Vinyl compounds, methods for producing vinyl compounds, vinyl compositions, cured vinyl resins, prepregs, resin-coated films, resin-coated metal foils, metal-clad laminates, and printed circuit boards.

Abstract

To provide a novel compound that can produce a resin suitable as a constituent material of a printed wiring board, having high thermal conductivity and low dielectric loss.SOLUTION: Provided is a vinyl compound represented by formula (1) (In the formula, A1, A2 and A3 are the same or different and represent a saturated or unsaturated 6-membered cyclic group described under formula (1). Q1 and Q2 are the same or different and represent a single bond, a linear or a branched alkylene group having 1 to 18 carbon atoms, or a divalent group represented by formula (2). Ar represents an aromatic group.).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to vinyl compounds, a method for producing vinyl compounds, vinyl compositions, cured vinyl resins, prepregs, resin-coated films, resin-coated metal foils, metal-clad laminates, and printed wiring boards.

Background Art

[0002] The amount of data and communication speed handled by communication devices are increasing year by year. Along with this, high-speed communication technologies for improving the signal transmission speed are actively being researched. When the amount of data handled by a communication device is large, the amount of heat generated by the electronic arithmetic components in the communication device increases, and if heat accumulates in the printed wiring board, problems will occur. Therefore, high heat dissipation is required for printed wiring boards.

[0003] As a printed wiring board with high heat dissipation, for example, a so-called thick copper substrate is known in which the thickness of the copper (i.e., copper pattern) forming the circuit is made thicker than conventional ones, enabling more heat to be released through this copper. However, this thick copper substrate has the problem that it is not suitable for communication devices that require miniaturization and weight reduction because the overall thickness increases.

[0004] As a printed wiring board with high heat dissipation, a so-called metal base substrate is also known in which a metal plate is provided on one surface thereof, enabling more heat to be released through this metal plate. However, this metal base substrate has the problem that the number of manufacturing steps during its production increases, resulting in an increase in the manufacturing cost of communication devices.

[0005] On the other hand, similar to printed wiring boards, members mainly composed of resin and having high heat dissipation are known to contain fillers with high thermal conductivity. However, materials containing fillers have the problem that they are not suitable for the production of printed wiring boards because of their poor processability.

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

[0007] [Patent Document 1] U.S. Patent Application Publication No. 2019 / 0194408 [Overview of the Initiative] [Problems that the invention aims to solve]

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

[0009] The present invention aims to provide a novel compound that is suitable as a constituent material for printed circuit boards and can be used to produce a resin with high thermal conductivity and low dielectric loss. [Means for solving the problem]

[0010] This invention employs the following configuration. [1] Formula (1)

[0011] [ka] (In the formula, A 1 , A 2 and A 3 Each of them is either the same or different, as shown below.

[0012] [ka] represents any of the divalent groups shown below. Here, R represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 18 carbon atoms. The alkyl group and the alkoxy group may be linear or branched, and in the alkyl group and the alkoxy group, one or more non-adjacent methylene groups may be replaced by an oxygen atom. a represents an integer of 1 to 10, b and c represent integers of 1 to 8, d, e, f, and g represent integers of 1 to 6, and h represents an integer of 1 to 4. In the divalent group, when there are a plurality of Rs, all the Rs may represent the same group or different groups. Q 1 and Q 2 are each the same or different and represent a single bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a divalent group represented by the formula (2)

[0013]

Chemical formula

[0014]

Chemical formula

[0015] 3]

Chemical formula

[0016] [ka] (In the formula, A 1 , A 2 and A 3 These terms represent the same meaning as above. The compound shown by and formula (5)

[0017] [ka] (In the formula, Q 1 This has the same meaning as above, X 1 (This represents a halogen atom.) The compound shown by and formula (6)

[0018] [ka] (In the formula, Q 2 This has the same meaning as above, X 2 represents a halogen atom, and the above X 1 It may be the same as, or it may be different from, this. A method for producing a vinyl compound, comprising reacting a compound shown with a base in the presence of a base. A vinyl composition containing a vinyl compound as described in any one of the items [5][1] to [3]. A vinyl resin cured product obtained by curing a vinyl compound described in any one of items [6], [1] to [3], or a vinyl composition described in [5]. A prepreg comprising a vinyl compound or semi-cured product thereof as described in any one of [7][1] to [3], or a vinyl composition or semi-cured product thereof as described in [5], and a fibrous substrate. A resin-coated film comprising a resin layer containing a vinyl compound or a semi-cured product thereof as described in any one of items [8][1] to [3], or a vinyl composition or a semi-cured product thereof as described in [5], and a support film. A resin-coated metal foil comprising a resin layer containing a vinyl compound or a semi-cured product thereof as described in any one of items [9][1] to [3], or a vinyl composition or a semi-cured product thereof as described in [5], and a metal foil. A metal-clad laminate comprising an insulating layer containing a cured vinyl compound according to any one of items

[10] , [1] to [3], a cured vinyl composition according to [5], or a cured prepreg according to [7], and a metal foil. A printed wiring board comprising an insulating layer containing a cured vinyl compound according to any one of items

[11] to [3], a cured vinyl composition according to [5], or a cured prepreg according to [7], and conductive wiring. [Effects of the Invention]

[0019] According to the present invention, a novel compound is provided that is suitable as a constituent material for printed circuit boards and can be used to produce a resin with high thermal conductivity and low dielectric loss. [Brief explanation of the drawing]

[0020] [Figure 1] This is a schematic cross-sectional view showing an example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention. [Figure 2] This is a schematic cross-sectional view showing another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention. [Figure 3] This is a schematic cross-sectional view showing yet another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention. [Figure 4] This is a schematic cross-sectional view showing yet another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention. [Modes for carrying out the invention]

[0021] <<Vinyl Compounds>> The vinyl compound of this embodiment is of formula (1)

[0022] [ka] (In the formula, A 1 , A 2 and A 3 Each of them is either the same or different, as shown below.

[0023] [ka] This represents one of the divalent groups shown by . Here, R represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 18 carbon atoms, and the alkyl group and alkoxy group may be linear or branched, and in the alkyl group and alkoxy group, one or more non-adjacent methylene groups may be replaced by oxygen atoms. a represents an integer from 1 to 10, b and c represent integers from 1 to 8, d, e, f and g represent integers from 1 to 6, and h represents an integer from 1 to 4. In the divalent group, when there are multiple Rs, all Rs may represent the same group or different groups. Q 1 and Q 2 Each is either identical or distinct, and consists of a single bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or formula (2)

[0024] [ka] This represents a divalent group. Here, Ar represents an aromatic group. The methylene group in formula (2) is bonded to the oxygen atom in formula (1). This is shown. In this specification, the vinyl compound represented by formula (1) in this embodiment may be referred to as "vinyl compound (1)".

[0025] The vinyl compound of this embodiment (vinyl compound (1)) is a polymerizable monomer, and by polymerization (also referred to as "curing" in this specification), it forms a vinyl resin cured product, which will be described later.

[0026] In vinyl compound (1), the A 1 , A 2 and A 3 The linked structure is a mesogenic skeleton, and for example, compared to a conventional mesogenic skeleton with two linked hydrocarbon rings, the degree of orientation is higher due to the larger number of linked hydrocarbon rings. The resin, which is a cured product of vinyl compound (1), has high thermal conductivity due to having such a highly oriented structure.

[0027] On the other hand, resins having hydroxyl groups at or near their ends are known to have high dielectric loss. For example, a resin that is a cured product of a compound (monomer) having epoxy groups at its ends has hydroxyl groups at or near its ends, and therefore has high dielectric loss. In contrast, vinyl compound (1) has vinyl groups (ethenyl groups) at both ends and does not have epoxy groups or hydroxyl groups, so the resin that is its cured product also does not have hydroxyl groups at or near its ends, and such a resin has low dielectric loss.

[0028] Examples of C1-C18 alkyl groups in R include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, and 2,2-dimethylpentyl Examples include linear or branched alkyl groups having 1 to 18 carbon atoms, such as 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentyl group, 3-ethylpentyl group, 2,2,3-trimethylbutyl group, n-octyl group, isooctyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, and n-octadecyl group.

[0029] Examples of the alkoxy groups having 1 to 18 carbon atoms in R include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, n-hexyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, n-heptyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 2,2-dimethylpentyloxy, 2, Examples include linear or branched alkoxy groups having 1 to 18 carbon atoms, such as 3-dimethylpentyloxy group, 2,4-dimethylpentyloxy group, 3,3-dimethylpentyloxy group, 3-ethylpentyloxy group, 2,2,3-trimethylbutyloxy group, n-octyloxy group, isooctyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group, and n-octadecyloxy group.

[0030] In the alkyl group having 1 to 18 carbon atoms and the alkoxy group having 1 to 18 carbon atoms in R, one or more non-adjacent methylene groups (-CH2-) may be replaced by oxygen atoms (-O-). In the alkyl and alkoxy groups, if a methylene group is replaced by an oxygen atom, the number of such replacements (the number of methylene groups replaced by oxygen atoms) is less than the number of carbon atoms in the alkyl and alkoxy groups, and is determined according to the number of carbon atoms, but is usually preferably 1 to 3.

[0031] A 1 and A 3 These are either identical or different, and are expressed in the following formula

[0032] [ka] (In the formula, R and h have the same meanings as above.) It is preferable that the divalent group is represented by , and more preferably it is the same or different 1,4-phenylene group, 3-methyl-1,4-phenylene group, or 2-methyl-1,4-phenylene group.

[0033] A 2 The formula is as follows:

[0034] [ka] It is preferable that it be one of the divalent groups shown by . Here, R, a, c, and h have the same meanings as above.

[0035] The aforementioned Q 1 and Q 2 Examples of linear or branched alkylene groups having 1 to 18 carbon atoms include methylene group, ethylene group, trimethylene group (1,3-propylene group), 1,2-propylene group, tetramethylene group, 1-methyl-1,3-propylene group, 2-methyl-1,3-propylene group, 2-methyl-1,2-propylene group, pentamethylene group, 1-methyl-1,4-butylene group, Examples include 2-methyl-1,4-butylene group, hexamethylene group, heptamethylene group, octamethylene group, 2-ethyl-1,6-hexylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group, tridecamethylene group, tetradecamethylene group, pentadecamethylene group, hexadecamethylene group, heptadecamethylene group, octadecamethylene group, and the like.

[0036] The aromatic group in Ar is a divalent aromatic group, and specific examples include the 1,4-phenylene group and the 1,3-phenylene group.

[0037] The aforementioned Q 1 or Q 2If is a divalent group represented by formula (2), then the methylene group (-CH2-) in formula (2) is bonded to the oxygen atom in formula (1), and the Ar (aromatic group) in formula (2) is bonded to the vinyl group (CH2=CH-) in formula (1).

[0038] The aforementioned Q 1 and Q 2 Preferably, each of these is the same or different divalent group represented by formula (2), and more preferably, each of these is the same or different divalent group represented by formula (2) when the Ar is a 1,4-phenylene group or a 1,3-phenylene group.

[0039] The vinyl compound (1) is of formula (3)

[0040] [ka] (In the formula, A 4 The formula is as follows:

[0041] [ka] Represents any of the divalent groups shown by R, a, c, h, Q 1 and Q 2 (This has the same meaning as above.) Preferably, the vinyl compound is one represented by (which may be referred to as "vinyl compound (3)" in this specification).

[0042] In the vinyl compound (3), Q 1 and Q 2 Preferably, each of these is the same or different divalent group represented by formula (2), and more preferably, each of these is the same or different divalent group represented by formula (2) when the Ar is a 1,4-phenylene group or a 1,3-phenylene group.

[0043] <<Method for producing vinyl compounds>> Vinyl compound (1) is, for example, formula (4)

[0044] [ka] (In the formula, A 1 , A 2 and A 3 These terms represent the same meaning as above. The compound shown in (which may be referred to as "compound (4)" in this specification) and formula (5)

[0045] [ka] (In the formula, Q 1 This has the same meaning as above, X 1 (This represents a halogen atom.) The compound shown in (which may be referred to as "compound (5)" in this specification) and formula (6)

[0046] [ka] (In the formula, Q 2 This has the same meaning as above, X 2 represents a halogen atom, and the above X 1 It may be the same as, or it may be different from, this. It can be produced by reacting the compound shown (which may be referred to as "compound (6)" in this specification) with a base in the presence of a base.

[0047] Examples of the compound (4) include 1,4-bis(4-hydroxyphenyl)-1-cyclohexene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene, 1,4-bis(4-hydroxyphenyl)-2-cyclohexene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-2-cyclohexene, 1,4-bis(4-hydroxyphenyl)-2,5-cyclohexadiene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-2,5-cyclohexadiene, 1,4-bis(4-hydroxyphenyl)-1,5-cyclohexadiene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)- Examples include 1,5-cyclohexadiene, 1,4-bis(4-hydroxyphenyl)-1,4-cyclohexadiene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1,4-cyclohexadiene, 1,4-bis(4-hydroxyphenyl)-1,3-cyclohexadiene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1,3-cyclohexadiene, 1,4-bis(4-hydroxyphenyl)benzene, 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)benzene, 1,4-bis(4-hydroxyphenyl)cyclohexane, and 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)cyclohexane. Compound (4) can be manufactured in accordance with known methods described in, for example, Japanese Patent Publication No. 1-168632, Japanese Patent Publication No. 1-168634, U.S. Patent No. 3,461,098, Japanese Patent Publication No. 2-212449, Japanese Patent Publication No. 2002-234856, Japanese Patent Publication No. 2002-308809, Japanese Patent Publication No. 2002-363117, Japanese Patent Publication No. 2003-12585, etc.

[0048] The aforementioned X 1 and X 2 This represents a halogen atom, either identical or distinct, and examples of such halogen atoms include chlorine, bromine, and iodine atoms. Compound (5) and compound (6) may be the same as or different from each other. Examples of compounds (5) and (6) include 2-vinylbenzyl bromide, 3-vinylbenzyl bromide, 4-vinylbenzyl bromide, vinyl chloride, vinyl 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, 1-heptenyl chloride, 1-heptenyl bromide, 1-octenyl chloride, 1-octenyl bromide, Examples include 1-nonenyl chloride, 1-nonenyl bromide, 1-decenyl chloride, 1-decenyl bromide, 1-undecenyl chloride, 1-undecenyl bromide, 1-dodecenyl chloride, 1-dodecenyl bromide, 1-tridecenyl chloride, 1-tridecenyl bromide, 1-tetradecenyl chloride, 1-tetradecenyl bromide, 1-pentadecenyl chloride, 1-pentadecenyl bromide, 1-hexadecenyl chloride, 1-hexadecenyl bromide, 1-heptadecenyl chloride, 1-heptadecenyl bromide, 1-octadecenyl chloride, 1-octadecenyl bromide, and the like.

[0049] When compound (5) and compound (6) are the same, the amount used is usually preferably 2 to 100 molar times, more preferably 2 to 50 molar times, relative to compound (4). When compound (5) and compound (6) are different, the amount used for compound (5) is usually preferably 1 to 50 molar times, more preferably 1 to 25 molar times, relative to compound (4), and the amount used for compound (6) is usually preferably 1 to 50 molar times, more preferably 1 to 25 molar times, relative to compound (4).

[0050] The base may be either an inorganic base or an organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as sodium carbonate and potassium carbonate. Examples of the organic base include pyridine. The amount of base used is usually preferably 2 to 5 molar times the amount of compound (4). When using an organic base that is liquid under the reaction conditions, such organic base may be used in excess to also serve as the reaction solvent.

[0051] The reaction between compound (4), compound (5), and compound (6) is usually carried out by mixing compound (4), compound (5), compound (6), and a base in a solvent. The order of mixing is not particularly limited.

[0052] The solvent is not particularly limited as long as it is a solvent that is inert to the reaction, but a hydrophilic solvent is preferred in that the formation of by-products is easily suppressed. 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 mixtures. Furthermore, as described above, if an organic base that is liquid under the reaction conditions is used as the base, the organic base may also be used as the reaction solvent. Among these, ether-based solvents, aprotic polar solvents, and mixtures thereof are preferred solvents, aprotic polar solvents are more preferred, and N,N-dimethylformamide is particularly preferred. The amount of solvent used is preferably 1 to 20 mL per gram of compound (4), and more preferably 2 to 10 mL.

[0053] Regardless of whether compound (5) and compound (6) are the same, the reaction between compound (4) and compound (5); the reaction between the intermediate, which is a reaction product of compound (4) and compound (5), and compound (6); the reaction between compound (4) and compound (6); and the reaction between the intermediate, which is a reaction product of compound (4) and compound (6), and compound (5) may all be carried out via a halogen exchange reaction in the presence of a catalyst. Examples of the catalyst include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide. When a catalyst is used, the amount used is usually preferably 0.05 to 1 times the mass of compound (4), and more preferably 0.1 to 0.5 times the mass of compound (4).

[0054] The reaction between compound (4), compound (5), and compound (6) may be carried out in the presence of a polymerization inhibitor. Examples of polymerization inhibitors include 2,6-di(tert-butyl)-p-cresol. When a polymerization inhibitor is used, the amount used is usually preferably 0.002 to 0.05 times the mass of compound (5) and compound (6), and more preferably 0.004 to 0.02 times the mass of compound (5) and compound (6).

[0055] The reaction may be carried out under atmospheric pressure or reduced pressure. The reaction temperature is usually preferably 10 to 150°C. In this reaction, water may be produced as a by-product as the reaction progresses. In such cases, it is preferable to remove the by-product water from the reaction system while carrying out the reaction, and it is preferable to carry out the reaction at a reaction temperature and pressure that allows for azeotropic removal of the water. The reaction time is usually preferably 1 to 24 hours.

[0056] After the reaction is complete, for example, the reaction mixture is cooled, water or a water-containing mixed solvent is added, the precipitated solid is filtered off, and if necessary, known post-treatment operations are performed one or more times to obtain the vinyl compound (1). Examples of such post-treatment operations include stirring and washing the solid in water, a water-containing mixed solvent, or an organic solvent; and extraction (liquid-liquid extraction) of the solution in which the solid is dissolved. The obtained vinyl compound (1) may be further purified by conventional purification means if necessary.

[0057] The structure of the obtained vinyl compound (1) can be confirmed by known methods, such as nuclear magnetic resonance (NMR) spectroscopy.

[0058] <<Vinyl composition>> The vinyl composition of this embodiment contains vinyl compound (1). In this specification, the vinyl composition of this embodiment may be referred to as "vinyl composition (1)".

[0059] The vinyl composition (1) is curable and may contain only the vinyl compound (1), or it may contain the vinyl compound (1) and other components other than the vinyl compound (1) to the extent that it does not impair the effects of the present invention. The vinyl compound (1) hardens when heated. When hardening the vinyl compound (1), pressure may be applied to the vinyl compound (1).

[0060] The vinyl compound (1) contained in the vinyl composition (1) may be one type or two or more types.

[0061] <Other ingredients> Other components contained in the vinyl composition (1) include, for example, radical initiators; fillers; additives; solvents; vinyl compounds other than vinyl compound (1) (referred to as "other vinyl compounds" in this specification); and resins other than polymers (cured products) of vinyl compound (1) (referred to as "other resins" in this specification).

[0062] Examples of the aforementioned additives include silane coupling agents, colorants, low-stress components, mold release agents, antioxidants, defoamers, and flow regulators.

[0063] Examples of the radical initiators include azo compounds and organic peroxides.

[0064] Examples of fillers include silica powders such as molten crushed silica powder, molten spherical silica powder, crystalline silica powder, and secondary aggregated silica powder; metal oxides such as alumina, titanium oxide, zinc oxide, tungsten carbide, and magnesium oxide; glass cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, and titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; mica, etc.

[0065] Examples of the silane coupling agent include γ-glycidoxypropyltrimethoxysilane. Examples of the coloring agent include carbon black. Examples of the low-stress components include silicone oil and silicone rubber. Examples of the mold release agent include natural waxes, synthetic waxes, higher fatty acids, metal salts of higher fatty acids, and paraffin.

[0066] Examples of solvents contained in the vinyl composition (1) include ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as dimethyl sulfoxide and N-methylpyrrolidone; ester solvents such as butyl acetate; glycol solvents such as propylene glycol monomethyl ether; and aromatic solvents such as toluene.

[0067] The aforementioned other vinyl compounds are not particularly limited, as long as they have a vinyl group and do not fall under vinyl compound (1). The aforementioned other resin is not particularly limited as long as it is a resin other than a polymer of vinyl compound (1).

[0068] The other components contained in the vinyl composition (1) may be one or two or more.

[0069] The content of the other components in the vinyl composition (1) can be arbitrarily selected depending on the type of the other components. In the vinyl composition (1), the ratio of the content of vinyl compound (1) to the total content of components other than the solvent is preferably 80% by mass or more, for example, it may be 85% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, or 99% by mass or more. On the other hand, the ratio is 100% by mass or less. In a vinyl composition (1) where the ratio is 80% by mass or more, the effects obtained by containing vinyl compound (1) are more pronounced.

[0070] The vinyl compound (1) obtained by the above method can be used as is as a vinyl composition (1). A vinyl composition (1) containing the other components can be obtained by mixing the vinyl compound (1) with the other components.

[0071] <<Cured vinyl resin product>> The vinyl resin cured product of this embodiment is obtained by curing a vinyl compound (1) or a vinyl composition (1). In this specification, the vinyl resin cured product of this embodiment may be referred to as "vinyl resin cured product (1)".

[0072] Because the vinyl resin cured product uses a vinyl compound (1), it has high thermal conductivity and low dielectric loss, making it suitable as a component material for printed circuit boards, and in particular suitable as an insulating material for printed circuit boards.

[0073] If the vinyl resin cured product (1) is a cured product of a vinyl compound (1), the vinyl resin cured product (1) may be a cured product of one type of vinyl compound (1), or it may be a cured product of two or more types of vinyl compounds (1). If the vinyl resin cured product (1) is a cured product of a vinyl composition (1), the vinyl resin cured product (1) may be a cured product of one type of vinyl composition (1), or it may be a cured product of a mixture of two or more types of vinyl compositions (1).

[0074] The cured vinyl resin product (1) can be manufactured by, for example, a method of curing a vinyl compound (1) or vinyl composition (1) by heating it directly at a predetermined temperature; a method of pouring the powder of the vinyl compound (1) or vinyl composition (1) directly, or melting it as needed, into a mold and heating it for a predetermined time while applying pressure with a press or the like; a method of heating and melting the vinyl compound (1) or vinyl composition (1) and pouring it into a mold, then further heating the mold to form the product; a method of melting the vinyl compound (1) or vinyl composition (1) and injecting the resulting molten material into a preheated mold to cure it; a method of partially curing the vinyl compound (1) or vinyl composition (1), crushing the resulting partially cured material to obtain a powder, filling a mold with the powder, and melt-molding the filling powder; a method of partially curing the vinyl compound (1) or vinyl composition (1) directly, or dissolving it in a solvent as needed, partially curing it while stirring, casting the resulting solution, drying and removing the solvent by air drying or the like, and heating it for a predetermined time while applying pressure with a press or the like as needed.

[0075] The heating temperature (curing temperature) when heating and curing the vinyl compound (1) or vinyl composition (1) is not particularly limited, but it is preferably 140°C or higher, and more preferably 150°C or higher, in that it results in a higher degree of curing of the vinyl compound (1) or vinyl composition (1). The heating temperature is preferably 200°C or lower in that it avoids excessive heating.

[0076] The heating time (curing time) when heating and curing the vinyl compound (1) or vinyl composition (1) is not particularly limited, but it is preferably 1 hour or more, and more preferably 2 hours or more, in that the degree of curing of the vinyl compound (1) or vinyl composition (1) is higher. The heating time is preferably 10 hours or less in that unnecessary curing work can be avoided.

[0077] The pressure applied when curing the vinyl compound (1) or vinyl composition (1) is not particularly limited, but it is preferably 0.7 MPa or higher, and more preferably 1.2 MPa or higher, in that it results in a higher degree of curing of the vinyl compound (1) or vinyl composition (1). The pressure applied is preferably 3 MPa or lower in that it avoids excessive pressure.

[0078] The thermal diffusivity of the cured vinyl resin product (1) is 2.0 × 10⁻⁶. -7 m 2 It is preferable that it is 2.2 × 10⁻⁶ or more. -7 m 2 It is more preferable that it be 2.4 × 10⁻⁶ or more. -7 m 2 It is even more preferable that the thermal diffusivity of the cured vinyl resin (1) is 4.0 × 10⁻⁶. The upper limit of the thermal diffusivity of the cured vinyl resin (1) is not particularly limited, and the thermal diffusivity is 4.0 × 10⁻⁶. -7 m 2 / s or less is also acceptable, or 3.6 × 10 -7 m 2 It may be less than / s, or 3.2 × 10 -7 m 2 It may be less than / s. The thermal diffusivity of the cured vinyl resin product (1) is, for example, 2.0 × 10⁻⁶ -7 ~4.0×10 -7 m 2 / s, 2.2 × 10 -7 ~3.6×10 -7 m 2 / s, and 2.4 × 10 -7 ~3.2×10 -7 m 2 It can be either / s or any other.

[0079] The thermal diffusivity of the cured vinyl resin product (1) can be measured by thermal wave analysis (TWA).

[0080] At a frequency of 100 MHz, the dielectric loss tangent of the vinyl resin cured product (1) 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 (1) is not particularly limited, and the dielectric loss tangent may be 0.001 or more, 0.002 or more, or 0.003 or more. At a frequency of 100 MHz, the dielectric loss tangent of the vinyl resin cured product (1) may be, for example, 0.001 to 0.005, 0.002 to 0.0048, and 0.003 to 0.0046. However, these are just examples of the dielectric loss tangent of the vinyl resin cured product (1).

[0081] The dielectric loss tangent of the vinyl resin cured product (1) at a frequency of 100 MHz can be measured by the 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

[0082] <<Prepreg>> The prepreg of this embodiment comprises a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and a fibrous substrate. In this specification, the prepreg of this embodiment may be referred to as "prepreg (1)". By using prepreg (1), laminates and the like can be easily manufactured by conventional methods. For example, multiple prepreg (1) sheets are stacked to form a laminate, and this laminate is molded and integrated by heating and pressing it, thereby obtaining the desired laminate. The printed circuit board (resin layer in the printed circuit board) obtained using the prepreg (1) or the laminate has high thermal conductivity and low dielectric loss due to the use of the vinyl compound (1).

[0083] The prepreg (1) can be manufactured by applying or impregnating a fibrous substrate with a solution of vinyl compound (1) dissolved in a solvent, or by applying or impregnating a fibrous substrate with vinyl composition (1) or a diluted solution of vinyl composition (1) diluted in a solvent, and then heating the fibrous substrate after application or impregnation to partially cure the vinyl compound (1) or vinyl composition (1).

[0084] The heating temperature (partial curing temperature) and heating time (partial curing time) when partially curing the vinyl compound (1) or vinyl composition (1) can be appropriately set, taking into consideration the curing conditions (heating temperature and heating time) of the vinyl compound (1) or vinyl composition (1), so as not to cause the vinyl compound (1) or vinyl composition (1) to fully cure.

[0085] The fibrous base material is not particularly limited as long as it is a fibrous base material, and may be a known material. More specifically, examples of fibrous base materials include woven and nonwoven fabrics of inorganic fibers such as glass fibers, and woven and nonwoven fabrics of organic fibers such as polyester.

[0086] <<Resin-coated film>> The resin-coated film of this embodiment comprises a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and a support film. More specifically, as the resin-coated film of this embodiment, for example, a resin-coated film comprising the resin layer and the support film provided on one or both sides of the resin layer can be mentioned. By using a plurality of resin-coated films of this embodiment, removing the support film, stacking them to form a laminate, and molding and integrating this laminate by heating and pressing, a laminated sheet can be obtained. The resin layer in the resin-coated film of this embodiment, and the printed circuit board (resin layer in the printed circuit board) obtained using the resin layer or laminated sheet, have high thermal conductivity and low dielectric loss because they use a vinyl compound (1).

[0087] Examples of the support film include polyethylene terephthalate (PET) film. In a resin-coated film, if support films are provided on both sides of the resin layer, these support films may be identical or different. In this specification, not limited to resin-coated films, when two support films are said to be different, it means that at least one of the materials and thicknesses of the two support films is different.

[0088] The resin-coated film of this embodiment can be manufactured by applying a solution of vinyl compound (1) dissolved in a solvent to the support film, or by applying vinyl composition (1) or a diluted solution of vinyl composition (1) diluted in a solvent to the support film, and then heating the layer of this coating to partially cure the vinyl compound (1) or vinyl composition (1) in the coating. The conditions for partially curing the vinyl compound (1) or vinyl composition (1) at this time are the same as the conditions for manufacturing the prepreg described above.

[0089] <<Metal foil with resin coating>> The resin-coated metal foil of this embodiment comprises a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and a metal foil. More specifically, as the resin-coated metal foil of this embodiment, for example, a resin-coated metal foil comprising the resin layer and the metal foil provided on one or both sides of the resin layer can be mentioned. For example, using the resin-coated metal foil of this embodiment, the semi-cured product can be further cured to a cured product, and the metal foil can be patterned to form circuits, thereby creating a printed circuit board. Alternatively, using the resin-coated metal foil of this embodiment, circuits can be formed by patterning the metal foil, and resin layers containing such circuits can be stacked with the circuit orientations aligned, and the semi-cured product can be further cured by heating and pressurizing, thereby creating a multilayer printed circuit board having a resin layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1) as an insulating layer. The resin layer in the resin-coated metal foil of this embodiment, and the printed circuit board obtained using the resin-coated metal foil (the resin layer in the printed circuit board), have high thermal conductivity and low dielectric loss due to the use of a vinyl compound (1).

[0090] Examples of the aforementioned metal foil include copper foil. In a resin-coated metal foil, if metal foil is provided on both sides of the resin layer, these metal foils may be identical or different. In this specification, not limited to the case of resin-coated metal foil, when two layers of metal foil are said to be different, it means that at least one of the materials and thicknesses of the two layers of metal foil are different.

[0091] The resin-coated metal foil of this embodiment can be manufactured in the same manner as the resin-coated film, except that the metal foil is used instead of the support film.

[0092] <<Metal-clad laminate>> The metal-clad laminate of this embodiment comprises an insulating layer containing a cured vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and a metal foil. More specifically, as the metal-clad laminate of this embodiment, an example is a metal-clad laminate comprising the insulating layer and the metal foil provided on one or both sides of the insulating layer. The metal-clad laminate of this embodiment can be made into a printed circuit board by, for example, patterning the metal foil within it to form conductive wiring (circuits). Furthermore, multiple such printed circuit boards can be laminated via a separately prepared insulating layer and pressed while heated to create a multilayer printed circuit board. The insulating layer in the metal-clad laminate of this embodiment, and the printed circuit board obtained using the metal-clad laminate (insulating layer in the printed circuit board), have high thermal conductivity and low dielectric loss due to the use of the vinyl compound (1).

[0093] The metal foil in the metal-clad laminate of this embodiment is the same as the metal foil in the resin-coated metal foil described above. In a metal-clad laminate, if metal foils are provided on both sides of the insulating layer, these metal foils may be identical or different from each other.

[0094] The insulating layer used separately when laminating the printed circuit board may be a known material, the resin layer in the resin-coated film described above, the laminated sheet which is a laminate of multiple resin layers, the prepreg (1) described above, or the laminated board obtained by stacking multiple prepregs (1). Alternatively, the insulating layer may be a vinyl compound (1) or vinyl composition (1) that has been further cured in one of these resin layers, laminated sheets, prepregs (1), or laminated boards.

[0095] The metal-clad laminate of this embodiment can be manufactured, for example, by laminating metal foil on one or both sides of a prepreg (1), and then heating and pressurizing the resulting laminate to further cure the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product in the prepreg (1), thereby forming an insulating layer and fusing the prepreg (1) with the metal foil. The metal-clad laminate of this embodiment may be manufactured by, for example, producing a prepreg (1) using a vinyl compound (1) or vinyl composition (1) in the manner described above, and then using this prepreg (1) in the manner described above. The metal-clad laminate of this embodiment can also be manufactured, for example, by heating the resin-coated metal foil described above to further cure the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product, in the resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1).

[0096] <<Printed Wiring Board>> The printed circuit board of this embodiment comprises an insulating layer containing a cured vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and conductive wiring. More specifically, as the printed circuit board of this embodiment, an example is a printed circuit board comprising the insulating layer and the conductive wiring provided on one or both sides of the insulating layer. Multiple printed circuit boards of this embodiment can be laminated with a separately prepared insulating layer in between and pressurized while heating to form a multilayer printed circuit board. The printed circuit board of this embodiment (the insulating layer in the printed circuit board) has high thermal conductivity and low dielectric loss because it uses a vinyl compound (1).

[0097] The material of the conductor wiring is the same as the metal of the metal foil provided in the metal-clad laminate described above. The insulating layer used separately when laminating the printed circuit board in this embodiment is the insulating layer described earlier. In a printed circuit board, if conductive wiring is provided on both sides of the insulating layer, the material and thickness of these conductive wirings may be the same or different.

[0098] The printed circuit board of this embodiment can be manufactured, for example, by patterning metal foil on the metal-clad laminate described above to form conductive wiring (circuits). The printed circuit board of this embodiment can also be manufactured, for example, by heating the resin-coated metal foil described above to further cure the vinyl compound (1) or its semi-cured product, or the vinyl composition (1) or its semi-cured product in the resin layer, thereby forming an insulating layer containing a cured product of the vinyl compound (1) or a cured product of the vinyl composition (1), and further by patterning the metal foil to form conductive wiring (circuits). Metal foil can be patterned using known methods such as etching.

[0099] Figure 1 is a schematic cross-sectional view showing an example of a laminated structure of this embodiment obtained using vinyl compound (1). Note that, for convenience in order to make the features of the present invention easier to understand, the figures used in the following description may be enlarged to show the essential parts, and the dimensional ratios of each component may not be the same as in reality.

[0100] The laminated structure 1 shown herein 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 using a vinyl compound (1). The second layer 12 is selected according to the type of laminated structure 1. Both the first layer 11 and the second layer 12 are in the form of a film or a sheet. The second layer 12 may be provided over the entire surface 11a of the first layer 11, or in a part of it.

[0101] When the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 is a support film, the laminated structure 1 is a resin-coated film. When the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 is a metal foil, the laminated structure 1 is a resin-coated metal foil. When the first layer 11 is an insulating layer containing a cured vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and the second layer 12 is a metal foil, the laminated structure 1 is a metal-clad laminate.

[0102] Figure 2 is a schematic cross-sectional view showing another example of the laminated structure of this embodiment obtained using vinyl compound (1). In Figures 2 and subsequent figures, the same components as those shown in previously described figures are denoted by the same reference numerals as in those previously described figures, and their detailed descriptions are omitted.

[0103] 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 in Figure 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 two or more. The laminated structure 2 is the same as the laminated structure 1 shown in Figure 1, except that it has a linear second layer 22 instead of a film-like second layer 12. The laminated structure 2 is a printed circuit board when the first layer 11 is an insulating layer containing a cured vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and the second layer 22 is a conductive wiring.

[0104] Both the laminated structure 1 and the laminated structure 2 shown in Figures 1 and 2 have nothing on the other surface 11b of the first layer 11, but they may have a layer similar to the second layer 12 or the second layer 22.

[0105] Figure 3 is a schematic cross-sectional view showing yet another example of the laminated structure of this embodiment obtained using vinyl compound (1). The laminated structure 3 shown herein comprises 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 a sheet, and, like the second layer 12, is selected according to the type of laminated structure 1. The arrangement of the third layer 13 on the other surface 11b of the first layer 11 is the same as the arrangement 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 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 in a part of the area.

[0106] When the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 and third layer 13 are support films, the laminated structure 3 is a resin-coated film. When the first layer 11 is a resin layer containing a vinyl compound (1) or a semi-cured product thereof, or a vinyl composition (1) or a semi-cured product thereof, and the second layer 12 and 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 vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and the second layer 12 and third layer 13 are metal foils, the laminated structure 3 is a metal-clad laminate.

[0107] Figure 4 is a schematic cross-sectional view showing yet another example of the laminated structure of this embodiment obtained using vinyl compound (1). The laminated structure 4 shown herein 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 in Figure 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 the same as 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 two or more. The laminated structure 4 is a printed circuit board when the first layer 11 is an insulating layer containing a cured vinyl compound (1), a cured vinyl composition (1), or a cured prepreg (1), and the second layer 22 and third layer 23 are conductive wiring. [Examples]

[0108] The present invention will be described in more detail below with reference to specific examples. However, the present invention is not limited in any way to the examples shown below.

[0109] [Example 1] <<Manufacturing of vinyl compounds>> In a 200 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 20 g of 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene, 0.2 g of 2,6-di(tert-butyl)-p-cresol, 40 g of potassium carbonate, 4.5 g of sodium iodide, 110 mL of N,N-dimethylformamide, and 32.6 g of vinylbenzyl chloride were charged and reacted at an internal temperature of approximately 80°C for 4.5 hours. The vinylbenzyl chloride used here was a mixture of 3-vinylbenzyl chloride and 4-vinylbenzyl chloride.

[0110] After the reaction was complete, the mixture was cooled to room temperature, 200 mL of water was added, and the precipitated solid was filtered and washed with water. The washed solid obtained above was suspended in a mixture of 180 mL of methanol, 180 mL of water, and 0.5 g of 2,6-di(tert-butyl)-p-cresol, stirred, filtered, and washed with water. The resulting solid was suspended in 180 mL of isopropyl alcohol and stirred at an internal temperature of 60°C for 2 hours. The solid in the suspension was then filtered and dried under reduced pressure.

[0111] After drying, 14.3 g of the solid obtained was mixed with 0.15 g of 2,6-di(tert-butyl)-p-cresol, 334 g of toluene, and 71.7 g of silica gel. The mixture was stirred at an internal temperature of 45°C for 30 minutes, and then filtered to remove insoluble matter. Toluene was removed from the resulting solution under reduced pressure, and then 158 g of methanol was added dropwise while stirring at an internal temperature of 50°C. The mixture was stirred for a further 1 hour, and then cooled to room temperature. The precipitated crystals were collected by filtration, washed with methanol, and dried under reduced pressure to obtain 8.6 g of vinyl compound (1)-1 represented by the following formula (1)-1. The purity of vinyl compound (1)-1 was 91.4% by area percentage in the analysis data obtained by high-performance liquid chromatography.

[0112] [ka]

[0113] Vinyl compound (1)-1 1 The H-NMR data is shown below. 1 1H NMR (δ: ppm, CDCl3 solvent): 7.54-7.34(m,8H),7.30-7.17(m,4H),7.01-6.92(m,2H),6.90-6.83(m,1H),6.82-6.70(m,2H),6.13(bs,1H),5.85-5.74(m,2H),5 .33-5.25(m,2H),5.13-5.05(m,4H)2.91-2.79(m,1H),2.62-2.44(m,3H),2.39-2.27(m,4H),2.16-2.05(m,1H),1.97-1.81(m,1H)

[0114] <<Manufacturing of cured vinyl resin products>> The vinyl compound (1)-1 obtained above was poured into the hollow plate portion of the mold and cured under reduced pressure at 160°C for 1 hour at a pressure of 1.5 MPa, and then further cured at 180°C for 2 hours while maintaining a pressure of 1.5 MPa. Thus, a cured vinyl resin product (1)-1 was obtained.

[0115] [Example 2] <<Manufacturing of vinyl compounds>> In a 200 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 5.0 g of 1-(3-methyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene, 0.05 g of 2,6-di(tert-butyl)-p-cresol, 9.9 g of potassium carbonate, 1.1 g of sodium iodide, 33 mL of N,N-dimethylformamide, and 8.2 g of 4-vinylbenzyl chloride were charged and reacted at an internal temperature of approximately 60°C for 3 hours.

[0116] After the reaction was complete, the mixture was cooled to room temperature. Then, 41 mL of heptane and 41 mL of water were added and stirred for 20 minutes. The precipitated solid was filtered and washed with heptane. The entire amount of the obtained solid was mixed with 0.05 g of 2,6-di(tert-butyl)-p-cresol, 340 g of toluene, and 46 g of silica gel. The mixture was stirred at 50°C for 30 minutes, and then filtered to remove insoluble matter. Water was added to the resulting solution, and after three liquid-liquid extractions, the toluene was removed under reduced pressure. 336 g of toluene was added to the obtained solid and stirred at 50°C, then cooled to 10°C. The precipitated crystals were filtered, washed with toluene, and dried under reduced pressure to obtain 6.4 g of vinyl compound (1)-2, represented by the following formula (1)-2. The purity of vinyl compound (1)-2 was 96.2% by area percentage in the analysis data obtained by high-performance liquid chromatography.

[0117] [ka]

[0118] Vinyl compound (1)-2 1 The H-NMR data is shown below. 1 1H NMR (δ: ppm, CDCl3 solvent): 7.50-7.39(m,8H),7.31-7.17(m,4H),7.00-6.92(m,2H),6.86(d,J=8.4Hz,1H),6.79(dd,J =11.1Hz,J=1.2Hz,1H),6.73(dd,J=10.8Hz,J=1.2Hz,1H),6.16-6.10(m,1H),5.79(d,J=17 .7Hz,2H),5.29(dd,2H,J=10.8Hz,J=0.6Hz,2H),5.11(s,2H),5.07(s,2H),2.92-2.79(m,1 H),2.62-2.44(m,3H),2.41-2.24(m,1H),2.32(s,3H),2.16-2.05(m,1H),1.97-1.80(m,1H)

[0119] <<Manufacturing of cured vinyl resin products>> Vinyl resin cured product (1)-2 was obtained in the same manner as in Example 1, except that vinyl compound (1)-2 obtained above was used instead of vinyl compound (1)-1.

[0120] [Comparative Example 1] <<Manufacturing of vinyl compounds>> In a 200 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 6.0 g of 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl, 0.06 g of 2,6-di(tert-butyl)-p-cresol, 12 g of potassium carbonate, 1.3 g of sodium iodide, 34 mL of N,N-dimethylformamide, and 10 g of 4-vinylbenzyl chloride were charged and reacted at an internal temperature of approximately 60°C for 3 hours. After the reaction was complete, 121 g of toluene and 34 mL of water were added and stirred, and the mixture was filtered to remove insoluble matter. The resulting solution was separated and washed three times with water. After filtering the resulting solution to remove insoluble matter, toluene was removed under reduced pressure. 56 mL of methanol and 0.07 g of 2,6-di(tert-butyl)-p-cresol were added to the resulting 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 (R)-1 represented by the following formula (R)-1. The purity of vinyl compound (R)-1 was 99.1% as an area percentage in the analysis data obtained by high-performance liquid chromatography.

[0121] [ka]

[0122] Vinyl compound (R)-1 1 The H-NMR data is shown below. 1 1H NMR (δ: ppm, CDCl3 solvent): 7.52-7.44(m,8H),6.81(s,2H),6.76(dd,J=17.7Hz,J=10.8Hz,2H),5.79(dd,J=17.7Hz,J=0.9 Hz,2H),5.27(dd,J=10.8Hz,J=0.9Hz,2H),4.83(s,4H),2.30(s,6H),2.27(s,6H),1.93(s,6H)

[0123] <<Manufacturing of cured vinyl resin products>> Vinyl compound (R)-1 obtained above was used instead of vinyl compound (1)-1, and compound 1 was obtained in the same manner as in Example 1.

[0124] [Comparative Example 2] <<Manufacturing of epoxy compounds>> According to Example 1 of Japanese Patent Publication No. 2009-249299, 1-(3-methyl-4-oxyranylmethoxyphenyl)-4-(4-oxyranylmethoxyphenyl)-1-cyclohexene represented by the following formula (R)-2 (hereinafter referred to as "epoxy compound (R)-2") was obtained.

[0125] [ka]

[0126] Epoxy compound (R)-2 1 The H-NMR data is shown below. 1 1H NMR (δ: ppm, CDCl3 solvent): 7.26-7.15(m,4H),6.91-6.85(m,2H),6.77(d,J=8.7Hz,1H),6.12-6.07(m,1H),4.27-4.16(m,2H),4.02-3.93(m,2H),3.41-3.32(m ,2H),2.94-2.88(m,2H),2.89-2.74(m,3H),2.58-2.41(m,3H),2.34-2.21(m,1H),2.26(s,3H),2.12-2.02(m,1H),1.93-1.78(m,1H)

[0127] <<Manufacturing of epoxy compositions, manufacturing of cured epoxy resins>> An epoxy composition was obtained by mixing 20 parts by mass of epoxy compound (R)-2 obtained in Comparative Example 2 with 5 parts by mass of 4,4'-diaminodiphenylmethane (curing agent). This molten epoxy composition was poured into the hollow plate-shaped part of a mold, degassed at 140°C, then kept at 140°C for 1 hour, and then kept at 180°C for 2 hours to cure it. As a result, epoxy resin cured product (R)-2 was obtained.

[0128] <<Evaluation of cured vinyl resin and cured epoxy resin>> <Measurement of thermal diffusivity> For the vinyl resin cured product (1)-1, vinyl resin cured product (1)-2, vinyl resin cured product (R)-1, and epoxy resin cured product (R)-2 obtained above, the thermal diffusivity (m) was determined by thermal wave thermal analysis (TWA method) using a thermal diffusivity measuring device (ai-phase mobile, manufactured by i-phase Co., Ltd.). 2 The time ( / s) was measured. The results are shown in Table 1.

[0129] <Measurement of dielectric loss tangent> The dielectric loss tangent at a frequency of 100 MHz was measured for the vinyl resin cured products (1)-1, (1)-2, (R)-1, and (R)-2 obtained above, under the following conditions. The results are shown in Table 1. • Measurement method: Capacitance method (Equipment: Impedance analyzer (Agilent, Model: E4991A)) ·Electrode model: 16453A • Measurement environment: 23℃, 50%RH • Applied voltage: 1V

[0130] [Table 1]

[0131] In Examples 1 and 2, vinyl compound (1) was used, and the thermal diffusivity of vinyl resin cured product (1)-1 and vinyl resin cured product (1)-2 was 2.43 × 10⁻⁶. -7 m 2 The temperature was above / s, which was sufficiently high, and the dielectric loss tangents of vinyl resin cured product (1)-1 and vinyl resin cured product (1)-2 were 0.0044 or less, which was sufficiently small.

[0132] In contrast, Comparative Example 1 used vinyl compound (R)-1, which is not vinyl compound (1). The thermal diffusivity of vinyl resin cured product (R)-1 was lower than that of vinyl resin cured product (1)-1 and vinyl resin cured product (1)-2, and the dielectric loss tangent of vinyl resin cured product (R)-1 was higher than that of vinyl resin cured product (1)-1 and vinyl resin cured product (1)-2.

[0133] In Comparative Example 2, epoxy compound (R)-2, which is not vinyl compound (1), was used, and the dielectric loss tangent of epoxy resin cured product (R)-2 was significantly higher than that of vinyl resin cured product (1)-1 and vinyl resin cured product (1)-2. The only difference between vinyl compound (1)-1 and vinyl compound (1)-2 and epoxy compound (R)-2 is the functional group at the molecular ends. When the group having a vinyl group (in Examples 1 and 2) is replaced with a group having an epoxy group (in Comparative Example 2), the dielectric loss tangent of the cured resin is significantly increased. This confirms that the presence of a vinyl group at the molecular ends of vinyl compound (1) significantly reduces the dielectric loss tangent of the cured vinyl resin (1).

[0134] The difference between vinyl compounds (1)-1 and (1)-2 and vinyl compound (R)-1 lies in the number of links in the ring structure located near the center of the molecule's length, which constitutes the mesogenic skeleton. It was confirmed that a higher number of these links improves the thermal diffusivity and dielectric loss tangent of the cured vinyl resin. [Industrial applicability]

[0135] The present invention can be used in printed circuit boards in communication equipment, and is particularly suitable for use in printed circuit boards when communication equipment is expected to handle a large amount of data and generate a large amount of heat. [Explanation of symbols]

[0136] 1, 2, 3, 4... Laminated structure, 11... First layer, 11a... One side of the first layer, 11b... The other side of the first layer, 12, 22... Second layer, 13, 23... Third layer

Claims

1. Formula (1) 【Chemistry 1】 (In the formula, A １ A ２ and A ３ Each of them is either the same or different, as shown below. 【Chemistry 2】 This represents one of the divalent groups indicated by . Here, the two lines at the para position of the cyclic structure represent the bonding position with other structural sites. R represents a hydrogen atom or a methyl group. a represents an integer from 1 to 10, b and c represent integers from 1 to 8, d, e, f and g represent integers from 1 to 6, and h represents an integer from 1 to 4. In the aforementioned divalent group, when there are multiple Rs, all Rs may represent the same group or may represent different groups. １ and Q ２ These are either identical or different, as in equation (2) 【Transformation 3】 This represents a divalent group. Here, Ar represents an aromatic group. The methylene group in formula (2) is bonded to the oxygen atom in formula (1). A vinyl compound represented by [the symbol].

2. The vinyl compound represented by formula (1) is, 【Chemistry 4】 (In the formula, A ４ The formula is as follows: 【Transformation 5】 Represents any of the divalent groups shown by R, a, c, h, Q １ and Q ２ The above has the same meaning, and in the divalent group, the two lines located at the para position of the cyclic structure represent the bonding positions with other structural parts. The vinyl compound according to claim 1, which is a vinyl compound represented by .

3. A method for producing the vinyl compound described in claim 1, wherein formula (4) 【Transformation 6】 (wherein, A １ , A ２ and A ３ each represent the same meaning as described above.) The compound shown by and formula (5) 【Transformation 7】 (In the formula, Q １ This expresses the same meaning as above, X １ (This represents a halogen atom.) The compound shown by and formula (6) 【Transformation 8】 (In the formula, Q ２ This expresses the same meaning as above, X ２ represents a halogen atom, and the above X １ (It may be the same as, or it may be different.) A method for producing a vinyl compound, comprising reacting a compound shown with a base in the presence of a base.

4. A vinyl composition containing the vinyl compound described in claim 1 or 2.

5. A cured vinyl resin obtained by curing the vinyl compound according to claim 1 or 2, or the vinyl composition according to claim 4.

6. A prepreg comprising a vinyl compound or a semi-cured product thereof according to claim 1 or 2, or a vinyl composition or a semi-cured product thereof according to claim 4, and a fibrous substrate.

7. A resin-coated film comprising a resin layer containing a vinyl compound or a semi-cured product thereof according to claim 1 or 2, or a vinyl composition or a semi-cured product thereof according to claim 4, and a support film.

8. A resin-coated metal foil comprising a resin layer containing a vinyl compound or a semi-cured product thereof according to claim 1 or 2, or a vinyl composition or a semi-cured product thereof according to claim 4, and a metal foil.

9. A metal-clad laminate comprising an insulating layer containing a cured vinyl compound according to claim 1 or 2, a cured vinyl composition according to claim 4, or a cured prepreg according to claim 6, and a metal foil.

10. A printed wiring board comprising an insulating layer containing a cured vinyl compound according to claim 1 or 2, a cured vinyl composition according to claim 4, or a cured prepreg according to claim 6, and conductive wiring.

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