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

Abstract

The present invention addresses the problem of providing a novel compound capable of producing a resin which is suitable as a constituent material for a printed wiring board and which has high thermal conductivity and low dielectric loss. The present invention relates to a vinyl compound represented by formula (A). (In formula (A), Q represents any group selected from the group consisting of formulae (1) to (3); a1, A2, A3, and A4 are selected from the group consisting of a divalent aromatic group, a divalent cycloalkylene or cycloalkylene group, a divalent group in which two or more divalent aromatic groups are linked by a single bond, and a divalent group in which two or more divalent cycloalkylene or cycloalkylene groups are linked by a single bond; and one or more divalent groups in which one or more divalent aromatic groups and one or more substituted or unsubstituted divalent cycloalkylene or cycloalkylene groups are linked by a single bond, X1, X2, and X3 are any one selected from the group consisting of a single bond, an ester group, and a carbonyl group, and when at least one of Y1 and Y2 is a vinyl group, X1, X2, and X3 are any one selected from the group consisting of a single bond, an ester group, and a carbonyl group. In the formula, at least one of X1, X2 and X3 constituting Q is an ester group or a carbonyl group, at least one of A1, A2, A3 and A4 is a cyclohexyl ring, and n1 and n2 are integers from 1 to 20) # imgabs 0 # imgabs 1 #.

Description

Technical Field

[0001] This invention relates to vinyl compounds, vinyl compositions, vinyl resin cured products, prepregs, resin-coated films, resin-coated metal foils, metal-clad laminates, and printed circuit boards. Background Technology

[0002] The amount of data processed and the communication speed of communication equipment are increasing year by year. Along with this, high-speed communication technologies to improve signal transmission speed are being actively researched. With the large amount of data processed by communication equipment, the heat generated in the electronic processing components increases. If this heat accumulates in the printed circuit board (PCB), it can cause malfunctions. Therefore, PCBs require high heat dissipation capabilities.

[0003] As a type of printed circuit board with high heat dissipation, there are known thick copper substrates, which can release more heat through the copper forming the circuit (i.e., the copper pattern) by making it thicker than before. However, the overall thickness of the thick copper substrate makes it unsuitable for communication devices that require miniaturization and lightweight design.

[0004] As a type of printed circuit board with high heat dissipation, there is also a so-called metal substrate, which can dissipate more heat through a metal plate placed on one side. However, the increased number of manufacturing steps in the production of this metal substrate leads to increased manufacturing costs for communication devices.

[0005] On the other hand, similar to printed circuit boards, components containing highly thermally conductive filler materials are known to be components with high heat dissipation, as they are mainly composed of resin. However, materials containing filler materials have poor processability, making them unsuitable for the manufacture of printed circuit boards.

[0006] As a material capable of solving these problems, a resin with high thermal conductivity has been disclosed (Patent Document 1). For electronic materials used in high-speed communication equipment, in addition to high heat dissipation, low dielectric loss is also required. The resin disclosed in Patent Document 1 has both high thermal conductivity and low dielectric loss.

[0007] Existing technical documents

[0008] Patent documents

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

[0010] The problem that the invention aims to solve

[0011] However, the thermal conductivity of the resin disclosed in Patent Document 1 is not sufficient and there is room for improvement.

[0012] The object of this invention is to provide a novel compound that can be used to manufacture resins with high thermal conductivity and low dielectric loss, suitable for use as constituent materials of printed circuit boards.

[0013] Methods for solving problems

[0014] The present invention adopts the following structure.

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

[0016] [Chemical Formula 1]

[0017]

[0018] (In the above formula (A), Y) 1 and Y 2 Whether they are the same or different, they are any groups selected from vinyl and vinylbenzyl.

[0019] Q is any group selected from formulas (1) to (3).

[0020] [Chemical Formula 2]

[0021]

[0022] In the above equations (1) to (3),

[0023] A 1 A 2 A 3 and A 4 Whether they are the same or different, they are selected from substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups).

[0024] Substituted or unsubstituted divalent cycloalkyl groups

[0025] A divalent group formed by two or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) linked by a single bond.

[0026] A divalent group consisting of two or more substituted or unsubstituted divalent cycloalkyl or cycloolefin groups linked by a single bond, and

[0027] Any one of the following: a divalent group consisting of one or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) linked by one or more substituted or unsubstituted divalent cycloalkyl or cycloolefin groups via single bonds.

[0028] X 1 X 2 and X 3Whether they are the same or different, they are selected from any one of single bonds, ester groups, and carbonyl groups.

[0029] In Y 1 and Y 2 When at least one of them is a vinyl group, X 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.

[0030] n1 and n2 may be the same or different, representing integers from 1 to 20.

[0031] [2] According to the vinyl compound described in [1], wherein the above-mentioned X 1 X 2 and X 3 At least one of them is an ester group.

[0032] [3] According to the vinyl compound described in [1] or [2], wherein the above-mentioned A 1 A 2 A 3 and A 4 It is a divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups).

[0033] [4] The vinyl compound described in any one of [1] to [3] is used in printed circuit boards.

[0034] [5] A vinyl composition comprising any one of the vinyl compounds described in [1] to [3].

[0035] [6] A vinyl resin cured product, which is formed by curing the vinyl compound described in any one of [1] to [3] or the vinyl composition described in [5].

[0036] [7] A prepreg comprising a vinyl compound or a semi-cured product thereof described in any one of [1] to [3] or a vinyl composition or a semi-cured product thereof described in [5], and a fibrous substrate.

[0037] [8] A resin-containing membrane having a resin layer and a support membrane, the resin layer comprising a vinyl compound or a semi-cured product thereof described in any one of [1] to [3], or a vinyl composition or a semi-cured product thereof described in [5].

[0038] [9] A resin-coated metal foil comprising a resin layer and a metal foil, wherein the resin layer comprises a vinyl compound or a semi-cured product thereof described in any one of [1] to [3], or a vinyl composition or a semi-cured product thereof described in [5].

[0039]

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

[0040]

[11] A metal-clad laminate having an insulating layer and a metal foil, the insulating layer comprising a cured form of the prepreg described in [7].

[0041]

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

[0042]

[13] A printed circuit board having an insulating layer and conductive wiring, the insulating layer comprising a cured form of the prepreg described in [7].

[0043] Invention Effects

[0044] According to the present invention, a novel compound is provided that can be used to manufacture resins with high thermal conductivity and low dielectric loss, suitable for use as constituent materials of printed circuit boards. Furthermore, when manufacturing resins and molded articles such as printed circuit boards from this novel compound, the manufacturing process is simplified due to its low melting point. Attached Figure Description

[0045] Figure 1 This is a cross-sectional view schematically illustrating an example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention.

[0046] Figure 2 This is a cross-sectional view schematically illustrating another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention.

[0047] Figure 3 This is a cross-sectional view schematically illustrating yet another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention.

[0048] Figure 4 This is a cross-sectional view schematically illustrating yet another example of a laminated structure obtained using a vinyl compound according to one embodiment of the present invention. Detailed Implementation

[0049] <Vinyl Compounds>

[0050] The vinyl compound of this embodiment is represented by the following formula (A). In this specification, the vinyl compound shown in (A) above is sometimes referred to as "vinyl compound (A)".

[0051] [Chemical Formula 3]

[0052]

[0053] Y in vinyl compound (A) 1 and Y 2 Whether they are the same or different, they are any groups selected from vinyl and vinylbenzyl.

[0054] Furthermore, Q has a mesocrystalline framework structure, consisting of two or more hydrocarbon rings linked together. The number of carbon atoms in Q is not particularly limited; in one example, it can be 12 or more, preferably 13 or more. In formula (A) above, Q is any group selected from formulas (1) to (3).

[0055] [Chemical Formula 4]

[0056]

[0057] In the above equations (1) to (3),

[0058] A 1 A 2 A 3 and A 4 Whether they are the same or different, they are selected from substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups).

[0059] Substituted or unsubstituted divalent cycloalkyl groups

[0060] A divalent group formed by two or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) linked by a single bond.

[0061] A divalent group consisting of two or more substituted or unsubstituted divalent cycloalkyl or cycloolefin groups linked by a single bond, and

[0062] Any one of the following: a divalent group consisting of one or more substituted or unsubstituted divalent aromatic groups (excluding nitrogen-containing aromatic heterocyclic groups) linked by one or more substituted or unsubstituted divalent cycloalkyl or cycloolefin groups via a single bond.

[0063] In Y 1 and Y 2 If at least one of them is a vinyl group, then X constitutes Q. 1 X 2 and X 3At 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.

[0064] n1 and n2 can be the same or different, representing integers from 1 to 20.

[0065] In this specification, the aromatic ring can be a monocyclic ring, a fused ring, or a heterocyclic ring, but a monocyclic ring is preferred. When the aromatic ring is a heterocyclic ring, examples of heteroatoms other than nitrogen atoms, such as oxygen and sulfur atoms, can be included. From the viewpoint of suppressing dielectric loss or reducing the dielectric loss tangent, the aromatic ring preferably does not contain heteroatoms. The aromatic ring is preferably a monocyclic or fused ring, and more preferably a monocyclic ring.

[0066] The number of carbon atoms in the unsubstituted divalent aromatic group is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0067] Specific examples of unsubstituted divalent aromatic rings include benzene, naphthalene, anthracene, phenanthrene, pyrene, benzo[9,10]phenanthrene, perylene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, and dibenzothiophene.

[0068] 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 hydroxyl group, for example, one or more groups selected from alkyl groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms.

[0069] Known alkyl groups can be cited as alkyl groups having 1 to 20 carbon atoms. The number of carbon atoms in the alkyl group is preferably 1 to 8, and more preferably 1 to 4. Specific examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.

[0070] Examples of alkoxy groups having 1 to 20 carbon atoms include known alkoxy groups. The preferred carbon number of the alkoxy group is 1 to 8, more preferably 1 to 4. Specific examples of alkoxy groups having 1 to 4 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, and isobutoxy.

[0071] In this specification, cycloalkane rings and cycloalkene rings can be monocyclic, fused, or heterocyclic. When the cycloalkane or cycloalkene ring is a heterocyclic ring, examples of heteroatoms included in the heterocyclic ring include oxygen, nitrogen, and sulfur atoms. From the viewpoint of suppressing dielectric loss or achieving the dielectric loss tangent, aromatic rings preferably do not contain heteroatoms. Aromatic rings are preferably monocyclic or fused, and more preferably monocyclic.

[0072] In addition, in this specification, the cycloalkylene and cycloalkenylene groups can be cis-isophores, trans-isophores, or mixtures thereof, with a higher proportion of trans-isophores preferred in the case of mixtures.

[0073] The number of carbon atoms in the unsubstituted divalent cycloalkyl and cycloalkenyl groups is not particularly limited, but is preferably 3 to 20, more preferably 6 to 16, and even more preferably 6 to 14.

[0074] Specific examples of unsubstituted cycloalkane rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane, cyclopentadecanane, cyclohexadecane, cycloheptadecane, cyclooctadecane, cyclononadecanane, cycloeicosane, decahydronaphthalene, adamantane, oxacyclobutane, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 1,3-dioxane, aziridine, pyrrolidine, piperidine, piperazine, morpholine, tetrahydrothiophene, and cyclopentane sulfide (Japanese: チアン).

[0075] Specific examples of unsubstituted cyclic olefin rings include cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, and cyclodecene.

[0076] When divalent cycloalkyl and cycloolefinic groups have substituents, the substituents have the same meaning as the substituents that divalent aromatic groups can have.

[0077] In compounds formed by two or more substituted or unsubstituted aromatic rings linked by single bonds, the number of substituted or unsubstituted aromatic rings linked by single bonds is not particularly limited if it is 2 or more, preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0078] Specific examples of compounds consisting of two or more unsubstituted aromatic rings linked by single bonds include biphenyl, ortho-terphenyl, meta-terphenyl, para-terphenyl, meta-tetraphenyl, and para-tetraphenyl.

[0079] In compounds formed by two or more substituted or unsubstituted cycloalkane rings or cycloalkene rings linked by single bonds, the number of substituted or unsubstituted cycloalkane rings or cycloalkene rings linked by single bonds is not particularly limited if it is 2 or more, preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0080] Specific examples of compounds consisting of two or more unsubstituted cycloalkane or cycloalkene rings linked by single bonds include cyclopropylcyclohexane, bicyclohexane, 1,3-dicyclohexylcyclohexane, 1,4-dicyclohexylcyclohexane, 1-cyclohexylpyrrolidine, and 4-cyclohexylmorpholine.

[0081] In compounds formed by one or more substituted or unsubstituted aromatic rings linked to one or more substituted or unsubstituted cycloalkane or cycloalkene rings via single bonds, the number of substituted or unsubstituted aromatic rings linked by single bonds is not particularly limited if it is 1 or more, but preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Furthermore, the total number of substituted or unsubstituted aromatic rings linked by single bonds to the number of substituted or unsubstituted cycloalkane or cycloalkene rings is preferably 2 to 10, more preferably 2 to 4, and even more preferably 2.

[0082] Specific examples of compounds formed by one or more unsubstituted aromatic rings linked to one or more unsubstituted cycloalkane or cycloalkene rings via single bonds include cyclopropylbenzene, cyclopentylbenzene, cyclohexylbenzene, 1-cyclohexylnaphthalene, 2-cyclohexylnaphthalene, 2-phenyltetrahydrofuran, 1-phenyladamantane, 1,3-diphenyladamantane, 1,3,5,7-tetraphenyladamantane, 2-cyclohexylfuran, 4-phenylpiperidine, 2-cyclohexylthiophene, and 4-phenylmorpholine, 1,1'-(1-cyclohexene-1,4-diyl)-bisbenzene, 1-(4-phenyl-1-cyclohexene-1-yl)-3-methylbenzene, etc.

[0083] 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 cycloalkyl or cycloalkenyl group is a residue obtained by removing two hydrogen atoms from any position of a substituted or unsubstituted cycloalkane or cycloalkene ring.

[0084] From the perspective of improving thermal conductivity, A 1 A 2 A 3 and A 4 Preferably, it is a divalent aromatic group (excluding nitrogen-containing aromatic heterocyclic groups).

[0085] In formula (A), X 1 X 2 and X 3 Whether they are the same or different, they are selected from single bonds, ester groups ( -COO- or -OCO- ; , Indicates with A 1 A 2 A 3 and A 4 The bonding position of any of the groups. ) and either the carbonyl group, preferably an ester group or a carbonyl group, more preferably an ester group. By making X 1 X 2 and X 3 The vinyl group is an ester group, thus vinyl resin cured products containing vinyl compounds can exhibit excellent heat transfer properties.

[0086] In formula (A), n1 and n2 may be the same or different, preferably integers from 1 to 10, and more preferably integers from 2 to 8. In this embodiment, in addition to the mesocrystalline framework, alkyl spacer groups with a carbon number of n1 and n2 are introduced into the vinyl compound, thereby enabling the production of a low-melting-point vinyl compound.

[0087] The melting point of the vinyl compound (A) is preferably 50–150°C or less, more preferably 80–140°C or less, even more preferably 90–130°C, and particularly preferably 95–120°C. If the melting point of the vinyl compound is within the above range, processing based on melt blending or the like becomes easier, and the energy required for processing can also be suppressed.

[0088] Vinyl compound (A) is polymerizable and, through polymerization (also referred to as "curing" in this specification), can form a cured vinyl resin as described later. Therefore, vinyl compound (A) is suitable for use as a constituent material for insulating layers, heat dissipation materials, etc., of printed circuit boards.

[0089] On the other hand, resins containing hydroxyl groups tend to have high dielectric losses. For example, resins that are cured products of compounds (monomers) with epoxy groups at their ends have hydroxyl groups and thus exhibit high dielectric losses. In contrast, the vinyl compound (A) does not have either epoxy or hydroxyl groups at its ends, but rather a vinyl group (vinyl). Therefore, the cured product (polymer) of the vinyl compound (A) does not have hydroxyl groups in the resin and thus exhibits low dielectric losses.

[0090] <Method for manufacturing vinyl compound (A)>

[0091] Vinyl compound (A) can be prepared, for example, by reacting a compound of formula (B) (sometimes referred to as "compound (B)" in this specification) with a compound of formula (C) or formula (D) (sometimes referred to as "compound (C)" or "compound (D)" in the presence of a base.

[0092] [Chemical Formula 5]

[0093]

[0094] (In the formula, Q has the same meaning as above.)

[0095] [Chemical Formula 6]

[0096]

[0097] (where Z) 1 This represents a halogen atom. Additionally, n represents an integer from 1 to 20.

[0098] Examples of the above-mentioned compound (B) include 1-1'-(1-1'-biphenyl)-4-4'-dimethylbis(4-hydroxybenzoate), (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), etc.

[0099] The above Z 1 This refers to a halogen atom. Examples of halogen atoms include chlorine, bromine, and iodine.

[0100] Examples of compounds (C) or (D) include 2-vinylbenzyl bromide ether, 3-vinylbenzyl bromide ether, 4-vinylbenzyl bromide ether, chloroalkyl vinyl ether, bromoalkyl vinyl ether, 2-vinylbenzyl chloroalkyl ether, 3-vinylbenzyl chloroalkyl ether, 4-vinylbenzyl chloroalkyl ether, etc. Compound (C) and compound (D) may be used individually or in any combination and ratio of two or more.

[0101] The amount of compound (C) or compound (D) used relative to compound (B) is generally preferably 2 to 100 equivalents, more preferably 2 to 50 equivalents.

[0102] The base used in the reaction can be either an inorganic base or an organic base.

[0103] Examples of inorganic bases 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.

[0104] Examples of organic bases mentioned above include pyridine. The amount of base used relative to compound (B) is generally preferred to be 2 to 5 equivalents. When using an organic base that is liquid under reaction conditions, it may also be used in excess as a reaction solvent.

[0105] The reaction of compound (B) with compound (C) or compound (D) is usually carried out by mixing compound (B) with compound (C) or compound (D) with a base in a solvent. There is no particular requirement for the order of mixing.

[0106] The solvents mentioned above are not particularly limited to those that are inactive in the reaction; however, hydrophilic solvents are preferred from the perspective of easily suppressing the formation of byproducts. Examples of such hydrophilic solvents include alcohols such as methanol, ethanol, propanol, butanol, ethylene glycol, and propylene glycol; ketones such as methyl ethyl ketone and methyl isobutyl ketone; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone; and ethers such as tetrahydrofuran, dioxane, methoxymethyl ether, and diethoxyethane, either alone or in combination. Furthermore, as mentioned above, when using an organic base that is liquid under the reaction conditions as the base, the aforementioned organic bases can be used as the reaction solvent.

[0107] 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.

[0108] The amount of solvent used is preferably 1 to 20 mL per 1 g of compound (B), more preferably 2 to 10 mL.

[0109] The reaction of compound (B) with compound (C) or compound (D) can be carried out via halogen exchange reaction in the presence of a catalyst.

[0110] Examples of catalysts mentioned above include alkali metal halides such as sodium iodide and potassium iodide; and quaternary ammonium halides such as tetrabutylammonium iodide.

[0111] When using a catalyst, its amount is preferably 0.05 to 1 times by mass relative to the amount of compound (B), more preferably 0.1 to 0.5 times by mass.

[0112] The reaction of compound (B) with compound (C) or compound (D) can be carried out in the presence of a polymerization inhibitor. Examples of such polymerization inhibitors include 2,6-bis(tert-butyl)-p-cresol. When using a polymerization inhibitor, its amount used is generally preferably 0.002 to 0.05 times by mass relative to the amount used of compound (C) or compound (D), and more preferably 0.004 to 0.02 times by mass.

[0113] The reaction can be carried out under normal or reduced pressure. The preferred reaction temperature is typically 10–150°C. It should be noted that water may sometimes be produced as a byproduct of this reaction. In such cases, it is preferable to remove the produced water from the reaction system while carrying out the reaction, preferably at the reaction temperature and pressure at which the water is removed by azeotropic reaction. The preferred reaction time is typically 1–24 hours.

[0114] After the reaction is complete, for example, the reaction solution is cooled, water or a mixed solvent containing water is added, the precipitated solid is filtered off, and one or more known post-treatment operations are performed as needed to obtain vinyl compound (A). Examples of such post-treatment operations include, for instance, stirring and washing the solid in water, a mixed solvent containing water, or an organic solvent; extraction (liquid extraction) of the solution containing the solid, etc. The obtained vinyl compound (A) can be further purified as needed using conventional purification methods.

[0115] The structure of the obtained vinyl compound (A) can be confirmed, for example, by known methods such as nuclear magnetic resonance (NMR).

[0116] <Vinyl Composition>

[0117] The vinyl composition of this embodiment contains vinyl compound (A).

[0118] In this specification, the vinyl composition of this embodiment is sometimes referred to as "vinyl composition (A)".

[0119] The above-described vinyl composition (A) is curable and may contain only vinyl compound (A), or may contain vinyl compound (A) and other components other than vinyl compound (A) to a extent that does not impair the effects of the present invention. Vinyl compound (A) can be cured by heating or by light irradiation. In the following embodiments, it is cured by heating. Pressure may be applied to vinyl compound (A) during curing.

[0120] The vinyl composition (A) may contain only one vinyl compound (A) or two or more vinyl compounds.

[0121] When the vinyl composition (A) contains two or more vinyl compounds (A), the vinyl compounds (A) are preferably a mixture of multiple vinyl compounds (A) whose vinyl groups, which are terminal groups, have different positions of vinyl groups and are the same in all other parts except for the vinyl group.

[0122] For example, in a vinyl composition (A) containing two or more vinyl compounds (A), when the total molar number of all vinyl benzyl groups of all vinyl compounds (A) is set to 100, the molar number of vinyl benzyl groups at the meta position is preferably 30 to 90, more preferably 40 to 90, further preferably 50 to 90, even more preferably 60 to 80, and particularly preferably 70 to 80. Furthermore, for example, the ratio of the molar number of vinyl benzyl groups at the para position to the molar number of vinyl benzyl groups at the meta position (molar number of para-vinyl benzyl groups / molar number of meta-vinyl benzyl groups; sometimes referred to as the "p / m ratio" in this specification) is preferably 10 / 90 to 70 / 30, more preferably 10 / 90 to 60 / 40, further preferably 10 / 90 to 50 / 50, even more preferably 20 / 80 to 40 / 60, and particularly preferably 20 / 80 to 30 / 70. By setting the number of moles of meta-vinylbenzyl groups or the p / m ratio within the range described above, the mixture of vinyl compounds (A) melts at a lower temperature, thereby improving the processability of the vinyl compounds.

[0123] <Other Ingredients>

[0124] Other components contained in the vinyl composition (A) may include, for example, free radical initiators; fillers; additives; solvents; vinyl compounds other than vinyl compound (A) (sometimes referred to as "other vinyl compounds" in this specification); resins other than the polymer (cured product) of vinyl compound (A) (sometimes referred to as "other resins" in this specification), etc.

[0125] Examples of such additives include silane coupling agents, colorants, low-stress components, release agents, antioxidants, defoamers, and flow regulators.

[0126] Examples of free radical initiators include azo compounds and organic peroxides.

[0127] Examples of filler materials include, for example, molten and crushed silica powder, molten spherical silica powder, crystalline silica powder, and secondary agglomerated silica powder; metal oxides such as alumina, titanium dioxide, zinc oxide, tungsten carbide, and magnesium oxide; glass fiber cloth (glass fiber); carbon fiber; nitrides such as boron nitride, aluminum nitride, silicon nitride, and titanium nitride; silicon carbide; aluminum hydroxide; talc; clay; and mica.

[0128] Examples of silane coupling agents include γ-epoxypropoxypropyltrimethoxysilane.

[0129] Examples of such coloring agents include carbon black.

[0130] Examples of low-stress components mentioned above include silicone oil and silicone rubber.

[0131] Examples of release agents include natural waxes, synthetic waxes, higher fatty acids, metal salts of higher fatty acids, and paraffin wax.

[0132] Examples of solvents contained in the vinyl composition (A) include ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone; nonprotic polar solvents such as dimethyl sulfoxide and N-methylpyrrolidone; ester solvents such as butyl acetate; diol solvents such as propylene glycol monomethyl ether; and aromatic solvents such as toluene.

[0133] The other vinyl compounds mentioned above are not particularly limited if they are compounds having vinyl groups and not belonging to vinyl compound (A).

[0134] The other resins mentioned above are not particularly limited if they are resins other than polymers of vinyl compound (A).

[0135] The other components contained in the vinyl composition (A) may be only one or more.

[0136] The content of the other components in the vinyl composition (A) can be arbitrarily selected according to the types of the other components.

[0137] In the vinyl composition (A), the proportion of vinyl compound (A) relative to the total content of components other than the solvent is preferably 80% by mass or more, for example, it can be any one of 85% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, and 99% by mass or more. On the other hand, the above proportion is 100% by mass or less. The vinyl composition (A) with the above proportion of 80% by mass or more has a further improved effect due to the presence of vinyl compound (A).

[0138] The vinyl compound (A) obtained by the above method can be used directly as a vinyl composition (A). The vinyl composition (A) containing the other components mentioned above is obtained by mixing the vinyl compound (A) with the other components mentioned above.

[0139] <Vinyl Resin Cured Products>

[0140] The vinyl resin cured product of this embodiment is formed by curing a vinyl compound (A) or a vinyl composition (A).

[0141] In this specification, the vinyl resin cured product of this embodiment is sometimes referred to as "vinyl resin cured product (A)".

[0142] Vinyl resin cured products, through the use of vinyl compounds (A), possess high thermal conductivity and low dielectric loss, making them suitable as constituent materials for printed circuit boards (PCBs), and particularly suitable as insulating materials for PCBs. Furthermore, the low melting point of vinyl resin cured products simplifies the manufacturing process.

[0143] When the vinyl resin cured product (A) is a cured product of a vinyl compound (A), the vinyl resin cured product (A) can be a cured product of one vinyl compound (A) or a cured product of two or more vinyl compounds (A).

[0144] When the vinyl resin cured product (A) is a cured product of a vinyl composition (A), the vinyl resin cured product (A) can be a cured product of one vinyl composition (A) or a cured product of a mixture of two or more vinyl compositions (A).

[0145] Vinyl resin cured product (A) can be manufactured, for example, by: directly filling a vinyl compound (A) or vinyl composition (A) into a mold, heating for a specified time for initial curing, and further heating for a specified time while applying pressure with a press or the like for complete curing; a method of curing the vinyl compound (A) or vinyl composition (A) by directly heating it at a specified temperature; a method of directly or as needed melting a powder of the vinyl compound (A) or vinyl composition (A) and injecting it into a mold, while applying pressure with a press or the like for a specified time and heating for a specified time; or a method of heating and melting the vinyl compound (A) or vinyl composition (A) and injecting it into a mold. Methods for further heating the mold to form the product; methods for melting vinyl compound (A) or vinyl composition (A) and injecting the resulting melt into a preheated mold for solidification; methods for partially solidifying vinyl compound (A) or vinyl composition (A), pulverizing the partially solidified product, filling the resulting powder into a mold, and melting the filling powder to form the product; methods for dissolving vinyl compound (A) or vinyl composition (A) directly or as needed in a solvent, partially solidifying it while stirring as needed, casting the resulting solution, drying and removing the solvent by ventilation or drying, and heating for a specified time while pressing with a press or the like as needed.

[0146] The heating temperature (curing temperature) at which the vinyl compound (A) or vinyl composition (A) is heated to cure it is not particularly limited, but from the viewpoint of achieving a higher degree of curing of the vinyl compound (A) or vinyl composition (A), it is preferably 100°C or higher, more preferably 140°C or higher. From the viewpoint of avoiding overheating, the above heating temperature is preferably 200°C or lower.

[0147] The heating time (curing time) for curing the vinyl compound (A) or vinyl composition (A) is not particularly limited, but from the viewpoint of achieving a higher degree of curing of the vinyl compound (A) or vinyl composition (A), it is preferably 1 hour or more, more preferably 2 hours or more. From the viewpoint of avoiding unnecessary curing operations, the above heating time is preferably 10 hours or less.

[0148] The pressure applied when the vinyl compound (A) or vinyl composition (A) is pressed to cure it is not particularly limited, but from the viewpoint of achieving a higher degree of curing of the vinyl compound (A) or vinyl composition (A), it is preferably 0.7 MPa or more, more preferably 1.2 MPa or more. From the viewpoint of avoiding excessive pressure, the above-mentioned pressure is preferably 3 MPa or less.

[0149] The thermal diffusivity of the cured vinyl resin (A) is preferably 1.4 × 10⁻⁶. -7 m 2 / s or higher, more preferably 1.8×10 - 7 m 2 / s or higher, further preferably 1.95×10 -7 m 2 / s or higher. If the thermal diffusivity is within the above range, there is a tendency for high thermal conductivity. There is no particular upper limit to the thermal diffusivity of the vinyl resin cured product (A), and the above-mentioned thermal diffusivity can be 4.0 × 10⁻⁶. -7 m 2 For speeds below / s, it can also be 3.6 × 10. -7 m 2 Below / s, it can also be 3.2×10 -7 m 2 / s or less.

[0150] The thermal diffusivity of the vinyl resin cured product (A) can be, for example, 1.4 × 10⁻⁶. -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 Any of / s.

[0151] The thermal diffusivity of vinyl resin cured products (A) can be determined by the temperature wave thermal analysis (TWA) method, which is standardized in ISO 22007-3:2008 (for transfer-analytical films).

[0152] The dielectric loss tangent of the vinyl resin cured product (A) at a frequency of 100MHz 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; the dielectric loss tangent may be 0.001 or more, 0.002 or more, or 0.003 or more.

[0153] The dielectric loss tangent of the vinyl resin cured product (A) at a frequency of 100 MHz can be, for example, any one of 0.001–0.005, 0.002–0.0048, and 0.003–0.0046. However, these are just examples of the aforementioned dielectric loss tangent of the vinyl resin cured product (A).

[0154] The dielectric loss tangent of vinyl resin cured product (A) at a frequency of 100 MHz can be determined by capacitance method using an impedance analyzer under the following conditions.

[0155] • Determination method: Volumetric method

[0156] Electrode model: 16453A

[0157] • Measurement environment: 23℃, 50%RH

[0158] • Applied voltage: 1V

[0159] <Prepreg>

[0160] The prepreg of this 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 substrate.

[0161] In this specification, the prepreg used in this embodiment is sometimes referred to as "prepreg (A)". By using prepreg (A), laminates and the like can be easily manufactured using conventional methods. For example, multiple sheets of prepreg (A) are stacked to form a laminate, and the laminate is shaped by heating and pressing to make it integral, thereby obtaining the target laminate.

[0162] Printed circuit boards (resin layers in printed circuit boards) obtained using prepreg (A) or the above-mentioned laminates have high thermal conductivity and low dielectric loss due to the use of vinyl compounds (A).

[0163] The prepreg (A) can be manufactured by coating or impregnating a solution obtained by dissolving the vinyl compound (A) in a solvent onto a fibrous substrate, or by coating or impregnating the vinyl composition (A) or a diluent obtained by diluting the vinyl composition (A) with a solvent onto a fibrous substrate, and then heating the coated or impregnated fibrous substrate to semi-cure the vinyl compound (A) or the vinyl composition (A).

[0164] Regarding the heating temperature (semi-curing temperature) and heating time (semi-curing time) for semi-curing the vinyl compound (A) or vinyl composition (A), the above-mentioned curing conditions (heating temperature and heating time) of the vinyl compound (A) or vinyl composition (A) can be taken into account and appropriately set in a way that the vinyl compound (A) or vinyl composition (A) is not fully cured.

[0165] The aforementioned fibrous substrate is not particularly limited as long as it is a fibrous substrate, and can be any known substrate. More specifically, examples of fibrous substrates include woven and nonwoven fabrics made of inorganic fibers such as glass fibers, and woven and nonwoven fabrics made of organic fibers such as polyester.

[0166] <Resin-coated membrane>

[0167] The resin-bearing film 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 support film. More specifically, as a resin-bearing film of this embodiment, a resin-bearing film comprising the above-described resin layer and the above-described support film disposed on one or both sides of the above-described resin layer can be cited as an example. Using multiple resin-bearing films of this embodiment, the support film is removed, and they are overlapped to form a laminate. The laminate is then shaped by heating and pressing, and integrated to obtain a laminated sheet. The resin layer in the resin-bearing film of this embodiment, and the printed circuit board (resin layer in the printed circuit board) obtained using the above-described resin layer or laminated sheet, have high thermal conductivity and low dielectric loss due to the use of vinyl compound (A).

[0168] Examples of supporting films include polyethylene terephthalate (PET) films.

[0169] In a resin-coated membrane, where support films are provided on both sides of the resin layer, these support films may be identical or different from each other. In this specification, the invention is not limited to the resin-coated membrane; "two support films different from each other" means that at least one of the materials and thicknesses of the two support films is different.

[0170] The resin-coated film of this embodiment can be manufactured by coating the support film with a solution obtained by dissolving a vinyl compound (A) in a solvent, or by coating the support film with a vinyl composition (A) or a diluted product of a vinyl composition (A) diluted with a solvent, and then heating the coated layer to semi-cure the vinyl compound (A) or vinyl composition (A) in the coated material. The conditions for semi-cure of the vinyl compound (A) or vinyl composition (A) are the same as those for manufacturing the prepreg described above.

[0171] <Resin-coated metal foil>

[0172] The resin-coated 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, as the resin-coated metal foil of this embodiment, an example is a resin-coated metal foil comprising the aforementioned resin layer and the aforementioned metal foil disposed on one or both sides of the aforementioned resin layer. For example, using the resin-coated metal foil of this embodiment, the aforementioned semi-cured product is further cured to form a cured product, and the metal foil is patterned to form a circuit, thereby enabling the fabrication of a printed circuit board. Alternatively, using the resin-coated metal foil of this embodiment, the metal foil is patterned to form a circuit, and resin layers having such a circuit are stacked one on top of the other in a manner consistent with the circuit direction. While heating and applying pressure, the aforementioned semi-cured product is further cured, thereby enabling the fabrication of a multilayer printed circuit board having a resin layer comprising a cured product containing a vinyl compound (A) or a cured product containing a vinyl composition (A) as an insulating layer. The resin layer in the resin-coated metal foil of this embodiment, and the printed circuit board (resin layer in the printed circuit board) obtained by using the above-mentioned resin-coated metal foil, have high thermal conductivity and low dielectric loss by using vinyl compound (A).

[0173] Examples of such metal foils include copper foil.

[0174] In resin-coated metal foils, where metal foils are disposed on both sides of the resin layer, these metal foils may be identical or different from each other. In this specification, the invention is not limited to resin-coated metal foils; "two layers of metal foils are different" means that at least one of the materials and thicknesses of the two layers of metal foils is different from each other.

[0175] The resin-coated metal foil of this embodiment can be manufactured in the same way as the resin-coated film, except that the metal foil described above is used instead of the support film.

[0176] <Metal-clad laminate>

[0177] The metal-clad laminate of this embodiment comprises: an insulating layer containing a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and a metal foil. More specifically, as a metal-clad laminate of this embodiment, an example is a metal-clad laminate having the aforementioned insulating layer and the aforementioned metal foil disposed on one or both sides of the aforementioned insulating layer. The metal-clad laminate of this embodiment can be used to form conductor wiring (circuit) by patterning the metal foil therein, thereby producing a printed circuit board. Furthermore, multiple such printed circuit boards can be stacked with a separately prepared insulating layer in between, and heated and pressurized to produce a multilayer printed circuit board. The insulating layer in the metal-clad laminate of this embodiment, and the printed circuit board obtained using the aforementioned metal-clad laminate (the insulating layer in the printed circuit board), have high thermal conductivity and low dielectric loss due to the use of vinyl compound (A).

[0178] The metal foil in the metal-clad laminate of this embodiment is the same as the metal foil in the resin-coated metal foil.

[0179] In a metal-clad laminate, when metal foils are provided on both sides of the insulating layer, these metal foils may be the same or different from each other.

[0180] The insulating layer used separately during the lamination of the printed circuit board can be a known layer, or it can be the resin layer in the resin-containing film, or the laminate as a stack of multiple resin layers, or it can be the prepreg (A), or the laminate obtained by overlapping multiple prepregs (A). Alternatively, the insulating layer can also be a substance formed by further curing a vinyl compound (A) or a vinyl composition (A) in these resin layers, laminates, prepregs (A), or laminates.

[0181] The metal-clad laminate of this embodiment can be manufactured, for example, by laminating metal foil on one or both sides of a prepreg (A), heating and pressing the resulting laminate to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the prepreg (A), to form a cured product, thereby forming an insulating layer, and fusing the prepreg (A) with the metal foil.

[0182] The metal-clad laminate of this embodiment can be manufactured, for example, using a vinyl compound (A) or a vinyl composition (A), by producing a prepreg (A) using the previously described method, and then using the prepreg (A) to manufacture the laminate by the method described above.

[0183] The metal-clad laminate of this embodiment can also be manufactured by heating the resin-coated metal foil to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the resin layer, thereby forming an insulating layer containing a cured vinyl compound (A) or a cured vinyl composition (A).

[0184] Printed Circuit Boards

[0185] The printed circuit board of this embodiment includes: an insulating layer comprising a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and conductor wiring. More specifically, a printed circuit board having the aforementioned insulating layer and conductor wiring disposed on one or both sides of the insulating layer can be cited as an example of this embodiment. Multiple printed circuit boards of this embodiment can be stacked with a separately prepared insulating layer in between, and heated and pressurized to form a multilayer printed circuit board. The printed circuit board of this embodiment (the insulating layer in the printed circuit board) uses a vinyl compound (A), resulting in high thermal conductivity and low dielectric loss.

[0186] The material of the conductor wiring described above is the same as the metal of the metal foil in the metal-clad laminate described above. The insulating layer used separately during the lamination of the printed circuit board in this embodiment is the insulating layer described above.

[0187] In printed circuit boards, when conductor wiring is provided on both sides of the insulating layer, the material and thickness of these conductor wirings can be the same or different from each other.

[0188] The printed circuit board of this embodiment can be manufactured, for example, by patterning metal foil in the above-mentioned metal-clad laminate to form conductor wiring (circuit).

[0189] The printed circuit board of this embodiment can also be manufactured in the following manner: heating the above-mentioned resin-containing metal foil to further cure the vinyl compound (A) or its semi-cured product, or the vinyl composition (A) or its semi-cured product in the resin layer, thereby forming an insulating layer containing the cured product of the vinyl compound (A) or the cured product of the vinyl composition (A), and further, patterning the metal foil to form conductor wiring (circuit).

[0190] Metal foil can be patterned using known methods such as etching.

[0191] Figure 1This is a cross-sectional view schematically illustrating an example of a laminated structure of this embodiment obtained using vinyl compound (A). It should be noted that in the figures used in the following description, for ease of understanding of the features of the invention and for convenience, some parts that would otherwise be considered major components are shown enlarged, and the dimensional ratios of the constituent elements are not necessarily the same as in reality.

[0192] The laminated structure 1 shown here comprises a first layer 11 and a second layer 12 disposed 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 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 disposed over the entire area of ​​one surface 11a of the first layer 11 or over a portion thereof.

[0193] 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-containing film.

[0194] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 is a metal foil, the laminated structure 1 is a metal foil with resin.

[0195] When the first layer 11 is an insulating layer containing a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and the second layer 12 is a metal foil, the laminate structure 1 is a metal-clad laminate.

[0196] Figure 2 This is a cross-sectional view schematically illustrating another example of the laminated structure of this embodiment obtained using vinyl compound (A). It should be noted that... Figure 2 In subsequent drawings, components that are identical to those shown in the previously described drawings will be labeled with the same symbols as in the previously described drawings, and their detailed descriptions will be omitted.

[0197] The stacked structure 2 shown here comprises a first layer 11 and a second layer 22 disposed on a surface 11a of the first layer 11. The second layer 22 is linear. Figure 2 In this structure, the cross-section of the laminated structure 2 is formed to include a section along the linear length direction of the second layer 22. The number of linear second layers 22 can be one or more. The laminated structure 2, in addition to having linear second layers 22 instead of membrane-like second layers 12, is similar to... Figure 1 The layered structure shown is the same as 1.

[0198] The first layer 11 is an insulating layer containing a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and the second layer 22 is a laminated structure 2 for conductor wiring, which is a printed circuit board.

[0199] Figures 1-2 The stacked structures 1 and 2 shown are empty on the other side 11b of the first layer 11, but may have the same layers as the second layer 12 or the second layer 22.

[0200] Figure 3 This is a cross-sectional view schematically illustrating another example of the laminated structure of this embodiment obtained using vinyl compound (A).

[0201] The laminated structure 3 shown here comprises a first layer 11, a second layer 12 disposed on one surface 11a of the first layer 11, and a third layer 13 disposed on the other surface 11b of the first layer 11. The third layer 13 is in the form of a film or sheet, and is selected according to the type of 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 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 those of the second layer 12. For example, the third layer 13 may be disposed over the entire area of ​​the other surface 11b of the first layer 11, or it may be disposed over a portion of the area.

[0202] 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-containing film.

[0203] When the first layer 11 is a resin layer containing a vinyl compound (A) or a semi-cured product thereof or a vinyl composition (A) or a semi-cured product thereof, and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal foil with resin.

[0204] When the first layer 11 is an insulating layer containing a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and the second layer 12 and the third layer 13 are metal foils, the laminated structure 3 is a metal-clad laminate.

[0205] Figure 4 This is a cross-sectional view schematically illustrating another example of the laminated structure of this embodiment obtained using vinyl compound (A).

[0206] The stacked structure 4 shown here comprises a first layer 11, a second layer 22 disposed on one surface 11a of the first layer 11, and a third layer 23 disposed on the other surface 11b of the first layer 11. The third layer 23 is linear. Figure 4 In this structure, the cross-section of the stacked structure 4 is formed to include both a cross-section along the length of the second layer 22 and a cross-section along the length of the third layer 23. The arrangement of the third layer 23 on the other face 11b of the first layer 11 is the same as the arrangement of the second layer 22 on one face 11a of the first layer 11. The composition, length, thickness, and number of the third layer 23 can be the same as or different from those of the second layer 22. For example, the number of linear third layers 23 can be one or more.

[0207] The first layer 11 is an insulating layer containing a cured vinyl compound (A), a cured vinyl composition (A), or a cured prepreg (A), and the second layer 22 and the third layer 23 are the stacked structure 4 for conductor wiring, which is a printed circuit board.

[0208] Example

[0209] The present invention will be described in more detail below through embodiments, but the present invention is not limited to these embodiments.

[0210] The conditions for determining the melting point of vinyl compounds are shown.

[0211] Using a differential scanning calorimeter (METTLER TLEDO FP84HT), a glass disk filled with a vinyl compound was heated under the following conditions, and the temperature of the endothermic peak was taken as the melting point. In the case of multiple endothermic peaks, the temperature of the endothermic peak at the lower temperature side was taken as the melting point.

[0212] The test conditions for the cured product are shown.

[0213] (1) Thermal diffusivity

[0214] The thermal diffusivity was measured using the "ai-phase mobile" (manufactured by AI-Phase Co., Ltd.) device via the TWA method.

[0215] Example 1

[0216] 8.8 g of sodium hydride was added to a 300 mL four-necked flask equipped with a thermometer, condenser, and stirrer, and the flask was washed with hexane. Then, 90 mL of THF, 0.2 g of 2,6-di(tert-butyl)-p-cresol, 18.5 g of 6-chloro-1-hexanol, and 4-vinylbenzyl chloride were added, and the mixture was reacted at an internal temperature of approximately 60 °C for 3 hours.

[0217] After the reaction was complete, the mixture was cooled to room temperature, 8 mL of water was added, and the insoluble matter was removed by filtration. The resulting solution was washed with water, and the solution was removed under reduced pressure. The solution was then dried under reduced pressure to obtain 34.3 g of chlorine compound 1.

[0218] In a 300 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 5.0 g of 1,1'-(1,1'-biphenyl)-4,4'-dimethylbis(4-hydroxybenzoate), 0.05 g of 2,6-bis(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 chlorine compound 1 were added, and the mixture was reacted at an internal temperature of approximately 80 °C for 8 hours.

[0219] After the reaction was complete, the mixture was cooled to room temperature, and 33 mL of water was added. The precipitated solid was then filtered off. The resulting solid was mixed with acetone and stirred, and then filtered off. The solid was dissolved in THF to remove insoluble matter, and the solution was removed under reduced pressure to obtain 6.8 g of vinyl compound 1. Purity: 74.5% (LC area percentage).

[0220] Example 2

[0221] In a 200 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 4.8 g of sodium hydride, 0.1 g of 2,6-bis(tert-butyl)-p-cresol, 12.0 g of vinylbenzyl chloride (a mixture of meta and para isomers), and 90 mL of dehydrated N,N-dimethylformamide were added and the flask was cooled to approximately 0 °C. After adding 9.8 g of a solution of dehydrated N,N-dimethylformamide containing 3-chloro-1-propanol dropwise, the mixture was reacted at room temperature for 3 hours.

[0222] After the reaction was complete, the mixture was cooled to approximately 0°C, and the remaining sodium hydride was quenched with water. The solution was then removed under reduced pressure. The resulting liquid was dissolved in ethyl acetate, washed with water, and the solution was removed under reduced pressure. The solution was dried under reduced pressure to obtain 18.7 g of chlorine compound 2.

[0223] In a 200 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 3.4 g of 1,1'-(1,1'-biphenyl)-4,4'-dimethylbis(4-hydroxybenzoate), 0.03 g of 2,6-bis(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 chlorine compound 2 were added, and the mixture was reacted at an internal temperature of approximately 80 °C for 14 hours.

[0224] After the reaction was complete, the mixture was cooled to room temperature, and 100 mL of water was added. The mixture was stirred for 10 minutes. The precipitated solid was filtered off and washed with water, heptane, and methanol. The resulting solid was suspended in a small amount of THF, mixed with acetone, stirred, and then filtered off. The resulting solid was dried under reduced pressure to give 2.5 g of vinyl compound 2. Purity: 70.1% (LC area percentage).

[0225] Example 3

[0226] In a 200 mL four-necked flask equipped with a thermometer, condenser, and 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 a chlorine compound were added and reacted at an internal temperature of approximately 60–80 °C for 22 hours. After the reaction was complete, the mixture was cooled to room temperature. Toluene was then added, and the mixture was washed with water and the solution was removed under reduced pressure. Methanol was added to the resulting liquid and stirred, and the precipitated solid was filtered off. The resulting solid was dissolved in acetone and filtered to remove insoluble matter. A portion of the solution was removed under reduced pressure, methanol was added and stirred, and the precipitated solid was filtered off and washed with methanol. The resulting solid was dried under reduced pressure to give 3.7 g of vinyl compound 3. Purity: 72.4% (LC area percentage).

[0227] Example 4

[0228] In a 500 mL four-necked flask equipped with a thermometer, condenser, and stirrer, 19.0 g of (trans-4-(phenylene)cyclohexyl)bis(4-hydroxybenzoate), 42.0 g of potassium carbonate, 1.8 g of sodium iodide, 250 mL of N,N-dimethylformamide, and 26.5 g of 2-chloroethyl vinyl ether were added. The reaction was carried out at an internal temperature of approximately 60 °C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, 250 mL of water was added, and the precipitated solid was collected by filtration. The obtained solid was washed with 50 wt% methanol-water and isopropanol, and dried under reduced pressure to obtain 25.8 g of vinyl compound 4. Purity: 97.7% (LC area percentage). The melting point of vinyl compound 4, determined by the above method, was 128 °C.

[0229] Reference Example 1

[0230] 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 added 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. The mixture was then 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 off and dried under reduced pressure to obtain 9.4 g of vinyl compound 5. Purity: 99.1% (LC area percentage).

[0231] In Examples 5-7 and Comparative Example 1, the vinyl compounds prepared in Examples 1-4 and Reference Example 1 as shown in Table 1 were added to the plate-shaped hollow part of the mold. After heating for 1 hour at the first curing temperature shown in Table 1 under reduced pressure, the product was heated at 180°C for 2 hours while applying a pressure of 1.5 MPa, thereby obtaining the cured product.

[0232] The melting point of the vinyl compound and the thermal diffusivity of the cured product are shown in Table 1.

[0233] [Table 1]

[0234]

[0235] Industrial availability

[0236] This invention can be used in printed circuit boards in communication equipment, and is particularly suitable for printed circuit boards designed for situations where communication equipment processes large amounts of data and generates a lot of heat.

[0237] Explanation of reference numerals in the attached figures

[0238] Layered structure 1, 2, 3, 4

[0239] 11. Level 1

[0240] 11a A face of the first layer

[0241] 11b The other side of the first layer

[0242] 12, 22, 2nd floor

[0243] 13, 23, 3rd floor

Claims

1. A vinyl compound represented by formula (A), In the formula (A), Y 1 and Y 2 are the same or different and are any group selected from vinyl and vinylbenzyl, Q is any group selected from formula (1) to (3), In the above formulas (1) to (3), A 1 , A 2 , A 3 and A 4 are the same or different and are selected from substituted or unsubstituted divalent aromatic groups excluding nitrogen-containing aromatic heterocyclic groups, a substituted or unsubstituted divalent cycloalkylene group, A divalent group formed by connecting two or more substituted or unsubstituted divalent aromatic groups excluding a nitrogen-containing aromatic heterocyclic group via a single bond, A divalent group formed by connecting two or more substituted or unsubstituted divalent cycloalkylene groups or cycloalkenylene groups via a single bond, and Any of divalent groups formed by connecting 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 via a single bond, X 1 , X 2 and X 3 are the same or different, and are any one selected from a single bond, an ester group and a carbonyl group, In Y 1 and Y 2 When at least one of X is vinyl, X constituting Q 1 , X 2 and X 3 At least one of 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 the same as or different from each other and represent an integer of 1 to 20.

2. The vinyl compound according to claim 1, wherein The X 1 , X 2 and X 3 At least one of the groups is an ester group.

3. The vinyl compound according to claim 1, wherein The A 1 , A 2 , A 3 and A 4 It is a divalent aromatic group, but does not include a nitrogen-containing aromatic heterocyclic group.

4. The vinyl compound according to any one of claims 1 to 3, which is used for a printed wiring board. A vinyl composition comprising the vinyl compound according to claim 1. 6 . A cured vinyl resin obtained by curing the vinyl compound according to claim 1 or the vinyl composition according to claim 5 . 7 . A prepreg comprising the vinyl compound or semi-cured product thereof according to claim 1 , or the vinyl composition or semi-cured product thereof according to claim 5 , and a fibrous base material. 8 . A film with a resin, comprising a resin layer and a support film, wherein the resin layer comprises the vinyl compound or a semi-cured product thereof according to claim 1 , or the vinyl composition or a semi-cured product thereof according to claim 5 . 9 . A metal foil with resin, comprising a resin layer and a metal foil, wherein the resin layer comprises the vinyl compound or a semi-cured product thereof according to claim 1 , or the vinyl composition or a semi-cured product thereof according to claim 5 . 10 . A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the vinyl compound according to claim 1 or a cured product of the vinyl composition according to claim 5 . 11 . A metal-clad laminate comprising an insulating layer and a metal foil, wherein the insulating layer comprises a cured product of the prepreg according to claim 7 . 12 . A printed wiring board comprising an insulating layer and a conductor wiring, wherein the insulating layer comprises a cured product of the vinyl compound according to claim 1 or a cured product of the vinyl composition according to claim 5 . 13 . A printed wiring board comprising an insulating layer and conductive wiring, wherein the insulating layer comprises a cured product of the prepreg according to claim 7 .

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