Resin composition, cured object, prepreg, resin composite sheet, printed wiring board, and semiconductor device

Abstract

Provided are a resin composition, a cured object, a prepreg, a metal-foil-clad laminate board, a resin composite sheet, a printed wiring board, and a semiconductor device. The resin composition according to the present disclosure comprises 10-90 parts by mass of a resin (A) and 90-10 parts by mass of a maleimide compound (B) represented by formula (M4), wherein the resin (A) is represented by formula (T).

Description

Resin composition, cured product, prepreg, resin composite sheet, printed wiring board, and semiconductor device

[0001] The present invention relates to a resin composition, a cured product, a prepreg, a resin composite sheet, a printed wiring board, and a semiconductor device.

[0002] In recent years, the integration and miniaturization of semiconductor elements used in mobile terminals, electronic devices, communication devices, and the like have accelerated. Accordingly, technologies enabling high-density packaging of semiconductor elements are required, and improvements are also being sought for printed wiring boards, such as substrates for mounting semiconductor elements, which play an important role in this process. Meanwhile, the applications of electronic devices and the like are continuing to diversify and expand. Accordingly, the properties required for printed wiring boards, such as substrates for mounting semiconductor elements, and for the metal foil-clad laminates and prepregs used therein, are becoming more diverse and stricter. Taking these required properties into consideration, various materials and processing methods have been proposed to obtain improved printed wiring boards. One example is the development of improved resin materials for prepregs and resin composite sheets. Such materials are described in Patent Documents 1 to 4.

[0003] JP 2022-058409 A JP 2021-187893 A International Publication No. 2019 / 188189 JP 2018-090728 A

[0004] As described above, the applications of electronic devices and the like are diversifying and expanding, and new resin materials for use in prepregs and the like are also required. In particular, further development of materials is required for resin compositions capable of providing cured products with a low thermal expansion coefficient. The present invention aims to solve the above-mentioned problems by providing a resin composition capable of providing a cured product with a low thermal expansion coefficient, as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.

[0005] In light of the above-mentioned problems, the present inventors have conducted research and found that a resin composition capable of providing a cured product with a low thermal expansion coefficient can be obtained by using a resin having a specific isopropenyl group in combination with a specific maleimide compound. Specifically, the above-mentioned problems have been solved by the following means: [1] A resin composition comprising 10 to 90 parts by mass of a resin (A) and 90 to 10 parts by mass of a maleimide compound (B) represented by formula (M4), wherein the resin (A) is a resin represented by formula (T). (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and R represents a divalent group.) (In formula (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. [2] The resin composition according to [1], wherein R is a group containing an indane structure. [3] The resin composition according to [1] or [2], wherein R is a group containing the following structure: (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Ma each independently represent a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups via *, and the structural units may be bonded randomly.) [4] The resin composition according to [3], wherein the parameter α calculated from formula (α) in the resin (A) is 0.20 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less, and the number average molecular weight of the resin (A) is 400 to 3,000. (The brackets in formula (α) are: １ The integral between the corresponding chemical shift values ​​in H-NMR is shown, and the value in parentheses in formula (β) is １The integral between the corresponding chemical shift values ​​in H-NMR is shown.) [5] The resin composition according to any one of [1] to [4], wherein the compound represented by formula (M4) includes the following compound: (In the above formula, Me is a methyl group, and Et is an ethyl group.) [6] The resin composition according to any one of [1] to [5], wherein R is a group containing the following structure, and the parameter α calculated from formula (α) in the resin (A) is 0.20 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less, and the number average molecular weight of the resin (A) is 400 to 3000, and the compound represented by formula (M4) includes the following compound: (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) (The brackets in formula (α) are: １ The integral between the corresponding chemical shift values ​​in H-NMR is shown, and the value in parentheses in formula (β) is １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In the above formula, Me is a methyl group, and Et is an ethyl group.) [7] The resin composition according to any one of [1] to [6], further comprising a compound represented by formula (BV): (In formula (BV), Md each independently represents a hydrocarbon group having 1 to 12 carbon atoms. w represents an integer of 0 to 4. r represents an integer of 0 to 6.) [8] The resin composition according to any one of [1] to [7], further comprising a filler. [9] The resin composition according to any one of [1] to [8], further comprising at least one selected from the group consisting of an ultraviolet absorber, an antioxidant, a photopolymerization initiator, a fluorescent brightening agent, a photosensitizer, a dye, a pigment, a thickener, a flow modifier, a lubricant, an antifoaming agent, a leveling agent, a gloss agent, and a polymerization inhibitor.

[10] The resin composition according to any one of [1] to [9], which is for use in a printed wiring board. [X] The resin composition according to any one of the above, which has the following structure (X) when the resin composition is cured at 200°C: (In formula (X), R ｉ is a group derived from resin (A), and R ｍ is a group derived from a compound represented by formula (M4).

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

[10] and [X].

[12] A prepreg formed from a substrate and the resin composition according to any one of [1] to

[10] and [X].

[13] A metal foil-clad laminate comprising at least one prepreg according to

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

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

[10] and [X], disposed on a surface of the support.

[15] A printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from the resin composition according to any one of [1] to

[10] and [X].

[16] A semiconductor device comprising the printed wiring board according to

[15] .

[0006] The present invention makes it possible to provide a resin composition capable of providing a cured product having a low coefficient of thermal expansion, as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.

[0007] Synthesis Example 1 1 The H-NMR chart of the resin obtained in Synthesis Example 1 is shown below. 11 is a diagram showing peak values ​​of parameter α and parameter β in a H-NMR chart.

[0008] Hereinafter, a detailed description will be given of an embodiment of the present invention (hereinafter simply referred to as "the present embodiment"). The following embodiment is merely an example for explaining the present invention, and the present invention is not limited to this embodiment. In this specification, the term "to" is used to mean that the numerical values ​​before and after the term "to" include the upper and lower limits. In this specification, various physical property values ​​and characteristic values ​​are those at 23°C, unless otherwise specified. In the description of a group (atomic group), a notation that does not specify whether it is substituted or unsubstituted encompasses both a group (atomic group) that has no substituent and a group (atomic group) that has a substituent. For example, the term "alkyl group" encompasses not only an alkyl group that has no substituent (an unsubstituted alkyl group) but also an alkyl group that has a substituent (a substituted alkyl group). In this specification, when a notation that does not specify whether it is substituted or unsubstituted is used, unsubstituted is preferred. In this specification, the term "dielectric constant" refers to the ratio of the dielectric constant of a substance to the dielectric constant of a vacuum. In this specification, the term "dielectric constant" may also be simply referred to as "dielectric constant." Furthermore, in this specification, the term "dielectric constant" refers to the dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method, unless otherwise specified. In this specification, "(meth)acrylic" refers to both or either of acrylic and methacrylic. "(meth)allyl" refers to both or either of allyl and methallyl. When the measurement method, etc. of the specifications shown in this specification differ depending on the year, they are based on the specifications as of January 1, 2024, unless otherwise specified.

[0009] In this specification, the term "resin solids" refers to components excluding fillers and solvents, and is intended to include the resin (A), the maleimide compound (B) represented by formula (M4), and other thermosetting compounds that are blended as necessary, as well as other resin additive components (additives such as flame retardants, etc.).

[0010] The resin composition of the present embodiment is characterized in that it contains 90 to 10 parts by mass of a maleimide compound (B) represented by formula (M4) relative to 10 to 90 parts by mass of a resin (A), and the resin (A) is a resin represented by formula (T). (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and R represents a divalent group.) (In formula (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group.

[0011] The above-described configuration allows for the production of a resin composition capable of providing a cured product with a low thermal expansion coefficient. The inventors conducted research and speculated that the reason for this is as follows. Specifically, when resin (A) was subjected to a curing reaction at 200°C in the absence of a catalyst, a satisfactory cured product was not obtained. Similarly, when maleimide compound (B) represented by formula (M4) was subjected to a curing reaction at 200°C in the absence of a catalyst, a satisfactory cured product was not obtained. However, when a mixture of resin (A) and maleimide compound (B) represented by formula (M4) was subjected to a curing reaction at 200°C in the absence of a catalyst, a satisfactory cured product was obtained. Furthermore, when a mixture of resin (A) and maleimide compound (B) represented by formula (M4) was subjected to a curing reaction at 200°C in the presence of a polymerization inhibitor for radical polymerization, a satisfactory cured product was also obtained. Generally, a radical polymerization reaction between a compound having a vinyl bond and a maleimide compound proceeds through addition polymerization of the vinyl group. However, from the above experimental results, it was inferred that the curing of the resin (A) and the maleimide compound (B) represented by formula (M4) proceeds not only by a radical polymerization reaction but also by other reactions, such as the following reactions: R ｉ０ The compound containing R ｍ０The compound containing R is a maleimide compound (B) represented by formula (M4). It is presumed that the resin (A) and the maleimide compound (B) represented by formula (M4) form a rigid structure by the Diels-Alder reaction as described above. ｉ is a group derived from resin (A), and R ｍ is derived from the group represented by formula (M4). ｉ and R ｍ Ma and x have the same meanings as Ma and x in formula (T).

[0012] Hereinafter, the embodiments of the present invention will be described in detail. However, the explanation of the constituent elements described below is an example of an embodiment of the present invention, and the present invention is not limited to these contents.

[0013] <Resin (A)> The resin (A) in this embodiment is a resin represented by formula (T). (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and R represents a divalent group.)

[0014] In formula (T), each Ma is preferably a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, more preferably a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and even more preferably a hydrocarbon group having 1 to 3 carbon atoms which may be substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom, and a fluorine atom or a chlorine atom is preferred. Each Ma is preferably a hydrocarbon group having 1 to 12 carbon atoms which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. A methyl group or an ethyl group is particularly preferred as Ma.

[0015] x is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0016] In formula (T), R is a divalent group, and is —S—, —O—, or C(═O)—NH ２ -, or a hydrocarbon group, or a group consisting of a combination of two or more of these (these groups may have a substituent), more preferably a hydrocarbon group, more preferably a group containing an indane structure, and further preferably containing a group represented by formula (Tx). (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.)

[0017] In formula (Tx), n, o, and p each represent the average number of repeating units in all molecules in the resin. In formula (Tx), the sum of n, o, and p is preferably 1.1≦n+o+p, more preferably 1.2≦n+o+p, even more preferably 1.5≦n+o+p, even more preferably 2.0≦n+o+p, even more preferably 2.5≦n+o+p, even more preferably 3.0≦n+o+p, and particularly preferably 3.3≦n+o+p. In formula (Tx), the sum of n, o, and p is also preferably n+o+p≦20.0, more preferably n+o+p≦10.0, even more preferably n+o+p≦8.0, even more preferably n+o+p≦7.0, even more preferably n+o+p≦6.4, and may be n+o+p≦4.0. The sum of n, o and p can be calculated by the method described in the Examples below.

[0018] In formula (Tx), n is preferably 0.2 or more, more preferably 0.6 or more, even more preferably 1.0 or more, still more preferably 1.2 or more, still more preferably 1.6 or more, and may be 2.2 or more or 2.4 or more, and is preferably 18.0 or less, more preferably 12.0 or less, still more preferably 9.0 or less, still more preferably 7.0 or less, still more preferably 6.0 or less, and may be 5.0 or less, 4.0 or less, or 3.0 or less. In formula (Tx), o is preferably 0 or more, more preferably 0.01 or more, even more preferably 0.03 or more, still more preferably 0.05 or more, and even more preferably 0.07 or more, and is preferably 10.0 or less, more preferably 5.0 or less, even more preferably 4.0 or less, even more preferably 2.0 or less, and even more preferably 1.0 or less, and may be 0.8 or less, 0.5 or less, 0.3 or less, 0.2 parts or less, or 0.1 parts or less. In formula (Tx), p is preferably 0 or more, more preferably 0.01 or more, even more preferably 0.1 or more, even more preferably 0.2 or more, and even more preferably 0.3 or more, and is preferably 18.0 or less, more preferably 10.0 or less, even more preferably 5.0 or less, even more preferably 4.0 or less, and even more preferably 3.0 or less, and may be 2.5 or less, 2.0 or less, 1.0 or less, or 0.5 or less.

[0019] Furthermore, in formula (Tx), n / (n+o+p) is, for example, 0.2 or more, 0.25 or more, 0.3 or more, 0.34 or more, 0.4 or more, 0.45 or more, 0.5 or more, 0.55 or more, 0.6 or more, or 0.7 or more, and is 1.0 or less. Of the structural units (a) to (c) contained in formula (Tx), the structural unit (a), which has the smallest activation energy and the largest free energy change, is preferentially produced. When the R moiety in formula (T) is taken as 100 parts by mass, the proportion of the structural unit represented by formula (Tx) (i.e., any one of the structural units (a), (b), and (c)) is preferably 80 parts by mass, more preferably 90 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 97 parts by mass or more, even more preferably 99 parts by mass or more, and is 100 parts by mass or less. In formula (Tx), Ma and x each independently have the same meaning as Ma and x in formula (T), and the preferred ranges are also the same.

[0020] The resin represented by formula (T) preferably has a parameter α calculated from formula (α) of 0.20 or more and 1.00 or less, and a parameter β calculated from formula (β) of 0.20 or more and 3.00 or less. By setting parameters α and β within the above ranges, the obtained cured product tends to have low dielectric properties (Dk and / or Df) and excellent heat resistance. (The brackets in formula (α) are: １ The integral between the corresponding chemical shift values ​​in H-NMR is shown, and the value in parentheses in formula (β) is １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.)

[0021] Here, α indicates the ratio of the structural unit having an indane skeleton (structural unit (a) in formula (Tx)) in the resin represented by formula (T). More specifically, it is presumed that by adjusting the structural unit having an indane skeleton so as to satisfy the above-mentioned range of parameter α, the resulting resin molecules will have high rigidity and a high glass transition temperature. Furthermore, since highly rigid molecules have lower mobility than less rigid molecules, it is presumed that the relaxation time during dielectric relaxation will be longer and Df will be lower. When synthesizing the resin represented by formula (T), α can be increased by conditions such as diluting the concentration of raw materials, using a highly polar solvent, increasing the amount of catalyst, and raising the reaction temperature. Meanwhile, β defines the ratio of terminal double bonds in the resin represented by formula (T). More specifically, it is presumed that the number of crosslinking points with the functional group of the maleimide compound (B) increases, making it easier to form a network upon thermal curing, resulting in a cured product with a high glass transition temperature, a low thermal expansion coefficient, and a low Df. The value β can be increased by reducing the amount of catalyst, lowering the reaction temperature, using a low-polarity solvent, or other conditions when synthesizing the resin represented by formula (T).

[0022] More specifically, for the resin of Synthesis Example 1 described below, the 2.55 ppm to 2.31 ppm corresponds to the peak derived from structural unit (a), the 6.24 ppm to 5.91 ppm corresponds to the peak derived from structural unit (b), the 2.98 ppm to 2.55 ppm corresponds to the peak derived from structural unit (c), the 5.49 ppm to 4.89 ppm corresponds to the peak derived from the isopropenyl group and structural unit (c), the 4.89 ppm to 4.45 ppm corresponds to the peak derived from structural unit (c), and the 2.31 ppm to 1.96 ppm corresponds to the peak derived from the isopropenyl group and structural unit (a). More specifically, H used in calculating the parameters α and β is shown in the following structural formula: Used to calculate the above parameters α and β １ The H-NMR peaks can be assigned as follows using the H atoms described above: 2.55 ppm to 2.31 ppm: H a1・6.24 ppm to 5.91 ppm: H b1 ・2.98 ppm to 2.55 ppm: H c1 ・5.49 ppm to 4.89 ppm: H i2 and H i3 and H c2 ・4.89 ppm to 4.45 ppm: H c3 ・2.31 ppm to 1.96 ppm: H a2 and H i1

[0023] From the above, the formula for parameters α and β is written by the amount of each hydrogen atom as shown below. That is, parameter α is H a1 The greater the amount of H in the isopropenyl group, i.e., the greater the number of five-membered rings in the structural unit (a), the greater the parameter β. i1 The quantity of H i2 and H i3 The formula is shown so that the numerator is 1.5 times the total amount of (H i2 and H i3 1.5 times the total amount of H i1 The total amount of the resin obtained in Synthesis Example 1 (described later) is 1. 1 The peak values ​​of the parameters α and β are shown in the H-NMR chart.

[0024] When synthesizing the resin represented by formula (T), the parameters α and β of the resin represented by formula (T) can be adjusted using the method for increasing the parameters α and β described above. Of course, the parameters α and β may also be adjusted by a method other than the above.

[0025] The parameter α is preferably 0.20 or more, more preferably 0.25 or more, even more preferably 0.34 or more, still more preferably 0.45 or more, even more preferably 0.50 or more, even more preferably 0.55 or more, still more preferably 0.57 or more, and preferably 0.59 or more, 0.60 or more, or 0.62 or more, and may be 0.65 or more, 0.70 or more, 0.75 or more, or 0.80 or more depending on the application, etc. By setting the parameter α to be equal to or more than the above lower limit, the heat resistance of the obtained cured product tends to be further improved. The parameter α is preferably larger because the resulting cured product tends to have excellent low dielectric properties (Dk and / or Df) and heat resistance, but may be 1.00 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.82 or less, 0.80 or less, 0.77 or less, 0.75 or less, 0.74 or less, 0.70 or less, or 0.65 or less, depending on the application, etc. The parameter β is preferably 0.20 or more, more preferably 0.25 or more, even more preferably 0.30 or more, even more preferably 0.35 or more, still more preferably 0.40 or more, even more preferably 0.43 or more, particularly preferably 0.50 or more, or may be 0.60 or more, 0.65 or more, 0.70 or more, 0.77 or more, 0.80 or more, 0.90 or more, or 0.95 or more. By setting the parameter β to the above lower limit or more, the heat resistance of the obtained cured product tends to be improved and Df tends to be lower. The parameter β is preferably 3.00 or less, more preferably 2.50 or less, even more preferably 2.00 or less, even more preferably 1.50 or less, even more preferably 1.30 or less, even more preferably 1.20 or less, particularly more preferably 1.10 or less, and may even be 1.00 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.83 or less, or 0.80 or less. By setting the parameter β to the above upper limit or less, the heat resistance of the obtained cured product tends to be improved and Df tends to be lower.

[0026] Examples of raw materials that can be used in synthesizing the resin represented by formula (T) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0027] When m-bis(α-hydroxyisopropyl)benzene or p-bis(α-hydroxyisopropyl)benzene is used as an example of a raw material for synthesizing the resin represented by formula (T), 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene can be generated in the system by a dehydration reaction. Furthermore, the resin represented by formula (T) can be directly synthesized without isolating 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene. The resulting 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene can also be purified by distillation or the like before use.

[0028] The pressure when synthesizing the resin represented by formula (T) is preferably normal pressure, but it can also be carried out under reduced or increased pressure conditions.

[0029] Examples of steps for removing the solid catalyst when synthesizing the resin represented by formula (T) include filtration and decantation. These steps can be performed alone or in combination depending on the purpose.

[0030] Examples of the equipment include a centrifuge, a pressure filter, a vacuum filter, and an atmospheric pressure filter, and the equipment may be equipped with heating and vacuuming equipment to dry the filtered residue.

[0031] A filter aid may be used for the filtration. Examples of the filter aid include diatomaceous earth, cellulose, and perlite. These may be used alone or in combination.

[0032] When synthesizing 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene, which are raw materials for the resin represented by formula (T), it is preferable to ventilate or introduce an inert gas such as nitrogen into the liquid in order to efficiently advance the dehydration reaction.

[0033] The catalyst used in synthesizing the resin represented by formula (T) can be added all at once or in portions.

[0034] The temperature rise rate when synthesizing the resin represented by formula (T) is preferably 0.2° C. / min or more, more preferably 0.4° C. / min or more, even more preferably 0.7° C. / min or more, and may be 1.0° C. / min or more, 1.5° C. / min or more, 2.0° C. / min or more, or 2.5° C. / min or more. The temperature rise rate is preferably 5° C. / min or less, and more preferably 4° C. / min or less.

[0035] The material of the filter medium used when synthesizing the resin represented by formula (T) is preferably a material that is resistant to aromatic solvents such as toluene.

[0036] Examples of the stirring device used in the synthesis step of the resin represented by formula (T) include a mechanical stirring device, a magnetic stirring device, and an ultrasonic stirring device.

[0037] As a temperature control means used in the synthesis step of the resin represented by formula (T), a jacketed reaction vessel, a circulation device capable of heating or cooling, an infrared heating device, a microwave heating device, or a device combining these can be used.

[0038] The polystyrene-equivalent number average molecular weight (Mn) of resin (A) measured by GPC (gel permeation chromatography) (details follow the method described in the Examples below) is preferably 400 or more, more preferably 500 or more, even more preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By setting the number average molecular weight to the above lower limit or higher, the heat resistance of the obtained cured product tends to be improved and the Df tends to be lower. Furthermore, the upper limit of the polystyrene-equivalent number average molecular weight (Mn) of resin (A) measured by GPC (gel permeation chromatography) is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, even more preferably 1250 or less, and may be 1000 or less or 800 or less depending on the application, etc. By setting the number average molecular weight to the above upper limit or less, the heat resistance of the resulting cured product tends to be improved, and the dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower. Furthermore, the polystyrene-equivalent weight average molecular weight (Mw) of the resin (A) measured by GPC (details follow the method described in the Examples below) is preferably 500 or more, more preferably 800 or more, even more preferably 900 or more, and even more preferably 1000 or more. By setting the weight average molecular weight to the above lower limit or more, the heat resistance of the resulting cured product tends to be improved, and the Df tends to be lower. The upper limit of the polystyrene-equivalent weight average molecular weight (Mw) of the resin (A) measured by GPC (details follow the method described in the Examples below) is preferably 6000 or less, more preferably 5000 or less, even more preferably 4000 or less, even more preferably 3000 or less, and even more preferably 2800 or less. It may be 2500 or less, 2000 or less, or 1500 or less, depending on the application, etc. By adjusting the weight average molecular weight to the above upper limit or less, the heat resistance of the obtained cured product tends to be improved, and the relative dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower.

[0039] The resin (A) preferably has a Mw / Mn ratio, which is the ratio of weight average molecular weight to number average molecular weight, of 1.1 to 3.0. The Mw / Mn of the resin (A) is more preferably 1.2 or more, even more preferably 1.3 or more, even more preferably 1.4 or more, even more preferably 1.5 or more, and even more preferably 1.6 or more. The Mw / Mn of the resin (A) is more preferably 2.5 or less, even more preferably 2.4 or less, and may be 2.3 or less, 2.0 or less, or 1.8 or less. The weight average molecular weight and number average molecular weight are measured according to the methods described in the Examples below.

[0040] In this embodiment, the functional group equivalent (isopropenyl group equivalent) of the resin (A) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, still more preferably 250 g / eq. or more, even more preferably 275 g / eq. or more, still more preferably 300 g / eq. or more, and is preferably 7500 eq. or less, more preferably 5000 eq. or less, even more preferably 4000 eq. or less, still more preferably 3000 g / eq. or less, still more preferably 2000 g / eq. or less, still more preferably 1500 g / eq. or less, particularly still more preferably 1000 g / eq. or less, or may even be 800 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, or 500 g / eq. or less. By setting the functional group equivalent of resin (A) to the above lower limit or more, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly Df) and better peel strength. Furthermore, by setting the functional group equivalent of resin (A) to the above upper limit or less, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly Df), better heat resistance (particularly glass transition temperature), and a lower coefficient of thermal expansion. The functional group equivalent of resin (A) (isopropenyl group equivalent) is determined according to the method described in the Examples below.

[0041] The content of resin (A) in the resin composition of this embodiment is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and even more preferably 20 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more. By setting the content of resin (A) to the above-mentioned lower limit or more, the Df of the resulting cured product tends to be lower. Furthermore, the upper limit of the content of resin (A) is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and even more preferably 80 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 75 parts by mass or less, 70 parts by mass or less, 65 parts by mass or less, 60 parts by mass or less, 55 parts by mass or less, or 50 parts by mass or less. By setting the content of resin (A) to the above-mentioned upper limit or less, the moldability of the resin composition and the heat resistance of the resulting cured product tend to be improved. The resin composition of the present embodiment may contain only one type of resin (A), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0042] The method for producing the resin (A) in this embodiment is not particularly limited, and resins obtained by known production methods can be used. Furthermore, the raw materials, reaction temperature, catalyst type, catalyst amount, reaction solvent, raw material concentration, etc., used in synthesizing the resin (A) are not particularly limited, and can be appropriately selected or controlled depending on the desired physical properties described above.

[0043] <Maleimide Compound (B) Represented by Formula (M4)> The resin composition of the present embodiment contains a maleimide compound (B) represented by formula (M4). (In formula (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. An example of the maleimide compound (B) represented by formula (M4) is ５６ are each independently a methyl group or an ethyl group, and R ５７ is a methyl group. ５６More preferably, R is a methyl group and R is an ethyl group on each of the two benzene rings. ５６ and R ５７ is a hydrogen atom. In this embodiment, the maleimide compound (B) represented by formula (M4) preferably contains the following compound: In the above formula, Me represents a methyl group and Et represents an ethyl group.

[0044] The maleimide compound represented by formula (M4) may be a commercially available product, for example, "BMI-70" manufactured by K.I. Chemical Industry Co., Ltd. or "BMI-5100" manufactured by Daiwa Chemical Industry Co., Ltd.

[0045] The content of the maleimide compound (B) represented by formula (M4) in the resin composition of this embodiment is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and may be 20 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the intended use, it may be 25 parts by mass or more, 30 parts by mass or more, 35 parts by mass or more, 40 parts by mass or more, 45 parts by mass or more, or 50 parts by mass or more. By setting the content of the maleimide compound (B) represented by formula (M4) to the above-mentioned lower limit or more, the heat resistance of the resulting cured product tends to be improved and Df can be reduced. Furthermore, the upper limit of the content of the maleimide compound (B) represented by formula (M4) is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and even more preferably 80 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the intended use, it may be 70 parts by mass or less, or 65 parts by mass or less. By setting the content of the maleimide compound (B) represented by formula (M4) to the above upper limit or less, the moldability of the resin composition tends to be improved, and the thermal expansion coefficient of the obtained cured product tends to be lower. The resin composition of this embodiment may contain only one type of maleimide compound (B) represented by formula (M4), or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0046] The resin composition of this embodiment preferably contains 90 to 10 parts by mass of the maleimide compound (B) represented by formula (M4) per 10 to 90 parts by mass of the resin (A), 90 to 20 parts by mass of the maleimide compound (B) represented by formula (M4) per 10 to 80 parts by mass of the resin (A), more preferably 80 to 30 parts by mass of the maleimide compound (B) represented by formula (M4) per 20 to 70 parts by mass of the resin (A), and even more preferably 70 to 35 parts by mass of the maleimide compound (B) represented by formula (M4) per 30 to 65 parts by mass of the resin (A). An example of the resin composition of this embodiment is one in which the total amount of the resin (A) and the maleimide compound (B) represented by formula (M4) per 100 parts by mass of the resin solids contained in the resin composition is 90 parts by mass or more, preferably 95 parts by mass or more, more preferably 97 parts by mass or more, and may even be 98 parts by mass or more.

[0047] <Other Thermosetting Compounds> The resin composition of this embodiment may contain another thermosetting compound other than the resin (A) and the maleimide compound represented by formula (M4). The other thermosetting compound is typically a thermosetting resin. The type and other aspects of the other thermosetting compound are not particularly limited, but it is preferable that the other thermosetting compound contains at least one selected from the group consisting of other maleimide compounds other than the maleimide compound represented by formula (M4) (hereinafter referred to as "other maleimide compounds"), aromatic-containing resins having a terminal carbon-carbon double bond, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenolic compounds, oxetane resins, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group. It is more preferable that the resin composition contains at least one selected from the group consisting of a carboxylate compound, an epoxy compound, a phenol compound, an oxetane resin, a benzoxazine compound, an arylcyclobutene compound, a perfluorovinyl ether resin, a polyimide compound, and a compound having a vinylene group, and it is even more preferable that the resin composition contains at least one selected from the group consisting of another maleimide compound, an aromatic-containing resin having a terminal carbon-carbon double bond, and a cyanate ester compound, and it is even more preferable that the resin composition contains at least one selected from the group consisting of another maleimide compound and an aromatic-containing resin having a terminal carbon-carbon double bond, and it is even more preferable that the resin composition contains an aromatic-containing resin having a terminal carbon-carbon double bond.

[0048] The content of the other thermosetting compound 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 30 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. It may be 60 parts by mass or more, 65 parts by mass or more, and preferably 99 parts by mass or less, more preferably 95 parts by mass or less, even more preferably 90 parts by mass or less, even more preferably 85 parts by mass or less, and may be less than 80 parts by mass. By setting the content of the other thermosetting compound to the lower limit or more, heat resistance tends to be further improved. Furthermore, by setting the content of the other thermosetting compound to the upper limit or less, low thermal expansion tends to be further improved. The resin composition of this embodiment may contain only one type of other thermosetting compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0049] <<Other Maleimide Compounds>> The resin composition of this embodiment preferably contains another maleimide compound. In this embodiment, the other maleimide compound is preferably a compound having one or more (preferably two or more, more preferably 2 to 12, even more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and still more preferably 2) maleimide groups in one molecule. In this embodiment, the other maleimide compound preferably comprises one or more selected from the group consisting of compounds represented by formula (M0), compounds represented by formula (M1), compounds represented by formula (M2), compounds represented by formula (M3), compounds represented by formula (M5), other maleimide compounds (M6), other maleimide compounds (M7), and other maleimide compounds (M8), more preferably comprises one or more selected from the group consisting of compounds represented by formula (M0), compounds represented by formula (M1), compounds represented by formula (M2), compounds represented by formula (M3), and compounds represented by formula (M5), still more preferably comprises one or more selected from the group consisting of compounds represented by formula (M1), compounds represented by formula (M2), and compounds represented by formula (M5), and even more preferably comprises a compound represented by formula (M1) and / or a compound represented by formula (M2). The use of these other maleimide compounds in materials for printed wiring boards (e.g., metal foil-clad laminates) can impart excellent heat resistance.

[0050] (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １ represents an integer of 1 or more.) R ５１ are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５２ is preferably a methyl group.１ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and even more preferably 1. Specifically, the following compounds are preferred examples of formula (M0). In the above formula, R ８ each independently represents a hydrogen atom, a methyl group, or an ethyl group, and is preferably a methyl group.

[0051] The compound represented by formula (M0) may be a single compound or a mixture of two or more compounds. Examples of the mixture include compounds such as １ a mixture of compounds with different R ５１ and / or R ５２ a mixture of compounds having different types of substituents, a mixture of compounds having different bonding positions (meta, para, or ortho positions) of the maleimide group and the oxygen atom relative to the benzene ring, and a mixture of compounds having a combination of two or more of the above differences. The same applies to the compounds represented by formulas (M1) to (M8) below.

[0052] (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.

[0053] R in the formula Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１ and R Ｍ３ are each independently preferably an alkyl group, and R Ｍ２ and R Ｍ４ is preferably a hydrogen atom. Ｍ５ and R Ｍ６ Each of Ar independently represents a hydrogen atom or an alkyl group, and an alkyl group is preferable. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferable. Ｍ represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or an anthracenediyl group, more preferably a phenylene group, and even more preferably an m-phenylene group. Ｍ may have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ A is preferably a 4- to 6-membered alicyclic group, more preferably a 5-membered alicyclic group (preferably a group that forms an indane ring when combined with a benzene ring).Ｍ７ and R Ｍ８ are each independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group, with an alkyl group being more preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１２ and R Ｍ１３ are each independently preferably an alkyl group, and R Ｍ１１ and R Ｍ１４ is preferably a hydrogen atom. Ｍ１５each independently represent an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and is preferably an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms. px represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. nx represents an integer of 1 to 20. nx may be an integer of 10 or less. The resin composition of this embodiment may contain only one or more compounds represented by formula (M1) having at least different values ​​of nx. When two or more types are contained, the average value of nx (average number of repeating units) n in the compound represented by formula (M1) in the resin composition is preferably 0.92 or more, more preferably 0.95 or more, even more preferably 1.0 or more, and even more preferably 1.1 or more, in order to have a low melting point (low softening point), low melt viscosity, and excellent handleability. Furthermore, n is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 7.0 or less, even more preferably 6.0 or less, and may be 5.0 or less. The same applies to formula (M1-1) described later.

[0054] The compound represented by formula (M1) is preferably a compound represented by the following formula (M1-1): (In formula (M1-1), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group; and nx represents an integer of 1 or more and 20 or less.

[0055] R in the formula Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ２１ and R Ｍ２３ is preferably an alkyl group, and R Ｍ２２ and R Ｍ２４ is preferably a hydrogen atom. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferred. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents a hydrogen atom or an organic group, preferably a hydrogen atom. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferred. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ３３ and R Ｍ３６ is preferably a hydrogen atom, and R Ｍ３４ and R Ｍ３５ is preferably an alkyl group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group, with an alkyl group being preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. nx represents an integer of 1 to 20. nx may also be an integer of 10 or less.

[0056] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-2): (In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group; and nx represents an integer of 1 or more and 20 or less.

[0057] In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and nx are R in formula (M1-1), respectively. Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and nx, and the preferred ranges are also the same.

[0058] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-3), and more preferably a compound represented by the following formula (M1-4). (In formula (M1-3), nx represents an integer of 1 or more and 20 or less.) nx may be an integer of 10 or less. (In formula (M1-4), nx represents an integer of 1 or more and 20 or less.) nx may be an integer of 10 or less.

[0059] The molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By making the molecular weight equal to or greater than the lower limit, the low dielectric properties (Dk and / or Df) and low water absorption of the resulting cured product tend to be further improved. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, even more preferably 5,000 or less, and even more preferably 4,000 or less. By making the molecular weight equal to or less than the upper limit, the heat resistance and handleability of the resulting cured product tend to be further improved.

[0060] For other details of the compound represented by formula (M1), please refer to the descriptions in International Publication No. 2020-217679, the contents of which are incorporated herein by reference.

[0061] (In formula (M2), R ５４ each independently represents a hydrogen atom or a methyl group; n ４ represents an integer of 1 or more. ４ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. In the compound represented by formula (M2), n ４ It may be, and is preferably, a mixture of compounds in which the other moieties are different. Furthermore, as described in the compound represented by formula (M0), it may be a mixture of compounds in which the other moieties are different.

[0062] (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n ５ represents an integer of 1 or more and 10 or less.) R ５５are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５ is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2. In the compound represented by formula (M3), n ５ It may be, and is preferably, a mixture of compounds in which the other moieties are different. Furthermore, as described in the compound represented by formula (M0), it may be a mixture of compounds in which the other moieties are different.

[0063] (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n ６ represents an integer of 1 or more.) R ５８ are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５９ is preferably a methyl group. ６ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. In the compound represented by formula (M5), n ６ The compound represented by formula (M0) may be a mixture of compounds having different moieties, and is preferably a mixture. As described in the compound represented by formula (M0), the compound may be a mixture of compounds having different moieties.

[0064] Another maleimide compound (M6) is a compound having a structure represented by formula (M6) and maleimide groups at both ends of the molecular chain. (In formula (M6), R ６１ represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６２ represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６３ Each independently represents a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. Each n independently represents an integer of 0 to 10.) For details of other maleimide compounds (M6) and methods for producing them, please refer to paragraphs 0061 to 0066 of WO 2020 / 262577, the contents of which are incorporated herein by reference.

[0065] The other maleimide compound (M7) is a maleimide compound obtained by reacting an aromatic amine compound (a1) having from 1 to 3 alkyl groups on an aromatic ring, an aromatic divinyl compound (a2) having two ethenyl groups, and maleic anhydride as reaction raw materials (1). The other maleimide compound (M7) is preferably a compound having a structure represented by formula (M7). (In the above formula (M7), R １ each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４ one of which is a hydrogen atom and the other is a methyl group, and R ５ and R ６ one of which is a hydrogen atom and the other is a methyl group, １ are each independently represented by the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group, and R ９ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, and t represents an integer of 0 to 4. １ X per benzene ring to which １ is the average number of substitutions, and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

[0066] For details of the other maleimide compound (M7) used in this embodiment, refer to the description in Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0067] The other maleimide compound (M8) is a bismaleimide compound having a hydrocarbon group in which 8 or more atoms are linearly linked, and is preferably a compound represented by formula (M8): Such other maleimide compound (M8) tends to have a higher stress relaxation ability, and as a result, the thermal expansion coefficient of the obtained cured product tends to be lower, and the electrical properties such as the dielectric constant and the dielectric loss tangent tend to be more excellent. (In formula (M8), R １ and R ３ each independently represents a hydrocarbon group having 8 or more atoms linked in a linear chain, R ２ each independently represents a substituted or unsubstituted cyclic hydrocarbon group having 4 to 10 atoms constituting the ring, which may contain a heteroatom, and n represents a number from 1 to 10.

[0068] In formula (M8), R １ and R ３ is an octylene group, and R ２is preferably a cycloalkylene group having an alkyl group having 6 to 8 carbon atoms as a substituent.

[0069] For other maleimide compounds (M8), the descriptions in paragraphs 0014 to 0022 of JP-A-2018-083893 and paragraphs 0012 to 0022 of JP-A-2018-090728 can be referred to, the contents of which are incorporated herein by reference.

[0070] The other maleimide compounds may be produced by known methods, or commercially available products may be used. Commercially available products include, for example, "BMI-80" manufactured by K.I. Chemical Industry Co., Ltd. as the compound represented by formula (M0), "NE-X-9470S" and "NE-X-9480S" manufactured by DIC Corporation as the compound represented by formula (M1), "BMI-2300" manufactured by Daiwa Kasei Kogyo Co., Ltd. as the compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M3), "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M5), "MIZ-001" manufactured by Nippon Kayaku Co., Ltd. as the maleimide compound (M6), "NE-X-9500" manufactured by DIC Corporation as the maleimide compound (M7), and "SFR" manufactured by Resonac Inc. as another maleimide compound (M8). Examples of suitable ion exchangers include "BMI-689," "BMI-1500," "BMI-2500," "BMI-3000," and "BMI-5000" manufactured by INC.

[0071] Furthermore, examples of other maleimide compounds besides those mentioned above include N-phenylmaleimide, N-cyclohexylmaleimide, phenylmethanemaleimide oligomers, m-phenylenebismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane, 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, prepolymers thereof, and prepolymers of these maleimides and amines. In addition to the above, the compounds described in paragraphs 0051 to 0068 of WO 2020 / 262577 and the maleimide compounds described in paragraphs 0009 to 0096 of JP-A 2025-9839 can be referred to, the contents of which are incorporated herein by reference.

[0072] The maleimide group equivalent of the other maleimide compound is preferably 130 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 170 g / eq. or more, even more preferably 180 g / eq. or more, even more preferably 200 g / eq. or more, even more preferably 290 g / eq. or more, and preferably 1000 g / eq. or less, more preferably 800 g / eq. or less, even more preferably 700 g / eq. or less, even more preferably 600 g / eq. or less, and even more preferably 500 g / eq. or less. By setting it to be equal to or greater than the lower limit, the low dielectric properties (Dk and / or Df, particularly Df) of the obtained cured product tend to be better. Furthermore, by setting it to be equal to or less than the upper limit, the peel strength of the obtained cured product tends to be better and the thermal expansion coefficient tends to be lower.

[0073] When the resin composition of the present embodiment contains another maleimide compound, the lower limit of the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the intended use, etc., it may be 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more. When the content of the other maleimide compound is 1 part by mass or more, the flame resistance of the resulting cured product tends to be improved. Furthermore, the upper limit of the content of the other maleimide compound is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, even more preferably 55 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the intended use, etc., it may even be 50 parts by mass or less, 45 parts by mass or less. When the content of the other maleimide compound is 90 parts by mass or less, the peel strength and low water absorbency tend to be improved. The resin composition of the present embodiment may contain only one type of other maleimide compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0074] The resin composition of this embodiment may also be configured to be substantially free of maleimide compounds other than the maleimide compound (B) represented by formula (M4). "Substantially free" means that the content of maleimide compounds other than the maleimide compound (B) represented by formula (M4) is less than 10% by mass of the content of the maleimide compound (B) represented by formula (M4), preferably less than 5% by mass, more preferably less than 3% by mass, and even more preferably less than 1% by mass. This configuration allows the thermal expansion coefficient of the resulting cured product to be further reduced.

[0075] <<Aromatic-Containing Resin Having a Terminal Carbon-Carbon Double Bond>> The aromatic-containing resin having a terminal carbon-carbon double bond is, for example, a compound that has a terminal carbon-carbon double bond and contains an aromatic ring, and is a compound that cures when heated. By using the aromatic-containing resin having a terminal carbon-carbon double bond in combination with the elastomer (A), the compatibility between the two is improved, and the thermal expansion coefficient of the resulting cured product can be reduced. Specifically, the aromatic-containing resin having a terminal carbon-carbon double bond preferably includes one or more compounds selected from the group consisting of polyphenylene ether compounds having a terminal carbon-carbon unsaturated double bond and polymers having a structural unit represented by formula (V), and more preferably includes a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond.

[0076] When the resin composition of this embodiment contains an aromatic-containing resin having a terminal carbon-carbon double bond, the content thereof is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, and even more preferably 20 parts by mass or more, per 100 parts by mass of the resin solids in the resin composition. Depending on the application, it is even more preferable to be 25 parts by mass or more, and it is also preferably 95 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less. Depending on the application, it is even more preferable to be 55 parts by mass or less, even more preferably 50 parts by mass or less, and may even be 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less. By setting the content of the aromatic-containing resin having a terminal carbon-carbon double bond to be equal to or greater than the above-mentioned lower limit, compatibility and heat resistance tend to be further improved. Furthermore, by setting the content of the aromatic-containing resin having a terminal carbon-carbon double bond to be equal to or less than the above-mentioned upper limit, low thermal expansion properties tend to be further improved. The resin composition of the present embodiment may contain only one type of aromatic-containing resin having a terminal carbon-carbon double bond, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0077] <<<<Polyphenylene Ether Compound Having a Terminal Carbon-Carbon Unsaturated Double Bond>>> The resin composition of this embodiment preferably contains a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, and more preferably contains a polyphenylene ether compound containing two or more terminal carbon-carbon unsaturated double bonds. The polyphenylene ether compound containing two or more terminal carbon-carbon unsaturated double bonds preferably contains a polyphenylene ether compound having two or more groups (preferably vinylbenzyl groups) represented by formula (Rx-1) described below at its terminals. Use of these polyphenylene ether compounds tends to more effectively improve the low dielectric properties (Dk and / or Df) and low water absorption of printed wiring boards and the like. These properties are described in detail below.

[0078] Examples of polyphenylene ether compounds having a terminal carbon-carbon unsaturated double bond include compounds having a phenylene ether skeleton represented by the following formula (X1).

[0079] (In formula (X1), R ２４ , R ２５ , R ２６ , and R ２７ may be the same or different and represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.

[0080] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is represented by the formula (X2): (In formula (X2), R ２８ , R ２９ , R ３０ , R ３４ , and R ３５ may be the same or different and represent an alkyl group having 6 or less carbon atoms or a phenyl group. ３１ , R ３２ , and R ３３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and / or a repeating unit represented by formula (X3): (In formula (X3), R ３６ , R３７ , R ３８ , R ３９ , R ４０ , R ４１ , R ４２ , and R ４３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0081] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is preferably a modified polyphenylene ether compound in which some or all of the terminals are functionalized with ethylenically unsaturated groups (hereinafter, sometimes referred to as "modified polyphenylene ether compound (g)"), and more preferably a modified polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acryloyl groups and vinylbenzyl groups at the terminals. By using such a modified polyphenylene ether compound (g), it is possible to further reduce the dielectric dissipation factor (Df) of the cured product of the resin composition, and to improve the low water absorption and peel strength. These modified polyphenylene ether compounds (g) may be used alone or in combination of two or more.

[0082] The modified polyphenylene ether compound (g) may be a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, and —(Y—O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (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 a bonding site with an oxygen atom. Each Mc 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.

[0083] The aromatic group represented by X may or may not have a substituent on the benzene ring, but preferably has one. When the aromatic group has a substituent, examples thereof include the above-mentioned substituent Z, and the substituent is preferably at least one selected from the group consisting of an alkyl group having 6 or less carbon atoms, an aryl group, and a halogen atom, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. In addition, the -(Y-O)n １ The polyphenylene ether structure represented by - may or may not have a substituent on the benzene ring, but preferably has one. When it has a substituent, examples of the substituent Z include the above-mentioned substituent Z, but it is preferably an alkyl group having 6 or less carbon atoms or a phenyl group, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. １ and / or n ２ When n is an integer of 2 or more, １ n structural units (Y-O) and / or n ２ The n constitutional units may be the same or different. ２ is preferably 2 or more, more preferably 2.

[0084] In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ R each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. １ is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. ２ and R ３ are each 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. １ , R ２ , and R ３ The number of carbon atoms in each of the alkyl group, alkenyl group, and alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0085] In formula (Rx-1), r represents an integer of 0 to 6, and may be an integer of 1 or more, and is preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, still more preferably 1 or 2, and even more preferably 1.

[0086] In formula (Rx-1), each 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, still 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 formula (Rx-1), z represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and still more preferably 0.

[0087] 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.

[0088] The resin composition of the present embodiment preferably contains, as the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, a compound represented by formula (OP), which contains both a polyphenylene ether compound having a group represented by formula (Rx-1) and a polyphenylene ether compound having a group represented by formula (Rx-2).

[0089] The modified polyphenylene ether compound (g) includes a compound represented by formula (OP-1). (In formula (OP-1), X represents an aromatic group, and —(Y—O)n ２ - represents a polyphenylene ether structure, and R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group; n １ represents an integer of 0 to 6, n ２represents an integer from 1 to 100, and n ３ represents an integer of 1 to 4.) The aromatic group represented by X may or may not have a substituent on the benzene ring, but preferably has one. When the aromatic group has a substituent, examples thereof include the above-mentioned substituent Z, but it is preferably at least one selected from the group consisting of an alkyl group having 6 or less carbon atoms, an aryl group, and a halogen atom, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. In addition, the -(Y-O)n ２ The polyphenylene ether structure represented by - may or may not have a substituent on the benzene ring, but preferably has one. When it has a substituent, examples of the substituent Z include the above-mentioned substituent Z, but it is preferably an alkyl group having 6 or less carbon atoms or a phenyl group, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. ２ and / or n ３ When n is an integer of 2 or more, ２ n structural units (Y-O) and / or n ３ The n constitutional units may be the same or different. ３ is preferably 2 or more, more preferably 2.

[0090] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). Here, -(O-X-O)- represents the formula (OP-3): (In formula (OP-3), R ４ , R ５ , R ６ , R １０ , and R １１ may be the same or different and are alkyl groups or phenyl groups having 6 or less carbon atoms. ７ , R ８ , and R ９ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and / or a group represented by formula (OP-4): (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 are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0091] In addition, -(Y-O)- represents a group represented by formula (OP-5): (In formula (OP-5), R ２０ , R ２１ may be the same or different and are alkyl groups or phenyl groups having 6 or less carbon atoms. ２２ , R ２３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. ２０ and R ２１ are each independently a group having one or more methyl groups and / or cyclohexyl groups, the rigidity of the resulting resin molecules is increased, and since highly rigid molecules have lower mobility than less rigid molecules, the relaxation time during dielectric relaxation is longer, resulting in excellent low dielectric properties (Dk and / or Df, particularly Dk), which is preferable. An example of formula (OP-5) is the following structure. For the polyphenylene ether compound having the above structure, the description in JP-A-2019-194312 can be referred to, the contents of which are incorporated herein by reference.

[0092] In formula (OP-2), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100. a and b each independently represent an integer of 0 to 50, more preferably an integer of 1 to 30, and preferably an integer of 1 to 10. When a and / or b is an integer of 2 or greater, two or more -(Y-O)- groups may each independently represent an arrangement of one type of structure, or two or more types of structures may be arranged in blocks or randomly. Furthermore, when a compound represented by formula (OP-2) is contained, the average value of a preferably satisfies 1<a<10, and the average value of b preferably satisfies 1<b<10.

[0093] 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 to these.

[0094] Among the compounds represented by the above formula (OP-2), R ４ , R ５ , R ６ , R １０ , R １１ , R ２０ , and R ２１ is an alkyl group having 3 or less carbon atoms, and R ７ , R ８ , R ９ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , R １８ , R １９ , R ２２ , and R ２３is a hydrogen atom or an alkyl group having 3 or less carbon atoms, and it is particularly preferred that -(O-X-O)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and that -(Y-O)- 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 two or more -(Y-O)- may each independently be 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 blocks or randomly.

[0095] (In formula (OP-10), R ４４ , R ４５ , R ４６ , and R ４７ may be the same or different and are a hydrogen atom or a methyl group. -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms. Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4). (In formula (OP-11), -B- represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.) Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4).

[0096] The modified polyphenylene ether compound (g) is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and even more preferably a compound represented by formula (OP-15). (In formula (OP-14), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) a and b in formula (OP-14) each independently have the same meanings as a and b in formula (OP-2), and the preferred ranges are also the same. (In formula (OP-15), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) a and b in formula (OP-15) each independently have the same meanings as a and b in formula (OP-2), and the preferred ranges are also the same.

[0097] In addition, the polyphenylene ether compound used in this embodiment may also be a compound represented by formula (OP-16). (In formula (OP-16), each x independently represents an integer of 0 to 100, and at least one of the two x's is an integer of 1 to 100.)

[0098] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "SA9000" manufactured by SABIC Innovative Plastics, which is a modified polyphenylene ether compound having a terminal methacryloyl group. Examples of modified polyphenylene ether compounds having a terminal vinylbenzyl group include "OPE-2St1200" and "OPE-2St2200" manufactured by Mitsubishi Gas Chemical Company, Inc. Examples of modified polyphenylene ether compounds having a terminal vinylbenzyl group include polyphenylene ether compounds having a terminal hydroxyl group, such as "SA90" manufactured by SABIC Innovative Plastics, which are modified to a vinylbenzyl group using vinylbenzyl chloride or the like.

[0099] In addition, for details of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, see JP 2006-028111 A, JP 2018-131519 A, WO 2019-138992, WO 2022-054303, and JP 2024-544483 A, paragraphs 0015 to 0048, and paragraphs 0027 to 0122 of Japanese Patent No. 7530718, the contents of which are incorporated herein by reference.

[0100] The polystyrene-equivalent number average molecular weight (GPC) of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond (preferably, a modified polyphenylene ether compound (g)) is preferably 500 or more and 3,000 or less (details follow the method described in the Examples below). A number average molecular weight of 500 or more tends to further suppress stickiness when the resin composition of the present 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 polystyrene-equivalent weight average molecular weight (GPC) of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond (preferably, a modified polyphenylene ether compound (g)) is preferably 800 or more and 10,000 or less, more preferably 800 or more and 5,000 or less (details follow the method described in the Examples below). When the weight-average molecular weight is equal to or greater than the lower limit, the dielectric constant (Dk) and dielectric dissipation factor (Df) of the cured product of the resin composition tend to be lower, and when the weight-average molecular weight is equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents when preparing varnishes, etc., as described below, tend to be further improved. Furthermore, the terminal carbon-carbon unsaturated double bond equivalent of the polyphenylene ether compound (preferably, the modified polyphenylene ether compound (g)) having a terminal carbon-carbon unsaturated double bond is preferably 400 to 5,000 g, more preferably 400 to 2,500 g, per carbon-carbon unsaturated double bond. When the terminal carbon-carbon unsaturated double bond equivalent is equal to or greater than the lower limit, the dielectric constant (Dk) and dielectric dissipation factor (Df) of the cured product of the resin composition tend to be lower, and when the weight-average molecular weight is equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents tend to be further improved.

[0101] The functional group equivalent (equivalent of carbon-carbon unsaturated double bond) in a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is calculated from the reciprocal of the amount of double bonds determined from the results of measurement using an infrared spectrometer. The double bond equivalent [g / eq.] was determined as follows: A powder of the polyphenylene ether compound is weighed and the weight is recorded. This powder is placed in a measuring flask and then diluted to a predetermined amount with carbon disulfide to prepare a measurement sample. This sample liquid is placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Subsequently, infrared spectroscopy of the sample liquid is performed. In the case of a vinyl group in a polyphenylene ether compound, the IR spectrum of 905 cm is －１ When the carbon-carbon unsaturated double bond is a methacrylic group, the peak area of ​​the spectrum around 1640 cm is recorded. －１ The peak area of ​​the spectrum near the peak is recorded. The double bond concentration [mol / L] is calculated from this area value and the calibration curve. The double bond equivalent is then calculated using the following formula: Double bond equivalent [g / eq.] = Powder weight in measurement sample [g] / Double bond concentration [mol / L] × Measurement sample liquid volume [L]. The functional group equivalent of thermosetting compounds other than polyphenylene ether compounds having terminal carbon-carbon unsaturated double bonds can also be measured using the same method. However, for compounds (monomers) that can be expressed by a single molecular weight, the value calculated by (theoretical molecular weight ÷ number of functional groups) is used as the functional group equivalent. When two or more other thermosetting compounds are included, the functional group equivalent of the other thermosetting compounds is the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each of the other thermosetting compounds by their mass fraction.

[0102] When the resin composition of this embodiment contains a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, the lower limit of the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, and even more preferably 20 parts by mass or more, per 100 parts by mass of the resin solids in the resin composition, and may even be 25 parts by mass or more depending on the application, etc. By setting the content of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond to be equal to or greater than the above-mentioned lower limit, the moldability of the resin composition and the heat resistance, low water absorbency, and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less, per 100 parts by mass of the resin solids in the resin composition. Depending on the application, it may be 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less. By setting the content of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond to the above upper limit or less, the low dielectric properties (particularly low dielectric dissipation factor) and chemical resistance of the obtained cured product tend to be improved. The resin composition in this embodiment may contain only one type of polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range.

[0103] <<<Polymer Having a Structural Unit Represented by Formula (V)>>> The resin composition of the present embodiment may contain a polymer having a structural unit represented by formula (V). By containing a polymer having a structural unit represented by formula (V), a resin composition with excellent low dielectric properties (low relative dielectric constant, low dielectric loss tangent) can be obtained. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) The aromatic hydrocarbon linking group may be a group consisting only of aromatic hydrocarbons which may have a substituent, or a group consisting of a combination of aromatic hydrocarbons which may have a substituent and other linking groups, and is preferably a group consisting only of aromatic hydrocarbons which may have a substituent. Examples of the substituent that the aromatic hydrocarbon may have include the substituent Z (e.g., an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, an amino group, a carboxy group, a halogen atom, etc.). It is also preferable that the aromatic hydrocarbon does not have a substituent. The aromatic hydrocarbon linking group is usually a divalent linking group.

[0104] Specific examples of the aromatic hydrocarbon linking group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a biphenyldiyl group, and a fluorenediyl group, each of which may have a substituent, and among these, a phenylene group which may have a substituent is preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferable that the above-mentioned phenylene group and other groups do not have a substituent.

[0105] It is more preferable that the polymer having a structural unit represented by formula (V) contains at least one of a structural unit represented by formula (V1) below, a structural unit represented by formula (V2) below, and a structural unit represented by formula (V3) below. In the formulas below, * represents a bonding position. Furthermore, hereinafter, the structural units represented by formulas (V1) to (V3) may be collectively referred to as "structural unit (a)."

[0106] In formulas (V1) to (V3), L １is an aromatic hydrocarbon linking group (preferably having 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 10 carbon atoms). Specific examples include phenylene groups, naphthalenediyl groups, anthracenediyl groups, phenanthrenediyl groups, biphenyldiyl groups, and fluorenediyl groups, each of which may have a substituent. Of these, phenylene groups, which may have a substituent, are preferred. Examples of the substituent include the aforementioned substituent Z, but it is preferable that the aforementioned groups, such as the phenylene group, be unsubstituted. The compound forming the structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene. Of these, divinylbenzene is particularly preferred. These divinyl aromatic compounds may be used alone, or two or more types may be used as necessary. That is, the structural unit (a) is preferably a structural unit derived from a divinyl aromatic compound.

[0107] As mentioned above, the polymer having the structural unit represented by formula (V) may be a homopolymer of the compound forming the structural unit (a), but may also be a copolymer with a structural unit derived from another monomer.When the polymer having the structural unit represented by formula (V) is a copolymer, its copolymerization ratio is preferably 3 mol% or more of the structural unit (a), more preferably 5 mol% or more, even more preferably 10 mol% or more, and may even be 15 mol% or more.The upper limit is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, particularly more preferably 30 mol% or less, and may even be 25 mol% or less, 20 mol% or less.

[0108] An example of a structural unit derived from another monomer is a structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0109] The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[0110] In formula (V4), L ２ is an aromatic hydrocarbon linking group, and preferred examples thereof include the above L １ Examples include the following. * indicates the bonding position. R Ｖ１ is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). Ｖ１ When R is a hydrocarbon group, it preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. Ｖ１ and L ２ may have the above-mentioned substituent Z.

[0111] When the polymer having a structural unit represented by formula (V) is a copolymer containing a structural unit (b) derived from a monovinyl aromatic compound, examples of the monovinyl aromatic compound include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinylbiphenyl; and nuclear alkyl-substituted vinyl aromatic compounds such as o-methylstyrene, m-methylstyrene, p-methylstyrene, o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, and ethylvinylbiphenyl. The monovinyl aromatic compounds exemplified here may optionally have the aforementioned substituent Z. Furthermore, these monovinyl aromatic compounds may be used alone or in combination with two or more. Among these, the structural unit (b) preferably contains a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene. It is more preferable that the structural unit (b) further contains a structural unit derived from styrene in addition to a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene.

[0112] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (b), the copolymerization ratio of the structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may further be 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, or 75 mol% or more. The upper limit is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.

[0113] A polymer having a structural unit represented by formula (V) may have structural units other than the structural unit (a) and the structural unit (b). Examples of such structural units include structural unit (c) derived from a cycloolefin compound. Examples of cycloolefin compounds include hydrocarbons having a double bond within the ring structure. Specific examples include monocyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, as well as compounds having a norbornene ring structure such as norbornene and dicyclopentadiene, and cycloolefin compounds having condensed aromatic rings such as indene and acenaphthylene. Examples of norbornene compounds include those described in paragraphs 0037 to 0043 of JP 2018-039995 A, the contents of which are incorporated herein by reference. The cycloolefin compounds exemplified here may further have the aforementioned substituent Z.

[0114] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (c), the copolymerization ratio of the structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, and even more preferably 70 mol% or less, and may be 50 mol% or less, or may be 30 mol% or less.

[0115] A polymer having a structural unit represented by formula (V) may further incorporate a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as "other polymerizable compound"). Examples of other polymerizable compounds (monomers) include compounds containing three vinyl groups. Specific examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate, butadiene (e.g., 1,3-butadiene), and isoprene. The copolymerization ratio of the structural unit (d) derived from other polymerizable compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0116] An example of an embodiment of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a) and contains at least one of the structural units (b) and (c). Further, an example is an embodiment in which the total of the structural units (a) to (c) accounts for 90 mol% or more, even 95 mol% or more, and particularly 98 mol% or more of all structural units. Another example of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a) and contains at least one of the structural units (b) to (d). Further, an example is an embodiment in which the total of the structural units (a) to (d) accounts for 95 mol% or more, even 98 mol% or more of all structural units. Another example of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a), and of all structural units excluding the terminals, preferably 90 mol% or more, more preferably 95 mol% or more, and even 100 mol%. In calculating the mole percentage per total structural units, one structural unit is considered to be derived from one molecule of a monomer (e.g., a divinyl aromatic compound, a monovinyl aromatic compound, etc.) used in producing a polymer having a structural unit represented by formula (V).

[0117] The method for producing a polymer having a structural unit represented by formula (V) is not particularly limited and may be a conventional method, but examples thereof include polymerizing a raw material containing a divinyl aromatic compound (optionally in the presence of a monovinyl aromatic compound, a cycloolefin compound, etc.) in the presence of a Lewis acid catalyst. The Lewis acid catalyst may be a metal fluoride such as boron trifluoride or a complex thereof.

[0118] The structure of the chain end of the polymer having the structural unit represented by formula (V) is not particularly limited, but in terms of the group derived from the divinyl aromatic compound, it may have a structure represented by the following formula (E1). １ is the same as defined in the above formula (V1). * represents the bonding position. *-CH=CH-L １ -CH=CH ２ (E1)

[0119] When a group derived from a monovinyl aromatic compound is at the chain end, the structure may be that of the following formula (E2): ２ and R Ｖ１ are the same as defined in the formula (V4). * represents a bonding position. *-CH=CH-L ２ -R Ｖ１ (E2)

[0120] The molecular weight of the polymer having the structural unit represented by formula (V) is preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and even more preferably 1,500 or more, in number average molecular weight (Mn). The upper limit of the number average molecular weight is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, even more preferably 100,000 or less, and may be 30,000 or less, 10,000 or less, or 5,000 or less. The molecular weight of the polymer having the structural unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 10,000 or more, in weight average molecular weight (Mw). By setting the weight average molecular weight to be equal to or greater than the lower limit, the excellent low dielectric properties (Dk and / or Df), particularly Df and dielectric properties after moisture absorption, possessed by the polymer having the structural unit represented by formula (V) can be effectively exhibited in the cured product of the resin composition. The upper limit of the weight-average molecular weight Mw is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less. By setting the weight-average molecular weight to the above upper limit or less, poor embedding tends to be less likely when the prepreg or resin sheet is laminated on a circuit-forming substrate. The monodispersity (Mw / Mn), expressed as the ratio of the weight-average molecular weight (Mw) to the number-average molecular weight (Mn), is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and may be 15 or less, or even 12 or less. As for the lower limit, a practical value is 1.1 or more, preferably 2.0 or more, more preferably 4 or more, even more preferably 5 or more, even more preferably 7 or more, and even more preferably 8 or more. The Mw and Mn are measured according to the description in the Examples below. When the resin composition of the present embodiment contains two or more polymers having a structural unit represented by formula (V), it is preferable that the Mw, Mn and Mw / Mn of the mixture satisfy the above ranges.

[0121] The vinyl group equivalent of the polymer having a structural unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, even more preferably 250 g / eq. or more, and may be 300 g / eq. or more, or 350 g / eq. or more. The vinyl group equivalent is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and may further be 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 350 g / eq. or less. When the vinyl group equivalent is above the lower limit, the storage stability of the resin composition is improved and the fluidity of the resin composition tends to be improved. Therefore, moldability is improved, voids are less likely to occur when forming a prepreg, etc., and a more reliable printed wiring board tends to be obtained. On the other hand, when the vinyl group equivalent is equal to or less than the upper limit, the heat resistance of the resulting cured product tends to be improved.

[0122] The cured product of a polymer having a structural unit represented by formula (V) preferably has excellent low dielectric properties (Dk and / or Df). For example, the cured product of the polymer having a structural unit represented by formula (V) used in this embodiment preferably has a relative dielectric constant (Dk) of 2.80 or less, more preferably 2.60 or less, even more preferably 2.50 or less, and even more preferably 2.40 or less, at 10 GHz, measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the relative dielectric constant is, for example, 1.80 or more. Furthermore, the cured product of the polymer having a structural unit represented by formula (V) preferably has a dielectric loss tangent (Df) of 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less, at 10 GHz, measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the dielectric loss tangent is, for example, 0.0001 or more. The relative dielectric constant (Dk) and the dielectric loss tangent (Df) are measured by the following method. 4.5 g of resin powder was spread in a stainless steel mold frame measuring 100 mm x 30 mm x 1.0 mm high, placed in a vacuum press (Kitagawa Seiki Co., Ltd.), and held at 200 ° C for 2 hours, pressing at a surface pressure of 3.0 MPa to produce a cured plate. The cured plate was then downsized to a width of 1.0 mm, dried at 120 ° C for 60 minutes, and then measured for its relative permittivity (Dk) and dielectric loss tangent (Df) at 10 GHz using a perturbation cavity resonator. The measurement temperature was 23 ° C.

[0123] For polymers having a structural unit represented by formula (V) in this specification, the compounds described in paragraphs 0029 to 0058 of WO 2017 / 115813 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0013 to 0058 of JP-A 2018-039995 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0008 to 0043 of JP-A 2018-168347 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0014 to 0042 of JP-A 2006-070136 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0014 to 0061 of JP-A 2006-089683 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0008 to 0036 of JP-A 2008-248001 and their synthesis reaction conditions, etc. can be referenced, and are incorporated herein. The polymer having the structural unit represented by formula (V) may be a commercially available product, such as LF-310T50 manufactured by Nippon Steel Chemical & Material Co., Ltd.

[0124] When the resin composition of this embodiment contains a polymer having a structural unit represented by formula (V), the lower limit of its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. By setting the content of the polymer having a structural unit represented by formula (V) to the above lower limit or more, low dielectric properties, particularly a low relative dielectric constant, tend to be effectively achieved. Furthermore, the upper limit of the content of the polymer having a structural unit represented by formula (V) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and may be 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, 35 parts by mass or less, or 30 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the polymer having the structural unit represented by formula (V) to the above upper limit or less, the metal foil peel strength and low water absorption tend to be improved. The resin composition in this embodiment may contain only one type of polymer having the structural unit represented by formula (V), or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range. Furthermore, the resin composition in this embodiment may be configured to be substantially free of a polymer having a structural unit represented by formula (V). "Substantially free" means that the content of the polymer having the structural unit represented by formula (V) is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0125] <<Other Compounds Having a Terminal Carbon-Carbon Unsaturated Double Bond (Compound (XC))>> The resin composition of this embodiment may contain another compound (compound (XC)) having a terminal carbon-carbon unsaturated double bond other than those described above. An example of compound (XC) is a low-molecular-weight aromatic vinyl compound. Examples of aromatic vinyl compounds include methylstyrene (e.g., 4-methylstyrene), ethylvinylbenzene, diethyl 4-vinylbenzylphosphonate, 4-vinylbenzyl glycidyl ether, α-methylstyrene, 4-tert-butylstyrene, divinylbenzene, vinylbenzyl ether, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene, with 4-methylstyrene, 4-tert-butylstyrene, and divinylbenzene being preferred. Further examples include resins having an isopropenyl group described in WO 2022 / 210095 (e.g., the compounds described in Synthesis Examples 1, 2, 7, and 8 of that publication), the contents of which are incorporated herein by reference.

[0126] Another example of another compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) is vinylbenzyl ether. Examples of vinylbenzyl ether include reaction products produced by reacting 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), hexamethylbiphenol (2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol), 2,6-dihydroxynaphthalene, or the like with vinylbenzyl chloride and / or vinylbenzyl bromide. Further, resorcinol, catechol, hydroquinone, 2,7-dihydroxynaphthalene, 2-(diphenylphosphoryl)hydroquinone, bis(2,6-dimethylphenol), 2,2'-biphenol, 4,4-biphenol, 2,2',6,6'-tetramethylbiphenol, 3,3',5,5'-tetrabromo-2,2',6,6'-tetramethylbiphenol, 3,3'-dibromo-2,2',6,6'-tetramethylbiphenol, 4,4'-isopropylidenebis(2,6-dibromophenol) (tetrabromobisphenol A), 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), 4,4'-isopropylidenebis(2-methylphenol), 4,4'-isopropylidenebis(2-allylphenol), 4 ,4'(1,3-phenylenediisopropylidene)bisphenol (bisphenol M), 4,4'-isopropylidenebis(3-phenylphenol), 4,4'-(1,4-phenylenediisopropylidene)bisphenol (bisphenol P), 4,4'-ethylidenediphenol (bisphenol E), 4,4'-oxydiphenol, 4,4'-thiodiphenol, 4,4'-thiobis(2,6-dimethylphenol), 4,4'-sulfonyldiphenol, 4,4'-sulfonylbis(2,6-dimethylphenol), 4,4'-sulfinyldiphenol, 4,4'-hexafluoroisopropylidene)bisphenol (bisphenol AF), 4,4'(1-phenylethylidene)bisphenol (bisphenol AP), bis(4-hydroxyphenyl)-2,2-Dichloroethylene (bisphenol C), bis(4-hydroxyphenyl)methane (bisphenol-F), bis(2,6-dimethyl-4-hydroxyphenyl)methane, 4,4'-(cyclopentylidene)diphenol, 4,4'-(cyclohexylidene)diphenol (bisphenol Z), 4,4'-(cyclododecylidene)diphenol, 4,4'-(bicyclo[2.2.1]heptylidene)diphenol, 4,4'-(9H-fluorene -9,9-diyl)diphenol, 3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one, 1-(4-hydroxyphenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol, 1-(4-hydroxy-3,5-dimethylphenyl)-1,3,3,4,6-pentamethyl-2,3-dihydro-1H-inden-5-ol, 3,3,3',3'-tetramethyl-2,2',3,3'-tetrahydro-1,1 Examples of vinylbenzyl ethers include those produced by reacting 5,6'-spirobi[indene]-5,6'-diol (spirobiindane), dihydroxybenzophenone (bisphenol K), tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)propane, tris(4-hydroxyphenyl)butane, tris(3-methyl-4-hydroxyphenyl)methane, tris(3,5-dimethyl-4-hydroxyphenyl)methane, tetrakis(4-hydroxyphenyl)ethane, tetrakis(3,5-dimethyl-4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)phenylphosphine oxide, dicyclopentadienylbis(2,6-dimethylphenol), dicyclopentadienylbis(o-cresol), dicyclopentadienylbisphenol, or the like with vinylbenzyl chloride or vinylbenzyl bromide. In addition to the above, vinylbenzyl compounds also include the vinylbenzyl ether compounds described in paragraph 0041 of JP 2019-194312 A, and the compounds described in paragraphs 0008 to 0032 of Japanese Patent No. 7551036 and paragraphs 0007 to 0057 of Japanese Patent No. 7530537, the contents of which are incorporated herein by reference.

[0127] In this embodiment, the vinylbenzyl compound may particularly include a compound represented by formula (BV). By including the compound represented by formula (BV), thermal expansion of the cured product can be effectively suppressed. (In formula (BV), each Md independently represents a hydrocarbon group having 1 to 12 carbon atoms; w represents an integer of 0 to 4; and r represents an integer of 0 to 6.)

[0128] In formula (BV), Md each independently represent a hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group, more preferably a straight-chain alkyl group, and even more preferably a methyl group or an ethyl group. In formula (BV), w represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0. In formula (BV), r represents an integer of 0 to 6, preferably 1 or more, more preferably 2 or more, and preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, and even more preferably 2 or less. In this embodiment, the compound represented by formula (BV) is particularly preferably the following compound.

[0129] In addition to the above, compounds having vinylphenyl at the terminal described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 12 to 16 of the same publication), paragraphs 0029 to 0039 of JP-A-2022-85610, paragraphs 0023 to 0043 of JP-A-2024-107328, paragraphs 0022 to 0039 of JP-A-2024-7493, JP-A-2024-139678 paragraphs 0010 to 0053 copolymers described in paragraphs 0041 of JP-A-2019-194312 vinyl benzyl ether resins, copolymerized oligomers described in paragraphs 0013 to 0027 of WO 2022 / 014599 can also be used, the contents of which are incorporated herein by reference.

[0130] The content of the other compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and may be 15 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, etc., it may be 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, 35 parts by mass or more, 40 parts by mass or more, or 45 parts by mass or more. By setting the content of the other compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) to the above-mentioned lower limit or more, the Df of the obtained cured product tends to be lower. Furthermore, the upper limit of the content of the other compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, etc., it may be 70 parts by mass or less, 65 parts by mass or less, or 55 parts by mass or less. By setting the content of the other compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) to the above upper limit or less, the moldability of the resin composition and the heat resistance of the obtained cured product tend to be improved. The resin composition of this embodiment may contain only one type of other compound having a terminal carbon-carbon unsaturated double bond (compound (XC)), or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0131] <<<<Other aromatic-containing resins having a terminal carbon-carbon double bond>>> In addition to the above, examples of aromatic-containing resins having a terminal carbon-carbon double bond include the descriptions in paragraphs 0011 to 0025 of WO 2023 / 176766, the descriptions in paragraphs 0012 to 0033 of WO 2023 / 176764, the descriptions in paragraphs 0012 to 0033 of WO 2023 / 176763, and the descriptions in paragraphs 0026 to 0043 of WO 2023 / 176765. The contents of these descriptions are incorporated herein by reference.

[0132] <<Cyanate Ester Compound>> The resin composition of this embodiment may contain a cyanate ester compound. The cyanate ester compound of this embodiment is not particularly limited as long as it contains one or more cyanate groups (cyanato groups) in one molecule (preferably two or more, more preferably 2 to 12, even more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2), and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Furthermore, the cyanate ester compound is preferably a compound in which the cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Preferred examples of the cyanate ester compound in this embodiment include at least one selected from the group consisting of phenol novolac-type cyanate ester compounds, naphthol aralkyl-type cyanate ester compounds (naphthol aralkyl-type cyanates), naphthylene ether-type cyanate ester compounds, biphenyl aralkyl-type cyanate ester compounds, xylene resin-type cyanate ester compounds, trisphenolmethane-type cyanate ester compounds, adamantane skeleton-type cyanate ester compounds, bisphenol M-type cyanate ester compounds, bisphenol A-type cyanate ester compounds, and diallyl bisphenol A-type cyanate ester compounds. Among these, from the viewpoint of further improving the low water absorption of the obtained cured product, at least one selected from the group consisting of phenol novolac cyanate ester compounds, naphthol aralkyl cyanate ester compounds, naphthylene ether cyanate ester compounds, xylene resin cyanate ester compounds, bisphenol M cyanate ester compounds, bisphenol A cyanate ester compounds, and diallyl bisphenol A cyanate ester compounds is more preferable, at least one selected from the group consisting of phenol novolac cyanate ester compounds and naphthol aralkyl cyanate ester compounds is even more preferable, and naphthol aralkyl cyanate ester compounds are even more preferable. These cyanate ester compounds may be prepared by known methods, or commercially available products may be used.In addition, cyanate ester compounds having a naphthol aralkyl skeleton, a naphthylene ether skeleton, a xylene skeleton, a trisphenolmethane skeleton, or an adamantane skeleton have a relatively large functional group equivalent weight and a small number of unreacted cyanate ester groups, so that cured products of resin compositions using these compounds tend to have even more excellent low water absorption. Furthermore, mainly due to the presence of an aromatic skeleton or an adamantane skeleton, plating adhesion tends to be even more improved.

[0133] As the naphthol aralkyl cyanate ester compound, a compound represented by the following formula (1) is more preferred. (In formula (1), R ３ each independently represents a hydrogen atom or a methyl group, and n3 represents an integer of 1 or greater.

[0134] In formula (1), R ３ each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferred. In formula (1), n3 represents an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0135] The novolac-type cyanate ester compound is not particularly limited, but is preferably, for example, a compound represented by the following formula (VII). (In formula (VII), R ６ each independently represents a hydrogen atom or a methyl group, and n7 represents an integer of 1 or greater.

[0136] In formula (VII), R ６ each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferable. In formula (VII), n7 represents an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0137] As the bisphenol A type cyanate ester compound, one or more compounds selected from the group consisting of 2,2-bis(4-cyanatophenyl)propane and prepolymers of 2,2-bis(4-cyanatophenyl)propane may be used.

[0138] The resin composition of this embodiment preferably contains a cyanate ester compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a cyanate ester compound, the lower limit of the cyanate ester compound content is preferably 0.1 parts by mass or more, more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the cyanate ester compound content is 0.1 parts by mass or more, the heat resistance, flame resistance, chemical resistance, low dielectric properties (low dielectric constant, low dielectric dissipation factor), and insulating properties of the resulting cured product tend to be improved. When the resin composition of this embodiment contains a cyanate ester compound, the upper limit of the cyanate ester compound content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of cyanate ester compound, or may contain two or more types of cyanate ester compounds. When two or more types are contained, the total amount is preferably within the above range.

[0139] <<(Meth)allyl Compound>> The resin composition of this embodiment may contain a (meth)allyl compound. The (meth)allyl compound preferably contains an allyl compound. The (meth)allyl compound is preferably a compound containing two or more (meth)allyl groups, more preferably a compound containing two or more allyl groups. The (meth)allyl compound preferably contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a tri(meth)allyl cyanurate compound, a (meth)allyl group-substituted nadimide compound, a (meth)allyl compound having a glycoluril structure, and a diallyl phthalate. More preferably, the (meth)allyl compound contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a (meth)allyl group-substituted nadimide compound, and a (meth)allyl compound having a glycoluril structure. Still more preferably, the (meth)allyl isocyanurate compound and / or a (meth)allyl group-substituted nadimide compound is further preferred. Still more preferably, the (meth)allyl group-substituted nadimide compound is further preferred.

[0140] Examples of the tri(meth)allyl cyanurate compound include tri(meth)allyl cyanurate compounds (for example, triallyl cyanurate having the structure shown below). Examples of the (meth)allyl compound include resins having an allyl group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 3, 4, 6, 20, and 22 of the same publication), the contents of which are incorporated herein by reference.

[0141] When the resin composition of this embodiment contains a (meth)allyl compound, its molecular weight is preferably 195 or more, more preferably 300 or more, and may be 400 or more, or even 500 or more. By making the molecular weight equal to or greater than the lower limit, low dielectric properties and heat resistance tend to be further improved. The molecular weight of the (meth)allyl compound is also preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By making the molecular weight equal to or less than the upper limit, low thermal expansion properties tend to be further improved.

[0142] When the resin composition of this embodiment contains a (meth)allyl compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound to be equal to or greater than the above-mentioned lower limit, excellent moldability and heat resistance tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound to be equal to or less than the above-mentioned upper limit, low thermal expansion tends to be further improved. The resin composition of this embodiment may contain only one type of (meth)allyl compound, or may contain two or more types. When two or more types are contained, the total amount preferably falls within the above-mentioned range.

[0143] <<<(Meth)allyl isocyanurate compound>>> The (meth)allyl isocyanurate compound is not particularly limited as long as it is a compound having two or more (meth)allyl groups and an isocyanurate ring (nurate skeleton). Because (meth)allyl isocyanurate compounds have a large number of (meth)allyl groups that serve as crosslinking points, they tend to be strongly cured with other thermosetting compounds such as aromatic-containing resins having terminal carbon-carbon double bonds and maleimide compounds, and to produce cured products with low dielectric properties (Dk and / or Df) and excellent heat resistance. As the (meth)allyl isocyanurate compound, a compound represented by formula (TA) is preferred. Formula (TA) (In formula (TA), R Ａ represents a substituent).

[0144] In formula (TA), R Ａ represents a substituent, and is more preferably a substituent having a formula weight of 15 to 500.

[0145] R ＡA first example is an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using an allyl compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, a resin composition can be provided that is excellent in crosslinkability and can yield a cured product with high toughness. This can prevent cracking during etching or other processes, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 3 or more, more preferably 8 or more, and may even be 12 or more or 18 or less. This improves the resin flow properties of the resin composition, which is believed to result in improved circuit filling properties when using the resin composition of this embodiment to fabricate a multilayer circuit board or the like.

[0146] R Ａ A second example of R is a group containing an allyl isocyanurate group. Ａ When the compound represented by formula (TA) contains an allyl isocyanurate group, the compound represented by formula (TA) is preferably a compound represented by formula (TA-1). (In formula (TA-1), R Ａ２ is a divalent linking group.

[0147] In formula (TA-1), R Ａ２ is preferably a divalent linking group having a formula weight of 54 to 250, more preferably a divalent linking group having a formula weight of 54 to 250 and both ends of which are carbon atoms, and even more preferably an aliphatic hydrocarbon group having 2 to 20 carbon atoms (however, the aliphatic hydrocarbon group may contain an ether group or may have a hydroxyl group). More specifically, R Ａ２ is preferably a group represented by any one of the following formulas (i) to (iii): (In formulas (i) to (iii), p ｃ１ represents the number of repeating methylene units and is an integer of 2 to 18. ｃ２ represents the number of repeating units of the oxyethylene group, and is 0 or 1. * represents a bonding site. ｃ１is preferably an integer of 2 to 10, more preferably an integer of 3 to 8, and even more preferably an integer of 3 to 5. ｃ２ may be 0 or 1, but is preferably 1.

[0148] R Ａ A third example is a phosphorus-based substituent.

[0149] R Ａ２ is preferably the first example.

[0150] In this embodiment, the reactive group (allyl group) equivalent of the compound represented by formula (TA) is preferably 1000 g / eq. or less. If the equivalent is 1000 g / eq. or less, it is believed that a high Tg can be more reliably obtained.

[0151] Examples of the alkyl group having 1 to 22 carbon atoms include linear or branched alkyl groups, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl groups. Examples of the alkenyl group having 2 to 22 carbon atoms include allyl and decenyl groups.

[0152] Specific examples of the compound represented by formula (TA) include triallyl isocyanurate, 5-octyl-1,3-diallyl isocyanurate, 5-dodecyl-1,3-diallyl isocyanurate, 5-tetradecyl-1,3-diallyl isocyanurate, 5-hexadecyl-1,3-diallyl isocyanurate, 5-octadecyl-1,3-diallyl isocyanurate, 5-eicosyl-1,3-diallyl isocyanurate, 5-docosyl-1,3-diallyl isocyanurate, and 5-decenyl-1,3-diallyl isocyanurate. These may be used alone or in combination of two or more, or may be used as a prepolymer.

[0153] The method for producing the compound represented by formula (TA) is not particularly limited, but for example, the compound can be obtained by reacting diallyl isocyanurate with an alkyl halide in an aprotic polar solvent such as N,N'-dimethylformamide, in the presence of a basic substance such as sodium hydroxide, potassium carbonate, or triethylamine, at a temperature of about 60°C to 150°C.

[0154] Furthermore, commercially available compounds represented by formula (TA) can also be used. Commercially available compounds include, but are not limited to, L-DAIC manufactured by Shikoku Chemical Industries Ltd., and P-DAIC having a phosphorus-based substituent manufactured by Shikoku Chemical Industries Ltd. An example of triallyl isocyanurate is TAIC manufactured by Shinryo Corporation. An example of a compound represented by formula (TA-1) is DD-1 manufactured by Shikoku Chemical Industries Ltd.

[0155] The molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 200 or more, more preferably 300 or more, and may be 400 or more, or even 500 or more. By setting the molecular weight to be equal to or greater than the above-mentioned lower limit, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to be equal to or less than the above-mentioned upper limit, the low thermal expansion properties of the obtained cured product tend to be further improved.

[0156] When the resin composition of this embodiment contains a (meth)allyl isocyanurate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl isocyanurate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)allyl isocyanurate compound, or may contain two or more types of (meth)allyl isocyanurate compounds. When two or more types are contained, the total amount is preferably within the above range.

[0157] <<<<(Meth)allyl Group-Substituted Nadimide Compound>>> The (meth)allyl group-substituted nadimide compound is not particularly limited as long as it is a compound having two or more (meth)allyl group-substituted nadimide groups in the molecule. Specific examples include compounds represented by the following formula (AN-1): (In formula (AN-1), R １ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ２ represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by formula (AN-2) or (AN-3). (In formula (AN-2), R ３ represents a methylene group, an isopropylidene group, —C(═O)—, —O—, —S—, or —S(═O) ２ represents a group represented by the formula: (In formula (AN-3), R ４each independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.

[0158] Furthermore, commercially available compounds represented by formula (AN-1) can also be used. Examples of commercially available compounds include, but are not limited to, the compound represented by formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and the compound represented by formula (AN-5) (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). These compounds may be used alone or in combination of two or more. Formula (AN-4)

[0159] The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 400 or more, more preferably 500 or more, and may be 550 or more. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above-mentioned lower limit or more, low dielectric properties, low thermal expansion, and heat resistance tend to be further improved. The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above-mentioned upper limit or less, moldability and peel strength tend to be further improved.

[0160] When the resin composition of the present embodiment contains a (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or greater than the above-mentioned lower limit, excellent moldability and further improved low dielectric properties, low thermal expansion, and heat resistance tend to be achieved. Furthermore, the upper limit of the content of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or less than the above-mentioned upper limit, moldability and peel strength tend to be further improved. The resin composition of the present embodiment may contain only one (meth)allyl group-substituted nadimide compound, or may contain two or more (meth)allyl group-substituted nadimide compounds. When two or more (meth)allyl group-substituted nadimide compounds are contained, the total amount is preferably in the above range.

[0161] <<<<(Meth)allyl Compound Having a Glycoluril Structure>>> The (meth)allyl compound having a glycoluril structure is not particularly limited as long as it contains a glycoluril structure and two or more (meth)allyl groups. When a (meth)allyl compound having a glycoluril structure is blended into a resin composition, the number of (meth)allyl groups can be increased, i.e., the number of crosslinking points can be increased. Therefore, similar to (meth)allyl isocyanurate compounds, it tends to be firmly cured with other thermosetting compounds such as aromatic-containing resins having terminal carbon-carbon double bonds and maleimide compounds, and to produce cured products with low dielectric properties (Dk and / or Df) and excellent heat resistance. In this embodiment, the (meth)allyl compound having a glycoluril structure is preferably a compound represented by formula (GU). Formula (GU) (In formula (GU), R １ are each independently a hydrogen atom or a substituent, and R１ At least two of R are groups containing a (meth)allyl group. ２ each independently represents a hydrogen atom, an alkyl group, or an aryl group. １ are each independently preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, more preferably an alkenyl group having 2 to 5 carbon atoms, more preferably a (meth)allyl group, and even more preferably an allyl group. １ In formula (GU), it is preferable that three or four of R are groups containing a (meth)allyl group, and it is more preferable that four of R are groups containing a (meth)allyl group. ２ are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, more preferably a hydrogen atom or a methyl group, and two R ２ It is more preferable that all of are hydrogen atoms.

[0162] Specific examples of the compound represented by formula (GU) include 1,3,4,6-tetraarylglycoluril (in formula (GU), R １ are all allyl groups, and R ２ are all hydrogen atoms).

[0163] The (meth)allyl compound having a glycoluril structure may be commercially available, and examples thereof include, but are not limited to, TA-G manufactured by Shikoku Chemicals Corporation.

[0164] The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, even more preferably 250 or more, and may be 300 or more, or 400 or more. By setting the molecular weight of the (meth)allyl compound having a glycoluril structure to the above-mentioned lower limit or more, the heat resistance and low thermal expansion of the obtained cured product tend to be further improved. The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl compound having a glycoluril structure to the above-mentioned upper limit or less, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved.

[0165] When the resin composition of the present embodiment contains a (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure to be equal to or greater than the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure to be equal to or less than the above-mentioned upper limit, the low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one (meth)allyl compound having a glycoluril structure, or may contain two or more (meth)allyl compounds. When two or more compounds are contained, the total amount is preferably in the above range.

[0166] <<<(Meth)acrylate Compound>>> The resin composition of this embodiment may contain a (meth)acrylate compound. In this specification, the (meth)acrylate compound, which also corresponds to the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond described above, is defined as a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond. The (meth)acrylate compound used in this embodiment may be a monofunctional (meth)acrylate compound containing one (meth)acryloyloxy group in one molecule, or a polyfunctional (meth)acrylate compound containing two or more (meth)acryloyloxy groups in one molecule. In this embodiment, a polyfunctional (meth)acrylate compound is preferred.

[0167] The polyfunctional (meth)acrylate compound used in this embodiment is preferably a compound having three to five (meth)acryloyloxy groups, more preferably a compound having three or four (meth)acryloyloxy groups, and even more preferably a compound having three (meth)acryloyloxy groups. The (meth)acrylate compound is preferably a compound having a methacryloyloxy group. Because polyfunctional (meth)acrylate compounds have a large number of (meth)acrylate groups that serve as crosslinking points, they are firmly cured with other thermosetting compounds such as aromatic-containing resins having terminal carbon-carbon double bonds and maleimide compounds, resulting in a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. The polyfunctional (meth)acrylate compound is preferably a compound represented by formula (MA). Formula (MA) (In formula (MA), R １ represents a hydrogen atom or a substituent, R ２ each independently represents a hydrogen atom or a methyl group.

[0168] In formula (MA), R １ represents a hydrogen atom or a substituent, and is more preferably a substituent having a formula weight of 15 to 500, more preferably a substituent having a formula weight of 15 to 300, even more preferably a substituent having a formula weight of 15 to 100, and even more preferably a substituent having a formula weight of 15 to 50.

[0169] R １is preferably a hydrocarbon group or a (meth)acryloyloxy group, more preferably a hydrocarbon group having 22 or fewer carbon atoms, and even more preferably an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using a compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, a resin composition can be provided that is excellent in crosslinkability and can yield a cured product with high toughness. This can prevent cracking during etching or other processes, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 2 or more, and may be 8 or more, or even 12 or more and 18 or less. This is thought to improve the resin flow properties of the resin composition, resulting in improved circuit filling properties when using the resin composition of this embodiment to fabricate a multilayer circuit board or the like.

[0170] In this embodiment, the (meth)acrylic group equivalent of the compound represented by formula (MA) is preferably 1000 g / eq. or less. If the equivalent is 1000 g / eq. or less, a high Tg tends to be more reliably obtained. The lower limit of the (meth)acrylic group equivalent is, for example, 99 g / eq. or more.

[0171] The alkyl group having 1 to 22 carbon atoms is preferably a linear alkyl group having 1 to 22 carbon atoms or a branched alkyl group having 3 to 22 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a docosyl group, etc. The alkenyl group having 2 to 22 carbon atoms is preferably an alkenyl group having 2 to 15 carbon atoms, such as an allyl group, a decenyl group, etc.

[0172] Specific examples of the compound represented by formula (MA) include trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetra(meth)acrylate, etc. These may be used alone or in combination of two or more, or may be used as a prepolymer.

[0173] The compound represented by formula (MA) may also be commercially available. Although there is no particular limitation on the commercially available product, an example of the commercially available product is trimethylolpropane trimethacrylate, such as "NK Ester TMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.

[0174] The molecular weight of the polyfunctional (meth)acrylate compound is preferably 200 or more, more preferably 300 or more, and may be 330 or more, 400 or more, or 500 or more. By setting the molecular weight to the above-mentioned lower limit or more, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)acrylate compound (preferably a compound represented by formula (MA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to the above-mentioned upper limit or less, the low thermal expansion properties of the obtained cured product tend to be further improved.

[0175] In addition to the above, (meth)acrylate compounds include resins having a (meth)acrylic group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 5 and 21 of the same publication) and resins having a (meth)acrylic group described in Japanese Patent No. 6,962,507 (for example, compounds described in Examples 1 to 9), compounds described in paragraph 0049 of JP-A 2019-194312, and resins having a (meth)acrylic group described in paragraphs 0010 to 0096 of JP-A 2024-159338. The contents of this specification are incorporated herein by reference.

[0176] When the resin composition of this embodiment contains a (meth)acrylate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)acrylate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)acrylate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)acrylate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)acrylate compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above-mentioned range.

[0177] <<Epoxy Compound>> The resin composition of this embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having one or more epoxy groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and still more preferably 2) per molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the epoxy compound include phenol novolac epoxy resins, bisphenol A novolac epoxy resins, glycidyl ester epoxy resins, aralkyl novolac epoxy resins, biphenyl aralkyl epoxy resins, naphthylene ether epoxy resins, cresol novolac epoxy resins, multifunctional phenol epoxy resins, naphthalene epoxy resins, anthracene epoxy resins, naphthalene skeleton-modified novolac epoxy resins, phenol aralkyl epoxy resins, naphthol aralkyl epoxy resins, dicyclopentadiene epoxy resins, biphenyl epoxy resins, alicyclic epoxy resins, polyol epoxy resins, phosphorus-containing epoxy resins, glycidyl amines, glycidyl esters, compounds in which the double bonds of butadiene or the like have been epoxidized, and compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin. Use of these compounds improves the moldability and adhesion of the resin composition. Among these, from the viewpoint of further improving flame retardancy and heat resistance, the epoxy compound is preferably at least one selected from the group consisting of biphenylaralkyl epoxy resins, naphthylene ether epoxy resins, polyfunctional phenolic epoxy resins, and naphthalene epoxy resins, and more preferably a biphenylaralkyl epoxy resin.

[0178] When the resin composition of this embodiment contains an epoxy compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. When the epoxy compound content is 0.1 parts by mass or more, the metal foil peel strength and toughness tend to be improved. The upper limit of the epoxy compound content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less, and may be 8 parts by mass or less, or 5 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. When the epoxy compound content is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition of this embodiment may contain only one type of epoxy compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The resin composition of this embodiment may also be configured to be substantially free of epoxy compounds. "Substantially free" means that the content of the epoxy compound is less than 0.1 parts by mass, preferably less than 0.01 parts by mass, and may even be less than 0.001 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0179] <<Phenol Compound>> The resin composition of this embodiment may contain a phenolic compound. The phenolic compound is not particularly limited as long as it has one or more phenolic hydroxyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) per molecule. A wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the phenolic compound include phenol novolac resins, bisphenol A novolac phenolic resins, glycidyl ester phenolic resins, aralkyl novolac phenolic resins, biphenyl aralkyl phenolic resins, cresol novolac phenolic resins, multifunctional phenolic resins, naphthol resins, naphthol novolac resins, multifunctional naphthol resins, anthracene phenolic resins, naphthalene skeleton-modified novolac phenolic resins, phenol aralkyl phenolic resins, naphthol aralkyl phenolic resins, dicyclopentadiene phenolic resins, biphenyl phenolic resins, alicyclic phenolic resins, polyol phenolic resins, phosphorus-containing phenolic resins, and hydroxyl group-containing silicone resins. Among these, from the viewpoint of further improving the flame resistance of the resulting cured product, it is preferable to select at least one selected from the group consisting of biphenyl aralkyl phenolic resins, naphthol aralkyl phenolic resins, phosphorus-containing phenolic resins, and hydroxyl group-containing silicone resins. In addition, as for the phenolic compound, the description in paragraphs 0012 to 0025 of WO 2023 / 176765 can also be taken into consideration, and the contents thereof are incorporated herein by reference.

[0180] When the resin composition of this embodiment contains a phenolic compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, still more preferably 10 parts by mass or less, and may even be 5 parts by mass or less. The resin composition of this embodiment may contain only one type of phenolic compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The resin composition of this embodiment may also be configured to be substantially free of phenolic compounds. "Substantially free" means that the content of phenolic compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0181] <<Oxetane Compound>> The resin composition of this embodiment may contain an oxetane compound. The oxetane compound is not particularly limited as long as it is a compound having one or more oxetanyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the oxetane compound include oxetane, alkyloxetane (e.g., 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3,3-di(trifluoromethyl)oxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), and OXT-121 (manufactured by Toagosei Co., Ltd.).

[0182] The resin composition of this embodiment preferably contains an oxetane compound to a degree that does not impair the effects of the present invention. When the resin composition of this embodiment contains an oxetane compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane compound is 0.1 parts by mass or more, the metal foil peel strength and toughness of the resulting cured product tend to be improved. When the resin composition of this embodiment contains an oxetane compound, the upper limit of the content of the oxetane compound is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane compound is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition of this embodiment may contain only one oxetane compound, or may contain two or more oxetane compounds. When two or more types are contained, the total amount is preferably in the above range. Furthermore, the resin composition in this embodiment may be configured to be substantially free of oxetane compounds. "Substantially free" means that the content of the oxetane compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0183] <<Benzoxazine Compound>> The resin composition of this embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it is a compound having two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings per molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of benzoxazine compounds include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0184] The resin composition of this embodiment preferably contains a benzoxazine compound to the extent that the effects of the present invention are not impaired. When the resin composition of this embodiment contains a benzoxazine compound, the content thereof is preferably 0.1 parts by mass or more and preferably 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of a benzoxazine compound. "Substantially free" means that the content of the benzoxazine compound is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0185] <<Compound Having a Vinylene Group>> The resin composition of this embodiment may contain a compound having a vinylene group. Examples of compounds having a vinylene group include compounds containing one or more -CH=CH- groups in the molecule, and compounds containing one -CH=CH- group in the molecule are preferred. Furthermore, compounds having a vinylene group that also qualify as maleimide compounds are referred to as maleimide compounds. Specific examples of compounds having a vinylene group include preferred acenaphthylene and pyracylene, and more preferred is acenaphthylene. In this specification, compounds that also qualify as compounds having a vinylene group but are explicitly listed as components other than compounds having a vinylene group (e.g., radical polymerization initiators), such as the imidazole compounds described above, are not considered to be compounds having a vinylene group.

[0186] <Flame Retardant> The resin composition of the present embodiment may contain a flame retardant. Examples of the flame retardant include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, and phosphorus-based flame retardants are preferred. As the flame retardant, known ones can be used, for example, halogen-based flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, and chlorinated paraffin; phosphorus-containing flame retardants such as red phosphorus; tricresyl phosphate, triphenyl phosphate, 2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, cresyl diphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl) phosphorus-based flame retardants such as monomeric phosphate esters such as phosphazene, phenoxyphosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), xylenebisdiphenylphosphine oxide of the bisdiphenylphosphine oxide type, condensed phosphate esters of dixylenyl phosphate, 6H-dibenz[c,e][1,2]oxaphosphorine,6,6'-[1,4-phenylenebis(methylene)]bis-,6,6'-dioxide, and condensed phosphate esters such as phosphinate metal salts of dialkylphosphinic aluminum salts; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, partial boehmite, boehmite, zinc borate, and antimony trioxide; and silicone-based flame retardants such as silicone rubber and silicone resin. In this embodiment, among these, 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferred because it does not impair the low dielectric properties (Dk and / or Df).

[0187] When the resin composition of this embodiment contains a flame retardant, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and preferably 30 parts by mass or less, more preferably 25 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The flame retardant may be used alone or in combination of two or more. When two or more types are used, the total amount is within the above range.

[0188] <Active ester compound> The resin composition of the present embodiment may contain an active ester compound within a range that does not impair the effects of the present invention. The active ester compound is not particularly limited, and for example, the description in paragraphs 0064 to 0066 of WO 2021 / 172317 can be referred to, the contents of which are incorporated herein by reference.

[0189] When the resin composition of this embodiment contains an active ester compound, the amount is preferably 1 part by mass or more and preferably 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of an active ester compound. "Substantially free" means that the content of the active ester compound is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0190] <Dispersant> The resin composition of this embodiment may contain a dispersant. As the dispersant, those generally used for paints can be suitably used, and the type is not particularly limited. As the dispersant, a copolymer-based wetting dispersant is preferably used, and specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, and W940, manufactured by BYK Japan K.K.

[0191] When the resin composition of this embodiment contains a dispersant, the lower limit of the content is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and may be 0.3 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The upper limit of the dispersant content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and may be 3 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The dispersants can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0192] <Solvent> The resin composition of this embodiment may contain a solvent, and preferably contains an organic solvent. When a solvent is contained, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the various resin solid components described above are dissolved or compatible in the solvent. The solvent is not particularly limited as long as it is a polar organic solvent or a non-polar organic solvent that can dissolve or compatible at least a portion, preferably all, of the various resin solid components described above. 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, dimethylformamide, etc.). Examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). The solvents may be used alone or in combination of two or more. When two or more solvents are used, the total amount falls within the above range.

[0193] <Curing Accelerator> The resin composition of the present embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, and examples thereof include imidazoles such as 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, and triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, α,α'-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitriles (for example, azobisisobutyronitrile) and 2,2-azobis(2,4,4-trimethylpentane); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, and 2-N-ethylanilinoethanol. tertiary amines such as tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition type radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetonate; compounds obtained by dissolving these organic metal salts in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organic tin compounds such as dioctyltin oxide, other alkyltins, and alkyltin oxides. Among these, a preferred curing accelerator is at least one selected from the group consisting of imidazoles, organic metal salts, and organic peroxides, more preferably at least one selected from the group consisting of imidazoles and organic peroxides, and even more preferably an organic peroxide.

[0194] When the resin composition of this embodiment contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.05 parts by mass or more, and even more preferably 0.08 parts by mass or more, per 100 parts by mass of the resin solids in the resin composition. The upper limit of the curing accelerator content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, even more preferably 2 parts by mass or less, even more preferably 1.0 parts by mass or less, even more preferably 0.8 parts by mass or less, even more preferably 0.5 parts by mass or less, and even more preferably 0.3 parts by mass or less, and may be 0.2 parts by mass or less, 0.15 parts by mass or less, depending on the application. The resin composition of this embodiment is preferred because the resin composition can be sufficiently cured even when the content of the curing accelerator is below the upper limit. The curing accelerators can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0195] <Filler> The resin composition of this embodiment may contain a filler. By including a filler, the dielectric properties (dielectric constant and / or dielectric dissipation factor), flame resistance, low thermal expansion, and other physical properties of the resin composition and its cured product can be further improved. Furthermore, the filler used in this embodiment preferably has excellent low dielectric properties (Dk and / or Df). For example, the filler used in this embodiment preferably has a dielectric constant (Dk) of 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less at a frequency of 10 GHz, as measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the dielectric constant is, for example, 2.0 or more. Furthermore, the filler used in this embodiment preferably has a dielectric dissipation factor (Df) of 0.05 or less, more preferably 0.01 or less at a frequency of 10 GHz, as measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the dielectric dissipation factor is, for example, 0.0001 or more.

[0196] The filler used in this embodiment is not particularly limited in type, and can suitably be used as the one generally used in this industry.Specifically, silica such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, etc. metal oxide, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, etc. composite oxide, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, etc. nitride, aluminum hydroxide, aluminum hydroxide heat treatment product (aluminum hydroxide is heat treated, and part of crystal water is reduced), boehmite, magnesium hydroxide, etc. metal hydroxide (including hydrate), acid Examples of fillers include molybdenum compounds such as molybdenum chloride 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, short glass fibers (including fine glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, and spherical glass, as well as 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. In this embodiment, inorganic fillers are preferred, and more preferably contain one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. From the viewpoint of low dielectric properties (Dk and / or Df), more preferably contain one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferably contain silica. By using these inorganic fillers, the properties of the cured product of the resin composition, such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy, are further improved.

[0197] The content of the filler in the resin composition of this embodiment can be appropriately set depending on the desired properties and is not particularly limited. It is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 30 parts by mass or more, 50 parts by mass or more, 100 parts by mass or more, or 120 parts by mass or more. By setting it at or above the lower limit, the low thermal expansion and low dielectric loss tangent of the resulting cured product tend to be more excellent. Furthermore, the upper limit of the filler content is preferably 300 parts by mass or less, more preferably 250 parts by mass or less, even more preferably 200 parts by mass or less, and even more preferably 180 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 150 parts by mass or less, or 100 parts by mass or less. Setting it at or below the upper limit tends to further improve the moldability of the resin composition. In the resin composition of this embodiment, as an example of a preferred embodiment, the content of the filler is 1 to 95% by mass of the components excluding the solvent, preferably 10 to 50% by mass, and more preferably 10 to 30% by mass. The resin composition of this embodiment may contain only one type of filler, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0198] When a filler, particularly an inorganic filler, is used in the resin composition of this embodiment, a silane coupling agent may be further contained. The inclusion of a silane coupling agent tends to further improve the dispersibility of the filler and the adhesive strength between the resin component and the filler and the substrate described below. The silane coupling agent is not particularly limited, and examples thereof include silane coupling agents generally used for the surface treatment of inorganic substances, such as aminosilane compounds (e.g., γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, etc.), epoxysilane compounds (e.g., γ-glycidoxypropyltrimethoxysilane, etc.), vinylsilane compounds (e.g., vinyltrimethoxysilane, vinyltriethoxysilane, tetravinylsilane, triethylvinylsilane, 1,3-vinyltetramethylsiloxane, etc.), styrylsilane compounds (e.g., 4-vinylphenyltrimethoxysilane, etc.), acrylicsilane compounds (e.g., γ-acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds. Among these, it is preferable to include at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylicsilane compounds, with vinylsilane compounds being more preferable. The silane coupling agent may be used alone or in combination of two or more. The content of the silane coupling agent is not particularly limited, but may be 0.1 to 5.0 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0199] <Elastomer> The resin composition of this embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but is preferably thermoplastic. The elastomer of this embodiment is not particularly limited, and examples thereof include at least one selected from the group consisting of 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, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. Examples of elastomers include oligomers or polymers having a curable vinyl functional group and polybutadiene resins described in paragraphs 0044 and 0045 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0200] The number-average molecular weight of the elastomer (preferably a thermoplastic elastomer) used in this embodiment is preferably 1,000 or more. By setting the number-average molecular weight to 1,000 or more, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent). The number-average molecular weight is preferably 1,500 or more, more preferably 2,000 or more, and may be 600,000 or more, 700,000 or more, or 800,000 or more depending on the application. The upper limit of the number-average molecular weight of the elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. Setting the number-average molecular weight below the upper limit tends to improve the solubility of the elastomer component in the resin composition. When the resin composition of this embodiment contains two or more elastomers, it is preferable that the number-average molecular weight of the mixture thereof falls within the above range.

[0201] The elastomer used in this embodiment may be a resin containing a polybutadiene structure. The polybutadiene structure may be partially or completely hydrogenated. Specific examples include B-1000, B-2000, B-3000, BI-2000, and BI-3000 manufactured by Nippon Soda Co., Ltd., and Ricon 100, Ricon 130, Ricon 131, Ricon 142, Ricon 150, Ricon 181, and Ricon 184 manufactured by CRAY VALLEY.

[0202] The elastomer used in this embodiment may be a resin having a poly(meth)acrylate structure, such as Teisan Resin manufactured by Nagase ChemteX Corporation, and ME-2000, W-197C, KG-15, and KG-3000 manufactured by Negami Chemical Industrial Co., Ltd.

[0203] The elastomer used in this embodiment may be a resin having a polycarbonate structure. Resins having a polycarbonate structure are sometimes referred to as "polycarbonate resins." Examples of such resins include carbonate resins without reactive groups, hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, urethane group-containing carbonate resins, and epoxy group-containing carbonate resins. Here, the term "reactive group" refers to a functional group capable of reacting with other components, such as a hydroxyl group, a phenolic hydroxyl group, a carboxyl group, an acid anhydride group, an isocyanate group, a urethane group, or an epoxy group. Specific examples of polycarbonate resins include FPC0220 and FPC2136 manufactured by Mitsubishi Gas Chemical Company, Inc., and T6002 and T6001 (polycarbonate diol) manufactured by Asahi Kasei Corporation.

[0204] The elastomer used in this embodiment is a resin having a polysiloxane structure, such as SMP-2006, SMP-2003PGMEA, SMP-5005PGMEA, KR-510, and SMP-7014-3S manufactured by Shin-Etsu Silicones Co., Ltd.

[0205] The elastomer used in this embodiment may be a resin having a polyalkylene structure and / or a polyalkyleneoxy structure. The polyalkyleneoxy structure is preferably a polyalkyleneoxy structure having 2 to 15 carbon atoms, more preferably a polyalkyleneoxy structure having 3 to 10 carbon atoms, and particularly preferably a polyalkyleneoxy structure having 5 to 6 carbon atoms. Specific examples of resins having a polyalkylene structure and / or a polyalkyleneoxy structure include PTXG-1000 and PTXG-1800 manufactured by Asahi Kasei Fibers Corporation.

[0206] The elastomer used in this embodiment is a resin having a polyisoprene structure, such as KL-610 and KL613 manufactured by Kuraray Co., Ltd.

[0207] The elastomer used in this embodiment is a resin having a polyisobutylene structure, such as SIBSTAR-073T (styrene-isobutylene-styrene triblock copolymer) and SIBSTAR-042D (styrene-isobutylene diblock copolymer), both manufactured by Kaneka Corporation.

[0208] In this embodiment, the elastomer is preferably an elastomer containing styrene monomer units and conjugated diene monomer units (hereinafter referred to as "elastomer (e)"). By using such elastomer (e), the low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent) of the resulting cured product are more excellent.

[0209] The elastomer (e) contains a styrene monomer unit. The inclusion of the styrene monomer unit improves the solubility of the elastomer (e) in the resin composition. Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Among these, styrene, α-methylstyrene, and p-methylstyrene are preferred from the standpoints of availability and productivity. Of these, styrene is particularly preferred. The content of the styrene monomer unit in the elastomer (e) is preferably 10% by mass or more, more preferably 13% by mass or more, and even more preferably 15% by mass or more, of the total monomer units, and is preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less. By ensuring that the content of the styrene monomer unit is equal to or less than the above upper limit, adhesion and tackiness to substrates and the like are improved. Furthermore, when the content of the styrene monomer unit is equal to or greater than the lower limit, the adhesion can be suppressed, adhesive residue and stop marks are less likely to occur, and the adhesive surfaces tend to be easily peeled from each other, which is preferable. The elastomer (e) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range. The method for measuring the content of the styrene monomer unit in the elastomer (e) of this embodiment can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the conjugated diene monomer units and the like described below.

[0210] The elastomer (e) contains a conjugated diene monomer unit. The inclusion of the conjugated diene monomer unit improves the solubility of the elastomer (e) in a resin composition. The conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds. Examples of the conjugated diene monomer include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene. 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. The elastomer (e) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

[0211] In the elastomer (e), the mass ratio of the styrene monomer units to the conjugated diene monomer units (styrene monomer units / conjugated diene monomer units) is preferably in the range of 5 / 95 to 80 / 20, more preferably 7 / 93 to 77 / 23, and even more preferably 10 / 90 to 70 / 30. When the mass ratio of the styrene polymer units to the conjugated diene monomer units is in the range of 5 / 95 to 80 / 20, it is possible to suppress the increase in adhesion, maintain high adhesive strength, and improve the ease of peeling between adhesive surfaces.

[0212] The conjugated diene bonds of the elastomer (e) may be entirely hydrogenated, partially hydrogenated, or not hydrogenated at all.

[0213] The elastomer (e) may or may not contain other monomer units in addition to the styrene monomer units and the conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than styrene monomer units. The total of the styrene monomer units and the conjugated diene monomer units in the elastomer (e) is preferably 90% by mass or more, more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more, of the total monomer units. As described above, the elastomer (e) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0214] The elastomer (e) used in this embodiment may be a block polymer or a random polymer. It may be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, an unhydrogenated elastomer in which no hydrogenation is performed, or a partially hydrogenated elastomer in which only a portion of the conjugated diene monomer units are hydrogenated. An unhydrogenated elastomer or a partially hydrogenated elastomer is preferred. In one embodiment of this embodiment, the elastomer (e) is a hydrogenated elastomer. Here, the term "hydrogenated elastomer" refers to an elastomer in which the double bonds based on the conjugated diene monomer units in the elastomer are hydrogenated, and includes elastomers with a hydrogenation rate (hydrogenation rate) of 80% or more as well as elastomers with a hydrogenation rate (hydrogenation rate) of 100%. The hydrogenation rate of the hydrogenated elastomer is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more. In this embodiment, the hydrogenation rate is 1It is calculated from the results of H-NMR spectrum measurement. In one embodiment of this embodiment, the elastomer (e) is an unhydrogenated elastomer. Here, the unhydrogenated elastomer refers to an elastomer in which the proportion of hydrogenated double bonds based on conjugated diene monomer units in the elastomer, i.e., the hydrogenation rate (hydrogenation rate) is 20% or less. The hydrogenation rate is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less. On the other hand, a partially hydrogenated elastomer refers to an elastomer in which some of the double bonds based on conjugated diene monomer units in the elastomer are hydrogenated, and typically refers to an elastomer in which the hydrogenation rate (hydrogenation rate) is less than 80% but more than 20%.

[0215] Examples of commercially available elastomers (e) used in this embodiment include SEPTON (registered trademark) 2104, V9461, and S8104 manufactured by Kuraray Co., Ltd., S.O.E. (registered trademark) S1606, S1613, S1609, and S1605 manufactured by Asahi Kasei Corporation, Tuftec (registered trademark) H1041, H1043, P2000, and MP10 manufactured by Asahi Kasei Corporation, and DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Corporation.

[0216] The elastomer used in this embodiment may also be a liquid diene. Liquid diene refers to a liquid elastomer containing a conjugated diene monomer unit. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene. 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. Examples of liquid dienes used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, liquid acrylonitrile-butadiene copolymer, and liquid styrene-butadiene copolymer. The number average molecular weight of the liquid diene is not particularly limited as long as it is liquid at 20°C, but is preferably 500 or more and 10,000 or less.

[0217] The elastomer used in this embodiment may be the elastomer described in JP-A-2022-33057, for example, MD3501 manufactured by Kraton Corporation, as a commercially available product.

[0218] When the resin composition of this embodiment contains an elastomer (preferably elastomer (e)), the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 10 parts by mass or more, 12 parts by mass or more. By setting the content at or above the lower limit, the dielectric properties (low dielectric tangent) tend to be further improved. Furthermore, the upper limit of the elastomer content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 20 parts by mass or less, 15 parts by mass or less. Setting the content at or below the upper limit tends to further improve heat resistance. The resin composition of this embodiment may contain only one type of elastomer, or may contain two or more types. When two or more types of elastomers are contained, the total amount is preferably within the above range. The resin composition of the present embodiment may be configured to be substantially free of elastomer. "Substantially free" means that the content of elastomer is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0219] <Other Components> In addition to the above components, the resin composition of this embodiment may contain various polymeric compounds such as thermoplastic resins and their oligomers, petroleum resins, and various additives. Examples of additives include at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow control agents, lubricants, antifoaming agents, leveling agents, gloss agents, and polymerization inhibitors. Examples of polymerization inhibitors include quinones, phenols, nitroso, hydroxyamines, organic boric acid compounds, and compounds having a phenolic hydroxyl group. Specifically, 2-nitrophenol, 4-methoxyphenol, 4-tert-butylpyrocatechol, pyrogallol, tert-butylhydroquinone, 1,4-benzoquinone, 2-hydroxybenzophenone, cuprous chloride, phenothiazine, chloranil, naphthylamine, β-naphthol, 2,6-di-t-butyl-4-cresol, 2,2′-methylenebis(4-methyl- 6-t-butylphenol), pyridine, nitrobenzene, dinitrobenzene, picric acid, 4-toluidine, methylene blue, copper and organic chelating agent reaction products, methyl salicylate, dibutylhydroxytoluene, 1,1-diphenyl-2-picrylhydrazyl free radical, hydroquinone, hydroquinone monomethyl ether, mequinol, N-nitroso-N-phenylhydroxylamine aluminum, triethyl borate, tributyl borate, triisopropyl borate, 2,3-dihydroxynaphthalene, 4-methoxy-1-naphthol, methylhydroquinone, and the like. The polymerization inhibitor used is not limited to the above. The resin composition of this embodiment may also be substantially free of radical polymerization initiators (including those corresponding to photopolymerization initiators and those corresponding to curing accelerators). "Substantially free" means that the content of the radical polymerization initiator contained in the resin composition is less than 0.005 parts by mass, preferably less than 0.003 parts by mass, more preferably less than 0.001 parts by mass, and even more preferably less than 0.0001 parts by mass, per 100 parts by mass of the resin solid content.In the resin composition according to the present embodiment, the total content of the polyphenylene ether compound other than the polyphenylene ether compound described in the above section <<<Polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond>>> and the thermoplastic elastomer other than the elastomer described in the above section <<Elastomer>>> is preferably 3% by mass or less, more preferably 1% by mass or less, of the resin solids. This configuration allows the effects of the present invention to be more effectively exhibited. Furthermore, the total content of the polyphenylene ether compound other than the polyphenylene ether compound described in the above section <<<Polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond>>> and the butadiene-based elastomer not containing a styrene skeleton is preferably 3% by mass or less, more preferably 1% by mass or less, of the resin solids. This configuration allows the effects of the present invention to be more effectively exhibited. Furthermore, the total content of the polyphenylene ether compound other than the polyphenylene ether compound represented by formula (OP) and the butadiene-based elastomer not containing a styrene skeleton is preferably 3% by mass or less, more preferably 1% by mass or less, of the resin solids. By adopting such a configuration, the effects of the present invention can be more effectively exhibited.

[0220] <Applications> 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-tangent material, such as an insulating layer for a printed wiring board, a semiconductor package material, or other electronic material resin composition. The resin composition of this embodiment can be suitably used as a material for a prepreg, a metal foil-clad laminate using a prepreg, a resin composite sheet, and a printed wiring board.

[0221] The resin composition of this embodiment preferably has a low dielectric constant (Dk) and dielectric loss tangent (Df) when cured. The resin composition of this embodiment, when molded into a 1.0 mm thick cured plate (without metal foil), preferably has a dielectric constant (Dk) of 2.50 or less at a frequency of 10 GHz, as measured by a cavity resonator perturbation method. The lower limit of the dielectric constant (Dk) is not particularly specified, but a practical value is, for example, 0.01 or more. Furthermore, the dielectric loss tangent (Df) at a frequency of 10 GHz, as measured by a cavity resonator perturbation method, when molded into a 1.0 mm thick cured plate (without metal foil) is preferably 0.0020 or less, more preferably 0.0015 or less. The lower limit of the dielectric loss tangent (Df) is not particularly specified, but a practical value is, for example, 0.0001 or more. This can also be achieved by curing the resin composition by radical curing. Radical curing tends to cure rapidly within a specific temperature range, allowing the resin composition to be cured more densely, thereby improving the low dielectric properties (Dk and / or Df) of the resulting cured product. That is, an example of the resin composition of this embodiment is a radically curable resin composition. More specifically, the dielectric loss tangent (Df) and relative dielectric constant (Dk) of the cured product are measured by the method described in the Examples below.

[0222] The resin composition of this embodiment also preferably has a small coefficient of thermal expansion when cured. When the resin composition of this embodiment is molded into a 1.0 mm thick cured plate (without metal foil), the temperature is raised from 25 ° C to 303 ° C at a rate of 10 ° C per minute, cooled, and then heated again from 25 ° C to 303 ° C. The thermal expansion coefficient from 260 ° C to 280 ° C is preferably 200 ppm / ° C or less, more preferably 160 ppm / ° C or less, and even more preferably 100 ppm / ° C or less, and practically 0 ppm / ° C or more. Furthermore, when the same sample is measured in the same manner as above, the thermal expansion coefficient from 50 ° C to 280 ° C is preferably 100 ppm / ° C or less, more preferably 70 ppm / ° C or less, and practically 0 ppm / ° C or more.

[0223] The resin composition of this embodiment also desirably has a high glass transition temperature (Tan σ) when cured. When the resin composition of this embodiment is molded into a 1.0 mm thick cured plate (without metal foil), the glass transition temperature (Tan δ) measured using a dynamic mechanical analyzer (DMA) in accordance with JIS C6481 5.17.2 is preferably 250°C or higher. The upper limit of the glass transition temperature (Tan δ) is not particularly specified, but is, for example, 400°C or lower.

[0224] The resin composition of this embodiment is used as a layered material (including film and sheet forms) such as a prepreg or resin composite sheet that serves as an insulating layer for a printed wiring board. When used as such a layered material, the thickness is preferably 5 μm or more, more preferably 10 μm or more. The upper limit of the thickness is preferably 200 μm or less, more preferably 180 μm or less. Note that the thickness of the layered material refers to the thickness including the glass cloth, for example, when the resin composition of this embodiment is impregnated into glass cloth or the like. Materials formed from the resin composition of this embodiment may be used in applications where a pattern is formed by exposure and development, or in applications where exposure and development are not required. They are particularly suitable for applications where exposure and development are not required.

[0225] <<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 can be obtained, for example, by applying the resin composition of this embodiment to the substrate (e.g., by impregnation and / or coating) and then semi-curing by heating (e.g., by drying at 120 to 220°C for 2 to 15 minutes). In this case, the amount of resin composition attached to the substrate, i.e., the amount of resin composition (including filler) relative to the total amount of semi-cured prepreg, is preferably in the range of 20 to 99% by mass, and more preferably in the range of 20 to 80% by mass.

[0226] The substrate is not particularly limited as long as it is a substrate used in various printed wiring board materials. Examples of the material of the substrate 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 examples include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc. These substrates may be used alone or in combination of two or more. Among these substrates, from the viewpoint of dimensional stability, woven fabrics that have been subjected to an ultra-opening treatment and a clogging treatment are preferred. 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 / m ２ The following glass woven fabrics are preferred, and from the viewpoint of moisture absorption and heat resistance, glass woven fabrics that have been surface-treated with epoxy silane, amino silane, or the like are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers exhibiting a low relative dielectric constant and low dielectric dissipation factor, such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. Examples of substrates with a low relative dielectric constant include substrates with a relative dielectric constant of 5.0 or less (preferably, 3.0 to 4.9). Examples of substrates with a low dielectric dissipation factor include substrates with a dielectric dissipation factor of 0.006 or less (preferably, 0.001 to 0.005). The relative dielectric constant and dielectric dissipation factor are values ​​measured at a frequency of 10 GHz using a perturbation method cavity resonator.

[0227] <<Metal Foil-Clad Laminate>> The metal foil-clad laminate of this embodiment includes at least one layer formed from the prepreg of this embodiment and a metal foil disposed on one or both sides of the layer formed from the prepreg. Examples of methods for producing the metal foil-clad laminate of this embodiment include a method in which at least one prepreg of this embodiment (preferably two or more prepregs) is disposed, and a metal foil is disposed on one or both sides of the prepreg, followed by laminate molding. More specifically, the laminate can be produced by disposing a metal foil, such as copper or aluminum, on one or both sides of the prepreg and then laminating the prepreg. The number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil may be any foil suitable for use in printed wiring boards, including, but not limited to, copper foils 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 approximately 1.5 to 70 μm. Furthermore, when copper foil is used as the metal foil, the copper foil preferably has a surface roughness Rz of 0.2 to 4.0 μm, as measured in accordance with JIS B0601:2013. By adjusting the surface roughness Rz to 0.2 μm or more, the copper foil surface roughness becomes appropriate, and the copper foil peel strength tends to be further improved. On the other hand, by adjusting the surface roughness Rz to 4.0 μm or less, the copper foil surface roughness becomes appropriate, and the dielectric loss tangent characteristics of the resulting cured product tend to be further improved. From the viewpoint of the dielectric loss tangent characteristics and copper foil peel strength of the resulting cured product, the copper foil surface roughness Rz is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, particularly preferably 0.7 μm or more, and more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0228] Examples of laminate molding methods include those commonly used when molding printed wiring board laminates and multilayer boards. More specifically, examples include methods using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, or the like, at a temperature of about 180 to 350°C, a heating time of about 100 to 300 minutes, and a surface pressure of about 1 to 10 MPa. A multilayer board can also be produced by combining the prepreg of this embodiment with a separately prepared inner layer wiring board for laminate molding. A multilayer board can be produced, for example, by placing copper foil of about 35 μm on both sides of a single prepreg of this embodiment, laminating using the molding method described above, forming an inner layer circuit, and blackening this circuit to form an inner layer circuit board. Then, this inner layer circuit board and the prepreg of this embodiment are alternately arranged one by one, and copper foil is placed on the outermost layer. This laminate molding can be carried out under the above conditions, preferably under vacuum, to produce a multilayer board. The metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.

[0229] 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 5.7 "Peel Strength" of JIS C6481. There is no particular upper limit to the peel strength, but even if it is 2.00 kN / m or less, the required performance is sufficiently met.

[0230] As described above, the resin composition for electronic materials obtained using the resin composition of the present embodiment (a resin composition including a combination of specific components) can produce a cured product that has low dielectric properties (low dielectric constant, low dielectric dissipation factor), low thermal expansion, heat resistance, and excellent appearance of the cured product, as well as excellent properties such as moisture absorption and heat resistance, peel strength against metal foil, desmear resistance, crack resistance, and high-density processability.

[0231] <<Printed Wiring Board>> The printed wiring board of this embodiment includes an insulating layer and a conductor 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 wiring board can be manufactured using conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is described below. First, a metal foil-clad laminate, such as the copper foil-clad laminate described above, is prepared. Next, the surface of the metal foil-clad laminate is etched to form an inner layer circuit, thereby producing an inner layer substrate. If necessary, the surface of the inner layer circuit of this inner layer substrate is subjected to a surface treatment to increase adhesive strength. Next, a required number of the prepregs described above are stacked on the surface of the inner layer circuit, and metal foil for an outer layer circuit is further laminated on the outside, followed by heating and pressurizing to form an integral mold. In this way, a multilayer laminate is manufactured, in which an insulating layer composed of a substrate 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, this multilayer laminate is subjected to hole drilling for through holes or via holes, and then a plated metal film that connects the inner layer circuit and the metal foil for the outer layer circuit is formed on the wall surface of the hole, and the metal foil for the outer layer circuit is further etched to form the outer layer circuit, thereby producing a printed wiring board.

[0232] The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of this insulating layer, and the insulating layer contains the resin composition of the present embodiment described above and / or its cured product. That is, the prepreg of the present embodiment described above (for example, a prepreg formed from a base material and the resin composition of the present embodiment impregnated or applied thereto), or the layer formed from the resin composition of the metal foil-clad laminate of the present embodiment described above, serves as the insulating layer of the present embodiment. This embodiment also relates to a semiconductor device including the printed wiring board. For details of the semiconductor device, please refer to paragraphs 0200 to 0202 of JP 2021-021027 A, the contents of which are incorporated herein by reference.

[0233] Furthermore, it is preferable that the insulating layer formed from the cured product of the resin composition of this embodiment has a small surface roughness after roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after 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 may be, for example, 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 magnification lens. The non-contact surface roughness meter used is a WYKONT3300 manufactured by Veeco Instruments.

[0234] <<Resin Composite Sheet>> The resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment and 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. There are no particular limitations on the method for producing the resin composite sheet, but examples include a method of obtaining a resin composite sheet by applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent to a support and drying the applied solution.

[0235] Examples of the support used here include, but are not limited to, polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and release films obtained by applying a release agent to the surface of these films, organic film substrates such as polyimide film, conductive foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, FRP (Fiber-Reinforced Plastics), and other plate-shaped materials.

[0236] Examples of application methods (coating methods) include methods in which a solution of the resin composition of this embodiment dissolved in a solvent is applied to a support using a bar coater, die coater, doctor blade, baker applicator, or the like. Furthermore, after drying, a single-layer sheet can be obtained by peeling or etching the support from a resin composite sheet in which the support and the resin composition are laminated. It should be noted that a single-layer sheet can also be obtained without using a support by supplying a solution of the resin composition of this embodiment dissolved in a solvent into a mold having a sheet-shaped cavity and drying it to form it into a sheet.

[0237] In the production of the monolayer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited. However, because low temperatures tend to leave the solvent in the resin composition, and high temperatures accelerate curing of the resin composition, drying conditions of 20°C to 200°C for 1 to 90 minutes are preferred. The monolayer 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-staged) state as needed. Furthermore, the thickness of the resin layer in the monolayer sheet or resin composite sheet of this embodiment can be adjusted by the concentration and coating thickness of the solution of the resin composition of this embodiment used for coating (coating). While not particularly limited, a thickness of 0.1 to 500 μm is preferred because a thicker coating thickness generally leads to more solvent remaining during drying.

[0238] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing 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 the like, measurements can be made using other instruments with equivalent performance.

[0239] <Measurement of Weight-Average Molecular Weight and Number-Average Molecular Weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of compounds (including resins) were measured by gel permeation chromatography (GPC) using a liquid pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Showa Denko K.K., GPC KF-801, 802, 803, 804), with tetrahydrofuran as the solvent, a flow rate of 1.0 mL / min, and a column temperature of 40°C, using a calibration curve prepared using monodisperse polystyrene.

[0240] <Measurement of parameters α and β> The parameters α and β in the resin (A) are determined by the following methods: １ The calculated values ​​were calculated by H-NMR measurement. The synthesized resin was dissolved in a mixed solvent of heptane and methanol, and the procedure of drying and solidifying was repeated to remove the residual solvent contained in the recovered solid. Then, the recovered solid was dissolved in CDCl ３ (containing 0.03% by volume of TMS (tetramethylsilane)), １ H-NMR measurement was carried out. １ In H-NMR, the parameters α and β of each resin were calculated using the following formula, where the peak position of TMS (tetramethylsilane) was set to 0 ppm. (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.)

[0241] Synthesis Example 1: Synthesis of Resin (A1) A flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 0.75 g of activated clay, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), and a stirrer, and the mixture was heated to an internal temperature of 50°C while stirring. The mixture was then gradually heated to an internal temperature of 70°C over 5 hours and allowed to react for an additional hour at an internal temperature of 70°C. After allowing the mixture to cool, the activated clay was removed by filtration, and the solvent was distilled off under reduced pressure with heating to obtain 129 g of a solid resin. The resulting resin (A) had an Mw of 1193, an Mn of 693, and an Mw / Mn ratio of 1.7. In formula (Tx), the parameter α was 0.63, the parameter β was 1.07, and n + o + p was 3.4. The structures in parentheses (a), (b), and (c) in formula (Tx) all have the same molecular weight, and n+o+p was calculated assuming that Mn of the synthesized resin is the average molecular weight. Furthermore, GPC analysis confirmed that the residual monomer was 1% by mass or less. The obtained resin (A1) was analyzed using the following formula (Tx) in Figure 1. １ The H-NMR chart is shown.

[0242] Synthesis Example 2: Synthesis of Resin (A2) A flask equipped with a thermometer, a Dean-Stark apparatus, and a stirrer was charged with 184.5 g of m-bis(α-hydroxyisopropyl)benzene (product name: Metadiol, manufactured by Sumitomo Chemical Co., Ltd.), 125 g of toluene, 0.12 g of p-toluenesulfonic acid monohydrate, and 0.4 g of pure water. The internal temperature was raised to 120°C while aerating nitrogen, and the reaction was carried out for 4 hours. 1,3-diisopropenylbenzene was generated by the dehydration reaction (the amount of dehydration was 34.1 g, almost the theoretical amount). After cooling, 300 g of toluene and 200 g of pure water were added, and the waste liquid was repeatedly washed with 200 g of pure water until it became neutral, thereby obtaining a product in the form of a solution. The system was reduced in pressure and concentrated, yielding 300 g of a toluene solution containing 1,3-diisopropenylbenzene. A flask equipped with a thermometer, a condenser, and a stirrer was charged with 260 g of toluene and 1.5 g of activated clay, and the mixture was heated to an internal temperature of 70°C while stirring. Subsequently, 150 g of the aforementioned 1,3-diisopropenylbenzene-containing toluene solution was added dropwise, controlling the rate of addition so that the internal temperature did not exceed 80°C. After the addition, the mixture was stirred until the internal temperature dropped to 70°C. Subsequently, 150 g of the aforementioned 1,3-diisopropenylbenzene-containing toluene solution was added dropwise in the same manner, and the mixture was allowed to react for an additional 1.5 hours after the completion of the addition. At the end of the reaction, 400 g of toluene was added, and the solid matter was removed by filtration. The filtrate was heated under reduced pressure to distill off the solvent, yielding 123 g of a solid resin. The resulting resin (A2) had an Mw of 1980, an Mn of 890, and an Mw / Mn of 2.2. In formula (Tx), the parameter α was 0.66, the parameter β was 0.78, and n + o + p was 4.6. The structures in parentheses represented by (a), (b), and (c) in formula (Tx) all have the same molecular weight, and n + o + p was calculated assuming that Mn of the synthesized resin was the average molecular weight. Furthermore, GPC analysis confirmed that the residual monomer was 1% by mass or less. The functional group equivalent (isopropenyl group equivalent) of the obtained resin (A2) was 571 g / eq. The functional group equivalent (g / eq.) of resin (A2) was calculated by (number average molecular weight (Mn) ÷ 2) ÷ β.

[0243] Synthesis Example 3: Synthesis of Resin (A3) A flask equipped with a thermometer, a Dean-Stark apparatus, and a stirrer was charged with 184.5 g of m-bis(α-hydroxyisopropyl)benzene (product name: Metadiol, manufactured by Sumitomo Chemical Co., Ltd.), 125 g of toluene, 0.12 g of p-toluenesulfonic acid monohydrate, and 0.4 g of pure water. The internal temperature was raised to 120°C while aerating nitrogen, and the reaction was carried out for 4 hours. 1,3-diisopropenylbenzene was generated by the dehydration reaction (the amount of dehydration was 34.1 g, almost the theoretical amount). After cooling, 300 g of toluene and 200 g of pure water were added, and the waste liquid was repeatedly washed with 200 g of pure water until it became neutral, thereby obtaining a product in the form of a solution. The system was reduced in pressure and concentrated, yielding 300 g of a toluene solution containing 1,3-diisopropenylbenzene. A flask equipped with a thermometer, a condenser, and a stirrer was charged with 130 g of toluene, 0.3 g of activated clay, and 300 g of the aforementioned 1,3-diisopropenylbenzene-containing toluene solution, and the mixture was heated to an internal temperature of 50 °C while stirring. The mixture was then gradually heated to an internal temperature of 80 °C over 5 hours and allowed to react for an additional hour at an internal temperature of 80 °C. After cooling, the catalyst was removed by filtration, and the solvent was distilled off under reduced pressure with heating to obtain 129 g of a solid resin. The resulting resin (A3) had an Mw of 1,380, an Mn of 710, an Mw / Mn ratio of 1.9, and in formula (Tx), the parameter α was 0.81, the parameter β was 0.88, and n + o + p was 3.5. The structures in parentheses represented by (a), (b), and (c) in formula (Tx) all have the same molecular weight, and n + o + p was calculated assuming that the Mn of the synthesized resin was the average molecular weight. Furthermore, GPC analysis confirmed that the residual monomer content was 1% by mass or less. The functional group equivalent (isopropenyl group equivalent) of the resulting resin (A3) was 403 g / eq. The functional group equivalent (g / eq.) of resin (A3) was calculated by (number average molecular weight (Mn) ÷ 2) ÷ β.

[0244] Example 1 37 parts by mass of the resin (A1) obtained in Synthesis Example 1 above and 63 parts by mass of resin (B1) (BMI-70, manufactured by K.I. Chemical Co., Ltd.) were dissolved in methyl ethyl ketone and toluene and mixed to obtain a varnish. The blending amounts of each component mentioned above are expressed as solid content values.

[0245] <Production of 1.0 mm Thick Cured Plate Test Pieces> The solvent was evaporated and removed from the resulting varnish to obtain a resin composition powder. Using the resulting resin composition powder, a cured plate was produced as follows. 4.5 g of the resin composition powder was placed in a stainless steel mold frame measuring 100 mm x 30 mm x 1.0 mm high, placed in a vacuum press (manufactured by Kitagawa Seiki Co., Ltd.), and held at 200°C for 2 hours, pressing at a surface pressure of 3.0 MPa. The resulting cured plate was used to evaluate the dielectric constant (Dk), dielectric loss tangent (Df), coefficient of thermal expansion (CTE), and glass transition temperature (Tg). The evaluation results are shown in the table below.

[0246] <Measurement and Evaluation Methods> <Dielectric Properties> The obtained cured plate was downsized to a width of 1.0 mm and then dried at 120°C for 60 minutes. The relative permittivity (Dk) and dielectric loss tangent (Df) at a frequency of 10 GHz were measured for the dried sample using a perturbation method cavity resonator. The measurement temperature was 23°C. The measurement results were evaluated as follows. The perturbation method cavity resonator used was a P5005A manufactured by Keysight Technologies.

[0247] <<Relative permittivity (Dk)>> A: 2.50 or less B: More than 2.50 <<Dielectric loss tangent (Df)>> A: 0.0015 or less B: More than 0.0015 and 0.0020 or less C: More than 0.0020

[0248] <Coefficient of linear thermal expansion (CTE)> The cured plate (cured at 200°C) was downsized to a 3.0 mm square sample, and the coefficient of thermal expansion was measured by the TMA (Thermo-Mechanical Analysis) method in accordance with JIS C 6481 5.19 to determine the value. The unit is ppm / °C. A thermomechanical analyzer, TMAQ400, manufactured by TA Instruments Co., Ltd., was used, and the sample was heated from 25°C to 303°C at a rate of 10°C per minute, cooled, and then heated again from 25°C to 303°C for measurement. The measurement results were evaluated as follows. α ２ indicates the thermal expansion coefficient at 260 to 280°C, and α ｔｏｔａｌindicates the thermal expansion coefficient from 50 to 280°C. The measurement results were evaluated as follows: (α ２ ) A: 100ppm / °C or less B: More than 100ppm / °C and 160ppm / °C or less C: More than 160ppm / °C and 200ppm / °C or less D: More than 200ppm / °C (α ｔｏｔａｌ ) A: 70ppm / °C or less B: More than 70ppm / °C and 100ppm / °C or less C: More than 100ppm / °C

[0249] <Glass Transition Temperature (Tg)> The cured sheet was downsized to 12.7 mm x 30 mm, and a sample was measured using a dynamic viscoelasticity measuring device by the DMA (Dynamic Mechanical Analysis) bending method in accordance with JIS C6481 5.17.2. The peak temperature of the obtained loss tangent (Tan δ) was taken as the glass transition temperature. The unit is °C. The dynamic viscoelasticity analyzer used was a DMA 850 manufactured by TA Instruments Co., Ltd. The measurement results were evaluated as follows: A: 250°C or higher B: Less than 250°C C: The sample broke during measurement and could not be measured.

[0250] Example 2 The same procedure as in Example 1 was carried out, except that the content of resin (A1) was changed to 50 parts by mass and the content of resin (B1) was changed to 50 parts by mass.

[0251] Example 3 The same procedure as in Example 1 was carried out, except that the content of resin (A1) was changed to 60 parts by mass and the content of resin (B1) was changed to 40 parts by mass.

[0252] Example 4 The same procedure as in Example 1 was carried out except that 1 part by mass of 2-nitrophenol (polymerization inhibitor, manufactured by Tokyo Chemical Industry Co., Ltd.) was added.

[0253] Example 5 The same procedure as in Example 1 was carried out except that the content of resin (A1) was changed to 29 parts by mass, the content of resin (B1) was changed to 57 parts by mass, and 13 parts by mass of 1,2-bis(4-vinylphenyl)ethane (manufactured by Angene International) was added.

[0254] Example 6 The same procedure as in Example 1 was carried out except that the resin (A1) was not blended, 50 parts by mass of the resin (A2) obtained in Synthesis Example 2 was blended, and the content of the resin (B1) was 50 parts by mass.

[0255] Example 7 The same procedure as in Example 1 was carried out except that no resin (A1) was added, 50 parts by mass of resin (A2) obtained in Synthesis Example 2 was added, the content of resin (B1) was 50 parts by mass, and the content of manganese octylate (manufactured by Nippon Chemical Industry Co., Ltd.) was 0.1 parts by mass.

[0256] Example 8 The same procedure as in Example 1 was carried out except that the resin (A1) was not blended, 50 parts by mass of the resin (A3) obtained in Synthesis Example 3 was blended, and the content of the resin (B1) was 50 parts by mass.

[0257] Comparative Example 1 The same procedures as in Example 1 were carried out, except that the content of resin (A1) was changed to 45 parts by mass, resin (B1) was not blended, and 55 parts by mass of resin (B2) (NE-X-9470S, manufactured by DIC Corporation, a maleimide compound corresponding to formula (M1)) was blended.

[0258] Comparative Example 2 The same procedures as in Example 1 were carried out except that the content of resin (A1) was changed to 50 parts by mass, resin (B1) was not blended, and 50 parts by mass of resin (B3) (NE-X-9500 manufactured by DIC Corporation, equivalent to maleimide compound (M7)) was blended.

[0259] Comparative Example 3 The same procedures as in Example 1 were carried out, except that the content of resin (A1) was changed to 60 parts by mass, resin (B1) was not blended, and 40 parts by mass of resin (B4) (manufactured by Nippon Kayaku Co., Ltd., MIR-3000-70MT, a maleimide compound corresponding to formula (M3)) was blended.

[0260] Comparative Example 4 The same procedure as in Example 1 was carried out, except that resin (B1) was not blended and 63 parts by mass of resin (B2) was blended.

[0261] Comparative Example 5 The same procedures as in Example 1 were carried out except that the content of resin (A1) was changed to 45 parts by mass, resin (B1) was not blended, and 55 parts by mass of resin (B4) was blended.

[0262]

[0263]

[0264]

[0265] Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various modifications can be made without departing from the spirit and scope of the invention.

Claims

1. A resin composition comprising 10 to 90 parts by mass of a resin (A) and 90 to 10 parts by mass of a maleimide compound (B) represented by formula (M4), wherein the resin (A) is a resin represented by formula (T). (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and R represents a divalent group.) (In formula (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group.

2. The resin composition according to claim 1, wherein R is a group containing an indane structure.

3. The resin composition according to claim 1, wherein R is a group containing the following structure: (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) 4. The resin composition according to claim 3, wherein the parameter α calculated from formula (α) in resin (A) is 0.20 or more and 1.00 or less, the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less, and the number average molecular weight of resin (A) is 400 to 3,000. (The brackets in formula (α) are: １ The integral between the corresponding chemical shift values ​​in H-NMR is shown, and the value in parentheses in formula (β) is １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) 5. The resin composition according to claim 1, wherein the compound represented by formula (M4) includes the following compound: (In the above formula, Me is a methyl group and Et is an ethyl group.) 6. The resin composition according to claim 1, wherein R is a group containing the following structure, wherein the parameter α calculated from formula (α) in resin (A) is 0.20 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less, and the number average molecular weight of resin (A) is 400 to 3,000, and the compound represented by formula (M4) includes the following compound: (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) (The brackets in formula (α) are: １ The integral between the corresponding chemical shift values ​​in H-NMR is shown, and the value in parentheses in formula (β) is １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In the above formula, Me is a methyl group and Et is an ethyl group.) 7. The resin composition according to any one of claims 1 to 6, further comprising a compound represented by formula (BV). (In formula (BV), each Md independently represents a hydrocarbon group having 1 to 12 carbon atoms; w represents an integer of 0 to 4; and r represents an integer of 0 to 6.) 8. The resin composition according to any one of claims 1 to 6, further comprising a filler.

9. The resin composition according to any one of claims 1 to 6, further comprising at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brightening agents, photosensitizers, dyes, pigments, thickeners, flow adjusters, lubricants, antifoaming agents, leveling agents, gloss agents, and polymerization inhibitors.

10. The resin composition according to any one of claims 1 to 6, which is used for a printed wiring board.

11. A cured product of the resin composition according to any one of claims 1 to 6.

12. A prepreg formed from a substrate and the resin composition according to any one of claims 1 to 6.

13. A metal foil clad laminate comprising at least one prepreg according to claim 12 and metal foil disposed on one or both sides of said prepreg.

14. A resin composite sheet comprising a support and a layer formed from the resin composition according to any one of claims 1 to 6, disposed on the surface of said support.

15. A printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of said insulating layer, wherein said insulating layer comprises a layer formed from the resin composition according to any one of claims 1 to 6.

16. A semiconductor device comprising the printed wiring board according to claim 15.

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