Compound, resin composition, cured product, prepreg, resin composite sheet, printed wiring board, semiconductor device, and low dielectric filler

Abstract

Provided are a compound, and a resin composition, a cured product, a prepreg, a resin composite sheet, a printed wiring board, a semiconductor device, and a low dielectric filler. The compound according to the present disclosure is a compound represented by formula (1A) and / or is represented by formula (1B).

Description

Compounds, resin compositions, cured products, prepregs, resin composite sheets, printed circuit boards, semiconductor devices, and low-dielectric fillers

[0001] The present invention relates to compounds, resin compositions, cured products, prepregs, resin composite sheets, printed circuit boards, semiconductor devices, and low-dielectric fillers.

[0002] In recent years, the integration and miniaturization of semiconductor elements used in mobile devices, electronic equipment, and communication devices has accelerated. Consequently, technologies enabling high-density mounting of semiconductor elements are required, and improvements are needed in printed circuit boards, such as substrates for mounting semiconductor elements, which play a crucial role in this process. Meanwhile, the applications of electronic equipment are diversifying and expanding. As a result, the various characteristics required of printed circuit boards, such as substrates for mounting semiconductor elements, and the metal foil laminates and prepregs used therein, have become more diverse and stringent. To obtain improved printed circuit boards while considering these required characteristics, various materials and processing methods have been proposed. One example is the development of improved resin materials that constitute prepregs and resin composite sheets. Such materials are described in Patent Documents 1 to 4.

[0003] Japanese Patent Publication No. 2022-058409, Japanese Patent Publication No. 2021-187893, International Publication No. 2019 / 188189, Japanese Patent Publication No. 2018-090728

[0004] As described above, the applications of electronic devices and the like are diversifying and expanding, and new materials are needed for the resin materials that make up prepregs and the like. Here, the resin materials are required to exhibit low dielectric properties (Dk and / or Df) when cured. The present invention aims to solve this problem and to provide compounds that can achieve low dielectric properties when compounded with resin, as well as resin compositions, cured products, prepregs, resin composite sheets, printed circuit boards, semiconductor devices, and low dielectric fillers.

[0005] Under these circumstances, the inventors conducted extensive research and found that the above problems can be solved by using a compound represented by formula (1A) and / or a compound represented by formula (1B), as described below. Specifically, the above problems were solved by the following means: [1] A compound represented by formula (1A) and / or a compound represented by formula (1B). Formula (1A) Formula (1B) [2] The compound according to [1], wherein the compound is at least one of the compound represented by formula (2A), the compound represented by formula (2B), and the compound represented by formula (2C). Formula (2A) Formula (2B) Formula (2C) [3] The compound according to [1] or [2], wherein the compound is a compound represented by formula (3A) and / or a compound represented by formula (3B). Formula (3A) Formula (3B) [4] A resin composition comprising a compound described in any of [1] to [3] and a thermosetting compound. [5] The resin composition according to [4], wherein the thermosetting compound comprises at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group. [6] The resin composition according to [4] or [5], further comprising a filler. [7] The resin composition according to any one of [4] to [6], further comprising at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors. [8] A resin composition according to any one of [4] to [7], for use in printed circuit boards. [9] A resin composition according to any one of [4] to [8], wherein the thermosetting compound comprises at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group, further comprising a filler, and further comprising at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors, for use in printed circuit boards.

[10] A cured product of the resin composition according to any one of [4] to [9].

[11] A base material and a prepreg formed from any one of the resin compositions described in [4] to [9].

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

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

[13] A resin composite sheet comprising a support and a layer formed from any one of the resin compositions described in [4] to [9] disposed on the surface of the support.

[14] A printed wiring board comprising an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from any one of the resin compositions described in [4] to [9].

[15] A semiconductor device comprising the printed wiring board described in

[14] .

[16] A low dielectric filler comprising the compound described in any one of [1] to [3].

[0006] The present invention makes it possible to provide compounds that can achieve low dielectric properties when incorporated into resins, as well as resin compositions, cured products, prepregs, resin composite sheets, printed circuit boards, semiconductor devices, and low dielectric fillers.

[0007] The compound represented by formula (3A) was isolated from the compound obtained in Synthesis Example 1. １ The 1H-NMR chart is shown. The compound represented by formula (3B) was isolated from the compound obtained in Synthesis Example 1. １ The H-NMR chart is shown. The solid obtained in Synthesis Example 1 １ The H-NMR chart is shown. The GPC chart of the solid obtained in Synthesis Example 1 is shown. The GPC chart of the solid obtained in Synthesis Example 2 is shown. １ The H-NMR chart is shown. The GPC chart of the solid obtained in Synthesis Example 3 is shown. １ The H-NMR chart is shown.

[0008] Hereinafter, embodiments for carrying out the present invention (hereinafter simply referred to as "this embodiment") will be described in detail. Note that the following embodiments are illustrative examples for explaining the present invention, and the present invention is not limited to these embodiments. In this specification, "~" is used to mean that the numerical values ​​before and after it include the lower and upper limits. "A~B" means A or greater and B or less. Furthermore, any combination of the upper and lower limits of numerical values ​​in this specification is given as an example of this embodiment. In this specification, various physical properties and characteristic values ​​are given at 23°C unless otherwise specified. In the notation of groups (atomic groups) in this specification, notations that do not specify substitution and unsubstituted include both groups (atomic groups) with substituents and groups (atomic groups) without substituents. For example, "alkyl group" includes not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups). In this specification, when notations that do not specify substitution and unsubstituted are used, unsubstituted is preferred. Examples of substituents in this specification are preferably halogen atoms, cyano groups, nitro groups, hydroxyl groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclic oxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, acyl groups, or amino groups; more preferably halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, alkenyl groups, or acyl groups; even more preferably alkyl groups, aryl groups, aryloxy groups, or alkenyl groups; and even more preferably alkyl groups. The formula weight of these substituents is preferably 15 or more, and preferably 200 or less. Formula weight refers to, for example, a methyl group (-CH ３ If so, the result is 15. These substituents may have further substituents, but it is preferable that they do not have substituents.

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

[0010] In this specification, relative permittivity refers to the ratio of the dielectric constant of a material to the dielectric constant of a vacuum. In this specification, relative permittivity may also be simply referred to as "dielectric constant." Furthermore, unless otherwise specified, relative permittivity in this specification refers to the relative permittivity at a frequency of 10 GHz measured according to the cavity resonance perturbation method. In this specification, weight-average molecular weight and number-average molecular weight are measured according to paragraph 0259 of International Publication No. 2024 / 101237 unless otherwise specified. If the standards shown in this specification differ in measurement methods, etc., from year to year, unless otherwise specified, the standards as of January 1, 2024 shall be used.

[0011] In this specification, resin solids refer to components excluding fillers and solvents, and include thermosetting compounds and, if necessary, other thermosetting compounds and other resin additive components (such as flame retardants). The compound represented by formula (1A) and / or the compound represented by formula (1B) are considered fillers. In this specification, unless otherwise specified, fillers refer to fillers other than the compound represented by formula (1A) and / or the compound represented by formula (1B).

[0012] The embodiments of the present invention will be described in detail below, but the description of the constituent elements described below is merely one example of an embodiment of the present invention and is not limited to these.

[0013] The compounds of this embodiment are compounds represented by formula (1A) and / or compounds represented by formula (1B). Formula (1A) Formula (1B) Because such compounds exhibit excellent low dielectric properties, when they are incorporated into a resin composition and the resin composition is cured, the resulting cured product can achieve low dielectric properties (Dk and / or Df).

[0014] The compound represented by formula (1A) and / or the compound represented by formula (1B) is preferably at least one of the compound represented by formula (2A), the compound represented by formula (2B), and the compound represented by formula (2C), and more preferably the compound represented by formula (3A) and / or the compound represented by formula (3B). Formula (2A) Formula (2B) Formula (2C) Formula (3A) Formula (3B)

[0015] Furthermore, since the above compound can be obtained in powder form at 23°C, it can also be used as a low-dielectric filler. In addition, the above compound can be used as a chain transfer agent or molecular weight modifier in the production of polymers. The compound represented by formula (1A) and / or the compound represented by formula (1B) may be a single compound or a mixture.

[0016] An example of the application of the compounds of this embodiment is a resin composition containing the compound represented by formula (1A) and / or the compound represented by formula (1B), and a thermosetting compound. The details of the resin composition of this embodiment will be described below.

[0017] <Compound represented by formula (1A) and / or compound represented by formula (1B)> As described above, the resin composition of this embodiment contains the compound represented by formula (1A) and / or the compound represented by formula (1B). Formula (1A) Formula (1B)

[0018] In the resin composition of this embodiment, the content of the compound represented by formula (1A) and / or formula (1B) is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, even more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, and also 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 even more preferably 50 parts by mass or less. Setting the content above the lower limit tends to further improve the low dielectric properties (Dk and / or Df) of the resulting cured product. Setting the content below the upper limit tends to further improve the heat resistance of the resulting cured product. The compound represented by formula (1A) and / or formula (1B) contained in the resin composition of this embodiment may be a mixture of two or more stereoisomers or may be a single compound.

[0019] The method for producing the compound represented by formula (1A) and / or the compound represented by formula (1B) in the resin composition of this embodiment is not particularly limited, and the raw materials, reaction temperature, catalyst species, catalyst amount, reaction solvent, raw material concentration, etc., when synthesizing the compounds represented by formula (1A) and / or formula (1B) can be appropriately adjusted.

[0020] Examples of raw materials that can be used when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) include m-bis(α-hydroxyisopropyl)benzene and 1,3-diisopropenylbenzene.

[0021] When m-bis(α-hydroxyisopropyl)benzene is used as a starting material for synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B), 1,3-diisopropenylbenzene can be generated in situ by a dehydration reaction. Furthermore, the compound represented by formula (1A) and / or the compound represented by formula (1B) can be synthesized directly without isolating 1,3-diisopropenylbenzene. The generated 1,3-diisopropenylbenzene can also be purified by distillation or other means before use.

[0022] The pressure used when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) is preferably atmospheric pressure, but the synthesis can also be carried out under reduced pressure or increased pressure.

[0023] When synthesizing 1,3-diisopropenylbenzene, which is a raw material for the compound represented by formula (1A) and / or the compound represented by formula (1B), it is preferable to pass an inert gas such as nitrogen through the mixture or introduce it into the liquid in order to efficiently carry out the dehydration reaction.

[0024] The catalyst used when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) can be added all at once or in stages.

[0025] When synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B), the heating rate 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. Furthermore, the heating rate is preferably 5°C / min or less, and preferably 4°C / min or less.

[0026] Examples of stirring devices used in the synthesis process of the compound represented by formula (1A) and / or the compound represented by formula (1B) include mechanical stirring devices, magnetic stirring devices, and ultrasonic stirring devices.

[0027] As a temperature control means used in the synthesis process of the compound represented by formula (1A) and / or the compound represented by formula (1B), a jacketed reaction vessel, a circulating device capable of heating or cooling, an infrared heating device, a microwave heating device, or a device combining these may be used.

[0028] The reaction temperature when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) is preferably 40°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, preferably 100°C or lower, more preferably 90°C or lower, and even more preferably 80°C or lower. By setting the temperature within this range, it is possible to achieve both improved yield and improved reaction rate of the compound represented by formula (1A) and / or the compound represented by formula (1B). Furthermore, the reaction temperature does not need to be the same from the start to the end of the reaction, and the temperature may be varied. In this case, it is preferable that the average reaction temperature for the entire process is within the above range.

[0029] The catalyst species used when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) is not specifically defined, but acid catalysts are exemplified. Examples of acid catalysts include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; organic acids such as oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, and fluoromethanesulfonic acid; solid acids such as activated clay, acid clay, silica alumina, and zeolite; heteropolyhydrochloric acid; and strongly acidic ion exchange resins. When a catalyst is used, its amount is typically 0.01 parts by mass or more and 50.0 parts by mass or less per 100 parts by mass of the raw materials for the compound represented by formula (1A) and / or the compound represented by formula (1B). The catalyst may be used alone or in combination of two or more types. When used in combination, the total amount is preferably within the above range. Furthermore, the catalyst may be added directly to the reaction system, or it may be dissolved in a solvent such as water or an organic solvent before being added.

[0030] The reaction solvent used when synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B) is not particularly specified in terms of type, but examples include at least one selected from the group consisting of aromatic hydrocarbon solvents such as toluene, benzene, chlorobenzene, and xylene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; aliphatic hydrocarbon solvents such as hexane, heptane, and octane; ester solvents such as ethyl acetate and propyl acetate; amide solvents such as dimethylformamide and dimethylacetamide; alcohol solvents; and ketone solvents. A mixture with water may also be used. Examples of alcohol solvents include methanol, ethanol, butanol, propanol, methylpropylene glycol, and propylpropylene glycol, and examples of ketone solvents include acetone, methyl ethyl ketone, diethyl ketone, methyl butyl ketone, and methyl isobutyl ketone. Other examples include tetrahydrofuran and dioxane, but are not limited to these. An example of a reaction solvent in this embodiment is that it includes an aromatic hydrocarbon solvent.

[0031] When synthesizing the compound represented by formula (1A) and / or the compound represented by formula (1B), the concentration of the raw materials is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 50% by mass or more, preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, based on 100% by mass of the reaction solution. By setting the concentration within the above range, it is possible to achieve both an improvement in the yield of the compound represented by formula (1A) and / or the compound represented by formula (1B) and an improvement in the reaction rate. Furthermore, the concentration does not need to be the same from the start to the end of the reaction, and the concentration may be varied. If the concentration changes from the start to the end of the reaction, it is preferable that the concentration at the point in time when the raw material concentration is highest falls within the above range.

[0032] Furthermore, the synthetic solution containing the compound represented by formula (1A) and / or the compound represented by formula (1B) synthesized by the above synthesis method may be used after being purified by dehydration or other treatments. The content of the compound represented by formula (1A) and / or the compound represented by formula (1B) in the synthetic solution is not particularly limited, but is preferably 30% by mass or more, more preferably 40% by mass or more, preferably 70% by mass or less, and more preferably 60% by mass or less, based on 100% by mass of the solid content in the synthetic solution. Satisfying the above range tends to improve the crystallization yield of the compound represented by formula (1A) and / or the compound represented by formula (1B), which will be described later.

[0033] Furthermore, known techniques may be used to separate the compound represented by formula (1A) and / or the compound represented by formula (1B) from a synthesis solution containing the compound represented by formula (1A) and / or the compound represented by formula (1B) synthesized by the above synthesis method. For example, a method may be used in which the synthesis solution is concentrated and heated after production, and then cooled to crystallize only the above compound, or a method may be used in which the synthesis solution is dehydrated and then a large amount of an organic solvent with low solubility of the above compound is added to crystallize only the above compound. The heating temperature is preferably 30°C or higher, more preferably 40°C or higher, even more preferably 50°C or higher, preferably 100°C or lower, more preferably 90°C or lower, and even more preferably 80°C or lower. By setting the temperature within the above range, the reaction of solids in the synthesis solution can be suppressed and the crystallization yield can be improved. Furthermore, the low-solubility organic solvent is not particularly limited as long as it is a solvent in which the solubility of the compound is lower than that of the selected reaction solvent. Examples include alcohol solvents such as methanol, ethanol, and propanol, and aliphatic hydrocarbon solvents such as hexane, heptane, and octane.

[0034] <Other Low Molecular Weight Compounds Having Cyclic Compounds> In addition to the above, the resin composition of this embodiment may also contain other low molecular weight compounds having cyclic compounds. Including such compounds tends to further improve at least one of the low dielectric properties (Dk and / or Df), heat resistance, peel strength, low thermal expansion, low water absorption, handling properties, and flame retardancy of the resulting cured product. Furthermore, at least one of the compatibility, solubility, low viscosity, and moldability of each component in the resin composition tends to further improve. Examples of other low molecular weight compounds having cyclic compounds include compounds having a structural unit represented by formula (AA), and compounds forming a cyclic structure in which only the structural unit represented by formula (AA) is bonded are preferred. The number average molecular weight of low molecular weight compounds having cyclic compounds is usually 300 to less than 1300. (In formula (AA), n, o, p, q, and r are repeating units, each independently representing a number from 0 to 8, and 3 ≤ n + o + p + q + r ≤ 8. Constituent units (a), (b), (c), (d), and (e) are each linked by * to other constituent units (a), (b), (c), (d), and (e), and each constituent unit may be linked randomly.)

[0035] The following is an example of a compound having a structural unit represented by formula (AA). Note that low molecular weight compounds containing cyclic compounds include, in addition to the compounds shown below, compounds in which the bonding order of the structural units (a), (b), (c), (d), and (e) in formula (AA) differs from that of the structural formula shown below.

[0036] If the resin composition of this embodiment contains the above-mentioned other low-molecular-weight compounds, the content thereof is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, even more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, and also 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 even more preferably 50 parts by mass or less. The resin composition of this embodiment may contain only one of the above-mentioned other low-molecular-weight compounds, or it may contain two or more. If it contains two or more, it is preferable that the total amount is within the above range.

[0037] <Thermosetting Compound> The resin composition of this embodiment contains a thermosetting compound, and more preferably contains a thermosetting resin. The thermosetting compound preferably contains at least one selected from the group consisting of maleimide compounds, aromatic resins having carbon-carbon double bonds at the terminals, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having vinylene groups; more preferably contains at least one selected from the group consisting of maleimide compounds, aromatic resins having carbon-carbon double bonds at the terminals, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, and phenol compounds; even more preferably contains at least one selected from the group consisting of maleimide compounds, aromatic resins having carbon-carbon double bonds at the terminals, and cyanate ester compounds; even more preferably contains at least one selected from the group consisting of maleimide compounds and aromatic resins having carbon-carbon double bonds at the terminals; and even more preferably contains an aromatic resin having carbon-carbon double bonds at the terminals.

[0038] Among the thermosetting compounds contained in the resin composition of this embodiment, compounds that fall under two or more of the compounds listed above shall be considered as examples of specific compounds, as specified herein. On the other hand, among the thermosetting compounds contained in the resin composition of this embodiment, compounds that fall under two or more of the compounds listed above but are not specified herein shall be classified as the compounds listed above, unless otherwise specified. For example, a compound that falls under both maleimide compounds and epoxy compounds shall be considered a maleimide compound.

[0039] The content of the 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, and may be 60 parts by mass or more, 65 parts by mass or more, and also 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. Setting the content above the lower limit tends to further improve the heat resistance and peel strength of the resulting cured product. Setting the content below the upper limit tends to further improve the low dielectric properties (Dk and / or Df) of the resulting cured product. The resin composition of this embodiment may contain only one type of thermosetting compound or two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0040] <<Maleimide Compound>> The resin composition of this embodiment preferably contains a maleimide compound. In this embodiment, the maleimide compound preferably has one or more (preferably two or more, more preferably 2 to 12, still more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2 maleimide groups in one molecule). In this embodiment, the maleimide compound is a compound 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), maleimide compound (M6), maleimide compound (M7), and maleimide compound (M8), preferably contains 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), and a compound represented by formula (M5), more preferably contains 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 (M3), a compound represented by formula (M4), and a compound represented by formula (M5), still more preferably contains one or more selected from the group consisting of a compound represented by formula (M1), a compound represented by formula (M3), and a compound represented by formula (M5), even more preferably contains one or more selected from the group consisting of a compound represented by formula (M1) and / or a compound represented by formula (M3). When these maleimide compounds are used in a material for a printed wiring board (for example, a metal foil-clad laminate), excellent heat resistance can be imparted.

[0041] (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and R ５２ each independently represents a hydrogen atom or a methyl group, and n １ represents an integer of 1 or more.) R ５１Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５２ It is preferable that it is a methyl group. １ The integer is preferably between 1 and 10, more preferably between 1 and 5, even more preferably between 1 and 3, even more preferably 1 or 2, and even more preferably 1. Specifically, the following compounds are examples of preferred values ​​of formula (M0). In the above formula, R ８ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and a methyl group is preferred.

[0042] The compound represented by formula (M0) may be a single compound or a mixture of two or more compounds. An example of a mixture is n １ A mixture of different compounds, R ５１ and / or R ５２ Examples include mixtures of compounds with different types of substituents, mixtures of compounds with different bonding positions (meta, para, ortho) between the maleimide group and the oxygen atom on the benzene ring, and mixtures of compounds in which two or more of the above differences are combined. The same applies to compounds represented by formulas (M1) to (M8) below.

[0043] (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4-6 membered alicyclic group. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. Ｍ９ and R Ｍ１０Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. Ｍ１５ Each of these 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 from 0 to 3. nx represents an integer from 1 to 20.

[0044] R in the formula Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these 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, ethyl group, propyl group, or butyl group, with the methyl group being particularly preferred. Ｍ１ and R Ｍ３ Each of these is independently preferably an alkyl group, R Ｍ２ and R Ｍ４ A hydrogen atom is preferred. Ｍ５ and R Ｍ６ Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ Ar represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or anthracenediyl group, more preferably a phenylene group, and even more preferably an m-phenylene group. ＭAr may have substituents, preferably alkyl groups, more preferably alkyl groups having 1 to 12 carbon atoms, even more preferably alkyl groups having 1 to 6 carbon atoms, even more preferably methyl groups, ethyl groups, propyl groups, and butyl groups, with methyl groups being particularly preferred. However, Ar Ｍ It is preferable that it is unsubstituted. A is a 4- to 6-membered alicyclic group, and a 5-membered alicyclic group (preferably a group that combines with a benzene ring to form an indan ring) is more preferable. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R Ｍ９ and R Ｍ１０ Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being more preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these 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, ethyl group, propyl group, or butyl group, with the methyl group being particularly preferred. Ｍ１２ and R Ｍ１３ Each of these is independently preferably an alkyl group, R Ｍ１１ and R Ｍ１４ A hydrogen atom is preferred. Ｍ１５Each of these 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 from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0. nx represents an integer from 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) with at least two or more compounds having different nx values. When two or more types are included, the average value of nx (average number of repeating units) in the compound represented by formula (M1) in the resin composition is preferably 0.92 or higher, more preferably 0.95 or higher, even more preferably 1.0 or higher, and even more preferably 1.1 or higher, in order to obtain a low melting point (low softening point), low melt viscosity, and excellent handling properties. 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 also be 5.0 or less. The same applies to formula (M1-1), etc., which will be described later.

[0045] The compound represented by formula (M1) is preferably the compound represented by the following formula (M1-1). (In formula (M1-1), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ Each of these independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ Each of these independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２Each independently represents a hydrogen atom or an alkyl group. R Ｍ３３ R Ｍ３４ R Ｍ３５ and R Ｍ３６ Each independently represents a hydrogen atom or an organic group. R Ｍ３７ R Ｍ３８ and R Ｍ３９ Each independently represents a hydrogen atom or an alkyl group. nx represents an integer of 1 or more and 20 or less.)

[0046] In the formula, R Ｍ２１ R Ｍ２２ R Ｍ２３ and R Ｍ２４ 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, still 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 Ｍ２１ and R Ｍ２３ are preferably alkyl groups, and R Ｍ２２ and R Ｍ２４ are preferably hydrogen atoms. R Ｍ２５ and R Ｍ２６ Each independently represents a hydrogen atom or an alkyl group, and an alkyl group is preferable. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more 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 Ｍ３０ Each independently represents a hydrogen atom or an organic group, and a hydrogen atom is preferable. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still 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 Ｍ３２Each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more 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, still more preferably an alkyl group having 1 to 6 carbon atoms, even 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 are preferably a hydrogen atom, and R Ｍ３４ and R Ｍ３５ are preferably an alkyl group. R Ｍ３７ R Ｍ３８ and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more 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.

[0047] The compound represented by the formula (M1-1) is preferably a compound represented by the following formula (M1-2). (In the formula (M1-2), R Ｍ２１ R Ｍ２２ R Ｍ２３ and R Ｍ２４ each independently represents a hydrogen atom or an organic group. R Ｍ２５ and R Ｍ２６ each independently represents a hydrogen atom or an alkyl group. R Ｍ２７ R Ｍ２８ R Ｍ２９ and R Ｍ３０ each independently represents a hydrogen atom or an organic group. R Ｍ３１ and R Ｍ３２Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ Each of these independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ Each of these independently represents either a hydrogen atom or an alkyl group. nx represents an integer between 1 and 20.

[0048] 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 equation (M1-1), respectively. Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and are synonymous with nx, and the preferred range is also similar.

[0049] The compound represented by formula (M1-1) is preferably the compound represented by the following formula (M1-3), and more preferably the compound represented by the following formula (M1-4). (In equation (M1-3), nx represents an integer between 1 and 20.) nx may also be an integer less than or equal to 10. (In equation (M1-4), nx represents an integer between 1 and 20.) nx may also be an integer less than or equal to 10.

[0050] 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. Setting it above the lower limit tends to further improve the low dielectric properties (Dk and / or Df) and low water absorption of the resulting cured product. 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. Setting it below the upper limit tends to further improve the heat resistance and handling properties of the resulting cured product.

[0051] Further details of the compound represented by formula (M1) can be found in International Publication No. 2020-217679, which is incorporated herein by reference.

[0052] (In formula (M2), R ５４ Each of these independently represents a hydrogen atom or a methyl group, n ４ n represents an integer greater than or equal to 1. ４ n is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and may be 1. The compound represented by formula (M2) is n ４ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0053] (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10.) ５５Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５ n is preferably an integer between 1 and 5, more preferably an integer between 1 and 3, and even more preferably 1 or 2. The compound represented by formula (M3) is n ５ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0054] (In formula (M4), R ５６ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and R ５７ Each of these independently represents either a hydrogen atom or a methyl group.) An example of a compound represented by formula (M4) is R ５６ Each is independently a methyl group or an ethyl group, R ５７ The R is a methyl group. ５６ It is more preferable that the two benzene rings are a methyl group and an ethyl group, respectively. Another example of a compound represented by formula (M4) is R ５６ and R ５７ The fact is that it is a hydrogen atom.

[0055] (In formula (M5), R ５８ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５９ Each of these independently represents a hydrogen atom or a methyl group, n ６ (This represents an integer greater than or equal to 1.) R ５８Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５９ It is preferable that it is a methyl group. ６ n is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and may be 1. The compound represented by formula (M5) is n ６ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0056] Maleimide compounds (M6) are compounds having the structure represented by formula (M6) and maleimide groups at both ends of the molecular chain. (In formula (M6), R ６１ R 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 R 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 independently represents an integer from 0 to 10.) Details of the maleimide compound (M6) and its preparation method can be found in paragraphs 0061 to 0066 of International Publication No. 2020 / 262577, which are incorporated herein by reference.

[0057] Maleimide compound (M7) is a maleimide compound obtained by using 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 2 ethenyl groups, and maleic anhydride. Preferably, maleimide compound (M7) is a compound having the structure represented by formula (M7). (In the above formula (M7), R １ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, and R ２ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group. ３ , R ４ , R ５ and R ６ Each of these independently represents a hydrogen atom or a methyl group, and R ３ and R ４ One side is a hydrogen atom, and the other side is a methyl group, R ５ and R ６ One side is a hydrogen atom, and the other side is a methyl group, X １ These are expressed independently as follows (x): (In formula (x), R ７ and R ８ Each of these independently represents a hydrogen atom or a methyl group, and R ７ and R ８ One side is a hydrogen atom, and the other side is a methyl group, R ９ Each of these 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, where t represents an integer from 0 to 4. ) represents a substituent represented by X １ X per benzene ring to which is bonded １ (This is the average number of substitutions, representing numbers from 0 to 4, where 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.)

[0058] Details of the maleimide compound (M7) used in this embodiment can be found in Japanese Patent No. 7160151, which is incorporated herein by reference.

[0059] The maleimide compound (M8) is a bismaleimide compound having a hydrocarbon group in which eight or more atoms are linked in a linear chain, 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 dielectric constant and dielectric loss tangent tend to be better. (In formula (M8), R １ and R ３ Each of these independently represents a hydrocarbon group in which eight or more atoms are linked in a linear chain, and R ２ Each of these independently represents a substituted or unsubstituted cyclic hydrocarbon group that may contain 4 to 10 heteroatoms constituting the ring, and n represents a number from 1 to 10.

[0060] In equation (M8), R １ and R ３ However, it is an octylene group, R ２ However, it is preferable that the cycloalkylene group has an alkyl group having 6 to 8 carbon atoms as a substituent.

[0061] For maleimide compounds (M8), refer to the descriptions in paragraphs 0014 to 0022 of Japanese Patent Publication No. 2018-083893 and paragraphs 0012 to 0022 of Japanese Patent Publication No. 2018-090728, the contents of which are incorporated herein by reference.

[0062] Maleimide compounds may be manufactured by known methods or commercially available products may be used. Examples of commercially available products include "BMI-80" manufactured by K.I. Chemicals Co., Ltd. as a compound represented by formula (M0), "NE-X-9470S" and "NE-X-9480S" manufactured by DIC Corporation as compounds represented by formula (M1), "BMI-2300" manufactured by Yamato Chemical Industries Co., Ltd. as a compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M3), and a compound represented by formula (M4) Examples of compounds include "BMI-70" manufactured by Kei-I Kasei Co., Ltd., "BMI-5100" manufactured by Yamato Kasei Kogyo 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.

[0063] Other maleimide compounds include, for example, oligomers of N-phenylmaleimide, N-cyclohexylmaleimide, phenylmethanemaleimide, 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, and their prepolymers, as well as 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 Japanese Patent Publication No. 2025-9839 can also be referenced, and this information is incorporated herein.

[0064] 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 also 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. Setting it above the lower limit tends to result in better low dielectric properties (Dk and / or Df, particularly Df) of the resulting cured product. Setting it below the upper limit tends to result in better peel strength of the resulting cured product.

[0065] When the resin composition of this embodiment contains a maleimide compound, the lower limit of its 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, depending on the application, etc., it may be 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more. When the maleimide compound content is 1 part by mass or more, the flame resistance of the resulting cured product tends to improve. Furthermore, the upper limit of the maleimide compound content 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 even more preferably 55 parts by mass or less, depending on the application, etc., it may be 50 parts by mass or less, or 45 parts by mass or less, based on 100 parts by mass of resin solids in the resin composition. When the maleimide compound content is 90 parts by mass or less, the peel strength and low water absorption tend to improve. The resin composition in this embodiment may contain only one maleimide compound or two or more. When two or more are included, it is preferable that the total amount is within the above range.

[0066] <<Aromatic Resins Having Carbon-Carbon Double Bonds at the Terminals>> An aromatic resin having carbon-carbon double bonds at the terminals is, for example, a compound having carbon-carbon double bonds at the terminals and containing an aromatic ring, and is a compound that hardens with heat. By using an aromatic resin having carbon-carbon double bonds at the terminals in combination with an elastomer, the compatibility between the two is improved, and the coefficient of thermal expansion of the resulting cured product can be made smaller. Specifically, the aromatic resin having carbon-carbon double bonds at the terminals preferably includes one or more selected from the group consisting of a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminals, a polymer having a structural unit represented by formula (V), and a resin having an end group represented by formula (T1) and an indan skeleton, and more preferably includes a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminals and / or a resin having an end group represented by formula (T1) and an indan skeleton.

[0067] When the resin composition of this embodiment contains an aromatic resin having carbon-carbon double bonds at its ends, the content 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, even more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more depending on the application, and also preferably 95 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, even more preferably 55 parts by mass or less depending on the application, even more preferably 50 parts by mass or less, and may also 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 resin having carbon-carbon double bonds at its ends to above the lower limit, compatibility and heat resistance tend to improve further. Furthermore, by setting the content of the aromatic resin having carbon-carbon double bonds at its ends to below the upper limit, low thermal expansion tend to improve further. The resin composition of this embodiment may contain only one aromatic resin having a carbon-carbon double bond at its terminus, or it may contain two or more aromatic resins. When two or more aromatic resins are included, it is preferable that the total amount is within the above range.

[0068] <<<Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals>>> The resin composition of this embodiment preferably contains a polyphenylene ether compound having carbon-carbon unsaturated double bonds at the terminals, and more preferably contains a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminals. The polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminals preferably contains a polyphenylene ether compound having two or more groups represented by the formula (Rx-1) described later (preferably vinylbenzyl groups) at the terminals. By using these polyphenylene ether compounds, it is possible to more effectively improve the low dielectric properties (Dk and / or Df) and low water absorption of printed circuit boards and the like. The details of these will be explained below.

[0069] Examples of polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal include compounds having a phenylene ether skeleton represented by the following formula (X1).

[0070] (In formula (X1), R ２４ , R ２５ , R ２６ , and, R ２７ (These may be the same or different characters, and represent an alkyl group, aryl group, halogen atom, or hydrogen atom having six or fewer carbon atoms.)

[0071] A polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus is given by formula (X2): (In formula (X2), R ２８ , R ２９ , R ３０ , R ３４ , and, R ３５ R may be the same or different, and represents an alkyl group or phenyl group having 6 or fewer carbon atoms. ３１ , R ３２ , and, R ３３ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) A repeating unit represented by formula (X3): (In formula (X3), R ３６ , R ３７ , R ３８ , R ３９ , R ４０ , R ４１ , R ４２ , and, R ４３ ) may be the same or different, and is a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. -A- is a straight, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms. ) may further contain repeating units represented by ).

[0072] The polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus is preferably a modified polyphenylene ether compound (hereinafter sometimes referred to as "modified polyphenylene ether compound (g)") in which part or all of the terminus is functionalized with an ethylenically unsaturated group, 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 its terminus. By employing such a modified polyphenylene ether compound (g), it is possible to further reduce the dielectric loss tangent (Df) of the cured resin composition and to improve water absorption and peel strength. These modified polyphenylene ether compounds (g) may be used individually or in combination of two or more.

[0073] Examples of modified polyphenylene ether compounds (g) include polyphenylene ether compounds represented by formula (OP). (In formula (OP), X represents an aromatic group, and -(Y-O) ｎ１ The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bonding site with the oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0074] The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferable that it be at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Also, the -(Y-O)n １The polyphenylene ether structure represented by - may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. １ and / or n ２ If n is an integer greater than or equal to 2, １ individual constituent units (Y-O) and / or n ２ Each constituent unit may be identical or different. ２ The number is preferably 2 or more, and more preferably 2.

[0075] In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. １ A hydrogen atom or an alkyl group is preferred, a hydrogen atom or a methyl group is more preferred, and a hydrogen atom is even more preferred. ２ and R ３ Each of these is independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. １ , R ２ , and, R ３ The number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0076] In formula (Rx-1), r represents an integer from 0 to 6, and may be an integer of 1 or more, preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, even more preferably 1 or 2, and even more preferably 1.

[0077] In formula (Rx-1), Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In formula (Rx-1), z represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0078] A specific example of the group represented by formula (Rx-1) is the vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is the (meth)acryloyl group.

[0079] The resin composition of this embodiment is a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus, and is preferably a compound represented by formula (OP), which may include 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).

[0080] Examples of modified polyphenylene ether compounds (g) include the compound represented by formula (OP-1). (In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents the polyphenylene ether structure, R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, and n １ n represents an integer from 0 to 6, and n ２ n represents an integer between 1 and 100, and n ３(where represents an integer from 1 to 4.) The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferable that it be at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Also, the -(Y-O)n ２ The polyphenylene ether structure represented by - may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. ２ and / or n ３ If n is an integer greater than or equal to 2, ２ individual constituent units (Y-O) and / or n ３ Each constituent unit may be identical or different. ３ The number is preferably 2 or more, and more preferably 2.

[0081] In this embodiment, the modified polyphenylene ether compound (g) is preferably a compound represented by formula (OP-2). Here, -(O-X-O)- is equation (OP-3): (In formula (OP-3), R ４ , R ５ , R ６ , R １０ , and, R １１ These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. ７ , R ８ , and, R ９ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) and / or formula (OP-4): (In formula (OP-4), R １２ , R １３ , R １４ , R１５ , R １６ , R １７ , R １８ , and, R １９ (These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.

[0082] Also, -(Y-O)- is given by equation (OP-5): (In formula (OP-5), R ２０ , R ２１ These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. ２２ , R ２３ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. It is preferable that it be represented as ). In particular, R ２０ and R ２１ Each of these groups independently has one or more methyl and / or cyclohexyl groups. This increases the rigidity of the resulting resin molecule. Since molecules with high rigidity have lower mobility than molecules with low rigidity, the relaxation time during dielectric relaxation is longer, resulting in excellent low dielectric properties (Dk and / or Df, especially Dk), which is therefore preferable. An example of formula (OP-5) is shown below. For polyphenylene ether compounds having the above structure, please refer to the description in Japanese Patent Application Publication No. 2019-194312, which is incorporated herein by reference.

[0083] In formula (OP-2), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are integers from 0 to 50, more preferably from 1 to 30, and preferably from 1 to 10. When a and / or b are integers of 2 or more, the 2 or more -(Y-O)- may each independently consist of one type of structure, or two or more structures may be arranged in a block or randomly. Furthermore, when multiple 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.

[0084] Examples of the -A- in formula (OP-4) include, but are not limited to, divalent organic groups such as methylene group, ethylidene group, 1-methylethylidene group, 1,1-propyridene group, 1,4-phenylenebis(1-methylethylidene) group, 1,3-phenylenebis(1-methylethylidene) group, cyclohexylidene group, phenylmethylene group, naphthylmethylene group, and 1-phenylethylidene group.

[0085] Among the compounds represented by the above formula (OP-2), R ４ , R ５ , R ６ , R １０ , R １１ , R ２０ , and, R ２１ is an alkyl group having 3 or fewer carbon atoms, 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 ２３A polyphenylene ether compound in which is a hydrogen atom or an alkyl group having 3 or fewer carbon atoms is preferred, and in particular, the -(O-X-O)- represented by formula (OP-3) or formula (OP-4) is preferably formula (OP-9), formula (OP-10), and / or formula (OP-11), and the -(Y-O)- represented by formula (OP-5) is preferably formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the 2 or more -(Y-O)- may each independently be a structure in which two or more of formula (OP-12) and / or formula (OP-13) are arranged, or a structure in which formula (OP-12) and formula (OP-13) are arranged in a block or randomly.

[0086] (In formula (OP-10), R ４４ , R ４５ , R ４６ , and, R ４７ A is a hydrogen atom or a methyl group, and may be the same or different. B is a straight, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms. Specific examples of B are the same as the specific examples of A in formula (OP-4). (In formula (OP-11), -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.) Specific examples of -B- are the same as the specific examples of -A- in formula (OP-4).

[0087] The modified polyphenylene ether compound (g) is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and even more preferably a compound represented by formula (OP-15). (In formula (OP-14), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.) In formula (OP-14), a and b are each independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same. (In formula (OP-15), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.) In formula (OP-15), a and b are each independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same.

[0088] Furthermore, the polyphenylene ether compound used in this embodiment may also be a compound represented by formula (OP-16). (In equation (OP-16), each x independently represents an integer between 0 and 100, and at least one of the two x values ​​is an integer between 1 and 100.)

[0089] Polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal may be produced by known methods or commercially available products may be used. Examples of commercially available products include SA9000 from SABIC Innovative Plastics, which is a modified polyphenylene ether compound with a methacryloyl group at the terminal. Examples of modified polyphenylene ether compounds with a vinylbenzyl group at the terminal include OPE-2St1200 and OPE-2St2200 from Mitsubishi Gas Chemical Company. Furthermore, as a modified polyphenylene ether compound with a vinylbenzyl group at the terminal, it is also possible to use a polyphenylene ether compound with a hydroxyl group at the terminal, such as SA90 from SABIC Innovative Plastics, which has been modified to have a vinylbenzyl group using vinylbenzyl chloride or the like.

[0090] Further details regarding polyphenylene ether compounds having a terminal carbon-carbon unsaturated double bond can be found in Japanese Patent Publication No. 2006-028111, Japanese Patent Publication No. 2018-131519, International Publication No. 2019-138992, International Publication No. 2022-054303, paragraphs 0015-0048 of Japanese Patent Publication No. 2024-544483, and paragraphs 0027-0122 of Japanese Patent No. 7530718, the contents of which are incorporated herein by reference.

[0091] The number-average molecular weight in polystyrene terms of a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus (preferably a modified polyphenylene ether compound (g)) is preferably 500 to 3,000, as determined by GPC (gel permeation chromatography). A number-average molecular weight of 500 or more tends to further suppress stickiness when the resin composition of this embodiment is formed into a coating film. Furthermore, a number-average molecular weight of 3,000 or less tends to further improve solubility in solvents. In addition, the weight-average molecular weight in polystyrene terms of a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus (preferably a modified polyphenylene ether compound (g)) as determined by GPC is preferably 800 to 10,000, and more preferably 800 to 5,000. When the weight-average molecular weight is above the lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, low viscosity, and moldability of the resin composition when producing varnishes, etc., as described later tend to be improved. Furthermore, for polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals (preferably modified polyphenylene ether compounds (g)), the equivalent amount of the terminal carbon-carbon unsaturated double bonds is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, and more preferably 400 to 2500 g. When the equivalent amount of the terminal carbon-carbon unsaturated double bonds is above the lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, low viscosity, and moldability of the resin composition tend to be improved.

[0092] The functional group equivalent (equivalent of carbon-carbon unsaturated double bond) in polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal is calculated by determining the amount of double bond from the measurement results using an infrared spectrometer and then calculating the reciprocal. The double bond equivalent [g / eq.] was determined as follows: The weight of the polyphenylene ether powder was weighed and recorded. After placing this powder in a volumetric flask, the measurement sample was prepared by making up the volume with carbon disulfide to a predetermined amount. This sample solution was placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Subsequently, infrared spectroscopic measurement of the sample solution was performed. In the case of vinyl groups in polyphenylene ether compounds, the value was 905 cm⁻¹. －１ Record the peak area of ​​the spectrum in the vicinity. When the carbon-carbon unsaturated double bond is a methacrylic group, the peak area is 1640 cm⁻¹. －１ The peak area of ​​the spectrum in the vicinity is recorded. From this area value and the calibration curve, the double bond concentration [mol / L] is determined as a measured value. Next, the double bond equivalent is calculated using the following formula: Double bond equivalent [g / eq.] = Powder weight in the measurement sample [g] / Double bond concentration [mol / L] × Volume of measurement sample liquid [L] The functional group equivalent of other thermosetting compounds other than polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals can also be measured following the above method. However, for compounds (monomers) that can be expressed by a single molecular weight, the value obtained by (theoretical molecular weight ÷ number of functional groups) shall be used preferentially. If two or more other thermosetting compounds are included, the functional group equivalent of the other thermosetting compounds shall be the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each other thermosetting compound by its mass fraction.

[0093] When the resin composition of this embodiment contains a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus, the lower limit of its 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, even more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, and may be 25 parts by mass or more depending on the application. By setting the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus to be above the lower limit, the moldability of the resin composition, the heat resistance, low water absorption, and low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. Furthermore, the upper limit of the content of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends 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 resin solids in the resin composition. Depending on the application, it may also be 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less. By keeping the content of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends below the above upper limit, the low dielectric properties (especially low dielectric loss tangent) and chemical resistance of the resulting cured product tend to improve. The resin composition in this embodiment may contain only one type of polyphenylene ether compound having carbon-carbon unsaturated double bonds at the ends, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0094] <<<Polymer having a constituent unit represented by formula (V)>>> The resin composition of this embodiment may contain a polymer having a constituent unit represented by formula (V). By including a polymer having a constituent unit represented by formula (V), a resin composition with excellent low dielectric properties (low relative permittivity, low dielectric loss tangent) can be obtained. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents the bond position.) An aromatic hydrocarbon linking group may consist only of an aromatic hydrocarbon which may have substituents, or it may consist of a combination of an aromatic hydrocarbon which may have substituents and another linking group, and it is preferable that it consists only of an aromatic hydrocarbon which may have substituents. The substituents that the aromatic hydrocarbon may have include substituent Z (for example, alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxyl groups, amino groups, carboxyl groups, halogen atoms, etc.). Furthermore, it is preferable that the above aromatic hydrocarbon does not have substituents. The aromatic hydrocarbon linking group is usually a divalent linking group.

[0095] Aromatic hydrocarbon linking groups specifically include phenylene groups, naphthalenediyl groups, anthracenediyl groups, phenanthrenediyl groups, biphenyldiyl groups, and fluoroorangeyl groups, which may have substituents, with the phenylene group being preferred among them, which may have substituents. The substituent Z mentioned above is an example of a substituent, but it is preferable that groups such as the phenylene group mentioned above do not have substituents.

[0096] A polymer having a structural unit represented by formula (V) more preferably contains at least one of the structural units represented by formula (V1), formula (V2), and formula (V3). * in the following formulas represents a bond position. Furthermore, the structural units represented by formulas (V1) to (V3) are sometimes collectively referred to as "structural unit (a)".

[0097] In formulas (V1) to (V3), L １The linking group is an aromatic hydrocarbon linking group (preferably with 6 to 22 carbon atoms, more preferably with 6 to 18 carbon atoms, and even more preferably with 6 to 10 carbon atoms). Specifically, examples include phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrenediyl group, biphenyldiyl group, and fluoradiyl group, which may have substituents, and among these, the phenylene group, which may have substituents, is preferred. The substituents are exemplified by the substituent Z mentioned above, but it is preferable that groups such as the phenylene group mentioned above do not have substituents. The compound forming the structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, divinylphenanthrene, and 1,2-bis(4-vinylphenyl)ethane. Among these, divinylbenzene and 1,2-bis(4-vinylphenyl)ethane are particularly preferred. One of these divinyl aromatic compounds may be used, or two or more may be used as needed. In other words, it is preferable that the constituent unit (a) is a constituent unit derived from a divinyl aromatic compound.

[0098] As described above, the polymer having the constituent unit represented by formula (V) may be a homopolymer of the compound forming the constituent unit (a), or it may be a copolymer with a constituent unit derived from another monomer. When the polymer having the constituent unit represented by formula (V) is a copolymer, the copolymerization ratio 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, even more preferably 30 mol% or less, and may also be 25 mol% or less or 20 mol% or less.

[0099] Other monomer-derived structural units include structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0100] The constituent unit (b) derived from the monovinyl aromatic compound is preferably a constituent unit represented by the following formula (V4).

[0101] In formula (V4), L ２ is an aromatic hydrocarbon linking group, and a specific example of a preferred one is the above L １ Examples include the following. * indicates the bonding position. R Ｖ１ R is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). Ｖ１ When it is a hydrocarbon group, its number of carbon atoms is preferably 1 to 6, and more preferably 1 to 3. Ｖ１ and L ２ It may have the substituent Z described above.

[0102] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (b) derived from a monovinyl aromatic compound, examples of monovinyl aromatic compounds 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 above-mentioned substituent Z. Furthermore, one or more of these monovinyl aromatic compounds may be used. Among these, structural unit (b) preferably contains structural units derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene, and more preferably further contains structural units derived from styrene in addition to structural units derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene.

[0103] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (b), the copolymerization ratio of structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may 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.

[0104] A polymer having a structural unit represented by formula (V) may have other structural units besides structural units (a) and (b). Examples of other structural units include structural unit (c) derived from a cycloolefin compound. Examples of cycloolefin compounds include hydrocarbons having a double bond in the ring structure. Specifically, examples include monocyclic cyclic 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 in which aromatic rings are fused, such as indene and acenaphthylene. Examples of norbornene compounds are those described in paragraphs 0037 to 0043 of Japanese Patent Application Publication No. 2018-039995, the contents of which are incorporated herein by reference. The cycloolefin compounds exemplified herein may further have the substituent Z described above.

[0105] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (c), the copolymerization ratio of 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, even more preferably 70 mol% or less, and may also be 50 mol% or less, or 30 mol% or less.

[0106] A polymer having a structural unit represented by formula (V) may also incorporate 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. Specifically, 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), isoprene, etc. The copolymerization ratio of structural unit (d) derived from the other polymerizable compound is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0107] As one embodiment of a polymer having a structural unit represented by formula (V), a polymer is provided in which structural unit (a) is essential and at least one of structural units (b) and (c) is included. Furthermore, an embodiment is provided in which the sum of structural units (a) to (c) accounts for 90 mol% or more, more preferably 95 mol% or more, and particularly preferably 98 mol% or more of the total structural units. As another embodiment of a polymer having a structural unit represented by formula (V), a polymer is provided in which structural unit (a) is essential and at least one of structural units (b) to (d) is included. Furthermore, an embodiment is provided in which the sum of structural units (a) to (d) accounts for 95 mol% or more, more preferably 98 mol% or more of the total structural units. As yet another embodiment of a polymer having a structural unit represented by formula (V), structural unit (a) is essential, and it is preferable that the polymer contains 90 mol% or more of structural units including aromatic rings among all structural units excluding the terminals, more preferably 95 mol% or more, and may also be a polymer of 100 mol%. In calculating the mole percentage per total constituent unit, one constituent unit is defined as one molecule of the monomer (e.g., divinyl aromatic compound, monovinyl aromatic compound, etc.) used in the production of a polymer having a constituent unit represented by formula (V).

[0108] The method for producing a polymer having a constituent unit represented by formula (V) is not particularly limited and can be carried out by conventional methods. For example, a raw material containing a divinyl aromatic compound (and, if necessary, a monovinyl aromatic compound, a cycloolefin compound, etc.) can be polymerized in the presence of a Lewis acid catalyst. As the Lewis acid catalyst, a metal fluoride such as boron trifluoride or a complex thereof can be used.

[0109] The structure of the chain ends of a polymer having a constituent unit represented by formula (V) is not particularly limited, but with respect to the group derived from the above divinyl aromatic compound, it can take the structure of formula (E1) below. Note that L in formula (E1) １ This is the same as defined in formula (V1) above. * indicates the bond position. *-CH=CH-L １ -CH=CH ２ (E1)

[0110] When a group derived from a monovinyl aromatic compound becomes the chain terminus, it can take the structure shown in formula (E2) below. ２ and R Ｖ１ These have the same meaning as defined in equation (V4) above. * represents the bond position. *-CH=CH-L ２ -R Ｖ１ (E2)

[0111] The molecular weight of the polymer having the constituent unit represented by formula (V) is preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and even more preferably 1,500 or more, in terms of number average molecular weight (Mn). The upper limit of the number average molecular weight is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, even more preferably 100,000 or less, and may also be 30,000 or less, 10,000 or less, or 5,000 or less. The molecular weight of the polymer having the constituent 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 to be above the lower limit, the excellent low dielectric properties (Dk and / or Df), particularly Df and dielectric properties after moisture absorption, of the polymer having the constituent unit represented by formula (V) can be effectively exhibited in the cured product of the resin composition. The upper limit of the weight-average molecular weight Mw is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less. By keeping the weight-average molecular weight below the above upper limit, when the prepreg or resin sheet is laminated onto a circuit forming substrate, embedding defects tend to be less likely to occur. The monodispersity (Mw / Mn), expressed as the ratio of the weight-average molecular weight (Mw) to the number-average molecular weight (Mn), is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and may also be 15 or less or 12 or less. As a lower limit, it is practical to be 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. When the resin composition of this embodiment contains two or more polymers having a constituent unit represented by formula (V), it is preferable that the Mw, Mn, and Mw / Mn of the mixture satisfy the above ranges.

[0112] The equivalent amount of vinyl groups in a polymer having a constituent 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. Furthermore, the equivalent amount of vinyl groups is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and may be 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 350 g / eq. or less. When the equivalent amount of vinyl groups is above the above lower limit, the storage stability of the resin composition is improved and the fluidity of the resin composition tends to improve. As a result, moldability is improved, voids are less likely to occur when forming prepregs, etc., and a more reliable printed circuit board tends to be obtained. On the other hand, when the vinyl group equivalent is below the aforementioned upper limit, the heat resistance of the resulting cured product tends to improve.

[0113] Polymers having a constituent unit represented by formula (V) preferably have cured products with excellent low dielectric properties (Dk and / or Df). For example, the cured product of a polymer having a constituent unit represented by formula (V) used in this embodiment preferably has a relative permittivity (Dk) at 10 GHz measured according to the cavity resonator perturbation method 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. Furthermore, a practical lower limit for the relative permittivity is, for example, 1.80 or more. Furthermore, the cured product of a polymer having a constituent unit represented by formula (V) preferably has a dielectric loss tangent (Df) at 10 GHz measured according to the cavity resonator perturbation method of 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less. Furthermore, a practical lower limit for the dielectric loss tangent is, for example, 0.0001 or more. The relative permittivity (Dk) and dielectric loss tangent (Df) are measured by the following method. 4.5 g of resin powder is spread into a stainless steel mold measuring 100 mm x 30 mm x 1.0 mm high, and placed in a vacuum press (manufactured by Kitagawa Seiki Co., Ltd.). The mold is held at 200°C for 2 hours and pressed at a surface pressure of 3.0 MPa to produce a cured plate. After downsizing the cured plate to a width of 1.0 mm, it is dried at 120°C for 60 minutes. The relative permittivity (Dk) and dielectric loss tangent (Df) after drying are then measured at 10 GHz using a perturbation cavity resonator. The measurement temperature is 23°C.

[0114] With respect to polymers having a constituent unit represented by formula (V) in this specification, reference can be made to and incorporated herein to the compounds and their synthesis reaction conditions described in paragraphs 0029 to 0058 of International Publication No. 2017 / 115813, the compounds and their synthesis reaction conditions described in paragraphs 0013 to 0058 of Japanese Patent Application Publication No. 2018-039995, the compounds and their synthesis reaction conditions described in paragraphs 0008 to 0043 of Japanese Patent Application Publication No. 2018-168347, the compounds and their synthesis reaction conditions described in paragraphs 0014 to 0042 of Japanese Patent Application Publication No. 2006-070136, the compounds and their synthesis reaction conditions described in paragraphs 0014 to 0061 of Japanese Patent Application Publication No. 2006-089683, and the compounds and their synthesis reaction conditions described in paragraphs 0008 to 0036 of Japanese Patent Application Publication No. 2008-248001. A polymer having the constituent unit represented by formula (V) can be a commercially available product, such as LF-310T50 manufactured by Nippon Steel Chemical & Material Co., Ltd.

[0115] 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, even more preferably 10 parts by mass or more, and may be 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more, depending on the application. By setting the content of the polymer having a structural unit represented by formula (V) to the above lower limit, it tends to be possible to effectively achieve low dielectric properties, in particular, a low relative permittivity. 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, based on 100 parts by mass of resin solids in the resin composition. By keeping the content of polymers having the structural unit represented by formula (V) below the above upper limit, the metal foil peel strength and low water absorption tend to improve. The resin composition in this embodiment may contain only one type of polymer having the structural unit represented by formula (V), or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range. Furthermore, the resin composition in this embodiment may also be configured to substantially not contain polymers having the structural unit represented by formula (V). Substantially not containing polymers means that the content of polymers having the structural unit represented by formula (V) is less than 1 part by mass per 100 parts by mass of resin solids in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0116] << (In formula (T1), Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may be independently substituted with a halogen atom, and x represents an integer from 0 to 4. * represents the bonding position with other sites.)

[0117] In formula (T1), Ma is preferably, independently, a C1-C10 hydrocarbon group which may be substituted with a halogen atom, more preferably a C1-C5 hydrocarbon group which may be substituted with a halogen atom, and even more preferably a C1-C3 hydrocarbon group which may be substituted with a halogen atom. Examples of halogen atoms include fluorine, chlorine, and bromine atoms, with fluorine or chlorine atoms being preferred. Ma is preferably, independently, a C1-C12 hydrocarbon group which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. Methyl and ethyl groups are particularly preferred for Ma.

[0118] x is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, even more preferably 0 or 1, and even more preferably 0.

[0119] Resin (A) may have terminal groups represented by formula (T1) at all of its ends, or at only some of its ends, for each resin molecule. Preferably, the resin molecule of resin (A) contains two terminal groups represented by formula (T1).

[0120] Resin (A) has an indan skeleton. While it is not particularly limited as long as at least one of the resin molecules contained in resin (A) has at least one indan skeleton, the number of indan skeletons in the resin molecules of resin (A) is preferably one or more per molecule, and more preferably 1 to 20. This configuration tends to more effectively exhibit the effects of the present invention.

[0121] The resin (A) preferably contains a constituent unit represented by formula (Txn). (In formula (T x n), n is the average number of repeating units, representing a number greater than 0 and less than or equal to 20. Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may be independently substituted with halogen atoms. x represents an integer from 0 to 4.)

[0122] In formula (Txn), Ma is preferably, independently, a C1-C10 hydrocarbon group which may be substituted with a halogen atom, more preferably a C1-C5 hydrocarbon group which may be substituted with a halogen atom, and even more preferably a C1-C3 hydrocarbon group which may be substituted with a halogen atom. Examples of halogen atoms include fluorine, chlorine, and bromine atoms, with fluorine or chlorine atoms being preferred. Ma is preferably, independently, a C1-C12 hydrocarbon group which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. Methyl and ethyl groups are particularly preferred for Ma.

[0123] x is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, even more preferably 0 or 1, and even more preferably 0.

[0124] The proportion of the constituent unit represented by formula (Txn) in 100 parts by mass of resin (A) is preferably 20 parts by mass or more, more preferably 25 parts by mass or more, even more preferably 34 parts by mass or more, even more preferably 45 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, and even more preferably 60 parts by mass or more, 65 parts by mass or more, and may also be 70 parts by mass or more, 75 parts by mass or more, and also preferably 100 parts by mass or less, and may be 95 parts by mass or less, 90 parts by mass or less, 85 parts by mass or less, 82 parts by mass or less, or 80 parts by mass or less.

[0125] Resin (A) more preferably contains a resin represented by formula (T1-1), and more preferably contains a resin represented by formula (T1-1-2). (In formula (T1-1), R is a group containing the constituent unit represented by formula (Tx). Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may each be independently substituted with a halogen atom. x is an integer from 0 to 4.) In formula (T1-1), Ma and x are the same as Ma and x in formula (T1), and the preferred ranges are also the same. (In formula (T1-1-2), R is a group containing the constituent unit represented by formula (Tx).) (In formula (Tx), n, o, and p are the average number of repeating units, where n is a number greater than 0 and less than or equal to 20, and o and p each independently represent numbers from 0 to 20, with 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms, which may be substituted with halogen atoms. x represents an integer from 0 to 4. Constituent units (a), (b), and (c) are each bonded to constituent units (a), (b), (c), or other groups by *, and each constituent unit may be bonded randomly.)

[0126] 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 especially even more preferably 3.3 ≤ n + o + p. Furthermore, in formula (Tx), the sum of n, o, and p is 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, and even more preferably n + o + p ≤ 6.4. The sum of n, o, and p can be calculated by the method described in the examples of International Publication No. 2023 / 176766.

[0127] In formula (Tx), n is preferably 0.2 or greater, more preferably 0.6 or greater, even more preferably 1.0 or greater, even more preferably 1.2 or greater, even more preferably 1.6 or greater, and may also be 2.2 or greater, 2.4 or greater, and may also be 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 or less, and may also be 5.0 or less, 4.0 or less, or 3.0 or less. In formula (Tx), o is preferably 0 or greater, more preferably 0.01 or greater, even more preferably 0.03 or greater, even more preferably 0.05 or greater, even more preferably 0.07 or greater, and also 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, 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 greater, more preferably 0.01 or greater, even more preferably 0.1 or greater, even more preferably 0.2 or greater, even more preferably 0.3 or greater, and also 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, 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.

[0128] Furthermore, in formula (Tx), n / (n+o+p) is, for example, 0.2 or more, 0.25 or more, 0.3 or more, 0.34 or more, 0.4 or more, 0.45 or more, 0.5 or more, 0.55 or more, 0.6 or more, or 0.7 or more, and is also 1.0 or less. Among the constituent units (a) to (c) included in formula (Tx), constituent unit (a) which has the smallest activation energy and the largest free energy change is preferentially produced. In formula (T1-1), the proportion (total amount) of the constituent unit represented by formula (Tx) (i.e., any of the constituent units (a), (b), or (c)) in 100 parts by mass of R is preferably 80 parts by mass or more, more preferably 90 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 97 parts by mass or more, even more preferably 99 parts by mass or more, and also 100 parts by mass or less.

[0129] In equation (Tx), Ma and x are equivalent to Ma and x in equation (Txn), respectively, and the preferred ranges are also the same.

[0130] Furthermore, resin (A) may contain constituent units represented by formula (Ty).

[0131] The resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)) is preferably further characterized in that the parameter α calculated from formula (α) is between 0.30 and 1.00. Furthermore, the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)) is preferably characterized in that the parameter β calculated from formula (β) is between 0.20 and 3.00. By setting the parameters α and β within the above ranges, the resulting cured product tends to have excellent low dielectric properties (Dk and / or Df) and heat resistance. (The terms in parentheses in equations (α) and (β) are, １ (This shows the integral value between the corresponding chemical shift values ​​in 1H-NMR.)

[0132] Here, α represents the ratio of constituent units having an indan skeleton (constituent unit (a) in formula (Tx)) in the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)). More specifically, it is presumed that by adjusting the constituent units having an indan skeleton to satisfy the range of the above parameter α, the rigidity of the resulting resin molecules can be increased and the glass transition temperature can be increased. Furthermore, since molecules with high rigidity have lower mobility than molecules with low rigidity, it is presumed that the relaxation time during dielectric relaxation will be longer, and Df can be lowered. α can be increased when synthesizing the resin represented by formula (T1-1) by conditions such as diluting the concentration of the raw materials, using a highly polar solvent, increasing the amount of catalyst, or increasing the reaction temperature. On the other hand, β defines the ratio of terminal double bonds in the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)). 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 during thermal curing, resulting in a cured product with a high glass transition temperature and low Df. β can be increased when synthesizing the resin represented by formula (T1-1) by reducing the amount of catalyst, lowering the reaction temperature, or using a low-polarity solvent.

[0133] More specifically, the 2.55 ppm to 2.31 ppm range corresponds to the peak originating from constituent unit (a), the 6.24 ppm to 5.91 ppm range corresponds to the peak originating from constituent unit (b), the 2.98 ppm to 2.55 ppm range corresponds to the peak originating from constituent unit (c), the 5.49 ppm to 4.89 ppm range corresponds to the peak originating from the isopropenyl group and constituent unit (c), the 4.89 ppm to 4.45 ppm range corresponds to the peak originating from constituent unit (c), and the 2.31 ppm to 1.96 ppm range corresponds to the peak originating from the isopropenyl group and constituent unit (a).

[0134] More specifically, the H used in the calculation of parameters α and β is shown in the following structural formula. The above parameters α and β are used in the calculation １The H-NMR peaks can be assigned to each H as described above, as follows: • 2.55 ppm to 2.31 ppm: H a1 6.24 ppm to 5.91 ppm: H b1 ・2.98 ppm to 2.55 ppm: H c1 ・5.49 ppm to 4.89 ppm: H i2 and H i3 and H c2 4.89 ppm to 4.45 ppm: H c3 ・2.31 ppm to 1.96 ppm: H a2 and H i1

[0135] From the above, the equations for parameters α and β are described by the amounts of each hydrogen atom shown below. That is, parameter α is H a1 The greater the amount, that is, the more five-membered rings there are in the constituent unit (a), the larger the parameter β becomes. Also, the parameter β is related to the H in the isopropenyl group. i1 The amount is the denominator, H i2 and H i3 The formula is shown such that the numerator is 1.5 times the total amount of . That is, ideally (H i2 and H i3 (1.5 times the total amount) ÷ (H i1 The total amount of ( ) becomes 1. When synthesizing the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)), the parameters α and β of the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)) 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 methods other than those described above. The parameters α and β can be measured by the following formulas (α) and (β), respectively. (The terms in parentheses in equations (α) and (β) are, １ (This shows the integral value between the corresponding chemical shift values ​​in 1H-NMR.)

[0136] Parameter α is preferably 0.35 or higher, more preferably 0.40 or higher, even more preferably 0.45 or higher, even more preferably 0.50 or higher, and may be 0.55 or higher, 0.60 or higher, 0.70 or higher, or 0.75 or higher. Setting it above the lower limit tends to further improve the heat resistance of the resulting cured product. Since a larger parameter α is generally preferable because it tends to result in superior low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product, it may also be 0.95 or lower, 0.90 or lower, 0.85 or lower, 0.82 or lower, 0.80 or lower, 0.77 or lower, 0.75 or lower, or 0.74 or lower. The parameter β is preferably 0.25 or higher, more preferably 0.30 or higher, even more preferably 0.35 or higher, even more preferably 0.40 or higher, even more preferably 0.43 or higher, even more preferably 0.50 or higher, and may also be 0.60 or higher, 0.65 or higher, 0.70 or higher, 0.77 or higher, 0.80 or higher, 0.90 or higher, or 0.95 or higher. Setting it to be above the lower limit improves the heat resistance of the resulting cured product and tends to lower Df. The parameter β is preferably 2.50 or lower, more preferably 2.00 or lower, even more preferably 1.50 or lower, even more preferably 1.30 or lower, even more preferably 1.20 or lower, even more preferably 1.10 or lower, and may also be 1.00 or lower, 0.95 or lower, 0.90 or lower, 0.85 or lower, 0.83 or lower, or 0.80 or lower. By setting parameter β to below the aforementioned upper limit, the heat resistance of the resulting cured product improves, and Df tends to decrease.

[0137] The number-average molecular weight (Mn) of resin (A) as polystyrene equivalent, measured by GPC (gel permeation chromatography), is preferably 400 or more, more preferably 500 or more, even more preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By setting the number-average molecular weight above the lower limit, the heat resistance of the resulting cured product is improved, and the Df tends to decrease. Furthermore, the upper limit of the number-average molecular weight (Mn) of resin (A) as polystyrene equivalent, measured by GPC (gel permeation chromatography), is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, and even more preferably 1250 or less. Depending on the application, it may also be 1000 or less, or 800 or less. By setting the number-average molecular weight below the upper limit, the heat resistance of the resulting cured product is improved, and the relative permittivity (Dk) and dielectric loss tangent (Df) tend to decrease. Furthermore, the weight-average molecular weight (Mw) of resin (A) in polystyrene equivalent by GPC (details are as 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 above the lower limit, the heat resistance of the resulting cured product is improved and the Df tends to decrease. The upper limit of the weight-average molecular weight (Mw) of resin (A) in polystyrene equivalent by GPC 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. Depending on the application, it may also be 2500 or less, 2000 or less, or 1500 or less. By setting the weight-average molecular weight below the upper limit, the heat resistance of the resulting cured product is improved and the relative permittivity (Dk) and dielectric loss tangent (Df) tend to decrease.

[0138] The resin (A) preferably has a Mw / Mn ratio, which is the ratio of weight-average molecular weight to number-average molecular weight, of 1.1 to 3.0. More preferably, the Mw / Mn of resin (A) is 1.2 or higher, even more preferably 1.3 or higher, even more preferably 1.4 or higher, even more preferably 1.5 or higher, and even more preferably 1.6 or higher. Furthermore, the Mw / Mn of resin (A) is more preferably 2.5 or lower, even more preferably 2.4 or lower, and may be 2.3 or lower, 2.0 or lower, or 1.8 or lower.

[0139] In this embodiment, the functional group equivalent (isopropenyl group equivalent) of resin (A) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, even more preferably 250 g / eq. or more, even more preferably 275 g / eq. or more, even more preferably 300 g / eq. or more, and also preferably 7500 g / eq. or less, more preferably 5000 g / eq. or less, even more preferably 4000 g / eq. or less, even more preferably 3000 g / eq. or less, even more preferably 2000 g / eq. or less, even more preferably 1500 g / eq. or less, and especially even more preferably 1000 g / eq. or less. Furthermore, it may also be 800 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, or 500 g / eq. or less. By setting the functional group equivalent of resin (A) to above the lower limit, the low dielectric properties (Dk and / or Df, especially Df) of the resulting cured product are improved, and the heat resistance over time (low dielectric properties after heating (Dk and / or Df, especially Df)) of the resulting cured product can be maintained more effectively. Furthermore, by setting the functional group equivalent of resin (A) to below the upper limit, the low dielectric properties (Dk and / or Df, especially Df) of the resulting cured product tend to be improved, and the heat resistance (especially the glass transition temperature) tends to be improved. The isopropenyl group equivalent (g / eq.) of resin (A) is calculated from (number average molecular weight (Mn) ÷ 2) ÷ β.

[0140] The method for producing 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 the synthesis of resin (A) are not particularly limited and can be appropriately selected or controlled according to the desired physical properties described above.

[0141] In this embodiment, examples of raw materials used when synthesizing resin (A) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0142] In addition to the above, as aromatic resins having carbon-carbon double bonds at their terminals, the compounds described in International Publication No. 2021 / 100658, the compounds described in Japanese Patent Publication No. 2024-086554, Japanese Patent Publication No. 2023-104784, Japanese Patent Publication No. 2023-104785, and the copolymer described in Japanese Patent Publication No. 2024-007493 can be considered, and this information is incorporated herein by reference.

[0143] <<<Other compounds having carbon-carbon unsaturated double bonds at the terminals (compound (XC))>>> The resin composition of this embodiment may also contain other compounds having carbon-carbon unsaturated double bonds at the terminals other than those mentioned above (compound (XC)). An example of compound (XC) is a low molecular weight aromatic vinyl compound (excluding those that fall under the category of other low molecular weight compounds having cyclic compounds as described above). Examples of aromatic vinyl compounds include methylstyrene (e.g., 4-methylstyrene), ethyl vinylbenzene, diethyl 4-vinylbenzylphosphonate, 4-vinylbenzylglycidyl ether, α-methylstyrene, 4-tert-butylstyrene, vinylbenzyl ether, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene, with 4-methylstyrene, 4-tert-butylstyrene, divinylbenzene, and 1,2-bis(4-vinylphenyl)ethane being preferred. Furthermore, resins having isopropenyl groups as described in International Publication No. 2022 / 210095 (for example, the compounds described in Synthesis Examples 1, 2, 7, and 8 of the same publication) are exemplified and incorporated herein.

[0144] Another example of a compound (compound (XC)) having a carbon-carbon unsaturated double bond at its terminus is vinylbenzyl ether. Examples of vinylbenzyl ethers include reaction products produced from the reaction of 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, etc., 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 (bisphenol P), 4,4'-ethylidenediphenol (bisphenol E), 4,4'-oxydiphenol, 4,4'-thiodiphenol, 4,4'-thiobis(2,6-dimethylphenol), 4,4'-sulfonyldiphenol, 4,4'-sulfonylbis(2,6-dimethylphenol), 4,4'-sulfinyldiphenol, 4,4'-hexafluoroisopropylidene)bisphenol (bisphenol AF), 4,4'(1-phenylethylidene)bisphenol (bisphenol AP), bis(4-hydroxyphenyl)-2,2-Dichloroethylene (bisphenol C), bis(4-hydroxyphenyl)methane (bisphenol-F), bis(2,6-dimethyl-4-hydroxyphenyl)methane, 4,4'-(cyclopentylidene)diphenol, 4,4'-(cyclohexylidene)diphenol (bisphenol Z), 4,4'-(cyclododecylidene)diphenol, 4,4'-(bicyclo[2.2.1]heptylidene)diphenol, 4,4'-(9H-fluoren-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[inden]-5,6'-diol (spirobindan), dihydroxybenzophenone (bisphenol K), tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)propane, tris(4-hydroxyphenyl)butane, tris(3-methyl-4-hydroxyphenyl)methane, tris(3,5-dimethyl-4-hydroxyphenyl)methane, tetrakis(4-hydroxyphenyl)ethane, tetrakis(3,5-dimethyl-4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)phenylphosphine oxide, dicyclopentadienylbis(2,Examples include vinyl benzyl ethers produced by the reaction of 6-dimethylphenol, dicyclopentadienylbis(o-cresol), dicyclopentadienylbisphenol, etc., with vinyl benzyl chloride or vinyl benzyl bromide. In addition to the above, vinyl benzyl compounds also include vinyl benzyl ether compounds described in paragraph 0041 of Japanese Patent Publication No. 2019-194312, resins having styryl groups described in paragraphs 0008-0032 of Japanese Patent No. 7551036, paragraphs 0007-0057 of Japanese Patent No. 7530537, and International Publication No. 2022 / 210095 (for example, compounds described in synthesis examples 12-16 of the same publication), resins having styryl groups described in International Publication No. 2024 / 101237, resins having styryl groups described in International Publication No. 2024 / 101238, and resins having styryl groups described in International Publication No. 2023 / 176765, the contents of which are incorporated herein by reference.

[0145] In addition to the above, copolymers described in paragraphs 0029 to 0039 of Japanese Patent Publication No. 2022-85610, paragraphs 0023 to 0043 of Japanese Patent Publication No. 2024-107328, paragraphs 0022 to 0039 of Japanese Patent Publication No. 2024-7493, and paragraphs 0010 to 0053 of Japanese Patent Publication No. 2024-139678, vinyl benzyl ether resins described in paragraphs 0012 to 0027 of Japanese Patent Publication No. 2024-84377, and paragraph 0041 of Japanese Patent Publication No. 2019-194312, copolymer oligomers described in paragraphs 0036 to 0061 of International Publication No. 2024 / 143509 and paragraphs 0013 to 0027 of International Publication No. 2022 / 014599, etc., can also be used, and the contents of these are incorporated herein.

[0146] The content of other compounds having a carbon-carbon unsaturated double bond at the end (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, depending on the application, etc., and 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 other compounds having a carbon-carbon unsaturated double bond at the end (compound (XC))) to be above the lower limit, the Df of the resulting cured product tends to be lower. Furthermore, the upper limit of the content of other compounds having a carbon-carbon unsaturated double bond at the end (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, depending on the application, etc., and may be 70 parts by mass or less, 65 parts by mass or less, or 55 parts by mass or less, depending on the application, etc. By keeping the content of other compounds (compound (XC)) having a carbon-carbon unsaturated double bond at the terminal below the upper limit, the moldability of the resin composition and the heat resistance of the resulting cured product tend to improve. The resin composition of this embodiment may contain only one other compound (compound (XC)) having a carbon-carbon unsaturated double bond at the terminal, or it may contain two or more. When two or more are included, it is preferable that the total amount is within the above range.

[0147] <<Cyanate Ester Compounds>> The resin composition of this embodiment may contain cyanate ester compounds. The cyanate ester compound in this embodiment is not particularly limited as long as it contains one or more cyanate groups (preferably two or more, more preferably two to twelve, even more preferably two to six, even more preferably two to four, even more preferably two or three, and even more preferably two) in one molecule, and compounds commonly used in the field of printed circuit boards can be widely used. Furthermore, it is preferable that the cyanate ester compound is a compound in which the cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Preferred cyanate ester compounds in this embodiment include, for example, 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, bisphenol E type cyanate ester compounds, diallylbisphenol A type cyanate ester compounds, and indancyanate compounds. Among these, from the viewpoint of further improving the low water absorption of the resulting cured product, it is more preferable to use 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 diallylbisphenol A type cyanate ester compounds. It is even more preferable to use at least one selected from the group consisting of phenol novolac type cyanate ester compounds and naphthol aralkyl type cyanate ester compounds, and even more preferable to use a naphthol aralkyl type cyanate ester compound. These cyanate ester compounds may be prepared by known methods or commercially available products may be used.Furthermore, cyanate ester compounds having a naphthol aralkyl skeleton, naphthylene ether skeleton, xylene skeleton, trisphenolmethane skeleton, or adamantane skeleton tend to have a relatively large number of functional group equivalents and fewer unreacted cyanate ester groups, resulting in cured resin compositions using these compounds exhibiting even greater low water absorption. In addition, the presence of an aromatic skeleton or adamantane skeleton tends to further improve plating adhesion.

[0148] As naphthol aralkyl type cyanate ester compounds, compounds represented by the following formula (1) are more preferred. (In formula (1), R ３ Each of these independently represents either a hydrogen atom or a methyl group, and n3 represents an integer greater than or equal to 1.

[0149] In formula (1), R ３ Each of these independently represents either a hydrogen atom or a methyl group, with hydrogen atoms being preferred. In formula (1), n3 is an integer of 1 or more, preferably an integer between 1 and 20, more preferably an integer between 1 and 10, and even more preferably an integer between 1 and 6.

[0150] Furthermore, while the novolac-type cyanate ester compound is not particularly limited, for example, a compound represented by the following formula (VII) is preferred. (In formula (VII), R ６ Each of these independently represents either a hydrogen atom or a methyl group, and n7 represents an integer greater than or equal to 1.

[0151] In formula (VII), R ６ Each of these independently represents either a hydrogen atom or a methyl group, with hydrogen atoms being preferred. In formula (VII), n7 is an integer of 1 or more, preferably an integer between 1 and 20, more preferably an integer between 1 and 10, and even more preferably an integer between 1 and 6.

[0152] 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 2,2-bis(4-cyanatophenyl)propane prepolymers may be used.

[0153] Examples of indanthyanate compounds include those represented by the following formula (a): Formula (a) (In equation (a), n is the average number of repetitions, and is a number between 3.0 and 15.0.)

[0154] In addition to the above, the compounds described in paragraphs 0035 to 0061 of Japanese Patent Application No. 2024-110099 can also be used as cyanate ester compounds, and this is incorporated herein by reference.

[0155] The resin composition of this embodiment preferably contains a cyanate ester compound in 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 its 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 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 relative permittivity, low dielectric loss tangent), and insulation properties of the resulting cured product tend to improve. When the resin composition of this embodiment contains a cyanate ester compound, the upper limit of its 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 resin solids in the resin composition. The resin composition of this embodiment may contain only one type of cyanate ester compound, or it may contain two or more types. If two or more types are included, it is preferable that the total amount falls within the above range.

[0156] <<(Meth)allyl Compounds>> The resin composition of this embodiment may contain (meth)allyl compounds. The (meth)allyl compound preferably contains an allyl compound. Furthermore, 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 contains at least one selected from the group consisting of (meth)allyl isocyanurate compounds, tri(meth)allyl cyanurate compounds, (meth)allyl group-substituted nadiimide compounds, (meth)allyl compounds having a glycoluryl structure, and diallyl phthalate. It is more preferably a (meth)allyl isocyanurate compound and / or a (meth)allyl group-substituted nadiimide compound.

[0157] Examples of tri(meth)allyl cyanurate compounds include tri(meth)allyl cyanurate compounds (for example, triallyl cyanurate, whose structure is shown below). Furthermore, examples of (meth)allyl compounds include resins having an allyl group as described in International Publication No. 2022 / 210095 (for example, the compounds described in Synthesis Examples 3, 4, 6, 20, and 22 of the same publication), and this information is incorporated herein by reference.

[0158] 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 500 or more. Setting it above the lower limit tends to further improve low dielectric properties and heat resistance. 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. Setting it below the upper limit tends to further improve low thermal expansion properties.

[0159] When the resin composition of this embodiment contains a (meth)allyl compound, its content 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 resin solids in the resin composition. Setting the (meth)allyl compound content above the lower limit tends to improve moldability and heat resistance. Furthermore, the upper limit of the (meth)allyl compound content 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 resin solids in the resin composition. Setting the (meth)allyl compound content below the upper limit tends to improve low thermal expansion. The resin composition of this embodiment may contain only one type of (meth)allyl compound, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0160] <<<(Meth)allyl isocyanurate compounds>>> As for (meth)allyl isocyanurate compounds, there are no specific restrictions as long as they are compounds having two or more (meth)allyl groups and an isocyanurate ring (nulate skeleton). Because (meth)allyl isocyanurate compounds have a large number of (meth)allyl groups that act as crosslinking points, they tend to harden firmly with other thermosetting compounds such as aromatic resins and maleimide compounds that have carbon-carbon double bonds at the terminals, resulting in cured products with excellent low dielectric properties (Dk and / or Df) and heat resistance. As for (meth)allyl isocyanurate compounds, compounds represented by formula (TA) are preferred. Formula (TA) (In formula (TA), R Ａ (This represents a substituent.)

[0161] In formula (TA), R Ａ represents a substituent, and it is more preferable that the substituent has a formula weight of 15 to 500.

[0162] R ＡThe 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 can produce a cured product with excellent crosslinking properties and high toughness. As a result, even if the resin composition does not contain a substrate such as glass cloth, cracking during etching and other processes can be suppressed. From the viewpoint of improving handling properties, 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, or 18 or less. As a result, the resin flowability of the resin composition is improved, and it is thought that the circuit filling properties when using the resin composition of this embodiment to manufacture multilayer circuit boards and the like will be improved.

[0163] R Ａ A second example is a group containing an allyl isocyanurate group. Ａ If the compound contains an allyl isocyanurate group, the compound represented by formula (TA) is preferably the compound represented by formula (TA-1). Formula (TA-1) (In formula (TA-1), R Ａ２ (This is a divalent linking group.)

[0164] In formula (TA-1), R Ａ２ It is preferably a divalent linking group with a formula weight of 54 to 250, more preferably a divalent linking group with a formula weight of 54 to 250 and both ends being 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 and may also have a hydroxyl group). More specifically, R Ａ２ It is preferable that the group is represented by any of the following formulas (i) to (iii). (In formulas (i) to (iii), p ｃ１ The number of repeating units in the methylene group is an integer between 2 and 18. ｃ２ represents the number of repeating units of the oxyethylene group, which is 0 or 1. * represents the bonding site.) The above p ｃ１The integer p is preferably an integer between 2 and 10, more preferably an integer between 3 and 8, and even more preferably an integer between 3 and 5. ｃ２ This value may be 0 or 1, but is preferably 1.

[0165] R Ａ A third example is phosphorus substituents.

[0166] R Ａ２ The first example is preferable.

[0167] In this embodiment, it is preferable that the equivalent amount of the reactive group (allyl group) of the compound represented by formula (TA) is 1000 g / eq. or less. It is believed that a high Tg can be obtained more reliably if the equivalent amount is 1000 g / eq. or less.

[0168] Examples of the C1-C22 alkyl group 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 C2-C22 alkenyl group include allyl and decenyl groups.

[0169] Specific examples of compounds 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 individually or in combination of two or more, and may also be used as prepolymers.

[0170] The method for producing the compound represented by formula (TA) is not particularly limited, but for example, it can be obtained by reacting diallyl isocyanurate and 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.

[0171] Furthermore, commercially available compounds can also be used as compounds represented by formula (TA). Commercially available compounds are not particularly limited, but examples include L-DAIC manufactured by Shikoku Chemicals Co., Ltd., and P-DAIC manufactured by Shikoku Chemicals Co., Ltd., which has a phosphorus substituent. As for triallyl isocyanurate, for example, TAIC manufactured by Shinryo Co., Ltd. As for the compound represented by formula (TA-1), for example, DD-1 manufactured by Shikoku Chemicals Co., Ltd.

[0172] The molecular weight of the (meth)allyl isocyanurate compound (preferably the compound represented by formula (TA)) is preferably 200 or more, more preferably 300 or more, and may be 400 or more or 500 or more. Setting the molecular weight above the lower limit tends to further improve the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product. Furthermore, the molecular weight of the (meth)allyl isocyanurate compound (preferably the 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. Setting the molecular weight below the upper limit tends to further improve the low thermal expansion properties of the resulting cured product.

[0173] When the resin composition of this embodiment contains a (meth)allyl isocyanurate compound, its content 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 resin solids in the resin composition. By setting the content of the (meth)allyl isocyanurate compound to be above the lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion of the resulting 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 be 20 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. By setting the content of the (meth)allyl isocyanurate compound to be below the upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)allyl isocyanurate compound, or it may contain two or more types. If two or more types are included, it is preferable that the total amount falls within the above range.

[0174] <<<(Meth)allyl-substituted nadiimide compounds>>> (Meth)allyl-substituted nadiimide compounds are not particularly limited as long as they have two or more (meth)allyl-substituted nadiimide groups in their molecule. A specific example is the compound represented by the following formula (AN-1). (In formula (AN-1), R １ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ２ This represents an alkylene group, phenylene group, biphenylene group, naphthylene group having 1 to 6 carbon atoms, or a group represented by formula (AN-2) or (AN-3). (In formula (AN-2), R ３ These are methylene groups, isopropylidene groups, -C(=O)-, -O-, -S-, or -S(=O) ２ (Represents the base shown by -.) (In formula (AN-3), R ４(Each of these independently represents either an alkylene group with 1 to 4 carbon atoms, or a cycloalkylene group with 5 to 8 carbon atoms.)

[0175] Furthermore, commercially available compounds can also be used as the compound represented by formula (AN-1). While not particularly limited, commercially available compounds include, for example, the compound represented by formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and the compound represented by formula (AN-5) (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). These may be used individually or in combination of two or more. Formula (AN-4)

[0176] The molecular weight of the (meth)allyl group-substituted nadiimide compound (preferably the compound represented by formula (AN)) is preferably 400 or more, more preferably 500 or more, and may be 550 or more. Setting the molecular weight of the (meth)allyl group-substituted nadiimide compound to be above the lower limit tends to further improve low dielectric properties, low thermal expansion, and heat resistance. The molecular weight of the (meth)allyl group-substituted nadiimide compound (preferably the compound represented by formula (AN)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less or 600 or less. Setting the molecular weight of the (meth)allyl group-substituted nadiimide compound to be below the upper limit tends to further improve moldability and peel strength.

[0177] When the resin composition of this embodiment contains a (meth)allyl group-substituted nadiimide compound (preferably a compound represented by formula (AN)), its content 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 resin solids in the resin composition. By setting the content of the (meth)allyl group-substituted nadiimide compound to or above the above lower limit, moldability, low dielectric properties, low thermal expansion, and heat resistance tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl group-substituted nadiimide 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 be 20 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. By setting the content of the (meth)allyl group-substituted nadiimide compound to or below the above upper limit, moldability and peel strength tend to be further improved. The resin composition of this embodiment may contain only one (meth)allyl group-substituted nadiimide compound, or it may contain two or more. When two or more are included, it is preferable that the total amount is within the above range.

[0178] <<<(Meth)allyl Compounds Having a Glycoluryl Structure>>> The (meth)allyl compound having a glycoluryl structure is not particularly limited as long as it contains a glycoluryl structure and two or more (meth)allyl groups. When a (meth)allyl compound having a glycoluryl structure is incorporated into a resin composition, the number of (meth)allyl groups can be increased, i.e., the number of crosslinking points can be increased. Therefore, similar to (meth)allyl isocyanurate compounds, it tends to harden firmly with other thermosetting compounds such as aromatic resins and maleimide compounds having carbon-carbon double bonds at the terminals, resulting in a cured product with excellent low dielectric properties (Dk and / or Df) and heat resistance. In this embodiment, the (meth)allyl compound having a glycoluryl structure is preferably a compound represented by formula (GU). Formula (GU) (In formula (GU), R １ Each is independently a hydrogen atom or a substituent, and R１ At least two of these are groups containing a (meth)allyl group. ２ Each of these independently represents a hydrogen atom, an alkyl group, or an aryl group.) In formula (GU), R １ Each of these is preferably independently a hydrogen atom, a C1-C5 alkyl group, or a C2-C5 alkenyl group, more preferably a C2-C5 alkenyl group, more preferably a (meth)allyl group, and even more preferably an allyl group. In formula (GU), R １ It is preferable that three or four of the groups contain (meth)allyl groups, and more preferably that four of the groups contain (meth)allyl groups. In formula (GU), R ２ Each of these is preferably independently a hydrogen atom, a C1-C4 alkyl group, or a phenyl group, more preferably a hydrogen atom or a methyl group, and two R ２ It is even more preferable that all of them are hydrogen atoms.

[0179] A specific example of a compound represented by formula (GU) is 1,3,4,6-tetraallyl glycoluryl (in formula (GU), R １ All of them are allyl groups, R ２ Examples include compounds in which all atoms are hydrogen atoms.

[0180] (Meth)allyl compounds having a glycoluryl structure can also be commercially available. Examples of commercially available compounds, though not particularly limited, include TA-G manufactured by Shikoku Chemicals Co., Ltd.

[0181] The molecular weight of the (meth)allyl compound having a glycoluryl structure (preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, even more preferably 250 or more, and may be 300 or more, or 400 or more. By setting the molecular weight of the (meth)allyl compound having a glycoluryl structure to be above the lower limit above, the heat resistance and low thermal expansion properties of the resulting cured product tend to be further improved. The molecular weight of the (meth)allyl compound having a glycoluryl structure (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl compound having a glycoluryl structure to be below the upper limit above, the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product tend to be further improved.

[0182] When the resin composition of this embodiment contains a (meth)allyl compound having a glycoluryl structure (preferably represented by formula (GU)), its content 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 resin solids in the resin composition. By setting the content of the (meth)allyl compound having a glycoluryl structure to be above the above lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion of the resulting cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound having a glycoluryl structure (preferably 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 be 20 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. By setting the content of the (meth)allyl compound having a glycoluryl structure to be below the above upper limit, the low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. The resin composition of this embodiment may contain only one (meth)allyl compound having a glycoluryl structure, or it may contain two or more. When it contains two or more, it is preferable that the total amount is within the above range.

[0183] <<(meth)acrylate compound>> The resin composition of this embodiment may contain a (meth)acrylate compound. In this specification, the (meth)acrylate compound that also corresponds to the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal as described above is defined as the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal. 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.

[0184] The polyfunctional (meth)acrylate compound used in this embodiment is preferably a compound having three to five (meth)acryloyloxy groups, more preferably a compound having three or four (meth)acryloyloxy groups, and even more preferably a compound having three (meth)acryloyloxy groups. The (meth)acrylate compound is preferably a compound having methacryloyloxy groups. Because the polyfunctional (meth)acrylate compound has a large number of (meth)acrylate groups that act as crosslinking points, it hardens firmly with other thermosetting compounds such as aromatic resins and maleimide compounds having carbon-carbon double bonds at their terminals, resulting in a cured product with excellent low dielectric properties (Dk and / or Df) and heat resistance. As the polyfunctional (meth)acrylate compound, a compound represented by formula (MA) is preferred. Formula (MA) (In formula (MA), R １ R represents a hydrogen atom or substituent. ２ (Each of these independently represents either a hydrogen atom or a methyl group.)

[0185] In formula (MA), R １ represents a hydrogen atom or substituent, more preferably a substituent with a formula weight of 15 to 500, more preferably a substituent with a formula weight of 15 to 300, even more preferably a substituent with a formula weight of 15 to 100, and even more preferably a substituent with a formula weight of 15 to 50.

[0186] R １Preferably, the alkyl group is a hydrocarbon group or a (meth)acryloyloxy group, more preferably a hydrocarbon group having 22 or fewer carbon atoms, and even more preferably an alkyl group having 1 to 22 carbon atoms, or an alkenyl group having 2 to 22 carbon atoms. By using a compound having an alkyl group having 1 to 22 carbon atoms, or an alkenyl group having 2 to 22 carbon atoms, it is possible to provide a resin composition that can produce a cured product with excellent crosslinking properties and high toughness. This makes it possible to suppress cracking during etching and other processes, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handling properties, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 2 or more, may be 8 or more, and may be 12 or more, or 18 or less. This is thought to improve the resin flowability of the resin composition, and to improve circuit filling properties when using the resin composition of this embodiment to manufacture multilayer circuit boards and the like.

[0187] In this embodiment, it is preferable that the (meth)acrylic group equivalent of the compound represented by formula (MA) is 1000 g / eq. or less. When the equivalent is 1000 g / eq. or less, a higher Tg tends to be obtained more reliably. The lower limit of the (meth)acrylic group equivalent is, for example, 99 g / eq. or more.

[0188] The C1-C22 alkyl group is preferably a linear C1-C22 alkyl group or a branched C3-C22 alkyl group, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl groups. The C2-C22 alkenyl group is preferably a C2-C15 alkenyl group, such as allyl and decenyl groups.

[0189] Specific examples of compounds represented by formula (MA) include, for example, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, and pentaerythritol tetra(meth)acrylate. These may be used individually or in combination of two or more, and may also be used as prepolymers.

[0190] Furthermore, commercially available compounds can also be used as the compound represented by formula (MA). While not particularly limited, commercially available products include, for example, "NK Ester TMPT" manufactured by Shin-Nakamura Chemical Industry Co., Ltd., which is trimethylolpropane trimethacrylate.

[0191] 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. Setting the molecular weight above the lower limit tends to further improve the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product. 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. Setting the molecular weight below the upper limit tends to further improve the low thermal expansion properties of the resulting cured product.

[0192] In addition to the above, the (meth)acrylate compounds may also include resins having (meth)acrylic groups as described in International Publication No. 2022 / 210095 (for example, the compounds described in Synthesis Examples 5 and 21 of the same publication), resins having (meth)acrylic groups as described in Japanese Patent No. 6962507 (for example, the compounds described in Examples 1 to 9), the compounds described in paragraph 0049 of Japanese Patent Application Publication No. 2019-194312, resins having (meth)acrylic groups as described in paragraphs 0010 to 0096 of Japanese Patent Application Publication No. 2024-159338, resins having methacrylic groups as described in International Publication No. 2023 / 089976, and resins having methacrylic groups as described in International Publication No. 2022 / 234455, and this information is incorporated herein by reference.

[0193] When the resin composition of this embodiment contains a (meth)acrylate compound, its content 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 resin solids in the resin composition. By setting the content of the (meth)acrylate compound to be above the lower limit above, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion of the resulting 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 resin solids in the resin composition. By setting the content of the (meth)acrylate compound to be below the upper limit above, the heat resistance and low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)acrylate compound, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0194] <<Epoxy Compound>> The resin composition of this embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having one or more epoxy groups in one molecule (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and compounds commonly used in the field of printed circuit boards can be widely used. Examples of the epoxy compounds include phenol novolac type epoxy resins, bisphenol A novolac type epoxy resins, glycidyl ester type epoxy resins, aralkyl novolac type epoxy resins, biphenyl aralkyl type epoxy resins, naphthylene ether type epoxy resins, cresol novolac type epoxy resins, polyfunctional phenol type epoxy resins, naphthalene type epoxy resins, anthracene type epoxy resins, naphthalene skeleton-modified novolac type epoxy resins, phenol aralkyl type epoxy resins, naphthol aralkyl type epoxy resins, dicyclopentadiene type epoxy resins, biphenyl type epoxy resins, alicyclic epoxy resins, polyol type epoxy resins, phosphorus-containing epoxy resins, compounds in which double bonds of glycidylamine, glycidyl esters, butadiene, etc. are epoxidized, and compounds obtained by the reaction of hydroxyl group-containing silicone resins with epichlorohydrin. Using these 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 resin, naphthylene ether epoxy resin, polyfunctional phenolic epoxy resin, and naphthalene epoxy resin, and more preferably a biphenylaralkyl epoxy resin.

[0195] If the resin composition of this embodiment contains an epoxy compound, its content 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 resin solids in the resin composition. A content of 0.1 parts by mass or more of the epoxy compound tends to improve the metal foil peel strength and toughness. 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, even more preferably 10 parts by mass or less, and may also be 8 parts by mass or less, or 5 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. A content of 50 parts by mass or less of the epoxy compound tends to improve the electrical properties of the resulting cured product. The resin composition of this embodiment may contain only one type of epoxy compound, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range. Furthermore, the resin composition of this embodiment may also be configured to substantially not contain any epoxy compound. "Substantially contained" means that the epoxy compound content is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition, preferably less than 0.01 parts by mass, and even more preferably less than 0.001 parts by mass.

[0196] <<Phenol Compounds>> The resin composition of this embodiment may contain phenol compounds. The phenol compound is not particularly limited as long as it is a phenol compound 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) phenolic hydroxyl groups in one molecule, and compounds commonly used in the field of printed circuit boards can be widely used. Examples of the phenol compound include phenol novolac resins, bisphenol A type novolac type phenol resins, glycidyl ester type phenol resins, aralkyl novolac phenol resins, biphenyl aralkyl type phenol resins, cresol novolac type phenol resins, polyfunctional phenol resins, naphthol resins, naphthol novolac resins, polyfunctional naphthol resins, anthracene type phenol resins, naphthalene skeleton-modified novolac type phenol resins, phenol aralkyl type phenol resins, naphthol aralkyl type phenol resins, dicyclopentadiene type phenol resins, biphenyl type phenol resins, alicyclic phenol resins, polyol type phenol resins, phosphorus-containing phenol resins, hydroxyl group-containing silicone resins, and the like. Among these, from the viewpoint of further improving the flame resistance of the resulting cured product, it is preferable to select at least one from the group consisting of biphenyl aralkyl type phenol resin, naphthol aralkyl type phenol resin, phosphorus-containing phenol resin, and hydroxyl group-containing silicone resin.

[0197] Furthermore, as for phenolic compounds, the descriptions in paragraphs 0012-0025 of International Publication No. 2023 / 176765 can also be referenced, and this content is incorporated herein.

[0198] If the resin composition of this embodiment contains a phenol compound, its content 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 resin solids in the resin composition. It is also 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 may be 5 parts by mass or less. The resin composition of this embodiment may contain only one type of phenol compound or may contain two or more types. If it contains two or more types, it is preferable that the total amount is within the above range. Furthermore, the resin composition of this embodiment may also be configured to be substantially free of phenol compounds. Substantially free means that the content of the phenol compound is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0199] <<Oxetane Compounds>> The resin composition of this embodiment may contain oxetane compounds. The oxetane compound is not particularly limited as long as it is a compound having one or more oxetanyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and compounds commonly used in the field of printed circuit boards can be widely used. Examples of oxetane compounds include oxetane, alkyl oxetane (e.g., 2-methyl oxetane, 2,2-dimethyl oxetane, 3-methyl oxetane, 3,3-dimethyl oxetane, etc.), 3-methyl-3-methoxymethyl oxetane, 3,3-di(trifluoromethyl)oxetane, 2-chloromethyl oxetane, 3,3-bis(chloromethyl)oxetane, biphenyl-type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), OXT-121 (manufactured by Toagosei Co., Ltd.), etc.

[0200] The resin composition of this embodiment preferably contains an oxetane compound in a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an oxetane compound, its content 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 resin solids in the resin composition. When the oxetane compound content is 0.1 parts by mass or more, the metal foil peel strength and toughness of the resulting cured product tend to improve. The upper limit of the oxetane compound content when the resin composition of this embodiment contains an 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 resin solids in the resin composition. When the oxetane compound content is 50 parts by mass or less, the electrical properties of the resulting cured product tend to improve. The resin composition of this embodiment may contain only one type of oxetane compound, or it may contain two or more types. When two or more types are included, it is preferable that the total amount be within the above range. Furthermore, the resin composition in this embodiment may also be configured to be substantially free of oxetane compounds. Substantially free means that the content of oxetane compounds is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0201] <<Benzoxazine Compounds>> The resin composition of this embodiment may contain benzoxazine compounds. The benzoxazine compound is not particularly limited as long as it is a compound having two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings in one molecule, and compounds commonly used in the field of printed circuit boards can be widely 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.).

[0202] The resin composition of this embodiment preferably contains a benzoxazine compound in a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a benzoxazine compound, the content is preferably 0.1 parts by mass or more, and preferably 50 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. The resin composition of this embodiment may contain only one type of benzoxazine compound, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the above range. Furthermore, the resin composition of this embodiment may also be configured to substantially not contain a benzoxazine compound. Substantially not containing a benzoxazine compound means that the content of the benzoxazine compound is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0203] <<Arylcyclobutene Compounds>> The resin composition of this embodiment may contain arylcyclobutene compounds. Details of this include the arylcyclobutene resin described in paragraph 0042 of Japanese Patent Application Publication No. 2019-194312, and this information is incorporated herein by reference.

[0204] The resin composition of this embodiment preferably contains an arylcyclobutene compound in a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an arylcyclobutene compound, its content is preferably 0.1 parts by mass or more, and preferably 50 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. The resin composition of this embodiment may contain only one type of arylcyclobutene compound, or it may contain two or more types. When it contains two or more types, it is preferable that the total amount is within the above range. Furthermore, the resin composition of this embodiment may also be configured to substantially not contain an arylcyclobutene compound. Substantially not containing an arylcyclobutene compound means that the content of the arylcyclobutene compound is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0205] <<Perfluorovinyl ether resin>> The resin composition of this embodiment may also contain a perfluorovinyl ether resin. Examples of perfluorovinyl ether resins include perfluorovinyl benzyl ether resin. Details of this include perfluorovinyl ether resins described in paragraph 0043 of Japanese Patent Application Publication No. 2019-194312, and this information is incorporated herein by reference.

[0206] <<Polyimide Compounds>> The resin composition of this embodiment may contain a polyimide compound, and may also contain a thermosetting polyimide compound. Details therein can be found in paragraph 0064 of Japanese Patent No. 6951829, which is incorporated herein by reference.

[0207] The resin composition of this embodiment preferably contains a polyimide compound in a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a polyimide compound, the content is preferably 0.1 parts by mass or more, and preferably 50 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. The resin composition of this embodiment may contain only one type of polyimide compound, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the above range. Furthermore, the resin composition of this embodiment may also be configured to substantially not contain a polyimide compound. Substantially not containing a polyimide compound means that the content of the polyimide compound is less than 0.1 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0208] <<Compounds Having a Vinylene Group>> The resin composition of this embodiment may contain compounds having a vinylene group. Examples of compounds having a vinylene group include compounds containing one or more -CH=CH- groups in the molecule, with compounds containing one -CH=CH- group in the molecule being preferred. Compounds having a vinylene group that also fall under the category of maleimide compounds are defined as maleimide compounds. Specific examples of compounds having a vinylene group include acenaphthylene and pyrasilen, with acenaphthylene being more preferred. In this specification, compounds that also correspond to compounds having a vinylene group, such as the imidazole compounds mentioned above, but are explicitly listed as components other than compounds having a vinylene group (e.g., radical polymerization initiators), are not considered compounds having a vinylene group.

[0209] <Flame Retardant> The resin composition of this embodiment may contain a flame retardant. Examples of flame retardants include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, with phosphorus-based flame retardants being preferred. As flame retardants, known substances can be used, for example, halogenated 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-pentabromopentane, chlorinated polystyrene, chlorinated paraffin, etc., phosphorus-containing flame retardants such as red phosphorus, tricresyl phosphate, triphenyl phosphate, 2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, cresyldiphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroeth Examples of phosphorus-based flame retardants include monomer-type phosphate esters such as phosphates, phosphazenes, phenoxyphosphazenes, 1,3-phenylenebis(2,6-dixylenyl phosphate), xylenebisdiphenylphosphine oxide of the bisdiphenylphosphine oxide type, condensed phosphate esters of dixylenyl phosphate of the phosphate ester type, 6H-dibenz[c,e][1,2]oxaphosphorine, 6,6'-[1,4-phenylenebis(methylene)]bis-,6,6'-dioxide, condensed phosphate esters of phosphinate metal salts of phosphinate aluminum dialkylphosphinate of the phosphinate type, 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).

[0210] When the resin composition of the present embodiment contains a flame retardant, its content is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and preferably 30 parts by mass or less, more preferably 25 parts by mass or less, further preferably 20 parts by mass or less, still more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. The flame retardant can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0211] <Active ester compound> The resin composition of the present embodiment may contain an active ester compound as long as the effects of the present invention are not impaired. The active ester compound is not particularly limited. For example, the descriptions in paragraphs 0064 to 0066 of WO 2021 / 172317 can be referred to, and this content is incorporated herein.

[0212] When the resin composition of the present embodiment contains an active ester compound, it is preferably 1 part by mass or more, and preferably 50 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one kind of active ester compound or two or more kinds. When two or more kinds are contained, it is preferable that the total amount is within the above range. Also, the resin composition in the present embodiment can be configured to substantially not contain an active ester compound. Substantially not containing 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, based on 100 parts by mass of the resin solid content in the resin composition.

[0213] <Dispersant> The resin composition of this embodiment may contain a dispersant. As the dispersant, those generally used for paints can be preferably used, and the type thereof is not particularly limited. Preferably, a copolymer-based wetting dispersant is used as the dispersant. Specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, W940, etc. manufactured by BYK Japan Co., Ltd.

[0214] When the resin composition of this embodiment contains a dispersant, the lower limit of its 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 with respect to 100 parts by mass of the resin solid content in the resin composition. Also, the upper limit of the content of the dispersant 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 with respect to 100 parts by mass of the resin solid content in the resin composition. The dispersant can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0215] <Solvent> The resin composition of this embodiment may contain a solvent, and preferably an organic solvent. When a solvent is included, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the above-mentioned resin solids are dissolved or miscible with the solvent. The solvent is not particularly limited as long as it is a polar or nonpolar organic solvent capable of dissolving or miscible at least a portion, preferably all, of the above-mentioned resin solids. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), cellosolves (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and amides (e.g., dimethoxyacetamide, dimethylformamides, etc.). Examples of nonpolar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). The solvent can be used individually or in combination of two or more types. When using two or more types, the total amount must be within the above range.

[0216] <Curing accelerator> The resin composition of this embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, but examples 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)hexine-3; azo compounds such as azobisnitrile (e.g., azobisisobutyronitrile) and 2,2-azobis(2,4,4-trimethylpentane); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, and 2-N-ethylanilinoethanol Examples include 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 radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organometallic salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octoate, manganese octoate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetone; compounds obtained by dissolving these organometallic salts in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organotin compounds such as dioctyl tin oxide, other alkyltins, and alkyltin oxides. Among these, preferred curing accelerators are at least one selected from the group consisting of imidazoles, organometallic salts, and organic peroxides, with at least one selected from the group consisting of organometallic salts and organic peroxides being more preferred, and organic peroxides being even more preferred.

[0217] If the resin composition of this embodiment contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.05 parts by mass or more, and even more preferably 0.08 parts by mass or more, per 100 parts by mass of 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 part 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 depending on the application, it may be 0.2 parts by mass or less, or 0.15 parts by mass or less. The resin composition of this embodiment is preferable in that it can sufficiently cure the resin composition even if the curing accelerator content is below the above upper limit. The curing accelerator can be used alone or in combination of two or more types. If two or more types are used, the total amount will be within the above range.

[0218] <Filler> The resin composition of this embodiment may also contain a filler other than the compound represented by formula (1A) and / or the compound represented by formula (1B). By including a filler, the physical properties of the resin composition and its cured product, such as dielectric properties (relative permittivity and / or dielectric loss tangent), flame resistance, and low thermal expansion, can be further improved. Furthermore, it is more preferable that the filler used in this embodiment has excellent low dielectric properties (Dk and / or Df). For example, the filler used in this embodiment preferably has a relative permittivity (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, the lower limit of the relative permittivity is practically 2.0 or more. Furthermore, the filler used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, and 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 higher.

[0219] The type of filler used in this embodiment is not particularly limited, and those commonly used in the industry can be suitably used. Specifically, silica such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, etc.; metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, etc.; composite oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, etc.; nitrides such as boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, etc.; aluminum hydroxide, heat-treated aluminum hydroxide (aluminum hydroxide that has been heat-treated to reduce some of the crystal water), boehmite, magnesium hydroxide, etc. (including hydrates); acid Examples of inorganic fillers include molybdenum compounds such as molybdenum molasses and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (including glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, 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 include 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), it is more preferable to include one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferable to include silica. By using these inorganic fillers, the properties of the cured resin composition, such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy, are further improved.

[0220] The filler content in the resin composition of this embodiment can be appropriately set according to the desired properties and is not particularly limited, but is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and 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, depending on the application, etc. Setting it above the lower limit tends to result in better low thermal expansion and low dielectric loss tangent of the resulting cured product. 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, and may be 150 parts by mass or less or 100 parts by mass or less, depending on the application, etc. Setting it below the upper limit tends to result in better moldability of the resin composition. In the resin composition of this embodiment, as an example of a preferred embodiment, there is a configuration in which the filler content is 1 to 95% by mass of the components excluding the solvent, with a preferred configuration of 10% to 50% by mass, and a more preferred configuration of 10% to 30% by mass. The resin composition of this embodiment may contain only one type of filler, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0221] In the resin composition of this embodiment, when a filler, particularly an inorganic filler, is used, a silane coupling agent may be further included. Including 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 later. Silane coupling agents are not particularly limited and generally include silane coupling agents used for surface treatment of inorganic materials, 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.), cationicsilane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds. Among these, it is preferable to include at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylicsilane compounds, with vinylsilane compounds being more preferable. The silane coupling agent can 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 resin solids in the resin composition.

[0222] <Elastomer> The resin composition of this embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but it is preferably thermoplastic. The elastomer in this embodiment is not particularly limited and includes, for example, at least one selected from the group consisting of polyisoprene, polybutadiene, styrenebutadiene, butyl rubber, ethylenepropylene rubber, styrenebutadieneethylene, styrenebutadienestyrene, styreneisoprenestyrene, styreneethylenebutylenestyrene, styrenepropylenestyrene, styreneethylenepropylenestyrene, fluororubber, silicone rubber, their hydrogenated compounds, their alkyl compounds, and their copolymers. Furthermore, examples of elastomers include oligomers or polymers having curable vinyl functional groups as described in paragraphs 0044 and 0045 of Japanese Patent Publication No. 2019-194312, polybutadiene resins, compounds as described in Japanese Patent Publication No. 2022-085610, and 1,2-SBS-L42 (liquid 1,2-SBS) and 1,2-SBS-P35 (solid 1,2-SBS) manufactured by Nippon Soda Co., Ltd., the details of which are incorporated herein by reference.

[0223] 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 loss tangent) of the resulting cured product tend to be better. 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. 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. By setting it below the above upper limit, the solubility of the elastomer component in the resin composition tends to improve. When the resin composition of this embodiment contains two or more elastomers, it is preferable that the number-average molecular weight of the mixture thereof satisfies the above range.

[0224] The elastomer used in this embodiment is a resin containing a polybutadiene structure. The polybutadiene structure may be partially or entirely hydrogenated. Specific examples include B-1000, B-2000, B-3000, BI-2000, BI-3000 from Nippon Soda Co., Ltd., and Ricon 100, Ricon 130, Ricon 131, Ricon 142, Ricon 150, Ricon 181, Ricon 184 from CRAY VALLEY.

[0225] The elastomer used in this embodiment is a resin having a poly(meth)acrylate structure. Specific examples include Teisan Resin manufactured by Nagase ChemteX Corporation, and ME-2000, W-197C, KG-15, and KG-3000 manufactured by Negami Kogyo Co., Ltd.

[0226] The elastomer used in this embodiment is a resin having a polycarbonate structure. A resin having a polycarbonate structure is sometimes called a "polycarbonate resin." Examples of such resins include carbonate resins without reactive groups, carbonate resins containing hydroxyl groups, carbonate resins containing phenolic hydroxyl groups, carbonate resins containing carboxyl groups, carbonate resins containing acid anhydride groups, carbonate resins containing isocyanate groups, carbonate resins containing urethane groups, and carbonate resins containing epoxy groups. Here, a reactive group refers to a functional group that can react with other components, such as a hydroxyl group, phenolic hydroxyl group, carboxyl group, acid anhydride group, isocyanate group, urethane group, and epoxy group. Specific examples of polycarbonate resins include FPC0220 and FPC2136 manufactured by Mitsubishi Gas Chemical Co., Ltd., and T6002 and T6001 (polycarbonate diol) manufactured by Asahi Kasei Corporation.

[0227] The elastomer used in this embodiment is a resin having a polysiloxane structure. Specific examples include SMP-2006, SMP-2003PGMEA, SMP-5005PGMEA, KR-510, and SMP-7014-3S, all manufactured by Shin-Etsu Silicone Co., Ltd.

[0228] The elastomer used in this embodiment is a resin having a polyalkylene structure and / or a polyalkylene oxy structure. The polyalkylene oxy structure is preferably a polyalkylene oxy structure having 2 to 15 carbon atoms, more preferably a polyalkylene oxy structure having 3 to 10 carbon atoms, and particularly preferably a polyalkylene oxy structure having 5 to 6 carbon atoms. Specific examples of resins having a polyalkylene structure and / or a polyalkylene oxy structure include PTXG-1000 and PTXG-1800 manufactured by Asahi Kasei Fibers Co., Ltd.

[0229] The elastomer used in this embodiment is a resin having a polyisoprene structure. Specific examples include KL-610 and KL613 manufactured by Kuraray Co., Ltd.

[0230] The elastomer used in this embodiment is a resin having a polyisobutylene structure. Specific examples include SIBSTAR-073T (styrene-isobutylene-styrene triblock copolymer) and SIBSTAR-042D (styrene-isobutylene diblock copolymer) manufactured by Kaneka Corporation.

[0231] 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, in particular low dielectric loss tangent) of the resulting cured product are further improved.

[0232] The above elastomer (e) contains styrene monomer units. The inclusion of styrene monomer units improves the solubility of 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 viewpoint of availability and productivity. Styrene is particularly preferred among these. The content of styrene monomer units in the above elastomer (e) is preferably 10% by mass or more, more preferably 13% by mass or more, even more preferably 15% by mass or more, and preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less. By keeping the content of styrene monomer units below the above upper limit, adhesion and tackiness to the substrate are improved. Furthermore, it is preferable that the styrene monomer unit content is above the lower limit, as this suppresses increased adhesion, reduces the likelihood of adhesive residue and stop marks, and improves the ease of peeling between adhesive surfaces. Elastomer (e) may contain only one type of styrene monomer unit, or it may contain two or more types. If it contains two or more types, it is preferable that the total amount is within the above range. The method for measuring the styrene monomer unit content in elastomer (e) of this embodiment can be based on the description in International Publication No. 2017 / 126469, and this content is incorporated herein. The same applies to conjugated diene monomer units, etc., which will be described later.

[0233] The above elastomer (e) contains conjugated diene monomer units. The inclusion of conjugated diene monomer units improves the solubility of 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 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, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred. Elastomer (e) may contain only one type of conjugated diene monomer unit, or it may contain two or more types.

[0234] In the above elastomer (e), the mass ratio of styrene monomer units to conjugated diene monomer units is preferably in the range of styrene monomer units / conjugated diene monomer units = 5 / 95 to 80 / 20, more preferably in the range of 7 / 93 to 77 / 23, and even more preferably in the range of 10 / 90 to 70 / 30. If the mass ratio of styrene polymer units to conjugated diene monomer units is in the range of 5 / 95 to 80 / 20, adhesion enhancement can be suppressed and high adhesive strength can be maintained, and the ease of peeling between adhesive surfaces is good.

[0235] The above elastomer (e) may have all of its conjugated diene bonds hydrogenated, partially hydrogenated, or not hydrogenated at all.

[0236] The above elastomer (e) may or may not contain other monomer units in addition to styrene monomer units and conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than styrene monomer units. The above elastomer (e) preferably contains 90% by mass or more of the total styrene monomer units and conjugated diene 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 conjugated diene monomer unit, or two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0237] The elastomer (e) used in this embodiment may be a block polymer or a random polymer. Furthermore, it may be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, an unhydrogenated elastomer in which the units are not hydrogenated, or a partially hydrogenated elastomer in which the units are partially hydrogenated, and it is preferable that it be an unhydrogenated elastomer or a partially hydrogenated elastomer. In one embodiment of this embodiment, the elastomer (e) is a hydrogenated elastomer. Here, a hydrogenated elastomer means, for example, one in which the double bonds based on the conjugated diene monomer units in the elastomer are hydrogenated, and includes not only those with a hydrogenation rate (hydrogenation rate) of 100% but also those 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 1It is calculated from the measurement results of the H-NMR spectrum measurement. In one embodiment of this embodiment, elastomer (e) is an unhydrogenated elastomer. Here, an unhydrogenated elastomer refers to one in which the proportion of double bonds based on conjugated diene monomer units in the elastomer that are hydrogenated, i.e., the 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 one in which some of the double bonds based on conjugated diene monomer units in the elastomer are hydrogenated, and usually refers to one in which the hydrogenation rate is less than 80% and more than 20%.

[0238] Examples of commercially available elastomers (e) used in this embodiment include SEPTON® 2104, V9461, S8104 from Kuraray Co., Ltd., S.O.E.® S1606, S1613, S1609, S1605 from Asahi Kasei Corporation, ToughTec® H1041, H1043, P2000, MP10 from Asahi Kasei Corporation, and DYNARON® 9901P, TR2250 from JSR Corporation.

[0239] The elastomer used in this embodiment may also be a liquid diene. A liquid diene means a liquid elastomer containing conjugated diene monomer units. 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, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred. Examples of liquid dienes used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, liquid acrylonitrile-butadiene copolymer, and liquid styrene-butadiene copolymer. Furthermore, 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 to 10,000.

[0240] The elastomer used in this embodiment may also be the elastomer described in Japanese Patent Application Publication No. 2022-33057. For example, Kraton's MD3501 can be used as such a commercially available product.

[0241] If the resin composition of this embodiment contains an elastomer (preferably elastomer (e)), the content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 8 parts by mass or more, and may be 10 parts by mass or more, or 12 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. Setting it above the lower limit tends to further improve dielectric properties (low dielectric loss tangent). The upper limit of the elastomer content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less, and may be 20 parts by mass or less, or 15 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. Setting it below the upper limit tends to further improve heat resistance. The resin composition of this embodiment may contain only one type of elastomer, or it may contain two or more types. If it contains two or more types, it is preferable that the total amount is within the above range. Furthermore, the resin composition in this embodiment may also be substantially free of elastomers. Substantially free means that the elastomer content is less than 1 part by mass per 100 parts by mass of resin solids in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0242] <Petroleum Resin> The resin composition of this embodiment may contain a petroleum resin. By containing a petroleum resin, the melt viscosity can be lowered. A petroleum resin is a resin obtained by polymerizing the remaining components obtained by pyrolyzing petroleum naphtha and collecting the necessary fractions without isolating unsaturated hydrocarbons without a catalyst or in the presence of a catalyst. As the remaining fraction, mainly, a fraction containing a C5 fraction (isoprene, piperylene, cyclopentadiene, pentenes, pentanes, etc.) or a C9 fraction (vinyltoluene, indene, dicyclopentadiene, etc.) is included.

[0243] The catalyst used for producing the petroleum resin is preferably an acidic catalyst. Specifically, Lewis acids such as boron trifluoride phenol complex, boron trifluoride ether complex, aluminum chloride, aluminum bromide, iron(III) chloride, iron(III) bromide, solid acids such as zeolite, silica, montmorillonite, alumina, ion exchange resins such as sulfonic acid group-containing fluororesin, sulfonic acid group-containing polystyrene resin, and proton acids such as sulfuric acid, hydrochloric acid, acetic acid, phosphoric acid, oxalic acid, nitric acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. can be used. Among these, it is preferable to use Lewis acids and solid acids because side reactions are less likely to occur and the reaction rate is fast, and various complexes of boron trifluoride and aluminum chloride are more preferable in terms of easy availability and high reactivity.

[0244] The weight average molecular weight of the petroleum resin is not particularly limited, but is preferably 500 to 10,000, more preferably 500 to 5,000. By setting it below the upper limit value, it tends to be more compatible with other resins and also has higher solubility in solvents. By setting it above the lower limit value, the heat resistance and mechanical strength of the obtained cured product tend to be further improved.

[0245] The softening point of the petroleum resin is not particularly limited, but it is preferably high, preferably 80°C or higher, more preferably 100°C or higher. By setting it above the lower limit value, the heat resistance of the obtained cured product tends to be improved.

[0246] Examples of petroleum resins include aliphatic petroleum resins, aromatic petroleum resins, copolymer petroleum resins, and dicyclopentadiene petroleum resins, with dicyclopentadiene petroleum resins being preferred. Examples of dicyclopentadiene petroleum resins include resins obtained by polymerizing dicyclopentadiene fractions such as dicyclopentadiene, isopropenylnorbornene, dimethyldicyclopentadiene, and tricyclopentadiene, and resins obtained by polymerizing dicyclopentadiene fractions with other monomers having unsaturated bonds, preferably unsaturated cyclic olefins.

[0247] Examples of the aforementioned unsaturated cyclic olefins include cyclopentadiene; norbornene monomers such as 2-norbornene, 5-methyl-2-norbornene, 5-ethylidene-2-norbornene, 5-phenylnorbornene, 5-propenyl-2-norbornene, and 5-ethylidene-2-norbornene; and further, as norbornene monomers of three or more rings, examples include tricyclic compounds other than dicyclopentadiene fractions such as diethyldicyclopentadiene and dihydrodicyclopentadiene, tetracyclic compounds such as tetracyclododecene, pentacyclic compounds such as tricyclopentadiene, heptacyclic compounds such as tetracyclopentadiene, and alkyl-substituted, alkylidene-substituted, and aryl-substituted polycyclic compounds thereof. Examples of alkyl-substituted polycyclic compounds include methyl, ethyl, propyl, and butyl-substituted compounds, while examples of alkylidene-substituted polycyclic compounds include ethylidene-substituted compounds, and examples of aryl-substituted polycyclic compounds include phenyl, tolyl, and naphthyl-substituted compounds.

[0248] Furthermore, as monomers having unsaturated bonds other than unsaturated cyclic olefins, olefins having 3 to 12 carbon atoms may be copolymerized. Examples include α-olefins such as propylene, butene-1, pentene-1, 1,3-pentadiene, hexene-1, heptene-1, octene-1, diisobutylene, nonene-1, decene-1, 4-phenylbutene-1, 6-phenylhexene-1, 3-methylbutene-1, 4-methylpentene-1, 3-methylpentene-1, 3-methylhexene-1, 4-methylhexene-1, 5-methylhexene-1, 3,3-dimethylpentene-1, 3,4-dimethylpentene-1, 4,4-dimethylpentene-1, vinylcyclohexane, and vinylcyclohexene; and halogen-substituted α-olefins such as hexafluoropropene, 2-fluoropropene, 3-fluoropropene, and 3,4-dichlorobutene-1.

[0249] Other monomers having unsaturated bonds besides those mentioned above include, for example, ethylene, tetrafluoroethylene, fluoroethylene, 1,1-difluoroethylene, trifluoroethylene; alkylstyrenes such as styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, 3,4-dimethylstyrene, 3,5-dimethylstyrene, and p-t-butylstyrene; halogenated styrenes such as p-chlorostyrene, m-chlorostyrene, o-chlorostyrene, p-bromostyrene, m-bromostyrene, o-bromostyrene, p-fluorostyrene, m-fluorostyrene, o-fluorostyrene, and o-methyl-p-fluorostyrene; and maleic anhydride, maleic acid, fumaric acid, allyl alcohol, 3-buten-2-ol, methylbuten-1-ol, vinyl acetate, and vinyl chloride.

[0250] The monomer may be used alone or in combination of two or more types.

[0251] Commercially available petroleum resins can be used as appropriate. Aliphatic petroleum resins include Quinton A100, Quinton B170, Quinton K100, Quinton M100, Quinton R100, and Quinton C200S from Zeon Corporation, and Marcaretz T-100AS and Marcaretz R-100AS from Maruzen Petrochemical Co., Ltd. Aromatic petroleum resins include Neopolymer L-90 and Neopolymer 120 from JXTG Energy Corporation. Remar 130, Neopolymer 140, Neopolymer 150, Neopolymer 170S, Neopolymer 160, Neopolymer E-100, Neopolymer E-130, Neopolymer 130S, Neopolymer S, Tosoh Corporation's Petocol LX, Petocol LX-HS, Petocol 100T, Petocol 120, Petocol 120HS, Petocol 130, Petocol 140, Petocol 140HM, Petocol 140HM5, Petocol 150, Peto Coal 150AS, copolymer petroleum resins include Quinton D100, Quinton N180, Quinton P195N, Quinton S100, Quinton S195, Quinton U185, Quinton G100B, Quinton G115, Quinton D200, Quinton E200SN, Quinton N295 from Nippon Zeon Corporation, and Petrotac 60, Petrotac 70, Petrotac 90, Petrotac 90V, Petrotac 100 from Tosoh Corporation. Examples of petroleum resins include PetroTac 100V, PetroTac 90HM, and DCPD (dicyclopentadiene)-based petroleum resins such as Marcaretz M-890A and Marcaretz M-845A from Maruzen Petrochemical Co., Ltd., Quinton 1325, Quinton 1345, Quinton 1500, Quinton 1525L, and Quinton 1700 from Nippon Zeon Corporation, and HA085, HA103, HA105, HA125, HB103, and HB125 from ENEOS Corporation. In addition, petroleum resins described in Organic Synthesis Chemistry, Vol. 25, No. 6 (1967) can also be used.

[0252] When the resin composition of this embodiment contains petroleum resin, the lower limit of its 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, even more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. Setting it above the lower limit tends to decrease the melt viscosity. The upper limit of the petroleum resin content is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, and may be 40 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. Setting it below the upper limit tends to decrease Df. The resin composition of this embodiment may contain only one type of petroleum resin, or it may contain two or more types. When it contains two or more types, it is preferable that the total amount is within the above range. The resin composition of this embodiment may also be configured to substantially not contain petroleum resin. "Substantially contained" means that the petroleum resin content is less than 1 part by mass per 100 parts by mass of resin solids in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0253] <Other Components> In addition to the components described above, the resin composition of this embodiment may also contain various polymer compounds such as thermoplastic resins and their oligomers, and various additives. Examples of additives include at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors. The content of other components in the resin composition of this embodiment (various polymer compounds such as thermoplastic resins and their oligomers, various additives, etc.) other than the components described above is preferably 0 parts by mass or more and less than 10 parts by mass, more preferably 0 parts by mass or more and less than 5 parts by mass, even more preferably 0 parts by mass or more and less than 3 parts by mass, and may be 0 parts by mass or more and less than 1 part by mass, per 100 parts by mass of resin solids. The total amount of additives is preferably 0 parts by mass or more and less than 5 parts by mass, more preferably 0 parts by mass or more and less than 3 parts by mass, even more preferably 0 parts by mass or more and less than 1 part by mass, and may also be 0 parts by mass or more and less than 0.5 parts by mass, per 100 parts by mass of resin solids.

[0254] Polymerization inhibitors include, for example, quinones, phenols, nitrosos, hydroxyamines, organoboric acid compounds, and compounds having phenolic hydroxyl groups. Specifically, these include 2-nitrophenol, 4-methoxyphenol, 4-tert-butylpyrocatechol, pyrogallol, 4,4'-butylidenebis(6-tert-butyl-m-cresol), tert-butylhydroquinone, 1,4-benzoquinone, 2-hydroxybenzophenone, cuprous chloride, phenothiazine, chloranil, naphthylamine, β-naphthol, 2,6-di-t-butyl-4-cresol, and 2,2'-methylenebis(4-methyl- Examples include 6-t-butylphenol, pyridine, nitrobenzene, dinitrobenzene, picric acid, 4-toluidine, methylene blue, copper and organic chelating agent reaction products, methyl salicylate, dibutylhydroxytoluene, 1,1-diphenyl-2-picrylhydrazyl free radical, hydroquinone, hydroquinone monomethyl ether, mequinol, N-nitroso-N-phenylhydroxylamine aluminum, triethyl borate, tributyl borate, triisopropyl borate, 2,3-dihydroxynaphthalene, 4-methoxy-1-naphthol, methylhydroquinone, and the like. Furthermore, the polymerization inhibitors used are not limited to those listed above.

[0255] In the resin composition according to this embodiment, the total content of polyphenylene ether compounds other than the polyphenylene ether compounds described in <<<Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends>>> above, and thermoplastic elastomers other than the elastomers described in the <Elastomer> section above, is preferably 3% by mass or less, and more preferably 1% by mass or less, of the resin solids. By having such a configuration, the effects of the present invention are more effectively exhibited. Furthermore, the total content of polyphenylene ether compounds other than the polyphenylene ether compounds described in <<<Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends>>> above, and butadiene elastomers that do not contain a styrene skeleton, is preferably 3% by mass or less, and more preferably 1% by mass or less, of the resin solids. By having such a configuration, the effects of the present invention are more effectively exhibited. Moreover, the total content of polyphenylene ether compounds other than the polyphenylene ether compounds represented by the above formula (OP), and butadiene elastomers that do not contain a styrene skeleton, is preferably 3% by mass or less, and more preferably 1% by mass or less, of the resin solids. By adopting this configuration, the effects of the present invention are more effectively realized.

[0256] <Applications> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low dielectric constant material and / or a low dielectric loss tangent material, as a resin composition for electronic materials such as insulating layers for printed circuit boards and materials for semiconductor packages. The resin composition of this embodiment can be suitably used as a prepreg, a metal foil-clad laminate using a prepreg, a resin composite sheet, and a material for printed circuit boards.

[0257] The resin composition of this embodiment preferably has a low relative permittivity (Dk) and dielectric loss tangent (Df) in its cured product. When the resin composition of this embodiment is molded into a cured plate (without metal foil) with a thickness of 1.0 mm, the relative permittivity (Dk) at a frequency of 10 GHz, measured according to the cavity resonator perturbation method, is preferably 2.50 or less. There is no particular lower limit for the relative permittivity (Dk), but for example, 0.01 or more is practical. Furthermore, when the resin composition of this embodiment is molded into a cured plate (without metal foil) with a thickness of 1.0 mm, the dielectric loss tangent (Df) at a frequency of 10 GHz, measured according to the cavity resonator perturbation method, is preferably 0.0030 or less, more preferably 0.0025 or less, even more preferably 0.0020 or less, even more preferably less than 0.0019, even more preferably 0.0015 or less, even more preferably 0.0013 or less, and even more preferably 0.0012 or less. While there is no specific lower limit for the dielectric loss tangent (Df), a value of 0.0001 or higher is practical. Furthermore, radical curing, which is also achieved by curing the resin composition by radical curing, tends to cure rapidly within a specific temperature range. This allows for denser curing of the resin composition, thereby improving the low dielectric properties (Dk and / or Df) of the resulting cured product. That is, one example of the resin composition in this embodiment is a radical-curable resin composition. Another example of the resin composition in this embodiment is a cationic-curable resin composition. The dielectric loss tangent (Df) and relative permittivity (Dk) of the cured product are measured more specifically by the method described in the examples below.

[0258] The resin composition of this embodiment preferably has a low coefficient of thermal expansion when cured. When the resin composition of this embodiment is molded into a cured plate (without metal foil) with a thickness of 1.0 mm, 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 when the temperature is raised from 25°C to 303°C at 10°C per minute, cooled, and then raised again from 25°C to 303°C. Furthermore, when a similar sample is measured in the same manner as above, the thermal expansion coefficient at 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.

[0259] The resin composition of this embodiment is used as a layered material (including film-like, sheet-like, etc.) such as a prepreg or resin composite sheet to form an insulating layer of a printed circuit board. When used as such a layered material, its thickness is preferably 5 μm or more, and more preferably 10 μm or more. The upper limit of the thickness is preferably 200 μm or less, and more preferably 180 μm or less. Note that the thickness of the layered material refers to the thickness including the glass cloth, for example, when the resin composition of this embodiment is impregnated into glass cloth. The material formed from the resin composition of this embodiment may be used for applications where exposure and development are performed to form a pattern, or it may be used for applications where exposure and development are not performed. It is particularly suitable for applications where exposure and development are not performed.

[0260] <<Prepreg>> The prepreg of this embodiment is formed from a substrate (prepreg substrate) and the resin composition of this embodiment. The prepreg of this embodiment is obtained, for example, by applying the resin composition of this embodiment to the substrate (e.g., impregnation and / or coating) and then partially curing it by heating (e.g., drying at 120 to 220°C for 2 to 15 minutes). In this case, the amount of resin composition adhering to the substrate, i.e., the amount of resin composition (including filler) relative to the total amount of prepreg after partial curing, is preferably in the range of 20 to 99% by mass, and more preferably in the range of 20 to 80% by mass.

[0261] The substrate is not particularly limited as long as it is a substrate used in various printed circuit board materials. Examples of substrate materials include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, NER-glass, NEZ-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited and includes woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surfacing mats. These substrates may be used individually or in combination of two or more. Among these substrates, woven fabrics that have undergone ultra-opening treatment and densification treatment are preferred from the viewpoint of dimensional stability, and from the viewpoint of strength and low water absorption, the substrate should have a thickness of 200 μm or less and a mass of 250 g / m². ２ The following glass woven fabrics are preferred, and from the viewpoint of moisture absorption and heat resistance, glass woven fabrics surface-treated with epoxysilane, aminosilane, or the like are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers exhibiting low relative permittivity and low dielectric loss tangent, such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. Examples of low relative permittivity substrates include substrates with a relative permittivity of 5.0 or less (preferably 3.0 to 4.9). Examples of low dielectric loss tangent substrates include substrates with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The relative permittivity and dielectric loss tangent are values ​​measured at a frequency of 10 GHz using a perturbation cavity resonator.

[0262] <<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. As a method for manufacturing the metal foil clad laminate of this embodiment, for example, one method is to arrange at least one sheet of the prepreg of this embodiment (preferably two or more sheets stacked) and arrange metal foil on one or both sides thereof and then laminate-form it. More specifically, it can be manufactured by arranging metal foil such as copper or aluminum on one or both sides of the prepreg and then laminating it. The number of prepreg sheets is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil is not particularly limited as long as it is used as a material for printed circuit boards, but examples include copper foil such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited and may be about 1.5 to 70 μm. Furthermore, when copper foil is used as the metal foil, it is preferable that the surface roughness Rz of the copper foil, measured according to JIS B0601:2013, is adjusted to 0.2 to 4.0 μm. Setting the surface roughness Rz of the copper foil to 0.2 μm or more results in an appropriate surface roughness, which tends to further improve the copper foil peel strength. On the other hand, setting the surface roughness Rz of the copper foil to 4.0 μm or less results in an appropriate surface roughness, which tends to further improve the dielectric loss tangent properties of the resulting cured product. From the viewpoint of the dielectric loss tangent properties of the resulting cured product and the copper foil peel strength, the surface roughness Rz of the copper foil is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, particularly preferably 0.7 μm or more, even more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0263] The lamination method includes methods commonly used when forming laminates and multilayer boards for printed circuit boards. More specifically, it includes a method using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, etc., at a temperature of approximately 180 to 350°C, a heating time of approximately 100 to 300 minutes, and a surface pressure of approximately 1 to 10 MPa. Furthermore, a multilayer board can be made by laminating the prepreg of this embodiment with a separately manufactured inner layer wiring board. As a method for manufacturing a multilayer board, for example, copper foil of approximately 35 μm is placed on both sides of one prepreg of this embodiment, and after lamination using the above molding method, an inner layer circuit is formed, and this circuit is subjected to a blackening treatment to form an inner layer circuit board. After that, this inner layer circuit board and the prepreg of this embodiment are arranged alternately one by one, and then copper foil is placed as the outermost layer, and a multilayer board can be manufactured by lamination under the above conditions, preferably under vacuum. The metal foil-clad laminate of this embodiment can be suitably used as a printed circuit board.

[0264] The metal foil-clad laminate of this embodiment preferably has a peel strength of 0.30 kN / m or more, more preferably 0.35 kN / m or more, and even more preferably 0.50 kN / m or more, measured in accordance with the provisions of JIS C6481 5.7 "Peel Strength". There is no upper limit to the peel strength, but for example, even if it is 2.00 kN / m or less, it will sufficiently satisfy the required performance.

[0265] As described above, the resin composition for electronic materials obtained using the resin composition of this embodiment (a resin composition consisting of a combination of specific components) can have cured products that are excellent in low dielectric properties (low dielectric constant, low dielectric loss tangent), low thermal expansion, heat resistance, and appearance of the cured product, as well as excellent moisture absorption and heat resistance, peel strength against metal foil, desmear resistance, crack resistance, and high-density processability.

[0266] <<Printed Wiring Board>> The printed wiring board of this embodiment includes an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition of this embodiment and a layer formed from the prepreg of this embodiment. Such a printed wiring board can be manufactured according to conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is shown below. First, a metal foil laminate such as the copper foil laminate described above is prepared. Next, an etching treatment is performed on the surface of the metal foil laminate to form an inner layer circuit and produce an inner layer substrate. Surface treatment is performed on the inner layer circuit surface of this inner layer substrate to increase the adhesive strength as needed, then the required number of prepregs described above are stacked on the inner layer circuit surface, and then metal foil for the outer layer circuit is laminated on the outside thereafter, and the substrate is heated and pressed to form an integral molded product. In this way, a multilayer laminate is produced in which an insulating layer made of a base material and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, after drilling holes for through-holes and via-holes in this multilayer laminate, a plated metal film is formed on the walls of these holes to provide electrical connectivity between the inner layer circuit and the metal foil for the outer layer circuit. Furthermore, the metal foil for the outer layer circuit is etched to form the outer layer circuit, thereby manufacturing a printed circuit board.

[0267] The printed circuit board obtained in the above manufacturing example has an insulating layer and a conductive layer formed on the surface of the insulating layer, wherein the insulating layer contains the resin composition of this embodiment and / or its cured product. That is, the prepreg of this embodiment described above (for example, a prepreg formed from a substrate and the resin composition of this embodiment impregnated or coated thereon), and the layer formed from the resin composition of the metal foil laminate of this embodiment described above, become the insulating layer of this embodiment. This embodiment also relates to a semiconductor device including the printed circuit board. Details of the semiconductor device can be found in paragraphs 0200 to 0202 of Japanese Patent Application Publication No. 2021-021027, the contents of which are incorporated herein.

[0268] Furthermore, it is preferable to reduce the surface roughness of the insulating layer formed from the cured resin composition of this embodiment after the roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after the roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but for example it may be 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x lens. The non-contact surface roughness meter used is the WYKONT 3300 manufactured by Bee Instruments.

[0269] <<Resin Composite Sheet>> The resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment disposed on the surface of the support. The resin composite sheet can be used as a build-up film or a dry film solder resist. The method for manufacturing the resin composite sheet is not particularly limited, but for example, one method is to obtain a resin composite sheet by applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent onto a support and drying it.

[0270] Examples of supports used here include, but are not limited to, polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and organic film substrates such as polyimide film, release films obtained by coating the surface of these films with a release agent, conductive foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, and FRP (Fiber-Reinforced Plastics).

[0271] As for the coating method, for example, a solution obtained by dissolving the resin composition of this embodiment in a solvent is applied onto a support using a bar coater, die coater, doctor blade, baker applicator, etc. Alternatively, after drying, the support can be peeled off or etched from the resin composite sheet in which the support and the resin composition are laminated to form a single-layer sheet. Furthermore, a single-layer sheet can also be obtained without using a support by supplying the above-mentioned solution obtained by dissolving the resin composition of this embodiment in a solvent into a mold having a sheet-shaped cavity and drying it to form a sheet.

[0272] In the production of the single-layer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited, but since low temperatures tend to leave solvent residue in the resin composition, and high temperatures cause the resin composition to harden, a temperature of 20°C to 200°C for 1 to 90 minutes is preferred. Furthermore, the single-layer sheet or resin composite sheet can be used in an uncured state after the solvent has been dried, or it can be used in a semi-cured (B-stage) state as needed. In addition, the thickness of the resin layer in the single-layer sheet or resin composite sheet of this embodiment can be adjusted by the concentration of the resin composition solution of this embodiment used for coating and the coating thickness, and is not particularly limited, but generally, a thickness of 0.1 to 500 μm is preferred because a thicker coating thickness tends to leave solvent residue during drying.

[0273] The present invention will be described in more detail below with reference to examples. The materials, amounts used, proportions, processing content, processing procedures, etc., shown in the following examples can be modified as appropriate, as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments, etc., used in the examples are difficult to obtain due to discontinuation or other reasons, measurements can be taken using other instruments with equivalent performance.

[0274] <Measurement of Weight-Average and Number-Average Molecular Weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) were measured by gel permeation chromatography (GPC). A liquid delivery pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Resonac Corporation, GPC KF-801, 802, 803, 804) were used. Tetrahydrofuran was used as the solvent, and the flow rate was 1.0 mL / min at a column temperature of 40°C. A calibration curve was prepared using monodisperse polystyrene.

[0275] <Synthesis Example 1> A mixture of compounds represented by formulas (3A) and (3B) was synthesized by the following method. 60 g of 1,3-diisopropenylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.), 140 g of toluene, and 3 g of p-toluenesulfonic acid monohydrate were placed in a flask equipped with a thermometer, condenser, and stirrer. The mixture was heated to an internal temperature of 65°C and reacted for 25 hours. After cooling, 140 g of toluene and 200 g of water were added, and the mixture was repeatedly washed with 200 g of water until the waste liquid became neutral, thereby obtaining the product as a solution (residual monomer 5.7%, number-average molecular weight of compounds other than the residual monomer in polystyrene equivalent by GPC method 279, weight-average molecular weight in polystyrene equivalent by GPC method 317). 117 g of concentrated solution was obtained by removing the solvent from the obtained solution under reduced pressure. The obtained solution was left to stand at 5°C for one week, causing precipitate to form in the solution. After suction filtration, the solution was vacuum-dried at 25°C for 24 hours to obtain 10.4 g of a white solid. The GPC chart of the obtained solid is shown in Figure 4. Next, the portion equivalent to the dimer of 1,3-diisopropenylbenzene (molecular weight 316) was obtained by GPC preparative procedure. A GPC apparatus manufactured by Shimadzu Corporation was used, with columns LF-804 and K-801, chloroform as the solvent, and the procedure was performed at a flow rate of 1.0 mL / min and a column temperature of 40°C. A RID-10A detector was used. Subsequently, measurement by LC revealed the presence of two isomers. A Shimadzu Corporation LC apparatus was used, with the column L-Column 2 ODS and H2 as the solvent. ２The procedure was performed using O:Acetonitrile = 20:80 (v / v%) at a flow rate of 1.0 mL / min and a column temperature of 40°C. A RID-10A detector was used. Each component was acquired by preparative extraction. １ Structural analysis using H-NMR revealed that one component is the compound represented by formula (3A) and the other component is the compound represented by formula (3B). １ The 1H-NMR chart is shown in Figure 1, and the compound represented by formula (3B) １ The H-NMR chart is shown in Figure 2. The above analysis revealed that the obtained solid consists of 90% of the compound represented by formula (3A) and 10% of the compound represented by formula (3B). １ This was determined from the H-NMR chart. １ The H-NMR chart is shown in Figure 3. The calculation method was based on the fact that the integral value of 7.5 ppm derived from the structure (3A) (1.00) represents one H peak, and the integral value of 5.1 ppm derived from the structure (3B) (0.23) represents two H peaks. Therefore, the calculation was performed using the following formula: Formula (3A): Formula (3B) = 1.00 / 1 : 0.23 / 2 = 90 : 10 Formula (3A) Formula (3B)

[0276] <Synthesis Example 2> 130 g of 1,3-diisopropenylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.), 80 g of toluene, and 4.69 g of a 64% aqueous solution of p-toluenesulfonic acid monohydrate (of which the mass of p-toluenesulfonic acid monohydrate is 3 g) were charged into a flask equipped with a thermometer, condenser, and stirrer. The temperature was raised to 60°C and the mixture was reacted for 10 hours. After cooling, 150 g of toluene and 200 g of water were added, and the mixture was repeatedly washed with 200 g of water until the waste liquid became neutral, thereby obtaining the product as a solution (residual monomer 1.6%, number-average molecular weight of compounds other than the residual monomer in polystyrene equivalent by GPC method is 269, weight-average molecular weight in polystyrene equivalent by GPC method is 308). 261 g of concentrated solution was obtained by removing the solvent from the obtained solution under reduced pressure. The obtained solution was left to stand at 5°C for one week, causing precipitate to form in the solution. After suction filtration, the solution was vacuum dried at 25°C for 24 hours to obtain 22.2 g of a white solid. The GPC chart of the obtained solid is shown in Figure 5. Similar to Synthesis Example 1, １ Structural analysis using H-NMR revealed that the obtained solid consisted of 95% of the compound represented by formula (3A) and 5% of the compound represented by formula (3B). １ This was determined from the H-NMR chart. １ The H-NMR chart is shown in Figure 6. The calculation method was based on the fact that the integral value of 7.5 ppm derived from the structure (3A) (0.96) represents one H peak, and the integral value of 5.1 ppm derived from the structure (3B) (0.10) represents two H peaks. Therefore, the calculation was performed using the following formula: Formula (3A): Formula (3B) = 0.96 / 1 : 0.10 / 2 = 95 : 5 Formula (3A) Formula (3B)

[0277] <Synthesis Example 3> 130 g of 1,3-diisopropenylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.), 80 g of toluene, and 4.69 g of a 64% aqueous solution of benzenesulfonic acid monohydrate (of which the mass of benzenesulfonic acid monohydrate is 3 g) were charged into a flask equipped with a thermometer, condenser, and stirrer. The temperature was raised to 60°C and the mixture was reacted for 12.5 hours. After cooling, 150 g of toluene and 200 g of water were added, and the mixture was repeatedly washed with 200 g of water until the waste liquid became neutral, thereby obtaining the product as a solution (residual monomer 2.4%, number-average molecular weight of compounds other than the residual monomer in polystyrene equivalent by GPC method is 255, weight-average molecular weight in polystyrene equivalent by GPC method is 256). 249 g of concentrated solution was obtained by removing the solvent from the obtained solution under reduced pressure. The obtained solution was left to stand at 5°C for one week, causing precipitates to form in the solution. After suction filtration, the solution was vacuum dried at 25°C for 24 hours to obtain 19.3 g of a white solid. The GPC chart of the obtained solid is shown in Figure 7. Similar to Synthesis Example 1, １ Structural analysis using H-NMR revealed that the obtained solid consisted of 97% of the compound represented by formula (3A) and 3% of the compound represented by formula (3B). １ This was determined from the H-NMR chart. １ The H-NMR chart is shown in Figure 8. The calculation method was based on the fact that the integral value of 7.5 ppm derived from the structure (3A) (1.01) represents one H peak, and the integral value of 5.1 ppm derived from the structure (3B) (0.06) represents two H peaks. Therefore, the calculation was performed using the following formula: Formula (3A): Formula (3B) = 1.01 / 1 : 0.06 / 2 = 97 : 3 Formula (3A) Formula (3B)

[0278] <Synthesis Example 2: Synthesis of Modified Polyphenylene Ether Compounds> <<Synthesis of Bifunctional Phenylene Ether Oligomers>> CuBr was placed in a 12 L vertical reactor equipped with a stirrer, thermometer, air inlet tube, and baffle plate. ２9.36 g (42 mmol) of 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 were charged and stirred at an internal temperature of 40°C. In response, 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, pre-dissolved in 2300 g of methanol, was added dropwise over 230 minutes while bubbling a gas mixture 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 complete, 1500 g of water in which 48.1 g (130 mmol) of tetrasodium ethylenediaminetetraacetate was dissolved was added to stop the reaction. The aqueous layer and the organic layer were separated, and the organic layer was washed with 1 M hydrochloric acid solution, and then with pure water. The obtained solution was concentrated to 50% by mass using an evaporator to obtain 1980 g of toluene solution A1 of phenylene ether resin. The number-average molecular weight in polystyrene equivalent by GPC method was 1975, the weight-average molecular weight in polystyrene equivalent by GPC method was 3514, and the hydroxyl group equivalent was 990 g / eq.

[0279] <<Synthesis of Modified Polyphenylene Ether Compound>> In a reactor equipped with a stirrer, thermometer, and reflux tubing, 833 g of toluene solution A1 of the phenylene ether resin obtained above, 76.7 g (0.50 mol) of vinyl benzyl 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 30.5% by mass NaOH aqueous solution were charged, and the mixture was stirred at a reaction temperature of 40°C. After stirring for 24 hours, the organic layer was washed with 1 M hydrochloric acid aqueous solution, and then with pure water. The obtained solution was concentrated and added dropwise to methanol to solidify it, and the solid was recovered by filtration and vacuum dried to obtain 450 g of a polyphenylene ether compound mainly composed of the compound represented by formula (OP-15). The number-average molecular weight in polystyrene equivalents according to the GPC method was 2250, the weight-average molecular weight in polystyrene equivalents according to 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.

[0280] Example 1: 20 parts by mass of the compound obtained in Synthesis Example 1 and 80 parts by mass of the polyphenylene ether resin obtained in Synthesis Example 2 were dissolved and mixed using methyl ethyl ketone and toluene to obtain a varnish. The amounts of each component mentioned above are shown in terms of solid content.

[0281] <Preparation of 1.0 mm thick cured plate test specimens> The solvent was evaporated from the obtained varnish to obtain a resin composition powder. Using the obtained resin composition powder, a cured plate was prepared as follows: 4.5 g of the resin composition powder was spread in a stainless steel mold measuring 100 mm x 30 mm x 1.0 mm high, and set in a vacuum press (manufactured by Kitagawa Seiki Co., Ltd.). It was held at 200°C for 2 hours and pressed at a surface pressure of 3.0 MPa. The dielectric constant (Dk) and dielectric loss tangent (Df) were measured using the obtained cured plate. The measurement results are shown in the table below.

[0282] <Measurement Method> <Dielectric Properties> The obtained cured plate was downsized to a width of 1.0 mm and then dried at 120°C for 60 minutes. The relative permittivity (Dk) and dielectric loss tangent (Df) at a frequency of 10 GHz were measured for the dried sample using a perturbation cavity resonator. The measurement temperature was 23°C. A Keysight Technologies P5005A perturbation cavity resonator was used.

[0283] Example 2 The procedure was the same as in Example 1, except that the polyphenylene ether resin obtained in Synthesis Example 2 was replaced with 1,2-bis(4-vinylphenyl)ethane.

[0284] Example 3 was carried out in the same manner as in Example 2, except that the amount of the compound obtained in Synthesis Example 2 was changed to 57 parts by mass, and the amount of 1,2-bis(4-vinylphenyl)ethane as the vinyl compound was changed to 43 parts by mass.

[0285] Example 4 The procedure was carried out in the same manner as in Example 1, except that 48 parts by mass of the compound obtained in Synthesis Example 2 was added, and 52 parts by mass of BMI-2300 (manufactured by Yamato Chemical Industries, Ltd.) was added as the maleimide compound.

[0286] Example 5 The procedure was carried out in the same manner as in Example 1, except that 26 parts by mass of the compound obtained in Synthesis Example 3 was added and 74 parts by mass of NE-X-9470S (manufactured by DIC Corporation) was added as the maleimide compound.

[0287] Example 6 The procedure was carried out in the same manner as in Example 1, except that 32 parts by mass of the compound obtained in Synthesis Example 3 was added and 68 parts by mass of NE-X-9500 (manufactured by DIC Corporation) was added as the maleimide compound.

[0288] Comparative Example 1 In Example 1, the compound represented by formula (1A) was not incorporated, and 100 parts by mass of the polyphenylene ether resin obtained in Synthesis Example 2 were used, with the rest of the procedure being the same.

[0289] Comparative Example 2 The procedure was the same as in Example 2, except that the compound represented by formula (1A) was not included, and 1,2-bis(4-vinylphenyl)ethane was used as the vinyl compound (100 parts by mass).

[0290] Comparative Example 3 The procedure was carried out in the same manner as in Example 4, except that the compound represented by formula (1A) was not included, and 100 parts by mass of BMI-2300 (manufactured by Yamato Chemical Industries, Ltd.) was used as the maleimide compound.

[0291] Comparative Example 4 The procedure was carried out in the same manner as in Example 5, except that the compound represented by formula (1A) was not included, and 100 parts by mass of NE-X-9470S (manufactured by DIC Corporation) was used as the maleimide compound.

[0292] Comparative Example 5 The procedure was carried out in the same manner as in Example 6, except that the compound represented by formula (1A) was not included, and NE-X-9500 (manufactured by DIC Corporation) was used as the maleimide compound in the form of 100 parts by mass.

[0293]

[0294] As is clear from the comparison between the above examples and comparative examples, the cured product obtained from the resin composition containing the compound of the present invention exhibited significantly improved low dielectric properties.

[0295] Although the present invention has been described in detail using specific embodiments, it will be apparent to those skilled in the art that various modifications are possible without departing from the intent and scope of the invention.

Claims

1. A compound represented by formula (1A), and / or a compound represented by formula (1B). Formula (1A) Formula (1B) 2. The compound according to claim 1, wherein the compound is at least one of the compound represented by formula (2A), the compound represented by formula (2B), and the compound represented by formula (2C). Formula (2A) Formula (2B) Formula (2C) 3. The compound according to claim 1, wherein the compound is a compound represented by formula (3A) and / or a compound represented by formula (3B). Formula (3A) Formula (3B) 4. A resin composition comprising a compound according to any one of claims 1 to 3 and a thermosetting compound.

5. The resin composition according to claim 4, wherein the thermosetting compound comprises at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group.

6. The resin composition according to claim 4, further comprising a filler.

7. The resin composition according to claim 4, further comprising at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors.

8. The resin composition according to claim 4, for use in printed circuit boards.

9. The resin composition according to claim 4, wherein the thermosetting compound comprises at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group, further comprising a filler, and further comprising at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors, and is for use in printed circuit boards.

10. A cured product of the resin composition according to claim 4.

11. A prepreg formed from a substrate and the resin composition described in claim 4.

12. A metal foil-clad laminate comprising at least one prepreg according to claim 11 and a metal foil disposed on one or both sides of the prepreg.

13. A resin composite sheet comprising a support and a layer formed from the resin composition according to claim 4, disposed on the surface of the support.

14. A printed wiring board comprising an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from the resin composition described in claim 4.

15. A semiconductor device comprising a printed circuit board as described in claim 14.

16. A low-dielectric filler comprising the compound described in any one of claims 1 to 3.

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