Arylalkyl-modified indene composition, curable resin material, prepreg, resin film, metal-clad laminate, printed wiring board, and semiconductor package

Abstract

Provided is an arylalkyl-modified indene composition that contains a plurality of types of compounds having an arylalkyl group on an indene ring, the compounds having different numbers of arylalkyl groups in one molecule, wherein: the content of a compound in which the number of arylalkyl groups in one molecule is 1 is 1% or less as calculated from the area ratio of the GPC chart; at least one of the arylalkyl groups present in the composition has a polymerizable unsaturated bond-containing group; and at least one of the arylalkyl groups present in the composition does not have a polymerizable unsaturated bond-containing group.

Description

Aryl alkyl-modified indene composition, curable resin material, prepreg, resin film, metal-clad laminate, printed wiring board, and semiconductor package

[0001] The present disclosure relates to an aryl alkyl-modified indene composition, a curable resin material, a prepreg, a resin film, a metal-clad laminate, a printed wiring board, and a semiconductor package.

[0002] Metal-clad laminates, such as copper-clad laminates, prepregs that can be used with metal-clad laminates, and semiconductor packages that use metal-clad laminates are used in a variety of electronic devices, including mobile communication devices such as smartphones, their base station equipment, servers, routers, large servers, and other network infrastructure devices, as well as large computers, personal computers, and industrial computers. They are also used in electronic devices installed in home appliances, automobiles, and other devices. With the spread of 5G, there is a growing demand for electronic communication devices to process massive amounts of data at high speeds.

[0003] When electronic devices process huge amounts of data at high speed, they require circuit board materials with low transmission loss in the high-frequency range. While resins with low dielectric constants and low dielectric loss tangents are used as circuit board materials and provide circuit boards with low transmission loss, recent advances in communication technology have created a demand for the development of resins with even lower dielectric constants and dielectric loss tangents.

[0004] Patent Document 1 discloses a compound having an indene ring structure into which a vinylbenzyl group has been introduced, as a curable vinylbenzyl compound that can give a cured product excellent in low dielectric constant, low dielectric dissipation factor, high heat resistance, and low water absorption.

[0005] Japanese Patent Application Laid-Open No. 2003-277440

[0006] An object of the present disclosure is to provide an aryl alkyl-modified indene composition that exhibits excellent dielectric properties even when the cured product is exposed to a high-humidity environment, a curable resin material, and prepregs, resin films, metal-clad laminates, printed wiring boards, and semiconductor packages that use these.

[0007] The present disclosure includes the following embodiments. The present disclosure is not limited to the following embodiments. One embodiment relates to an arylalkyl-modified indene composition, which is a composition containing a plurality of compounds having different numbers of arylalkyl groups per molecule, among compounds having an arylalkyl group on an indene ring, wherein the content of compounds having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

[0008] Another embodiment relates to an arylalkyl-modified indene composition, which is a composition containing a plurality of compounds represented by the following general formula (1), each of which has a different number of arylalkyl groups per molecule, wherein the content of the compound having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

[0009]

[0010] [In general formula (1), R １ , R ２ and R ３ are each independently a hydrogen atom or an arylalkyl group, and R １ , R ２ and R ３ At least one of R is an arylalkyl group. ４ represents a monovalent substituent, and n is 0 or an integer of 1 to 4. When n is an integer of 2 or greater, the multiple R4s present in the formula may all be different, or some or all may be the same.]

[0011] The present disclosure makes it possible to provide aryl alkyl-modified indene compositions and curable resin materials that exhibit excellent dielectric properties even when the cured product is exposed to a high-humidity environment, as well as prepregs, resin films, metal-clad laminates, printed wiring boards, and semiconductor packages that use these compositions.

[0012] FIG. 1 is a GPC chart of the indene composition (1) produced in Example 1. FIG. 2 is a GPC chart of the indene composition (2) produced in Example 2. FIG. 3 is a GPC chart of the indene composition (3) produced in Example 3. FIG. 4 is a GPC chart of the indene composition (4) produced in Example 4. FIG. 5 is a GPC chart of the indene composition (5) produced in Example 5. FIG. 6 is a GPC chart of the indene composition (6) produced in Example 6. FIG. 7 is a GPC chart of the indene composition (7) produced in Example 7. FIG. 8 is a GPC chart of the indene composition (8) produced in Example 8. FIG. 9 is a GPC chart of the indene composition (9) produced in Example 9.

[0013] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments.

[0014] In the present disclosure, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit of a certain numerical range may be replaced with the upper or lower limit of another numerical range. Furthermore, the upper or lower limit of a numerical range described in the present disclosure may be replaced with a value shown in an example.

[0015] In the present disclosure, unless otherwise specified, each component may contain one or more corresponding substances.

[0016] In the present disclosure, the content of each component in a curable resin material means, unless otherwise specified, the total amount of the multiple substances present in the curable resin material when multiple substances corresponding to each component are present in the curable resin material.

[0017] [Arylalkyl-Modified Indene Composition] The arylalkyl-modified indene composition, which is one embodiment of the present disclosure, is a composition containing a plurality of types of compounds having an arylalkyl group on an indene ring, each type of compound differing in the number of arylalkyl groups per molecule, in which the content of compounds having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

[0018] In a compound having an arylalkyl group on an indene ring (hereinafter sometimes referred to as an "indene compound"), the arylalkyl group is a structural moiety in which one of the hydrogen atoms in the alkyl group is substituted with an aryl group.

[0019] The alkyl group in the arylalkyl group may be either linear or branched. The number of carbon atoms in the alkyl group is not particularly limited, but may be, for example, in the range of 1 to 6. Examples of alkyl groups having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a pentyl group, an isopentyl group, a neopentyl group, a hexyl group, and a cyclohexyl group. The alkyl group may be an alkyl group having 1 to 3 carbon atoms, or may be a methyl group.

[0020] Examples of the aryl group in the arylalkyl group include a phenyl group, a naphthyl group, an anthryl group, and these groups having one or more substituents on the aromatic ring. The aryl group in the arylalkyl group may be a phenyl group, a naphthyl group, or a phenyl group. Examples of the substituent on the aromatic ring include a halogen atom, an alkyl group, an alkoxy group, and a group containing a polymerizable unsaturated bond.

[0021] Specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0022] The alkyl group may be either linear or branched. The number of carbon atoms in the alkyl group is not particularly limited, but may be, for example, in the range of 1 to 6. Examples of alkyl groups having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a pentyl group, an isopentyl group, a neopentyl group, a hexyl group, and a cyclohexyl group. The alkyl group may be an alkyl group having 1 to 3 carbon atoms, or may be a methyl group.

[0023] The alkoxy group is, for example, a group represented by RO-, where R is the alkyl group described above.

[0024] The specific structure of the polymerizable unsaturated bond-containing group is not particularly limited, and examples thereof include a structural moiety in which one or more C-C bonds in the alkyl group or alkoxy group described above are replaced with double bonds or triple bonds, a structural moiety in which one or more hydrogen atoms in the alkyl group or alkoxy group described above are replaced with (meth)acryloyloxy groups, (meth)acryloyl groups, (meth)acryloyloxy groups, etc. The polymerizable unsaturated bond-containing group may be any of an allyl group, allyloxy group, vinyl group, vinyloxy group, (meth)acryloyl group, and (meth)acryloyloxy group, and may be a vinyl group or vinyloxy group, or may be a vinyl group.

[0025] The indene compound may have one or more substituents other than the arylalkyl group. The type of the substituent is not particularly limited, but examples thereof include a halogen atom, an alkyl group, an alkoxy group, and a polymerizable unsaturated bond-containing group. Specific examples of these include those exemplified as the substituents on the aromatic ring of the arylalkyl group. The indene compound may have no substituents other than the arylalkyl group.

[0026] The number of arylalkyl groups in the indene compound is not particularly limited, but may be, for example, 1, 2, or 3.

[0027] The specific structure of the indene compound is not particularly limited, but may be, for example, a compound represented by the following general formula (1).

[0028]

[0029] [In general formula (1), R １ , R ２ and R ３ are each independently a hydrogen atom or an arylalkyl group, and R １ , R ２ and R ３ At least one of R is an arylalkyl group. ４ represents a monovalent substituent, and n is 0 or an integer of 1 to 4. When n is an integer of 2 or more, a plurality of R ４ may all be different, or some or all may be the same.]

[0030] R in general formula (1) １ , R ２ and R ３ The details of the arylalkyl group are as explained above. ４ is a monovalent substituent, specific examples of which include the various substituents described above as substituents other than arylalkyl groups. n in general formula (1) is an integer of 1 to 4. n may also be 0.

[0031] The arylalkyl-modified indene composition (hereinafter sometimes referred to as the "indene composition") contains a plurality of compounds having an arylalkyl group on an indene ring, each of which has a different number of arylalkyl groups per molecule. Specifically, the indene composition may contain two or more compounds selected from the group consisting of an indene compound having one arylalkyl group per molecule (hereinafter sometimes referred to as the "indene compound (1)"), an indene compound having two arylalkyl groups per molecule (hereinafter sometimes referred to as the "indene compound (2)"), and an indene compound having three arylalkyl groups per molecule (hereinafter sometimes referred to as the "indene compound (3)"). The indene composition preferably contains the indene compound (2) and the indene compound (3).

[0032] The content of compounds having one arylalkyl group per molecule in the indene composition, i.e., the content of indene compound (1), is 1% or less as calculated from the area ratio in the GPC chart. Furthermore, the content of indene compound (1) may be less than 0.9%, 0.85% or less, or 0.8% or less. Furthermore, the content of indene compound (1) in the indene composition may be below the detection limit. The indene composition does not necessarily contain indene compound (1), but may contain indene compound (1) in an amount of 0.05% or more, or even 0.1% or more. The content of indene compound (1) in the indene composition may be in the range of 0.05 to 1%.

[0033] In the present disclosure, the GPC conditions for calculating the content of each compound in the indene composition are as follows.

[0034] Apparatus: High-speed GPC apparatus "HLC-8420GPC" (Tosoh Corporation, trade name) Detector: Ultraviolet absorption detector "UV-8420" (Tosoh Corporation, trade name) Column: Guard column; TSKgel guard column SuperHZ-L, Column; TSKgel SuperHZ4000 + TSKgel SuperHZ2500 + TSKgel SuperHZ1000 (3 columns), Reference column; None (Resistor tube) (all Tosoh Corporation, trade names) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column) Eluent: Tetrahydrofuran Sample concentration: 1 mg / 1 mL Injection volume: 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40°C

[0035] The content of the indene compound (2) in the indene composition may be 3% or more, 5% or more, or 10% or more, as calculated from the area ratio in the GPC chart. It may also be 25% or less, 20% or less, or 19% or less. The content of the indene compound (2) in the indene composition may be in the range of 3 to 25%.

[0036] The content of the indene compound (3) in the indene composition is preferably 80% or more as calculated from the area ratio in the GPC chart. Alternatively, it may be 95% or less, 90% or less, or 85% by mass or less. The content of the indene compound (3) in the indene composition may be in the range of 80 to 95%.

[0037] The total content of the indene compound (2) and the indene compound (3) in the indene composition is preferably 99% or more as calculated from the area ratio in the GPC chart.

[0038] In the indene composition, at least one of the aryl alkyl groups present in the composition is an aryl alkyl group having a polymerizable unsaturated bond-containing group, which allows the indene composition to function as a curable composition and results in an aryl alkyl-modified indene composition that exhibits excellent dielectric properties even when the cured product is exposed to a high-humidity environment.

[0039] Of the arylalkyl groups present in the indene composition, the proportion of arylalkyl groups having a polymerizable unsaturated bond-containing group may be 50 mol % or more, 55 mol % or more, or 60 mol % or more. It may also be 95 mol % or less, 90 mol % or less, or 80 mol % or less. Of the arylalkyl groups present in the indene composition, the proportion of arylalkyl groups having a polymerizable unsaturated bond-containing group may be in the range of 50 to 95 mol %.

[0040] The specific structure of the arylalkyl group having a polymerizable unsaturated bond-containing group is not particularly limited, but a particularly preferred example is a vinylbenzyl group. The vinylbenzyl group may be any of an o-vinylbenzyl group, an m-vinylbenzyl group, and a p-vinylbenzyl group. Among these, a p-vinylbenzyl group or an m-vinylbenzyl group is preferred because it results in an indene composition with excellent dielectric properties in the cured product. The indene composition may contain both a p-vinylbenzyl group and an m-vinylbenzyl group. The proportion of p-vinylbenzyl groups among the vinylbenzyl groups contained in the indene composition may be 10 mol% or more, 20 mol% or more, or 30 mol% or more. It may also be 100 mol% or less, 80 mol% or less, or 70 mol% or less. The proportion of p-vinylbenzyl groups among the vinylbenzyl groups contained in the indene composition may be in the range of 10 to 100 mol%. When the proportion of p-vinylbenzyl groups among the vinylbenzyl groups contained in the indene composition is less than 100 mol %, the remainder may be m-vinylbenzyl groups.

[0041] In the indene composition, at least one of the aryl alkyl groups present in the composition is an aryl alkyl group that does not have a polymerizable unsaturated bond-containing group, which further improves the moisture resistance of the cured product and more significantly enhances the effect of exhibiting excellent dielectric properties even when exposed to a high-humidity environment.

[0042] Of the arylalkyl groups present in the indene composition, the proportion of arylalkyl groups not having a polymerizable unsaturated bond-containing group may be 5 mol % or more, 10 mol % or more, or 20 mol % or more. It may also be 50 mol % or less, 45 mol % or less, or 40 mol % or less. Of the arylalkyl groups present in the indene composition, the proportion of arylalkyl groups not having a polymerizable unsaturated bond-containing group may be in the range of 1 to 50 mol %.

[0043] The specific structure of the arylalkyl group not having a polymerizable unsaturated bond-containing group is not particularly limited, but a particularly preferred example is a tolylmethyl group. The tolylmethyl group may be any of an o-tolylmethyl group, an m-tolylmethyl group, and a p-tolylmethyl group. Of these, a p-tolylmethyl group or an m-tolylmethyl group is preferred because it results in an indene composition having excellent dielectric properties in a cured product. The proportion of p-tolylmethyl groups among the tolylmethyl groups contained in the indene composition may be 60 mol% or more, 80 mol% or more, 90 mol% or more, or even 100 mol%.

[0044] The method for producing the aryl alkyl-modified indene composition is not particularly limited, and any method may be used, such as a method of reacting a compound having an indene ring with an aryl alkylating agent in the presence of a basic compound.

[0045] The compound having an indene ring may be, for example, a compound represented by the following general formula (2): The compound having an indene ring may be used alone or in combination of two or more kinds.

[0046]

[0047] [In general formula (2), R ４ and n is R in general formula (1). ４ and n are synonymous with each other.]

[0048] The aryl alkylating agent is not particularly limited as long as it is a compound capable of introducing an aryl alkyl group onto an indene ring, and examples thereof include aryl alkyl halides such as chloromethylstyrene and α-chloroxylene. One type of aryl alkylating agent may be used alone, or two or more types may be used in combination.

[0049] Since at least one of the aryl alkyl groups present in the indene composition is an aryl alkyl group having a polymerizable unsaturated bond-containing group, it is preferable that at least a portion of the aryl alkylating agent has a polymerizable unsaturated bond-containing group. The proportion of aryl alkylating agents having a polymerizable unsaturated bond-containing group may be 50 mol% or more, 55 mol% or more, or 60 mol% or more. It may also be 95 mol% or less, 90 mol% or less, or 80 mol% or less. The proportion of aryl alkylating agents having a polymerizable unsaturated bond-containing group may be in the range of 50 to 95 mol%.

[0050] Furthermore, since at least one of the aryl alkyl groups present in the composition is an aryl alkyl group that does not have a polymerizable unsaturated bond-containing group, it is preferable that at least a portion of the aryl alkylating agent does not have a polymerizable unsaturated bond-containing group. The proportion of aryl alkylating agents that do not have a polymerizable unsaturated bond-containing group may be 5 mol% or more, 10 mol% or more, or even 20 mol% or more. It may also be 50 mol% or less, 45 mol% or less, or 40 mol% or less. The proportion of aryl alkylating agents that do not have a polymerizable unsaturated bond-containing group may be in the range of 5 to 50 mol%.

[0051] The ratio of the aryl alkylating agent to 1 mole of the compound having an indene ring is preferably 2 moles or more, more preferably 2.5 moles or more, and more preferably 2.8 moles or more, since the effect of improving the dielectric properties becomes more pronounced. The upper limit is not particularly limited, but may be, for example, 3.2 moles or less, or 3.0 moles or less.

[0052] Examples of the basic compound include alkali metal hydroxides and alkali metal alkoxides. One basic compound may be used alone, or two or more basic compounds may be used in combination. The basic compound may be used as a solid or as an aqueous solution.

[0053] A phase transfer catalyst may be used in the above reaction. The phase transfer catalyst may be used alone or in combination of two or more. Examples of the phase transfer catalyst 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 hydrogen sulfate; and quaternary phosphonium salts such as tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, benzyltriphenylphosphonium chloride, and benzyltriphenylphosphonium bromide.

[0054] A polymerization inhibitor may be used in the above reaction. One type of polymerization inhibitor may be used alone, or two or more types may be used in combination. Examples of the polymerization inhibitor include hydroquinone, methylhydroquinone, tert-butylhydroquinone, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, hydroquinone monomethyl ether, 1,4-benzoquinone, 2-tert-butyl-1,4-benzoquinone, 2-tert-butylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butylphenol, cresol, catechol, and 4-tert-butylcatechol. Chole, pyrogallol, 4-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, bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl)sebacate, and the like.

[0055] The reaction may be carried out in a solvent. Examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene. One type of solvent may be used alone, or two or more types may be used in combination.

[0056] After the reaction is complete, the reaction product may be purified by a known method such as concentration, reprecipitation, or washing, if necessary.

[0057] The indene composition preferably has a dielectric loss tangent (Df) of 0.0020 or less, more preferably 0.0015 or less, and particularly preferably 0.0013 or less in the cured product. The lower the dielectric loss tangent, the better. There is no particular restriction on the lower limit, but the Df may be, for example, 0.0001 or more, or 0.0002 or more.

[0058] The cured product used for measuring the dielectric loss tangent can be obtained, for example, by the method described in the Examples. The dielectric loss tangent is a value measured at 25°C and 10 GHz in accordance with the SPDR (split post dielectric resonator) method. The measuring device that can be used is, for example, a "10 GHz SPDR" manufactured by Vega Technology.

[0059] [Curable Resin Material] A curable resin material according to one embodiment of the present disclosure comprises the aryl alkyl-modified indene composition described above. Examples of other components that the curable resin material may contain, in addition to the aryl alkyl-modified indene composition, include other curable compounds other than the indene composition, elastomers, fillers, curing accelerators, flame retardants, antioxidants, heat stabilizers, antistatic agents, UV absorbers, pigments, colorants, lubricants, and solvents. Each of these other components may be used singly or in combination.

[0060] Examples of other curable compounds include compounds having a polymerizable unsaturated bond, epoxy resins, phenolic resins, cyanate resins, isocyanate resins, benzoxazine resins, oxetane resins, amino resins, dicyclopentadiene resins, silicone resins, triazine resins, melamine resins, etc. Examples of the compound having a polymerizable unsaturated bond include compounds having a maleimide group, polyarylene ether compounds having a polymerizable unsaturated bond-containing group, styrene, divinylbenzene, triallyl isocyanurate, etc.

[0061] Examples of compounds having a maleimide group include compounds having one or more N-substituted maleimide groups and derivatives thereof.

[0062] Examples of the compound having one or more N-substituted maleimide groups include aromatic maleimide compounds which are compounds having an N-substituted maleimide group directly bonded to an aromatic ring, aromatic bismaleimide compounds which are compounds having two N-substituted maleimide groups directly bonded to an aromatic ring, aromatic polymaleimide compounds which are compounds having three or more N-substituted maleimide groups directly bonded to an aromatic ring, and aliphatic maleimide compounds which are compounds having an N-substituted maleimide group directly bonded to an aliphatic hydrocarbon.

[0063] Specific examples of the compound having one or more N-substituted maleimide groups include N,N'-ethylene bismaleimide, N,N'-hexamethylene bismaleimide, 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, 3,3'-dimethyl-5, 5'-Diethyl-4,4'-diphenylmethane bismaleimide, 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]propanol Pan, 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-maleimidophenyl)disulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfide, bis[4-(4-maleimidophenoxy)phenyl]sulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfoxide, bis 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-dimethylbenzyl]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, 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, polyphenylmethane maleimide, aromatic bismaleimide compounds having an indane skeleton, biphenylaralkyl maleimide compounds, etc.

[0064] Examples of derivatives of compounds having one or more N-substituted maleimide groups include aminomaleimide compounds containing structural units derived from the above-described compounds having one or more N-substituted maleimide groups and structural units derived from diamine compounds.

[0065] Examples of derivatives of compounds having one or more N-substituted maleimide groups include aminomaleimide compounds containing structural units derived from the above-described compounds having one or more N-substituted maleimide groups and structural units derived from diamine compounds.

[0066] Regarding the polyarylene ether compound having a polymerizable unsaturated bond-containing group, the arylene group is not particularly limited, and examples thereof include a phenylene group, a naphthylene group, and structures in which one or more alkyl groups, alkyloxy groups, halogen atoms, etc. are substituted on the aromatic carbon of these groups. Examples of the polymerizable unsaturated bond-containing group include a vinyl group, a vinyloxy group, an allyl group, an allyloxy group, a (meth)acryloyl group, a (meth)acryloyloxy group, a vinylbenzyl group, and a vinylbenzyloxy group. The polyarylene ether compound having a polymerizable unsaturated bond-containing group may have a structural moiety other than the polyarylene ether structure. Specifically, the molecular chain may contain an acrylic polymerization moiety, a (poly)urethane moiety, a (poly)ester moiety, etc. The number of polymerizable unsaturated bond-containing groups in one molecule of the polyarylene ether compound is not particularly limited, and the substitution position of the polymerizable unsaturated bond-containing group is also not particularly limited. For example, the polyarylene ether compound may have a polymerizable unsaturated bond-containing group at the molecular terminal, or may have a polymerizable unsaturated bond-containing group at both terminals.

[0067] Specific examples of the polyarylene ether compound having a polymerizable unsaturated bond-containing group include compounds represented by the following general formula (3).

[0068] [In general formula (4), R ５ is a hydrogen atom or a methyl group; l and m are integers of 1 or more; and X is a divalent organic group.

[0069] X in general formula (3) is a divalent organic group, and the specific structure is not particularly limited. Examples of the divalent organic group include a hydrocarbon group having 1 to 6 carbon atoms, a halogenated hydrocarbon group, an oxygen atom, a sulfur atom, a carbonyl group, and a sulfonyl group.

[0070] The molecular weight of the polyarylene ether compound having a radical polymerizable group is not particularly limited, but the number average molecular weight (Mn) may be in the range of 1,000 to 5,000, for example.

[0071] The ratio of the indene composition to the total mass of the curable components of the curable resin material is arbitrary, but may be, for example, 10 mass% or more, 30 mass% or more, 50 mass% or more, 80 mass% or more, or 100 mass%.

[0072] Examples of the elastomer include polyether elastomers, styrene elastomers, conjugated diene elastomers, urethane elastomers, polyester elastomers, polyamide elastomers, acrylic elastomers, and silicone elastomers.

[0073] The filler may be either an organic filler or an inorganic filler, but an inorganic filler is preferred. Examples of inorganic fillers include silica (SiO ２ ), alumina (Al ２ O ３ ), titanium oxide, barium titanate, strontium titanate, potassium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, aluminum borate, silicon carbide, mica, beryllia, clay, talc, etc. Silica is preferred from the viewpoint of dielectric properties.

[0074] The shape and size of the filler are not particularly limited. The average particle size of the filler may be, for example, 0.01 to 20 μm, or 0.1 to 10 μm. Here, the average particle size of the filler is the particle size at a point corresponding to an integrated value of 50% in a volume-based particle distribution measured by a laser diffraction scattering method.

[0075] As the curing accelerator, for example, a radical polymerization initiator can be used. 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 the polymerization initiator include azo-based polymerization initiators and organic peroxide-based polymerization initiators. Examples of azo-based 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-carbonitrile), and dimethyl 1,1'-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-tridecafluorooctyl 4-cyanopentanoate), and the like. Examples of organic peroxide polymerization initiators include dicumyl peroxide, dibenzoyl peroxide, 2-butanone peroxide, tert-butyl perbenzoate, di-tert-butyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, α,α'-di(t-butylperoxy)diisopropylbenzene, and tert-butyl hydroperoxide.

[0076] Examples of the flame retardant include phosphorus-based flame retardants, nitrogen-based flame retardants, silicone-based flame retardants, and inorganic flame retardants.

[0077] The curable resin material may be solvent-free or may contain a solvent. The solvent can adjust the viscosity of the curable resin material to further improve the coatability. The solvent is preferably an organic solvent.

[0078] Examples of the organic solvent 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.

[0079] The method for producing the curable resin material is not particularly limited. One example of a method for producing the curable resin material is a method in which an indene composition and optional components used as needed are added and mixed. When mixing, the indene composition and optional components used as needed may be directly blended and mixed, or the indene composition and optional components used as needed may be dissolved or dispersed in a solvent and mixed. The conditions for mixing the components, such as the order of mixing, temperature, and time, are not particularly limited and may be appropriately adjusted depending on the type of raw materials, production scale, production equipment, etc.

[0080] [Prepreg] According to one embodiment, a prepreg including 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 regard to the semi-cured product of the curable resin material, in the present disclosure, the B-stage state in JIS K 6800 (1985) can be cited as one indicator of the semi-cured product. The prepreg may, for example, contain 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 the curable resin material may be partially or entirely semi-cured.

[0081] Prepregs can be obtained, for example, by impregnating a fiber substrate with a curable resin material and then drying the fiber substrate impregnated with the curable resin material. Drying is preferably carried out at a temperature at which volatile components such as solvents that may be contained in the curable resin material are removed, or at a temperature at which the curable components contained in the curable resin material are semi-cured, depending on the application. Furthermore, drying is preferably adjusted so that the thermosetting resin contained in the curable resin material is not completely cured. From this perspective, 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.

[0082] The fiber substrate may be any of woven fabric, knitted fabric, and nonwoven fabric. The fiber substrate may be provided in the form of chopped strand mat, roving, etc. The fiber material may be any of inorganic fiber and organic fiber. Examples of inorganic fiber include glass fiber and carbon fiber. Examples of glass fiber include E-glass, NE-glass, D-glass, S-glass, Q-glass, etc. Examples of organic fiber include polyimide, polyester, tetrafluoroethylene, etc. The fiber substrate may be made of one type of these fibers alone or a combination of two or more types of these fibers. From the viewpoints of dielectric properties and heat resistance, the material of the fiber substrate is preferably inorganic fiber, and more preferably glass fiber.

[0083] The fiber substrate may be appropriately selected depending on the application of the prepreg, but a sheet-like fiber substrate is preferred. Examples of the sheet-like fiber substrate include various sheet-like fiber substrates used in known laminates for electrical insulating materials. The thickness of the sheet-like fiber substrate is not particularly limited, but is preferably 0.01 to 0.1 mm, for example. Here, the thickness is measured at five points at equal distances across the entire surface of the sheet-like fiber substrate, and the arithmetic average of the five measurements is used.

[0084] [Resin Film] According to one embodiment, a resin film containing a curable resin material or a semi-cured product of the curable resin material can be provided. The resin film can be obtained, for example, by applying a curable resin material to a substrate and drying or semi-curing the material. Drying or semi-curing can be performed in the same manner as in the prepreg manufacturing method described above. After drying the resin film on the substrate, a product can be provided as a combination of the resin film and the substrate. For example, this method can provide a resin film as a surface protective film, interlayer insulating film, etc. in a printed wiring board. In another method, after drying the resin film on the substrate, the resin film can be peeled off from the substrate to provide the resin film as a product.

[0085] The substrate may be either an inorganic substrate or an organic substrate, and examples thereof include glass substrates, metal substrates such as metal foils and metal plates, plastic substrates such as plastic plates and plastic films, and paper substrates, as well as the fiber substrates described above for the prepreg. A substrate having a release layer formed on its surface may be used so that the resin film can be peeled off from the substrate.

[0086] [Metal-clad laminate] According to one embodiment, a metal-clad laminate can be provided, which includes a cured product of a curable resin material and a metal foil. Regarding the cured product of the curable resin material, in the present disclosure, one indicator of the cured product is the C-stage state according to JIS K 6800 (1985).

[0087] In the metal-clad laminate, the cured product of the curable resin material may be contained as a cured product of the curable resin material itself, or may be contained in the form of a prepreg. The metal-clad laminate preferably includes a prepreg layer and a metal foil disposed on at least one side of the prepreg layer. The prepreg layer is a cured product of the prepreg described above, and may be formed by using a single prepreg or by laminating multiple prepregs. The metal-clad laminate may also be formed by disposing metal foil on one side of the cured prepreg, or by disposing metal foil on both sides of the cured prepreg. The metal-clad laminate may be manufactured by disposing metal foil on at least one side of a single sheet-like prepreg, or by laminating two or more sheet-like prepregs and disposing metal foil on at least one of the outermost surfaces of the laminate. The metal-clad laminate may also be manufactured by laminating two or more sheet-like prepregs and disposing metal foil on both sides of the laminate.

[0088] Hereinafter, as a specific example of a method for producing a metal-clad laminate, a method in which a metal foil is arranged on a laminate of two or more sheet-like prepregs will be described.

[0089] 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 to each other, or some or all of them may be different. In the laminate, it is sufficient that at least one of the two or more sheet-like prepregs is obtained using the curable resin material according to one embodiment.

[0090] Next, a metal foil is placed on at least one surface of this laminate. The laminate with the metal foil placed thereon is heated and pressurized. This progresses the curing reaction of the sheet-like prepreg, resulting in a cured prepreg. Furthermore, adjacent sheet-like prepregs can be fixed together. The heating and pressurizing conditions are not particularly limited, but may be, for example, a temperature of 100 to 300°C, a time of 10 to 300 minutes, and a pressure of 0.5 to 50 MPa. Furthermore, after heating and pressurizing, reheating may be performed to further promote the curing of the prepreg. In this case, the reheating temperature may be 100 to 300°C. Examples of pressurizing methods that can be used include an autoclave molding machine, a multi-stage press, a multi-stage vacuum press, and a continuous molding machine.

[0091] The metal for the metal foil is not particularly limited, and examples thereof include copper, nickel, aluminum, gold, silver, platinum, molybdenum, ruthenium, tungsten, iron, titanium, chromium, and alloys containing two or more of these metal elements. Industrially, the metals copper, nickel, and aluminum are preferred. By using copper as the metal foil, a copper-clad laminate can be provided.

[0092] [Printed Wiring Board] According to one embodiment, a printed wiring board containing a cured product of a curable resin material can be provided. In the printed wiring board, the cured product of the curable resin material may be contained as a cured product of the curable resin material itself, or may be contained 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 the metal-clad laminate are as described above. The printed wiring board may be either a single-layer printed wiring board or a multilayer printed wiring board.

[0093] [Semiconductor Package] According to one embodiment, a semiconductor package can be provided that includes a printed wiring board and a semiconductor element. More specifically, for example, a semiconductor package can be provided that includes a printed wiring board that includes a cured product of a prepreg and a semiconductor element. The semiconductor package can be manufactured, for example, by mounting the semiconductor element, memory, etc. on the printed wiring board by a known method.

[0094] Examples of embodiments are given below. The present invention is not limited to the following embodiments. <1> An arylalkyl-modified indene composition, which is a composition containing a plurality of compounds having an arylalkyl group on an indene ring and differing in the number of arylalkyl groups per molecule, wherein the content of compounds having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

[0095] <2> The arylalkyl-modified indene composition according to <1>, wherein the content of compounds having 3 arylalkyl groups per molecule is 80% or more as calculated from the area ratio in a GPC chart.

[0096] <3> The arylalkyl-modified indene composition according to <1> or <2>, wherein the proportion of arylalkyl groups having a polymerizable unsaturated bond-containing group among the arylalkyl groups present in the composition is in the range of 50 to 95 mol %.

[0097] <4> An arylalkyl-modified indene composition, comprising a composition containing a plurality of compounds represented by the following general formula (1), each of which has a different number of arylalkyl groups per molecule, wherein the content of the compound having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

[0098]

[0099] [In general formula (1), R １ , R ２ and R ３ are each independently a hydrogen atom or an arylalkyl group, and R １ , R ２ and R ３ At least one of R is an arylalkyl group. ４ represents a monovalent substituent, and n is 0 or an integer of 1 to 4. When n is an integer of 2 or more, a plurality of R ４ may all be different, or some or all may be the same.]

[0100] <5> A curable resin material containing the arylalkyl-modified indene composition according to any one of <1> to <4>.

[0101] <6> A prepreg comprising the curable resin material or a semi-cured product of the curable resin material according to <5>.

[0102] <7> A resin film comprising the curable resin material according to <5> or a semi-cured product of the curable resin material.

[0103] <8> A metal-clad laminate comprising a cured product of the curable resin material according to <5> above and a metal foil.

[0104] <9> A printed wiring board comprising a cured product of the curable resin material according to <5>.

[0105] <10> A semiconductor package comprising the printed wiring board according to <9> above and a semiconductor element.

[0106] <11> A semiconductor package comprising a semiconductor element and a cured product of the curable resin material according to <5> that encapsulates the semiconductor element.

[0107] <12> A printed wiring board comprising at least one of a surface protective film and an interlayer insulating film formed from the curable resin material according to <5>.

[0108] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to the following examples.

[0109] Examples 1 to 9 Indene compositions (1) to (9) were produced in the following manner and subjected to various evaluation tests.

[0110] [Production of Indene Compositions (1) to (9)] A 500 ml reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen inlet was charged with indene, chloromethylstyrene (*1), tetra-n-butylammonium bromide (manufactured by Kanto Chemical Co., Inc.) as a phase transfer catalyst, phenothiazine as a polymerization inhibitor, and toluene as a solvent in the amounts shown in Table 1 below, and the mixture was heated and stirred at 40°C while blowing in nitrogen at a flow rate of 50 ml / min. Next, an aqueous sodium hydroxide solution (concentration: 48% by mass) in the amount shown in Table 1 was added. The mixture was allowed to react at 70°C, １ After confirming the disappearance of chloromethylstyrene by H-NMR, α-chloro-p-xylene was added in the amount shown in Table 1. The reaction was further carried out at 70°C. １ The disappearance of α-chloro-p-xylene was confirmed by H-NMR, and the reaction was terminated. Nitrogen was continuously blown in during the reaction. The reaction mixture was cooled to room temperature (25°C), neutralized with a 10% aqueous hydrochloric acid solution, and then washed twice with pure water. Toluene was distilled off under reduced pressure, and the resulting viscous liquid was washed with methanol and vacuum-dried to obtain indene compositions (1) to (9).

[0111] (*1): AGC Seimi Chemical Co., Ltd. "CMS-P", a mixture of m- and p-isomers, m-isomer content 50% by mass, p-isomer content 50% by mass

[0112] The indene composition was analyzed using "ECX400II" manufactured by JEOL RESONANCE Co., Ltd. １ H-NMR spectrum (400 MHz, CDCl ３ ) was measured, a shift or disappearance of the raw material peak was observed, indicating that a reaction had occurred in which a vinylbenzyl group was bonded to one of the 1st to 3rd positions of the indene ring and a methylbenzyl group was bonded to one of the 1st to 3rd positions of the indene ring.

[0113] [Calculation of the content of each compound in the indene composition] The content of each compound was calculated from the area ratio of the GPC chart measured under the following conditions. The GPC charts of each indene composition are shown in Figures 1 to 9. The calculation results of the content of each compound are shown in Table 1.

[0114] Apparatus: High-speed GPC apparatus "HLC-8420GPC" (Tosoh Corporation, trade name) Detector: Ultraviolet absorption detector "UV-8420" (Tosoh Corporation, trade name) Column: Guard column; TSKgel guard column SuperHZ-L, Column; TSKgel SuperHZ4000 + TSKgel SuperHZ2500 + TSKgel SuperHZ1000 (3 columns), Reference column; None (Resistor tube) (all Tosoh Corporation, trade names) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column) Eluent: Tetrahydrofuran Sample concentration: 1 mg / 1 mL Injection volume: 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40°C

[0115] [Measurement of Volatile Content of Indene Composition] The indene composition was left in an incubator at 170°C for 15 minutes. The proportion of volatile components contained in the indene composition was calculated from the difference in mass before and after the test, and evaluated according to the following criteria: A: Less than 1 mass% B: 1 mass or more but less than 1.5 mass% C: 1.5 mass% or more

[0116]

[0117] [Measurement of dielectric properties after exposing cured product to high humidity environment] Cured products of each indene composition were prepared in the following manner, and the dielectric properties were measured after exposing them to a high humidity environment. The results are shown in Table 2.

[0118] [Production of Cured Product] A low-profile copper foil ("SI-VSP-18" manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 18 μm) was placed with the S-side (shiny side) facing up, and a Teflon (registered trademark) sheet die-cut to a size of 1.0 mm thick x 20 mm long x 20 mm wide was placed on top of it. Next, a viscous liquid of an indene composition was poured into the die-cut section, and the low-profile copper foil was placed on top of it with the S-side (shiny side) facing down (the viscous liquid side of the indene composition). The resin composition was cured by vacuum heating and pressure molding at a temperature of 150°C, a pressure of 1.5 to 2.0 MPa, and a time of 120 minutes, followed by further hot molding at a temperature of 180°C for 300 minutes. The copper foil on both sides was then peeled off to obtain a cured product (thickness of cured product: 1 mm).

[0119] [Measurement of Dielectric Properties (Dielectric Loss Tangent (Df))] The cured product obtained above was cut to prepare 1 mm x 50 mm test pieces. After drying at 105°C for 1 hour, the test pieces were left to stand in an environment with an ambient temperature of 25°C and a humidity of 50% RH for 24 hours. The test pieces were then placed in an oven at 125°C for 1000 hours. After returning the test pieces to room temperature, the dielectric loss tangent (Df) was measured in the 10 GHz band at an ambient temperature of 25°C according to the cavity resonator perturbation method. The measurement device used was a "PNA Network Analyzer N5222B" from Agilent Technologies.

[0120] Comparative Example 1: Using "OPE-2St" (an oligo-phenylene ether resin having a vinylbenzyl group at the end, number average molecular weight (Mn) 1200) manufactured by Mitsubishi Gas Chemical Company, Inc., the dielectric properties of the cured product were measured after exposure to a high humidity environment in the same manner as in the examples described above. The results are also shown in Table 2.

[0121]

[0122] As shown in Table 2, the indene compositions (1) to (9) of Examples 1 to 9 had lower dielectric tangent values ​​in the cured products after exposure to a high humidity environment than the compound of Comparative Example 1, and exhibited excellent dielectric properties.

[0123] [Evaluation of Glass Transition Temperature (Tg) of Cured Product] Test pieces measuring 30 mm in length and 5 mm in width were cut from the cured product obtained above, and subjected to dynamic mechanical analysis (DMA) using a Rheogel-E4000 manufactured by UBM Corporation. The measurement conditions were a tensile mode with a heating rate of 5°C / min. The glass transition temperature (Tg) was determined from the peak of tan δ and evaluated according to the following criteria. The results are shown in Table 3. A: 200°C or higher B: 190°C or higher but less than 200°C C: Less than 190°C

[0124] [Evaluation of Thermal Expansion Coefficient of Cured Product] Test pieces measuring 5 mm square were cut from the cured product obtained above, and the thermal expansion coefficient was measured from 30 to 120°C using a thermomechanical analyzer (TMA) ("Q400" manufactured by TA Instruments Japan Co., Ltd.). The measurement was conducted twice in accordance with the IPC (The Institute for Interconnecting and Packaging Electronic Circuits) standard, under the conditions of a temperature range of 30 to 260°C, a load of 5 g, and a heating rate of 10°C / min. The average thermal expansion coefficient in the thickness direction of the test pieces in the temperature range of 30 to 120°C in the second measurement was evaluated according to the following criteria. The results are shown in Table 3. A: 50 ppm / °C or less B: More than 50 ppm / °C to 55 ppm / °C or less C: More than 55 ppm / °C

[0125]

[0126] As shown in Table 3, the indene compositions (1) to (9) of Examples 1 to 9 also have excellent heat resistance and thermal expansion resistance in the cured products.

[0127] The disclosure of this application is related to the subject matter described in PCT / JP2024 / 022558, filed on June 21, 2024, the disclosures of which are incorporated herein by reference.

Claims

1. An arylalkyl-modified indene composition, which is a composition containing a plurality of compounds having an arylalkyl group on an indene ring, each of which has a different number of arylalkyl groups per molecule, wherein the content of compounds having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group.

2. The arylalkyl-modified indene composition according to claim 1, wherein the content of compounds having three arylalkyl groups per molecule is 80% or more as calculated from the area ratio in a GPC chart.

3. The arylalkyl-modified indene composition according to claim 1, wherein the proportion of arylalkyl groups having a polymerizable unsaturated bond-containing group among the arylalkyl groups present in the composition is in the range of 50 to 95 mol %.

4. An arylalkyl-modified indene composition comprising a plurality of compounds represented by the following general formula (1), each of which has a different number of arylalkyl groups per molecule, wherein the content of the compound having one arylalkyl group per molecule is 1% or less as calculated from the area ratio in a GPC chart, and at least one of the arylalkyl groups present in the composition is an arylalkyl group having a polymerizable unsaturated bond-containing group, and at least one of the arylalkyl groups present in the composition is an arylalkyl group not having a polymerizable unsaturated bond-containing group. [In general formula (1), R １ , R ２ and R ３ are each independently a hydrogen atom or an arylalkyl group, and R １ , R ２ and R ３ At least one of R is an arylalkyl group. ４ represents a monovalent substituent, and n is 0 or an integer of 1 to 4. When n is an integer of 2 or more, a plurality of R ４ may all be different, or some or all may be the same.] 5. A curable resin material comprising the arylalkyl-modified indene composition according to any one of claims 1 to 4.

6. A prepreg comprising the curable resin material according to claim 5 or a semi-cured product of said curable resin material.

7. A resin film comprising the curable resin material according to claim 5 or a semi-cured product of the curable resin material.

8. A metal-clad laminate comprising a cured product of the curable resin material according to claim 5 and a metal foil.

9. A printed wiring board comprising a cured product of the curable resin material according to claim 5.

10. A semiconductor package comprising the printed wiring board according to claim 9 and a semiconductor element.

11. A semiconductor package comprising a semiconductor element and a cured product of the curable resin material according to claim 5 that encapsulates the semiconductor element.

12. A printed wiring board comprising at least one of a surface protection film and an interlayer insulating film formed from the curable resin material according to claim 5.

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