Resin composition, prepreg, laminate, resin film, multilayer printed wiring board, semiconductor package, method for producing resin composition, and modified conjugated diene polymer

Abstract

To provide a resin composition having excellent dielectric properties in a high frequency band of 10 GHz or more, excellent compatibility and flame-retardancy and a method for producing the same, and provide a prepreg, a laminate, a resin film, a multilayer printed wiring board and a semiconductor package, as well as a modified conjugated diene polymer each of which includes the resin composition.SOLUTION: The present invention discloses a resin composition that contains (A) at least one selected from the group consisting of a maleimide compound having one or more N-substituted maleimide groups and a derivative thereof and (B) a modified conjugated diene polymer that results from a reaction between (b1) a conjugated diene polymer having a vinyl group in a side chain and (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond, and a method for producing the same. There are also provided a prepreg, a laminate, a resin film, a multilayer printed wiring board and a semiconductor package, as well as a modified conjugated diene polymer each of which includes the resin composition.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present embodiment relates to a resin composition and a method for producing the same, a prepreg, a laminate, a resin film, a multilayer printed wiring board, a semiconductor package, and a modified conjugated diene polymer. [Background technology]

[0002] The speed and capacity of signals used in electronic devices such as mobile phones, their base station equipment, servers, routers, and other network infrastructure equipment, and mainframe computers are increasing year by year. As signal speeds and capacity increase, the substrate materials for printed wiring boards used in electronic devices are required to have dielectric properties (hereinafter sometimes referred to as "high-frequency properties") that can reduce transmission loss of high-frequency signals, i.e., low dielectric constant and low dielectric dissipation factor. In recent years, in addition to the electronic devices mentioned above, new systems that handle high-frequency wireless signals have been put into practical use or are planned for practical use in the fields of intelligent transport systems (ITS) related to automobiles and transportation systems, as well as in the field of indoor short-range communications. Therefore, it is expected that there will be an increasing need for substrate materials with excellent high-frequency characteristics for the printed wiring boards used in these fields.

[0003] Patent Document 1 aims to provide a thermosetting resin composition that has a low dielectric loss tangent, low thermal expansion, and excellent wiring embedding properties and flatness, and discloses a technology in which a polybutadiene-based elastomer modified with an acid anhydride is blended into a thermosetting resin composition that contains an inorganic filler and a polyimide compound having a structural unit derived from a maleimide compound having at least two N-substituted maleimide groups and a structural unit derived from a diamine compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2018-012747 Summary of the Invention [Problem to be solved by the invention]

[0005] Recently, there has been a demand for substrate materials to be used in fifth-generation mobile communication system (5G) antennas, which use radio waves in the frequency band above 6 GHz, and millimeter-wave radars, which use radio waves in the frequency band from 30 to 300 GHz. To this end, it is necessary to develop resin compositions with further improved dielectric properties in the 10 GHz band and above. While maleimide compounds used as thermosetting resins have excellent heat resistance, their dielectric properties remain subject to improvement due to the presence of highly polar groups. One effective method for improving dielectric properties is to add a low-polarity component, such as a polybutadiene-based elastomer, to a resin composition containing a maleimide compound, as described in Patent Document 1. However, low-polarity components, such as polybutadiene-based elastomers, may separate within the resin composition due to their low compatibility with the highly polar maleimide compound. Such separation not only prevents the dielectric properties from being fully improved, but also leads to various problems, such as reduced quality stability and poor handling due to bleed-out. Furthermore, low-polarity components, such as polybutadiene-based elastomers, are prone to combustion, making it difficult to achieve sufficient flame retardancy.

[0006] The technology of Patent Document 1 aims to improve compatibility with maleimide compounds by introducing an acid anhydride into a polybutadiene elastomer as a polar group. However, the introduction of an acid anhydride increases the polarity of the polybutadiene elastomer, which hinders the effect of improving dielectric properties. Furthermore, even with this method, it is difficult to solve the problem of reduced flame retardancy. Therefore, with the technology disclosed in Patent Document 1, it has been difficult to improve the dielectric properties while maintaining good compatibility and flame retardancy.

[0007] In view of the current situation, an object of the present embodiment is to provide a resin composition having excellent dielectric properties, compatibility, and flame retardancy in a high frequency band of 10 GHz or more, a method for producing the same, a prepreg, a laminate, a resin film, a multilayer printed wiring board, and a semiconductor package, which use the resin composition, and a modified conjugated diene polymer. [Means for solving the problem]

[0008] As a result of investigations conducted by the present inventors to solve the above-mentioned problems, they found that the above-mentioned problems can be solved by blending a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in the side chain with a compound having a phosphorus atom and an ethylenically unsaturated bond with a maleimide compound. That is, this embodiment relates to the following [1] to

[13] . [1] (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; A resin composition comprising: [2] The resin composition according to the above [1], wherein the component (b2) is a compound having a phosphine oxide group and an ethylenically unsaturated bond. [3] The resin composition according to the above [2], wherein the compound having a phosphine oxide group and an ethylenically unsaturated bond is a phosphine oxide group-containing (meth)acrylate compound. [4] The resin composition according to any one of the above [1] to [3], wherein the component (b1) is a polybutadiene having a 1,2-vinyl group. [5] The resin composition according to any one of the above [1] to [4], further comprising a styrene-based elastomer. [6] The resin composition according to any one of the above [1] to [5], wherein the component (A) is at least one selected from the group consisting of maleimide compounds and derivatives thereof, each of which contains a condensed ring of an aromatic ring and an aliphatic ring in its molecular structure and has two or more N-substituted maleimide groups. [7] A prepreg comprising the resin composition according to any one of [1] to [6] above. [8] A laminate comprising the prepreg according to [7] above and a metal foil. [9] A resin film comprising the resin composition according to any one of the above [1] to [6].

[10] A multilayer printed wiring board comprising one or more members selected from the group consisting of the prepreg described in [7] above, the laminate described in [8] above, and the resin film described in [9] above.

[11] A semiconductor package comprising the multilayer printed wiring board according to

[10] above and a semiconductor element mounted thereon.

[12] A method for producing the resin composition according to any one of [1] to [6] above, (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; A method for producing a resin composition, comprising mixing the above components.

[13] A modified conjugated diene polymer obtained by reacting (b1) a conjugated diene polymer having a vinyl group in the side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond. [Effects of the Invention]

[0009] According to the present embodiment, it is possible to provide a resin composition having excellent dielectric properties, compatibility, and flame retardancy in a high frequency band of 10 GHz or more, a method for producing the same, a prepreg, a laminate, a resin film, a multilayer printed wiring board, and a semiconductor package, all of which use the resin composition, and a modified conjugated diene polymer. DETAILED DESCRIPTION OF THE INVENTION

[0010] In this specification, 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. For example, the expression "X to Y" (X and Y are real numbers) means a range of values ​​that is equal to or greater than X and equal to or less than Y. In this specification, the expression "equal to or greater than X" means X and a value greater than X, and this also applies when the values ​​are different. In this specification, the expression "equal to or less than Y" means Y and a value less than Y. The lower and upper limits of any numerical range described herein may be combined with any lower or upper limit of any other numerical range. In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with values ​​shown in the examples.

[0011] Unless otherwise specified, each of the components and materials exemplified in this specification may be used alone or in combination of two or more. In this specification, the content of each component in a resin composition means the total amount of the multiple substances present in the resin composition, unless otherwise specified, when multiple substances corresponding to each component are present in the resin composition. In this specification, the term "resin composition" includes a mixture of the components described below and a semi-cured product of the mixture.

[0012] In this specification, the term "solid content" refers to non-volatile content excluding volatile substances such as solvents, and refers to components that remain without volatilization when the resin composition is dried, including those that are liquid, syrup-like, or waxy at room temperature. Here, in this specification, room temperature refers to 25°C.

[0013] The term "compatible" as used herein means that the resins are not necessarily miscible at the molecular level, but are miscible with each other at the nano- or micro-level, or in appearance. In this specification, "(meth)acrylate" means "acrylate" and its corresponding "methacrylate." Similarly, "(meth)acrylic" means "acrylic" and its corresponding "methacrylic," and "(meth)acryloyl" means "acryloyl" and its corresponding "methacryloyl." The number average molecular weight in this specification refers to a value measured in terms of polystyrene by gel permeation chromatography (GPC). Specifically, the number average molecular weight in this specification can be measured by the method described in the Examples.

[0014] The mechanism of action described in this specification is speculation and does not limit the mechanism by which the resin composition according to this embodiment exhibits its effects. Any combination of the features described in this specification is also included in this embodiment.

[0015] [Resin composition] The resin composition of the present embodiment is (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; The resin composition contains:

[0016] In the following description, one or more compounds selected from the group consisting of (A) maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof may be referred to as "maleimide resin (A)" or "component (A)." Furthermore, a modified conjugated diene polymer obtained by reacting (B)(b1) a conjugated diene polymer having a vinyl group in the side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond may be referred to as a "modified conjugated diene polymer (B)" or a "(B) component." Furthermore, (b1) a conjugated diene polymer having a vinyl group in its side chain may be referred to as "conjugated diene polymer (b1)" or "component (b1)". Furthermore, (b2) the compound having a phosphorus atom and an ethylenically unsaturated bond may be referred to as "phosphorus-containing monomer (b2)" or "component (b2)".

[0017] The reason why the resin composition of this embodiment has excellent dielectric properties, compatibility, and flame retardancy in the high frequency band of 10 GHz or higher is not clear, but is presumed to be as follows. The resin composition of the present embodiment contains a maleimide-based resin (A) that is excellent in heat resistance and the like. However, as described above, the maleimide-based resin (A) is inherently incompatible with compounds with low polarity, such as conjugated diene polymers. On the other hand, it is presumed that the modified conjugated diene polymer (B) contained in the resin composition of this embodiment is obtained by reacting the conjugated diene polymer (b1) with the phosphorus-containing monomer (b2), thereby partially increasing the polarity of the conjugated diene polymer (b1), thereby improving its compatibility with the maleimide-based resin (A). Furthermore, the phosphorus-containing monomer (b2) reacted with the conjugated diene polymer (b1) contains a phosphorus atom, which contributes to improved flame retardancy. Therefore, for example, even if part or all of a conventionally used flame retardant is replaced with the modified conjugated diene polymer (B), flame retardancy equivalent to or better than that of the conventional one can be achieved. In other words, since the modified conjugated diene polymer (B) has excellent compatibility and can simultaneously improve both flame retardancy and dielectric properties, it is presumed that the resin composition of this embodiment containing the modified conjugated diene polymer (B) has excellent dielectric properties, compatibility, and flame retardancy. Hereinafter, each component that may be contained in the resin composition of the present embodiment will be described in order.

[0018] <Maleimide resin (A)> The maleimide resin (A) is at least one selected from the group consisting of maleimide compounds having at least one N-substituted maleimide group and derivatives thereof. The maleimide resin (A) may be used alone or in combination of two or more. In the following description, a maleimide compound having one or more N-substituted maleimide groups may be referred to as a "maleimide compound (AX)" or a "(AX) component." Furthermore, a derivative of a maleimide compound having one or more N-substituted maleimide groups may be referred to as a "maleimide compound derivative (AY)" or "(AY) component."

[0019] (Maleimide compound (AX)) The maleimide compound (AX) is not particularly limited as long as it is a maleimide compound having one or more N-substituted maleimide groups. From the viewpoints of dielectric properties, conductor adhesion, and heat resistance, the maleimide compound (AX) is preferably a maleimide compound having a condensed ring of an aromatic ring and an aliphatic ring in its molecular structure and having two or more N-substituted maleimide groups [hereinafter, sometimes referred to as "maleimide compound (A1)" or "component (A1)"].

[0020] [Maleimide compound (A1)] From the viewpoints of dielectric properties, conductor adhesion, and heat resistance, the maleimide compound (A1) is preferably an aromatic maleimide compound having a condensed ring of an aromatic ring and an aliphatic ring in its molecular structure and having two or more N-substituted maleimide groups. Moreover, the maleimide compound (A1) is more preferably an aromatic bismaleimide compound containing a condensed ring of an aromatic ring and an aliphatic ring in the molecular structure and having two N-substituted maleimide groups. In this specification, the term "aromatic maleimide compound" refers to a compound having an N-substituted maleimide group directly bonded to an aromatic ring, and the term "aromatic bismaleimide compound" refers to a compound having two N-substituted maleimide groups directly bonded to an aromatic ring.

[0021] The fused ring contained in the maleimide compound (A1) preferably has a fused bicyclic structure, more preferably an indane ring, from the viewpoints of dielectric properties, adhesion to a conductor, and ease of production. The maleimide compound (A1) containing an indane ring is preferably an aromatic bismaleimide compound containing an indane ring. In this specification, the term "indan ring" refers to a fused bicyclic structure of an aromatic six-membered ring and a saturated aliphatic five-membered ring. At least one of the ring-forming carbon atoms forming the indan ring has a linking group for bonding to another group constituting the maleimide compound (A1). The ring-forming carbon atom having the linking group and the other ring-forming carbon atoms may not have a linking group, a substituent, or the like other than the above-mentioned linking group, but it is preferable that they have a linking group other than the above to form a divalent group.

[0022] In the maleimide compound (A1), the indane ring is preferably contained as a divalent group represented by the following general formula (A1-1).

[0023] [ka] (In the formula, R a1 is an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. a1 is an integer between 0 and 3. a2 ~R a4 are each independently an alkyl group having 1 to 10 carbon atoms. * represents a bonding site.

[0024] R in the above general formula (A1-1) a1 Examples of the alkyl group having 1 to 10 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, etc. These alkyl groups may be either linear or branched. R a1Examples of the alkyl group contained in the alkyloxy group having 1 to 10 carbon atoms and the alkylthio group having 1 to 10 carbon atoms represented by the following formula include the same as the alkyl group having 1 to 10 carbon atoms described above. R a1 Examples of the aryl group having 6 to 10 carbon atoms represented by the formula (I) include a phenyl group and a naphthyl group. R a1 Examples of the aryl group contained in the aryloxy group having 6 to 10 carbon atoms and the arylthio group having 6 to 10 carbon atoms represented by the following formula include the same as the aryl group having 6 to 10 carbon atoms described above. R a1 Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by the formula (I) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. In the above general formula (A1-1), n a1 is an integer between 1 and 3, R a1 From the viewpoint of solvent solubility and reactivity, alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, and aryl groups having 6 to 10 carbon atoms are preferred, and alkyl groups having 1 to 4 carbon atoms are more preferred.

[0025] R a2 ~R a4 Examples of the alkyl group having 1 to 10 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. These alkyl groups may be either linear or branched. Among these, R a2 ~R a4 is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. In the above general formula (A1-1), n a1 is an integer from 0 to 3, and n a1 When is 2 or 3, multiple R a1 They may be the same or different.

[0026] Among the above, the divalent group represented by the general formula (A1-1) is, from the viewpoint of ease of production, a1 is 0 and R a2 ~R a4 is a methyl group, a divalent group represented by the following formula (A1-1a) is preferred.

[0027] [ka] (In the formula, * represents a binding site.)

[0028] As the maleimide compound (A1) containing a divalent group represented by the above general formula (A1-1), one represented by the following general formula (A1-2) is preferred from the viewpoints of dielectric properties, conductor adhesion, heat resistance, and ease of production.

[0029] [ka] (In the formula, R a1 ~R a4 and n a1 is the same as in the general formula (A1-1). a5 are each independently an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxyl group, or a mercapto group. a2 are each independently an integer of 0 to 4. a3 is a number between 0.95 and 10.0.)

[0030] In the general formula (A1-2), multiple R a1 Multiple n a1 R a5 Multiple n a2 Each of the two may be the same or different. n a3 If is greater than 1, multiple R a2 Ra3 R a4 Each of the two may be the same or different.

[0031] R in the above general formula (A1-2) a5 Examples of the alkyl group having 1 to 10 carbon atoms represented by include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, etc. These alkyl groups may be either linear or branched. R a5 Examples of the alkyl group contained in the alkyloxy group having 1 to 10 carbon atoms and the alkylthio group having 1 to 10 carbon atoms represented by the following formula include the same as the alkyl group having 1 to 10 carbon atoms described above. R a5 Examples of the aryl group having 6 to 10 carbon atoms represented by the formula (I) include a phenyl group and a naphthyl group. R a5 Examples of the aryl group contained in the aryloxy group having 6 to 10 carbon atoms and the arylthio group having 6 to 10 carbon atoms represented by the following formula include the same as the aryl group having 6 to 10 carbon atoms described above. R a5 Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by the formula (I) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. Among these, R a5 From the viewpoints of solvent solubility and ease of production, the alkyl group having 1 to 4 carbon atoms, the cycloalkyl group having 3 to 6 carbon atoms, and the aryl group having 6 to 10 carbon atoms are preferred, the alkyl group having 1 to 3 carbon atoms is more preferred, and the methyl group is even more preferred.

[0032] In the above general formula (A1-2), n a2 is an integer of 0 to 4, and is preferably an integer of 1 to 3, more preferably 2 or 3, and even more preferably 2, from the viewpoints of compatibility with other resins, dielectric properties, conductor adhesion, and ease of production. In addition, n a2When n is 1 or more, the benzene ring and the N-substituted maleimide group have a twisted conformation, and intermolecular stacking is suppressed, which tends to further improve solvent solubility. a2 If is greater than or equal to 1, R a5 The substitution position is preferably the ortho position relative to the N-substituted maleimide group. In the above general formula (A1-2), n a3 From the viewpoints of dielectric properties, conductor adhesion, solvent solubility, handling properties, and heat resistance, n is preferably a number from 0.98 to 8.0, more preferably a number from 1.0 to 7.0, and even more preferably a number from 1.1 to 6.0. a3 represents the average number of structural units containing an indane ring.

[0033] From the viewpoints of dielectric properties, adhesion to conductors, solvent solubility, and ease of production, the maleimide compound (A1) represented by the above general formula (A1-2) is more preferably one represented by the following general formula (A1-3).

[0034] [ka] (In the formula, R a1 ~R a5 and n a1 and n a3 is the same as in the general formula (A1-2) above.

[0035] Examples of the maleimide compound (A1) represented by the general formula (A1-3) include a compound represented by the following general formula (A1-3-1), a compound represented by the following general formula (A1-3-2), and a compound represented by the following general formula (A1-3-3).

[0036] [ka] (In the formula, n a3 is the same as in the general formula (A1-2) above.

[0037] The number average molecular weight of the maleimide compound (A1) is not particularly limited, but from the viewpoints of compatibility with other resins, conductor adhesion, and heat resistance, it is preferably 600 to 3,000, more preferably 800 to 2,000, and even more preferably 1,000 to 1,500.

[0038] The maleimide compound (A1) can be produced, for example, by a method of reacting an intermediate amine compound containing a fused ring of an aromatic ring and an aliphatic ring (hereinafter, sometimes simply referred to as an "intermediate amine compound") with maleic anhydride (hereinafter, sometimes referred to as a "maleimidization reaction").

[0039] Hereinafter, a method for producing the maleimide compound (A1) will be described taking as an example a maleimide compound containing an indane ring as a condensed ring of an aromatic ring and an aliphatic ring. An intermediate amine compound of a maleimide compound containing an indan ring can be obtained as a compound represented by the following general formula (A1-6) by reacting, for example, a compound represented by the following general formula (A1-4) [hereinafter, sometimes referred to as "compound A"] with a compound represented by the following general formula (A1-5) [hereinafter, sometimes referred to as "compound B"] in the presence of an acid catalyst [hereinafter, sometimes referred to as "cyclization reaction"].

[0040] [ka] (In the formula, R a1 and n a1 is the same as in the general formula (A1-1). a6 are each independently a group represented by the above formula (A1-4-1) or (A1-4-2), and two R a6 At least one of the R a6 The ortho position of is a hydrogen atom.)

[0041] [ka] (In the formula, R a5 and n a2is the same as in the above general formula (A1-2), provided that at least one of the ortho- and para-positions of the amino group is a hydrogen atom.

[0042] [ka] (In the formula, R a1 , R a5 and n a1 ~n a3 is the same as in the general formula (A1-2) above.

[0043] Examples of compound A include p- or m-diisopropenylbenzene, p- or m-bis(α-hydroxyisopropyl)benzene, 1-(α-hydroxyisopropyl)-3-isopropenylbenzene, 1-(α-hydroxyisopropyl)-4-isopropenylbenzene, mixtures thereof, nuclear alkyl group-substituted products of these compounds, and nuclear halogen-substituted products of these compounds. Examples of the above-mentioned alkyl group-substituted nuclei include diisopropenyltoluene and bis(α-hydroxyisopropyl)toluene. Examples of the nuclear halogen-substituted compounds include chlorodiisopropenylbenzene and chlorobis(α-hydroxyisopropyl)benzene. These compounds A may be used alone or in combination of two or more.

[0044] Examples of compound B include aniline, dimethylaniline, diethylaniline, diisopropylaniline, ethylmethylaniline, cyclobutylaniline, cyclopentylaniline, cyclohexylaniline, chloroaniline, dichloroaniline, toluidine, xylidine, phenylaniline, nitroaniline, aminophenol, methoxyaniline, ethoxyaniline, phenoxyaniline, naphthoxyaniline, aminothiol, methylthioaniline, ethylthioaniline, phenylthioaniline, etc. These compounds B may be used alone or in combination of two or more.

[0045] In the cyclization reaction, for example, compound A and compound B are charged in a molar ratio (compound B / compound A) of preferably 0.1 to 2.0, more preferably 0.15 to 1.5, and even more preferably 0.2 to 1.0, and then the first-stage reaction is carried out. Next, it is preferable to add compound B at a molar ratio (additional compound B / compound A) relative to the previously added compound A of preferably 0.5 to 20, more preferably 0.6 to 10, and even more preferably 0.7 to 5, to carry out the second-stage reaction.

[0046] Examples of acid catalysts used in the cyclization reaction include inorganic acids such as phosphoric acid, hydrochloric acid, and sulfuric acid; organic acids such as oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, and fluoromethanesulfonic acid; solid acids such as activated clay, acid clay, silica alumina, zeolite, and strongly acidic ion exchange resins; heteropolyhydrochloric acid, etc. These may be used alone or in combination of two or more. From the viewpoints of reaction rate and reaction uniformity, the amount of the acid catalyst to be added is preferably 5 to 40 parts by mass, more preferably 5 to 35 parts by mass, and even more preferably 5 to 30 parts by mass, relative to 100 parts by mass of the total amount of Compound A and Compound B initially charged.

[0047] The reaction temperature for the cyclization reaction is preferably 100 to 300°C, more preferably 130 to 250°C, and even more preferably 150 to 230°C, from the viewpoints of reaction rate and reaction uniformity. The reaction time for the cyclization reaction is preferably 2 to 24 hours, more preferably 4 to 16 hours, and even more preferably 8 to 12 hours, from the viewpoints of productivity and allowing the reaction to proceed sufficiently. However, these reaction conditions can be appropriately adjusted depending on the types of raw materials used, and are not particularly limited. In the cyclization reaction, a solvent such as toluene, xylene, chlorobenzene, etc. may be used as needed. In addition, when water is produced as a by-product in the cyclization reaction, the dehydration reaction may be promoted by using a solvent that can be azeotropically dehydrated.

[0048] Next, the intermediate amine compound obtained above is reacted with maleic anhydride in an organic solvent to perform a maleimide reaction in which the primary amino group of the intermediate amine compound is converted to a maleimide group, thereby obtaining maleimide compound (A1). The equivalent ratio of maleic anhydride to the primary amino group equivalent of the intermediate amine compound in the maleimidation reaction (maleic anhydride / primary amino group) is not particularly limited, but from the viewpoint of reducing the amount of unreacted primary amino groups and the amount of unreacted maleic anhydride, it is preferably 1.0 to 1.5, more preferably 1.05 to 1.3, and even more preferably 1.1 to 1.2. The amount of organic solvent used in the maleimidation reaction is not particularly limited, but from the viewpoint of the reaction rate and reaction uniformity, it is preferably 50 to 5,000 parts by mass, more preferably 70 to 2,000 parts by mass, and even more preferably 100 to 500 parts by mass per 100 parts by mass of the total amount of the intermediate amine compound and maleic anhydride.

[0049] The maleimidation reaction is preferably carried out by reacting an intermediate amine compound with maleic anhydride in two steps. The reaction temperature in the first stage reaction is preferably 10 to 100°C, more preferably 20 to 70°C, and even more preferably 30 to 50°C. The reaction time in the first stage reaction is preferably 0.5 to 12 hours, more preferably 0.7 to 8 hours, and even more preferably 1 to 4 hours. The second stage reaction is preferably carried out after the completion of the first stage reaction and after adding a catalyst such as toluenesulfonic acid. The reaction temperature in the second stage reaction is preferably 90 to 130°C, more preferably 100 to 125°C, and even more preferably 105 to 120°C. The reaction time in the second stage reaction is preferably 2 to 24 hours, more preferably 4 to 15 hours, and even more preferably 6 to 10 hours. However, the above reaction conditions can be appropriately adjusted depending on the types of raw materials used, and are not particularly limited. After the reaction, if necessary, purification such as washing with water may be carried out to remove unreacted raw materials and other impurities.

[0050] The maleimide compound (A1) obtained by the above method may contain a maleimide compound not containing an indane ring as a by-product. Examples of the maleimide compound not containing an indane ring include the maleimide compound represented by n in the above general formula (A1-2). a3 is a compound in which The content of the maleimide compound not containing an indane ring, which is a by-product, in the reaction product can be measured, for example, by measuring the reaction product by GPC. a3 Using compounds in which n is 0 to 4, a3 After creating a calibration curve of the elution time versus the number of compounds, the n of compounds contained in the reaction product was determined from the elution times of the peaks observed in the GPC chart of the reaction product. a3 The number and average value of each peak can be determined by the area ratio of each peak. a3 It is possible to grasp the content ratio of compounds having the number of The maleimide compound (A1) preferably has a small content of maleimide compounds not containing an indan ring as by-products, and therefore, in a GPC chart of the reaction product, the area ratio of maleimide compounds not containing an indan ring as by-products to the peak area of ​​the entire reaction product is preferably 40% or less, more preferably 30% or less, even more preferably 20% or less, and particularly preferably 10% or less.

[0051] The maleimide compound (AX) may be a maleimide compound (A2) other than the above-mentioned maleimide compound (A1) [hereinafter, sometimes referred to as "maleimide compound (A2)" or "component (A2)"].

[0052] [Maleimide compound (A2)] The maleimide compound (A2) is preferably a maleimide compound represented by the following general formula (A2-1).

[0053] [ka] (In the formula, X a11 is a divalent organic group that does not contain a fused ring of an aromatic ring and an aliphatic ring.

[0054] X in the above general formula (A2-1) a11 is a divalent organic group that does not contain a fused ring of an aromatic ring and an aliphatic ring. X in the above general formula (A2-1) a11 Examples of the divalent organic group represented by the formula (A2-2) include a divalent group represented by the following formula (A2-3), a divalent group represented by the following formula (A2-4), a divalent group represented by the following formula (A2-5), and a divalent group represented by the following formula (A2-6).

[0055] [ka] (In the formula, R a11 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. a11 is an integer from 0 to 4. * represents a binding site.

[0056] R in the above general formula (A2-2) a11 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl; alkenyl groups having 1 to 5 carbon atoms, and alkynyl groups having 1 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. The aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. n in the above general formula (A2-2) a11 is an integer of 0 to 4, and from the viewpoint of availability, is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. n a11 is an integer equal to or greater than 2, multiple R a11 They may be the same or different.

[0057] [ka] (In the formula, R a12 and R a13 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. a12 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond, or a divalent group represented by the following general formula (A2-3-1): a12 and n a13 are each independently an integer of 0 to 4. * represents a binding site.

[0058] R in the above general formula (A2-3) a12 and R a13 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl; alkenyl groups having 1 to 5 carbon atoms, and alkynyl groups having 1 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. From the viewpoints of compatibility with other resins and suppressing gelation of the product during the reaction, the aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred, alkyl groups having 1 to 3 carbon atoms are more preferred, and methyl and ethyl groups are even more preferred. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0059] X in the above general formula (A2-3) a12Examples of the alkylene group having 1 to 5 carbon atoms represented by include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc. The alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and even more preferably a methylene group.

[0060] X in the above general formula (A2-3) a12 Examples of the alkylidene group having 2 to 5 carbon atoms represented by include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, an isopentylidene group, etc. Among these, an alkylidene group having 2 to 4 carbon atoms is preferred, an alkylidene group having 2 or 3 carbon atoms is more preferred, and an isopropylidene group is even more preferred.

[0061] n in the above general formula (A2-3) a12 and n a13 are each independently an integer of 0 to 4, and from the viewpoints of availability, compatibility with other resins, and suppression of gelation of the product during the reaction, they are preferably integers of 1 to 3, more preferably 1 or 2, and even more preferably 2. n a12 +n a13 is preferably an integer of 1 to 8, more preferably an integer of 2 to 6, and even more preferably 4, from the viewpoints of availability, compatibility with other resins, and suppression of gelation of the product during the reaction. n a12 or n a13 is an integer equal to or greater than 2, multiple R a12 R a13 They may be the same or different from each other.

[0062] X in the above general formula (A2-3) a12 The divalent group represented by the general formula (A2-3-1) is as follows:

[0063] [ka] (In the formula, R a14 and R a15 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. a13 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. a14 and n a15 are each independently an integer of 0 to 4. * represents a binding site.

[0064] R in the above general formula (A2-3-1) a14 and R a15 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl; alkenyl groups having 1 to 5 carbon atoms, and alkynyl groups having 1 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. The aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0065] X in the above general formula (A2-3-1) a13 Examples of the alkylene group having 1 to 5 carbon atoms represented by include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc. The alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and even more preferably a methylene group.

[0066] X in the above general formula (A2-3-1) a13Examples of the alkylidene group having 2 to 5 carbon atoms represented by include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, an isopentylidene group, etc. Among these, an alkylidene group having 2 to 4 carbon atoms is preferred, an alkylidene group having 2 or 3 carbon atoms is more preferred, and an isopropylidene group is even more preferred.

[0067] X in the above general formula (A2-3-1) a13 Among the above options, alkylidene groups having 2 to 5 carbon atoms are preferred, alkylidene groups having 2 to 4 carbon atoms are more preferred, and an isopropylidene group is even more preferred.

[0068] n in the above general formula (A2-3-1) a14 and n a15 are each independently an integer of 0 to 4, and from the viewpoint of availability, are each preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. n a14 or n a15 is an integer equal to or greater than 2, multiple R a14 R a15 They may be the same or different from each other.

[0069] X in the above general formula (A2-3) a12 Among the above options, alkylene groups having 1 to 5 carbon atoms, alkylidene groups having 2 to 5 carbon atoms, and divalent groups represented by the above general formula (A2-3-1) are preferred, alkylene groups having 1 to 5 carbon atoms are more preferred, and methylene groups are even more preferred.

[0070] [ka] (In the formula, n a16 is an integer between 0 and 10. * represents a binding site.

[0071] n in the above general formula (A2-4) a16is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3, from the viewpoint of availability.

[0072] [ka] (In the formula, n a17 is a number between 0 and 5. * represents a binding site.

[0073] [ka] (In the formula, R a16 and R a17 are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. a18 is an integer from 1 to 8. * represents a binding site.

[0074] R in the above general formula (A2-6) a16 and R a17 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; alkenyl groups having 1 to 5 carbon atoms; and alkynyl groups having 1 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. n in the above general formula (A2-6) a18 is an integer of 1 to 8, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1. a18 is an integer equal to or greater than 2, multiple R a16 R a17 They may be the same or different from each other.

[0075] Examples of the maleimide compound (A2) include aromatic maleimide compounds having two N-substituted maleimide groups, aromatic polymaleimide compounds, and aliphatic maleimide compounds. Specific examples of the maleimide compound (A2) 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-maleimidophenyl) 1,1-bis[4-(3-maleimidophenoxy)phenyl]ethane, 1,1-bis[4-(4-maleimidophenoxy)phenyl]ethane, 1,2-bis[4-(3-maleimidophenoxy)phenyl]ethane, 1,2-bis[4-(4-maleimidophenoxy)phenyl]ethane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]propane , 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 4,4-bis(3-maleimidophenoxy)biphenyl, 4,4-bis(4-maleimidophenoxy)biphenyl, bis[4-(3-maleimidophenoxy)phenyl]ketone, bis[4-(4-maleimidophenoxy)phenyl]ketone, bis(4-maleimidophenyl)disulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfide, bis[4-(4-maleimidophenoxy)phenyl]sulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfoxide, bis[4-(4-maleimidophenoxy)phenyl]sulfoxide, bis[4-(3-maleimidophenoxy)phenyl]sulfone, bis[4-(4-maleimidophenoxy)phenyl]sulfone, bis[4-(3-maleimidophenoxy)phenyl]ether, bis[4-(4-maleimidophenoxy)phenyl]ether, 1,4-bis[4-(4-maleimidophenoxy)-α,α -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, and the like. ,

[0076] (Maleimide compound derivatives (AY)) The maleimide compound derivative (AY) is preferably an aminomaleimide compound having a structural unit derived from the above-mentioned maleimide compound (AX) and a structural unit derived from a diamine compound [hereinafter, sometimes referred to as "aminomaleimide compound (A3)" or "component (A3)"].

[0077] [Aminomaleimide compound (A3)] The aminomaleimide compound (A3) has a structural unit derived from the maleimide compound (AX) and a structural unit derived from a diamine compound (hereinafter, sometimes referred to as "diamine compound (a)" or "component (a)").

[0078] <Structural units derived from maleimide compounds (AX)> An example of a structural unit derived from the maleimide compound (AX) is a structural unit formed by a Michael addition reaction between at least one N-substituted maleimide group of the maleimide compound (AX) and an amino group of the diamine compound. The structural unit derived from the maleimide compound (AX) contained in the aminomaleimide compound (A3) may be of one type alone or of two or more types.

[0079] The content of the structural unit derived from the maleimide compound (AX) in the aminomaleimide compound (A3) is not particularly limited, but is preferably 5 to 95 mass%, more preferably 30 to 93 mass%, and even more preferably 60 to 90 mass%. When the content of the structural unit derived from the maleimide compound (AX) in the aminomaleimide compound (A3) is within the above range, the dielectric properties and film handling properties tend to be better.

[0080] <Structural units derived from diamine compound (a)> Examples of the structural unit derived from the diamine compound (a) include a structural unit formed by a Michael addition reaction between one or both of the two amino groups contained in the diamine compound (a) and an N-substituted maleimide group contained in the maleimide compound (AX). The structural unit derived from the diamine compound (a) contained in the aminomaleimide compound (A3) may be of one type alone or may be of two or more types.

[0081] The amino group contained in the diamine compound (a) is preferably a primary amino group. Examples of the structural unit derived from the diamine compound (a) having two primary amino groups include a group represented by the following general formula (a-1) and a group represented by the following general formula (a-2).

[0082] [ka] (In the formula, X a21 is a divalent organic group, and * represents a bonding site.

[0083] X in the above general formula (a-1) and the above general formula (a-2) a21 is a divalent organic group, and corresponds to the divalent group obtained by removing two amino groups from the diamine compound (a).

[0084] X in the above general formula (a-1) and the above general formula (a-2) a21 is preferably a divalent group represented by the following general formula (a-3).

[0085] [ka] (In the formula, R a21 and R a22 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a hydroxyl group, or a halogen atom. a22 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a fluorenylene group, a single bond, or a divalent group represented by the following general formula (a-3-1) or (a-3-2): a21 and n a22 are each independently an integer of 0 to 4. * represents a binding site.

[0086] [ka] (In the formula, R a23 and R a24are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. a23 represents an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an m-phenylenediisopropylidene group, a p-phenylenediisopropylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. a23 and n a24 are each independently an integer of 0 to 4. * represents a binding site.

[0087] [ka] (In the formula, R a25 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. a24 and X a25 are each independently an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. a25 is an integer from 0 to 4. * represents a binding site.

[0088] R in the above general formula (a-3), the above general formula (a-3-1), and the above general formula (a-3-2) a21 , R a22 , R a23 , R a24 and R a25 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl; alkenyl groups having 1 to 5 carbon atoms, and alkynyl groups having 1 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. The aliphatic hydrocarbon group having 1 to 5 carbon atoms is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group or an ethyl group. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0089] X in the above general formula (a-3) a22 , X in the above general formula (a-3-1) a23 and X in the above general formula (a-3-2) a24 and X a25 Examples of the alkylene group having 1 to 5 carbon atoms represented by include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc. The alkylene group having 1 to 5 carbon atoms is preferably an alkylene group having 1 to 3 carbon atoms, more preferably an alkylene group having 1 or 2 carbon atoms, and even more preferably a methylene group.

[0090] X in the above general formula (a-3) a22 , X in the above general formula (a-3-1) a23 and X in the above general formula (a-3-2) a24 and X a25 Examples of the alkylidene group having 2 to 5 carbon atoms represented by include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, an isopentylidene group, etc. The alkylidene group having 2 to 5 carbon atoms is preferably an alkylidene group having 2 to 4 carbon atoms, more preferably an alkylidene group having 2 or 3 carbon atoms, and even more preferably an isopropylidene group.

[0091] n in the above general formula (a-3) a21 and n a22 are each independently an integer of 0 to 4, and from the viewpoint of availability, are all preferably integers of 0 to 3, more preferably integers of 0 to 2, and even more preferably 0 or 2. n a21 or n a22 is an integer equal to or greater than 2, multiple R a21 R a22 They may be the same or different from each other.

[0092] n in the above general formula (a-3-1) a23 and n a24are each independently an integer of 0 to 4, and from the viewpoint of availability, are each preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. n a23 or n a24 is an integer equal to or greater than 2, multiple R a23 R a24 They may be the same or different from each other.

[0093] n in the above general formula (a-3-2) a25 is an integer of 0 to 4, and from the viewpoint of availability, is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. n a25 is an integer equal to or greater than 2, multiple R a25 They may be the same or different from each other.

[0094] The content of the structural units derived from the diamine compound (a) in the aminomaleimide compound (A3) is not particularly limited, but is preferably 5 to 95 mass%, more preferably 7 to 70 mass%, and even more preferably 10 to 40 mass%. When the content of the structural units derived from the diamine compound (a) in the aminomaleimide compound (A3) is within the above range, the dielectric properties, heat resistance, flame retardancy, and glass transition temperature tend to be better.

[0095] Examples of the diamine compound (a) include 4,4'-diaminodiphenylmethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ketone, 4,4'-diaminobiphenyl, 3,3' -dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)propane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 1,3 -bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, 1,3-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 1,4-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 4,4'-[1, [3-phenylenebis(1-methylethylidene)]bisaniline, 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline, 3,3'-[1,3-phenylenebis(1-methylethylidene)]bisaniline, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, 9,9-bis(4-aminophenyl)fluorene, and the like.

[0096] Among these, 4,4'-diaminodiphenylmethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisaniline, and 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline are preferred as diamine compound (a) from the viewpoints of excellent solubility in organic solvents, reactivity, and heat resistance. Furthermore, 3,3'-dimethyl-5,5'-diethyl-4,4'-diaminodiphenylmethane is preferred as diamine compound (a) from the viewpoints of excellent dielectric properties and low water absorption. In addition, the diamine compound (a) is preferably 2,2-bis[4-(4-aminophenoxy)phenyl]propane from the viewpoint of high adhesion to conductors and excellent mechanical properties such as elongation and breaking strength. Furthermore, the diamine compound (a) is preferably 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisaniline or 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline from the viewpoints of excellent solubility in organic solvents, reactivity during synthesis, heat resistance, high adhesion to conductors, as well as excellent dielectric properties and low moisture absorption.

[0097] In the aminomaleimide compound (A3), the equivalent ratio (Ta2 / Ta1) of the total equivalent (Ta2) of groups (including -NH2) derived from the -NH2 group of the diamine compound (a) to the total equivalent (Ta1) of groups derived from the N-substituted maleimide group of the maleimide compound (AX) is not particularly limited, but from the viewpoints of dielectric properties, heat resistance, flame retardancy, and glass transition temperature, it is preferably 0.05 to 10, more preferably 0.5 to 7, and even more preferably 1 to 5. The group derived from the -NH2 group of the diamine compound (a) is intended to include -NH2 itself. Furthermore, the group derived from the N-substituted maleimide group of the maleimide compound (AX) is intended to include the N-substituted maleimide group itself.

[0098] The number average molecular weight of the aminomaleimide compound (A3) is not particularly limited, but from the viewpoint of handleability and moldability, it is preferably 400 to 10,000, more preferably 500 to 5,000, and even more preferably 600 to 2,000.

[0099] (Method for producing aminomaleimide compound (A3)) The aminomaleimide compound (A3) can be produced, for example, by reacting the maleimide compound (AX) with the diamine compound (a) in an organic solvent. By reacting the maleimide compound (AX) with the diamine compound (a), an aminomaleimide compound (A3) is obtained through a Michael addition reaction between the maleimide compound (AX) and the diamine compound (a).

[0100] When the maleimide compound (AX) is reacted with the diamine compound (a), a reaction catalyst may be used as needed. Examples of the reaction catalyst include acidic catalysts such as p-toluenesulfonic acid, amines such as triethylamine, pyridine, and tributylamine, imidazoles such as methylimidazole and phenylimidazole, and phosphorus-based catalysts such as triphenylphosphine. These may be used alone or in combination of two or more. The amount of the reaction catalyst to be added is not particularly limited, but from the viewpoint of the reaction rate and reaction uniformity, it is preferably 0.01 to 5 parts by mass, more preferably 0.05 to 3 parts by mass, and even more preferably 0.1 to 2 parts by mass, relative to 100 parts by mass of the total amount of the maleimide compound (AX) and the diamine compound (a).

[0101] The reaction temperature for the Michael addition reaction is preferably 50 to 160°C, more preferably 60 to 150°C, and even more preferably 70 to 140°C, from the viewpoints of workability such as reaction rate, and suppression of gelation of the product during the reaction. The reaction time for the Michael addition reaction is preferably 0.5 to 10 hours, more preferably 1 to 8 hours, and even more preferably 2 to 6 hours, from the viewpoints of productivity and allowing the reaction to proceed sufficiently. However, these reaction conditions can be appropriately adjusted depending on the types of raw materials used, and are not particularly limited.

[0102] In the Michael addition reaction, the solids concentration and solution viscosity of the reaction solution may be adjusted by adding or concentrating an organic solvent. The solids concentration of the reaction solution is not particularly limited, but is preferably 10 to 90% by mass, more preferably 15 to 85% by mass, and even more preferably 20 to 80% by mass. When the solids concentration of the reaction raw materials is equal to or greater than the lower limit, a good reaction rate is obtained, and productivity tends to be improved. Furthermore, when the solids concentration of the reaction raw materials is equal to or less than the upper limit, better solubility is obtained, stirring efficiency is improved, and gelation of the product during the reaction tends to be more effectively suppressed.

[0103] Among the above-described components (A), from the viewpoints of dielectric properties, conductor adhesion, and heat resistance, it is preferable that the component (A) be one or more compounds selected from the group consisting of maleimide compounds and derivatives thereof that contain a fused ring of an aromatic ring and an aliphatic ring in the molecular structure and have two or more N-substituted maleimide groups.

[0104] <Modified conjugated diene polymer (B)> The resin composition of the present embodiment contains a modified conjugated diene polymer obtained by reacting (b1) a conjugated diene polymer having a vinyl group in the side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond. The modified conjugated diene polymer (B) may be used singly or in combination of two or more kinds.

[0105] (Conjugated diene polymer (b1)) In this specification, the term "conjugated diene polymer" means a polymer of a conjugated diene compound. Examples of conjugated diene compounds include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 2-phenyl-1,3-butadiene, and 1,3-hexadiene. The conjugated diene polymer (b1) may be a polymer of one kind of conjugated diene compound, or may be a polymer of two or more kinds of conjugated diene compounds. The conjugated diene polymer (b1) may also be a copolymer of one or more conjugated diene compounds and one or more monomers other than the conjugated diene compounds. When the conjugated diene polymer (b1) is a copolymer, the polymerization mode is not particularly limited, and may be any of random polymerization, block polymerization, and graft polymerization. The conjugated diene polymer (b1) may be used singly or in combination of two or more kinds.

[0106] As the conjugated diene polymer (b1), a conjugated diene polymer having a plurality of vinyl groups in the side chain is preferred from the viewpoints of compatibility with other resins and dielectric properties. The number of vinyl groups that the conjugated diene polymer (b1) has in one molecule is not particularly limited, but from the viewpoints of compatibility with other resins and dielectric properties, it is preferably 3 or more, more preferably 5 or more, and even more preferably 10 or more. The upper limit of the number of vinyl groups that the conjugated diene polymer (b1) has in one molecule is not particularly limited, but may be 100 or less, 80 or less, or 60 or less.

[0107] Examples of the conjugated diene polymer (b1) include polybutadiene having 1,2-vinyl groups, butadiene-styrene copolymer having 1,2-vinyl groups, and polyisoprene having 1,2-vinyl groups. Among these, from the viewpoint of dielectric properties and heat resistance, polybutadiene having 1,2-vinyl groups and butadiene-styrene copolymer having 1,2-vinyl groups are preferred, and polybutadiene having 1,2-vinyl groups is more preferred. Furthermore, as the polybutadiene having 1,2-vinyl groups, polybutadiene homopolymer having 1,2-vinyl groups is preferred. The 1,2-vinyl group derived from butadiene contained in the conjugated diene polymer (b1) is a vinyl group contained in a structural unit derived from butadiene represented by the following formula (b1-1).

[0108] [ka]

[0109] When the conjugated diene polymer (b1) is a polybutadiene having a 1,2-vinyl group, the content of structural units having a 1,2-vinyl group relative to all structural units derived from butadiene constituting the polybutadiene [hereinafter, sometimes referred to as the "vinyl group content"] is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric properties, and heat resistance, it is preferably 50 mol% or more, more preferably 70 mol% or more, and even more preferably 85 mol% or more. There is no particular upper limit to the vinyl group content, and it may be 100 mol% or less, 95 mol% or less, or even 90 mol% or less. As the structural unit having a 1,2-vinyl group, a butadiene-derived structural unit represented by the above formula (b1-1) is preferred. From the same viewpoint, the polybutadiene having a 1,2-vinyl group is preferably a 1,2-polybutadiene homopolymer.

[0110] The number average molecular weight of the conjugated diene polymer (b1) is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric properties, and heat resistance, it is preferably 400 to 3,000, more preferably 600 to 2,000, and even more preferably 800 to 1,500.

[0111] (Phosphorus-containing monomer (b2)) The phosphorus-containing monomer (b2) is not particularly limited as long as it is a compound having a phosphorus atom and an ethylenically unsaturated bond. The phosphorus-containing monomer (b2) may be used alone or in combination of two or more.

[0112] In this specification, the term "ethylenically unsaturated bond" means a carbon-carbon double bond capable of undergoing an addition reaction, and does not include double bonds in aromatic rings. In addition, in this specification, a substituent containing an "ethylenically unsaturated bond" may be referred to as an "ethylenically unsaturated bond-containing group." Examples of the ethylenically unsaturated bond-containing group contained in the phosphorus-containing monomer (b2) include unsaturated aliphatic hydrocarbon groups not containing heteroatoms, such as vinyl groups, isopropenyl groups, allyl groups, 1-methylallyl groups, and 3-butenyl groups; and substituents containing heteroatoms, such as maleimide groups and (meth)acryloyl groups. Among these, from the viewpoints of dielectric properties and reactivity, vinyl groups and (meth)acryloyl groups are preferred, and (meth)acryloyl groups are more preferred. The (meth)acryloyl group may be present as a (meth)acryloyloxy group, and in that case, the phosphorus-containing monomer (b2) has a (meth)acryloyloxy group as the ethylenically unsaturated bond-containing group. The number of ethylenically unsaturated bond-containing groups that the phosphorus-containing monomer (b2) has in one molecule is not particularly limited, but from the viewpoint of suppressing gelation of the product during the reaction, it is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0113] The phosphorus-containing monomer (b2) preferably contains a P=O bond in the molecule. The number of P=O bonds contained in one molecule of the phosphorus-containing monomer (b2) is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0114] From the viewpoints of reactivity and flame retardancy, the phosphorus-containing monomer (b2) is preferably a compound represented by the following general formula (b2-1):

[0115] [ka] (In the formula, R b1 and R b2 are each independently an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a hydrogen atom. b1 and R b2 may be bonded to each other to form a ring. b1and n b2 are each independently 0 or 1. b1 is an organic group containing an ethylenically unsaturated bond.

[0116] R in the above general formula (b2-1) b1 and R b2 The alkyl group having 1 to 10 carbon atoms represented by the formula (I) preferably has 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 or 2 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, etc. Among these, a methyl group and an ethyl group are preferred, and a methyl group is more preferred. The alkyl group having 1 to 10 carbon atoms may be linear, branched or cyclic. The alkyl group having 1 to 10 carbon atoms may or may not have a substituent. Examples of the substituent include a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, a cyano group, an aryl group, an alkoxy group, and groups in which these substituents are linked. When the alkyl group having 1 to 10 carbon atoms has a substituent, the number of carbon atoms of the alkyl group includes the number of carbon atoms of the substituent.

[0117] R in the above general formula (b2-1) b1 and R b2 The aryl group having 6 to 20 carbon atoms represented by the formula (I) preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and an anthranyl group. Among these, a phenyl group and a naphthyl group are preferred, and a phenyl group is more preferred. The phenyl group is preferably an unsubstituted phenyl group. The aryl group having 6 to 20 carbon atoms may or may not have a substituent. Examples of the substituent include a hydroxyl group, a carboxyl group, a halogen atom, an amino group, an amide group, a cyano group, an alkyl group, an alkoxy group, and groups in which these substituents are linked. When the aryl group having 6 to 20 carbon atoms has a substituent, the number of carbon atoms of the aryl group includes the number of carbon atoms of the substituent.

[0118] R in the above general formula (b2-1) b1 and R b2 Among the above options, an aryl group having 6 to 20 carbon atoms is preferred, and a phenyl group is more preferred.

[0119] n in the above general formula (b2-1) b1 and n b2 is 0 or 1, and is preferably 0. b1 or n b2 is 0, R b1 or R b2 This means that the bond is directly to the phosphorus atom.

[0120] Z in the above general formula (b2-1) b1 is an organic group containing an ethylenically unsaturated bond, and examples thereof include groups represented by the following general formula (b2-2):

[0121] [ka] (In the formula, X b1 is a divalent hydrocarbon group having 1 to 12 carbon atoms. b1 is a vinyl group or a (meth)acryloyloxy group, n b3 is 0 or 1. * represents the site of binding to the phosphorus atom in the above general formula (b2-1).

[0122] X in the above general formula (b2-2) b1 Examples of the divalent hydrocarbon group having 1 to 12 carbon atoms represented by include alkylene groups having 1 to 12 carbon atoms and arylene groups having 6 to 12 carbon atoms. Examples of the alkylene group having 1 to 12 carbon atoms include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc. As the alkylene group having 1 to 12 carbon atoms, an alkylene group having 1 to 5 carbon atoms is preferred, an alkylene group having 1 or 2 carbon atoms is more preferred, and a methylene group is even more preferred. Examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a naphthylene group, a biphenylene group, etc. As the arylene group having 6 to 12 carbon atoms, an arylene group having 6 to 10 carbon atoms is preferred, an arylene group having 6 to 8 carbon atoms is more preferred, and a phenylene group is even more preferred.

[0123] In addition, R in the above general formula (b2-1) b1 and R b2 Examples of the phosphorus-containing monomer (b2) having a structure formed by bonding together include phosphorus-containing monomers having a structure represented by the following general formula (b2-3):

[0124] [ka] (In the formula, Z b1 is as explained in the above general formula (b2-1).

[0125] As the compound represented by the above general formula (b2-1), a compound represented by the following general formula (b2-4) is more preferred.

[0126] [ka] (R in the above general formula (b2-4) b3 and R b4 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, a halogen atom, or a hydroxyl group. b1 and n b2 are each independently 1 or 0. b4 and n b5 are each independently an integer of 0 to 5. b2is a group represented by the above general formula (b2-4-1) or a group represented by the above formula (b2-4-2). b5 is a hydrogen atom or a methyl group. * in the above general formula (b2-4-1) and the above formula (b2-4-2) represents the site of bonding to the phosphorus atom in the above general formula (b2-4).

[0127] R in the above general formula (b2-4) b3 and R b4 Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, etc. The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group. R b3 and R b4 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. n in the above general formula (b2-4) b1 and n b2 is 0 or 1, and is preferably 0. n in the above general formula (b2-4) b4 and n b5 are each independently an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0. n b4 or n b5 is an integer equal to or greater than 2, multiple R b3 R b4 They may be the same or different from each other. R in the above general formula (b2-4-1) b5 is a hydrogen atom or a methyl group, and is preferably a methyl group.

[0128] Examples of the phosphorus-containing monomer (b2) include a compound having a phosphate ester group and an ethylenically unsaturated bond, a compound having a phosphonate ester group and an ethylenically unsaturated bond, a compound having a phosphinate ester group and an ethylenically unsaturated bond, and a compound having a phosphine oxide group and an ethylenically unsaturated bond. Examples of the compound having a phosphate ester group and an ethylenically unsaturated bond include phosphate ester group-containing (meth)acrylate compounds such as 2-(meth)acryloyloxyethyl phosphate, dimethyl-(2-(meth)acryloyloxyethyl)phosphate, diethyl-(2-(meth)acryloyloxyethyl)phosphate, and diphenyl-(2-(meth)acryloyloxyethyl)phosphate; phosphate ester group-containing vinyl compounds; and phosphate ester group-containing styryl compounds. Examples of the compound having a phosphonate ester group and an ethylenically unsaturated bond include diphenyl-((meth)acryloyloxymethyl)phosphonate, diphenyl-(2-((meth)acryloyloxy)ethyl)phosphonate, diphenyl-(3-((meth)acryloyloxy)propyl)phosphonate, diphenyl-(4-((meth)acryloyloxy)butyl)phosphonate, dimethyl-((meth)acryloyloxymethyl)phosphonate, dimethyl-(2-((meth)acryloyloxy)ethyl)phosphonate, dimethyl-(3-((meth)acryloyloxy)propyl)phosphonate, dimethyl-(4-((meth)acryloyloxy)butyl)phosphonate, diethyl-((meth)acryloyloxymethyl)phosphonate, diethyl-(2-((meth)acryloyloxy)ethyl)phosphonate, and diethyl-(3-((meth)acryloyloxy)propyl)phosphonate. and diethyl-(4-((meth)acryloyloxy)butyl)phosphonate; vinyl phosphonate compounds such as diphenyl vinyl phosphonate, dimethyl vinyl phosphonate, diethyl vinyl phosphonate, dipropyl vinyl phosphonate, dibutyl vinyl phosphonate, dipentyl vinyl phosphonate, and dihexyl vinyl phosphonate; and phosphonate group-containing styrene compounds such as diphenyl styrylphosphonate, dimethyl styrylphosphonate, diethyl styrylphosphonate, diphenyl styrylmethylphosphonate, dimethyl styrylmethylphosphonate, diethyl styrylmethylphosphonate, diphenyl styrylethylphosphonate, dimethyl styrylethylphosphonate, diethyl styrylethylphosphonate, diphenyl styrylpropylphosphonate, dimethyl styrylpropylphosphonate, and diethyl styrylpropylphosphonate. Examples of the compound having a phosphinic acid ester group and an ethylenically unsaturated bond include diphenyl-((meth)acryloyloxymethyl)phosphinate, diphenyl-(2-((meth)acryloyloxy)ethyl)phosphinate, diphenyl-(3-((meth)acryloyloxy)propyl)phosphinate, diphenyl-(4-((meth)acryloyloxy)butyl)phosphinate, dimethyl-((meth)acryloyloxymethyl)phosphinate, dimethyl-(2-((meth)acryloyloxy)ethyl)phosphinate, dimethyl-(3-((meth)acryloyloxy)propyl)phosphinate,

[0033] Examples of the phosphinate ester group-containing (meth)acrylate compounds include phosphinate ester group-containing vinyl compounds and phosphinate ester group-containing styrene compounds, such as dimethyl-(4-((meth)acryloyloxy)propyl)phosphinate, dimethyl-(4-((meth)acryloyloxy)butyl)phosphinate, diethyl-((meth)acryloyloxymethyl)phosphinate, diethyl-(2-((meth)acryloyloxy)ethyl)phosphinate, diethyl-(3-((meth)acryloyloxy)propyl)phosphinate, and diethyl-(4-((meth)acryloyloxy)butyl)phosphinate. Examples of the compound having a phosphine oxide group and an ethylenically unsaturated bond include diphenyl-((meth)acryloyloxymethyl)phosphine oxide, diphenyl-(2-((meth)acryloyloxy)ethyl)phosphine oxide, diphenyl-(3-((meth)acryloyloxy)propyl)phosphine oxide, diphenyl-(4-((meth)acryloyloxy)butyl)phosphine oxide, dimethyl-((meth)acryloyloxymethyl)phosphine oxide, dimethyl-(2-((meth)acryloyloxy)ethyl)phosphine oxide, dimethyl-(3-((meth)acryloyloxy)propyl)phosphine oxide, dimethyl-(4-((meth)acryloyloxy)butyl)phosphine oxide, diethyl-((meth)acryloyloxymethyl)phosphine oxide, diethyl-(2-((meth)acryloyloxy)ethyl)phosphine oxide, diethyl- Examples of the phosphine oxide group-containing (meth)acrylate compounds include (3-((meth)acryloyloxy)propyl)phosphine oxide and diethyl-(4-((meth)acryloyloxy)butyl)phosphine oxide; phosphine oxide group-containing styrene compounds include styryldiphenylphosphine oxide, styryldimethylphosphine oxide, styryldiethylphosphine oxide, (styrylmethyl)diphenylphosphine oxide, (styrylmethyl)dimethylphosphine oxide, (styrylmethyl)diethylphosphine oxide, (styrylethyl)diphenylphosphine oxide, (styrylethyl)dimethylphosphine oxide, (styrylethyl)diethylphosphine oxide, (styrylpropyl)diphenylphosphine oxide, (styrylpropyl)dimethylphosphine oxide and (styrylpropyl)diethylphosphine oxide; and vinylphosphine oxide compounds. Among these, the compound having a phosphine oxide group and an ethylenically unsaturated bond is preferably a phosphine oxide group-containing (meth)acrylate compound.

[0129] The modified conjugated diene polymer (B) preferably has, in its side chain, a substituent (hereinafter sometimes referred to as "substituent (x)") formed by reaction of a vinyl group contained in the conjugated diene polymer (b1) with an ethylenically unsaturated bond-containing group contained in the phosphorus-containing monomer (b2). The substituent (x) is preferably a group containing a structure represented by the following general formula (B-1).

[0130] [ka] (In the formula, R b1 , R b2 , n b1 and n b2 is as explained in the above general formula (b2-1). * represents a binding site.

[0131] The number average molecular weight of the modified conjugated diene polymer (B) is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric properties, and heat resistance, it is preferably 1,000 to 6,000, more preferably 1,500 to 5,000, and even more preferably 2,000 to 3,000.

[0132] The modified conjugated diene polymer (B) can be produced by reacting a conjugated diene polymer (b1) with a phosphorus-containing monomer (b2). The method for reacting the conjugated diene polymer (b1) with the phosphorus-containing monomer (b2) is not particularly limited. For example, the conjugated diene polymer (b1), the phosphorus-containing monomer (b2), a reaction catalyst, and an organic solvent are charged into a reaction vessel, and the reaction is carried out while heating, keeping the temperature, stirring, etc., as necessary, to obtain the modified conjugated diene polymer (B).

[0133] The reaction temperature for the above reaction is preferably 70 to 120°C, more preferably 80 to 110°C, and even more preferably 85 to 105°C, from the viewpoints of workability and suppressing gelation of the product during the reaction. The reaction time for the above reaction is preferably 0.5 to 15 hours, more preferably 1 to 10 hours, and even more preferably 3 to 7 hours, from the viewpoints of productivity and allowing the reaction to proceed sufficiently. However, these reaction conditions can be appropriately adjusted depending on the types of raw materials used, and are not particularly limited.

[0134] Examples of organic solvents used in the above reaction include alcohol-based solvents such as methanol, ethanol, butanol, butyl cellosolve, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aromatic hydrocarbon-based solvents such as toluene, xylene, and mesitylene; ester-based solvents such as methoxyethyl acetate, ethoxyethyl acetate, butoxyethyl acetate, and ethyl acetate; and nitrogen-containing solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. The organic solvent may be used alone or in combination of two or more. Among these, toluene is preferred from the viewpoint of resin solubility.

[0135] When the reaction is carried out in an organic solvent, the total content of the conjugated diene polymer (b1) and the phosphorus-containing monomer (b2) in the reaction solution is not particularly limited, but is preferably 10 to 70% by mass, more preferably 15 to 60% by mass, and even more preferably 20 to 50% by mass. When the total content of the conjugated diene polymer (b1) and the phosphorus-containing monomer (b2) is equal to or greater than the lower limit, a good reaction rate is obtained, and productivity tends to be improved. On the other hand, when the total content of the conjugated diene polymer (b1) and the phosphorus-containing monomer (b2) is equal to or less than the upper limit, better solubility is obtained, stirring efficiency is improved, and gelation of the product during the reaction tends to be more effectively suppressed.

[0136] As the reaction catalyst, from the viewpoint of obtaining sufficient reactivity while suppressing gelation of the product during the reaction, organic peroxides are preferred, and α,α'-bis(t-butylperoxy)diisopropylbenzene is more preferred. The reaction catalyst may be used alone or in combination of two or more. The amount of the reaction catalyst used is not particularly limited, but from the viewpoint of the reaction rate and reaction uniformity, it is preferably 0.01 to 1 part by mass, more preferably 0.03 to 0.5 parts by mass, and even more preferably 0.05 to 0.2 parts by mass, relative to 100 parts by mass of the total amount of the conjugated diene polymer (b1) and the phosphorus-containing monomer (b2).

[0137] When the above reaction is carried out, the number of moles of side chain vinyl groups in the conjugated diene polymer (b1) (M v ) 、 The number of moles of ethylenically unsaturated bonds in the phosphorus-containing monomer (b2) (M m ) ratio (M m / M v ) is not particularly limited, but is preferably 0.001 to 0.5, more preferably 0.003 to 0.1, and even more preferably 0.005 to 0.05, from the viewpoints of compatibility of the resulting modified conjugated diene polymer (B) with other resins and suppression of gelation of the product during the reaction.

[0138] The amount of the phosphorus-containing monomer (b2) to be added when carrying out the above reaction is not particularly limited, but from the viewpoints of compatibility of the resulting modified conjugated diene polymer (B) with other resins and suppression of gelation of the product during the reaction, it is preferably 0.5 to 40 parts by mass, more preferably 1 to 30 parts by mass, and even more preferably 2 to 20 parts by mass per 100 parts by mass of the conjugated diene polymer (b1).

[0139] <Contents of Maleimide Resin (A) and Modified Conjugated Diene Polymer (B) and Their Content Ratios> In the resin composition of this embodiment, the content of the maleimide resin (A) is not particularly limited, but is preferably 5 to 70 parts by mass, more preferably 10 to 50 parts by mass, and even more preferably 20 to 40 parts by mass, per 100 parts by mass of the total resin components in the resin composition of this embodiment. When the content of the maleimide resin (A) is at least the above-mentioned lower limit, the heat resistance, moldability, processability, and conductor adhesion tend to be better. On the other hand, when the content of the maleimide resin (A) is at most the above-mentioned upper limit, the dielectric properties tend to be better.

[0140] In this specification, the term "resin component" refers to a resin and a compound that forms a resin through a curing reaction. For example, in the resin composition of this embodiment, the maleimide resin (A) and the modified conjugated diene polymer (B) correspond to the resin components. When the resin composition of the present embodiment contains, as optional components, a resin or a compound that forms a resin through a curing reaction in addition to the above components, these optional components are also included in the resin component. On the other hand, inorganic fillers and flame retardants are not included in the resin components.

[0141] In the resin composition of this embodiment, the content of the modified conjugated diene polymer (B) is not particularly limited, but is preferably 5 to 70 parts by mass, more preferably 10 to 50 parts by mass, and even more preferably 20 to 40 parts by mass, per 100 parts by mass of the total resin components in the resin composition of this embodiment. When the content of the modified conjugated diene polymer (B) is at least the above-mentioned lower limit, the dielectric properties and flame retardancy tend to be better. On the other hand, when the content of the modified conjugated diene polymer (B) is at most the above-mentioned upper limit, the heat resistance, moldability, processability, and conductor adhesion tend to be better.

[0142] In the resin composition of this embodiment, the content ratio [(A) / (B)] of the maleimide resin (A) to the modified conjugated diene polymer (B) is not particularly limited, but is preferably 0.1 to 9, more preferably 0.25 to 4, and even more preferably 0.3 to 3, by mass. When the content ratio [(A) / (B)] of the maleimide resin (A) to the modified conjugated diene polymer (B) is at least the above lower limit, the heat resistance, moldability, processability, and conductor adhesion tend to be improved. Furthermore, when the content ratio [(A) / (B)] of the maleimide resin (A) to the modified conjugated diene polymer (B) is at most the above upper limit, the dielectric properties and flame retardancy tend to be improved.

[0143] The content of the resin component in the resin composition of this embodiment is not particularly limited, but from the viewpoints of low thermal expansion, heat resistance, flame retardancy, and conductor adhesion, it is preferably 10 to 70 mass%, more preferably 20 to 65 mass%, and even more preferably 30 to 60 mass%.

[0144] <Other ingredients> The resin composition of the present embodiment may further contain components other than the above components depending on the desired performance. Examples of other components include one or more selected from the group consisting of a styrene elastomer (C), an inorganic filler (D), a flame retardant (E), and a curing accelerator (F). However, the resin composition of the present embodiment may not contain one or more selected from the group consisting of the styrene-based elastomer (C), the inorganic filler (D), the flame retardant (E), and the curing accelerator (F), depending on the desired performance. These components are described in detail below.

[0145] <Styrene-based elastomer (C)> The styrene elastomer (C) [hereinafter sometimes referred to as "component (C)"] is not particularly limited as long as it is an elastomer having a structural unit derived from a styrene compound. The styrene-based elastomer (C) may be used alone or in combination of two or more. In this specification, the term "elastomer" refers to a polymer having a glass transition temperature of 25°C or lower as measured by differential scanning calorimetry in accordance with JIS K 6240:2011.

[0146] The styrene-based elastomer (C) is preferably one having a structural unit derived from styrene represented by the following general formula (C-1).

[0147] [ka] (In the formula, R c1 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R c2 is an alkyl group having 1 to 5 carbon atoms. c1 is an integer between 0 and 5.)

[0148] R in the above general formula (C-1) c1 and R c2 Examples of the alkyl group having 1 to 5 carbon atoms represented by include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, etc. The alkyl group having 1 to 5 carbon atoms may be either linear or branched. Among these, an alkyl group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 or 2 carbon atoms is more preferred, and a methyl group is even more preferred. n in the above general formula (C-1) c1 is an integer of 0 to 5, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0149] The styrene elastomer (C) may contain structural units other than those derived from styrene compounds. Examples of structural units other than those derived from styrene compounds that the styrene elastomer (C) has include structural units derived from butadiene, structural units derived from isoprene, structural units derived from maleic acid, and structural units derived from maleic anhydride. The butadiene-derived structural units and the isoprene-derived structural units may be hydrogenated. When hydrogenated, the butadiene-derived structural units become structural units in which ethylene units and butylene units are mixed, and the isoprene-derived structural units become structural units in which ethylene units and propylene units are mixed.

[0150] Examples of the styrene elastomer (C) include hydrogenated styrene-butadiene-styrene block copolymers, hydrogenated styrene-isoprene-styrene block copolymers, and styrene-maleic anhydride copolymers. Examples of hydrogenated styrene-butadiene-styrene block copolymers include SEBS, which is obtained by completely hydrogenating the carbon-carbon double bonds in the butadiene block, and SBBS, which is obtained by partially hydrogenating the carbon-carbon double bonds at 1,2-bond sites in the butadiene block. In SEBS, completely hydrogenated usually means 90% or more, 95% or more, 99% or more, or even 100% of the total carbon-carbon double bonds. In SBBS, the partial hydrogenation rate is, for example, 60 to 85% of the total carbon-carbon double bonds. Hydrogenated styrene-isoprene-styrene block copolymers are obtained as SEPS by hydrogenating the polyisoprene portion. Among these, SEBS and SEPS are preferred, and SEBS is more preferred, from the viewpoints of dielectric properties, conductor adhesion, heat resistance, glass transition temperature, and low thermal expansion.

[0151] In the SEBS, the content of structural units derived from styrene (hereinafter, may be referred to as "styrene content") is not particularly limited, but is preferably 5 to 60 mass%, more preferably 7 to 40 mass%, and even more preferably 10 to 20 mass%.

[0152] The melt flow rate (MFR) of SEBS is not particularly limited, but is preferably 0.1 to 20 g / 10 min, more preferably 1 to 10 g / 10 min, and even more preferably 3 to 7 g / 10 min, measured under the conditions of 230° C. and a load of 2.16 kgf (21.2 N).

[0153] Examples of commercially available SEBS products include the Tuftec (registered trademark) H series and M series manufactured by Asahi Kasei Corporation, the Septon (registered trademark) series manufactured by Kuraray Co., Ltd., and the Kraton (registered trademark) G Polymer series manufactured by Kraton Polymer Japan Co., Ltd.

[0154] The number average molecular weight of the styrene elastomer (C) is not particularly limited, but is preferably 10,000 to 500,000, more preferably 50,000 to 350,000, and even more preferably 100,000 to 200,000.

[0155] When the resin composition of the present embodiment contains the styrene-based elastomer (C), the content thereof is not particularly limited, but is preferably 10 to 80 parts by mass, more preferably 20 to 60 parts by mass, and even more preferably 30 to 50 parts by mass, per 100 parts by mass of the total of the resin components in the resin composition of the present embodiment. When the content of the styrene-based elastomer (C) is equal to or greater than the lower limit, the dielectric properties and moisture absorption resistance tend to be better, whereas when the content of the styrene-based elastomer (C) is equal to or less than the upper limit, the heat resistance, moldability, processability, and flame retardancy tend to be better.

[0156] When the resin composition of the present embodiment contains a styrene-based elastomer (C), the content ratio of the modified conjugated diene polymer (B) to the styrene-based elastomer (C) [(B) / (C)] is not particularly limited, but from the viewpoints of compatibility, dielectric properties, and flame retardancy, it is preferably 0.1 to 10, more preferably 0.2 to 5, and even more preferably 0.5 to 1.

[0157] (Inorganic filler (D)) The resin composition of the present embodiment tends to have further improved low thermal expansion properties, heat resistance, and flame retardancy by containing an inorganic filler (D) [hereinafter, sometimes referred to as "component (D)"]. The inorganic filler (D) may be used alone or in combination of two or more kinds.

[0158] Examples of the inorganic filler (D) include silica, alumina, titanium oxide, mica, beryllia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay, talc, aluminum borate, silicon carbide, etc. Among these, from the viewpoints of low thermal expansion, heat resistance, and flame retardancy, silica, alumina, mica, and talc are preferred, silica and alumina are more preferred, and silica is even more preferred. Examples of silica include precipitated silica produced by a wet method and having a high water content, and dry-process silica produced by a dry method and containing almost no bound water, etc. Dry-process silica further includes crushed silica, fumed silica, fused silica, etc., depending on the production method.

[0159] The average particle size of the inorganic filler (D) is not particularly limited, but from the viewpoint of dispersibility of the inorganic filler and fine wiring properties, it is preferably 0.01 to 20 μm, more preferably 0.1 to 10 μm, even more preferably 0.2 to 1 μm, and particularly preferably 0.3 to 0.8 μm. In this specification, the average particle size of the inorganic filler (D) refers to the particle size at the point corresponding to 50% volume when a cumulative frequency distribution curve of particle sizes is calculated, with the total volume of the particles being 100%. The average particle size of the inorganic filler (D) can be measured, for example, with a particle size distribution analyzer using a laser diffraction scattering method. The shape of the inorganic filler (D) may be, for example, spherical or crushed, with spherical being preferred.

[0160] When the resin composition of this embodiment contains an inorganic filler (D), the content of the inorganic filler (D) in the resin composition is not particularly limited, but is preferably 10 to 70 mass%, more preferably 20 to 65 mass%, and even more preferably 30 to 60 mass%, based on the total solid content of the resin composition. When the content of the inorganic filler (D) is equal to or greater than the above lower limit, low thermal expansion, heat resistance, and flame retardancy tend to be improved. On the other hand, when the content of the inorganic filler (D) is equal to or less than the above upper limit, moldability and conductor adhesion tend to be improved.

[0161] When the resin composition of this embodiment contains an inorganic filler (D), a coupling agent may be used to improve the dispersibility of the inorganic filler (D) and its adhesion to the organic component. Examples of the coupling agent include a silane coupling agent and a titanate coupling agent. Among these, a silane coupling agent is preferred. Examples of the silane coupling agent include an aminosilane coupling agent, a vinylsilane coupling agent, and an epoxysilane coupling agent.

[0162] When a coupling agent is used in the resin composition of this embodiment, the surface treatment method of the inorganic filler (D) may be an integral blend treatment method in which the inorganic filler (D) is blended into the resin composition and then the coupling agent is added, or a method in which the inorganic filler (D) is previously surface-treated with the coupling agent in a dry or wet manner. Among these, the method in which the inorganic filler (D) is previously surface-treated with the coupling agent in a dry or wet manner is preferred from the viewpoint of more effectively exhibiting the characteristics of the inorganic filler (D). For the purpose of improving dispersibility in the resin composition, the inorganic filler (D) may be dispersed in an organic solvent in advance to form a slurry, which may then be mixed with other components.

[0163] (Flame retardant (E)) The resin composition of this embodiment tends to have improved flame retardancy by containing a flame retardant (E) [hereinafter, sometimes referred to as "component (E)"]. However, since the resin composition of the present embodiment contains the modified conjugated diene polymer (B) having a flame retardant effect, it may not contain the flame retardant (E). The flame retardant (E) may be used alone or in combination of two or more. The resin composition of the present embodiment may also contain a flame retardant aid as needed.

[0164] Examples of the flame retardant (E) include phosphorus-based flame retardants, metal hydrates, and halogen-based flame retardants, and from the viewpoint of environmental issues, phosphorus-based flame retardants and metal hydrates are preferred.

[0165] -Phosphorus-based flame retardants- The phosphorus-based flame retardant is not particularly limited as long as it contains a phosphorus atom and is one that is generally used as a flame retardant. The phosphorus-based flame retardant may be an inorganic phosphorus-based flame retardant or an organic phosphorus-based flame retardant. From the viewpoint of environmental issues, it is preferable that the phosphorus-based flame retardant does not contain a halogen atom.

[0166] Examples of inorganic phosphorus-based flame retardants include red phosphorus; ammonium phosphates such as monoammonium phosphate, diammonium phosphate, triammonium phosphate, and ammonium polyphosphate; inorganic nitrogen-containing phosphorus compounds such as phosphoric acid amide; phosphoric acid; and phosphine oxide.

[0167] Examples of organic phosphorus-based flame retardants include aromatic phosphate esters, mono-substituted phosphonic acid diesters, di-substituted phosphinic acid esters, metal salts of di-substituted phosphinic acids, organic nitrogen-containing phosphorus compounds, and cyclic organic phosphorus compounds. Among these, aromatic phosphate ester compounds and metal salts of di-substituted phosphinic acids are preferred. Examples of metal salts include lithium salts, sodium salts, potassium salts, calcium salts, magnesium salts, aluminum salts, titanium salts, and zinc salts. Among these, aluminum salts are preferred. Furthermore, among organic phosphorus-based flame retardants, aromatic phosphate esters are preferred.

[0168] Examples of aromatic phosphate esters include triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, cresyl di-2,6-xylenyl phosphate, resorcinol bis(diphenyl phosphate), 1,3-phenylene bis(di-2,6-xylenyl phosphate), bisphenol A bis(diphenyl phosphate), and 1,3-phenylene bis(diphenyl phosphate).

[0169] Examples of the mono-substituted phosphonic acid diester include divinyl phenylphosphonate, diallyl phenylphosphonate, and bis(1-butenyl) phenylphosphonate. Examples of the disubstituted phosphinate ester include phenyl diphenylphosphinate and methyl diphenylphosphinate.

[0170] Examples of metal salts of disubstituted phosphinic acids include metal salts of dialkylphosphinic acids, metal salts of diallylphosphinic acids, metal salts of divinylphosphinic acids, metal salts of diarylphosphinic acids, etc. Of these metal salts, aluminum salts are preferred.

[0171] Examples of organic nitrogen-containing phosphorus compounds include phosphazene compounds such as bis(2-allylphenoxy)phosphazene and dicresylphosphazene; melamine phosphate; melamine pyrophosphate; melamine polyphosphate; and melam polyphosphate.

[0172] Examples of the cyclic organic phosphorus compound include 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and the like.

[0173] Among the above organic phosphorus-based flame retardants, aromatic phosphate esters and metal salts of disubstituted phosphinic acids are preferred, 1,3-phenylenebis(di-2,6-xylenyl phosphate) and aluminum salts of dialkylphosphinic acids are more preferred, and aluminum trisdiethylphosphinate is even more preferred.

[0174] -Metal hydrate- Examples of metal hydrates include aluminum hydroxide hydrate and magnesium hydroxide hydrate.

[0175] -Halogen-based flame retardants- Examples of halogen-based flame retardants include chlorine-based flame retardants, bromine-based flame retardants, etc. Examples of chlorine-based flame retardants include chlorinated paraffin, etc.

[0176] When the resin composition of this embodiment contains a flame retardant (E), the content of the flame retardant (E) is not particularly limited, but is preferably 1 to 15 parts by mass, more preferably 4 to 12 parts by mass, and even more preferably 6 to 10 parts by mass, per 100 parts by mass of the total resin components in the resin composition of this embodiment. When the content of the flame retardant (E) is equal to or greater than the above-mentioned lower limit, the flame retardancy tends to be better. On the other hand, when the content of the flame retardant (E) is equal to or less than the above-mentioned upper limit, the dielectric properties, moldability, and conductor adhesion tend to be better.

[0177] Examples of the flame retardant aid include inorganic flame retardant aids such as antimony trioxide and zinc molybdate. When the resin composition of the present embodiment contains a flame retardant aid, the content thereof is not particularly limited, but is preferably 0.01 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, and even more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the total resin components in the resin composition of the present embodiment. When the content of the flame retardant aid is within the above range, better chemical resistance tends to be obtained.

[0178] (Curing accelerator (F)) By including the curing accelerator (F), the resin composition of the present embodiment has improved curability, and tends to have better dielectric properties, heat resistance, conductor adhesion, and the like. The curing accelerator (F) may be used alone or in combination of two or more.

[0179] Examples of the curing accelerator (F) include acidic catalysts such as p-toluenesulfonic acid; amine compounds such as triethylamine, pyridine, and tributylamine; imidazole compounds such as methylimidazole and phenylimidazole; isocyanate-masked imidazole compounds such as the addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole; tertiary amine compounds; quaternary ammonium compounds; phosphorus compounds such as triphenylphosphine; organic peroxides such as dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, and α,α'-bis(t-butylperoxy)diisopropylbenzene; and carboxylates of manganese, cobalt, zinc, and the like. Among these, from the viewpoint of heat resistance and storage stability, imidazole compounds, isocyanate-masked imidazole compounds, organic peroxides, and carboxylates are preferred, organic peroxides are more preferred, and dicumyl peroxide is even more preferred.

[0180] When the resin composition of this embodiment contains a curing accelerator (F), the content of the curing accelerator (F) is not particularly limited, but is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 7 parts by mass, and even more preferably 0.5 to 5 parts by mass, per 100 parts by mass of the total resin components in the resin composition of this embodiment. When the content of the curing accelerator (F) is at least the above-mentioned lower limit, the dielectric properties, heat resistance, and conductor adhesion tend to be better. Furthermore, when the content of the curing accelerator (F) is at most the above-mentioned upper limit, the storage stability tends to be better.

[0181] The resin composition of the present embodiment may further contain, as necessary, one or more optional components selected from the group consisting of resin materials other than the above-mentioned components, antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, colorants, lubricants, and other additives. The above-mentioned optional components may each be used alone or in combination of two or more. The content of the above-described optional components in the resin composition of this embodiment is not particularly limited, and they may be used as needed within a range that does not impair the effects of this embodiment. Furthermore, the resin composition of the present embodiment may not contain the above-mentioned optional components depending on the desired performance.

[0182] (organic solvent) The resin composition of the present embodiment may contain an organic solvent from the viewpoint of facilitating handling and facilitating production of a resin film and a prepreg. The organic solvent may be used alone or in combination of two or more kinds. In this specification, a resin composition containing an organic solvent may be referred to as a resin varnish.

[0183] Examples of organic solvents include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve, 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. Among these, from the viewpoint of solubility, alcohol solvents, ketone solvents, nitrogen atom-containing solvents, and aromatic hydrocarbon solvents are preferred, aromatic hydrocarbon solvents are more preferred, and toluene is even more preferred.

[0184] When the resin composition of this embodiment contains an organic solvent, the solids concentration of the resin composition is not particularly limited, but is preferably 30 to 90% by mass, more preferably 35 to 80% by mass, and even more preferably 40 to 60% by mass. When the solids concentration is within the above range, the resin composition is easy to handle, and the coating properties onto a support and the impregnation properties into a substrate tend to be improved. Furthermore, the solids concentration of the resin in the prepreg can be easily adjusted, which tends to make it easier to produce a prepreg having a desired thickness.

[0185] The dielectric constant (Dk) at 10 GHz of the cured product of the resin composition of this embodiment is not particularly limited, but from the viewpoint of low transmission loss, it is preferably 3.0 or less, more preferably 2.9 or less, and even more preferably 2.8 or less. The smaller the dielectric constant (Dk) of the cured product, the better, and there is no particular restriction on the lower limit, but in consideration of the balance with other physical properties, it may be, for example, 2.3 or more, 2.4 or more, or 2.5 or more. The conditions for obtaining a cured product from the resin composition of this embodiment can be the conditions described in the Examples. The above-mentioned relative dielectric constant (Dk) is a value based on the cavity resonator perturbation method, and more specifically, is a value measured by the method described in the examples.

[0186] The dielectric loss tangent (Df) at 10 GHz of the cured product of the resin composition of this embodiment is not particularly limited, but from the viewpoint of low transmission loss, it is preferably 0.0040 or less, more preferably 0.0030 or less, and even more preferably 0.0020 or less. The smaller the dielectric loss tangent (Df) of the cured product, the better, and there is no particular restriction on the lower limit, but in consideration of the balance with other physical properties, it may be, for example, 0.0010 or more, 0.0012 or more, or 0.0014 or more. The conditions for obtaining a cured product from the resin composition of this embodiment can be the conditions described in the Examples. The dielectric loss tangent (Df) is a value based on the cavity resonator perturbation method, and more specifically, is a value measured by the method described in the examples.

[0187] [Prepreg] The prepreg of this embodiment is a prepreg containing the resin composition of this embodiment. The prepreg of this embodiment is preferably obtained by impregnating or coating a sheet-like fiber-reinforced substrate with the resin composition of this embodiment and then B-staging the composition. In this specification, B-staging refers to bringing the composition into a B-stage state as defined in JIS K6900 (1994), and is also called semi-curing.

[0188] As the sheet-like fiber-reinforced substrate contained in the prepreg of this embodiment, a known sheet-like fiber-reinforced substrate used in various laminates for electrical insulating materials can be used. Examples of materials for the sheet-like fiber-reinforced substrate include inorganic fibers such as E-glass, D-glass, S-glass, and Q-glass; organic fibers such as polyimide, polyester, and tetrafluoroethylene; and mixtures thereof. These sheet-like fiber-reinforced substrates have shapes such as woven fabric, nonwoven fabric, roving, chopped strand mat, and surfacing mat. The thickness of the sheet-like fiber-reinforced substrate is not particularly limited, but from the viewpoint of mechanical strength and thinning of the prepreg, it is preferably 0.01 to 0.5 mm, more preferably 0.02 to 0.3 mm, and even more preferably 0.03 to 0.1 mm. The sheet-like fiber-reinforced substrate may be surface-treated with a coupling agent or the like, or may be mechanically subjected to fiber-opening treatment, from the viewpoints of impregnation with the resin composition, heat resistance, moisture absorption resistance, and processability when formed into a laminate.

[0189] The prepreg of this embodiment can be produced, for example, by impregnating or applying the resin composition of this embodiment to a sheet-like fiber-reinforced substrate, and then drying it as necessary. As a method for impregnating or applying the resin composition of this embodiment to a sheet-like fiber-reinforced substrate, for example, a hot melt method, a solvent method, or the like can be used.

[0190] The hot melt method is a method in which a resin composition containing no organic solvent is impregnated into or coated on a sheet-like fiber-reinforced substrate. One aspect of the hot melt method is to coat the resin composition of the present embodiment, which does not contain an organic solvent, onto coated paper with good peelability, and then laminate the coated resin composition onto a sheet-like fiber-reinforced substrate. Another embodiment of the hot melt method is a method in which the resin composition of the present embodiment, which does not contain an organic solvent, is directly applied to a sheet-like fiber-reinforced substrate using a die coater or the like.

[0191] The solvent method is a method of impregnating or coating a sheet-shaped fiber-reinforced substrate with a resin composition containing an organic solvent. Specifically, for example, a method of immersing a sheet-shaped fiber-reinforced substrate in the resin composition of this embodiment containing an organic solvent and then drying it can be mentioned. By drying, the organic solvent in the resin composition can be removed and the resin composition can be brought into a B-stage. The drying temperature is not particularly limited, but from the viewpoint of productivity and appropriately bringing the resin composition of this embodiment into a B-stage, it is preferably 50 to 200°C, more preferably 100 to 190°C, and even more preferably 150 to 180°C. The drying time is not particularly limited, but from the viewpoint of productivity and appropriately bringing the resin composition of this embodiment into a B-stage, it is preferably 1 to 30 minutes, more preferably 2 to 15 minutes, and even more preferably 3 to 10 minutes.

[0192] The solids concentration derived from the resin composition in the prepreg of this embodiment is not particularly limited, but from the viewpoint of obtaining better moldability when made into a laminate, it is preferably 20 to 90 mass%, more preferably 25 to 80 mass%, and even more preferably 30 to 75 mass%.

[0193] The thickness of the prepreg of this embodiment is not particularly limited, but from the viewpoint of enabling moldability and high-density wiring, it is preferably 0.01 to 0.5 mm, more preferably 0.02 to 0.3 mm, and even more preferably 0.03 to 0.1 mm.

[0194] [Resin film] The resin film of the present embodiment is a resin film containing the resin composition of the present embodiment. The resin film of this embodiment can be produced, for example, by applying the resin composition of this embodiment containing an organic solvent, that is, a resin varnish, to a support and then drying it by heating.

[0195] Examples of the support include a plastic film, a metal foil, and a release paper. Examples of plastic films include polyolefin films such as polyethylene, polypropylene, and polyvinyl chloride; polyester films such as polyethylene terephthalate (hereinafter sometimes referred to as "PET") and polyethylene naphthalate; polycarbonate films; and polyimide films. Among these, polyethylene terephthalate films are preferred from the viewpoints of economy and ease of handling. Examples of metal foils include copper foil and aluminum foil. When copper foil is used as the support, the copper foil itself can be used as a conductor layer to form a circuit. In this case, rolled copper foil, electrolytic copper foil, etc. can be used as the copper foil. When a thin copper foil is used, a copper foil with a carrier may be used from the viewpoint of improving workability. The support may be subjected to a surface treatment such as matte treatment or corona treatment, or may be subjected to a release treatment using a silicone resin-based release agent, an alkyd resin-based release agent, a fluororesin-based release agent, or the like. The thickness of the support is not particularly limited, but from the viewpoints of ease of handling and economy, it is preferably 10 to 150 μm, more preferably 20 to 100 μm, and even more preferably 25 to 50 μm.

[0196] The coating device for applying the resin varnish may be any coating device known to those skilled in the art, such as a comma coater, bar coater, kiss coater, roll coater, gravure coater, die coater, etc. These coating devices may be appropriately selected depending on the film thickness to be formed. The drying conditions after applying the resin varnish may be appropriately determined depending on the content, boiling point, etc. of the organic solvent, and are not particularly limited. For example, in the case of a resin varnish containing 40 to 60 mass % of an aromatic hydrocarbon solvent, the drying temperature is not particularly limited, but from the viewpoints of productivity and appropriately bringing the resin composition of the present embodiment into a B-stage, it is preferably 50 to 200°C, more preferably 100 to 190°C, and even more preferably 150 to 180°C. Furthermore, in the case of the above-mentioned resin varnish, the drying time is not particularly limited, but from the viewpoints of productivity and appropriately bringing the resin composition of this embodiment into a B-stage, it is preferably 1 to 30 minutes, more preferably 2 to 15 minutes, and even more preferably 3 to 10 minutes.

[0197] The thickness of the resin film of this embodiment can be determined appropriately depending on the application of the resin film, but from the viewpoint of formability and enabling high-density wiring, it is preferably 5 to 150 μm, more preferably 10 to 100 μm, and even more preferably 15 to 60 μm.

[0198] The resin film of this embodiment may have a protective film. The protective film is provided on the surface of the resin film of this embodiment opposite to the surface on which the support is provided, and is used for the purpose of preventing adhesion of foreign matter and scratches to the resin film. The protective film is peeled off before the resin film of this embodiment is laminated, heat pressed, or the like onto a circuit board or the like.

[0199] The resin film of this embodiment is preferably used to form an insulating layer when producing a multilayer printed wiring board. For example, when a multilayer printed wiring board is produced, the resin film of this embodiment is a layer that melts and flows when laminated onto a circuit board, thereby serving to embed the circuit board. Furthermore, when a circuit board has through holes, via holes, etc., the resin film of this embodiment flows into the holes and fills them.

[0200] [Laminate] The laminate of this embodiment is a laminate containing the prepreg of this embodiment and a metal foil. Note that a laminate having a metal foil is sometimes called a metal-clad laminate. The metal of the metal foil is not particularly limited as long as it is used as an electrical insulating material, and examples thereof include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing one or more of these metal elements. Examples of alloys include copper-based alloys, aluminum-based alloys, and iron-based alloys. Examples of copper-based alloys include copper-nickel alloys. Examples of iron-based alloys include iron-nickel alloys. Among these, from the viewpoints of conductivity and availability, copper, nickel, aluminum, and iron-nickel alloys are preferred, copper and aluminum are more preferred, and copper is even more preferred. The thickness of the metal foil is not particularly limited, but is preferably 1 to 200 μm, more preferably 2 to 100 μm, and even more preferably 3 to 50 μm.

[0201] The laminate of this embodiment can be produced, for example, by placing metal foil on one or both sides of the prepreg of this embodiment and then molding it under heat and pressure. Usually, the prepreg in a semi-cured state is cured by this heat and pressure molding to obtain the laminate of this embodiment. In the heat and pressure molding, only one prepreg may be used, or two or more prepregs may be laminated together. In addition to the prepreg and metal foil, a substrate with inner layer circuitry may also be included in the heat and pressure molding. For the hot pressure molding, for example, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, or the like can be used. The heating temperature for hot pressing is not particularly limited, but is preferably 100 to 300°C, more preferably 150 to 280°C, and even more preferably 200 to 250°C. The heating and pressing time for the hot and pressure molding is not particularly limited, but is preferably 10 to 300 minutes, more preferably 30 to 200 minutes, and even more preferably 80 to 150 minutes. The pressure for the hot pressing is not particularly limited, but is preferably 1.5 to 5 MPa, more preferably 1.7 to 3 MPa, and even more preferably 1.8 to 2.5 MPa. However, these conditions can be adjusted appropriately depending on the type of raw material used, and are not particularly limited.

[0202] [Multilayer printed wiring board] The multilayer printed wiring board of the present embodiment comprises one or more members selected from the group consisting of the prepreg of the present embodiment, the resin film of the present embodiment, and the laminate of the present embodiment. That is, the multilayer printed wiring board of this embodiment includes at least a multilayer structure containing a cured product of the prepreg of this embodiment, a cured product of the resin film of this embodiment, or a laminate of this embodiment, and a conductor circuit layer. A method for producing a multilayer printed wiring board of this embodiment using the resin film of this embodiment will be described below.

[0203] When a multilayer printed wiring board is manufactured using the resin film of this embodiment, the resin film of this embodiment is first laminated onto one or both sides of a circuit board. After the resin film of this embodiment is placed so as to be in contact with the circuit board, the resin film of this embodiment can be laminated onto the circuit board by, for example, pressing the circuit board while applying pressure and heat using a vacuum laminator. Examples of circuit boards used in multilayer printed wiring boards include glass epoxy, metal, polyester, polyimide, BT resin, and thermosetting polyphenylene ether substrates, each having a patterned conductor layer (circuit) formed on one or both sides thereof. From the viewpoint of adhesiveness, the surface of the conductor layer of the circuit board may be previously roughened by blackening or the like.

[0204] Next, after peeling off the support of the resin film as necessary, the resin film is cured by heating to form an insulating layer. The heating temperature during heat curing is not particularly limited, but is preferably 100 to 300°C, more preferably 120 to 280°C, and even more preferably 150 to 250°C. The heating time for heat curing is not particularly limited, but is preferably 2 to 300 minutes, more preferably 5 to 200 minutes, and even more preferably 10 to 150 minutes.

[0205] After forming the insulating layer by the above method, drilling may be performed as needed. Drilling is a process in which holes are drilled in the circuit board and the formed insulating layer by a drill, laser, plasma, or a combination of these methods to form via holes, through holes, etc. Examples of lasers used for drilling include carbon dioxide lasers, YAG lasers, UV lasers, and excimer lasers.

[0206] Next, the surface of the insulating layer may be roughened with an oxidizing agent. Furthermore, if via holes, through holes, etc. are formed in the insulating layer and the circuit board, the so-called "smear" that occurs when these holes are formed may be removed with an oxidizing agent. The roughening treatment and smear removal can be performed simultaneously. The roughening treatment can form uneven anchors on the surface of the insulating layer. Examples of the oxidizing agent include permanganates such as potassium permanganate and sodium permanganate, dichromates, ozone, hydrogen peroxide, sulfuric acid, nitric acid, etc. Among these, preferred are aqueous solutions of sodium hydroxide of potassium permanganate and aqueous solutions of sodium hydroxide of sodium permanganate, which are oxidizing agents commonly used in the manufacture of multilayer printed wiring boards by the build-up method.

[0207] Next, a conductor layer is formed on the roughened surface of the insulating layer. The conductor layer can be formed by, for example, plating. Examples of plating methods include electroless plating and electrolytic plating. Examples of metals for plating include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing at least one of these metal elements. Among these, copper and nickel are preferred, and copper is more preferred. Alternatively, a plating resist having a reverse pattern to the wiring pattern may be formed first, and then the wiring pattern may be formed only by electroless plating. Furthermore, after the conductor layer is formed, an annealing treatment may be carried out, which tends to further improve and stabilize the adhesive strength between the interlayer insulating layer and the conductor layer.

[0208] Methods that can be used to pattern the conductor layer and form a circuit include known methods such as a subtractive method, a full-additive method, a semi-additive method (SAP: Semi-Additive Process), and a modified semi-additive method (m-SAP: modified Semi-Additive Process).

[0209] [Semiconductor Package] The semiconductor package of this embodiment is formed by mounting a semiconductor on the multilayer printed wiring board of this embodiment. The semiconductor package of this embodiment can be manufactured, for example, by mounting a semiconductor chip, memory, etc. on the multilayer printed wiring board of this embodiment by a known method.

[0210] [Method of producing resin composition] The method for producing the resin composition of the present embodiment includes: (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; The method for producing a resin composition includes mixing the above components. The detailed explanation of each component is as above. When mixing the components, the components may be dissolved or dispersed while being stirred. The mixing conditions, such as the order in which the raw materials are mixed, the mixing temperature, and the mixing time, are not particularly limited and may be set arbitrarily depending on the types of raw materials, etc. [Example]

[0211] The present embodiment will be specifically described below with reference to examples, although the present embodiment is not limited to the following examples.

[0212] In each example, the number average molecular weight was measured by the following procedure. (Method for measuring number average molecular weight) The number average molecular weight was calculated by gel permeation chromatography (GPC) using a calibration curve prepared using standard polystyrene. The calibration curve was approximated by a cubic equation using standard polystyrene: TSKstandard POLYSTYRENE (Types: A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40) [manufactured by Tosoh Corporation, trade name]. The GPC measurement conditions are shown below. [GPC measurement conditions] Equipment: High-speed GPC equipment HLC-8320GPC Detector: UV-8320 ultraviolet absorption detector [manufactured by Tosoh Corporation] Column: Guard column: TSK Guardcolumn SuperHZ-L + Column: TSKgel SuperHZM-N + TSKgel SuperHZM-M + TSKgel SuperH-RC (all manufactured by Tosoh Corporation, product names) Column dimensions: 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 / 5mL Injection volume: 25μL Flow rate: 1.00mL / min Measurement temperature: 40℃

[0213] [Production of modified conjugated diene polymer] Manufacturing Examples 1-3 The amounts of raw materials and toluene as an organic solvent shown in Table 1 were placed in a 2 L glass flask equipped with a thermometer, a reflux condenser, and a stirrer and capable of being heated and cooled. The mixture was then reacted under a nitrogen atmosphere at 90 to 100°C for 5 hours with stirring to obtain solutions of modified conjugated diene polymers 1 to 3 (solid content concentration: 35% by mass). The number average molecular weights of the resulting modified conjugated diene polymers are shown in Table 1. In Table 1, the amount of each component means the amount of solid content.

[0214] [Table 1]

[0215] The details of each component listed in Table 1 are as follows: [(b1) component] Polybutadiene 1:1,2-polybutadiene homopolymer, number average molecular weight = 1,200, vinyl group content = 85% or more [(b2) component] Phosphorus-containing monomer 1: Diphenyl-(methacryloyloxymethyl)phosphine oxide [Reaction catalyst] Organic peroxide: α,α'-bis(t-butylperoxy)diisopropylbenzene

[0216] [Preparation of Resin Composition] Examples 1 to 3, Comparative Examples 1 to 2 Each component shown in Table 2 was blended with toluene in the amounts shown in Table 2, and then the mixture was stirred and mixed at 25° C. or while heating to 50 to 80° C. to prepare a resin composition with a solids concentration of approximately 50% by mass. In Table 2, the blend amount of each component is expressed in parts by mass, and in the case of a solution, it means parts by mass converted into solids content.

[0217] [Manufacturing resin film and resin boards with double-sided copper foil] The resin composition obtained in each example was applied to a 38 μm thick PET film (Teijin Limited, product name: G2-38), and then heated and dried for 5 minutes at 170° C. to produce a B-stage resin film. The resin film was peeled off from the PET film and then pulverized to obtain a B-stage resin powder. The resin powder obtained above was placed on a Teflon® sheet die-cut to a size of 1 mm thick x 50 mm long x 35 mm wide, and 18 μm thick low-profile copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., product name: 3EC-VLP-18) was placed on top and bottom of it. The low-profile copper foil was placed with the M side facing the resin powder. Next, this pre-heat-pressure-molded laminate was heat-pressurized at a temperature of 230°C, a pressure of 2.0 MPa, and a time of 120 minutes, forming the resin powder into a resin plate and curing it, thereby producing a resin plate with copper foil on both sides. The resin plate portion of the resulting double-sided copper foil-covered resin plate had a thickness of 1 mm.

[0218] [Measurement and evaluation methods] The resin compositions and resin sheets with copper foil on both sides obtained in the above examples and comparative examples were subjected to measurements and evaluations according to the following methods. The results are shown in Table 2.

[0219] (1. Evaluation of Compatibility of Resin Compositions) The resin compositions obtained in each example were visually observed, and compatibility (presence or absence of macroscopic (macro) phase separation and precipitates) was evaluated according to the following criteria. A: Even after leaving for one week or more, no macroscopic phase separation or precipitates were observed. B: No change occurred after leaving it for one day, but after leaving it for three days or more, no precipitate was observed, but some macroscopic phase separation occurred. C: After leaving it for one day, no precipitate was found, but macroscopic phase separation occurred. D: After standing for 1 day, precipitates were observed.

[0220] (2. Measurement of the dielectric constant and dielectric loss tangent of the cured product) The resin sheet with copper foil on both sides obtained in each example was immersed in a 10 mass % solution of ammonium persulfate (manufactured by Mitsubishi Gas Chemical Company, Inc.), which is a copper etching solution, to remove the copper foil and prepare a 2 mm × 50 mm test piece. Next, the relative permittivity (Dk) and dielectric loss tangent (Df) of the test piece were measured in the 10 GHz band at an ambient temperature of 25°C according to the cavity resonator perturbation method.

[0221] (3. Evaluation of flame retardancy) The outer copper foil of the double-sided copper-clad laminate was removed by immersion in a copper etching solution (a 10% by mass solution of ammonium persulfate, manufactured by Mitsubishi Gas Chemical Company, Inc.), and the specimen was cut to a length of 127 mm and a width of 12.7 mm to serve as a test specimen. Next, in accordance with the UL94 test method (V method), a 20 mm flame was applied twice for 10 seconds to the bottom end of the vertically held specimen, and the flame retardancy was evaluated in accordance with the standards of UL94 V method. If the specimen was burned during the test, it was marked "X."

[0222] [Table 2]

[0223] The details of each component shown in Table 2 are as follows: [Component (A)] Aromatic bismaleimide compound containing an indan ring: Number average molecular weight = 1,300 [(B) Component] Modified conjugated diene polymer 1: Modified conjugated diene polymer 1 obtained in Production Example 1 Modified conjugated diene polymer 2: Modified conjugated diene polymer 2 obtained in Production Example 2 Modified conjugated diene polymer 3: Modified conjugated diene polymer 3 obtained in Production Example 3 [(B') component] Conjugated diene polymer: 1,2-polybutadiene homopolymer, number average molecular weight = 1,200, vinyl group content = 85% or more [(C) component] Styrene-based elastomer: trade name "Tuftec (registered trademark) H1221" (manufactured by Asahi Kasei Corporation), hydrogenated styrene-based thermoplastic elastomer (SEBS; styrene-ethylene-butylene-styrene copolymer), styrene unit content = 12% by mass, MFR = 4.5 g / 10 min under measurement conditions of 230°C and a load of 2.16 kgf, number average molecular weight = 170,000

[0224] From Table 2, it can be seen that the resin compositions obtained in Examples 1 to 3 of this embodiment have low dielectric constants and dielectric loss tangents, and have excellent compatibility and flame retardancy. This demonstrates that the resin compositions of this embodiment have excellent dielectric properties, compatibility, and flame retardancy in high frequency bands of 10 GHz or higher. On the other hand, the resin composition obtained in Comparative Example 1 was poor in dielectric properties, compatibility, and flame retardancy, and the resin composition obtained in Comparative Example 2 was poor in compatibility and flame retardancy. [Industrial Applicability]

[0225] A cured product produced from the resin composition of this embodiment has excellent dielectric properties, compatibility, and flame retardancy in high frequency bands of 10 GHz or higher, making the resin composition of this embodiment useful for applications such as fifth-generation mobile communication system (5G) antennas that use radio waves in frequency bands above 6 GHz and multilayer printed wiring boards used in millimeter-wave radars that use radio waves in the frequency band of 30 to 300 GHz.

Claims

1. (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; A resin composition comprising:

2. The resin composition according to claim 1, wherein the component (b2) is a compound having a phosphine oxide group and an ethylenically unsaturated bond.

3. The resin composition according to claim 2, wherein the compound having a phosphine oxide group and an ethylenically unsaturated bond is a phosphine oxide group-containing (meth)acrylate compound.

4. The resin composition according to any one of claims 1 to 3, wherein the component (b1) is a polybutadiene having a 1,2-vinyl group.

5. The resin composition according to any one of claims 1 to 4, further comprising a styrene-based elastomer.

6. The resin composition according to any one of claims 1 to 5, wherein the component (A) is at least one selected from the group consisting of maleimide compounds and derivatives thereof, each of which contains a fused ring of an aromatic ring and an aliphatic ring in its molecular structure and has two or more N-substituted maleimide groups.

7. A prepreg comprising the resin composition according to any one of claims 1 to 6.

8. A laminate comprising the prepreg according to claim 7 and a metal foil.

9. A resin film comprising the resin composition according to any one of claims 1 to 6.

10. A multilayer printed wiring board comprising at least one member selected from the group consisting of the prepreg according to claim 7, the laminate according to claim 8, and the resin film according to claim 9.

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

12. A method for producing the resin composition according to any one of claims 1 to 6, comprising: (A) one or more compounds selected from the group consisting of maleimide compounds having one or more N-substituted maleimide groups and derivatives thereof; (B) (b1) a modified conjugated diene polymer obtained by reacting a conjugated diene polymer having a vinyl group in a side chain with (b2) a compound having a phosphorus atom and an ethylenically unsaturated bond; A method for producing a resin composition, comprising mixing the above components.

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