, or 1:1.0 to 1.2 from the viewpoint of improving the yield of the product or suppressing the isomerization reaction, More preferably, it is 1:1.0 to 1.1.

The reactant with the glycidyl (alkyl) acrylate compound is preferably a compound represented by the formula X-SH when X has a triazole structure, and a compound represented by the formula X-NH ₂ when X has a tetrazole structure. The compounds represented are preferred.

｛式中、Ｒ¹は、上記式（２）及び（２Ａ－１）において定義されたとおりである｝
で表される化合物、又は３－アミノ－５－メルカプト－１，２，４－トリアゾールであることが好ましく、より好ましくは、３－メルカプト－１，２，４－トリアゾール、又は３－アミノ－５－メルカプト－１，２，４－トリアゾールである。 The compound represented by the formula X-SH has the following formula when X has a triazole structure:

{Wherein, R ¹ is as defined in formulas (2) and (2A-1) above}
or 3-amino-5-mercapto-1,2,4-triazole, more preferably 3-mercapto-1,2,4-triazole or 3-amino-5 - mercapto-1,2,4-triazole.

The compound represented by the formula X-NH ₂ is preferably 5-aminotetrazole when X has a tetrazole structure.

A basic catalyst or a strong basic catalyst is preferably used for the reaction of the glycidyl(alkyl)acrylate compound with the compounds of formula X-SH and/or X-NH ₂ . When a basic catalyst or a strong base catalyst is used, the molar ratio of the glycidyl (alkyl) acrylate compound to the catalyst (glycidyl (alkyl) acrylate compound:catalyst) is 1:1 from the viewpoint of suppressing the formation of isomers. It is preferably 0.09 to 0.13, more preferably 1:0.10 to 0.13. From the same point of view, the molar ratio of the glycidyl (alkyl) acrylate compound, the compound represented by the formula X-SH or X-NH ₂ and the catalyst (glycidyl (alkyl) acrylate compound: formula X-SH or X-NH ₂ The ratio of the represented compound:catalyst) is preferably 1:1.0-1.3:0.09-0.13.

While not wishing to be bound by theory, primary, secondary and tertiary amino groups are known to differ greatly in their reactivity towards epoxy groups, with primary amino groups being the least reactive. The strongest, secondary amino groups are weakly reactive, and tertiary amines do not have active hydrogens, so they do not react with epoxy groups, either with each other or with other functional groups (e.g., primary amino group, mercapto group, alcoholic hydroxyl group, etc.). Thus, the use of tertiary amines such as triethylamine (TEA) as basic catalysts can promote the reaction of mercapto groups by catalysis of tertiary amines, or compounds with primary amino groups and glycidyl Tertiary amines can be used catalytically without interfering with the reaction with (alkyl)acrylate compounds.

In addition, if a tertiary amine such as TEA is used as a catalyst in the reaction for obtaining the heterocyclic compound according to the present embodiment, the isomerization reaction can be suppressed and the yield of the predetermined heterocyclic compound can be easily improved. A tendency was found.

In the reaction for obtaining the heterocyclic compound according to the present embodiment, when it is desired to suppress the progress of the crosslinking reaction or curing reaction of epoxy groups derived from GA, GMA, GEA, or a combination thereof, polyamino compounds and polymercapto compounds are used. It is preferable to avoid contamination with polyfunctional compounds such as

On the other hand, depending on the application of the heterocyclic compound according to this embodiment, it may be preferable to proceed with the crosslinking reaction or curing reaction of the epoxy groups derived from 2 mol of the glycidyl(alkyl)acrylate compound. In that case, during the reaction to obtain the heterocyclic compound or after the reaction, in situ or in a separate reaction system, the curing reaction or cross-linking reaction of the heterocyclic compound and another cross-linking agent is promoted to obtain the heterocyclic compound. It is preferable to form a cured product or crosslinked network containing structural units derived from a cyclic compound.

<Resin composition>
Another aspect of the invention comprises the following components:
(A) the heterocyclic compound according to this embodiment described above;
(B) a resin having an ethylenically unsaturated group; and (C) a polymerization initiator.

The resin composition containing components (A) to (C) is used in the lamination of the cured product with a support, the production of metal-clad laminates, the production of printed wiring boards, the production of modules for high-speed communication, and the like. It has the advantage of achieving both adhesion to a support and rust prevention when the support or substrate has a metal surface while maintaining dielectric properties. If desired, the resin composition may further contain (D) solvents, additives, etc. in addition to components (A) to (C).

Component (A) is, as explained above, a heterocyclic compound represented by general formula (1), preferably a compound represented by any one of formulas (I) to (III).

Component (B) is a resin having an ethylenically unsaturated group, the dielectric properties of the cured product when the resin composition is cured, and the chemical bond with the acryloyl group, methacryloyl group or ethacryloyl group of component (A) From the viewpoint of , it is preferably at least one resin selected from the group consisting of polyphenylene ether, polystyrene, a resin having an alicyclic structure, a polybenzoxazole precursor resin, a polyimide precursor resin, and a phenol resin.

The mass ratio (A:B) of component (A) and component (B) in the resin composition is not particularly limited, but is, for example, 1:7 to 50, 1:8 to 46, or 1:9. ~44 is fine.

Component (C) is a polymerization initiator, and from the viewpoint of exposure and/or curing of the resin composition, it is preferably at least one selected from the group consisting of oxime esters and peroxides.

Examples of oxime esters include 1-phenyl-1,2-propanedione-2-O-benzoyloxime and 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime.

The peroxide is preferably an organic peroxide such as benzoyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 2,5-dimethyl-2,5-dihydroperoxide, (t-butylperoxy)hexyne-3, di-t-butylperoxide, t-butylcumylperoxide, di(2-t-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di( t-butylperoxy)hexane, dicumyl peroxide, di-t-butylperoxyisophthalate, t-butylperoxybenzoate, 2,2-bis(t-butylperoxy)butane, 2,2-bis( t-butylperoxy)octane, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, di(trimethylsilyl)peroxide, trimethylsilyltriphenylsilylperoxide and the like. A radical generator such as 2,3-dimethyl-2,3-diphenylbutane can also be used as a reaction initiator for the resin composition.

The content of component (C) is preferably 0.05 from the viewpoint of increasing the reaction rate of the photopolymerization reaction or curing reaction, based on the total content of components (A) and (B) being 100% by mass. % by mass or more, more preferably 0.5% by mass or more or 1% by mass or more, still more preferably 1.5% by mass or more, and from the viewpoint of keeping the dielectric constant and dielectric loss tangent of the resulting cured product low, it is preferable is 5% by mass or less, more preferably 4.5% by mass or less, and still more preferably 4.0% by mass or less.

In addition to components (A) to (C), the photosensitive resin composition includes, for example, a cross-linking agent (eg, triallyl isocyanurate, α,α'-di(t-butylperoxy)diisopropylbenzene, etc.), an elastomer Additives such as additives such as (e.g. hydrogenated styrene thermoplastic resin), flame retardants, inorganic fillers (e.g. silica fillers), heat stabilizers, antioxidants, UV absorbers, surfactants, lubricants, etc. may contain. The content of the additive is preferably 0.01 to 100% by mass, more preferably 0.1 to 80% by mass, based on the total content of component (A) and component (B) being 100% by mass. and more preferably 1 to 50 mass.

When the resin composition contains (D) a solvent, it can be in the form of a varnish in which solid components in the resin composition are dissolved or dispersed in the solvent.

As the solvent, from the viewpoint of solubility, at least one of aromatic compounds such as toluene and xylene; alcohols such as methanol and ethanol; acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, propylene glycol monomethyl ether, and chloroform preferable. These solvents are used singly or in combination of two or more.

(D) From the viewpoint of suitably dissolving the component (A) and / or component (B) in the solvent and easily ensuring suitable fluidity of the resin composition even at about room temperature, the (D) solvent is preferably a solvent of an aromatic compound such as toluene or xylene. For example, a mixed solvent of toluene/methyl ethyl ketone, a mixed solvent of toluene/cyclohexane, a mixed solvent of toluene/cyclopentanone, and the like are more preferable. Toluene alone is also preferable as the solvent (D) from the viewpoint of impregnating the substrate.

(D) The amount of the solvent used is arbitrary depending on, for example, the predetermined viscosity of the resin composition, the means of applying the resin composition to the support, the material of the support, the level of roughening of the support surface, and the like. can be determined to

<Laminate>
In one embodiment, a laminate is provided comprising a resin composition or varnish thereof as described above and a support or substrate. When a laminate is used as a material for an electronic circuit board such as a printed wiring board, the laminate is preferably formed using the varnish described above. The laminate can be designed to suit the material of the support or base material, or the method of application to the support or base material. a body (hereinafter also referred to as "prepreg"), a resin-coated metal foil, a metal-clad laminate, or a laminate containing at least one of these.

The method of applying the resin composition or its varnish to the support or substrate is not particularly limited, but for example, coating, application or spraying of the resin composition onto the support or substrate; Bonding or lamination of molded article, cured product or dry film resist with support or substrate; immersion of support or substrate in resin composition; impregnation of support or substrate with resin composition; support transfer or replacement of the resin composition from the body to the substrate; other composites; and drying of the resin composition or varnish. The application methods listed above can be used singly or in any combination.

Examples of the support include polyolefins such as polyethylene, polypropylene and polyvinyl chloride; polyesters such as polyethylene terephthalate and polyethylene naphthalate; polycarbonates; polyimides; metal foils such as copper foil and aluminum foil;

When the support is subsequently removed from the cured product of the resin composition, it may be subjected to chemical or physical treatment such as matting, corona treatment, release treatment and the like. On the other hand, when the support has a metal surface such as copper or aluminum, or when the cured product of the resin composition is used for producing a printed wiring board or high-speed communication module, components contained in the resin composition (A), that is, from the viewpoint of optimizing the effect of the heterocyclic compound represented by the general formula (1), a low roughness surface (for example, 1.2 μm ≤ Rz < 1.4 μm) or an ultra-low roughness surface ( 0.9 μm≦Rz<1.2 μm) or not roughened (eg Rz<0.9 μm).

The laminate has the following properties (i) and/or (ii)
(i) Peel strength of the cured product of the resin composition against the support ≥ 0.4 N
(ii) Df2 - Df1 ≤ 0.001
{In the formula, Df2 represents the dielectric loss tangent of the cured product of the resin composition containing the above component (A), and Df1 represents the dielectric loss tangent of the cured product of the resin composition excluding the above component (A).)
and more preferably properties (i) and (ii).

Regarding the characteristic (i), when the peel strength of the cured product of the resin composition to the support is 0.4 N or more, in the production process of the laminate using the resin composition, the adhesive strength or adhesion of the adherend to the metal surface It tends to be easy to secure strength. From the viewpoint of further improving the adhesive strength or adhesion strength, the peel strength of the cured product of the resin composition to the support is more preferably 0.5 N or more.

As for the characteristic (ii), the value obtained by subtracting Df1 from Df2 is an index showing the influence of the addition of the heterocyclic compound to the resin composition, and is within the range of Df2−Df1≦0.001. As described above, even if the heterocyclic compound represented by the general formula (1) is contained in the resin composition, deterioration of the dielectric properties tends to be suppressed. From this point of view, Df2-Df1<0.0005 is more preferable.

The resin film can be obtained by coating the varnish described above alone or on a support such as a support film and then removing the organic solvent in the resin varnish by drying to form a film. The resin film can be suitably used as an interlayer insulation sheet, an adhesive film, etc. of a laminate such as a multilayer printed wiring board.

A prepreg includes a base material and the resin composition of the present embodiment impregnated or applied to the base material. The prepreg is obtained by, for example, impregnating a base material such as a glass cloth with the varnish and then removing the solvent by drying with a hot air dryer or the like.

Various glass cloths such as roving cloth, cloth, chopped mat, surfacing mat, etc.; asbestos cloth, metal fiber cloth, and other synthetic or natural inorganic fiber cloth; wholly aromatic polyamide fiber, wholly aromatic Woven or non-woven fabrics obtained from liquid crystal fibers such as group polyester fibers and polybenzoxazole fibers; Natural fiber fabrics such as cotton, linen, and felt; Carbon fiber cloth, kraft paper, cotton paper, and paper-glass mixed yarn. natural cellulosic substrates such as cloth; and polytetrafluoroethylene porous films. These substrates are used singly or in combination of two or more.

The resin composition solid content in the prepreg is preferably 30 to 80% by mass, more preferably 40 to 70% by mass. When the resin composition has a solid content of 30% by mass or more, the prepreg tends to be more excellent in insulation reliability when used for electronic substrates and the like. When the solid content of the resin composition is 80% by mass or less, mechanical properties such as bending elastic modulus tend to be more excellent in applications such as electronic substrates.

The metal-clad laminate according to this embodiment is obtained by laminating and curing the resin composition or prepreg of this embodiment and metal foil. The metal-clad laminate preferably has a form in which a cured prepreg (also referred to as a "cured composite") and a metal foil are laminated and adhered to each other, and is suitably used as a material for electronic circuit boards. Examples of metal foil include aluminum foil and copper foil, and among these, copper foil is preferable because of its low electrical resistance. The cured product composite to be combined with the metal foil may be one sheet or a plurality of sheets, and depending on the application, the metal foil is laminated on one side or both sides of the composite and processed into a laminate.

As a method for producing a metal-clad laminate, for example, a resin composition, a substrate, and a composite (for example, the prepreg described above) are formed, and after stacking this with a metal foil, the resin composition is cured. , a method of obtaining a laminate in which a cured product laminate and a metal foil are laminated. One particularly preferred application for the laminate is printed wiring boards. At least part of the metal foil is preferably removed from the metal-clad laminate of the printed wiring board.

<Printed wiring board>
The printed wiring board according to the present embodiment includes at least one laminate described above, thereby having excellent electrical properties (for example, low dielectric constant and low dielectric loss tangent) and insulation reliability, and It can have rust resistance. From the viewpoint of electrical properties, the printed wiring board is preferably configured such that a portion of the metal foil is removed from the metal-clad laminate.

The printed wiring board of the present embodiment is typically manufactured by a method of pressurizing and heating molding using the prepreg of the present embodiment described above; can be formed. Wiring patterning of the metal foil can be performed, for example, by physical etching, chemical etching, plating, dipping, and the like.

Since the printed wiring board according to the present embodiment is excellent in electrical properties, insulation reliability and rust prevention, it is preferably mounted on a high-speed communication module. A high-speed communication module is a terminal that, when incorporated into a product, enables high-speed communication of product information such as location information and operating status. High-speed communication modules are specifically incorporated into high-frequency transmission or 5th generation (5G) communication systems, and used for information communication, remote control of industrial devices and equipment, Internet of Things (IoT), etc. can be done.

<Example 1>

(Synthetic reaction)
A synthetic reaction was carried out according to Scheme 1 below.

52 g of acetone (non-volatile component concentration = 38.5%) was added as a solvent to a three-necked flask, and 13.0 g of 3-mercapto-1,2,4-triazole (3MTA) and 18.27 g of glycidyl methacrylate (GMA) were added as reaction components. In addition, 1.30 g of triethylamine (TEA) was added as a catalyst and reacted for 24 hours under draft drying. After that, the solvent was distilled off by an evaporator to obtain the product in the flask. The product was identified by ¹ H-NMR (“ECS-400” manufactured by JEOL Ltd., heavy DMSO), and a heterocyclic compound I was obtained. A ¹ H-NMR chart of the heterocyclic compound I is shown in FIG.

In FIG. 1, the ratio of the peaks derived from methacrylate that can be confirmed near 5.7 ppm and 6.1 ppm and the peak derived from the triazole ring near 8.4 ppm is about 1:1. was determined to be obtained. The reason why the above ratio is not exactly 1:1 is presumed to be that a mixture of isomer A and isomer B was obtained instead of a single compound.

(Influence of reaction conditions on heterocyclic compound I)
Reactions (a) and (b) were carried out in the same manner as in Scheme 1 above, except that the reaction conditions were changed as shown in Table 1.

Synthesis time for reaction (a) was 117 hours. However, the synthesis time is 42 Hr. The reaction system was sampled at . Synthesis time for reaction (b) was 42 hours. until synthesis time 19Hr. The reaction system was sampled at . Analyze the raw material (3MTA) alone, the sampling product and final product of reaction (a), and the sampling product and final product of reaction (b) by gel permeation chromatography (GPC, developing solvent THF). The resulting GPC chart is shown in FIG. 2 and was identified by ¹ H-NMR (“ECS-400” manufactured by JEOL Ltd., heavy DMSO).

From the comparison of the ¹ H-NMR charts (not shown) of reactions (a) and (b), based on the presence or absence of a peak around 14 ppm, which is presumed to be derived from —SH, in the presence of ethanol as a solvent, without using a catalyst. It was found that isomer A and isomer B were obtained at a ratio of about 1:1 (molar ratio) in some cases, whereas isomer B was obtained almost exclusively when a catalyst was used.

From FIG. 2, the following possibilities (i) and (ii) are suggested:
(i) 19 hr. of reaction (a). and 42 hr. Since the raw material peaks disappeared at the time of , there is a possibility that the reaction ended earlier than the sampling time in any reaction.
(ii) In reaction (a), the number of peaks derived from high-molecular-weight components is significantly small, and almost no increase over time is observed. On the other hand, in reaction (b), two peaks derived from high-molecular-weight components are observed, and they increase over time. Therefore, when using a catalyst in the presence of the solvent ethanol, the reaction sites may increase.

<Example 2>

(Synthetic reaction)
A synthetic reaction was carried out according to Scheme 2 below.

60 g of ethanol (non-volatile component concentration = 36.5%) was added as a solvent to a three-necked flask, and 15.0 g of 3-amino-5-mercapto-1,2,4-triazole (3A5MTA) and glycidyl methacrylate were added as reaction components at room temperature. 18.27 g of (GMA) was added, and 1.30 g of triethylamine (TEA) was added as a catalyst, and reacted for 24 hours under draft drying. After that, the solvent was distilled off by an evaporator to obtain the product in the flask. The product was identified by ¹ H-NMR (JEOL "ECS-400", heavy DMSO) to obtain heterocyclic compound II. A ¹ H-NMR chart of the heterocyclic compound II is shown in FIG.

In FIG. 3, the ratio of the peaks derived from the methacrylate that can be confirmed near 5.7 ppm and 6.1 ppm and the peak derived from the heterocyclic compound near 12 ppm is about 1: 1. Therefore, the heterocyclic compound II is judged to have been obtained. The reason why the above ratio is not exactly 1:1 is presumed to be that a mixture of isomer C and isomer D was obtained instead of a single compound.

(Effect of reaction conditions on heterocyclic compound II)
Using a 20 mL bottle as a reaction vessel at room temperature under the reaction conditions shown in Table 2, in the same manner as in Scheme 2 above except that stirring is performed using a stirrer, synthesis reactions (c) to (e) are carried out. did

In reaction (c), the product after drying was insoluble in DMSO, so as post-treatment c, the undried product left overnight in a fume hood was sampled and subjected to ¹ H-NMR (manufactured by JEOL Ltd. "ECS- 400", heavy DMSO).

^In reaction (d), the product after drying was insoluble in DMSO. 400", heavy DMSO).

In reaction (e), the reaction time was 24 hours. After the passage of , the stirring was stopped and the ²⁰ mL bottle was left to stand, and a precipitate was observed. After the measurement, the stirring was resumed, and the whole mixture was sampled and subjected to ¹ H-NMR measurement.

The undried product left overnight in the fume hood of reaction (d), the supernatant of reaction (e), and the stirred sample of the product of reaction (e) yielded ¹ H-NMR peaks (not shown). ) were almost the same, and the reaction reproducibility was confirmed.

Furthermore, when the ^{1 H-NMR charts (not shown) of reactions (d) and (e) are compared with the 1 H} -NMR charts (not shown) of reaction (c), reactions (d) and (o) , the peak near 6 ppm became broader, and a broad peak was observed near 5.5 ppm, suggesting the possibility of the presence of multiple products, such as isomer C and isomer D. be done.

<Example 3>

(Synthetic reaction)
A synthetic reaction was carried out according to Scheme 3 below.

Add 60 g of ethanol (non-volatile component concentration = 33.7%) as a solvent to a three-necked flask, add 11.0 g of 5-aminotetrazole (5ATz) and 18.27 g of glycidyl methacrylate (GMA) as reaction components at room temperature, and further add a catalyst. 1.3 g of triethylamine (TEA) was added as a solution and reacted under vacuum drying with stirring for 24 hours. After that, the solvent was removed by an evaporator to obtain a product. The product was identified by ¹ H-NMR (JEOL "ECS-400", heavy DMSO) to obtain heterocyclic compound III. A ¹ H-NMR chart of the heterocyclic compound III is shown in FIG.

In FIG. 4, the ratio of the peaks derived from methacrylate that can be confirmed near 5.7 ppm and 6.1 ppm and the peak derived from the heterocyclic compound near 6.6 ppm is about 1:1. It was judged that compound III was obtained. The reason why the above ratio is not exactly 1:1 is presumed to be that a mixture of isomer E and isomer F was obtained instead of a single compound.

(Effect of reaction conditions on heterocyclic compound III)
Synthesis reaction (f) and (g) was performed.

Not only the DMSO solution obtained as per Table 3 is subjected to ¹ H-NMR analysis, but also the EtOH solution is sampled and subjected to ¹ H-NMR analysis when the product is processed, if necessary. For identification of isomer E, if necessary, it is dissolved in a mixed solution of DMSO and PGME and analyzed.

<Preparation of varnish>
Glass cloth, copper foil and compounding components were prepared as shown in Table 4, and according to the composition shown in Table 5, a heterocyclic compound having an ethylenically unsaturated group, a PPE component, and an elastomer were mixed with toluene as a solvent. , and other additives were added and stirring continued until dissolved. Then, a cross-linking agent and an initiator were added to the melt and thoroughly stirred to obtain a varnish.

<Production of resin-coated copper foil>
The obtained varnish was coated on a copper foil so that the film thickness after drying was 25 μm, and dried in an air blowing oven at 90° C. for 10 minutes to prepare a resin-coated copper foil.
Furthermore, the two resin-coated copper foils thus obtained are laminated together so that the resin sides are in contact with each other, heated from room temperature at a temperature rising rate of 2°C/min, and vacuum press laminated at 200°C for 60 minutes at a pressure of 10 kg/cm ² . Thus, a double-sided copper-clad board was produced.

<Production of prepreg>
In addition, after impregnating the obtained varnish with a glass cloth base material, the excess varnish is scraped off by passing it through a predetermined slit, and it is dried in a drying oven at 120 ° C. for a predetermined time to remove toluene. Got the prepreg. This prepreg was cut into a predetermined size.

<Preparation of copper-clad laminate>
A predetermined number of the obtained prepregs were stacked, and metal foils were placed on both sides of the stacked prepregs, and vacuum pressing was performed to obtain a copper-clad laminate. In this vacuum pressing step, the temperature conditions were as follows: heating from room temperature at a temperature rising rate of 2° C./min, holding at 200° C. for 60 minutes, and pressurization at a pressure of 40 kg/cm ² .

<Metal layer adhesion strength>
The stress was measured when the copper foil was peeled off at a constant speed from the double-sided copper-clad plate and the copper-clad laminate formed by the vacuum press. Specifically, a double-sided copper-clad board or a copper-clad laminate was cut into a size of 10 mm width×100 mm length. Using an autograph (AG-5000D, manufactured by Shimadzu Corporation), the average value of the load when the copper foil was peeled off from the copper-clad laminate at an angle of 90 ° C. at a rate of 50 mm / min was measured. An average value of the measurements was obtained. The calculated average value was taken as the peel strength between the prepreg and the copper foil, or the metal layer adhesion strength. The metal layer adhesive strength was ranked according to the following criteria.
◎ (remarkably good) 0.45 ≤ metal layer adhesion strength (N)
〇 (good) 0.4 ≤ metal layer adhesion strength (N) < 0.45
× (defective) Metal layer adhesion strength (N) < 0.4

<Rust prevention/migration resistance>
An inner-layer circuit substrate having positive and negative electrode wiring patterns alternately arranged with a wiring width of 100 μm and an inter-wiring width of 100 μm was produced on the copper-clad laminate obtained above. The resin-coated copper foil or the prepreg and copper foil are overlaid on this inner layer circuit substrate, and the temperature is raised from room temperature at a rate of 2 ° C./min, and the pressure is 40 kg / cm ² at 200 ° C. for 60 minutes. Lamination was carried out under vacuum press conditions, and then a lead-out electrode portion was formed from the inner layer circuit to prepare a sample for migration evaluation. Migration resistance was measured by applying a DC voltage of 50 V under conditions of a temperature of 85° C. and a relative humidity of 85%, observing changes in insulation resistance and the presence or absence of growth of copper dendrites, and ranking them according to the following criteria.
◯ (Good): The insulation resistance value after 500 hours exceeded 1×10 8 Ω, and no dendrite growth was observed.
Δ (Acceptable): The insulation resistance value after 500 hours exceeded 1×10 8 Ω, or no dendrite growth was observed.
x (defective): The insulation resistance value after 500 hours was less than 1 x 108Ω, and dendrite growth was observed.

<Dielectric constant and dielectric loss tangent>
The dielectric constant and dielectric loss tangent at 10 GHz of the laminated plate and the glass sample were measured by cavity resonance method. A network analyzer (N5230A, manufactured by Agilent Technologies) and a cavity resonator (Cavity Resonator CP series, manufactured by Kanto Denshi Applied Development Co., Ltd.) were used as measurement devices. A laminate or glass sample having a thickness of about 0.5 mm was cut into a size of about 2 mm in width and 50 mm in length so that the warp of the glass cloth of the laminate was on the long side. Next, the sample was placed in an oven at 105° C.±2° C., dried for 2 hours, and then allowed to stand for 96±5 hours in an environment with a temperature of 23° C. and a relative humidity of 50±5%. After that, the dielectric constant and dielectric loss tangent of the sample were measured by using the above-described measuring apparatus under an environment of temperature 23° C. and relative humidity 50±5%.

In addition, for each of the copper foil grades a to c, the heterocyclic compound having an ethylenically unsaturated group is included in the dielectric loss tangent Df1 of the comparative example using a varnish that does not contain a heterocyclic compound having an ethylenically unsaturated group. The difference in dielectric loss tangent Df2 of the examples using varnish was calculated and ranked according to the following criteria.
〇 (Good) Df2 - Df1 ≤ 0.0005
△ (allowable) 0.0005 < Df2 - Df1 ≤ 0.001
× (bad) Df2 - Df1 > 0.001

<Evaluation results>
Table 5 shows the evaluation results of the copper-clad laminates obtained in Examples and Comparative Examples as described above.

Abbreviations used herein are as follows:
<Explanation of abbreviations>
3MTA: 3-mercapto-1,2,4-triazole 3A5MTA: 3-amino-5-mercapto-1,2,4-triazole 5ATz: 5-aminotetrazole GA: glycidyl acrylate GMA: glycidyl methacrylate GEA: glycidyl ethacrylate TEA: triethylamine DMSO: dimethylsulfoxide heavy DMSO: dimethylsulfoxide _- D6
EtOH: ethanol PGME: propylene glycol monomethyl ether TAIC: triallyl isocyanurate

Claims (8)

The following general formula (1):

{In the formula, R ² is a monovalent hydrocarbon group or a hydrogen atom, R ³ is a hydrogen atom, a methyl group, or an ethyl group, and X is the following general formula (2):

(wherein R ¹ is a monovalent hydrocarbon group or a hydrogen atom), and Y is a sulfur atom or an NH group}
A heterocyclic compound represented by (A) the heterocyclic compound of claim 1;
(B) a resin having an ethylenically unsaturated group;
(C) a polymerization initiator; and (D) a solvent;
A resin composition comprising: The (B) resin having an ethylenically unsaturated group is at least one selected from the group consisting of polyphenylene ether, polystyrene, a resin having an alicyclic structure, a polybenzoxazole precursor resin, a polyimide precursor resin, and a phenolic resin. 3. The resin composition of claim 2, which is a seed resin. The resin composition according to claim 2 or 3, wherein the (C) polymerization initiator is at least one selected from the group consisting of oxime esters and peroxides. A laminate comprising the resin composition according to any one of claims 2 to 4 and a support or substrate. The following characteristics:
(i) peel strength ≥ 0.4N;
(ii) Df2 - Df1 ≤ 0.001;
{In the formula, Df2 represents the dielectric loss tangent of the cured product of the resin composition containing the component (A), and Df1 represents the cured product of the resin composition excluding the component (A) from the resin composition. 6. The laminate according to claim 5, which satisfies the dielectric loss tangent of . A printed wiring board comprising the laminate according to claim 5 or 6. A high-speed communication module comprising the printed wiring board according to claim 7 .

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