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

Abstract

The present invention addresses the problem of providing a novel compound which can be used as a constituent material for a printed wiring board, exhibits a low melting point and high solubility, and is capable of providing a resin having high thermal conductivity and low dielectric loss by curing. The present invention relates to a vinyl compound represented by formula (1) or formula (2) (R is a (meth) acryloyl group or a vinylbenzyl group; a1 represents a chain saturated aliphatic hydrocarbon group or a group comprising at least one selected from an aromatic group and a cycloalkane group; a2 represents one or more groups selected from the group consisting of an aromatic group, a cycloalkane group, and a cycloalkylene group; x1 represents a single bond, an ester group, a carbonyl group, or an ether group; m is an integer from 3 to 6; and n is an integer from 1 to 20) # imgabs0 #.

Description

Technical Field

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

[0002] The amount of data processed by communication equipment and the communication speed are increasing year by year. In line with this, high-speed communication technology for increasing the transmission speed of signals is being actively studied. When the amount of data processed by communication equipment is large, the heat generated in the electronic computing components in the communication equipment increases. If the heat is accumulated in the printed circuit board, it will cause adverse conditions. Therefore, the printed circuit board is required to have high heat dissipation performance.

[0003] As a printed circuit board with high heat dissipation, for example, a so-called thick copper substrate is known, which can release more heat through the copper by making the thickness of the copper (i.e., the copper pattern) forming the circuit thicker than before. However, the thick copper substrate is thicker as a whole, so there is a problem that it is not suitable for communication equipment that requires miniaturization and lightness.

[0004] As a printed circuit board with high heat dissipation, a so-called metal base substrate is also known. The metal base substrate is provided with a metal plate on one surface thereof so that more heat can be released through the metal plate. However, the metal base substrate has a problem of increasing the manufacturing cost of the communication device due to the increase in the number of steps during its manufacturing.

[0005] On the other hand, as with printed wiring boards, there are known components that contain a filler (filler) with high thermal conductivity as a main component of a resin and have high heat dissipation properties. However, materials containing fillers have poor processability and are therefore not suitable for the manufacture of printed wiring boards.

[0006] As a material that can solve these problems, a resin with high thermal conductivity is disclosed (Patent Document 1). Electronic materials used in high-speed communication equipment are required to have low dielectric loss in addition to high heat dissipation. The resin disclosed in Patent Document 1 has thermal conductivity and low dielectric loss.

[0007] Prior art literature

[0008] Patent Literature

[0009] Patent Document 1: U.S. Patent Application Publication No. 2019 / 0194408 Summary of the invention

[0010] Problems to be solved by the invention

[0011] However, the thermal conductivity of the resin disclosed in Patent Document 1 cannot be said to be sufficient and there is room for improvement. In addition, when manufacturing heat-dissipating components such as printed wiring boards, the monomer compound used as the resin raw material is expected to have good processability, and therefore is also required to have a low melting point and high solubility in organic solvents for processing.

[0012] An object of the present invention is to provide a novel compound which can be used as a constituent material of a printed wiring board and which has a low melting point and high solubility.

[0013] Another object of the present invention is to provide a composition comprising the novel compound and capable of providing a cured product having high thermal conductivity.

[0014] Means for solving problems

[0015] The present invention adopts the following configuration.

[0016] [1] A vinyl compound represented by formula (1) or formula (2).

[0017] [Chemical formula 1]

[0018]

[0019] (Where,

[0020] R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and a plurality of Rs may be the same or different from each other.

[0021] 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 formed by two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocyclic rings) connected by a single bond, an m-valent group formed by two or more substituted or unsubstituted cycloalkane rings connected by a single bond, an m-valent group formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings connected by a single bond, a substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group, R 1 (OR 2 - ) The group shown in 3, R 1 (R 2 - ) The group shown in 3, R 3 C (OR 2 - ) a group represented by 3, or R 3 C(R 2 - ) The group shown in 3,

[0022] R1 is a substituted or unsubstituted trivalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups),

[0023] R 2 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, -R 4 (R 5 ) p R 4 - The group shown, or - (R 6 O) q R 6 - The groups shown, multiple R 2 They can be the same or different from each other.

[0024] R 3 is a hydrogen atom or a methyl group,

[0025] R 4 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, and a plurality of R 4 They can be the same or different from each other.

[0026] R 5 is a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups). When p is 2 or 3, multiple R 5 They can be the same or different from each other.

[0027] R 6 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, and a plurality of R 6 They can be the same or different from each other.

[0028] p is an integer from 1 to 3,

[0029] q is an integer from 1 to 3,

[0030] For X 1 The bonding position of

[0031] is bonded to R 1 The bonding position of the oxygen atom and R 1 The bonding position of 3 The bonding position of the oxygen atom of C or R 3 The bonding position of C.

[0032] A 2The divalent group is 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 heterocyclic rings) are connected by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are connected by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are connected by a single bond, or one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are connected by a single bond. A divalent group formed by a single bond, a divalent group formed by a single bond between one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloolefin rings, a divalent group formed by a single bond between one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings, a divalent group formed by a single bond between 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, -B 1 Y 1 B 2 - The groups shown, -B 1 Y 1 B 2 Y 2 B 3 - The group shown, or -B 1 Y 1 B 2 Y 2 B 3 Y 3 B 4 - The groups shown, multiple A 2 They can be the same or different from each other.

[0033] B 1 ~B 4Each of the above is 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 heterocyclic 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 two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, or one or more substituted or unsubstituted aromatic rings and one a divalent group in which at least one substituted or unsubstituted cycloalkane ring is linked via a single bond, a divalent group in which at least one substituted or unsubstituted aromatic ring is linked to at least one substituted or unsubstituted cycloalkene ring via a single bond, a divalent group in which at least one substituted or unsubstituted cycloalkane ring is linked to at least one substituted or unsubstituted cycloalkene ring via a single bond, or a divalent group in which at least one substituted or unsubstituted aromatic ring is linked to at least one substituted or unsubstituted cycloalkane ring and at least one substituted or unsubstituted cycloalkene ring via a single bond,

[0034] Y 1 ~Y 3 are each an ester group, a carbonyl group, or an ether group,

[0035] For X 1 The bonding position of

[0036] is the bonding position to the acryloyloxy group, methacryloyloxy group, or vinylbenzyloxy group in formula (1), or is the bonding position to the acryloyloxyalkoxy group, methacryloyloxyalkoxy group, or vinylbenzyloxyalkoxy group in formula (2),

[0037] X 1 is a single bond, an ester group, a carbonyl group, or an ether group, and multiple X 1 They can be the same or different from each other.

[0038] m is an integer from 3 to 6,

[0039] n is an integer from 1 to 20, and multiple n's may be the same or different.)

[0040] [2] The vinyl compound according to [1], wherein A 1 and A 2 It is a group having 14 or less carbon atoms (the above carbon number does not include the carbon number of the substituent).

[0041] [3] The vinyl compound according to [1] or [2], which is used for a printed wiring board.

[0042] [4] A vinyl composition comprising the vinyl compound described in any one of [1] to [3].

[0043] [5] A cured vinyl resin obtained by curing the vinyl compound described in any one of [1] to [3] or the vinyl composition described in [4].

[0044] [6] A prepreg comprising the vinyl compound or semi-cured product thereof described in any one of [1] to [3] or the vinyl composition or semi-cured product thereof described in [4], and a fibrous base material.

[0045] [7] A resin-coated film comprising a resin layer and a support film, wherein the resin layer comprises the vinyl compound or semi-cured product thereof described in any one of [1] to [3], or the vinyl composition or semi-cured product thereof described in [4].

[0046] [8] A metal foil with a resin, comprising a resin layer and a metal foil, wherein the resin layer comprises the vinyl compound or semi-cured product thereof described in any one of [1] to [3], or the vinyl composition or semi-cured product thereof described in [4].

[0047] [9] A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the vinyl compound described in any one of [1] to [3] or a cured product of the vinyl composition described in [4].

[0048]

[10] A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the prepreg according to [6].

[0049]

[11] A printed wiring board comprising an insulating layer and a conductive wiring, wherein the insulating layer comprises a cured product of the vinyl compound described in any one of [1] to [3], or a cured product of the vinyl composition described in [4].

[0050]

[12] A printed wiring board comprising an insulating layer and conductive wiring, wherein the insulating layer comprises a cured product of the prepreg described in [6].

[0051] Effects of the Invention

[0052] According to the present invention, a novel compound which can be used as a constituent material of a printed wiring board and which exhibits a low melting point and high solubility can be provided.

[0053] In addition, a composition can be provided which contains the novel compound and can provide a cured product having high thermal conductivity. BRIEF DESCRIPTION OF THE DRAWINGS

[0054] Figure 1This is a cross-sectional view schematically showing an example of a laminate structure obtained using the vinyl compound according to one embodiment of the present invention.

[0055] Figure 2 This is a cross-sectional view schematically showing another example of a laminate structure obtained using the vinyl compound according to one embodiment of the present invention.

[0056] Figure 3 This is a cross-sectional view schematically showing another example of a laminate structure obtained using the vinyl compound according to one embodiment of the present invention.

[0057] Figure 4 This is a cross-sectional view schematically showing another example of a laminate structure obtained using the vinyl compound according to one embodiment of the present invention. DETAILED DESCRIPTION

[0058] Hereinafter, preferred embodiments of the present invention will be described in detail.

[0059] <<Vinyl compounds>>

[0060] The vinyl compound of this embodiment is represented by formula (1) or formula (2).

[0061] [Chemical formula 2]

[0062]

[0063] In the formula (1) and the formula (2), R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and a plurality of Rs may be the same as or different from each other.

[0064] In formula (1) and formula (2), preferably at least one of the m Rs is a vinylbenzyl group, more preferably m-1 of the m Rs is a vinylbenzyl group, and even more preferably all of the m Rs are vinylbenzyl groups.

[0065] The vinylbenzyl group represented by R is o-vinylbenzyl, m-vinylbenzyl, or p-methylbenzyl, preferably m-vinylbenzyl or p-methylbenzyl, and more preferably m-vinylbenzyl from the viewpoint of lowering the melting point of the vinyl compound. It should be noted that the positions of the vinyl groups of the m vinylbenzyl groups in formula (1) or (2) may be the same or different.

[0066] In formula (1) and formula (2), A 1is 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 formed by two or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocyclic rings) connected by a single bond, an m-valent group formed by two or more substituted or unsubstituted cycloalkane rings connected by a single bond, an m-valent group formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings connected by a single bond, a substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group, R 1 (OR 2 - ) The group shown in 3, R 1 (R 2 - ) The group shown in 3, R 3 C (OR 2 - ) a group represented by 3, or R 3 C(R 2 - ) The group shown in 3.

[0067] A 1 The substituted or unsubstituted m-valent aromatic group shown is a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted aromatic ring.

[0068] 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, heteroatoms other than nitrogen atoms, such as oxygen atoms and sulfur atoms, may be mentioned as heteroatoms contained in the heterocyclic ring. From the viewpoint of suppressing dielectric loss or reducing dielectric loss tangent, the aromatic ring preferably does not contain heteroatoms.

[0069] A 1 The substituted or unsubstituted m-valent aromatic group shown is preferably a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted monocyclic or condensed aromatic ring, and more preferably a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted monocyclic aromatic ring.

[0070] A 1 The carbon number of the unsubstituted m-valent aromatic group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and further preferably 6 to 14. The carbon number of the unsubstituted aromatic ring has the same meaning as the carbon number of the unsubstituted m-valent aromatic group, and preferred aspects thereof are also the same.

[0071] Specific examples of the unsubstituted aromatic ring include benzene, naphthalene, anthracene, phenanthrene, pyrene, benzo[9,10]phenanthrene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene, and benzene is preferred.

[0072] In A 1 When the m-valent aromatic group shown has a substituent, that is, when the aromatic ring has a substituent, the substituent is preferably a substituent other than a hydroxyl group, for example, one or more groups selected from an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms.

[0073] As the alkyl group having 1 to 20 carbon atoms, a known alkyl group may be used. Specific examples of the alkyl group 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-eicosyl. The number of carbon atoms in the alkyl group is preferably 1 to 8, more preferably 1 to 4. Specific examples of these preferred alkyl groups are the same as the alkyl groups having the corresponding number of carbon atoms in the specific examples described above.

[0074] As the alkoxy group having 1 to 20 carbon atoms, a known alkoxy group may be used. Specific examples of the alkoxy group having 1 to 20 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, isobutoxy, n-pentoxy, neopentoxy, n-hexoxy, n-octoxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-dodecyloxy, n-tetradecyloxy, n-hexadecyloxy, n-octadecyloxy, and n-eicosyloxy. The number of carbon atoms in the alkoxy group is preferably 1 to 8, more preferably 1 to 4. Specific examples of these preferred alkyl groups are the same as the alkyl groups having the corresponding number of carbon atoms in the specific examples described above.

[0075] As A 1 Suitable specific examples of the unsubstituted m-valent aromatic group shown in For X 1 bonding position. ).

[0076] [Chemical formula 3]

[0077]

[0078] A 1 The substituted or unsubstituted m-valent cycloalkane group shown is a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted cycloalkane ring.

[0079] 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 heteroatoms contained in the heterocyclic ring include oxygen atoms, nitrogen atoms, and sulfur atoms. From the viewpoint of suppressing dielectric loss or reducing dielectric loss tangent, the cycloalkane ring preferably does not contain heteroatoms. The cycloalkane ring is preferably a monocyclic ring or a condensed ring, and more preferably a monocyclic ring.

[0080] In the present specification, the cycloalkane group and the cycloalkane ring may be a cis isomer, a trans isomer, or a mixture thereof. In the case of a mixture, the ratio of the trans isomer is preferably higher.

[0081] The carbon number of the unsubstituted m-valent cycloalkane group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and further preferably 6 to 14. The carbon number of the unsubstituted cycloalkane ring has the same meaning as that of the unsubstituted m-valent cycloalkane group, and preferred embodiments thereof are also the same.

[0082] Specific examples of the unsubstituted cycloalkane ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane, cyclopentadecane, cyclohexadecane, cycloheptadecane, cyclooctadecane, cyclononadecane, cycloeicosane, decahydronaphthalene, adamantane, oxetane, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 1,3-dioxane, aziridine, pyrrolidine, piperidine, piperazine, morpholine, tetrahydrothiophene, and cyclopentyl sulfide.

[0083] In A 1 When the m-valent cycloalkane group shown in FIG. 1 has a substituent, that is, when the cycloalkane ring has a substituent, the substituent is the same as A. 1 The substituents which the m-valent aromatic group shown may have have the same meanings.

[0084] As A 1 Suitable specific examples of the substituted or unsubstituted m-valent cycloalkane group shown in For X 1 bonding position. ).

[0085] [Chemical formula 4]

[0086]

[0087] A 1The m-valent group formed by connecting two or more substituted or unsubstituted aromatic rings by a single bond is a group obtained by removing m hydrogen atoms from any position of a compound formed by connecting two or more substituted or unsubstituted aromatic rings by a single bond. The substituted or unsubstituted aromatic ring connected by a single bond has the same meaning 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 the connecting bond of the substituted or unsubstituted m-valent aromatic group), and its preferred embodiment is also the same.

[0088] In the compound having two or more substituted or unsubstituted aromatic rings linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0089] Specific examples of the compound in which two or more unsubstituted aromatic rings are linked by a single bond include biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, m-quaterphenyl, and p-quaterphenyl.

[0090] A 1 The m-valent group formed by connecting two or more substituted or unsubstituted cycloalkane rings by a single bond is a group obtained by removing m hydrogen atoms from any position of a compound formed by connecting two or more substituted or unsubstituted cycloalkane rings by a single bond. The substituted or unsubstituted cycloalkane ring connected 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 bonding a hydrogen atom to the connecting bond of the substituted or unsubstituted m-valent cycloalkane group), and its preferred embodiment is also the same.

[0091] In the compound in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0092] Specific examples of the compound in which two or more unsubstituted cycloalkane rings are linked by a single bond include cyclopropylcyclohexane, bicyclohexylcyclohexane, 1,3-dicyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

[0093] A 1The m-valent group formed by connecting one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings by a single bond is a group obtained by removing m hydrogen atoms from any position of a compound formed by connecting one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings by a single bond. The substituted or unsubstituted aromatic ring and the substituted or unsubstituted cycloalkane ring connected by a single bond have the same meaning 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 a hydrogen atom bonded to the connecting bond of the 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 a hydrogen atom bonded to the connecting bond of the substituted or unsubstituted m-valent cycloalkane group), and the preferred embodiments thereof are also the same.

[0094] In the 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 number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited if it is 1 or more, and 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 a single bond is not particularly limited if it is 1 or more, and 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 and the number of substituted or unsubstituted cycloalkane rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0095] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are linked by a single bond include 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.

[0096] A 1 The substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group shown is a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted chain saturated aliphatic hydrocarbon, and is preferably a group obtained by removing one hydrogen atom bonded to each of m different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon.

[0097] In the present specification, the chain saturated aliphatic hydrocarbon may be a straight chain saturated aliphatic hydrocarbon or a branched chain saturated aliphatic hydrocarbon.

[0098] A 1The substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group is preferably a group obtained by removing m hydrogen atoms from any position of a substituted or unsubstituted branched aliphatic hydrocarbon.

[0099] A 1 The number of carbon atoms in the unsubstituted m-valent chain saturated aliphatic hydrocarbon group is not particularly limited, but is preferably 1 to 10, more preferably 3 to 9, and even more preferably 5 to 8.

[0100] As A 1 Specific examples of the unsubstituted linear saturated aliphatic hydrocarbons 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, preferably 2,2-dimethylpropane.

[0101] In A 1 When the m-valent chain saturated aliphatic hydrocarbon group shown in FIG. 1 has a substituent, that is, when the chain saturated aliphatic hydrocarbon has a substituent, the substituent is the same as A. 1 The substituents which the m-valent aromatic group shown may have have the same meanings.

[0102] As A 1 Suitable specific examples of the substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group include the following groups ( For X 1 bonding position. ).

[0103] [Chemical formula 5]

[0104]

[0105] In A 1 For R 1 (OR 2 - ) The group shown in 3 or R 1 (R 2 - ) In the case of the group shown in 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 chain saturated aliphatic hydrocarbon group, -R 4 (R 5 ) p R 4 - The group shown, or - (R 6O) q R 6 - The group shown; R 4 is a substituted or unsubstituted divalent chain 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 chain saturated aliphatic hydrocarbon group; p is an integer of 1 to 3; q is an integer of 1 to 3. 2 They may be the same or different from each other. 4 They may be the same or different from each other. When p is 2 or 3, multiple R 5 They may be the same or different from each other. 6 They may be the same or different from each other. 2 Among the groups shown, For X 1 The bonding position of A 1 For R 1 (OR 2 - ) In the case of the group shown in 3, is bonded to R 1 The bonding position of the oxygen atom in A 1 For R 1 (R 2 - ) In the case of the group shown in 3, For R 1 bonding position.

[0106] R 1 The substituted or unsubstituted trivalent aromatic group shown in 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in the figure (that is, a substituted or unsubstituted aromatic ring formed by a hydrogen atom bonded to the connecting bond of the substituted or unsubstituted m-valent aromatic group) has the same meaning, and its preferred embodiment is also the same.

[0107] R 2 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown in 1The substituted or unsubstituted chain saturated aliphatic hydrocarbon mentioned in the description of the substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group shown in the above (i.e., a substituted or unsubstituted chain saturated aliphatic hydrocarbon in which a hydrogen atom is bonded to a connecting bond of the substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group) has the same meaning as R 2 Preferred embodiments and specific examples of the substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group are as follows.

[0108] R 2 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown is preferably a group obtained by removing one hydrogen atom bonded to two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon, respectively, and is also preferably a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

[0109] R 2 The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group is not particularly limited, but is preferably 1 to 20, more preferably 2 to 16, and even more preferably 3 to 12.

[0110] As R 2 Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group include trimethylene, tetramethylene, pentamethylene, hexamethylene, 3-methylpentane-1,5-diyl, heptamethylene, octamethylene, and dodecamethylene.

[0111] In R 2 When the divalent chain saturated aliphatic hydrocarbon group shown in 1 The substituents which the m-valent aromatic group shown may have have the same meanings and preferred aspects thereof are also the same.

[0112] In R 2 for -R 4 (R 5 ) p R 4 - In the case of the groups shown, R 4 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group and R 2 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown has the same meaning, and preferred embodiments and specific examples thereof are as follows.

[0113] R 4The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown is preferably a group obtained by removing one hydrogen atom bonded to two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon, respectively, and is also preferably a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

[0114] R 4 The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group is not particularly limited, but is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1.

[0115] As R 4 Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group.

[0116] In R 2 for -R 4 (R 5 ) p R 4 - In the case of the groups shown, R 5 The substituted or unsubstituted divalent aromatic group shown in is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in the figure (that is, a substituted or unsubstituted aromatic ring formed by a hydrogen atom bonded to the connecting bond of the substituted or unsubstituted m-valent aromatic group) has the same meaning, and its preferred embodiment is also the same.

[0117] As -R 4 (R 5 ) p R 4 - Preferable specific examples of the group shown include the following groups.

[0118] [Chemical formula 6]

[0119]

[0120] In R 2 for - (R 6 O) q R 6 - In the case of the groups shown, R 6The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group and R 2 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown has the same meaning, and preferred embodiments and specific examples thereof are as follows.

[0121] R 6 The substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group shown is preferably a group obtained by removing one hydrogen atom bonded to two different carbon atoms of a substituted or unsubstituted chain saturated aliphatic hydrocarbon, respectively, and is also preferably a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted straight-chain saturated aliphatic hydrocarbon.

[0122] R 6 The number of carbon atoms in the unsubstituted divalent chain saturated aliphatic hydrocarbon group is not particularly limited, but is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 to 2.

[0123] As R 6 Specific examples of the unsubstituted divalent chain saturated aliphatic hydrocarbon group include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group.

[0124] In R 2 for - (R 6 O) q R 6 - In the case of the group represented by , q is an integer of 1 to 3, and preferably 2.

[0125] As - (R 6 O) q R 6 - Suitable specific examples of the group shown include -CH2CH2OCH2CH2- , -(CH2CH2O)2CH2CH2- , -CH(CH3)CH2OCH(CH3)CH2- ,and -(CH(CH3)CH2O)2CH(CH3)CH2- wait.

[0126] As R 1 (OR 2- ) As suitable specific examples of the group represented by 3, the following groups can be mentioned.

[0127] [Chemical formula 7]

[0128]

[0129] As R 1 (R 2 - ) As suitable specific examples of the group represented by 3, the following groups can be mentioned.

[0130] [Chemical formula 8]

[0131]

[0132] In A 1 For R 3 C(OR 2 - )3 or R 3 C(R 2 - ) In the case of the group shown in 3, R 2 With R 1 (OR 2 - ) R in the group shown in 3 2 The meaning is the same, and the preferred mode is also the same. In this case, in R 2 Among the groups shown, For X 1 The bonding position of A 1 For R 3 C(OR 2 - ) In the case of the group shown in 3, is bonded to R 3 The bonding position of the oxygen atom of C is 1 For R 3 C(R 2 - ) In the case of the group shown in 3, For R 3 C bonding position. In addition, R 3 A hydrogen atom or a methyl group.

[0133] As R 3 C(OR 2 - ) As suitable specific examples of the group represented by 3, the following groups can be mentioned.

[0134] [Chemical formula 9]

[0135]

[0136] [Chemical formula 10]

[0137]

[0138] As R 3 C(R 2 - ) As suitable specific examples of the group represented by 3, the following groups can be mentioned.

[0139] [Chemical formula 11]

[0140]

[0141] [Chemical formula 12]

[0142]

[0143] In formula (1) and formula (2), A 2 The divalent group is 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 heterocyclic rings) are connected by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are connected by a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are connected by a single bond, or one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are connected by a single bond. A divalent group formed by a single bond, a divalent group formed by a single bond between one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) and one or more substituted or unsubstituted cycloolefin rings, a divalent group formed by a single bond between one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings, a divalent group formed by a single bond between 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, -B 1 Y 1 B 2 - The groups shown, -B 1 Y 1 B 2 Y 2 B 3 - The group shown, or -B 1 Y 1 B 2 Y 2 B 3 Y 3 B 4 - The groups shown. 2 They may be the same or different from each other. 2 Among the groups shown, For X 1 The bonding position of It is a bonding position to an acryloyloxy group, a methacryloyloxy group, or a vinylbenzyloxy group in formula (1), or a bonding position to an acryloyloxyalkoxy group, a methacryloyloxyalkoxy group, or a vinylbenzyloxyalkoxy group in formula (2).

[0144] From the viewpoint that the degree of orientation becomes high due to the π-π stacking interaction, and as a result, a cured product having high thermal conductivity can be provided, A 2 Preferably contains a double bond. Thus, A 2 Preferably, it is 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 are linked by a single bond to one or more substituted or unsubstituted cycloalkane rings, a divalent group in which one or more substituted or unsubstituted aromatic rings are linked by a single bond to one or more substituted or unsubstituted cycloalkene rings, a divalent group in which one or more substituted or unsubstituted cycloalkane rings are linked by a single bond to one or more substituted or unsubstituted cycloalkene rings, or a divalent group in which one or more substituted or unsubstituted aromatic rings (excluding nitrogen-containing aromatic heterocycles) are linked by a single bond to one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings. In addition, from the viewpoint of ease of synthesis, A 2Preferably, it 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, or 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 one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkene rings are linked by a single bond. The divalent group is 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.

[0145] A 2 The substituted or unsubstituted divalent aromatic group shown in is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in FIG. 1 (i.e., a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a connecting bond of a substituted or unsubstituted m-valent aromatic group) has the same meaning and its preferred embodiment is also the same. 2 Preferred embodiments of the substituted or unsubstituted divalent aromatic group are as follows.

[0146] A 2 The substituted or unsubstituted divalent aromatic group shown is preferably a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted monocyclic or condensed aromatic ring, and is also preferably a group obtained by removing two hydrogen atoms from any position of an unsubstituted aromatic ring.

[0147] A 2 The number of carbon atoms in the substituted or unsubstituted divalent aromatic group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0148] Specific examples of the unsubstituted aromatic ring include benzene, naphthalene, anthracene, phenanthrene, pyrene, benzo[9,10]phenanthrene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene, and preferably benzene or naphthalene.

[0149] In A 2When the divalent aromatic group shown has a substituent, the substituent is preferably selected from an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms.

[0150] As mentioned above, A 2 The divalent aromatic group shown is preferably unsubstituted, or, when having a substituent, the substituent is selected from an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms. 2 When the divalent aromatic group is unsubstituted or has a substituent with little steric hindrance, the π-π stacking interaction between the mesogenic skeletons is less likely to be inhibited, the degree of orientation becomes high, and as a result, a cured product having high thermal conductivity can be provided.

[0151] As A 2 Preferred specific examples of the substituted or unsubstituted divalent aromatic group include the following groups.

[0152] [Chemical formula 13]

[0153]

[0154] A 2 The substituted or unsubstituted divalent cycloalkane group shown in 1 The substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloalkane ring in which a hydrogen atom is bonded to a connecting bond of the substituted or unsubstituted m-valent cycloalkane group) has the same meaning as well as the same preferred embodiment.

[0155] As A 2 Preferred specific examples of the substituted or unsubstituted divalent cycloalkane group include the following groups.

[0156] [Chemical formula 14]

[0157]

[0158] A 2 The substituted or unsubstituted divalent cycloolefin group shown is a group obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted cycloolefin ring.

[0159] In the present specification, the cycloolefin ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring. When the cycloolefin ring is a heterocyclic ring, examples of heteroatoms contained in the heterocyclic ring include oxygen atoms, nitrogen atoms, and sulfur atoms. From the viewpoint of suppressing dielectric loss or reducing dielectric loss tangent, the cycloolefin ring preferably does not contain heteroatoms. The cycloolefin ring is preferably a monocyclic ring or a condensed ring, more preferably a monocyclic ring. The number of double bonds contained in one cycloolefin ring is not particularly limited, and is preferably 1 to 3, more preferably 1 to 2, and further preferably 1. In addition, the position of the double bonds contained in the cycloolefin ring is not particularly limited.

[0160] In the present specification, the cycloolefin group and the cycloolefin ring may be a cis-isomer, a trans-isomer, or a mixture thereof. In the case of a mixture, the ratio of the trans-isomer is preferably higher.

[0161] The carbon number of the unsubstituted divalent cycloolefin group is not particularly limited, but is preferably 4 to 20, more preferably 5 to 16, and further preferably 6 to 14. The carbon number of the unsubstituted cycloolefin ring has the same meaning as that of the unsubstituted divalent cycloolefin group, and preferred embodiments thereof are also the same.

[0162] Specific examples of the unsubstituted cycloolefin ring include cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclopentadiene, 1,3-cyclohexadiene, 1,4-cyclohexadiene, 1,3-cycloheptadiene, 1,4-cycloheptadiene, 1,3-cyclooctadiene, 1,5-cyclooctadiene, 1,6-cyclodecadiene, 1,5-cyclododecadiene, 1,3,5-cycloheptatriene, 1,3,5-cyclooctatriene, and 1,5,9-cyclododecatriene.

[0163] When the divalent cycloolefin group has a substituent, that is, when the cycloolefin ring has a substituent, the substituent and A 1 The substituents which the m-valent aromatic group shown may have have the same meanings.

[0164] As A 2 Preferred specific examples of the substituted or unsubstituted divalent cycloolefin group include the following groups.

[0165] [Chemical formula 15]

[0166]

[0167] A 2 The divalent group formed by two or more substituted or unsubstituted aromatic rings connected by a single bond is a group obtained by removing two hydrogen atoms from any position of the compound formed by two or more substituted or unsubstituted aromatic rings connected by a single bond. 1The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in the figure (that is, a substituted or unsubstituted aromatic ring formed by a hydrogen atom bonded to the connecting bond of the substituted or unsubstituted m-valent aromatic group) has the same meaning, and its preferred embodiment is also the same.

[0168] In the compound having two or more substituted or unsubstituted aromatic rings linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0169] Specific examples of the compound in which two or more unsubstituted aromatic rings are linked by a single bond include biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, m-quaterphenyl, and p-quaterphenyl.

[0170] A 2 The divalent group formed by connecting two or more substituted or unsubstituted cycloalkane rings via a single bond is a group obtained by removing two hydrogen atoms from any position of a compound formed by connecting two or more substituted or unsubstituted cycloalkane rings via a single bond. 1 The substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloalkane ring in which a hydrogen atom is bonded to a connecting bond of the m-valent cycloalkane group) has the same meaning and preferred embodiments thereof are also the same.

[0171] In the compound in which two or more substituted or unsubstituted cycloalkane rings are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0172] Specific examples of the compound in which two or more unsubstituted cycloalkane rings are linked by a single bond include cyclopropylcyclohexane, bicyclohexylcyclohexane, 1,3-dicyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

[0173] A 2 The divalent group formed by connecting two or more substituted or unsubstituted cycloolefin rings via a single bond is a group obtained by removing two hydrogen atoms from any position of a compound formed by connecting two or more substituted or unsubstituted cycloolefin rings via a single bond. 2The substituted or unsubstituted cycloolefin ring mentioned in the description of the substituted or unsubstituted divalent cycloolefin group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloolefin ring in which a hydrogen atom is bonded to the connecting bond of the substituted or unsubstituted divalent cycloolefin group) has the same meaning, and preferred embodiments thereof are also the same.

[0174] In the compound having two or more substituted or unsubstituted cycloolefin rings linked by a single bond, the number of substituted or unsubstituted cycloolefin rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0175] A 2 The divalent group formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings connected by a single bond as shown in the formula is a group obtained by removing two hydrogen atoms from any position of a compound formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings connected by a single bond. The substituted or unsubstituted aromatic ring and the substituted or unsubstituted cycloalkane ring connected by a single bond are respectively connected to A 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in the figure (that is, a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to the connecting bond of the substituted or unsubstituted m-valent aromatic group) and A 1 The substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloalkane ring in which a hydrogen atom is bonded to a connecting bond of the substituted or unsubstituted m-valent cycloalkane group) has the same meaning as well as the same preferred embodiment.

[0176] 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 a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 1 or more, and 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 a single bond is not particularly limited as long as it is 1 or more, and 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 and the number of substituted or unsubstituted cycloalkane rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0177] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are linked by a single bond include 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.

[0178] As A 2 Preferred specific examples of the divalent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are linked via a single bond include the following groups.

[0179] [Chemical formula 16]

[0180]

[0181] A 2 The divalent group formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloolefin rings connected by a single bond as shown in the formula is a group obtained by removing two hydrogen atoms from any position of a compound formed by one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloolefin rings connected by a single bond. The substituted or unsubstituted aromatic ring and the substituted or unsubstituted cycloolefin ring connected by a single bond are respectively connected to A 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in the figure (that is, a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to the connecting bond of the substituted or unsubstituted m-valent aromatic group) and A 2 The substituted or unsubstituted cycloolefin ring mentioned in the description of the substituted or unsubstituted divalent cycloolefin group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloolefin ring in which a hydrogen atom is bonded to the connecting bond of the substituted or unsubstituted divalent cycloolefin group) has the same meaning, and preferred embodiments thereof are also the same.

[0182] As A 2 Preferred specific examples of the divalent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloolefin rings are linked via a single bond include the following groups.

[0183] [Chemical formula 17]

[0184]

[0185] In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloolefin rings are linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited if it is 1 or more, and is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. The number of substituted or unsubstituted cycloolefin rings linked by a single bond is not particularly limited if it is 1 or more, and 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 and the number of substituted or unsubstituted cycloolefin rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0186] A 2 The divalent group formed by one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloolefin rings connected by a single bond as shown in the formula is a group obtained by removing two hydrogen atoms from any position of a compound formed by one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloolefin rings connected by a single bond. The substituted or unsubstituted cycloalkane ring and the substituted or unsubstituted cycloolefin ring connected by a single bond are respectively connected to A 1 The substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloalkane ring in which a hydrogen atom is bonded to a connecting bond of the substituted or unsubstituted m-valent cycloalkane group) and A 2 The substituted or unsubstituted cycloolefin ring mentioned in the description of the substituted or unsubstituted divalent cycloolefin group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloolefin ring in which a hydrogen atom is bonded to the connecting bond of the substituted or unsubstituted divalent cycloolefin group) has the same meaning, and preferred embodiments thereof are also the same.

[0187] In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloolefin rings are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings linked by a single bond is not particularly limited as long as it is 1 or more, and is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. The number of substituted or unsubstituted cycloalkene rings linked by a single bond is not particularly limited as long as it is 1 or more, and 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 the number of substituted or unsubstituted cycloalkene rings linked by a single bond is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0188] A 2The divalent group formed by 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 connected by a single bond as shown is a group obtained by removing two hydrogen atoms from any position of a compound formed by 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 connected by a single bond. The substituted or unsubstituted aromatic ring, substituted or unsubstituted cycloalkane ring, and substituted or unsubstituted cycloalkene ring connected by a single bond are respectively connected to A 1 The substituted or unsubstituted aromatic ring mentioned in the description of the substituted or unsubstituted m-valent aromatic group shown in (that is, a substituted or unsubstituted aromatic ring formed by bonding a hydrogen atom to a connecting bond of the substituted or unsubstituted m-valent aromatic group), A 1 A substituted or unsubstituted cycloalkane ring mentioned in the description of the substituted or unsubstituted m-valent cycloalkane group (that is, a substituted or unsubstituted cycloalkane ring in which a hydrogen atom is bonded to a connecting bond of the substituted or unsubstituted m-valent cycloalkane group), and A 2 The substituted or unsubstituted cycloolefin ring mentioned in the description of the substituted or unsubstituted divalent cycloolefin group shown in FIG. 1 (i.e., a substituted or unsubstituted cycloolefin ring in which a hydrogen atom is bonded to the connecting bond of the substituted or unsubstituted divalent cycloolefin group) has the same meaning, and preferred embodiments thereof are also the same.

[0189] 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 a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited if it is 1 or more, and 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 a single bond is not particularly limited if it is 1 or more, and is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. The number of substituted or unsubstituted cycloalkene rings linked by a single bond is not particularly limited if it is 1 or more, and is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. In addition, the total of the number of substituted or unsubstituted aromatic rings, the number of substituted or unsubstituted cycloalkane rings, and the number of substituted or unsubstituted cycloalkene rings linked by a single bond is preferably 3 to 10, more preferably 3 to 4, and even more preferably 3.

[0190] In A 2 for -B 1 Y 1 B 2 - The groups shown, -B 1 Y1 B 2 Y 2 B 3 - The group shown, or -B 1 Y 1 B 2 Y 2 B 3 Y 3 B 4 - In the case of the group shown, B 1 ~B 4 Each of the above is 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 heterocyclic 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 two or more substituted or unsubstituted cycloalkene rings are linked by a single bond, or one or more substituted or unsubstituted aromatic rings and one Y is a divalent group in which at least one substituted or unsubstituted cycloalkane ring is linked via a single bond, a divalent group in which at least one substituted or unsubstituted aromatic ring is linked to at least one substituted or unsubstituted cycloalkene ring via a single bond, a divalent group in which at least one substituted or unsubstituted cycloalkane ring is linked to at least one substituted or unsubstituted cycloalkene ring via a single bond, or a divalent group in which at least one substituted or unsubstituted aromatic ring is linked to at least one substituted or unsubstituted cycloalkane ring and at least one substituted or unsubstituted cycloalkene ring via a single bond; 1 ~Y 3 Each is an ester group, a carbonyl group, or an ether group.

[0191] B 1 ~B 4a 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 heterocyclic 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 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 aromatic rings are linked by a single bond A divalent group in which at least one substituted or unsubstituted cycloalkane ring is connected to at least one substituted or unsubstituted cycloalkene ring through a single bond, a divalent group in which at least one substituted or unsubstituted cycloalkane ring is connected to at least one substituted or unsubstituted cycloalkene ring through a single bond, a divalent group in which at least one substituted or unsubstituted cycloalkane ring is connected to at least one substituted or unsubstituted cycloalkene ring through a single bond, and a divalent group in which at least one substituted or unsubstituted aromatic ring, at least one substituted or unsubstituted cycloalkane ring and at least one substituted or unsubstituted cycloalkene ring are connected to each other through a single bond. 2 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 heterocyclic 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 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 substituted or The divalent group in which unsubstituted cycloalkane rings are linked via a single bond, the divalent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkene rings are linked via a single bond, the divalent group in which one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings are linked via a single bond, and the 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 via a single bond have the same meaning, and preferred embodiments thereof are also the same.

[0192] Y 1 ~Y 3 Each is an ester group (—COO— or —OCO—), a carbonyl group (—CO—), or an ether group (—O—), and is preferably an ester group.

[0193] From the viewpoint of obtaining a vinyl compound with a low melting point, A 1 and A 2Among the above groups, groups having 3 to 14 carbon atoms or groups having 6 to 14 carbon atoms are also preferred. However, the carbon number does not include the carbon number of the substituent.

[0194] 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, more preferably an ester group. 1 They can be the same or different from each other.

[0195] In formula (1) and formula (2), m is an integer of 3 to 6, preferably an integer of 3 to 5, more preferably 3 or 4, and even more preferably 3.

[0196] In formula (2), n is an integer of 1 to 20, preferably an integer of 1 to 12, more preferably an integer of 1 to 8, and further preferably an integer of 2 to 6. A plurality of n may be the same as or different from each other.

[0197] In this specification, the vinyl compound represented by formula (1) or (2) of this embodiment may be referred to as “vinyl compound (1)”. The vinyl compound (1) has a low melting point and high solubility.

[0198] The melting point of the vinyl compound (1) is more preferably less than 160° C., preferably 80° C. or more and less than 160° C., more preferably 90 to 155° C., and further preferably 100 to 155° C. When the melting point of the vinyl compound is within the above range, processing by melt kneading or the like becomes easy, and the energy required for processing can also be reduced.

[0199] The vinyl compound (1) has high solubility in an organic solvent when subjected to processing such as coating of a coating solution prepared by dissolving the vinyl compound in an organic solvent, and therefore has excellent workability and processability.

[0200] 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.

[0201] As shown in the examples described below, the vinyl compound (1) has a higher solubility in ether solvents than conventionally known vinyl compounds. Specifically, the vinyl compound 1 and the vinyl compound 2 of the examples have solubilities in ether solvents that are about 7 times and about 3 times higher than conventionally known vinyl compounds, respectively.

[0202] The vinyl compound (1) is polymerizable and can form a cured vinyl resin described below by polymerization (also referred to as "curing" in this specification). Therefore, the vinyl compound (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.

[0203] In formula (1), in A 1 When a chain saturated aliphatic hydrocarbon group is included, A 2 is the mesogenic skeleton in the vinyl compound (1). On the other hand, in the formula (1), 1 When there is no chain saturated aliphatic hydrocarbon group in A 1 , X 1 and A 2 The structure formed by the connection is a mesogenic skeleton in the vinyl compound (1). The mesogenic skeleton of the vinyl compound (1) has a larger number of connected hydrocarbon rings than a conventional mesogenic skeleton having a structure formed by connecting two hydrocarbon rings, and thus has a higher degree of orientation. The resin as a cured product of the vinyl compound (1) exhibits high thermal conductivity by having such a structure with a high degree of orientation.

[0204] On the other hand, resins having hydroxyl groups tend to have high dielectric loss. For example, a resin that is a cured product of a compound (monomer) having an epoxy group at the end has a hydroxyl group in the resin and has high dielectric loss. In contrast, the end of the vinyl compound (1) is not an epoxy group or a hydroxyl group but a vinyl group (vinyl group). Therefore, the cured product (polymer) of the vinyl compound (1) does not have a hydroxyl group and therefore exhibits low dielectric loss.

[0205] <<Method for producing vinyl compound>>

[0206] 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 the present specification) with a compound represented by formula (5) (sometimes referred to as “compound (B)” in the present specification) in the presence of a base.

[0207] [Chemical formula 18]

[0208]

[0209] (Where A 1 , X 1 , A 2 , m, and n respectively have the same meanings as above. )

[0210] XR (5)

[0211] (In the formula, X represents a halogen atom; R represents the same meaning as above.)

[0212] 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-hydroxyphenyl)benzene, 1-(4-hydroxyphenyl)-3,5-bis(3-methyl-4-hydroxyphenyl)benzene, 1-(3-methyl-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)benzene, and 1,3,5-tris(4-hydroxyphenyl)cyclohexane. )benzene, 1,3,5-tris(4-hydroxyphenyl)1,3,5-cyclohexanetricarboxylate, 1,3,5-tris(3-methyl-4-hydroxyphenyl)1,3,5-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)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) )benzene, 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-hydroxyphenylcarbonyl)cyclohexane, 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, their 2-hydroxyethyl ethers, their 3-hydroxypropyl ethers, and their 4-hydroxybutyl ethers. Compound (A) can be produced by a known organic synthesis method, such as an ester synthesis method, a ketone synthesis method, an ether synthesis method, or a method based on these methods, alone or in combination. ,

[0213] The above-mentioned X represents a halogen atom, and examples of the above-mentioned halogen atom include a chlorine atom, a bromine atom, an iodine atom and the like.

[0214] Examples of the 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. The compound (B) may be used alone or in any combination and ratio.

[0215] The amount of the compound (B) used is usually preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents, based on the amount of the compound (A).

[0216] The above-mentioned base may be any of an inorganic base and an organic base.

[0217] Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as sodium carbonate and potassium carbonate.

[0218] Examples of the organic base include pyridine, etc. The amount of the base used is preferably 2 to 5 equivalents relative to compound (A). When an organic base that is liquid under the reaction conditions is used, the organic base may be used in excess and also serve as a reaction solvent.

[0219] The reaction of compound (A) and compound (B) is usually carried out by mixing compound (A), compound (B) and a base in a solvent. The order of mixing is not particularly limited.

[0220] The above-mentioned solvent is not particularly limited as long as it is a solvent inactive to the reaction. From the aspect of easily suppressing the formation of by-products, a hydrophilic solvent is preferred. As the above-mentioned hydrophilic solvent, for example, alcohol solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, and propylene glycol; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone; ether solvents such as tetrahydrofuran, dioxane, methoxymethyl ether, and diethoxyethane, etc., alone or in a mixed solvent. In addition, when an organic base that is liquid under the reaction conditions is used as a base, the above-mentioned organic base can be used as a reaction solvent.

[0221] Among them, the solvent is preferably an ether solvent, an aprotic polar solvent, and a mixed solvent thereof, more preferably an aprotic polar solvent, and particularly preferably N,N-dimethylformamide.

[0222] The amount of the solvent used is preferably 1 to 20 mL, more preferably 2 to 10 mL, per 1 g of compound (A).

[0223] The reaction of the compound (A) and the compound (B) can be carried out via a halogen exchange reaction in the presence of a catalyst.

[0224] Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide.

[0225] When a catalyst is used, the amount thereof 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.

[0226] The reaction of 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 and the like. When a polymerization inhibitor is used, the amount used is preferably 0.002 to 0.05 times by weight, more preferably 0.004 to 0.02 times by weight, relative to the amount used of compound (B).

[0227] The reaction can be carried out under normal pressure or under reduced pressure. The reaction temperature is usually preferably 10 to 150° C. It should be noted that in this reaction, as the reaction proceeds, water is sometimes produced as a by-product. In this case, it is preferred to react while removing the by-product water outside the reaction system, preferably at a reaction temperature and reaction pressure at which water is removed azeotropically. The reaction time is usually preferably 1 to 24 hours.

[0228] After the reaction is completed, for example, the reaction solution is cooled, water or a mixed solvent containing water is added, the precipitated solid is filtered out, and a known post-treatment operation is performed once or twice as needed to obtain a 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; extracting (liquid separation) a solution in which the solid is dissolved, etc. The obtained vinyl compound (1) can be further purified by a conventional purification method as needed.

[0229] The structure of the obtained vinyl compound (1) can be confirmed by a known method such as a nuclear magnetic resonance (NMR) method.

[0230] <<Vinyl composition>>

[0231] The vinyl composition of the present embodiment contains a vinyl compound (1).

[0232] In this specification, the vinyl composition of this embodiment may be referred to as "vinyl composition (1)".

[0233] The vinyl composition (1) is curable and may contain only the vinyl compound (1) or may contain 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 below, the vinyl composition (1) is cured by heating. When curing the vinyl composition (1), pressure may be applied to the vinyl composition (1). The vinyl composition (1) may be suitably used for forming a constituent material such as an insulating layer of a printed wiring board or a heat dissipation material.

[0234] <Vinyl compounds (1)>

[0235] The vinyl composition (1) may contain one type of the vinyl compound (1) alone, or may contain two or more types in any combination and ratio.

[0236] When the vinyl composition (1) contains two or more vinyl compounds (1) in which two or more R in one molecule are vinyl benzyl groups, the two or more vinyl compounds (1) are preferably a mixture of a plurality of vinyl compounds (1) in which the positions of the vinyl groups of the vinyl benzyl groups as terminal groups are different and the parts other than the vinyl benzyl groups are the same.

[0237] For example, in a vinyl composition (1) containing two or more vinyl compounds (1) in which two or more R in one molecule are vinyl benzyl groups, when the number of moles of all vinyl benzyl groups in the vinyl compounds (1) in which two or more R in one molecule are vinyl benzyl groups is 100, the number of moles of vinyl benzyl groups in which the vinyl position is meta-position is preferably 30 to 90, more preferably 40 to 90, further preferably 50 to 90, further preferably 60 to 80, and particularly preferably 70 to 80. For example, the ratio of the number of moles of vinylbenzyl groups having a vinyl group at the para position to the number of moles of vinylbenzyl groups having a vinyl group at the meta position (the number of moles of paravinylbenzyl groups / the number of moles of metavinylbenzyl groups; in this specification, sometimes referred to as the "p / m ratio") is preferably 10 / 90 to 70 / 30, more preferably 10 / 90 to 60 / 40, further preferably 10 / 90 to 50 / 50, further preferably 20 / 80 to 40 / 60, and particularly preferably 20 / 80 to 30 / 70. By setting the number of moles of vinylbenzyl groups having a vinyl group at the meta position or the p / m ratio within the above range, the mixture of the vinyl compound (1) melts at a lower temperature, thereby improving the processability of the vinyl compound.

[0238] <Other ingredients>

[0239] Examples of the other components contained in the vinyl composition (1) include free radical initiators; fillers; additives; solvents; vinyl compounds other than the vinyl compound (1) (sometimes referred to as "other vinyl compounds" in this specification); resins other than polymers (cured products) of the vinyl compound (1) (sometimes referred to as "other resins" in this specification), and the like.

[0240] Examples of the additives include a silane coupling agent, a colorant, a low stress component, a release agent, an antioxidant, a defoaming agent, and a flow regulator.

[0241] Examples of the radical initiator include azo compounds and organic peroxides.

[0242] Examples of the filler include silica powders such as molten crushed silica powder, molten spherical silica powder, crystalline silica powder, and secondary agglomerated silica powder; metal oxides such as aluminum oxide, titanium oxide, zinc oxide, tungsten carbide, and magnesium oxide; glass fiber cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, and titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; mica, and the like.

[0243] As said silane coupling agent, γ-glycidoxypropyltrimethoxysilane etc. are mentioned, for example.

[0244] Examples of the colorant include carbon black and the like.

[0245] Examples of the low stress component include silicone oil and silicone rubber.

[0246] Examples of the release agent include natural wax, synthetic wax, higher fatty acid, metal salt of higher fatty acid, paraffin wax, and the like.

[0247] Examples of the solvent contained in the vinyl composition (1) include ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as dimethyl sulfoxide and N-methylpyrrolidone; ester solvents such as butyl acetate; glycol solvents such as propylene glycol monomethyl ether; aromatic solvents such as toluene, etc.

[0248] The other vinyl compound is not particularly limited as long as it has a vinyl group and does not belong to the vinyl compound (1).

[0249] The other resin is not particularly limited as long as it is a resin other than the polymer of the vinyl compound (1).

[0250] The vinyl composition (1) may contain only one of the other components or two or more of them.

[0251] The content of the other components in the vinyl composition (1) can be arbitrarily selected depending on the types of the other components.

[0252] In the vinyl composition (1), the content of the vinyl compound (1) is preferably 80% by mass or more, for example, 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 above ratio is 100% by mass or less. The vinyl composition (1) having the above ratio of 80% by mass or more is preferred because the effect obtained by containing the vinyl compound (1) is further improved.

[0253] The vinyl compound (1) obtained by the above method can be used as a vinyl composition (1) as it is. The vinyl composition (1) containing the above other components is obtained by mixing the vinyl compound (1) and the above other components.

[0254] <<Cured vinyl resin>>

[0255] The cured vinyl resin of the present embodiment is obtained by curing the vinyl compound (1) or the vinyl composition (1).

[0256] In this specification, the cured vinyl resin material of this embodiment may be referred to as a "cured vinyl resin material (1)".

[0257] The cured vinyl resin has high thermal conductivity by using the vinyl compound (1), and is suitable as a constituent material of a printed wiring board, and is particularly suitable as an insulating material constituting a printed wiring board. The cured vinyl resin has a tendency to have lower dielectric loss than epoxy resins used in conventional substrate applications by using the vinyl compound (1).

[0258] When the cured vinyl resin (1) is a cured product of a vinyl compound (1), the cured vinyl resin (1) may be a cured product of one type of vinyl compound (1) or a cured product of two or more types of vinyl compounds (1).

[0259] When the cured vinyl resin (1) is a cured product of a vinyl composition (1), the cured vinyl resin (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).

[0260] The cured vinyl resin (1) can be produced, for example, by the following methods: a method in which the vinyl compound (1) or the vinyl composition (1) is directly filled into a mold, and if necessary, the mold is pressurized at a predetermined pressure by a press machine or the like, and heated for a predetermined time to perform primary curing, and further, the mold is pressurized at a predetermined pressure by a press machine or the like, and heated for a predetermined time to perform complete curing; a method in which the vinyl compound (1) or the vinyl composition (1) is directly heated at a predetermined temperature to perform curing; a method in which a powder of the vinyl compound (1) or the vinyl composition (1) is directly or as necessary melted, and injected into a mold, and the mold is pressurized at a predetermined pressure by a press machine or the like, and heated for a predetermined time; a method in which the vinyl compound (1) or the vinyl composition (1) is completely cured by heating at a predetermined temperature to perform curing. ) is heated and melted and injected into a mold, etc., and the mold is further heated to thereby form a method; a method of melting a vinyl compound (1) or a vinyl composition (1), injecting the obtained melt into a preheated mold to solidify it; a method of partially solidifying a vinyl compound (1) or a vinyl composition (1), pulverizing the obtained partially solidified product, filling the obtained powder into a mold, and melting the filled powder to form a method; a method of dissolving a vinyl compound (1) or a vinyl composition (1) in a solvent directly or as needed, partially solidifying it while stirring as needed, casting the obtained solution, drying and removing the solvent by ventilation drying, etc., and heating for a specified time while applying pressure at a specified pressure using a press as needed, etc.

[0261] The heating temperature when the vinyl compound (1) or the vinyl composition (1) is heated to cure (curing temperature; when curing is performed in multiple stages, the complete curing temperature) is not particularly limited, but is preferably 140° C. or higher, more preferably 150° C. or higher, from the viewpoint of increasing the degree of cure of the vinyl compound (1) or the vinyl composition (1). From the viewpoint of avoiding excessive heating, the heating temperature is preferably 200° C. or lower.

[0262] 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 to cure is not particularly limited, but is preferably 1 hour or more, more preferably 2 hours or more, from the viewpoint of increasing the degree of cure of the vinyl compound (1) or the vinyl composition (1). From the viewpoint of avoiding unnecessary curing operations, the heating time is preferably 10 hours or less.

[0263] The pressure applied when the vinyl compound (1) or the vinyl composition (1) is pressurized to cure (pressure during curing) is not particularly limited, but is preferably 0.7 MPa or more, more preferably 1.2 MPa or more, from the viewpoint of increasing the degree of cure of the vinyl compound (1) or the vinyl composition (1). From the viewpoint of avoiding excessive pressurization, the pressure applied is preferably 3 MPa or less.

[0264] The thermal diffusivity of the cured vinyl resin (1) is preferably 1.75×10 -7 m 2 / s or more, more preferably 1.80×10 -7 m 2 / s or more, more preferably 1.85×10 -7 m 2 / s or more. When the thermal diffusivity is within the above range, the thermal conductivity tends to be high. The upper limit of the thermal diffusivity of the cured vinyl resin (1) is not particularly limited, and the thermal diffusivity may be 4.00×10 -7 m 2 / s or less, or 3.00×10 -7 m 2 / s or less, and can also be 2.50×10 -7 m 2 / s or less.

[0265] The thermal diffusivity of the cured vinyl resin (1) can be, for example, 1.75×10 -7 ~4.00×10 -7 m 2 / s, 1.80×10 -7 ~3.00×10-7 m 2 / s and 1.85×10 -7 ~2.50×10 -7 m 2 / s.

[0266] The thermal diffusivity of the cured vinyl resin (1) can be measured by temperature wave thermal analysis (TWA). In this example, the thermal diffusivity was measured using a commercially available thermal diffusivity measuring device "ai-phase mobile" (manufactured by AI-Phase Co., Ltd.).

[0267] The dielectric loss tangent of the cured vinyl resin (1) at a frequency of 100 MHz is preferably 0.0050 or less, more preferably 0.0048 or less, and further preferably 0.0046 or less. The lower limit of the dielectric loss tangent of the cured vinyl resin (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.

[0268] The dielectric loss tangent of the cured vinyl resin (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. However, these are only examples of the dielectric loss tangent of the cured vinyl resin (1).

[0269] The dielectric loss tangent of the cured vinyl resin (1) at a frequency of 100 MHz can be measured by a capacitance method using an impedance analyzer under the following conditions.

[0270] ·Determination method: Volumetric method

[0271] Electrode model: 16453A

[0272] ·Measurement environment: 23℃, 50%RH

[0273] Applied voltage: 1V

[0274] <<Prepreg>>

[0275] The prepreg of the present embodiment comprises 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.

[0276] In this specification, the prepreg of this embodiment is sometimes referred to as "prepreg (1)". By using the prepreg (1), a laminated board or the like can be easily manufactured by a conventional method. For example, a plurality of prepregs (1) are stacked to form a laminate, and the laminate is formed while being heated and pressurized to be integrated, thereby obtaining a target laminated board.

[0277] A printed wiring board (resin layer in the printed wiring board) obtained by using the prepreg (1) or the above-mentioned laminate has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (1).

[0278] The prepreg (1) can be produced by a method in which a solution obtained by dissolving a vinyl compound (1) in a solvent is applied to or impregnated into a fibrous base material; or a method in which a vinyl composition (1) or a dilution obtained by diluting the vinyl composition (1) with a solvent is applied to or impregnated into a fibrous base material and then the applied or impregnated fibrous base material is heated to semi-cure the vinyl compound (1) or the vinyl composition (1).

[0279] The heating temperature (semi-curing temperature) and heating time (semi-curing time) for 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.

[0280] The fibrous substrate is not particularly limited as long as it is a fibrous substrate, and may be a known substrate. More specifically, for example, woven and nonwoven fabrics of inorganic fibers such as glass fibers, woven and nonwoven fabrics of organic fibers such as polyester, etc. may be cited.

[0281] <<Film with resin>>

[0282] The resin-bearing film of the present 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. As the resin-bearing film of the present embodiment, more specifically, for example, a resin-bearing film comprising the above-mentioned resin layer and the above-mentioned support film arranged on one surface or both surfaces of the above-mentioned resin layer can be cited. Using a plurality of resin-bearing films of the present embodiment, the support film is removed, and the layers are overlapped to form a laminate, and the laminate is formed by heating and pressurizing, and integrated to obtain a laminate. The resin layer in the resin-bearing film of the present embodiment, and the printed wiring board (resin layer in the printed wiring board) obtained by using the above-mentioned resin layer or laminate have high thermal conductivity and low dielectric loss by using the vinyl compound (1).

[0283] Examples of the support film include polyethylene terephthalate (PET) films and the like.

[0284] In the case of a film with resin, when support films are provided on both sides of the resin layer, these support films may be the same as or different from each other. In this specification, not limited to the case of a film with resin, two layers of support films being different from each other means that at least one of the material and thickness of the two layers of support films is different from each other.

[0285] The film with resin of the present embodiment can be produced by applying a solution obtained by dissolving a vinyl compound (1) in a solvent to the above-mentioned support film, or applying a vinyl composition (1) or a dilution obtained by diluting a vinyl composition (1) with a solvent to the above-mentioned support film, and then heating the layer of the coated material to semi-cure the vinyl compound (1) or the vinyl composition (1) in the coated material. The conditions for semi-curing the vinyl compound (1) or the vinyl composition (1) are the same as the conditions for producing the prepreg described above.

[0286] <<Metal foil with resin>>

[0287] The metal foil with resin of the present 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. As the metal foil with resin of the present embodiment, more specifically, for example, a metal foil with resin comprising the above-mentioned resin layer and the above-mentioned metal foil arranged on one surface or both surfaces of the above-mentioned resin layer can be cited. For example, the metal foil with resin of the present embodiment is used to further cure the above-mentioned semi-cured product to form a cured product, and the metal foil is patterned to form a circuit, thereby making it possible to make a printed wiring board. In addition, the metal foil with resin of the present embodiment is used to pattern the metal foil to form a circuit, and the resin layers having such a circuit are stacked in a manner consistent with the direction of the circuit, and the semi-cured product is further cured while being heated and pressurized, thereby making it possible to make a multilayer printed wiring board having a resin layer containing a cured product of a vinyl compound (1) or a cured product of a vinyl composition (1) as an insulating layer. The resin layer in the metal foil with resin according to the present embodiment and the printed wiring board (resin layer in the printed wiring board) obtained by using the metal foil with resin have high thermal conductivity and low dielectric loss by using the vinyl compound (1).

[0288] As said metal foil, copper foil etc. are mentioned, for example.

[0289] In the case of a metal foil with resin, when metal foils are provided on both sides of the resin layer, these metal foils may be the same as or different from each other. In this specification, not limited to the case of a metal foil with resin, two layers of metal foils being different from each other means that at least one of the material and thickness of the two layers of metal foils is different from each other.

[0290] The metal foil with resin according to the present embodiment can be produced by the same method as in the case of the film with resin described above, except that the metal foil described above is used instead of the support film.

[0291] <<Metal-clad laminate>>

[0292] The metal-clad laminate of the present embodiment comprises: an insulating layer comprising 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. As the metal-clad laminate of the present embodiment, more specifically, for example, a metal-clad laminate comprising the above-mentioned insulating layer and the above-mentioned metal foil disposed on one surface or both surfaces of the above-mentioned insulating layer can be cited. The metal-clad laminate of the present embodiment can be made into a printed wiring board, for example, by patterning the metal foil therein to form a conductor wiring (circuit). In addition, such a plurality of printed wiring boards can be stacked with an insulating layer prepared separately, heated and pressurized at the same time, thereby making a multilayer printed wiring board. The insulating layer in the metal-clad laminate of the present embodiment and the printed wiring board (insulating layer in the printed wiring board) obtained using the above-mentioned metal-clad laminate have high thermal conductivity and low dielectric loss by using the vinyl compound (1).

[0293] The metal foil included in the metal-clad laminate of the present embodiment is the same as the metal foil included in the metal foil with resin.

[0294] In the metal-clad laminate, when metal foils are provided on both surfaces of the insulating layer, these metal foils may be the same as or different from each other.

[0295] The insulating layer used separately when laminating the printed wiring board may be a known layer, or may be the resin layer in the resin-bearing film, or the laminated sheet which is a laminate of a plurality of the resin layers, or may be the prepreg (1), or the laminated board obtained by laminating a plurality of prepregs (1). Alternatively, in these resin layers, laminated sheets, prepregs (1), or laminated boards, a material obtained by further curing the vinyl compound (1) or the vinyl composition (1) may be the insulating layer.

[0296] The metal-clad laminate of the present embodiment can be manufactured, for example, by laminating a metal foil on one or both surfaces of a prepreg (1), and heating and pressurizing the resulting laminate, thereby further curing the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product in the prepreg (1) to form a cured product, forming an insulating layer, and fusing the prepreg (1) to the metal foil.

[0297] The metal-clad laminate of the present embodiment can be produced by, for example, using the vinyl compound (1) or the vinyl composition (1) to produce a prepreg (1) by the method described above, and using the prepreg (1) to produce the metal-clad laminate by the method described above.

[0298] The metal-clad laminate of the present embodiment can also be manufactured, for example, by heating the above-mentioned metal foil with resin to further cure the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product in the above-mentioned 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).

[0299] <<Printed circuit board>>

[0300] The printed wiring board of this embodiment comprises: an insulating layer comprising 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, as the printed wiring board of this embodiment, for example, there can be cited a printed wiring board comprising the above-mentioned insulating layer and the above-mentioned conductor wiring arranged on one surface or both surfaces of the above-mentioned insulating layer. A plurality of printed wiring boards of this embodiment can be stacked with an insulating layer prepared separately therebetween, and heated and pressurized to thereby prepare a multilayer printed wiring board. The printed wiring board of this embodiment (the insulating layer in the printed wiring board) has high thermal conductivity and low dielectric loss by using a vinyl compound (1).

[0301] The material of the conductor wiring is the same as the metal of the metal foil provided in the metal-clad laminate. The insulating layer used separately when laminating the printed wiring board of the present embodiment is the insulating layer described above.

[0302] In a printed wiring board, when conductor wiring is provided on both surfaces of an insulating layer, the material and thickness of these conductor wiring may be the same as or different from each other.

[0303] The printed wiring board of the present embodiment can be produced, for example, by patterning a metal foil in the above-mentioned metal-clad laminate to form a conductor wiring (circuit).

[0304] The printed wiring board of the present embodiment can also be manufactured, for example, by heating the above-mentioned metal foil with resin to further cure the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product in the above-mentioned 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 further patterning the metal foil to form a conductor wiring (circuit).

[0305] The metal foil can be patterned by a known method such as etching.

[0306] Figure 1 1 is a cross-sectional view schematically showing an example of a laminated structure of the present embodiment obtained by using a vinyl compound (1). It should be noted that in the drawings used in the following description, in order to facilitate understanding of the features of the present invention, the main parts are sometimes enlarged for convenience, and the dimensional ratios of the various components are not necessarily the same as the actual ones.

[0307] The laminated structure 1 shown here comprises 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 by using a vinyl compound (1). The second layer 12 is selected according to the type of the laminated structure 1. The first layer 11 and the second layer 12 are both in the form of a film or a sheet. The second layer 12 may be provided on the entire area of ​​one surface 11a of the first layer 11 or may be provided on a partial area.

[0308] When the first layer 11 is a resin layer containing the vinyl compound (1) or a semi-cured product thereof or the vinyl composition (1) or a semi-cured product thereof, and the second layer 12 is a support film, the laminated structure 1 is a film with a resin.

[0309] When 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 laminated structure 1 is a metal foil with resin.

[0310] When the first layer 11 is an insulating layer comprising 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 laminated structure 1 is a metal-clad laminate.

[0311] Figure 2 is a cross-sectional view schematically showing another example of the laminated structure of the present embodiment obtained by using the vinyl compound (1). Figure 2 In the following drawings, the same components as those shown in the already described drawings are denoted by the same reference numerals as those in the already described drawings, and their detailed description is omitted.

[0312] The laminated structure 2 shown here comprises 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 Figure 2 In the embodiment, the cross section of the stacked structure 2 is formed to include a cross section along the linear length direction of the second layer 22. The number of the linear second layer 22 may be one or more. The stacked structure 2 is similar to the structure of FIG. 1 except that the linear second layer 22 is provided instead of the film-like second layer 12. Figure 1 The stacked structures 1 shown are identical.

[0313] When the first layer 11 is an insulating layer comprising 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 laminated structure 2 is a printed wiring board.

[0314] Figure 1-2 The illustrated stacked structures 1 and 2 have nothing on the other surface 11 b of the first layer 11 , but may have the same layer as the second layer 12 or the second layer 22 .

[0315] Figure 3 This is a cross-sectional view schematically showing another example of the laminated structure of the present embodiment obtained using the vinyl compound (1).

[0316] The stacked structure 3 shown here comprises a first layer 11, a second layer 12 disposed on one surface 11a of the first layer 11, and a third layer 13 disposed on the other surface 11b of the first layer 11. The third layer 13 is in the form of a film or a sheet, and is selected according to the type of the stacked structure 1 in the same manner as the second layer 12. The configuration of the third layer 13 on the other surface 11b of the first layer 11 is the same as the configuration of the second layer 12 on 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 those of the second layer 12. For example, the third layer 13 may be disposed on the entire area of ​​the other surface 11b of the first layer 11, or may be disposed on a partial area.

[0317] When the first layer 11 is a resin layer containing the vinyl compound (1) or a semi-cured product thereof or the 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 film with resin.

[0318] When 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 metal foil with resin.

[0319] When the first layer 11 is an insulating layer comprising 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.

[0320] Figure 4 This is a cross-sectional view schematically showing another example of the laminated structure of the present embodiment obtained using the vinyl compound (1).

[0321] The laminated structure 4 shown here comprises 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 Figure 4 In the embodiment, the cross section of the stacked structure 4 is formed to include both the cross section along the linear length direction of the second layer 22 and the cross section along the linear length direction of the third layer 23. The configuration of the third layer 23 on the other surface 11b of the first layer 11 is the same as the configuration of the second layer 22 on the 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 the linear third layer 23 may be one or more.

[0322] When the first layer 11 is an insulating layer comprising 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 laminated structure 4 is a printed wiring board.

[0323] Example

[0324] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.

[0325] It should be noted that, in the following examples, "room temperature" refers to a temperature range of 15 to 40°C.

[0326] The conditions for measuring the melting point of the vinyl compound are shown.

[0327] Using a differential scanning calorimeter (FP84HT manufactured by METTLER TLEDO), a glass dish filled with a vinyl compound was kept at 50°C for 2 minutes, then the temperature was raised by 5°C per minute and kept at 250°C for 2 minutes, and the endothermic peak temperature was taken as the melting point. If there were multiple endothermic peaks, the endothermic peak temperature on the lower temperature side was taken as the melting point.

[0328] The measurement conditions of the solubility of the vinyl compound are shown.

[0329] At room temperature, 50 mg of the vinyl compound is placed in a screw tube, ТHF stored at room temperature is added dropwise, and the weight of the solution when the monomer is completely dissolved is measured. The value of 50 mg / weight (mg) of the solution is taken as the solubility (wt%).

[0330] The test conditions of the cured product are shown.

[0331] (1) Thermal diffusivity

[0332] 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 Co., Ltd.).

[0333] Example 1

[0334] In a 500 mL four-necked 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.

[0335] 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 filtered out and washed with methanol. The obtained 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.

[0336] In a 200 mL four-necked flask equipped with a thermometer, a condenser and a stirrer, 5.0 g of 1,3,5-tris(trans-4-(4-hydroxyphenyl)cyclohexyl)1,3,5-benzenetricarboxylate, 0.05 g of 2,6-di(tert-butyl)-p-cresol, 7.2 g of potassium carbonate, 0.3 g of sodium iodide, 35 mL of N,N-dimethylformamide and 4.6 g of vinylbenzyl chloride (a mixture of meta- and para-isomers) were added and reacted at an internal temperature of about 60° C. for 6 hours.

[0337] 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 filtered out and washed with hexane, water and methanol. The obtained solid was dissolved in toluene and washed with water. After a portion of the solution was removed under reduced pressure from the obtained solution, methanol was added to the obtained concentrated solution and stirred, the precipitated solid was filtered out, and it was dried under reduced pressure to obtain 4.5 g of vinyl compound 1. Purity: 96.5% (liquid chromatography area percentage value).

[0338] [Chemical formula 19]

[0339]

[0340] Example 2

[0341] In a 300 mL four-necked flask equipped with a thermometer, a condenser, and a stirrer, 2.7 g of 1,3,5-benzenetricarboxylic acid 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.

[0342] After the reaction was completed, the solvent was distilled off, and the obtained solid was purified using a silica gel column to obtain 1.3 g of 1,3,5-tris(4-hydroxyphenyl)1,3,5-benzenetricarboxylate.

[0343] In a 100 mL four-necked flask equipped with a thermometer, a condenser and a stirrer, 1.3 g of 1,3,5-tris(4-hydroxyphenyl)1,3,5-benzenetricarboxylate, 0.01 g of 2,6-di(tert-butyl)-p-cresol, 2.8 g of potassium carbonate, 0.1 g of sodium iodide, 25 mL of N,N-dimethylformamide and 1.9 g of vinylbenzyl chloride (a mixture of meta- and para-isomers) were added and reacted at an internal temperature of about 60°C for 13 hours.

[0344] 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 filtered out and washed with hexane, water, and methanol. The obtained solid was dissolved in toluene, methanol was added and stirred, and the precipitated solid was filtered out and dried under reduced pressure to obtain 0.4 g of vinyl compound 2. Purity: 70.6% (liquid chromatography area percentage value).

[0345] [Chemical formula 20]

[0346]

[0347] Example 3

[0348] In a 300 mL four-necked flask equipped with a thermometer, a condenser and a stirrer were added 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, and reacted at an internal temperature of about 180° C. for 14 hours.

[0349] After the reaction was completed, the reaction mixture was cooled to room temperature, the supernatant of the reaction solution was removed by decantation, and the solid was washed with methanol. The obtained solid was dried under reduced pressure to obtain solid A. Water was added to the methanol used for washing, the precipitated solid was filtered out, and it was dried under reduced pressure to obtain solid B. Solid A and solid B were combined to obtain 6.0 g of compound 1.

[0350] In a 200 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 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 (a mixture of meta- and para-isomers) were added and reacted at an internal temperature of about 60° C. for 8 hours.

[0351] After the reaction was completed, the mixture was cooled to room temperature, 40 mL of water and 30 mL of hexane were added, and after stirring, the precipitated solid was filtered out and washed with hexane, water, and methanol. The obtained solid was dissolved in toluene and washed with water. After a portion of the solution was removed from the obtained solution under reduced pressure, methanol was added to the obtained concentrated solution and stirred, and the precipitated solid was filtered out and dried under reduced pressure to obtain 4.0 g of vinyl compound 3. Purity: 73.4% (liquid chromatography area percentage value).

[0352] [Chemical formula 21]

[0353]

[0354] Comparative Example 1

[0355] In a 200 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl 6.0 g, 2,6-di(tert-butyl)-p-cresol 0.06 g, potassium carbonate 12 g, sodium iodide 1.3 g, N,N-dimethylformamide 34 mL and 4-vinylbenzyl chloride 10 g were added and reacted at an internal temperature of about 60°C for 3 hours. After the reaction was completed, 121 g of toluene and 34 mL of water were added and stirred, and the insoluble matter was removed by filtration. The obtained solution was separated and washed with water three times. After the obtained solution was filtered to remove the insoluble matter, toluene was removed under reduced pressure. Methanol 56 mL and 2,6-di(tert-butyl)-p-cresol 0.07 g were added to the obtained solid and stirred at room temperature. The solid in the suspension was filtered and dried under reduced pressure to obtain 9.4 g of vinyl compound 4. Purity: 99.1% (HPLC area percentage value).

[0356] [Chemical formula 22]

[0357]

[0358] The vinyl compound obtained in Example 1, Example 2, Example 3 and Comparative Example 1 was added to the plate-shaped hollow part of the mold, and after being pressurized at a pressure of 1.5 MPa under reduced pressure and heated at the primary curing temperature shown in Table 1 for 1 hour, it was heated at 180°C for 2 hours while applying a pressure of 1.5 MPa, thereby obtaining a cured product with a thickness of 150 to 250 μm.

[0359] Table 1 shows the melting points of the vinyl compounds and the thermal diffusivities of the cured products.

[0360]

[0361] Industrial Applicability

[0362] The present invention can be used for a printed wiring board in a communication device, and is particularly suitable for use as a printed wiring board in a case where the communication device is expected to process a large amount of data and generate a large amount of heat.

[0363] Description of Reference Numerals

[0364] 1, 2, 3, 4-layer structure

[0365] 11. Layer 1

[0366] 11a One surface of layer 1

[0367] 11b The other side of layer 1

[0368] 12, 22 Layer 2

[0369] 13, 23 Layer 3

Claims

1. A vinyl compound represented by formula (1) or formula (2), In the formula, R is an acryloyl group, a methacryloyl group, or a vinylbenzyl group, and a plurality of Rs may be the same or different from each other. A 1 is a substituted or unsubstituted m-valent aromatic group excluding a nitrogen-containing aromatic heterocyclic group, a substituted or unsubstituted m-valent cycloalkane group, an m-valent group formed by connecting two or more substituted or unsubstituted aromatic rings excluding a nitrogen-containing aromatic heterocyclic ring through a single bond, an m-valent group formed by connecting two or more substituted or unsubstituted cycloalkane rings through a single bond, an m-valent group formed by connecting one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings through a single bond, a substituted or unsubstituted m-valent chain saturated aliphatic hydrocarbon group, R 1 (OR 2 - ) The group shown in 3, R 1 (R 2 - ) The group shown in 3, R 3 C(OR 2 - ) a group represented by 3, or R 3 C(R 2 - ) The group shown in 3, R 1 is a substituted or unsubstituted trivalent aromatic group, wherein Does not include nitrogen-containing aromatic heterocyclic groups, R 2 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, -R 4 (R 5 ) p R 4 - The group shown, or - (R 6 O) q R 6 - The groups shown, multiple R 2 can be the same or different from each other, R 3 is a hydrogen atom or a methyl group, R 4 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, and a plurality of R 4 can be the same or different from each other, R 5 is a substituted or unsubstituted divalent aromatic group excluding a nitrogen-containing aromatic heterocyclic group. When p is 2 or 3, a plurality of R 5 can be the same or different from each other, R 6 is a substituted or unsubstituted divalent chain saturated aliphatic hydrocarbon group, and a plurality of R 6 can be the same or different from each other, p is an integer from 1 to 3, q is an integer from 1 to 3, For X 1 The bonding position of is bonded to R 1 The bonding position of the oxygen atom and R 1 The bonding position of 3 The bonding position of the oxygen atom of C or R 3 The bonding position of C, A 2 is a substituted or unsubstituted divalent aromatic group excluding a nitrogen-containing aromatic heterocyclic group, 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 a nitrogen-containing aromatic heterocyclic ring are connected via a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkane rings are connected via a single bond, a divalent group in which two or more substituted or unsubstituted cycloalkene rings are connected via a single bond, or a divalent group in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings are connected via a single bond. a divalent group formed by a single bond, a divalent group formed by a single bond between one or more substituted or unsubstituted aromatic rings excluding nitrogen-containing aromatic heterocycles and one or more substituted or unsubstituted cycloalkene rings, a divalent group formed by a single bond between one or more substituted or unsubstituted cycloalkane rings and one or more substituted or unsubstituted cycloalkene rings, a divalent group formed by a single bond between 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, -B 1 Y 1 B 2 - The groups shown, -B 1 Y 1 B 2 Y 2 B 3 - The group shown, or -B 1 Y 1 B 2 Y 2 B 3 Y 3 B 4 - The groups shown, multiple A 2 can be the same or different from each other, B 1 ~B 4 Each of the above is a substituted or unsubstituted divalent aromatic group excluding a nitrogen-containing aromatic heterocyclic group, a substituted or unsubstituted divalent cycloalkane group, a substituted or unsubstituted divalent cycloalkene group, a divalent group formed by connecting two or more substituted or unsubstituted aromatic rings excluding a nitrogen-containing aromatic heterocyclic ring via a single bond, a divalent group formed by connecting two or more substituted or unsubstituted cycloalkane rings via a single bond, a divalent group formed by connecting two or more substituted or unsubstituted cycloalkene rings via a single bond, or a divalent group formed by connecting one or more substituted or unsubstituted aromatic rings to one or more substituted or 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 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 and 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 ~Y 3 are each an ester group, a carbonyl group, or an ether group, For X 1 The bonding position of is the bonding position to the acryloyloxy group, methacryloyloxy group, or vinylbenzyloxy group in formula (1), or is 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 multiple X 1 can be the same or different from each other, m is an integer from 3 to 6, n is an integer of 1 to 20, and a plurality of n may be the same or different from each other.

2. The vinyl compound according to claim 1, wherein A 1 and A 2 The group has 14 or less carbon atoms, wherein the carbon number does not include the carbon number of the substituent.

3. The vinyl compound according to claim 1, which is used for a printed wiring board. A vinyl composition comprising the vinyl compound according to claim 1. 5 . A cured vinyl resin obtained by curing the vinyl compound according to claim 1 or the vinyl composition according to claim 4 . 6 . A prepreg comprising the vinyl compound or a semi-cured product thereof according to claim 1 , or the vinyl composition or a semi-cured product thereof according to claim 4 , and a fibrous base material. 7 . A film with a resin, comprising a resin layer and a support film, wherein the resin layer comprises the vinyl compound or a semi-cured product thereof according to claim 1 , or the vinyl composition or a semi-cured product thereof according to claim 4 . 8 . A metal foil with a resin, comprising a resin layer and a metal foil, wherein the resin layer comprises the vinyl compound or a semi-cured product thereof according to claim 1 , or the vinyl composition or a semi-cured product thereof according to claim 4 . 9 . A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the vinyl compound according to claim 1 or a cured product of the vinyl composition according to claim 4 . 10 . A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the prepreg according to claim 6 . 11 . A printed wiring board comprising an insulating layer and a conductor wiring, wherein the insulating layer comprises a cured product of the vinyl compound according to claim 1 or a cured product of the vinyl composition according to claim 4 . 12 . A printed wiring board comprising an insulating layer and conductive wiring, wherein the insulating layer comprises a cured product of the prepreg according to claim 6 .

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