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 and which exhibits a low melting point. The present invention relates to a vinyl compound represented by formula (A). (In formula (A), each of Y1 and Y2 represents a vinyl benzyl group, an acryloyl group, or a 1-alkenyl group having 3-6 carbon atoms, Q represents a group represented by any of formulae (1)-(4), and in formulae (1)-(4), each of Y1 and Y2 represents a vinyl benzyl group, an acryloyl group, or a 1-alkenyl group having 3-6 carbon atoms. A1, A2, A3 and A4 represent a divalent aromatic group, a divalent cycloalkylene group, a divalent group formed by connecting two or more divalent aromatic groups by a single bond, a divalent group formed by connecting two or more divalent cycloalkylene groups by a single bond, or a divalent group formed by connecting one or more divalent aromatic groups and one or more divalent cycloalkylene groups by a single bond; and each of X1, X2 and X3 represents an ester bond or a carbonyl group) # 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, when manufacturing heat-dissipating members such as printed wiring boards, the monomer compound as a raw material of the resin is expected to have good processability, and therefore is required to have a low melting point.

[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.

[0013] Means for solving problems

[0014] The present invention adopts the following configuration.

[0015] [1] A vinyl compound represented by the formula (A).

[0016] [Chemical formula 1]

[0017]

[0018] (In the above formula (A),

[0019] Y 1 and Y 2 are all vinylbenzyl, (meth)acryloyl, or 5-hexenyl,

[0020] Q is a group represented by any one of the formulae (1) to (4),

[0021] [Chemical formula 2]

[0022]

[0023] In the above formulas (1) to (4),

[0024] A 1 , A 2 , A 3 and A 4 The same or different,

[0025] is a substituted or unsubstituted divalent aromatic group (excluding aromatic groups containing hydroxyl groups),

[0026] A substituted or unsubstituted divalent cycloalkylene group (excluding cycloalkylene groups containing a hydroxyl group),

[0027] A divalent group formed by connecting two or more substituted or unsubstituted divalent aromatic groups (excluding aromatic groups containing a hydroxyl group) via a single bond,

[0028] A divalent group formed by connecting two or more substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) via a single bond, or

[0029] A divalent group formed by connecting one or more substituted or unsubstituted divalent aromatic groups (excluding aromatic groups containing a hydroxyl group) and one or more substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) via a single bond,

[0030] X 1 , X 2 and X 3 are the same or different, and are ester bonds or carbonyl groups,

[0031] In Y 1 and Y 2 When all are vinylbenzyl groups and Q is a group represented by formula (1), A 1 is a divalent group formed by connecting two substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) via a single bond, or a divalent group formed by connecting one substituted or unsubstituted divalent aromatic group (excluding aromatic groups containing a hydroxyl group) and one substituted or unsubstituted divalent cycloalkylene group (excluding cycloalkylene groups containing a hydroxyl group) via a single bond,

[0032] In Y 1 and Y 2 When all are (meth)acryloyl groups, Q is a group represented by formula (2), and A 1 and A 2 One of them is a substituted or unsubstituted divalent aromatic group (excluding an aromatic group containing a hydroxyl group), and the other is a divalent group formed by a substituted or unsubstituted divalent aromatic group (excluding an aromatic group containing a hydroxyl group) and a substituted or unsubstituted divalent cycloalkylene group (excluding a cycloalkylene group containing a hydroxyl group) connected by a single bond,

[0033] In Y 1 and Y 2 When all are 5-hexenyl, Q is a group represented by formula (2), and A 1 and A 2 Any one of them is a substituted or unsubstituted divalent aromatic group, and the other is a divalent group formed by a substituted or unsubstituted divalent aromatic group (excluding aromatic groups containing hydroxyl groups) and a substituted or unsubstituted divalent cycloalkylene group (excluding cycloalkylene groups containing hydroxyl groups) connected by a single bond.

[0034] [2] The vinyl compound according to [1], wherein X 1 , X 2 and X 3 It is an ester bond.

[0035] [3] The vinyl compound according to [1] or [2], which is used for a printed wiring board.

[0036] [4] A vinyl composition comprising the vinyl compound described in any one of [1] to [3].

[0037] [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].

[0038] [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.

[0039] [7] A film with a resin, 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].

[0040] [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].

[0041] [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].

[0042]

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

[0043]

[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 described in any one of [1] to [3] or a cured product of the vinyl composition described in [4].

[0044]

[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].

[0045] Effects of the Invention

[0046] According to the present invention, a novel compound which can be used as a constituent material of a printed wiring board and has a low melting point can be provided. In addition, according to the present invention, 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

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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

[0051] Hereinafter, preferred embodiments of the present invention will be described in detail.

[0052] <Vinyl compound (A)>

[0053] The vinyl compound of the present embodiment is represented by the following formula (A). In the present specification, the vinyl compound represented by the above formula (A) may be referred to as “vinyl compound (A)”.

[0054] [Chemical formula 3]

[0055]

[0056] Y in the vinyl compound (A) 1 and Y 2 is a group having a vinyl group (vinyl group) at the terminal. 1 and Y 2 All of them are vinylbenzyl, acryloyl, methacryloyl or 5-hexenyl, and from the viewpoint of ease of polymerization, vinylbenzyl, acryloyl or methacryloyl is preferred, and from the viewpoint of low dielectric constant, vinylbenzyl is more preferred.

[0057] Vinylbenzyl is 2-vinylbenzyl, 3-vinylbenzyl, or 4-vinylbenzyl, preferably 3-vinylbenzyl or 4-vinylbenzyl. 1 and Y 2 In the case of a vinylbenzyl group, the positions of the vinyl groups may be the same as or different from each other.

[0058] The structure of Q in the vinyl compound (A) is a mesogen skeleton having a structure in which two or more hydrocarbon rings are connected. In the above formula (A), Q is a group represented by any one of formulas (1) to (4),

[0059] [Chemical formula 4]

[0060]

[0061] In the above formulas (1) to (4),

[0062] A 1 , A 2 , A 3 and A 4 The same or different,

[0063] is a substituted or unsubstituted divalent aromatic group (excluding aromatic groups containing hydroxyl groups),

[0064] A substituted or unsubstituted divalent cycloalkylene group (excluding cycloalkylene groups containing a hydroxyl group),

[0065] A divalent group formed by connecting two or more substituted or unsubstituted divalent aromatic groups (excluding aromatic groups containing a hydroxyl group) via a single bond,

[0066] A divalent group formed by connecting two or more substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) via a single bond, or

[0067] A divalent group formed by connecting one or more substituted or unsubstituted divalent aromatic groups (excluding aromatic groups containing a hydroxyl group) and one or more substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) via a single bond.

[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, examples of heteroatoms contained in the heterocyclic ring include oxygen atoms, nitrogen atoms, and sulfur atoms. From the perspective of dielectric loss suppression or dielectric loss tangent, the aromatic ring preferably does not contain heteroatoms. The aromatic ring is preferably a monocyclic ring or a condensed ring, more preferably a monocyclic ring.

[0069] The number of carbon atoms in the unsubstituted divalent aromatic group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0070] Specific examples of the unsubstituted divalent aromatic ring include benzene, naphthalene, anthracene, phenanthrene, pyrene, benzo[9,10]phenanthrene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene.

[0071] When the divalent aromatic group has a substituent, that is, when the aromatic group has a substituent, the substituent is 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. This is because the polarity of the aromatic ring containing a hydroxyl group as a substituent is high, which may cause an increase in the dielectric loss of the cured product.

[0072] 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.

[0073] 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.

[0074] 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 perspective of dielectric loss suppression or 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.

[0075] 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.

[0076] The number of carbon atoms in the unsubstituted divalent cycloalkylene group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0077] Specific examples of the unsubstituted divalent 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.

[0078] When the divalent cycloalkylene group has a substituent, the substituent has the same meaning as the substituent which the divalent aromatic group may have.

[0079] In a divalent group in which two or more substituted or unsubstituted divalent aromatic groups are linked by a single bond, the number of substituted or unsubstituted aromatic rings linked by a single bond is not particularly limited as long as it is 2 or more, but is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0080] 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.

[0081] In the divalent group formed by two or more substituted or unsubstituted divalent cycloalkane rings 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.

[0082] 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.

[0083] In a divalent group in which one or more substituted or unsubstituted divalent aromatic rings and one or more substituted or unsubstituted divalent cycloalkane rings are linked by 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.

[0084] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings are connected 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.

[0085] The substituted or unsubstituted divalent aromatic group is a residue obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted aromatic ring. The substituted or unsubstituted divalent cycloalkylene group is a residue obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted cycloalkane ring.

[0086] In formula (A), X 1 , X 2 and X 3 are the same or different, and are ester bonds ( -COO- or -OCO- ; , Indicates that 1 , A 2 , A 3 and A 4 ) or a carbonyl group, preferably an ester bond or a carbonyl group, more preferably an ester bond. By making X 1 , X 2 and X 3 The cured vinyl resin containing the vinyl compound having an ester bond can exhibit excellent thermal conductivity.

[0087] In Y 1 and Y 2 When all are vinylbenzyl groups and Q is a group represented by formula (1), A 1 It is a divalent group in which two substituted or unsubstituted divalent cycloalkylene groups (excluding cycloalkylene groups containing a hydroxyl group) are linked via a single bond, or a divalent group in which one substituted or unsubstituted divalent aromatic group (excluding aromatic groups containing a hydroxyl group) and one substituted or unsubstituted divalent cycloalkylene group (excluding cycloalkylene groups containing a hydroxyl group) are linked via a single bond.

[0088] In Y 1 and Y 2 When all are (meth)acryloyl groups, Q is a group represented by formula (2), and A 1 and A 2One of them is a substituted or unsubstituted divalent aromatic group (excluding a hydroxyl group-containing aromatic group), and the other is a divalent group in which a substituted or unsubstituted divalent aromatic group (excluding a hydroxyl group-containing aromatic group) and a substituted or unsubstituted divalent cycloalkylene group (excluding a hydroxyl group-containing cycloalkylene group) are connected by a single bond.

[0089] In Y 1 and Y 2 When all are 5-hexenyl, Q is a group represented by formula (2), and A 1 and A 2 One of them is a substituted or unsubstituted divalent aromatic group (excluding a hydroxyl group-containing aromatic group), and the other is a divalent group in which a substituted or unsubstituted divalent aromatic group (excluding a hydroxyl group-containing aromatic group) and a substituted or unsubstituted divalent cycloalkylene group (excluding a hydroxyl group-containing cycloalkylene group) are connected by a single bond.

[0090] The melting point of the vinyl compound (A) is preferably 50 to 150° C., more preferably 80 to 140° C., further preferably 85 to 135° C., and particularly preferably 90 to 130° C. When the melting point of the vinyl compound is within the above range, processing by melt kneading or the like becomes easy, and the energy required for processing can be reduced.

[0091] The vinyl compound (A) 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 (A) can be suitably used to form a constituent material such as an insulating layer of a printed wiring board and a heat dissipation material.

[0092] On the other hand, resins having hydroxyl groups in the resin 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 (A) is not an epoxy group or a hydroxyl group, but a vinyl group (vinyl group). Therefore, the cured product (polymer) of the vinyl compound (A) does not have a hydroxyl group in the resin and therefore shows low dielectric loss.

[0093] <Method for producing vinyl compound (A)>

[0094] The vinyl compound (A) can be produced, for example, by reacting a compound represented by formula (a) (sometimes referred to as “compound (a)” in the present specification), a compound represented by formula (b) (sometimes referred to as “compound (b)” in the present specification), and a compound represented by formula (c) (sometimes referred to as “compound (c)” in the present specification) in the presence of a base.

[0095] [Chemical formula 5]

[0096]

[0097] (In the formula, Q has the same meaning as above.)

[0098] [Chemical formula 6]

[0099]

[0100] (Where Y 1 Means the same as above, Z 1 represents a halogen atom. )

[0101] [Chemical formula 7]

[0102]

[0103] (Where Y 2 Means the same as above, Z 2 represents a halogen atom, which can be combined with the above Z 1 The same or different.)

[0104] Examples of the compound (a) include 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-methylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3-ethylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-2-propylbenzoate, 4-(4-hydroxyphenyl)cyclohexyl-4-hydroxy-3,5-dimethylbenzoate, 1,1-(2-methyl-1,4-phenylene)bis(4-hydroxybenzoate) Esters), 1,4-phenylene-bis(4-hydroxybenzoate), 1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxybenzoate), 2-methoxy-1,4-phenylene-bis(4-hydroxybenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-2-methylbenzoate), 2-Methyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2-methyl-1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,6-dimethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), 2,3,6-trimethyl-1,4-phenylene -bis(4-hydroxybenzoate), 2,3,6-trimethyl-1,4-phenylene-bis(4-hydroxy-2,6-dimethylbenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxy-3-methylbenzoate), 2,3,5,6-tetramethyl-1,4-phenylene-bis(4-hydroxy-3,5-dimethylbenzoate), (4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 4-(4-hydroxycyclohexyl)phenol, and 4,4'-bicyclohexanol. Compound (a) may also be a commercially available product, and may be produced according to a known method described in Japanese Patent Application Laid-Open No. 2011-74366 or Japanese Patent Application Laid-Open No. 2010-241797.

[0105] The above Z 1 and Z 2The same as or different from each other means a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, an iodine atom, etc. Compound (b) and compound (c) may be the same as or different from each other.

[0106] Examples of compound (b) and compound (c) include 2-vinylbenzyl bromide, 3-vinylbenzyl bromide, 4-vinylbenzyl bromide, 2-vinylbenzyl chloride, 3-vinylbenzyl chloride, 4-vinylbenzyl chloride, 1-propenyl chloride, 1-propenyl bromide, 1-butenyl chloride, 1-butenyl bromide, 1-pentenyl chloride, 1-pentenyl bromide, 1-hexenyl chloride, 1-hexenyl bromide, acryloyl bromide, acryloyl chloride, methacryloyl bromide, and methacryloyl chloride. Compound (b) and compound (c) may be used alone or in any combination and ratio.

[0107] When compound (b) and compound (c) are the same, the amount of compound (b) used is usually preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents, relative to compound (a). When compound (b) and compound (c) are different, the amount of compound (b) used is usually preferably 1 to 50 equivalents, more preferably 1 to 25 equivalents, relative to compound (a), and the amount of compound (c) used is usually preferably 1 to 50 equivalents, more preferably 1 to 25 equivalents, relative to compound (a).

[0108] The above-mentioned base may be any of an inorganic base and an organic base.

[0109] 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.

[0110] 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.

[0111] The reaction of compound (a), compound (b) and compound (c) is usually carried out by mixing compound (a), compound (b), compound (c) and a base in a solvent. The order of mixing is not particularly limited.

[0112] 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.

[0113] 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.

[0114] The amount of the solvent used is preferably 1 to 20 mL, more preferably 2 to 10 mL, per 1 g of compound (a).

[0115] Regardless of whether compound (b) and compound (c) are the same, the reaction of compound (a) with compound (b); the reaction of an intermediate which is a product of the reaction of compound (a) with compound (b) with compound (c); the reaction of compound (a) with compound (c); and the reaction of an intermediate which is a product of the reaction of compound (a) with compound (c) with compound (b) can be carried out via a halogen exchange reaction in the presence of a catalyst.

[0116] Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide.

[0117] 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.

[0118] The reaction of compound (a), compound (b) and compound (c) can 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 total amount used of compound (b) and compound (c).

[0119] 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.

[0120] 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 or more as needed to obtain a vinyl compound (A). 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 (A) can be further purified by a conventional purification method as needed.

[0121] The structure of the obtained vinyl compound (A) can be confirmed by a known method such as a nuclear magnetic resonance (NMR) method.

[0122] <Vinyl composition>

[0123] The vinyl composition of the present embodiment contains a vinyl compound (A).

[0124] In this specification, the vinyl composition of this embodiment may be referred to as "vinyl composition (A)".

[0125] The vinyl composition (A) is curable and may contain only the vinyl compound (A) or may contain other components other than the vinyl compound (A) within a range that does not impair the effect of the present invention. The vinyl compound (A) may be cured by heating or by light irradiation. In the following examples, the vinyl composition (A) is cured by heating. When curing the vinyl composition (A), pressure may be applied to the vinyl composition (A). The vinyl composition (A) may be suitably used for forming a constituent material such as an insulating layer of a printed wiring board, a heat dissipation material, etc.

[0126] The vinyl compound (A) contained in the vinyl composition (A) may be only one kind or two or more kinds.

[0127] The vinyl composition (A) contains two or more kinds of Y 1 and Y 2In the case of the vinyl compound (A) in which at least one of the vinyl compounds is a vinyl benzyl group, the vinyl composition (A) preferably contains a mixture of a plurality of vinyl compounds (A) having different positions of the vinyl groups of the vinyl benzyl groups as terminal groups and having the same parts other than the vinyl benzyl groups.

[0128] For example, in the case of a mixture containing two or more Y 1 and Y 2 In the vinyl composition (A) of the vinyl compound (A) in which at least one of the vinyl compounds is a vinyl benzyl group, when the number of moles of all vinyl benzyl groups in all the vinyl compounds (A) is 100, the number of moles of the vinyl benzyl groups in which the vinyl group is at the 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. In addition, for example, the ratio of the number of moles of the vinyl benzyl groups in which the vinyl group is at the para-position to the number of moles of the vinyl benzyl groups in which the vinyl group is at the meta-position (the number of moles of p-vinyl benzyl groups / the number of moles of m-vinyl benzyl 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 molar number or p / m ratio of the vinyl benzyl group in which the vinyl group is at the meta-position within the above range, the mixture of the vinyl compound (A) melts at a lower temperature, thereby improving the processability of the vinyl compound.

[0129] <Other ingredients>

[0130] Examples of the other components contained in the vinyl composition (A) include free radical initiators; fillers; additives; solvents; vinyl compounds other than the vinyl compound (A) (sometimes referred to as "other vinyl compounds" in this specification); resins other than polymers (cured products) of the vinyl compound (A) (sometimes referred to as "other resins" in this specification), and the like.

[0131] 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.

[0132] Examples of the radical initiator include azo compounds and organic peroxides.

[0133] 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.

[0134] As said silane coupling agent, γ-glycidoxypropyltrimethoxysilane etc. are mentioned, for example.

[0135] Examples of the colorant include carbon black and the like.

[0136] Examples of the low stress component include silicone oil and silicone rubber.

[0137] Examples of the release agent include natural wax, synthetic wax, higher fatty acid, metal salt of higher fatty acid, paraffin wax, and the like.

[0138] Examples of the solvent contained in the vinyl composition (A) 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.

[0139] The other vinyl compound is not particularly limited as long as it has a vinyl group and does not belong to the vinyl compound (A).

[0140] The other resin is not particularly limited as long as it is a resin other than the polymer of the vinyl compound (A).

[0141] The vinyl composition (A) may contain only one of the above-mentioned other components, or two or more of them.

[0142] The content of the other components in the vinyl composition (A) can be arbitrarily selected depending on the types of the other components.

[0143] In the vinyl composition (A), the ratio of the content of the vinyl compound (A) relative to the total content of the components other than the solvent 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 (A) having the above ratio of 80% by mass or more is preferred because the effect obtained by containing the vinyl compound (A) is further improved.

[0144] The vinyl compound (A) obtained by the above method can be used as a vinyl composition (A) as it is. The vinyl composition (A) containing the above other components is obtained by mixing the vinyl compound (A) and the above other components.

[0145] <Cured vinyl resin>

[0146] The cured vinyl resin of the present embodiment is obtained by curing the vinyl compound (A) or the vinyl composition (A).

[0147] In this specification, the cured vinyl resin material of this embodiment may be referred to as a "cured vinyl resin material (A)".

[0148] The cured vinyl resin has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A), and is therefore suitable as a constituent material of a printed wiring board, and particularly suitable as an insulating material constituting a printed wiring board.

[0149] When the cured vinyl resin (A) is a cured product of a vinyl compound (A), the cured vinyl resin (A) may be a cured product of one type of vinyl compound (A) or a cured product of two or more types of vinyl compounds (A).

[0150] When the cured vinyl resin (A) is a cured product of a vinyl composition (A), the cured vinyl resin (A) may be a cured product of one type of vinyl composition (A) or a cured product of a mixture of two or more types of vinyl compositions (A).

[0151] The cured vinyl resin (A) can be produced, for example, by the following methods: a method in which the vinyl compound (A) or the vinyl composition (A) is directly filled into a mold, and heated for a predetermined time as required to perform primary curing, and further heated for a predetermined time while applying pressure at a predetermined pressure using a press or the like to perform complete curing; a method in which the vinyl compound (A) or the vinyl composition (A) is directly heated at a predetermined temperature to cure it; a method in which a powder of the vinyl compound (A) or the vinyl composition (A) is directly or as required melted, and injected into a mold, and heated for a predetermined time while applying pressure at a predetermined pressure using a press or the like; a method in which the vinyl compound (A) or the vinyl composition (A) is heated and melted and injected into a mold; A method of forming by heating the mold in a mold, etc.; a method of melting a vinyl compound (A) or a vinyl composition (A), injecting the obtained melt into a preheated mold for solidification; a method of partially solidifying a vinyl compound (A) or a vinyl composition (A), pulverizing the obtained partially solidified product, filling the obtained powder into a mold, and melting the filled powder to form a mold; a method of dissolving a vinyl compound (A) or a vinyl composition (A) 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, etc. as needed, etc.

[0152] The heating temperature when the vinyl compound (A) or the vinyl composition (A) is heated to cure (curing temperature; when curing is performed in multiple stages, the complete curing temperature) is not particularly limited, but is preferably 120° C. or higher, more preferably 150° C. or higher, from the viewpoint of increasing the degree of cure of the vinyl compound (A) or the vinyl composition (A). From the viewpoint of avoiding excessive heating, the heating temperature is preferably 200° C. or lower.

[0153] The heating time (curing time; when curing is performed in multiple stages, the heating time at the complete curing temperature) when the vinyl compound (A) or the vinyl composition (A) 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 (A) or the vinyl composition (A). From the viewpoint of avoiding unnecessary curing operations, the heating time is preferably 10 hours or less.

[0154] The pressure applied when the vinyl compound (A) or the vinyl composition (A) 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 (A) or the vinyl composition (A). From the viewpoint of avoiding excessive pressurization, the pressure applied is preferably 3 MPa or less.

[0155] The thermal diffusivity of the cured vinyl resin (A) is preferably 1.75×10 -7 m 2 / s or more, more preferably 1.80×10 -7 m 2 / s or more, more preferably 1.90×10 -7 m 2 When the thermal diffusivity is within the above range, the thermal conductivity tends to be high. The upper limit of the thermal diffusivity of the cured vinyl resin (A) is not particularly limited, and the thermal diffusivity may be 4.00×10 -7 m 2 / s or less, and can also be 3.60×10 -7 m 2 / s or less, and can also be 3.20×10 -7 m 2 / s or less.

[0156] The thermal diffusivity of the cured vinyl resin (A) can be, for example, 1.70×10 -7 ~4.00×10 -7 m 2 / s, 1.80×10 -7 ~3.60×10 -7 m 2 / s and 1.90×10 -7 ~3.20×10 -7 m 2 / s.

[0157] The thermal diffusivity of the cured vinyl resin (A) can be measured by temperature wave thermal analysis (TWA method).

[0158] The dielectric loss tangent of the cured vinyl resin (A) at a frequency of 100 MHz is preferably 0.0310 or less, more preferably 0.0200 or less, and further preferably 0.0100 or less. The lower limit of the dielectric loss tangent of the cured vinyl resin (A) is not particularly limited, and the dielectric loss tangent may be 0.0010 or more, 0.0020 or more, or 0.0030 or more.

[0159] The dielectric loss tangent of the cured vinyl resin (A) at a frequency of 100 MHz may be, for example, any one of 0.0010 to 0.0310, 0.0020 to 0.0200, and 0.0030 to 0.0100. However, these are only examples of the dielectric loss tangent of the cured vinyl resin (A).

[0160] The dielectric loss tangent of the cured vinyl resin (A) at a frequency of 100 MHz can be measured by a capacitance method using an impedance analyzer under the following conditions.

[0161] ·Determination method: Volumetric method

[0162] Electrode model: 16453A

[0163] ·Measurement environment: 23℃, 50%RH

[0164] Applied voltage: 1V

[0165] <Prepreg>

[0166] The prepreg of the present embodiment includes a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a fibrous base material.

[0167] In this specification, the prepreg of this embodiment is sometimes referred to as "prepreg (A)". By using the prepreg (A), a laminated board or the like can be easily manufactured by a conventional method. For example, a plurality of prepregs (A) 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.

[0168] The printed wiring board (resin layer in the printed wiring board) obtained by using the prepreg (A) or the above-mentioned laminate has high thermal conductivity and low dielectric loss by using the vinyl compound (A).

[0169] The prepreg (A) can be produced by the following method: a method in which a solution obtained by dissolving a vinyl compound (A) in a solvent is applied to or impregnated on a fibrous base material; or a method in which a vinyl composition (A) or a dilution obtained by diluting the vinyl composition (A) with a solvent is applied to or impregnated on a fibrous base material, and then the applied or impregnated fibrous base material is heated to semi-cure the vinyl compound (A) or the vinyl composition (A).

[0170] The heating temperature (semi-curing temperature) and heating time (semi-curing time) when semi-curing the vinyl compound (A) or the vinyl composition (A) can be appropriately set in consideration of the above-mentioned curing conditions (heating temperature and heating time) of the vinyl compound (A) or the vinyl composition (A) so that the vinyl compound (A) or the vinyl composition (A) is not completely cured.

[0171] 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.

[0172] <Film with resin>

[0173] The resin-bearing film of the present embodiment comprises: a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a support film. 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 while being heated and pressurized, 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 using the above-mentioned resin layer or laminate have high thermal conductivity and low dielectric loss by using a vinyl compound (A).

[0174] Examples of the support film include polyethylene terephthalate (PET) films and the like.

[0175] 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.

[0176] The film with resin of the present embodiment can be manufactured by applying a solution obtained by dissolving a vinyl compound (A) in a solvent to the above-mentioned support film, or applying a vinyl composition (A) or a dilution obtained by diluting the vinyl composition (A) with a solvent to the above-mentioned support film, and then heating the layer of the coated material to semi-cure the vinyl compound (A) or the vinyl composition (A) in the coated material. The conditions for semi-curing the vinyl compound (A) or the vinyl composition (A) are the same as the conditions for manufacturing the prepreg described above.

[0177] <Metal foil with resin>

[0178] The metal foil with resin of the present embodiment comprises a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a metal foil. As the metal foil with resin of the present embodiment, more specifically, for example, a metal foil with resin having 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 (A) or a cured product of a vinyl composition (A) 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 due to the use of the vinyl compound (A).

[0179] As said metal foil, copper foil etc. are mentioned, for example.

[0180] 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.

[0181] 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.

[0182] <Metal-clad laminate>

[0183] The metal-clad laminate of the present embodiment comprises: an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and a metal foil. As the metal-clad laminate of the present embodiment, more specifically, for example, a metal-clad laminate having 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 circuit board, for example, by patterning the metal foil therein to form a conductor wiring (circuit). In addition, such a plurality of printed circuit boards can be stacked across an insulating layer prepared separately, and pressurized while heating, thereby making a multilayer printed circuit board. The insulating layer in the metal-clad laminate of the present embodiment and the printed circuit board (insulating layer in the printed circuit board) obtained using the above-mentioned metal-clad laminate have high thermal conductivity and low dielectric loss by using a vinyl compound (A).

[0184] 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.

[0185] 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.

[0186] 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 as a laminate of a plurality of the resin layers, or may be the prepreg (A), or the laminated board obtained by laminating a plurality of prepregs (A). Alternatively, in these resin layers, laminated sheets, prepregs (A), or laminated boards, a substance obtained by further curing the vinyl compound (A) or the vinyl composition (A) may also be the insulating layer.

[0187] 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 (A), and heating and pressurizing the resulting laminate to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the prepreg (A) to form a cured product, thereby forming an insulating layer, and fusing the prepreg (A) to the metal foil.

[0188] The metal-clad laminate of the present embodiment can be produced by, for example, using the vinyl compound (A) or the vinyl composition (A) to produce a prepreg (A) by the method described above, and using the prepreg (A) to produce the metal-clad laminate by the method described above.

[0189] 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 (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the above-mentioned resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A).

[0190] <Printed circuit board>

[0191] The printed wiring board of this embodiment comprises: an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and conductor wiring. As a printed wiring board of this embodiment, more specifically, for example, 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 can be cited. A plurality of printed wiring boards of this embodiment can be stacked with an insulating layer prepared separately, and pressurized while being heated, thereby making 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 (A).

[0192] 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.

[0193] 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.

[0194] 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).

[0195] The printed wiring board of this embodiment can also be manufactured, for example, by heating the above-mentioned metal foil with resin to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the above-mentioned resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A), and further patterning the metal foil to form a conductor wiring (circuit).

[0196] The metal foil can be patterned by a known method such as etching.

[0197] Figure 11 is a cross-sectional view schematically showing an example of a laminated structure of the present embodiment obtained by using a vinyl compound (A). 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, for convenience, the main parts are sometimes enlarged, and the size ratios of the components are not necessarily the same as the actual ones.

[0198] 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 (A). 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.

[0199] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a support film, the laminated structure 1 is a film with a resin.

[0200] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a metal foil, the laminated structure 1 is a metal foil with resin.

[0201] When the first layer 11 is an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 is a metal foil, the laminated structure 1 is a metal-clad laminate.

[0202] Figure 2 is a cross-sectional view schematically showing another example of the laminated structure of the present embodiment obtained using the vinyl compound (A). 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.

[0203] 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.

[0204] When the first layer 11 is an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 22 is a conductor wiring, the laminated structure 2 is a printed wiring board.

[0205] 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 .

[0206] 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 (A).

[0207] 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.

[0208] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are support films, the laminated structure 3 is a film with resin.

[0209] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal foil with resin.

[0210] When the first layer 11 is an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal-clad laminate.

[0211] 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 (A).

[0212] 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.

[0213] When the first layer 11 is an insulating layer comprising a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 22 and the third layer 23 are conductor wirings, the laminated structure 4 is a printed wiring board.

[0214] Example

[0215] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.

[0216] It should be noted that, in the following examples, "room temperature" refers to a temperature range of 15 to 40°C.

[0217] The conditions for measuring the melting point of the vinyl compound are shown.

[0218] A glass dish filled with a vinyl compound was heated under the following conditions using a differential scanning calorimeter (FP84HT manufactured by METTLER TLEDO), and the endothermic peak temperature was taken as the melting point. When there were multiple endothermic peaks, the endothermic peak temperature on the lower temperature side was taken as the melting point.

[0219] The test conditions of the cured product are shown.

[0220] (1) Thermal diffusivity

[0221] 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.).

[0222] [Example 1]

[0223] In a 5 L bottomless four-necked flask equipped with a thermometer, a condenser and a stirrer, 230 g of trans-4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 2.3 g of 2,6-di(tert-butyl)-p-cresol, 407 g of potassium carbonate, 22.1 g of sodium iodide, 1 L of N,N-dimethylformamide and 337.6 g of vinylbenzyl chloride (a mixture of meta- and para-isomers) were added and reacted at an internal temperature of about 80° C. for 2 hours.

[0224] After the reaction was completed, the mixture was cooled to room temperature, 1500 mL of water and 1500 mL of hexane were added, the precipitated solid was filtered out, and washed with hexane. The obtained solid was dissolved in a mixed solution of toluene and THF, and washed with water. After the solvent was removed from the obtained solution under reduced pressure, 180 mL of methanol and 2,6-di(tert-butyl)-p-cresol were added to the obtained concentrated solution and stirred, and then filtered out and dried under reduced pressure.

[0225] A portion of the obtained solid (15.0 g), 2,6-di(tert-butyl)-p-cresol (0.15 g), toluene (680 g), and silica gel (75 g) were mixed, stirred at an internal temperature of 45°C for 40 minutes, and then filtered to remove insoluble matter. Toluene was removed from the obtained solution under reduced pressure, and then stirred at an internal temperature of 50°C to completely dissolve it, and then cooled at 10°C. The precipitated crystals were filtered out, washed with methanol, and dried under reduced pressure to obtain 5.4 g of the vinyl compound 1 represented by the following formula (A-1). Purity: 99.3% (liquid chromatography area percentage value).

[0226] [Chemical formula 8]

[0227]

[0228] [Example 2]

[0229] In a 300 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 7.3 g of 1,1-(2-methyl-1,4-phenylene)bis(4-hydroxybenzoate), 0.07 g of 2,6-di(tert-butyl)-p-cresol, 14.0 g of potassium carbonate, 0.6 g of sodium iodide, 140 mL of N,N-dimethylformamide and 18.0 g of vinylbenzyl chloride (a mixture of meta and para isomers) were added and reacted at an internal temperature of about 60°C for 3 hours. After the reaction was completed, it was cooled to room temperature. Then, 41 mL of heptane and 41 mL of water were added, and after stirring for 10 minutes, the precipitated solid was filtered out and washed with water, heptane and methanol. The obtained solid was mixed with 1 L of toluene and filtered to remove the insoluble matter. 0.07 g of 2,6-di(tert-butyl)-p-cresol was added to the filtrate, and after a part of the solvent was removed under reduced pressure, it was heated to 50°C, methanol was added, and it was cooled to room temperature while stirring. The precipitated crystals were collected by filtration, washed with methanol, and then dried under reduced pressure to obtain 3.6 g of a vinyl compound 2 represented by the following formula (A-2). Purity: 97.7% (liquid chromatography area percentage value).

[0230] [Chemical formula 9]

[0231]

[0232] [Example 3]

[0233] In a 200 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 4.3 g of (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 0.04 g of 2,6-di(tert-butyl)-p-cresol, 6.9 g of potassium carbonate, 0.3 g of sodium iodide, 60 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. After the reaction was completed, it was cooled to room temperature. Then, 30 mL of heptane and 40 mL of water were added, and after stirring for 10 minutes, the precipitated solid was filtered out and washed with water, heptane and methanol. The obtained solid was dried under reduced pressure to obtain 5.8 g of the vinyl compound 3 represented by the following formula (A-3). Purity: 84.6% (liquid chromatography area percentage value).

[0234] [Chemical formula 10]

[0235]

[0236] [Example 4]

[0237] In a 500 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 36.0 g of trans-4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 0.4 g of 2,6-di(tert-butyl)-p-cresol, 28.0 g of triethylamine and 156 mL of N,N-dimethylformamide were added, and 25.1 g of acryloyl chloride was added at an internal temperature of about 10°C, and the reaction was carried out at an internal temperature of about 20°C for 4 hours. After the reaction was completed, the internal temperature was cooled to about 10°C, and 72 mL of water was added. The obtained suspension was mixed with 500 mL of water, and the precipitated solid was filtered out and washed with water and methanol. The obtained solid was dissolved in a mixed solution of toluene and heptane, and filtered while heating to an internal temperature of about 50°C, and the obtained solution was cooled at an internal temperature of about 5°C. The precipitated solid was filtered out and dried under reduced pressure to obtain 28.9 g of the vinyl compound 4 represented by the following formula (A-4). Purity: 84.9% (HPLC area percentage).

[0238] [Chemical formula 11]

[0239]

[0240] [Example 5]

[0241] In a 500 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 8.3 g of sodium hydride and 56 mL of N,N-dimethylformamide were added, and a mixture of 10.0 g of 4-(trans-4-hydroxycyclohexyl)phenol and 84 mL of N,N-dimethylformamide was added dropwise at an internal temperature of about 5°C, and stirred at room temperature for 1 hour. 3.8 g of tetrabutylammonium iodide, 31.8 g of 4-vinylbenzyl chloride and 0.1 g of 2,6-di(tert-butyl)-p-cresol were added, and stirred at room temperature for 6 hours. Water and toluene were added to the obtained suspension to separate the liquid. The obtained organic layer was cooled to about 5°C, the precipitated solid was filtered out, and it was dried under reduced pressure to obtain the vinyl compound 5 represented by the following formula (A-5). Purity: 99.3% (liquid chromatography area percentage).

[0242] [Chemical formula 12]

[0243]

[0244] [Example 6]

[0245] In a 500 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 10.0 g of 4,4'-bicyclohexanol and 108 mL of N,N-dimethylformamide were added, and after heating to an internal temperature of about 50°C, a suspension of N,N-dimethylformamide containing 8.1 g of sodium hydride was added, and stirred for 1 hour. After cooling to room temperature, 7.4 g of tetrabutylammonium iodide, 30.8 g of 4-vinylbenzyl chloride, 0.1 g of 2,6-di(tert-butyl)-p-cresol and 14 mL of N,N-dimethylformamide were added, and stirred at an internal temperature of about 50°C for 24 hours. Water and toluene were added to the obtained suspension to separate the liquids. The obtained organic layer was cooled to about 5°C, the precipitated solid was filtered out, and it was dried under reduced pressure to obtain a vinyl compound 6 represented by the following formula (A-6). Purity: 92.7% (liquid chromatography area percentage).

[0246] [Chemical formula 13]

[0247]

[0248] [Example 7]

[0249] In a 500 mL four-necked flask equipped with a thermometer, a condenser and a stirring device, 19.0 g of trans-4-(4-hydroxyphenyl)cyclohexyl-4-hydroxybenzoate, 42.0 g of potassium carbonate, 1.8 g of sodium iodide and 250 mL of N,N-dimethylformamide were added, and after heating to an internal temperature of about 60°C, 31.5 g of 1-hexenyl bromide was added and stirred for 15 hours. After cooling to room temperature, 250 mL of water was added and filtered, and toluene was added to the obtained solution for liquid separation. After the solvent was removed from the obtained organic layer under reduced pressure, 600 mL of isopropanol was added and stirred at 60°C. After cooling to 0°C, the solid obtained by filtering the suspension was dried under reduced pressure to obtain the vinyl compound 7 represented by the following formula (A-7). Purity: 99.3% (liquid chromatography area percentage).

[0250] [Chemical formula 14]

[0251]

[0252] [Comparative Example 1]

[0253] 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 8 represented by the following formula (B). Purity: 99.1% (LC area percentage value).

[0254] [Chemical formula 15]

[0255]

[0256] Table 1 shows the melting points of the vinyl compounds.

[0257] [Table 1]

[0258]

[0259] The vinyl compounds obtained in Examples 1 to 3, 5, 6 and Comparative Example 1 were added to the plate-shaped hollow portion of the mold, and heated at the primary curing temperature shown in Table 2 for 1 hour while applying a pressure of 1.5 MPa under reduced pressure, and then heated at 180°C for 2 hours while applying a pressure of 1.5 MPa, thereby obtaining a cured product.

[0260] The vinyl compound obtained in Example 4 was added to the plate-shaped hollow portion of the mold, heated at the primary curing temperature shown in Table 1 for 1 hour, and then heated at 180° C. for 2 hours to obtain a cured product.

[0261] Table 2 shows the thermal diffusivity values ​​of the cured products.

[0262] [Table 2]

[0263]

[0264] Industrial Applicability

[0265] 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.

[0266] Description of Reference Numerals

[0267] 1, 2, 3, 4-layer structure

[0268] 11. Layer 1

[0269] 11a One surface of layer 1

[0270] 11b The other side of layer 1

[0271] 12, 22 Layer 2

[0272] 13, 23 Layer 3

Claims

1. A vinyl compound represented by formula (A), In the formula (A), Y 1 and Y 2 are all vinylbenzyl, (meth)acryloyl or 5-hexenyl, Q is a group represented by any one of the formulae (1) to (4), In the above formulas (1) to (4), A 1 , A 2 , A 3 and A 4 The same or different, is a substituted or unsubstituted divalent aromatic group excluding an aromatic group containing a hydroxyl group, a substituted or unsubstituted divalent cycloalkylene group excluding a cycloalkylene group containing a hydroxyl group, A divalent group formed by connecting two or more substituted or unsubstituted divalent aromatic groups excluding a hydroxyl-containing aromatic group via a single bond, A divalent group formed by connecting two or more substituted or unsubstituted divalent cycloalkylene groups, excluding a cycloalkylene group containing a hydroxyl group, via a single bond, or a divalent group formed by connecting one or more substituted or unsubstituted divalent aromatic groups not including a hydroxyl group and one or more substituted or unsubstituted divalent cycloalkylene groups not including a hydroxyl group through a single bond, X 1 , X 2 and X 3 are the same or different, and are ester bonds or carbonyl groups, In Y 1 and Y 2 When all are vinylbenzyl groups and Q is a group represented by formula (1), A 1 is a divalent group formed by connecting two substituted or unsubstituted divalent cycloalkylene groups which do not include a cycloalkylene group containing a hydroxyl group via a single bond, or a divalent group formed by connecting one substituted or unsubstituted divalent aromatic group which does not include a cycloalkylene group containing a hydroxyl group and one substituted or unsubstituted divalent cycloalkylene group which does not include a cycloalkylene group containing a hydroxyl group via a single bond, In Y 1 and Y 2 When all are (meth)acryloyl groups, Q is a group represented by formula (2), and A 1 and A 2 Any one of them is a substituted or unsubstituted divalent aromatic group that does not include a hydroxyl group-containing aromatic group, and the other is a divalent group formed by a substituted or unsubstituted divalent aromatic group that does not include a hydroxyl group and a substituted or unsubstituted divalent cycloalkylene group that does not include a hydroxyl group-containing aromatic group connected via a single bond, In Y 1 and Y 2 When all are 5-hexenyl, Q is a group represented by formula (2), and A 1 and A 2 Any one of them is a substituted or unsubstituted divalent aromatic group, and the other is a divalent group in which a substituted or unsubstituted divalent aromatic group that does not include a hydroxyl group and a substituted or unsubstituted divalent cycloalkylene group that does not include a hydroxyl group are linked via a single bond.

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

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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