Vinyl compound, vinyl composition, vinyl resin cured product, prepreg, film with resin, metal foil with resin, metal-clad laminate, and printed wiring board

Abstract

The present invention addresses the problem of providing a novel compound which can be used as a constituent material for a printed wiring board and exhibits a low melting point.　The present invention pertains to a vinyl compound which is represented by formula (A). (In formula (A), one of P1 and P2 represents a vinylbenzyl group, and the other represents an acryloyl group, a methacryloyl group, or a vinylbenzyl group, W represents a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by any one of the group B, m represents an integer of 1 to 5, Y1 and Y2 each represent an oxygen atom, an ester bond, or a carbonyl bond, and Q1 and Y2 each represent a group that is represented by any one of formulae (1) to (4). In formulae (1) to (4), A1, A2, A3 and A4 each represent a group to which two or more hydrocarbon rings including one or more groups selected from the group consisting of an aromatic group, a cycloalkylene group, and a cycloalkenylene group are linked, and X1, X2 and X3 each represent an ester bond or a carbonyl group.)

Description

Vinyl compounds, vinyl compositions, cured vinyl resins, prepregs, resin-coated films, resin-coated metal foils, metal-clad laminates, and printed wiring boards

[0001] The present invention relates to a vinyl compound, a vinyl composition, a cured vinyl resin, a prepreg, a resin-coated film, a resin-coated metal foil, a metal-clad laminate, and a printed wiring board.

[0002] The amount of data handled by communication devices and their communication speeds are increasing year by year, and as a result, research into high-speed communication technologies to improve signal transmission speeds is being actively conducted. When communication devices handle large amounts of data, the amount of heat generated by the electronic computing components in the devices increases, and if this heat accumulates on printed wiring boards, malfunctions occur. Therefore, printed wiring boards are required to have high heat dissipation properties.

[0003] As a printed wiring board with high heat dissipation properties, for example, a so-called thick copper board is known, which is made by increasing the thickness of the copper (i.e., copper pattern) forming the circuit to enable more heat to be dissipated through the copper. However, this thick copper board has a problem in that it is not suitable for communication devices, which require miniaturization and light weight, because it is thick overall.

[0004] A known example of a printed wiring board with high heat dissipation properties is a metal-based substrate, which has a metal plate on one side that allows it to dissipate more heat. However, this metal-based substrate requires an increased number of manufacturing steps, which increases the manufacturing costs of the communication device.

[0005] On the other hand, similar to printed wiring boards, materials that contain resin as the main constituent material and have high heat dissipation properties are known to contain fillers with high thermal conductivity. However, materials containing fillers have the problem of being unsuitable for manufacturing printed wiring boards due to their poor processability.

[0006] A resin with high thermal conductivity has been disclosed as a material that can solve these problems (Patent Document 1). Electronic materials used in high-speed communication devices are required to have not only high heat dissipation but also low dielectric loss, and the resin disclosed in Patent Document 1 itself has high thermal conductivity and low dielectric loss.

[0007] US Patent Application Publication No. 2019 / 0194408

[0008] However, the thermal conductivity of the resin disclosed in Patent Document 1 is not sufficient and there is room for improvement. Furthermore, in producing heat dissipation components such as printed wiring boards, it is desirable for the monomer compound, which is the raw material of the resin, to have good processability, and therefore a low melting point is required.

[0009] An object of the present invention is to provide a novel compound that exhibits a low melting point and can be used as a constituent material for printed wiring boards. Another object of the present invention is to provide a composition containing the novel compound that can give a cured product with high thermal conductivity.

[0010] The present invention employs the following features: [1] A vinyl compound represented by formula (A). (In the formula (A), P １ and P ２ one of the above is a vinylbenzyl group and the other is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, W is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms or any group represented by Group B, [Group B] [In the formula of the above group B, * represents Y １ or Y ２represents the bonding position with, n1 represents an integer from 1 to 10, n2 to n5 are the same or different and each represent 0 or 1, n6 to n7 are the same or different and each represent an integer from 0 to 4, n8 to n9 are the same or different and each represent an integer from 0 to 3, n10 to n11 are the same or different and each represent an integer from 0 to 4, n12 represents 0 or 1, R is an alkyl group or aryl group having 1 to 20 carbon atoms, and multiple Rs may be the same or different, S is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, some of the carbon atoms of which may be substituted with oxygen atoms, and multiple Ss may be the same or different.] m represents an integer from 1 to 5, Y １ and Y ２ are the same or different, and are an oxygen atom, an ester bond, or a carbonyl bond; Q １ and Q ２ are the same or different, and are a group represented by any one of formulas (1) to (4), [In the formulas (1) to (4), A １ , A ２ , A ３ and A ４are each the same or different and are a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkylene group, a substituted or unsubstituted divalent cycloalkenylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, １ , X ２ and X ３ are the same or different and each represent an ester bond or a carbonyl group, and when Q is a group represented by formula (1), A １is a substituted or unsubstituted divalent fused ring group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, or [2] The vinyl compound according to [1], wherein m represents an integer of 2 to 5. [3] The vinyl compound according to [1], wherein m is 1. [4] The vinyl compound according to [1], wherein P １ and P ２ [5] The vinyl compound according to [2] or [4], wherein each of X is a vinylbenzyl group. １ , X ２ and X ３ is an ester bond. [6] The vinyl compound according to any one of [1] to [5], which is used for a printed wiring board. [7] A vinyl composition containing the vinyl compound according to any one of [1] to [6]. [8] The vinyl compound according to [7], which further contains a vinyl compound represented by formula (B). (In the formula (B), P ３ and P ４ are each an acryloyl group, a methacryloyl group, a vinylbenzyl group, or a 5-hexenyl group, and Q ３ is a group represented by any one of formulas (5) to (8). [In the formulas (5) to (8), A ５, A ６ , A ７ and A ８ are the same or different and are a substituted or unsubstituted divalent aromatic group (excluding hydroxy group-containing aromatic groups), a substituted or unsubstituted divalent cycloalkylene group (excluding hydroxy group-containing cycloalkylene groups), a divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding hydroxy group-containing aromatic groups) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxy group-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups (excluding hydroxy group-containing aromatic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxy group-containing cycloalkylene groups) are linked by a single bond; and X ４ , X ５ and X ６ are the same or different and each represents an ester bond or a carbonyl group, ３ and P ４ are both vinylbenzyl groups, and Q ３ is a group represented by formula (5), A ５ is a divalent group in which two substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, and P ３ and P ４ When both are acryloyl groups or methacryloyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６one of the above is a substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups), and the other is a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, and P ３ and P ４ When both are 5-hexenyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６

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[12] A resin-coated metal foil comprising a resin layer containing the vinyl compound according to any one of [1] to [6] or a semi-cured product thereof, or the vinyl composition according to [7] or [8] or a semi-cured product thereof, and a metal foil.

[13] A metal-clad laminate comprising an insulating layer containing the cured product of the vinyl compound according to any one of [1] to [6] or the vinyl composition according to [7] or [8], and a metal foil.

[14] A metal-clad laminate comprising an insulating layer containing the cured product of the prepreg according to

[10] , and a metal foil.

[15] A printed wiring board comprising an insulating layer containing the cured product of the vinyl compound according to any one of [1] to [6], or the vinyl composition according to [7] or [8], and a conductor wiring.

[16] A printed wiring board comprising an insulating layer containing the cured product of the prepreg according to

[10] , and a conductor wiring.

[0011] According to the present invention, there is provided a novel compound that can be used as a constituent material for printed wiring boards and exhibits a low melting point. Furthermore, according to the present invention, there is provided a composition containing the novel compound, which can give a cured product with high thermal conductivity.

[0012] Fig. 1 is a cross-sectional view schematically showing an example of a laminate structure obtained using a vinyl compound according to one embodiment of the present invention. Fig. 2 is a cross-sectional view schematically showing another example of a laminate structure obtained using a vinyl compound according to one embodiment of the present invention. Fig. 3 is a cross-sectional view schematically showing yet another example of a laminate structure obtained using a vinyl compound according to one embodiment of the present invention. Fig. 4 is a cross-sectional view schematically showing yet another example of a laminate structure obtained using a vinyl compound according to one embodiment of the present invention.

[0013] Preferred embodiments of the present invention will now be described in detail.

[0014] <Vinyl Compound (A)> The vinyl compound of the present embodiment is represented by the following formula (A): In this specification, the vinyl compound represented by the following formula (A) may be referred to as "vinyl compound (A)".

[0015]

[0016] W in the vinyl compound (A) is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, or any group represented by Group B described below. When W is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, W is preferably a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, more preferably a linear or branched alkylene group having 1 to 20 carbon atoms, even more preferably a linear or branched alkylene group having 2 to 14 carbon atoms, and even more preferably a linear alkylene group having 2 to 14 carbon atoms.

[0017] Examples of the linear or branched alkylene group having 1 to 20 carbon atoms include a methylene group, an ethylene group, a trimethylene group (1,3-propylene group), a 1,2-propylene group, a tetramethylene group, a 1-methyl-1,3-propylene group, a 2-methyl-1,3-propylene group, a 2-methyl-1,2-propylene group, a pentamethylene group, a 1-methyl-1,4-butylene group, a 2-methyl-1,4-butylene group, a hexamethylene group, Examples of the alkyl group include a methyl group, a 3-methyl-1,5-pentamethylene group, a heptamethylene group, an octamethylene group, a 2-ethyl-1,6-hexylene group, a nonamethylene group, a decamethylene group, an undecamethylene group, a dodecamethylene group, a tridecamethylene group, a tetradecamethylene group, a pentadecamethylene group, a hexadecamethylene group, a heptadecamethylene group, an octadecamethylene group, a nonadecamethylene group, and an icosamethylene group.

[0018] W in the vinyl compound (A) may be any group represented by Group B. [Group B]

[0019] In the formula for Group B, * represents Y １ or Y ２ n1 represents a bonding position with n1, n2 to n5 are the same or different and represent 0 or 1, n6 to n7 are the same or different and represent an integer of 0 to 4, n8 to n9 are the same or different and represent an integer of 0 to 3, n10 to n11 are the same or different and represent an integer of 0 to 4, n12 represents 0 or 1, R is an alkyl group or aryl group having 1 to 20 carbon atoms, and multiple Rs may be the same or different from one another, and S is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, some of the carbon atoms of which may be substituted with oxygen atoms, and multiple Ss may be the same or different from one another.

[0020] In the formulae of Group B, n1 is preferably an integer of 1 to 5, and more preferably an integer of 2 to 4, n3 to n4 are preferably 0 from the viewpoint of ease of synthesis, and n6 to n11 are the same or different and are each preferably an integer of 0 to 2. In the formulae of Group B, R is preferably an alkyl group or aryl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 8 carbon atoms, and even more preferably an alkyl group having 1 carbon atom. In the formulae of Group B, S is preferably a group obtained by removing S from any of the groups represented by Group B, or a linear or branched alkylene group having 1 to 20 carbon atoms, and more preferably a linear alkylene group having 1 to 20 carbon atoms.

[0021] In the vinyl compound (A), m represents an integer of 1 to 5, and may be an integer of 2 to 5 or 1.

[0022] Y in the vinyl compound (A) １ and Y ２ are the same or different and each represents an oxygen atom, an ester bond, or a carbonyl bond, and are preferably an oxygen atom or an ester bond.

[0023] P in the vinyl compound (A) １ and P ２ is a group having a vinyl group (ethenyl group) at the terminal end. １ and P ２ is a vinylbenzyl group, and the other is an acryloyl group, a methacryloyl group, or a vinylbenzyl group. From the viewpoint of dielectric properties, P １ and P ２ Preferably, all of the groups are vinylbenzyl groups.

[0024] The vinylbenzyl group is a 2-vinylbenzyl group, a 3-vinylbenzyl group, or a 4-vinylbenzyl group, and preferably a 3-vinylbenzyl group or a 4-vinylbenzyl group. １ and P ２ When both of the above are vinylbenzyl groups, the positions of the vinyl groups may be the same or different.

[0025] Q in the vinyl compound (A) １ and Q ２ The structure of formula (A) is a mesogenic skeleton, and has a structure in which two or more hydrocarbon rings are linked together. １ and Q ２ are the same or different and are groups represented by any one of formulas (1) to (4), In the formulas (1) to (4), A １ , A ２ , A ３ and A ４ are each the same or different and are a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkylene group, a substituted or unsubstituted divalent cycloalkenylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, １ , X ２ and X ３ are the same or different and each represent an ester bond or a carbonyl group, and when Q is a group represented by formula (1), A １is a substituted or unsubstituted divalent fused ring group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, or A divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond.

[0026] In this specification, the aromatic ring may be a monocyclic ring, a fused ring, or a heterocyclic ring. When the aromatic ring is a heterocyclic ring, examples of heteroatoms contained in the heterocyclic ring include an oxygen atom, a nitrogen atom, and a sulfur atom. From the viewpoint of suppressing dielectric loss or dielectric tangent, it is preferable that the aromatic ring does not contain a heteroatom. The aromatic ring is preferably a monocyclic ring or a fused ring, more preferably a monocyclic ring.

[0027] A substituted or unsubstituted divalent aromatic group is a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted aromatic ring. That is, the substituted or unsubstituted divalent aromatic group may be a divalent monocyclic group, a divalent fused ring group, or a divalent heterocyclic group.

[0028] The number of carbon atoms in the unsubstituted divalent aromatic group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0029] Specific examples of the unsubstituted aromatic ring include benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene.

[0030] When the divalent aromatic group has a substituent, that is, when the aromatic ring has a substituent, the substituent is a substituent other than a hydroxy group, for example, one or more groups selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms. This is because an aromatic ring containing a hydroxy group as a substituent has high polarity and may cause an increase in the dielectric loss of the cured product.

[0031] The alkyl group having 1 to 20 carbon atoms may be a known alkyl group. Specific examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, an n-pentyl group, a neopentyl group, an n-hexyl group, an n-octyl group, a 2-ethylhexyl group, an n-nonyl group, an n-decyl group, an n-dodecyl group, an n-tetradecyl group, an n-hexadecyl group, an n-octadecyl group, and an n-icosyl group. The number of carbon atoms in the alkyl group is preferably 1 to 8, and more preferably 1 to 4. Specific examples of these preferred alkyl groups are the same as the alkyl groups having the corresponding number of carbon atoms among the specific examples described above.

[0032] The alkoxy group having 1 to 20 carbon atoms may be a known alkoxy group. Specific examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an isobutyloxy group, an n-pentyloxy group, a neopentyloxy group, an n-hexyloxy group, an n-octyloxy group, a 2-ethylhexyloxy group, an n-nonyloxy group, an n-decyloxy group, an n-dodecyloxy group, an n-tetradecyloxy group, an n-hexadecyloxy group, an n-octadecyloxy group, and an n-icosyloxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 8, and more preferably 1 to 4. Specific examples of these preferred alkyl groups are the same as the alkyl groups having the corresponding number of carbon atoms among the specific examples described above.

[0033] Specific examples of suitable unsubstituted divalent aromatic groups include the following groups (+ indicates the bonding position):

[0034]

[0035] In this specification, the cycloalkane ring may be a monocyclic ring, a fused ring, or a heterocyclic ring. When the cycloalkane ring is a heterocyclic ring, examples of heteroatoms contained in the heterocyclic ring include an oxygen atom, a nitrogen atom, and a sulfur atom. From the viewpoint of suppressing dielectric loss or dielectric tangent, it is preferable that the cycloalkane ring does not contain a heteroatom. The cycloalkane ring is preferably a monocyclic ring or a fused ring, and more preferably a monocyclic ring. Furthermore, in this specification, the cycloalkane group and the cycloalkane ring may be cis-isomers, trans-isomers, or mixtures thereof, but in the case of a mixture, it is preferable that the proportion of trans-isomers is high.

[0036] The substituted or unsubstituted divalent cycloalkylene group is a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted monocyclic, fused ring, or heterocyclic cycloalkane ring.

[0037] The number of carbon atoms in the unsubstituted divalent cycloalkylene group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0038] Specific examples of the unsubstituted cycloalkane ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane, cyclopentadecane, cyclohexadecane, cycloheptadecane, cyclooctadecane, cyclononadecane, cycloicosane, decalin, oxetane, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 1,3-dioxane, aziridine, pyrrolidine, piperidine, piperazine, morpholine, tetrahydrothiophene, and thiane.

[0039] When the divalent cycloalkylene group has a substituent, that is, when the cycloalkane ring has a substituent, the substituent has the same meaning as the substituent that the divalent aromatic group may have.

[0040] Specific preferred examples of the unsubstituted divalent cycloalkylene group include the following groups.

[0041]

[0042] In this specification, the cycloalkene ring may be a monocycle, a fused ring, or a heterocycle. When the cycloalkene ring is a heterocycle, examples of heteroatoms contained in the heterocycle include an oxygen atom, a nitrogen atom, and a sulfur atom. From the viewpoint of suppressing dielectric loss or dielectric tangent, it is preferable that the cycloalkene ring does not contain a heteroatom. The cycloalkene ring is preferably a monocycle or a fused ring, and more preferably a monocycle. The number of double bonds contained in one cycloalkene ring is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. Furthermore, the position of the double bond contained in the cycloalkene ring is not particularly limited.

[0043] A substituted or unsubstituted divalent cycloalkenylene group is a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted monocyclic, fused ring, or heterocyclic cycloalkene ring.

[0044] The number of carbon atoms in the unsubstituted divalent cycloalkenylene group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0045] Specific examples of the unsubstituted cycloalkene ring include cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclopentadiene, 1,3-cyclohexadiene, 1,4-cyclohexadiene, 1,3-cycloheptadiene, 1,4-cycloheptadiene, 1,3-cyclooctadiene, 1,5-cyclooctadiene, 1,6-cyclodecadiene, 1,5-cyclododecadiene, 1,3,5-cycloheptatriene, 1,3,5-cyclooctatriene, and 1,5,9-cyclododecatriene.

[0046] When the divalent cycloalkenylene group has a substituent, that is, when the cycloalkene ring has a substituent, the substituent has the same meaning as the substituent that the divalent aromatic group may have.

[0047] Specific preferred examples of the unsubstituted divalent cycloalkenylene group include the following groups.

[0048]

[0049] A divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond is a group in which two hydrogen atoms are removed from any position of a compound in which two or more substituted or unsubstituted aromatic rings are single-bonded. The substituted or unsubstituted aromatic rings linked by a single bond have the same meaning as the substituted or unsubstituted aromatic rings mentioned in the description of the above-mentioned substituted or unsubstituted divalent aromatic group, and preferred embodiments thereof are also the same.

[0050] In a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by single bonds, the number of substituted or unsubstituted aromatic rings linked by single bonds is not particularly limited as long as it is two or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0051] Specific examples of the compound in which two or more unsubstituted aromatic rings are linked by a single bond include compounds in which two or more identical or different aromatic rings are linked by a single bond, among the compounds exemplified as the specific examples of the aromatic rings described above, such as biphenyl, m-terphenyl, p-terphenyl, m-quarterphenyl, and p-quarterphenyl.

[0052] A divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond is a group in which two hydrogen atoms have been removed from any position of a compound in which two or more substituted or unsubstituted cycloalkane rings are single-bonded. The substituted or unsubstituted cycloalkane rings linked by a single bond have the same meaning as the substituted or unsubstituted cycloalkane rings mentioned in the description of the above-mentioned substituted or unsubstituted divalent cycloalkylene group, and preferred embodiments thereof are also the same.

[0053] In a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is two or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0054] Specific examples of the compound in which two or more unsubstituted cycloalkane rings are linked by a single bond include compounds in which two or more of the same or different cycloalkane rings are linked by a single bond, among the compounds listed as the specific examples of the unsubstituted cycloalkane ring described above, such as cyclopropylcyclohexane, bicyclohexyl, 1,3-dicyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

[0055] A divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond is a group in which two hydrogen atoms have been removed from any position of a compound in which two or more substituted or unsubstituted cycloalkene rings are single-bonded. The substituted or unsubstituted cycloalkene rings linked by a single bond have the same meaning as the substituted or unsubstituted cycloalkene ring mentioned in the description of the above-mentioned substituted or unsubstituted divalent cycloalkenylene group, and preferred embodiments thereof are also the same.

[0056] In a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, the number of substituted or unsubstituted cycloalkene rings linked by a single bond is not particularly limited as long as it is two or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0057] Specific examples of the compound in which two or more unsubstituted cycloalkene rings are linked by a single bond include compounds in which two or more identical or different cycloalkene rings are linked by a single bond, among the compounds exemplified as the specific examples of the cycloalkene rings described above.

[0058] The divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond is a group in which two hydrogen atoms are removed from any position of a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are linked by a single bond. The substituted or unsubstituted aromatic rings and substituted or unsubstituted cycloalkane rings linked by a single bond are respectively synonymous with the substituted or unsubstituted aromatic rings mentioned in the description of the above-mentioned substituted or unsubstituted aromatic groups, and the substituted or unsubstituted cycloalkane rings mentioned in the description of the above-mentioned substituted or unsubstituted cycloalkylene groups, and the preferred embodiments thereof are also the same.

[0059] In a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 to 2, and the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Furthermore, the total number of substituted or unsubstituted aromatic rings and substituted or unsubstituted cycloalkane rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0060] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are linked by a single bond include compounds in which one or more aromatic rings among the compounds exemplified as the specific examples of the unsubstituted aromatic rings described above and one or more cycloalkane rings among the compounds exemplified as the specific examples of the unsubstituted cycloalkane rings are linked by a single bond, such as cyclopropylbenzene, cyclopentylbenzene, cyclohexylbenzene, 1-cyclohexylnaphthalene, 2-cyclohexylnaphthalene, 2-phenyltetrahydrofuran, 2-cyclohexylfuran, 4-phenylpiperidine, 2-cyclohexylthiophene, and 4-phenylmorpholine.

[0061] Specific preferred examples of the divalent group in which one or more unsubstituted divalent aromatic groups and one or more unsubstituted divalent cycloalkylene groups are linked via a single bond include the following groups.

[0062]

[0063] A divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond is a group in which two hydrogen atoms have been removed from any position of a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond. The substituted or unsubstituted aromatic rings and substituted or unsubstituted cycloalkene rings linked by a single bond are respectively synonymous with the substituted or unsubstituted aromatic rings mentioned in the description of the above-mentioned substituted or unsubstituted aromatic groups and the substituted or unsubstituted cycloalkene rings mentioned in the description of the above-mentioned substituted or unsubstituted cycloalkenylene groups, and preferred embodiments thereof are also the same.

[0064] In a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 2, and the number of substituted or unsubstituted cycloalkene rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Furthermore, the total number of substituted or unsubstituted aromatic rings and substituted or unsubstituted cycloalkene rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0065] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkene rings are linked via a single bond include compounds in which one or more aromatic rings among the compounds exemplified as the specific examples of the unsubstituted aromatic rings described above are linked via a single bond to one or more cycloalkene rings among the compounds exemplified as the specific examples of the unsubstituted cycloalkene rings described above.

[0066] Specific preferred examples of the divalent group in which one or more unsubstituted divalent aromatic groups and one or more unsubstituted divalent cycloalkenylene groups are linked via a single bond include the following groups.

[0067]

[0068] A divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond is a group in which two hydrogen atoms have been removed from any position of a compound in which one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond. The substituted or unsubstituted cycloalkane ring and substituted or unsubstituted cycloalkene ring linked by a single bond are respectively synonymous with the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted cycloalkylene group above, and the substituted or unsubstituted cycloalkene ring mentioned in the description of the substituted or unsubstituted cycloalkenylene group above, and preferred embodiments thereof are also the same.

[0069] In a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1, and the number of substituted or unsubstituted cycloalkene rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Furthermore, the total number of substituted or unsubstituted cycloalkane rings and substituted or unsubstituted cycloalkene rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0070] Specific examples of the compound in which one or more unsubstituted cycloalkane rings and one or more unsubstituted cycloalkene rings are linked via a single bond include compounds in which one or more cycloalkane rings among the compounds listed as the specific examples of the unsubstituted cycloalkane rings described above are linked via a single bond to one or more cycloalkene rings among the compounds listed as the specific examples of the unsubstituted cycloalkene rings described above.

[0071] A divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond is a group in which two hydrogen atoms are removed from any position of a compound in which one or more substituted or unsubstituted aromatic rings, one or more substituted or unsubstituted cycloalkane rings, and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond. The substituted or unsubstituted aromatic rings linked by a single bond, the substituted or unsubstituted cycloalkane rings, and the substituted or unsubstituted cycloalkene rings linked by a single bond are respectively synonymous with the substituted or unsubstituted aromatic rings mentioned in the description of the substituted or unsubstituted aromatic groups above, the substituted or unsubstituted cycloalkane rings mentioned in the description of the substituted or unsubstituted cycloalkylene groups above, and the substituted or unsubstituted cycloalkene rings mentioned in the description of the substituted or unsubstituted cycloalkenylene groups above, and preferred embodiments thereof are also the same.

[0072] In a divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by single bonds, the number of substituted or unsubstituted aromatic rings linked by single bonds is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. The number of substituted or unsubstituted cycloalkane rings linked by single bonds is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. The number of substituted or unsubstituted cycloalkene rings linked by single bonds is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Furthermore, the sum of the number of substituted or unsubstituted aromatic rings, the number of substituted or unsubstituted cycloalkane rings, and the number of substituted or unsubstituted cycloalkene rings linked by single bonds is preferably 3 to 10, more preferably 3 to 4, and even more preferably 3.

[0073] Specific examples of the compound in which one or more substituted or unsubstituted aromatic rings, one or more unsubstituted cycloalkane rings, and one or more unsubstituted cycloalkene rings are linked by a single bond include compounds in which one or more aromatic rings among the compounds listed as the specific examples of the unsubstituted aromatic rings described above, one or more cycloalkane rings among the compounds listed as the specific examples of the unsubstituted cycloalkane rings described above, and one or more cycloalkene rings among the compounds listed as the specific examples of the unsubstituted cycloalkene rings described above are linked by a single bond.

[0074] A １ , A ２ , A ３ and A ４ are each the same or different, from the viewpoint of ease of synthesis of the vinyl compound, and are preferably a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkylene group, a substituted or unsubstituted divalent cycloalkenylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond.

[0075] When Q is a group represented by formula (1), A １From the viewpoint of ease of synthesis of the vinyl compound, is preferably a substituted or unsubstituted divalent fused ring group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond.

[0076] In formula (A), X １ , X ２ and X ３ are the same or different and each represent an ester bond (*-COO-** or *-OCO-**; * and ** represent A １ , A ２ , A ３ and A ４ ) or a carbonyl group, preferably an ester bond. X １ , X ２ and X ３ is an ester bond, the vinyl resin cured product containing the vinyl compound can exhibit excellent heat conductivity.

[0077] The melting point of the vinyl compound (A) is preferably 50 to 150° C., more preferably 60 to 140° C., even more preferably 70 to 135° C., and particularly preferably 80 to 130° C. When the melting point of the vinyl compound is within the above range, processing by melt-kneading or the like becomes easy, and the energy required for processing can also be reduced.

[0078] The vinyl compound (A) is polymerizable and can form a vinyl resin cured product (described later) by polymerization (also referred to as "curing" in this specification). Therefore, the vinyl compound (A) can be suitably used to form a constituent material for an insulating layer of a printed wiring board, a heat dissipation material, etc.

[0079] On the other hand, resins having hydroxyl groups tend to have high dielectric loss. For example, a resin that is a cured product of a compound (monomer) having an epoxy group at its terminal has a hydroxyl group in the resin, and its dielectric loss is high. In contrast, the terminal of the vinyl compound (A) is not an epoxy group or a hydroxy group, but a vinyl group (ethenyl group). Therefore, a cured product (polymer) of the vinyl compound (A) does not have a hydroxy group in the resin, and therefore exhibits low dielectric loss.

[0080] <Method for Producing Vinyl Compound (A)> Vinyl compound (A) can be produced, for example, by reacting a compound represented by formula (a1) (sometimes referred to herein as "compound (a1)"), a compound represented by formula (a2) (sometimes referred to herein as "compound (a2)"), a compound represented by formula (b) (sometimes referred to herein as "compound (b)"), a compound represented by formula (c1) (sometimes referred to herein as "compound (c1)"), and a compound represented by formula (c2) (sometimes referred to herein as "compound (c2)") in the presence of a base, or by transesterification in the absence of a base. As an alternative to compound (c1) and compound (c2), compound (c') from which compound (c1) and compound (c2) can be synthesized by a known organic synthesis method may be used.

[0081] (Compound (a1) represented by formula (a1) and compound (a2) represented by formula (a2)) (In the formula, P １ has the same meaning as above, Z １ represents a halogen atom.)

[0082] (In the formula, P ２ has the same meaning as above, Z ２ represents a halogen atom, and Z １ may be the same as or different from

[0083] Said Z １ and Z ２ represents a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

[0084] Examples of the compound (a1) and the compound (a2) include 2-vinylbenzyl bromide, 3-vinylbenzyl bromide, 4-vinylbenzyl bromide, 2-vinylbenzyl chloride, 3-vinylbenzyl chloride, 4-vinylbenzyl chloride, acryloyl bromide, acryloyl chloride, methacryloyl bromide, and methacryloyl chloride. The compound (a1) and the compound (a2) may be used singly or in any combination and ratio of two or more kinds.

[0085] (Compound (b) represented by formula (b)) (Wherein, W has the same meaning as above, T １ and T ２ are the same or different and each represent a hydroxy group or a halogen atom.

[0086] Said T １ and T ２ are the same or different and represent a hydroxy group or a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

[0087] Examples of compound (b) include 1,3-dibromopropane, 1,3-dichloropropane, 1,3-propanediol, 1,4-dibromobutane, 1,4-dichlorobutane, 1,4-butanediol, 1,5-dibromopentane, 1,5-dichloropentane, 1,5-pentanediol, 1,5-dibromo-3-methylpentane, 1,5-dichloro-3-methylpentane, 3-methylpentane-1,5-diol, 1,6-dibromohexane, 1,6-dichlorohexane, 1,6-hexanediol, 1,7-dibromoheptane, 1,7-dichloroheptane, 1,7-heptanediol, 1,8-dibromooctane, 1,8-dichlorooctane, and 1,8-octanedioic acid. ethanol, 1,9-dibromononane, 1,8-dichlorononane, 1,9-nonanediol, 1,10-dibromodecane, 1,10-dichlorodecane, 1,10-decanediol, 1,11-dibromoundecane, 1,11-dichloroundecane, 1,11-undecanediol, 1,12-dibromododecane, 1,12-dichlorododecane, 1,12-dodecanediol, 1,2-bis(2-bromoethoxy)ethane, 1,2-bis(2-chloroethoxy)ethane, 2,2'-(ethane-1,2-diylbis(oxy))bis(ethan-1-ol), bis(2-chloroethyl ether), bis(2-bromoethyl ether), diethylene glycol, diethylene glycol Bis(2-chloroethyl)ether, diethylene glycol bis(2-bromoethyl)ether, tetraethylene glycol, 1,2-bis(bromomethyl)benzene, 1,2-bis(chloromethyl)benzene, 1,2-phenylenedimethanol, 1,3-bis(bromomethyl)benzene, 1,3-bis(chloromethyl)benzene, 1,3-phenylenedimethanol, 1,4-bis(bromomethyl)benzene, 1,4-bis(chloromethyl)benzene, 1,4-phenylenedimethanol, 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene, 2,4-bis(chloromethyl)-1,3,5-trimethylbenzene, (2,4,6-trimethyl-1,3-phenylene)dimethanol, 4,4'-bis(bromomethyl)-1,1'-biphenyl, 4,4'-bis(chloromethyl)-1,1'-biphenyl, [1,1'-biphenyl]-4,4'-diyldimethanol, 1,4-Dibromobenzene, 1,4-dichlorobenzene, hydroquinone, 1,3-dibromobenzene, 1,3-dichlorobenzene, resorcinol, 1,4-dibromo-2-methylbenzene, 1,4-dichloro-2-methylbenzene, 2-methylbenzene-1,4-diol, 1,4-dibromo-2,3,5-trimethylbenzene, 1,4-dichloro-2,3,5-trimethylbenzene, 2,3,5-tribenzene-1,4-diol, 1,4-dibromo-2,5-di-tert-butylbenzene, 1,4-dichloro-2,5-di-tert-butylbenzene, 2,5-di-tert-butylbenzene-1,4-diol, 1,5-dibromonaphthalene, 1,5-dichloronaphthalene, naphthalene-1,5-diol, 2,7-dibromonaphthalene , 2,7-dichloronaphthalene, naphthalene-2,7-diol, 1,6-dibromonaphthalene, 1,6-dichloronaphthalene, naphthalene-1,6-diol, 2,6-dibromonaphthalene, 2,6-dichloronaphthalene, naphthalene-2,6-diol, 4,4'-(propane-2,2-diyl)bis(bromobenzene), 4,4'-(propane-2,2-diyl)bis(chlorobenzene), 4,4'-(propane-2,2-diyl)diphenol (also known as bisphenol A), 1,4-bis(2-(4-bromophenyl)propan-2-yl)benzene, 1,4-bis(2-(4-chlorophenyl)propan-2-yl)benzene, and 4,4'-(1,4-phenylenebis(propane-2,2-diyl))diphenol. The compound (b) may be used alone or in any combination and ratio of two or more kinds.

[0088] (Compound (c1) represented by formula (c1) and compound (c2) represented by formula (c2)) (In the formula, Q １ has the same meaning as above, and U １１ and U １２ are the same or different and each represent a hydroxy group, a methoxycarbonyl group, a carboxy group, or an acetyl group.

[0089] (In the formula, Q ２ has the same meaning as above, and U ２１ and U２２ are the same or different and each represents a hydroxy group, a methoxycarbonyl group, a carboxy group, or an acetyl group; １１ and U １２ may be the same or different.)

[0090] Said U １１ , U １２ , U ２１ , and U ２２ are the same or different and preferably represent a hydroxy group or a methoxycarbonyl group.

[0091] Examples of the compound (c1) and the compound (c2) include methyl 6-hydroxy-2-naphthoate, 4-(trans-4-hydroxycyclohexyl)phenol, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-ethylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-ethylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-propylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3,5-dimethylbenzoate, (2-methyl-1,4-phenylene)bis(4-hydroxybenzoate), 1,4-phenylene-bis(4-hydroxybenzoate), 1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate) ), 1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxybenzoate), 2-methoxy-1,4-phenylene-bis(4-hydroxybenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2-methyl-1,4-phenylene- Bis(4-hydroxy-2,6-dimethylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2,3,6-trimethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,3,6-trimethyl-1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2,3,5,Examples include 6-tetramethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), (4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 4-(4-hydroxycyclohexyl)phenol, and 4,4'-bicyclohexanol, as well as the following compounds. Compound (c1) and compound (c2) may be used alone, or two or more may be used in any combination and ratio. Compound (c1) and compound (c2) may be commercially available products, or may be produced according to known methods described in JP-A 2011-74366 or 2010-241797.

[0092]

[0093] As an alternative to compound (c1) and compound (c2), compound (c') may be used, which can be synthesized from compound (c1) and compound (c2) by a known organic synthesis method or a known method described in JP-A-2002-363117. Examples of compound (c') include hydroquinone, methyl 4-hydroxybenzoate, and the following compounds. Compound (c') may be used alone or in any combination and ratio of two or more.

[0094]

[0095] The amount of compound (b) used is usually preferably 0.01 to 3.0 equivalents, more preferably 0.05 to 1.5 equivalents, based on the total amount of compound (c1) and compound (c2) used.

[0096] The total amount of compound (c1) and compound (c2) used is usually preferably 0.1 to 5.0 equivalents, more preferably 0.1 to 2.5 equivalents, relative to the total amount of compound (a1) and compound (a2). When compound (c') is used instead of compound (c1) and compound (c2), the amount of compound (c') used can be adjusted depending on the preferred total amount of compound (c1) and compound (c2) used above.

[0097] The base may be either an inorganic base or an organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as sodium carbonate and potassium carbonate. Examples of the organic base include pyridine. The amount of the base used is preferably 2 to 5 equivalents relative to the total amount of compound (a1) and compound (a2) used. When an organic base that is liquid under the reaction conditions is used, such an organic base may be used in excess to double as a reaction solvent.

[0098] The reaction of compound (a1), compound (a2), compound (b), compound (c1), and compound (c2), or the reaction of compound (a1), compound (a2), compound (b), and compound (c'), is usually carried out in a solvent by mixing compound (a1), compound (a2), compound (b), compound (c1), and compound (c2), and optionally a base, or by mixing compound (a1), compound (a2), compound (b), and compound (c'), and optionally a base. The order of mixing is not particularly limited.

[0099] The solvent is not particularly limited as long as it is inert to the reaction. However, in the case of a reaction using compound (a1) and compound (a2), a hydrophilic solvent is preferred because it is more likely to suppress the production of by-products. Examples of the hydrophilic solvent include alcohol-based solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, and propylene glycol; ketone-based solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone; and ether-based solvents such as tetrahydrofuran, dioxane, methoxymethyl ether, and diethoxyethane; and the like, either alone or in mixtures. Furthermore, when an organic base that is liquid under the reaction conditions is used as the base, the organic base may be used as the reaction solvent. Among these, the solvent is preferably an ether-based solvent, an aprotic polar solvent, or a mixed solvent thereof, more preferably an aprotic polar solvent, and particularly preferably N,N-dimethylformamide.

[0100] In the case of a reaction using compound (a1) and compound (a2), the amount of solvent used is preferably 1 to 50 mL, and more preferably 2 to 30 mL, per 1 g of the total amount of compound (a1) and compound (a2).

[0101] In the case of a reaction using compound (b), compound (c1), and compound (c2), the solvent may be the hydrophilic solvent described above, or a non-polar solvent such as toluene or p-chlorotoluene.

[0102] In the case of a reaction using compound (b), compound (c1), and compound (c2), the amount of the solvent used is preferably 0.5 to 50 mL, and more preferably 1 to 30 mL, per 1 g of the total amount of compound (b), compound (c1), and compound (c2).

[0103] The reaction of the compound (a1) and the compound (a2) with the compound (c1) and the compound (c2); the reaction of an intermediate that is a reaction product of the compound (a1) and the compound (a2) with the compound (c1) and the compound (c2) with the compound (b); the reaction of the compound (b) with the compound (c1) and the compound (c2); the reaction of an intermediate that is a reaction product of the compound (b) with the compound (c1) and the compound (c2) with the compound (a1) and the compound (a2); the reaction of the compound (a1) and the compound (a2) with the compound (c'); the reaction of the compound (b) with the compound (c'); and the reaction of the intermediate that is a reaction product of the compound (a1) and the compound (a2) with the compound (c') with the intermediate that is a reaction product of the compound (b) and the compound (c') may all be carried out via a halogen exchange reaction, an esterification reaction, or a transesterification reaction in the presence of a catalyst or a reaction aid.

[0104] Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide, quaternary ammonium halides such as tetrabutylammonium iodide, N,N-dimethylaminopyridine, dibutyltin oxide, etc. When a catalyst is used, the amount used is preferably 0.01 to 0.2 times by mass, more preferably 0.02 to 0.15 times by mass, relative to the total amount of compound (a1) and compound (a2) used.

[0105] Examples of the reaction aid include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and N,N-dicyclocarbodiimide.

[0106] The reaction of compound (a1) and compound (a2) with compound (b), compound (c1), and compound (c2), or the reaction of compound (a1) and compound (a2) with compound (c'), the reaction of an intermediate that is a reaction product of compound (b), (c1), and compound (c2) with compound (a1) and compound (a2), or the reaction of an intermediate that is a reaction product of compound (a1), compound (a2), and compound (c') with an intermediate that is a reaction product of compound (b) and compound (c') may be carried out in the presence of a polymerization inhibitor. Examples of the polymerization inhibitor include 2,6-di(tert-butyl)-p-cresol. When a polymerization inhibitor is used, the amount used is preferably 0.0005 to 0.02 times by mass, more preferably 0.001 to 0.01 times by mass, relative to the total amount of compound (a1) and compound (a2).

[0107] The reaction may be carried out under normal pressure conditions or under reduced pressure conditions. The reaction temperature is usually preferably 10 to 150°C. In this reaction, water or methanol may be by-produced as the reaction proceeds. In such cases, it is preferable to carry out the reaction while removing the by-produced water or methanol from the reaction system, and it is preferable to carry out the reaction at a reaction temperature and reaction pressure at which water or methanol is removed azeotropically. The reaction time is usually preferably 1 to 24 hours.

[0108] After the reaction is complete, for example, the reaction solution is cooled, water or a mixed solvent containing water is added, and the precipitated solid is filtered off. If necessary, known post-treatment procedures are carried out once or twice or more times to obtain vinyl compound (A). Examples of the post-treatment procedures include stirring and washing the solid in water, a mixed solvent containing water, or an organic solvent; and extraction (liquid separation) of the solution in which the solid is dissolved. If necessary, the obtained vinyl compound (A) may be further purified by a conventional purification means.

[0109] The structure of the obtained vinyl compound (A) can be confirmed by a known method such as nuclear magnetic resonance (NMR) spectroscopy.

[0110] <Vinyl composition> The vinyl composition of the present embodiment contains a vinyl compound (A). In this specification, the vinyl composition of the present embodiment may be referred to as "vinyl composition (A)".

[0111] The vinyl composition (A) is curable and may contain only the vinyl compound (A), or may contain the vinyl compound (A) and other components in addition to the vinyl compound (A) as long as the effects of the present invention are not impaired. The vinyl compound (A) may be cured by heating or by light irradiation. In the following examples, the vinyl composition (A) is cured by heating. When curing the vinyl composition (A), pressure may be applied to the vinyl composition (A). The vinyl composition (A) can be suitably used to form a constituent material such as an insulating layer of a printed wiring board or a heat dissipation material.

[0112] The vinyl compound (A) contained in the vinyl composition (A) may be one kind or two or more kinds. From the viewpoint of increasing the thermal conductivity of the cured product, the vinyl composition (A) contains Q １ and Q ２ The vinyl composition (A) preferably contains a mixture of multiple types of vinyl compounds (A) in which the positions of the vinyl groups in the vinylbenzyl groups that are terminal groups are different and the portions other than the vinylbenzyl groups are the same.

[0113] <Other Components> Examples of the other components contained in the vinyl composition (A) include a radical initiator; a filler; an additive; a solvent; a vinyl compound other than the vinyl compound (A) (sometimes referred to as "other vinyl compounds" in this specification); and a resin other than a polymer (cured product) of the vinyl compound (A) (sometimes referred to as "other resins" in this specification).

[0114] Examples of the additives include silane coupling agents, colorants, low-stress components, mold release agents, antioxidants, antifoaming agents, and flow control agents.

[0115] Examples of the radical initiator include azo compounds and organic peroxides.

[0116] Examples of the filler include silica powders such as fused crushed silica powder, fused spherical silica powder, crystalline silica powder, and secondary agglomerated silica powder; metal oxides such as alumina, titanium oxide, zinc oxide, tungsten carbide, and magnesium oxide; glass cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, and titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; and mica.

[0117] Examples of the silane coupling agent include γ-glycidoxypropyltrimethoxysilane. Examples of the colorant include carbon black. Examples of the low-stress component include silicone oil and silicone rubber. Examples of the release agent include natural wax, synthetic wax, higher fatty acid, metal salt of higher fatty acid, paraffin, etc.

[0118] Examples of the solvent contained in the vinyl composition (A) include ketone-based solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as dimethyl sulfoxide and N-methylpyrrolidone; ester-based solvents such as butyl acetate; glycol-based solvents such as propylene glycol monomethyl ether; and aromatic solvents such as toluene.

[0119] The other vinyl compound is not particularly limited as long as it has a vinyl group and does not fall under the category of vinyl compound (A), and examples thereof include vinyl compound (B) described below. The other resin is not particularly limited as long as it is a resin other than a polymer of vinyl compound (A).

[0120] The vinyl composition (A) may contain only one type of other component, or two or more types of other components.

[0121] The content of the other components in the vinyl composition (A) can be arbitrarily selected depending on the type of the other components. In the vinyl composition (A), the content ratio of the vinyl compound (A) to the total content of components other than the solvent is preferably 80% by mass or more, and may be, for example, 85% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, or 99% by mass or more. Meanwhile, the ratio is 100% by mass or less. A vinyl composition (A) having the ratio of 80% by mass or more is preferred because the effects obtained by containing the vinyl compound (A) are more enhanced.

[0122] The vinyl compound (A) obtained by the above method can be used as it is as the vinyl composition (A). The vinyl composition (A) containing the other components can be obtained by mixing the vinyl compound (A) with the other components.

[0123] <Vinyl Compound (B)> Examples of the other vinyl compounds contained in the vinyl composition (A) include vinyl compounds represented by the following formula (B): In this specification, the vinyl compound represented by the following formula (B) may be referred to as "vinyl compound (B)."

[0124]

[0125] P in the vinyl compound (B) ３ and P ４ is a group having a vinyl group (ethenyl group) at the terminal. ３ and P ４ are all acryloyl groups, methacryloyl groups, vinylbenzyl groups, or 5-hexenyl groups, and from the viewpoint of ease of polymerization, they are preferably acryloyl groups, methacryloyl groups, or vinylbenzyl groups, and from the viewpoint of low dielectric constant, they are more preferably vinylbenzyl groups.

[0126] The vinylbenzyl group is a 2-vinylbenzyl group, a 3-vinylbenzyl group, or a 4-vinylbenzyl group, and preferably a 3-vinylbenzyl group or a 4-vinylbenzyl group. ３ and P ４is a vinylbenzyl group, the positions of the vinyl groups may be the same or different.

[0127] Q in the vinyl compound (B) ３ The structure of formula (B) is a mesogenic skeleton, and has a structure in which two or more hydrocarbon rings are linked together. ３ is a group represented by any one of formulas (5) to (8), In the formulas (5) to (8), A ５ , A ６ , A ７ and A ８ are the same or different and are a substituted or unsubstituted divalent aromatic group (excluding hydroxy group-containing aromatic groups), a substituted or unsubstituted divalent cycloalkylene group (excluding hydroxy group-containing cycloalkylene groups), a divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding hydroxy group-containing aromatic groups) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxy group-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups (excluding hydroxy group-containing aromatic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxy group-containing cycloalkylene groups) are linked by a single bond; and X ４ , X ５ and X ６ are the same or different and each represents an ester bond or a carbonyl group, ３ and P ４ are both vinylbenzyl groups, and Q ３ is a group represented by formula (5), A ５ is a divalent group in which two substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, and P３ and P ４ When both are acryloyl groups or methacryloyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６ one of the above is a substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups), and the other is a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond, and P ３ and P ４ When both are 5-hexenyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６ one of the above is a substituted or unsubstituted divalent aromatic group, and the other is a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxy group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxy group-containing cycloalkylene groups) are linked by a single bond.

[0128] Specific examples and preferred embodiments of the number of carbon atoms in the unsubstituted divalent aromatic group, specific examples and preferred embodiments of the unsubstituted divalent aromatic ring, and specific examples and preferred embodiments of the substituent when the divalent aromatic group has a substituent are the same as the respective specific examples and preferred embodiments in the vinyl compound (A).

[0129] Specific examples and preferred embodiments of the number of carbon atoms in the unsubstituted divalent cycloalkylene group, specific examples and preferred embodiments of the unsubstituted divalent cycloalkane ring, and specific examples and preferred embodiments of the substituent when the divalent cycloalkylene group has a substituent are the same as the respective specific examples and preferred embodiments in the vinyl compound (A).

[0130] In a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by single bonds, specific examples and preferred embodiments of the number of substituted or unsubstituted aromatic rings linked by single bonds, as well as specific examples and preferred embodiments of a compound in which two or more unsubstituted aromatic rings are linked by single bonds, are the same as the respective specific examples and preferred embodiments in the vinyl compound (A).

[0131] In a divalent group in which two or more substituted or unsubstituted divalent cycloalkane rings are linked by single bonds, specific examples and preferred embodiments of the number of substituted or unsubstituted cycloalkane rings linked by single bonds, as well as specific examples and preferred embodiments of a compound in which two or more unsubstituted cycloalkane rings are linked by single bonds, are the same as the respective specific examples and preferred embodiments of the vinyl compound (A).

[0132] In a divalent group in which one or more substituted or unsubstituted divalent aromatic rings and one or more substituted or unsubstituted divalent cycloalkane rings are linked by single bonds, specific examples and preferred embodiments of the number of substituted or unsubstituted aromatic rings linked by single bonds, as well as specific examples and preferred embodiments of a compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are linked by single bonds, are the same as the respective specific examples and preferred embodiments in the vinyl compound (A).

[0133] In formula (B), X ４ , X ５ and X ６ are the same or different and each represents an ester bond (*'-COO-**' or *'-OCO-**'; *' and **' represent A ５ , A ６ , A ７ and A ８ ) or a carbonyl group, preferably an ester bond or a carbonyl group, more preferably an ester bond. X ４ , X ５ and X ６ is an ester bond, the vinyl resin cured product containing the vinyl compound can exhibit excellent heat conductivity.

[0134] <Method for producing vinyl compound (B)> The vinyl compound (B) can be produced, for example, by reacting a compound represented by formula (ba) (sometimes referred to herein as “compound (ba)”), a compound represented by formula (bb) (sometimes referred to herein as “compound (bb)”), and a compound represented by formula (bc) (sometimes referred to herein as “compound (bc)”) in the presence of a base.

[0135] (In the formula, Q ３ has the same meaning as above.)

[0136] (In the formula, P ３ has the same meaning as above, Z ３ represents a halogen atom.)

[0137] (In the formula, P ４ has the same meaning as above, Z ４ represents a halogen atom, and Z ３ may be the same as or different from

[0138] Examples of the compound (ba) include 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-ethylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-propyl ... xyl-4-hydroxy-3,5-dimethylbenzoate, (2-methyl-1,4-phenylene)bis(4-hydroxybenzoate), 1,4-phenylene-bis(4-hydroxybenzoate), 1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2-methyl-1,4-phenylene -bis(4-hydroxybenzoate), 2-methoxy-1,4-phenylene-bis(4-hydroxybenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy hydroxybenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2,3,6-trimethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,3,6-trimethyl-1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,3,5,6-tetramethyl-1,Examples of the compound (ba) include 4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), (4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 4-(4-hydroxycyclohexyl)phenol, and 4,4'-bicyclohexanol. Compound (ba) can be commercially available or can be produced according to the known method described in JP-A 2011-74366 or 2010-241797.

[0139] Said Z ３ and Z ４ are the same or different and represent a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, an iodine atom, etc. Compound (bb) and compound (bc) may be the same or different from each other.

[0140] Examples of compound (bb) and compound (bc) include 2-vinylbenzyl bromide, 3-vinylbenzyl bromide, 4-vinylbenzyl bromide, 2-vinylbenzyl chloride, 3-vinylbenzyl chloride, 4-vinylbenzyl chloride, 1-propenyl chloride, 1-propenyl bromide, 1-butenyl chloride, 1-butenyl bromide, 1-pentenyl chloride, 1-pentenyl bromide, 1-hexenyl chloride, 1-hexenyl bromide, acryloyl bromide, acryloyl chloride, methacryloyl bromide, and methacryloyl chloride. Compound (bb) and compound (bc) may be used singly or in any combination and ratio of two or more.

[0141] When compound (bb) and compound (bc) are the same, the amount thereof to be used is usually preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents, relative to compound (ba). When compound (bb) and compound (bc) are different, the amount of compound (bb) to be used is usually preferably 1 to 50 equivalents, more preferably 1 to 25 equivalents, relative to compound (ba), and the amount of compound (bc) to be used is usually preferably 1 to 50 equivalents, more preferably 1 to 25 equivalents, relative to compound (ba).

[0142] Specific examples of the base are the same as those in the production method for vinyl compound (A). The amount of base used is preferably 2 to 5 equivalents relative to compound (ba). When an organic base that is liquid under reaction conditions is used, such organic base may be used in excess, also serving as a reaction solvent.

[0143] The reaction of compound (ba), compound (bb), and compound (bc) is usually carried out by mixing compound (ba), compound (bb), compound (bc), and a base in a solvent. The order of mixing is not particularly limited.

[0144] Specific examples and preferred embodiments of the solvent are the same as those in the reaction using the compound (a1) and the compound (a2) in the production method of the vinyl compound (A).

[0145] The amount of the solvent used is preferably 1 to 20 mL, more preferably 2 to 10 mL, per 1 g of compound (ba).

[0146] Regardless of whether compound (bb) and compound (bc) are the same or not, the reaction between compound (ba) and compound (bb); the reaction between compound (bc) and an intermediate that is a reaction product of compound (ba) and compound (bb); the reaction between compound (ba) and compound (bc); and the reaction between compound (bb) and an intermediate that is a reaction product of compound (ba) and compound (bc) may all be carried out via a halogen exchange reaction in the presence of a catalyst. Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide. When a catalyst is used, the amount used is preferably 0.05 to 1 times, and more preferably 0.1 to 0.5 times, the amount of compound (ba) used.

[0147] The reaction of compound (ba), compound (bb), and compound (bc) may be carried out in the presence of a polymerization inhibitor. Examples of the polymerization inhibitor include 2,6-di(tert-butyl)-p-cresol. When a polymerization inhibitor is used, the amount used is preferably 0.002 to 0.05 times by mass, more preferably 0.004 to 0.02 times by mass, relative to the total amount of compound (bb) and compound (bc).

[0148] The reaction may be carried out under normal pressure conditions or under reduced pressure conditions. The reaction temperature is usually preferably 10 to 150°C. In this reaction, water may be produced as a by-product as the reaction proceeds. In such cases, it is preferable to carry out the reaction while removing the by-product water from the reaction system, and it is preferable to carry out the reaction at a reaction temperature and pressure at which water is removed azeotropically. The reaction time is usually preferably 1 to 24 hours.

[0149] After the reaction is complete, for example, the reaction solution is cooled, water or a mixed solvent containing water is added, and the precipitated solid is filtered off. If necessary, known post-treatment procedures are carried out once or twice or more times to obtain vinyl compound (A). Examples of the post-treatment procedures include stirring and washing the solid in water, a mixed solvent containing water, or an organic solvent; and extraction (liquid separation) of the solution in which the solid is dissolved. If necessary, the obtained vinyl compound (B) may be further purified by a conventional purification method.

[0150] The structure of the obtained vinyl compound (B) can be confirmed by a known method such as nuclear magnetic resonance (NMR) spectroscopy.

[0151] <Cured vinyl resin product> The cured vinyl resin product of the present embodiment is obtained by curing the vinyl compound (A) or the vinyl composition (A). In this specification, the cured vinyl resin product of the present embodiment may be referred to as the "cured vinyl resin product (A)."

[0152] The vinyl resin cured product has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A), and is therefore suitable as a constituent material for printed wiring boards, and is particularly suitable as an insulating material for forming printed wiring boards.

[0153] When the vinyl resin cured product (A) is a cured product of a vinyl compound (A), the vinyl resin cured product (A) may be a cured product of one type of vinyl compound (A) or two or more types of vinyl compounds (A). When the vinyl resin cured product (A) is a cured product of a vinyl composition (A), the vinyl resin cured product (A) may be a cured product of one type of vinyl composition (A) or a cured product of a mixture of two or more types of vinyl compositions (A).

[0154] The vinyl resin cured product (A) can be prepared, for example, by filling the vinyl compound (A) or the vinyl composition (A) as is into a mold, heating it for a predetermined time if necessary to effect primary curing, and then heating it for a predetermined time while applying pressure at a predetermined pressure with a press or the like to effect complete curing; by heating the vinyl compound (A) or the vinyl composition (A) as is at a predetermined temperature to effect curing; by pouring a powder of the vinyl compound (A) or the vinyl composition (A) as is, or after melting it as necessary, into a mold and heating it for a predetermined time while applying pressure at a predetermined pressure with a press or the like; or by heating the vinyl compound (A) or the vinyl composition (A) by melting it and pouring it into a mold or the like, and then closing the mold. a method of melting the vinyl compound (A) or the vinyl composition (A) and injecting the resulting melt into a preheated mold to cure it; a method of partially curing the vinyl compound (A) or the vinyl composition (A), pulverizing the resulting partially cured product, filling a mold with the resulting powder, and melt-molding the filled powder; a method of dissolving the vinyl compound (A) or the vinyl composition (A) directly or as needed in a solvent, partially curing while stirring as needed, casting the resulting solution, and then drying and removing the solvent by forced air drying or the like, and heating for a predetermined time while applying pressure at a predetermined pressure using a press or the like as needed.

[0155] The heating temperature (curing temperature; when curing is performed in multiple stages, the complete curing temperature) when the vinyl compound (A) or the vinyl composition (A) is heated to be cured is not particularly limited, but is preferably 120° C. or higher, more preferably 150° C. or higher, in order to increase the degree of curing of the vinyl compound (A) or the vinyl composition (A). The heating temperature is preferably 200° C. or lower, in order to avoid excessive heating.

[0156] The heating time (curing time; in the case of multi-stage curing, the heating time at the complete curing temperature) when the vinyl compound (A) or the vinyl composition (A) is heated and cured is not particularly limited, but is preferably 1 hour or more, more preferably 2 hours or more, in order to increase the degree of curing of the vinyl compound (A) or the vinyl composition (A). The heating time is preferably 10 hours or less, in order to avoid unnecessary curing operations.

[0157] The pressure applied when pressing and curing the vinyl compound (A) or the vinyl composition (A) (pressure during curing) is not particularly limited, but is preferably 0.7 MPa or more, more preferably 1.2 MPa or more, in order to increase the degree of curing of the vinyl compound (A) or the vinyl composition (A). The pressure applied is preferably 3 MPa or less, in order to avoid excessive pressurization.

[0158] The thermal diffusivity of the cured vinyl resin (A) is 1.75 × 10 －７ m ２ / s or more, and 1.80 × 10 －７ m ２ / s or more, and more preferably 1.90 × 10 －７ m ２ When the thermal diffusivity is within the above range, the thermal conductivity tends to be high. The upper limit of the thermal diffusivity of the vinyl resin cured product (A) is not particularly limited, and the thermal diffusivity is preferably 4.00×10 －７ m ２ / s or less, or 3.60 × 10 －７ m ２ / s or less, or 3.20 × 10 －７ m ２ The thermal diffusivity of the vinyl resin cured material (A) may be, for example, 1.70 × 10 －７ ~4.00 x 10 －７ m ２ / s, 1.80 × 10 －７ ~3.60 x 10 －７ m ２ / s, and 1.90 × 10 －７ ~3.20 x 10 －７ m ２ / s.

[0159] The thermal diffusivity of the vinyl resin cured product (A) can be measured by temperature wave thermal analysis (TWA).

[0160] The upper limit of the dielectric dissipation factor of the cured vinyl resin (A) at a frequency of 100 MHz is preferably 0.0310 or less, more preferably 0.0200 or less, and even more preferably 0.0100 or less. The lower limit of the dielectric dissipation factor of the cured vinyl resin (A) is not particularly limited, and the dielectric dissipation factor may be 0.0010 or more, 0.0020 or more, or 0.0030 or more. The dielectric dissipation factor of the cured vinyl resin (A) at a frequency of 100 MHz may be, for example, any of 0.0010 to 0.0310, 0.0020 to 0.0200, and 0.0030 to 0.0100. However, these are just examples of the dielectric dissipation factor of the cured vinyl resin (A).

[0161] The dielectric loss tangent of the cured vinyl resin (A) at a frequency of 100 MHz can be measured by a capacitance method using an impedance analyzer under the following conditions: Measurement method: capacitance method; Electrode type: 16453A; Measurement environment: 23°C, 50% RH; Applied voltage: 1 V

[0162] <Prepreg> The prepreg of this embodiment includes a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a fibrous base material. In this specification, the prepreg of this embodiment may be referred to as "prepreg (A)." By using the prepreg (A), a laminate or the like can be easily produced by a conventional method. For example, the desired laminate can be obtained by stacking multiple prepregs (A) to form a laminate, and then molding and integrating the laminate under heat and pressure. A printed wiring board (resin layer in the printed wiring board) obtained using the prepreg (A) or the laminate has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0163] The prepreg (A) can be produced by a method of coating or impregnating a fibrous substrate with a solution prepared by dissolving the vinyl compound (A) in a solvent; or by a method of coating or impregnating a fibrous substrate with the vinyl composition (A) or a dilution prepared by diluting the vinyl composition (A) with a solvent, and then heating the coated or impregnated fibrous substrate to semi-cure the vinyl compound (A) or the vinyl composition (A).

[0164] The heating temperature (semi-curing temperature) and heating time (semi-curing time) when semi-curing the vinyl compound (A) or the vinyl composition (A) can be appropriately set in consideration of the above-mentioned curing conditions (heating temperature and heating time) of the vinyl compound (A) or the vinyl composition (A) so that the vinyl compound (A) or the vinyl composition (A) is not completely cured.

[0165] The fibrous substrate is not particularly limited as long as it is a fibrous substrate, and may be a known one. More specifically, examples of the fibrous substrate include woven and nonwoven fabrics of inorganic fibers such as glass fibers, and woven and nonwoven fabrics of organic fibers such as polyester.

[0166] <Resin-Coated Film> The resin-coated film of this embodiment includes a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a support film. More specifically, examples of the resin-coated film of this embodiment include a resin-coated film including the resin layer and the support film provided on one or both sides of the resin layer. A laminate sheet can be obtained by using multiple resin-coated films of this embodiment, removing the support film, stacking them to form a laminate, and molding and integrating this laminate under heat and pressure. The resin layer in the resin-coated film of this embodiment and the printed wiring board (resin layer in the printed wiring board) obtained using the resin layer or laminate sheet have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0167] Examples of the support film include a polyethylene terephthalate (PET) film. In a resin-coated film, when support films are provided on both sides of the resin layer, these support films may be the same or different. In this specification, not limited to the case of a resin-coated film, the term "two layers of support films that are different from each other" means that at least one of the material and thickness of the two layers of support films is different from each other.

[0168] The resin-coated film of this embodiment can be produced by coating the support film with a solution of the vinyl compound (A) dissolved in a solvent, or by coating the support film with the vinyl composition (A) or a diluted version of the vinyl composition (A) diluted with a solvent, and then heating the coating layer to semi-cure the vinyl compound (A) or vinyl composition (A) in the coating. The conditions for semi-curing the vinyl compound (A) or vinyl composition (A) are the same as those for producing the prepreg described above.

[0169] <Resin-Coated Metal Foil> The resin-coated metal foil of this embodiment includes a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a metal foil. More specifically, the resin-coated metal foil of this embodiment includes a resin layer and a metal foil provided on one or both sides of the resin layer. For example, a printed wiring board can be produced by using the resin-coated metal foil of this embodiment to further cure the semi-cured product to form a cured product, and then patterning the metal foil to form a circuit. Furthermore, a multilayer printed wiring board can be produced by using the resin-coated metal foil of this embodiment to pattern the metal foil to form a circuit, laminating resin layers containing such circuits with the circuit orientation aligned, and applying heat and pressure to further cure the semi-cured product, thereby producing a resin layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A) as an insulating layer. The resin layer in the resin-coated metal foil of this embodiment and the printed wiring board (resin layer in the printed wiring board) obtained using the resin-coated metal foil have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0170] Examples of the metal foil include copper foil. In a resin-coated metal foil, when metal foils are provided on both sides of a resin layer, these metal foils may be the same or different. In this specification, not limited to the case of a resin-coated metal foil, the term "two layers of metal foils are different from each other" means that at least one of the material and thickness of the two layers of metal foil is different from each other.

[0171] The resin-coated metal foil of this embodiment can be produced in the same manner as the resin-coated film, except that the metal foil is used instead of the support film.

[0172] <Metal-clad laminate> The metal-clad laminate of this embodiment comprises an insulating layer containing a cured product of the vinyl compound (A), a cured product of the vinyl composition (A), or a cured product of the prepreg (A), and a metal foil. More specifically, the metal-clad laminate of this embodiment may comprise, for example, the insulating layer and the metal foil provided on one or both sides of the insulating layer. The metal-clad laminate of this embodiment can be made into a printed wiring board by, for example, patterning the metal foil therein to form a conductor wiring (circuit). Furthermore, a multilayer printed wiring board can be made by stacking multiple such printed wiring boards via a separately prepared insulating layer and applying heat and pressure. The insulating layer in the metal-clad laminate of this embodiment and the printed wiring board obtained using the metal-clad laminate (the insulating layer in the printed wiring board) have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0173] The metal foil provided in the metal-clad laminate of this embodiment is the same as the metal foil provided in the resin-coated metal foil described above. In the metal-clad laminate, when metal foils are provided on both sides of the insulating layer, these metal foils may be the same as or different from each other.

[0174] The insulating layer used separately when laminating the printed wiring board may be a known layer, the resin layer in the resin-coated film described above, the laminate sheet which is a laminate of a plurality of the resin layers, the prepreg (A) described above, or the laminate obtained by overlapping a plurality of prepregs (A). Alternatively, the insulating layer may be a resin layer, a laminate sheet, a prepreg (A), or a laminate obtained by further curing the vinyl compound (A) or the vinyl composition (A) in the resin layer, the laminate sheet, the prepreg (A), or the laminate.

[0175] The metal-clad laminate of this embodiment can be produced, for example, by laminating a metal foil on one or both sides of a prepreg (A), and then heating and pressing the resulting laminate to further cure the vinyl compound (A) or a semi-cured product thereof, or the vinyl composition (A) or a semi-cured product thereof, in the prepreg (A) to form a cured product, and fusing the prepreg (A) and the metal foil. The metal-clad laminate of this embodiment may also be produced, for example, by producing a prepreg (A) using the vinyl compound (A) or the vinyl composition (A) by the method described above, and then using this prepreg (A) to produce the prepreg (A) by the method described above. The metal-clad laminate of this embodiment can also be produced, for example, by heating the resin-coated metal foil described above to further cure the vinyl compound (A) or a semi-cured product thereof, or the vinyl composition (A) or a semi-cured product thereof, in the resin layer, to form an insulating layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A).

[0176] <Printed Wiring Board> The printed wiring board of this embodiment comprises an insulating layer containing a cured product of the vinyl compound (A), a cured product of the vinyl composition (A), or a cured product of the prepreg (A), and conductor wiring. More specifically, the printed wiring board of this embodiment may be, for example, a printed wiring board comprising the insulating layer and the conductor wiring provided on one or both sides of the insulating layer. A multilayer printed wiring board can be formed by stacking multiple printed wiring boards of this embodiment via a separately prepared insulating layer and applying pressure while heating. The printed wiring board of this embodiment (the insulating layer in the printed wiring board) has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0177] The material of the conductor wiring is the same as the metal of the metal foil provided in the metal-clad laminate described above. The insulating layer used separately when laminating the printed wiring board of this embodiment is the insulating layer described above. In the printed wiring board, when conductor wiring is provided on both sides of the insulating layer, the material and thickness of these conductor wirings may be the same as or different from each other.

[0178] The printed wiring board of this embodiment can be produced, for example, by patterning the metal foil in the above-mentioned metal-clad laminate to form conductor wiring (circuits). The printed wiring board of this embodiment can also be produced, for example, by heating the above-mentioned resin-coated metal foil to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product, in the resin layer to form an insulating layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A), and then patterning the metal foil to form conductor wiring (circuits). The metal foil can be patterned by a known method such as etching.

[0179] Fig. 1 is a cross-sectional view schematically illustrating an example of a laminate structure of the present embodiment obtained using a vinyl compound (A). In the drawings used in the following description, for the sake of convenience, essential parts may be shown enlarged in order to make the features of the present invention easier to understand, and the dimensional ratios of each component may not necessarily be the same as those in reality.

[0180] The laminate structure 1 shown here is configured to include a first layer 11 and a second layer 12 provided on one surface 11a of the first layer 11. The first layer 11 is a layer obtained using a vinyl compound (A). The second layer 12 is selected depending on the type of laminate structure 1. Both the first layer 11 and the second layer 12 are in the form of a film or a sheet. The second layer 12 may be provided over the entire surface 11a of the first layer 11, or may be provided in a partial region.

[0181] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a support film, the laminate structure 1 is a resin-coated film. When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a metal foil, the laminate structure 1 is a resin-coated metal foil. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 is a metal foil, the laminate structure 1 is a metal-clad laminate.

[0182] Fig. 2 is a cross-sectional view schematically showing another example of the laminate structure of the present embodiment obtained using the vinyl compound (A). In Fig. 2 and subsequent figures, the same components as those shown in the figures already described are denoted by the same reference numerals as in the figures already described, and detailed description thereof will be omitted.

[0183] The laminate structure 2 shown here is configured to include a first layer 11 and a second layer 22 provided on one surface 11a of the first layer 11. The second layer 22 is linear, and in FIG. 2, the cross section of the laminate structure 2 is formed to include a cross section along the linear length direction of the second layer 22. The number of linear second layers 22 may be one or may be two or more. The laminate structure 2 is the same as the laminate structure 1 shown in FIG. 1 except that the laminate structure 2 includes a linear second layer 22 instead of the film-like second layer 12. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 22 is a conductor wiring, the laminate structure 2 is a printed wiring board.

[0184] Both the laminate structure 1 and the laminate structure 2 shown in Figures 1 and 2 have nothing on the other surface 11b of the first layer 11, but may have a layer similar to the second layer 12 or the second layer 22.

[0185] FIG. 3 is a cross-sectional view schematically illustrating another example of a laminate structure according to this embodiment obtained using a vinyl compound (A). The laminate structure 3 shown here includes a first layer 11, a second layer 12 provided on one surface 11a of the first layer 11, and a third layer 13 provided on the other surface 11b of the first layer 11. The third layer 13 is film- or sheet-shaped and, like the second layer 12, is selected depending on the type of laminate structure 1. The arrangement of the third layer 13 on the other surface 11b of the first layer 11 is similar to the arrangement of the second layer 12 on the one surface 11a of the first layer 11. The composition, shape, thickness, and size of the third layer 13 may be the same as or different from the composition, shape, thickness, and size of the second layer 12. For example, the third layer 13 may be provided over the entire area of ​​the other surface 11b of the first layer 11, or may be provided in a partial region.

[0186] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are support films, the laminate structure 3 is a resin-coated film. When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are metal foils, the laminate structure 3 is a resin-coated metal foil. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 and the third layer 13 are metal foils, the laminate structure 3 is a metal-clad laminate.

[0187] FIG. 4 is a cross-sectional view schematically illustrating another example of a laminate structure according to this embodiment, obtained using a vinyl compound (A). The laminate structure 4 shown here includes a first layer 11, a second layer 22 provided on one surface 11a of the first layer 11, and a third layer 23 provided on the other surface 11b of the first layer 11. The third layer 23 is linear, and in FIG. 4 , the cross section of the laminate structure 4 includes both a cross section along the linear length of the second layer 22 and a cross section along the linear length of the third layer 23. The arrangement of the third layer 23 on the other surface 11b of the first layer 11 is similar to the arrangement of the second layer 22 on one surface 11a of the first layer 11. The composition, length, thickness, and number of the third layer 23 may be the same as or different from the composition, length, thickness, and number of the second layer 22. For example, the number of linear third layers 23 may be 1 or 2 or more. When the first layer 11 is an insulating layer containing a cured product of the vinyl compound (A), a cured product of the vinyl composition (A), or a cured product of the prepreg (A), and the second layer 22 and the third layer 23 are conductor wirings, the laminate structure 4 is a printed wiring board.

[0188] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the following examples, "room temperature" refers to a temperature range of 15 to 40°C.

[0189] The conditions for measuring the melting point of a vinyl compound are as follows. An aluminum pan filled with a vinyl compound was heated under the following conditions using a temperature-modulated differential scanning calorimeter (Discovery DSC250 manufactured by TA Instruments), and the endothermic peak temperature in the reversing heat flow was taken as the melting point. When there were multiple endothermic peaks, the endothermic peak temperature on the lower side was taken as the melting point. Heating conditions: held at 40°C for 5 minutes, heated to 300°C at a rate of 3°C / min, and then held at 300°C for 5 minutes. Modulation period: 60 seconds. Modulation amplitude: 1.0°C.

[0190] The test conditions for the cured product are as follows: (1) Thermal diffusivity: Measurement was performed at room temperature by the TWA method using a thermal diffusivity measuring device "ai-phase mobile" (manufactured by ai-phase Co., Ltd.).

[0191] Example 1 Synthesis of Compound 1 A 500 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer was charged with 33.5 g of methyl 4-hydroxybenzoate, 30.4 g of potassium carbonate, 3.3 g of sodium iodide, 0.3 g of 2,6-di(tert-butyl)-p-cresol, 38.0 g of vinylbenzyl chloride (a mixture of m,p positional isomers), and 220 mL of methanol, and the mixture was reacted at an internal temperature of about 60° C. for 7 hours.

[0192] After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate and water, adjusted to pH 3 with 1N aqueous hydrochloric acid, and then extracted with ethyl acetate. The resulting solution was concentrated, and then 0.1 g of 2,6-di(tert-butyl)-p-cresol, 100 mL of methanol, 100 mL of water, 50 mL of THF, and 17.6 g of sodium hydroxide were added and reacted at 50°C for 4 hours. The reaction solution was concentrated, and the organic solvent was distilled off. Then, 1N aqueous HCl solution was added to the resulting aqueous layer to adjust the pH to 1, and the mixture was filtered. The resulting solid was washed with water and then dried under reduced pressure, yielding 28.9 g of Compound 1 below.

[0193]

[0194] (Synthesis of Compound 2) 101.2 g of hydroquinone, 38.11 g of potassium carbonate, 2.8 g of sodium iodide, 300 mL of N,N-dimethylformamide, and 25.0 g of 1,8-dibromooctane were placed in a 1 L four-neck flask equipped with a thermometer and a stirrer, and the mixture was reacted at an internal temperature of approximately 60°C for 8 hours. After completion of the reaction, the mixture was cooled to room temperature, and 100 mL of water was added. The mixture was filtered and washed with water. The obtained solid was dried under reduced pressure, yielding 25.5 g of Compound 2 below.

[0195]

[0196] (Synthesis of Compound 3) A 300 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer was charged with 8.9 g of compound 1, 4.6 g of compound 2, 0.1 g of N,N-dimethylaminopyridine, 10.0 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and 75 mL of N,N-dimethylformamide, and the mixture was reacted at room temperature for 23 hours, and then at an internal temperature of approximately 50°C for 8 hours. After completion of the reaction, the mixture was cooled to room temperature, and 180 mL of water was added. The precipitated solid was collected by filtration and washed with water. Methanol, 2,6-di(tert-butyl)-p-cresol, and water were added to the obtained solid, and the mixture was stirred at room temperature for 1 hour and then filtered. The obtained solid was washed with methanol and then dried under reduced pressure, yielding 3.6 g of the following compound 3.

[0197]

[0198] (Synthesis of Vinyl Compound 1) A 300 mL four-neck flask equipped with a thermometer and a stirrer was charged with 3.6 g of Compound 3, 7.3 g of Compound 1, 0.4 g of N,N-dimethylaminopyridine, 5.1 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 0.1 g of 2,6-di(tert-butyl)-p-cresol, and 155 mL of dehydrated THF, and the mixture was reacted for 27 hours at an internal temperature of 40° C. After completion of the reaction, 50 mL of water was charged, and the precipitated solid was collected by filtration, washed with water and methanol, and then dried under reduced pressure to obtain 2.2 g of the following vinyl compound 1.

[0199]

[0200] Example 2 Synthesis of Compound 4 A 300 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer was charged with 2.9 g of 1,8-octanediol, 12.1 g of methyl 6-hydroxy-2-naphthoate, 0.3 g of dibutyltin oxide, and 150 mL of p-chlorotoluene, and the mixture was reacted for 28 hours at an internal temperature of about 170° C. After completion of the reaction, the mixture was cooled to room temperature, methanol and water were added, and the mixture was filtered. The resulting solid was washed with toluene and then dried under reduced pressure, yielding 12.5 g of Compound 4 below.

[0201]

[0202] (Synthesis of Vinyl Compound 2) 4.9 g of compound 4, 6.9 g of potassium carbonate, 0.3 g of sodium iodide, 0.05 g of 2,6-di(tert-butyl)-p-cresol, 65 mL of N,N-dimethylformamide, and 4.9 g of vinylbenzyl chloride (a mixture of m,p positional isomers) were placed in a 200 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, and the mixture was allowed to react at an internal temperature of approximately 60°C for 9 hours. After completion of the reaction, the mixture was cooled to room temperature, and 40 mL of heptane and 40 mL of water were added. The precipitated solid was collected by filtration and washed with water, heptane, and methanol. The resulting solid was dissolved in toluene, filtered, and then washed with water. Methanol was added to the resulting toluene solution, and the precipitated solid was collected by filtration, washed with methanol, and then dried under reduced pressure to obtain 2.2 g of vinyl compound 2 below.

[0203]

[0204] Example 3 Synthesis of Compound 5 A 300 mL four-neck flask equipped with a thermometer and a stirrer was charged with 15.9 g of 4-(trans-4-hydroxycyclohexyl)phenol, 15.6 g of potassium carbonate, 1.2 g of sodium iodide, 100 mL of N,N-dimethylformamide, and 10.2 g of 1,8-dibromooctane, and the mixture was allowed to react at an internal temperature of approximately 60°C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, and 100 mL of water was added. The precipitated solid was collected by filtration, washed with water and methanol, and dried under reduced pressure to obtain 13.4 g of the following compound 5.

[0205]

[0206] (Synthesis of Compound 6) 4.0 g of compound 5, 1.7 g of sodium hydride, 100 mL of dehydrated THF, and 20 mL of dehydrated N,N-dimethylformamide were charged into a 300 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, and the mixture was allowed to react for 20 minutes at an internal temperature of approximately 0°C. Then, 7.8 g of p-vinylbenzyl chloride, 10 mL of dehydrated N,N-dimethylformamide, 0.3 g of sodium iodide, and 0.01 g of 2,6-di(tert-butyl)-p-cresol were charged, and the mixture was allowed to react for 23 hours at an internal temperature of approximately 60°C. After completion of the reaction, the mixture was cooled to 0°C, and 50 mL of water and 50 mL of heptane were charged. The precipitated solid was collected by filtration and washed with water, heptane, and methanol. The resulting solid was dissolved in toluene, filtered, and then washed with water to obtain the following compound 6.

[0207]

[0208] (Synthesis of vinyl compound 3) A 200 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer was charged with 3.8 g of vinyl compound 6, 1.7 g of sodium hydride, 0.2 g of sodium iodide, 0.01 g of 2,6-di(tert-butyl)-p-cresol, 100 mL of dehydrated THF, and 100 mL of dehydrated N,N-dimethylformamide. The mixture was allowed to react for 30 minutes at an internal temperature of approximately 0°C, and then 9.3 g of p-vinylbenzyl chloride was added and the mixture was allowed to react for 12 hours at an internal temperature of approximately 70°C. After completion of the reaction, the mixture was cooled to 0°C, and 50 mL of water and 100 mL of heptane were added. The precipitated solid was collected by filtration and washed with water, heptane, and methanol. The resulting solid was dissolved in toluene and washed with water. The solvent was concentrated under reduced pressure, and then washed with methanol. The resulting solid was dried under reduced pressure to obtain 1.4 g of vinyl compound 3 shown below.

[0209]

[0210] Example 4 Synthesis of Vinyl Composition 1 A 200 mL four-neck flask equipped with a thermometer and a stirrer was charged with 1.1 g of hydroquinone, 4.0 g of 1,3-dibromopropane, 20.7 g of potassium carbonate, 0.9 g of sodium iodide, 0.1 g of 2,6-di(tert-butyl)-p-cresol, and 120 mL of N,N-dimethylformamide, and the mixture was allowed to react for 5 hours at an internal temperature of approximately 60°C. 9.4 g of 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate was then added, and the mixture was allowed to react for 5 hours at an internal temperature of approximately 60°C. The mixture was then cooled to an internal temperature of approximately 5°C, and 2.0 g of methacryloyl chloride was added, and the mixture was allowed to react for 3 hours at an internal temperature of approximately 60°C. 13.7 g of vinylbenzyl chloride (a mixture of m,p positional isomers) was then added, and the mixture was allowed to react for 9 hours at an internal temperature of approximately 60°C. After completion of the reaction, the mixture was cooled to room temperature, and 180 mL of water was added. The precipitated solid was collected by filtration, washed with water and n-heptane, and dried under reduced pressure to obtain 15.1 g of crude product 1. 60 mL of toluene was added to the obtained crude product 1, and the insoluble components were filtered off. Methanol was further added, and the precipitated solid was filtered off. 2,6-di(tert-butyl)-p-cresol was added to the obtained filtrate, and the solution was concentrated under reduced pressure. The obtained solid was washed with methanol to obtain 5.7 g of vinyl composition 1 containing the following two types of vinyl compound (A) and vinyl compound (B).

[0211] (In the formula, m1 and m2 are the same or different and each represent an integer of 1 to 5.)

[0212] Comparative Example 1 Synthesis of Vinyl Compound 4 A 200 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer was charged with 6.0 g of 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl, 0.06 g of 2,6-di(tert-butyl)-p-cresol, 12 g of potassium carbonate, 1.3 g of sodium iodide, 34 mL of N,N-dimethylformamide, and 10 g of 4-vinylbenzyl chloride, and the mixture was allowed to react at an internal temperature of approximately 60°C for 3 hours. After completion of the reaction, 121 g of toluene and 34 mL of water were added, stirred, and filtered to remove insoluble matter. The resulting solution was separated and washed three times with water. The resulting solution was filtered to remove insoluble matter, and the toluene was then removed under reduced pressure. 56 mL of methanol and 0.07 g of 2,6-di(tert-butyl)-p-cresol were added to the resulting solid, and the mixture was stirred at room temperature. The solid in the suspension was collected by filtration and dried under reduced pressure to obtain 9.4 g of vinyl compound 4 below.

[0213]

[0214] The melting points of vinyl compounds 1 to 4 and vinyl composition 1 are shown in Table 1.

[0215]

[0216] In Examples 5 to 7 and Comparative Example 2, vinyl compounds 1 to 4 obtained in Examples 1 to 3 and Comparative Example 1, respectively, were placed in the hollow plate-shaped portion of a mold, heated under reduced pressure at the primary curing temperature shown in Table 2 for 1 hour, and then heated at 180°C for 2 hours while applying a pressure of 1.5 MPa, thereby obtaining cured products.

[0217] In Example 8, the vinyl composition 1 (100 parts by mass) obtained in Example 7 and dicumyl peroxide (0.4 parts by mass) were mixed in THF, and the resulting solution was placed on a PET film and dried for 10 minutes at 65° C. The resulting solid was placed in the hollow plate of a mold and heated under reduced pressure at the primary curing temperature shown in Table 2 for 1 hour, and then heated at 180° C. for 2 hours while applying a pressure of 1.5 MPa, to obtain a cured product.

[0218] The thermal diffusivity values ​​of the cured products are shown in Table 2.

[0219]

[0220] The present invention can be used for printed wiring boards in communication devices, and is particularly suitable for use in printed wiring boards in which the communication devices handle large amounts of data and are expected to generate a large amount of heat.

[0221] 1, 2, 3, 4...Laminated structure 11...First layer 11a...One surface of the first layer 11b...Other surface of the first layer 12, 22...Second layer 13, 23...Third layer

Claims

1. A vinyl compound represented by formula (A): (In the above formula (A), P １ and P ２ one of the above is a vinylbenzyl group, and the other is an acryloyl group, a methacryloyl group, or a vinylbenzyl group; W is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, or any of the groups represented by Group B; [Group B] [In the formula of the above group B, * represents Y １ Or Y ２ represents a bonding position with, n1 represents an integer of 1 to 10, n2 to n5 are each the same or different and represent 0 or 1, n6 to n7 are each the same or different and represent an integer of 0 to 4, n8 to n9 are each the same or different and represent an integer of 0 to 3, n10 to n11 are each the same or different and represent an integer of 0 to 4, n12 represents 0 or 1, R is an alkyl group or aryl group having 1 to 20 carbon atoms, and a plurality of R may be the same or different from each other, S is a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, some of the carbon atoms of which may be substituted with oxygen atoms, and a plurality of S may be the same or different from each other.] m represents an integer of 1 to 5, Y １ and Y ２ are the same or different and each is an oxygen atom, an ester bond, or a carbonyl bond; Q １ and Q. ２ are the same or different and are groups represented by any one of formulas (1) to (4). [In the above formulas (1) to (4), A １ , A ２ , A ３ and A ４ are each the same or different and are a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkylene group, a substituted or unsubstituted divalent cycloalkenylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by a single bond, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together via a single bond, １ , X ２ and X ３ are the same or different and each is an ester bond or a carbonyl group, and when Q is a group represented by formula (1), A １ represents a substituted or unsubstituted divalent fused ring group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by single bonds, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups are linked by single bonds, a divalent group in which two or more substituted or unsubstituted divalent cycloalkenylene groups are linked by single bonds, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene groups are linked by single bonds, a divalent group in which one or more substituted or unsubstituted divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by single bonds, a divalent group in which one or more substituted or unsubstituted divalent cycloalkylene groups and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked by single bonds, or is a divalent group in which one or more substituted or unsubstituted divalent aromatic groups, one or more substituted or unsubstituted divalent cycloalkylene groups, and one or more substituted or unsubstituted divalent cycloalkenylene groups are linked together by a single bond.

2. The vinyl compound according to claim 1, wherein m is an integer of 2 to 5.

3. The vinyl compound according to claim 1, wherein m is 1.

4. P. １ and P ２ and each of the above is a vinylbenzyl group.

5. The above X １ , X ２ and X ３ The vinyl compound according to claim 1, wherein is an ester bond.

6. The vinyl compound according to claim 1, which is used in a printed wiring board.

7. A vinyl composition comprising the vinyl compound according to claim 1.

8. The vinyl composition according to claim 7, further comprising a vinyl compound represented by formula (B): (In the above formula (B), P ３ and P ４ each represents an acryloyl group, a methacryloyl group, a vinylbenzyl group, or a 5-hexenyl group; ３ is a group represented by any one of formulas (5) to (8). [In the formulas (5) to (8), A ５ , A ６ , A ７ and A ８ are each the same or different and are a substituted or unsubstituted divalent aromatic group (excluding hydroxyl-containing aromatic groups), a substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl-containing cycloalkylene groups), a divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding hydroxyl-containing aromatic groups) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxyl-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one or more substituted or unsubstituted divalent aromatic groups (excluding hydroxyl-containing aromatic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxyl-containing cycloalkylene groups) are linked by a single bond; ４ , X ５ and X ６ are the same or different and each is an ester bond or a carbonyl group; P ３ and P ４ are both vinylbenzyl groups, and Q ３ is a group represented by formula (5), A ５ represents a divalent group in which two substituted or unsubstituted divalent cycloalkylene groups (excluding hydroxyl-containing cycloalkylene groups) are linked by a single bond, or a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl-containing cycloalkylene groups) are linked by a single bond, P ３ and P ４ When both are acryloyl groups or methacryloyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６ one of the above is a substituted or unsubstituted divalent aromatic group (excluding hydroxyl-containing aromatic groups), and the other is a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl-containing cycloalkylene groups) are linked by a single bond, ３ and P ４ When both are 5-hexenyl groups, Q ３ is a group represented by formula (6), and A ５ and A ６ one of the above is a substituted or unsubstituted divalent aromatic group, and the other is a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding hydroxyl group-containing aromatic groups) and one substituted or unsubstituted divalent cycloalkylene group (excluding hydroxyl group-containing cycloalkylene groups) are linked by a single bond.

9. A vinyl resin cured product obtained by curing the vinyl compound according to any one of claims 1 to 6, or the vinyl composition according to claim 7 or 8.

10. A prepreg comprising the vinyl compound or semi-cured product thereof according to any one of claims 1 to 6, or the vinyl composition or semi-cured product thereof according to claim 7 or 8, and a fibrous base material.

11. A resin-attached film comprising a resin layer containing the vinyl compound or semi-cured product thereof according to any one of claims 1 to 6, or the vinyl composition or semi-cured product thereof according to claim 7 or 8, and a support film.

12. A resin-coated metal foil comprising a resin layer containing the vinyl compound or semi-cured product thereof according to any one of claims 1 to 6, or the vinyl composition or semi-cured product thereof according to claim 7 or 8, and a metal foil.

13. A metal-clad laminate comprising an insulating layer comprising a cured product of the vinyl compound according to any one of claims 1 to 6, or a cured product of the vinyl composition according to claim 7 or 8, and a metal foil.

14. A metal-clad laminate comprising an insulating layer containing the cured product of the prepreg according to claim 10 and a metal foil.

15. A printed wiring board comprising an insulating layer containing a cured product of the vinyl compound according to any one of claims 1 to 6, or a cured product of the vinyl composition according to claim 7 or 8, and a conductor wiring.

16. A printed wiring board comprising an insulating layer containing the cured product of the prepreg according to claim 10 and a conductor wiring.

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