Resin compositions, cured products, resin composite sheets, prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices.

Abstract

To provide a resin composition that can improve fluidity during molding while achieving low dielectric properties when cured. To provide cured products, resin composite sheets, prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices. [Solution] The resin composition according to the present disclosure is a resin composition comprising a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and a compound represented by formula (B), wherein the content of the compound represented by formula (B) is 1.0 to 15 parts by mass per 100 parts by mass of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus. In formula (B), R 1 L is a group that has a carbon-carbon unsaturated double bond at its terminal end. L is a linking group that has one or two atoms connecting a single bond or two benzene rings. TIFF0007887007000060.tif47170

Description

[Technical Field]

[0001] The present invention relates to resin compositions, cured products, resin composite sheets, prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices. [Background technology]

[0002] Phenylene ether resins possess excellent dielectric properties, heat resistance, flame retardancy, toughness, processability, and low water absorption, making them widely used in various industrial fields such as electrical and electronics and automotive, for applications including molding, bonding, and painting. In particular, in the electrical and electronic fields, as the operating frequency band increases, there is an ever-growing demand for substrate materials in printed circuit boards used in various electronic devices that possess increasingly superior dielectric properties.

[0003] For example, Patent Document 1 describes a phenylene ether resin composition having a number average molecular weight (Mn) of 800 to 3,000, comprising a resin α represented by the following general formula (1) and a resin β represented by the following general formula (2), characterized in that the content of resin β relative to resin α (content of resin β / content of resin α) is 20 to 200 ppm. General formula (1) [ka] [In general formula (1), A represents a single bond or a linear, branched, or cyclic hydrocarbon having 10 or fewer carbon atoms. Z1 and Z2 may be the same or different, and represent a unit containing a hydrogen atom or a polymerizable double bond group. R1~R 16 R1~R 16 At least one of them represents a methyl group. General formula (2) [ka] [In general formula (2), A, Z1, Z2, R1~R 16 m and n are the same as in general formula (1) above. L1 to L8 may be the same or different, and are represented by a hydrogen atom, a halogen atom, a linear, branched, or cyclic alkyl group having 6 or fewer carbon atoms, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group, a substituted aryl group, or the following general formula (3). At least one of L1 to L8 is represented by the following general formula (3). General formula (3) [ka] [In general formula (3), X is selected from the group consisting of a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 6 or fewer carbon atoms, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group, and a substituted aryl group. * represents a bond.] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2024 / 024730 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] As mentioned above, polyphenylene ether resins are known to exhibit excellent low dielectric properties (especially low dielectric loss tangent) when cured. However, even polyphenylene ether resins that exhibit low dielectric properties have limited applications if their processability, particularly their fluidity during molding, is poor. The present invention aims to solve these problems and provides a resin composition that can improve fluidity during molding while achieving low dielectric properties when cured. Furthermore, the objective is to provide cured products, resin composite sheets, prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices using the aforementioned resin composition. [Means for solving the problem]

[0006] Based on the above problems, the inventors conducted research and found that the above problems can be solved by blending a predetermined low-molecular-weight compound with a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminal. Specifically, the above problem was solved by the following means. [1] A resin composition comprising a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and a compound represented by formula (B), A resin composition in which the content of the compound represented by formula (B) is 1.0 to 15 parts by mass per 100 parts by mass of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus. [ka] (In formula (B), R 1 R is a group having a carbon-carbon unsaturated double bond at its terminal end. 2 and R 3 Each of the following is independently an alkyl group or phenyl group having 1 to 3 carbon atoms; m1 and m2 are independently integers from 0 to 4; and m3 and m4 are either 0 or 1, except that neither m3 nor m4 can be 1. m5 is either 0 or 1, except that if m5 is 0, then m3 is 1. L is a linking group with one or two atoms connecting a single bond or two benzene rings. [2] The resin composition according to [1], wherein in formula (B), L is a single bond, a methylene group, an ether group, or a group consisting of a combination of a methylene group and an ether group. [3] The resin composition according to [1], wherein the compound represented by formula (B) comprises the compound represented by formula (B1). [ka] (In formula (B1), R 1is a group having a carbon-carbon unsaturated double bond at the terminal, Me is a methyl group, m1 and m2 are each independently an integer of 0 to 4, m3 and m4 are 0 or 1. However, neither m3 nor m4 can be 1. m5 is 0 or 1. However, when m5 is 0, m3 is 1. L 1 is a group consisting of a single bond, a methylene group, an ether group, or a combination of a methylene group and an ether group. ) [4] The resin composition according to [1], wherein the compound represented by the formula (B) contains at least one of the compounds shown below. [Chemical formula] [5] The resin composition according to any one of [1] to [4], wherein the number average molecular weight of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at the terminal is 500 to 3000. [6] In the formula (B), R 1 is a vinyl group, a (meth)allyl group, or a (meth)acryloyl group, and the resin composition according to any one of [1] to [5]. [7] The resin composition according to any one of [1] to [6], wherein the molecular weight of the compound represented by the formula (B) is 150 to 400. [8] The resin composition according to any one of [1] to [7], wherein the polyphenylene ether resin having a carbon-carbon unsaturated double bond at the terminal contains a compound represented by the formula (OP). [Chemical formula] (In the formula (OP), X represents an aromatic group, -(Y - O) n1 - represents a polyphenylene ether structure, n1 represents an integer of 1 to hundred, and n2 represents an integer of 1 to 4. Rx is a group represented by the formula (Rx-1) or the formula (Rx-2). ) [Chemical formula] (In the formula (Rx-1) and the formula (Rx-2), R 1 , R 2 , and R 3Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bond site with the oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6. [9] The resin composition according to any one of [1] to [8], wherein the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus comprises a compound represented by formula (OP-1). [ka] (In formula (OP-1), X represents an aromatic group, -(YO)n2- represents a polyphenylene ether structure, R 1 , R 2 , and, R 3 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, where n1 represents an integer from 0 to 6, n2 represents an integer from 1 to 100, and n3 represents an integer from 1 to 4.

[10] The resin composition according to any one of [1] to [9], wherein the total content of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and the compound represented by formula (B) in the resin composition is 90 to 100% by mass of the resin solids contained in the resin composition.

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

[10] , wherein the compound represented by formula (B) is the compound described below. [ka]

[12] The polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus has a number-average molecular weight of 500 to 3000. The polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus contains a compound represented by formula (OP-1), The total content of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and the compound represented by formula (B) in the resin composition is 90 to 100% by mass of the resin solids contained in the resin composition. The compound represented by formula (B) includes the following compounds: A resin composition according to any one of [1] to

[11] . [ka] (In formula (OP-1), X represents an aromatic group, -(YO)n2- represents a polyphenylene ether structure, R 1 , R 2 , and, R 3 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, where n1 represents an integer from 0 to 6, n2 represents an integer from 1 to 100, and n3 represents an integer from 1 to 4. [ka] A cured product of any one of the resin compositions described in

[13] [1] to

[12] .

[14] A resin composite sheet comprising a support and a layer formed from any one of the resin compositions described in [1] to

[12] disposed on the surface of the support.

[15] A prepreg formed from a substrate and a resin composition described in any one of [1] to

[12] .

[16] A metal foil-clad laminate comprising at least one prepreg described in

[15] and a metal foil disposed on one or both sides of the prepreg.

[17] A printed circuit board comprising an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from any one of the resin compositions described in [1] to

[12] . A semiconductor device including a printed circuit board as described in

[18]

[17] . [Effects of the Invention]

[0007] The present invention makes it possible to provide a resin composition that can improve fluidity during molding while achieving low dielectric strength when cured, as well as cured products, resin composite sheets, prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices using the resin composition. [Modes for carrying out the invention]

[0008] The following describes in detail embodiments for carrying out the present invention (hereinafter simply referred to as "this embodiment"). Note that the following embodiment is illustrative for explaining the present invention, and the present invention is not limited to this embodiment. In this specification, "~" is used to mean that the numerical values ​​before and after it are included as the lower and upper limits. Furthermore, the upper and lower limits of the numerical values ​​in this specification are given as examples of this embodiment, regardless of the combination of upper and lower limits. In this specification, a preferred combination of embodiments is a more preferred embodiment. In this specification, all physical properties and characteristic values ​​shall be those at 23°C unless otherwise specified. In this specification, when groups (atomic groups) are not specified as substituted or unsubstituted, the notation includes both groups (atomic groups) with and without substituents. For example, "alkyl group" includes not only unsubstituted alkyl groups but also substituted alkyl groups. In this specification, when notation is not specified as substituted or unsubstituted, unsubstituted is preferred. Examples of substituents in this specification are preferably halogen atoms, cyano groups, nitro groups, hydroxyl groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclic oxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, acyl groups, or amino groups; more preferably halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, alkenyl groups, or acyl groups; even more preferably alkyl groups, aryl groups, aryloxy groups, or alkenyl groups; and even more preferably alkyl groups. The formula weight of these substituents is preferably 15 or more, and preferably 200 or less. For example, the formula weight of a methyl group (-CH3) is 15. These substituents may have further substituents, but it is preferable that they have no substituents.

[0009] In this specification, "(meth)allyl" refers to both allyl and methallyl, or either of them; "(meth)acrylate" refers to both acrylate and methacrylate, or either of them; "(meth)acrylic" refers to both acrylic and methacrylic, or either of them; and "(meth)acryloyl" refers to both acryloyl and methacryloyl, or either of them.

[0010] In this specification, relative permittivity refers to the ratio of the permittivity of a material to the permittivity of a vacuum. Furthermore, in this specification, relative permittivity may be simply referred to as "permittivity." In addition, unless otherwise specified, relative permittivity in this specification refers to the relative permittivity at a frequency of 10 GHz measured according to the cavity resonator perturbation method.

[0011] In this specification, resin solids refer to components other than fillers and solvents, and include thermosetting resins, crosslinking agents, and elastomers, dispersants, flame retardants, silane coupling agents, curing accelerators, etc. If the measurement methods, etc., described in the standards shown in this specification differ from year to year, unless otherwise specified, the standards as of January 1, 2025 shall apply. If the measurement methods, etc., described in the standards shown in this specification are obsolete as of January 1, 2025, the standards in effect at the time of obsolete shall apply.

[0012] The resin composition of this embodiment is a resin composition comprising a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and a compound represented by formula (B), characterized in that the content of the compound represented by formula (B) is 1.0 to 15 parts by mass per 100 parts by mass of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus. [ka] (In formula (B), R 1 R is a group having a carbon-carbon unsaturated double bond at its terminal end. 2 and R 3Each of the following is independently an alkyl group or phenyl group having 1 to 3 carbon atoms; m1 and m2 are independently integers from 0 to 4; and m3 and m4 are either 0 or 1, except that neither m3 nor m4 can be 1. m5 is either 0 or 1, except that if m5 is 0, then m3 is 1. L is a linking group with one or two atoms connecting a single bond or two benzene rings.

[0013] This configuration allows for low dielectric properties in the cured product while improving the fluidity of the resin composition during molding. The superior fluidity makes it possible to provide a resin composition with improved overall processability.

[0014] The fluidity of the resin composition is achieved by adding components with a small molecular weight, such as the compound represented by formula (B). However, components with a small molecular weight tend to volatilize during solvent removal or molding. Therefore, in this embodiment, a compound having a predetermined structure and containing a group having a carbon-carbon unsaturated double bond at its terminus, such as a vinyl group (a compound represented by formula (B)), was blended into a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus. The carbon-carbon unsaturated double bond of the compound represented by formula (B) acts as a reaction site with the polyphenylene ether resin, and it is presumed that this effectively suppressed the volatilization of the compound represented by formula (B) during molding. Furthermore, in this embodiment, by employing a compound with a larger molecular weight than styrene, it is presumed that volatilization under vacuum was less likely to occur, effectively suppressing volatilization from the resin composition during curing and the formation of voids in the molded product. On the other hand, if there are two or more reaction sites, as with divinylbenzene, the crosslinking density of the composition tends to increase when heated above a certain temperature, leading to a faster thickening rate and thus poor fluidity. In this embodiment, it is presumed that this issue was avoided by employing a compound having one group with a carbon-carbon unsaturated double bond at its terminal end.

[0015] Furthermore, in this embodiment, the compound represented by formula (B) has a rigid structure in which benzene rings are bonded at a relatively short distance, and it is presumed that this rigid structure enabled the achievement of low dielectric properties. Moreover, unlike phenol and the like, the compound represented by formula (B) does not have hydroxyl groups at its terminals, which is presumed to have effectively suppressed the increase in dielectric properties. As a result of thorough investigation into the above points, we obtained a resin composition that maintains low dielectric properties when cured while exhibiting excellent fluidity.

[0016] The embodiments of the present invention will be described in detail below, but the description of the constituent elements described below is just one example of an embodiment of the present invention and is not limited to these.

[0017] <Polyphenylene ether resin with carbon-carbon unsaturated double bonds at its terminus> The resin composition of this embodiment contains a polyphenylene ether resin having carbon-carbon unsaturated double bonds at its terminals, and more preferably contains a polyphenylene ether resin having carbon-carbon unsaturated double bonds at both terminals. Polyphenylene ether resins having carbon-carbon unsaturated double bonds at their terminals preferably include polyphenylene ether resins having two or more groups represented by formula (Rx-1), described later (preferably vinylbenzyl groups), at their terminals. Using these polyphenylene ether resins tends to more effectively improve low dielectric properties (Dk and / or Df, especially Df) and low water absorption of printed circuit boards and the like. The following details will explain these points.

[0018] Examples of polyphenylene ether resins having a carbon-carbon unsaturated double bond at the terminal include compounds having a phenylene ether skeleton represented by the following formula (X1).

[0019] [ka] (In formula (X1), R 24 , R25 , R 26 , and, R 27 (These may be the same or different characters, and represent an alkyl group, aryl group, halogen atom, or hydrogen atom having 6 or fewer carbon atoms.)

[0020] Polyphenylene ether resins having carbon-carbon unsaturated double bonds at their terminals are given by formula (X2): [ka] (In formula (X2), R 28 , R 29 , R 30 , R 34 , and, R 35 R may be the same or different, and represents an alkyl group or phenyl group having 6 or fewer carbon atoms. 31 , R 32 , and, R 33 (These may be the same or different atoms, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) The repeating unit represented by and / or formula (X3): [ka] (In formula (X3), R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , and, R 43 ) may be the same or different, and is a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. -A- is a straight, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms. The repeating unit represented by ) may further be included.

[0021] The polyphenylene ether resin having a carbon-carbon unsaturated double bond at the terminal is preferably a modified polyphenylene ether resin (hereinafter sometimes referred to as "modified polyphenylene ether resin (g)") in which part or all of the terminal is functionalized with ethylenically unsaturated groups, and more preferably a modified polyphenylene ether resin having two or more vinylbenzyl groups at the terminal. By using such a modified polyphenylene ether resin (g), it is possible to reduce the dielectric loss tangent (Df) of the cured resin composition and to improve water absorption and peel strength. These modified polyphenylene ether resins (g) may be used individually or in combination of two or more.

[0022] Examples of modified polyphenylene ether resins (g) include polyphenylene ether resins represented by formula (OP). [ka] (In formula (OP), X represents an aromatic group, and -(YO) n1 The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). [ka] (In equations (Rx-1) and (Rx-2), R 1 , R 2 , and, R 3 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bond site with the oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0023] The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above is an example, but it is preferable that it is at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Furthermore, the polyphenylene ether structure represented by -(YO)n1- may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. If n1 and / or n2 are integers greater than or equal to 2, the n1 constituent units (YO) and / or the n2 constituent units may be identical or different. n2 is preferably greater than or equal to 2, and more preferably 2.

[0024] In formula (OP), Rx is preferably expressed as (Rx-1). In equations (Rx-1) and (Rx-2), R 1 , R 2 , and, R 3 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. R 1 A hydrogen atom or an alkyl group is preferred, a hydrogen atom or a methyl group is more preferred, and a hydrogen atom is even more preferred. R 2 and R 3 Each of these is independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. R 1 , R 2 , and, R 3 The number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0025] In equation (Rx-1), r represents an integer between 0 and 6, and may be an integer greater than or equal to 1. It is preferably an integer less than or equal to 5, more preferably an integer less than or equal to 4, even more preferably an integer less than or equal to 3, even more preferably 1 or 2, and even more preferably 1.

[0026] In formula (Rx-1), Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In equation (Rx-1), z represents an integer between 0 and 4, preferably between 0 and 3, more preferably between 0 and 2, even more preferably 0 or 1, and even more preferably 0.

[0027] A specific example of the group represented by formula (Rx-1) is the vinylbenzyl group.

[0028] Examples of modified polyphenylene ether resins (g) include compounds represented by formula (OP-1). [ka] (In formula (OP-1), X represents an aromatic group, -(YO)n2- represents a polyphenylene ether structure, R 1 , R 2 , and, R 3 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, where n1 represents an integer from 0 to 6, n2 represents an integer from 1 to 100, and n3 represents an integer from 1 to 4. The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above is an example, but it is preferable that it is at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Furthermore, the polyphenylene ether structure represented by -(YO)n2- may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. If n2 and / or n3 are integers greater than or equal to 2, the n2 constituent units (YO) and / or the n3 constituent units may be identical or different. n3 is preferably greater than or equal to 2, and more preferably 2.

[0029] In this embodiment, the modified polyphenylene ether resin (g) is preferably a compound represented by formula (OP-2). [ka] Here, -(OXO)- is given by equation (OP-3): [ka] (In equation (OP-3), R 4 , R 5 , R 6 , R 9 , R 10 , and, R 11 These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. 7 , and, R 9 (These may be the same or different atoms, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) and / or formula (OP-4): [ka] (In formula (OP-4), R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and, R 19 ) may be the same or different, and is a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. -A- is a straight, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms. ) is preferably represented as ).

[0030] Also, -(YO)- is given by equation (OP-5): [ka] (In formula (OP-5), R 20 , R 21 These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. 22 , R 23 These may be the same or different, and are preferably a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. Especially R 20 and R 21 Each of these groups independently has one or more methyl and / or cyclohexyl groups. This increases the rigidity of the resulting resin molecule. Since molecules with high rigidity have lower mobility than molecules with low rigidity, the relaxation time during dielectric relaxation is longer, resulting in excellent low dielectric properties (Dk and / or Df, especially Dk), which is therefore preferable. An example of formula (OP-5) is shown below. [ka] For polyphenylene ether resins having the above structure, please refer to the description in Japanese Patent Application Publication No. 2019-194312, which is incorporated herein by reference.

[0031] In formula (OP-2), 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 each independently are integers from 0 to 50, more preferably integers from 1 to 30, and still more preferably integers from 1 to 10. When a and / or b is an integer of 2 or more, two or more -(Y-O)- may each independently be an arrangement of one kind of structure, or two or more kinds of structures may be arranged in blocks or randomly. Further, when a plurality of compounds represented by formula (OP-2) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0032] Examples of -A- in formula (OP-4) 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 thereto.

[0033] Among the compounds represented by the above formula (OP-2), R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are alkyl groups having 3 or fewer carbon atoms, and R 7 , R 8 , R 22 , and R 23A polyphenylene ether resin in which is a hydrogen atom or an alkyl group having 3 or fewer carbon atoms is preferred, and in particular, it is preferred that the -(OXO)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and the -(YO)- represented by formula (OP-5) is formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the 2 or more -(YO)- may each be independently a structure in which two or more of formula (OP-12) and / or formula (OP-13) are arranged, or a structure in which formula (OP-12) and formula (OP-13) are arranged in a block or randomly.

[0034] [ka] [ka] (In formula (OP-10), R 44 , R 45 , R 46 , and, R 47 (These may be the same or different atoms, and are either a hydrogen atom or a methyl group.) (-B- is a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.) -B- is the same as the specific example of -A- in equation (OP-4). [ka] (In formula (OP-11), -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.) -B- is the same as the specific example of -A- in equation (OP-4). [ka] [ka]

[0035] The modified polyphenylene ether resin (g) is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and more preferably a compound represented by formula (OP-15). [ka] (In equation (OP-14), a and b each independently represent integers between 0 and 100, and at least one of a and b is an integer between 1 and 100.) In formula (OP-14), a and b are independently equivalent to a and b in formula (OP-2), and the preferred ranges are also similar. [ka] (In equation (OP-15), a and b each independently represent integers between 0 and 100, and at least one of a and b is an integer between 1 and 100.) In formula (OP-15), a and b are independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same.

[0036] Furthermore, the polyphenylene ether resin used in this embodiment may also be a compound represented by formula (OP-16). [ka] (In equation (OP-16), a and b each independently represent integers between 0 and 100, and at least one of the two as and bs is an integer between 1 and 100.)

[0037] Polyphenylene ether resins having carbon-carbon unsaturated double bonds at the ends may be manufactured by known methods or commercially available products may be used. Examples of commercially available products include "OPE-2St1200" and "OPE-2St2200" from Mitsubishi Gas Chemical Company, which are modified polyphenylene ether resins with vinyl benzyl groups at the ends. Alternatively, as modified polyphenylene ether resins with vinyl benzyl groups at the ends, such as "SA9000" from SABIC Innovative Plastics, can be used, which are polyphenylene ether resins with hydroxyl groups at the ends that have been modified to vinyl benzyl groups using vinyl benzyl chloride or the like.

[0038] Further details regarding polyphenylene ether resins having carbon-carbon unsaturated double bonds at their terminals can be found in Japanese Patent Publication No. 2006-028111, Japanese Patent Publication No. 2018-131519, International Publication No. 2019-138992, and International Publication No. 2022-054303, the contents of which are incorporated herein by reference.

[0039] The number-average molecular weight (in polystyrene terms) of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at the terminal (preferably, modified polyphenylene ether resin (g)) as determined by GPC (gel permeation chromatography) (details are as described in the examples below) is preferably 500 to 3000. A number-average molecular weight of 500 or more tends to further suppress stickiness when the resin composition of this embodiment is formed into a coating film. Furthermore, a number-average molecular weight of 3,000 or less tends to further improve solubility in solvents. Furthermore, the weight-average molecular weight of the polystyrene-based polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus (preferably modified polyphenylene ether resin (g)) calculated by GPC (details are as described in the examples below) is preferably 800 or more, more preferably 1000 or more, and depending on the application, it may be 1500 or more, 1800 or more, or 2000 or more, and preferably 2800 or less, and depending on the application, it may be 2000 or less, 1800 or less, or 1500 or less. When the weight-average molecular weight is above the lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, viscosity, and moldability of the resin composition when producing varnishes, etc., as described later tend to be improved.

[0040] Furthermore, for polyphenylene ether resins having carbon-carbon unsaturated double bonds at their terminals (preferably modified polyphenylene ether resins (g)), the equivalent amount of the terminal carbon-carbon unsaturated double bonds is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, and more preferably 400 to 2500 g. When the equivalent amount of the terminal carbon-carbon unsaturated double bonds is above the lower limit, the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, viscosity, and moldability of the resin composition tend to be improved.

[0041] The functional group equivalent (carbon-carbon unsaturated double bond equivalent) of a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus is calculated by determining the amount of double bonds from the measurement results using an infrared spectrometer and then taking the reciprocal of that amount. The double bond equivalent [g / eq.] was determined as follows. The weight of the polyphenylene ether resin powder is weighed and recorded. This powder is placed in a volumetric flask, and the measurement sample is prepared by making up the volume with carbon disulfide. This sample solution is placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Then, infrared spectroscopy of the sample solution is performed. For vinyl groups in polyphenylene ether resin, the reading is 905 cm⁻¹. -1 Record the peak area of ​​the spectrum in the vicinity. When the carbon-carbon unsaturated double bond is a methacrylic group, the peak area is 1640 cm⁻¹. -1 The peak area of ​​the spectrum in the vicinity is recorded. From this area value and the calibration curve, the double bond concentration [mol / L] is determined as a measured value. Next, the double bond equivalent is calculated using the following formula. Double bond equivalent [g / eq.] = Weight of powder in the sample [g] / Double bond concentration [mol / L] × Volume of sample liquid [L] The functional group equivalents of thermosetting compounds other than polyphenylene ether resins having carbon-carbon unsaturated double bonds at their terminals can also be measured following the method described above. However, for compounds (monomers) that can be expressed by a single molecular weight, the value obtained by (theoretical molecular weight ÷ number of functional groups) shall be given priority. If two or more other thermosetting compounds are included, the functional group equivalents of the other thermosetting compounds shall be the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalents of each other thermosetting compound by their mass fraction.

[0042] The content of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus in the resin composition of this embodiment is preferably 1 part by mass or more, more preferably 10 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 80 parts by mass or more, and preferably 99 parts by mass or more, per 100 parts by mass of the resin solids in the resin composition. The resin composition in this embodiment may contain only one polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range. In particular, resin compositions in which the content of polyphenylene ether resin having a carbon-carbon unsaturated double bond at the terminal is 85% by mass or more, preferably 90% by mass or more, of the resin composition can be preferably used as a substitute for known polyphenylene ether resins.

[0043] <Compound represented by formula (B)> The resin composition of this embodiment contains a compound represented by formula (B). By including such a compound, a resin composition with excellent fluidity can be obtained while maintaining low dielectric properties of the resulting cured product. [ka] (In formula (B), R 1R is a group having a carbon-carbon unsaturated double bond at its terminal end. 2 and R 3 Each of the following is independently an alkyl group or phenyl group having 1 to 3 carbon atoms; m1 and m2 are independently integers from 0 to 4; and m3 and m4 are either 0 or 1, except that neither m3 nor m4 can be 1. m5 is either 0 or 1, except that if m5 is 0, then m3 is 1. L is a linking group with one or two atoms connecting a single bond or two benzene rings.

[0044] In formula (B), R 1 The group is a group having a carbon-carbon unsaturated double bond at its terminal end, and is preferably a vinyl group, a (meth)allyl group, or a (meth)acryloyl group, more preferably a (meth)allyl group or a vinyl group, and even more preferably a vinyl group.

[0045] In formula (B), R 2 and R 3 Each of these is independently an alkyl group having 1 to 3 carbon atoms or a phenyl group, with alkyl groups having 1 to 3 carbon atoms being preferred, and methyl groups being more preferred. In equation (B), m1 and m2 are independent integers between 0 and 4, and m3 and m4 are either 0 or 1, except that neither m3 nor m4 can be 1. m5 is either 0 or 1, except that if m5 is 0, then m3 is 1.

[0046] For example, in equation (B), if m3 is 0, m4 is 1, and m5 is 1, the structure will be as follows. [ka] Furthermore, for example, in equation (B), if m3 is 1 and m5 is 0, the structure will be as follows. [ka] Furthermore, for example, in equation (B), if m3 is 0, m4 is 0, and m5 is 1, the structure will be as follows. [ka] In this embodiment, it is preferable that in formula (B), m3 is 0, m4 is 0, and m5 is 1.

[0047] In formula (B), L is a linking group that has one or two atoms connecting a single bond or two benzene rings. The number of atoms connecting two benzene rings is, for example, in the compound below, L is -CH2-C(CH3)H-, and the atoms connecting the two benzene rings are carbon 1 and carbon 2, so the number is 2. In this way, by creating a rigid structure in the compound represented by formula (B) in which the benzene rings are bonded over a relatively short distance, a low dielectric constant of the resulting cured product can be achieved. It goes without saying that one of the two benzene rings may be the benzene ring portion included in the naphthalene ring. Furthermore, equation (B) can be expressed as shown below, for example, R 1 It is preferable that it is bonded to L in a para position. [ka]

[0048] In formula (B), L is preferably a single bond, a methylene group, an ether group, or a group consisting of a combination of a methylene group and an ether group, and more preferably -CH2-O-.

[0049] The compound represented by formula (B) preferably includes the compound represented by formula (B1). [ka] (In formula (B1), R 1 L is a group having a carbon-carbon unsaturated double bond at its terminal end, Me is a methyl group, m1 and m2 are independently integers from 0 to 4, and m3 and m4 are either 0 or 1. However, neither m3 nor m4 can be 1. m5 is either 0 or 1. However, if m5 is 0, then m3 is 1. 1(A group consists of a single bond, a methylene group, an ether group, or a combination of a methylene group and an ether group.)

[0050] In the above formula (B1), R 1 m1, m2, m3, m4, and m5 are R in equation (B), respectively. 1 These are synonymous with m1, m2, m3, m4, and m5, and the preferred range is also the same.

[0051] In this embodiment, the compound represented by formula (B) is preferably composed only of carbon atoms, hydrogen atoms, and optionally selected oxygen atoms. If the compound represented by formula (B) contains oxygen atoms, it is preferable that they are contained only in L of formula (B). By adopting such a configuration, the low dielectric properties of the resulting cured product can be further improved.

[0052] The molecular weight of the compound represented by formula (B) is preferably 150 or more, more preferably 200 or more, preferably 400 or less, more preferably 350 or less, and even more preferably 300 or less. Setting it above the lower limit tends to more effectively suppress volatilization during processing. Furthermore, setting it below the upper limit can further improve the fluidity of the resulting resin composition.

[0053] The following are preferred examples of compounds represented by formula (B) used in this embodiment. It goes without saying that the present invention is not limited to these examples. [ka]

[0054] Furthermore, the following compounds are also preferably used as compounds represented by formula (B). [ka]

[0055] [ka]

[0056] In this embodiment, the compound represented by formula (B) more preferably includes the following compounds. [ka]

[0057] The content of the compound represented by formula (B) in the resin composition of this embodiment is 1.0 part by mass or more, preferably 1.2 parts by mass or more, more preferably 1.3 parts by mass or more, and 15 parts by mass or less, preferably 12 parts by mass or less, even more preferably 10 parts by mass or less, and most preferably 6 parts by mass or less, per 100 parts by mass of polyphenylene ether resin having a terminal carbon-carbon unsaturated double bond. Setting the content above the lower limit tends to further improve the embedding properties of the resin composition. Setting the content below the upper limit tends to further improve the effect of suppressing excessive resin flow. The resin composition of this embodiment may contain only one compound represented by formula (B), or it may contain two or more compounds. When it contains two or more compounds, it is preferable that the total amount is within the above range.

[0058] In this embodiment, the resin composition preferably contains a total amount of polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and the compound represented by formula (B) of 90 to 100% by mass of the resin solids contained in the resin composition, more preferably 95 to 100% by mass, even more preferably 97 to 100% by mass, and may also be 99 to 100% by mass. Such resin compositions can be used as superior alternative materials to known polyphenylene ether resins having carbon-carbon unsaturated double bonds at their ends.

[0059] The resin composition of this embodiment can be composed of low molecular weight compounds that substantially do not contain compounds having two or more carbon-carbon unsaturated double bonds at their ends. Low molecular weight means, for example, a polyfunctional compound with a molecular weight of less than 400, and may even be a compound with a molecular weight of less than 300. For low molecular weight compounds that have two or more carbon-carbon unsaturated double bonds at their ends, the lower limit of the molecular weight is substantially 54 or higher. Furthermore, the resin composition of this embodiment may also be configured to substantially not contain compounds with a molecular weight of less than 150 and which have one carbon-carbon unsaturated double bond at one end. The lower limit of the molecular weight of the said compounds is substantially 28 or higher. "Substantially not containing" means that the content of the relevant compound in the resin composition is less than 1% by mass, and may be less than 0.1% by mass, less than 0.01% by mass, or even 0% by mass. This configuration tends to allow the effects of the present invention to be exhibited more effectively.

[0060] <Other thermosetting resins> Examples of other thermosetting resins include at least one selected from the group consisting of aromatic vinyl resins, maleimide compounds, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane resins, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, compounds having vinylene groups, and resins having an indan skeleton (excluding polyphenylene ether resins having carbon-carbon unsaturated double bonds at the terminals). These details can be found in paragraphs 0020-0047, 0074-0140, and 0147-0155 of International Publication No. 2025 / 115610, and in paragraphs 0013-0059 and 0085-0164 of International Publication No. 2025 / 058029, the contents of which are incorporated herein by reference.

[0061] <Resin additives> The resin composition of this embodiment may contain resin additives. Examples of resin additives include at least one selected from the group consisting of curing accelerators, flame retardants, active ester compounds, dispersants, silane coupling agents, ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, gloss agents, and polymerization inhibitors. These details can be found in paragraphs 0156-0187, 0189, and 0190-0193 of International Publication No. 2025 / 115610 and paragraphs 0176-0209 of International Publication No. 2025 / 058029, the contents of which are incorporated herein by reference. The total amount of the additive is preferably 0 parts by mass or more and less than 5 parts by mass, more preferably 0 parts by mass or more and less than 3 parts by mass, even more preferably 0 parts by mass or more and less than 1 part by mass, and may be 0 parts by mass or more and less than 0.5 parts by mass, per 100 parts by mass of resin solids.

[0062] <Filling material> The resin composition in this embodiment may contain a filler. By including a filler, the properties of the resin composition and its cured product, such as dielectric properties (relative permittivity and / or dielectric loss tangent), flame resistance, and low thermal expansion, can be further improved.

[0063] The type of filler used in this embodiment is not particularly limited, and those commonly used in the industry can be suitably used. Specifically, silica such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, etc.; metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, etc.; composite oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, etc.; nitrides such as boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, etc.; aluminum hydroxide, heat-treated aluminum hydroxide (aluminum hydroxide that has been heat-treated to reduce some of its crystal water), boehmite, magnesium hydroxide, etc. (including hydrates); acid Examples of inorganic fillers include molybdenum compounds such as molybdenum molasses and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (including glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, spherical glass, and organic fillers such as styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell-type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders.

[0064] Further details regarding the filler can be found in paragraphs 0165-0169 of International Publication No. 2025 / 058029, which are incorporated herein by reference.

[0065] The filler content in the resin composition in this embodiment can be appropriately set according to the desired properties and is not particularly limited, but is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and preferably 300 parts by mass or less, and may also be 40 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. Setting it below the above upper limit tends to further improve the moldability of the resin composition. The resin composition in this embodiment may contain only one type of filler, or it may contain two or more types. When it contains two or more types of fillers, it is preferable that the total amount is within the above range.

[0066] <Solvent> The resin composition of this embodiment may contain a solvent, and preferably an organic solvent. When a solvent is included, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the above-mentioned resin solids are dissolved or miscible with the solvent. The solvent is not particularly limited as long as it is a polar or nonpolar organic solvent capable of dissolving or miscible at least a portion, preferably all, of the above-mentioned resin solids. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), cellosolves (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and amides (e.g., dimethoxyacetamide, dimethylformamides, etc.). Examples of nonpolar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). Solvents can be used individually or in combination of two or more. When using two or more solvents, the total amount must be within the above range.

[0067] <Application> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low dielectric constant material and / or a low dielectric loss tangent material, as a resin composition for electronic materials such as insulating layers for printed circuit boards and materials for semiconductor packages. As described above, the resin composition of this embodiment may be a resin composition containing 90% by mass or more of a polyphenylene ether resin having carbon-carbon unsaturated double bonds at its ends and a compound represented by formula (B), or it may be a resin composition containing other thermosetting resins, resin additives, fillers, and solvents. The resin composition of this embodiment can be suitably used as a material for resin composite sheets, prepregs, metal foil-clad laminates, and printed circuit boards.

[0068] The resin composition of this embodiment preferably has a low dielectric loss tangent (Df) of its cured product. Specifically, the resin composition of this embodiment is spread in a 100 mm x 30 mm frame, vacuum pressed, held at 200°C for 1.5 hours, and pressed at a surface pressure of 1.9 MPa. The dielectric loss tangent (Df) of the cured product obtained by this process is preferably 0.0025 or less, more preferably 0.0015 or less, and the lower limit may be 0, but 0.0015 or more is practical. The dielectric loss tangent (Df) of the cured product described above is measured more specifically by the method described in the examples below.

[0069] <<Resin composite sheet>> The resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment disposed on the surface of the support. The resin composite sheet can be used as a build-up film or a dry film solder resist. Resin composite sheets typically do not contain a base material. Here, "base material" refers to the base material described in the prepreg section below.

[0070] Examples of supports used here include, but are not limited to, resin films such as polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, and ethylene tetrafluoroethylene copolymer film, as well as release films obtained by coating the surface of these resin films with a release agent, organic film substrates such as polyimide film, conductive foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, and FRP (Fiber-Reinforced Plastics). One form of the resin composite sheet of this embodiment is a resin composite sheet in which a resin film is provided on one side of a layer formed from the resin composition of this embodiment and a release film is provided on the other side, or a resin composite sheet in which a release film is provided on one side of a layer formed from the resin composition of this embodiment and a metal foil (preferably copper foil) is provided on the other side.

[0071] The method for manufacturing the resin composite sheet is not particularly limited, but one example is to obtain the resin composite sheet by applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent onto a support and drying it. As for the coating method, for example, a solution obtained by dissolving the resin composition of this embodiment in a solvent is applied onto a support using a bar coater, die coater, doctor blade, baker applicator, etc. Alternatively, after drying, the support can be peeled off or etched from the resin composite sheet in which the support and the resin composition are laminated to form a single-layer sheet. Furthermore, a single-layer sheet can also be obtained without using a support by supplying the above-mentioned solution obtained by dissolving the resin composition of this embodiment in a solvent into a mold having a sheet-shaped cavity and drying it to form a sheet.

[0072] In the production of the single-layer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited, but since low temperatures tend to leave solvent residue in the resin composition, and high temperatures cause the resin composition to harden, a temperature of 20°C to 200°C for 1 to 90 minutes is preferred. Furthermore, the single-layer sheet or resin composite sheet can be used in an uncured state after the solvent has been dried, or it can be used in a semi-cured (B-stage) state as needed. In addition, the thickness of the resin layer in the single-layer sheet or resin composite sheet of this embodiment can be adjusted by the concentration of the resin composition solution of this embodiment used for coating and the coating thickness, and is not particularly limited, but generally, a thickness of 0.1 to 500 μm is preferred because a thicker coating thickness tends to leave solvent residue during drying.

[0073] <<Prepreg>> The prepreg of this embodiment is formed from a substrate (prepreg substrate) and the resin composition of this embodiment. The prepreg of this embodiment is obtained, for example, by applying the resin composition of this embodiment to the substrate (e.g., impregnation and / or coating), and then partially curing it by heating (e.g., drying at 120 to 220°C for 2 to 15 minutes). In this case, the amount of resin composition adhering to the substrate, i.e., the amount of resin composition (including hollow silica and filler) relative to the total amount of prepreg after partial curing, is preferably in the range of 20 to 99% by mass, and more preferably in the range of 20 to 80% by mass.

[0074] The substrate is not particularly limited as long as it is a substrate used in various printed circuit board materials. Examples of substrate materials include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, NER-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited and includes woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surfacing mats. These substrates may be used individually or in combination of two or more. Among these substrates, woven fabrics that have undergone ultra-opening treatment and densification treatment are preferred from the viewpoint of dimensional stability, and from the viewpoint of strength and low water absorption, the substrate should have a thickness of 200 μm or less and a mass of 250 g / m². 2 The following glass woven fabrics are preferred, and from the viewpoint of moisture absorption and heat resistance, glass woven fabrics surface-treated with silane coupling agents such as epoxysilane and aminosilane are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers exhibiting low dielectric constant and low dielectric loss tangent, such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. Examples of substrates with low dielectric constant include those with a dielectric constant of 5.0 or less (preferably 3.0 to 4.9). Examples of substrates with low dielectric loss tangent include those with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The dielectric constant and dielectric loss tangent are values ​​measured at a frequency of 10 GHz using a perturbation cavity resonator.

[0075] <<Metal foil-clad laminate>> The metal foil-clad laminate of this embodiment includes the prepreg of this embodiment and metal foil arranged on one or both sides of the prepreg. A method for manufacturing the metal foil-clad laminate of this embodiment includes, for example, arranging at least one sheet of the prepreg of this embodiment (preferably two or more sheets stacked together), and then laminating the metal foil on one or both sides thereof. More specifically, it can be manufactured by laminating the metal foil, such as copper or aluminum, on one or both sides of the prepreg. The number of prepreg sheets is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil is not particularly limited as long as it is used as a material for printed circuit boards, but examples include copper foil such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited and may be about 1.5 to 70 μm. When copper foil is used as the metal foil, it is preferable that the surface roughness Rz of the copper foil, measured according to JIS B0601:2013, is adjusted to 0.2 to 4.0 μm. Setting the surface roughness Rz of the copper foil to 0.2 μm or more results in an appropriate surface roughness, which tends to further improve the copper foil peel strength. On the other hand, setting the surface roughness Rz of the copper foil to 4.0 μm or less results in an appropriate surface roughness, which tends to further improve the dielectric loss tangent properties of the resulting cured product. The surface roughness Rz of the copper foil is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, particularly preferably 0.7 μm or more, more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less, from the viewpoint of the dielectric loss tangent characteristics of the resulting cured product and the copper foil peel strength.

[0076] The lamination method includes methods commonly used when forming laminates and multilayer boards for printed circuit boards. More specifically, it includes a method using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, etc., where lamination is performed at a temperature of approximately 180 to 350°C, a heating time of approximately 100 to 300 minutes, and a surface pressure of approximately 1 to 10 MPa. Furthermore, a multilayer board can be made by laminating the prepreg of this embodiment with a separately manufactured inner layer wiring board. As a method for manufacturing a multilayer board, for example, copper foil of approximately 35 μm is placed on both sides of one prepreg of this embodiment, and after lamination is performed using the above molding method, an inner layer circuit is formed, and this circuit is subjected to a blackening treatment to form an inner layer circuit board. After that, this inner layer circuit board and the prepreg of this embodiment are arranged alternately one by one, and then copper foil is placed as the outermost layer. A multilayer board can be manufactured by lamination under the above conditions, preferably under vacuum. The metal foil-clad laminate of this embodiment can be suitably used as a printed circuit board.

[0077] The metal foil-clad laminate of this embodiment preferably has a peel strength of 0.30 kN / m or more, more preferably 0.35 kN / m or more, and even more preferably 0.50 kN / m or more, measured in accordance with the provisions of JIS C6481 5.7 "Peel Strength". There is no upper limit to the peel strength, but for example, even if it is 2.00 kN / m or less, it will sufficiently satisfy the required performance.

[0078] As described above, the resin composition for electronic materials obtained using the resin composition of this embodiment (a resin composition consisting of a combination of specific components) can have cured products that are excellent in low dielectric properties (low dielectric constant, low dielectric loss tangent, especially low dielectric constant), flame retardancy, and low warping, as well as excellent moisture absorption and heat resistance and heat resistance.

[0079] <<Printed Wiring Board>> The printed circuit board of this embodiment includes an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition of this embodiment and a layer formed from the prepreg of this embodiment. Such a printed circuit board can be manufactured according to conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed circuit board is shown below. First, a metal foil laminate such as the copper foil laminate described above is prepared. Next, an etching treatment is performed on the surface of the metal foil laminate to form an inner layer circuit and produce an inner layer substrate. Surface treatment is performed on the inner layer circuit surface of this inner layer substrate to increase the adhesive strength as needed, and then the required number of prepregs or resin sheets described above are stacked on the inner layer circuit surface, and then metal foil for the outer layer circuit is laminated on the outside thereafter, and the substrate is heated and pressed to form an integral molded product. In this way, a multilayer laminate is produced in which an insulating layer made of a base material and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, after drilling holes for through-holes and via-holes in this multilayer laminate, a plated metal film is formed on the walls of these holes to provide electrical connectivity between the inner layer circuit and the metal foil for the outer layer circuit. Furthermore, the metal foil for the outer layer circuit is etched to form the outer layer circuit, thereby manufacturing a printed circuit board.

[0080] The printed circuit board obtained in the above manufacturing example has an insulating layer and a conductive layer formed on the surface of the insulating layer, wherein the insulating layer contains the resin composition of this embodiment and / or its cured product. That is, the prepreg of this embodiment described above (for example, a prepreg formed from a substrate and the resin composition of this embodiment impregnated or coated thereon), and the layer formed from the resin composition of the metal foil laminate of this embodiment described above, become the insulating layer of this embodiment. Furthermore, this embodiment also relates to a semiconductor device including the printed circuit board. Details of the semiconductor device can be found in paragraphs 0200 to 0202 of Japanese Patent Application Publication No. 2021-021027, and these contents are incorporated herein by reference.

[0081] Furthermore, it is preferable to reduce the surface roughness of the insulating layer formed from the cured resin composition of this embodiment after the roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after the roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but for example, it may be 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x lens. The non-contact surface roughness meter used is the WYKONT3300 manufactured by B-In Instruments. [Examples]

[0082] The present invention will be described in more detail below with reference to examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate, as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments used in the examples are difficult to obtain due to discontinuation or other reasons, measurements can be taken using other instruments with equivalent performance.

[0083] <Measurement of number-average molecular weight and weight-average molecular weight> A high-performance liquid chromatograph, model HLC-8320GPC, manufactured by Tosoh Techno Systems Co., Ltd., was used as the measuring instrument. A calibration curve was prepared using standard polystyrene, and the number-average molecular weight (Mn) and weight-average molecular weight (Mw) of phenylene ether resin were measured using this calibration curve. The standard polystyrene used had molecular weights of 706,000, 96,400, 5,970, 474, 370, and 266. The column consisted of four TSKgel SuperMultiporeHZ-N columns, manufactured by Tosoh Corporation, connected together. Tetrahydrofuran was used as the solvent, with a solvent flow rate of 0.35 mL / min and a column temperature of 40°C. For the measurement sample, 0.02 g of phenylene ether solution was dissolved in 3 g of tetrahydrofuran solution. Detection was performed using the built-in radioisotope detector.

[0084] <Synthesis Example 1: Synthesis of Polyphenylene Ether Resin (i)> (Synthesis of phenylene ether oligomers) The polymerization reaction was carried out using the following procedure. A vertical reactor equipped with a stirring device, thermometer, air inlet pipe and baffle plate 2,2',3,3',5,5'-Hexamethyl-(1,1'-biphenyl)-4,4'-diol 46.21g (171 mmol), 2,6-Dimethylphenol 104.4g (855 mmol), CuBr 21.37g (6.1 mmol), N,N'-di-t-butylethylenediamine 1.59g (9.2 mmol), n-butyldimethylamine 9.26g (92 mmol), 1,000g of toluene, and Methanol 500g The ingredients were prepared and stirred at a reaction temperature of 40°C to dissolve. Then, a mixture of nitrogen and air, adjusted to an oxygen concentration of 8% by volume, was added to the resulting mixed solution and stirred for 230 minutes while bubbling. Next, 580 g of water containing 4.72 g (10 mmol) of tetrasodium ethylenediaminetetraacetate was added to stop the reaction. The aqueous layer and the organic layer were separated, and the organic layer was washed with 670 g of pure water. 1,310 g of a toluene solution of phenylene ether resin was obtained. The number-average molecular weight in polystyrene terms, calculated by GPC, was 950, and the weight-average molecular weight in polystyrene terms, calculated by GPC, was 1,050.

[0085] (Terminal denaturation reaction of phenylene ether oligomers) The terminal denaturation reaction was performed using the following procedure. A reactor equipped with a stirring device, a thermometer and a reflux tubing, 1,300 g of the obtained phenylene ether resin in a toluene solution, Vinyl benzyl chloride (manufactured by AGC Seimi Chemical Co., Ltd., "CMS-P") 58.0g (380 mmol), Tetrabutylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 26g, Benzyldimethylamine 6.20g (0.046mol), 117 g of 48% by mass sodium hydroxide aqueous solution, 180g of purified water, and 70g of toluene The mixture was prepared and stirred at a reaction temperature of 70°C. After stirring for 3 hours, the aqueous layer and the organic layer were separated, and the organic layer was washed with 1% by mass sulfuric acid, and then with pure water. The solvent contained in the resulting solution was removed to obtain 200 g of phenylene ether resin (i) with styryl groups at the ends. The number-average molecular weight in polystyrene terms, calculated by GPC, was 1,220, and the weight-average molecular weight in polystyrene terms, calculated by GPC, was 1,560. In phenylene ether resin (i), the structure of the main resin is as follows. [ka]

[0086] <Synthesis Example 2: Synthesis of Polyphenylene Ether Resin (ii)> (Synthesis of phenylene ether oligomers) The polymerization reaction was carried out using the following procedure. Except for changing the amount of 2,6-dimethylphenol used to 313.4 g (2,565 mmol), the same procedure as in Synthesis Example 1 was followed to obtain 1,500 g of a toluene solution of phenylene ether resin. The number-average molecular weight in polystyrene terms, calculated by GPC, was 1,975, and the weight-average molecular weight in polystyrene terms, calculated by GPC, was 3,514.

[0087] (Terminal denaturation reaction of phenylene ether oligomers) The terminal denaturation reaction was performed using the following procedure. Except for changing the amount of toluene solution of phenylene ether resin used to 1,200 g, the same procedure as in Synthesis Example 1 was used to obtain 300 g of phenylene ether resin (ii) modified with styryl groups at the ends. The number-average molecular weight in polystyrene terms, calculated by GPC, was 2,250, and the weight-average molecular weight in polystyrene terms, calculated by GPC, was 3,920.

[0088] <Synthesis Example 3: Synthesis of Low Molecular Weight Compound (i) (Compound represented by formula (B))> A reactor equipped with a stirring device, a thermometer and a reflux tubing, 2,6-Xylenol 46.43g (380 mmol), Vinyl benzyl chloride (manufactured by AGC Seimi Chemical Co., Ltd., "CMS-P") 58.0g (380 mmol), Tetrabutylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 26g, Benzyldimethylamine 6.20g (0.046mol), 117g of 48% by mass sodium hydroxide aqueous solution, 180g of purified water, and Toluene 1,000g The mixture was prepared and stirred at a reaction temperature of 70°C. After stirring for 3 hours, the aqueous layer and the organic layer were separated, and the organic layer was washed with 1% by mass sulfuric acid, and then with pure water. The solvent contained in the resulting solution was removed to obtain 70 g of compound (i), in which the 2,6-xylenol terminus was modified to a styryl group. The structure of the obtained low molecular weight compound (i) is as follows. [ka]

[0089] <Synthesis Example 4: Synthesis of Low Molecular Weight Compounds (ii) (Compounds represented by formula (B))> A reactor equipped with a stirring device, a thermometer and a reflux tubing, 2,6-Diphenylphenol 93.60g (380 mmol), Vinyl benzyl chloride (manufactured by AGC Seimi Chemical Co., Ltd., "CMS-P") 58.0g (380 mmol), Tetrabutylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 26g, Benzyldimethylamine 6.20g (0.046mol), 117g of 48% by mass sodium hydroxide aqueous solution, 180g of purified water, and Toluene 1,000g The mixture was prepared and stirred at a reaction temperature of 70°C. After stirring for 3 hours, the aqueous layer and the organic layer were separated, and the organic layer was washed with 1% by mass sulfuric acid, and then with pure water. The solvent contained in the resulting solution was removed to obtain 100 g of compound (ii), in which the 2,6-diphenylphenol terminus was modified to a styryl group. The structure of the obtained low molecular weight compound (ii) is as follows. [ka]

[0090] The low molecular weight compounds used in the following examples and comparative examples are as follows: Low molecular weight compound (iii): 4-vinyl biphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.) Low molecular weight compound (iv): 1-Vinylnaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.) Low molecular weight compound (v): 1,4-Divinylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) Low molecular weight compound (vi): 1,2-bis(4-vinylphenyl)ethane Low molecular weight compound (vii): Acenaphthylene (manufactured by Tokyo Chemical Industry Co., Ltd.) Low molecular weight compound (viii): 2,6-Xylenol (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0091] Examples 1-9, Comparative Examples 1-11 <Preparation of resin composition> The materials and their quantities (in parts by mass) used in Examples 1-9 and Comparative Examples 1-11 are shown in Tables 1-4 below. A phenylene ether resin (i) or (ii) obtained in Synthesis Examples 1-2, one of the low molecular weight compounds (i)-(viii), 55 parts by mass of toluene, and 45 parts by mass of methyl ethyl ketone were charged into a 12 mL glass vial and mixed to obtain a homogeneous resin composition. The gel time, moldability, and dielectric loss tangent of this resin composition were evaluated and are shown in Tables 1-4.

[0092] <Geltime evaluation> 1.5 parts by mass of a crosslinking agent (Perhexine® 25B, manufactured by NOF Corporation) was added to 100 parts by mass of the resin composition obtained above and mixed to obtain a resin composition containing a curing agent. The obtained resin composition was dropped onto a hot plate of a gel time measuring instrument (manufactured by Nisshin Kagaku Co., Ltd.) that had been preheated to 170°C, and the time until the resin lost its fluidity while being stirred with a glass rod was defined as the gel time T (seconds). This time until gelation was measured and evaluated according to the following criteria. The gel time was measured in accordance with JIS C2161 B. [Evaluation Criteria] A: 20 seconds≦T≦40 seconds C:T < 20 seconds or T > 40 seconds (outside practical limits)

[0093] <Preparation of hardened material> The resin compositions obtained in the examples and comparative examples were subjected to solvent removal, and the resulting powders were used to prepare fallout as follows. 4.5g of resin composition powder was spread into a 100mm x 30mm stainless steel mold, set in a vacuum press (manufactured by Oji Machinery Co., Ltd.), and pressed at 200°C for 1.5 hours with a surface pressure of 1.9MPa.

[0094] <Evaluation of moldability> We evaluated whether it is possible to mold a cured product without the low-molecular-weight compound (compound represented by formula (B)) volatilizing or sublimating during pressing in the aforementioned <production of cured resin products>. 1.5 parts by mass of a crosslinking agent (Perhexine® 25B, manufactured by NOF Corporation) was added to 100 parts by mass of the resin composition obtained above and mixed to obtain a resin composition containing a curing agent. An aluminum container containing 1 g of this composition was placed in a dryer heated to 130°C, and after removing the solvent over 1 hour, the aluminum container was removed from the heating furnace. This resin-containing aluminum container was placed in a dryer heated to 170°C and cured over 15 minutes. After that, the aluminum container was weighed, and the volatility of the low molecular weight compound was evaluated by the weight loss rate calculated using the following formula. Weight loss rate (%) = Weight loss before and after heating (g) / Amount of low molecular weight compounds contained in the composition before heating (g) × 100 A lower weight loss rate indicates that the low-molecular-weight compound (the compound represented by formula (B)) was able to form the cured product without volatilization or sublimation. A rating of C indicates that no cured product was formed. [Evaluation Criteria] A: Weight reduction rate <20% B:20%≦weight reduction rate≦70% C: Weight reduction rate>70%

[0095] <Measurement of dielectric loss tangent> The dielectric loss tangent (Df) of the cured resin obtained in the above-mentioned <Preparation of Cured Resin> was measured at a frequency of 10 GHz using a perturbation cavity resonator (Agilent 8722ES, manufactured by Agilent Technologies, Inc.). The measurement temperature was 23°C. Based on the measurement results, the following criteria were used for evaluation. Comparative Examples 10 and 11 could not be evaluated because the cured products could not be molded. [Evaluation Criteria] A: 0.0015 ≤ Df ≤ 0.0025 B:Df>0.0025

[0096] [Table 1]

[0097] [Table 2]

[0098] [Table 3]

[0099] [Table 4]

[0100] Although the present invention has been described in detail using specific embodiments, it will be apparent to those skilled in the art that various modifications are possible without departing from the intent and scope of the invention.

Claims

1. A resin composition comprising a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and a compound represented by formula (B), The content of the compound represented by formula (B) is 1.0 to 15 parts by mass per 100 parts by mass of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminal, A resin composition in which the molecular weight of the compound represented by formula (B) is 150 to 400. 【Chemistry 1】 (In formula (B), R １ R is a group having a carbon-carbon unsaturated double bond at its terminal end. ２ and R ３ Each of the following is independently an alkyl group or phenyl group having 1 to 3 carbon atoms; m1 and m2 are independently integers from 0 to 4; and m3 and m4 are 0 or 1. However, neither m3 nor m4 can be 1. m5 is 0 or 1. However, if m5 is 0, then m3 is 1. L is a single bond, a methylene group, an ethylene group, an ether group, a group represented as -CH2-C(CH3)H-, or a group consisting of one methylene group and one ether group.

2. A resin composition comprising a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and a compound represented by formula (B), A resin composition in which the content of the compound represented by formula (B) is 1.0 to 15 parts by mass per 100 parts by mass of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminal, and R1 is a vinyl group, a (meth)allyl group, or a (meth)acryloyl group. 【Chemistry 2】 (In formula (B), R ２ and R ３ Each of the following is independently an alkyl group or phenyl group having 1 to 3 carbon atoms; m1 and m2 are independently integers from 0 to 4; and m3 and m4 are 0 or 1. However, neither m3 nor m4 can be 1. m5 is 0 or 1. However, if m5 is 0, then m3 is 1. L is a single bond, a methylene group, an ethylene group, an ether group, a group represented as -CH2-C(CH3)H-, or a group consisting of one methylene group and one ether group.

3. The resin composition according to claim 1 or 2, wherein the compound represented by formula (B) includes the compound represented by formula (B1). 【Transformation 3】 (In formula (B1), R １ m1 is a vinyl group, a (meth)allyl group, or a (meth)acryloyl group, Me is a methyl group, m1 and m2 are each independently integers from 0 to 4, and m3 and m4 are 0 or 1. However, neither m3 nor m4 can be 1. m5 is 0 or 1. However, if m5 is 0, then m3 is 1. １ This refers to a group represented by a single bond, a methylene group, an ethylene group, an ether group, -CH₂-C(CH₃)H-, or a group consisting of a combination of one methylene group and one ether group.

4. A resin composition comprising 100 parts by mass of a polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus, and at least one of the compounds shown below, in a total amount of 1.0 to 15 parts by mass. 【Chemistry 4】

5. The resin composition according to any one of claims 1, 2, and 4, wherein the number average molecular weight of the polyphenylene ether resin having carbon-carbon unsaturated double bonds at its termini is 500 to 3000.

6. The resin composition according to any one of claims 1, 2, and 4, wherein the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus comprises a compound represented by formula (OP). 【Transformation 5】 (In formula (OP), X represents an aromatic group, and -(Y-O) ｎ１ The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). 【Transformation 6】 (In Formula (Rx-1) and Formula (Rx-2), R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bonding site with an oxygen atom. Mc each independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.)

7. The resin composition according to any one of claims 1, 2, and 4, wherein the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus comprises a compound represented by formula (OP-1). 【Transformation 7】 (In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents the polyphenylene ether structure, R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, and n １ n represents an integer from 0 to 6, and n ２ n represents an integer between 1 and 100, and n ３ (This represents an integer between 1 and 4.)

8. The resin composition according to claim 1 or 2, wherein the total content of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and the compound represented by formula (B) in the resin composition is 90 to 100% by mass of the resin solids contained in the resin composition.

9. The resin composition according to claim 1 or 2, wherein the compound represented by formula (B) includes the following compounds. 【Transformation 8】

10. The polyphenylene ether resin having carbon-carbon unsaturated double bonds at its termini has a number-average molecular weight of 500 to 3000. The polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus contains a compound represented by formula (OP-1), The total content of the polyphenylene ether resin having a carbon-carbon unsaturated double bond at its terminus and the compound represented by formula (B) in the resin composition is 90 to 100% by mass of the resin solids contained in the resin composition. The compound represented by formula (B) includes the following compounds: The resin composition according to claim 1. 【Chemistry 9】 (In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents the polyphenylene ether structure, R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, and n １ n represents an integer from 0 to 6, and n ２ n represents an integer between 1 and 100, and n ３ (This represents an integer between 1 and 4.) 【Chemistry 10】

11. A cured product of the resin composition according to claim 1, 2, 4, or 10.

12. A resin composite sheet comprising a support and a layer formed from the resin composition according to claim 1, 2, 4, or 10 disposed on the surface of the support.

13. A prepreg formed from a substrate and the resin composition according to claim 1, 2, 4, or 10.

14. A metal foil-clad laminate comprising at least one prepreg according to claim 13 and a metal foil disposed on one or both sides of the prepreg.

15. A printed circuit board comprising an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from the resin composition described in claim 1, 2, 4, or 10.

16. A semiconductor device including a printed circuit board as described in claim 15.

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