Resin composition, prepreg, laminate, resin film, multilayer printed wiring board, and semiconductor package

Abstract

To provide a resin composition that can express excellent dielectric properties in a high frequency band of 10 GHz or higher while having excellent heat resistance, a prepreg including the resin composition, a laminate, a resin film, a multilayer printed wiring board and a semiconductor package.SOLUTION: A resin composition has (A) a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group, (B) at least one selected from the group consisting of a maleimide compound having two or more N-substituted maleimide groups and a derivative thereof, (C) a conjugated diene polymer or a modified conjugated diene polymer, (D) a styrenic thermoplastic elastomer, and (E) an imidazole compound or a modified imidazole compound. There are also provided a prepreg including the resin composition, a laminate, a resin film, a multilayer printed wiring board and a semiconductor package.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin composition, a prepreg, a laminate, a resin film, a multilayer printed wiring board, and a semiconductor package. [Background technology]

[0002] In mobile communication devices such as mobile phones, their base station equipment, network infrastructure devices such as servers and routers, and large computers, the speed and capacity of signals used are increasing year by year. Accordingly, the printed wiring boards mounted on these electronic devices must be compatible with higher frequencies, and there is a demand for board materials with excellent dielectric properties (low dielectric constant and low dielectric tangent; hereinafter, sometimes referred to as high-frequency properties) in high-frequency bands that enable reduction in transmission loss. In recent years, in addition to the above-mentioned electronic devices, new systems that handle high-frequency wireless signals in the ITS field (related to automobiles and traffic systems) and in the field of indoor short-range communication have been put into practical use or are planned to be put into practical use as applications that handle such high-frequency signals, and it is expected that in the future, there will be an increased demand for low-transmission-loss board materials for printed wiring boards mounted on these devices.

[0003] Conventionally, thermoplastic polymers with excellent high frequency characteristics have been used for printed wiring boards that require low transmission loss. For example, thermoplastic polymers that do not have polar groups in the molecule, such as polyphenylene ether and polybutadiene, are effective for reducing the dielectric loss tangent. However, these thermoplastic polymers have low compatibility with other resins, and when made into a resin composition, they are separated from other components, which makes them difficult to handle.

[0004] As a method for improving the compatibility of thermoplastic polymers, a method of including a copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic anhydride as a compatibilizing component in a resin composition has been studied. Patent Document 1 aims to provide a thermosetting resin composition having excellent heat resistance, low thermal expansion, low relative dielectric constant and low dielectric tangent, and discloses a thermosetting resin composition containing (A) an addition reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups in one molecule and an amine compound (a2) having at least two primary amino groups in one molecule, (B) polybutadiene, and (C) a copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic anhydride. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2019-99711 A Summary of the Invention [Problem to be solved by the invention]

[0006] The resin composition described in Patent Document 1 has improved compatibility with thermoplastic polymers and also has excellent dielectric properties in high frequency bands. However, in recent years, there has been a demand for substrate materials to be applied to fifth generation mobile communication system (5G) antennas that use radio waves in a frequency band exceeding 6 GHz and millimeter wave radars that use radio waves in a frequency band of 30 to 300 GHz. To this end, it is necessary to develop a resin composition with further improved dielectric properties in the 10 GHz band or higher, but with the technology of Patent Document 1, it is difficult to achieve further improvement in dielectric properties while maintaining various properties in good condition.

[0007] In view of the current situation, an object of the present invention is to provide a resin composition that has good heat resistance and is also capable of exhibiting excellent dielectric properties in a high frequency band of 10 GHz or more, and a prepreg, a laminate, a resin film, a multilayer printed wiring board, and a semiconductor package that use the resin composition. [Means for solving the problem]

[0008] As a result of investigations conducted by the present inventors to solve the above problems, they have found that the problems can be solved by the present invention described below. That is, the present invention relates to the following [1] to

[15] . [1] (A) a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group, (B) one or more selected from the group consisting of maleimide compounds having two or more N-substituted maleimide groups and derivatives thereof; (C) a conjugated diene polymer or a modified conjugated diene polymer; (D) a styrene-based thermoplastic elastomer; (E) an imidazole compound or a modified imidazole compound, A resin composition comprising: [2] The resin composition according to the above [1], wherein the component (E) is a modified imidazole compound represented by the following general formula (e-1) or the following general formula (e-2). [ka] (In the formula, R e1 , R e2 , R e3 and R e4 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a phenyl group; X e1 is an alkylene group or a divalent aromatic hydrocarbon group. [ka] (In the formula, R e5 , R e6 , R e7 and Re8 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a phenyl group; X e2 is an alkylene group, an alkylidene group, an ether group, or a sulfonyl group. [3] The resin composition according to the above [1] or [2], wherein the component (A) contains a structure represented by the following general formula (a-1): [ka] (In the formula, R a1 is an ethylenically unsaturated bond-containing group having 2 to 10 carbon atoms. n1 is 1 or 2, and n2 is 0 or 1. * indicates the bonding position to other structures.) [4] The resin composition according to any one of the above [1] to [3], wherein the ethylenically unsaturated bond-containing group of the component (A) is a vinyl group, an isopropenyl group, an allyl group, a 1-methylallyl group, or a 3-butenyl group. [5] The resin composition according to any one of the above [1] to [4], wherein the component (C) is a modified conjugated diene polymer obtained by modifying (c1) a conjugated diene polymer having a vinyl group in the side chain with (c2) a maleimide compound having two or more N-substituted maleimide groups. [6] The resin composition according to the above [5], wherein the component (C) has, in a side chain, a substituent (x) formed by reaction between a vinyl group in the component (c1) and an N-substituted maleimide group in the component (c2). [7] The resin composition according to the above [6], wherein the substituent (x) is a group containing a structure represented by the following general formula (C-11) or the following general formula (C-12) as a structure derived from the component (c2). [ka] (In the formula, X C1 is a divalent organic group, * C1 is the site at which the (c1) component bonds to the carbon atom derived from the vinyl group in the side chain. C2 is the site of attachment to another atom.) [8] The resin composition according to any one of the above [5] to [7], wherein the component (c1) is a polybutadiene having a 1,2-vinyl group. [9] The resin composition according to any one of the above [1] to [8], further comprising an inorganic filler (F).

[10] A prepreg comprising the resin composition according to any one of [1] to [9] above.

[11] A laminate comprising the prepreg according to

[10] above and a metal foil.

[12] A resin film comprising the resin composition according to any one of the above [1] to [9].

[13] A multilayer printed wiring board comprising at least one member selected from the group consisting of the prepreg described in

[10] above, the laminate described in

[11] above, and the resin film described in

[12] above.

[14] A multilayer printed wiring board for a millimeter wave radar, comprising one or more members selected from the group consisting of the prepreg described in

[10] above, the laminate described in

[11] above, and the resin film described in

[12] above.

[15] A semiconductor package comprising a multilayer printed wiring board according to

[13] or

[14] above and a semiconductor mounted thereon. Effect of the Invention

[0009] According to the present invention, it is possible to provide a resin composition that has good heat resistance and is capable of exhibiting excellent dielectric properties in a high frequency band of 10 GHz or more, and a prepreg, a laminate, a resin film, a multilayer printed wiring board, and a semiconductor package that use the resin composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with the values ​​shown in the examples. In addition, the lower and upper limits of the numerical ranges may be arbitrarily combined with the lower or upper limit of other numerical ranges. In addition, each component and material exemplified in this specification may be used alone or in combination of two or more types, unless otherwise specified. In this specification, the content of each component in the composition means the total amount of the multiple substances present in the composition when multiple substances corresponding to each component are present in the composition, unless otherwise specified. The present invention also includes any combination of the features described in this specification.

[0011] [Resin composition] The resin composition of the present embodiment is (A) a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group (hereinafter, may be abbreviated as "polyphenylene ether derivative (A)" or "component (A)"); (B) one or more selected from the group consisting of maleimide compounds having two or more N-substituted maleimide groups and derivatives thereof [hereinafter, sometimes abbreviated as "maleimide compound (B)" or "component (B)"], (C) a conjugated diene polymer or a modified conjugated diene polymer (hereinafter, sometimes abbreviated as "conjugated diene polymer or a modified product thereof (C)" or "component (C)"); (D) a styrene-based thermoplastic elastomer (hereinafter, sometimes abbreviated as "styrene-based thermoplastic elastomer (D)" or "component (D)"); (E) an imidazole compound or a modified imidazole compound (hereinafter, sometimes abbreviated as "imidazole compound or its modified product (E)" or "component (E)"); The resin composition comprises: Hereinafter, each component contained in the resin composition of the present embodiment will be described in detail.

[0012] <Polyphenylene ether derivative (A)> The polyphenylene ether derivative (A) has an ethylenically unsaturated bond-containing group, that is, the polyphenylene ether derivative (A) can be said to be a polyphenylene ether into which an ethylenically unsaturated bond-containing group has been introduced. 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, and the term "ethylenically unsaturated bond-containing group" means a substituent containing the above-mentioned ethylenically unsaturated bond. The component (A) may be used alone or in combination of two or more types.

[0013] The position of the ethylenically unsaturated bond-containing group is not particularly limited, and may be, for example, at one end or both ends of the component (A). The component (A) may be a mixture of a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at one end and a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at both ends, but it is preferable that the component (A) contains at least a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at one end, and more preferably is itself a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at one end. When the component (A) contains a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at one terminal, the content of the polyphenylene ether derivative having an ethylenically unsaturated bond-containing group at one terminal in the component (A) may be 30 mass% or more, 45 mass% or more, 55 mass% or more, 70 mass% or more, 90 mass% or more, or may be substantially 100 mass%.

[0014] Examples of the ethylenically unsaturated bond-containing group contained in component (A) include unsaturated aliphatic hydrocarbon groups such as vinyl groups, isopropenyl groups, allyl groups, 1-methylallyl groups, and 3-butenyl groups; and heteroatom-containing substituents such as maleimide groups and (meth)acryloyl groups. Among these, from the viewpoint of dielectric properties in high frequency bands of 10 GHz or more, unsaturated aliphatic hydrocarbon groups or maleimide groups are preferred, allyl groups or maleimide groups are more preferred, and allyl groups are even more preferred. In this specification, groups which contain an unsaturated aliphatic hydrocarbon group in part but cannot be considered an unsaturated aliphatic hydrocarbon group when viewed as a whole, such as a maleimide group or a (meth)acryloyl group, are not included in the above-mentioned "unsaturated aliphatic hydrocarbon group".

[0015] Next, the polyphenylene ether derivative having an unsaturated aliphatic hydrocarbon group as the ethylenically unsaturated bond-containing group will be described in more detail.

[0016] From the viewpoint of dielectric properties in a high frequency band of 10 GHz or more, the number of unsaturated aliphatic hydrocarbon groups that component (A) has in one molecule is preferably 2 or more, more preferably 4 or more, and there is no particular upper limit, and it may be 8 or less, or 6 or less. Furthermore, from the viewpoint of dielectric properties in a high frequency band of 10 GHz or more, the number of unsaturated aliphatic hydrocarbon groups that component (A) has at one end is preferably 2 or more, more preferably 4 or more, and there is no particular upper limit, and it may be 8 or less, or 6 or less. It is most preferable that the number of unsaturated aliphatic hydrocarbon groups contained in component (A) and the number of unsaturated aliphatic hydrocarbon groups contained at one terminal of component (A) are both four.

[0017] From the viewpoint of dielectric properties in the high frequency band of 10 GHz or more, the component (A) preferably contains a structure represented by the following general formula (a-1).

[0018] [ka] (In the formula, R a1 are each independently an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms. n1 is 1 or 2, and n2 is 0 or 1. * indicates the bonding position to another structure.)

[0019] In the above general formula (a-1), R a1Examples of the unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms represented by include a vinyl group, an isopropenyl group, an allyl group, a 1-methylallyl group, a 3-butenyl group, etc. Among these, from the viewpoint of dielectric properties in a high frequency band of 10 GHz or more, an unsaturated aliphatic hydrocarbon group having 2 to 5 carbon atoms is preferred, and an allyl group is more preferred.

[0020] From the viewpoint of dielectric properties in the high frequency band of 10 GHz or higher, the component (A) also preferably has a structure represented by the following general formula (a-2).

[0021] [ka] (In the formula, R a2 and R a3 are each independently an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms. * indicates the bonding position to other structures.)

[0022] In the above general formula (a-2), R a2 and R a3 The unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms represented by R a1 The same as those mentioned above can be mentioned, and the same are preferred.

[0023] From the viewpoint of dielectric properties in a high frequency band of 10 GHz or more, the component (A) more preferably contains a structure represented by any one of the following general formulas (a-3) to (a-5), and even more preferably contains a structure represented by the following general formula (a-5).

[0024] [ka] (In the formula, R a4 is an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms. * indicates the bonding position to other structures.)

[0025] [ka] (In the formula, R a5 and R a6 are each independently an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms. a1 is a divalent aliphatic hydrocarbon group having 1 to 6 carbon atoms. * indicates the bonding position to other structures.)

[0026] [ka] (In the formula, R a7 ~R a10 are each independently an unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms. a2 is a divalent organic group. * indicates the bonding position to other structures.)

[0027] R in the above general formulas (a-3) to (a-5) a4 ~R a10 The unsaturated aliphatic hydrocarbon group having 2 to 10 carbon atoms represented by R a1 The same can be mentioned as in the above, and the preferred ones are also the same. X in the above general formula (a-4) a1 Examples of the divalent aliphatic hydrocarbon group having 1 to 6 carbon atoms represented by include alkylene groups having 1 to 6 carbon atoms, such as a methylene group, an ethylene group, and a trimethylene group; and alkylidene groups having 2 to 6 carbon atoms, such as an isopropylidene group. Among these, a methylene group and an isopropylidene group are preferred, and an isopropylidene group is more preferred. X in the above general formula (a-5) a2 Examples of the divalent organic group represented by include an aliphatic hydrocarbon group which may contain a heteroatom in a portion thereof, an alicyclic hydrocarbon group which may contain a heteroatom in a portion thereof, an aromatic hydrocarbon group which may contain a heteroatom in a portion thereof, and groups consisting of any combination thereof. Examples of the heteroatom include an oxygen atom, a nitrogen atom, and a sulfur atom. X a2The divalent organic group represented by is preferably a group containing no heteroatoms, more preferably an aliphatic hydrocarbon group containing no heteroatoms or an alicyclic hydrocarbon group containing no heteroatoms, and even more preferably a group consisting of a combination of an aliphatic hydrocarbon group containing no heteroatoms and an alicyclic hydrocarbon group containing no heteroatoms.

[0028] More preferred embodiments of the structures represented by the above general formula (a-3), (a-4) or (a-5) are structures represented by the following formulas (a-3'), (a-4') or (a-5'), respectively, from the viewpoint of dielectric properties in a high frequency band of 10 GHz or more. Among these, from the viewpoint of dielectric properties in a high frequency band of 10 GHz or more, the structures represented by the following formulas (a-4') or (a-5') are more preferred, and the structures represented by the following formula (a-5') are even more preferred.

[0029] [ka] (In the formula, X a2 represents X in the above general formula (a-5). a2 (The symbol * indicates the position of attachment to another structure.)

[0030] Since the component (A) is a polyphenylene ether derivative, it naturally also has a phenylene ether bond, and it preferably has a structural unit represented by the following general formula (a-10).

[0031] [ka] (In the formula, R a11 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom; and n3 is an integer of 0 to 4.

[0032] R in the above general formula (a-10) a11are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. Examples of the aliphatic hydrocarbon group 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, and an n-pentyl group. Examples of the aliphatic hydrocarbon group include an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and a methyl group is more preferable. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among the above, R a11 is preferably an aliphatic hydrocarbon group having 1 to 5 carbon atoms. n3 is an integer of 0 to 4, and may be an integer of 1 or 2, or may be 2. When n3 is 1 or 2, R a11 may be substituted at the ortho position on the benzene ring (based on the substitution position of the oxygen atom). In addition, when n3 is 2 or more, multiple R a11 They may be the same or different. The structural unit represented by the above general formula (a-10) may specifically be a structural unit represented by the following general formula (a-10').

[0033] [ka]

[0034] The component (A) may contain a polyphenylene ether derivative represented by any one of the following general formulas (a-6) to (a-8), and particularly preferably contains a polyphenylene ether derivative represented by the following general formula (a-7) or (a-8), and more preferably contains a polyphenylene ether derivative represented by the following general formula (a-8).

[0035] [ka] (In the formula, X a2 represents X in the above general formula (a-5). a2 Each of n4 to n6 is independently an integer of 1 to 200.

[0036] In the above general formulas (a-6) to (a-8), n4 to n6 are each independently an integer of 1 to 200, and from the viewpoint of the dielectric properties in a high frequency band of 10 GHz or more and the compatibility with the resin composition, are preferably an integer of 1 to 150, more preferably an integer of 1 to 120, and even more preferably an integer of 1 to 100. In any of the above general formulas (a-6) to (a-8), the polyphenylene ether derivatives having different values ​​of n4 to n6 may be a mixture, and usually tend to be a mixture.

[0037] [Number average molecular weight (Mn) of component (A)] The number average molecular weight of the polyphenylene ether derivative (A) is preferably 1,000 to 25,000. When the number average molecular weight of the polyphenylene ether derivative (A) is 1,000 or more, the dielectric properties in a high frequency band of 10 GHz or more tend to be further improved, and when it is 25,000 or less, the compatibility with the resin composition tends to be good and separation tends to be difficult even when left for a long period of time. From the same viewpoint, the number average molecular weight of the polyphenylene ether derivative (A) is more preferably 2,000 to 20,000, further preferably 3,000 to 10,000, and particularly preferably 4,000 to 6,000. In this specification, the number average molecular weight is a value calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC), and more specifically, a value determined by the measurement method described in the Examples.

[0038] [Method for producing component (A)] One embodiment of a method for producing the component (A) will be described below, but the method is not limited to the following description. For example, a phenol compound containing a structure represented by any one of the above general formulae (a-1) to (a-5) [hereinafter sometimes abbreviated as "unsaturated aliphatic hydrocarbon group-containing phenol compound (1)"] and a polyphenylene ether having a number average molecular weight of 3,000 to 30,000 [hereinafter sometimes abbreviated as "raw material polyphenylene ether"] are subjected to a redistribution reaction in an organic solvent, thereby producing a polyphenylene ether derivative (A) while decreasing the molecular weight of the polyphenylene ether.

[0039] The above redistribution reaction is, for example, a reaction in which an unsaturated aliphatic hydrocarbon group-containing phenolic compound (1) is mixed with a raw material polyphenylene ether already produced by polymerization, and a reaction catalyst described below is added as necessary, so that an oxy radical of the unsaturated aliphatic hydrocarbon group-containing phenolic compound (1) attacks a carbon atom to which an oxygen atom in the raw material polyphenylene ether is bonded, whereby the O-C bond is broken and the molecular weight is reduced. At that time, the oxy radical of the unsaturated aliphatic hydrocarbon group-containing phenolic compound (1) that attacked bonds with the carbon atom whose bond has been broken, and is incorporated into the structure of the polyphenylene ether. A known method can be used and applied for the redistribution reaction.

[0040] The molecular weight of the polyphenylene ether derivative (A) can be controlled by the amount of the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) used, and the more the amount of the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) used, the lower the molecular weight of the (A) component. In other words, the amount of the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) used can be appropriately adjusted so that the number average molecular weight of the final product (A) component is within a suitable range. The amount of the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) used is not particularly limited, but for example, when the number average molecular weight of the raw material polyphenylene ether to be reacted with the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) is 3,000 to 30,000, the unsaturated aliphatic hydrocarbon group-containing phenol compound (1) is used in an amount such that the number of hydroxyl groups per mole of the raw material polyphenylene ether is 1 to 10 moles, preferably 2 to 6 moles, to obtain the (A) component having a number average molecular weight within the above-mentioned preferred range.

[0041] The organic solvent used in the production process of the polyphenylene ether derivative (A) is not particularly limited, and examples thereof include alcohols such as methanol, ethanol, butanol, butyl cellosolve, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and mesitylene; esters such as methoxyethyl acetate, ethoxyethyl acetate, butoxyethyl acetate, and ethyl acetate; and nitrogen-containing compounds such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. These may be used alone or in combination of two or more.

[0042] In addition, in the production process of the polyphenylene ether derivative (A), as described above, a reaction catalyst can be used as necessary. For example, from the viewpoint of obtaining the (A) component with a stable number average molecular weight with good reproducibility, it is preferable to use an organic peroxide such as t-butylperoxyisopropyl monocarbonate in combination with a metal carboxylate such as manganese naphthenate or manganese octylate. In addition, the amount of the reaction catalyst used is not particularly limited. From the viewpoint of the reaction rate and gelation suppression in producing the (A) component, for example, the organic peroxide may be 0.5 to 5 parts by mass and the metal carboxylate may be 0.05 to 0.5 parts by mass per 100 parts by mass of the raw material polyphenylene ether to be reacted with the unsaturated aliphatic hydrocarbon group-containing phenol compound (1).

[0043] The above-mentioned unsaturated aliphatic hydrocarbon group-containing phenol compound (1), the above-mentioned raw material polyphenylene ether having a number average molecular weight of 3,000 to 30,000, an organic solvent and, if necessary, a reaction catalyst are charged in predetermined amounts into a reactor, and the mixture is reacted while being heated, kept warm and stirred, to obtain the polyphenylene ether derivative (A). The reaction temperature and reaction time in this step can be appropriately adjusted using reaction conditions for a known redistribution reaction. From the viewpoints of workability and suppression of gelation, and from the viewpoint of obtaining the component (A) having the desired number average molecular weight, for example, the reaction temperature may be set to 70 to 110°C and the reaction time to 1 to 8 hours.

[0044] The solids concentration during the reaction in the production process of component (A) [hereinafter also referred to as "reaction concentration"] is not particularly limited, but may be, for example, 10 to 60% by mass, or 20 to 50% by mass. When the reaction concentration is 10% by mass or more, the reaction rate does not become too slow and tends to be more advantageous in terms of production costs, while when it is 60% by mass or less, better solubility tends to be obtained, and further, the solution viscosity is low, stirring efficiency is good, and gelation tends to be less likely.

[0045] The solution of the polyphenylene ether derivative (A) produced as described above may be concentrated to remove a part of the organic solvent, or may be diluted by adding an organic solvent, if necessary.

[0046] The resin composition of the present embodiment tends to have more excellent dielectric properties in the high frequency band of 10 GHz or more than a resin composition containing the raw material polyphenylene ether instead of component (A).

[0047] The content of component (A) in the resin composition of the present embodiment is not particularly limited, but from the viewpoint of dielectric properties in the high frequency band of 10 GHz or more, it is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 10 parts by mass, even more preferably 0.7 to 5 parts by mass, and particularly preferably 1 to 3 parts by mass, relative to 100 parts by mass of the total of the resin components in the resin composition. In this specification, the term "resin components" refers to the components (A), (B), (C) and (D).

[0048] <Maleimide compound (B)> The maleimide compound (B) is at least one selected from the group consisting of maleimide compounds having two or more N-substituted maleimide groups and derivatives thereof. Examples of the "derivative of a maleimide compound having two or more N-substituted maleimide groups" include an addition reaction product between the maleimide compound having two or more N-substituted maleimide groups and an amine compound such as the diamine compound (b2) described later. The component (B) may be used alone or in combination of two or more types.

[0049] As the maleimide compound (B), from the viewpoints of compatibility with other resins, adhesion to conductors, and dielectric properties, (i) a maleimide compound (b1) having two or more N-substituted maleimide groups (hereinafter, sometimes simply referred to as "maleimide compound (b1)" or "(b1) component"); and (ii) A polyaminobismaleimide compound having a structural unit derived from a maleimide compound (b1) and a structural unit derived from a diamine compound (b2) [hereinafter, sometimes abbreviated as "polyaminobismaleimide compound (B1)" or "component (B1)".] One or more selected from the group consisting of are preferred.

[0050] (Maleimide compound (b1)) Specific examples of the component (b1) are not particularly limited as long as they are maleimide compounds having two or more N-substituted maleimide groups, and include aromatic maleimide compounds having two N-substituted maleimide groups in the molecule, such as bis(4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)sulfone, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, m-phenylene bismaleimide, and 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane; aromatic polymaleimide compounds having three or more N-substituted maleimide groups in the molecule, such as polyphenylmethane maleimide and biphenyl aralkyl maleimide; and aliphatic maleimide compounds, such as 1,6-bismaleimido-(2,2,4-trimethyl)hexane and pyrophosphate binder type long chain alkyl bismaleimide. Among these, from the viewpoints of compatibility with other resins, adhesion to conductors, heat resistance, low thermal expansion, and mechanical properties, aromatic maleimide compounds having two N-substituted maleimide groups in the molecule and aromatic polymaleimide compounds having three or more N-substituted maleimide groups in the molecule are preferred. As an aromatic maleimide compound having two N-substituted maleimide groups in the molecule, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide is more preferred, and as an aromatic polymaleimide compound having three or more N-substituted maleimide groups in the molecule, biphenylaralkyl maleimide is more preferred. The component (b1) may be used alone or in combination of two or more kinds.

[0051] The component (b1) is preferably a bismaleimide compound represented by the following general formula (b1-1).

[0052] [ka] (In the formula, X b1 is a divalent organic group.

[0053] X in the above general formula (b1-1)b1 is a divalent organic group, which corresponds to the residue of component (b1). The residue of component (b1) refers to the structure of the portion remaining after removing the N-substituted maleimide group from component (b1). X b1 Examples of the divalent organic group represented by the formula include groups represented by the following general formula (b1-2), (b1-3), (b1-4), (b1-5) or (b1-6).

[0054] [ka] (In the formula, R b1 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. p1 is an integer of 0 to 4.

[0055] R b1 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 may be an aliphatic hydrocarbon group having 1 to 3 carbon atoms or may be a methyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. p1 is an integer of 0 to 4, and from the viewpoint of availability, may be an integer of 0 to 2, may be 0 or 1, or may be 0. When p1 is an integer of 2 or more, a plurality of R b1 They may be the same or different.

[0056] [ka] (In the formula, R b2 and R b3 Each of X is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. b2is 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 (b1-3-1). p2 and p3 each independently represent an integer of 0 to 4.

[0057] R b2 and R b3 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R b1 The aliphatic hydrocarbon group may be an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and may be a methyl group, an ethyl group, or an ethyl group. X b2 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. From the viewpoints of compatibility with other resins, adhesion to a conductor, heat resistance, low thermal expansion, and mechanical properties, the alkylene group may be an alkylene group having 1 to 3 carbon atoms or a methylene group. X b2 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 isopropylidene group may be used from the viewpoints of compatibility with other resins, adhesion to a conductor, heat resistance, low thermal expansion, and mechanical properties. X b2 Among the above options, may be an alkylene group having 1 to 5 carbon atoms or an alkylidene group having 2 to 5 carbon atoms. p2 and p3 are each independently an integer of 0 to 4, and from the viewpoint of availability, may be either an integer of 0 to 2, or may be 0 or 2. When p2 or p3 is an integer of 2 or more, a plurality of R b2 Friends or R b3 They may be the same or different. In addition, X b2 The divalent group represented by general formula (b1-3-1) is as follows.

[0058] [ka] (In the formula, R b4 and R b5 Each of X is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. b3 represents 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. p4 and p5 each independently represent an integer of 0 to 4.

[0059] R b4 and R b5 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R b1 This is explained in the same way as in the case of X b3 The alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by X b2 Examples of the alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by the formula (I) are the same as those represented by the formula (I). X b3 As the alkylidene group, an alkylidene group having 2 to 5 carbon atoms may be selected from the above options. p4 and p5 are each independently an integer of 0 to 4. From the viewpoint of availability, each may be an integer of 0 to 2, or may be 0 or 1, or may be 0. When p4 or p5 is an integer of 2 or more, a plurality of R b4 Friends or R b5 They may be the same or different.

[0060] [ka] (In the formula, p6 is an integer of 0 to 10.)

[0061] p6 may be an integer of 0 to 5, or an integer of 0 to 3, from the viewpoint of availability.

[0062] [ka] (In the formula, p7 is a number from 0 to 5.)

[0063] [ka] (In the formula, R b6 and R b7 are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. p8 is an integer of 1 to 8.

[0064] R b6 and R b7 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R b1 This is explained in the same way as in the case of p8 is an integer of 1 to 8, and may be an integer of 1 to 3, or may be 1. If p8 is an integer equal to or greater than 2, multiple R b6 Friends or R b7 They may be the same or different.

[0065] (Polyaminobismaleimide compound (B1)) The polyaminobismaleimide compound (B1) is a polyaminobismaleimide compound having a structural unit derived from a maleimide compound (b1) and a structural unit derived from a diamine compound (b2). The component (b1) may be used alone or in combination of two or more kinds.

[0066] Examples of the structural unit derived from the component (b1) include one or more types selected from the group consisting of groups represented by the following general formula (b1-7) and groups represented by the following general formula (b1-8).

[0067] [ka] (In the formula, X b1 is a divalent organic group, and * indicates the bonding position to other structures.)

[0068] X in the above general formula (b1-7) and general formula (b1-8) b1 The explanation for X in the above general formula (b1-1) is b1 This is the same as the explanation for . The total content of the structural units derived from the (b1) component in the polyaminobismaleimide compound (B1) is preferably 5 to 95 mass%, more preferably 30 to 93 mass%, further preferably 60 to 90 mass%, and particularly preferably 75 to 90 mass%. When the content of the structural units derived from the (b1) component is within the above range, the dielectric properties in the high frequency band of 10 GHz or more are improved, and good film handling properties tend to be obtained.

[0069] There are no particular limitations on the component (b2), so long as it is a compound having two amino groups. The component (b2) may be 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. The component (b2) may be used alone or in combination of two or more kinds.

[0070] Among these, the (b2) component is preferably 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, from the viewpoints of excellent solubility in organic solvents, reactivity with the (b1) component, and heat resistance. Also, the (b2) component is preferably 3,3'-dimethyl-5,5'-diethyl-4,4'-diaminodiphenylmethane, from the viewpoints of excellent dielectric properties and low water absorption. From the viewpoints of excellent mechanical properties such as high adhesion to the conductor, elongation, and breaking strength, the component (b2) is preferably 2,2-bis[4-(4-aminophenoxy)phenyl]propane. Furthermore, from the viewpoints of excellent solubility in the above organic solvents, reactivity during synthesis, heat resistance, high adhesion to the conductor, as well as excellent dielectric properties and low moisture absorption, the component (b2) is preferably 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisaniline or 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline.

[0071] Examples of the structural unit derived from the component (b2) include one or more types selected from the group consisting of groups represented by the following general formula (b2-1) and groups represented by the following general formula (b2-2).

[0072] [ka] (In the formula, X b4 is a divalent organic group, and * indicates the bonding position to other structures.)

[0073] X in the above general formulae (b2-1) and (b2-2) b4 is a divalent organic group, which corresponds to the residue of component (b2). The residue of component (b2) refers to the structure of the portion of component (b2) excluding the functional group used in the bond, i.e., the amino group.

[0074] X in the above general formula (b2-1) and the above general formula (b2-2) b4 is preferably a divalent group represented by the following general formula (b2-3).

[0075] [ka] (In the formula, R b11 and R b12 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. b5 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 (b2-3-1) or (b2-3-2). p8 and p9 are each independently an integer of 0 to 4.

[0076] [ka] (In the formula, R b13 and R b14 Each of X is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. b6 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. p10 and p11 each independently represent an integer of 0 to 4.

[0077] [ka] (In the formula, R b15 Each of X is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. b7 and X b8each independently represents 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. p12 is an integer of 0 to 4.

[0078] R in the above general formula (b2-3), (b2-3-1) or (b2-3-2) b11 , R b12 , R b13 , R b14 and R b15 The aliphatic hydrocarbon group having 1 to 5 carbon atoms or the halogen atom represented by R b1 The aliphatic hydrocarbon group may be an aliphatic hydrocarbon group having 1 to 3 carbon atoms, or may be a methyl group or an ethyl group. X in the above general formula (b2-3) b5 In the above general formula (b2-3-1), X b6 And X in the above general formula (b2-3-2) b7 and X b8 The alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by X in the above general formula (b1-3) are b2 This is explained in the same way as in the case of In the general formula (b2-3), p8 and p9 are each independently an integer of 0 to 4. From the viewpoint of availability, each may be an integer of 0 to 2, or may be 0 or 2. When p8 or p9 is an integer of 2 or more, multiple R b11 Friends or R b12 They may be the same or different. In the above general formula (b2-3-1), p10 and p11 are each independently an integer of 0 to 4. From the viewpoint of availability, each may be an integer of 0 to 2, or may be 0 or 1, or may be 0. When p10 or p11 is an integer of 2 or more, a plurality of R b13 Friends or R b14 They may be the same or different. In the above general formula (b2-3-2), p12 is an integer of 0 to 4. From the viewpoint of availability, it may be an integer of 0 to 2, or may be 0. When p12 is an integer of 2 or more, a plurality of R b15 They may be the same or different.

[0079] The total content of the structural units derived from the (b2) component in the polyaminobismaleimide compound (B1) is preferably 5 to 95 mass%, more preferably 7 to 70 mass%, further preferably 10 to 40 mass%, and particularly preferably 10 to 25 mass%. When the total content of the structural units derived from the (b2) component is within the above range, excellent dielectric properties, and better heat resistance, flame retardancy, and glass transition temperature tend to be obtained.

[0080] The content ratio of the structural unit derived from the component (b1) and the structural unit derived from the component (b2) in the polyamino bismaleimide compound (B1) is such that the equivalent ratio (Tb2 / Tb1) of the total equivalent (Tb2) of the groups (including -NH2) derived from the -NH2 group of the component (b2) in the polyamino bismaleimide compound (B1) to the total equivalent (Tb1) of the groups (including N-substituted maleimide groups) derived from the N-substituted maleimide group of the component (b1) is preferably 0.05 to 10, more preferably 1 to 5. When the equivalent ratio (Tb2 / Tb1) is within the above range, excellent dielectric properties, and better heat resistance, flame retardancy, and glass transition temperature tend to be obtained.

[0081] From the viewpoints of dielectric properties, solubility in organic solvents, high adhesion to conductors, and moldability of resin films, it is preferable that the polyaminobismaleimide compound (B1) contains a polyaminobismaleimide compound represented by the following general formula (b2-4):

[0082] [ka] (In the formula, X b1 and X b4 is as explained above.)

[0083] (Production method of polyaminobismaleimide compound (B1)) The component (B1) can be produced, for example, by reacting the components (b1) and (b2) in an organic solvent. When the polyaminobismaleimide compound (B1) is produced by reacting the components (b1) and (b2), a reaction catalyst can be used as necessary. The reaction catalyst is not particularly limited, but examples thereof include acid catalysts such as p-toluenesulfonic acid, amines such as triethylamine, pyridine, tributylamine, imidazoles such as methylimidazole, phenylimidazole, phosphorus catalysts such as triphenylphosphine, etc. These may be used alone or in combination of two or more. The amount of the reaction catalyst used is not particularly limited, but may be, for example, 0.01 to 5 parts by mass per 100 parts by mass of the total amount of the components (b1) and (b2).

[0084] The polyaminobismaleimide compound (B1) is obtained by feeding the (b1) component, the (b2) component, and other components as necessary in a synthesis vessel in predetermined amounts, and subjecting the (b1) component and the (b2) component to a Michael addition reaction. The reaction conditions in this step are not particularly limited, but from the viewpoints of workability such as reaction rate, and suppression of gelation during the reaction, the reaction temperature is preferably 50 to 160°C, and the reaction time is preferably 1 to 10 hours. In this step, the organic solvent can be added or concentrated to adjust the solid content concentration and solution viscosity of the reaction raw materials. The solid content concentration of the reaction raw materials is not particularly limited, but is preferably 10 to 90 mass%, more preferably 20 to 80 mass%. When the solid content concentration of the reaction raw materials is 10 mass% or more, the reaction rate does not become too slow, and there is a tendency that it is advantageous in terms of production costs. Furthermore, when the solid content concentration of the reaction raw materials is 90 mass% or less, better solubility is obtained, stirring efficiency is improved, and gelation tends to be less likely.

[0085] The number average molecular weight of the polyaminobismaleimide compound (B1) is not particularly limited, but is preferably 400 to 10,000, more preferably 500 to 5,000, further preferably 600 to 2,000, and particularly preferably 700 to 1,500. In this specification, the number average molecular weight means a value measured by gel permeation chromatography (GPC) in terms of polystyrene, and specifically, it can be measured by the method described in the examples.

[0086] The content of the (B) component in the resin composition of the present embodiment is not particularly limited, but from the viewpoint of heat resistance and dielectric properties in a high frequency band of 10 GHz or more, it is preferably 10 to 90 parts by mass, more preferably 20 to 80 parts by mass, even more preferably 30 to 70 parts by mass, and particularly preferably 40 to 60 parts by mass, relative to 100 parts by mass of the total of the resin components in the resin composition.

[0087] <Conjugated diene polymer or modified conjugated diene polymer (C)> The conjugated diene polymer or modified product thereof (C) is not particularly limited, but may be (c1) a conjugated diene polymer having a vinyl group in the side chain (hereinafter, sometimes abbreviated as "component (c1)"); or A modified conjugated diene polymer (C1) [hereinafter sometimes abbreviated as "modified conjugated diene polymer (C1)" or "component (C1)"] obtained by modifying (c1) a conjugated diene polymer having a vinyl group in the side chain with (c2) a maleimide compound having two or more N-substituted maleimide groups [hereinafter sometimes abbreviated as "component (c2)"] is preferred. The component (C) may use one type alone, or two or more types in combination.

[0088] ((c1) Conjugated diene polymer having vinyl groups in the side chains) The component (c1) is not particularly limited as long as it is a conjugated diene polymer having a vinyl group in the side chain, but it is preferably a conjugated diene polymer having a plurality of vinyl groups in the side chain. From the viewpoints of dielectric properties and heat resistance, the number of vinyl groups contained in one molecule of the component (c1) is preferably 3 or more, more preferably 5 or more, and even more preferably 10 or more. The component (c1) may be used alone or in combination of two or more kinds.

[0089] In this specification, the conjugated diene polymer means a polymer of a conjugated diene compound. Examples of the conjugated diene compound 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 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 may be a copolymer of one or more conjugated diene compounds and one or more monomers other than the conjugated diene compounds. In this case, the polymerization method is not particularly limited and may be any of random polymerization, block polymerization, and graft polymerization.

[0090] Specific examples of the (c1) component include polybutadiene having a 1,2-vinyl group, butadiene-styrene copolymer having a 1,2-vinyl group, polyisoprene having a 1,2-vinyl group, etc. Among these, from the viewpoint of dielectric properties and heat resistance, polybutadiene having a 1,2-vinyl group and butadiene-styrene copolymer having a 1,2-vinyl group are preferred, and polybutadiene having a 1,2-vinyl group is more preferred. As the polybutadiene having a 1,2-vinyl group, butadiene homopolymer having a 1,2-vinyl group is preferred. The butadiene-derived 1,2-vinyl group contained in the component (c1) is a vinyl group contained in a structural unit derived from butadiene represented by the following formula (c1-1).

[0091] [ka]

[0092] When the component (c1) is a polybutadiene having a 1,2-vinyl group, the content of structural units having a 1,2-vinyl group (structural units represented by the above general formula (c1-1)) relative to all structural units derived from butadiene constituting the polybutadiene [hereinafter sometimes abbreviated as "vinyl group content"] is preferably 50 mol % or more, more preferably 60 mol % or more, even more preferably 70 mol % or more, particularly preferably 80 mol % or more, and most preferably 85 mol % or more, from the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion property, and heat resistance. From the same viewpoint, the polybutadiene having a 1,2-vinyl group is preferably a 1,2-polybutadiene homopolymer.

[0093] From the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion and heat resistance, the number average molecular weight of the (c1) component is preferably 400 to 2,500, more preferably 500 to 2,000, even more preferably 600 to 1,800, and particularly preferably 700 to 1,500.

[0094] (Modified conjugated diene polymer (C1)) The modified conjugated diene polymer (C1) is a modified conjugated diene polymer obtained by modifying the component (c1) with (c2) a maleimide compound having two or more N-substituted maleimide groups.

[0095] The component (c2) may be any maleimide compound having two or more N-substituted maleimide groups, and those listed above as the maleimide compound (B) can be used. The component (c2) may be used alone or in combination of two or more types.

[0096] Among these, as the component (c2), from the viewpoints of solubility in organic solvents and suppression of gelation during the reaction, as well as compatibility with other resins of the resultant component (C1), dielectric properties, low thermal expansion, and heat resistance, aromatic bismaleimide compounds substituted with an aliphatic hydrocarbon group are preferred, and a compound represented by the following general formula (c2-1) is more preferred.

[0097] [ka] (In the formula, R c1 and R c2 are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms. c1 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 (c2-1-1): q1 and q2 each independently represent an integer of 0 to 4, and q1+q2 is an integer of 1 or greater.

[0098] R c1 and R c2 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. As the aliphatic hydrocarbon group, from the viewpoints of compatibility with other resins and suppression of gelation during the reaction, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and an ethyl group or a methyl group is even more preferred.

[0099] X c1 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. As the alkylene group, an alkylene group having 1 to 3 carbon atoms is preferable, and a methylene group is more preferable. X c1 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, and an isopentylidene group. Each of q1 and q2 is independently an integer of 0 to 4, and q1+q2 is an integer of 1 or more. From the viewpoints of availability, compatibility with other resins, and suppression of gelation during the reaction, each of them is preferably an integer of 0 to 2, more preferably 1 or 2, and even more preferably 2. When q1 or q2 is an integer of 2 or more, a plurality of R c1Friends or R c2 They may be the same or different. In addition, X c1 The divalent group represented by general formula (c2-1-1) is as follows.

[0100] [ka] (In the formula, R c3 and R c4 Each of X is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. c2 represents 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. q3 and q4 each independently represent an integer of 0 to 4.

[0101] R c3 and R c4 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R c1 This is explained in the same way as in the case of X c2 The alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by X c1 Examples of the alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by the formula (I) are the same as those represented by the formula (I). q3 and q4 are each independently an integer of 0 to 4. From the viewpoint of availability, each may be an integer of 0 to 2, or may be 0 or 1, or may be 0. When q3 or q4 is an integer of 2 or more, a plurality of R c3 Friends or R c4 They may be the same or different.

[0102] Examples of the compound represented by the general formula (c2-1) include 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, etc. Among these, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide is preferred from the viewpoints of solubility in organic solvents and suppression of gelation during the reaction, as well as compatibility with other resins of the obtained component (C1), dielectric properties, low thermal expansion, and heat resistance.

[0103] (Reaction conditions) The method of reacting the components (c1) and (c2) is not particularly limited, and for example, the component (C1) can be obtained by charging predetermined amounts of the components (c1), (c2), a reaction catalyst, and an organic solvent into a reaction vessel and reacting them while heating, keeping warm, stirring, etc. as necessary. The reaction conditions in this step can be appropriately adjusted depending on the types of raw materials used, etc., but from the viewpoints of workability and suppression of gelation during the reaction, the reaction temperature is preferably 70 to 120°C, more preferably 80 to 110°C, and even more preferably 85 to 105°C, and the reaction time is preferably 0.5 to 15 hours, more preferably 1 to 10 hours, and even more preferably 3 to 7 hours.

[0104] The organic solvent used in the above reaction is not particularly limited, but includes alcohols such as methanol, ethanol, butanol, butyl cellosolve, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and mesitylene; esters such as methoxyethyl acetate, ethoxyethyl acetate, butoxyethyl acetate, and ethyl acetate; and nitrogen-containing compounds such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. These may be used alone or in combination of two or more. Among these, toluene is preferred from the viewpoint of resin solubility.

[0105] When the reaction is carried out in an organic solvent, the total content (solid content concentration) of the (c1) component and the (c2) component 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. If the total content is 10% by mass or more, the reaction rate does not become too slow, and there is a tendency that it is more advantageous in terms of production costs. In addition, if the total content is 70% by mass or less, better solubility is obtained, and the solution viscosity is low, the stirring efficiency is good, and gelation tends to be more suppressed.

[0106] As the reaction catalyst, from the viewpoint of obtaining sufficient reactivity while suppressing gelation during the reaction, an organic peroxide is preferable, and α,α'-bis(t-butylperoxy)diisopropylbenzene is more preferable. The reaction catalyst may be used alone or in combination of two or more kinds. The amount of the reaction catalyst used is not particularly limited, but is preferably 0.01 to 1.2 parts by mass, more preferably 0.03 to 1.0 part by mass, and even more preferably 0.05 to 0.8 part by mass, relative to 100 parts by mass of the total amount of the components (c1) and (c2).

[0107] The amounts of the components (c1) and (c2) used in the above reaction are determined based on the moles of the side chain vinyl groups (M v ) for 、 (c2) The number of moles of N-substituted maleimide groups in the component (M m ) ratio (M m / M v ) is preferably an amount of 0.01 to 0.5, more preferably 0.02 to 0.4, and even more preferably 0.04 to 0.3.

[0108] Through the above reaction, at least a portion of the vinyl groups in the side chain of the component (c1) reacts with the N-substituted maleimide groups in the component (c2), producing the component (C1). The resulting component (C1) has a substituent (x) in the side chain formed by reaction between the vinyl group in component (c1) and the N-substituted maleimide group in component (c2). From the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion, and heat resistance, the substituent (x) is preferably a group containing a structure represented by the following general formula (C-11) or the following general formula (C-12) as a structure derived from the component (c2).

[0109] [ka] (In the formula, X C1 is a divalent organic group, * C1 is the site at which component (c1) bonds to the carbon atom derived from the vinyl group in the side chain. C2 is the site of attachment to another atom.)

[0110] X in the above general formulas (C-11) and (C-12) C1 The explanation for X in the above general formula (b1-1) is b1 This is the same as the explanation for .

[0111] From the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion, and heat resistance, the substituent (x) is more preferably a group containing a structure represented by the following general formula (C-21) or (C-22) as a structure derived from the component (c2).

[0112] [ka] (In the formula, R c1、 R c2 , X c1 The explanation for q1 and q2 is as described above for general formula (c2-1). C1 and* C2 The explanation for is as described above for general formulas (C-11) and (C-12).

[0113] The (C1) component preferably has a substituent (x) and a vinyl group (y) in the side chain. In this case, the ratio of the number of the substituents (x) to the total number of the substituents (x) and the vinyl groups (y) in one molecule [x×100 / (x+y)] [hereinafter, sometimes referred to as the "vinyl group modification rate"] is preferably 10 to 60%, more preferably 20 to 55%, and even more preferably 30 to 50%, from the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion, and heat resistance. The vinyl group (y) is preferably a 1,2-vinyl group possessed by a structural unit derived from butadiene.

[0114] The number average molecular weight of component (C) is not particularly limited, but from the standpoints of compatibility with other resins, dielectric properties, low thermal expansion, and heat resistance, it is preferably 700 to 6,000, more preferably 800 to 5,000, even more preferably 900 to 4,500, and particularly preferably 1,000 to 4,000.

[0115] The content of the (C) component in the resin composition of the present embodiment is not particularly limited, but from the viewpoints of compatibility with other resins, dielectric properties, low thermal expansion, and heat resistance, it is preferably 1 to 50 parts by mass, more preferably 5 to 40 parts by mass, even more preferably 10 to 30 parts by mass, and particularly preferably 15 to 25 parts by mass, relative to 100 parts by mass of the total of the resin components in the resin composition.

[0116] <Styrene-based thermoplastic elastomer (D)> The styrene-based thermoplastic elastomer (D) is not particularly limited as long as it is a thermoplastic elastomer having a structural unit derived from a styrene-based compound, and may have a structural unit represented by the following general formula (d-1).

[0117] [ka] (In the formula, R d1 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R d2 is an alkyl group having 1 to 5 carbon atoms. k is an integer of 0 to 5.

[0118] R d1 and R d2 Examples of the alkyl group having 1 to 5 carbon atoms represented by include a methyl group, an ethyl group, and an n-propyl group, and the alkyl group may be an alkyl group having 1 to 3 carbon atoms or a methyl group. k may be an integer of 0 to 2, or may be 0 or 1, or may be 0.

[0119] Examples of structural units contained in component (D) other than those derived from styrene-based compounds 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 component (D) may be used alone or in combination of two or more types. The butadiene-derived structural unit and the isoprene-derived structural unit may be hydrogenated. When hydrogenated, the butadiene-derived structural unit is a structural unit having a mixture of ethylene units and butylene units, and the isoprene-derived structural unit is a structural unit having a mixture of ethylene units and propylene units.

[0120] From the viewpoints of dielectric properties, adhesion to a conductor, heat resistance, glass transition temperature, and thermal expansion coefficient, the (D) component is preferably at least one selected from the group consisting of hydrogenated styrene-butadiene-styrene block copolymers (SEBS, SBBS), hydrogenated styrene-isoprene-styrene block copolymers (SEPS), and styrene-maleic anhydride copolymers (SMA), more preferably at least one selected from the group consisting of hydrogenated styrene-butadiene-styrene block copolymers (SEBS) and hydrogenated styrene-isoprene-styrene block copolymers (SEPS), and even more preferably hydrogenated styrene-butadiene-styrene block copolymers (SEBS).

[0121] In the above SEBS, the content of structural units derived from styrene [hereinafter sometimes abbreviated as "styrene content"] is preferably 5 to 80 mass%, more preferably 10 to 75 mass%, further preferably 15 to 70 mass%, and particularly preferably 20 to 50 mass%, from the viewpoints of dielectric characteristics, adhesion to a conductor, heat resistance, glass transition temperature, and thermal expansion coefficient. The melt flow rate (MFR) of SEBS is not particularly limited, but may be 0.1 to 20 g / 10 min, or 0.5 to 15 g / 10 min, when measured under conditions of 230°C and a load of 2.16 kgf (21.2 N). 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, Ltd.

[0122] The weight average molecular weight (Mw) of the component (D) is not particularly limited, but is preferably from 12,000 to 1,000,000, more preferably from 30,000 to 500,000, still more preferably from 50,000 to 120,000, and particularly preferably from 70,000 to 100,000. In this specification, the weight average molecular weight (Mw) refers to a value measured by gel permeation chromatography (GPC) in terms of polystyrene.

[0123] The content of the (D) component in the resin composition of the present embodiment is not particularly limited, but from the viewpoints of dielectric properties, heat resistance, moldability, and compatibility, it is preferably 10 to 60 parts by mass, more preferably 15 to 50 parts by mass, even more preferably 20 to 40 parts by mass, and particularly preferably 25 to 30 parts by mass, per 100 parts by mass of the total of the resin components in the resin composition.

[0124] <Imidazole compound or modified compound thereof (E)> The resin composition of the present embodiment contains the component (E), and while having good heat resistance, can also exhibit excellent dielectric properties in high frequency bands of 10 GHz or higher. Examples of the imidazole compound or its modified product (E) include 2-methylimidazole, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1,2-dimethylimidazole, 2-ethyl-1-methylimidazole, 1,2-diethylimidazole, 1-ethyl-2-methylimidazole, 2-ethyl-4-methylimidazole, 4-ethyl-2-methylimidazole, 1-isobutyl-2-methylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2- imidazole compounds such as phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 2,4-diamino-6-[2'-methylimidazolyl-(1')]ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]ethyl-s-triazine, and 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]ethyl-s-triazine; isocyanate-masked imidazole, epoxy-masked imidazole, salts of the above imidazole compounds with trimellitic acid; salts of the above imidazole compounds with isocyanuric acid; and modified imidazole compounds such as salts of the above imidazole compounds with hydrobromic acid. The component (E) may be used alone or in combination of two or more types.

[0125] The modified imidazole compound is preferably a modified imidazole compound represented by the following general formula (e-1) or (e-2).

[0126] [ka] (In the formula, R e1 , R e2 , R e3and R e4 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a phenyl group; X e1 is an alkylene group or a divalent aromatic hydrocarbon group.

[0127] [ka] (In the formula, R e5 , R e6 , R e7 and R e8 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a phenyl group; X e2 is an alkylene group, an alkylidene group, an ether group, or a sulfonyl group.

[0128] The resin composition of the present embodiment contains the modified imidazole compound represented by the general formula (e-1) or the general formula (e-2) and thus has excellent compatibility with the resin components. Although the reason for this is unclear, these modified imidazole compounds have a highly polar imidazolyl group and a less polar hydrocarbon group (in the general formula (e-1), "-CH2-X e1 -CH2-" in the general formula (e-2), "-Ph-X e2 Since the maleimide compound (B) has a polar group, it is believed that the maleimide compound (B) functions as a compatibilizer between the maleimide compound (B) having high polarity and the thermoplastic polymer having low polarity. In addition, the resin composition containing the modified imidazole compound represented by the general formula (e-1) tends to have good heat resistance and excellent dielectric properties in particular. In addition, the resin composition containing the modified imidazole compound represented by the general formula (e-2) tends to have improved dielectric properties and excellent heat resistance in particular. In the present embodiment, the term "compatible" means that the resins are not necessarily compatible with each other on a molecular level, but are miscible with each other on a nano- or micro-level.

[0129] R in the above general formula (e-1) e1 , R e2 , Re3 and R e4 The aliphatic hydrocarbon group represented by has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and further preferably 1 or 2 carbon atoms. R e1 , R e2 , R e3 and R e4 Examples of the aliphatic hydrocarbon group represented by include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and stearyl; alkenyl groups; and alkynyl groups. These aliphatic hydrocarbon groups may be linear or branched. Among these, methyl and ethyl groups are preferred. X in the above general formula (e-1) e1 The alkylene group represented by the formula (I) preferably has 1 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 3 to 5 carbon atoms. X e1 Examples of the alkylene group represented by include a methylene group, an ethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, a 1,6-hexamethylene group, etc. Among these, a 1,4-tetramethylene group is preferred. X e1 The divalent aromatic hydrocarbon group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, and further preferably 6 to 12 carbon atoms. X e1 Examples of the divalent aromatic hydrocarbon group represented by include a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, and an anthrylene group.

[0130] R in the above general formula (e-2) e5 , R e6 , R e7 and R e8 The aliphatic hydrocarbon group represented by has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and further preferably 1 or 2 carbon atoms. R e5 , R e6 , Re7 and R e8 Examples of the aliphatic hydrocarbon group represented by include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and stearyl groups; alkenyl groups; and alkynyl groups. These aliphatic hydrocarbon groups may be linear or branched. R e5 , R e6 , R e7 and R e8 Among the atoms or groups represented by R e5 and R e6 is preferably a hydrogen atom, and R e7 and R e8 is preferably a phenyl group. X in the above general formula (e-2) e2 The alkylene group represented by the formula (I) preferably has 1 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 3 to 5 carbon atoms. X e2 Examples of the alkylene group represented by include a methylene group, an ethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, and a 1,6-hexamethylene group. X e2 The alkylidene group represented by the formula (I) preferably has 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms, and further preferably 3 to 5 carbon atoms. X e2 Examples of the alkylidene group represented by the formula (I) 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, a propylidene group is preferred.

[0131] The content of the (E) component in the resin composition of the present embodiment is not particularly limited, but from the viewpoints of compatibility, dielectric properties, and heat resistance, it is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 6 parts by mass, even more preferably 0.5 to 4 parts by mass, and particularly preferably 0.8 to 2 parts by mass, relative to 100 parts by mass of the total of the resin components in the resin composition.

[0132] <Inorganic filler (F)> By including an inorganic filler (F) [hereinafter sometimes abbreviated as "component (F)"] in the resin composition of this embodiment, the thermal expansion coefficient, elastic modulus, heat resistance, and flame retardancy tend to be improved. However, the resin composition of this embodiment may not include an inorganic filler (F) depending on the desired performance.

[0133] The (F) component is not particularly limited, and examples thereof 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 (calcined clay, etc.), talc, aluminum borate, and silicon carbide. These may be used alone or in combination of two or more. Among these, silica, alumina, mica, and talc are preferred, silica and alumina are more preferred, and silica is even more preferred, from the viewpoints of thermal expansion coefficient, elastic modulus, heat resistance, and flame retardancy. Examples of silica include precipitated silica produced by a wet method and having a high water content, and dry method silica produced by a dry method and containing almost no bound water, etc., and examples of dry method silica include crushed silica, fumed silica, fused silica (fused spherical silica), etc., depending on the production method.

[0134] The shape and particle size of the inorganic filler (F) are not particularly limited, but for example, the particle size 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. Here, the particle size refers to the average particle size, and is the particle size at the point corresponding to 50% volume when a cumulative frequency distribution curve is calculated based on the particle size, with the total volume of the particles being 100%. The particle size of the inorganic filler (F) can be measured using a particle size distribution measuring device using a laser diffraction scattering method, or the like.

[0135] When the resin composition of the present embodiment contains the (F) component, the content of the (F) component in the resin composition is not particularly limited, but from the viewpoints of the thermal expansion coefficient, elastic modulus, heat resistance, and flame retardancy, it is preferably 10 to 70 mass%, more preferably 20 to 65 mass%, even more preferably 30 to 60 mass%, and particularly preferably 40 to 55 mass%.

[0136] When the component (F) is used, a coupling agent may be used in combination as necessary for the purpose of improving the dispersibility of the component (F) and the adhesion between the component (F) and the organic components in the resin composition.

[0137] <Flame retardant (G)> By including a flame retardant (G) (hereinafter sometimes abbreviated as "component (G)") in the resin composition of this embodiment, the flame retardancy of the resin composition tends to be improved. Examples of the (G) component include phosphorus-based flame retardants, metal hydrates, and halogen-based flame retardants. From the viewpoint of environmental issues, phosphorus-based flame retardants and metal hydrates are also acceptable. The flame retardant (G) may be used alone or in combination of two or more. Furthermore, a flame retardant assistant may be included as necessary.

[0138] - Phosphorus-based flame retardants - The phosphorus-based flame retardant is not particularly limited as long as it contains phosphorus atoms among those generally used as flame retardants, and 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 it does not contain halogen atoms. From the viewpoints of dielectric properties in a high frequency band of 10 GHz or more, adhesion to a conductor, heat resistance, glass transition temperature, thermal expansion coefficient, and flame retardancy, it may be an organic phosphorus-based flame retardant. 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. 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 acid, organic nitrogen-containing phosphorus compounds, and cyclic organic phosphorus compounds. Among these, aromatic phosphate esters and metal salts of di-substituted phosphinic acid are preferred. Here, the metal salt may be any of lithium salts, sodium salts, potassium salts, calcium salts, magnesium salts, aluminum salts, titanium salts, and zinc salts, or may be aluminum salts. In addition, aromatic phosphate esters are preferred among organic phosphorus-based flame retardants.

[0139] 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). 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. Examples of the metal salt of disubstituted phosphinic acid include metal salts of dialkylphosphinic acid, metal salts of diallylphosphinic acid, metal salts of divinylphosphinic acid, metal salts of diarylphosphinic acid, etc. These metal salts may be any of lithium salts, sodium salts, potassium salts, calcium salts, magnesium salts, aluminum salts, titanium salts, and zinc salts, and aluminum salts may be selected. Examples of the organic nitrogen-containing phosphorus compound include phosphazene compounds such as bis(2-allylphenoxy)phosphazene and dicresylphosphazene; melamine phosphate; melamine pyrophosphate; melamine polyphosphate; and melam polyphosphate. 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. Among these, aromatic phosphates and metal salts of disubstituted phosphinic acids are preferred, and 1,3-phenylenebis(di-2,6-xylenyl phosphate) and aluminum salts of dialkylphosphinic acids are preferred.

[0140] -Metal hydrate- Examples of metal hydrates include aluminum hydroxide hydrates and magnesium hydroxide hydrates. These may be used alone or in combination of two or more. The metal hydroxides may also be inorganic fillers, but are classified as flame retardants when they are materials that can impart flame retardancy. -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.

[0141] When the resin composition of this embodiment contains a phosphorus-based flame retardant as component (G), the content of the phosphorus-based flame retardant in the resin composition is not particularly limited, but from the viewpoints of flame retardancy, moldability, heat resistance, etc., the content is preferably 0.2 to 10 parts by mass, more preferably 0.3 to 7 parts by mass, even more preferably 0.5 to 5 parts by mass, and particularly preferably 1 to 3 parts by mass, calculated as phosphorus atoms, per 100 parts by mass of the total of the resin components in the resin composition.

[0142] <Other Ingredients (H)> The resin composition of the present embodiment may further contain another component (H) other than the above [hereinafter, sometimes abbreviated as "component (H)".] Examples of the other component (H) include thermosetting resins, thermoplastic polymers, curing accelerators, flame retardants, additives, organic solvents, and the like other than the above components. One type of component (H) may be used alone, or two or more types may be used in combination.

[0143] Other examples of the curing accelerator as component (H) include acidic catalysts such as p-toluenesulfonic acid; amine compounds such as triethylamine, pyridine, and tributylamine; 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. The additives as other component (H) may be appropriately selected and contained from antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, colorants, lubricants, etc. These may be used alone or in combination of two or more. The amounts of these used are not particularly limited, and may be used within a range that does not impair the effects of the present invention.

[0144] (Organic solvent) The resin composition of the present embodiment may contain an organic solvent from the viewpoint of facilitating handling by dilution and from the viewpoint of facilitating production of a prepreg, which will be described later. A resin composition containing an organic solvent is generally referred to as a resin varnish or varnish. The organic solvent is not particularly limited, but examples thereof 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 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, and nitrogen atom-containing solvents are preferred, ketone solvents are more preferred, acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone are further preferred, and methyl ethyl ketone is particularly preferred. The organic solvent may be used alone or in combination of two or more kinds.

[0145] When the resin composition of the present embodiment contains an organic solvent, the solid content concentration is, for example, 30 to 90% by mass, or may be 35 to 80% by mass, or may be 40 to 60% by mass. By using a resin composition having a solid content concentration within the above range, the handling becomes easy, the impregnation into the substrate and the appearance of the produced prepreg are good, the solid content concentration of the resin in the prepreg described below is easily adjusted, and the production of a prepreg having a desired thickness tends to be easier.

[0146] <Method of producing resin composition> The resin composition of this embodiment can be produced by mixing the (A), (B), (C), (D), (E), (F) and (G) components, which are used in combination as necessary, and other components, by a known method. At this time, each component may be dissolved or dispersed while stirring. The mixing order, temperature, time, and other conditions are not particularly limited and may be set arbitrarily depending on the type of raw material, etc.

[0147] <Physical properties of resin composition> (Dielectric properties) The dielectric constant (Dk) at 10 GHz of the cured product of the resin composition of this embodiment (a laminate and a cured product of a resin film not including a fiber substrate such as glass cloth) 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), 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, 2.4 or more, or 2.5 or more. The dielectric loss tangent (Df) at 10 GHz of the cured product of the resin composition of this embodiment (a laminate not including a fiber substrate such as glass cloth and a cured product of a resin film) is preferably 0.0050 or less, more preferably 0.0040 or less, even more preferably 0.0030 or less, particularly preferably 0.0025 or less, and most preferably 0.0022 or less. The smaller the dielectric loss tangent (Df), 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, or 0.0015 or more. The dielectric constant (Dk) and the dielectric loss tangent (Df) are values ​​based on the cavity resonator perturbation method, and more specifically, are values ​​measured by the method described in the Examples. In this specification, the term "dielectric constant" simply refers to the relative dielectric constant.

[0148] (glass transition temperature) The resin composition of the present embodiment has a glass transition temperature measured by the method described in the examples of preferably 190° C. or higher, more preferably 200° C. or higher, and further preferably 210° C. or higher. The higher the glass transition temperature, the more preferable it is, but from the viewpoint of ease of production, it may be 250° C. or lower.

[0149] [Prepreg] The prepreg of the present embodiment is a prepreg containing the resin composition of the present embodiment. The prepreg of this embodiment contains, for example, the resin composition of this embodiment and a sheet-like fiber reinforced substrate. The prepreg is formed using the resin composition of this embodiment and a sheet-like fiber reinforced substrate, and can be obtained, for example, by impregnating or coating the resin composition of this embodiment into a sheet-like fiber reinforced substrate and drying it. More specifically, for example, the prepreg of this embodiment can be produced by heating and drying for 1 to 30 minutes at a temperature of 80 to 200 ° C. in a drying oven and semi-curing (B-stage). The amount of the resin composition used can be determined so that the solid content concentration derived from the resin composition in the prepreg after drying is 30 to 90 mass%. By setting the solid content concentration in the above range, better moldability tends to be obtained when it is made into a laminate.

[0150] As the sheet-like fiber reinforcing substrate of the prepreg, known ones used in various laminates for electrical insulating materials are used. The material of the sheet-like reinforcing substrate can be inorganic fibers such as E glass, D glass, S glass, Q glass, etc.; organic fibers such as polyimide, polyester, tetrafluoroethylene, etc.; mixtures thereof, etc. These sheet-like reinforcing substrates have shapes such as woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc. The thickness of the sheet-like fiber-reinforced substrate is not particularly limited, but may be, for example, 0.02 to 0.5 mm. In addition, from the viewpoints of impregnation with the resin composition, heat resistance, moisture absorption resistance, and processability when formed into a laminate, the sheet-like fiber reinforcement substrate may be surface-treated with a coupling agent or the like, or may be mechanically subjected to fiber opening treatment.

[0151] The resin composition can be impregnated or coated on the sheet-like reinforcing substrate by the following hot melt method or solvent method. The hot melt method is a method in which the resin composition does not contain an organic solvent, and (1) the resin composition is first coated onto a coated paper that has good peelability from the resin composition, and then the coated paper is laminated onto a sheet-like reinforcing substrate, or (2) the resin composition is directly coated onto a sheet-like reinforcing substrate using a die coater. On the other hand, the solvent method is a method in which an organic solvent is added to a resin composition, a sheet-like reinforcing substrate is immersed in the obtained resin composition to impregnate the sheet-like reinforcing substrate with the resin composition, and then the substrate is dried.

[0152] [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 the present embodiment can be produced, for example, by applying a resin composition containing an organic solvent, that is, a resin varnish, to a support and drying it by heating. Examples of the support include polyolefin films such as polyethylene, polypropylene, and polyvinyl chloride; polyester films such as polyethylene terephthalate (hereinafter also referred to as "PET") and polyethylene naphthalate; and various plastic films such as polycarbonate films and polyimide films. Metal foils such as copper foil and aluminum foil, and release paper may also be used as the support. The support may be subjected to a surface treatment such as a matte treatment or a corona treatment. The support may also 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 is preferably 10 to 150 μm, and more preferably 25 to 50 μm.

[0153] The method of applying the resin varnish to the support is not particularly limited, and any coating device known to those skilled in the art, such as a comma coater, a bar coater, a kiss coater, a roll coater, a gravure coater, a die coater, etc., can be used. These coating devices may be appropriately selected depending on the film thickness. The drying temperature and drying time may be appropriately determined depending on the amount of organic solvent used and the boiling point of the organic solvent used. For example, in the case of a resin varnish containing about 40 to 60 mass % of organic solvent, a resin film can be suitably formed by drying at 50 to 150°C for about 3 to 10 minutes.

[0154] [Laminate] The laminate of the present embodiment is a laminate containing the prepreg of the present embodiment and a metal foil. The laminate of this embodiment can be produced, for example, by disposing a metal foil on one or both sides of a single prepreg of this embodiment, or by disposing a metal foil on one or both sides of a prepreg obtained by stacking two or more prepregs of this embodiment, and then molding them under heat and pressure. 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 for electrical insulating material applications. From the viewpoint of electrical conductivity, the metal may be copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, or an alloy containing one or more of these metal elements, with copper and aluminum being preferred, and copper being more preferred. The conditions for hot and pressure molding are not particularly limited, but may be, for example, a temperature of 100 to 300° C., a pressure of 0.2 to 10 MPa, and a time of 0.1 to 5 hours. In addition, the hot and pressure molding may be performed using a vacuum press or the like to maintain a vacuum state for 0.5 to 5 hours.

[0155] [Multilayer printed wiring board] The multilayer printed wiring board of the present embodiment contains one or more selected from the group consisting of the prepreg of the present embodiment, the laminate of the present embodiment, and the resin film of the present embodiment. The multilayer printed wiring board of the present embodiment can be manufactured by performing a circuit formation process and a multilayer adhesive process by a known method, such as a hole punching process, a metal plating process, and an etching process of a metal foil, using one or more 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.

[0156] The resin composition, prepreg, laminate, resin film, and multilayer printed wiring board of the present embodiment can be suitably used in electronic devices that handle high-frequency signals of 10 GHz or more. In particular, the multilayer printed wiring board is useful as a multilayer printed wiring board for millimeter-wave radar.

[0157] [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 by mounting a semiconductor chip, a memory, etc. at predetermined positions on the multilayer printed wiring board of this embodiment.

[0158] Although the preferred embodiments of the present invention have been described above, these are merely examples for the purpose of explaining the present invention, and the scope of the present invention is not limited to these embodiments. The present invention can be embodied in various forms different from the above-described embodiments without departing from the gist of the present invention. EXAMPLES

[0159] The present invention will be specifically described below with reference to examples, although the present invention is not limited to the following examples.

[0160] 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) from a calibration curve using standard polystyrene. The calibration curve was approximated by a cubic equation using standard polystyrene: TSKstandard POLYSTYRENE (Type; A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40) [manufactured by Tosoh Corporation, product name]. The measurement conditions for GPC are shown below. 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 product names manufactured by Tosoh Corporation) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column), 6.0 x 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10mg / 5mL ·Injection volume: 25μL ·Flow rate: 1.00mL / min ·Measurement temperature: 40℃

[0161] [Production Example 1: Production of polyphenylene ether derivative] Into a 2 L glass flask equipped with a thermometer, a reflux condenser, and a stirrer, capable of heating and cooling, toluene, 1 mol of polyphenylene ether "Zylon (registered trademark) S203A" (trade name, manufactured by Asahi Kasei Corporation, number average molecular weight = 12,000, hereinafter also referred to as "raw PPE"), and an allyl group-containing compound represented by the following general formula (1) were added so that the hydroxyl group equivalent relative to the raw PPE was 6, and dissolved with stirring at 90 to 100°C. The amount of toluene used was an amount that gave a reaction concentration of 35% by mass.

[0162] [ka] (In the formula, X a2 is a divalent organic group, and X in the above general formula (a-5) a2 It is explained similarly to the above.)

[0163] After visually confirming that the allyl group-containing compound had dissolved, 2 parts by mass of t-butylperoxyisopropyl monocarbonate per 100 parts by mass of raw PPE and 1.11 parts by mass of manganese octylate per 100 parts by mass of raw PPE were added, and the solution was subjected to a redistribution reaction at a solution temperature of 90 to 100°C for 6 hours, and then cooled to 40°C to obtain a polyphenylene ether derivative having an allyl group at the molecular end. A small amount of this reaction solution was taken out and subjected to GPC measurement (polystyrene equivalent, eluent: tetrahydrofuran), and the double peak derived from the allyl group-containing compound became a single peak, and the number average molecular weight of the polyphenylene ether derivative was 4,200.

[0164] [Production Example 2: Production of modified conjugated diene polymer] In a 2L glass flask equipped with a thermometer, reflux condenser and stirrer, 33.5 parts by mass of 1,2-polybutadiene homopolymer (number average molecular weight = 1,200, vinyl group content = 85% or more), 1.47 parts by mass of 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, a reaction catalyst and an organic solvent were added, and the mixture was reacted under a nitrogen atmosphere at 90 to 100 ° C for 5 hours while stirring to obtain a modified conjugated diene polymer solution (solid content concentration: 35% by mass). The vinyl group modification rate of the obtained modified conjugated diene polymer was 40%, and the number average molecular weight was 3,500.

[0165] [Preparation of resin composition] Examples 1 to 3, Comparative Example 1 Each component shown in Table 1 was stirred and mixed while heating at room temperature or at 50 to 80°C according to the compounding amount (unit: parts by mass) shown in Table 1 to prepare a resin composition having a solids (non-volatile content) concentration of approximately 50% by mass. The resin composition obtained in each example was applied to a PET film (manufactured by Teijin Limited, product name: G2-38) having a thickness of 38 μm, and then heated and dried at 170° C. for 5 minutes to produce a resin film in a B-stage state. This resin film was peeled off from the PET film and then crushed to produce a resin powder. Next, the above-mentioned resin powder was put into a Teflon (registered trademark) sheet cut into a size of 1 mm thick x 50 mm long x 35 mm wide, and low-profile copper foils having a thickness of 18 μm (manufactured by Furukawa Electric Co., Ltd., product name: BF-ANP18) were placed on the top and bottom of the Teflon (registered trademark) sheet so that the M side was in contact with the put-in resin powder, and the resin composition was cured by heating and pressing under conditions of a temperature of 230° C., a pressure of 2.0 MPa, and a time of 120 minutes to produce a resin plate with copper foils on both sides (resin plate thickness: 1 mm).

[0166] [Evaluation and measurement methods] The 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 1.

[0167] (1.Method of measuring dielectric constant and dielectric loss tangent) The resin board 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.) as a copper etching solution to remove the copper foil, and from this evaluation board, a 2 mm x 50 mm evaluation board was produced. The dielectric constant (Dk) and dielectric loss tangent (Df) of the evaluation substrate were measured in the 10 GHz band in accordance with the cavity resonator perturbation method.

[0168] (2. Method for measuring glass transition temperature) The copper foil on both sides of the resin board with copper foil on both sides obtained in each example was removed by etching to obtain a 5 mm square test piece, and measurements were performed using a thermomechanical analyzer (TMA) [Model Q400, manufactured by TA Instruments Japan, Inc.] in accordance with the IPC (The Institute for Interconnecting and Packaging Electronic Circuits) standard.

[0169] [Table 1]

[0170] The details of each component listed in Table 1 are as follows. [Component (A)] Polyphenylene ether derivative: Polyphenylene ether derivative produced in Production Example 1

[0171] [(B) Component] Maleimide compound (B-1): biphenylaralkyl-type maleimide (manufactured by Nippon Kayaku Co., Ltd., product name "MIR-3000") Maleimide compound (B-2): 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide

[0172] [(C) component] Modified conjugated diene polymer: Modified conjugated diene polymer produced in Production Example 2

[0173] [(D) component] Hydrogenated styrene-based thermoplastic elastomer: styrene-ethylene-butylene-styrene (SEBS) copolymer (Kraton Polymer Japan Co., Ltd., product name "Kraton (registered trademark) MD1653", melt flow rate 5.0 g / 10 min, styrene content 30%, hydrogenation rate 100%)

[0174] [(E) component] Modified imidazole compound represented by general formula (e-1): R in general formula (e-1) e1 , R e2 is a methyl group, R e3 , R e4 is an ethyl group, X e1 Compounds in which is a 1,4-tetramethylene group Modified imidazole compound represented by general formula (e-2): R in general formula (e-2) e5 , R e6 is a hydrogen atom, R e7 and R e8 is a phenyl group, X e1 Compounds in which is a propylidene group 2-Ethyl-4-methylimidazole

[0175] [Component (F)] Silica: Spherical fused silica, average particle size = 0.5 μm

[0176] [(G) component] 1,3-phenylenebis(di-2,6-xylenyl phosphate): phosphorus content 9.0% by mass Phosphate metal salt: aluminum dialkylphosphinate, metal salt of disubstituted phosphinic acid, phosphorus content 23.5% by mass (manufactured by Clariant, product name "OP-935") Paraxylylenebisdiphenylphosphine oxide: phosphorus content 12.0% by mass

[0177] [(H) component] α,α'-Bis(t-butylperoxy)diisopropylbenzene

[0178] As is clear from Table 1, the cured products obtained in Examples 1 to 3 of this embodiment have excellent heat resistance and are superior to the cured product obtained in Comparative Example 1 in dielectric properties in the high frequency band of 10 GHz. [Industrial Applicability]

[0179] The laminate produced from the resin composition of the present invention has excellent heat resistance and dielectric properties in high frequency bands of 10 GHz or higher, and is therefore useful for multilayer printed wiring boards used in fifth-generation mobile communication system (5G) antennas that use radio waves in a frequency band exceeding 6 GHz and millimeter-wave radars that use radio waves in a frequency band of 30 to 300 GHz.

Claims

1. (A) a polyphenylene ether derivative having an ethylenically unsaturated bond-containing group; (B) one or more selected from the group consisting of maleimide compounds having two or more N-substituted maleimide groups and derivatives thereof; (C) a conjugated diene polymer or a modified conjugated diene polymer; (D) a styrene-based thermoplastic elastomer; (E) a modified imidazole compound; The composition comprises The component (E) is a modified imidazole compound represented by the following general formula (e-1): the ethylenically unsaturated bond-containing group of the component (A) is a vinyl group, an isopropenyl group, an allyl group, a 1-methylallyl group, or a 3-butenyl group, The resin composition, wherein the component (D) is at least one selected from the group consisting of a hydrogenated styrene-butadiene-styrene block copolymer and a hydrogenated styrene-isoprene-styrene block copolymer. 【Chemistry 1】 (In the formula, R ｅ１ , R ｅ２ , R ｅ３ and R ｅ４ each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a phenyl group; X ｅ１ is an alkylene group or a divalent aromatic hydrocarbon group.

2. X in the general formula (e-1) ｅ１ The resin composition according to claim 1 , wherein is an alkylene group.

3. The resin composition according to claim 1 or 2, wherein the component (A) includes a structure represented by the following general formula (a-1): 【Chemistry 3】 (In the formula, R ａ１ is an ethylenically unsaturated bond-containing group having 2 to 10 carbon atoms. n1 is 1 or 2, and n2 is 0 or 1. * indicates the bonding position to other structures.)

4. The resin composition according to any one of claims 1 to 3, wherein the ethylenically unsaturated bond-containing group contained in the component (A) is a vinyl group or an allyl group.

5. The resin composition according to any one of claims 1 to 4, wherein the component (C) is a modified conjugated diene polymer obtained by modifying (c1) a conjugated diene polymer having a vinyl group in a side chain with (c2) a maleimide compound having two or more N-substituted maleimide groups.

6. The (C) component has a substituent (x) in a side chain formed by reaction of a vinyl group in the (c1) component with an N-substituted maleimide group in the (c2) component. The resin composition according to claim 5.

7. The substituent (x) is a group containing a structure represented by the following general formula (C-11) or the following general formula (C-12) as a structure derived from the component (c2). The resin composition according to claim 6. 【Chemistry 4】 (In the formula, X Ｃ１ is a divalent organic group, * Ｃ１ is the site at which the component (c1) bonds to a carbon atom derived from a vinyl group in the side chain. Ｃ２ is the site of attachment to another atom.)

8. The resin composition according to any one of claims 5 to 7, wherein the component (c1) is a polybutadiene having a 1,2-vinyl group.

9. The resin composition according to any one of claims 1 to 8, further comprising an inorganic filler (F).

10. A prepreg comprising the resin composition according to any one of claims 1 to 9.

11. A laminate comprising the prepreg according to claim 10 and a metal foil.

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

13. A multilayer printed wiring board comprising at least one member selected from the group consisting of the prepreg according to claim 10, the laminate according to claim 11, and the resin film according to claim 12.

14. A multilayer printed wiring board for a millimeter wave radar, comprising at least one selected from the group consisting of the prepreg according to claim 10, the laminate according to claim 11, and the resin film according to claim 12.

15. A semiconductor package comprising the multilayer printed wiring board according to claim 13 or 14 and a semiconductor mounted thereon.

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