Curable resin material, prepreg, resin film, metal-clad laminate, printed wiring board, and semiconductor package

Abstract

This curable resin material comprises a polymerizable group-containing compound (A) and an inorganic filler (B), wherein the polymerizable group-containing compound (A) includes a resin (A1) containing an indene ring, a vinylbenzyl group, and an arylalkyl group other than the vinylbenzyl group.

Description

Curable resin materials, prepregs, resin films, metal-clad laminates, printed circuit boards, and semiconductor packages 【0001】 This disclosure relates to curable resin materials, prepregs, resin films, metal-clad laminates, printed circuit boards, and semiconductor packages. 【0002】 In various electronic devices such as smartphones and other mobile communication devices, their base station equipment, servers, routers and other network infrastructure equipment, personal computers, industrial computers, large-scale computers, home appliances, and automobiles, the development of communication technology is leading to faster and larger data transmission speeds and capacities, and there is a need for the development of semiconductor-related materials that can cope with these changes. 【0003】 For example, resin materials used in printed circuit boards such as motherboards, package substrates, optical communication modules, daughterboards, and server boards require the development of materials with lower dielectric constants and dielectric loss tangents, and lower transmission loss, in order to support high-speed and high-capacity information transmission in the high-frequency range. Furthermore, with the increasing integration of semiconductors, the enlargement of substrate sizes, and the transformation of package structures such as chiplets, lowering the coefficient of thermal expansion (CTE) of the substrate material is also an important performance requirement, enabling reduced warping and improved connection reliability. 【0004】 Patent Document 1 discloses a resin composition for circuit boards that can improve the flame retardancy of the cured product while reducing its dielectric loss tangent, comprising polyphenylene ether, a bismaleimide compound and triallyl isocyanurate which are crosslinking agents that react with the polyphenylene ether, a filler, and a cyclic urea compound. 【0005】 Japanese Patent Publication No. 2022-39594 【0006】 Patent Document 1 measures the dielectric loss tangent and thermal expansion coefficient (CTE) in a prepreg containing a cured resin composition, but the dielectric loss tangent value does not meet current market requirements. Furthermore, regarding the thermal expansion coefficient (CTE), there is no mention of the thermal expansion coefficient in the Z-axis direction, where the constraint by glass fibers is small and expansion is more likely. 【0007】One of the objectives of this disclosure is to provide curable resin materials, prepregs, resin films, metal-clad laminates, printed circuit boards, and semiconductor packages that have low dielectric loss tangent and low coefficient of thermal expansion (CTE) in the cured product. 【0008】 This disclosure includes, but is not limited to, the following embodiments. One embodiment relates to a curable resin material comprising a polymerizable group-containing compound (A) and an inorganic filler (B), wherein the polymerizable group-containing compound (A) comprises a resin (A1) containing an indene ring, a vinylbenzyl group, and an arylalkyl group other than a vinylbenzyl group. 【0009】 This disclosure makes it possible to provide curable resin materials, prepregs, resin films, metal-clad laminates, printed circuit boards, and semiconductor packages that have low dielectric loss tangent and low coefficient of thermal expansion (CTE) in the cured product. 【0010】 The curable resin material of one embodiment has the characteristic of having a small coefficient of thermal expansion in the Z direction when made into a prepreg. Therefore, for example, it can ensure the reliability of thermal cycling in high-density stacked laser vias. 【0011】 The embodiments of the present invention will be described in detail below. The present invention is not limited to the embodiments described below. 【0012】 In this disclosure, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described stepwise in this disclosure, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range. Furthermore, the upper or lower limits of numerical ranges described in this disclosure may be replaced with the values ​​shown in the examples. In this disclosure, each component may contain one or more of the corresponding substances unless otherwise specified. In this disclosure, the content of each component in the curable resin material means the total amount of the multiple substances present in the curable resin material if there are multiple substances corresponding to each component in the curable resin material, unless otherwise specified. 【0013】In the present disclosure, unless otherwise specified, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) are values measured by the following procedure. The weight-average molecular weight and number-average molecular weight are converted from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). The calibration curve is approximated by a cubic equation using standard polystyrene: TSKstandard POLYSTYRENE (Type; A-2500, A-5000, F-20, F-80) (manufactured by Tosoh Corporation, trade name). The conditions of GPC are shown below. 【0014】 Apparatus: High-speed GPC apparatus "HLC-8320GPC" (manufactured by Tosoh Corporation, trade name) Detector: Ultraviolet absorption detector "UV-8320" (manufactured by Tosoh Corporation, trade name) Column: Guard column; TSKgel guardcolumn Super (HZ)-M+, Column; TSKgel SuperMultipore HZ-M (two), Reference column; TSKgel SuperH-RC (two) (all manufactured by Tosoh Corporation, trade name) Column size: 4.6×20 mm (guard column), 4.6×150 mm (column), 6.0×150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10 mg / 1 mL Injection volume: 20 μL or 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40 °C 【0015】 The curable resin material which is one embodiment of the present disclosure contains a polymerizable group-containing compound (A) and an inorganic filler (B), and the polymerizable group-containing compound (A) contains a resin (A1) containing an indene ring, a vinylbenzyl group, and an arylalkyl group other than the vinylbenzyl group (hereinafter this may be referred to as "resin (A1)"), and is a curable resin material. 【0016】 The resin (A1) contained in the polymerizable group-containing compound (A) is not limited with respect to the specific structure, molecular weight, etc. of the resin as long as it contains an indene ring, a vinylbenzyl group, and an arylalkyl group other than the vinylbenzyl group in the resin. The resin (A1) contained in the polymerizable group-containing compound (A) may be one kind or two or more kinds. In the resin (A1), the vinylbenzyl group and the arylalkyl group other than the vinylbenzyl group may be directly bonded to the indene ring. 【0017】 Regarding the vinylbenzyl group contained in the resin (A1), the vinylbenzyl group may be any of an o-vinylbenzyl group, a m-vinylbenzyl group, or a p-vinylbenzyl group. Among them, since it becomes a compound excellent in dielectric properties in the cured product, a p-vinylbenzyl group is preferable. The proportion of the p-vinylbenzyl group in all the vinylbenzyl groups contained in the resin (A1) may be 10 mol% or more, may be 20 mol% or more, and may be 30 mol% or more. Also, it may be 100 mol% or less, may be 80 mol% or less, and may be 70 mol% or less. The proportion of the p-vinylbenzyl group in all the vinylbenzyl groups contained in the resin (A1) may be in the range of 10 to 100 mol%. When the proportion of the p-vinylbenzyl group is less than 100 mol%, the remaining vinylbenzyl group may be a m-vinylbenzyl group. 【0018】 Regarding the arylalkyl group other than the vinylbenzyl group contained in the resin (A1) (hereinafter this may be referred to as "arylalkyl group"), the number of carbon atoms of the alkyl group in the arylalkyl group is not particularly limited, but may be, for example, in the range of 1 to 6. Also, the alkyl group may be linear or may have a branched structure. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, an n-hexyl group, an isohexyl group, etc. Among them, since it becomes a compound excellent in dielectric properties, it is preferable that the alkyl group in the arylalkyl group has a relatively small number of carbon atoms. For example, the alkyl group in the arylalkyl group may be a methyl group or an ethyl group, and may be a methyl group. 【0019】The aryl group in the arylalkyl group is not particularly limited as long as it is other than a styryl group. Examples thereof include a phenyl group, a naphthyl group, and a structural moiety having one or more substituents on these aromatic rings. Examples of the substituent on the aromatic ring include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, an n-hexyl group, or an isohexyl group; an alkoxy group represented by RO—, where R is the aforementioned alkyl group; a polymerizable group such as a vinyl group, a vinyloxy group, an allyl group, an allyloxy group, a (meth)acryloyl group, or a (meth)acryloyloxy group; an aryl group such as a phenyl group, a tolyl group, a xylyl group, a mesityl group, or a naphthyl group; an aryloxy group such as a phenyloxy group, a tolyloxy group, a xylyloxy group, a mesityloxy group, or a naphthyloxy group, and the like. 【0020】 The arylalkyl group may not have a polymerizable group. The aryl group in the arylalkyl group may be a phenyl group, a naphthyl group, or a group having 1 to 3 alkyl groups having 1 to 3 carbon atoms on these aromatic rings. 【0021】 As an example of the resin (A1), at least two compounds having different structures among the compounds represented by the following general formula (1) are included, and R present in the resin １ , R ２ and R ３ Among them, at least one is a vinylbenzyl group, and the resin (A1-1) in which at least one of R １ , R ２ and R ３ is an arylalkyl group other than a vinylbenzyl group can be mentioned. 【0022】 【0023】 [In the general formula (1), R １ , R ２ and R ３Each of these is independently a hydrogen atom, a vinylbenzyl group, or an arylalkyl group other than a vinylbenzyl group. ４ is a hydrogen atom, a monovalent organic group, or a halogen atom, and has four R ４ All of them may be different from each other, and there are four R's. ４ Two or more of them may be identical. 【0024】 R in general formula (1) １ , R ２ and R ３ Each of these is independently a hydrogen atom, a vinylbenzyl group, or an arylalkyl group other than a vinylbenzyl group. Details of the arylalkyl groups other than a vinylbenzyl group are as described above. 【0025】 R in general formula (1) ４ The atoms are hydrogen atoms, monovalent organic groups, or halogen atoms. Examples of monovalent organic groups include alkyl groups with 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and isohexyl groups; alkoxy groups represented as RO-, where R is one of the aforementioned alkyl groups; polymerizable unsaturated bond-containing groups, such as vinyl, vinyloxy, allyl, allyloxy, (meth)acryloyl, and (meth)acryloyloxy groups; aryl groups, such as phenyl, tolyl, xylyl, mesityl, and naphthyl groups; and aryloxy groups, such as phenyloxy, tolyloxy, xylyloxy, mesityloxy, and naphthyloxy groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R in general formula (1) ４ All of them may be hydrogen atoms. 【0026】 In resin (A1-1), R present in the resin １ , R ２ and R ３ At least one of them is a vinylbenzyl group, and at least one is an arylalkyl group. The resin (A1-1) is R in general formula (1). １ , R ２ and R ３A compound in which one of the atoms is a vinylbenzyl group, one is an arylalkyl group, and one is a hydrogen atom, R １ , R ２ and R ３ A compound in which two of the groups are vinylbenzyl groups and one is an arylalkyl group, R １ , R ２ and R ３ A compound in which one of the groups is a vinylbenzyl group and the other two are arylalkyl groups, R １ , R ２ and R ３ A compound in which 1 to 3 of the groups are vinylbenzyl groups and the others are hydrogen atoms, R １ , R ２ and R ３ A compound in which one to three of the atoms are arylalkyl groups and the others are hydrogen atoms, R １ , R ２ and R ３ The compound may contain at least two compounds in which all atoms are hydrogen atoms. In a compound having multiple arylalkyl groups in one molecule, the arylalkyl groups may all be different, or some or all of them may be the same. 【0027】 In resin (A1-1), the average of the total number of vinylbenzyl groups and arylalkyl groups in one molecule is preferably 1.5 or higher, more preferably 1.8 or higher, and particularly preferably 2.0 or higher, as this results in excellent curability. It may also be 3.0 or lower, 2.8 or lower, or 2.5 or lower. The average of the total number of vinylbenzyl groups and arylalkyl groups in one molecule may be in the range of 1.5 to 3.0. 【0028】 Furthermore, the ratio of vinylbenzyl groups to the total number of vinylbenzyl groups and arylalkyl groups present in the resin (A1-1) may be 30 mol% or more, 60 mol% or more, or 85 mol% or more. It may also be 99 mol% or less, 95 mol% or less, or 80 mol% or less. The ratio of vinylbenzyl groups to the total number of vinylbenzyl groups and arylalkyl groups may be in the range of 30 to 99 mol%. 【0029】 Resin (A1-1) is a compound identified by its molecular structure, and its manufacturing method is not particularly limited. One example of a method for producing resin (A1-1) is to react indene, styrene having a methyl halide group, and an aromatic compound having an alkyl halide corresponding to an arylalkyl group in the presence of a basic compound. 【0030】 Examples of styrenes having a methyl halide group include o-chloromethylstyrene, m-chloromethylstyrene, and p-chloromethylstyrene. These may be used individually or in combination of two or more. Examples of aromatic compounds having an alkyl halide include α-chlorotoluene, α-chloroxylene, and 1-(chloromethyl)naphthalene. These may be used individually or in combination of two or more. 【0031】 The ratio of styrene having a methyl halide group to the total number of moles of styrene having a methyl halide group and aromatic compounds having an alkyl halide group may be 30 mol% or more, 60 mol% or more, or 85 mol% or more. It may also be 99 mol% or less, 95 mol% or less, or 80 mol% or less. The ratio of styrene having a methyl halide group to the total number of moles of styrene having a methyl halide group and aromatic compounds having an alkyl halide group may be in the range of 30 to 99 mol%. 【0032】 The total number of moles of styrene having a methyl halide group and an aromatic compound having an alkyl halide per mole of indene may be 1.5 moles or more, 1.8 moles or more, or 2.0 moles or more. It may also be 3.0 moles or less, 2.8 moles or less, or 2.5 moles or less. The total number of moles of styrene having a methyl halide group and an aromatic compound having an alkyl halide per mole of indene may be in the range of 1.5 to 3.0 moles. 【0033】Examples of basic compounds include alkali metal hydroxides and alkali metal alkoxides. These may be used individually or in combination of two or more. 【0034】 A phase-transfer catalyst may be used in the above reaction. Examples of phase transfer catalysts include quaternary ammonium salts such as tetra-n-butylammonium chloride, tetra-n-butylammonium bromide (tetra-n-butylammonium bromide), tetraethylammonium chloride, tetraethylammonium bromide, tetrapropylammonium chloride, tetrapropylammonium bromide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltributylammonium chloride, benzyltributylammonium bromide, benzyldimethyltetradecylammonium chloride, tricaprylmethylammonium chloride, tetradecyltrimethylammonium bromide, hexadecyltrimethylammonium bromide, trioctylmethylammonium chloride, and tetra-n-butylammonium bisulfate; and quaternary phosphonium salts such as tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, benzyltriphenylphosphonium chloride, and benzyltriphenylphosphonium bromide. These may be used individually or in combination of two or more types. 【0035】 The above reaction may be carried out, for example, under heating and stirring conditions. The heating temperature may be around 50 to 100°C. The above reaction can also be carried out by solution polymerization. The solvent used is not particularly limited as long as it can dissolve the reaction raw materials and has a boiling point above the reaction temperature, but examples include aromatic hydrocarbon solvents such as toluene, xylene, and mesitylene. These may be used individually or in combination of two or more. 【0036】Polymerization inhibitors may be used in the reaction system as needed. Examples of polymerization inhibitors include hydroquinone, methylhydroquinone, t-butylhydroquinone, 2,6-di-t-butylhydroquinone, 2,5-di-t-butylhydroquinone, hydroquinone monomethyl ether, 1,4-benzoquinone, 2-t-butyl-1,4-benzoquinone, 2-t-butylphenol, 2,4-di-t-butylphenol, 2,6-di-t-butylphenol, cresol, catechol, 4-t-butylcatechol, pyrogallol, and 4 Examples include methoxyphenol, thiodiphenylamine, phenothiazine, 3,7-dioctylphenothiazine, 3,7-dicumylphenothiazine, 2,2,6,6-tetramethylpiperidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate. These may be used individually or in combination of two or more. 【0037】 The product obtained from the above reaction may be purified by known methods such as concentration, reprecipitation, and washing, if necessary. 【0038】 Another example of resin (A1) is a prepolymer (A1-2) obtained by polymerizing some of the vinyl groups in resin (A1-1). In this disclosure, a prepolymer is a polymer in which some of the polymerizable groups in the raw material remain without undergoing a polymerization reaction, and which has curability due to the remaining polymerizable groups. 【0039】 The prepolymer (A1-2) may be prepared by combining resin (A1-1) with other reaction materials other than resin (A1-1). The proportion of resin (A1-1) in the total reaction materials of the prepolymer (A1-2) may be 50 mol% or more, 80 mol% or more, or 100 mol%. 【0040】The method for producing the prepolymer (A1-2) is not particularly limited and can be produced by polymerizing reaction materials containing resin (A1-1) using a general method. One example of such a method is radical polymerization. 【0041】 Polymerization initiators used in radical polymerization are not particularly limited, and examples include azo polymerization initiators and organic peroxide polymerization initiators. Examples of azo polymerization initiators include 2,2'-azobis(2,4,4-trimethylpentane), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 1,1'-azobis(cyclohexane-1-carbonitride), and dimethyl-1 Examples include 1'-azobis(1-cyclohexanecarboxylate), 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 4,4'-azobis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl4-cyanopentanoate), etc. Examples of organic peroxide polymerization initiators include dicumyl peroxide, dibenzoyl peroxide, 2-butanone peroxide, t-butyl perbenzoate, di-t-butyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, bis(t-butylperoxyisopropyl)benzene, and t-butyl hydroperoxide. These may be used individually or in combination of two or more. 【0042】 Polymerization reactions may be carried out in a solvent. Examples of solvents that can be used include toluene and xylene. These may be used individually or in combination of two or more. 【0043】The weight-average molecular weight (Mw) of the prepolymer (A1-2) is not particularly limited, but for example, from the viewpoint of ease of manufacture and ease of handling of the curable resin material, it may be 1,000 or more, 2,000 or more, or 3,000 or more. It may also be 15,000 or less, 10,000 or less, or 8,000 or less. The weight-average molecular weight (Mw) of the prepolymer (A1-2) may be in the range of 1,000 to 15,000. 【0044】 Examples of polymerizable group-containing compounds (A) other than resin (A1) include compounds having a maleimide group, polyarylene ether compounds having polymerizable groups, aromatic compounds having a vinyl group, triallyl isocyanurate, and the like. 【0045】 Examples of compounds having a maleimide group include bismaleimide compounds and maleimide resins. 【0046】Specific examples of bismaleimide compounds include, for example, N,N'-ethylenebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'-[1,3-(2-methylphenylene)]bismaleimide, N,N'-[1,3-(4-methylphenylene)]bismaleimide, N,N'-(1,4-phenylene)bismaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4-maleimidophenyl)methane, and 3,3'-dimethyl-5,5'-die Tyl-4,4'-diphenylmethanebismaleimide, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)sulfone, bis(4-maleimidophenyl)sulfide, bis(4-maleimidophenyl)ketone, bis(4-maleimidocyclohexyl)methane, 1,4-bis(4-maleimidophenyl)cyclohexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,4-bis(maleimidomethyl)benzene, 1,3-bis(4-maleimidophenoxy)benzene, 1,3-bis(3- Maleimidophenoxy)benzene, bis[4-(3-maleimidophenoxy)phenyl]methane, bis[4-(4-maleimidophenoxy)phenyl]methane, 1,1-bis[4-(3-maleimidophenoxy)phenyl]ethane, 1,1-bis[4-(4-maleimidophenoxy)phenyl]ethane, 1,2-bis[4-(3-maleimidophenoxy)phenyl]ethane, 1,2-bis[4-(4-maleimidophenoxy)phenyl]ethane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]propane , 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 4,4-bis(3-maleimidophenoxy)biphenyl, 4,4-bis(4-maleimidophenoxy)biphenyl, bis[4-(3-maleimidophenoxy)phenyl]ketone, bis[4-(4-maleimidophenoxy)phenyl]ketone, bis(4-maleimidophenoxy)disulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfide, bis[4-(4-maleimidophenoxy)phenyl]sulfide, bis[4-(3-maleimidophenoxy)phenyl ] sulfoxide, bis[4-(4-maleimidophenoxy)phenyl] sulfoxide, bis[4-(3-maleimidophenoxy)phenyl] sulfone, bis[4-(4-maleimidophenoxy)phenyl] sulfone, bis[4-(3-maleimidophenoxy)phenyl] ether, bis[4-(4-maleimidophenoxy)phenyl] ether, 1,4-bis[4-(4-maleimidophenoxy)-α,α-dimethicone Rubenzyl]benzene, 1,3-bis[4-(4-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(3-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(3-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(4-maleimidophenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene Examples include 1,3-bis[4-(4-maleimidophenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(3-maleimidophenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(3-maleimidophenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, and aromatic bismaleimide compounds having an indane skeleton. 【0047】 Specific examples of maleimide resins include, for example, polyphenylmethane maleimide, maleimide resins having an indan skeleton, and biphenyl aralkyl type maleimide resins. 【0048】 Maleimide resins having an indan skeleton include, for example, those represented by the following general formula (2). 【0049】 【0050】 [R in general formula (2)]５ [where a is a hydrogen atom or a methyl group, and a is an integer of 1 or more.] 【0051】 Examples of biphenylaralkyl-type maleimide resins include those represented by the following general formula (3). 【0052】 【0053】 [In general formula (3), b is an integer greater than or equal to 1.] 【0054】 Regarding polyarylene ether compounds having polymerizable groups, the arylene group is not particularly limited and examples include phenylene groups, naphthylene groups, and structures in which one or more alkyl groups, alkyloxy groups, halogen atoms, etc., are substituted on the aromatic carbons thereof. Examples of polymerizable groups include vinyl groups, vinyloxy groups, allyl groups, allyloxy groups, (meth)acryloyl groups, (meth)acryloyloxy groups, vinylbenzyl groups, vinylbenzyloxy groups, etc. Polyarylene ether compounds having polymerizable groups may have structural parts other than the polyarylene ether structure. Specifically, they may have acrylic polymerization sites, (poly)urethane sites, (poly)ester sites, etc., in the molecular chain. The number of polymerizable groups in one molecule of a polyarylene ether compound is not particularly limited, nor is the substitution position of the polymerizable groups particularly limited. For example, a polyarylene ether compound may have polymerizable groups at the molecular end, or it may have polymerizable groups at both ends. 【0055】 Specific examples of polyarylene ether compounds having polymerizable groups include, for example, resins represented by the following general formula (4). 【0056】 【0057】 [In general formula (4), R ６ R is a hydrogen atom or a methyl group. ７ [x] is one of the following: vinylbenzyl group, acryloyl group, or methacryloyl group. c and d are integers of 1 or greater. X is a directly bonded or divalent organic group. 【0058】In general formula (4), X is a directly bonded or divalent organic group, and its specific structure is not particularly limited, but examples include hydrocarbon groups having 1 to 6 carbon atoms, halogenated hydrocarbon groups, oxygen atoms, sulfur atoms, carbonyl groups, sulfonyl groups, etc. 【0059】 The molecular weight of the polyarylene ether compound having polymerizable groups is not particularly limited, but for example, the number average molecular weight (Mn) may be in the range of 1,000 to 5,000. 【0060】 Aromatic compounds having a vinyl group include, for example, styrene, divinylbenzene, and 1,2-bis(4-vinylphenyl)ethane. 【0061】 When a curable resin material contains polymerizable group-containing compounds (A) other than resin (A1), the proportion of resin (A1) in polymerizable group-containing compounds (A) is arbitrary. For example, the proportion of resin (A1) to the total mass of polymerizable group-containing compounds (A) may be 20% by mass or more, 30% by mass or more, or 40% by mass or more. It may also be 95% by mass or less, 90% by mass or less, or 80% by mass or less. The proportion of resin (A1) to the total mass of polymerizable group-containing compounds (A) may be in the range of 20 to 95% by mass, for example. 【0062】 Inorganic filler (B) is, for example, silica (SiO ２ ), alumina (Al ２ O ３Examples include titanium dioxide, barium titanate, strontium titanate, potassium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, aluminum borate, silicon carbide, mica, beryllia, clay, and talc. Among these, silica is preferred from the viewpoint of dielectric properties. The type of silica is not particularly limited and may be crystalline silica or amorphous silica, and may be natural silica or synthetic silica. The method of producing synthetic silica is also not particularly limited and may be wet silica such as colloidal silica, fumed silica (dry silica), or fused silica. The shape of silica is also not particularly limited and may be spherical silica, crushed silica, solid silica, porous silica, or hollow silica. Of these, spherical silica is preferred in that it becomes a curable resin material with excellent fluidity. Hollow silica is preferred in that the dielectric loss tangent in the cured product is lower. 【0063】 The shape and size of the filler are not particularly limited. The average particle diameter of the filler may be, for example, 0.01 to 20 μm, or 0.1 to 10 μm. Here, the average particle diameter of the filler is the particle diameter at the point corresponding to 50% of the cumulative value in the volume-based particle distribution obtained by laser diffraction scattering. 【0064】 In a curable resin material, the ratio of polymerizable group-containing compound (A) to inorganic filler (B) is arbitrary, but from the viewpoint of obtaining a curable resin material with even lower dielectric loss tangent and coefficient of thermal expansion (CTE) in the cured product, it is preferable that the ratio of inorganic filler (B) to 100 parts by mass of total polymerizable group-containing compound (A) be 110 parts by mass or more, more preferably 150 parts by mass or more, and particularly preferable 180 parts by mass or more. It may also be 300 parts by mass or less, 250 parts by mass or less, or 230 parts by mass or less. The ratio of inorganic filler (B) to 100 parts by mass of total polymerizable group-containing compound (A) may be in the range of 110 to 300 parts by mass, and is preferably in the range of 180 to 230 parts by mass. 【0065】The curable resin material may, if necessary, contain other components besides the polymerizable group-containing compound (A) and the inorganic filler (B). Examples of other components include other thermosetting compounds having reactive groups other than polymerizable groups, elastomers, curing accelerators, flame retardants, antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, colorants, lubricants, solvents, etc. Each of these other components may be used individually or in combination of two or more types. 【0066】 Other thermosetting compounds include, for example, epoxy resins, phenolic resins, cyanate resins, benzoxazine resins, oxetane resins, amino resins, silicone resins, triazine resins, melamine resins, and the like. The ratio of polymerizable group-containing compound (A) to the total mass of polymerizable group-containing compound (A) and other thermosetting compounds may be 60% by mass or more, 80% by mass or more, 90% by mass or more, or 100% by mass. 【0067】 Examples of elastomers include polyether-based elastomers, styrene-based elastomers, conjugated diene-based elastomers, urethane-based elastomers, polyester-based elastomers, polyamide-based elastomers, acrylic-based elastomers, and silicone-based elastomers. 【0068】 Generally, elastomers have low dielectric loss tangents, and by adding them, the dielectric loss tangent of the curable resin material can be kept low. On the other hand, in the curable resin material of one embodiment, since the dielectric loss tangent of the cured resin (A1) is low, a curable resin material with a sufficiently low dielectric loss tangent can be obtained even if no elastomer is added or only a small amount is added. 【0069】Furthermore, while adding a high proportion of inorganic filler (B) is effective in keeping the coefficient of thermal expansion (CTE) of the curable resin material low, elastomers generally have large molecular weights, and curable resin materials containing a large amount of elastomers tend to have high melt viscosity, thus limiting the amount of inorganic filler (B) that can be added. When a large amount of elastomer is included and an inorganic filler is added in a high proportion, there is a concern that moldability problems may occur due to insufficient resin flow. As described above, in the curable resin material of one embodiment, the dielectric loss tangent of the cured resin (A1) is sufficiently low, and there is no need to add a large amount of elastomer, so it becomes possible to add inorganic filler (B) in a high proportion, and as a result, a curable resin material can be obtained in which both the dielectric loss tangent and the coefficient of thermal expansion (CTE) of the cured product are low. 【0070】 The elastomer content of the curable resin material may be 10% by mass or less, 5% by mass or less, or 1% by mass or less, based on the total mass of the polymerizable group-containing compound (A). Furthermore, the curable resin material may not contain elastomer at all. 【0071】For example, a radical polymerization initiator can be used as a curing accelerator. The radical polymerization initiator may be a thermal radical polymerization initiator or a photoradical polymerization initiator, but a thermal radical polymerization initiator is preferred. Specific examples of polymerization initiators include azo polymerization initiators and organic peroxide polymerization initiators. Examples of azo polymerization initiators include 2,2'-azobis(2,4,4-trimethylpentane), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 1,1'-azobis(cyclohexane-1-carbonitride), and dimethyl-1,1'-azobis(1-cyclohexanecarboxylate). Examples include 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and 4,4'-azobis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl4-cyanopentanoate). Examples of organic peroxide polymerization initiators include dicumyl peroxide, dibenzoyl peroxide, 2-butanone peroxide, t-butyl perbenzoate, di-t-butyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyn-3, α,α'-di(t-butylperoxy)diisopropylbenzene, and t-butyl hydroperoxide. 【0072】 The content of the curing accelerator in the curable resin material is not particularly limited, but for example, it may be 0.05 parts by mass or more, 0.1 parts by mass or more, or 0.5 parts by mass or more, per 100 parts by mass of the polymerizable group-containing compound (A). Alternatively, it may be 8 parts by mass or less, 5 parts by mass or less, or 3 parts by mass or less. The content of the curing accelerator may be in the range of 0.05 to 8 parts by mass per 100 parts by mass of the polymerizable group-containing compound (A). 【0073】 Examples of flame retardants include phosphorus-based flame retardants, nitrogen-based flame retardants, silicone-based flame retardants, and inorganic flame retardants. The amount of flame retardant added is adjusted as appropriate depending on the type of flame retardant, the intended use of the curable composition, and the desired physical properties. For example, when using a phosphorus-based flame retardant, the amount can be adjusted by the phosphorus atom content in the curable resin material. Specifically, the phosphorus atom content relative to the total mass of the resin components in the curable resin material, that is, the total mass of the components excluding the inorganic filler (B) and optionally used solvent from the curable resin material, may be 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more. It may also be 20% by mass or less, 10% by mass or less, or 5% by mass or less. The phosphorus atom content relative to the total mass of the resin components in the curable resin material may be in the range of 0.1 to 20% by mass, for example. 【0074】 The curable resin material may be solvent-free or may contain a solvent. The solvent can adjust the viscosity of the curable resin material and further improve its coating properties. Organic solvents are preferred as the solvent. 【0075】 Examples of organic solvents include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, ethylene glycol monobutyl ether, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether-based solvents such as tetrahydrofuran; aromatic hydrocarbon-based solvents such as toluene, xylene, and mesitylene; nitrogen-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents such as dimethyl sulfoxide; and ester-based solvents such as γ-butyrolactone. 【0076】 If the curable resin material contains a solvent, the solid content of the curable resin material may be, for example, in the range of 30 to 95% by mass. 【0077】The method for producing curable resin materials is not particularly limited. One example of a method for producing curable resin materials is to add and mix a polymerizable group-containing compound (A), an inorganic filler (B), and optional components as needed. When mixing, the polymerizable group-containing compound (A), the inorganic filler (B), and optional components as needed may be mixed as is, or they may be dissolved or dispersed in a solvent before mixing. The mixing order of each component, temperature, time, and other conditions are not particularly limited and may be adjusted as appropriate according to the type of raw materials, production scale, production equipment, etc. 【0078】 [Prepreg] According to one embodiment, a prepreg containing a curable resin material or a semi-cured product of a curable resin material can be provided. This prepreg can be formed, for example, using a curable resin material and a fibrous substrate. With respect to the semi-cured product of the curable resin material, in this disclosure, the B-stage state in JIS K 6800 (1985) can be cited as one indicator of the semi-cured state. The prepreg may contain, for example, a curable resin material or a semi-cured product of a curable resin material and a fibrous substrate such as a sheet-like fibrous substrate. In the prepreg, the curable resin material may be in an uncured state, or it may be in a partially or entirely semi-cured state. 【0079】 A prepreg can be obtained, for example, by impregnating a fibrous substrate with a curable resin material and then drying it. Drying is preferably carried out at a temperature above which volatile components such as solvents that may be contained in the curable resin material are removed, and may also be carried out at a temperature above which the curable components contained in the curable resin material are partially cured, depending on the application. Furthermore, it is preferable that the drying is adjusted so that the curable resin contained in the curable resin material is not completely cured. From this viewpoint, the drying temperature may be, for example, 80 to 200°C, and the drying time may be, for example, 1 to 30 minutes, depending on the drying temperature, drying equipment, and its scale. 【0080】The fibrous base material may be woven, knitted, or nonwoven fabric. The fibrous base material may be provided in the form of chopped strand mat, roving, etc. The fiber material may be either inorganic or organic fiber. Examples of inorganic fibers include glass fiber and carbon fiber. Examples of glass fiber include E glass, NE glass, D glass, S glass, and Q glass. Examples of organic fibers include polyimide, polyester, and tetrafluoroethylene. The fibrous base material may use one type of fiber alone, or two or more types in combination. From the viewpoint of dielectric properties and heat resistance, inorganic fibers are preferred for the fibrous base material, and glass fibers are more preferred. 【0081】 The fibrous substrate can be appropriately selected depending on the application of the prepreg, but a sheet-like fibrous substrate is preferred. The sheet-like fibrous substrate may be, for example, various sheet-like fibrous substrates used in known laminates for electrical insulating materials. The thickness of the sheet-like fibrous substrate is not particularly limited, but for example, 0.01 to 0.1 mm is preferred. Here, the thickness is determined by measuring the thickness at five points at equal distances across the entire surface of the sheet-like fibrous substrate and taking the arithmetic mean of the five points. 【0082】 [Resin Film] According to one embodiment, a resin film can be provided that includes a curable resin material or a semi-cured product of a curable resin material. The resin film can be obtained, for example, by coating a material to be coated with a curable resin material and drying or semi-curing it. Drying or semi-curing can be carried out in the same manner as the manufacturing method of the prepreg described above. After drying the resin film on the material to be coated, the product may be provided as a combination of the resin film and the material to be coated. For example, in this method, the resin film can be provided as a surface protective film, an interlayer insulating film, etc., on a printed circuit board. In another method, after drying the resin film on the material to be coated, the resin film may be peeled off the material to provide the resin film as a product. 【0083】The material to be coated may be either an inorganic or organic substrate, and examples include glass substrates, metal foils, metal plates and other metal substrates, plastic plates, plastic films and other plastic substrates, paper substrates, and even fibrous substrates as described in the prepreg section above. In order to peel the resin film from the material to be coated and provide it, a material to be coated that has a release layer formed on its surface may be used. 【0084】 [Metal-clad laminate] According to one embodiment, a metal-clad laminate containing a cured product of a curable resin material and a metal foil can be provided. With respect to the cured product, in this disclosure, the state of the C-stage in JIS K 6800 (1985) can be cited as one indicator of the cured product. 【0085】 In a metal-clad laminate, the cured product of the curable resin material may be included as the cured product of the curable resin material itself, or it may be included in the form of a prepreg. The metal-clad laminate may include a prepreg layer and a metal foil placed on at least one surface of the prepreg layer. The prepreg layer is the cured product of the prepreg described above, and may consist of a single prepreg or multiple prepregs laminated together. Furthermore, the metal-clad laminate may have the metal foil placed on one surface of the curable resin material or the cured prepreg, or it may have the metal foil placed on both surfaces of the curable resin material or the cured prepreg. The metal-clad laminate may be manufactured by placing the metal foil on at least one surface of a single sheet-like prepreg, or it may be manufactured by laminating two or more sheet-like prepregs and placing the metal foil on at least one surface of the outermost layer of the laminate. A metal-clad laminate may be manufactured by laminating two or more sheet-like prepregs and arranging metal foil on both sides of this laminate. 【0086】 The following describes a specific method for manufacturing metal-clad laminates, which involves arranging metal foil on a laminate of two or more sheet-like prepregs. 【0087】First, two or more sheet-like prepregs are laminated to obtain a laminate. In this laminate, the two or more sheet-like prepregs may be identical, or they may be partially or completely different. In the laminate, it is sufficient that at least one of the two or more sheet-like prepregs is obtained using a curable resin material according to one embodiment. 【0088】 Next, a metal foil is placed on at least one surface of the laminate. The laminate with the metal foil is then heated and pressurized. This causes the sheet-like prepreg to harden, and a hardened prepreg product can be obtained. Adjacent sheet-like prepregs can also be bonded together. The heating and pressurizing conditions are not particularly limited, but for example, the temperature can be 100 to 300°C, the time 10 to 300 minutes, and the pressure 0.5 to 50 MPa. After heating and pressurizing, reheating may be performed to further harden the prepreg. In this case, the reheating temperature can be 100 to 300°C. As for the pressurizing method, for example, an autoclave molding machine, a multi-stage press machine, a multi-stage vacuum press machine, a continuous molding machine, etc., can be used. 【0089】 The metal used for the metal foil is not particularly limited and can include, for example, copper, nickel, aluminum, gold, silver, platinum, molybdenum, ruthenium, tungsten, iron, titanium, chromium, and alloys containing two or more of these metal elements. Industrially, it is preferable to use elemental copper, nickel, or aluminum. By using copper as the metal foil, a copper-clad laminate can be provided. 【0090】[Printed Wiring Board] According to one embodiment, a printed wiring board containing a cured product of a curable resin material can be provided. The curable resin material of one embodiment has the characteristic of having low dielectric loss tangent and low coefficient of thermal expansion (CTE) in the cured product, and can therefore be suitably used for substrate materials where a higher level of reduction in dielectric loss tangent and coefficient of thermal expansion (CTE) is required, such as for package substrates, optical communication modules, motherboards, daughterboards, server substrates, and other printed circuit boards. In the printed wiring board, the cured product of the curable resin material may be included as the cured product of the curable resin material itself, or it may be included in the form of a prepreg. The printed wiring board can be manufactured using a curable resin material, a prepreg, a metal-clad laminate, or a combination thereof. For example, a printed wiring board can be provided by forming wiring using a metal-clad laminate by a known method. Details of the prepreg and metal-clad laminate are as described above. The printed wiring board may be either a single-layer printed wiring board or a multi-layer printed wiring board. 【0091】 [Semiconductor Package] According to one embodiment, a semiconductor package can be provided that includes a printed circuit board and a semiconductor element. More specifically, for example, a semiconductor package can be provided that includes a printed circuit board containing a cured product of a curable resin material and a semiconductor element. The semiconductor package can be manufactured, for example, by mounting a semiconductor element, memory, etc., on a printed circuit board by a known method. 【0092】 Examples of embodiments are given below. The present invention is not limited to the following embodiments. <1> A curable resin material comprising a polymerizable group-containing compound (A) and an inorganic filler (B), wherein the polymerizable group-containing compound (A) comprises a resin (A1) containing an indene ring, a vinylbenzyl group, and an arylalkyl group other than a vinylbenzyl group. 【0093】 <2> The curable resin material according to <1>, wherein the inorganic filler (B) is contained in an amount of 180 to 230 parts by mass per 100 parts by mass of the polymerizable group-containing compound (A). 【0094】<3> The curable resin material according to <1> or <2>, which does not contain elastomers, or the ratio of elastomers to the total mass of the polymerizable group-containing compound (A) is 10% by mass or less. 【0095】 <4> The resin (A1) contains at least two compounds that have different structures from the compounds represented by the following general formula (1), and R is present in the resin. １ , R ２ and R ３ At least one of them is a vinylbenzyl group, and R present in the resin １ , R ２ and R ３ A curable resin material according to any one of <1> to <3> above, comprising a resin (A1-1) in which at least one of the members is an arylalkyl group other than a vinylbenzyl group. 【0096】 【0097】 [In general formula (1), R １ , R ２ and R ３ Each of these is independently a hydrogen atom, a vinylbenzyl group, or an arylalkyl group other than a vinylbenzyl group. ４ is a hydrogen atom, a monovalent organic group, or a halogen atom, and has four R ４ All of them may be different from each other, and there are four R's. ４ Two or more of them may be identical. 【0098】 <5> The curable resin material according to any one of <1> to <4> above, wherein the arylalkyl group other than the vinylbenzyl group contained in the resin (A1) does not have a polymerizable group. 【0099】 <6> A prepreg comprising a curable resin material described in any one of <1> to <5> above, or a semi-cured product of the curable resin material. 【0100】 <7> A resin film comprising a curable resin material described in any one of <1> to <5> above, or a semi-cured product of the curable resin material. 【0101】<8> A metal-clad laminate comprising a cured product of any one of the curable resin materials described in <1> to <5> above, and a metal foil. 【0102】 <9> A printed circuit board comprising a cured product of a curable resin material, a surface protective film formed using a curable resin material, an interlayer insulating film formed using a curable resin material, or a combination thereof, wherein the curable resin material is the curable resin material described in any one of <1> to <5> above. 【0103】 <10> A printed circuit board as described in <9> above, for use with a motherboard. 【0104】 <11> A semiconductor package comprising the printed circuit board described in <9> above and a semiconductor element. 【0105】 <12> A semiconductor package comprising a semiconductor element and a cured product of any one of <1> to <5> above for sealing the semiconductor element. 【0106】 The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. 【0107】 Measurement Method for Weight-Average Molecular Weight (Mw) and Number-Average Molecular Weight (Mn) The weight-average molecular weight and number-average molecular weight were calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). The calibration curve was approximated by a cubic equation using standard polystyrene: TSK standard POLYSTYRENE (Type; A-2500, A-5000, F-20, F-80) (manufactured by Tosoh Corporation, trade name). The GPC conditions are shown below. 【0108】Instrument: High-speed GPC instrument "HLC-8320GPC" (Tosoh Corporation, product name) Detector: Ultraviolet absorption detector "UV-8320" (Tosoh Corporation, product name) Columns: Guard column; TSKgel guardcolumn Super(HZ)-M+, Column; TSKgel SuperMultipore HZ-M (2), Reference column; TSKgel SuperH-RC (2) (all Tosoh Corporation, product names) Column size: 4.6 × 20 mm (guard column), 4.6 × 150 mm (column), 6.0 × 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10 mg / 1 mL Injection volume: 20 μL or 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40°C 【0109】 [Production of resin (A1-1-1)] In a 500 mL reaction vessel equipped with a stirrer, thermometer, reflux tubing, and nitrogen inlet, 35.6 parts by mass of indene, 75.5 parts by mass of chloromethylstyrene (*1), 22.9 parts by mass of α-chloro-p-xylene, 7.1 parts by mass of tetra-n-butylammonium bromide as a phase transfer catalyst, 0.1 parts by mass of phenothiazine as a polymerization inhibitor, and 76.1 parts by mass of toluene as a solvent were charged, and the mixture was heated and stirred at 40°C while blowing in nitrogen at a flow rate of 50 mL / min. 【0110】 Chloromethylstyrene (*1): AGC Seimi Chemical Co., Ltd. "CMS-P", a mixture of m-isomer and p-isomer, m-isomer content approximately 50% by mass, p-isomer content approximately 50% by mass. 【0111】Next, 97.0 parts by mass of a 48% by mass aqueous sodium hydroxide solution was added dropwise over 20 minutes, and the mixture was stirred at 60°C for 9 hours. Nitrogen was continuously blown in during the reaction. After cooling to room temperature (25°C) and neutralizing with a 10% hydrochloric acid aqueous solution, the mixture was washed twice with pure water. After removing toluene by vacuum distillation, the resulting viscous liquid was washed with methanol and vacuum dried to obtain resin (A1-1-1). For resin (A1-1-1), the area ratios of the peaks corresponding to each component in the GPC chart measured under the following conditions were 10.1% for the compound with a total number of vinylbenzyl groups and tolylmethyl groups substituted on the indene ring (monosubstituted), 39.4% for the compound with a total number of vinylbenzyl groups and tolylmethyl groups substituted on the indene ring (disubstituted), and 50.5% for the compound with a total number of vinylbenzyl groups and tolylmethyl groups substituted on the indene ring (trisubstituted). 【0112】 Instrument: High-speed GPC instrument HLC-8320GPC (Tosoh Corporation, product name) Detector: Ultraviolet absorption detector UV-8320 (Tosoh Corporation, product name) Columns: Guard column; TSKgel guardcolumn Super(HZ)-M+, Column; TSKgel SuperMultipore HZ-M (2), Reference column; TSKgel SuperH-RC (2) (all Tosoh Corporation, product names) Column size: 4.6 × 20 mm (guard column), 4.6 × 150 mm (column), 6.0 × 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10 mg / 1 mL Injection volume: 20 μL or 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40°C 【0113】 [Production of resins (A1-1-2) and (A1-1-3)] Resins (A1-1-2) and (A1-1-3) were obtained in the same manner as resin (A1-1-1), except that the mass of each raw material used in the reaction was changed to the proportions shown in Table 1 below. 【0114】 【0115】[Production of Resin (A4)] In a reaction vessel equipped with a stirrer, thermometer, reflux tubing, and nitrogen inlet, 200 parts by mass of polyphenylene ether (*2), 30 parts by mass of chloromethylstyrene (*1), 1.2 parts by mass of tetra-n-butylammonium bromide as a phase transfer catalyst, 0.1 parts by mass of phenothiazine as a polymerization inhibitor, and 400 parts by mass of toluene as a solvent were charged, and the mixture was heated and stirred at 75°C while blowing nitrogen at a flow rate of 50 mL / min. Next, 500 parts by mass of 48% by mass aqueous sodium hydroxide solution was added dropwise over 20 minutes, and the mixture was stirred further at 75°C for 4 hours. Nitrogen blowing was continued throughout the reaction. After cooling to room temperature (25°C) and neutralization with 10% hydrochloric acid aqueous solution, the mixture was washed twice with pure water. After removing toluene under reduced pressure, the obtained viscous liquid was washed with methanol and vacuum dried to obtain the resin in the above general formula (4) R ６ A resin (A4) having a structure in which the group is a vinylbenzyl group was obtained. 【0116】 Polyphenylene ether (*2): SA90 manufactured by SABIC, number average molecular weight (Mn) 1,700 【0117】 [Production of Resin (A5)] 236.8 parts by mass of 2-bromoethylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 56.0 parts by mass of α,α'dichloro-p-xylene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added to a reaction vessel equipped with a stirrer, thermometer, reflux tubing, and nitrogen inlet, and the mixture was stirred. 14.7 parts by mass of methanesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), which had been melted by standing at 25°C, was added dropwise to the reaction vessel using a pipette. The reaction vessel was immersed in an oil bath, and the reaction was carried out at 130°C for 7 hours while stirring the contents of the reaction vessel. After removing the vessel from the oil bath and allowing it to cool naturally, 106.4 parts by mass of sodium hydroxide aqueous solution (48% by mass) was added dropwise to neutralize the mixture. 960 parts by mass of toluene was added and stirred to extract the toluene-soluble components. The resulting organic layer was removed and washed five times with water. The organic layer after washing was heated under reduced pressure to remove toluene and unreacted substances by distillation, yielding 112 parts by mass (yield 65%) of an intermediate having a 2-bromoethylbenzene structure. 【0118】In a reaction vessel equipped with a stirrer, thermometer, reflux tubing, and nitrogen inlet, 110 parts by mass of the intermediate obtained earlier, 250 parts by mass of toluene, 750 parts by mass of dimethyl sulfoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) melted by standing at 25°C, 75 parts by mass of water, and 25 parts by mass of solid sodium hydroxide (manufactured by Kanto Chemical Co., Ltd.) were added. The reaction vessel was immersed in an oil bath and reacted at 40°C for 5 hours while stirring the contents of the vessel. After removing it from the oil bath and allowing it to cool naturally, 500 parts by mass of toluene was added and stirred to extract the toluene-soluble components. The obtained organic layer was removed and washed five times with 500 parts by mass of water. The washed organic layer was heated under reduced pressure to remove the solvent and 65 parts by mass (yield 75%) of resin (A5) having the structure represented by the above general formula (5) were obtained. The obtained resin (A5) had a number-average molecular weight (Mn) of 443, a weight-average molecular weight (Mw) of 451, and the value of e in the above general formula (5) was between 1 and 2. 【0119】 [Production of Flame Retardant (1)] 432 parts by mass of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 251 parts by mass of bis(chloromethyl)biphenyl, and 2400 parts by mass of toluene were added to a reaction vessel equipped with a stirrer, thermometer, reflux tubing, and nitrogen inlet. The reaction was then continued at 170°C for 16 hours while stirring the contents of the reaction vessel. After the reaction mixture was cooled to room temperature, hexane was added to precipitate the product, which was then filtered. The resulting white crystals were dried at 120°C to obtain flame retardant (1) having the structure represented by the following structural formula. 【0120】 【0121】 [Examples 1-9 and Comparative Examples 1-3] Each component was blended in the proportions shown in Table 2, and the solid content was adjusted to approximately 65% ​​by mass with toluene to produce a curable resin material. For components that are solutions in Table 2, the blending amounts are calculated on a solid content basis. The following evaluation tests were performed on the obtained curable resin materials. The results are also shown in Table 2. 【0122】Details of each component listed in Table 2 are as follows: • Resin (A1-1-1): Resin (A1-1-1) obtained earlier • Resin (A1-1-2): Resin (A1-1-2) obtained earlier • Resin (A1-1-3): Resin (A1-1-3) obtained earlier • Resin (A2): Polymerizable group-containing aromatic polyether resin, "HC-G0037" manufactured by JSR Corporation • Resin (A3): Polyphenylene ether resin with methacryloyl groups at the ends, number average molecular weight (Mn) 1,700, "SA9000" manufactured by SABIC Corporation • Resin (A4): Resin (A4) obtained earlier • Resin (A5): Resin (A5) obtained earlier • Inorganic filler (B-1): Molten spherical silica, average particle size (D ５０ ) 0.5 μm ・Elastomer: Polybutadiene, number average molecular weight (Mn) 1,200, manufactured by Nippon Soda Co., Ltd. "B-1000" ・Flame retardant (1): The flame retardant obtained above ・Flame retardant (2): A phosphorus atom-containing compound represented by the following general formula (manufactured by Fushimi Pharmaceutical Co., Ltd. "Rabitol FP-72 (TP)") 【0123】 【0124】 [e is an integer between 3 and 8.] 【0125】 • Curing accelerator (1): α,α'-di(t-butylperoxy)diisopropylbenzene, manufactured by NOF Corporation as "Perbutyl P" • Curing accelerator (2): Dicumyl peroxide, manufactured by NOF Corporation as "Permil D" 【0126】 [Prepreg Preparation] A curable resin material was impregnated and coated onto glass cloth conforming to IPC standard #1078 (Nitto Boseki Co., Ltd.'s "NER1078"), and then heated and dried at 120°C for 10 minutes to obtain a prepreg. The solid content of the prepreg derived from the curable resin material was approximately 60% by mass. 【0127】 [Preparation of double-sided copper-clad laminate] Ten sheets of the obtained prepreg were stacked, and 18 μm thick electrolytic copper foil (SI-VSP-18, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides with the matte side facing the prepreg. This was then subjected to a load of 3 kg / cm². ２ A double-sided copper-clad laminate was obtained by heating and pressurizing under vacuum pressing conditions at 210°C for 80 minutes. 【0128】[Measurement of Dielectric Constant (Dk) and Dielectric Loss Tangent (Df)] A 100 mm x 40 mm test specimen was prepared by removing the copper foil from both sides of a double-sided copper-clad laminate by immersion in a copper etching solution (*3). The obtained test specimen was dried at 105°C for 1 hour, and then left to stand for 24 hours in an ambient temperature of 24.2°C and humidity of 54% RH. Next, the dielectric constant (Dk) and dielectric loss tangent (Df) were measured in the 10 GHz band at an ambient temperature of 25°C in accordance with the split-post dielectric resonator method. The measuring instrument used was the "PNA Network Analyzer N5222B" from agilent technologies. 【0129】 Copper etching solution (*3): 10% by mass solution of ammonium persulfate (manufactured by Mitsubishi Gas Chemical Company, Inc.) 【0130】 [Measurement of Thermal Expansion Coefficient (CTE)] The copper foil was removed from the double-sided copper-clad laminate obtained above by immersion in a copper etching solution (*3), and a test specimen measuring 5 mm in length (X direction), 5 mm in width (Y direction), and 0.6 mm in thickness (Z direction) was prepared. The thermal expansion coefficient in the Z direction of this test specimen was measured using a TMA test apparatus (TA Instruments, Q400). The heating rate was set to 10°C / min, and the average thermal expansion coefficient over a temperature range of 30 to 120°C was used for evaluation. 【0131】 [Heat Resistance Evaluation] Using a copper etching solution (*3), the copper foil on one side and half of the copper foil on the other side of a double-sided copper-clad laminate were removed to prepare 50 mm x 50 mm semi-copper coated test specimens. After being treated for 5 hours in a pressure cooker test (PCT) apparatus (manufactured by Hirayama Seisakusho Co., Ltd.) (conditions: 121°C, 2.2 atm), the semi-copper coated test specimens were immersed in a 288°C solder bath for 20 seconds each, and the solder heat resistance of the semi-copper coated test specimens after water absorption treatment was evaluated by visually observing their appearance. The evaluation results are shown in Table 2, with "A" indicating no blistering and "B" indicating blistering. 【0132】 【0133】 P mass% (*4): The flame retardant was added based on the phosphorus atom content relative to the total mass of the resin components (components excluding inorganic filler (B-1) and solvent) in the curable resin material. 【0134】 As shown in Table 1, the curable resin materials of Examples 1 to 9, which contain a polymerizable group-containing compound (A) and an inorganic filler (B), and in which the polymerizable group-containing compound (A) contains resin (A1), exhibited low dielectric loss tangent and thermal expansion coefficients in the cured product. The dielectric loss tangent and thermal expansion coefficient values ​​in Examples 1 to 9 of this application are applicable to applications that require a very high level of reduction in dielectric loss tangent and thermal expansion coefficient, such as motherboards. Comparative Examples 1 to 3 are examples in which the polymerizable group-containing compound (A) does not contain resin (A1). Comparative Examples 1 and 2 had low dielectric loss tangent due to the addition of elastomer, but had high thermal expansion coefficients. Comparative Example 3 had a considerably higher dielectric loss tangent compared to the examples, and also a slightly higher thermal expansion coefficient. 【0135】 The disclosures of this application are related to the subject matter described in Japanese Patent Application No. 2024-217512, filed on 12 December 2024, the disclosures of which are incorporated herein by reference.

Claims

1. A curable resin material comprising a polymerizable group-containing compound (A) and an inorganic filler (B), wherein the polymerizable group-containing compound (A) comprises a resin (A1) containing an indene ring, a vinylbenzyl group, and an arylalkyl group other than a vinylbenzyl group.

2. The curable resin material according to claim 1, comprising 160 to 210 parts by mass of an inorganic filler (B) with respect to a total of 100 parts by mass of the polymerizable group-containing compound (A).

3. The curable resin material according to claim 1, wherein it does not contain elastomers, or the proportion of elastomers to the total mass of the polymerizable group-containing compound (A) is 10% by mass or less.

4. The resin (A1) contains at least two compounds having different structures among the compounds represented by the following general formula (1), and R present in the resin １ , R ２ and R ３ Among them, at least one is a vinylbenzyl group, and R present in the resin １ , R ２ and R ３ Among them, at least one is an arylalkyl group other than a vinylbenzyl group. The curable resin material according to claim 1, which contains the resin (A1-1). [In the general formula (1), R １ , R ２ and R ３ are each independently a hydrogen atom, a vinylbenzyl group, or an arylalkyl group other than a vinylbenzyl group. R ４ is a hydrogen atom, a monovalent organic group, or a halogen atom, and all four R ４ may be different from each other, and two or more of the four R ４ may be the same as each other. ] 5. The curable resin material according to claim 1, wherein the arylalkyl group other than the vinylbenzyl group contained in the resin (A1) does not have a polymerizable group.

6. A prepreg comprising a curable resin material according to any one of claims 1 to 5 or a semi-cured product of the curable resin material.

7. A resin film comprising a curable resin material according to any one of claims 1 to 5 or a semi-cured product of the curable resin material.

8. A metal-clad laminate comprising a cured product of a curable resin material according to any one of claims 1 to 5 and a metal foil.

9. A printed circuit board comprising a cured product of a curable resin material, a surface protective film formed using a curable resin material, an interlayer insulating film formed using a curable resin material, or a combination thereof, wherein the curable resin material is the curable resin material described in any one of claims 1 to 5.

10. A printed circuit board according to claim 9, which is for use as a motherboard.

11. A semiconductor package comprising a printed circuit board according to claim 9 and a semiconductor element.

12. A semiconductor package comprising a semiconductor element and a cured product of a curable resin material according to any one of claims 1 to 5 for sealing the semiconductor element.

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