Resin composition, cured product, prepreg, copper-clad laminate, interlayer insulating film, and compound

Abstract

Provided are: a resin composition comprising a compound (A), which is at least one of a compound (A1) that has two or more partial structures represented by formula (1) and a compound (A2) that is represented by formula (2), and a polymer (B) which has an aromatic ring and a group that crosslinks with the compound (A); a cured product; a prepreg; a copper-clad laminate; an interlayer insulating film; and a compound which is a compound (A1) that has two or more partial structures represented by formula (1) or a compound (A2) that is represented by formula (2). The explanation for each substituent in the formulae is as described in the specification.

Description

Resin compositions, cured products, prepregs, copper-clad laminates, interlayer insulating films, and compounds

[0001] The present invention relates to resin compositions, cured products, prepregs, copper-clad laminates, interlayer insulating films, and compounds.

[0002] In recent years, the information and communication field has seen an increase in the frequency of signal bandwidths in information and communication equipment, in order to achieve high-speed and high-capacity transmission. To accommodate this increase in frequency, there is a growing demand for low dielectric constant and low dielectric loss tangent materials in insulators used in printed circuit boards and semiconductor packages.

[0003] To address this high-frequency application, materials such as polyolefin resins, styrene resins, fluororesins, polyphenylene ether resins, vinyl benzyl ether resins, or compositions using polyphenylene ether resins with epoxy compounds, cyanate ester compounds, maleimide compounds, and vinyl compounds as curable compounds have been proposed (see, for example, Patent Documents 1 to 6).

[0004] Japanese Patent Publication No. 7-188362, Japanese Patent Publication No. 2004-83680, Japanese Patent No. 3414556, Japanese Patent Publication No. 2003-306591, Japanese Patent No. 5649773, Japanese Patent Publication No. 2017-200997

[0005] However, while studies on low dielectric constant and low dielectric loss tangent have progressed for the resins that make up a large proportion of the composition in conventional materials such as the compositions described in Patent Documents 1 to 6, sufficient studies on low dielectric constant, low dielectric loss tangent and solubility have not been conducted for other components that make up a large proportion, especially crosslinking agents. Furthermore, for the resins described in Patent Documents 1 to 6, it is not enough to simply improve the low dielectric constant and low dielectric loss tangent; other performance characteristics must also be met. In addition, the composition described in Patent Document 6 had room for improvement in terms of low dielectric properties.

[0006] One embodiment of the present invention aims to solve the problem of providing a resin composition that yields a cured product with excellent solubility in solvents and low dielectric loss tangent. Another embodiment of the present invention aims to solve the problem of providing a cured product, prepreg, copper-clad laminate, and interlayer insulating film with low dielectric loss tangent. Another embodiment of the present invention aims to solve the problem of providing a novel compound.

[0007] The present inventors have diligently studied to solve the above problems and have found that the above problems can be solved by the following configuration example. The means for solving the above problems include the following embodiments: <1> A resin composition containing compound (A), which is at least one of compound (A1) having two or more substructures represented by the following formula (1) and compound (A2) represented by the following formula (2); and a polymer (B) having a group that crosslinks with compound (A) and an aromatic ring.

[0008]

[0009] In formula (1), Ar represents an aromatic ring having 6 to 10 carbon atoms, L is an oxygen atom, a methylene group, an alkylene group having 2 to 6 carbon atoms, or a group consisting of two or more groups selected from these groups, and R １１ Each of these is independently bonded to a carbon atom that is a member of the Ar ring to which L is bonded, and to an adjacent carbon atom that is a member of the Ar ring, and is a hydrogen atom or a monovalent organic group, except for two R １１ At least one of them is a monovalent organic group, R １３ is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms, m １２ is 0 or 1, * represents a bonding site with other structures, R Ｐｈ is a group represented by formula (1a), (1b), or (1c), where R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R Ｖrepresents a vinyl group, and ** represents the binding site to L in formula (1). Provided that when the total amount of groups represented by formula (1a), (1b) and (1c) contained in compound (A1) is 100 mol%, the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0010]

[0011] In formula (2), R ２１ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms, or two R ２１ are bonded to each other to form a ring structure having 5 to 10 ring members together with the carbon atoms to which they are bonded, and R ２２ and R ２３ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms, wherein at least one of said R ２２ and at least one of said R ２３ are each independently a group represented by the following formula (2-1a), (2-1b) or (2-1c). Provided that, in formula (2), at least one of the two substituents bonded to the two carbon atoms adjacent to R ２２ is an alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms, and in formula (2), at least one of the two substituents bonded to the two carbon atoms adjacent to R ２３ is an alkyl group having 1 to 10 carbon atoms or an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms.

[0012]

[0013] In said formula (2-1a), (2-1b) and (2-1c), L, R Ｖ , and R １２ have the same definitions as L, R Ｖ , and R １２ in said formula (1) or formula (1a), (1b) and (1c) respectively, and * represents R ２２ or R ２３This represents the bonding site with a carbon atom that is a ring member of the benzene ring to which the group is bonded. However, if the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%, then the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol% or less.

[0014] <2> The resin composition according to <1>, wherein the compound (A1) is a compound represented by the following formula (1-1) or the following formula (1-2).

[0015]

[0016] In formula (1-1), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １１ A valence group consisting of an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, or R １３ These can be combined with each other to form a ring structure with 3 to 20 members, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-1), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １１ R represents an integer between 2 and 4. In equation (1-1), R １１ , R １３ , L, and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２This is equivalent to the above. However, if the total amount of groups represented by formulas (1a), (1b), and (1c) contained in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0017]

[0018] In formula (1-2), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １２ A valence group, which represents an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-2), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １２ R represents an integer between 2 and 4. In equation (1-2), R １１ , R １３ , L and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, in formula (1-2), A is bonded to another carbon atom that is adjacent to the carbon atom that is a ring member of Ar to which L is bonded.

[0019]

[0020] In equations (10-1) to (10-3), * represents the bond site with Ar in equation (1-1) or equation (1-2).

[0021] <3> The resin composition according to <1> or <2>, wherein the polymer (B) is at least one resin selected from the group consisting of polyphenylene ether resin, polyfunctional vinyl aromatic copolymer, and heteroaromatic-aromatic ether resin. <4> The resin composition according to any one of <1> to <3>, further containing a polymerization initiator (C). <5> The resin composition according to any one of <1> to <4>, further containing an organic solvent (D). <6> A cured product made from the resin composition according to any one of <1> to <5>. <7> A prepreg obtained by impregnating a fibrous substrate with the resin composition according to any one of <1> to <6>. <8> A copper-clad laminate obtained by laminating the prepreg according to <7> with a copper substrate. <9> An interlayer insulating film made from the cured product according to <6>. <10> Compound (A), which is a compound (A1) having two or more substructures represented by the following formula (1) or a compound (A2) represented by the following formula (2).

[0022]

[0023] In formula (1), Ar represents an aromatic ring having 6 to 10 carbon atoms, L is an oxygen atom, a methylene group, an alkylene group having 2 to 6 carbon atoms, or a group consisting of two or more groups selected from these groups, and R １１ Each of these is independently bonded to a carbon atom that is a member of the Ar ring to which L is bonded, and to an adjacent carbon atom that is a member of the Ar ring, and is a hydrogen atom or a monovalent organic group, except for two R １１ At least one of them is a monovalent organic group, R １２ Each is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R １３ is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms, m １２ is 0 or 1, R Ｖ represents a vinyl group, * represents a bonding site with other structures, and R Ｐｈ is a group represented by formula (1a), (1b), or (1c), where R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R Ｖrepresents a vinyl group, and ** represents the bonding site with L in formula (1). However, if the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0024]

[0025] In formula (2), R ２１ Each of these independently consists of a hydrogen atom, a C1-C10 alkyl group, an unsubstituted or substituted C6-C10 aromatic group, or two R groups. ２１ These are combined with each other to form a ring structure with 5 to 10 members, R ２２ and R ２３ Each of these independently represents a hydrogen atom, a C1-C10 alkyl group, or an unsubstituted or substituted C6-C10 aromatic group, and the R ２２ At least one of the R ２３ At least one of them is independently a group represented by formula (2-1a), (2-1b), or (2-1c), where R in formula (2) ２２ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group, and R in formula (2) ２３ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group.

[0026]

[0027] In equations (2-1a), (2-1b), and (2-1c), L, R Ｖ , and, R １２ These are L and R in formula (1) or formulas (1a), (1b), and (1c), respectively. Ｖ , and, R １２ This is synonymous with R. ２２ or R ２３This represents the bonding site with a carbon atom that is a ring member of the benzene ring to which the group is bonded. However, if the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%, then the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol% or less.

[0028] <11> Compound (A) described in <10>, which is a compound represented by the following formula (1-1) or the following formula (1-2).

[0029]

[0030] In formula (1-1), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １１ A valence group is an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, or A is R １３ These can be combined with each other to form a ring structure with 3 to 20 members, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-1), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １１ R represents an integer between 2 and 4. In equation (1-1), R １１ , R １３ , L, and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２is synonymous with the above. However, when the total amount of groups represented by formula (1a), (1b) and (1c) contained in the compound is taken as 100 mol%, the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0031]

[0032] In formula (1-2), R Ｐｈ is any one of the groups represented by formula (1a), (1b) or (1c) in said formula (1), and each A is independently a single bond or an n １２ valent group, which represents an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any one of the following formulas (10-1) to (10-3), or a group obtained by combining two or more of these groups, and R １３ is an alkyl group having 1 to 10 carbon atoms, an allyl group or a vinyl group, and when R １３ is an alkyl group having 1 to 5 carbon atoms, R １３ may be a linking group bonded to a carbon atom that is another ring member of another Ar in formula (1-2), and -CH ２ - in said linking group may be substituted with -O- or -S-, and n １２ represents an integer of 2 to 4. In formula (1-2), R １１ , R １３ , L, and m １２ are each synonymous with R １１ , R １３ , L, and m １２ in formula (1), respectively. However, A in formula (1-2) is bonded to a carbon atom which is another ring member adjacent to the carbon atom which is the ring member of Ar to which L is bonded.

[0033]

[0034] In formulas (10-1) to (10-3), * represents a bonding site to Ar in formula (1-1) or formula (1-2).

[0035] According to one embodiment of the present invention, a resin composition is provided that yields a cured product with excellent solubility in solvents and a low dielectric loss tangent. Furthermore, according to another embodiment of the present invention, a cured product, prepreg, copper-clad laminate, and interlayer insulating film with a low dielectric loss tangent are provided. Also, according to another embodiment of the present invention, a novel compound is provided.

[0036] Preferred embodiments of the present invention will be described in detail below. It should be understood that the present invention is not limited to the embodiments described below, but also includes various modifications that do not alter the essence of the invention. In this specification, numerical ranges indicated using "~" include the numerical values ​​before and after "~" as the lower and upper limits, respectively. A resin composition, cured product, prepreg, copper-clad laminate, and interlayer insulating film according to one embodiment of the present invention will be described in detail below.

[0037] [Resin Composition] The resin composition according to the present invention contains compound (A), which is at least one of compound (A1) having two or more substructures represented by the following formula (1) and compound (A2) represented by the following formula (2), and polymer (B) having a group that crosslinks with compound (A) and an aromatic ring.

[0038] <Compound (A)> Compound (A) is a compound that is at least one of compound (A1) having two or more substructures represented by the following formula (1) and compound (A2) represented by the following formula (2). Compound (A) is a compound other than polymer (B) described later, and preferably contains a compound that functions as a crosslinking agent that hardens upon irradiation with heat or light (e.g., visible light, ultraviolet light, near-infrared light, far-infrared light), and preferably is a crosslinking agent. Compound (A1) having two or more substructures represented by the following formula (1) or compound (A2) represented by the following formula (2) is a novel compound. Compound (A1) and / or compound (A2) have good solubility in solvents, and when crosslinking is performed using these compounds, a cured product with a low dielectric loss tangent is obtained. Compound (A) may be used alone or two or more types may be used. When hardening using compound (A), a polymerization initiator (C) described later may be required. Furthermore, the resin composition may further contain curable compounds other than compound (A1) and compound (A2) and polymer (B) described later (other curable compounds).

[0039] Compound (A) is such that, when the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A1) is taken as 100 mol%, the content of the group represented by formula (1b) is 10 mol% or more and 100 mol%, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol%, and when the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is taken as 100 mol%, the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol%, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol%, respectively. The lower limit of the content of the group represented by formula (1b) in compound (A1) or the group represented by formula (2-1b) in compound (A2) is preferably 15 mol%, more preferably 25 mol%, even more preferably 35 mol%, and particularly preferably 45 mol%, and the upper limit of the content of the group represented by formula (1b) or the group represented by formula (2-1b) is 100 mol%, preferably 99 mol%, more preferably 98 mol%, and even more preferably 95 mol%. The lower limit of the content of the group represented by formula (1a) in compound (A1) or the group represented by formula (2-1a) in compound (A2) is 0 mol%, preferably 1 mol%, more preferably 5 mol%, and even more preferably 10 mol%, and the upper limit of the content of the group represented by formula (1a) or the group represented by formula (2-1a) is 80 mol%, preferably 70 mol%, more preferably 60 mol%, and even more preferably 50 mol%. However, the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A1) is 100 mol%, and the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%.

[0040] For the group represented by L, R Ｖ The proportion of groups whose bond position is at the m position (i.e., the group represented by formula (1b) or the group represented by formula (2-1b)) and the proportion of R relative to the group represented by L ＶWhen the content of groups whose bond position is at the p position (i.e., groups represented by formula (1a) or formula (2-1a)) is within the above range, the resulting cured product has a low dielectric loss tangent. The reason for this is not clear, but compound (A) is R Ｖ When the bond position of the group represented by is m, R Ｖ Compared to the case where the bond position of the group represented by is other than the m position, the polarity of compound (A) is lower, therefore, R Ｖ It is hypothesized that a cured film with a lower dielectric loss tangent can be obtained when the proportion of compounds in which the bond position of the group represented by is at the m position is above a certain level.

[0041] The lower limit of the content of the group represented by formula (1c) in formula (A1) or the group represented by formula (2-1c) in formula (A2) is preferably 0 mol%, more preferably 0.1 mol%, even more preferably 0.5 mol%, and particularly preferably 1 mol%, and the upper limit of the content of the group represented by formula (1c) or the group represented by formula (2-1c) is preferably 30 mol%, more preferably 15 mol%, and even more preferably 5 mol%. However, the total amount of the groups represented by formulas (1a), (1b), and (1c) in compound (A1) is 100 mol%, and the total amount of the groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%. It is preferable that the content ratio of the group represented by formula (1c) or the group represented by formula (2-1c) is within the above range because the resulting cured product will have a lower dielectric loss tangent.

[0042] [Compound (A1)] Compound (A1) is a compound having two or more substructures represented by the following formula (1).

[0043]

[0044] In formula (1), Ar represents an aromatic ring having 6 to 10 carbon atoms, L is an oxygen atom, a methylene group, an alkylene group having 2 to 6 carbon atoms, or a group consisting of two or more groups selected from these groups, and R １１ Each of these is independently bonded to a carbon atom adjacent to the carbon atom that is a ring member of the Ar to which L is bonded, and is a hydrogen atom or a monovalent organic group, except for the two R１１ At least one of them is a monovalent organic group, R １２ Each is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R １３ These are alkyl groups, allyl groups, and vinyl groups having 1 to 10 carbon atoms, and m １２ is 0 or 1, * represents a bonding site with other structures, R Ｐｈ is a group represented by formula (1a), (1b), or (1c), where R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R Ｖ represents a vinyl group, and ** represents the bonding site with L in formula (1). However, if the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0045] Examples of aromatic rings represented by Ar include benzene rings, naphthalene rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, and triazine rings.

[0046] [R Ｖ ] R Ｖ The vinyl group represented by *-CH=CH ２ The following are examples of groups represented by *. * represents the bonding site with a carbon atom that is a member of the benzene ring. The above *-CH=CH ２ The hydrogen atoms in R may be further substituted with known substituents, insofar as the effects of the present invention are obtained. Examples of substituents include C1-C10 alkyl groups represented by linear, branched, cyclic, or these combinations. Ｖ In the present invention, a vinyl group represented by the above-mentioned model may also be one of the preferred embodiments of the present invention, in which case the vinyl group may not have the above-mentioned substituent.

[0047] [L] The group represented by L is a combination of two or more groups selected from an oxygen atom, a methylene group, and an alkylene group having 2 to 6 carbon atoms, for example, -O-C ｍ H ２ｍ -, -(O-C)ｎ H ２ｎ ) ｐ - are examples. However, m is an integer from 1 to 6, n is 2 or 3, p is 2 or 3, and m is preferably 1 or 2, more preferably 1. From the viewpoint of having good curability, being able to increase the crosslinking density of the resulting cured product, and ensuring heat resistance even when the molecular weight of the polymer (B) described later is kept low, L is a methylene group or -O-C ｍ H ２ｍ A group represented by - (where m is 1 or 2) is preferred, and -O-C ｍ H ２ｍ A group represented by - (where m is 1 or 2) is more preferred, -O-CH ２ A group represented by - is even more preferable.

[0048] [R １１ ] The aforementioned R １１ Examples of monovalent organic groups represented by include allyl groups, vinyl groups, (meth)acryloyl groups, C1-C10 alkyl groups, C5-C10 cycloalkyl groups, unsubstituted or substituted C6-C10 aromatic groups, unsubstituted or substituted C3-C10 aromatic heterocyclic groups, and unsubstituted or substituted C7-C15 aralkyl groups.

[0049] Examples of the alkyl group include linear or branched alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl groups. Examples of the cycloalkyl group include monocyclic or polycyclic alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, and tricyclodecanyl groups. Examples of the aromatic heterocyclic group include nitrogen-containing aromatic heterocyclic groups represented by the following formula (RN).

[0050]

[0051] In formula (RN), CR represents an aromatic heterocycle having a nitrogen atom, and X １ is -N= or -CR ＣＲ２ = represents X ２ is = N- or, = CR ＣＲ３This represents -, and Y is = N- or = CR ＣＲ４ - represents R ＣＲ１ R represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms. ＣＲ１ R ＣＲ３ It may also bond with to form a ring structure, and * represents the bonding site with Ar in formula (1) above. ＣＲ１ and R ＣＲ３ The ring structure formed by the bonding of these elements is preferably an aromatic ring structure, and more preferably a benzene ring.

[0052] Examples of groups represented by the above formula (RN) include pyrazolyl group, imidazolyl group, triazolyl group, benzopyrazolyl group, benzimidazolyl group, and benzotriazolyl group.

[0053] Examples of the aromatic group include a phenyl group and a naphthyl group. Examples of the aralkyl group include a benzyl group and a naphthylmethyl group. Examples of substituents on the monocyclic or polycyclic alicyclic hydrocarbon group, aromatic group and aralkyl group include alkyl groups having 1 to 10 carbon atoms.

[0054] Compound (A1) is R １１ It is thought that the presence of restricts the movement of the styrene linked to L, thereby reducing the dielectric loss tangent of the resulting cured product. From the viewpoint of reducing the dielectric loss tangent and ease of synthesis, R １１ Preferred members include linear or branched alkyl groups, monocyclic or polycyclic cycloalkyl groups, aryl groups, and aralkyl groups; more preferably linear or branched alkyl groups, aryl groups, and aralkyl groups; and even more preferably linear or branched C1-C5 alkyl groups, aryl groups, and benzyl groups.

[0055] The aforementioned R １２ and R １３ The alkyl group having 1 to 10 carbon atoms, represented by R １１ The alkyl group is similar to the group in the example, and the preferred embodiment is also similar.

[0056] Compound (A1) is preferably a compound represented by the following formula (1-1) or formula (1-2).

[0057]

[0058] In formula (1-1), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １１ A valence group consisting of an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, or R １３ These can be combined with each other to form a ring structure with 3 to 20 members, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-1), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １１ R represents an integer between 2 and 4. In equation (1-1), R １１ , R １３ , L, and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, if the total amount of groups represented by formulas (1a), (1b), and (1c) contained in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less.

[0059]

[0060] In formula (1-2), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １２A valence group, which represents an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-2), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １２ R represents an integer between 2 and 4. In equation (1-2), R １１ , R １３ , L and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, in formula (1-2), A is bonded to another carbon atom that is adjacent to the carbon atom that is a ring member of Ar to which L is bonded.

[0061] [A] Examples of substituents on the methylene group represented by A include C1-C10 alkyl groups, C5-C10 cycloalkyl groups, and C6-C10 aromatic groups. The C1-C10 alkyl groups and C5-C10 cycloalkyl groups are each R in formula (1) above. １１ This is synonymous with alkyl groups and cycloalkyl groups represented by . Examples of the aromatic group having 6 to 10 carbon atoms include phenyl groups and naphthyl groups.

[0062] The alicyclic hydrocarbon group represented by A can be any of the monocyclic hydrocarbon groups having 5 to 12 carbon atoms, such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, and cyclododecane. １１ individual or n １２ From groups in which one hydrogen atom has been abstracted, such as norbornane, tricyclodecane, tetracyclododecane, and adamantane, which are polycyclic hydrocarbon groups １１ individual or n １２Examples include groups from which one hydrogen atom has been abstracted. These alicyclic hydrocarbon groups may be substituted with alkyl groups having 1 to 10 carbon atoms.

[0063] The aromatic hydrocarbon group represented by A may be monocyclic or polycyclic. From the viewpoint of having excellent heat resistance and a lower elongation rate in the resulting cured product, the aromatic hydrocarbon group may be an aromatic hydrocarbon group having 6 to 14 carbon atoms. １１ individual or n １２ A group from which one hydrogen atom has been abstracted is preferred, and from an aromatic hydrocarbon group having 10 to 14 carbon atoms, n １１ individual or n １２ A group from which one hydrogen atom has been abstracted is more preferable. Examples of such groups include n from benzene, naphthalene, and fluorene. １１ individual or n １２ Examples include groups from which one hydrogen atom has been abstracted. These aromatic hydrocarbon groups may be substituted with alkyl groups having 1 to 10 carbon atoms.

[0064] A is preferably an unsubstituted or substituted methylene group, an oxygen atom, a sulfur atom, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups. It is even more preferable that A is an oxygen atom, a sulfur atom, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining these groups with an unsubstituted or substituted methylene group (provided that Ar and methine are not directly bonded). When A is one of these groups, compound (A1) is less susceptible to oxidation, resulting in good curability, excellent heat resistance of the resulting cured product, and reduced elongation.

[0065]

[0066] In equations (10-1) to (10-3), * represents the bond site with Ar in equation (1-1) or equation (1-2).

[0067] The following exemplary compounds can be cited as the compound (A1), but the present invention is not limited to these. The exemplary compounds include mixtures of isomers, and when the total amount of the group represented by R below contained in the compound is 100 mol%, the substitution positions of the vinyl group in R are such that 10 mol% to 100 mol% are at the meta position relative to the methylene group described in R, and 0 mol% to 80 mol% are at the para position.

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] Preferred compounds (A1) include A-1-4, A-1-18 to A-1-21, A-1-34, A-1-46, A-1-49, and A-1-53.

[0078] [Compound (A2)] Compound (A2) is a compound represented by the following formula (2).

[0079]

[0080] In formula (2), R ２１ Each of these independently consists of a hydrogen atom, a C1-C10 alkyl group, an unsubstituted or substituted C6-C10 aromatic group, or two R groups. ２１ These are combined with each other to form a ring structure with 5 to 10 members, R ２２ and R ２３Each of these independently represents a hydrogen atom, a C1-C10 alkyl group, or an unsubstituted or substituted C6-C10 aromatic group, and the R ２２ At least one of and R ２３ At least one of them is independently a group represented by formulas (2-1a), (2-1b), and (2-1c), where R in formula (2) ２３ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group.

[0081]

[0082] In equations (2-1a), (2-1b), and (2-1c), L, R Ｖ , and, R １２ These are L and R in formula (1) or formulas (1a), (1b), and (1c), respectively. Ｖ , and, R １２ This is synonymous with R ２２ or R ２３ This represents the bonding site with a carbon atom that is a ring member of the benzene ring to which the group is bonded. However, if the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%, then the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol% or less.

[0083] R ２１ , R ２２ and R ２３ As an alkyl group having 1 to 10 carbon atoms represented by formula (1), R １１ This is synonymous with an alkyl group having 1 to 10 carbon atoms, and the preferred embodiment is the same. ２１ , R ２２ and R ２３ As an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms represented by formula (1), R １１ This is synonymous with the aromatic group represented by .

[0084] R ２１ , R ２２ and R ２３Examples of substituents on the aromatic group having 6 to 10 carbon atoms represented by include alkyl groups having 1 to 10 carbon atoms.

[0085] Two R's ２１ Examples of ring structures with 5 to 10 members, formed by combining these elements with the carbon atoms to which they bond, include alicyclic hydrocarbon structures such as cyclopentane, cyclohexane, and norbornane, and aromatic hydrocarbon structures such as benzene and naphthalene.

[0086] The following exemplary compounds can be cited as the compound (A2), but the present invention is not limited to these compounds. The exemplary compounds include mixtures of isomers, and when the total amount of the group represented by R below contained in the compound is 100 mol%, the substitution positions of the vinyl group in R are such that 10 mol% to 100 mol% are at the meta position relative to the methylene group described in R, and 0 mol% to 80 mol% are at the para position.

[0087]

[0088]

[0089] A-2-6 is preferred as the compound (A-2).

[0090] [Method for synthesizing compound (A)] There are no particular restrictions on the method for synthesizing compound (A), and known synthesis methods can be cited. An example of a method for synthesizing compound (A) is described below. The method for synthesizing compound (A) is not particularly limited, and for example, it may be synthesized by etherification reaction of a phenol compound in which R in the example compound is a hydrogen atom and a halogen compound represented by the following formula (3) using the Williamson method, which is a common method for synthesizing ethers.

[0091]

[0092] In equation (3), X represents a halogen atom, m １１ is 4, R １２ Each of these is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and L is synonymous with L in formula (1). R in formula (3)１２ R in equation (1a), (1b), or (1c) １２ This is synonymous with the above, and the preferred embodiment is similar. Because of its good reactivity and the availability of readily available raw materials, X is preferably a chlorine atom or a bromine atom, and more preferably a chlorine atom.

[0093] The content of compound (A) is preferably 15 parts by mass or more, more preferably 25 parts by mass or more, even more preferably 35 parts by mass or more, preferably 250 parts by mass or less, more preferably 200 parts by mass or less, and even more preferably 150 parts by mass or less, when the polymer (B) described later is 100 parts by mass.

[0094] When the content of compound (A) is within the above range, it is preferable that the electrical properties of the resulting cured product, such as dielectric constant and dielectric loss tangent, as well as heat resistance, adhesion, and curability, are further improved, and the elongation can be further reduced. Compound (A) may be used alone or in combination of two or more types.

[0095] When the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A) is set to 100 mol%, R Ｖ The substitution position of is m relative to L (i.e., the group represented by formula (1b)) and the content is 10 mol% or more and 100 mol% or less, R Ｖ There are no particular restrictions on the method for adjusting the content of the group whose substitution position is at the p position relative to the L of the phenyl group (i.e., the group represented by formula (1a)) to 0 mol% or more and 80 mol% or less, but for example, the R represented by formula (1-1) Ｐｈ R inside Ｖ The substitution position of is relative to L, and includes halogen compounds at the m position, halogen compounds at the p position, and R as needed. Ｖ One method for synthesizing compound (A) is to mix halogen compounds whose substitution position is at the o-position relative to L in any proportion within the range in which the effects of the present invention are achieved.

[0096] [Other Curable Compounds] Compound (A) may be used in combination with other curable compounds that function as crosslinking agents other than compound (A) and polymer (B) described later (hereinafter also referred to as "other curable compounds"). Examples of other curable compounds include vinyl compounds, maleimide compounds, allyl compounds, acrylic compounds, methacrylic compounds, thiol compounds, oxazine compounds, cyanate compounds, epoxy compounds, oxetane compounds, methylol compounds, benzocyclobutene compounds, propargyl compounds, and silane compounds. Particularly from the viewpoint of compatibility and reactivity with compound (A) and polymer (B), it is preferable that the other curable compound is at least one compound selected from the group consisting of vinyl compounds, maleimide compounds, and allyl compounds. When compound (A) and other curable compounds are used in combination, with compound (A) being 100 parts by mass, the content ratio of the other curable compounds is preferably 0 to 200 parts by mass, more preferably 0 to 100 parts by mass, and even more preferably 50 to 100 parts by mass.

[0097] <Polymer (B)> Polymer (B) is a polymer having a group that crosslinks with compound (A) and an aromatic ring. Preferably, polymer (B) is a polymer having one or more groups from the group consisting of vinyl groups, allyl groups, and (meth)acryloyl groups that crosslink with compound (A). Examples of such polymers (B) include polyphenylene ether polymers, polyfunctional vinyl aromatic copolymers, or heteroaromatic-aromatic ether polymers, which have one or more groups from the group consisting of vinyl groups, allyl groups, and (meth)acryloyl groups at the main chain ends or side chains of polymer (B). Hereinafter, these may be abbreviated as "modified polyphenylene ether polymer," "modified polyfunctional vinyl aromatic copolymer," and "modified heteroaromatic-aromatic ether polymer," respectively. These polymers (B) are polymers with excellent low dielectric constant and low dielectric loss tangent, and when used in combination with compound (A) having the specific structure described above, crosslinking proceeds efficiently even if polymer (B) is not in a high molecular weight state. This ensures heat resistance while maintaining low dielectric constant and low dielectric loss tangent in the resulting cured product. Furthermore, by adjusting the molecular weight of polymer (B), the dielectric loss tangent, fluidity, and adhesion of the resulting cured product to substrates can be designed to suit the application. Therefore, by containing polymer (B) having a crosslinking group and aromatic ring with compound (A) in the resin composition according to the present invention, the resulting cured product has a low dielectric loss tangent and a composition that exhibits a good balance of fluidity and the above-mentioned adhesion.

[0098] [Modified Heteroaromatic-Aromatic Ether Polymers (B1)] Heteroaromatic-aromatic ether polymers (B1) (hereinafter also referred to as "polymer (B1)") include, for example, polymers (B1) having a structural unit represented by formula (B1-1).

[0099]

[0100] In formula (B1-1), R ａ１ R is a divalent group represented by the following formula (B2), ａ２ The formula is as follows (R ａ２ -1), (R ａ２ -2) and (R ａ２-3) A divalent group represented by one of the types selected from the above.

[0101]

[0102] In formula (B2), Ar ａ１ and Ar ａ２ Each of these is independently an unsubstituted or substituted aromatic hydrocarbon group, and L is a single bond, -O-, -S-, -N(R) ８ )-, -C(O)-, -C(O)-O-, -C(O)-NH-, -S(O)-, -S(O) ２ -, -P(O)- or a divalent organic group, and the R ８ is a hydrogen atom, a monovalent organic group with 1 to 10 carbon atoms, y is an integer from 0 to 5, and if y is 2 or more, multiple Ar ａ１ And L are either the same or different, and R ａ６ and R ａ７ Each of these is independently a single bond, a methylene group, or an alkylene group having 2 to 4 carbon atoms.

[0103] [L] Examples of divalent organic groups in L include unsubstituted or substituted methylene groups, alkylene groups having 2 to 20 carbon atoms, arylene groups having 6 to 10 carbon atoms, groups consisting of two or more selected from the methylene groups, alkylene groups, and arylene groups, or groups represented by the following formula (L1).

[0104]

[0105] In formula (L1), R ｃ These are divalent groups derived from unsubstituted or substituted monocyclic or polycyclic divalent alicyclic hydrocarbon groups with 5 to 30 ring members, or divalent groups derived from compounds represented by the following formulas (L2) to (L4) (i.e., the group from which two hydrogen atoms have been removed in the following compounds).

[0106]

[0107] In formula (L2), R ８ and R ９ Each of these is independently a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group having 1 to 20 carbon atoms, and k is independently an integer from 0 to 4.

[0108] [y] In formula (B2), y is an integer from 0 to 5. From the viewpoint of structural stability of polymer (B1), y is preferably an integer from 0 to 3, and more preferably 0 or 1.

[0109] R in equation (B1-1) ａ１ Examples of monomers that serve as raw materials for the portion containing (i.e., the divalent group represented by formula (B2)) include, in addition to the compound represented by the following formula, diol compounds such as Preplast 1901, 1838, 3186, 3192, 3197, and 3199 (manufactured by Croda Japan Co., Ltd.). These monomers may be used individually or in combination of two or more.

[0110]

[0111]

[0112]

[0113] <R ａ２ > R ａ２ The formula is as follows (R ａ２ -1), (R ａ２ -2) and (R ａ２ -3) A divalent group represented by one of the types selected from the above.

[0114]

[0115] Formula (R ａ２ -1) to (R ａ２ -3) Medium, R １ Each of these is independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group, a cyano group, a primary to tertiary amino group, or a salt of a primary to tertiary amino group, and each of these is independently an integer from 0 to 2, and when n is 2, multiple R １ These are parts of a ring structure with 5 to 10 members, which are identical or different, and which combine with each other and are bonded together with carbon atoms.

[0116] R １From the viewpoint of improving polymerization reactivity and the solubility of the resulting polymer, halogen atoms, C1-C3 alkyl groups, or C6-C10 aromatic hydrocarbon groups are preferred, and fluorine atoms, chlorine atoms, methyl groups, ethyl groups, or phenyl groups are more preferred. From a similar viewpoint, n is preferably 0 or 1, and more preferably 0.

[0117] <<Groups that crosslink with compound (A)>> The heteroaromatic-aromatic ether polymer (B1) has a terminal group Y represented by the following formula (a) at the end of the structural unit represented by formula (B1-1) as a group that crosslinks with compound (A), or Ar in the above formula (B2) ａ１ and Ar ａ２ The unsubstituted or substituted aromatic hydrocarbon group represented by may have substituents such as an allyl group, a (meth)acryloyloxy group, or an alkenyl group.

[0118]

[0119] In formula (a), Y is a group containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 50 carbon atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or an unsubstituted nitrogen-containing heteroaromatic ring.

[0120] Preferred terminal groups Y include groups containing an ethylenically unsaturated double bond having 3 to 50 carbon atoms, such as aromatic ring-containing groups like 3-isopropenylphenyl, 4-isopropenylphenyl, 2-allylphenyl, 2-methoxy-4-allylphenyl, 4-(1-propenyl)-2-methoxyphenyl, 4-vinylbenzyl, 3-vinylbenzyl, 2-vinylbenzyl, 2-vinylphenyl, 3-vinylphenyl, and 4-vinylphenyl, as well as allyl groups, acrylic groups, and methacrylic groups.

[0121] There are no particular restrictions on the method for forming polymer (B1) in which the ends of polymer (B1) are sealed with terminal groups Y, and known methods can be used.

[0122] In addition to the monomer that gives the structural unit of formula (B1-1) above, polymer (B1) may also contain a structural unit represented by the following formula (B1-2) by copolymerizing a monomer that gives a branched structure.

[0123]

[0124] In formula (B1-2), R ａ２ The above formula (R ａ２ -1), (R ａ２ -2) and (R ａ２ -3) A divalent group represented by one selected from the above, R １２ Each of these independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group, R １３ represents a hydrocarbon group with 1 to 20 carbon atoms, m represents an integer from 1 to 6, and ** represents a bond with other structural units in the polymer (B1).

[0125] Examples of polymers (B1) include the following exemplary compounds, but the present invention is not limited to these.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] In the example compounds above, [ ] represents a repeating unit, * represents bonding with any of **, and formula (Y) represents bonding with any of **.

[0138] In the example compounds below, [ ] represents a repeating unit, * represents a binding site with ** or ***, ** represents a binding site with *, and *** represents a binding site with *. Both ends of the example compounds below have a structure in which *** and * are bonded.

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] The lower limit of the weight-average molecular weight (Mw) of polymer (B1) is preferably 1,000, more preferably 3,000, and particularly preferably 5,000 in terms of polystyrene equivalent, and the upper limit of the weight-average molecular weight (Mw) of polymer (B1) is preferably 500,000, more preferably 100,000, even more preferably 30,000, and particularly preferably 15,000 in terms of polystyrene equivalent. When the weight-average molecular weight (Mw) of polymer (B1) is within the above range, it exhibits a well-balanced and excellent moldability, including adhesion, heat resistance, impregnation into glass cloth, and resin flow. The weight-average molecular weight (Mw) is determined by measurement using gel permeation chromatography (GPC) under the conditions described in the examples below.

[0145] [Modified polyphenylene ether polymer (B2)] Modified polyphenylene ether polymer (B2) can be a polymer (B2) having a structural unit represented by the following formula (B2-1).

[0146]

[0147] In formula (B2-1), R ｂ１１ and R ｂ１２ Each of these independently represents an alkyl group; R ｂ１３ , R ｂ１４ , R ｂ２１ , R ｂ２２ , R ｂ２３ and R ｂ２４Each independently represents either a hydrogen atom or an alkyl group; R ｂ３１ and R ｂ３２ Each independently represents either a vinylphenyl group or a (meth)acryloyl group; L ｂ２１ This is a single bond, -C(Ry) ２ -, -O-, -CO-, -S-, -SO-, or -SO ２ - indicates; Ry independently represents a hydrogen atom or an alkyl group; Z represents a single bond or an alkylene group; n ｂ２１ and m ｂ２１ Each of these independently represents an integer greater than or equal to 1; p ｂ２１ n represents 0 or 1. ｂ２１ Units and m ｂ２１ The units may be the same for each unit, or they may be different.

[0148] Examples of commercially available modified polyphenylene ether polymers (B2) include "OPE-2St 1200" and "OPE-2St 2200" (vinyl benzyl modified polyphenylene ether polymers) from Mitsubishi Gas Chemical Co., Ltd., and "SA9000" and "SA9000-111" (methacrylic modified polyphenylene ether polymers) from SABIC Innovative Plastics Co., Ltd.

[0149] <Other Components> The resin composition according to the present invention (hereinafter sometimes simply referred to as "this composition") contains a compound (A) which is at least one of a compound (A1) having two or more substructures represented by formula (1) above and a compound (A2) represented by formula (2) above, and the polymer (B) above which has a group that crosslinks with compound (A) and an aromatic ring. In addition to compound (A) and polymer (B), other components may be further contained to the extent that they do not impair the effects of the present invention.

[0150] Examples of the other components mentioned above include polymerization initiators (C), organic solvents (D), additives for imparting various functions, and fillers (F). Furthermore, the composition may also contain thermoplastic resins as polymers other than compound (A) and polymer (B) to adjust the physical properties of the composition, such as fluidity, heat resistance, and electrical properties. Each of these other components may be used individually or in combination of two or more.

[0151] [Polymerization Initiator (C)] The composition preferably further contains a polymerization initiator (C). Examples of polymerization initiators (C) include thermal or photoradical initiators, cationic curing agents, and anionic curing agents. Among these, thermal radical initiators are preferred as polymerization initiators (C).

[0152] Examples of thermal radical initiators include organic peroxides such as dicumyl peroxide, 1,1-di(t-butylperoxy)cyclohexane, di(t-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, and benzoyl peroxide; and azo compounds such as azobisbutyronitrile, 1,1'-azobis(1-acetoxy-1-phenylethane), 2,2'-azobis(2,4-dimethylvaleronitrile), 1,1'-azobis(cyclohexane-1-carbonitride), dimethyl-2,2'-azobis(isobutyrate), and 2,2'-azobis(2-methylbutyronitrile).

[0153] If the composition contains a polymerization initiator (C), the content of the polymerization initiator (C) is preferably within a range that allows the composition to cure well and a cured product to be obtained. Specifically, it is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, preferably 20 parts by mass or less, and more preferably 10 parts by mass or less, based on 100 parts by mass of the total solid content of compound (A) and polymer (B). The polymerization initiator (C) may be a single type or two or more types may be used in combination.

[0154] [Organic Solvent (D)] The composition preferably further contains an organic solvent (D). Examples of organic solvent (D) include amide solvents, ester solvents, ketone solvents, ether solvents, sulfone solvents, hydrocarbon solvents such as benzene, toluene, and xylene, polyfunctional solvents such as 1-methoxy-2-propanol and propylene glycol methyl ether acetate, trialkoxybenzene (number of carbon atoms in the alkoxy group: 1 to 4), and methylene chloride.

[0155] If the composition contains an organic solvent (D), the proportion of the solvent in the composition is not particularly limited. For example, it is preferably 0 to 2000 parts by mass, more preferably 0 to 1000 parts by mass, based on 100 parts by mass of the total solid content of compound (A) and polymer (B). Furthermore, if compound (A) and polymer (B) have high solubility in the organic solvent (D), the proportion of the organic solvent (D) in the composition may be 50 to 200 parts by mass. The organic solvent (D) may be a single type or two or more types may be used in combination.

[0156] [Hydrogenated Styrene Thermoplastic Elastomer (E)] This composition may further contain hydrogenated styrene thermoplastic elastomer (E) (hereinafter sometimes simply referred to as "elastomer (E)"). The elastomer (E) refers to an elastomer in which some or all of the double bonds of a styrene thermoplastic elastomer are hydrogenated. By including hydrogenated styrene thermoplastic elastomer (E) in this composition, it is easier to obtain cured products with lower dielectric constant and lower dielectric loss tangent. Elastomer (E) may be used alone or in combination of two or more types.

[0157] [Additives] Additives used to impart the various functions mentioned above include, for example, antioxidants, flame retardants, adhesion aids, and fillers such as organic fillers and inorganic fillers. Specific compounds include, for example, hindered phenol compounds, phosphorus compounds, sulfur compounds, metal compounds, hindered amine compounds, and silica compounds such as natural silica, fused silica, and amorphous silica. Among these, hindered phenol compounds and silica compounds are preferred.

[0158] [Method for preparing the composition] There are no particular restrictions on the method for preparing the composition, and known preparation methods can be used. For example, it can be prepared by uniformly mixing compound (A), polymer (B), and the other components. In this case, there are no particular restrictions on the order of mixing each component, the mixing conditions, etc., and a conventionally known mixer may be used for mixing.

[0159] <<Cured Product>> A cured product according to one embodiment of the present invention (hereinafter also referred to as "the cured product") consists of the above-described composition. The cured product is a cured body of the above-described composition, and is obtained by curing the above-described composition. The cured product may be, for example, a partially cured product of the composition obtained by drying the solvent from the composition.

[0160] [Glass Transition Temperature (Tg)] The lower limit of the Tg of the cured product is preferably 170°C, more preferably 200°C, and the upper limit is, for example, 400°C. Having Tg within this range makes melt molding easier and allows for the easy acquisition of a cured product with excellent heat resistance.

[0161] Tg is determined by preparing a test specimen (width: 3 mm x length: 1 cm) and measuring its temperature under nitrogen conditions from 50°C to 300°C at a heating rate of 10°C / min and 1 Hz using a dynamic viscoelasticity analyzer (Seiko Instruments Inc., model number "EXSTAR4000"). The tanδ value obtained during this process is then used as the glass transition temperature (Tg). If two or more tanδ values ​​are present, the lowest value is used as the Tg.

[0162] The dielectric loss tangent (tanδ) of the cured product is preferably 0.0025 or less, more preferably 0.0018 or less, and even more preferably 0.0015 or less, from the viewpoint of reducing transmission loss, and although there is no particular lower limit, it is preferably 0.0005 or more. The dielectric loss tangent can be measured specifically by the method described in the following examples.

[0163] The elongation of the cured product, as determined by the same method as in the examples, is 10% or less, more preferably 5% or less, and even more preferably 3% or less, with no particular lower limit. When the elongation is within the above range, the difference in elongation between the cured product and metal types such as copper wiring can be reduced. The elongation is determined by the method described in the examples below.

[0164] The shape of the cured product is not particularly limited, and a suitable shape can be appropriately selected depending on the application and purpose. Examples of cured product shapes include film, plate, and rod shapes. For example, a film-shaped cured product can be obtained by melt molding or cast molding of this composition.

[0165] The thickness of the cured product is not particularly limited and can be appropriately selected according to the desired application. The thickness of the cured product is, for example, 10 μm or more, preferably 30 μm or more, and for example, 2 mm or less, preferably 1 mm or less.

[0166] The laminate may comprise a layer of the cured material (cured material layer) and a substrate. The laminate may have two or more substrate layers, two or more cured material layers, or other conventionally known layers other than the substrate and cured material layers. When the laminate has two or more substrate layers, cured material layers, and other layers, these may be the same layer (plate) or different layers (plates).

[0167] Examples of substrates include inorganic substrates, metal substrates, and resin substrates, from the viewpoint of adhesion and practicality. The substrate may also be a prepreg. Examples of inorganic substrates include those containing silicon, silicon carbide, silicon nitride, alumina, glass, and gallium nitride. Examples of metal substrates include those containing copper, aluminum, gold, silver, nickel, and palladium. The shape of the metal substrate is not particularly limited and may be in the form of a plate or metal foil.

[0168] <Copper-clad laminate> The copper-clad laminate according to the present invention is a laminate of a prepreg and a copper substrate, as described later, and preferably a laminate of a prepreg and copper foil, as described later.

[0169] Examples of the resin substrate include resin substrates composed of liquid crystal polymers, polyimides, polyphenylene sulfide, polyether ether ketones, polyamides (nylon), polyethylene terephthalate, polyethylene naphthalate, cycloolefin polymers, polyolefins, and the like.

[0170] The cured layer can be formed, for example, by curing it using the method described in the section on cured materials. The thickness of the cured layer is not particularly limited, but is, for example, 1 μm to 3 mm.

[0171] <<Prepreg>> The prepreg according to the present invention is obtained by impregnating a fibrous base plate with the above composition. There are no particular restrictions on the base plate, but fibrous base plates such as glass cloth, aramid nonwoven fabric, and polyester nonwoven fabric are preferred. The prepreg may also be a cured prepreg.

[0172] <<Applications>> This composition and its cured product can be suitably used in structural materials used in the transportation industry, such as the aircraft and automobile industries, and in electrical and electronic materials used in the electrical and electronic industry. Specifically, for example, it can be suitably used as a encapsulant for electrical and electronic components, an interlayer insulating film, a stress-relieving primer; in laminate applications (e.g., prepregs, copper-clad laminates, (multilayer) printed circuit boards, interlayer adhesives, solder resists, solder pastes); in adhesive applications (e.g., adhesive sheets for forming insulating layers, thermally conductive adhesives, adhesive sheets); in structural adhesives and prepregs used in various structural materials; in various coatings and optical component applications (e.g., optical films such as waveplates and phase difference plates, various special lenses such as conical lenses, spherical lenses, and cylindrical lenses, lens arrays), and in insulating films for printed circuit boards. In particular, interlayer insulating films made from the above cured product have excellent low dielectric loss tangent, adhesion, and heat resistance.

[0173] Examples of the aforementioned electronic components include circuit boards, semiconductor packages, or display boards. The cured product (cured film) can be used as a prepreg, copper-clad laminate, printed wiring board, adhesive sheet for forming an insulating layer, surface protective film, redistribution layer, or planarization film for these electronic components. Since the cured product can maintain its insulating properties even under high temperature and high humidity conditions, electronic components equipped with the cured product can protect circuit patterns from external environmental factors such as dust, heat, and moisture, and can also exhibit excellent insulation reliability between circuit patterns, enabling stable operation over many years.

[0174] The cured material can be used to form a redistribution layer by, for example, filling the gaps between patterns formed on the cured material (cured film) with metal by plating or the like, and, if necessary, repeatedly layering more cured material (cured film) and filling with metal. This makes it possible to manufacture an electronic component having a substrate and a redistribution layer including metal wiring and an insulating film.

[0175] The present invention will be described in more detail below based on examples, but the present invention is not limited in any way to these examples.

[0176] [Example 1] <<Synthesis of Compound A1>> In a glass reaction vessel equipped with a stirrer, thermometer, nitrogen inlet tube and condenser tube, 26.49 g of a bisphenol compound represented by the following formula (PA1-1) (manufactured by Honshu Chemical Industry Co., Ltd., BisOC-FL), 23.37 g of chloromethylstyrene with vinyl groups at the o, m, and p positions in a molar ratio (mol%) of 1:55:44, and 19.35 g of potassium carbonate were weighed in. Next, 79.48 g of N-methyl-2-pyrrolidone was added, and the mixture was reacted at 80°C for 4 hours under a nitrogen atmosphere. After the container was allowed to cool to room temperature, the salt was removed by filtration, and the resulting solution was added to methanol (2250 g). The precipitated solid was filtered off, and the solid was washed with a small amount of methanol. Then, the mixture was dried under reduced pressure at 40°C for 12 hours using a vacuum dryer to obtain a pale yellow solid compound A1. １ Identification by 1H-NMR (400 mHz) confirmed that compound A1 has the structure shown in Table 2.

[0177]

[0178] [Example 7] <<Synthesis of Compound A7>> In a glass reaction vessel equipped with a stirrer, thermometer, nitrogen inlet tube and condenser tube, weighed in the compound represented by the following formula (PA1-54) (47.77 g) (manufactured by Tokyo Chemical Industry Co., Ltd.), chloromethylstyrene (24.21 g) with vinyl groups at the o, m, and p positions (bonding mode (Y-1-4)) having a content ratio (mol%) of 1:51:48, and potassium carbonate (13.53 g), then N-methyl-2-pyrrolidone (71.65 g) was added, and the mixture was reacted at 80°C for 4 hours under a nitrogen atmosphere. After the container was allowed to cool to room temperature, the salt was removed by filtration, and the resulting solution was added to methanol (2250 g). The precipitated solid was filtered off, and the solid was washed with a small amount of methanol. Then, the mixture was dried under reduced pressure at 40°C for 12 hours using a vacuum dryer to obtain a pale yellow solid compound. １ When the 1H-NMR (400 MHz) spectrum was measured, the chemical shift shown below was confirmed, and the target compound A7 having the structure shown below was obtained.

[0179]

[0180]

[0181] The chemical shifts of the protons in A7 above were as follows: Hydrogen of No. 9: 0.76 ppm (18H) Hydrogen of No. 7: 1.34 ppm (12H) Hydrogen of No. 8: 1.72 ppm (4H) Hydrogen of No. 4: 4.17–4.26 ppm (2H) Hydrogen of No. 3: 4.35–4.46 ppm (4H) Hydrogen of No. 15: 5.08–5.20 ppm (2H) Hydrogen of No. 16: 5.51–5.67 ppm (2H) Hydrogen of No. 14: 6.45–6.64 ppm (2H) Hydrogen of No. 10–13: 6.87–7.22 ppm (8H) Hydrogen in cell 6: 7.23–7.29 ppm (2H) No. 1 Hydrogen in cell 1: 7.41–7.48 ppm (4H) No. 5 Hydrogen in cell 5: 7.63–7.70 ppm (2H) No. 2 Hydrogen in cell 2: 7.93–8.01 ppm (4H)

[0182] [Examples 2-6 and 10 and Comparative Examples 1-4 and 6] The synthesis was carried out in the same manner as in Example 1, except that the type of chloromethylstyrene (CMS) used in the synthesis was changed to the chloromethylstyrene (CMS) listed in Table 2 or Table 3, and the type of bisphenol compound was changed to the bisphenol compound corresponding to the compound listed in Table 2 or Table 3. The content ratio (mol%) of structural isomers of chloromethylstyrene (CMS) listed in Table 2 or Table 3 is as shown in Table 1. The obtained compounds were identified in the same manner as in Example 1 and confirmed to be the target compounds shown in Table 2 or Table 3.

[0183] [Examples 8 and 9 and Comparative Example 5] The synthesis was carried out in the same manner as in Example 7, except that the type of chloromethylstyrene (CMS) used in the synthesis was changed to the chloromethylstyrene (CMS) listed in Table 2 or Table 3, and the type of bisphenol compound was changed to the bisphenol compound corresponding to the compound listed in Table 2 or Table 3. The obtained compounds were identified in the same manner as in Example 7 and confirmed to be the target compounds shown in Table 2 or Table 3.

[0184]

[0185] Hereinafter, chloromethylstyrene with the vinyl group bonded at the orthogonal position (2-(chloromethyl)styrene) may also be called "o-chloromethylstyrene," chloromethylstyrene with the vinyl group bonded at the m-position (3-(chloromethyl)styrene) may be called "m-chloromethylstyrene," and chloromethylstyrene with the vinyl group bonded at the orthogonal position (4-(chloromethyl)styrene) may be called "p-chloromethylstyrene."

[0186] The chloromethylstyrene Y-1-1 to Y-1-4 and y-1-1 to y-1-4, whose structural isomer content ratios are shown in Table 1 above, were prepared by mixing reagents with a purity of 98% or higher for o-chloromethylstyrene, m-chloromethylstyrene, and p-chloromethylstyrene, respectively, in the content ratios shown in Table 1. The content ratios of each of o-chloromethylstyrene, m-chloromethylstyrene, and p-chloromethylstyrene in chloromethylstyrene are as follows: １３ Confirmation was made by 13C-NMR. The o-chloromethylstyrene and m-chloromethylstyrene reagents were manufactured by RR Scientific LLC, and the p-chloromethylstyrene used was manufactured by Oakwood Products Inc.

[0187] [Identification of the content ratio of structural isomers] The identification of the content ratio of structural isomers in chloromethylstyrene is as follows: １３ Chemical shifts were determined by 13C-NMR measurements, using the following carbon integral values ​​for o-chloromethylstyrene, m-chloromethylstyrene, and p-chloromethylstyrene: o-chloromethylstyrene No. 9: 44.1 ppm; m-chloromethylstyrene No. 9: 46.6 ppm; p-chloromethylstyrene No. 9: 46.2 ppm.

[0188]

[0189]

[0190]

[0191] In Tables 2 and 3, R represents the vinylbenzyl group represented by the following formula. The wavy lines in the formula indicate the linkage with the oxygen atom (O) in the chemical formulas in the tables.

[0192]

[0193] <<Synthesis of Polymer (B)>> The monomers used in the synthesis of polymer (B), which will be described later, are shown below.

[0194]

[0195] [Synthesis Example 1] <<Synthesis of Polymer (B1)>> In a four-necked separable flask equipped with a stirring device, weighed in monomer A-1 (34.09 g), monomer B-2 (12.81 g), monomer B-1 (2.83 g), and potassium carbonate (19.23 g), and added N-methyl-2-pyrrolidone (42.50 g). The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, the container was cooled to 10°C, and monomer Y-1 (chloromethylstyrene with a molar ratio of m-chloromethylstyrene to p-chloromethylstyrene of 15:85) (11.53 g) was added dropwise, followed by reaction at 100°C for 4 hours. N-methyl-2-pyrrolidone (55.00 g) was added to the resulting reaction solution to dilute it. After removing the salt by filtration, the resulting solution was added to methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered again to recover, and then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain polymer (B1) represented by the following formula (B1), which has a weight-average molecular weight (Mw) of 3100 and a number-average molecular weight (Mn) of 1500.

[0196]

[0197] In formula (B1), ** represents the bonding position with *.

[0198] [Synthesis Examples 2-4] <<Synthesis of Polymers (B2)-(B4)>> Polymers were obtained in the same manner as in Synthesis Example 1, except that the monomers used were changed to those listed in Table 4 and in quantities. The numbers in parentheses in Table 4 represent the mass of each monomer used. The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of each obtained polymer are shown in Table 4.

[0199] [Synthesis Example 5] <<Synthesis of Polymer (B5)>> In a four-necked separable flask equipped with a stirring device, monomer A-1 (30.35 g), monomer B-5 (30.60 g), and potassium carbonate (19.23 g) were weighed in, and N-methyl-2-pyrrolidone (42.50 g) was added. The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, the container was cooled to 10°C, and m-hydroxystyrene (5.57 g) was added dropwise, followed by reaction at 100°C for 4 hours. N-methyl-2-pyrrolidone (55.00 g) was added to the resulting reaction solution to dilute it. After removing the salt by filtration, the resulting solution was added to methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered again and recovered, and then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain polymer (B5) represented by the following formula. Table 4 shows the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of polymer (B5). In the formulas below, [ ] represents a repeating unit, * represents a binding site with **, and ** represents a binding site with *.

[0200] Polymer (B5)

[0201]

[0202] [Weight-average molecular weight (Mw) and number-average molecular weight (Mn)] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of polymers (B1) to (B4) synthesized in the above synthesis example were measured using a GPC instrument (Tosoh Corporation, model number: "HLC-8320") under the following conditions: • Column: A combination of "TSKgelα-M" and "TSKgelguardcolumnα" manufactured by Tosoh Corporation • Developing solvent: N-methyl-2-pyrrolidone • Column temperature: 40°C • Flow rate: 1.0 mL / min • Sample concentration: 0.75% by mass • Sample injection volume: 50 μL • Detector: Refractometer • Standard substance: Monodisperse polystyrene • Concentration of the sample for measurement: 0.1% by mass

[0203] [Example 101] A resin composition was prepared by mixing 30 parts by mass of compound A1 obtained above, 70 parts by mass of polymer (B3) obtained above, 0.5 parts by mass of dicumyl peroxide (manufactured by NOF Corporation) as a polymerization initiator (C), and toluene as an organic solvent (D) in a mixing rotor to obtain a solid content concentration of 50% by mass.

[0204] [Examples 102-112 and Comparative Examples 101-106] In Example 101, the types of compound (A) and polymer (B) were changed to those listed in Table 5 below, and the mixture was prepared to achieve the solid content concentration listed in Table 5. The mixture was then mixed in a mix rotor in the same manner as in Example 101 to prepare a resin composition.

[0205]

[0206] <Preparation of Cured Film> The resin compositions obtained in Examples 101 to 112 and Comparative Examples 101 to 106 were coated onto copper foil (model number: CF-T49A-DS-HD2, manufactured by Fukuda Metal Co., Ltd.) using a baker-type applicator (gap: 125 μm), heated at 100°C for 5 minutes, and then dried at 140°C for 5 minutes to form a coating film. A copper foil (model number: CF-T49A-DS-HD2, manufactured by Fukuda Metal Co., Ltd.) was placed on top of the obtained coating film, vacuum pressed at 160°C for 10 minutes, and then baked under nitrogen at 200°C for 2 hours to produce a copper foil-attached cured film (copper foil: 18 μm, cured film: 50 μm). The obtained copper foil-attached cured film was immersed in a 40% by mass iron chloride solution to remove the copper foil, washed with water, and dried in an oven at 80°C for 30 minutes to produce a cured film with a thickness of 50 μm.

[0207] <Dielectric Loss Tangent> A test piece (width: 6 cm x length: 6 cm) was cut from the fabricated hardened film, and the dielectric loss tangent (Df) of the test piece at 10 GHz was measured using the cavity resonator method (TE mode resonator, dielectric constant measurement system, manufactured by AET Co., Ltd.) and evaluated according to the following criteria. The results are shown in Table 6. If the evaluation criterion is "3" or higher (i.e., if the dielectric loss tangent (Df) is 0.0025 or less), it can be said that the dielectric loss tangent is low. (Evaluation Criteria) 1: 0.0030 < Df 2: 0.0025 < Df ≤ 0.0030 3: 0.0020 < Df ≤ 0.0025 4: 0.0015 < Df ≤ 0.0020 5: Df ≤ 0.0015

[0208] <Solubility in Solvents> For Examples 101-112 and Comparative Examples 101-106, all components of the resin composition used were dissolved in toluene (TL) at the following concentrations. The dissolution rate was evaluated as follows: 5 if all components of the resin composition dissolved in TL at 50% by mass or more; 4 if dissolved in TL at 30% by mass or more and less than 50% by mass; 3 if dissolved in TL at 20% by mass or more and less than 30% by mass; and 2 if dissolved in TL at less than 20% by mass. The results are shown in Table 6.

[0209]

Claims

1. A resin composition comprising: a compound (A) which is at least one of a compound (A1) having two or more partial structures represented by the following formula (1) and a compound (A2) represented by the following formula (2); and a polymer (B) having an aromatic ring and a group that crosslinks with the compound (A). In formula (1), Ar represents an aromatic ring having 6 to 10 carbon atoms; L is an oxygen atom, a methylene group, an alkylene group having 2 to 6 carbon atoms, or a group formed by combining two or more groups selected from these groups; R １１ is each independently bonded to a carbon atom which is a ring member of Ar and adjacent to a carbon atom that is a ring member of Ar to which L is bonded, and is a hydrogen atom or a monovalent organic group, provided that two R １１ at least one of which is a monovalent organic group, and R １３ is an alkyl group having 1 to 10 carbon atoms, an allyl group or a vinyl group, and m １２ is 0 or 1, * represents a bonding site to another structure, and R Ｐｈ is a group represented by formula (1a), (1b) or (1c); in formulas (1a), (1b) and (1c), R １２ each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R Ｖ represents a vinyl group, and ** represents a bonding site to L in formula (1). Provided that when the total amount of groups represented by formula (1a), (1b) and (1c) contained in compound (A1) is 100 mol%, the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less. In formula (2), R ２１ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms, or two R ２１ taken together with the carbon atom to which they are bonded represent a ring structure having 5 to 10 ring members, R ２２ and R ２３ each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aromatic group having 6 to 10 carbon atoms, wherein at least one R ２２ and at least one R ２３ At least one of these is independently a group represented by the following formulas (2-1a), (2-1b), or (2-1c), where R in formula (2) ２２ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group, and R in formula (2) ２３ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group. In formulas (2-1a), (2-1b), and (2-1c), L, R Ｖ , and, R １２ These are L and R in formula (1) or formulas (1a), (1b), and (1c), respectively. Ｖ , and, R １２ This is synonymous with R. ２２ or R ２３ This represents the bonding site with a carbon atom that is a ring member of the benzene ring to which the group is bonded. However, if the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%, then the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol% or less.

2. The resin composition according to claim 1, wherein the compound (A1) is a compound represented by the following formula (1-1) or the following formula (1-2). In formula (1-1), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １１ A valence group consisting of an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, or R １３ These can be combined with each other to form a ring structure with 3 to 20 members, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-1), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １１ R represents an integer between 2 and 4. In equation (1-1), R １１ , R １３ , L, and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, if the total amount of groups represented by formulas (1a), (1b), and (1c) contained in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less. In formula (1-2), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １２ A valence group, which represents an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-2), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １２ R represents an integer between 2 and 4. In equation (1-2), R １１ , R １３ , L and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, in formula (1-2), A is bonded to another carbon atom that is adjacent to the carbon atom that is a ring member of Ar to which L is bonded. In equations (10-1) to (10-3), * represents the bond site with Ar in equation (1-1) or equation (1-2).

3. The resin composition according to claim 1 or 2, wherein the polymer (B) is at least one resin selected from the group consisting of polyphenylene ether resins, polyfunctional vinyl aromatic copolymers, and heteroaromatic-aromatic ether resins.

4. The resin composition according to claim 1, further comprising a polymerization initiator (C).

5. The resin composition according to claim 1, further comprising an organic solvent (D).

6. A cured product comprising the resin composition described in claim 1.

7. A prepreg obtained by impregnating a fibrous substrate with the resin composition described in claim 1.

8. A copper-clad laminate obtained by laminating the prepreg described in claim 7 with a copper substrate.

9. An interlayer insulating film made of the cured product according to claim 6.

10. Compound (A), which is a compound (A1) having two or more substructures represented by the following formula (1), or a compound (A2) represented by the following formula (2). In formula (1), Ar represents an aromatic ring having 6 to 10 carbon atoms, L is an oxygen atom, a methylene group, an alkylene group having 2 to 6 carbon atoms, or a group consisting of two or more groups selected from these groups, and R １１ Each of these is independently bonded to a carbon atom that is a member of the Ar ring to which L is bonded, and to an adjacent carbon atom that is a member of the Ar ring, and is a hydrogen atom or a monovalent organic group, except for two R １１ At least one of them is a monovalent organic group, R １２ Each is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R １３ is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms, m １２ is 0 or 1, R Ｖ represents a vinyl group, * represents a bonding site with other structures, and R Ｐｈ is a group represented by formula (1a), (1b), or (1c), where R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R Ｖ represents a vinyl group, and ** represents the bonding site with L in formula (1). However, if the total amount of groups represented by formulas (1a), (1b), and (1c) in compound (A1) is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less. In formula (2), R ２１ Each of these independently consists of a hydrogen atom, a C1-C10 alkyl group, an unsubstituted or substituted C6-C10 aromatic group, or two R groups. ２１ These are combined with each other to form a ring structure with 5 to 10 members, R ２２ and R ２３ Each of these independently represents a hydrogen atom, a C1-C10 alkyl group, or an unsubstituted or substituted C6-C10 aromatic group, and the R ２２ At least one of the R ２３ At least one of them is independently a group represented by formula (2-1a), (2-1b), or (2-1c), where R in formula (2) ２２ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group, and R in formula (2) ２３ At least one of the two substituents bonded to the two carbon atoms adjacent to it is a C1-C10 alkyl group or an unsubstituted or substituted C6-C10 aromatic group. In equations (2-1a), (2-1b), and (2-1c), L, R Ｖ , and, R １２ These are L and R in formula (1) or formulas (1a), (1b), and (1c), respectively. Ｖ , and, R １２ This is synonymous with R. ２２ or R ２３ This represents the bonding site with a carbon atom that is a ring member of the benzene ring to which the group is bonded. However, if the total amount of groups represented by formulas (2-1a), (2-1b), and (2-1c) in compound (A2) is 100 mol%, then the content of the group represented by formula (2-1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (2-1a) is 0 mol% or more and 80 mol% or less.

11. Compound (A) according to claim 10, which is a compound represented by the following formula (1-1) or the following formula (1-2). In formula (1-1), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １１ A valence group is an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, or A is R １３ These can be combined with each other to form a ring structure with 3 to 20 members, R １３ R is an alkyl group, allyl group, or vinyl group having 1 to 10 carbon atoms. １３ If R is an alkyl group having 1 to 5 carbon atoms, １３ The linking group may be bonded to a carbon atom that is another Ar ring member in formula (1-1), and the -CH in the linking group ２ - may be replaced with -O- or -S-, n １１ R represents an integer between 2 and 4. In equation (1-1), R １１ , R １３ , L, and m １２ These are R in equation (1), respectively. １１ , R １３ , L, and m １２ This is equivalent to the above. However, if the total amount of groups represented by formulas (1a), (1b), and (1c) in the compound is 100 mol%, then the content of the group represented by formula (1b) is 10 mol% or more and 100 mol% or less, and the content of the group represented by formula (1a) is 0 mol% or more and 80 mol% or less. In formula (1-2), R Ｐｈ is one of the groups represented by formula (1a), (1b), or (1c) in formula (1), where A is a single bond or n １２ A valence group, which represents an oxygen atom, a sulfur atom, an unsubstituted or substituted methylene group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a group represented by any of the following formulas (10-1) to (10-3), or a group formed by combining two or more of these groups, R １３ is an alkyl group having 1 to 10 carbon atoms, an allyl group or a vinyl group, and R １３ is an alkyl group having 1 to 5 carbon atoms, R １３ may be a linking group bonded to a carbon atom which is another ring member of Ar in formula (1-2), and -CH ２ - in said linking group may be substituted with -O- or -S-, and n １２ represents an integer of 2 to 4. In formula (1-2), R １１ , R １３ , L, and m １２ each have the same definitions as R １１ , R １３ , L, and m １２ in formula (1), respectively. Provided that, in formula (1-2), A is bonded to a carbon atom which is another ring member adjacent to a carbon atom which is a ring member of Ar to which L is bonded. In formulas (10-1) to (10-3), * represents a binding site to Ar in formula (1-1) or formula (1-2).

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