Resin composition containing substituted polyphenylene sulfide resin

Abstract

To provide a resin composition which has a low dielectric loss tangent and can be cured at a low temperature. Provided is a resin composition containing a substituted polyphenylene sulfide resin (A) containing a structural unit represented by general formula (I): [in formula (I), R1, R2, R3, and R4 are each independently H, an alkyl group, an alkoxy group, an aryl group, or an alkenyl group-containing organic group, and one or more of R1, R2, R3, and R4 is an alkyl group or an alkoxy group], and a radically polymerizable compound (B) and / or a styrene (co)polymer (C).

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 have discovered that substituted polyphenylene sulfide (substituted PPS) resins can achieve a lower dielectric tangent than PPE resins or unsubstituted PPS resins. However, it has been found that substituted PPS resins do not easily generate the active species necessary for curing unless the temperature exceeds 240°C, and therefore they are difficult to cure unless the temperature is high.

[0007] An object of the present disclosure is to provide a resin composition that has a low dielectric tangent and can be cured at low temperatures.

[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 a substituted polyphenylene sulfide resin (A) containing a structural unit represented by the formula (I), wherein one or more of the formula (I) is an alkyl group or an alkoxy group; a radical polymerizable compound (B), and / or a styrene-based (co)polymer (C). [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 [3-1]. [4] Fourth Aspect [4-1] A printed wiring board, comprising the resin composition according to [1-1]. [5] Fifth Aspect [5-1] A method for producing a wiring board, comprising curing a resin composition, wherein the resin composition is a compound represented by the 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 ４wherein 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:

[0009] According to the present disclosure, it is possible to provide a resin composition that has a low dielectric tangent and can be cured at low temperatures.

[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 ４wherein one or more of the following is an alkyl group or an alkoxy group; a radical polymerizable compound (B), and / or a styrene-based (co)polymer (C).

[0012] By including the substituted PPS resin (A), the radical polymerizable compound (B), and / or the styrene-based (co)polymer (C), a resin composition can be obtained that has a low dielectric dissipation factor and can be cured at low temperatures. "Low temperature" refers to a temperature lower than the temperature at which the substituted PPS resin (A) is cured alone, such as a temperature of 240°C or lower. A non-limiting mechanism is believed to be that the substituted PPS resin (A) is compatible with the radical polymerizable compound (B) and / or the styrene-based (co)polymer (C), thereby becoming molten at a heating temperature of 240°C or lower (e.g., about 200°C), thereby generating the active species necessary for curing. As a result, the substituted PPS resin (A) is believed to cure at a low curing temperature while maintaining its low dielectric dissipation factor. Resin compositions that cure at 240°C or lower can be cured using a general heating and drying device without requiring a special curing device. It has not been known until now that the radical polymerizable compound (B) and the styrene (co)polymer (C) have the effect of lowering the curing temperature while maintaining the low dielectric tangent property 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 ４The 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 ２ Even 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 R４ 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 ４ One 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 ４ Those 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)}. In one embodiment, in formula (IV), R 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] (Radical Polymerizable Compound (B)) The resin composition preferably contains a radically polymerizable compound (B). By containing the radically polymerizable compound (B), the curing temperature of the resin composition containing the substituted PPS resin (A) tends to be lowered while maintaining the low dielectric tangent characteristic of the substituted PPS resin (A). In other words, the radically polymerizable compound (B) can act as a curing temperature lowering agent for the resin composition containing the substituted PPS resin (A).

[0055] The radically polymerizable compound (B) 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 (B)" is used to distinguish it from the substituted PPS resin (A). That is, the radically polymerizable compound (B) does not include the substituted PPS resin (A). In one embodiment, the radically polymerizable compound (B) does not have the structural structure represented by the above-described general formula (I). In another embodiment, the radically polymerizable compound (B) does not have a PPS skeleton.

[0056] Examples of the radical polymerizable compound (B) include compounds having at least one selected from the group consisting of a carbon-carbon unsaturated double bond and a maleimide group.

[0057] 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.

[0058] Examples of the radical polymerizable compound (B) 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 (B) preferably contains one or more compounds selected from the compounds exemplified above. The radical polymerizable compound (B) may be used alone or in combination of two or more.

[0059] The molecular weight (weight average molecular weight) of the radical polymerizable compound (B) 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.

[0060] (Styrene-based (co)polymer (C)) The resin composition preferably contains a styrene-based (co)polymer (C). In the present disclosure, the term "styrene-based (co)polymer (C)" 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 (C) can also be referred to as a styrene-based homopolymer or a styrene-based copolymer. By containing the styrene-based (co)polymer (C), the curing temperature of the resin composition containing the substituted PPS resin (A) tends to be lowered while maintaining the low dielectric tangent property of the substituted PPS resin (A). In other words, the styrene-based (co)polymer (C) can act as a curing temperature lowering agent for the resin composition containing the substituted PPS resin (A). In addition, the toughness of the resin composition tends to be improved. As a result, cracks are less likely to occur even when the film-like cured product is deformed.

[0061] In one embodiment, the resin composition preferably contains a substituted polyphenylene sulfide resin (A) and a styrene-based (co)polymer (C). By containing the substituted polyphenylene sulfide resin (A) and the styrene-based (co)polymer (C), the resin composition is likely to have a low dielectric tangent, is easily cured at low temperatures, and is easily produced with excellent toughness. In one embodiment, the resin composition preferably contains the substituted polyphenylene sulfide resin (A), a radically polymerizable compound (B), and a styrene-based (co)polymer (C). By containing the substituted polyphenylene sulfide resin (A), the radically polymerizable compound (B), and the styrene-based (co)polymer (C), the resin composition is likely to have a low dielectric tangent, is easily cured at low temperatures, and is easily produced with excellent toughness.

[0062] Examples of the styrene-based (co)polymer (C) include general-purpose polystyrene (GPPS), high-impact polystyrene (HIPS), and styrene-based thermoplastic elastomers. The styrene-based (co)polymer (C) may be one type or may contain two or more types. 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 at least one 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.

[0063] 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.

[0064] In one embodiment, the styrene-based (co)polymer (C) 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 (C) preferably contains a hydrogenated styrene-based copolymer.

[0065] The content of styrene units contained in the styrene (co)polymer (C) (hereinafter also referred to as the "styrene ratio") is preferably 20 to 100% by mass, more preferably 20 to 90% by mass, even more preferably 25 to 80% by mass, and particularly preferably 30 to 70% by mass, based on the total monomer units (100% by mass). In one embodiment, the styrene ratio may be 45 to 100% by mass or 50 to 100% by mass. In one embodiment, the styrene ratio may be 30% by mass, 49% by mass, 62% by mass, 67% by mass, 68% by mass, or 100% by mass, or a range combining these values, or a range with these values ​​as the upper or lower limit of the above range. A styrene ratio of 20% by mass or more makes it easier for the resin composition to have a low dielectric tangent. A styrene ratio of 90% by mass or less makes it easier for the resin composition to achieve a lower dielectric constant. The styrene ratio can also be calculated from the amount of raw material monomers used, and the resin composition may be １ It can also be measured by analysis using H-NMR.

[0066] The weight average molecular weight (Mw) of the styrene (co)polymer (C) 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.

[0067] (Contents of Components A to C) Hereinafter, the substituted PPS resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C) are also collectively referred to as components (A) to (C). The content of the substituted PPS resin (A) in the resin composition is preferably 30 to 95 parts by mass, more preferably 35 to 93 parts by mass, even more preferably 40 to 92 parts by mass, even more preferably 43 to 90 parts by mass, and particularly preferably 45 to 90 parts by mass, relative to 100 parts by mass of the total of the components (A) to (C). When the content of the substituted PPS resin (A) in the resin composition is 30 to 95 parts by mass relative to 100 parts by mass of the total of the components (A) to (C), the effect of the low dielectric tangent possessed by the substituted PPS resin (A) is easily manifested, and by blending the radical polymerizable compound (B) and the styrene-based (co)polymer (C), the resin fluidity at low temperatures is easily increased, and the effect of lowering the curing temperature is more easily obtained. In one embodiment, the content of the substituted PPS resin (A) in the resin composition may be 48 parts by mass, 70 parts by mass, 80 parts by mass, or 90 parts by mass, relative to 100 parts by mass of the total of the components (A) to (C), or may be any combination thereof, or may be a range with these as the upper or lower limit of the above range.

[0068] The content of the substituted PPS resin (A) in the resin composition is preferably 30% by mass or more relative to the total resin composition (100% by mass), from the viewpoint that the resin composition is likely to have a desired dielectric loss tangent. When the content is 30% by mass or more, it may be 40% by mass or more, or 45% by mass or more.

[0069] 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) and the styrene-based (co)polymer (C). However, from the viewpoint of easily having a low dielectric tangent and easily curing at low temperatures, the total content of the substituted PPS resin (A) and the styrene-based (co)polymer (C) 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.

[0070] In one embodiment, the content ratio of the substituted PPS resin (A) to the radically polymerizable compound (B) is preferably 1.2 to 6.0, more preferably 1.3 to 5.5, and even more preferably 1.5 to 4.7, as the ratio (A / B) of (content of substituted PPS resin (A)) / (content of radically polymerizable compound (B)). In one embodiment, the ratio (A / B) may be 1.5 or 4.7, or may be within a range with these values ​​as the upper or lower limit of the above numerical range.

[0071] In one embodiment, the content ratio of the substituted PPS resin (A) to the styrene-based (co)polymer (C) is preferably 1.5 to 10.0, more preferably 2.0 to 9.5, and even more preferably 2.3 to 9.0, as expressed as the ratio (A / C) of (content of substituted PPS resin (A)) / (content of styrene-based (co)polymer (C)). In one embodiment, the value (A / C) may be 2.3, 2.4, 4.0, 4.7, or 9.0, or may be within the upper or lower limit of the above-mentioned range, or may be a combination of these.

[0072] The content of the radical polymerizable compound (B) in the resin composition is preferably 0 to 40 parts by mass, more preferably 5 to 40 parts by mass, even more preferably 8 to 38 parts by mass, even more preferably 10 to 35 parts by mass, and particularly preferably 15 to 35 parts by mass, per 100 parts by mass of the total of components (A) to (C). When the content of the radical polymerizable compound (B) is 5 parts by mass or more per 100 parts by mass of the total of components (A) to (C), the resin composition is more likely to cure at low temperatures. When the content is 40 parts by mass or less, the resin composition is more likely to have a low dielectric tangent. In one embodiment, the content of the radical polymerizable compound (B) in the resin composition may be 15 parts by mass or 32 parts by mass per 100 parts by mass of the total of components (A) to (C), or any combination thereof, or may be a range with the upper or lower limit of the above range.

[0073] The content of the styrene-based (co)polymer (C) in the resin composition is preferably 5 to 40 parts by mass, more preferably 5 to 35 parts by mass, even more preferably 8 to 33 parts by mass, and particularly preferably 10 to 30 parts by mass, relative to 100 parts by mass of the total of components (A) to (C). When the content of the styrene-based (co)polymer (C) is 5 parts by mass or more relative to 100 parts by mass of the total of components (A) to (C), the toughness of the resin composition is likely to be improved. When the content is 40 parts by mass or less, an excessive decrease in the glass transition temperature can be prevented. In one embodiment, the content of the styrene-based (co)polymer (C) in the resin composition may be 10 parts by mass, 15 parts by mass, 20 parts by mass, or 30 parts by mass, relative to 100 parts by mass of the total of components (A) to (C), or any combination thereof, or may be a range with the upper or lower limit of the above range.

[0074] When the resin composition contains a radically polymerizable compound (B) and a styrene-based (co)polymer (C), the content ratio of the radically polymerizable compound (B) to the styrene-based (co)polymer (C) 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 (B / C) of (content of radically polymerizable compound (B)) / (content of styrene-based (co)polymer (C)). By having the ratio (B content) / (C content) be 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.

[0075] In one embodiment, the total content of the substituted PPS resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C) in the resin composition (100% by mass) 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. In one embodiment, the total content of the substituted PPS resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C) in the resin composition (100% by mass) may be 95% by mass or more, 98% by mass or more, or even 100% by mass.

[0076] (Organic Peroxide (D)) The resin composition preferably contains an organic peroxide (D). By containing the organic peroxide (D), when the resin composition does not contain the radical polymerizable compound (B) but contains the styrene-based (co)polymer (C), the resin composition is more likely to have a low dielectric tangent and to be cured at a low temperature.

[0077] Examples of the organic peroxide (D) 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 (D) may be one type, or two or more types may be contained.

[0078] The content of the organic peroxide (D) is preferably 0 to 100 parts by mass, more preferably 0.1 to 10 parts by mass, and even more preferably 0.5 to 5 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). When the content of the organic peroxide (D) is 0.1 parts by mass or more 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), the resin composition is likely to cure at low temperatures. When the content is 10 parts by mass or less, the resin composition is likely to have a low dielectric tangent.

[0079] (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.

[0080] (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).

[0081] 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.

[0082] (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 the mixture may be 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.

[0083] In one embodiment, the resin composition has a dielectric loss tangent at 10 GHz of preferably 0.003 or less, more preferably 0.002 or less, even 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 0.003 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.

[0084] In one embodiment, the resin composition has a dielectric loss tangent at 40 GHz of preferably 0.003 or less, more preferably 0.002 or less, and even more preferably less than 0.002. When the resin composition has a dielectric loss tangent at 40 GHz of 0.003 or less, transmission loss at 40 GHz can be easily suppressed when the resin composition is used as a material for a wiring board.

[0085] 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.

[0086] 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.

[0087] In one embodiment, the toughness of the resin composition, as measured by a simple mandrel test on a film-like cured product having a thickness of 100 μm, is preferably 40 mm or less in diameter, more preferably 30 mm or less in diameter, and even more preferably 20 mm or less in diameter. When the resin composition is used as a material for a wiring board, the wiring board is less likely to break even when stress is applied.

[0088] [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.

[0089] (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 the above-mentioned 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.

[0090] (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.

[0091] (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.

[0092] (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.

[0093] [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.

[0094] [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.

[0095] 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 ４are 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:

[0096] The resin composition can be cured at low temperatures, and therefore can be cured at a lower temperature than when the substituted PPS resin (A) is cured alone.

[0097] 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.

[0098] 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.

[0099] 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 ４ a resin composition comprising a substituted polyphenylene sulfide resin (A) containing a structural unit represented by the formula: [wherein one or more of the groups represented by the formula: is an alkyl group or an alkoxy group], a radical polymerizable compound (B), and / or a styrene-based (co)polymer (C). [2] The resin composition according to [1], which contains the substituted polyphenylene sulfide resin (A) and the styrene-based (co)polymer (C). [3] The resin composition according to [1] or [2], which contains the substituted polyphenylene sulfide resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C). [4] The resin composition according to any of [1] to [3], wherein the content of the substituted polyphenylene sulfide resin (A) is 30 to 95 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). [5] The resin composition according to any one of [1] to [4], wherein the content of the radical polymerizable compound (B) is 0 to 40 parts by mass relative to 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). [6] The resin composition according to any one of [1] to [5], wherein the content of the styrene-based (co)polymer (C) is 5 to 40 parts by mass relative to 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). [7] The resin composition according to any one of [1] to [6], wherein the substituted polyphenylene sulfide resin (A) contains an organic peroxide (D). [8] The substituted polyphenylene sulfide resin (A) is a compound represented by 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, and R ５ａ , R ６ａ , R ７ａ and R ８ａ

[0023] The resin composition according to any one of [1] to [7], containing a structural unit represented by the formula (I):

[0024] . [9] The resin composition according to any one of [1] to [8], wherein the styrene ratio of the styrene-based (co)polymer (C) is 20 to 100 mass%.

[10] The resin composition according to any one of [1] to [9], containing a solvent.

[11] An article for a wiring board, containing the resin composition according to any one of [1] to [9].

[12] The article according to

[11] , which is an interlayer insulating film, a prepreg, a metal-clad laminate, or a substrate.

[13] A wiring board, containing the resin composition according to any one of [1] to [9].

[14] A printed wiring board, containing the resin composition according to any one of [1] to [9] and an electronic component.

[15] A method for producing a printed wiring board, comprising curing a resin composition, wherein the resin composition is a structural unit represented by the 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 substituted polyphenylene sulfide resin (A) containing a structural unit represented by the formula:

[0100] 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.

[0101] Synthesis Example 1: Preparation of DMPPS In an argon atmosphere, 4.0 L of dichloromethane was introduced into a 10 L four-neck flask. 3,3',5,5'-tetramethyldiphenyl disulfide (1 kg, 3.64 mol), 2,3-dichloro-5,6-dicyano-parabenzoquinone (DDQ, 3.64 mol), and trifluoromethanesulfonic acid (2.55 mol) were added thereto, and the mixture was stirred at room temperature for 2 hours to carry out oxidative polymerization. The reaction solution was added dropwise to methanol acidified with hydrochloric acid, and the powder was collected by filtration. The powder was then washed with an aqueous potassium hydroxide solution (0.1 M) and pure water and dried under vacuum to obtain 2,6-dimethyl PPS resin (DMPPS) as a polymer corresponding to substituted PPS resin (A). This substituted PPS resin (A) is a polymer represented by the general formula (I) R １ and R ４ is a methyl group, and R ２ and R ４ has a structural unit in which １ The content of the methyl group-containing structural unit was calculated by H-NMR and found to be 100 mol% in the substituted PPS resin. The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resulting polymer were measured by gel permeation chromatography (GPC), and found to be Mw 26,000 and Mn 5,800.

[0102] Synthesis Example 2: 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 2% 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 ４ is H.１ The content of each structural unit was calculated by H-NMR, and it was found that the content of structural unit A (vinyl group- and methyl group-containing structural unit) in the substituted PPS resin was 2 mol %, and the content of structural unit B (methyl group-containing structural unit) in the substituted PPS resin was 98 mol %. The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the obtained polymer were measured by gel permeation chromatography (GPC), and it was found that Mw was 30,000 and Mn was 8,600.

[0103] [Materials] The materials used in the examples and comparative examples are as follows: (Main component) A1: Polyphenylene ether (PPE), "SA9000" manufactured by SABIC A2: Polymer obtained in Synthesis Example 2 (VDMPPS: 2,6-dimethyl PPS resin in which 7% of the methyl groups are substituted with vinyl groups) A3: Polymer obtained in Synthesis Example 1 (DMPPS: 2,6-dimethyl PPS resin)

[0104] (Radical polymerizable compounds) B1: triallyl isocyanurate, "TAIC" manufactured by Nippon Kasei Chemical Industry Co., Ltd., molecular weight 249.7 B2: "DD-1" manufactured by Shikoku Chemical Industry Co., Ltd. B3: 1,2-bis(4-vinylphenyl)ethane (BVPE), molecular weight 234.3

[0105] (Styrene-based (co)polymers) C1: Hydrogenated methylstyrene (ethylene / ethylenepropylene) methylstyrene copolymer, "Septon (registered trademark) V9461" manufactured by Kuraray Co., Ltd., styrene ratio (catalog value) 30% by mass. C2: Styrene-ethylene / butadiene-styrene copolymer, "Septon (registered trademark) 8007L" manufactured by Kuraray Co., Ltd., styrene ratio (catalog value) 30% by mass. C3: General-purpose polystyrene (PS), weight average molecular weight (Mw) 150,000, styrene ratio 100% by mass. C4: Styrene-ethylene / butadiene-styrene (SEBS), "Tuftec (registered trademark) P5051" manufactured by Asahi Kasei Corporation, styrene ratio (catalog value) 49% by mass. C5: Styrene-ethylene / butadiene-styrene (SEBS), "Tuftec (registered trademark) P2000" manufactured by Asahi Kasei Corporation, styrene ratio (catalog value) 68% by mass. C6: Styrene-ethylene / butadiene-styrene (SEBS), Asahi Kasei Corporation's "Tuftec (registered trademark) S1609", styrene ratio (catalog value) 68% by mass. C7: Styrene-ethylene / butadiene-styrene (SEBS), Asahi Kasei Corporation's "Tuftec (registered trademark) S1611", styrene ratio (catalog value) 62% by mass. C8: Styrene-ethylene / butadiene-styrene (SEBS), Asahi Kasei Corporation's "Tuftec (registered trademark) H1043", styrene ratio (catalog value) 67% by mass.

[0106] (Organic peroxide) D1: 1,3-bis(butylperoxyisopropyl)benzene (NOF Corporation, "Perbutyl P") (Solvent) Toluene

[0107] Example 1 The VMPPS (4.8 g) obtained in Synthesis Example 2 was dissolved in toluene (10 g). Further, a radically polymerizable compound B2 (DD-1 manufactured by Shikoku Chemical Industry Co., Ltd., 3.2 g), a styrene-based thermoplastic elastomer D1 (Hybler 8007L manufactured by Kuraray Co., Ltd., 2.0 g), and an organic peroxide D1 (Perbutyl P manufactured by NOF Corporation, 0.2 g) were added, and the mixture was stirred at 50°C for 2 hours to obtain a varnish, which is a resin composition.

[0108] Examples 2 to 10, Comparative Examples 1 to 9 Using the blending amounts shown in Table 1 or 2, a varnish, which is a resin composition, was obtained in the same manner as in Example 1.

[0109] Comparative Example 10 The DMPPS powder obtained in Synthesis Example 1 was used alone.

[0110] Comparative Example 11 The VMPPS powder obtained in Synthesis Example 2 was used alone.

[0111] [Preparation of Cured Product] (Drying Step) The varnishes obtained in Examples 1 to 10 and Comparative Examples 1 to 9 were poured into polytetrafluoroethylene petri dishes and dried on a hot plate at 130° C. for 5 minutes. The obtained film-like solid was crushed and dried again on a hot plate at 130° C. for 5 minutes to obtain a powdery solid.

[0112] (Curing step) The powder solid (approximately 1 g) obtained in the drying step and a 120 μm polyimide film as a spacer were sandwiched between polytetrafluoroethylene films and vacuum-pressed using a vacuum press. The temperature was raised from 80° C. at a rate of 20° C. / min and held 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 100 μm and a diameter of approximately 10 cm.

[0113] For Comparative Examples 10 and 11, the DMPPS powder obtained in Synthesis Example 1 (Comparative Example 10) or the VMPPS powder obtained in Synthesis Example 2 (Comparative Example 11) was used directly without a drying step to obtain a film-like cured product. Specifically, the DMPPS powder obtained in Synthesis Example 1 (or the VMPPS powder obtained in Synthesis Example 2) and a 120 μm polyimide film as a spacer were sandwiched between polytetrafluoroethylene films and vacuum-pressed using a vacuum press. The temperature was increased from 160°C at a rate of 20°C / min and held at 245°C for 2 hours. A pressure of 2 kN was applied when the hot plate temperature was 235°C, and a pressure of 5 kN was applied at 245°C, obtaining a film-like cured product with a thickness of approximately 100 μm and a diameter of approximately 10 cm.

[0114] [Evaluation] Various physical properties were measured by the following methods. The results are shown in Tables 1 to 3. (Measurement of dielectric loss tangent and dielectric constant) The dielectric loss tangent and dielectric constant were measured using the film-like cured products obtained by the above methods. The dielectric loss tangent and dielectric constant were 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%.

[0115] (Toughness) Cylindrical tubes with diameters of 50 mm, 40 mm, 27 mm, 18 mm, 10 mm, or 5 mm were prepared, and the cured products (thickness: approximately 100 μm) obtained from the resin compositions of Examples 1 to 10 and Comparative Examples 10 and 11 were wrapped around the tubes so that they covered half of the circumference. If no cracks occurred, the result was rated "pass", and if cracks occurred, the result was rated "fail". Evaluation was performed in descending order of diameter, and if cracks occurred, evaluation of smaller diameters was not performed.

[0116] (Transparency) The film-like cured products (thickness: approximately 100 μm) obtained by the above method were visually observed for cloudiness, and the film-like cured products were placed on a piece of paper with letters of font size 14 written on it to determine whether the letters could be read visually. Film-like cured products that were not cloudy or that had cloudiness but the letters were readable were rated as "transparent," and films that were cloudy and the letters were unreadable were rated as "cloudy." Transparent film-like cured products are compatible with resins and can be preferably used in applications requiring high insulation reliability.

[0117]

[0118] As shown in Table 1, the resin compositions of Examples 1 to 10 all had a dielectric dissipation factor of 0.002 or less at 10 GHz, thereby achieving a low dielectric dissipation factor. Furthermore, they could be cured at a low temperature of 200°C. Furthermore, as shown in Table 3, the resin compositions of Examples 1 to 10 did not crack even when wound around a narrow tube with a diameter of 27 mm, providing the additional benefit of excellent toughness. By adjusting the styrene ratio and content of the styrene (co)polymer (C) as in Examples 1, 3, and 6, no cracks occurred even when wound around a tube with an even narrower diameter of 10 mm, providing the additional benefit of excellent toughness. In contrast, the resin compositions of Comparative Examples 1 to 9 were examples using a substituted PPE resin, resulting in a dielectric dissipation factor exceeding 0.003. Comparative Examples 10 and 11 were examples using a substituted PPS resin alone (i.e., without the radical polymerizable compound (B) and / or the styrene (co)polymer (C)), and they did not cure unless the temperature exceeded 240°C. Furthermore, as shown in Table 3, the resin compositions of Comparative Examples 10 and 11 cracked even when wrapped around a thick tube having a diameter of 50 mm or 40 mm, resulting in poor toughness.

[0119] The resin composition of the present embodiment has a low dielectric loss tangent and can be cured at low temperatures, 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, comprising the substituted polyphenylene sulfide resin (A) and the styrene-based (co)polymer (C).

3. The resin composition according to claim 1, comprising the substituted polyphenylene sulfide resin (A), the radical polymerizable compound (B), and the styrene-based (co)polymer (C).

4. The resin composition according to claim 1, wherein the content of the substituted polyphenylene sulfide resin (A) is 30 to 95 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).

5. The resin composition according to claim 1, wherein the content of the radical polymerizable compound (B) is 0 to 40 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).

6. The resin composition according to claim 1, wherein the content of the styrene-based (co)polymer (C) is 5 to 40 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).

7. The resin composition according to any one of claims 1 to 6, further comprising an organic peroxide (D).

8. 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 The resin composition according to claim 1 , comprising a structural unit represented by the following formula:

9. The resin composition according to any one of claims 1 to 6, wherein the styrene ratio of the styrene-based (co)polymer (C) is 20 to 100 mass%.

10. The resin composition according to any one of claims 1 to 6, further comprising a solvent.

11. An article for wiring boards, comprising the resin composition according to any one of claims 1 to 6.

12. The article of claim 11, which is an interlaminar dielectric film, a prepreg, a metal clad laminate, or a substrate.

13. A wiring board comprising the resin composition according to any one of claims 1 to 6.

14. A printed wiring board comprising the resin composition according to any one of claims 1 to 6 and an electronic component.

15. A method for producing a resin composition comprising curing a resin composition, the resin composition being 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, R １ , R ２ , R ３ , and R ４ wherein one or more of the radical polymerizable group is an alkyl group or an alkoxy group; and a radical polymerizable compound (B), and / or a styrene-based (co)polymer (C), wherein the curing step comprises heating the resin composition at a temperature of 240° C. or less.

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