Resin composition, prepreg and metal foil-clad laminate each using the same, and method for producing resin composition

Abstract

To provide a uniform resin composition containing a polyphenylene ether compound and a maleimide compound.SOLUTION: According to one embodiment, there is provided a resin composition containing 100 pts.mass of a polyphenylene ether compound having a carbon-carbon double bond at a terminal, 30-300 pts.mass of a maleimide compound, 10-160 pts.mass of an aromatic organic solvent, 10-500 pts.mass of a cycloketone, and 10-310 pts.mass of an amide-based solvent.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin composition, a prepreg and a metal foil-clad laminate using the same, and a method for producing the resin composition. [Background technology]

[0002] In recent years, the progress of large capacity and high speed information communication has been remarkable, and there is a demand for development and improvement of materials used in electronic devices and communication devices. In particular, polyphenylene ether compounds have excellent electrical properties and are widely used as materials for printed wiring boards of electronic devices. Among them, many resin compositions using polyphenylene ether compounds have been proposed. In order to realize high speed signal transmission speed for information communication, it is desirable to reduce the dielectric constant of the material. In addition, in order to reduce signal loss during signal transmission, it is desirable to reduce the dielectric tangent. In order to reduce such dielectric constant and signal loss, it is known that it is preferable to add a maleimide compound having excellent heat resistance as a crosslinking compound to a resin composition containing a polyphenylene ether compound.

[0003] However, maleimide compounds have a problem of low solubility in solvents. As a solvent for a resin composition for use in electronic devices, communication devices, etc., aromatic organic solvents are often selected because they have high solubility of additives such as elastomers with excellent electrical properties. The above-mentioned polyphenylene ether compound also has high solubility in aromatic organic solvents. On the other hand, maleimide compounds generally have low solubility in aromatic organic solvents, and when a resin composition containing a polyphenylene ether compound and a maleimide compound is prepared, the maleimide compound precipitates, and a uniform resin composition cannot be prepared. In addition, ketone solvents such as methyl ethyl ketone are often selected as a solvent for a resin composition for use in electronic devices, communication devices, etc. While maleimide compounds have high solubility in ketone solvents, polyphenylene ether compounds have low solubility in ketone solvents, and when a resin composition containing a polyphenylene ether compound and a maleimide compound is prepared using methyl ethyl ketone, the polyphenylene ether compound precipitates, and a uniform resin composition cannot be prepared. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] US Patent No. 2014 / 275377 [Patent Document 2] US Patent No. 2014 / 322545 [Patent Document 3] US Patent No. 2014 / 349090 [Patent Document 4] US Patent No. 2015 / 44485 [Patent Document 5] US Patent No. 2018 / 208765 [Patent Document 6] US Patent No. 2020 / 71477 Summary of the Invention [Problem to be solved by the invention]

[0005] Under the above circumstances, there is a need to provide a homogeneous resin composition containing a polyphenylene ether compound and a maleimide compound. [Means for solving the problem]

[0006] Means for Solving the Problems As described above, the present inventors conducted intensive research and found that, when a polyphenylene ether compound and a maleimide compound are mixed in a predetermined ratio with a predetermined solvent, residual insoluble matter and precipitation are suppressed, and a homogeneous resin composition can be obtained. The present invention is, for example, as follows. [1] 100 parts by mass of a polyphenylene ether compound having a terminal carbon-carbon double bond; 30 to 300 parts by mass of a maleimide compound, 10 to 160 parts by mass of an aromatic organic solvent; 10 to 500 parts by mass of a cycloketone; 10 to 310 parts by mass of an amide solvent; A resin composition comprising: [2] The resin composition according to [1], wherein (total parts by mass of aromatic organic solvent + cycloketone + amide solvent) / (total parts by mass of polyphenylene ether compound + maleimide compound)=0.65 to 9.7. [3] The resin composition according to [1] or [2], wherein cycloketone (parts by mass) / maleimide compound (parts by mass)=0.2 to 8.0, and amide solvent (parts by mass) / maleimide compound (parts by mass)=0.2 to 4.0. [4] The resin composition according to any one of [1] to [3], wherein the polyphenylene ether compound has a structure represented by the following general formula (1): [ka] [In formula (1), X represents a group containing an aromatic ring; -(YO) n1 - represents a polyphenylene ether structure which may have a substituent; n1 represents an integer from 1 to 100; n2 represents an integer from 1 to 4; Rx is a group represented by the following formula (Rx-1) or formula (Rx-2); [ka] In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, and an alkynyl group, each of which may have a substituent; * is the bond site to the oxygen atom; Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent; z represents an integer from 0 to 4; and r represents an integer from 1 to 4. [4-1] The resin composition according to [4], wherein in the compound represented by the formula (1), X has a structure represented by the following formula (X1) or (X2): [ka] [In formula (X1), R 11 , R 12 , R 13 , R 16 , R 17 and R 18 R each independently represents an alkyl group having 6 or less carbon atoms or a phenyl group. 14 and R 15 each independently represents a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. Each of these may further have a substituent.] [ka] [In formula (X2), R 19 , R 20 , R 25 and R26 R each independently represents an alkyl group having 6 or less carbon atoms or a phenyl group. 21 , R 22 , R 23 , R 24 each independently represents a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- represents a linear, branched, or cyclic hydrocarbon group having 20 or less carbon atoms. Each of these may further have a substituent.] [4-2] The resin composition according to [4] or [4-1], wherein, in the formula (1), Y has a structure represented by the formula (Y1): [ka] [In formula (Y1), R 7 , R 8 , R 9 , and R 10 each independently represents an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom. Each of these may further have a substituent, and examples of the substituent include the above-mentioned R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the same as the substituents that Mc may have.] [4-3] The resin composition according to [4] to [4-2], wherein the polyphenylene ether compound is a compound represented by the following formula (3) or formula (4): [ka] [ka] [In the formulas (3) and (4), X has a structure represented by the above formula (X1) or (X2), and Y has a structure represented by the above formula (Y1)]. [5] The resin composition according to any one of [1] to [4-3], wherein the polyphenylene ether compound has a number average molecular weight (Mn) of 500 to 5,000. [6] The resin composition according to any one of [1] to [5], wherein the maleimide compound is a compound having two or more maleimide groups. [7] The resin composition according to [1], wherein the maleimide compound has a structure represented by the following general formula (M-1): [ka] [In formula (M-1), Z is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR 21 -, -C(=O)-, -C(=O)-O-, -C(=O)NR 21 -, a divalent group derived from indan, a group represented by formula (m1), and combinations thereof, each of which may have a substituent (wherein R 21 is a hydrogen atom or a methyl group). [ka] [7-1] The resin composition according to [7], wherein Z contains a moiety represented by the following formula (m2): [ka] [In formula (m2), Ra and Rb are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aromatic ring group, and combinations thereof, each of which may have a substituent; Each Rc is independently selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxyl group, a cycloalkoxyl group, a maleimide group, a hydroxyl group, an aryl group, an aryloxy group, an allyl ether group, a 2-propenyl group, and combinations thereof, each of which may have a substituent; Each p is independently an integer of 0 to 4. [7-2] The resin composition according to [7], wherein Z is a phenylene group which may have a substituent. [8] The resin composition according to any one of [1] to [7], wherein the maleimide compound has a structure represented by the following general formula (M-2): [ka] [In formula (M-2), W is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR 21 -, -C(=O)-, -C(=O)-O-, -C(=O)NR 21 -, a divalent group derived from indan, and combinations thereof, each of which may have a substituent (wherein R 21 is a hydrogen atom or a methyl group); each t is independently selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxyl group, a cycloalkoxyl group, a maleimide group, a hydroxyl group, an aryl group, an aryloxy group, an allyl ether group, a 2-propenyl group, and combinations thereof, each of which may have a substituent; and m is independently an integer of 0 to 4. [8-1] The resin composition according to any one of [1] to [7], wherein the maleimide compound is selected from the following: [ka] [9] The resin composition according to any one of [1] to [8-1], wherein the cycloketone is selected from the group consisting of cyclohexanone, cyclopentanone, and cycloheptanone.

[10] The resin composition according to any one of [1] to [9], wherein the amide solvent is selected from the group consisting of N,N-dimethylacetamide, N,N-dimethylformamide, and N-methyl-2-pyrrolidinone.

[11] The resin composition according to any one of [1] to

[10] , further comprising a crosslinking agent.

[12] The resin composition according to

[11] , wherein the crosslinking agent is selected from the group consisting of an alkenyl isocyanurate compound, a (meth)allyl isocyanurate compound, a tri(meth)allyl cyanurate compound, a polyfunctional methacrylate compound, a polyfunctional acrylate compound, a polyfunctional vinyl compound, a polyfunctional vinylphenyl group compound, a styrene derivative, and a polyfunctional isocyanate compound.

[13] A prepreg produced using a substrate and the resin composition according to any one of [1] to

[12] .

[14] A metal foil-clad laminate comprising at least one layer formed from the prepreg according to

[13] and a metal foil disposed on one or both sides of the layer formed from the prepreg.

[15] A method of mixing a maleimide compound, a cycloketone and an amide-based solvent to obtain a mixture; Next, a polyphenylene ether compound having a terminal carbon-carbon double bond and an aromatic organic solvent are added to the mixture and mixed. Including, With respect to 100 parts by mass of the polyphenylene ether compound, 30 to 300 parts by mass of the maleimide compound, 10 to 160 parts by mass of the aromatic organic solvent, 10 to 500 parts by mass of the cycloketone, and 10 to 310 parts by mass of the amide solvent are added. A method for producing a resin composition. Effect of the Invention

[0007] According to the present invention, it is possible to provide a homogeneous resin composition containing a polyphenylene ether compound and a maleimide compound. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] Hereinafter, embodiments of the present invention will be described. Note that the materials, configurations, etc. described below do not limit the present invention, and various modifications can be made within the scope of the present invention. In this specification, various physical properties and characteristic values ​​are those at 23° C. unless otherwise specified. In the description of groups (atomic groups) in this specification, any notation that does not indicate whether they are substituted or unsubstituted includes both groups (atomic groups) that have no substituents and groups (atomic groups) that have a substituent. In this specification, (meth)acrylate means methacrylate and / or acrylate, and (meth)acryloyl group means methacryloyl group and / or acryloyl group. Other similar descriptions are to be interpreted as above.

[0009] 1.Resin composition A resin composition according to one embodiment of the present invention comprises the following components: 100 parts by mass of a polyphenylene ether compound having a terminal carbon-carbon double bond; 30 to 300 parts by mass of a maleimide compound; 10 to 160 parts by mass of an aromatic organic solvent; 10 to 500 parts by mass of a cycloketone; and 10 to 310 parts by mass of an amide solvent.

[0010] As described above, a resin composition containing a polyphenylene ether compound and a maleimide compound can be a material having excellent electrical properties and heat resistance, but has a problem with solubility in a solvent. Under such circumstances, the present inventors have found that a resin composition having the above composition has excellent solubility in a solvent, and as a result, a uniform resin composition can be obtained. A resin composition containing solid matter due to insoluble residue or precipitation has poor moldability and may cause defects in appearance in a molded product. In addition, when solid matter is present in a resin composition, if the resin composition is impregnated into a glass cloth to produce a prepreg, a defect called "cissing" may occur due to the resin not being uniformly impregnated. In contrast, according to the invention related to the above embodiment, a uniform resin composition substantially free of solid matter can be obtained, so that the occurrence of such defects can be suppressed. A member using such a resin composition can be suitably used in electronic devices, communication devices, etc.

[0011] Hereinafter, each component contained in the resin composition according to the embodiment will be described in order. (1) Polyphenylene ether compounds The resin composition according to the embodiment contains a polyphenylene ether compound having a terminal carbon-carbon double bond. The polyphenylene ether compound contributes to properties such as low dielectric properties (Dk and / or Df) and low water absorption in a cured product (molded product) obtained by curing the resin composition.

[0012] The polyphenylene ether compound having a terminal carbon-carbon double bond is represented, for example, by the following formula (1): In particular, it is preferable that the polyphenylene ether compound has, as the terminal Rx, a group represented by the following formula (Rx-1), such as a vinylbenzyl group, and / or a group represented by the following formula (Rx-2), such as a (meth)acrylic group. [ka] In formula (1), X represents a group containing an aromatic ring, -(YO) n1 - represents a polyphenylene ether structure which may have a substituent, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by the following formula (Rx-1) or formula (Rx-2). [ka] In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group and an alkynyl group, each of which may have a substituent. * is a bonding site to an oxygen atom. Mc are each independently a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. z is an integer of 0 to 4. r is an integer of 1 to 4.

[0013] R 1 , R 2 , R 3 , R4 , R 5 , R 6 and the substituent that Mc may have, are not particularly limited, and examples thereof include an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a hydroxyl group, an amino group, and the like.

[0014] In formula (Rx-1), r represents an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 1 or 2, and further preferably 1. In formula (Rx-1), Mc each independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 8 carbon atoms, and more preferably a linear or branched alkyl group having 1 to 4 carbon atoms. Examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group. In formula (Rx-1), z represents an integer of 0 to 4, preferably 0 or 1, and more preferably 0.

[0015] A specific example of the group represented by formula (Rx-1) is a vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is a (meth)acryloyl group.

[0016] In the compound represented by formula (1), X preferably has a structure represented by the following formula (X1) or (X2). [ka] In formula (X1), R 11 , R 12 , R 13 , R 16 , R 17 and R 18 R each independently represents an alkyl group having 6 or less carbon atoms or a phenyl group. 14 and R 15each independently represents a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. Each of these may further have a substituent, and examples of the substituent include those described above for R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the same as the substituents that Mc may have. [ka] In formula (X2), R 19 , R 20 , R 25 and R 26 R each independently represents an alkyl group having 6 or less carbon atoms or a phenyl group. 21 , R 22 , R 23 , R 24 each independently represents a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; -A- is a linear, branched, or cyclic hydrocarbon group having 20 or less carbon atoms. Each of these may further have a substituent, and examples of the substituent include the above-mentioned R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the same as the substituents that Mc may have. Examples of -A- include divalent organic groups such as a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, a 1,3-phenylenebis(1-methylethylidene) group, a cyclohexylidene group, a phenylmethylene group, a naphthylmethylene group, and a 1-phenylethylidene group, but are not limited to these.

[0017] In formula (1), Y preferably has a structure represented by formula (Y1). [ka] In formula (Y1), R 7 , R 8 , R 9 , and R 10 each independently represents an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom. Each of these may further have a substituent, and examples of the substituent include the above-mentioned R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the same as the substituents that Mc may have.

[0018] When n1 and / or n2 are integers of 2 or more, the structural units modified by n1 and n2 may be the same or different. n1 is preferably an integer of 0 to 50, more preferably an integer of 1 to 30, and particularly preferably an integer of 1 to 10. n2 is preferably an integer of 2 to 4, more preferably 2 or 3, and particularly preferably 2.

[0019] The polyphenylene ether compound is preferably a compound represented by the following formula (3), and more preferably a compound represented by the following formula (4). [ka] [ka] In formulas (3) and (4), X preferably has a structure represented by the above formula (X1) or (X2), and Y preferably has a structure represented by the above formula (Y1).

[0020] In formulas (3) and (4), a and b each independently represent an integer from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are each independently an integer from 0 to 50, more preferably an integer from 1 to 30, and particularly preferably an integer from 1 to 10. When a and / or b is an integer of 2 or more, the two or more -(Y-O)- may each independently have one kind of structure arranged, or may have two or more kinds of structures arranged in blocks or randomly. Also, when a plurality of compounds represented by formula (3) or (4) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10. Rx in formula (3) has the same meaning as Rx in formula (1), and the preferred range is also the same.

[0021] The number average molecular weight (Mn) in terms of polystyrene of the polyphenylene ether compound by GPC (gel permeation chromatography) is preferably 500 to 4000, more preferably 800 to 3000. Also, the weight average molecular weight (Mw) is not particularly limited, but is preferably 500 to 8000, more preferably 800 to 6000. Being within the above range is preferable because it can achieve both prevention of stickiness when forming the resin composition into a coating film and solubility of the polyphenylene ether compound in a solvent.

[0022] (2) Maleimide compound The resin composition according to the embodiment contains a maleimide compound. The maleimide compound particularly contributes to the heat resistance of the cured product (molded body) obtained by curing the resin composition.

[0023] The maleimide compound is preferably a compound having two or more maleimide groups, more preferably a compound having 2 to 12 maleimide groups, further preferably 2 to 6 maleimide groups, and particularly preferably 2 to 4 maleimide groups.

[0024] The maleimide compound preferably has a structure represented by the following general formula (M-1): [ka] [In formula (M-1), Z is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR 21 -, -C(=O)-, -C(=O)-O-, -C(=O)NR 21 -, a divalent group derived from indan, a group represented by the following formula (m1), and combinations thereof, each of which may have a substituent (wherein R 21 is a hydrogen atom or a methyl group). [ka]

[0025] Z is preferably a group formed by combining two or more of an alkylene group, an arylene group, -O-, a divalent group derived from indan, and a group represented by the above formula (3). For example, Z more preferably contains a portion represented by the following formula (m2). [ka]

[0026] In formula (m2), Ra and Rb are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aromatic ring group, and a combination thereof, each of which may have a substituent.Ra and Rb are preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an aromatic ring group, and more preferably a hydrogen atom or a methyl group. Each Rc is independently selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxyl group, a cycloalkoxyl group, a maleimide group, a hydroxyl group, an aryl group, an aryloxy group, an allyl ether group, a 2-propenyl group, and a combination thereof, each of which may have a substituent. Rc is preferably an alkyl group having 1 to 3 carbon atoms, an aryl group, a maleimide group, or a combination thereof, and more preferably a methyl group or a maleimide group. Also preferred is an embodiment in which Z is a phenylene group which may have a substituent.

[0027] Substituents that Z, Ra, Rb, and Rc may further have are not particularly limited, and examples thereof include an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a maleimide group, a hydroxyl group, and an amino group. Each p is independently an integer of 0 to 4, preferably 0 to 3, and more preferably 0 to 2.

[0028] The maleimide compound more preferably has a structure represented by the following general formula (M-2): [ka] [In formula (M-2), W is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR 21 -, -C(=O)-, -C(=O)-O-, -C(=O)NR 21 -, a divalent group derived from indan, and combinations thereof, each of which may have a substituent (wherein R 21 is a hydrogen atom or a methyl group); each t is independently selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxyl group, a cycloalkoxyl group, a maleimide group, a hydroxyl group, an aryl group, an aryloxy group, an allyl ether group, a 2-propenyl group, and combinations thereof, each of which may have a substituent; and m is independently an integer of 0 to 4.

[0029] The divalent linking group of W is preferably an alkylene group, an arylene group, a divalent group derived from indane, or a combination thereof, more preferably an alkylene group having 1 to 4 carbon atoms, a phenylene group, a group derived from indane, or a combination thereof, and particularly preferably a methylene group, a phenylene group, or a combination thereof. The substituent that the divalent linking group of W may have is not particularly limited, and examples thereof include an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a maleimide group, and a hydroxyl group. Among these, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a maleimide group are preferred, and a methyl group, an ethyl group, a phenyl group, and a maleimide group are more preferred.

[0030] t is preferably selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a maleimide group, an allyl ether group, a 2-propenyl group, and a combination thereof, more preferably an alkyl group having 1 to 10 carbon atoms, and particularly preferably a methyl group or an ethyl group. The substituent that t may further have is the same as the substituent of W described above. m is preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.

[0031] The maleimide compound may have a structure represented by the following general formula (M-3): [ka] [In formula (M-3), t and m are as defined in formula (M-2)].

[0032] Examples of the maleimide compound include (4,4'-methylenediphenyl)bismaleimide [e.g., BMI-1000, BMI-1000H, BMI-1000S, BMI-1100, or BMI-1100H manufactured by Daiwa Chemical Industry Co., Ltd.], phenylmaleimide oligomers [e.g., BMI-2000 and BMI-2300 manufactured by Daiwa Chemical Industry Co., Ltd.], m-phenylene bismaleimide [e.g., BMI-3000 manufactured by Daiwa Chemical Industry Co., Ltd.], 2,2-bis-[4-(4-maleimidophenoxy)phenyl]propane [e.g., Examples of the bismaleimide include BMI-80 manufactured by K.I. Kasei Co., Ltd. and BMI-4000 manufactured by Daiwa Kasei Kogyo Co., Ltd., 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylethane bismaleimide [e.g., BMI-70 manufactured by K.I. Kasei Co., Ltd. and BMI-5100 manufactured by Daiwa Kasei Kogyo Co., Ltd.], (4-methyl-1,3'-phenylene) bismaleimide [e.g., BMI-7000 manufactured by Daiwa Kasei Kogyo Co., Ltd.], and phenylmaleimide oligomer [e.g., MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.]. These may be used alone or in combination of two or more kinds.

[0033] Particularly preferred maleimide compounds are shown below. [ka]

[0034] The amount of the maleimide compound contained in the resin composition is 30 to 300 parts by mass, preferably 30 to 150 parts by mass, more preferably 30 to 110 parts by mass, and particularly preferably 30 to 100 parts by mass, relative to 100 parts by mass of the polyphenylene ether compound. By containing the maleimide compound in such a ratio, in addition to advantages such as heat resistance inherently obtained by adding the maleimide compound, a uniform composition can be obtained by combining with appropriate types and amounts of other components.

[0035] (3) Aromatic organic solvents The resin composition according to the embodiment includes an aromatic organic solvent. The type of aromatic organic solvent is not particularly limited, and can be selected from those commonly used in the field. Specific examples include toluene, benzene, and xylene, and it is preferable to use toluene or xylene. The aromatic organic solvent may be used alone or in combination of two or more kinds. The amount of aromatic organic solvent contained in the resin composition is 10 to 160 parts by mass, preferably 20 to 120 parts by mass, more preferably 50 to 120 parts by mass, and particularly preferably 50 to 90 parts by mass, relative to 100 parts by mass of the polyphenylene ether compound. By including the aromatic organic solvent in such a ratio, a uniform composition can be obtained by combining with other components of appropriate types and amounts.

[0036] (4) Cycloketone The resin composition according to the embodiment contains a cycloketone. The type of cycloketone is not particularly limited, and can be selected from those usually used as solvents in the relevant field. Specific examples include cyclohexanone, cyclopentanone, cycloheptanone, etc., and it is preferable to use cyclohexanone or cyclopentanone. The cycloketone may be used alone or in combination of two or more kinds. The amount of cycloketone contained in the resin composition is 10 to 500 parts by mass, preferably 85 to 300 parts by mass, more preferably 85 to 200 parts by mass, and particularly preferably 90 to 130 parts by mass, relative to 100 parts by mass of the polyphenylene ether compound. By containing the cycloketone in such a ratio, a uniform composition can be obtained by combining with other components of appropriate types and amounts.

[0037] (5) Amide solvents The resin composition according to the embodiment includes an amide-based solvent. The type of amide-based solvent is not particularly limited, and can be selected from those usually used as solvents in the field. Specific examples include N,N-dimethylacetamide, N,N-dimethylformamide, and N-methyl-2-pyrrolidinone, and it is preferable to use N,N-dimethylacetamide or N-methyl-2-pyrrolidinone. The amide-based solvent may be used alone or in combination of two or more kinds. The amount of the amide-based solvent contained in the resin composition is 10 to 300 parts by mass, preferably 10 to 150 parts by mass, and more preferably 10 to 80 parts by mass, relative to 100 parts by mass of the polyphenylene ether compound. By including the amide-based solvent in such a ratio, a uniform composition can be obtained by combining with other components of appropriate types and amounts.

[0038] According to one embodiment, (total parts by mass of aromatic organic solvent + cycloketone + amide solvent) / (total parts by mass of polyphenylene ether compound + maleimide compound)=0.65 to 9.7. The above value is preferably 1.0 to 4.0, more preferably 1.1 to 3.1, and particularly preferably 1.1 to 2.2. By setting the range as described above, there is an advantage that the resin can be dissolved to produce a composition free of resin solids. Cycloketone (parts by mass) / maleimide compound (parts by mass) is preferably 0.2 to 8.0, more preferably 0.5 to 7.0, even more preferably 0.7 to 6.6, and particularly preferably 0.9 to 3.7. Alternatively, the above numerical value may be 0.7 to 2.9. Also, amide-based solvent (parts by mass) / maleimide compound (parts by mass) is preferably 0.2 to 4.0, more preferably 0.3 to 2.0, even more preferably 0.4 to 1.5, and particularly preferably 0.4 to 1.0. By setting the ratio within such a range, there is an advantage that the resin can be dissolved to produce a composition free of resin solids.

[0039] (6) Other ingredients The resin composition of the present invention may further contain additives such as a crosslinking agent, a flame retardant, an inorganic or organic filler, a coupling agent, an elastomer, etc. Furthermore, general additives for resin compositions used in the manufacture of electronic devices such as printed wiring boards may be added.

[0040] From the viewpoint of the crosslinking reaction, the crosslinking agent preferably has an average of two or more carbon-carbon unsaturated double bonds in the molecule. The crosslinking agent may be composed of one type of compound, or may be composed of two or more types of compounds. Examples of the crosslinking agent include alkenyl isocyanurate compounds, (meth)allyl isocyanurate compounds, tri(meth)allyl cyanurate compounds, polyfunctional methacrylate compounds having two or more methacrylic groups in the molecule, polyfunctional acrylate compounds having two or more acrylic groups in the molecule, polyfunctional vinyl compounds having two or more vinyl groups in the molecule, polyfunctional vinylphenyl group compounds having two or more vinylphenyl groups in the molecule, styrene derivatives, polyfunctional isocyanate compounds having an isocyanate group in the molecule, and the like.

[0041] As the crosslinking agent, an alkenyl isocyanurate compound may be used, and examples of such compounds include compounds having an isocyanurate structure and an alkenyl group in the molecule. For example, a triallyl isocyanurate compound such as triallyl isocyanurate (e.g., TAICROS (registered trademark) manufactured by Evonik Japan Co., Ltd.) can be used.

[0042] As the flame retardant, a brominated organic compound, for example, an aromatic bromine compound, can be used. Specifically, decabromodiphenylethane, 4,4-dibromobiphenyl, ethylenebistetrabromophthalimide, etc. can be used. Preferably, the brominated organic compound is contained in an amount such that the bromine content is 8% by mass or more and 20% by mass or less based on the total amount of the resin composition. When the bromine content is 8% by mass or more, the flame retardancy of the prepreg is not decreased and the flame retardancy of the UL standard 94V-0 level can be maintained.On the other hand, when the bromine content is 20% by mass or less, bromine does not dissociate when the prepreg is heated, so that a prepreg having heat resistance can be obtained.

[0043] From the viewpoint of environmental issues, a flame retardant of a phosphorus compound may be used. Among flame retardants generally used as flame retardants, there is no particular limitation as long as it contains a phosphorus atom, and it may be an inorganic phosphorus compound or an organic phosphorus compound. Examples of inorganic phosphorus compounds include red phosphorus, ammonium phosphate, phosphoric acid amide, phosphoric acid, and phosphine oxide. Examples of organic phosphorus compounds include aromatic phosphates, substituted phosphinates, nitrogen-containing phosphorus compounds, and cyclic organic phosphorus compounds. The flame retardants may be used alone or in combination of two or more kinds.

[0044] Examples of the filler include fibrous fillers such as glass fiber, carbon fiber, aramid fiber, silicon carbide fiber, alumina fiber, and boron fiber; inorganic whiskers such as silicon carbide, silicon nitride, magnesium oxide, potassium titanate, and aluminoborate; inorganic needle-like fillers such as wollastonite, zonolite, phosphate fiber, and sepiolite; spherical inorganic fillers such as ground silica, fused silica, talc, alumina, barium titanate, mica, and glass beads; and organic fillers such as fine particle polymers obtained by crosslinking (meth)acrylic esters, styrene, etc. Adding an inorganic filler (hereinafter referred to as inorganic filler) can reduce the thermal expansion coefficient of the prepreg and improve its rigidity. Examples of inorganic fillers that can be used include metal oxides, nitrides, silicides, and borides such as silica, boron nitride, wollastonite, talc, kaolin, clay, mica, alumina, zirconia, and titania. In particular, adding a low dielectric constant filler such as silica or boron nitride is expected to lower the dielectric constant of the resin composition.

[0045] The dielectric constant of the prepreg can be reduced by adding a filler made of an organic material (hereinafter referred to as an organic filler). As the organic filler, fluorine-based, polystyrene-based, divinylbenzene-based, polyimide-based, etc. can be used. As the fluorine-based filler (filler of a fluorine-containing compound), polytetrafluoroethylene (PTFE), polyperfluoroalkoxy resin, polyfluorinated ethylene propylene resin, polytetrafluoroethylene-polyethylene copolymer, polyvinylidene fluoride, polychlorotrifluoroethylene resin, etc. can be used. As the organic filler, hollow polymer particles can be used. In particular, by using hollow bodies whose shells are made of a material with a low dielectric constant, such as divinylbenzene or divinylbiphenyl, it is possible to achieve a low dielectric constant for the prepreg. As the inorganic or organic filler, fine particles having an average particle size of 10 μm or less can be used. The average particle size here may be a value listed in a catalog or other document of the filler to be added, or may be the average or median value of multiple fillers randomly selected. By setting the average particle size of the filler under the above conditions, a prepreg with high smoothness and reliability can be obtained. The filler may be used alone or in combination of two or more types.

[0046] Examples of the coupling agent include silane-based coupling agents such as vinyltrichlorosilane, vinyltriethoxysilane, vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, β(3,4-epoxycyclohexyl)ethyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, N-β(aminoethyl)γ-aminopropylmethylmethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, and γ-chloropropyltrimethoxysilane, titanate-based coupling agents, aluminum-based coupling agents, zircoaluminate-based coupling agents, silicone-based coupling agents, and fluorine-based coupling agents. The coupling agents may be used alone or in combination of two or more.

[0047] The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but is preferably thermoplastic. By including an elastomer, peel strength can be improved. Usable elastomers are not particularly limited, but examples thereof include polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. The elastomers may be used alone or in combination of two or more.

[0048] 2. Manufacturing method of resin composition According to one embodiment, mixing a maleimide compound, a cycloketone, and an amide solvent to obtain a mixture; Next, a polyphenylene ether compound having a terminal carbon-carbon double bond and an aromatic organic solvent are added to the mixture and mixed. A method for producing a resin composition comprising the steps of: In the above production method, 30 to 300 parts by mass of the maleimide compound, 10 to 160 parts by mass of the aromatic organic solvent, 10 to 500 parts by mass of the cycloketone, and 10 to 310 parts by mass of the amide solvent are added relative to 100 parts by mass of the polyphenylene ether compound.

[0049] The method for producing the resin composition according to the embodiment is not limited to the above method as long as it is possible to mix all materials to prepare a uniform resin composition. However, by adopting the above method, there is an advantage that the resin composition can be obtained in a shorter time.

[0050] 3.Applications (1) Film The resin composition according to the embodiment can be cured and used as a resin film. Examples of a method for processing the resin composition into a film include a method in which the resin composition according to the embodiment is applied to a release film or a conductor foil such as copper foil, and then dried.

[0051] The drying conditions for drying the solvent are not particularly limited, but since low temperatures tend to leave the solvent in the film, and high temperatures cause the curing of the phenylene ether resin to proceed, drying is preferably performed for 1 to 90 minutes at a temperature of 80° C. to 200° C. The thickness of the film can be adjusted by the concentration of the resin composition solution and the coating thickness, but since a thicker coating thickness tends to leave the solvent during drying, the film thickness is preferably 0.1 to 500 μm.

[0052] (2) Prepreg The resin composition according to the embodiment can also be used as a prepreg. According to one embodiment, a prepreg is provided that is made using a substrate and the resin composition according to the embodiment. When a prepreg is made using the resin composition according to the embodiment, there is substantially no residual maleimide compound or precipitation, so that it is possible to suppress the occurrence of defects caused by the resin not being uniformly impregnated, which is called "cissing."

[0053] In the preparation of the prepreg, the resin composition according to the embodiment and other additives as necessary are mixed to form a varnish. A suitable organic solvent, such as ketones such as methyl ethyl ketone, ethers such as dibutyl ether, and esters such as ethyl acetate, may be further added. The concentration of the resin solids in the varnish may be adjusted depending on the operation of impregnating the base material with the varnish, and may be, for example, from 40% by mass to 90% by mass. A prepreg can be obtained by impregnating a substrate with the above varnish and then drying by heating to remove the organic solvent and semi-cure the resin in the substrate.

[0054] The amount of varnish impregnated into the substrate is preferably set so that the mass ratio of the resin solid content in the prepreg is 35% by mass or more. Since the dielectric constant of the substrate is greater than that of the resin, in order to reduce the dielectric constant of the printed wiring board obtained using this prepreg, the content of the resin solid content in the prepreg may be greater than the above mass ratio. The substrate impregnated with the varnish can be heated at a temperature of 80°C or more and 200°C or less for 1 to 10 minutes. At this time, the substrate is heated so that the minimum melt viscosity of the resin composition in the prepreg is 10000 Pa·s or less. For example, when heating at a temperature of 150°C, the heating time is preferably 3 to 10 minutes, and more preferably 5 to 9 minutes. The heating conditions for the substrate impregnated with the varnish are not limited to the above conditions, but are determined so that the minimum melt viscosity of the resin composition in the prepreg is 10000 Pa·s or less. Here, the minimum melt viscosity of the resin composition in the prepreg refers to the minimum value of the melt viscosity of the resin composition in the prepreg in the temperature range from room temperature to 200°C. When heated at low temperature for a short time, the solvent remains and the melt viscosity decreases, but the dielectric loss tangent of the laminate may deteriorate. When heated at high temperature for a long time, the curing may progress and the melt viscosity may become too high. Therefore, from the viewpoint of reducing the amount of remaining solvent and suppressing the increase in melt viscosity due to heating, it is desirable that the minimum melt viscosity of the resin composition before heating is low.

[0055] The substrate is not particularly limited, and known materials used in various printed wiring board materials can be appropriately selected and used depending on the intended use and performance. Specific examples of fibers constituting the substrate are not particularly limited, and include glass fibers such as E glass, D glass, S glass, Q glass, NE glass, L glass, and T glass; inorganic fibers other than glass such as quartz; wholly aromatic polyamides such as polyparaphenylene terephthalamide (Kevlar (registered trademark), manufactured by DuPont Co., Ltd.) and copolyparaphenylene-3,4'-oxydiphenylene-terephthalamide (Technora (registered trademark), manufactured by Teijin Techno Products Co., Ltd.); polyesters such as 2,6-hydroxynaphthoic acid-parahydroxybenzoic acid (Vectran (registered trademark), manufactured by Kuraray Co., Ltd.) and Zexion (registered trademark, manufactured by KB Seiren Co., Ltd.); organic fibers such as polyparaphenylene benzoxazole (Zylon (registered trademark), manufactured by Toyobo Co., Ltd.) and polyimide. Among these, E glass, T glass, S glass, Q glass, and organic fiber are preferred from the viewpoint of low thermal expansion coefficient. The substrate may be used alone or in combination of two or more kinds.

[0056] The shape of the substrate is not particularly limited, but examples thereof include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc. The weaving method of the woven fabric is not particularly limited, but examples thereof include plain weave, sash weave, twill weave, etc., and these known weaves can be appropriately selected and used depending on the intended use and performance. In addition, glass woven fabrics that have been subjected to fiber opening treatment or surface treatment with a silane coupling agent or the like are preferably used. The thickness and mass of the substrate are not particularly limited, but typically, those of about 0.01 to 0.3 mm are preferably used. In particular, from the viewpoint of strength and water absorbency, the substrate should have a thickness of 200 μm or less and a mass of 250 g / m 2 The following glass woven fabrics are preferred, and glass woven fabrics made of glass fibers such as E-glass, S-glass, and T-glass are more preferred.

[0057] (3) Laminated board The prepreg described above can be used to prepare a laminate. According to one embodiment, there is provided a metal foil clad laminate comprising at least one layer formed from the prepreg described above and a metal foil disposed on one or both sides of the layer formed from the prepreg. In the production of a laminate, first, one or more prepregs are stacked, and then a metal foil such as copper foil is stacked on both sides or one side of the prepregs, followed by heating and pressure molding. This molding makes it possible to produce a laminate having metal foil on both sides or one side (e.g., a copper-clad laminate). A printed wiring board can be obtained by patterning and etching the metal foil of this laminate to form a circuit. Also, a multilayered printed wiring board can be produced by stacking multiple prepregs with metal foil having a circuit formed thereon between them, followed by heating and pressure molding.

[0058] The conditions for hot and press molding vary depending on the content ratio of the raw materials of the resin composition according to the present invention, but are generally 170°C to 230°C and a pressure of 1.0 MPa to 6.0 MPa (10 kg / cm 2 More than 60kg / cm 2 It is preferable to apply heat and pressure under the conditions described below for an appropriate period of time. The metal foil used in the laminate may be a copper foil having a surface roughness (ten-point average roughness: Rz) of 10 μm or less, the surface on which the resin layer is formed by the prepreg (the surface in contact with the prepreg) being treated with zinc or a zinc alloy for rust prevention and to improve adhesion with the resin layer, and further treated with a coupling agent such as a vinyl group-containing silane coupling agent. Such copper foil has good adhesion with the resin layer (insulating layer), and a printed wiring board having excellent high-frequency characteristics can be obtained. When the copper foil is treated with zinc or a zinc alloy, zinc or a zinc alloy can be formed on the surface of the copper foil by plating. The laminates and printed wiring boards thus obtained have favorable properties such as low dielectric constant and low dielectric loss tangent. In addition, laminates and printed wiring boards having moldability, water resistance, moisture resistance, moisture absorption and heat resistance, and high glass transition points can be obtained. In particular, when the minimum melt viscosity of the prepreg is 10,000 Pa s or less, good moldability can be obtained. EXAMPLES

[0059] The present invention will be described in detail below with reference to examples, but the content of the present invention is not limited thereto. The materials used in the following examples and comparative examples are as follows. Polyphenylene ether compound (1): OPE-2St2200 / toluene solution (manufactured by Mitsubishi Gas Chemical Company, solid content 63%, number average molecular weight (Mn): 2,200) Polyphenylene ether compound (2): Noryl (trademark) SA9000 (manufactured by Savic Innovative Plastics) Maleimide compound (1): BMI-70 (K.I. Chemical Co., Ltd.) Maleimide compound (2): BMI-80 (K.I. Chemical Co., Ltd.) Maleimide compound (3): MIR-3000-70MT (manufactured by Nippon Kayaku Co., Ltd.) Maleimide compound (4): BMI-1000 (Daiwa Chemical Industry Co., Ltd.) (Meth)allyl isocyanurate compound: TAICROS (registered trademark) (manufactured by Evonik Japan Co., Ltd.)

[0060] (Examples 1 to 3, 6 to 14) The materials and amounts thereof used in each example are as shown in Tables 1 and 2 below. A maleimide compound, a cycloketone solvent, and an amide solvent were charged into a 100 mL glass vial and stirred at 25°C and 1,000 rpm for 30 minutes. Then, a polyphenylene ether compound and an aromatic solvent were charged and stirred at 25°C and 1,000 rpm for 30 minutes to obtain a resin composition. The polyphenylene ether compound (1) used in Example 3 was one that had been powdered by removing the solvent. The maleimide compound (3) (MIR-3000-70MT) was one that had been powdered by removing the solvent.

[0061] (Examples 4 and 5) A maleimide compound, a cycloketone solvent, and an amide solvent were charged into a 100 mL glass vial and stirred at 25°C and 1,000 rpm for 30 minutes. Then, a polyphenylene ether compound and an aromatic solvent were charged into the glass vial and stirred at 25°C and 1,000 rpm for 30 minutes. Furthermore, a (meth)allyl isocyanurate compound (TAICROS) was charged into the glass vial and stirred at 25°C and 1,000 rpm for 30 minutes to obtain a resin composition.

[0062] Comparative Example 1 A maleimide compound and 229 parts by mass of toluene were placed in a 100 mL glass vial and stirred at 1,000 rpm at 25° C. for 30 minutes. Then, a polyphenylene ether compound and 59 parts by mass of toluene were added and stirred at 1,000 rpm at 25° C. for 30 minutes to obtain a resin composition. (Comparative Examples 2 to 4 and 6) A maleimide compound and methyl ethyl ketone were placed in a 100 mL glass vial and stirred at 1,000 rpm at 25° C. for 30 minutes. Then, a polyphenylene ether compound was added and stirred at 1,000 rpm at 25° C. for 30 minutes to obtain a resin composition. The polyphenylene ether compound (1) and the maleimide compound (3) (MIR-3000-70MT) were used after removing the solvent and powdering them.

[0063] Comparative Example 5 A resin composition was prepared in the same manner as in Comparative Example 1, except that the materials listed in the following table were used. When charging the maleimide compound, 461 parts by mass of toluene were charged, and when charging the polyphenylene ether compound (1), 59 parts by mass of toluene were charged. The maleimide compound (3) (MIR-3000-70MT) was used after removing the solvent and powdering it. (Comparative Examples 7 to 9) Except for using the solvents shown in the following table, resin compositions were prepared in the same manner as in Example 1. When methyl ethyl ketone was used, it was added at the same time as the maleimide compound was added. (Comparative Examples 10 to 12) Except for using the solvents shown in the following table, resin compositions were prepared in the same manner as in Example 4. When methyl ethyl ketone was used, the methyl ethyl ketone was also added at the same time as the maleimide compound was added.

[0064] The resin compositions obtained in the Examples and Comparative Examples were allowed to stand for 10 minutes after stirring, and then visually inspected for the presence or absence of solid matter. [Evaluation Criteria] No solids: A Solids included: B The results are shown in the following Tables 1 to 4. In Tables 1 to 4, the values ​​relating to the amount of each component are in "parts by mass." [Table 1] [Table 2] [Table 3] [Table 4]

[0065] From the results of Tables 1 to 4, it can be seen that homogeneous resin compositions without solid content were obtained in the examples. Therefore, when a molded body is formed using the resin composition according to the examples, a molded body with excellent appearance can be obtained, and even when a prepreg is produced, a defect called "cissing" is suppressed. Since the resin composition containing the polyphenylene ether compound and the maleimide compound has excellent electrical properties and heat resistance, the member using the resin composition according to the examples can be suitably used in electronic devices, communication devices, etc.

Claims

1. 100 parts by mass of a polyphenylene ether compound having a terminal carbon-carbon double bond; 30 to 300 parts by mass of a maleimide compound; 10 to 160 parts by mass of an aromatic organic solvent; 10 to 500 parts by mass of a cycloketone; 10 to 310 parts by mass of an amide solvent; A resin composition comprising:

2. The resin composition according to claim 1, wherein (total parts by mass of aromatic organic solvent + cycloketone + amide solvent) / (total parts by mass of polyphenylene ether compound + maleimide compound) = 0.65 to 9.

7.

3. The resin composition according to claim 1, wherein cycloketone (parts by mass) / maleimide compound (parts by mass) = 0.2 to 8.0, and amide solvent (parts by mass) / maleimide compound (parts by mass) = 0.2 to 4.

0.

4. The resin composition according to claim 1, wherein the polyphenylene ether compound has a structure represented by the following general formula (1): 【Chemistry 1】 [In formula (1), X represents a group containing an aromatic ring; -(Y-O) ｎ１ - represents a polyphenylene ether structure which may have a substituent; n1 represents an integer from 1 to 100; n2 represents an integer of 1 to 4; Rx is a group represented by the following formula (Rx-1) or formula (Rx-2); 【Chemistry 2】 In formula (Rx-1) and formula (Rx-2), R １ , R ２ , R ３ , R ４ , R ５ , and R ６ are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, and an alkynyl group, each of which may have a substituent; * is the bonding site for the oxygen atom; Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent; z represents an integer of 0 to 4; and r represents an integer of 1 to 4.

5. The resin composition according to claim 1, wherein the polyphenylene ether compound has a number average molecular weight (Mn) of 500 to 5,000.

6. The resin composition according to claim 1 , wherein the maleimide compound is a compound having two or more maleimide groups.

7. The resin composition according to claim 1, wherein the maleimide compound has a structure represented by the following general formula (M-1): 【Chemistry 3】 [In formula (M-1), Z is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR ２１ -, -C(=O)-, -C(=O)-O-, -C(=O)NR ２１ -, a divalent group derived from indan, a group represented by formula (m1), and combinations thereof, each of which may have a substituent (wherein R ２１ is a hydrogen atom or a methyl group). 【Chemistry 4】

8. The resin composition according to claim 1, wherein the maleimide compound has a structure represented by the following general formula (M-2): 【Chemistry 5】 [In formula (M-2), W is a divalent linking group, and the divalent linking group is an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, -O-, -S-, -NR ２１ -, -C(=O)-, -C(=O)-O-, -C(=O)NR ２１ -, a divalent group derived from indane, and combinations thereof, each of which may have a substituent (wherein R ２１ is a hydrogen atom or a methyl group; each t is independently selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxyl group, a cycloalkoxyl group, a maleimide group, a hydroxyl group, an aryl group, an aryloxy group, an allyl ether group, a 2-propenyl group, and combinations thereof, each of which may have a substituent; and m is independently an integer of 0 to 4.

9. The resin composition according to claim 1 , wherein the cycloketone is selected from the group consisting of cyclohexanone, cyclopentanone and cycloheptanone.

10. The resin composition according to claim 1, wherein the amide solvent is selected from the group consisting of N,N-dimethylacetamide, N,N-dimethylformamide, and N-methyl-2-pyrrolidinone.

11. The resin composition of claim 1 further comprising a crosslinking agent.

12. The resin composition according to claim 11, wherein the crosslinking agent is selected from the group consisting of an alkenyl isocyanurate compound, a (meth)allyl isocyanurate compound, a tri(meth)allyl cyanurate compound, a polyfunctional methacrylate compound, a polyfunctional acrylate compound, a polyfunctional vinyl compound, a polyfunctional vinylphenyl group compound, a styrene derivative, and a polyfunctional isocyanate compound.

13. A prepreg produced using a substrate and the resin composition according to any one of claims 1 to 12.

14. 14. A metal foil clad laminate comprising at least one layer formed from the prepreg of claim 13 and metal foil disposed on one or both sides of the layer formed from the prepreg.

15. mixing a maleimide compound, a cycloketone, and an amide solvent to obtain a mixture; Next, a polyphenylene ether compound having a terminal carbon-carbon double bond and an aromatic organic solvent are added to the mixture and mixed. Including, For 100 parts by mass of the polyphenylene ether compound, 30 to 300 parts by mass of the maleimide compound, 10 to 160 parts by mass of the aromatic organic solvent, 10 to 500 parts by mass of the cycloketone, and 10 to 310 parts by mass of the amide solvent are added. A method for producing a resin composition.

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