Polymerizable unsaturated bond-containing resin, resin composition, prepreg, resin film, metal-clad laminate, printed wiring board, and semiconductor package

Abstract

To provide a resin material which improves handleability of a semi-cured product.SOLUTION: There are used: a polymerizable unsaturated bond-containing resin which is a polymer using a polymerizable compound represented by the following formula (1) as a monomer component and has a weight average molecular weight (Mw) of 3,000 or more; and a resin composition containing the resin. In addition, there are provided a prepreg, a resin film, a metal-clad laminate, a printed wiring board, and a semiconductor package obtained using the resin or the resin composition. (In formula (1), Ar1 represents an aromatic ring structure and has one or more polymerizable unsaturated bond-containing groups on an aromatic ring; X represents a structure represented by the following formula (2); and n represents an integer of 1-10.) (In formula (2), R1 represents a C1-8 alkylene group; and Ar2 represents an aromatic ring structure.)SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to a polymerizable unsaturated bond-containing resin, a resin composition, a prepreg, a resin film, a metal-clad laminate, a printed wiring board, and a semiconductor package. [Background technology]

[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, such as mobile communication devices such as smartphones, base station equipment, network infrastructure devices such as servers, routers, and large servers, large computers, personal computers, industrial computers, etc. They are also used in electronic devices installed in home appliances, automobiles, etc. In particular, with the spread of 5G, there is an increasing demand for electronic communication devices to process huge amounts of data at high speeds.

[0003] When electronic devices process huge amounts of data at high speed, circuit board materials with low transmission loss in the high frequency range are required. Resins with low dielectric constants and low dielectric dissipation factors are used for circuit board materials, providing circuit boards with low transmission loss, but recent developments in communication technology have created a demand for the development of resins with even lower dielectric constants and dielectric dissipation factors.

[0004] Patent Document 1 discloses a thermosetting resin composition containing a vinylbenzyl compound and a polycarbodiimide compound as a material for electronic components for use in high frequency bands, and proposes that the resulting electronic components have improved adhesion to metal materials while maintaining excellent dielectric properties. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2005-325197 A Summary of the Invention [Problem to be solved by the invention]

[0006] Patent Document 1 discloses a resin composition containing a vinylbenzyl compound and a polycarbodiimide compound, which has dielectric properties suitable for high-frequency band applications. However, when a plurality of prepregs or semi-cured films formed using the resin composition are stacked, they tend to adhere to each other and become difficult to peel off. Therefore, there is a concern that the workability may decrease in the transportation of prepregs and the like and in the production of metal-clad laminates. In addition, there is room for improvement in the formability of metal-clad laminates.

[0007] An object of the present disclosure is to provide a resin and a resin composition that improve the handleability of a semi-cured product, and a prepreg, a resin film, a metal-clad laminate, a printed wiring board, and a semiconductor package obtained using the resin or the resin composition. [Means for solving the problem]

[0008] The present invention includes the following embodiments, but is not limited to the following embodiments. One embodiment relates to a polymerizable unsaturated bond-containing resin that is a polymer containing a polymerizable compound represented by the following formula (1) as a monomer component, and has a weight average molecular weight (Mw) of 3,000 or more.

[0009] [ka]

[0010] (Ar in the formula 1 represents an aromatic ring structure having one or more polymerizable unsaturated bonds on the aromatic ring. 1 may have a substituent other than a polymerizable unsaturated group. 1may all have different structures, or some or all may have the same structure. In the formula, X represents a structure represented by the following formula (2). When n is 2 or more, a plurality of X's in the formula may all have different structures, or some or all may have the same structure. n is an integer of 1 to 10.

[0011] [ka]

[0012] (R in the formula 1 represents an alkylene group having 1 to 8 carbon atoms. 1 may have different structures or may have the same structure. 2 represents an aromatic ring structure. 2 may have a substituent on the aromatic ring. Effect of the Invention

[0013] The present disclosure makes it possible to provide a resin and a resin composition that improve the handleability of a semi-cured product, and a prepreg, a resin film, a metal-clad laminate, a printed wiring board, and a semiconductor package obtained using the resin or the resin composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] Hereinafter, embodiments of the present disclosure will be described in detail. The present invention is not limited to the following embodiments.

[0015] In the present disclosure, the numerical range indicated by using "~" indicates a range including the numerical values ​​described before and after "~" as the minimum and maximum values, respectively. In the numerical ranges described in stages in the present disclosure, the upper limit or lower limit of a certain numerical range may be replaced with the upper limit or lower limit of another numerical range. In addition, the upper limit or lower limit of a numerical range described in the present disclosure may be replaced with a value shown in the examples. In the present disclosure, each component may contain one or more corresponding substances unless otherwise specified. In the present disclosure, the content of each component in the resin composition means the total amount of the multiple substances present in the resin composition when multiple substances corresponding to each component are present in the resin composition, unless otherwise specified.

[0016] In this 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 (Mw) and number average molecular weight (Mn) are converted from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). The calibration curve is approximated by a cubic equation using a set of five standard polystyrene samples (PStQuick MP-H, PStQuick B [product name by Tosoh Corporation]). The GPC conditions are shown below.

[0017] Equipment: High-speed GPC equipment "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 columns), reference column; TSKgel SuperH-RC (2 columns) (all products of Tosoh Corporation) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column), 6.0 x 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10mg / 1mL Injection volume: 20μL or 2μL Flow rate: 0.35mL / min Measurement temperature: 40℃

[0018] "Polymerizable unsaturated bond-containing resin" The polymerizable unsaturated bond-containing resin according to one embodiment of the present disclosure is a polymer having a polymerizable compound represented by the following formula (1) as a monomer component, and has a weight average molecular weight (Mw) of 3,000 or more. A part of the polymerizable unsaturated bond-containing group in the polymerizable compound remains.

[0019] [ka]

[0020] (Ar in the formula 1 represents an aromatic ring structure having one or more polymerizable unsaturated bond-containing groups on the aromatic ring. 1 may have a substituent other than the polymerizable unsaturated bond-containing group. 1 may all have different structures, or some or all may have the same structure. In the formula, X represents a structure represented by the following formula (2). When n is 2 or more, a plurality of X's in the formula may all have different structures, or some or all may have the same structure. n is an integer of 1 to 10.

[0021] [ka]

[0022] (R in the formula 1 represents an alkylene group having 1 to 8 carbon atoms. 1 may have different structures or may have the same structure. 2 represents an aromatic ring structure. 2 may have a substituent on the aromatic ring.

[0023] Regarding the polymerizable compound represented by the above formula (1), 1represents an aromatic ring structure, and has a polymerizable unsaturated bond-containing group on the aromatic ring. Examples of the aromatic ring structure include a benzene ring, a naphthalene ring, and an anthracene ring. Among these, a benzene ring is preferred from the viewpoint of handleability of the resulting semi-cured resin.

[0024] 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, and a (meth)acryloyloxy group. Among these, the vinyl group or the allyl group is preferred, and the vinyl group is more preferred, since the cured product will have excellent dielectric properties. 1 The number of polymerizable unsaturated bond-containing groups contained in is not particularly limited as long as it is 1 or more, but from the viewpoint of the balance between the ease of production of the resin and the curability, it is preferably 1 or 2, and more preferably 1. In addition, when the value is 2 or more, Ar 1 The types of the multiple polymerizable unsaturated bond-containing groups contained in may be different from each other.

[0025] Ar 1 may have a substituent other than the polymerizable unsaturated bond-containing group. Examples of the other substituent include alkyl groups such as methyl, ethyl, propyl, and butyl groups, alkyloxy groups such as methyloxy, ethyloxy, propyloxy, and butyloxy groups, halogen atoms such as fluorine, chlorine, and bromine atoms, aryl groups such as phenyl, tolyl, and xylyl groups, aralkyl groups such as benzyl and phenylethyl groups, and hydroxyl groups. Among these, from the viewpoints of the handleability of the resulting semi-cured resin and the dielectric properties of the cured product, Ar 1 It is preferred that the group does not have any other substituents.

[0026] In formula (1), multiple Ar 1 may all have the same structure or may have different structures. Among these, from the viewpoint of ease of production, it is preferable that all have the same structure.

[0027] In the above formula (2), R 1represents an alkylene group having 1 to 8 carbon atoms. Among them, from the viewpoint of handling properties of the resulting semi-cured resin, alkylene groups having 1 to 4 carbon atoms such as methylene, ethylene, ethylidene, trimethylene, propylidene, propylene, isopropylidene, butylene, and butylidene groups are preferred, and a methylene group is more preferred. 1 may be the same structure or may be different structures. In particular, from the viewpoint of the dielectric properties of the cured product, the two R 1 and preferably have the same structure, and more preferably both are methylene groups.

[0028] In the above formula (2), Ar 2 represents an aromatic ring structure. Examples of the aromatic ring structure include aromatic ring structures having 6 to 20 carbon atoms, such as a benzene ring, a naphthalene ring, and an anthracene ring. Ar 2 may have a substituent on the aromatic ring. Examples of the substituent include alkyl groups such as methyl, ethyl, propyl, and butyl groups, alkyloxy groups such as methyloxy, ethyloxy, propyloxy, and butyloxy groups, polymerizable unsaturated bond-containing groups such as vinyl, allyl, vinyloxy, and allyloxy groups, halogen atoms such as fluorine, chlorine, and bromine atoms, aryl groups such as phenyl, tolyl, and xylyl groups, aralkyl groups such as benzyl and phenylethyl groups, and hydroxyl groups. Among these, from the viewpoint of the handleability of the semi-cured product of the obtained resin, an aromatic ring structure having no substituent is preferred, and a benzene ring structure is more preferred. In addition, from the viewpoint of the handleability of the semi-cured product of the obtained resin and the dielectric properties of the cured product, it is preferable that the aromatic ring structure has no substituent.

[0029] In the above formula (2), Ar 2 R in 1 The bonding position of Ar is not particularly limited, and it may be bonded to any position of the aromatic ring structure. 2 When is a benzene ring structure, two R 1The bonding positions of the above are either the ortho-, meta-, or para-positions relative to each other. Among these, from the viewpoints of ease of production and handleability of the resulting semi-cured resin, the meta- or para-positions are preferred, and the para-position is more preferred.

[0030] In the above formula (1), when n is 2 or more, the multiple Xs in the formula (1) may all have the same structure or may have different structures. More specifically, between multiple Xs, R 1 may all be the same structure or may be different structures. 2 may all have the same structure or may have different structures. In particular, from the viewpoint of ease of production, it is preferable that the multiple Xs in formula (1) have the same structure. In that case, R 1 may all be methylene groups. 2 may all be aromatic rings having no substituents, or may be benzene.

[0031] Specific examples of the polymerizable compound represented by the above formula (1) include compounds represented by the following formula (1-1).

[0032] [ka]

[0033] In the above formula (1), n ​​is an integer of 1 to 10. Among them, 1 to 5 is preferred, and 1 to 3 is more preferred, since handling during the polymerization reaction is facilitated.

[0034] The polymerizable compound represented by the formula (1) may be a single compound consisting of components with the same value of n, or a mixture containing a plurality of components with different values ​​of n. In the latter case, the number average molecular weight (Mn) of the polymerizable compound is preferably in the range of 350 to 1,000. The weight average molecular weight (Mw) of the polymerizable compound is preferably in the range of 400 to 1,500.

[0035] The method for producing the polymerizable compound is not particularly limited, and the compound can be produced by a wide variety of methods. One example is a method in which an aromatic compound (A) having a halogenated alkyl group is reacted with a compound (B) represented by the following formula (3) under acidic conditions to obtain an intermediate, which is then subjected to a dehalogenation reaction. The aromatic compound (A) is represented by the Ar 1 and the compound (B) is a reaction raw material constituting X in the above formula (1).

[0036] YXY (3) [In the formula, X represents the structure represented by the above formula (2). Y represents a leaving group, such as a halogen atom, a hydroxyl group, an alkoxy group, or a tosyl group.]

[0037] The polymerizable unsaturated bond-containing resin is a polymer having the polymerizable compound represented by the formula (1) as a monomer component, but may have a structural portion derived from other polymerizable compounds. From the viewpoint of dielectric properties, heat resistance, handling, etc. of the cured product, the polymerizable unsaturated bond-containing resin preferably contains 50% by mass or more, and more preferably 50 to 100% by mass, of structural units derived from the polymerizable compound represented by the formula (1) relative to all constituent units. Furthermore, it is preferable that the resin contains 80 to 100% by mass or more, and more preferably 90 to 100% by mass.

[0038] The method for producing the polymerizable unsaturated bond-containing resin is not particularly limited, and the resin can be produced by a method in which a monomer component containing a polymerizable compound represented by the above formula (1) is polymerized by a general method. In the production, a polymerizable compound other than the polymerizable compound represented by the above formula (1) may be used as a monomer component. In particular, from the viewpoint of the dielectric properties, heat resistance, and handleability of the cured product of the obtained polymerizable unsaturated bond-containing resin, the proportion of the polymerizable compound represented by the above formula (1) in the monomer component used in the polymerization reaction is preferably 50 to 100 mass%, more preferably 80 to 100 mass%, and particularly preferably 90 to 100 mass%.

[0039] An example of a method for producing the polymerizable unsaturated bond-containing resin is radical polymerization. The radical polymerization initiator used is not particularly limited, and examples thereof 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), dimethyl 1,1'-azobis(1-cyclohexanecarboxylate), 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutyronitrile), and the like. nitrile), 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), etc. 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, bis(tert-butylperoxyisopropyl)benzene, tert-butyl hydroperoxide, etc.

[0040] The radical polymerization initiator may be used alone or in combination of two or more kinds. The amount of the radical polymerization initiator used can be appropriately adjusted depending on the desired degree of polymerization, etc., but from the viewpoint of easy reaction control, it is preferably in the range of 0.01 parts by mass to 5 parts by mass with respect to 100 parts by mass of the total of the monomer components as the reaction raw materials.

[0041] During the polymerization reaction, a polymerization inhibitor may be used as necessary, since it is easy to adjust the polymerization degree of the target polymerizable unsaturated bond-containing resin. 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, 4-tert-butylcaprylamide, methyl ether, tert-butyl ... Examples of the polymerization inhibitor include 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. In addition, as with the polymerization inhibitor, a chain transfer agent may be used if necessary, since it is easy to adjust the degree of polymerization of the target polymerizable unsaturated bond-containing resin. Examples of the chain transfer agent include α-methylstyrene dimer, S,S-dibenzyltrithiocarbonate, 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, 2-cyano-2-[(dodecylsulfanylthiocarbonyl)sulfanyl]propane, benzyldodecyl trithiocarbonate, 1-ethoxycarbonyl-1-phenylmethyl benzodithioate, and benzyl 4-methoxybenzodithioate.

[0042] The polymerization inhibitor and chain transfer agent may be used alone or in combination of two or more. The amount of the polymerization inhibitor and chain transfer agent used can be appropriately adjusted depending on the desired degree of polymerization, etc., but from the viewpoint of easy reaction control, it is preferable to use the amount in the range of 0.01 parts by mass to 10 parts by mass relative to 100 parts by mass of the total of the monomer components as the reaction raw materials.

[0043] The polymerization reaction may be carried out in a solvent. Examples of the solvent include toluene and xylene. These may be used alone or in the form of a mixed solvent of two or more. The amount of the solvent used is not particularly limited, but is preferably in the range of 30 to 500 parts by mass per 100 parts by mass of the monomer component as the reaction raw material, in order to facilitate reaction control.

[0044] The weight average molecular weight (Mw) of the polymerizable unsaturated bond-containing resin is 3,000 or more, which improves the handleability of the semi-cured product. Furthermore, the weight average molecular weight (Mw) is more preferably 10,000 or more, and may be 20,000 or more, 50,000 or more, 100,000 or more, 200,000 or more, 300,000 or more, or 400,000 or more. In addition, the upper limit is preferably 1,000,000 or less, and may be 800,000 or less, or 650,000 or less, from the viewpoints of solvent solubility, coatability, handleability, etc. The weight average molecular weight (Mw) of the polymerizable unsaturated bond-containing resin may be in the range of 3,000 to 1,000,000, 10,000 to 1,000,000, 50,000 to 1,000,000, 100,000 to 1,000,000, 200,000 to 1,000,000, 200,000 to 800,000, or 200,000 to 650,000.

[0045] The ratio (Mw / Mn) of the weight average molecular weight to the number average molecular weight of the polymerizable unsaturated bond-containing resin is not particularly limited, but from the viewpoints of solvent solubility, coatability, handleability, etc., it is preferably 30 or less, more preferably 25 or less. The lower limit is preferably 3 or more, more preferably 8 or more. The ratio (Mw / Mn) of the weight average molecular weight to the number average molecular weight of the polymerizable unsaturated bond-containing resin is preferably in the range of 3 to 30, more preferably 8 to 25.

[0046] From the viewpoint of ease of handling, the polymerizable unsaturated bond-containing resin is preferably liquid or fluid at 25° C., or soluble in the same volume of toluene at 25° C. The resin composition containing the polymerizable unsaturated bond-containing resin may be solvent-free and liquid at 5° C. Alternatively, the resin composition may be a resin composition containing the polymerizable unsaturated bond-containing resin and an organic solvent, in which the resin exists in a liquid or solution state at 25° C.

[0047] The polymerizable unsaturated bond-containing resin has excellent handling properties in the semi-cured product. It also has excellent dielectric properties and heat resistance in the cured product. Therefore, it can be suitably used as a main component of a resin material for electronic devices. It can also be used as a modifying additive to improve the handling properties of the resin material.

[0048] "Resin composition" The resin composition according to an embodiment of the present disclosure contains the polymerizable unsaturated bond-containing resin and other components, such as a solvent, a polymerizable compound other than the polymerizable unsaturated bond-containing resin, a curable compound having a functional group other than a polymerizable unsaturated group, an elastomer, a filler, a radical polymerization initiator, a flame retardant, an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, and a lubricant.

[0049] The above-mentioned solvent is mainly used to adjust the viscosity and coating property of the resin composition. Examples of the 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 dimethylsulfoxide; and ester-based solvents such as γ-butyrolactone. The solvent may be used alone or in the form of a mixed solvent of two or more kinds. When the resin composition contains a solvent, the amount of the solvent used is appropriately adjusted according to the properties of the intended use and purpose of the resin composition. In general, the components other than the solvent are solids, and the solids content may be 1 to 80 mass% or 50 to 80 mass% based on the total mass of the resin composition.

[0050] Examples of the other polymerizable compounds include styrene, divinylbenzene, triallyl isocyanurate, indene skeleton-containing polymerizable compounds, various maleimide compounds, and polymerizable unsaturated bond-containing polyphenylene ether compounds. These may be used alone or in combination of two or more. The amount of these other polymerizable compounds used is not particularly limited and can be appropriately adjusted according to the desired application and physical properties of the resin composition. For example, when the polymerizable unsaturated bond-containing resin is used as a main component of the resin material, the ratio of the polymerizable unsaturated bond-containing resin to the total mass of the polymerizable unsaturated bond-containing resin and other polymerizable compounds may be in the range of 40 to 100 mass%, 60 to 100 mass%, or 80 to 100 mass%.

[0051] "Cured product" According to one embodiment, a cured product of the polymerizable unsaturated bond-containing resin or the resin composition can be provided. Since the cured product is provided using the polymerizable unsaturated bond-containing resin, the tackiness of the semi-cured product can be improved and the occurrence of molding marks can be reduced in the cured product.

[0052] The cured product of the polymerizable unsaturated bond-containing resin or the resin composition preferably has a dielectric constant (Dk) of 4.0 or less at 25° C. and 10 GHz, more preferably 3.5 or less, and even more preferably 3.2 or less. More specifically, the cured product may have a dielectric constant (Dk) of 3.20 or less, 3.15 or less, or 3.10 or less at 25° C. and 10 GHz. The smaller the dielectric constant (Dk) of the cured product at 25° C. and 10 GHz, the more preferable, and there is no particular restriction on the lower limit, but it may be, for example, 2.3 or more, or 2.4 or more, taking into consideration the balance with other physical properties.

[0053] The dielectric loss tangent (Df) of the cured product of the polymerizable unsaturated bond-containing resin or the resin composition at 25° C. and 10 GHz is preferably 0.0080 or less, more preferably 0.0030 or less, and even more preferably 0.0025 or less. The smaller the dielectric loss tangent (Df) of the cured product at 25° C. and 10 GHz, the better, and there is no particular restriction on the lower limit, but it may be, for example, 0.0001 or more in consideration of the balance with other physical properties.

[0054] Furthermore, when the resin composition does not contain a filler, the cured product of the resin composition preferably has a relative dielectric constant (Dk) of 3.0 or less, more preferably 2.8 or less, and even more preferably 2.7 or less at 25° C. and 10 GHz. When the resin composition does not contain a filler, the cured product of the resin composition preferably has a dielectric loss tangent (Df) of 0.0050 or less, more preferably 0.0030 or less, and even more preferably 0.0025 or less at 25° C. and 10 GHz.

[0055] In the present disclosure, the dielectric constant (Dk) and dielectric loss tangent (Df) at 25°C and 10 GHz are measured in the 10 GHz band at 25°C in accordance with the SPDR method (split post dielectric resonator). The measurement device may be a "PNA Network Analyzer N5227A" (product name) from Agilent Technologies. The sample used for measuring the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product is a sample obtained by obtaining a cured product using the above-mentioned polymerizable unsaturated bond-containing resin or resin composition and molding it into a thickness of 1 mm and a size of 5 cm x 10 cm.

[0056] The sample to be measured for the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product is the above-mentioned polymerizable unsaturated bond-containing resin or resin composition cured to a C-stage state according to JIS K 6800 (1985).

[0057] "Prepreg" According to one embodiment, a prepreg containing the above polymerizable unsaturated bond-containing resin or a semi-cured product thereof, or the above resin composition or a semi-cured product thereof can be provided.

[0058] The prepreg may contain the above-mentioned polymerizable unsaturated bond-containing resin or a semi-cured product thereof, or the above-mentioned resin composition or a semi-cured product thereof, and a fiber substrate. In the prepreg, the above-mentioned polymerizable unsaturated bond-containing resin or resin composition may be in an uncured state, or may be in a partially or entirely semi-cured state.

[0059] The prepreg can be obtained, for example, by coating the polymerizable unsaturated bond-containing resin or resin composition on a fiber substrate and drying it. In another method, the prepreg can be obtained by impregnating a fiber substrate with the polymerizable unsaturated bond-containing resin or resin composition and drying it. Drying is preferably performed at a temperature at which volatile components such as solvents that may be contained in the resin composition are removed or higher, and may be performed in a temperature range at which the curing components in the polymerizable unsaturated bond-containing resin or resin composition are semi-cured depending on the application. In addition, drying is preferably adjusted so that the curing components in the polymerizable unsaturated bond-containing resin or resin composition are not completely cured. From this viewpoint, the drying temperature may be 80 to 200 ° C., and the drying time may be 1 to 30 minutes depending on the drying temperature, drying device, its scale, etc.

[0060] In the present disclosure, the semi-cured product of the polymerizable unsaturated bond-containing resin or resin composition means a state in which the polymerizable unsaturated bond-containing group of the curing component in the polymerizable unsaturated bond-containing resin or resin composition partially contributes to the curing reaction, and the remaining polymerizable unsaturated bond-containing group remains. The semi-cured product is further subjected to a heat treatment or the like to be in a state in which the curing reaction can continue. In the present disclosure, the B-stage state in JIS K 6800 (1985) can be cited as one index of the semi-cured product.

[0061] 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 a single fiber of these, or may be a blend of two or more of these. From the viewpoint of dielectric properties and heat resistance, the fiber substrate is preferably an inorganic fiber, and more preferably a glass fiber.

[0062] The fiber substrate may be appropriately selected according to the application of the prepreg, but a sheet-like fiber substrate is preferred. The sheet-like fiber substrate may be, for example, any of 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, for example, 0.02 to 0.25 mm. Here, the thickness is the arithmetic average value of the thicknesses measured at five points at equal distances over the entire surface of the sheet-like fiber substrate.

[0063] In the prepreg, the total mass of the polymerizable unsaturated bond-containing resin or resin composition (excluding the solvent) may be 20 to 90 mass% or 30 to 80 mass% based on the total mass of the prepreg. In this range, impregnation of the fiber base material with the resin in the prepreg can be performed more easily. In addition, the process of assembling the prepreg into a molded product and curing it can be performed more easily.

[0064] "Resin film" According to one embodiment, it is possible to provide a resin film containing the above polymerizable unsaturated bond-containing resin or a semi-cured product thereof, or the above resin composition or a semi-cured product thereof.

[0065] The resin film means a state in which the polymerizable unsaturated bond-containing resin or resin composition is molded into a film. In the resin film, the curing component in the polymerizable unsaturated bond-containing resin or resin composition may be in an uncured state, or may be in a partially or entirely semi-cured state. The resin film can be cured by heat treatment or the like to obtain a cured product.

[0066] The resin film can be obtained, for example, by coating the above-mentioned polymerizable unsaturated bond-containing resin or resin composition on a substrate and drying it. Drying may be performed in the same manner as in the manufacturing method of the prepreg. After drying the resin film on the substrate, a product may be provided as a combination of the resin film and the substrate. For example, in this method, a resin film can be provided as an insulating layer or the like in a printed wiring board. In another method, after drying the resin film on the substrate, the resin film may be peeled off from the substrate to provide the resin film as a product. The thickness of the resin film is appropriately adjusted according to the desired application and performance, but as an example, it can be in the range of 1 to 200 μm.

[0067] The substrate may be either an inorganic substrate or an organic substrate, and examples of the substrate include a glass substrate, a metal substrate such as a metal foil or a metal plate, a plastic substrate such as a plastic plate or a plastic film, a paper substrate, or a fiber substrate as described above for the prepreg. In order to peel the resin film from the substrate, a substrate having a release layer formed on the surface may be used.

[0068] The dielectric constant (Dk) and dielectric dissipation factor (Df) of the prepreg and resin film are not particularly limited, but each is preferably independently within the numerical range of the dielectric constant (Dk) and dielectric dissipation factor (Df) of the cured product of the resin composition described above.

[0069] In the present disclosure, the relative permittivity (Dk) and dielectric loss tangent (Df) of a prepreg at 25° C. and 10 GHz are measured in the 10 GHz band at 25° C. in accordance with the SPDR (split post dielectric resonator) method, as in the case of measuring the cured product described above. The measurement device used may be a “PNA Network Analyzer N5227A” (product name) from Agilent Technologies.

[0070] "Metal-clad laminate" According to one embodiment, it is possible to provide a metal-clad laminate comprising the above-mentioned unsaturated group-containing resin or cured resin composition and a metal foil.

[0071] The metal-clad laminate preferably has a resin cured product layer containing the unsaturated group-containing resin or resin composition and a metal foil formed on at least one side of the resin cured product layer. The resin cured product layer contains the cured product of the unsaturated group-containing resin or resin composition, but may be the cured product of the prepreg or resin film described above. In a more useful application, a metal foil is formed on at least one side of the cured product of the prepreg, and more preferably, a metal foil is formed on both sides of the cured product of the prepreg. The resin cured product layer may be one in which a metal foil is formed on at least one side of a sheet-like prepreg, or one in which two or more sheet-like prepregs are laminated and a metal foil is formed on at least one side of the outermost surface of the laminate. In a more useful application, the metal-clad laminate is one in which two or more sheet-like prepregs are laminated and a metal foil is formed on both sides of the laminate.

[0072] The metal-clad laminate can be produced, for example, by arranging a metal foil on one or both sides of a sheet-like prepreg, and then performing heat and pressure molding. This allows the curing reaction of the sheet-like prepreg to proceed, and a cured product of the prepreg can be obtained. When performing heat and pressure molding, only one prepreg may be used, or two or more prepregs may be laminated and used. The heat and pressure 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 1.5 to 5 MPa. After the heat and pressure are applied, reheating may be performed to further promote the curing of the prepreg. In this case, the reheating temperature may be 100 to 300°C. As the heat and pressure 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.

[0073] The metal of 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, it is preferable to use single metals such as copper, nickel, and aluminum. By using copper as the metal foil, a copper-clad laminate can be provided.

[0074] The dielectric properties of the cured product from the metal-clad laminate with the metal foil removed (also simply referred to as the relative dielectric constant of the metal-clad laminate or the dielectric tangent of the metal-clad laminate) are preferably as follows:

[0075] The dielectric constant (Dk) of the metal-clad laminate is preferably 4.0 or less, more preferably 3.5 or less, and even more preferably 3.2 or less, at 25° C. and 10 GHz. More specifically, the dielectric constant (Dk) of the metal-clad laminate may be 3.20 or less, 3.15 or less, or 3.10 or less, at 25° C. and 10 GHz. The smaller the dielectric constant (Dk) of the metal-clad laminate is at 25° C. and 10 GHz, the more preferable it is, and there is no particular limit to the lower limit, but it may be, for example, 2.3 or more, or 2.4 or more, taking into consideration the balance with other physical properties.

[0076] The dielectric loss tangent (Df) of the metal-clad laminate is preferably 0.0080 or less, more preferably 0.0012 or less, and even more preferably 0.0011 or less at 25° C. and 10 GHz. The smaller the dielectric loss tangent (Df) of the metal-clad laminate is, the more preferable it is at 25° C. and 10 GHz. There is no particular restriction on the lower limit, but it may be, for example, 0.0001 or more in consideration of the balance with other physical properties.

[0077] The method for measuring the dielectric constant (Dk) and dielectric loss tangent (Df) of metal-clad laminates is as described above. The metal foil is removed from the cured product by immersing the metal-clad laminate in an etching solution, and a 0.2 mm thick, 5 cm x 10 cm evaluation board is cut out from the test piece from which the metal foil has been removed.

[0078] "Printed wiring board" According to one embodiment, it is possible to provide a printed wiring board having a cured product of a polymerizable unsaturated bond-containing resin or a resin composition.

[0079] In the printed wiring board, the cured product of the polymerizable unsaturated bond-containing resin or resin composition can be manufactured using a polymerizable unsaturated bond-containing resin or resin composition, a prepreg, a resin film, a metal-clad laminate, or a combination thereof. For example, a printed wiring board can be provided by preparing a substrate of the printed wiring board using a cured product of the prepreg. In yet another example, a printed wiring board can be provided by using a metal-clad laminate as the substrate of the printed wiring board. Details of the prepreg, the resin film, and the metal-clad laminate are as described above.

[0080] The printed wiring board may be either a single-layer printed wiring board or a multi-layer printed wiring board.

[0081] "Semiconductor Package" According to one embodiment, a semiconductor package having a printed wiring board and a semiconductor element can be provided. The details of the printed wiring board are as described above. The semiconductor package can be manufactured, for example, by mounting a semiconductor element, a memory, and the like on the printed wiring board by a known method.

[0082] Examples of embodiments are given below. The present invention is not limited to the following embodiments. (1) A polymerizable unsaturated bond-containing resin which is a polymer having a polymerizable compound represented by the following formula (1) as a monomer component and has a weight average molecular weight (Mw) of 3,000 or more.

[0083] [ka]

[0084] (Ar in the formula 1 represents an aromatic ring structure having one or more polymerizable unsaturated bond-containing groups on the aromatic ring.1 may have a substituent other than the polymerizable unsaturated bond-containing group. 1 may all have different structures, or some or all may have the same structure. In the formula, X represents a structure represented by the following formula (2). In the formula, a plurality of X's may all have different structures, or some or all may have the same structure. n is an integer of 1 to 10.

[0085] [ka]

[0086] (R in the formula 1 represents an alkylene group having 1 to 8 carbon atoms. 1 may all have different structures, or may have some or all of the same structure. 2 represents an aromatic ring structure. 2 may have a substituent on the aromatic ring.

[0087] (2) The polymerizable unsaturated bond-containing resin according to (1) above, which has a weight average molecular weight (Mw) in the range of 200,000 to 1,000,000.

[0088] (3) The polymerizable unsaturated bond-containing resin according to (1) or (2) above, wherein the ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) is in the range of 5 to 30.

[0089] (4) The polymerizable unsaturated bond-containing resin according to any one of (1) to (3) above, which contains structural units derived from the polymerizable compound represented by formula (1) in an amount of 50 mass % or more based on all structural units.

[0090] (5) The polymerizable unsaturated bond-containing resin according to any one of (1) to (4), which has solubility in an equal volume of toluene at 25° C.

[0091] (6) A resin composition comprising the polymerizable unsaturated bond-containing resin according to any one of (1) to (5) above and other components.

[0092] (7) A prepreg comprising the polymerizable unsaturated bond-containing resin according to any one of (1) to (5) above or a semi-cured product thereof, or the resin composition according to (6) above or a semi-cured product thereof.

[0093] (8) A resin film comprising the polymerizable unsaturated bond-containing resin according to any one of (1) to (5) above or a semi-cured product thereof, or the resin composition according to (6) above or a semi-cured product thereof.

[0094] (9) A metal-clad laminate comprising a cured product of the polymerizable unsaturated bond-containing resin according to any one of (1) to (5) above or a cured product of the resin composition according to (6) above and a metal foil.

[0095] (10) A printed wiring board comprising a cured product of the polymerizable unsaturated bond-containing resin according to any one of (1) to (5) above or a cured product of the resin composition according to (6) above and a metal foil.

[0096] (11) A semiconductor package comprising the printed wiring board according to (10) above and a semiconductor element. EXAMPLES

[0097] 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.

[0098] "Method of measuring number average molecular weight (Mn) and weight average molecular weight (Mw)" The number average molecular weight (Mn) and weight average molecular weight (Mw) were calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC). The calibration curve was approximated by a third order equation using standard polystyrene: TSKstandard POLYSTYRENE (Type: A-2500, A-5000, F-20, F-80) (Tosoh Corporation, product name). The GPC measurement conditions are shown below.

[0099] Equipment: High-speed GPC equipment 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 columns), reference column; TSKgel SuperH-RC (2 columns) (all products of Tosoh Corporation) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column), 6.0 x 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10mg / 1mL Injection volume: 20μL or 2μL Flow rate: 0.35mL / min Measurement temperature: 40℃

[0100] "Preparation of polymerizable compounds" In a reaction vessel equipped with a stirrer, a thermometer, a reflux tube, and a nitrogen inlet, 236.8 g of 2-bromoethylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 56.0 g of α,α'-dichloro-p-xylene (manufactured by Fujifilm Wako Pure Chemical Industries Co., Ltd.) were added and stirred. 14.7 g of methanesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) that had been left to melt under 25°C conditions was dropped into 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 inside of the reaction vessel. After removing it from the oil bath and allowing it to cool naturally, 106.4 g of 48% NaOH aqueous solution was added dropwise to neutralize it. 960 g of toluene was added and stirred to extract toluene-soluble components. The resulting organic layer was taken out and washed five times with water. The washed organic layer was heated under reduced pressure to distill off toluene and unreacted substances, obtaining 112 g (yield 65%) of an intermediate having a 2-bromoethylbenzene structure.

[0101] Into a reaction vessel equipped with a stirrer, a thermometer, a reflux tube and a nitrogen inlet, 110 g of the intermediate obtained above, 250 g of toluene, 750 g of dimethyl sulfoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) that had been left to melt under 25°C conditions, 75 g of water, and 25 g of sodium hydroxide (solid) (manufactured by Kanto Chemical Co., Ltd.) were added. The reaction vessel was immersed in an oil bath, and the reaction was carried out at 40°C for 5 hours while stirring the contents of the reaction vessel. After being removed from the oil bath and allowed to cool naturally, 500 g of toluene was added and stirred to extract the toluene-soluble components. The obtained organic layer was taken out and washed five times with 500 g of water. The organic layer after washing was heated under reduced pressure conditions to distill off the solvent, and 65 g of the target polymerizable compound was obtained (yield 75%). The resulting polymerizable compound had a number average molecular weight (Mn) of 443 and a weight average molecular weight (Mw) of 451.

[0102] "Example 1: Production of polymerizable unsaturated bond-containing resin (1)" Into a reaction vessel equipped with a stirrer, a thermometer, a reflux tube and a nitrogen inlet, 100 g of the polymerizable compound obtained above, 5 g of α-methylstyrene dimer (manufactured by Goi Chemical Industry Co., Ltd.), and 150 g of toluene were put. The reaction vessel was immersed in an oil bath, and the inside of the reaction vessel was stirred at 300 rpm, and the temperature was raised by heating while flowing nitrogen at about 0.2 L / min. When the temperature reached 100°C, 0.1 g of 2,2'-azobis(2,4,4-trimethylpentane) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. "VR-110") was put in to start the polymerization reaction. During the reaction, toluene was appropriately added to maintain the initial liquid level and adjust the non-volatile content. The reaction was carried out for 4 hours to obtain a toluene solution of polymerizable unsaturated bond-containing resin (1) (non-volatile content 40% by mass). The number average molecular weight (Mn) of the polymerizable unsaturated bond-containing resin (1) was 54,000, the weight average molecular weight (Mw) was 619,000, the ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) was 11.5, and the monomer consumption rate was 10.6%.

[0103] "Example 2: Production of polymerizable unsaturated bond-containing resin (2)" Into a reaction vessel equipped with a stirrer, a thermometer, a reflux tube and a nitrogen inlet, 100 g of the polymerizable compound obtained above, 1 g of 2,2,6,6-tetramethylpiperidine 1-oxyl (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), and 150 g of toluene were put. The reaction vessel was immersed in an oil bath, and the inside of the reaction vessel was stirred at 300 rpm, and the temperature was raised by heating while flowing nitrogen at about 0.2 L / min. When the temperature reached 100°C, 2 g of 2,2'-azobis(2,4,4-trimethylpentane) (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd. "VR-110") was put in, and the temperature was further raised to 120°C to start the polymerization reaction. During the reaction, toluene was appropriately added to maintain the initial liquid level and adjust the non-volatile content. The reaction was carried out for 2.5 hours to obtain a toluene solution of polymerizable unsaturated bond-containing resin (2) (non-volatile content 40% by mass). The polymerizable unsaturated bond-containing resin (2) had a number average molecular weight (Mn) of 20,000, a weight average molecular weight (Mw) of 400,000, a ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) of 20, and a monomer consumption rate of 17.9%.

[0104] "Example 3: Production of polymerizable unsaturated bond-containing resin (3)" Into a reaction vessel equipped with a stirrer, a thermometer, a reflux tube and a nitrogen inlet, 100 g of the polymerizable compound obtained above, 1 g of 2,2,6,6-tetramethylpiperidine 1-oxyl (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), and 150 g of toluene were put. The reaction vessel was immersed in an oil bath, and the inside of the reaction vessel was stirred at 300 rpm, and the temperature was raised by heating while flowing nitrogen at about 0.2 L / min. When the temperature reached 120°C, 1.5 g of 2,2'-azobis(2,4,4-trimethylpentane) (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd. "VR-110") was put in to start the polymerization reaction. During the reaction, toluene was appropriately added to maintain the initial liquid level and adjust the non-volatile content. The reaction was allowed to proceed for 4.5 hours, and a toluene solution of polymerizable unsaturated bond-containing resin (3) (non-volatile content 40 mass%) was obtained. The number average molecular weight (Mn) of the polymerizable unsaturated bond-containing resin (3) was 25,000, the weight average molecular weight (Mw) was 433,000, the ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) was 17.3, and the monomer consumption rate was 18.3%.

[0105] "Resin for comparison" As a comparative resin, a 40 mass % toluene solution of a compound represented by the following formula (4) was used.

[0106] [ka]

[0107] The ratio of vinylbenzyl groups to hydrogen atoms is 2.4:0.6 on average per molecule.

[0108] Examples 4 to 6 and Comparative Example 1 The above polymerizable unsaturated bond-containing resins (1) to (3) and the comparative resin were subjected to evaluation tests according to the following procedures. The results are shown in Table 1.

[0109] "Preparation of semi-cured film" Using an applicator, the toluene solutions of the polymerizable unsaturated bond-containing resins (1) to (3) and the comparative resin obtained above were applied onto a 53 μm-thick PET film (without release treatment). The film was dried by heating in an oven at 120° C. for 10 minutes to form a semi-cured film with a thickness of about 55 μm.

[0110] "Evaluation of Handling" The two films with semi-cured films obtained above were stacked so that the semi-cured films were in contact with each other, and left at room temperature for 24 hours, and then left for an additional hour at 40° C. After leaving the films, the two films with semi-cured films were peeled off from each other, and the handleability was evaluated based on the state of the semi-cured films at that time. A: The semi-cured film was not torn and could be peeled off cleanly. B: The semi-cured film was torn.

[0111] "Preparation of prepregs" The toluene solutions of the polymerizable unsaturated bond-containing resins (1) to (3) and the comparative resin obtained above were applied to a 0.5 mm-thick NE glass cloth (manufactured by Nitto Boseki Co., Ltd.) by impregnation, and the cloth was dried by heating at 130°C for 4 minutes to obtain a prepreg having a resin-derived solid content of 70 mass%.

[0112] "Measurement of dielectric constant and dielectric loss tangent of prepreg" The prepreg obtained above was left to stand for 24 hours under conditions of 24.5°C and 25% relative humidity. The prepreg after standing was used as a sample and the relative dielectric constant (Dk) and dielectric loss tangent (Df) were measured at 25°C and 10 GHz using a "PNA Network Analyzer N5227A" (product name) manufactured by Agilent Technologies in accordance with the SPDR method (split post dielectric resonator). The measured values ​​were evaluated according to the following criteria. Dielectric constant (Dk) A: 2.70 or less B: Over 2.70 Dielectric loss tangent (Df) A: 0.0020 or less B: Over 0.0020

[0113] "Measurement of glass transition temperature in prepregs" The prepreg obtained above was used as a sample, and the glass transition temperature was measured by dynamic viscoelastic measurement (DMA) using "Rheogel-E4000" (product name) manufactured by UBM Corporation.

[0114] [Table 1]

[0115] As shown in Table 1, it can be seen that the use of the polymerizable unsaturated bond-containing resin of this embodiment improves the handleability of the semi-cured product. [Industrial Applicability]

[0116] The resin or resin composition according to some embodiments of the present disclosure can be used as a substrate material for metal-clad laminates such as copper-clad laminates, printed wiring boards, and the like in electronic devices that are expected to use high-speed signals and large capacity signals, such as mobile communication devices typified by smartphones, base station equipment thereof, servers, routers, and other network infrastructure devices, and large computers.

Claims

1. A polymerizable unsaturated bond-containing resin, which is a polymerized product having a polymerizable compound represented by the following formula (1) as a monomer component, and has a weight average molecular weight (Mw) of 3,000 or more: 【Chemistry 1】 (In the formula Ar １ represents an aromatic ring structure having one or more polymerizable unsaturated bond-containing groups on the aromatic ring. １ may have a substituent other than the polymerizable unsaturated bond-containing group. １ may all have different structures, or some or all may have the same structure. X in the formula represents a structure represented by the following formula (2). When n is 2 or more, a plurality of Xs in the formula may all have different structures, or some or all may have the same structure. n is an integer from 1 to 10. 【Chemistry 2】 (In the formula R １ represents an alkylene group having 1 to 8 carbon atoms. １ may have different structures or may have the same structure. ２ represents an aromatic ring structure. ２ may have a substituent on the aromatic ring.

2. 2. The polymerizable unsaturated bond-containing resin according to claim 1, which has a weight average molecular weight (Mw) in the range of 200,000 to 1,000,000.

3. 2. The polymerizable unsaturated bond-containing resin according to claim 1, wherein the ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) is in the range of 3 to 30.

4. The polymerizable unsaturated bond-containing resin according to claim 1 , which contains structural units derived from the polymerizable compound represented by formula (1) in an amount of 50 mass % or more based on all structural units.

5. 2. The polymerizable unsaturated bond-containing resin according to claim 1, which has solubility in an equal volume of toluene at 25°C.

6. A resin composition comprising the polymerizable unsaturated bond-containing resin according to claim 1 and other components.

7. A prepreg comprising the polymerizable unsaturated bond-containing resin according to any one of claims 1 to 5 or a semi-cured product thereof, or the resin composition according to claim 6 or a semi-cured product thereof.

8. A resin film comprising the polymerizable unsaturated bond-containing resin according to any one of claims 1 to 5 or a semi-cured product thereof, or the resin composition according to claim 6 or a semi-cured product thereof.

9. A metal-clad laminate comprising a cured product of the polymerizable unsaturated bond-containing resin according to any one of claims 1 to 5, or a cured product of the resin composition according to claim 6, and a metal foil.

10. A printed wiring board comprising a cured product of the polymerizable unsaturated bond-containing resin according to any one of claims 1 to 5, or a cured product of the resin composition according to claim 6.

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

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