Resin composition containing substituted polyphenylene sulfide resin

Abstract

Provided is a resin composition having a low dielectric loss tangent and a low thermal expansion coefficient. This resin composition comprises: a substituted polyphenylene sulfide resin (A) containing a structural unit represented by general formula (I) [wherein R1, R2, R3, and R4 each independently represent H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and at least one of R1, R2, R3, and R4 represents an alkyl group or an alkoxy group]; and a filler (B).

Description

Resin composition containing substituted polyphenylene sulfide resin

[0001] The present disclosure relates to a resin composition comprising a substituted polyphenylene sulfide resin.

[0002] In recent years, mobile communication systems have become faster and larger in capacity. With these advances in mobile communication systems, higher frequency bands have begun to be used for communication. For example, fifth-generation mobile communication systems, which have already begun practical use, use higher frequency bands than fourth-generation and earlier mobile communication systems. Mobile communication system terminals experience attenuation of electrical signals passing through printed wiring board circuits, known as transmission loss. Transmission loss also depends on the dielectric properties of the printed wiring board substrate (dielectric). Generally, the higher the frequency used, the greater the influence of the dielectric loss tangent, resulting in greater transmission loss. To enable faster mobile communication, suppression of transmission loss in printed wiring boards used for communication in high-frequency bands is required. Therefore, low transmission loss is also required for resins and resin compositions used as materials for printed wiring boards. To achieve low transmission loss, resins and resin compositions with low dielectric loss tangent are required.

[0003] Conventionally, resin compositions containing polyphenylene ether (PPE) resin (for example, Patent Document 1) or unsubstituted polyphenylene sulfide (PPS) resin as a main component have been used as materials for wiring substrates such as printed wiring boards.

[0004] Japanese Patent Application Laid-Open No. 2023-1134

[0005] However, wiring board materials using PPE resins or unsubstituted PPS resins tend to have high dielectric loss tangents, which may result in high transmission loss in high-frequency communication applications. Furthermore, since PPE resins themselves have low flame retardancy, they must be mixed with a flame-retardant material to impart flame retardancy to the resin composition in order to be used as wiring board materials.

[0006] The present inventors discovered that substituted polyphenylene sulfide (substituted PPS) resins can achieve a lower dielectric loss tangent than PPE resins or unsubstituted PPS resins. However, during the lamination process for use in wiring boards, the substituted PPS resins have a higher thermal expansion coefficient than other lamination materials, which makes them prone to warping in the laminate.

[0007] An object of the present disclosure is to provide a resin composition having a low dielectric loss tangent and a low thermal expansion coefficient.

[0008] The present disclosure includes the following aspects: [1] First aspect [1-1] General formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and R １ , R ２ , R ３ , and R ４ wherein one or more of the following is an alkyl group or an alkoxy group: and a filler (B). [2] Second Aspect [2-1] An article for a wiring board, comprising the resin composition according to [1-1]. [3] Third Aspect [3-1] A wiring board, comprising the resin composition according to [1-1]. [4] Fourth Aspect [4-1] A printed wiring board, comprising the resin composition according to [1-1].

[0009] According to the present disclosure, it is possible to provide a resin composition having a low dielectric loss tangent and a low thermal expansion coefficient.

[0010] An embodiment of the present disclosure will be described in detail below. However, each configuration and combination thereof in each embodiment is merely an example, and additions, omissions, substitutions, and other modifications of configurations are possible as appropriate within the scope of the gist of the present disclosure. Each aspect disclosed in this specification can be combined with any other feature disclosed in this specification. When multiple upper and lower limits are described for a particular parameter, any of these upper and lower limits can be combined to form a suitable numerical range. The lower and / or upper limits of a numerical range described in this disclosure are numerical values ​​within that range and may be replaced with numerical values ​​shown in the examples. The expression "X to Y" indicating a numerical range means "X or more and Y or less." If a specific description described for one embodiment also applies to other embodiments, that description may be omitted in other embodiments.

[0011] [First embodiment: Resin composition] The resin composition according to this embodiment (hereinafter also simply referred to as "resin composition") is a resin composition represented by the general formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and R １ , R ２ , R ３ , and R ４ wherein one or more of the following is an alkyl group or an alkoxy group; a filler (B); and

[0012] By including the substituted PPS resin (A) and the filler (B), a resin composition can be obtained that has a low dielectric loss tangent and a low thermal expansion coefficient. The term "low thermal expansion coefficient" means a thermal expansion coefficient that is lower than the thermal expansion coefficient when the substituted PPS resin (A) is cured alone. In one embodiment, the term "low thermal expansion coefficient" means a thermal expansion coefficient that is as low as that of other laminating materials in a wiring board. When used as a material for a wiring board, a resin composition with a low thermal expansion coefficient has a thermal expansion coefficient that is as low as that of other laminating materials such as metal foil, making it less likely for warping to occur in a laminate produced through a lamination process. It has not been previously known that the filler (B) has the effect of lowering the thermal expansion coefficient while maintaining the low dielectric loss tangent properties of the substituted PPS resin (A).

[0013] (Substituted Polyphenylene Sulfide Resin (A)) The substituted PPS resin (A) is a polyphenylene sulfide resin represented by the general formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably H, an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), and R １ , R ２ , R ３ , and R ４ The structural unit represented by general formula (I) may contain one type of structural unit, or may contain two or more types of structural units that differ in the type or number of substituents.

[0014] The alkyl group may be a linear, branched, or cyclic alkyl group, and is preferably a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms. Examples of linear, branched, or cyclic alkyl groups having 1 to 10 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an s-isobutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, an n-heptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decyl group, an isodecyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. The alkyl group may be one type, or two or more types may be contained. In one embodiment, the alkyl group is preferably a methyl group, an ethyl group, and / or an isopropyl group.

[0015] The alkoxy group may be a linear, branched, or cyclic alkoxy group, and is preferably a linear, branched, or cyclic alkoxy group having 1 to 10 carbon atoms. Examples of the linear or branched alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a tert-butoxy group, an s-butoxy group, an isobutoxy group, an n-pentyloxy group, an isopentyloxy group, a neopentyloxy group, an n-hexyloxy group, an isohexyloxy group, an s-hexyloxy group, a tert-hexyloxy group, a neohexyloxy group, an n-heptyloxy group, an n-octyloxy group, an isooctyloxy group, an n-nonyloxy group, an isononyloxy group, an n-decyloxy group, an isodecyloxy group, a cyclopropoxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a cyclononyloxy group, and a cyclodecyloxy group. One type of alkoxy group may be used, or two or more types may be contained. In one embodiment, the alkoxy group is preferably a methoxy group.

[0016] In one embodiment, in consideration of ease of synthesis of the substituted PPS resin (A), the alkyl group is preferably linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 5, and even more preferably 1 to 4. In one embodiment, the alkyl group may be an alkyl group having 4 carbon atoms, an alkyl group having 3 carbon atoms, an alkyl group having 2 carbon atoms, or an alkyl group having 1 carbon atom.

[0017] In one embodiment, in consideration of ease of synthesis of the substituted PPS resin (A), the alkoxy group is preferably linear or branched. The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 5, and even more preferably 1 to 4. In one embodiment, the alkoxy group may be an alkoxy group having 4 carbon atoms, an alkoxy group having 3 carbon atoms, an alkoxy group having 2 carbon atoms, or an alkoxy group having 1 carbon atom.

[0018] In consideration of the ease of synthesis of the substituted PPS resin (A), the alkyl group or alkoxy group is preferably an alkyl group, more preferably a linear alkyl group, even more preferably a linear alkyl group having 1 to 4 carbon atoms, still more preferably an ethyl group or a methyl group, and even more preferably a methyl group.

[0019] The substitution position of the alkyl group or alkoxy group in general formula (I) is not limited, and R １ , R ２ , R ３ , and R ４ It is sufficient that there is one or more of these, and it may be two or more, three or more, or even four.

[0020] When one alkyl group or alkoxy group is contained in general formula (I), the substitution position thereof is R １ , R ２ , R ３ , and R ４ The substitution position may be any one of R １ Even if R ２Even if R ３ Even if or R ４ When general formula (I) contains two or more alkyl groups and / or alkoxy groups in total, the combination of their substitution positions is not limited. For example, when two alkyl groups and / or alkoxy groups are contained, the substitution positions may be R １ and R ２ , R １ and R ３ , R １ and R ４ , R ２ and R ３ , R ２ and R ４ , R ３ and R ４ In one embodiment, the substitution positions of the alkyl and / or alkoxy groups may be any combination of R １ , R ３ , and R ４ The substitution positions may be any two of R １ , R ３ , and R ４ If any two of １ and R ３ , or R １ and R ４ When general formula (I) contains a total of three alkyl groups and / or alkoxy groups, R １ and R ２ and R ３ , R １ and R ２ and R ４ , R １ and R ３ and R ４ , or R ２ and R ３ and R ４ Any combination of the above may be used.

[0021] In one embodiment, the substituted PPS resin (A) contains a structural unit represented by general formula (I) in which R １ , R ２ , R ３ , and R ４One or more of the above may be an aryl group having 1 to 10 carbon atoms. Examples of the aryl group having 1 to 10 carbon atoms include a phenyl group and a naphthyl group.

[0022] When the general formula (I) contains one or more alkyl groups, alkoxy groups, and / or aryl groups, the dielectric loss tangent of the resin composition containing the substituted PPS resin (A) tends to be low.

[0023] In the constitutional unit represented by general formula (I), R １ , R ２ , R ３ , and R ４ At least one of R is an alkyl group or an alkoxy group. １ , R ２ , R ３ , and R ４ The case where one or more of the above groups that are not alkyl or alkoxy groups are aryl and / or alkenyl group-containing organic groups is also included.

[0024] In the substituted PPS resin (A), in formula (I), R １ , R ２ , R ３ , and R ４Those that are not alkyl or alkoxy groups may each independently be alkenyl group-containing organic groups. When the structural unit represented by formula (I) has an alkenyl group-containing organic group, the structural unit represented by formula (I) may also simultaneously satisfy formula (II). Here, the alkenyl group-containing organic group is not limited to a range containing one or more alkenyl groups within the substituent, and may be an alkenylene group interposed by a COO group (ester) or a CO group (ketone). The alkenyl group-containing organic group may be a linear, branched, or cyclic alkenyl group, and is preferably a linear, branched, or cyclic alkenyl group having 2 to 10 carbon atoms. Examples of linear, branched, or cyclic alkenyl groups having 2 to 10 carbon atoms include substituents containing one or more carbon-carbon double bonds in the chain of an alkyl group having 2 or more carbon atoms, and specific examples include vinyl groups, allyl groups, 1-propenyl groups, isopropenyl groups, 3-butenyl groups, 2-butenyl groups, 1-butenyl groups, 1,3-butadienyl groups, 4-pentenyl groups, 3-pentenyl groups, 2-pentenyl groups, 1-pentenyl groups, 1,3-pentadienyl groups, 2,4-pentadienyl groups, 1,1-dimethyl-2-propenyl groups, 1-ethyl-2-propenyl groups, 1,2-dimethyl-1-propenyl groups, 1-methyl-1-butenyl groups, and the like. Examples of the alkenyl group include thenyl, 5-hexenyl, 4-hexenyl, 2-hexenyl, 1-hexenyl, 1-methyl-1-hexenyl, 2-methyl-2-hexenyl, 3-methyl-1,3-hexadienyl, 1-heptenyl, 2-octenyl, 3-nonenyl, 4-decenyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, cyclodecenyl, acrylic (acryloyl), methacrylic (methacryloyl), acryloyloxyalkyl, and methacryloyloxyalkyl groups. The alkenyl group may be one type, or two or more types may be included. In one embodiment, the alkenyl group-containing organic group is preferably a vinyl group, an allyl group, and / or an acrylic group.

[0025] In one embodiment, in consideration of ease of synthesis of the substituted PPS resin (A), the alkenyl group-containing organic group is preferably linear or branched. The number of carbon atoms in the alkenyl group-containing organic group is preferably 2 to 6, more preferably 2 to 5, even more preferably 2 to 4, and still more preferably 2 to 3. In one embodiment, the alkenyl group-containing organic group may be an alkenyl group or acrylic group having 3 carbon atoms, or an alkenyl group having 2 carbon atoms.

[0026] In one embodiment, in the constitutional unit represented by general formula (I), R １ , R ２ , R ３ , and R ４ In the case where one or more of the structural units represented by general formula (I) are alkenyl group-containing organic groups, a resin composition containing the substituted PPS resin (A) is likely to exhibit thermosetting properties, even if the substituted PPS resin (A) is composed only of the structural unit represented by general formula (I) or contains one or more structural units other than the structural unit represented by general formula (I).

[0027] Furthermore, unsubstituted PPS resins have good flame retardancy. Therefore, a substituted PPS resin (A) containing a structural unit represented by general formula (I), which has the same basic skeleton as unsubstituted PPS, has good flame retardancy. This also applies to other structural units having a PPS skeleton which has the same basic skeleton as unsubstituted PPS. As described below, a substituted PPS resin (A) containing a structural unit represented by general formula (II) and a substituted PPS resin (A) containing a terminal structure represented by general formula (III) also have good flame retardancy. As a result, a resin composition containing the substituted PPS resin (A) has good flame retardancy.

[0028] In one embodiment, the substituted PPS resin (A) has the general formula (II): [In formula (II), R ５ａ , R ６ａ , R ７ａ and R ８ａare each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), and R ５ａ , R ６ａ , R ７ａ and R ８ａ wherein one or more of the structural units is an alkenyl group-containing organic group. By including the structural unit represented by general formula (II), a resin composition containing the substituted PPS resin (A) is likely to exhibit thermosetting properties. In addition, it is likely to exhibit good reflow resistance. The structural unit represented by general formula (II) may be of one type, or may include two or more types having different types or numbers of substituents.

[0029] The structural unit represented by general formula (II) represents a structural unit, among the structural units contained in the substituted PPS resin (A), other than the structural units located at the terminals of the resin, in which one or more of the substituents is an alkenyl group-containing organic group.

[0030] In the general formula (II), examples of the alkyl group, alkoxy group, aryl group, and alkenyl group-containing organic group and the number of carbon atoms are the same as those described for the general formula (I).

[0031] In consideration of the ease of synthesis of the substituted PPS resin, the number of carbon atoms in the alkenyl group-containing organic group in general formula (II) is preferably 2 to 6, more preferably 2 to 5, even more preferably 2 to 4, and even more preferably 2 to 3. In one embodiment, the alkenyl group-containing organic group may be an alkenyl group-containing organic group having 3 carbon atoms, or an alkenyl group-containing organic group having 2 carbon atoms, for example, an allyl group or an acryl group having 3 carbon atoms, and / or a vinyl group having 2 carbon atoms.

[0032] Here, the substitution position of the alkenyl group-containing organic group in general formula (II) is not limited, and R ５ａ , R ６ａ , R ７ａ and R ８ａIt is sufficient that there be one or more of these, or two or more, or three or more, or even four.

[0033] When one alkenyl-containing organic group is contained in general formula (II), the substitution position thereof is R ５ａ , R ６ａ , R ７ａ and R ８ａ The substitution position may be any one of R ５ａ Even if R ６ａ Even if R ７ａ Even if, or R ８ａ When general formula (II) contains two or more alkenyl group-containing organic groups, the combination of their substitution positions is not limited. For example, when two alkenyl group-containing organic groups are contained, the substitution positions may be R ５ａ and R ６ａ , R ５ａ and R ７ａ , R ５ａ and R ８ａ , R ６ａ and R ７ａ , R ６ａ and R ８ａ , R ７ａ and R ８ａ In one embodiment, the substitution position of the alkenyl group-containing organic group may be any combination of R ５ａ , R ６ａ , and R ７ａ and R ５ａ and R ７ａ , or R ６ａ and R ７ａ For example, when general formula (II) contains three alkenyl group-containing organic groups, the substitution positions are R ５ａ and R ６ａ and R ７ａ , R ５ａ and R ６ａ and R ８ａ , R ５ａ and R ７ａ and R ８ａ , or R ６ａ and R ７ａ and R ８ Any combination of the above may be used.

[0034] In general formula (II), R ５ａ , R ６ａ , R ７ａ and R ８ａ At least one of them is an alkenyl-containing organic group, but R ５ａ , R ６ａ , R ７ａ and R ８ａ The case where one or more of the non-alkenyl group-containing organic groups are alkyl or alkoxy groups is also included. The substitution position of the alkyl or alkoxy group in general formula (II) is ５ａ , R ６ａ , R ７ａ and R ８ａ Examples and preferred examples thereof include the substitution positions exemplified in the explanation of general formula (I). When the structural unit represented by formula (II) has an alkyl group or an alkoxy group, the structural unit represented by formula (II) can also satisfy formula (I).

[0035] In one embodiment, the substituted PPS resin (A) has the general formula (III-a): [In formula (III-a), each X is independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), at least one of which is an alkenyl group-containing organic group, and n is an integer of 1 to 5]. By including a terminal structure represented by general formula (III-a), the resin composition is likely to exhibit thermosetting properties. When the substituted PPS resin (A) includes a terminal structure represented by general formula (III-a), the substituted PPS resin (A) may include the terminal structure represented by general formula (III-a) at at least one of its terminals, or may include the terminal structure represented by general formula (III-a) at both its terminals. Even when the substituted PPS resin (A) does not have the terminal structure represented by general formula (III-a) at any of its terminals, as long as it is a resin containing one or more alkenyl group-containing organic groups in general formula (II), the resin composition is likely to exhibit the desired thermosetting properties as a material for wiring boards by using it in combination with an additive known to those skilled in the art for improving its curability, such as a crosslinking agent.

[0036] In one embodiment, the terminal structure represented by general formula (III-a) is represented by general formula (III-b): In formula (III-b), each X is independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), at least one of which is an alkenyl group-containing organic group, n is an integer of 1 to 5, and A is a compound represented by general formula (IV): {In formula (IV), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably an alkyl group, an alkoxy group, or an alkenyl group-containing organic group)}. １ , R ２ , R ３ , and R ４ One or more of may be an alkyl group or an alkoxy group.

[0037] In one embodiment, the terminal structure represented by general formula (III-a) is represented by general formula (III): In formula (III), X's are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), at least one of which is an alkenyl group-containing organic group, and n is an integer of 1 to 5.

[0038] The structural units represented by general formulas (III-a), (III-b), and (III) represent structural units contained in the substituted PPS resin (A) that are located at one or both of the terminals of the resin, in which one or more of the substituents is an alkenyl group-containing organic group. Examples of the alkyl group, alkoxy group, aryl group, and alkenyl group-containing organic group in general formulas (III-a), (III-b), and (III), and the number of carbon atoms thereof, are the same as those described for general formula (I).

[0039] In consideration of the ease of synthesis of the substituted PPS resin, the number of carbon atoms of the alkenyl group-containing organic group in general formulae (III-a), (III-b), and (III) is preferably 2 to 6, more preferably 2 to 5, even more preferably 2 to 4, and still more preferably 2 to 3. In one embodiment, the alkenyl group-containing organic group may be an alkenyl group-containing organic group having 3 carbon atoms, or an alkenyl group-containing organic group having 2 carbon atoms, for example, an allyl group or an acryl group having 3 carbon atoms, and / or a vinyl group having 2 carbon atoms.

[0040] In the general formulae (III-a), (III-b), and (III), one or more of X is an alkenyl group, but the case where one or more of the X that is not an alkenyl group-containing organic group is an alkyl group, an alkoxy group, or an aryl group is also included. The substitution position of the alkyl group, alkoxy group, or aryl group in the general formulae (III-a), (III-b), and (III) is not limited, and may be any of the five Xs.

[0041] The substitution position of the alkenyl group-containing organic group in general formula (III-a), (III-b), or (III) is not limited, and may be one or more of the five X. When general formula (III-a), (III-b), or (III) contains one alkenyl group-containing organic group, the substitution position may be the ortho position, meta position, or para position relative to S.

[0042] When general formula (III-a), (III-b), or (III) contains two or more alkenyl group-containing organic groups in total, the combination of their substitution positions is not limited. For example, when two alkenyl group-containing organic groups are contained, the substitution positions may be the 2,3-positions (or 5,6-positions), the 2,4-positions (or 4,6-positions), the 2,5-positions (or 3,6-positions), the 2,6-positions, the 3,4-positions (or 4,5-positions), or the 3,5-positions. For example, when three alkenyl group-containing organic groups are contained in general formula (III-a), (III-b), or (III), the substitution positions may be the 2,3,4-positions (or 4,5,6-positions), the 2,3,5-positions (or 3,5,6-positions), the 2,3,6-positions (or 2,5,6-positions), the 2,4,5-positions (or 3,4,6-positions), the 2,4,6-positions, or the 3,4,5-positions.

[0043] In one embodiment, the substituted PPS resin (A) has a polymer structure including two or more structural units (monomer units) capable of constituting a resin. The substituted PPS resin (A) includes a structural unit represented by general formula (I) as at least a portion of its structural units, and may also include one or more structural units represented by formulas other than general formula (I).

[0044] In the substituted PPS resin (A), the bonding order of the structural units is not limited, and for example, structural units represented by general formula (I) may be adjacent to each other but have the same combination of substituents, structural units represented by general formula (II) may be adjacent to each other but have different combinations of substituents, structural units represented by general formula (I) may be adjacent to each other but have different combinations of substituents, structural units represented by general formula (II) may be adjacent to each other but have different combinations of substituents, structural units represented by general formula (I) may be adjacent to a structural unit represented by general formula (II), a structural unit represented by general formula (I) may be adjacent to a structural unit represented by general formula (II), or a structural unit represented by general formula (I) or general formula (II) may be adjacent to a structural unit other than the structural unit represented by general formula (I) or (II). Furthermore, a terminal structure represented by general formula (III-a), (III-b), or (III) may be bonded to both or one of the ends of a plurality of structural units bonded in any of these orders.

[0045] In one embodiment, the substituted PPS resin can be, for example and without limitation, a substituted PPS resin represented by the general formula (I): １ and R ４ is an alkyl group having 1 to 5 carbon atoms, and R ２ and R ３ may contain a structural unit in which R ２ and R ３ is an alkyl group having 1 to 5 carbon atoms, and R １ and R ４ (3) In the general formula (I), R １ and R ３ is an alkyl group having 1 to 5 carbon atoms, and R ２ and R ４ (4) In the general formula (I), R ２ is an alkyl group having 1 to 5 carbon atoms, and R １ , R ３ , and R ４ (5) In the general formula (I), R １ is an alkyl group having 1 to 5 carbon atoms, and R ２ , R ３ , and R ４(6) In the general formula (I), R ２ and R ３ is an alkoxy group having 1 to 5 carbon atoms, and R １ and R ４ (7) In the general formula (I), R １ and R ４ is a methyl group, and R ２ and R ３ (8) In the general formula (I), R ２ and R ３ is a methyl group and R １ and R ４ (9) In the general formula (I), R １ and R ３ is a methyl group, and R ２ and R ４ (10) In the general formula (I), R ２ is a methyl group and R １ , R ３ , and R ４ (11) In the general formula (I), R １ is an isopropyl group and R ２ , R ３ , and R ４ (12) In the general formula (I), R ２ and R ３ is a methoxy group and R １ and R ４ In one embodiment, the substituted PPS resin may include a structural unit in which R is H. In one embodiment, the substituted PPS resin may include, but is not limited to, a structural unit in which R is H. １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is an alkyl group having 1 to 5 carbon atoms, and R １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is an alkenyl-containing organic group having 2 to 3 carbon atoms, and R２ and R ３ (In general formula (II), R ６ａ and R ７ａ (14) In general formula (I) or general formula (II), R ２ or R ３ (In general formula (II), R ６ａ or R ７ａ ) is an alkyl group having 1 to 5 carbon atoms, and R ２ or R ３ (In general formula (II), R ６ａ or R ７ａ ) is an alkenyl-containing organic group having 2 to 3 carbon atoms, and R １ and R ４ (In general formula (II), R ５ａ and R ８ａ(15) It may contain a structural unit in which in the general formula (III-a), (III-b), or (III), the 2-position and the 6-position are alkyl groups having 1 to 5 carbon atoms, and the X that is not an alkyl group is each H or an alkenyl-containing organic group having 2 to 3 carbon atoms; (16) It may contain a structural unit in the general formula (III-a), (III-b), or (III), the 2-position or the 6-position is an alkyl group having 1 to 5 carbon atoms, and the 2-position or the 6-position that is not an alkyl group is each H or an alkenyl-containing organic group having 2 to 3 carbon atoms; (17) It may contain a structural unit in the general formula (III-a), (III-b), or (III), the 2-position and the 6-position are methyl groups, and the X that is not a methyl group is each H or an alkenyl-containing organic group having 2 to 3 carbon atoms; (18) In the general formula (III-a), (III-b), or (III), the 3-position or 5-position may be an alkyl group having 1 to 5 carbon atoms, and the 3-position or 5-position that is not an alkyl group may be H or an alkenyl-containing organic group having 2 to 3 carbon atoms; (19) In the general formula (III-a), (III-b), or (III), the 3-position or 5-position may be a methyl group, and the 3-position or 5-position that is not a methyl group may be H or an alkenyl-containing organic group having 2 to 3 carbon atoms; (20) In the general formula (III-a), (III-b), or (III), at least one of the 2-position, 3-position, 4-position, 5-position, and 6-position is an alkenyl-containing organic group having 2 to 3 carbon atoms, and each X that is not an alkenyl-containing organic group is H or an alkyl group having 1 to 5 carbon atoms; and in the general formula (I), R ２ and R ３ is an alkyl group having 1 to 5 carbon atoms, and R １ and R ４ (21) A structural unit in which, in general formula (III-a), (III-b), or (III), at least one of the 2-, 3-, 4-, 5-, and 6-positions is an alkenyl group-containing organic group having 2 to 3 carbon atoms, and each X that is not an alkenyl group-containing organic group is H or an alkyl group having 1 to 5 carbon atoms, and in general formula (I), R １ and R ４is an alkyl group having 1 to 5 carbon atoms, and R ２ and R ３ (22) In general formula (I) or general formula (II), R １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is a methyl group, and R １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is a vinyl group, and R ２ and R ３ (In general formula (II), R ６ａ and R ７ａ (23) In the general formula (I) or the general formula (II), R ２ or R ３ (In general formula (II), R ６ａ or R ７ａ ) is a methyl group, and R ２ or R ３ (In general formula (II), R ６ａ or R ７ａ ) is a vinyl group, and R １ and R ４ (In general formula (II), R ５ａ and R ８ａ (24) A structural unit in which at least one of the 2-, 3-, 4-, and 5-positions in general formula (III-a), (III-b), or (III) is a vinyl group, and each of the Xs that are not vinyl groups is H or a methyl group, and in general formula (I), R ２ or R ３ is a methyl group and R １ and R ４ may contain a constitutional unit in which

[0046] In one embodiment, the substituted PPS resin may be, for example, a non-limiting example: (25) a structural unit in which, in general formula (III-a), (III-b), or (III), at least one of the 2-position and the 6-position is an alkenyl group-containing organic group having 2 to 3 carbon atoms, and each X that is not an alkenyl group-containing organic group is H or an alkyl group having 1 to 5 carbon atoms; and in general formula (I), R １ and R ４ is an alkyl group having 1 to 5 carbon atoms, and R ２ and R ３ (26) A structural unit in which at least one of the 2-position and the 6-position in the general formula (III-a), (III-b), or (III) is a vinyl group, and each of the Xs that are not vinyl groups is H or a methyl group, and a structural unit in which R １ or R ４ is a methyl group and R ２ and R ３ In one embodiment, the substituted PPS resin may include, but is not limited to, a structural unit in which, in general formula (III-a), (III-b), or (III), at least one of the 3-position and 5-position is an alkenyl group-containing organic group having 2 to 3 carbon atoms, and each X that is not an alkenyl group-containing organic group is H or an alkyl group having 1 to 5 carbon atoms; and in general formula (I), R ２ and R ３ is an alkyl group having 1 to 5 carbon atoms, and R １ and R ４ (28) A structural unit in which at least one of the 3-position and the 5-position in the general formula (III-a), (III-b), or (III) is a vinyl group, and each of the Xs that are not vinyl groups is H or a methyl group, and a structural unit in which R ２ or R ３ is a methyl group and R １ and R ４ may contain a constitutional unit in which

[0047] In one embodiment, the substituted PPS resin may have an alkenyl group-containing organic group at any substitution position in general formula (I), general formula (II), and / or general formula (III-a), (III-b), or (III), and the alkenyl group-containing organic group may have 2 to 3 carbon atoms or may be a vinyl group.

[0048] In one embodiment, the substituted PPS resin may be one or more selected from 2,6-dimethyl PPS resin, 3,5-dimethyl PPS resin, 2,5-dimethyl PPS resin, 3-monomethyl PPS resin, and 2-isopropyl PPS resin, which may have one or more alkenyl group-containing organic groups having 2 to 3 carbon atoms (preferably one or more alkenyl group-containing organic groups having 2 to 3 carbon atoms). In one embodiment, the substituted PPS resin may be one or more selected from 2,6-dimethyl PPS resin, 3,5-dimethyl PPS resin, 2,5-dimethyl PPS resin, 3-monomethyl PPS resin, and 2-isopropyl PPS resin, which may have one or more vinyl groups.

[0049] In one embodiment, the content of structural units containing alkyl groups and / or alkoxy groups in the substituted PPS resin (A) is preferably 30 mol% or more. When it is 30 mol% or more, it may be 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, 80 mol% or more, 90 mol% or more, or 100 mol%. The content of structural units containing alkyl groups and / or alkoxy groups in the substituted PPS resin (A) can be calculated from the amount of monomer charged. Also, １ When the content of structural units containing an alkyl group and / or an alkoxy group in the substituted PPS resin is 30 mol % or more, the dielectric loss tangent of the resin composition containing the substituted PPS resin (A) tends to be low.

[0050] In one embodiment, the content of the structural unit having an alkenyl group-containing organic group in the substituted PPS resin (A) is preferably one structural unit or more (e.g., two structural units or more) and 20 mol% or less, more preferably 0.1 to 20 mol% (e.g., 1 to 20 mol%), even more preferably 0.2 to 18 mol% (e.g., 1 to 18 mol%), even more preferably 0.5 to 15 mol% (e.g., 2 to 10 mol%), and particularly preferably 0.8 to 10 mol% (e.g., 2 to 7 mol%). In one embodiment, only one structural unit may have an alkenyl group-containing organic group. Even if only one structural unit of the substituted PPS resin (A) has an alkenyl group-containing organic group, the resin composition is likely to exhibit thermosetting properties. In one embodiment, the content of the structural unit having an alkenyl group-containing organic group in the substituted PPS resin (A) may be within a range that combines any of the above upper and lower limits. The content of the structural unit having an alkenyl group-containing organic group in the substituted PPS resin (A) can be calculated from the amount of the monomer charged. １ It can be measured by H-NMR analysis.

[0051] The glass transition temperature (Tg) of the substituted PPS resin (A) is preferably 250°C or lower, and more preferably 245°C or lower. When the substituted PPS resin (A) has a glass transition temperature (Tg) of 250°C or lower, the glass transition temperature (Tg) of a resin composition blended with the radical polymerizable compound (B) and / or the styrene (co)polymer (C), described below, tends to be lowered, making it easier to cure at low temperatures (240°C or lower). In one embodiment, the glass transition temperature (Tg) of the substituted PPS resin (A) is preferably 25 to 250°C (e.g., 90 to 250°C) or may be 30 to 245°C (e.g., 100 to 245°C). The glass transition temperature can be measured by differential scanning calorimetry (DSC) in accordance with JIS standards (JIS K 7121: Method for measuring transition temperatures of plastics) at a temperature increase rate of 20°C / min from room temperature.

[0052] The weight average molecular weight (Mw) of the substituted PPS resin (A) is preferably 1,000 to 33,000, and may be 3,000 to 33,000 (e.g., 10,000 to 33,000, 15,000 to 33,000, 20,000 to 30,000, or 23,000 to 30,000), 5,000 to 28,000 (e.g., 15,000 to 28,000), or 6,000 to 2,7000 (e.g., 10,000 to 27,000). When the weight average molecular weight (Mw) of the substituted PPS resin (A) is 1,000 or more, the dielectric loss tangent tends to be low. When the weight average molecular weight (Mw) of the substituted PPS resin (A) is 33,000 or less, the glass transition temperature tends to be a desired temperature. The weight average molecular weight (Mw) is a value calculated as a standard polystyrene by GPC measurement using tetrahydrofuran as a solvent.

[0053] The method for synthesizing the substituted PPS resin (A) is not limited, and the resin can be produced by a conventional method in the technical field, such as a method of mixing one or more monomer materials necessary for producing the desired substituted PPS resin (A) and polymerizing them under appropriate conditions to obtain a polymer structure, or a method of polymerizing a pre-prepared oligomer to obtain a polymer structure. When the resin contains a structural unit having an alkenyl group-containing organic group, the substituted PPS resin (A) can also be obtained by synthesizing a substituted PPS resin (A) containing a structural unit having an alkyl group and then eliminating protons from some of the alkyl groups to obtain a substituted PPS resin (A) substituted with an alkenyl group-containing organic group.

[0054] (Filler (B)) The resin composition preferably contains a filler (B). By containing the filler (B), the thermal expansion coefficient of the resin composition containing the substituted PPS resin (A) tends to be lowered. In other words, the filler (B) can act as an agent for lowering the thermal expansion coefficient of the resin composition containing the substituted PPS resin (A).

[0055] The type of filler is not particularly limited, but inorganic fillers are preferred. Examples of inorganic fillers include silica, titanium oxide, apatite, glass beads, calcium carbonate, carbon black, etc. (mainly spherical fillers), mica, talc, kaolin, calcined kaolin, glass flakes, etc. (mainly plate-like fillers), glass fibers, potassium titanate fibers, gypsum fibers, brass fibers, stainless steel fibers, steel fibers, ceramic fibers, and boron whisker fibers, etc. (mainly fibrous fillers). The shape of the filler may be spherical, plate-like, or fibrous. When the filler is silica, it is not limited by its preparation method or the presence or absence of a pore structure, and may be fused crushed silica, fused spherical silica, crystalline silica, amorphous silica, secondary agglomerated silica, finely divided silica, hollow silica, porous silica, etc. The filler is preferably a spherical inorganic filler, and more preferably a spherical filler of silica, alumina (aluminum hydroxide), or boron nitride. For example, when heat dissipation is desired, spherical fillers of boron nitride can be selected. The size of the filler can be determined appropriately by those skilled in the art, but the length (average) of the longest axis or side of the filler may be, for example, 10 μm or less, 5 μm or less, 1 μm or less, or 0.5 μm or less, but is preferably 0.1 μm to 8 μm, more preferably 0.2 μm to 5 μm, and even more preferably 0.3 μm to 3 μm. In the case of spherical fillers, the average particle size may be, for example, 10 μm or less, 5 μm or less, 1 μm or less, or 0.5 μm or less, but is preferably 0.1 μm to 8 μm, more preferably 0.2 μm to 5 μm, and even more preferably 0.3 μm to 3 μm. When the length (average value) of the longest axis or side of the filler or the average particle size of the spherical filler is 0.1 μm to 8 μm, the resin composition containing the substituted PPS resin (A) is likely to maintain a desired low dielectric tangent. Furthermore, even when the resin composition containing the substituted PPS resin (A) is used in a printed wiring board with a narrow wiring pitch (e.g., 20 μm to 80 μm), when the length of the longest axis or side of the filler or the average particle size of the spherical filler is 0.1 μm to 8 μm, migration defects are unlikely to occur.The filler may be surface-treated by a known method, and examples of the surface treatment agent include silane-based, titanate-based, and aluminate-based coupling agents. From the viewpoint of maintaining a low dielectric loss tangent of the resin composition containing the substituted PPS resin (A), the filler is preferably surface-treated with a silane-based surface treatment agent. Examples of the silane-based surface treatment agent include vinyl silane treatment agents, amino silane treatment agents, and phenyl silane treatment agents. For example, in consideration of adhesion to components other than the filler in the resin composition, the surface treatment agent is more preferably a vinyl silane treatment agent. The filler may be used alone or in combination of two or more types.

[0056] (Glass Cloth (C)) The resin composition is preferably impregnated into glass cloth (C). In one embodiment, the resin composition more preferably contains a substituted polyphenylene sulfide resin (A) and a filler (B), and is impregnated into glass cloth (C). By being impregnated into glass cloth (C), the thermal expansion coefficient of the resin composition containing the substituted PPS resin (A) is likely to be lowered. In other words, the glass cloth (C) can act as a thermal expansion coefficient reducer for the resin composition containing the substituted PPS resin (A). By containing filler (B) and impregnating glass cloth (C), the thermal expansion coefficient of the resin composition containing the substituted PPS resin (A) is likely to be lower than when only the filler (B) is contained or when only the glass cloth (C) is impregnated.

[0057] The type of glass cloth (C) is not particularly limited, and the dielectric properties, glass fiber diameter and thickness, density, glass material, surface treatment agent type, etc. can be appropriately selected depending on the purpose. However, considering the effects required of the resin composition containing the substituted PPS resin (A), a glass cloth having a low dielectric loss tangent and / or low dielectric properties is preferred. Commercially available glass cloths may also be used. Examples of such glass cloths include glass cloths using E glass and glass cloths using NE glass. Examples of glass cloths using NE glass include NE-2116 (manufactured by Nitto Boseki Co., Ltd.) and NE-1078 (manufactured by Nitto Boseki Co., Ltd.). Glass cloths using NE glass have low dielectric properties and low dielectric loss tangent, and are preferred when the resin composition containing the substituted PPS resin (A) is used for a wiring board. The filler may be used alone or in combination of two or more types.

[0058] (Contents of Components A to C) Hereinafter, the substituted PPS resin (A), the filler (B), and the glass cloth (C) are also collectively referred to as components (A) to (C).

[0059] The content of the substituted PPS resin (A) in the resin composition is preferably 30 to 80 parts by mass, more preferably 40 to 70 parts by mass, and even more preferably 50 to 70 parts by mass, per 100 parts by mass of the total of the components (A) and (B). When the content of the substituted PPS resin (A) in the resin composition is 30 to 80 parts by mass, per 100 parts by mass of the total of the components (A) and (B), the effect of the low dielectric tangent possessed by the substituted PPS resin (A) is easily manifested in the cured product of the resin composition, and the effect of lowering the thermal expansion coefficient by blending the filler (B) and / or glass cloth (C) is easily obtained. In one embodiment, the content of the substituted PPS resin (A) in the resin composition may be 51 parts by mass, 52 parts by mass, 55 parts by mass, 56 parts by mass, 61 parts by mass, 66 parts by mass, or 67 parts by mass, relative to 100 parts by mass of the total of the components (A) and (B), or may be a range obtained by combining these amounts, or may be a range in which these amounts are the upper or lower limit of the above range.

[0060] The content of the substituted PPS resin (A) in the resin composition is preferably 25% by mass or more relative to the total resin composition (excluding the solvent) (100% by mass), from the viewpoint that the resin composition is likely to have a desired dielectric tangent. When the content is 25% by mass or more, it may be 30% by mass or more, 35% by mass or more, 40% by mass or more, 45% by mass or more, or 50% by mass or more.

[0061] In one embodiment, the resin composition may contain other resin components such as unsubstituted PPS resin and unsubstituted or substituted PPE as resin components other than the substituted PPS resin (A). However, from the viewpoint of easily having a low dielectric tangent, the total content of the substituted PPS resin (A) is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, and particularly preferably 90% by mass or more, of all resin components (100% by mass) contained in the resin composition. In one embodiment, the content of the substituted PPS resin (A) in the thermoplastic resin contained in the resin composition may be 95% by mass or more, 98% by mass or more, or even 100% by mass.

[0062] The content of the filler (B) in the resin composition is preferably 20 to 70 parts by mass, more preferably 30 to 60 parts by mass, and even more preferably 30 to 50 parts by mass, relative to 100 parts by mass of the total of components (A) and (B). When it is 20 to 70 parts by mass, it may be 20 parts by mass, 33 parts by mass, 38 parts by mass, 44 parts by mass, 48 ​​parts by mass, or 70 parts by mass, and these may be the upper or lower limit of the range. When the content of the filler (B) in the resin composition is 20 to 70 parts by mass relative to 100 parts by mass of the substituted polyphenylene sulfide resin (A), the effect of low dielectric tangent possessed by the substituted PPS resin (A) is easily manifested, and the effect of reducing the thermal expansion coefficient possessed by the filler (B) is easily obtained.

[0063] When the resin composition is impregnated into glass cloth (C), the amount of glass cloth (C) is 10% by mass to 60% by mass, preferably 20% by mass to 50% by mass, and may be 22% by mass, relative to 100% by mass of the resin composition (excluding the solvent) containing the substituted polyphenylene sulfide resin (A). The resin composition containing the substituted polyphenylene sulfide resin (A) may also contain a "styrene (co)polymer (D)," a "radical polymerizable compound (E)," and / or an "organic peroxide (F)," which will be described below. When the amount of glass cloth (C) in the resin composition is 20% by mass to 50% by mass, relative to 100% by mass of the resin composition (excluding the solvent) containing the substituted polyphenylene sulfide resin (A), the thermal expansion coefficient tends to be low.

[0064] (Styrene-Based (Co)Polymer (D)) The resin composition preferably contains a styrene-based (co)polymer (D). In one embodiment, the resin composition contains a substituted polyphenylene sulfide resin (A) and a styrene-based (co)polymer (D), and may contain a filler (B) and / or may be impregnated into glass cloth (C). In one embodiment, the resin composition contains a substituted polyphenylene sulfide resin (A), a styrene-based (co)polymer (D), and a radically polymerizable compound (E), and may contain a filler (B) and / or may be impregnated into glass cloth (C). In one embodiment, the resin composition contains a substituted polyphenylene sulfide resin (A), a filler (B), a styrene-based (co)polymer (D), and a radically polymerizable compound (E), and may be impregnated into glass cloth (C).

[0065] In this disclosure, the term "styrene-based (co)polymer (D)" may include a homopolymer of a styrene-based monomer and a copolymer of a styrene-based monomer and another vinyl-based monomer. The styrene-based (co)polymer (D) can also be referred to as a styrene-based homopolymer or a styrene-based copolymer. By including the styrene-based (co)polymer (D), a resin composition containing the substituted PPS resin (A) can be cured at low temperatures while maintaining the low dielectric tangent characteristic of the substituted PPS resin (A). In other words, the styrene-based (co)polymer (D) can act as a curing temperature lowering agent for a resin composition containing the substituted PPS resin (A). Additionally, the toughness of the resin composition is likely to be improved. As a result, cracks are less likely to occur even when the film-shaped cured product is deformed. "Low temperature" refers to a temperature lower than the temperature at which the substituted PPS resin (A) is cured alone, and examples thereof include temperatures of 240°C or lower. Resin compositions that can be cured at 240°C or lower do not require special curing equipment and can be cured using a general heating and drying device.

[0066] In one embodiment, the resin composition preferably contains a substituted polyphenylene sulfide resin (A) and a styrene-based (co)polymer (D). By containing the substituted polyphenylene sulfide resin (A) and the styrene-based (co)polymer (D), the resin composition is likely to have a low dielectric tangent, is likely to cure at low temperatures, and is likely to have excellent toughness. In one embodiment, the resin composition preferably contains the substituted polyphenylene sulfide resin (A), a radically polymerizable compound (E), and a styrene-based (co)polymer (D). By containing the substituted polyphenylene sulfide resin (A), the radically polymerizable compound (E), and the styrene-based (co)polymer (D), the resin composition is likely to have a low dielectric tangent, is likely to cure at low temperatures, and is likely to have excellent toughness.

[0067] Examples of the styrene-based (co)polymer (D) include general-purpose polystyrene (GPPS), high-impact polystyrene (HIPS), and styrene-based thermoplastic elastomers. The styrene-based (co)polymer (D) may be one type, or two or more types may be included. Examples of the styrene-based thermoplastic elastomer include copolymers containing a styrene unit and a conjugated diene unit. The styrene unit is a structural unit derived from a styrene monomer. The styrene monomer may be selected from at least one type selected from the group consisting of styrene and styrenes having a substituent. Examples of the substituent include alkyl groups such as methyl groups. The conjugated diene unit is a structural unit derived from a conjugated diene monomer. Examples of the conjugated diene unit include an ethylene unit, a propylene unit, a butylene unit, an α-olefin unit, a butadiene unit, a hydrogenated butadiene unit, an isoprene unit, and a hydrogenated isoprene unit. It is particularly preferable that the olefin unit include a hydrogenated isoprene unit or a hydrogenated butadiene unit. The olefin unit may be one type or two or more types.

[0068] Specific examples of styrene-based thermoplastic elastomers include unhydrogenated styrene-conjugated diene copolymers such as styrene-butadiene copolymer, styrene-butadiene-styrene copolymer (SBS), styrene-butadiene-butylene-styrene copolymer, styrene-isoprene copolymer, styrene-isoprene-styrene copolymer (SIS), and styrene-ethylene-isoprene-styrene copolymer; hydrogenated styrene-conjugated diene copolymers such as styrene-ethylene / propylene-styrene copolymer (SEPS: hydrogenated product of styrene-isoprene-styrene copolymer), styrene-ethylene / butylene-styrene copolymer (SEBS: hydrogenated product of styrene-butadiene copolymer), and hydrogenated methylstyrene (ethylene / ethylene propylene) methylstyrene copolymer.

[0069] In one embodiment, the styrene-based (co)polymer (D) preferably contains a styrene-based thermoplastic elastomer. By containing a styrene-based thermoplastic elastomer, it is easy to achieve a lower dielectric constant and to exhibit better toughness. In one embodiment, the styrene-based (co)polymer (D) preferably contains a hydrogenated styrene-based copolymer.

[0070] The content of styrene units contained in the styrene (co)polymer (D) (hereinafter also referred to as the "styrene ratio") is preferably 20 to 100 mass% of all monomer units (100 mass%), more preferably 20 to 90 mass%, even more preferably 25 to 80 mass%, and particularly preferably 30 to 70 mass%. In one embodiment, the styrene ratio may be 45 to 100 mass% or 50 to 100 mass%. In one embodiment, the styrene ratio may be 30 mass%, 49 mass%, 62 mass%, 67 mass%, 68 mass%, or 100 mass%, or a range combining these, or a range with these as the upper or lower limit of the above range. A styrene ratio of 20 mass% or more makes the resin composition more likely to have a low dielectric tangent. A styrene ratio of 90 mass% or less makes the resin composition more likely to achieve a lower dielectric constant. The styrene ratio can also be calculated from the amount of raw material monomer used, and the resin composition may be １ It can also be measured by analysis using H-NMR.

[0071] The weight average molecular weight (Mw) of the styrene (co)polymer (D) may be, for example, not more than 150,000 or not more than 100,000. The method for measuring the weight average molecular weight (Mw) is as described above.

[0072] In one embodiment, the content ratio of the substituted PPS resin (A) to the styrene-based (co)polymer (C), expressed as the ratio (A / D) of (content of substituted PPS resin (A)) / (content of styrene-based (co)polymer (D)), is preferably 1.5 to 10.0, more preferably 2.0 to 9.5, and even more preferably 2.3 to 9.0. In one embodiment, the ratio (A / D) may be 1.7, 2.3, 2.4, 3.0, 4.0, 4.7, or 9.0, or may be within the upper or lower limit of the above numerical range, or may be a combination of these ranges. The content of the styrene-based (co)polymer (D) is preferably 10 to 100 parts by mass, more preferably 20 to 80 parts by mass, and even more preferably 30 to 70 parts by mass, per 100 parts by mass of the substituted polyphenylene sulfide resin (A). When the content is 30 to 70 parts by mass, it may be 30 parts by mass, 33 parts by mass, 60 parts by mass, or 70 parts by mass. When the content is 10 to 100 parts by mass, the curing temperature of the resin composition containing the substituted PPS resin (A) is likely to be low. In addition, the effect of the low dielectric tangent possessed by the substituted PPS resin (A) is likely to be exhibited, and the effect of reducing the thermal expansion coefficient due to the blending of the filler (B) and / or glass cloth (C) is likely to be obtained.

[0073] (Radical Polymerizable Compound (E)) The resin composition preferably contains a radically polymerizable compound (E). In one embodiment, the resin composition contains a substituted polyphenylene sulfide resin (A) and a radically polymerizable compound (E), and may also contain a filler (B) and / or be impregnated into glass cloth (C). In one embodiment, the resin composition contains a substituted polyphenylene sulfide resin (A), a filler (B), and a radically polymerizable compound (E), and may also be impregnated into glass cloth (C). By containing the radically polymerizable compound (E), the resin composition containing the substituted PPS resin (A) is likely to be cured at low temperatures while maintaining the low dielectric tangent characteristic of the substituted PPS resin (A). In other words, the radically polymerizable compound (E) can act as a curing temperature lowering agent for the resin composition containing the substituted PPS resin (A). "Low temperature" means a temperature lower than the temperature at which the substituted PPS resin (A) is cured alone, and examples thereof include temperatures of 240°C or lower. Resin compositions that are cured at 240° C. or less do not require special curing equipment and can be cured using a general heating and drying device.

[0074] The radically polymerizable compound (E) is a compound polymerizable by a thermal radical polymerization reaction and has a radically polymerizable unsaturated bond. The substituted PPS resin (A) is also a compound polymerizable by a thermal radical polymerization reaction, but in the present disclosure, the term "radically polymerizable compound (E)" is used to distinguish it from the substituted PPS resin (A). That is, the radically polymerizable compound (E) does not include the substituted PPS resin (A). In one embodiment, the radically polymerizable compound (E) does not have the structural structure represented by the above-described general formula (I). In another embodiment, the radically polymerizable compound (E) does not have a PPS skeleton.

[0075] Examples of the radical polymerizable compound (E) include compounds having at least one selected from the group consisting of a carbon-carbon unsaturated double bond and a maleimide group.

[0076] Examples of the carbon-carbon unsaturated double bond include double bonds contained in allyl groups, vinyl groups, acrylate groups, and methacrylate groups. Examples of the radically polymerizable compound (B) having a carbon-carbon unsaturated double bond include monofunctional compounds such as 1-octadecene, stearyl methacrylate, dicyclopentanyl methacrylate, and isobornyl methacrylate; and polyfunctional compounds such as divinylbenzene, 1,2-bis(4-vinylphenyl)ethane (BVPE), dicyclopentadiene, methylcyclopentadiene dimer, trivinylcyclohexane, triallyl isocyanurate (TAIC), dicyclopentadiene dimethanol dimethacrylate, nonanediol dimethacrylate, 1,3-diisopropenylbenzene, and trimethylolpropane triacrylate. An example of a commercially available radically polymerizable compound (B) is DD-1 manufactured by Shikoku Chemical Industry Co., Ltd.

[0077] Examples of the radical polymerizable compound (E) having a maleimide group include phenylmaleimide, cyclohexylmaleimide, 4,4'-diphenylmethane bismaleimide, m-phenylene bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, and 1,6-bismaleimide-(2,2,4-trimethyl)hexane. The radical polymerizable compound (E) preferably contains one or more compounds selected from the compounds exemplified above. The radical polymerizable compound (E) may be used alone or in combination of two or more.

[0078] The molecular weight (weight average molecular weight) of the radical polymerizable compound (E) is preferably 100 to 3,000, more preferably 130 to 2,000, even more preferably 150 to 1,000, and may be 180 to 500. When the molecular weight of the radical polymerizable compound (B) is 100 to 3,000, the crosslinking density increases and the glass transition temperature is less likely to decrease. The molecular weight can be measured or calculated by a conventional method. When the molecular weight is a weight average molecular weight, it is a value calculated in terms of standard polystyrene obtained by GPC measurement using tetrahydrofuran as a solvent.

[0079] In one embodiment, the content ratio of the substituted PPS resin (A) to the radically polymerizable compound (E), expressed as the ratio (A / E) of (content of substituted PPS resin (A)) / (content of radically polymerizable compound (E)), is preferably 1.2 to 6.0, more preferably 1.3 to 5.5, and even more preferably 1.5 to 4.7. In one embodiment, the ratio (A / E) may be 1.5, 1.9, 4.0, or 4.7, or may be within a range defined by the upper or lower limit of the numerical range. The content of the radically polymerizable compound (E) is preferably 20 to 100 parts by mass, more preferably 25 to 55 parts by mass, per 100 parts by mass of the substituted polyphenylene sulfide resin (A). When the amount is 20 to 100 parts by mass, the effect of low dielectric tangent of the substituted PPS resin (A) is easily exhibited, and the effect of reducing the thermal expansion coefficient due to the blending of the filler (B) and / or glass cloth is easily obtained. In addition, the curing temperature of the resin composition containing the substituted PPS resin (A) is easily reduced.

[0080] When the resin composition contains a radically polymerizable compound (E) and a styrene-based (co)polymer (D), the content ratio of the radically polymerizable compound (E) to the styrene-based (co)polymer (D) is preferably 0.8 to 2.0, more preferably 0.9 to 1.8, and even more preferably 1.0 to 1.6, as the ratio (E / D) of (content of radically polymerizable compound (E)) / (content of styrene-based (co)polymer (D)). When the ratio is 1.0 to 1.6, it may be 1.6 or 1.7. When the ratio of (content of E) / (content of D) is 0.8 to 2.0, the resin composition is likely to have a low dielectric tangent and be easily cured at low temperatures. Furthermore, toughness is likely to be improved.

[0081] (Organic Peroxide (F)) The resin composition preferably contains an organic peroxide (F). By containing the organic peroxide (F), the resin composition becomes more likely to be cured at low temperatures.

[0082] Examples of the organic peroxide (F) include 1,3-bis(t-butylperoxyisopropyl)benzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, di-t-butyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)-3-hexyne, benzoyl peroxide, 3,3',5,5'-tetramethyl-1,4-diphenoquinone, chloranil, 2,4,6-tri-t-butylphenoxyl, t-butylperoxyisopropyl monocarbonate, and azobisisobutyronitrile. The organic peroxide (F) may be one type, or two or more types may be contained.

[0083] The content of the organic peroxide (F) is preferably 1 to 10 parts by mass, more preferably 1 to 5 parts by mass, and even more preferably 1 to 3 parts by mass, relative to 100 parts by mass of the substituted polyphenylene sulfide resin (A). When the content is 1 to 3 parts by mass, it may be 1.6 parts by mass. When the content is 1 part by mass or more, the curing temperature of the resin composition containing the substituted PPS resin (A) is likely to be lowered. Furthermore, when the content is 10 parts by mass or less, the effect of the low dielectric tangent possessed by the substituted PPS resin (A) is likely to be exhibited, and the effect of reducing the thermal expansion coefficient due to the blending of the filler (B) and / or glass cloth is likely to be obtained.

[0084] (Solvent) The resin composition may contain a solvent. When a solvent is contained, the resin composition can be used as a varnish. The varnish is generally preferably a polymer solution in which a resin component is dissolved in an organic solvent. In one embodiment, it is sufficient that at least a portion of the polymer is dissolved at a liquid temperature of 25°C, but it is preferable that all of the polymer is dissolved. The organic solvent is not limited and can be selected by a person skilled in the art from organic solvents well known in the art. Examples include acetone, ethyl acetate, cyclohexane, heptane, tetrahydrofuran, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, ethylene glycol, cellosolve-based solvents, carbitol-based solvents, anisole, N-methylpyrrolidone, propylene glycol monomethyl ether, methyl ether acetate, toluene, cyclohexanone, methyl ethyl ketone, and methyl isobutyl ketone. The organic solvent may be used alone or in combination of two or more selected from these. The lower limit of the content of the solute (component other than the solvent) in the polymer solution is not limited as long as it is within a range in which a polymer solution that is easy to handle and sufficient for commercialization can be obtained, and may be, for example, 5 to 50% by mass, 7 to 45% by mass, 10 to 40% by mass, or 10 to 35% by mass relative to 100% by mass of the polymer solution.

[0085] (Other Additives) The resin composition may further contain additives such as inorganic fillers, silane coupling agents, antifoaming agents, antioxidants, heat stabilizers, antistatic agents, UV absorbers, dyes, pigments, and lubricants, as needed. Examples of inorganic fillers include silica, alumina, talc, aluminum hydroxide, magnesium hydroxide, titanium oxide, mica, aluminum borate, barium sulfate, boron nitride, forsterite, zinc oxide, magnesium oxide, and calcium carbonate. The inorganic filler may be surface-treated. When an inorganic filler is contained, the content thereof is preferably 30 to 80 parts by mass, more preferably 40 to 70 parts by mass, per 100 parts by mass of the total of the substituted polyphenylene sulfide resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C).

[0086] The resin composition may contain a flame retardant, but since the substituted PPS resin (A) has good flame retardancy as described above, the content of the flame retardant (for example, a flame retardant containing bromine or phosphorus) in the resin composition may be 10% by mass or less, less than 8% by mass, 5% by mass or less, 3% by mass or less, or 1% by mass or less. In one embodiment, the resin composition may not contain a flame retardant.

[0087] <Resin Composition> The method for producing the resin composition is not limited and can be carried out using equipment and methods generally used for preparing resin compositions. Generally, resin compositions containing a substituted PPS resin (A) are often prepared as a polymer solution (resin varnish) dissolved in an organic solvent. To prepare such a resin varnish, the substituted PPS resin (A), the radically polymerizable compound (B) and / or the styrene (co)polymer (C), and any other additives used as needed that are soluble in an organic solvent may be added to the organic solvent and mixed by stirring with a stirrer. Heating may be performed as necessary. Subsequently, a component that is insoluble in the organic solvent (e.g., an inorganic filler, etc.) may be added as appropriate, and dispersed using a ball mill, bead mill, planetary mixer, roll mill, or the like until a predetermined dispersion state is achieved, thereby preparing the resin varnish. Examples of organic solvents are the same as those described in the "Varnish" section below.

[0088] In one embodiment, the resin composition preferably has a dielectric loss tangent at 10 GHz of 0.002 or less, more preferably less than 0.002, and even more preferably 0.0018 or less. The lower the dielectric loss tangent, the easier it is to suppress transmission loss when the resin composition is used as a material for a wiring substrate. By having a dielectric loss tangent at 10 GHz of 0.002 or less, the easier it is to suppress transmission loss at 10 GHz when the resin composition is used as a material for a wiring substrate.

[0089] In one embodiment, the resin composition has a dielectric loss tangent at 40 GHz of preferably 0.003 or less, more preferably 0.0025 or less, which makes it easier to suppress transmission loss at 40 GHz when the resin composition is used as a material for a wiring board.

[0090] In one embodiment, the resin composition has a dielectric constant at 10 GHz of preferably less than 3.00, more preferably 2.80 or less, and even more preferably 2.60 or less. The lower the dielectric constant, the easier it is to suppress transmission loss when the resin composition is used as a material for a wiring substrate. A dielectric constant at 10 GHz of less than 3.00 makes it easier to suppress transmission loss at 10 GHz when the resin composition is used as a material for a wiring substrate. In one embodiment, the resin composition has a dielectric constant at 40 GHz of preferably less than 3.00, more preferably 2.90 or less, and even more preferably 2.85 or less. A dielectric constant at 40 GHz of less than 3.00 makes it easier to suppress transmission loss at 40 GHz when the resin composition is used as a material for a wiring substrate. The dielectric loss tangent and dielectric constant are measured at a predetermined frequency using a sheet of the resin composition with a vector network analyzer and a split cylinder resonator.

[0091] In one embodiment, the resin composition preferably has a glass transition temperature (Tg) of 240 ° C. or less, more preferably less than 240 ° C., even more preferably 230 ° C. or less, even more preferably 220 ° C. or less, and particularly preferably 200 ° C. or less. When the glass transition temperature (Tg) of the resin composition is 240 ° C. or less, it becomes easy to cure at low temperatures (240 ° C. or less). In one embodiment, the glass transition temperature (Tg) of the resin composition is preferably 25 to 240 ° C. (e.g., 90 to 240 ° C.), may be 30 to 230 ° C. (e.g., 100 to 230 ° C.), may be 40 to 220 ° C. (e.g., 120 to 220 ° C.), may be 50 to 210 ° C. (e.g., 150 to 210 ° C.), or may be 60 to 200 ° C. (e.g., 170 to 200 ° C.). The method for measuring the glass transition temperature is as described above.

[0092] In one embodiment, the resin composition preferably has a thermal expansion coefficient of 60 ppm / K or less, more preferably 30 ppm / K or less, as measured under the following conditions. A thermal expansion coefficient of 60 ppm / K or less makes it less likely for warping to occur in a laminate produced through a lamination process with other laminating materials such as metal foil when the resin composition is used as a material for a wiring board. The thermal expansion coefficient (α1 (region lower than Tg)) is determined from a strain-temperature curve obtained under the following conditions for a cured product of the resin composition. Measuring device: TMA SS7100 / Hitachi High-Tech Science Measurement mode: Tension Atmosphere: N ２ Temperature range: 1st heat: 0°C to 250°C, 2nd heat: 0°C to 250°C. Wait 20 minutes at the starting temperature. Heating rate: 5°C / min. Measurement load: 20mN.

[0093] [Second embodiment: wiring board article] The wiring board article according to this embodiment includes the resin composition described above. Because the wiring board article includes the resin composition described above, the wiring board formed using the wiring board article has a low dielectric loss tangent. Examples of wiring board articles include an interlayer insulating film, a prepreg, a metal-clad laminate, and a substrate.

[0094] (Interlayer insulating film) Examples of the interlayer insulating film include interlayer insulating films used in printed wiring boards and the like. The interlayer insulating film can also be used as a material for a multilayer printed wiring board. The interlayer insulating film can be produced, for example, by applying a varnish containing a resin composition and an organic solvent to other materials and volatilizing the solvent. This can also be used to prepare a laminate structure for a multilayer printed circuit board.

[0095] (Prepreg) An example of the prepreg is a prepreg obtained by impregnating a substrate with a varnish containing a resin composition and an organic solvent and drying the varnish. The substrate used for the prepreg is not limited and can be selected by a person skilled in the art from materials well known in the art, and examples include natural fiber substrates, organic synthetic fiber substrates, inorganic fiber substrates, etc.

[0096] (Metal-clad laminate) An example of a metal-clad laminate is a metal-clad laminate containing the above-mentioned prepreg. Such a metal-clad laminate can be obtained, for example, by stacking multiple prepregs, placing metal foil on one or both sides of the prepreg, and then hot-pressing and press-molding the prepreg. Examples of metal foil include copper foil, aluminum foil, tin foil, gold foil, silver foil, platinum foil, and nickel foil, and can be selected by a person skilled in the art according to the properties and applications required for the metal-clad laminate.

[0097] (Substrate) A substrate is a base used together with a semiconductor chip to protect the semiconductor chip, such as a CPU or memory, and to mount the semiconductor chip on a printed circuit board (PCB). For example, the substrate may be a substrate portion of an FC-BGA (Flip Chip-Ball Grid Array), an FC-CSP (Flip Chip Chip Scale Package), or the like. The substrate can be produced, for example, by molding a resin composition into a plate shape using a known molding device and method.

[0098] [Third Embodiment: Wiring Board] The wiring board according to this embodiment includes the resin composition described above. Since it includes the resin composition described above, the wiring board has a low dielectric loss tangent. The wiring board is a substrate for mounting electronic components such as semiconductors and providing wiring, and is not limited by its structure and / or use. In this specification, the wiring board includes parts of a printed wiring board other than electronic components such as semiconductors, and an example of a wiring board is a printed circuit board (PCB) of a printed wiring board. The printed board may be, for example, a multilayer printed board described above in the "interlayer insulating film." The printed board includes any of a rigid board, a flexible board, a rigid-flex board, a metal-based board, etc., and electronic components can be mounted on these printed boards to form a printed wiring board.

[0099] [Fourth Embodiment: Printed Wiring Board] The printed wiring board according to this embodiment includes the resin composition described above and electronic components. The structure and / or applications of the printed wiring board are not limited. For example, the printed wiring board may be a printed circuit board, such as a rigid board, a flexible board, a rigid-flex board, or a metal-based board, on which electronic components are mounted. Examples of electronic components are not limited, but include semiconductor chips, resistors, and capacitors. For example, the structure may include wiring and electronic components mounted on one or both sides of a wiring board (printed circuit board), or wiring and electronic components may be mounted between layers of a multilayer wiring board. For example, rigid printed wiring boards having electronic components mounted on a rigid board can be used in mobile communication system terminals, base stations, servers, routers, millimeter-wave radar, probe cards, and the like, while flexible printed wiring boards having electronic components mounted on a flexible board can be used in connection cables, antennas, antenna cables, and the like.

[0100] Fifth Embodiment: Method for Manufacturing a Wiring Board A method for manufacturing a wiring board according to this embodiment includes curing a resin composition, wherein the resin composition is a compound represented by general formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group (preferably H, an alkyl group, an alkoxy group, or an alkenyl group-containing organic group), and R １ , R ２ , R ３ , and R ４ wherein one or more of the following is an alkyl group or an alkoxy group: a substituted polyphenylene sulfide resin (A) containing a structural unit represented by the formula:

[0101] The resin composition containing the styrene-based (co)polymer (D) and / or the radically polymerizable compound (E) can be cured at a low temperature, and therefore can be cured at a lower temperature than when the substituted PPS resin (A) is cured alone.

[0102] Curing includes heating the resin composition at a temperature of 240° C. or less. The heating temperature is 240° C. or less, preferably 235° C. or less, more preferably 230° C. or less, even more preferably 225° C. or less, and particularly preferably 220° C. or less. The heating method is not limited, and heating can be performed using a known heating and drying device.

[0103] In one embodiment, the method for producing a wiring board may include, prior to the curing step, a step of preparing a varnish containing the resin composition, or a step of applying (or impregnating) the varnish to a substrate. In another embodiment, the method for producing a wiring board may include, prior to the curing step, a step of preparing a prepreg containing the resin composition. The method for producing a wiring board may further include a drying step.

[0104] A non-limiting list of exemplary embodiments and combinations of exemplary embodiments of the present disclosure is disclosed below: [1] General formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and R １ , R ２ , R ３ , and R ４a resin composition comprising a substituted polyphenylene sulfide resin (A) containing a structural unit represented by the formula (II), wherein one or more of the formula (II) is an alkyl group or an alkoxy group; and a filler (B). [2] The resin composition according to [1], impregnated into a glass cloth (C). [3] The resin composition according to [1] or [2], further containing a styrene-based (co)polymer (D). [4] The resin composition according to any one of [1] to [3], further containing a radically polymerizable compound (E). [5] The resin composition according to any one of [1] to [4], further containing an organic peroxide (F). [6] The resin composition according to any one of [1] to [5], wherein the contents of the substituted polyphenylene sulfide resin (A) and the filler (B) are 40 to 200 parts by mass per 100 parts by mass of the substituted polyphenylene sulfide resin (A). [7] The substituted polyphenylene sulfide resin (A) is a substituted polyphenylene sulfide resin represented by the formula (II): [In formula (II), R ５ａ , R ６ａ , R ７ａ and R ８ａ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and R ５ａ , R ６ａ , R ７ａ and R ８ａ wherein one or more of the following is an alkenyl group-containing organic group. [8] The resin composition according to any one of [1] to [7], containing a solvent. [9] An article for wiring boards, comprising the resin composition according to any one of [1] to [8].

[10] The article according to [9], which is an interlayer insulating film, a prepreg, a metal-clad laminate, or a substrate.

[11] A wiring board, comprising the resin composition according to any one of [1] to [8].

[12] A printed wiring board, comprising the resin composition according to any one of [1] to [8] and an electronic component.

[0105] The present disclosure will be explained in more detail below by showing examples, but interpretation of the present disclosure is not limited to these examples.

[0106] Synthesis Example 1: Preparation of MVPPS. Poly(2,6-dimethyl-1,4-phenylene sulfide) (285.0 g) obtained in Synthesis Example 1, N-bromosuccinimide (NBS) (0.05 mol, 8.94 g), and AIBN (0.06 mol, 10.3 g) were added to a 20 L four-neck flask, dissolved in chlorobenzene, and allowed to react under reflux for 24 hours. After the reaction, the solution was cooled with ice water, and the precipitated succinimide was filtered off using a glass filter. The filtrate was purified by precipitation using 5 wt % hydrochloric acid-acidified methanol, recovered using a glass filter, and vacuum dried to obtain bromo PPS (MXPPS) (yield: 85%, 853.3 g) in which some of the methyl protons had been brominated. Next, MXPPS (850 g) and triphenylphosphine (0.74 mol) were added to the four-neck flask, dissolved in THF, and heated to reflux for 24 hours. After cooling to room temperature, a 37 wt % aqueous formaldehyde solution (5.55 mol, 409 ml) was added to the reaction solution and stirred for 23 minutes, at which point the precipitate disappeared. Potassium t-butoxide (0.86 mol) was then added and the reaction was allowed to proceed for 17 hours. After the reaction was complete, the solution was concentrated to about half its original volume and purified by precipitation using hydrochloric acid-acidified methanol. After recovery by centrifugation and vacuum drying, a 2,6-dimethyl PPS resin (MVPPS) in which 7% of the total methyl groups had been substituted with vinyl groups, corresponding to substituted PPS resin (A), was obtained (yield: 95%, 810 g). This substituted PPS resin (A) has the following structural units A and B. Structural unit A: R in general formula (I) １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is a methyl group, and R １ or R ４ (In general formula (II), R ５ａ or R ８ａ ) is a vinyl group, and R ２ and R ３ (In general formula (II), R ６ａ or R ７ａ ) is H. Structural unit B: R in general formula (I) １ and R ４ is a methyl group, and R ２ and R ４is H. The content of the structural unit A (a structural unit containing a vinyl group and a methyl group) in the substituted PPS resin was 2 mol %, and the content of the structural unit B (a structural unit containing a methyl group) in the substituted PPS resin was 98 mol %. The weight average molecular weight (Mw) and number average molecular weight (Mn) of the obtained polymer, measured in terms of polystyrene, were found to be 30,000 and 8,600, respectively, by gel permeation chromatography (GPC).

[0107] [Materials] The materials used in the examples and comparative examples are as follows: (Main component) A1: Polyphenylene ether (PPE), "SA9000" manufactured by ABIC A2: Polymer obtained in Synthesis Example 1 (VDMPPS: 2,6-dimethyl PPS resin in which 7% of the methyl groups are substituted with vinyl groups)

[0108] (Filler) B1: Silica filler (vinylsilane treated, particle size 0.5 μm, manufactured by Admatechs Co., Ltd.)

[0109] (Glass cloth) C1: NE-1078 (manufactured by Nittobo)

[0110] (Styrene-based (co)polymer) D1: Styrene-ethylene / butadiene-styrene (SEBS), "Tuftec (registered trademark) P5051" manufactured by Asahi Kasei Corporation, styrene ratio (catalog value) 49% by mass

[0111] (Radical polymerizable compound) E1: triallyl isocyanurate, "TAIC" manufactured by Nippon Kasei Chemical Co., Ltd., molecular weight 249.7

[0112] (Organic peroxide) F1: 1,3-bis(butylperoxyisopropyl)benzene ("Perbutyl P" manufactured by NOF Corporation)

[0113] (Solvent) Toluene

[0114] Example 1: VMPPS (12.0 g) obtained in Synthesis Example 1 was dissolved in toluene (30 g). Further, styrene-based thermoplastic elastomer D1 (Tuftec® P5051, manufactured by Asahi Kasei Corporation, 7.2 g), organic peroxide F1 (Perbutyl P, manufactured by NOF Corporation, 0.19 g), and filler B1 (5SP-CT1, manufactured by Admatechs Co., Ltd., 70 wt % toluene solution, 36.2 g) were added and stirred at 50°C for 2 hours to obtain a varnish, a resin composition. (Drying Process) The resulting varnish was poured into a metal pad, and glass cloth (22% by weight of glass cloth per 100% by weight of the resin composition excluding toluene) cut to a width of 16 cm and a length of 25 cm was impregnated with the varnish. After impregnation, the mixture was dried at 100°C for 2 minutes and then at 140°C for 5 minutes to produce a prepreg. (Curing step) The obtained prepreg was sandwiched between Teflon sheets and pressed with a press to produce a cured product. The pressing conditions were as follows: 100°C was held for 20 minutes, the temperature was raised to 200°C at a rate of 5°C / min, and the prepreg was held at 200°C for 90 minutes. After holding at 100°C for 20 minutes, the pressure was raised to 4 MPa.

[0115] [Example 2] (Drying Step) After preparing the varnish using the method of Example 1, it was poured into a Teflon petri dish and dried on a hot plate at 120°C for 5 minutes. The resulting film-like solid was crushed and dried again on a hot plate at 120°C for 5 minutes to obtain a powdery solid. (Curing Step) The powdery solid (approximately 1 g) obtained in the drying step and a 120μ polyimide film as a spacer were sandwiched between Teflon films and vacuum-pressed using a vacuum press. The temperature was increased from 80°C at a rate of 20°C / min and maintained at 200°C for 2 hours. A pressure of 10 kN was applied when the hot plate temperature reached 110°C, yielding a film-like cured product with a thickness of approximately 100μ and a diameter of approximately 10 cm.

[0116] Comparative Example 1 A cured resin composition was obtained in the same manner as in Example 1, except that polyphenylene ether (PPE) was used in place of VMPPS in the amounts shown in Table 1.

[0117] Comparative Example 2 A cured resin composition was obtained in the same manner as in Example 2, except that polyphenylene ether (PPE) was used in place of VMPPS in the amounts shown in Table 1.

[0118] In Comparative Example 3, the VMPPS powder obtained in Synthesis Example 1 was used as is without a drying step to obtain a film-like cured product. Specifically, the VMPPS powder obtained in Synthesis Example 1 and a 120 μm polyimide film as a spacer were sandwiched between Teflon films and vacuum-pressed using a vacuum press. The temperature was increased from 160°C at a rate of 20°C / min and maintained at 245°C for 2 hours. A pressure of 5 kN was applied when the hot plate temperature reached 235°C, yielding a film-like cured product with a thickness of approximately 100 μm and a diameter of approximately 10 cm.

[0119] [Evaluation] Various physical properties were measured by the following methods. The results are shown in Table 1. (Measurement of dielectric loss tangent) The dielectric loss tangent was measured using the film-like cured product obtained by the above method. The dielectric loss tangent was measured at 10 GHz or 40 GHz by the cavity resonator perturbation method using a Keysight Technologies vector network analyzer (N5290A) and a split cylinder resonator under standard environmental conditions (23±2°C) and a relative humidity of 45 to 55%.

[0120] (Thermal expansion coefficient) For the film-like cured product obtained by the above method, the linear expansion coefficient (α1 (in the region lower than Tg)) was determined from the strain-temperature curve obtained under the following conditions. Measuring device: TMA SS7100 / Hitachi High-Tech Science Measuring mode: Tension Atmosphere: N ２ Temperature range: 1st heat / 0°C to 250°C, 2nd heat / 0°C to 250°C Wait 20 minutes at starting temperature Heating rate: 5°C / min Measurement load: 20 mN A thermal expansion coefficient of 60 ppm / K or less was rated as "good," a thermal expansion coefficient of 30 ppm / K or less was rated as "excellent," and a thermal expansion coefficient of more than 60 ppm / K was rated as "poor."

[0121]

[0122] As shown in Table 1, the film-like cured products containing VMPPS and a filler (Examples 1 and 2) had a dielectric dissipation factor of 0.002 or less at 10 GHz and a dielectric dissipation factor of 0.0025 or less at 40 GHz. On the other hand, the film-like cured products containing polyphenylene ether (PPE) and a filler (Comparative Examples 1 and 2) had a dielectric dissipation factor of more than 0.002 at 10 GHz and a dielectric dissipation factor of more than 0.003 at 40 GHz. These results demonstrate that the inclusion of VMPPS in a resin composition tends to lower the dielectric dissipation factor of the film-like cured product.

[0123] Furthermore, the thermal expansion coefficient of the cured film containing VMPPS and a filler (Examples 1 and 2) was evaluated as good or excellent. The thermal expansion coefficient of the cured film containing glass cloth in addition to VMPPS and a filler (Example 1) was evaluated as excellent. The thermal expansion coefficient of the cured film containing polyphenylene ether (PPE) and a filler (Comparative Examples 1 and 2) was also evaluated as good or excellent. The thermal expansion coefficient of the cured film containing glass cloth in addition to polyphenylene ether (PPE) and a filler (Comparative Example 1) was evaluated as excellent. On the other hand, the thermal expansion coefficient of the cured film containing VMPPS but not a filler or glass cloth (Comparative Example 3) was evaluated as poor. These results demonstrate that the inclusion of a filler or glass cloth in a resin composition tends to lower the thermal expansion coefficient of the cured film. In particular, the inclusion of a filler and glass cloth in a cured film tends to further lower the thermal expansion coefficient of the cured film.

[0124] It was shown that when the resin composition contains VMPPS and a filler or glass cloth, the film-like cured product tends to have a low dielectric tangent and a low thermal expansion coefficient.

[0125] The resin composition of this embodiment has a low dielectric loss tangent and a low thermal expansion coefficient, and therefore can be preferably used in the production of wiring boards and has industrial applicability.

Claims

1. General formula (I): [In formula (I), R １ , R ２ , R ３ , and R ４ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, R １ , R ２ , R ３ , and R ４ wherein one or more of the following is an alkyl group or an alkoxy group:

2. The resin composition according to claim 1, impregnated into a glass cloth (C).

3. The resin composition according to claim 1, further comprising a styrene-based (co)polymer (D).

4. The resin composition according to claim 1, further comprising a radically polymerizable compound (E).

5. The resin composition according to claim 1, further comprising an organic peroxide (F).

6. The resin composition according to claim 1, wherein the contents of the substituted polyphenylene sulfide resin (A) and the filler (B) are 40 parts by mass to 200 parts by mass per 100 parts by mass of the substituted polyphenylene sulfide resin (A).

7. The substituted polyphenylene sulfide resin (A) is represented by the general formula (II): [In formula (II), R ５ａ , R ６ａ , R ７ａ and R ８ａ are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, R ５ａ , R ６ａ , R ７ａ and R ８ａ and at least one of the above is an alkenyl-group-containing organic group.

8. The resin composition according to any one of claims 1 to 7, further comprising a solvent.

9. An article for wiring boards, comprising the resin composition according to any one of claims 1 to 7.

10. The article of claim 9 which is an interlaminar dielectric film, a prepreg, a metal clad laminate, or a substrate.

11. A wiring board comprising the resin composition according to any one of claims 1 to 7.

12. A printed wiring board comprising the resin composition according to any one of claims 1 to 7 and an electronic component.