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

Abstract

To provide a vinyl compound which enables production of a resin that is suitable as a component of a printed wiring board, and has high heat conductivity and low dielectric loss.SOLUTION: A vinyl compound is represented by a formula (A), wherein in the formula (A), Q is any one group of groups selected from a group consisting of formulae (1) to (3).SELECTED DRAWING: None

Description

[Technical field]

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

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

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

[0004] As a printed wiring board with high heat dissipation properties, a so-called metal-based substrate is known, which has a metal plate on one side thereof so that it can dissipate more heat through the metal plate. However, this metal-based substrate has a problem in that the number of manufacturing steps increases, which increases the manufacturing cost of the communication device.

[0005] On the other hand, as with printed wiring boards, materials that contain a filler with high thermal conductivity are known as components that have high heat dissipation properties and are primarily made of resin, similar to printed wiring boards. However, materials that contain fillers have poor processability, which is a problem in that they are not suitable for manufacturing printed wiring boards.

[0006] A resin with high thermal conductivity has been disclosed as a material that can solve these problems (Patent Document 1). Electronic materials used in high-speed communication devices are required to have high heat dissipation properties as well as low dielectric loss, and the resin disclosed in Patent Document 1 has high thermal conductivity and low dielectric loss by itself. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] US Patent Application Publication No. 2019 / 0194408 Summary of the Invention [Problem to be solved by the invention]

[0008] However, the thermal conductivity of the resin disclosed in Patent Document 1 cannot be said to be sufficient, and there is still room for improvement.

[0009] An object of the present invention is to provide a novel compound capable of producing a resin which is suitable as a constituent material for printed wiring boards and has high thermal conductivity and low dielectric loss. [Means for solving the problem]

[0010] The present invention employs the following configuration. [1] A vinyl compound represented by formula (A). [ka] (In the above formula (A), Y 1 and Y 2 are the same or different and each is a group selected from the group consisting of a vinyl group and a vinylbenzyl group, Q is any one of groups selected from the group consisting of formulas (1) to (3), [ka] In the formulas (1) to (3), A 1 , A 2 , A 3 and A 4 are the same or different and each represents a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) are linked by a single bond, A divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups are linked by a single bond, and a divalent group in which one or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups are linked via a single bond, Any one selected from the group consisting of: X 1 , X 2 and X 3 are the same or different and are selected from the group consisting of a single bond, an ester group, and a carbonyl group, Y 1 and Y 2 When at least one of the X constituting Q is a vinyl group, 1 , X 2 , and X 3 At least one of A is an ester group or a carbonyl group, and 1 , A 2 , A 3 , and A 4 at least one of is a cyclohexyl ring; n1 and n2 are the same or different and each represents an integer of 1 to 20. [2] X above 1 , X 2 and X 3 At least one of the vinyl groups is an ester group. [3] A 1 , A 2 , A 3 and A4 is a divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups). [4] The vinyl compound according to any one of [1] to [3], which is used for a printed wiring board. [5] A vinyl composition comprising the vinyl compound according to any one of [1] to [3]. [6] A vinyl resin cured product obtained by curing the vinyl compound according to any one of [1] to [3] and the vinyl composition according to [5]. [7] A prepreg comprising the vinyl compound or semi-cured product thereof according to any one of [1] to [3], or the vinyl composition or semi-cured product thereof according to [5], and a fibrous base material. [8] A resin-coated film comprising a resin layer comprising the vinyl compound or semi-cured product thereof according to any one of [1] to [3], or the vinyl composition or semi-cured product thereof according to [5], and a support film. [9] A vinyl compound or a semi-cured product thereof according to any one of [1] to [3], or 5] or a semi-cured product thereof; and a metal foil.

[10] A metal-clad laminate comprising an insulating layer containing a cured product of the vinyl compound according to any one of [1] to [3] or a cured product of the vinyl composition according to [5], and a metal foil.

[11] A metal-clad laminate comprising an insulating layer containing a cured product of the prepreg according to [7] and a metal foil.

[12] A printed wiring board comprising an insulating layer containing a cured product of the vinyl compound according to any one of [1] to [3] or a cured product of the vinyl composition according to [5], and a conductor wiring.

[13] A printed wiring board comprising an insulating layer containing a cured product of the prepreg according to [7] and conductive wiring. Effect of the Invention

[0011] According to the present invention, it is possible to provide a novel compound capable of producing a resin suitable as a constituent material of a printed wiring board, having high thermal conductivity and low dielectric loss. Furthermore, when the novel compound is used to produce a molded product such as a resin or a printed wiring board, the production process can be facilitated because the compound has a low melting point. [Brief description of the drawings]

[0012] [Figure 1] FIG. 1 is a cross-sectional view showing a schematic example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. [Diagram 2] FIG. 2 is a cross-sectional view showing a schematic diagram of another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. [Diagram 3] FIG. 2 is a cross-sectional view showing a schematic diagram of still another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. [Figure 4] FIG. 2 is a cross-sectional view showing a schematic diagram of still another example of a laminate structure obtained by using a vinyl compound according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] <Vinyl compounds> The vinyl compound of the present embodiment is represented by the following formula (A): In this specification, the vinyl compound represented by the above formula (A) may be referred to as "vinyl compound (A)". [ka]

[0014] Y in vinyl compound (A) 1 and Y 2 are the same or different and are either a group selected from the group consisting of a vinyl group and a vinylbenzyl group. The structure of Q is a mesogenic skeleton, and has a structure in which two or more hydrocarbon rings are linked. The number of carbon atoms in Q is not particularly limited, but may be 12 or more, for example, and is preferably 13 or more. In the formula (A), Q is any group selected from the group consisting of formulas (1) to (3), [ka] In the formulas (1) to (3), A 1 , A 2 , A 3 and A 4 are the same or different and each represents a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), a substituted or unsubstituted divalent cycloalkylene group, a divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) are linked by a single bond, A divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups are linked by a single bond, and a divalent group in which one or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups are linked by a single bond, It is any one selected from the group consisting of: Y 1 and Y 2 When at least one of the X constituting Q is a vinyl group, 1 , X 2 , and X 3 At least one of A is an ester group or a carbonyl group, and 1 , A 2 , A 3 , and A 4 At least one of the rings is a cyclohexyl ring. n1 and n2 are the same or different and each represents an integer of 1 to 20.

[0015] In this specification, the aromatic ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring, but is preferably a monocyclic ring.When the aromatic ring is a heterocyclic ring, the heteroatom contained in the heterocyclic ring may be a heteroatom other than a nitrogen atom, such as an oxygen atom and a sulfur atom.From the viewpoint of suppressing dielectric loss or reducing dielectric loss tangent, it is preferable that the aromatic ring does not contain a heteroatom.The aromatic ring is preferably a monocyclic ring or a condensed ring, and more preferably a monocyclic ring.

[0016] The number of carbon atoms in the unsubstituted divalent aromatic group is not particularly limited, but is preferably 3-20, more preferably 6-16, and even more preferably 6-14.

[0017] Specific examples of the unsubstituted divalent aromatic ring include benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene.

[0018] When the divalent aromatic group has a substituent, that is, when the aromatic ring has a substituent, the substituent is preferably a substituent other than a hydroxy group, and is, for example, one or more groups selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms.

[0019] Examples of the alkyl group having 1 to 20 carbon atoms include known alkyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 8, and more preferably 1 to 4. Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, and an isobutyl group.

[0020] Examples of the alkoxy group having 1 to 20 carbon atoms include known alkoxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 8, and more preferably 1 to 4. Specific examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, and an isobutyloxy group.

[0021] In this specification, the cycloalkane ring and the cycloalkene ring may be a monocyclic ring, a condensed ring, or a heterocyclic ring. When the cycloalkane ring or the cycloalkene ring is a heterocyclic ring, the heteroatom contained in the heterocyclic ring may be, for example, an oxygen atom, a nitrogen atom, and a sulfur atom. From the viewpoint of suppressing dielectric loss or dielectric tangent, it is preferable that the aromatic ring does not contain a heteroatom. The aromatic ring is preferably a monocyclic ring or a condensed ring, and more preferably a monocyclic ring. In addition, in this specification, the cycloalkylene group and the cycloalkenylene group may be in a cis form, a trans form, or a mixture thereof. In the case of a mixture, it is preferable that the proportion of the trans form is higher.

[0022] The number of carbon atoms in the unsubstituted divalent cycloalkylene group and cycloalkenylene group is not particularly limited, but is preferably 3-20, more preferably 6-16, and even more preferably 6-14.

[0023] Specific examples of unsubstituted cycloalkane rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane, cyclopentadecane, cyclohexadecane, cycloheptadecane, cyclooctadecane, cyclononadecane, cycloicosane, decalin, adamantane, oxetane, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 1,3-dioxane, aziridine, pyrrolidine, piperidine, piperazine, morpholine, tetrahydrothiophene, and thiane. Specific examples of the unsubstituted cycloalkene ring include cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, and cyclodecene.

[0024] When the divalent cycloalkylene group and cycloalkenylene group have a substituent, the substituent has the same meaning as the substituent that the divalent aromatic group may have.

[0025] In a compound in which two or more substituted or unsubstituted aromatic rings are linked by a single bond, the number of the 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.

[0026] 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-quarterphenyl, and p-quarterphenyl.

[0027] In a compound in which two or more substituted or unsubstituted cycloalkane rings or cycloalkene rings are linked by a single bond, the number of substituted or unsubstituted cycloalkane rings or cycloalkene 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.

[0028] Specific examples of compounds in which two or more unsubstituted cycloalkane or cycloalkene rings are linked by a single bond include cyclopropylcyclohexane, bicyclohexyl, 1,3-dicyclohexane, and cyclohexane. Examples include cyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

[0029] In a compound in which one or more substituted or unsubstituted aromatic rings and one or more substituted or unsubstituted cycloalkane rings or 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 as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1, and the number of substituted or unsubstituted cycloalkane rings or cycloalkene rings linked by a single bond is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. In addition, the total number of substituted or unsubstituted aromatic rings linked by a single bond and the number of substituted or unsubstituted cycloalkane rings or cycloalkene rings is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0030] Specific examples of the compound in which one or more unsubstituted aromatic rings and one or more unsubstituted cycloalkane rings or cycloalkene 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, 4-phenylmorpholine, 1,1'-(1-cyclohexene-1,4-diyl)-bisbenzene, 1-(4-phenyl-1-cyclohexen-1-yl)-3-methylbenzene, and the like.

[0031] A 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. A substituted or unsubstituted divalent cycloalkylene group or cycloalkenylene group is a residue obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted cycloalkane ring or cycloalkene ring.

[0032] A 1 , A 2 , A 3 and A 4From the viewpoint of improving thermal conductivity, it is preferable that is a divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups).

[0033] In formula (A), X 1 , X 2 and X 3 are the same or different and each represents a single bond, an ester group (*-COO-** or *-OCO-**; *, ** represents A 1 , A 2 , A 3 and A 4 and a carbonyl group, preferably an ester group or a carbonyl group, and more preferably an ester group. X 1 , X 2 and X 3 When the vinyl compound is an ester group, a cured vinyl resin material containing the vinyl compound can exhibit excellent heat conductivity.

[0034] In formula (A), n1 and n2 are the same or different and are preferably integers from 1 to 10, more preferably integers from 2 to 8. In this embodiment, by introducing alkyl spacers having carbon numbers of n1 and n2 into the vinyl compound in addition to the mesogenic skeleton, it is possible to obtain a vinyl compound with a low melting point.

[0035] The melting point of the vinyl compound (A) is preferably 50 to 150° C. or less, more preferably 80 to 140° C. or less, further preferably 90 to 130° C., and particularly preferably 95 to 120° 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.

[0036] The vinyl compound (A) has polymerizability and can form a vinyl resin cured product described later by polymerization (also referred to as "curing" in this specification). (A) can be suitably used to form components such as insulating layers and heat dissipation materials for printed wiring boards.

[0037] On the other hand, resins having hydroxyl groups in them 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 its dielectric loss is high. In contrast, the end of the vinyl compound (A) is neither an epoxy group nor a hydroxyl group, but a vinyl group (ethenyl group). Therefore, the cured product (polymer) of the vinyl compound (A) has no hydroxyl group in the resin, and therefore shows low dielectric loss.

[0038] <Production method of vinyl compound (A)> The vinyl compound (A) is, for example, a compound represented by the formula (B): [ka] (In the formula, Q has the same meaning as above.) (hereinafter, sometimes referred to as "compound (B)") represented by formula (C) or formula (D) [ka] (In the formula, Z 1 represents a halogen atom, and n represents an integer of 1 to 20. (hereinafter, may be referred to as "compound (C)" or "compound (D)") in the presence of a base.

[0039] Examples of the compound (B) include 1-1'-(1-1'-biphenyl)-4-4'-diyl bis(4-hydroxybenzoate), (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), and the like.

[0040] Said Z 1 represents a halogen atom, and examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom. Examples of the compound (C) or the compound (D) include 2-vinylbenzyl bromoalkyl ether, 3-vinylbenzyl bromoalkyl ether, 4-vinylbenzyl bromoalkyl ether, chloroalkyl vinyl ether, bromoalkyl vinyl ether, 2-vinylbenzyl chloroalkyl ether, 3-vinylbenzyl chloroalkyl ether, 4-vinylbenzyl chloroalkyl ether, etc. The compound (C) and the compound (D) may be used alone or in any combination and ratio of two or more kinds.

[0041] The amount of compound (C) or compound (D) used is usually preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents, relative to compound (B).

[0042] The base used in the reaction may be either an inorganic base or an organic base. Examples of the inorganic base include alkali metals such as sodium hydride and potassium hydride. Examples of the hydroxide include hydrides; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as sodium carbonate and potassium carbonate. Examples of the organic base include pyridine. The amount of the base used is usually preferably 2 to 5 equivalents relative to the compound (B). When an organic base that is liquid under reaction conditions is used, such an organic base may be used in an excess amount to serve as a reaction solvent.

[0043] The reaction of compound (B) with compound (C) or compound (D) is usually carried out in a solvent by mixing compound (B), compound (C) or compound (D), and a base. The order of mixing is not particularly limited.

[0044] The solvent is not particularly limited as long as it is a solvent inert to the reaction, but a hydrophilic solvent is preferred in that it is easy to suppress the generation of by-products. Examples of the hydrophilic solvent include alcohol-based solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, and propylene glycol; ketone-based solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone; and ether-based solvents such as tetrahydrofuran, dioxane, methoxymethyl ether, and diethoxyethane, either alone or in combination. In addition, as described above, when an organic base that is liquid under reaction conditions is used as a base, the organic base may be used as a reaction solvent. Among these, the solvent is preferably an ether solvent, an aprotic polar solvent, or a mixture thereof, more preferably an aprotic polar solvent, and particularly preferably N,N-dimethylformamide. The amount of the solvent used is preferably 1 to 20 mL, and more preferably 2 to 10 mL, per gram of compound (B).

[0045] The reaction between compound (B) and compound (C) or compound (D) may be carried out via a halogen exchange reaction in the presence of a catalyst. Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide. When a catalyst is used, the amount of the catalyst used is usually preferably 0.05 to 1 times by mass, more preferably 0.1 to 0.5 times by mass, relative to the amount of compound (B) used.

[0046] The reaction between compound (B) and compound (C) or compound (D) may be carried out in the presence of a polymerization inhibitor. Examples of the polymerization inhibitor include 2,6-di(tert-butyl)-p-cresol. When a polymerization inhibitor is used, the amount of the polymerization inhibitor is usually preferably 0.002 to 0.05 times by mass, more preferably 0.004 to 0.02 times by mass, relative to the amount of compound (C) or compound (D).

[0047] The reaction may be carried out under normal pressure conditions or under reduced pressure conditions. The reaction temperature is usually preferably 10 to 150°C. In this reaction, water may be by-produced as the reaction proceeds. In that case, it is preferable to carry out the reaction while removing the by-produced water from the reaction system, and it is preferable to carry out the reaction at a reaction temperature and reaction pressure at which water is removed azeotropically. The reaction time is usually preferably 1 to 24 hours.

[0048] 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 off, and if necessary, a known post-treatment operation is carried out once or twice or more times to obtain the 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; extraction (liquid separation) of the solution in which the solid is dissolved, and the like. If necessary, the obtained vinyl compound (A) can be purified by a conventional purification means. It may be further purified by

[0049] The structure of the obtained vinyl compound (A) can be confirmed by a known method such as a nuclear magnetic resonance (NMR) method.

[0050] <Vinyl composition> The vinyl composition of the present embodiment contains a vinyl compound (A). In this specification, the vinyl composition of the present embodiment may be referred to as "vinyl composition (A)".

[0051] The vinyl composition (A) has curability and may contain only the vinyl compound (A), or may contain the vinyl compound (A) and other components other than the vinyl compound (A) within the range that does not impair the effects of the present invention. The vinyl compound (A) may be cured by heating or by light irradiation. In the following examples, it is cured by heating. When the vinyl compound (A) is cured, pressure may be applied to the vinyl compound (A).

[0052] The vinyl composition (A) may contain only one type of vinyl compound (A), or may contain two or more types of vinyl compounds (A). When the vinyl composition (A) contains two or more types of vinyl compounds (A), the vinyl compounds (A) are preferably a mixture of multiple types of vinyl compounds (A) in which the positions of the vinyl groups in the terminal vinylbenzyl groups are different and the portions other than the vinylbenzyl groups are identical.

[0053] For example, in a vinyl composition (A) containing two or more kinds of vinyl compounds (A), when the mole number of all vinylbenzyl groups in all vinyl compounds (A) is taken as 100, the mole number of vinylbenzyl groups whose vinyl group position is m-position is preferably 30 to 90, more preferably 40 to 90, even more preferably 50 to 90, even more preferably 60 to 80, and particularly preferably 70 to 80. In addition, for example, the ratio of the mole number of vinylbenzyl groups whose vinyl group position is p-position to the mole number of vinylbenzyl groups whose vinyl group position is m-position (molar number of p-vinylbenzyl groups / molar number of m-vinylbenzyl groups; sometimes referred to as "p / m ratio" in this specification) is preferably 10 / 90 to 70 / 30, more preferably 10 / 90 to 60 / 40, even more preferably 10 / 90 to 50 / 50, even more preferably 20 / 80 to 40 / 60, and particularly preferably 20 / 80 to 30 / 70. When the molar number of vinylbenzyl groups at the m-position of the vinyl groups or the p / m ratio is within the above range, the mixture of vinyl compounds (A) melts at a lower temperature, thereby improving the processability of the vinyl compounds.

[0054] <Other ingredients> Examples of the other components contained in the vinyl composition (A) include a radical initiator; a filler; an additive; a solvent; a vinyl compound other than the vinyl compound (A) (sometimes referred to as "other vinyl compounds" in this specification); and a resin other than the polymer (cured product) of the vinyl compound (A) (sometimes referred to as "other resins" in this specification).

[0055] Examples of the additives include silane coupling agents, colorants, low stress components, release agents, antioxidants, antifoaming agents, and flow control agents.

[0056] Examples of the radical initiator include an azo compound and an organic peroxide.

[0057] Examples of the filler include silica powders such as fused crushed silica powder, fused spherical silica powder, crystalline silica powder, and secondary agglomerated silica powder; alumina, titanium oxide, zinc oxide, Examples of the material include metal oxides such as tungsten carbide and magnesium oxide; glass cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, and titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; and mica.

[0058] The silane coupling agent may, for example, be γ-glycidoxypropyltrimethoxysilane. The colorant may, for example, be carbon black. Examples of the low stress component include silicone oil and silicone rubber. Examples of the release agent include natural wax, synthetic wax, higher fatty acid, metal salt of higher fatty acid, and paraffin.

[0059] Examples of the solvent contained in the vinyl composition (A) include ketone-based solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as dimethyl sulfoxide and N-methylpyrrolidone; ester-based solvents such as butyl acetate; glycol-based solvents such as propylene glycol monomethyl ether; and aromatic solvents such as toluene.

[0060] The other vinyl compound is not particularly limited as long as it has a vinyl group and does not fall under the category of the vinyl compound (A). The other resin is not particularly limited as long as it is a resin other than a polymer of the vinyl compound (A).

[0061] The vinyl composition (A) may contain only one type of other component, or two or more types of other components.

[0062] The content of the other components in the vinyl composition (A) can be selected arbitrarily depending on the type of the other components. In the vinyl composition (A), the content ratio of the vinyl compound (A) to the total content of components other than the solvent is preferably 80% by mass or more, and may be, for example, any of 85% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, and 99% by mass or more. Meanwhile, the ratio is 100% by mass or less. The vinyl composition (A) having the ratio of 80% by mass or more has a higher effect obtained by containing the vinyl compound (A).

[0063] The vinyl compound (A) obtained by the above method can be used as it is as the vinyl composition (A). The vinyl composition (A) containing the other components can be obtained by mixing the vinyl compound (A) with the other components.

[0064] <Cured vinyl resin> The vinyl resin cured product of the present embodiment is obtained by curing a vinyl compound (A) or a vinyl composition (A). In this specification, the vinyl resin cured product of this embodiment may be referred to as "vinyl resin cured product (A)".

[0065] The vinyl resin cured product has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A), and is therefore suitable as a constituent material for printed wiring boards, particularly as an insulating material for printed wiring boards. In addition, the vinyl resin cured product has a low melting point, which makes the manufacturing process easier.

[0066] When the vinyl resin cured product (A) is a cured product of a vinyl compound (A), the vinyl resin cured product (A) may be a cured product of one type of vinyl compound (A) or a cured product of two or more types of vinyl compounds (A). When the vinyl resin cured product (A) is a cured product of the vinyl composition (A), the vinyl resin cured product (A) may be a cured product of one type of vinyl composition (A) or a cured product of a mixture of two or more types of vinyl compositions (A).

[0067] The vinyl resin cured product (A) can be prepared, for example, by filling the vinyl compound (A) or vinyl composition (A) as is into a mold, heating it for a predetermined time to perform primary curing, and further heating it for a predetermined time while applying a predetermined pressure with a press or the like to completely cure it; by heating the vinyl compound (A) or vinyl composition (A) as is at a predetermined temperature to cure it; by pouring the powder of the vinyl compound (A) or vinyl composition (A) as is or after melting as necessary into a mold and heating it for a predetermined time while applying a predetermined pressure with a press or the like; or by melting the vinyl compound (A) or vinyl composition (A) by heating and pouring it into a mold or the like and further pressing the mold. a method of partially curing the vinyl compound (A) or the vinyl composition (A), crushing the partially cured product, filling a mold with the powder obtained, and melt-molding the filled powder; a method of dissolving the vinyl compound (A) or the vinyl composition (A) in a solvent or as needed, partially curing the vinyl compound (A) while stirring as needed, casting the resulting solution, and then drying and removing the solvent by ventilation drying or the like, and heating for a predetermined time while applying a predetermined pressure with a press or the like as needed.

[0068] The heating temperature (curing temperature) when the vinyl compound (A) or the vinyl composition (A) is heated and cured is not particularly limited, but in terms of increasing the degree of curing of the vinyl compound (A) or the vinyl composition (A), it is preferably 100° C. or higher, and more preferably 140° C. or higher. In terms of avoiding excessive heating, the heating temperature is preferably 200° C. or lower.

[0069] The heating time (curing time) when the vinyl compound (A) or the vinyl composition (A) is heated and cured is not particularly limited, but is preferably 1 hour or more, more preferably 2 hours or more, in order to increase the degree of curing of the vinyl compound (A) or the vinyl composition (A). The heating time is preferably 10 hours or less, in order to avoid unnecessary curing operations.

[0070] The pressure applied when the vinyl compound (A) or the vinyl composition (A) is pressed and cured (pressure during curing) is not particularly limited, but is preferably 0.7 MPa or more, more preferably 1.2 MPa or more, in order to increase the degree of curing of the vinyl compound (A) or the vinyl composition (A). The pressure applied is preferably 3 MPa or less, in order to avoid excessive pressurization.

[0071] The thermal diffusivity of the cured vinyl resin (A) is 1.4 x 10 -7 m 2 / s or more is preferable, and 1.8×10 -7 m 2 / s or more is more preferable, and 1.95×10 -7 m 2 When the thermal diffusivity is within the above range, the thermal conductivity tends to be high. The upper limit of the thermal diffusivity of the vinyl resin cured product (A) is not particularly limited, and the thermal diffusivity is preferably 4.0×10 -7 m 2 / s or less, or 3.6 × 10 -7 m 2 / s or less, or 3.2 × 10 -7 m 2 / s or less. The thermal diffusivity of the vinyl resin cured material (A) is, for example, 1.4×10 -7 ~4.0×10 -7 m 2 / s, 1.8×10 -7 ~3.6×10 -7 m 2 / s, and 1.95 × 10 -7 ~3.2×10 -7 m 2 / s.

[0072] The thermal diffusivity of the vinyl resin cured material (A) can be measured by the temperature wave thermal analysis method (TWA method) standardized in ISO 22007-3:2008 (for transport analysis type thin films).

[0073] The dielectric loss tangent of the vinyl resin cured product (A) at a frequency of 100 MHz is preferably 0.005 or less, more preferably 0.0048 or less, and even more preferably 0.0046 or less. The lower limit of the dielectric loss tangent of the vinyl resin cured product (A) is not particularly limited, and the dielectric loss tangent may be 0.001 or more, 0.002 or more, or 0.003 or more. The dielectric loss tangent of the vinyl resin cured product (A) at a frequency of 100 MHz may be, for example, any one of 0.001 to 0.005, 0.002 to 0.0048, and 0.003 to 0.0046, although these are only examples of the dielectric loss tangent of the vinyl resin cured product (A).

[0074] The dielectric loss tangent of the vinyl resin cured material (A) at a frequency of 100 MHz can be measured by a capacitance method using an impedance analyzer under the following conditions. ·Measurement method: Capacitive method ·Electrode model: 16453A Measurement environment: 23℃, 50% RH Applied voltage: 1V

[0075] <Prepreg> The prepreg of the present embodiment comprises a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a fibrous base material. In this specification, the prepreg of this embodiment may be referred to as "prepreg (A)". By using the prepreg (A), a laminate or the like can be easily manufactured by a normal method. For example, a desired laminate can be obtained by stacking a plurality of prepregs (A) to form a laminate, and molding and integrating the laminate by applying pressure while heating. A printed wiring board (resin layer in the printed wiring board) obtained using the prepreg (A) or the laminate has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0076] The prepreg (A) can be produced by coating or impregnating a fibrous base material with a solution of the vinyl compound (A) dissolved in a solvent, or by coating or impregnating a fibrous base material with the vinyl composition (A) or a dilution of the vinyl composition (A) with a solvent, and then heating the coated or impregnated fibrous base material to semi-cure the vinyl compound (A) or the vinyl composition (A).

[0077] 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.

[0078] The fibrous substrate is not particularly limited as long as it is a fibrous substrate, and may be a known one. More specifically, examples of the fibrous substrate include woven and nonwoven fabrics of inorganic fibers such as glass fibers, and woven and nonwoven fabrics of organic fibers such as polyester.

[0079] <Film with resin> The resin-attached film of this embodiment includes a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and a support film. More specifically, the resin-attached film of this embodiment includes, for example, the resin layer and the resin and the support film provided on one or both sides of the resin layer. A laminate sheet is obtained by using a plurality of resin-attached films of this embodiment, removing the support film, stacking them to form a laminate, and molding and integrating this laminate by heating and pressing. The resin layer in the resin-attached film of this embodiment and the printed wiring board (resin layer in the printed wiring board) obtained by using the resin layer or the laminate sheet have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0080] The support film may be, for example, a polyethylene terephthalate (PET) film. In the case of a resin-attached film, when a support film is provided on both sides of a resin layer, these support films may be the same as each other or different from each other. In this specification, not only in the case of a resin-attached film, but also when two layers of support films are different from each other, it means that at least one of the material and thickness of the two layers of support films is different from each other.

[0081] The resin-attached film of this embodiment can be produced by coating the support film with a solution of the vinyl compound (A) dissolved in a solvent, or by coating the support film with the vinyl composition (A) or a dilution of the vinyl composition (A) diluted with a solvent, and then heating the layer of the coating to semi-cure the vinyl compound (A) or the vinyl composition (A) in the coating. The conditions for semi-curing the vinyl compound (A) or the vinyl composition (A) are the same as those for producing the prepreg described above.

[0082] <Metal foil with resin> The resin-attached metal foil of this 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. More specifically, the resin-attached metal foil of this embodiment may comprise the resin layer and the metal foil provided on one or both sides of the resin layer. For example, the resin-attached metal foil of this embodiment may be used to further cure the semi-cured product to form a cured product, and the metal foil may be patterned to form a circuit, thereby forming a printed wiring board. In addition, the resin-attached metal foil of this embodiment may be used to pattern the metal foil to form a circuit, and resin layers containing such circuits may be laminated together with the circuit orientation aligned, and the semi-cured product may be further cured by applying pressure while heating, thereby forming a multilayer printed wiring board having a resin layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A) as an insulating layer. The resin layer in the resin-coated metal foil of this embodiment and the printed wiring board (resin layer in the printed wiring board) obtained using the resin-coated metal foil have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0083] The metal foil may be, for example, a copper foil. In the case of the resin-coated metal foil, when the metal foil is provided on both sides of the resin layer, these metal foils may be the same or different from each other. In this specification, not only in the case of the resin-coated metal foil, but also in the case of the two layers of metal foil being different from each other, it means that at least one of the material and thickness of the two layers of metal foil is different from each other.

[0084] The resin-coated metal foil of this embodiment can be produced in the same manner as the resin-coated film, except that the metal foil is used instead of the support film.

[0085] <Metal-clad laminate> The metal-clad laminate of this embodiment includes an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and a metal foil. More specifically, the metal-clad laminate of this embodiment includes a metal-clad laminate having the insulating layer and the metal foil provided on one or both sides of the insulating layer. The metal-clad laminate of this embodiment can be made into a printed wiring board by, for example, patterning the metal foil therein to form a conductor wiring (circuit). Furthermore, a multi-layer printed wiring board can be made by stacking such multiple printed wiring boards via a separately prepared insulating layer and applying pressure while heating. The insulating layer in the metal-clad laminate of this embodiment and the printed wiring board obtained using the metal-clad laminate (the insulating layer in the printed wiring board) have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0086] The metal foil provided in the metal-clad laminate of this embodiment is the same as the metal foil provided in the resin-coated metal foil described above. In the metal-clad laminate, when metal foils are provided on both sides of the insulating layer, these metal foils may be the same as each other or different from each other.

[0087] The insulating layer used separately when laminating the printed wiring board may be a known one, the resin layer in the above-mentioned resin-attached film, the laminated sheet which is a laminate of a plurality of the resin layers, the above-mentioned prepreg (A), or the laminate obtained by overlapping a plurality of prepregs (A). Alternatively, the insulating layer may be a resin layer, a laminated sheet, a prepreg (A), or a laminate obtained by further curing the vinyl compound (A) or the vinyl composition (A) in the resin layer, the laminated sheet, the prepreg (A), or the laminate.

[0088] The metal-clad laminate of this embodiment can be produced, for example, by laminating a metal foil on one or both sides of a prepreg (A) and applying pressure while heating the resulting laminate to further cure the vinyl compound (A) or a semi-cured product thereof, or the vinyl composition (A) or a semi-cured product thereof in the prepreg (A) to form a cured product, thereby forming an insulating layer and fusing the prepreg (A) and the metal foil. The metal-clad laminate of this embodiment may be produced, for example, by producing a prepreg (A) using the vinyl compound (A) or the vinyl composition (A) by the method described above, and then using this prepreg (A) by the method described above. The metal-clad laminate of this embodiment can also be produced, for example, by heating the above-mentioned resin-coated metal foil to further cure the vinyl compound (A) or a semi-cured product thereof, or the vinyl composition (A) or a semi-cured product thereof in the 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).

[0089] <Printed wiring board> The printed wiring board of this embodiment comprises an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and a conductor wiring. More specifically, the printed wiring board of this embodiment may be, for example, a printed wiring board comprising the insulating layer and the conductor wiring provided on one or both sides of the insulating layer. A multi-layer printed wiring board can be formed by stacking a plurality of printed wiring boards of this embodiment via a separately prepared insulating layer and applying pressure while heating. The printed wiring board of this embodiment (the insulating layer in the printed wiring board) has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (A).

[0090] The material of the conductor wiring is the same as the metal of the metal foil included in the above-mentioned metal-clad laminate. The insulating layer used separately when laminating the printed wiring board of this embodiment is the insulating layer described above. In the case where conductor wiring is provided on both sides of an insulating layer in a printed wiring board, the material and thickness of these conductor wirings may be the same as or different from each other.

[0091] The printed wiring board of this embodiment can be produced, for example, by patterning the metal foil in the above-mentioned metal-clad laminate to form conductor wiring (circuits). The printed wiring board of the present embodiment can also be produced by, for example, heating the above-mentioned resin-coated metal foil to further cure the vinyl compound (A) or a semi-cured product thereof, or the vinyl composition (A) or a semi-cured product thereof in the resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (A) or a cured product of the vinyl composition (A), and then patterning the metal foil to form conductor wiring (circuits). The metal foil can be patterned by known methods such as etching.

[0092] Fig. 1 is a cross-sectional view showing an example of the laminated structure of the present embodiment obtained by using the vinyl compound (A). In addition, the drawings used in the following description may show the main parts in an enlarged manner for the sake of convenience in order to make the features of the present invention easier to understand, and the dimensional ratios of each component may not necessarily be the same as the actual ones.

[0093] The laminated structure 1 shown here is configured to include a first layer 11 and a second layer 12 provided on one surface 11a of the first layer 11. The first layer 11 is a layer obtained using a vinyl compound (A). The second layer 12 is selected depending on the type of the laminated structure 1. Both the first layer 11 and the second layer 12 are in the form of a film or sheet. The second layer 12 may be provided over the entire area of ​​one surface 11a of the first layer 11, or may be provided in a partial area.

[0094] 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 resin-attached film. When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a metal foil, the laminate structure 1 is a resin-coated metal foil. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 is a metal foil, the laminate structure 1 is a metal-clad laminate.

[0095] Fig. 2 is a cross-sectional view showing a schematic diagram of another example of the laminated structure of the present embodiment obtained by using the vinyl compound (A). In Fig. 2 and subsequent figures, the same components as those shown in the figures already described are given the same reference numerals as those in the figures already described, and detailed description thereof will be omitted.

[0096] The laminated structure 2 shown here is configured to include a first layer 11 and a second layer 22 provided on one surface 11a of the first layer 11. The second layer 22 is linear, and in FIG. 2, the cross section of the laminated structure 2 is formed to include a cross section along the linear length direction of the second layer 22. The number of linear second layers 22 may be one or may be two or more. The laminated structure 2 is the same as the laminated structure 1 shown in FIG. 1, except that the laminated structure 2 includes a linear second layer 22 instead of the film-like second layer 12. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 22 is a conductor wiring, the laminate structure 2 is a printed wiring board.

[0097] Both the laminate structure 1 and the laminate structure 2 shown in Figures 1 and 2 have nothing on the other surface 11b of the first layer 11, but may have a layer similar to the second layer 12 or the second layer 22.

[0098] FIG. 3 is a cross-sectional view that typically shows still another example of the laminate structure of the present embodiment obtained using the vinyl compound (A). The laminated structure 3 shown here is configured to include a first layer 11, a second layer 12 provided on one surface 11a of the first layer 11, and a third layer 13 provided on the other surface 11b of the first layer 11. The third layer 13 is in the form of a film or sheet, and is selected according to the type of the laminated structure 1, similar to the second layer 12. The arrangement of the third layer 13 on the other surface 11b of the first layer 11 is similar to the arrangement of the second layer 12 on the one surface 11a of the first layer 11. The composition, shape, thickness, and size of the third layer 13 may be the same as or different from the composition, shape, thickness, and size of the second layer 12. For example, the third layer 13 may be provided over the entire area of ​​the other surface 11b of the first layer 11, or may be provided in a partial area.

[0099] 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 resin-attached film. When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof, or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a resin-coated metal foil. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal-clad laminate.

[0100] FIG. 4 is a cross-sectional view that typically shows still another example of the laminate structure of the present embodiment obtained using the vinyl compound (A). The laminated structure 4 shown here is configured to include a first layer 11, a second layer 22 provided on one surface 11a of the first layer 11, and a third layer 23 provided on the other surface 11b of the first layer 11. The third layer 23 is linear, and in FIG. 4, the cross section of the laminated structure 4 is formed to include both a cross section along the linear length direction of the second layer 22 and a cross section along the linear length direction of the third layer 23. The arrangement of the third layer 23 on the other surface 11b of the first layer 11 is similar to the arrangement of the second layer 22 on one surface 11a of the first layer 11. The composition, length, thickness, and number of the third layer 23 may be the same as or different from the composition, length, thickness, and number of the second layer 22. For example, the number of linear third layers 23 may be one or more. When the first layer 11 is an insulating layer containing a cured product of a vinyl compound (A), a cured product of a vinyl composition (A), or a cured product of a prepreg (A), and the second layer 22 and the third layer 23 are conductor wirings, the laminate structure 4 is a printed wiring board. EXAMPLES

[0101] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0102] The conditions for measuring the melting point of vinyl compounds are shown below. A glass pan filled with a vinyl compound was heated under the following conditions using a differential scanning calorimeter (METTLER TLEDO FP84HT), and the endothermic peak temperature was taken as the melting point. When there were multiple endothermic peaks, the endothermic peak temperature on the lower side was taken as the melting point.

[0103] The test conditions for the cured product are as follows. (1) Thermal diffusivity Thermal diffusivity measuring device "ai-phase mobile" (manufactured by ai-phase Co., Ltd.) The measurements were performed using the TWA method.

[0104] Example 1 In a 300 mL four-neck flask equipped with a thermometer, condenser, and stirrer, add sodium hydride. 8.8 g of methanol was added and washed with hexane, and 90 mL of THF, 0.2 g of 2,6-di(tert-butyl)-p-cresol, 6-chloro-1-hexanol, and 18.5 g of 4-vinylbenzyl chloride were added and reacted at an internal temperature of about 60° C. for 3 hours.

[0105] After the reaction was completed, the mixture was cooled to room temperature, 8 mL of water was added, and the mixture was filtered to remove insoluble matters. The resulting solution was washed with water, and the solvent was removed under reduced pressure, followed by drying under reduced pressure to obtain 34.3 g of chloro compound 1.

[0106] In a 300 mL four-neck flask equipped with a thermometer, condenser, and stirrer, add 1,1'-( 5.0 g of 1,1'-biphenyl)-4,4'-diyl bis(4-hydroxybenzoate), 0.05 g of 2,6-di(tert-butyl)-p-cresol, 6.5 g of potassium carbonate, 0.7 g of sodium iodide, 35 mL of N,N-dimethylformamide, and 9.1 g of chloro compound 1 were charged and reacted at an internal temperature of about 80°C for 8 hours.

[0107] After the reaction was completed, the mixture was cooled to room temperature, 33 mL of water was added, and the precipitated solid was collected by filtration. The obtained solid was mixed with acetone and stirred, and then the solid was collected by filtration. The obtained solid was dissolved in THF to remove insoluble matters, and the solvent was removed under reduced pressure to obtain 6.8 g of vinyl compound 1. Purity: 74.5% (LC area percentage value).

[0108] Example 2 In a 200 mL four-neck flask equipped with a thermometer, condenser, and stirrer, add sodium hydride. A mixture of 4.8 g of vinylbenzyl chloride, 0.1 g of 2,6-di(tert-butyl)-p-cresol, 12.0 g of vinylbenzyl chloride (mixture of m,p positional isomers), and 90 mL of dehydrated N,N-dimethylformamide was charged and cooled to an internal temperature of about 0° C. A solution of 9.8 g of 3-chloro-1-propanol in dehydrated N,N-dimethylformamide was added dropwise, and the mixture was allowed to react at room temperature for 3 hours.

[0109] After the reaction was completed, the mixture was cooled to an internal temperature of about 0°C, and excess sodium hydride was quenched with water, after which the solvent was removed under reduced pressure. The resulting liquid was dissolved in ethyl acetate and washed with water, and the solvent was removed under reduced pressure and dried under reduced pressure to obtain 18.7 g of chloro compound 2.

[0110] In a 200 mL four-neck flask equipped with a thermometer, condenser, and stirrer, add 1,1'-( 3.4 g of 1,1'-biphenyl)-4,4'-diyl bis(4-hydroxybenzoate), 0.03 g of 2,6-di(tert-butyl)-p-cresol, 5.2 g of potassium carbonate, 0.5 g of sodium iodide, 65 mL of N,N-dimethylformamide, and 5.4 g of chloro compound 2 were charged and reacted at an internal temperature of about 80°C for 14 hours.

[0111] After the reaction was completed, the mixture was cooled to room temperature, 100 mL of water was added, and the mixture was stirred for 10 minutes. The precipitated solid was collected by filtration and washed with water, heptane, and methanol. The solid was suspended in a small amount of THF, mixed with acetone, stirred, and then collected by filtration. The solid was dried under reduced pressure to obtain 2.5 g of vinyl compound 2. Purity: 70.1% (LC area percentage value).

[0112] Example 3 In a 200 mL four-neck flask equipped with a thermometer, a condenser, and a stirrer, 2.5 g of (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 0.03 g of 2,6-di(tert-butyl)-p-cresol, 5.1 g of potassium carbonate, 0.5 g of sodium iodide, 23 mL of N,N-dimethylformamide, and 14.7 g of the chloro compound were charged and reacted for 22 hours at an internal temperature of about 60 to 80 ° C. After the reaction was completed, it was cooled to room temperature. Then, toluene was added and washed with water, and the solution was removed under reduced pressure. Methanol was added to the obtained liquid and stirred, and the precipitated solid was collected by filtration. The obtained solid was dissolved in acetone and filtered to remove insoluble matter. Part of the solution was removed under reduced pressure, methanol was added and stirred, and the precipitated solid was collected by filtration and washed with methanol. The obtained solid was dried under reduced pressure to obtain 3.7 g of vinyl compound 3. Purity: 72.4% (LC area percentage value).

[0113] Example 4 In a 500mL four-neck flask equipped with a thermometer, a condenser and a stirrer, 19.0g of (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 42.0g of potassium carbonate, 1.8g of sodium iodide, 250mL of N,N-dimethylformamide and 26.5g of 2-chloroethyl vinyl ether were charged and reacted for 12 hours at an internal temperature of about 60°C. After the reaction was completed, the mixture was cooled to room temperature, 250mL of water was added, and the precipitated solid was collected by filtration. The obtained solid was washed with 50wt% methanol water and isopropyl alcohol, and dried under reduced pressure to obtain 25.8g of vinyl compound 4. Purity: 97.7% (LC area percentage value). The melting point of vinyl compound 4 measured by the above method was 128°C.

[0114] Reference example 1 In a 200 mL four-neck flask equipped with a thermometer, condenser, and stirrer, add 6.0 g of 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl, 2,6 0.06g of 2,6-di(tert-butyl)-p-cresol, 12g of potassium carbonate, 1.3g of sodium iodide, 34mL of N,N-dimethylformamide and 10g of 4-vinylbenzyl chloride were charged and reacted at an internal temperature of about 60°C for 3 hours. After the reaction was completed, 121g of toluene and 34mL of water were added and stirred, and the mixture was filtered to remove insoluble matter. The resulting solution was separated and washed three times with water. The resulting solution was filtered to remove insoluble matter, and then the toluene was removed under reduced pressure. 56mL of methanol and 0.07g of 2,6-di(tert-butyl)-p-cresol were added to the resulting solid and stirred at room temperature. The solid in the suspension was filtered and dried under reduced pressure to obtain 9.4g of vinyl compound 5. Purity: 99.1% (LC area percentage value).

[0115] In Examples 5 to 7 and Comparative Example 1, the vinyl compounds prepared in Examples 1 to 4 and Reference Example 1 shown in Table 1 were placed in the hollow plate of a mold, heated under reduced pressure at the primary curing temperature shown in Table 1 for 1 hour, and then heated at 180°C for 2 hours while applying a pressure of 1.5 MPa to obtain cured products. Table 1 shows the melting points of the vinyl compounds and the thermal diffusivities of the cured products.

[0116] [Table 1] [Industrial Applicability]

[0117] The present invention can be used for printed wiring boards in communication devices, and is particularly suitable for use in printed wiring boards in which the communication devices handle large amounts of data and are expected to generate a large amount of heat. [Explanation of symbols]

[0118] 1, 2, 3, 4...Layered structure 11... 1st layer 11a...One side of the first layer 11b.....The other surface of the first layer 12, 22...2nd layer 13, 23...Third layer

Claims

1. A vinyl compound represented by formula (A). 【Chemical 1】 (In the formula (A), Y １ and Y ２ are each the same or different and are each any group selected from the group consisting of a vinyl group and a vinylbenzyl group.) Q is any one of the groups selected from the group consisting of formulas (1) to (3), 【Chemical 2】 In the above formulas (1) to (3), A １ , A ２ , A ３ and A ４ are each the same as or different from one another and are a substituted or unsubstituted divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups), A substituted or unsubstituted divalent cycloalkylene group, A divalent group in which two or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) are linked by a single bond, A divalent group in which two or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups are linked by a single bond, and One or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) and one or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkeni A divalent group in which a ren group is linked by a single bond, Is any one selected from the group consisting of, X １ , X ２ and X ３ are each independently the same or different and are each selected from the group consisting of a single bond, an ester group, and a carbonyl group, Y １ and Y ２ When at least one of them is a vinyl group, X that constitutes Q １ , X ２ , and X ３ At least one of them is an ester group or a carbonyl group, and A １ , A ２ , A ３ , and A ４ At least one of them is a cyclohexyl ring, n1 and n2 are each the same or different and represent an integer from 1 to 20.)

2. Said X １ , X ２ and X ３ is the vinyl compound according to claim 1, wherein at least one of them is an ester group.

3. Said A １ , A ２ , A ３ and A ４ The vinyl compound according to claim 1, wherein A, A, A and A are divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups).

4. The vinyl compound according to claim 1, wherein Y1 and Y2 are vinylbenzyl groups and the aromatic group does not contain a hetero atom.

5. The vinyl compound according to any one of claims 1 to 4, which is used for a printed wiring board.

6. A vinyl composition containing the vinyl compound according to claim 1.

7. A cured vinyl resin obtained by curing the vinyl compound according to any one of claims 1 to 4, or the vinyl composition according to claim 6.

8. A prepreg comprising the vinyl compound according to any one of claims 1 to 4 or a semi-cured product thereof, or the vinyl composition according to claim 6 or a semi-cured product thereof, and a fibrous substrate.

9. A resin-coated film comprising a resin layer containing the vinyl compound according to any one of claims 1 to 4 or a semi-cured product thereof, or the vinyl composition according to claim 6 or a semi-cured product thereof, and a support film.

10. A metal-clad laminate comprising a resin layer containing the vinyl compound according to any one of claims 1 to 4 or a semi-cured product thereof, or the vinyl composition according to claim 6 or a semi-cured product thereof, and a metal foil.

11. A metal-clad laminate comprising an insulating layer containing a cured product of the vinyl compound according to any one of claims 1 to 4, or a cured product of the vinyl composition according to claim 6, and a metal foil.

12. A metal-clad laminate comprising an insulating layer containing a cured product of the prepreg according to claim 8 and a metal foil.

13. A printed wiring board comprising an insulating layer containing a cured product of a vinyl compound according to any one of claims 1 to 4 or a cured product of a vinyl composition according to claim 6, and a conductor wiring.

14. A printed wiring board comprising an insulating layer containing a cured product of the prepreg according to claim 8 and a conductive wiring.

Images