WO2024085082A1

WO2024085082A1 - Vinyl compound, vinyl composition, vinyl resin cured product, prepreg, resin-attached film, resin-attached metal foil, metal-clad laminate, and printed wiring board

Info

Publication number: WO2024085082A1
Application number: PCT/JP2023/037192
Authority: WO
Inventors: 七瀬佐久川; 大貴田中
Original assignee: 住友化学株式会社
Priority date: 2022-10-19
Filing date: 2023-10-13
Publication date: 2024-04-25
Also published as: JP2024060593A

Abstract

The present invention addresses the problem of providing a novel compound that can be used as a constituent material for printed wiring boards, has a low melting point and high solubility, and can be cured to provide a resin having high thermal conductivity and low dielectric loss.　The present invention pertains to a vinyl compound represented by formula (1) or (2). (R is a (meth)acryloyl group or a vinylbenzyl group; A¹ is a chain-like saturated aliphatic hydrocarbon group, or a group containing at least one selected from the group consisting of an aromatic group and a cycloalkane group; A² is a group containing at least one selected from the group consisting of an aromatic group, a cycloalkane group, and a cycloalkene group; X¹ is a single bond, an ester group, a carbonyl group, or an ether group; m is an integer of 3-6; and n is an integer of 1-20.)

Description

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

The present invention relates to vinyl compounds, vinyl compositions, vinyl resin cured products, prepregs, resin-coated films, resin-coated metal foils, metal-clad laminates, and printed wiring boards.

The amount of data handled by communications devices and the communication speeds are increasing year by year, and as a result, there has been active research into high-speed communications technology to improve signal transmission speeds. When communications devices handle a large amount of data, the amount of heat generated by the electronic computing components in the devices increases, and if this heat accumulates in the printed wiring board, it can cause malfunctions. For this reason, printed wiring boards are required to have high heat dissipation properties.

A well-known example of a printed wiring board with high heat dissipation properties is the so-called thick copper board, which is made by making the copper (i.e. the copper pattern) that forms the circuit thicker than before, allowing more heat to be dissipated through the copper. However, this thick copper board has the problem that it is not suitable for communication devices, which require compactness and light weight, because it is thick overall.

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

On the other hand, like printed wiring boards, materials that contain resin as the main component and have high heat dissipation properties are known to contain a highly thermally conductive filler. However, materials that contain filler have poor processability, which is an issue in that they are not suitable for manufacturing printed wiring boards.

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 high heat dissipation properties as well as low dielectric loss, and the resin disclosed in Patent Document 1 itself has thermal conductivity and low dielectric loss.

US Patent Application Publication No. 2019/0194408

However, the thermal conductivity of the resin disclosed in Patent Document 1 is not sufficient, and there is room for improvement. In addition, when manufacturing heat dissipation components such as printed wiring boards, it is desirable for the monomer compound, which is the raw material for the resin, to have good processability, so it is also required that the resin have a low melting point and high solubility in organic solvents used for processing.

An object of the present invention is to provide a novel compound which can be used as a constituent material for printed wiring boards and which exhibits a low melting point and high solubility.
Another object of the present invention is to provide a composition containing the novel compound, which is capable of giving a cured product having high thermal conductivity.

The present invention employs the following configuration.
[1] A vinyl compound represented by formula (1) or formula (2):

(Wherein,
R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and a plurality of R may be the same or different from each other;
A ¹ is a substituted or unsubstituted m-valent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted m-valent cycloalkane group, an m-valent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocyclic rings) are linked by a single bond, an m-valent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, an m-valent group 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, a substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group, a group represented by R ¹ (OR ² -*) ₃ , a group represented by R ¹ (R ² -*) ₃ , a group represented by R ³ C(OR ² -*) ₃ , or a group represented by R ³ C(R ² -*) ₃ ;
R ¹ is a substituted or unsubstituted trivalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups);
R ² is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, a group represented by **-R ⁴ (R ⁵ ) _p R ⁴ -*, or a group represented by **-(R ⁶ O) _q R ⁶ -*, and multiple R ² may be the same or different from each other;
^R3 is a hydrogen atom or a methyl group;
^R4 is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, and multiple ^R4s may be the same or different from each other.
^R5 is a substituted or unsubstituted divalent aromatic group (excluding a nitrogen-containing aromatic heterocyclic group), and when p is 2 or 3, multiple ^R5s may be the same or different from each other;
R ⁶ is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, and multiple R ^6s may be the same or different from each other;
p is an integer from 1 to 3;
q is an integer from 1 to 3;
* is the bonding position to ^X1 ,
** represents the bonding position to the oxygen atom bonded to R ¹ , the bonding position to R ¹ , the bonding position to the oxygen atom bonded to R ³ C, or the bonding position to R ³ C.
^A2 represents a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles), one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group represented by *-B ¹ Y ¹ B ² -**, a group represented by *-B ¹ Y ¹ B ² Y ² B ³ -**, or ^a group represented by *-B ¹ Y ¹ B ² Y ² B ³ Y ³ B ⁴ -**,
B ¹ to B ⁴ each represent a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, one or more substituted or unsubstituted aromatic rings and one or more a divalent group 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, a divalent group 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, or a divalent group 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,
Y ¹ to Y ³ each represent an ester group, a carbonyl group, or an ether group;
* is the bonding position to ^X1 ,
** represents the bonding position to the acryloyloxy group, methacryloyloxy group, or vinylbenzyloxy group in formula (1), or the bonding position to the acryloyloxyalkoxy group, methacryloyloxyalkoxy group, or vinylbenzyloxyalkoxy group in formula (2),
X ¹ is a single bond, an ester group, a carbonyl group, or an ether group, and a plurality of X ¹ may be the same or different from each other;
m is an integer from 3 to 6,
n is an integer from 1 to 20, and multiple n's may be the same or different.
[2] A ¹ and A ² are groups having 14 or less carbon atoms (however, the number of carbon atoms does not include the number of carbon atoms of a substituent), The vinyl compound according to [1].
[3] The vinyl compound according to [1] or [2], which is used for a printed wiring board.
[4] A vinyl composition comprising the vinyl compound according to any one of [1] to [3].
[5] A vinyl resin cured product obtained by curing the vinyl compound according to any one of [1] to [3] or the vinyl composition according to [4].
[6] A prepreg comprising the vinyl compound or semi-cured product thereof according to any one of [1] to [3], or the vinyl composition or semi-cured product thereof according to [4], and a fibrous base material.
[7] A resin-attached film comprising a resin layer containing the vinyl compound or semi-cured product thereof according to any one of [1] to [3], or the vinyl composition or semi-cured product thereof according to [4], and a support film.
[8] A resin-coated metal foil comprising a resin layer containing the vinyl compound or semi-cured product thereof according to any one of [1] to [3], or the vinyl composition or semi-cured product thereof according to [4], and a metal foil.
[9] A metal-clad laminate comprising an insulating layer containing a cured product of the vinyl compound according to any one of [1] to [3] or a cured product of the vinyl composition according to [4], and a metal foil.
[10] A metal-clad laminate comprising an insulating layer containing a cured product of the prepreg according to [6] and a metal foil.
[11] A printed wiring board comprising an insulating layer containing a cured product of the vinyl compound according to any one of [1] to [3] or a cured product of the vinyl composition according to [4], and a conductor wiring.
[12] A printed wiring board comprising an insulating layer containing a cured product of the prepreg according to [6] and a conductor wiring.

According to the present invention, it is possible to provide a novel compound which can be used as a constituent material for printed wiring boards and which exhibits a low melting point and high solubility.
It is also possible to provide a composition that contains the novel compound and that can give a cured product with high thermal conductivity.

FIG. 1 is a cross-sectional view showing a schematic example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. FIG. 2 is a cross-sectional view showing a schematic diagram of another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. FIG. 2 is a cross-sectional view showing a schematic diagram of still another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. FIG. 2 is a cross-sectional view showing a schematic diagram of still another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention.

The following describes in detail a preferred embodiment of the present invention.

<<Vinyl compounds>>
The vinyl compound of the present embodiment is represented by formula (1) or formula (2).

In formula (1) and formula (2), R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and multiple Rs may be the same or different.

In formula (1) and formula (2), of the m R's, it is preferable that at least one is a vinylbenzyl group, more preferably m-1 is a vinylbenzyl group, and even more preferably all m are vinylbenzyl groups.

The vinylbenzyl group represented by R is an o-vinylbenzyl group, an m-vinylbenzyl group, or a p-methylbenzyl group, preferably an m-vinylbenzyl group or a p-methylbenzyl group, and more preferably an m-vinylbenzyl group from the viewpoint of lowering the melting point of the vinyl compound. Note that the positions of the vinyl groups of the m vinylbenzyl groups in formula (1) or formula (2) may be the same or different.

In formula (1) and formula (2), A ¹ is a substituted or unsubstituted m-valent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted m-valent cycloalkane group, an m-valent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocyclic rings) are linked by single bonds, an m-valent group in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds, an m-valent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are linked by single bonds, a substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group, a group represented by R ¹ (OR ² -*) ₃ , a group represented by R ¹ (R ² -*) ₃ , a group represented by R ³ C(OR ² -*) ₃ , or a group represented by R ³ C(R ² -*) ₃ .

The substituted or unsubstituted m-valent aromatic group represented by A ¹ is a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted aromatic ring.

In this specification, the aromatic ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring. When the aromatic ring is a heterocyclic ring, the heteroatom contained in the heterocyclic ring may be a heteroatom other than a nitrogen atom, such as an oxygen atom or a sulfur atom. From the viewpoint of suppressing dielectric loss or reducing the dielectric tangent, it is preferable that the aromatic ring does not contain a heteroatom.

The substituted or unsubstituted m-valent aromatic group represented by ^A1 is preferably a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted monocyclic or fused ring aromatic ring, and more preferably a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted monocyclic aromatic ring.

The number of carbon atoms in the unsubstituted m-valent aromatic group represented by ^A1 is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and further preferably 6 to 14. The number of carbon atoms in the unsubstituted aromatic ring is synonymous with the number of carbon atoms in the unsubstituted m-valent aromatic group, and the preferred embodiments thereof are also the same.

Specific examples of unsubstituted aromatic rings include benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene, with benzene being preferred.

When the m-valent aromatic group represented by ^A1 has a substituent, that is, when the aromatic ring has a substituent, the substituent is preferably a substituent other than a hydroxy group, and is, 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.

The alkyl group having 1 to 20 carbon atoms may be a known alkyl group. Specific examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-icosyl. 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 carbon numbers among the specific examples described above.

The alkoxy group having 1 to 20 carbon atoms may be a known alkoxy group. Specific examples of alkoxy groups having 1 to 20 carbon atoms include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, sec-butoxy, tert-butoxy, isobutyloxy, n-pentyloxy, neopentyloxy, n-hexyloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-dodecyloxy, n-tetradecyloxy, n-hexadecyloxy, n-octadecyloxy, and n-icosyloxy. 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 carbon numbers among the specific examples described above.

Specific preferred examples of the unsubstituted m-valent aromatic group represented by ^A1 include the following groups (* indicates the bonding position to ^X1 ).

The substituted or unsubstituted m-valent cycloalkane group represented by A ¹ is a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted cycloalkane ring.

In this specification, the cycloalkane ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring. When the cycloalkane ring is a heterocyclic ring, examples of the heteroatom contained in the heterocyclic ring include an oxygen atom, a nitrogen atom, and a sulfur atom. From the viewpoint of suppressing dielectric loss or reducing dielectric tangent, it is preferable that the cycloalkane ring does not contain a heteroatom. The cycloalkane ring is preferably a monocyclic ring or a condensed ring, and more preferably a monocyclic ring.
In addition, in this specification, the cycloalkane group and the cycloalkane ring may be in a cis form, a trans form, or a mixture thereof, and in the case of a mixture, it is preferable that the proportion of the trans form is higher.

The number of carbon atoms in the unsubstituted m-valent cycloalkane group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14. The number of carbon atoms in the unsubstituted cycloalkane ring is synonymous with the number of carbon atoms in the unsubstituted m-valent cycloalkane group, and the preferred embodiments are the same.

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

When the m-valent cycloalkane group represented by ^A1 has a substituent, that is, when the cycloalkane ring has a substituent, the substituent has the same meaning as the substituent that the m-valent aromatic group represented by ^A1 may have.

Preferred specific examples of the substituted or unsubstituted m-valent cycloalkane group represented by A ¹ include the following groups (* indicates the bonding position to X ¹ ).

The m-valent group represented by ^A1 in which two or more substituted or unsubstituted aromatic rings are linked by single bonds is a group obtained by removing m hydrogen atoms from any position of a compound in which two or more substituted or unsubstituted aromatic rings are linked by single bonds. The substituted or unsubstituted aromatic ring linked by a single bond is the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group (i.e., a substituted or unsubstituted aromatic ring formed by binding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group), and the preferred embodiments thereof are also the same.

In a compound in which two or more substituted or unsubstituted aromatic rings 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.

Specific examples of compounds in which two or more unsubstituted aromatic rings are linked by a single bond include biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, m-quarterphenyl, and p-quarterphenyl.

The m-valent group represented by ^A1 in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds is a group obtained by removing m hydrogen atoms from any position of a compound in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds. The substituted or unsubstituted cycloalkane ring linked by a single bond has the same meaning as the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group (i.e., a substituted or unsubstituted cycloalkane ring formed by binding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group), and the preferred embodiments thereof are also the same.

In a compound in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds, the number of substituted or unsubstituted cycloalkane 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.

Specific examples of compounds in which two or more unsubstituted cycloalkane rings are linked by single bonds include cyclopropylcyclohexane, bicyclohexyl, 1,3-dicyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

The m-valent group 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, represented by A ¹ , is a group obtained by removing m hydrogen atoms 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 ring and the substituted or unsubstituted cycloalkane ring linked by a single bond are respectively the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group) and the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group (i.e., a substituted or unsubstituted cycloalkane ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group), and the preferred embodiments thereof are also the same.

In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings 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, and 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. In addition, the total number of substituted or unsubstituted aromatic rings linked by single bonds and the number of substituted or unsubstituted cycloalkane rings is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

Specific examples of compounds in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are linked by a single bond include cyclopropylbenzene, cyclopentylbenzene, cyclohexylbenzene, 1-cyclohexylnaphthalene, 2-cyclohexylnaphthalene, 2-phenyltetrahydrofuran, 1-phenyladamantane, 1,3-diphenyladamantane, 1,3,5,7-tetraphenyladamantane, 2-cyclohexylfuran, 4-phenylpiperidine, 2-cyclohexylthiophene, and 4-phenylmorpholine.

The substituted or unsubstituted, m-valent, linear saturated aliphatic hydrocarbon group represented by ^A1 is a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted linear saturated aliphatic hydrocarbon, and is preferably a group in which one hydrogen atom bonded to m different carbon atoms of a substituted or unsubstituted linear saturated aliphatic hydrocarbon has been removed from each of the carbon atoms.

In this specification, the chain-like saturated aliphatic hydrocarbon may be a straight-chain saturated aliphatic hydrocarbon or a branched saturated aliphatic hydrocarbon.

The substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group represented by A ¹ is preferably a group in which m hydrogen atoms have been removed from any position of a substituted or unsubstituted branched aliphatic hydrocarbon.

The number of carbon atoms in the unsubstituted m-valent chain saturated aliphatic hydrocarbon group represented by ^A1 is not particularly limited, but is preferably 1 to 10, more preferably 3 to 9, and even more preferably 5 to 8.

Specific examples of the unsubstituted linear saturated aliphatic hydrocarbon represented by ^A1 include n-propane, n-butane, 2-methylpropane, n-pentane, 2-methylbutane, 2,2-dimethylpropane, n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, and 2,2,4,4-tetramethylpentane, and preferably 2,2-dimethylpropane.

When the m-valent linear saturated aliphatic hydrocarbon group represented by ^A1 has a substituent, that is, when the linear saturated aliphatic hydrocarbon has a substituent, the substituent has the same meaning as the substituent that the m-valent aromatic group represented by ^A1 may have.

Preferred specific examples of the substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group represented by A ¹ include the following groups (* indicates the bonding position to X ¹ ).

When A ¹ is a group represented by R ¹ (OR ² -*) ₃ or a group represented by R ¹ (R ² -*) ₃ , R ¹ is a substituted or unsubstituted trivalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups); R ² is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, a group represented by **-R ⁴ (R ⁵ ) _p R ⁴ -*, or a group represented by **-(R ⁶ O) _q R ⁶ -*; R ⁴ is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group; R ⁵ is a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups); R ⁶ is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group; p is an integer from 1 to 3; and q is an integer from 1 to 3. Multiple R ^2s may be the same or different from each other. Multiple R ⁴ may be the same or different from each other. When p is 2 or 3, multiple R ⁵ may be the same or different from each other. Multiple R ⁶ may be the same or different from each other. In addition, in the group represented by R ² , * is the bonding position to X ¹ ; ** is the bonding position to the oxygen atom bonded to R ¹ when A ¹ is a group represented by R ¹ (OR ² -*) ₃ , and is the bonding position to R ¹ when A ¹ is a group represented by R ¹ (R ² -*) ₃ .

The substituted or unsubstituted trivalent aromatic group represented by R ¹ is a group obtained by removing three hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. This substituted or unsubstituted aromatic ring is the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by A ¹ (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group), and the preferred embodiments thereof are also the same.

The substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group represented by ^R2 is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted linear saturated aliphatic hydrocarbon. This substituted or unsubstituted linear saturated aliphatic hydrocarbon is the same as the substituted or unsubstituted linear saturated aliphatic hydrocarbon mentioned in the description of the substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group represented by ^A1 (i.e., a substituted or unsubstituted linear saturated aliphatic hydrocarbon obtained by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group), but preferred embodiments and specific examples of the substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group represented by ^R2 are as follows.

The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R2 is preferably a group in which one hydrogen atom bonded to each of two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon has been removed from said carbon atoms, and is also preferably a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R2 is not particularly limited, but is preferably 1 to 20, more preferably 2 to 16, and even more preferably 3 to 12.

Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R2 include a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a 3-methylpentane-1,5-diyl group, a heptamethylene group, an octamethylene group, and a dodecamethylene group.

When the divalent chain saturated aliphatic hydrocarbon group represented by ^R2 has a substituent, the substituent has the same meaning as the substituent that the m-valent aromatic group represented by ^A1 may have, and preferred embodiments thereof are also the same.

When R ² is a group represented by **-R ⁴ (R ⁵ ) _p R ⁴ -*, the substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group represented by R ⁴ has the same meaning as the substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group represented by R ² , and preferred embodiments and specific examples thereof are as follows:

The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R4 is preferably a group in which one hydrogen atom bonded to each of two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon has been removed from said carbon atoms, and is also preferably a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R4 is not particularly limited, but is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1.

Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R4 include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group.

When ^R2 is a group represented by **- ^R4 ( ^R5 ) _pR4- *, ^the substituted or unsubstituted divalent aromatic group represented by ^R5 is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. The substituted or unsubstituted aromatic ring has the same meaning as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group), and the preferred embodiments thereof are also the same.

Specific preferred examples of the group represented by **-R ⁴ (R ⁵ ) _p R ⁴ -* include the following groups.

When R ² is a group represented by **-(R ⁶ O) _q R ⁶ -*, the substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by R ⁶ has the same meaning as the substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by R ² , and preferred embodiments and specific examples thereof are as follows:

The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R6 is preferably a group in which one hydrogen atom bonded to each of two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon has been removed from said carbon atoms, and is also preferably a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by R ⁶ is not particularly limited, but is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 to 2.

Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group represented by ^R6 include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group.

When R ² is a group represented by **-(R ⁶ O) _q R ⁶ -*, q is an integer of 1 to 3, and preferably 2.

Specific preferred examples of the group represented by **-(R ⁶ O) _q R ⁶ -* include **-CH ₂ CH ₂ OCH ₂ CH ₂ -*, **-(CH ₂ CH ₂ O) ₂ CH ₂ _{CH 2} -*, **-CH(CH ₃ )CH ₂ OCH(CH ₃ )CH ₂ -*, and **-(CH(CH ₃ )CH ₂ O) ₂ CH(CH ₃ )CH ₂ -*.

Specific preferred examples of the group represented by R ¹ (OR ² -*) ₃ include the following groups.

Specific preferred examples of the group represented by R ¹ (R ² -*) ₃ include the following groups.

When A ¹ is a group represented by R ³ C(OR ² -*) ₃ or R ³ C(R ² -*) ₃ , R ² has the same meaning as R ² in the group represented by R ¹ (OR ² -*) ₃ , and the preferred embodiments are also the same. However, in this case, in the group represented by R ² , * is the bonding position to X ¹ ; _** is the bonding position to the oxygen atom bonded to R ³ C when A ¹ is a group represented by R ³ C(OR ² -*) ₃ , and is the bonding position to R ³ C when A ¹ is a group represented by R ³ C(R ² -*) 3. R ³ is a hydrogen atom or a methyl group.

Preferred specific examples of the group represented by R ³ C(OR ² -*) ₃ include the following groups.

Preferred specific examples of the group represented by R ³ C(R ² -*) ₃ include the following groups.

In formula (1) and formula (2), ^A2 represents a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles), one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group represented by *-B ¹ Y ¹ B ² -**, a group represented by *-B ¹ Y ¹ B ² Y ² B ³ -**, or a group represented by *-B ¹ Y ¹ B ² Y ² B ³ Y ³ B ⁴ -**. Multiple A ² 's may be the same or different from each other. In the group represented by ^A2 , * denotes the bonding position to ^X1 ; ** denotes the bonding position to the acryloyloxy group, methacryloyloxy group, or vinylbenzyloxy group in formula (1), or the bonding position to the acryloyloxyalkoxy group, methacryloyloxyalkoxy group, or vinylbenzyloxyalkoxy group in formula (2).

^A2 preferably contains a double bond, since this increases the degree of orientation due to π-π stacking interactions, and as a result, a cured product having high thermal conductivity can be obtained. Therefore, A ² is preferably a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group 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, a divalent group 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, a divalent group 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, or a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond. From the viewpoint of ease of synthesis, ² is a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkane group, a divalent group in which two or more substituted or unsubstituted aromatic rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group 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, or a divalent group 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. and more preferably a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent cycloalkane group, a divalent group in which two substituted or unsubstituted aromatic rings are linked by a single bond, a divalent group in which two substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which one or more substituted or unsubstituted aromatic rings and one substituted or unsubstituted cycloalkane ring are linked by a single bond, or a divalent group in which two substituted or unsubstituted aromatic rings and one substituted or unsubstituted cycloalkene ring are linked by a single bond.

The substituted or unsubstituted divalent aromatic group represented by ^A2 is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. This substituted or unsubstituted aromatic ring is the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group.) and the preferred embodiments thereof are also the same. The preferred embodiments of the substituted or unsubstituted divalent aromatic group represented by ^A2 are as follows.

The substituted or unsubstituted divalent aromatic group represented by ^A2 is preferably a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted monocyclic or fused ring aromatic ring, and is also preferably a group in which two hydrogen atoms have been removed from any position of an unsubstituted aromatic ring.

The number of carbon atoms in the substituted or unsubstituted divalent aromatic group represented by ^A2 is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

Specific examples of unsubstituted aromatic rings include benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene, and preferably benzene or naphthalene.

When the divalent aromatic group represented by ^A2 has a substituent, the substituent is preferably selected from the group consisting of an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms.

As described above, the divalent aromatic group represented by ^A2 is unsubstituted, or if it has a substituent, the substituent is preferably selected from the group consisting of an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms. When the divalent aromatic group represented by ^A2 is unsubstituted or has a substituent with small steric hindrance, the π-π stacking interaction between mesogenic skeletons is less likely to be hindered, and the degree of orientation is increased, so that a cured product having high thermal conductivity can be obtained.

Specific preferred examples of the substituted or unsubstituted divalent aromatic group represented by ^A2 include the following groups.

The substituted or unsubstituted divalent cycloalkane group represented by ^A2 is a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted cycloalkane ring. This substituted or unsubstituted cycloalkane ring has the same meaning as the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group represented by ^A1 (i.e., a substituted or unsubstituted cycloalkane ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group), and the preferred embodiments thereof are also the same.

Preferred specific examples of the substituted or unsubstituted divalent cycloalkane group represented by ^A2 include the following groups.

The substituted or unsubstituted divalent cycloalkene group represented by ^A2 is a group in which two hydrogen atoms have been removed from any position of a substituted or unsubstituted cycloalkene ring.

In this specification, the cycloalkene ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring. When the cycloalkene 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 reducing dielectric tangent, it is preferable that the cycloalkene ring does not contain a heteroatom. The cycloalkene ring is preferably a monocyclic ring or a condensed ring, and more preferably a monocyclic ring. 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. In addition, the position of the double bond contained in the cycloalkene ring is not particularly limited.
In addition, in this specification, the cycloalkene group and the cycloalkene ring may be in a cis form, a trans form, or a mixture thereof, and in the case of a mixture, it is preferable that the proportion of the trans form is higher.

The number of carbon atoms in the unsubstituted divalent cycloalkene group is not particularly limited, but is preferably 4 to 20, more preferably 5 to 16, and even more preferably 6 to 14. The number of carbon atoms in the unsubstituted cycloalkene ring is synonymous with the number of carbon atoms in the unsubstituted divalent cycloalkene group, and the preferred embodiments are the same.

Specific examples of unsubstituted cycloalkene rings 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.

When the divalent cycloalkene group has a substituent, that is, when the cycloalkene ring has a substituent, the substituent has the same meaning as the substituent that the m-valent aromatic group represented by ^A1 may have.

Preferred specific examples of the substituted or unsubstituted divalent cycloalkene group represented by ^A2 include the following groups.

The divalent group represented by ^A2 in which two or more substituted or unsubstituted aromatic rings are linked by a single bond is a group obtained by removing two hydrogen atoms from any position of a compound in which two or more substituted or unsubstituted aromatic rings are linked by a single bond. The substituted or unsubstituted aromatic ring linked by a single bond is the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by binding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group), and the preferred embodiments thereof are also the same.

The divalent group represented by ^A2 in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds is a group obtained by removing two hydrogen atoms from any position of a compound in which two or more substituted or unsubstituted cycloalkane rings are linked by single bonds. The substituted or unsubstituted cycloalkane ring linked by a single bond is the same as the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group represented by ^A1 (i.e., a substituted or unsubstituted cycloalkane ring formed by binding a hydrogen atom to a bond of an m-valent cycloalkane group), and the preferred embodiments thereof are also the same.

The divalent group represented by ^A2 in which two or more substituted or unsubstituted cycloalkene rings are linked by single bonds is a group obtained by removing two hydrogen atoms from any position of a compound in which two or more substituted or unsubstituted cycloalkene rings are linked by single bonds. The substituted or unsubstituted cycloalkene ring linked by a single bond is the same as the substituted or unsubstituted cycloalkene ring mentioned in the description of the substituted or unsubstituted divalent cycloalkene group represented by ^A2 (i.e., a substituted or unsubstituted cycloalkene ring formed by binding a hydrogen atom to a bond of a substituted or unsubstituted divalent cycloalkene group), and the preferred embodiments thereof are also the same.

In a compound in which two or more substituted or unsubstituted cycloalkene rings are linked by single bonds, the number of substituted or unsubstituted cycloalkene 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.

The divalent group 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 represented by ^A2 is a group obtained by removing two hydrogen atoms 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 ring and the substituted or unsubstituted cycloalkane ring linked by a single bond are respectively the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group.) and the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group represented by ^A1 (i.e., a substituted or unsubstituted cycloalkane ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group.) and the preferred embodiments thereof are the same.

[0043] Specific preferred examples of the divalent group represented by ^A2 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 include the following groups.

The divalent group 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 represented by ^A2 is a group obtained by removing two hydrogen atoms 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 ring and the substituted or unsubstituted cycloalkene ring linked by a single bond are respectively the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group.) and the substituted or unsubstituted cycloalkene ring mentioned in the description of the substituted or unsubstituted divalent cycloalkene group represented by ^A2 (i.e., a substituted or unsubstituted cycloalkene ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted divalent cycloalkene group.) and the preferred embodiments thereof are the same.

[0043] Specific preferred examples of the divalent group represented by ^A2 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 include the following groups.

In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkene rings 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, and 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. In addition, the total number of substituted or unsubstituted aromatic rings linked by single bonds and the number of substituted or unsubstituted cycloalkene rings is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

The divalent group represented by ^A2 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 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 the 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 m-valent cycloalkane group represented by ^A1 (i.e., a substituted or unsubstituted cycloalkane ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group) and the substituted or unsubstituted cycloalkene ring mentioned in the description of the substituted or unsubstituted divalent cycloalkene group represented by ^A2 (i.e., a substituted or unsubstituted cycloalkene ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted divalent cycloalkene group), and preferred aspects thereof are also the same.

In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkene rings are linked by single bonds, 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, and 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. In addition, the total number of substituted or unsubstituted cycloalkane rings and substituted or unsubstituted cycloalkene rings linked by single bonds is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

The divalent group represented by ^A2 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 single bonds is a group obtained by removing two hydrogen atoms 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 single bonds. The substituted or unsubstituted aromatic ring, substituted or unsubstituted cycloalkane ring, and substituted or unsubstituted cycloalkene ring linked by a single bond are respectively the same as the substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group represented by ^A1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent aromatic group), the substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group represented by ^A1 (i.e., a substituted or unsubstituted cycloalkane ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted m-valent cycloalkane group), and the substituted or unsubstituted cycloalkene ring mentioned in the description of the substituted or unsubstituted divalent cycloalkene group represented by ^A2 (i.e., a substituted or unsubstituted cycloalkene ring formed by bonding a hydrogen atom to a bond of a substituted or unsubstituted divalent cycloalkene group), and the preferred embodiments thereof are also the same.

In 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 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, and 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. In addition, the total number of substituted or unsubstituted aromatic rings, substituted or unsubstituted cycloalkane rings, and substituted or unsubstituted cycloalkene rings linked by single bonds is preferably 3 to 10, more preferably 3 to 4, and even more preferably 3.

When A ² is a group represented by *-B ¹ Y ¹ B ² -**, a group represented by *-B ¹ Y ¹ B ² Y ² B ³ -**, or a group represented by *-B ¹ Y ¹ B ² Y ² B ³ Y ³ B ⁴ -**, B ¹ to B ⁴ are each a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group in which one or more substituted or unsubstituted aromatic rings and one or more a divalent group 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, a divalent group 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, or a divalent group 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; and Y ¹ to Y ³ each represent an ester group, a carbonyl group, or an ether group.

A substituted or unsubstituted divalent aromatic group represented by B ¹ to B ⁴ (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted A divalent group 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, a divalent group 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, and a divalent group 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 are each represented by the following formula: a substituted or unsubstituted divalent aromatic group represented by ^{the formula (2)} (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted and a divalent group 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, a divalent group 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, and a divalent group 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, and preferred aspects thereof are also the same.

Each of Y ¹ to Y ³ is an ester group (—COO— or —OCO—), a carbonyl group (—CO—) or an ether group (—O—), and is preferably an ester group.

From the viewpoint of obtaining a vinyl compound having a low melting point, ^A1 and ^A2 are also preferably, among the above-mentioned groups, a group having 3 to 14 carbon atoms or a group having 6 to 14 carbon atoms, provided that this number of carbon atoms does not include the number of carbon atoms of the substituent.

In formula (1) and formula (2), X ¹ is a single bond, an ester group (-COO- or -OCO-), a carbonyl group (-CO-), or an ether group (-O-), preferably an ester group or a carbonyl group, and more preferably an ester group. Multiple X ^1s may be the same or different from each other.

In formula (1) and formula (2), m is an integer from 3 to 6, preferably an integer from 3 to 5, more preferably 3 or 4, and even more preferably 3.

In formula (2), n is an integer from 1 to 20, preferably an integer from 1 to 12, more preferably an integer from 1 to 8, and even more preferably an integer from 2 to 6. Multiple n's may be the same or different.

In this specification, the vinyl compound represented by formula (1) or formula (2) of this embodiment may be referred to as "vinyl compound (1)." Vinyl compound (1) has a low melting point and high solubility.

The melting point of the vinyl compound (1) is preferably less than 160°C. It is preferably 80°C or higher and less than 160°C, more preferably 90 to 155°C, and even more preferably 100 to 155°C. If the melting point of the vinyl compound is within the above range, it becomes easy to process it by melt kneading or the like, and the energy required for processing can also be reduced.

The vinyl compound (1) has high solubility in organic solvents when a coating solution prepared by dissolving the vinyl compound in an organic solvent is applied, and therefore has excellent workability, processability, and the like.
The organic solvent is not particularly limited, and examples thereof include hydrocarbon solvents such as hexane, benzene, and toluene; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; ether solvents such as diethyl ether, isobutyl methyl ether, and tetrahydrofuran; and ester solvents such as methyl acetate, ethyl acetate, and isobutyl acetate.
As shown in the Examples below, vinyl compound (1) exhibits higher solubility in ether solvents than conventionally known vinyl compounds. Specifically, vinyl compound 1 and vinyl compound 2 in the Examples exhibit solubilities in ether solvents that are about 7 times and about 3 times, respectively, of conventionally known vinyl compounds.

The vinyl compound (1) 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 (1) can be suitably used to form a constituent material for the insulating layer of a printed wiring board, a heat dissipation material, and the like.

In formula (1), when A ¹ contains a chain-like saturated aliphatic hydrocarbon group, A ² is the mesogenic skeleton in vinyl compound (1). On the other hand, in formula (1), when A ¹ does not contain a chain-like saturated aliphatic hydrocarbon group, the structure in which A ¹ , X ¹ and A ² are linked is the mesogenic skeleton in vinyl compound (1). The mesogenic skeleton of vinyl compound (1) has a higher degree of orientation because it has a larger number of linked hydrocarbon rings than, for example, a conventional mesogenic skeleton having a structure in which two hydrocarbon rings are linked. The resin, which is the cured product of vinyl compound (1), exhibits high thermal conductivity due to having such a structure with a high degree of orientation.

On the other hand, resins that have hydroxyl groups tend to have high dielectric loss. For example, a resin that is a cured product of a compound (monomer) that has epoxy groups at its terminal has hydroxyl groups in the resin, and its dielectric loss is high. In contrast, the terminal of vinyl compound (1) is neither an epoxy group nor a hydroxy group, but a vinyl group (ethenyl group). Therefore, the cured product (polymer) of vinyl compound (1) has no hydroxy groups and therefore shows low dielectric loss.

<<Method of producing vinyl compound>>
The vinyl compound (1) can be produced, for example, by reacting a compound represented by formula (3) or formula (4) (sometimes referred to as "compound (A)" in this specification) with a compound represented by formula (5) (sometimes referred to as "compound (B)" in this specification) in the presence of a base.

(In the formula, A ¹ , X ¹ , A ² , m, and n each have the same meaning as above.)

XR (5)
(In the formula, X represents a halogen atom; R has the same meaning as above.)

Examples of the compound (A) include 1,3,5-tris(4-hydroxyphenyl)cyclohexane, 1,3,5-tris(3-methyl-4-hydroxyphenyl)cyclohexane, 1-(4-hydroxyphenyl)-3,5-bis(3-methyl-4-hydroxyphenyl)cyclohexane, 1-(3-methyl-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)cyclohexane, 1,3,5-tris(4-hydroxyphenyl)benzene, 1,3,5-tris(3-methyl-4- 1-(4-hydroxyphenyl)-3,5-bis(3-methyl-4-hydroxyphenyl)benzene, 1-(3-methyl-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)benzene, 1,3,5-tris(4-(4-hydroxyphenyl)cyclohexyl)benzene, 1,3,5-tris(4-hydroxyphenyl)-1,3,5-cyclohexanetricarboxylate, 1,3,5-tris(3-methyl-4-hydroxyphenyl)-1,3,5-cyclohexanetricarboxylate, Cyclohexanetricarboxylate, 1-(4-hydroxyphenyl)-3,5-bis(3-methyl-4-hydroxyphenyl)-1,3,5-cyclohexanetricarboxylate, 1-(3-methyl-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1,3,5-cyclohexanetricarboxylate, 1,3,5-tris(4-hydroxyphenyl)-1,3,5-benzenetricarboxylate, 1,3,5-tris(3-methyl-4-hydroxyphenyl)-1,3,5- Benzenetricarboxylate, 1-(3-methyl-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1,3,5-benzenetricarboxylate, 1-(4-hydroxyphenyl)-3,5-bis(3-methyl-4-hydroxyphenyl)-1,3,5-benzenetricarboxylate, 1,3,5-tris(4-(4-hydroxyphenyl)cyclohexyl)-1,3,5-benzenetricarboxylate, 1,3,5-tris(4-hydroxyphenylcarbonyloxy)cyclohexyl cyclohexane, 1,3,5-tris(3-methyl-4-hydroxyphenylcarbonyloxy)cyclohexane, 1-(4-hydroxyphenylcarbonyloxy)-3,5-bis(3-methyl-4-hydroxyphenylcarbonyloxy)cyclohexane, 1-(3-methyl-4-hydroxyphenylcarbonyloxy)-3,5-bis(4-hydroxyphenylcarbonyloxy)cyclohexane, 1,3,5-tris(4-hydroxyphenylcarbonyloxy)benzene, 1,3,5-tris(3-methyl-4-hydroxyphenylcarbonyloxy) 1-(4-hydroxyphenylcarbonyloxy)-3,5-bis(3-methyl-4-hydroxyphenylcarbonyloxy)benzene, 1-(3-methyl-4-hydroxyphenylcarbonyloxy)-3,5-bis(4-hydroxyphenylcarbonyloxy)benzene, 1,3,5-tris(4-(4-hydroxyphenyl)cyclohexylcarbonyloxy)benzene, 1,3,5-tris(4-hydroxyphenyl)cyclohexylcarbonyloxy)benzene, Examples of the hydroxyethyl ether include hexane, 1,3,5-tris(3-methyl-4-hydroxyphenylcarbonyl)cyclohexane, 1-(4-hydroxyphenylcarbonyl)-3,5-bis(3-methyl-4-hydroxyphenylcarbonyl)cyclohexane, 1-(3-methyl-4-hydroxyphenylcarbonyl)-3,5-bis(4-hydroxyphenylcarbonyl)cyclohexane, 1,3,5-tris(4-hydroxyphenylcarbonyl)benzene, 1,3,5-tris(3-methyl-4-hydroxyphenylcarbonyl)benzene, 1-(4-hydroxyphenylcarbonyl)-3,5-bis(3-methyl-4-hydroxyphenylcarbonyl)benzene, 1-(3-methyl-4-hydroxyphenylcarbonyl)-3,5-bis(4-hydroxyphenylcarbonyl)benzene, 1,3,5-tris(4-(4-hydroxyphenyl)cyclohexylcarbonyl)benzene, 2-hydroxyethyl ethers thereof, 3-hydroxypropyl ethers thereof, and 4-hydroxybutyl ethers thereof. Compound (A) can be produced by known organic synthesis methods, such as an ester synthesis method, a ketone synthesis method, an ether synthesis method, or methods similar thereto, either alone or in combination.

The X represents a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

Examples of compound (B) include acryloyl bromide, acryloyl chloride, methacryloyl bromide, methacryloyl chloride, o-vinylbenzyl bromide, m-vinylbenzyl bromide, p-vinylbenzyl bromide, o-vinylbenzyl chloride, m-vinylbenzyl chloride, and p-vinylbenzyl chloride. Compound (B) may be used alone or in any combination and ratio of two or more kinds.

The amount of compound (B) used is usually preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents, relative to compound (A).

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; alkali metal carbonates such as sodium carbonate and potassium carbonate; and the like.
Examples of the organic base include pyridine. The amount of the base used is preferably 2 to 5 equivalents relative to compound (A). When an organic base that is liquid under reaction conditions is used, such an organic base may be used in an excess amount to serve as a reaction solvent.

The reaction between compound (A) and compound (B) is usually carried out in a solvent by mixing compound (A), compound (B), and a base. The order of mixing is not particularly limited.

The solvent is not particularly limited as long as it is a solvent inert to the reaction, but a hydrophilic solvent is preferred in that it is easy to suppress the generation 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 combination. In addition, when an organic base that is liquid under reaction conditions is used as a base, the organic base may be used as a reaction solvent.
Among these, the solvent is preferably an ether solvent, an aprotic polar solvent, or a mixture thereof, more preferably an aprotic polar solvent, and particularly preferably N,N-dimethylformamide.

The amount of solvent used is preferably 1 to 20 mL, and more preferably 2 to 10 mL, per gram of compound (A).

The reaction between compound (A) and compound (B) may be carried out in the presence of a catalyst via a halogen exchange reaction.
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 of the catalyst used is preferably 0.05 to 1 times by mass, more preferably 0.1 to 0.5 times by mass, based on the amount of compound (A) used.

The reaction between compound (A) and compound (B) 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 of the polymerization inhibitor used is preferably 0.002 to 0.05 times, more preferably 0.004 to 0.02 times, by mass, the amount of compound (B) used.

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.

After the reaction is completed, for example, the reaction liquid is cooled, water or a mixed solvent containing water is added, the precipitated solid is filtered off, and if necessary, a known post-treatment operation is carried out once or twice or more times to obtain vinyl compound (1). Examples of the post-treatment operation include stirring and washing the solid in water, a mixed solvent containing water, or an organic solvent; extraction of the solution in which the solid is dissolved (liquid separation), and the like. The obtained vinyl compound (1) may be further purified by a conventional purification means if necessary.

The structure of the obtained vinyl compound (1) can be confirmed by a known method such as nuclear magnetic resonance (NMR) spectroscopy.

<<Vinyl Composition>>
The vinyl composition of the present embodiment contains a vinyl compound (1).
In this specification, the vinyl composition of the present embodiment may be referred to as "vinyl composition (1)."

The vinyl composition (1) has a curing property and may contain only the vinyl compound (1), or may contain the vinyl compound (1) and other components other than the vinyl compound (1) within a range that does not impair the effects of the present invention. The vinyl compound (1) may be cured by heating or by light irradiation. In the examples described later, it is cured by heating. When curing the vinyl composition (1), pressure may be applied to the vinyl composition (1). The vinyl composition (1) can be suitably used to form a constituent material such as an insulating layer of a printed wiring board or a heat dissipation material.

<Vinyl compound (1)>
The vinyl composition (1) may contain one type of vinyl compound (1) alone, or may contain two or more types in any combination and in any ratio.

When the vinyl composition (1) contains two or more vinyl compounds (1) in which two or more R in one molecule are vinylbenzyl groups, it is preferable that these two or more vinyl compounds (1) are a mixture of multiple vinyl compounds (1) in which the vinyl groups in the terminal vinylbenzyl groups are different in position and the portions other than the vinylbenzyl groups are identical.

For example, in a vinyl composition (1) containing two or more types of vinyl compounds (1) in which two or more R in one molecule are vinylbenzyl groups, if the total number of moles of vinylbenzyl groups in the vinyl compounds (1) in which two or more R in one molecule are vinylbenzyl groups is taken as 100, the number of moles of vinylbenzyl groups in the m-position of the vinyl group is preferably 30 to 90, more preferably 40 to 90, even more preferably 50 to 90, even more preferably 60 to 80, and particularly preferably 70 to 80. For example, the ratio of the number of moles of vinylbenzyl groups whose vinyl groups are in the p-position to the number of moles of vinylbenzyl groups whose vinyl groups are in the m-position (number of moles of p-vinylbenzyl groups/number of moles of m-vinylbenzyl groups; sometimes referred to as the "p/m ratio" in this specification) is preferably 10/90 to 70/30, more preferably 10/90 to 60/40, even more preferably 10/90 to 50/50, even more preferably 20/80 to 40/60, and particularly preferably 20/80 to 30/70. By having the number of moles of vinylbenzyl groups whose vinyl groups are in the m-position or the p/m ratio in the above range, the mixture of vinyl compounds (1) melts at a lower temperature, and the processability of the vinyl compounds can be improved.

<Other Ingredients>
Examples of the other components contained in the vinyl composition (1) include a radical initiator; a filler; an additive; a solvent; a vinyl compound other than the vinyl compound (1) (sometimes referred to as "other vinyl compounds" in this specification); and a resin other than a polymer (cured product) of the vinyl compound (1) (sometimes referred to as "other resins" in this specification).

The additives include, for example, silane coupling agents, colorants, low stress components, release agents, antioxidants, defoamers, flow control agents, etc.

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

The filler may, for example, be silica powder such as fused crushed silica powder, fused spherical silica powder, crystalline silica powder, or secondary agglomerated silica powder; metal oxides such as alumina, titanium oxide, zinc oxide, tungsten carbide, or magnesium oxide; glass cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, or titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; or mica.

The silane coupling agent may, for example, be γ-glycidoxypropyltrimethoxysilane.
The colorant may, for example, be 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, and paraffin.

The solvent contained in the vinyl composition (1) may, for example, be a ketone-based solvent such as methyl ethyl ketone or methyl isobutyl ketone; an aprotic polar solvent such as dimethyl sulfoxide or N-methylpyrrolidone; an ester-based solvent such as butyl acetate; a glycol-based solvent such as propylene glycol monomethyl ether; or an aromatic solvent such as toluene.

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 (1).
The other resin is not particularly limited as long as it is a resin other than a polymer of the vinyl compound (1).

The vinyl composition (1) may contain only one type of other component, or two or more types.

The content of the other components in the vinyl composition (1) can be selected arbitrarily depending on the type of the other components.
In the vinyl composition (1), the content ratio of the vinyl compound (1) to the total content of components other than the solvent is preferably 80% by mass or more, and may be, for example, any of 85% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, and 99% by mass or more. On the other hand, the ratio is 100% by mass or less. The vinyl composition (1) having the ratio of 80% by mass or more is preferable because the effect obtained by containing the vinyl compound (1) is higher.

The vinyl compound (1) obtained by the above method can be used as it is as vinyl composition (1). The vinyl composition (1) containing the other components can be obtained by mixing the vinyl compound (1) with the other components.

<<Cured vinyl resin>>
The vinyl resin cured product of the present embodiment is obtained by curing the vinyl compound (1) or the vinyl composition (1).
In this specification, the vinyl resin cured product of this embodiment may be referred to as "vinyl resin cured product (1)".

The vinyl resin cured product has high thermal conductivity due to the use of vinyl compound (1), making it suitable as a constituent material for printed wiring boards, and is particularly suitable as an insulating material for printed wiring boards. The vinyl resin cured product, due to the use of vinyl compound (1), tends to have lower dielectric loss than epoxy resins used for conventional circuit boards.

When the vinyl resin cured material (1) is a cured material of a vinyl compound (1), the vinyl resin cured material (1) may be a cured material of one type of vinyl compound (1) or may be a cured material of two or more types of vinyl compounds (1).
When the vinyl resin cured product (1) is a cured product of the vinyl composition (1), the vinyl resin cured product (1) may be a cured product of one type of vinyl composition (1) or a cured product of a mixture of two or more types of vinyl compositions (1).

The vinyl resin cured product (1) can be prepared, for example, by filling a mold with the vinyl compound (1) or the vinyl composition (1) as is, and, if necessary, applying pressure at a predetermined pressure with a press or the like while heating for a predetermined time to cause primary curing, and then further applying pressure at a predetermined pressure with a press or the like while heating for a predetermined time to cause complete curing; by heating the vinyl compound (1) or the vinyl composition (1) as is at a predetermined temperature to cause curing; by pouring the powder of the vinyl compound (1) or the vinyl composition (1) as is, or after melting it as necessary, into a mold and heating for a predetermined time while applying pressure at a predetermined pressure with a press or the like; by heating and melting the vinyl compound (1) and then applying pressure to a mold or the like while heating for a predetermined time to cause complete curing; and further heating the mold to form the molded product; a method of melting the vinyl compound (1) or vinyl composition (1) and injecting the resulting molten product into a preheated mold to harden it; a method of partially hardening the vinyl compound (1) or vinyl composition (1), grinding the resulting partially hardened product, filling the resulting powder into a mold, and melt-molding the filled powder; a method of dissolving the vinyl compound (1) or vinyl composition (1) as is or as necessary in a solvent, partially hardening it while stirring as necessary, casting the resulting solution, and then drying and removing the solvent by ventilation drying or the like, and heating it for a predetermined time while applying a predetermined pressure with a press or the like as necessary.

The heating temperature (curing temperature; complete curing temperature when curing is performed in multiple stages) when the vinyl compound (1) or the vinyl composition (1) is heated and cured is not particularly limited, but in order to increase the degree of curing of the vinyl compound (1) or the vinyl composition (1), it is preferably 140°C or higher, and more preferably 150°C or higher. In order to avoid excessive heating, the heating temperature is preferably 200°C or lower.

The heating time (curing time; when curing is performed in multiple stages, the heating time at the complete curing temperature) when the vinyl compound (1) or the vinyl composition (1) is heated and cured is not particularly limited, but in order to increase the degree of curing of the vinyl compound (1) or the vinyl composition (1), it is preferably 1 hour or more, and more preferably 2 hours or more. In order to avoid unnecessary curing operations, the heating time is preferably 10 hours or less.

The pressure applied when the vinyl compound (1) or the vinyl composition (1) is pressed and cured (pressure during curing) is not particularly limited, but in terms of increasing the degree of curing of the vinyl compound (1) or the vinyl composition (1), it is preferably 0.7 MPa or more, and more preferably 1.2 MPa or more. In terms of avoiding excessive pressurization, the pressure applied is preferably 3 MPa or less.

The thermal diffusivity of the vinyl resin cured product (1) is preferably 1.75×10 ⁻⁷ m ² /s or more, more preferably 1.80×10 ⁻⁷ m ² /s or more, and even more preferably 1.85×10 ⁻⁷ m ² /s or more. When the thermal diffusivity is in the above range, the thermal conductivity tends to be high. The upper limit of the thermal diffusivity of the vinyl resin cured product (1) is not particularly limited, and the thermal diffusivity may be 4.00×10 ⁻⁷ m ² /s or less, 3.00×10 ⁻⁷ m ² /s or less, or 2.50×10 ⁻⁷ m ² /s or less.
The thermal diffusivity of the vinyl resin cured product (1) may be, for example, any one of 1.75×10 ⁻⁷ to 4.00×10 ⁻⁷ m ² /s, 1.80× ¹⁰ −7 to 3.00×10 ⁻⁷ m ² /s, and 1.85×10 ⁻⁷ to 2.50×10 ⁻⁷ m ² /s.

The thermal diffusivity of the vinyl resin cured material (1) can be measured by temperature wave thermal analysis (TWA). In this example, the thermal diffusivity is measured using a commercially available thermal diffusivity measuring device, "ai-phase mobile" (manufactured by ai-phase Co., Ltd.).

The dielectric loss tangent of the vinyl resin cured product (1) at a frequency of 100 MHz is preferably 0.0050 or less, more preferably 0.0048 or less, and even more preferably 0.0046 or less. The lower limit of the dielectric loss tangent of the vinyl resin cured product (1) is not particularly limited, and the dielectric loss tangent may be 0.0010 or more, 0.0020 or more, or 0.0030 or more.
The dielectric loss tangent of the vinyl resin cured material (1) at a frequency of 100 MHz may be, for example, any one of 0.0010 to 0.0050, 0.0020 to 0.0048, and 0.0030 to 0.0046, although these are only examples of the dielectric loss tangent of the vinyl resin cured material (1).

The dielectric loss tangent of the vinyl resin cured material (1) 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: 1V

<<Prepreg>>
The prepreg of the present embodiment contains a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) 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 (1)". By using the prepreg (1), a laminate or the like can be easily manufactured by a normal method. For example, a desired laminate can be obtained by stacking a plurality of prepregs (1) to form a laminate, and molding and integrating the laminate by applying pressure while heating.
A printed wiring board (resin layer in a printed wiring board) obtained by using the prepreg (1) or the laminate has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (1).

The prepreg (1) can be produced by a method in which a solution of the vinyl compound (1) dissolved in a solvent is applied to or impregnated into a fibrous substrate; or a method in which the vinyl composition (1) or a dilution of the vinyl composition (1) diluted with a solvent is applied to or impregnated into a fibrous substrate, and the fibrous substrate after the application or impregnation is heated to semi-cure the vinyl compound (1) or the vinyl composition (1).

The heating temperature (semi-curing temperature) and heating time (semi-curing time) when semi-curing the vinyl compound (1) or the vinyl composition (1) can be appropriately set in consideration of the above-mentioned curing conditions (heating temperature and heating time) of the vinyl compound (1) or the vinyl composition (1) so that the vinyl compound (1) or the vinyl composition (1) is not completely cured.

The fibrous substrate is not particularly limited as long as it is a fibrous substrate, and may be any known substrate. More specific examples of fibrous substrates include woven and nonwoven fabrics of inorganic fibers such as glass fibers, and woven and nonwoven fabrics of organic fibers such as polyester.

<<Film with resin>>
The resin-attached film of this embodiment comprises a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and a support film. More specifically, the resin-attached film of this embodiment may be, for example, a resin-attached film comprising the resin layer and the support film provided on one or both sides of the resin layer. A laminate sheet is obtained by using a plurality of resin-attached films of this embodiment, removing the support film, stacking them together to form a laminate, and molding and integrating this laminate by heating and pressing. The resin layer in the resin-attached 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 (1).

The support film may be, for example, a polyethylene terephthalate (PET) film.
In the case of a resin-attached film, when a support film is provided on both sides of a resin layer, these support films may be the same as or different from each other. In this specification, not only in the case of a resin-attached film, but also in the case of two layers of support films being different from each other, it means that at least one of the material and thickness of the two layers of support films is different from each other.

The resin-attached film of this embodiment can be produced by applying a solution of vinyl compound (1) dissolved in a solvent to the support film, or by applying vinyl composition (1) or a dilution of vinyl composition (1) diluted with a solvent to the support film, and then heating the layer of the coating to semi-cure the vinyl compound (1) or vinyl composition (1) in the coating. The conditions for semi-cure of vinyl compound (1) or vinyl composition (1) at this time are the same as those for producing the prepreg described above.

<<Metal foil with resin>>
The resin-attached metal foil of this embodiment comprises a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and a metal foil. More specifically, the resin-attached metal foil of this embodiment may be, for example, a resin-attached metal foil comprising the resin layer and the metal foil provided on one or both sides of the resin layer. For example, the resin-attached metal foil of this embodiment may be used to further cure the semi-cured product to form a cured product, and the metal foil may be patterned to form a circuit, thereby forming a printed wiring board. In addition, the resin-attached metal foil of this embodiment may be used to pattern the metal foil to form a circuit, and resin layers having such circuits may be laminated together with the circuit orientation aligned, and the semi-cured product may be further cured by applying pressure while heating, thereby forming a multilayer printed wiring board having a resin layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1) 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 (1).

The metal foil may be, for example, a copper foil.
In the case of the resin-coated metal foil, when the metal foil is provided on both sides of the resin layer, these metal foils may be the same or different from each other. In this specification, not only in the case of the resin-coated metal foil, but also in the case of the two layers of metal foil being different from each other, it means that at least one of the material and the thickness of the two layers of metal foil is different from each other.

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

<<Metal-clad laminate>>
The metal-clad laminate of this embodiment comprises an insulating layer containing a cured product of a vinyl compound (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and a metal foil. More specifically, the metal-clad laminate of this embodiment may be, for example, a metal-clad laminate comprising 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 multi-layer printed wiring board can be made by stacking such a plurality of printed wiring boards via a separately prepared insulating layer and applying pressure while heating. 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 (1).

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 each other or different from each other.

The insulating layer used separately when laminating the printed wiring board may be a known one, may be the resin layer in the resin-attached film described above, or the laminate sheet which is a laminate of a plurality of the resin layers, or may be the prepreg (1) described above, or the laminate obtained by overlapping a plurality of prepregs (1). Alternatively, the insulating layer may be the resin layer, laminate sheet, prepreg (1), or laminate obtained by further curing the vinyl compound (1) or vinyl composition (1).

The metal-clad laminate of the present embodiment can be produced, for example, by laminating a metal foil on one or both sides of a prepreg (1), and applying pressure to the resulting laminate while heating, thereby further curing the vinyl compound (1) or a semi-cured product thereof, or the vinyl composition (1) or a semi-cured product thereof in the prepreg (1) to form a cured product, thereby forming an insulating layer and fusing the prepreg (1) and the metal foil.
The metal-clad laminate of the present embodiment may be produced, for example, by producing a prepreg (1) using the vinyl compound (1) or the vinyl composition (1) by the method described above, and then using this prepreg (1) by the method described above.
The metal-clad laminate of the present embodiment can also be produced, for example, by heating the above-mentioned resin-attached metal foil to further cure the vinyl compound (1) or a semi-cured product thereof, or the vinyl composition (1) or a semi-cured product thereof in the resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1).

<<Printed wiring board>>
The printed wiring board of this embodiment comprises an insulating layer containing a cured product of a vinyl compound (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and a 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 multi-layer printed wiring board can be formed by stacking a plurality of 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 (1).

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

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 the present embodiment can also be produced by, for example, heating the above-mentioned resin-attached metal foil to further cure the vinyl compound (1) or a semi-cured product thereof, or the vinyl composition (1) or a semi-cured product thereof in the resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1), and then patterning the metal foil to form a conductor wiring (circuit).
The metal foil can be patterned by known methods such as etching.

FIG. 1 is a cross-sectional view showing a schematic example of a laminated structure of the present embodiment obtained using vinyl compound (1). Note that the figures used in the following explanation may show enlarged essential parts for the sake of convenience 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 in reality.

The laminated 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 (1). The second layer 12 is selected according to the type of laminated structure 1. Both the first layer 11 and the second layer 12 are in the form of a film or sheet. The second layer 12 may be provided over the entire area of one surface 11a of the first layer 11, or may be provided in a partial area.

In the case where the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 is a support film, the laminate structure 1 is a resin-attached film.
In the case where the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) 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 (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and the second layer 12 is a metal foil, the laminate structure 1 is a metal-clad laminate.

FIG. 2 is a cross-sectional view showing a schematic diagram of another example of the laminated structure of this embodiment obtained using vinyl compound (1). In FIG. 2 and subsequent figures, the same components as those shown in the figures already described are given the same reference numerals as in the figures already described, and detailed description thereof will be omitted.

The laminated 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 laminated 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 laminated structure 2 is the same as the laminated structure 1 shown in FIG. 1, except that the laminated structure 2 includes a linear second layer 22 instead of the film-like second layer 12.
In the case where the first layer 11 is an insulating layer containing a cured product of a vinyl compound (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and the second layer 22 is a conductor wiring, the laminate structure 2 is a printed wiring board.

Both the laminated structure 1 and the laminated 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.

FIG. 3 is a cross-sectional view that illustrates still another example of the laminate structure of the present embodiment obtained by using the vinyl compound (1).
The laminated structure 3 shown here is configured to include 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 in the form of a film or sheet, and is selected according to the type of the laminated structure 1, similar to the second layer 12. 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 area.

In the case where the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are support films, the laminated structure 3 is a resin-attached film.
In the case where the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a resin-coated metal foil.
In the case where the first layer 11 is an insulating layer containing a cured product of a vinyl compound (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal-clad laminate.

FIG. 4 is a cross-sectional view that illustrates still another example of the laminate structure of the present embodiment obtained by using the vinyl compound (1).
The laminated structure 4 shown here is configured to include 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 laminated structure 4 is formed to include both a cross section along the linear length direction of the second layer 22 and a cross section along the linear length direction 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 one or more.
In the case where the first layer 11 is an insulating layer containing a cured product of a vinyl compound (1), a cured product of a vinyl composition (1), or a cured product of a prepreg (1), and the second layer 22 and the third layer 23 are conductor wirings, the laminate structure 4 is a printed wiring board.

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.

The conditions for measuring the melting point of vinyl compounds are shown below.
A glass pan filled with a vinyl compound was kept at 50° C. for 2 minutes using a differential scanning calorimeter (FP84HT manufactured by METTLER TLEDO), and then the temperature was raised by 5° C. per minute, and the pan was kept at 250° C. for 2 minutes, and the endothermic peak temperature 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.

The conditions for measuring the solubility of vinyl compounds are shown below.
At room temperature, 50 mg of a vinyl compound was placed in a screw tube, THF stored at room temperature was added dropwise, and the weight of the solution was measured when the monomer was completely dissolved. The value of 50 mg/weight (mg) of the solution was taken as the solubility (wt%).

The test conditions for the cured product are as follows.
(1) Thermal Diffusivity The thermal diffusivity was measured by the TWA method at room temperature using a thermal diffusivity measuring device "ai-phase mobile" (manufactured by ai-phase Corporation).

Example 1
Into a 500 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 24.0 g of

trimethyl

1,3,5-benzenetricarboxylate, 55.3 g of 4-(trans-4-hydroxycyclohexyl)phenol, 1.2 g of dibutyltin oxide, and 120 mL of p-chlorotoluene were added and reacted at an internal temperature of about 180° C. for 15 hours.

After the reaction was completed, the mixture was cooled to room temperature, 36 mL of methanol was added, and the mixture was stirred for 2 hours. The precipitated solid was then filtered and washed with methanol. The solid was dried under reduced pressure to obtain 34.8 g of 1,3,5-tris(trans-4-(4-hydroxyphenyl)cyclohexyl) 1,3,5-benzenetricarboxylate.

In a 200mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 5.0g of 1,3,5-tris(trans-4-(4-hydroxyphenyl)cyclohexyl) 1,3,5-benzenetricarboxylate, 0.05g of 2,6-di(tert-butyl)-p-cresol, 7.2g of potassium carbonate, 0.3g of sodium iodide, 35mL of N,N-dimethylformamide, and 4.6g of vinylbenzyl chloride (mixture of m,p positional isomers) were charged and reacted at an internal temperature of approximately 60°C for 6 hours.

After the reaction was completed, the mixture was cooled to room temperature, 40 mL of water and 30 mL of hexane were added, and the mixture was stirred for 10 minutes. The precipitated solid was then filtered and washed with hexane, water, and methanol. The resulting solid was dissolved in toluene and washed with water. After some of the solvent was removed from the resulting solution under reduced pressure, methanol was added to the resulting concentrated liquid and stirred. The precipitated solid was then filtered and dried under reduced pressure to obtain 4.5 g of vinyl compound 1. Purity: 96.5% (liquid chromatography area percentage value).

Example 2
Into a 300 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 2.7 g of 1,3,5-benzenetricarbonyl trichloride, 6.6 g of hydroquinone, 3 mL of pyridine, and 130 mL of tetrahydrofuran were added and reacted at room temperature for 3 days.

After the reaction was completed, the solvent was distilled off and the resulting solid was purified using a silica gel column to obtain 1.3 g of 1,3,5-tris(4-hydroxyphenyl) 1,3,5-benzenetricarboxylate.

In a 100mL four-neck flask equipped with a thermometer, condenser, and stirrer, 1.3g of 1,3,5-tris(4-hydroxyphenyl)-1,3,5-benzenetricarboxylate, 0.01g of 2,6-di(tert-butyl)-p-cresol, 2.8g of potassium carbonate, 0.1g of sodium iodide, 25mL of N,N-dimethylformamide, and 1.9g of vinylbenzyl chloride (mixture of m,p positional isomers) were charged and reacted at an internal temperature of approximately 60°C for 13 hours.

After the reaction was completed, the mixture was cooled to room temperature, 40 mL of water was added, and the mixture was stirred for 10 minutes. The precipitated solid was then filtered and washed with hexane, water, and methanol. The resulting solid was dissolved in toluene, methanol was added, and the mixture was stirred. The precipitated solid was then filtered and dried under reduced pressure to obtain 0.4 g of vinyl compound 2. Purity: 70.6% (liquid chromatography area percentage value).

Example 3
Into a 300 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 1.8 g of trimethylolethane, 13.7 g of methyl 6-hydroxy-2-naphthoate, 1.1 g of dibutyltin oxide, and 150 mL of p-chlorotoluene were added and reacted at an internal temperature of about 180° C. for 14 hours.

After the reaction was completed, the reaction solution was cooled to room temperature, the supernatant was removed by decantation, and the solid was washed with methanol. The resulting solid was dried under reduced pressure to obtain solid A. Water was added to the methanol used for washing, and the precipitated solid was collected by filtration and dried under reduced pressure to obtain solid B. Solid A and solid B were combined to obtain 6.0 g of compound 1.

6.0 g of compound 1, 0.06 g of 2,6-di(tert-butyl)-p-cresol, 9.8 g of potassium carbonate, 0.3 g of sodium iodide, 65 mL of N,N-dimethylformamide, and 7.3 g of vinylbenzyl chloride (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 for 8 hours at an internal temperature of approximately 60°C.

After the reaction was completed, the mixture was cooled to room temperature, 40 mL of water and 30 mL of hexane were added, and the mixture was stirred. The precipitated solid was then filtered and washed with hexane, water, and methanol. The resulting solid was dissolved in toluene and washed with water. After some of the solvent was removed from the resulting solution under reduced pressure, methanol was added to the resulting concentrated liquid and stirred. The precipitated solid was then filtered and dried under reduced pressure to obtain 4.0 g of vinyl compound 3. Purity: 73.4% (liquid chromatography area percentage value).

Comparative Example 1
In a 200 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 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 were charged and reacted for 3 hours at an internal temperature of about 60°C. After the reaction was completed, 121 g of toluene and 34 mL of water were added and stirred, and the mixture was 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 then the toluene was removed under reduced pressure. 56 mL of methanol and 0.07 g of 2,6-di(tert-butyl)-p-cresol were added to the obtained solid and 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. Purity: 99.1% (liquid chromatography area percentage value).

The vinyl compounds obtained in Examples 1, 2, 3, and Comparative Example 1 were placed in the hollow plate of a mold, and heated for 1 hour at the primary curing temperature shown in Table 1 while applying a pressure of 1.5 MPa under reduced pressure. After that, the compounds were heated for 2 hours at 180°C while applying a pressure of 1.5 MPa to obtain a cured product having a thickness of 150 to 250 μm.

The melting points of the vinyl compounds and the thermal diffusivities of the cured products are shown in Table 1.

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.

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

A vinyl compound represented by formula (1) or formula (2):

(Wherein,
R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and a plurality of R may be the same or different from each other;
A 1 is a substituted or unsubstituted m-valent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted m-valent cycloalkane group, an m-valent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocyclic rings) are linked by a single bond, an m-valent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, an m-valent group 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, a substituted or unsubstituted m-valent linear saturated aliphatic hydrocarbon group, a group represented by R 1 (OR 2 -*) 3 , a group represented by R 1 (R 2 -*) 3 , a group represented by R 3 C(OR 2 -*) 3 , or a group represented by R 3 C(R 2 -*) 3 ;
R 1 is a substituted or unsubstituted trivalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups);
R 2 is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, a group represented by **-R 4 (R 5 ) p R 4 -*, or a group represented by **-(R 6 O) q R 6 -*, and multiple R 2 may be the same or different from each other;
R3 is a hydrogen atom or a methyl group;
R4 is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, and multiple R4s may be the same or different from each other.
R5 is a substituted or unsubstituted divalent aromatic group (excluding a nitrogen-containing aromatic heterocyclic group), and when p is 2 or 3, multiple R5s may be the same or different from each other;
R 6 is a substituted or unsubstituted divalent linear saturated aliphatic hydrocarbon group, and multiple R 6s may be the same or different from each other;
p is an integer from 1 to 3;
q is an integer from 1 to 3;
* is the bonding position to X1 ,
** represents the bonding position to the oxygen atom bonded to R 1 , the bonding position to R 1 , the bonding position to the oxygen atom bonded to R 3 C, or the bonding position to R 3 C.
A2 represents a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a divalent group 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, a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles), one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond, a group represented by *-B 1 Y 1 B 2 -**, a group represented by *-B 1 Y 1 B 2 Y 2 B 3 -**, or a group represented by *-B 1 Y 1 B 2 Y 2 B 3 Y 3 B 4 -**,
B 1 to B 4 each represent a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group in which two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, one or more substituted or unsubstituted aromatic rings and one or more a divalent group 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, a divalent group 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, or a divalent group 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,
Y 1 to Y 3 each represent an ester group, a carbonyl group, or an ether group;
* is the bonding position to X1 ,
** represents the bonding position to the acryloyloxy group, methacryloyloxy group, or vinylbenzyloxy group in formula (1), or the bonding position to the acryloyloxyalkoxy group, methacryloyloxyalkoxy group, or vinylbenzyloxyalkoxy group in formula (2),
X 1 is a single bond, an ester group, a carbonyl group, or an ether group, and a plurality of X 1 may be the same or different from each other;
m is an integer from 3 to 6,
n is an integer from 1 to 20, and multiple n's may be the same or different.
The vinyl compound according to claim 1, wherein A 1 and A 2 are groups having 14 or less carbon atoms (provided that the number of carbon atoms does not include the number of carbon atoms of the substituents).
The vinyl compound according to claim 1, which is used in printed wiring boards.
A vinyl composition containing the vinyl compound according to claim 1.
A vinyl resin cured product obtained by curing the vinyl compound according to any one of claims 1 to 3 or the vinyl composition according to claim 4.
A prepreg comprising the vinyl compound or semi-cured product thereof according to any one of claims 1 to 3, or the vinyl composition or semi-cured product thereof according to claim 4, and a fibrous base material.
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 3, or the vinyl composition or semi-cured product thereof according to claim 4, and a support film.
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 3, or the vinyl composition or semi-cured product thereof according to claim 4, and a metal foil.
A metal-clad laminate comprising an insulating layer containing a cured product of the vinyl compound according to any one of claims 1 to 3 or a cured product of the vinyl composition according to claim 4, and a metal foil.
A metal-clad laminate comprising an insulating layer containing the cured prepreg of claim 6 and a metal foil.
A printed wiring board comprising an insulating layer containing a cured product of the vinyl compound according to any one of claims 1 to 3 or a cured product of the vinyl composition according to claim 4, and a conductor wiring.
A printed wiring board comprising an insulating layer containing the cured product of the prepreg according to claim 6 and conductor wiring.