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

Abstract

To provide a resin composition that enables provision of a cured product exhibiting 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.SOLUTION: A resin composition according to the present disclosure contains 10 to 90 pts.mass of a resin (A) and 90 to 10 pts.mass of a compound (B) represented by formula (BV), wherein the resin (A) is a resin represented by formula (T).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[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. [Background technology]

[0002] In recent years, there has been an accelerating trend toward higher integration and miniaturization of semiconductor elements used in mobile terminals, electronic devices, communication devices, etc. Accordingly, there is a demand for technology that enables high-density packaging of semiconductor elements, and there is also a demand for improvements in printed wiring boards, such as substrates for mounting semiconductor elements, which occupy an important position in such packaging. Meanwhile, the applications of electronic devices and the like are becoming more diverse and expanding. Accordingly, the properties required of printed wiring boards, such as substrates for mounting semiconductor elements, and 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 of such proposals is the development of improved resin materials for prepregs and resin composite sheets. Such materials are described in Patent Documents 1 to 4. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2022-058409 [Patent Document 2] Patent Publication No. 2021-187893 [Patent Document 3] International Publication No. 2019 / 188189 [Patent Document 4] Japanese Patent Application Publication No. 2018-090728 Summary of the Invention [Problem to be solved by the invention]

[0004] As mentioned above, the applications of electronic devices and the like are diversifying and expanding, and new resin materials are being demanded for use in prepregs, etc. In particular, there is a demand for further development of resin compositions that can provide cured products with low thermal expansion coefficients. The present invention aims to solve the above-mentioned problems, and aims to provide a resin composition capable of providing a cured product having 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. [Means for solving the problem]

[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 coefficient of thermal expansion can be obtained by using a resin having a specific isopropenyl group in combination with a specific divinyl aromatic compound. Specifically, the above problems were solved by the following means. [1] The composition contains 10 to 90 parts by mass of a resin (A) and 90 to 10 parts by mass of a compound (B) represented by formula (BV), A resin composition, wherein the resin (A) is a resin represented by formula (T): [ka] (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x1 represents an integer of 0 to 4, and R represents a divalent group.) [ka] (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.) [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: [ka] (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 [3], wherein the parameter α of the resin (A) calculated from the formula (α) is 0.20 or more and 1.00 or less, the parameter β of the resin (A) calculated from the 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.

number

number

[10] The resin composition according to any one of [1] to [9], which is for use in a printed wiring board.

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

[10] .

[12] A prepreg formed from a substrate and the resin composition according to any one of [1] to [7].

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

[12] and metal foil arranged 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] , disposed on the surface of the support.

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

[10] .

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

[15] . [Effects of the Invention]

[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. [Brief explanation of the drawings]

[0007] [Figure 1] 1H-NMR chart of Synthesis Example 1 is shown. [Figure 2] FIG. 1 is a diagram showing the peak values ​​of parameters α and β in the 1H-NMR chart of the resin obtained in Synthesis Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0008] Hereinafter, an embodiment for carrying out the present invention (hereinafter simply referred to as "the present embodiment") will be described in detail. Note that the present embodiment is an example for explaining the present invention, and the present invention is not limited to only this embodiment. In this specification, the symbol "to" is used to mean that the numerical values ​​before and after it are included as the lower limit and upper limit. In this specification, various physical properties and characteristic values ​​are those at 23°C unless otherwise specified. In the description of groups (atomic groups) in this specification, when a notation does not specify whether they are substituted or unsubstituted, it includes both groups (atomic groups) that have no substituents and groups (atomic groups) that have substituents. For example, the term "alkyl group" includes not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups). In this specification, when a notation does not specify whether they are substituted or unsubstituted, it is preferable that they be unsubstituted. In this specification, the dielectric constant refers to the ratio of the dielectric constant of a substance to the dielectric constant of a vacuum. In this specification, the dielectric constant may also be simply referred to as "dielectric constant." Furthermore, unless otherwise specified, the dielectric constant in this specification refers to the dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method. In this specification, "(meth)acrylic" refers to both or either of acrylic and methacrylic, and "(meth)allyl" refers to both or either of allyl and methallyl. If the standards shown in this specification differ depending on the year and the measurement method, etc., they will be based on the standards as of January 1, 2024, unless otherwise stated.

[0009] In this specification, the resin solids content refers to components excluding fillers and solvents, and is intended to include the resin (A), the compound (B) represented by formula (BV), other thermosetting compounds that are blended as necessary, and 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 compound (B) represented by formula (BV) relative to 10 to 90 parts by mass of a resin (A), and the resin (A) is a resin represented by formula (T). [ka] (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x1 represents an integer of 0 to 4, and R represents a divalent group.) [ka] (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.)

[0011] By adopting the above-mentioned constitution, a resin composition can be obtained that can provide a cured product with a low coefficient of thermal expansion. That is, resin (A) often does not cure sufficiently by itself. Therefore, it is considered to blend other curable components. Here, the present inventors investigated divinylbenzene to cure resin (A). However, divinylbenzene did not cure sufficiently. On the other hand, when a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond was blended with resin (A), curing proceeded but the thermal expansion coefficient was high. Under these circumstances, the present inventors conducted extensive research and found that blending a compound represented by formula (BV) with resin (A) enabled sufficient curing and effectively suppressed thermal expansion. The reason for this is presumed to be due to the structure of the compound represented by formula (BV), which has functional groups at a moderate distance from each other and a structure that allows for moderate mobility, compared to polyphenylene ether compounds and divinylbenzene, which have terminal carbon-carbon unsaturated double bonds. Divinylbenzene has the following structure, in which two vinyl groups are bonded to one benzene ring. [ka]

[0012] In contrast, compound (B) represented by formula (BV) has two vinyl groups bonded at a moderate distance, which is thought to reduce steric hindrance during polymerization. Furthermore, unlike divinylbenzene, it is possible for each vinyl group to rotate, which is thought to result in high flexibility. As a result, it is presumed that the thermal expansion of the cured product was effectively suppressed.

[0013] Furthermore, in this embodiment, by setting r of the compound (B) represented by formula (BV) to 1 or more, an aliphatic group is present between the benzene rings, which makes it difficult for functional groups to remain during the reaction, and further improves the crosslink density. As a result, it is presumed that the thermal expansion of the cured product can be more effectively suppressed.

[0014] 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.

[0015] <Resin (A)> The resin (A) in this embodiment is a resin represented by formula (T). [ka] (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.)

[0016] 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.

[0017] 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.

[0018] In formula (T), R is a divalent group, preferably -S-, -O-, C(=O)-NH2-, 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 even more preferably containing a group represented by formula (Tx). [ka] (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.)

[0019] 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.

[0020] In formula (Tx), n is preferably 0.2 or more, more preferably 0.6 or more, even more preferably 1.0 or more, even more preferably 1.2 or more, even 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, even more preferably 9.0 or less, even more preferably 7.0 or less, even 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, even more preferably 0.05 or more, and even more preferably 0.07 or more; it 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; it 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.

[0021] 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), structural unit (a), which has the smallest activation energy and the largest free energy change, is preferentially produced. When the R portion 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 structural units (a), (b), or (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, and 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.

[0022] 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.

number

[0023] Here, α represents 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, by adjusting the structural unit having an indane skeleton so that the parameter α falls within the range, it is presumed that the rigidity of the resulting resin molecules will be high and the glass transition temperature will be high. 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. On the other hand, 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 groups of the thermosetting compound increases, making it easier to form a network upon thermal curing, resulting in a cured product with a high glass transition temperature and low Df. 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).

[0024] 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 the structural unit (a), the 6.24 ppm to 5.91 ppm corresponds to the peak derived from the structural unit (b), the 2.98 ppm to 2.55 ppm corresponds to the peak derived from the structural unit (c), the 5.49 ppm to 4.89 ppm corresponds to the peak derived from the isopropenyl group and the structural unit (c), the 4.89 ppm to 4.45 ppm corresponds to the peak derived from the structural unit (c), and the 2.31 ppm to 1.96 ppm corresponds to the peak derived from the isopropenyl group and the structural unit (a). More specifically, H used to calculate the parameters α and β is shown in the following structural formula: [ka] [ka] Used to calculate the above parameters α and β 1 The H-NMR peaks can be assigned as follows using the above-described H peaks: 2.55ppm~2.31ppm:H a1 6.24ppm~5.91ppm:H b1 2.98ppm~2.55ppm:H c1 5.49ppm~4.89ppm:H i2 and H i3 and H c2 4.89ppm~4.45ppm:Hc3 2.31ppm~1.96ppm:H a2 and H i1

[0025] From the above, the formula for the parameters α and β is written in terms of the amount of each hydrogen atom shown below. That is, the parameter α is H a1 The greater the amount of (a), that is, the greater the number of five-membered rings in the structural unit (a), the greater the value. The parameter β is the H in the isopropenyl group. 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 In addition, Fig. 2 shows the resin obtained in Synthesis Example 1 described later. 1 The peak values ​​of parameters α and β are shown in the H-NMR chart.

[0026] 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 those described above.

[0027] 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 greater than the above lower limit, the heat resistance of the obtained cured product tends to be further improved. The parameter α is preferably large because the resulting cured product tends to have excellent low dielectric properties (Dk and / or Df) and heat resistance. However, depending on the application, the parameter α 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. 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, and 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 is 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, or 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.

[0028] Examples of raw materials that can be used to synthesize the resin represented by formula (T) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0029] When m-bis(α-hydroxyisopropyl)benzene or p-bis(α-hydroxyisopropyl)benzene is used as an example of a raw material for synthesizing a 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 synthesized directly 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.

[0030] 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.

[0031] The process for removing the solid catalyst during synthesis of the resin represented by formula (T) includes filtration and decantation. These processes can be carried out alone or in combination depending on the purpose.

[0032] 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.

[0033] 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.

[0034] 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 promote the dehydration reaction.

[0035] The catalyst used in synthesizing the resin represented by formula (T) can be added all at once or in portions.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The temperature control means used in the synthesis step of the resin represented by formula (T) may be 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.

[0040] The polystyrene-equivalent number-average molecular weight (Mn) of resin (A) measured by gel permeation chromatography (GPC) (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 adjusting the number-average molecular weight to the above-mentioned lower limit or higher, the heat resistance of the resulting 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 gel permeation chromatography (GPC) is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, and even more preferably 1250 or less. Depending on the application, it may be 1000 or less or 800 or less. By adjusting 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 relative dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower. Furthermore, the polystyrene-equivalent weight average molecular weight (Mw) of 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 at or above the lower limit, the heat resistance of the resulting cured product tends to be improved and Df tends to be lower. The upper limit of the polystyrene-equivalent weight average molecular weight (Mw) of 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, and may be 2500 or less, 2000 or less, or 1500 or less depending on the application, etc. By setting the weight average molecular weight at or below the upper limit, the heat resistance of the resulting cured product tends to be improved and the relative dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower.

[0041] The resin (A) preferably has a ratio of weight average molecular weight to number average molecular weight, Mw / Mn, of 1.1 to 3.0. The resin (A) preferably has a ratio of 1.2 or more, 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 resin (A) preferably has a ratio of 2.5 or less, even more preferably 2.4 or less, and may have a ratio of 2.3 or less, 2.0 or less, or 1.8 or less. The weight average molecular weight and the number average molecular weight are measured according to the method described in the Examples below.

[0042] 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, even 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 weight 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. By setting the functional group equivalent weight 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) and better heat resistance (particularly glass transition temperature). The functional group equivalent weight (isopropenyl group equivalent weight) of resin (A) is determined according to the method described in the Examples below.

[0043] The content of resin (A) in the resin composition of this embodiment is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 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 30 parts by mass or more, 35 parts by mass or more, or 45 parts by mass or more. By setting the content of resin (A) at or above the lower limit, the Df of the resulting cured product tends to be reduced. Furthermore, the upper limit of the content of resin (A) is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, and even more preferably 85 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 80 parts by mass or less, 75 parts by mass or less, 70 parts by mass or less, 65 parts by mass or less, 60 parts by mass or less, or 55 parts by mass or less. Setting the content of resin (A) at or below the upper limit tends to improve the moldability of the resin composition and the heat resistance of the resulting cured product. 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 within the above range.

[0044] 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.

[0045] <Compound (B) represented by formula (BV)> The resin composition of the present embodiment contains a compound (B) represented by formula (BV). By containing the compound (B) represented by formula (BV), thermal expansion of the cured product can be effectively suppressed. [ka] (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.)

[0046] In formula (BV), Md each independently represents a hydrocarbon group having 1 to 12 carbon atoms, is preferably an alkyl group, more preferably a linear alkyl group, and further preferably a methyl group or an ethyl group. In formula (BV), w is 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 is 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. [ka]

[0047] The content of the compound (B) represented by formula (BV) 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 intended use, 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 compound (B) represented by formula (BV) at or above the lower limit, the Df of the resulting cured product tends to be reduced. Furthermore, the upper limit of the content of the compound (B) represented by formula (BV) 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 intended use, it may be 70 parts by mass or less, 65 parts by mass or less, or 55 parts by mass or less. By adjusting the content of the compound (B) represented by formula (BV) to the above 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 compound (B) represented by formula (BV), or may contain two or more compounds. When two or more compounds are contained, the total amount is preferably in the above range.

[0048] Furthermore, the resin composition of this embodiment preferably contains 90 to 10 parts by mass of compound (B) represented by formula (BV) per 10 to 90 parts by mass of resin (A), 80 to 10 parts by mass of compound (B) represented by formula (BV) per 20 to 90 parts by mass of resin (A), more preferably 70 to 20 parts by mass of compound (B) represented by formula (BV) per 30 to 80 parts by mass of resin (A), and even more preferably 55 to 25 parts by mass of compound (B) represented by formula (BV) per 45 to 75 parts by mass of resin (A). Furthermore, an example of the resin composition of the present embodiment is one in which the total amount of resin (A) and compound (B) represented by formula (BV) is 90 parts by mass or more, preferably 95 parts by mass or more, more preferably 97 parts by mass or more, or may be 98 parts by mass or more, or even 100 parts by mass, per 100 parts by mass of the resin solid content contained in the resin composition.

[0049] <Other thermosetting compounds> The resin composition of the present embodiment may contain a thermosetting compound other than the resin (A) and the compound (B) represented by formula (BV). The other thermosetting compound is usually a thermosetting resin. The other thermosetting compounds are not particularly limited in type, but preferably contain at least one selected from the group consisting of maleimide compounds, aromatic-containing resins having a terminal carbon-carbon double bond, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane resins, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group, and the other thermosetting compounds are preferably at least one selected from the group consisting of maleimide compounds, aromatic-containing resins having a terminal carbon-carbon double bond, cyanate ester compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, It is more preferable that the resin composition contains at least one selected from the group consisting of a 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 a 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 a 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.

[0050] 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 solids in the resin composition, and may be 60 parts by mass or more, 65 parts by mass or more, and is 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 be equal to or greater than the above-mentioned lower limit, heat resistance tends to be further improved. Furthermore, by setting the content of the other thermosetting 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 the present 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 in the above range.

[0051] <<Maleimide compounds>> The resin composition of the present embodiment preferably contains a maleimide compound. In this embodiment, the 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 maleimide compound preferably includes one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), a maleimide compound (M6), a maleimide compound (M7), and a maleimide compound (M8), and the compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), and a compound represented by formula (M5) The maleimide compound preferably contains one or more compounds selected from the group consisting of compounds represented by formula (M0), compounds represented by formula (M1), compounds represented by formula (M3), compounds represented by formula (M4), and compounds represented by formula (M5), more preferably contains one or more compounds selected from the group consisting of compounds represented by formula (M1), compounds represented by formula (M3), and compounds represented by formula (M5), and even more preferably contains a compound represented by formula (M1) and / or a compound represented by formula (M3). When these maleimide compounds are used in materials for printed wiring boards (e.g., metal foil-clad laminates), they can impart excellent heat resistance.

[0052] [ka] (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, and n1 represents an integer of 1 or greater. 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. R 52 is preferably a methyl group. n1 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 the formula (M0): [ka] 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.

[0053] The compound represented by formula (M0) may be a single compound or a mixture of two or more compounds. Examples of the mixture include a mixture of compounds with different n1, 51 and / or R 52 Examples of such a mixture include 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 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.

[0054] [ka] (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 of Ar 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 , RM13 , and R M14 R each independently represents a hydrogen atom or an organic group. M15 each 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.

[0055] 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. R M5 and R M6 are each independently 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 particularly preferably a methyl group. Ar 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. Mmay 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 is preferably unsubstituted. A is a 4- to 6-membered alicyclic group, and 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, and is preferably 2. lx is 0 or 1, and is preferably 1. R M9 and R M10 are each independently a hydrogen atom or an alkyl group, more 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 particularly preferably a methyl group. R 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. R 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, 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 compound represented by formula (M1) or two or more compounds having different values ​​of nx. When two or more compounds are contained, the average value of nx (average number of repeating units) n in the compounds 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 achieve 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 below.

[0056] The compound represented by formula (M1) is preferably a compound represented by the following formula (M1-1). [ka] (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 , RM28 , R M29 , and R M30 R each independently represents a hydrogen atom or an organic group. M31 and R M32 R 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] 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. R M25 and R M26 are each independently 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 particularly preferably a methyl group. R M27 , R M28 , R M29 , and R M30each 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. R M31 and R M32 are each independently 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 particularly preferably a methyl group. R M33 , R M34 , R M35 , and R M36 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. R M33 and R M36 is preferably a hydrogen atom, and R M34 and R M35 is preferably an alkyl group. R M37 , R M38 , and R M39 are each independently 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 particularly preferably a methyl group. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.

[0058] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-2). [ka] (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 M32 R 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.

[0059] 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 , RM31 , 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.

[0060] 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). [ka] (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. [ka] (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.

[0061] 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.

[0062] 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.

[0063] [ka] (In formula (M2), R 54 each independently represents a hydrogen atom or a methyl group, and n4 represents an integer of 1 or greater. n4 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. The compound represented by formula (M2) may be, and preferably is, a mixture of compounds in which n4 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0).

[0064] [ka] (In formula (M3), R 55 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and n5 represents an integer of 1 or more and 10 or less. R 55 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. n5 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. The compound represented by formula (M3) may be, and preferably is, a mixture of compounds in which n5 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0).

[0065] [ka] (In formula (M4), R 56 each independently represents a hydrogen atom, a methyl group, or an ethyl group; R57 each independently represents a hydrogen atom or a methyl group. An example of a compound represented by formula (M4) is R 56 are each independently a methyl group or an ethyl group, and R 57 is a methyl group. 56 is more preferably a methyl group and an ethyl group on each of the two benzene rings. Another example of the compound represented by formula (M4) is R 56 and R 57 is a hydrogen atom.

[0066] [ka] (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, and n6 represents an integer of 1 or greater. 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. R 59 is preferably a methyl group. n6 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. The compound represented by formula (M5) may be, and preferably is, a mixture of compounds in which n6 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0).

[0067] The maleimide compound (M6) is a compound having a structure represented by formula (M6) and maleimide groups at both ends of the molecular chain. [ka] (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 the maleimide compound (M6) and its production method, please refer to paragraphs 0061 to 0066 of WO 2020 / 262577, the contents of which are incorporated herein by reference.

[0068] The maleimide compound (M7) is a maleimide compound obtained by reacting, as reaction raw materials (1), an aromatic amine compound (a1) having 1 to 3 alkyl groups on the aromatic ring, an aromatic divinyl compound (a2) having two ethenyl groups, and maleic anhydride. The maleimide compound (M7) is preferably a compound having a structure represented by formula (M7). [ka] (In the above formula (M7), R 1 each independently represents an alkyl group having 1 to 10 carbon atoms, and R 2 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 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, or 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, R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a methyl group, and R 3and R 4 One of the groups 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, X 1 are each independently represented by the following formula (x): [ka] (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 the groups 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. and r represents a substituent represented by X 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.

[0069] For details of the 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.

[0070] The maleimide compound (M8) is a bismaleimide compound having a hydrocarbon group in which eight or more atoms are linearly linked, and is preferably a compound represented by formula (M8): Such maleimide compounds (M8) tend to have higher stress relaxation ability, and as a result, the thermal expansion coefficient of the resulting cured product tends to be lower, and the electrical properties such as the dielectric constant and dielectric loss tangent tend to be more excellent. [ka] (In formula (M8), R 1 and R 3 each independently represents a hydrocarbon group having 8 or more atoms linked in a linear chain, and 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.

[0071] In formula (M8), R 1 and R 3 is an octylene group, and R 2 is preferably a cycloalkylene group having an alkyl group having 6 to 8 carbon atoms as a substituent.

[0072] For the maleimide compound (M8), the descriptions in paragraphs 0014 to 0022 of JP 2018-083893 A and paragraphs 0012 to 0022 of JP 2018-090728 A can be referred to, the contents of which are incorporated herein by reference.

[0073] The maleimide compound may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "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 Chemical Industry 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), and "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M4). Examples of compounds that can be used include "BMI-70" manufactured by K.I. Chemical Industry Co., Ltd. and "BMI-5100" manufactured by Daiwa Chemical Industry Co., Ltd.; "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M5); "MIZ-001" manufactured by Nippon Kayaku Co., Ltd. as a maleimide compound (M6); "NE-X-9500" manufactured by DIC Corporation as a maleimide compound (M7); "SFR" manufactured by Resonac Corporation; and "BMI-689," "BMI-1500," "BMI-2500," "BMI-3000," and "BMI-5000" manufactured by DESIGNER MOLECULES INC. as a maleimide compound (M8).

[0074] Furthermore, examples of maleimide compounds other than 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 International Publication No. 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.

[0075] The maleimide group equivalent of the 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 is 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 the above lower limit or more, the low dielectric properties (Dk and / or Df, especially Df) of the resulting cured product tend to be better. On the other hand, by setting it to the above upper limit or less, the peel strength of the resulting cured product tends to be better.

[0076] When the resin composition of this embodiment contains a maleimide compound, the lower limit of the content 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, the content of the maleimide compound in an amount of 1 part by mass or more tends to improve the flame resistance of the resulting cured product. Furthermore, the upper limit of the content of the 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, the content of the maleimide compound in an amount of 90 parts by mass or less tends to improve peel strength and low water absorbency. The resin composition of the present embodiment may contain only one maleimide compound or may contain two or more maleimide compounds. When two or more maleimide compounds are contained, the total amount is preferably in the above range.

[0077] <<Aromatic-containing resin with terminal carbon-carbon double bonds>> An aromatic-containing resin having a terminal carbon-carbon double bond is, for example, a compound having a terminal carbon-carbon double bond and containing an aromatic ring, and is a compound that cures when heated. By using an aromatic-containing resin having a terminal carbon-carbon double bond in combination with an elastomer, the compatibility between the two is improved, and the thermal expansion coefficient of the resulting cured product can be reduced. The aromatic-containing resin having a terminal carbon-carbon double bond here does not include the compound (B) represented by formula (BV). 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.

[0078] 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 preferably 25 parts by mass or more, and is 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 preferably 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 at or above the 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 at or below the 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, the total amount is preferably in the above range.

[0079] <<<Polyphenylene ether compound with terminal carbon-carbon unsaturated double bonds>>> The resin composition of the present embodiment preferably contains a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, and more preferably contains a polyphenylene ether compound having 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 terminal groups (preferably vinylbenzyl groups) represented by formula (Rx-1) described below. 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 will be explained in detail below.

[0080] 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).

[0081] [ka] (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.

[0082] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is represented by the formula (X2): [ka] (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): [ka] (In formula (X3), R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , and ,R 43 may be the same or different and 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.

[0083] 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.

[0084] The modified polyphenylene ether compound (g) includes a polyphenylene ether compound represented by formula (OP). [ka] (In formula (OP), X represents an aromatic group, -(YO) 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). [ka] (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. * is 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.

[0085] 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. The polyphenylene ether structure represented by -(YO)n1- may or may not have a substituent on the benzene ring, but preferably has one. When the polyphenylene ether structure has a substituent, examples thereof include the above-mentioned substituent Z, and the substituent is preferably an alkyl group or phenyl group having 6 or less carbon atoms, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. When n1 and / or n2 are integers of 2 or greater, the n1 structural units (YO) and / or n2 structural units may be the same or different. n2 is preferably 2 or greater, and more preferably 2.

[0086] 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. R 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. R 2 and R 3are 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. R 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.

[0087] In formula (Rx-1), r represents an integer of 0 to 6, and may be an integer of 1 or greater, 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.

[0088] 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 still 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.

[0089] 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.

[0090] 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).

[0091] The modified polyphenylene ether compound (g) includes a compound represented by formula (OP-1). [ka] (In formula (OP-1), X represents an aromatic group, -(YO)n2- 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, n1 represents an integer of 0 to 6, n2 represents an integer of 1 to 100, and n3 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, 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. The polyphenylene ether structure represented by -(YO)- may or may not have a substituent on the benzene ring, but preferably has one. When the polyphenylene ether structure has a substituent, examples thereof include the above-mentioned substituent Z, and the substituent is preferably an alkyl group or phenyl group having 6 or less carbon atoms, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. When n2 and / or n3 are integers of 2 or greater, the n2 structural units (YO) and / or n3 structural units may be the same or different. n3 is preferably 2 or greater, and more preferably 2.

[0092] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). [ka] where -(OXO)- is a compound of formula (OP-3): [ka] (In formula (OP-3), R 4 , R 5 , R 6 , R 10 , and ,R 11 R may be the same or different and is an alkyl group or a phenyl group 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 formula (OP-4): [ka] (In formula (OP-4), R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and ,R 19 may be the same or different and 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.

[0093] Also, -(YO)- is a group represented by the formula (OP-5): [ka] (In formula (OP-5), R 20 , R 21 R may be the same or different and is an alkyl group or a phenyl group 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. Especially R 20 and R 21Independently, by making the group have one or more methyl groups and / or cyclohexyl groups, the rigidity of the resulting resin molecules increases. Since molecules with high rigidity have lower mobility compared to molecules with low rigidity, the relaxation time during dielectric relaxation becomes longer, which is preferable because it exhibits excellent low dielectric properties (Dk and / or Df, particularly Dk). An example of formula (OP-5) has the following structure. [Chemical formula] Regarding the polyphenylene ether compound having the above structure, reference can be made to the description in JP-A-2019-194312, and this content is incorporated herein.

[0094] In formula (OP-2), a and b each independently represent an integer from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are each independently an integer from 0 to 50, more preferably an integer from 1 to 30, and still more preferably an integer from 1 to 10. When a and / or b is an integer of 2 or more, two or more -(Y-O)- may each independently have one kind of structure arranged, or two or more kinds of structures may be arranged in blocks or randomly. Further, when a plurality of compounds represented by formula (OP-2) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0095] Examples of -A- in formula (OP-4) include divalent organic groups such as a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, a 1,3-phenylenebis(1-methylethylidene) group, a cyclohexylidene group, a phenylmethylene group, a naphthylmethylene group, and a 1-phenylethylidene group, but are not limited thereto.

[0096] Among the compounds represented by the above formula (OP-2), R 4 , R 5 , R 6 , R10 , 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 23 is a hydrogen atom or an alkyl group having 3 or less carbon atoms, and it is particularly preferred that -(OXO)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and -(YO)- represented by formula (OP-5) is formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the two or more -(YO)- 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.

[0097] [ka] [ka] (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). [ka] (In formula (OP-11), -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). [ka] [ka]

[0098] 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). [ka] (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.) In formula (OP-14), a and b each independently have the same meaning as a and b in formula (OP-2), and the preferred ranges are also the same. [ka] (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.) In formula (OP-15), a and b each independently have the same meaning as a and b in formula (OP-2), and the preferred ranges are also the same.

[0099] Furthermore, the polyphenylene ether compound used in this embodiment may also be a compound represented by formula (OP-16). [ka] (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.)

[0100] 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 those obtained by modifying a terminal hydroxyl group, such as "SA90" manufactured by SABIC Innovative Plastics, with a vinylbenzyl group using vinylbenzyl chloride or the like.

[0101] In addition, for details of polyphenylene ether compounds having terminal carbon-carbon unsaturated double bonds, see JP 2006-028111 A, JP 2018-131519 A, WO 2019-138992, WO 2022-054303, 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.

[0102] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond (preferably a modified polyphenylene ether compound (g)) preferably has a polystyrene-equivalent number average molecular weight (details follow the method described in the Examples below) as measured by GPC (gel permeation chromatography) of 500 or more and 3,000 or less. A number average molecular weight of 500 or more tends to further reduce 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)) (details follow the method described in the Examples below) is preferably 800 to 10,000, more preferably 800 to 5,000. When the weight average molecular weight is equal to or greater than the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (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 a varnish or the like, which will be described later, tend to be improved. Furthermore, the terminal carbon-carbon unsaturated double bond equivalent of the polyphenylene ether compound (preferably a modified polyphenylene ether compound (g)) having a terminal carbon-carbon unsaturated double bond is preferably 400 to 5000 g, and more preferably 400 to 2500 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 relative permittivity (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower, while when it is equal to or less than the upper limit, the solubility in solvents, low viscosity, and moldability of the resin composition tend to be improved.

[0103] The functional group equivalent (carbon-carbon unsaturated double bond equivalent) 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 calculated as follows. The powder of the polyphenylene ether compound is weighed and the weight is recorded. This powder is placed in a measuring flask and then the flask is filled up to a predetermined volume 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). Next, the sample liquid is subjected to infrared spectroscopy. In the case of vinyl groups in the polyphenylene ether compound, the peak wavelength is 905 cm. -1If the carbon-carbon unsaturated double bond is a methacrylic group, the peak area of ​​the spectrum around 1640 cm -1 The area of ​​the peak in the spectrum near the peak is recorded. The double bond concentration [mol / L] can be calculated from this area and the calibration curve. Next, the double bond equivalent is calculated by 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 obtained by calculating the functional group equivalent by dividing the theoretical molecular weight by the number of functional groups is used as the preferred method. When two or more other thermosetting compounds are contained, 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 other thermosetting compound by its mass fraction.

[0104] 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 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 the above lower limit or more, 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, and 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, depending on the application, etc. 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 of the present embodiment may contain only one polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, or may contain two or more polyphenylene ether compounds. When two or more polyphenylene ether compounds are contained, the total amount is preferably within the above range.

[0105] <<<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 having excellent low dielectric properties (low relative dielectric constant, low dielectric loss tangent) can be obtained. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) The aromatic hydrocarbon linking group may be a group consisting of only 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 of only aromatic hydrocarbons which may have a substituent. The substituent that the aromatic hydrocarbon may have includes a 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.

[0106] 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, 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 have no substituent.

[0107] The polymer having a structural unit represented by formula (V) more preferably contains at least one of a structural unit represented by formula (V1), a structural unit represented by formula (V2), and a structural unit represented by formula (V3). In the formulae 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)."

[0108] [ka] 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, and among these, phenylene groups, which may have a substituent, are preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferable that the above-mentioned phenylene groups and other groups have no substituent. 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. Among these, divinylbenzene is particularly preferred. These divinyl aromatic compounds may be used alone or in combination of two or more types, as required. That is, the structural unit (a) is preferably a structural unit derived from a divinyl aromatic compound.

[0109] As described above, the polymer having the structural unit represented by formula (V) may be a homopolymer of the compound that forms the structural unit (a), or it may 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, the copolymerization ratio of the structural unit (a) is preferably 3 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, and may 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, or 20 mol% or less.

[0110] 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).

[0111] The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[0112] [ka] In formula (V4), L 2 is an aromatic hydrocarbon linking group, and specific examples of preferred groups 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.

[0113] When the polymer having the 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.

[0114] 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 even 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.

[0115] A polymer having a structural unit represented by formula (V) may have structural units other than structural unit (a) and 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.

[0116] 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.

[0117] 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.

[0118] An example of an embodiment of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains structural unit (a) and also contains at least one of structural units (b) and (c). Further, an example is an embodiment in which the total of structural units (a) to (c) accounts for 90 mol % or more, more preferably 95 mol % or more, and particularly 98 mol % or more of all structural units. Another embodiment of the polymer having the structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a) and also contains at least one of the structural units (b) to (d). A further example is one in which the total of the structural units (a) to (d) accounts for 95 mol % or more, and even 98 mol % or more, of all the structural units. Another embodiment of the polymer having a structural unit represented by formula (V) is a polymer in which the structural unit (a) is essential, and of all structural units excluding the terminals, structural units containing an aromatic ring are preferably 90 mol % or more, more preferably 95 mol % or more, and may be 100 mol %. In calculating the mole percent per total structural units, one structural unit is defined as being 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).

[0119] 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.

[0120] 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 above divinyl aromatic compound, it may have the structure of the following formula (E1). 1 is the same as defined in the above formula (V1). * represents the bonding position. *-CH=CH-L 1 -CH=CH2(E1)

[0121] 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) above. * represents a bonding position. *-CH=CH-L 2 -R V1 (E2)

[0122] The molecular weight of the polymer having a structural unit represented by formula (V) is, in number average molecular weight (Mn), preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and still more preferably 1,500 or more. 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, and still 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 terms of weight-average molecular weight Mw. By setting the weight-average molecular weight at or above the lower limit, the excellent low dielectric properties (Dk and / or Df) of the polymer having the structural unit represented by formula (V), particularly Df and dielectric properties after moisture absorption, 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. Setting the weight-average molecular weight at or below the upper limit tends to reduce embedding defects when the prepreg or resin sheet is laminated on a circuit-printing substrate. The monodispersity (Mw / Mn), which is the ratio of weight-average molecular weight (Mw) to 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 may be 12 or less. A practical lower limit 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 as described 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.

[0123] 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. Having a vinyl group equivalent equal to or greater than the lower limit tends to improve the storage stability of the resin composition and improve the flowability of the resin composition. This improves moldability, reduces the likelihood of voids occurring during the formation of prepregs, etc., and tends to result in more reliable printed wiring boards. On the other hand, having a vinyl group equivalent equal to or less than the upper limit tends to improve the heat resistance of the resulting cured product.

[0124] 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, measured at 10 GHz 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 a 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, measured at 10 GHz 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 permittivity (Dk) and the dielectric loss tangent (Df) are measured by the following method. 4.5 g of resin powder is spread into a stainless steel mold frame measuring 100 mm x 30 mm x 1.0 mm high, set in a vacuum press (Kitagawa Seiki Co., Ltd.), held at 200°C for 2 hours, and pressed at a surface pressure of 3.0 MPa to produce a hardened plate. The cured plate was reduced in width to 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 at 23°C.

[0125] For polymers having a structural unit represented by formula (V) in this specification, the compounds described in paragraphs 0029 to 0058 of International Publication No. 2017 / 115813 and their synthesis reaction conditions, etc., compounds described in paragraphs 0013 to 0058 of JP-A-2018-039995 and their synthesis reaction conditions, etc., compounds described in paragraphs 0008 to 0043 of JP-A-2018-168347 and their synthesis reaction conditions, etc., compounds described in paragraphs 0014 to 0042 of JP-A-2006-070136 and their synthesis reaction conditions, etc., compounds described in paragraphs 0014 to 0061 of JP-A-2006-089683 and their synthesis reaction conditions, etc., 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 by reference. The polymer having a constitutional unit represented by formula (V) may be a commercially available product, such as LF-310T50 manufactured by Nippon Steel Chemical & Material Co., Ltd.

[0126] 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 ensuring that the content of the polymer having a structural unit represented by formula (V) is equal to or greater than the above lower limit, 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 adjusting 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 absorbency tend to be improved. The resin composition in this embodiment may contain only one type of polymer having a structural unit represented by formula (V), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition in this embodiment may also 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 a structural unit represented by formula (V) 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.

[0127] <<<Other aromatic resins with terminal carbon-carbon double bonds>>> 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 paragraphs are incorporated herein by reference.

[0128] The resin composition of this embodiment may also be configured to be substantially free of an aromatic-containing resin having a terminal carbon-carbon double bond. "Substantially free" means that the content of the aromatic-containing resin having a terminal carbon-carbon double bond contained in the resin composition of this embodiment is less than 10 parts by mass, or may be less than 5 parts by mass, less than 1 part by mass, less than 0.1 parts by mass, or less than 0.01 parts by mass, per 100 parts by mass of the resin solid content contained in the resin composition.

[0129] <<Other compounds having a terminal carbon-carbon unsaturated double bond (compound (XC))>> The resin composition of the present embodiment may contain another compound (compound (XC)) having a carbon-carbon unsaturated double bond at a terminal other than those mentioned above. An example of the 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 (for example, compounds described in Synthesis Examples 1, 2, 7, and 8 of the same publication), the contents of which are incorporated herein by reference.

[0130] Another example of a compound having a terminal carbon-carbon unsaturated double bond (compound (XC)) is vinylbenzyl ether. Examples of vinylbenzyl ethers 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. Furthermore, 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 4,4'-Hexafluoroisopropylidene)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-fluoroisopropylidene)bisphenol (bisphenol AF), 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'-spirobi[indene]-5,6'-diol (spirobiindane), dihydroxybenzophenone (bisphenol K), tris(4-hydroxyphenyl)methane, tris(4-hydro Examples of vinylbenzyl ethers include those produced by reacting vinylbenzyl chloride or vinylbenzyl bromide with tetrakis(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. In addition to the above, the 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.

[0131] 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 intended use, 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 resulting 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 intended use, 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 the present embodiment may contain only one type of other compound (compound (XC)) having a terminal carbon-carbon unsaturated double bond, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0132] <<Cyanate ester compounds>> 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 (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) cyanate groups (cyanato groups) in one molecule, 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 type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds, naphthylene ether type cyanate ester compounds, xylene resin type cyanate ester compounds, bisphenol M type cyanate ester compounds, bisphenol A type cyanate ester compounds, and diallyl bisphenol A type cyanate ester compounds is more preferable, at least one selected from the group consisting of phenol novolac type cyanate ester compounds and naphthol aralkyl type cyanate ester compounds is even more preferable, and naphthol aralkyl type cyanate ester compounds are even more preferable. These cyanate ester compounds may be prepared by known methods, or commercially available products may be used. Note that 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] The naphthol aralkyl cyanate ester compound is more preferably a compound represented by the following formula (1). [ka] (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 is 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). [ka] (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 preferred. In formula (VII), n7 is 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 solids 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 solids in the resin composition. The resin composition of the present embodiment may contain only one type of cyanate ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0139] <<(Meth)allyl compounds>> The resin composition of the present 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, and more preferably a compound containing two or more allyl groups. The (meth)allyl compound preferably includes 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 includes 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; even more preferably includes a (meth)allyl isocyanurate compound and / or a (meth)allyl group-substituted nadimide compound; and even more preferably includes a (meth)allyl group-substituted nadimide compound.

[0140] Examples of the tri(meth)allyl cyanurate compound include tri(meth)allyl cyanurate compounds (for example, triallyl cyanurate having the structure shown below). [ka] In addition, examples of the (meth)allyl compound include resins having an allyl group described in WO 2022 / 210095 (for example, the 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 properties tend to be further improved. The resin composition of the present 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 is preferably in the above range.

[0143] <<<(Meth)allyl isocyanurate compounds>>> The (meth)allyl isocyanurate compound is not particularly limited as long as it has two or more (meth)allyl groups and an isocyanurate ring (nurate skeleton). Because the (meth)allyl isocyanurate compound has a large number of (meth)allyl groups that serve as crosslinking points, it tends 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. The (meth)allyl isocyanurate compound is preferably a compound represented by formula (TA): Formula (TA) [ka] (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 A A 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, it is possible to provide a resin composition that has excellent crosslinkability and is capable of giving a cured product having high toughness. This makes it possible to prevent cracking during etching or other treatments, 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 be 12 or more and 18 or less. This improves the resin flow properties of the resin composition, and is thought to result in better circuit filling properties when a multilayer circuit board or the like is produced using the resin composition of the present embodiment.

[0146] R A A second example of R is a group containing an allyl isocyanurate group. A When contains an allyl isocyanurate group, the compound represented by formula (TA) is preferably a compound represented by formula (TA-1). Formula (TA-1) [ka] (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). [ka] (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, which is either 0 or 1. * represents the bonding site. The above p c1 is 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. The above p 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] In addition, commercially available compounds represented by formula (TA) can also be used. Commercially available compounds are not particularly limited, but examples thereof include L-DAIC manufactured by Shikoku Chemical Industries Co., Ltd. and P-DAIC having a phosphorus-based substituent manufactured by Shikoku Chemical Industries Co., 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 Co., 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 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)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 the above-mentioned upper limit or less, 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 the present embodiment may contain only one type of (meth)allyl isocyanurate compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0157] <<<(Meth)allyl-substituted nadimide compounds>>> The (meth)allyl group-substituted nadimide compound is not particularly limited as long as it has two or more (meth)allyl group-substituted nadimide groups in the molecule, and specific examples thereof include the compound represented by the following formula (AN-1): [ka] In formula (AN-1), R1's each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R2's each independently represent 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). [ka] (In formula (AN-2), R3 represents a methylene group, an isopropylidene group, or a group represented by -C(=O)-, -O-, -S-, or -S(=O)2-.) [ka] (In formula (AN-3), each R4 independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.)

[0158] In addition, commercially available compounds represented by formula (AN-1) can also be used. Commercially available compounds include, but are not limited to, compounds represented by formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and compounds 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) [ka] [ka]

[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 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, and 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 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 types. When two or more types are contained, the total amount is preferably in the above range.

[0161] <<<(Meth)allyl compounds with 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, like (meth)allyl isocyanurate compounds, it tends 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. In this embodiment, the (meth)allyl compound having a glycoluril structure is preferably a compound represented by formula (GU). Formula (GU) [ka] (In formula (GU), R 1 are each independently a hydrogen atom or a substituent, and R 1 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. In formula (GU), R 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. In formula (GU), R 1 Preferably, three or four of the groups are groups containing a (meth)allyl group, and more preferably, four of the groups are groups containing a (meth)allyl group. In formula (GU), R 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] A specific example of the compound represented by formula (GU) is 1,3,4,6-tetraarylglycoluril (wherein R 1 are all aryl groups, and R 2 are all hydrogen atoms).

[0163] The (meth)allyl compound having a glycoluril structure can also be commercially available. Examples of commercially available compounds 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 even 400 or more. By adjusting the molecular weight of the (meth)allyl compound having a glycoluril structure to be equal to or greater than the above-mentioned lower limit, the heat resistance and low thermal expansion of the resulting 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 adjusting the molecular weight 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) and heat resistance of the resulting cured product tend to be further improved.

[0165] When the resin composition of this 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 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 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 at or below 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 type of (meth)allyl compound having a glycoluril structure, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0166] <<<(Meth)acrylate compounds>>> The resin composition of the present 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, 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 3 to 5 (meth)acryloyloxy groups, more preferably a compound having 3 or 4 (meth)acryloyloxy groups, and even more preferably a compound having 3 (meth)acryloyloxy groups. The (meth)acrylate compound is preferably a compound having a methacryloyloxy group. Since polyfunctional (meth)acrylate compounds have a large number of (meth)acrylate groups that serve as crosslinking points, they are strongly cured with other thermosetting compounds such as aromatic-containing resins having terminal carbon-carbon double bonds and maleimide compounds, and produce cured products with low dielectric properties (Dk and / or Df) and excellent heat resistance. As the polyfunctional (meth)acrylate compound, a compound represented by formula (MA) is preferred. Formula (MA) [ka] (In formula (MA), R 1 represents a hydrogen atom or a substituent, and 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 still 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 less 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, it is possible to provide a resin composition that has excellent crosslinkability and is capable of giving a cured product having high toughness. This makes it possible to suppress cracking during etching treatments and the like, 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 may be 12 or more and 18 or less. This improves the resin flow properties of the resin composition, and is thought to result in better circuit filling properties when a multilayer circuit board or the like is produced using the resin composition of the present embodiment.

[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 commercially available products, an example of such a 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, examples of (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), resins having a (meth)acrylic group described in Japanese Patent No. 6962507 (for example, compounds described in Examples 1 to 9), and resins having a (meth)acrylic group described in paragraph 0049 of JP 2019-194312 A and paragraphs 0010 to 0096 of JP 2024-159338 A, the contents of which 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 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 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 the present embodiment may contain only one type of (meth)acrylate compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0177] <<Epoxy compounds>> The resin composition of the present 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 (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) epoxy groups in one molecule, and a wide range 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 one or more 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 in the present 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 in the above range. The resin composition of the present embodiment may also be configured to be substantially free of epoxy compounds, which means that the content of the epoxy compounds is less than 0.1 parts by mass, preferably less than 0.01 parts by mass, and even less than 0.001 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0179] <<Phenol compounds>> The resin composition of the present embodiment may contain a phenol compound. The phenol compound is not particularly limited as long as it has one 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) phenolic hydroxyl groups in one molecule, and a wide range 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, polyfunctional phenolic resins, naphthol resins, naphthol novolac resins, polyfunctional 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, hydroxyl group-containing silicone resins, etc. 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. Furthermore, with regard to phenol compounds, the description in paragraphs 0012 to 0025 of WO 2023 / 176765 may also be taken into consideration, the contents of which are incorporated herein by reference.

[0180] When the resin composition of the present 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, relative to 100 parts by mass of the resin solid content in the resin composition, and 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 be 5 parts by mass or less. The resin composition of the present embodiment may contain only one type of phenol compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of phenolic compounds, meaning 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 compounds>> The resin composition of the present 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 still more preferably 2), and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of oxetane compounds 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-type 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 the extent that the effects of the present invention are not impaired. 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 the present embodiment may contain only one type of oxetane compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of oxetane compounds, meaning 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 compounds>> The resin composition of the present embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it has two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings in one molecule, and a wide range 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 the present embodiment preferably contains a benzoxazine compound within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains a benzoxazine compound, the content thereof is preferably 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of benzoxazine compounds, meaning that the content of the benzoxazine compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0185] <<Compounds containing vinylene groups>> The resin composition of the present embodiment may contain a compound having a vinylene group. Examples of compounds having a vinylene group include compounds containing one or more -CH=CH- in the molecule, and compounds containing one -CH=CH- in the molecule are preferred. Furthermore, compounds having a vinylene group that also fall under the category of maleimide compounds are considered maleimide compounds. Specific examples of the compound having a vinylene group are preferably acenaphthylene and pyracylene, and more preferably acenaphthylene. In this specification, a compound that also corresponds to a compound having a vinylene group, such as the above-mentioned imidazole compound, but is explicitly stated as a component other than a compound having a vinylene group (for example, a radical polymerization initiator) is not considered to be a compound having a vinylene group.

[0186] <Flame retardant> The resin composition of this 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 series, 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 phosphinic acid metal salts of dialkylphosphinic acid 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 the present 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 is 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 retardants 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.

[0188] <Active ester compounds> The resin composition of this 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 the present embodiment contains an active ester compound, the amount thereof is preferably 1 part by mass or more and 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of an active ester compound, which means that the content of the active ester compound 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.

[0190] <Dispersant> The resin composition of this embodiment may contain a dispersant. Dispersants commonly used in paints can be suitably used, and the type is not particularly limited. The dispersant is preferably a copolymer-based wetting dispersant, and specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, and W940, all 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, relative to 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, relative to 100 parts by mass of the resin solid content in the resin composition. The dispersant may 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, preferably 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 or 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 can 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 (e.g., 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 octoate, manganese octoate, 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 the 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] <Filling material> The resin composition of the present embodiment may contain a filler, which can further improve the physical properties of the resin composition and its cured product, such as the dielectric characteristics (dielectric constant and / or dielectric loss tangent), flame resistance, and low thermal expansion. 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 relative 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, measured according to the cavity resonator perturbation method. Furthermore, a practical lower limit for the relative dielectric constant is, for example, 2.0 or more. Furthermore, the filler used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, at a frequency of 10 GHz, measured according to the cavity resonator perturbation method. Furthermore, a practical lower limit for the dielectric loss tangent is, for example, 0.0001 or more.

[0196] The filler used in this embodiment is not particularly limited in type, and can be suitably used in the field of ordinary skill in the art.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, and other metal oxides, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, and other composite oxides, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, and other nitrides, aluminum hydroxide, aluminum hydroxide heat treatment product (aluminum hydroxide is heat treated and some of the crystal water is reduced), boehmite, magnesium hydroxide, and other metal hydroxides (including hydrates), acid Examples of fillers include inorganic fillers such as 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. The use of these inorganic fillers further improves the properties of the cured product of the resin composition, such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy.

[0197] The filler content 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 the filler content at or above the lower limit, the resulting cured product tends to have better low thermal expansion and low dielectric loss tangent. 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 the filler content below the upper limit tends to further improve the moldability of the resin composition. In the resin composition of the present embodiment, one preferred embodiment is one in which the content of the filler is 1 to 95 mass % of the components excluding the solvent, preferably 10 to 50 mass %, and more preferably 10 to 30 mass %. The resin composition of the present embodiment may contain only one type of filler, or may contain two or more types. When two or more types are contained, the total amount is preferably 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 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 use at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylic silane compounds, and vinylsilane compounds are more preferable.The silane coupling agents 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 the present embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but is preferably thermoplastic. The elastomer in 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. Further, 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 1000 or more. By setting the number-average molecular weight to 1000 or more, the low dielectric properties (Dk and / or Df, particularly low dielectric dissipation factor) of the resulting cured product tend to be more excellent. The number-average molecular weight is preferably 1500 or more, more preferably 2000 or more, and may be 600.00 or more, 700.00 or more, or 800.00 or more depending on the application, etc. 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 the present 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 hydroxy group, a phenolic hydroxyl group, a carboxy 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 may be 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 improved.

[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 viewpoints of availability and productivity. Among these, styrene is particularly preferred. The content of styrene monomer units in the elastomer (e) is preferably 10% by mass or more of all monomer units, more preferably 13% by mass or more, and even more preferably 15% by mass or more, 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 setting the content of styrene monomer units to the above upper limit or less, adhesion and tackiness to substrates and the like are improved. Furthermore, if the content of styrene monomer units is equal to or greater than the above lower limit, increased tack can be suppressed, adhesive residue and stop marks are less likely to occur, and easy peeling of adhesive surfaces from each other tends to be improved, 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, the total amount is preferably within the above range. The method for measuring the content of styrene monomer units 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 content of conjugated diene monomer units, etc., 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 the 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 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, adhesion can be suppressed, high adhesion strength can be maintained, and easy peeling of the adhesive surfaces can be improved.

[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 conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than the styrene monomer units. In the elastomer (e), the sum of styrene monomer units and conjugated diene monomer units preferably accounts for 90% by mass or more of all monomer units, more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more. As described above, the elastomer (e) may contain only one type of styrene monomer unit and one type of conjugated diene 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.

[0214] The elastomer (e) used in this embodiment may be a block polymer or a random polymer. It may also be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, an unhydrogenated elastomer in which the conjugated diene monomer units are not hydrogenated, or a partially hydrogenated elastomer in which the conjugated diene monomer units are partially hydrogenated, and is preferably an unhydrogenated elastomer or a partially hydrogenated elastomer. In one embodiment of this embodiment, the elastomer (e) is a hydrogenated elastomer. Here, the hydrogenated elastomer means, for example, an elastomer in which double bonds based on conjugated diene monomer units in the elastomer have been hydrogenated, and includes elastomers with a hydrogenation rate (hydrogenation rate) of 100% or more as well as elastomers with a hydrogenation rate of 80% or more. The hydrogenation rate in 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 1 It is calculated from the results of H-NMR spectroscopy. 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 means an elastomer in which some of the double bonds based on the conjugated diene monomer units in the elastomer have been hydrogenated, and usually 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 the present embodiment include SEPTON (registered trademark) 2104, V9461, and S8104 manufactured by Kuraray Co., Ltd., SOE (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 the liquid diene 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. As such a commercially available product, for example, MD3501 manufactured by Kraton Corporation may be used.

[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 intended use, the content may be 10 parts by mass or more, or 12 parts by mass or more. By setting the content at or above the lower limit, the dielectric properties (low dielectric loss 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, 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 intended use, the content may be 20 parts by mass or less, or 15 parts by mass or less. Setting the content at or below the upper limit tends to be further improved in heat resistance. The resin composition of the present embodiment may contain only one type of elastomer, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of elastomer, meaning 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 ingredients> 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, such as 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 the polymerization inhibitor include quinone, phenolic, nitroso, hydroxyamine, organic boric acid compounds, and compounds having a phenolic hydroxyl group. Specific examples include 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 reactants with organic chelating agents, 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, etc. The polymerization inhibitors that can be used are not limited to those mentioned above. 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, and 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. Furthermore, the total content of the polyphenylene ether compound other than the polyphenylene ether compound described above in <<<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, and more preferably 1% by mass or less, of the resin solids. By adopting such a configuration, the effects of the present invention are 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 solid content. By adopting such a configuration, the effects of the present invention can be more effectively exhibited.

[0220] <Application> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low-dielectric-constant material and / or a low-dielectric-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 prepregs, metal foil-clad laminates using prepregs, resin composite sheets, and printed wiring boards.

[0221] The resin composition of this embodiment preferably has a low relative 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 relative dielectric constant (Dk) of 2.50 or less at a frequency of 10 GHz, as measured by a cavity resonator perturbation method. There is no particular lower limit for the relative dielectric constant (Dk), but a practical value is, for example, 0.01 or more. Furthermore, when molded into a 1.0 mm thick cured plate (without metal foil), the dielectric loss tangent (Df) at a frequency of 10 GHz, as measured by a cavity resonator perturbation method, is preferably 0.0015 or less, more preferably 0.0010 or less, and even more preferably 0.008 or less. There is no particular lower limit for the dielectric loss tangent (Df), but a practical value is, for example, 0.0001 or more. Furthermore, radical curing of a resin composition can also be achieved by radically curing the resin composition, but this tends to result in rapid curing within a specific temperature range, allowing the resin composition to be cured more densely and further improving the low dielectric properties (Dk and / or Df) of the resulting cured product. That is, one 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 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 the temperature is raised again from 25°C to 303°C. The thermal expansion coefficient at 260°C to 280°C is preferably 200 ppm / °C or less, more preferably 120 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 150 ppm / °C or less, more preferably 120 ppm / °C or less, and practically 0 ppm / °C or more.

[0223] 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 when, for example, the resin composition of this embodiment is impregnated into glass cloth or the like. The material formed from the resin composition of the present embodiment may be used for applications in which a pattern is formed by exposure and development, or for applications in which no exposure and development is required. It is particularly suitable for applications in which no exposure and development is required.

[0224] <<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 the resin composition attached to the substrate, i.e., the amount of the resin composition (including filler) relative to the total amount of the semi-cured prepreg, is preferably in the range of 20 to 99% by mass, more preferably in the range of 20 to 80% by mass.

[0225] The substrate is not particularly limited as long as it is a substrate used in various printed wiring board materials. Examples of the substrate material 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, woven fabrics that have been subjected to an ultra-opening treatment and a clogging treatment are preferred from the viewpoint of dimensional stability. 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, etc. are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers that exhibit low relative permittivity and low dielectric loss tangent, such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. An example of a substrate with a low relative dielectric constant is a substrate with a relative dielectric constant of 5.0 or less (preferably 3.0 to 4.9). An example of a substrate with a low dielectric loss tangent is a substrate with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The relative dielectric constant and dielectric loss tangent are values ​​measured at a frequency of 10 GHz using a perturbation method cavity resonator.

[0226] <<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 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, metal foil is disposed on one or both sides of the prepreg, and laminate-molded. 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 metal foil. The number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil is not particularly limited as long as it is used as a material for printed wiring boards, and examples thereof include 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. 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 setting 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 setting 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 roughness Rz of the copper foil surface is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, and particularly preferably 0.7 μm or more, and is more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0227] Examples of lamination molding methods include those commonly used for molding printed wiring board laminates and multilayer boards. More specifically, examples include lamination molding 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. Alternatively, a multilayer board can be produced by combining the prepreg of this embodiment with a separately prepared inner layer wiring board and laminating it. For example, a multilayer board can be produced by placing copper foil of about 35 μm on both sides of a single prepreg of this embodiment, laminating it using the molding method described above, forming an inner layer circuit, blackening this circuit to form an inner layer circuit board, and then alternately arranging the inner layer circuit board and the prepreg of this embodiment one by one. Furthermore, copper foil is placed on the outermost layer, and lamination molding is performed 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.

[0228] 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 JIS C6481, Section 5.7 "Peel Strength." 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 fully satisfied.

[0229] 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 heat resistance, peel strength against metal foil, desmear resistance, crack resistance, and high-density processability.

[0230] <<Printed wiring boards>> 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 enhance 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 laminated on the outside of the prepreg. The resulting laminate is then integrally molded by heating and pressurizing. In this manner, a multilayer laminate is manufactured, in which an insulating layer consisting 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.

[0231] 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 this embodiment described above and / or its cured product. That is, the prepreg of this embodiment described above (for example, a prepreg formed from a base material and the resin composition of this embodiment impregnated or applied thereto), or the layer formed from the resin composition of the metal foil-clad laminate of this embodiment described above, serves as the insulating layer of this 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 Japanese Patent Application Laid-Open No. 2021-021027, the contents of which are incorporated herein by reference.

[0232] 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.

[0233] <<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 an example of a method for obtaining the resin composite sheet includes applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent to a support and drying the applied solution.

[0234] 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.

[0235] 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 onto 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.

[0236] 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, a temperature of 20°C to 200°C for 1 to 90 minutes is 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 generally tends to leave the solvent during drying. [Example]

[0237] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be appropriately changed 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.

[0238] <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 pump (Shimadzu Corporation, LC-20AD), a refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Showa Denko K.K., GPC KF-801, 802, 803, 804) at a flow rate of 1.0 mL / min and a column temperature of 40°C, using tetrahydrofuran as the solvent and a calibration curve prepared using monodisperse polystyrene.

[0239] <Measurement of parameters α and β> The parameters α and β in the resin (A) are: 1 The calculation was performed using H-NMR. The synthesized resin was dissolved in a mixed solvent of heptane and methanol, and the process of drying was repeated to remove the residual solvent contained in the recovered solid. The recovered solid was then dissolved in CDCl3 (containing 0.03% by volume of TMS (tetramethylsilane)), 1 H-NMR measurements were performed. 1 In H-NMR, the parameters α and β of each resin were calculated using the following formula: The peak position of TMS (tetramethylsilane) was set to 0 ppm.

number

[0240] <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 this internal temperature. After allowing the mixture to cool, the activated clay was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 129 g of a solid resin. The resulting resin (A) had an Mw of 1193, an Mn of 693, an Mw / Mn ratio of 1.7, and 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 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 resulting resin (A1) is shown in Figure 1. 1 The H-NMR chart is shown.

[0241] <Synthesis Example 2: Synthesis of Resin (A2)> A flask equipped with a thermometer, Dean-Stark apparatus, and 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 purified water. The internal temperature was raised to 120 °C while nitrogen was passed through the flask, and the reaction was carried out for 4 hours. 1,3-Diisopropenylbenzene was generated by the dehydration reaction (34.1 g of water was removed, almost the theoretical amount). After cooling, 300 g of toluene and 200 g of purified water were added, and the waste liquid was repeatedly washed with 200 g of purified water until it became neutral, yielding the product as a solution. The system was then reduced in pressure and concentrated, yielding 300 g of a toluene solution containing 1,3-diisopropenylbenzene. A flask equipped with a thermometer, condenser, and 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. Then, 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. Then, 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 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 remove 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 ratio of 2.2. In formula (Tx), the parameters α, β, and n+o+p were 0.66, 0.78, and 4.6, respectively. 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 the Mn of the synthesized resin was the average molecular weight. 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 (A2) was 571 g / eq. The functional group equivalent (g / eq.) of resin (A2) was calculated by (number average molecular weight (Mn) ÷ 2) ÷ β.

[0242] <Synthesis Example 3: Synthesis of Resin (A3)> A flask equipped with a thermometer, Dean-Stark apparatus, and 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 purified water. The internal temperature was raised to 120 °C while nitrogen was passed through the flask, and the reaction was carried out for 4 hours. 1,3-Diisopropenylbenzene was generated by the dehydration reaction (34.1 g of water was removed, almost the theoretical amount). After cooling, 300 g of toluene and 200 g of purified water were added, and the waste liquid was repeatedly washed with 200 g of purified water until it became neutral, yielding the product as a solution. The system was then 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 above-mentioned 1,3-diisopropenylbenzene-containing toluene solution, and heated to an internal temperature of 50°C with stirring. The mixture was then gradually heated to an internal temperature of 80°C over 5 hours and reacted at that temperature for an additional hour. After allowing to cool, the catalyst was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 129 g of a solid resin. The resulting resin (A3) had an Mw of 1,380, an Mn of 710, and an Mw / Mn ratio of 1.9. 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 (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. 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.

[0243] <Synthesis Example 4: Synthesis of modified polyphenylene ether compound> <<Synthesis of Difunctional Phenylene Ether Oligomers>> A 12 L vertical reactor equipped with a stirrer, a thermometer, an air inlet tube, and a baffle plate was charged with 9.36 g (42 mmol) of CuBr2 (copper bromide), 1.81 g (11 mmol) of N,N'-di-t-butylethylenediamine, 67.8 g (670 mmol) of n-butyldimethylamine, and 2600 g of toluene, and the mixture was stirred at an internal temperature of 40°C. A mixed solution of 129.3 g (0.48 mol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol, 878 g (7.2 mol) of 2,6-dimethylphenol, 1.22 g (7.2 mmol) of N,N'-di-t-butylethylenediamine, and 26.4 g (261 mmol) of n-butyldimethylamine, which had been dissolved in advance in 2300 g of methanol, was added dropwise over 230 minutes while bubbling a mixed gas of nitrogen and air adjusted to an oxygen concentration of 8% at a flow rate of 5.2 L / min, and the mixture was stirred at a reaction temperature of 40°C. After the dropwise addition was completed, 1500 g of water containing 48.1 g (130 mmol) of tetrasodium ethylenediaminetetraacetate was added to stop the reaction. The aqueous and organic layers were separated, and the organic layer was washed with a 1 M aqueous hydrochloric acid solution and then with pure water. The resulting solution was concentrated to 50% by mass using an evaporator, yielding 1980 g of a phenylene ether resin toluene solution A1. The number average molecular weight (GPC) was 1975 in terms of polystyrene, the weight average molecular weight (GPC) was 3514 in terms of polystyrene, and the hydroxyl equivalent was 990 g / eq.

[0244] <<Synthesis of modified polyphenylene ether compounds>> A reactor equipped with a stirrer, thermometer, and reflux condenser was charged with 833 g of the phenylene ether resin toluene solution A1 obtained above, 76.7 g (0.50 mol) of vinylbenzyl chloride (AGC Seimi Chemical Co., Ltd., "CMS-P"), 1600 g of methylene chloride, 6.20 g (0.046 mol) of benzyldimethylamine, 200 g of pure water, and 84 g of a 30.5 wt% NaOH aqueous solution, and the mixture was stirred at a reaction temperature of 40°C. After stirring for 24 hours, the organic layer was washed with a 1 M aqueous hydrochloric acid solution and then with pure water. The resulting solution was concentrated and added dropwise to methanol to solidify. The solid was collected by filtration and dried in vacuo to obtain 450 g of a polyphenylene ether compound primarily composed of a compound represented by formula (OP-15). The number average molecular weight calculated as polystyrene by the GPC method was 2250, the weight average molecular weight calculated as polystyrene by the GPC method was 3920, the double bond equivalent of the vinyl group was 1189 g / eq., and the hydroxyl group equivalent was 56250 g / eq.

[0245] Example 1 78 parts by mass of the resin (A1) obtained in Synthesis Example 1 above and 22 parts by mass of 1,2-bis(4-vinylphenyl)ethane (B1) (manufactured by Angene International) were dissolved in methyl ethyl ketone and toluene and mixed to obtain a varnish. The amount of each component mentioned above indicates the value of the solid content.

[0246] <Production of 1.0 mm thick hardened plate test specimens> The solvent was evaporated and removed from the resulting varnish to obtain a resin composition powder. The resulting resin composition powder was used to prepare a cured plate 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 (height), placed in a vacuum press (Kitagawa Seiki Co., Ltd.), and pressed at 200°C for 2 hours with a surface pressure of 3.0 MPa. The obtained cured plates were evaluated for dielectric constant (Dk), dielectric loss tangent (Df), and coefficient of thermal expansion (CTE). The evaluation results are shown in the table below.

[0247] <Measurement and evaluation methods> <Dielectric properties> The resulting cured plate was reduced in size 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) of the dried sample at a frequency of 10 GHz were measured using a perturbation 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. <<Dielectric constant (Dk)>> A: 2.50 or less B: Over 2.50 <<Dielectric loss tangent (Df)>> A: 0.0008 or less B: More than 0.0008 and less than 0.0010 C: More than 0.0010 and less than 0.0015 D: More than 0.0015

[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 thermal expansion coefficient was measured by the TMA (Thermo-Mechanical Analysis) method in accordance with JIS C 6481 5.19. The value was expressed in ppm / °C. The thermomechanical analyzer used was a TMAQ400 manufactured by TA Instruments, and the temperature was raised from 25°C to 303°C at a rate of 10°C per minute, cooled, and then raised again from 25°C to 303°C for measurement. The measurement results were evaluated as follows: α2 indicates the thermal expansion coefficient between 260 and 280°C, and α total indicates the thermal expansion coefficient from 50 to 280°C. The measurement results were evaluated as follows. (α2) A: 120ppm / ℃ or less B: More than 120ppm / ℃ and less than 200ppm / ℃ C: More than 200ppm / ℃ (α total ) A: 120ppm / ℃ or less B: More than 120ppm / ℃ and less than 150ppm / ℃ C: More than 150ppm / ℃

[0249] Example 2 The same procedures were carried out as in Example 1, except that the content of resin (A1) was changed to 70 parts by mass and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 30 parts by mass.

[0250] Example 3 The same procedures were carried out as in Example 1, except that the content of resin (A1) was changed to 50 parts by mass, and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 50 parts by mass.

[0251] Example 4 The same procedures were carried out as in Example 1, except that the content of resin (A1) was changed to 40 parts by mass and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 60 parts by mass.

[0252] Example 5 In Example 1, the content of resin (A1) was changed to 56 parts by mass, the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 11 parts by mass, and 33 parts by mass of BMI-70 (manufactured by K.I. Chemical Co., Ltd.) was added. The rest was the same.

[0253] Example 6 In Example 1, resin (A1) was not added, 70 parts by mass of resin (A2) obtained in Synthesis Example 2 was added, and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 30 parts by mass, but the rest was the same.

[0254] Example 7 In Example 1, resin (A1) was not added, 50 parts by mass of resin (A3) obtained in Synthesis Example 3 was added, and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 50 parts by mass, but the rest was the same.

[0255] Comparative Example 1 The same procedures were carried out as in Example 1, except that the content of resin (A1) was changed to 0 parts by mass and the content of 1,2-bis(4-vinylphenyl)ethane (B1) was changed to 100 parts by mass.

[0256] Comparative Example 2 The same procedures were carried out as in Example 1, except that the resin (A1) and 1,2-bis(4-vinylphenyl)ethane (B1) were not blended, and 100 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 4 was blended.

[0257] Comparative Example 3 In Example 1, the content of resin (A1) was 50 parts by mass, 1,2-bis(4-vinylphenyl)ethane (B1) was not added, and 50 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 4 was added, and the rest was the same.

[0258] Comparative Example 4 In Example 1, the content of resin (A1) was 40 parts by mass, 1,2-bis(4-vinylphenyl)ethane (B1) was not added, and 60 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 4 was added, and the other procedures were the same.

[0259] Comparative Example 5 The same procedure was carried out as in Example 1, except that 1,2-bis(4-vinylphenyl)ethane (B1) was not added, and 22 parts by mass of a mixture of m-divinylbenzene and p-divinylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd., functional group equivalent (vinyl group equivalent) was 65 g / eq.) was added. However, since molding was not possible, evaluation was not performed.

[0260] Comparative Example 6 The same procedure was repeated as in Example 1, except that resin (A1) and 1,2-bis(4-vinylphenyl)ethane (B1) were not blended, and 100 parts by mass of a mixture of m-divinylbenzene and p-divinylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd., functional group equivalent (vinyl group equivalent) was 65 g / eq.) was blended. However, molding was not possible, so evaluation was not performed.

[0261] [Table 1] [Table 2] [Table 3]

[0262] 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. The composition contains 90 to 10 parts by mass of a compound (B) represented by formula (BV) relative to 10 to 90 parts by mass of a resin (A), A resin composition, wherein the resin (A) is a resin represented by formula (T): 【Chemistry 1】 (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x1 represents an integer of 0 to 4, and R represents a divalent group.) 【Chemistry 2】 (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.)

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 having the following structure: 【Transformation 3】 (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 (A) has a parameter α calculated from formula (α) of 0.20 or more and 1.00 or less, a parameter β calculated from formula (β) of 0.20 or more and 3.00 or less, and the resin (A) has a number average molecular weight of 400 to 3000. The resin composition according to claim 3. [Equation 1] (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 in formula (BV), r represents an integer of 1 to 4.

6. The R is a group having the following structure: the parameter α of the resin (A) calculated from the formula (α) is 0.20 or more and 1.00 or less, the parameter β of the resin (A) calculated from the 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 resin composition according to claim 1, wherein in formula (BV), r represents an integer of 1 to 4. 【number】 (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.) Fat composition. [Equation 2] (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.)

7. the resin composition contains 45 to 75 parts by mass of the resin (A) and 55 to 25 parts by mass of the compound (B) represented by formula (BV), and the total amount of the resin (A) and the compound (B) represented by formula (BV) is 90 parts by mass or more per 100 parts by mass of resin solid content, The resin composition is molded into a sample having a thickness of 1.0 mm, and the dielectric loss tangent (Df) at a frequency of 10 GHz measured by a cavity resonator perturbation method in accordance with JIS C218:2007 is 0.0018 or less. The resin composition according to claim 6.

8. The resin composition according to any one of claims 1 to 7, further comprising a filler.

9. The resin composition according to any one of claims 1 to 7, 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 adjuster, a lubricant, an antifoaming agent, a leveling agent, a gloss agent, and a polymerization inhibitor.

10. The resin composition according to any one of claims 1 to 7, which is for use in a printed wiring board.

11. A cured product of the resin composition according to any one of claims 1 to 7.

12. A prepreg formed from a substrate and the resin composition according to any one of claims 1 to 7.

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 the 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 7, disposed on the surface of the support.

15. A printed wiring board including an insulating layer and a conductor layer disposed on a surface of the insulating layer, A printed wiring board, wherein the insulating layer comprises a layer formed from the resin composition according to any one of claims 1 to 7.

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

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