Resins, resin compositions, cured products, prepregs, metal foil-clad laminates, resin composite sheets, printed wiring boards, and semiconductor devices

Abstract

To provide a resin excellent in dielectric characteristics and heat resistance and having an indane skeleton, and to provide a composition, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.SOLUTION: The resin is represented by formula (T) and has a parameter α of 0.55 or more and 1.00 or less indicating the ratio of a constituent unit having an indane skeleton, and a parameter β of 0.20 or more and 3.00 or less indicating the ratio of terminal double bonds (where R is a group containing constituent units a, b and c.).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a resin, a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. [Background technology]

[0002] In recent years, there has been an accelerating trend toward higher integration and miniaturization of semiconductor elements used in mobile terminals, electronic devices, communication devices, etc. This has led to a demand for technology that enables high-density packaging of semiconductor elements, and there has also been a demand for improvements in printed wiring boards, which play an important role in this process. Meanwhile, the applications of electronic devices and other devices are becoming more diverse and expanding. Accordingly, the properties required of printed wiring boards, as well as the metal foil-clad laminates and prepregs used therein, are becoming more diverse and stricter. Taking these required properties into consideration, various materials and processing methods have been proposed to obtain improved printed wiring boards. One example of this is the development of improved resin materials that make up prepregs and resin composite sheets.

[0003] Patent Document 1 discloses a resin having an isopropenylphenyl group at its terminal and an indane skeleton as a material suitable for semiconductor encapsulation and printed wiring boards. Patent Document 2 discloses that when the weighted average degree of polymerization of an oligomer composed of 1,3- and 1,4-diisopropenylbenzene is 1.5 to 50, it is particularly suitable for use in polymer modification at elevated temperatures due to its low volatility and excellent crosslinking ability. Patent Document 3 discloses that the melt viscosity of a composition containing an indane skeleton can be reduced without impairing other properties of the composition, thereby improving the operability of the composition. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2021-143333 [Patent Document 2] Japanese Patent Application Publication No. 02-219809 [Patent Document 3] Japanese Patent Application Publication No. 03-252441 Summary of the Invention [Problem to be solved by the invention]

[0005] The present inventors have investigated the resins having an indane skeleton described in the above patent documents and have found that, for example, when used as electronic materials, the dielectric properties and heat resistance are insufficient. Specifically, in the resin specifically described in Patent Document 1, the parameters α and β defined in the present invention do not satisfy the ranges defined in the present invention, as will be described in detail later, and as a result, the properties for use in semiconductor encapsulation materials and printed wiring boards are insufficient. Furthermore, the parameters α and β of the resin specifically described in Patent Document 2 do not satisfy the ranges defined in the present invention, and as a result, the performance required for electronic material applications is insufficient. Furthermore, the resin described in Patent Document 3 also does not satisfy the parameters α and β specified in this patent, and therefore does not have sufficient performance required for electronic material applications. The present invention aims to solve the above-mentioned problems, and to provide a resin having an indane skeleton that has excellent dielectric properties and excellent heat resistance, as well as a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device that use the resin. [Means for solving the problem]

[0006] In light of the above-mentioned problems, it has been found that the above-mentioned problems can be solved by precisely adjusting the ratio of indane skeletons and double bonds in a resin. Specifically, the above-mentioned problems have been solved by the following means. <1> A resin represented by formula (T): The parameter α calculated from the formula (α) is 0.55 or more and 1.00 or less, A resin having a parameter β calculated from the formula (β) of 0.20 or more and 3.00 or less. [ka] (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x1 represents an integer of 0 to 4. R is a group containing a structural unit represented by formula (Tx).) [ka] (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.)

number

[0007] The present invention makes it possible to provide a resin having an indane skeleton that has excellent dielectric properties and heat resistance, as well as a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device that use the resin. [Brief explanation of the drawings]

[0008] [Figure 1] 1 shows an NMR chart of the resin obtained in Synthesis Example 1-1. [Figure 2] 1 shows an NMR chart of the resin obtained in Synthesis Example 1-2. [Figure 3] 1 shows an NMR chart of the resin obtained in Synthesis Example 1-3. [Figure 4] NMR charts of the resins obtained in Synthesis Examples 1-4 are shown. [Figure 5] 1 shows an NMR chart of the resin obtained in Comparative Synthesis Example 1-1. [Figure 6] 1 shows an NMR chart of the resin obtained in Comparative Synthesis Example 1-2. [Figure 7] 1 shows an NMR chart of the resin obtained in Comparative Synthesis Example 1-3. [Figure 8] 1 shows an NMR chart of the resin obtained in Comparative Synthesis Example 1-4. [Figure 9] 1 shows a GPC chart of the resin obtained in Synthesis Example 1-4. [Figure 10] 1 shows a GPC chart of the resin obtained in Comparative Synthesis Example 1-2. [Figure 11] NMR charts of the resins obtained in Synthesis Examples 1-5 are shown. [Figure 12] 1 shows an NMR chart of the resin obtained in Comparative Synthesis Example 1-5. DETAILED DESCRIPTION OF THE INVENTION

[0009] Hereinafter, an embodiment for carrying out the present invention (hereinafter simply referred to as "the present embodiment") will be described in detail. Note that the present embodiment is an example for explaining the present invention, and the present invention is not limited to only this embodiment. In this specification, the symbol "to" is used to mean that the numerical values ​​before and after it are included as the lower limit and upper limit. In this specification, various physical properties and characteristic values ​​are those at 23°C unless otherwise specified. In the description of groups (atomic groups) in this specification, when a notation does not specify whether they are substituted or unsubstituted, it includes both groups (atomic groups) that have no substituents and groups (atomic groups) that have substituents. For example, the term "alkyl group" includes not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups). In this specification, when a notation does not specify whether they are substituted or unsubstituted, it is preferable that they be unsubstituted. In this specification, the term "(meth)allyl group" refers to either or both of allyl and methallyl, "(meth)acrylate" refers to either or both of acrylate and methacrylate, "(meth)acrylic" refers to either or both of acrylic and methacrylic, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. In this specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved. If the measurement methods, etc. described in the standards shown in this specification differ from year to year, they will be based on the standards in effect as of January 1, 2022, unless otherwise stated.

[0010] In this specification, the resin solid content refers to components excluding fillers and solvents, and is intended to include the resin represented by formula (T), as well as other compounds (C) that are blended as necessary, and other resin additive components (additives such as flame retardants, etc.). In this specification, the terms relative permittivity and dielectric constant are used interchangeably.

[0011] The resin in this embodiment (hereinafter sometimes referred to as "resin represented by formula (T)") is a resin represented by formula (T), in which the parameter α calculated from formula (α) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less. [ka] (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x1 represents an integer of 0 to 4. R is a group containing a structural unit represented by formula (Tx).) [ka] (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.)

number

[0012] In formula (T), x1 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0. In formula (Tx), n, o, and p each represent the average number of repeating units in all molecules in the resin represented by formula (T). In formula (Tx), the sum of n, o, and p is preferably 1.1≦n+o+p, more preferably 1.2≦n+o+p, even more preferably 1.5≦n+o+p, even more preferably 2.0≦n+o+p, even more preferably 2.5≦n+o+p, even more preferably 3.0≦n+o+p, and particularly preferably 3.3≦n+o+p. 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≦7.4, 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 below.

[0013] In formula (T) and formula (Tx), each Ma is preferably a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, more preferably a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and even more preferably a hydrocarbon group having 1 to 3 carbon atoms which may be substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom, and a fluorine atom or a chlorine atom is preferred. Each Ma is preferably a hydrocarbon group having 1 to 12 carbon atoms which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, more preferably a linear alkyl group. As Ma, a methyl group and an ethyl group are particularly preferred.

[0014] In formula (Tx), x is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0015] The resin represented by formula (T) further has a parameter α calculated from formula (α) of 0.55 or more and 1.00 or less, and a parameter β calculated from formula (β) of 0.20 or more and 3.00 or less.

[0016] Here, α represents the ratio of the structural unit having an indane skeleton (structural unit (a) in formula (Tx)) in the resin represented by formula (T). More specifically, by adjusting the structural unit having an indane skeleton so that it satisfies the above-mentioned parameter α range, it is presumed that the rigidity of the resulting resin molecules is high and the glass transition temperature of the cured product can be increased. Furthermore, since highly rigid molecules have lower mobility than less rigid molecules, it is presumed that the relaxation time during dielectric relaxation is longer and the dielectric loss tangent (Df) can be reduced. When synthesizing the resin represented by formula (T), α can be increased by conditions such as diluting the concentration of raw materials, using a highly polar solvent, increasing the amount of catalyst, and raising the reaction temperature. On the other hand, β defines the ratio of terminal double bonds in the resin represented by formula (T). More specifically, for example, by adjusting the parameter β to satisfy the range, it is presumed that the number of crosslinking points with functional groups of other compounds (C) (especially thermosetting compounds) described below increases, making it easier to form a network upon curing, and resulting in a cured product with a high glass transition temperature and low Df. β can be increased by reducing the amount of catalyst, lowering the reaction temperature, using a low-polarity solvent, or other conditions when synthesizing the resin represented by formula (T). The parameters α and β of the resin represented by formula (T) are adjusted during synthesis using the method for increasing the parameters α and β described above. Of course, the parameters α and β may also be adjusted by a method other than those described above.

[0017] The parameter α is 0.55 or more, preferably 0.57 or more, more preferably 0.59 or more, even more preferably 0.60 or more, and even more preferably 0.62 or more, and may be 0.65 or more, 0.70 or more, 0.75 or more, or 0.80 or more. By setting the parameter α at or above the lower limit, the heat resistance of the resulting cured product tends to be further improved. The parameter α is substantially 1.00 or less, and the resulting cured product tends to have excellent low dielectric properties (low relative dielectric constant and / or low dielectric dissipation factor) and heat resistance. Therefore, the larger the parameter α, the better. However, the parameter α may be 0.95 or less, 0.90 or less, 0.85 or less, 0.82 or less, 0.80 or less, less than 0.79, 0.78 or less, 0.77 or less, 0.75 or less, 0.74 or less, or 0.70 or less. The parameter β is 0.20 or more, preferably 0.25 or more, more preferably 0.30 or more, even more preferably 0.35 or more, even more preferably 0.40 or more, even more preferably 0.43 or more, even more preferably 0.50 or more, and may be 0.60 or more, 0.65 or more, 0.70 or more, 0.77 or more, 0.80 or more, 0.90 or more, or 0.95 or more. By setting the parameter β to be above the lower limit, the heat resistance of the resulting cured product tends to be improved and the Df tends to be lower. The parameter β is 3.00 or less, preferably 2.50 or less, more preferably 2.00 or less, even more preferably 1.50 or less, even more preferably 1.30 or less, even more preferably 1.20 or less, even more preferably 1.10 or less, or even 1.00 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.83 or less, or 0.80 or less. By ensuring that the content is equal to or less than the upper limit, the heat resistance of the resulting cured product tends to be improved and Df tends to be lower.

[0018] The number average molecular weight (Mn) of the resin represented by formula (T) measured by gel permeation chromatography (GPC) in terms of polystyrene (details follow the method described in the Examples below) is preferably 400 or more, more preferably 500 or more, even more preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By measuring the Mn at or above the lower limit, the heat resistance of the resulting cured product tends to be improved and the Df tends to be lower. Furthermore, the upper limit of the number average molecular weight (Mn) of the resin represented by formula (T) measured by gel permeation chromatography (GPC) in terms of polystyrene (GPC) is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, and even more preferably 1250 or less. By measuring the Mn at or below the upper limit, the heat resistance of the resulting cured product tends to be improved and the Df tends to be lower. Furthermore, the weight average molecular weight (Mw) of the resin represented by formula (T) measured by GPC in terms of polystyrene (details follow the method described in the Examples below) is preferably 500 or more, more preferably 800 or more, even more preferably 900 or more, and even more preferably 1000 or more. By setting it to the lower limit or higher, the heat resistance of the resulting cured product tends to be improved and Df tends to be lower. The upper limit of the weight average molecular weight (Mw) of the resin represented by formula (T) measured by GPC in terms of polystyrene (details follow the method described in the Examples below) is preferably 6000 or less, more preferably 5000 or less, even more preferably 4000 or less, even more preferably 3000 or less, even more preferably 2900 or less, and even more preferably 2800 or less. By setting it to the upper limit or lower, the heat resistance of the resulting cured product tends to be improved and Df tends to be lower.

[0019] The resin represented by formula (T) preferably has a ratio of weight-average molecular weight to number-average molecular weight, Mw / Mn, of 1.1 to 3.0. The resin represented by formula (T) preferably has a ratio of 1.2 or more, more preferably 1.3 or more, even more preferably 1.4 or more, even more preferably 1.5 or more, and even more preferably 1.6 or more. The resin represented by formula (T) preferably has a ratio of 2.5 or less, even more preferably less than 2.5, even more preferably 2.4 or less, and may be 2.3 or less, less than 2.3, 2.2 or less, 2.0 or less, or 1.8 or less. The weight average molecular weight and the number average molecular weight are measured according to the method described in the Examples below. The resin represented by formula (T) is a compound having an isopropenylphenyl group at a terminal, and preferably contains, as a main component, two isopropenylphenyl groups per molecule. Specifically, more than 50% by mass of the resin represented by formula (T), preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more, contains two isopropenylphenyl groups per molecule.

[0020] The method for producing the resin represented by formula (T) is not particularly limited as long as the resulting resin satisfies the above-mentioned parameters α and β, and the raw materials, reaction temperature, catalyst type, catalyst amount, reaction solvent, raw material concentration, etc., used in synthesizing the resin represented by formula (T) can be appropriately adjusted.

[0021] Examples of raw materials that can be used to synthesize the resin represented by formula (T) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0022] The reaction temperature when synthesizing the resin represented by formula (T) is preferably 40°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, and may be 70°C or higher, 80°C or higher, 90°C or higher, 100°C or higher, 110°C or higher, or 120°C or higher. Setting the temperature at or above the lower limit tends to improve the reaction rate and the ratio of the indane skeleton (structural unit (a) in formula (Tx)), which is preferable. Furthermore, the reaction temperature is preferably 180°C or lower, more preferably 150°C or lower, and even more preferably 140°C or lower. Setting the temperature at or below the upper limit tends to effectively suppress the production of by-products. The reaction temperature does not need to be the same from the start to the end of the reaction, and may be varied. In this case, it is preferable that the average reaction temperature throughout the entire process is within the above range.

[0023] The catalyst used in synthesizing the resin represented by formula (T) is not particularly limited, but examples thereof include acid catalysts. Examples of acid catalysts that can be used 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; Lewis acids such as BF3 ether complexes, BF3 phenol complexes, aluminum chloride, zinc chloride, and indium chloride; solid acids such as activated clay, acid clay, silica alumina, and zeolites; heteropolyhydrochloric acid; and strongly acidic ion exchange resins. When a catalyst is used, the amount thereof is, for example, 0.01 to 20.0 parts by mass relative to 100 parts by mass of the raw material for the resin represented by formula (T). The catalyst is usually one type alone, but two or more types may be used in combination. When using a combination, it is preferable that the total amount is within the above range.

[0024] The reaction solvent used in synthesizing the resin represented by formula (T) is not particularly limited, but may be an aromatic hydrocarbon solvent such as toluene, benzene, chlorobenzene, or xylene, a halogenated hydrocarbon solvent such as methylene chloride or chloroform, an aliphatic hydrocarbon solvent such as hexane or heptane, an ester solvent such as ethyl acetate or propyl acetate, an amide solvent such as dimethylformamide or dimethylacetamide, an alcohol solvent, or a ketone solvent, or may contain water. Examples of alcohol solvents include methanol, ethanol, butanol, propanol, methylpropylene diglycol, diethylene glycol ethyl ether, butylpropylene glycol, and propylpropylene glycol. Examples of ketone solvents include acetone, methyl ethyl ketone, diethyl ketone, methyl butyl ketone, and methyl isobutyl ketone. Other examples include, but are not limited to, tetrahydrofuran and dioxane. An example of the reaction solvent in this embodiment includes an aromatic hydrocarbon solvent.

[0025] The concentration of the above-mentioned raw materials when synthesizing the resin represented by formula (T) is preferably 5% or more, more preferably 8% or more, and preferably 10% or more, and may be 12% or more, 15% or more, 17% or more, 20% or more, 22% or more, or 25% or more. By setting the concentration at or above the lower limit, the reaction rate and the ratio of the indane skeleton (structural unit (a) in formula (Tx)) tend to be improved, which is preferable. Furthermore, the concentration of the above-mentioned raw materials is preferably 49% or less, more preferably 40% or less. By setting the concentration at or below the upper limit, the production of by-products tends to be effectively suppressed. Furthermore, the concentration does not need to be the same from the start to the end of the reaction, and may be changed.

[0026] Patent Document 1 discloses a resin represented by formula (T) having an isopropenylphenyl group at a terminal and an indane skeleton as a suitable material for semiconductor encapsulation and printed wiring boards. The synthesis in the examples described in Patent Document 1 and the examples of this patent differ mainly in the concentration and amount of catalyst, and these conditions are optimized to adjust the parameters α and β. The resin described in the examples of Patent Document 1 does not satisfy the parameters α and β within the ranges of the present invention, and its properties are insufficient for use in semiconductor encapsulation and printed wiring boards. Patent Document 2 discloses that oligomers of 1,3- and 1,4-diisopropenylbenzene with a weighted average degree of polymerization of 1.5 to 50 are particularly suitable for use in polymer modification at elevated temperatures due to their low volatility and excellent crosslinking ability. The synthesis of the examples described in Patent Document 2 and the examples of the present invention differs mainly in the catalyst used and temperature conditions, and parameters α and β are adjusted by optimizing these conditions. The use of the resin described in the examples of Patent Document 2 differs from that of the present patent, and the parameters α and β do not satisfy the ranges of the present invention in terms of properties, resulting in insufficient performance for electronic material applications. Patent Document 3 discloses that the indane skeleton improves the operability of a composition by reducing its melt viscosity without impairing other properties of the composition. The synthesis examples in Patent Document 3 and those in this patent differ primarily in the concentration, catalyst amount, and temperature conditions, and these conditions are optimized to adjust the parameters α and β. Patent Document 3 also describes that thermoplastic engineering plastics are suitable for use in printed circuit boards due to their excellent electrical properties, but the resins described in the examples in Patent Document 3 do not satisfy the parameters α and β specified in this patent, making them unsuitable for electronic material applications.

[0027] This embodiment also discloses a resin composition containing the resin represented by the above formula (T). A cured product of such a resin composition can have high heat resistance and excellent dielectric properties. The content of the resin represented by formula (T) in the resin composition of this embodiment 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, per 100 parts by mass of the resin solid content in the resin composition. By setting the content at or above the lower limit, Df tends to be reduced. Furthermore, the upper limit of the content of the resin represented by formula (T) is preferably 90 parts by mass or less, even 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 50 parts by mass or less, and even more preferably 40 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content at or below the upper limit, heat resistance tends to be improved. The resin composition of the present embodiment may contain only one type of resin represented by formula (T), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0028] <Other Compounds (C)> The resin composition of this embodiment may contain, in addition to the resin of this embodiment (resin represented by formula (T)), another compound (C) (preferably another curable compound and / or plastic compound, more preferably another thermosetting compound and / or thermoplastic compound, and even more preferably another thermosetting compound). The resin composition of the present embodiment preferably contains at least one other compound (C) selected from the group consisting of maleimide compounds, polyphenylene ether compounds, polymers having a structural unit represented by formula (V), cyanate ester compounds, epoxy compounds, phenolic compounds, compounds containing a (meth)allyl group (e.g., alkenylnadiimide compounds), oxetane resins, benzoxazine compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, compounds having a styrene group other than the polyphenylene ether compounds, compounds having an isopropenyl group other than the resins represented by formula (T), polyfunctional (meth)acrylate compounds other than the polyphenylene ether compounds, elastomers, and petroleum resins. It is more preferable that the resin composition contain at least one other compound (C) selected from the group consisting of maleimide compounds, polyphenylene ether compounds, polymers having a structural unit represented by formula (V), cyanate ester compounds, epoxy compounds, phenolic compounds, alkenylnadiimide compounds, oxetane resins, and benzoxazine compounds. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) By including such other compound (C), the desired performance required for the printed wiring board can be more effectively exhibited. In this embodiment, it is preferable to contain a polyphenylene ether compound, more preferable to contain a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, and even more preferable to contain a compound represented by formula (OP-1) described below. In this embodiment, it is preferable to include a maleimide compound containing two or more maleimide groups, and it is more preferable to include a compound represented by formula (M1) described below.

[0029] When the resin composition of this embodiment contains other compounds (C) (preferably other curable compounds and / or plastic compounds, more preferably other thermosetting compounds and / or thermoplastic compounds, and even more preferably other thermosetting compounds), the content (total amount) thereof is preferably 1 part by mass or more, more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 30 parts by mass or more, or even 40 parts by mass or more, or even 50 parts by mass or more, per 100 parts by mass of the resin solids. By ensuring that the content is above the above lower limit, heat resistance, plating adhesion, low thermal expansion, etc. tend to be further improved. The upper limit of the content of the other compound (C) (preferably other curable compounds and / or plastic compounds, more preferably other thermosetting compounds and / or thermoplastic compounds, and even more preferably other thermosetting compounds) is preferably 99 parts by mass or less, more preferably 95 parts by mass or less, even more preferably 90 parts by mass or less, even more preferably 85 parts by mass or less, even more preferably 80 parts by mass or less, or even 75 parts by mass or less, 50 parts by mass or less, 45 parts by mass or less, or 40 parts by mass or less, per 100 parts by mass of the resin solids. By keeping the amount below the upper limit, low dielectric properties and low water absorption tend to be further improved. The resin composition of the present embodiment may contain only one type of other compound (C), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0030] <<Maleimide compounds>> The maleimide compound is not particularly limited as long as it contains 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 still more preferably) maleimide groups in the molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used. In this embodiment, the maleimide compound preferably includes one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), and a maleimide compound (M6), and more preferably includes one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), a maleimide compound (M6), and a maleimide compound (M7). The maleimide compound preferably contains one or more selected from the group consisting of 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), 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 a compound represented by formula (M1) and / or a compound represented by formula (M3), and even more preferably a compound represented by formula (M1). When used in materials for printed wiring boards (e.g., metal foil-clad laminates), etc., excellent heat resistance can be imparted.

[0031] [ka] (In formula (M0), R 51 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R 52 each independently represents a hydrogen atom or a methyl group, and n1 represents an integer of 1 or greater. R 51 are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. R 52 is preferably a methyl group. n1 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and even more preferably 1. Specifically, the following compounds are preferred examples of the formula (M0): [ka] In the above formula, R 8 each independently represents a hydrogen atom, a methyl group, or an ethyl group, and is preferably a methyl group.

[0032] The compound represented by formula (M0) may be a single compound or a mixture of two or more compounds. Examples of the mixture include a mixture of compounds with different n1, 51 and / or R 52 Examples of such a mixture include a mixture of compounds having different types of substituents, a mixture of compounds having different bonding positions (meta, para, or ortho positions) of the maleimide group and oxygen atom relative to the benzene ring, and a mixture of compounds having a combination of two or more of the above differences. The same applies to the compounds represented by formulas (M1) to (M6) below. [ka] (In formula (M1), R M1 , R M2 , R M3 , and R M4 R each independently represents a hydrogen atom or an organic group. M5 and R M6 each independently represents a hydrogen atom or an alkyl group. M represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R M7 and R M8 are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R M9 and R M10 R each independently represents a hydrogen atom or an alkyl group. M11 , R M12 , R M13 , and R M14R each independently represents a hydrogen atom or an organic group. M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.

[0033] R in the formula M1 , R M2 , R M3 , and R M4 R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. M1 and R M3 are each independently preferably an alkyl group, and R M2 and R M4 is preferably a hydrogen atom. R M5 and R M6 are each independently a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ar M represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or an anthracenediyl group, more preferably a phenylene group, and even more preferably an m-phenylene group. M may have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Mis preferably unsubstituted. A is a 4- to 6-membered alicyclic group, and more preferably a 5-membered alicyclic group (preferably a group that forms an indane ring when combined with a benzene ring). M7 and R M8 are each independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, and is preferably 2. lx is 0 or 1, and is preferably 1. R M9 and R M10 are each independently a hydrogen atom or an alkyl group, more preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M11 , R M12 , R M13 , and R M14 R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. M12 and R M13 are each independently preferably an alkyl group, and R M11 and R M14 is preferably a hydrogen atom. R M15 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and is preferably an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms. px represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. nx represents an integer of 1 to 20. nx may be an integer of 10 or less. The resin composition of this embodiment may contain only one or more compounds represented by formula (M1) having different values ​​of nx. When two or more compounds are contained, the average value of nx (average number of repeating units) n in the compounds represented by formula (M1) in the resin composition is preferably 0.92 or more, more preferably 0.95 or more, even more preferably 1.0 or more, and even more preferably 1.1 or more, to provide a low melting point (low softening point), low melt viscosity, and excellent handleability. Furthermore, n is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 7.0 or less, even more preferably 6.0 or less, and may even be 5.0 or less. The same applies to the compounds represented by formula (M1-2) and formula (M1-3) described below. The compound represented by formula (M1) is preferably a compound represented by the following formula (M1-1). [ka] (In formula (M1-1), R M21 , R M22 , R M23 , and R M24 R each independently represents a hydrogen atom or an organic group. M25 and R M26 R each independently represents a hydrogen atom or an alkyl group. M27 , R M28 , R M29 , and R M30 R each independently represents a hydrogen atom or an organic group. M31 and R M32 R each independently represents a hydrogen atom or an alkyl group. M33 , R M34 , R M35 , and R M36 R each independently represents a hydrogen atom or an organic group. M37, R M38 , and R M39 each independently represents a hydrogen atom or an alkyl group, and nx represents an integer of 1 or more and 20 or less.

[0034] R in the formula M21 , R M22 , R M23 , and R M24 R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. M21 and R M23 is preferably an alkyl group, and R M22 and R M24 is preferably a hydrogen atom. R M25 and R M26 are each independently a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M27 , R M28 , R M29 , and R M30 each independently represents a hydrogen atom or an organic group, preferably a hydrogen atom. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M31 and R M32 are each independently a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M33 , RM34 , R M35 , and R M36 each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M33 and R M36 is preferably a hydrogen atom, and R M34 and R M35 is preferably an alkyl group. R M37 , R M38 , and R M39 are each independently a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.

[0035] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-2). [ka] (In formula (M1-2), R M21 , R M22 , R M23 , and R M24 R each independently represents a hydrogen atom or an organic group. M25 and R M26 R each independently represents a hydrogen atom or an alkyl group. M27 , R M28 , R M29 , and R M30 R each independently represents a hydrogen atom or an organic group. M31 and R M32 R each independently represents a hydrogen atom or an alkyl group. M33 , R M34 , RM35 , and R M36 R each independently represents a hydrogen atom or an organic group. M37 , R M38 , and R M39 each independently represents a hydrogen atom or an alkyl group, and nx represents an integer of 1 or more and 20 or less.

[0036] In formula (M1-2), R M21 , R M22 , R M23 , R M24 , R M25 , R M26 , R M27 , R M28 , R M29 , R M30 , R M31 , R M32 , R M33 , R M34 , R M35 , R M36 , R M37 , R M38 , R M39 , and nx are R in formula (M1-1), respectively. M21 , R M22 , R M23 , R M24 , R M25 , R M26 , R M27 , R M28 , R M29 , R M30 , R M31 , R M32 , R M33 , R M34 , R M35 , R M36 , R M37 , R M38 , R M39 , and nx, and the preferred ranges are also the same.

[0037] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-3), and more preferably a compound represented by the following formula (M1-4). [ka] (In formula (M1-3), nx represents an integer of 1 or more and 20 or less.) nx may be an integer of 10 or less. [ka] (In formula (M1-4), nx represents an integer of 1 or more and 20 or less.) nx may be an integer of 10 or less.

[0038] The molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By making the molecular weight equal to or greater than the lower limit, the low dielectric properties (Dk and / or Df) and low water absorption of the resulting cured product tend to be further improved. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, even more preferably 5,000 or less, and even more preferably 4,000 or less. By making the molecular weight equal to or less than the upper limit, the heat resistance and handleability of the resulting cured product tend to be further improved.

[0039] The compound represented by formula (M1) preferably has a maleimide group equivalent of 50 g / eq. or more, more preferably 100 g / eq. or more, and even more preferably 200 g / eq. or more. The upper limit of the maleimide equivalent is preferably 2000 g / eq. or less, more preferably 1000 g / eq. or less, and even more preferably 800 g / eq. or less. Here, the maleimide group equivalent represents the mass of the maleimide compound per equivalent of maleimide group. When the maleimide group equivalent of the compound represented by formula (M1) is within the above range, the resulting cured product tends to have improved low dielectric properties (Dk and / or Df), low water absorption, heat resistance, and handleability.

[0040] The compound represented by formula (M1) preferably has a molecular weight distribution Mw / Mn calculated by gel permeation chromatography (GPC) measurement of 1.0 to 4.0, more preferably 1.1 to 3.8, even more preferably 1.2 to 3.6, and even more preferably 1.3 to 3.4. When the Mw / Mn of the compound represented by formula (M1) is within the above range, the resulting cured product tends to have further improved low dielectric properties (Dk and / or Df), low water absorbency, heat resistance, and handleability.

[0041] For other details of the compound represented by formula (M1), please refer to the descriptions in International Publication No. 2020-217679, the contents of which are incorporated herein by reference.

[0042] [ka] (In formula (M2), R 54 each independently represents a hydrogen atom or a methyl group, and n4 represents an integer of 1 or greater. n4 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. The compound represented by formula (M2) may be, and preferably is, a mixture of compounds in which n4 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0). [ka] (In formula (M3), R 55 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and n5 represents an integer of 1 or more and 10 or less. R 55are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. n5 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2. The compound represented by formula (M3) may be, and preferably is, a mixture of compounds in which n5 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0). [ka] (In formula (M4), R 56 each independently represents a hydrogen atom, a methyl group, or an ethyl group; R 57 each independently represents a hydrogen atom or a methyl group. R 56 are preferably each independently a methyl group or an ethyl group, and more preferably a methyl group and an ethyl group on each of the two benzene rings, and R 57 is preferably a methyl group.

[0043] [ka] (In formula (M5), R 58 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R 59 each independently represents a hydrogen atom or a methyl group, and n6 represents an integer of 1 or greater. R 58 are each independently preferably one selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. R 59 is preferably a methyl group. n6 is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. The compound represented by formula (M5) may be, and preferably is, a mixture of compounds in which n6 is different, or may be a mixture of compounds in which other moieties are different, as described for the compound represented by formula (M0).

[0044] The maleimide compound (M6) is a compound having a structural unit represented by formula (M6) and maleimide groups at both ends of the molecular chain. [ka] (In formula (M6), R 61 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. 62 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. 63 each independently represents a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. Each n independently represents an integer of 0 to 10. For details of the maleimide compound (M6) and its production method, please refer to paragraphs 0061 to 0066 of WO 2020 / 262577, the contents of which are incorporated herein by reference.

[0045] The maleimide compound (M7) is a maleimide compound obtained by reacting, as reaction raw materials (1), an aromatic amine compound (a1) having 1 to 3 alkyl groups on the aromatic ring, an aromatic divinyl compound (a2) having two ethenyl groups, and maleic anhydride. The maleimide compound (M7) is preferably a compound represented by the formula (M7). [ka] (In the above formula (M7), R 1 each independently represents the alkyl group; R 2 each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or a methyl group, and R 3 and R 4 One of the groups is a hydrogen atom and the other is a methyl group, and R 5 and R 6 one of which is a hydrogen atom and the other is a methyl group, X 1 is the following formula (x): [ka] (In formula (x), R 7 and R 8 each independently represents a hydrogen atom or a methyl group, and R 7 and R 8 One of the groups is a hydrogen atom and the other is a methyl group, and R 9 each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, and t represents an integer of 0 to 4. and r represents a substituent represented by X 1 X per benzene ring to which 1 is the average number of substitutions, and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

[0046] For details of the polymaleimide compound (M7) used in this embodiment, refer to the description in Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0047] The maleimide compound may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "BMI-80" manufactured by K.I. Chemical Industry Co., Ltd. as the compound represented by formula (M0), "NE-X-9470S" manufactured by DIC Corporation as the compound represented by formula (M1), "BMI-2300" manufactured by Daiwa Kasei Kogyo Co., Ltd. as the compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M3), "BMI-70" manufactured by K.I. Chemical Industry Co., Ltd. as the compound represented by formula (M4), "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M5), "MIZ-001" manufactured by Nippon Kayaku Co., Ltd. as the maleimide compound (M6), and "NE-X-9500" manufactured by DIC Corporation as the maleimide compound (M7).

[0048] Furthermore, examples of maleimide compounds other than those mentioned above include N-phenylmaleimide, N-cyclohexylmaleimide, phenylmethanemaleimide oligomers, m-phenylenebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, prepolymers thereof, and prepolymers of these maleimides and amines. In particular, when monofunctional maleimide compounds such as N-phenylmaleimide and N-cyclohexylmaleimide are used in combination with a polymer having a structural unit represented by the following formula (V), a resin composition capable of providing a cured product with excellent low dielectric properties tends to be obtained.

[0049] When the resin composition of this embodiment contains a maleimide compound, the lower limit of the content is preferably 1 part by mass or more, more preferably 10 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 50 parts by mass or more, and even more preferably 60 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the content of the maleimide compound is 1 part by mass or more, the low dielectric properties and flame resistance of the resulting cured product tend to be improved. Furthermore, the upper limit of the content of the maleimide compound is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and even 80 parts by mass or less, or even 75 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. When the content of the maleimide compound is 90 parts by mass or less, the metal foil peel strength and low water absorbency tend to be improved. The resin composition of the present embodiment may contain only one maleimide compound or may contain two or more maleimide compounds. When two or more maleimide compounds are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of a maleimide compound, meaning that the content of the maleimide compound is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0050] <<Polyphenylene ether compounds>> The resin composition of the present embodiment may contain a polyphenylene ether compound, and may further contain a polyphenylene ether compound (B) containing two or more carbon-carbon unsaturated double bonds. The polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond is preferably a polyphenylene ether compound having, at its terminal, a group selected from the group consisting of a group represented by formula (Rx-1), such as a vinylbenzyl group, a group represented by formula (Rx-2), such as a (meth)acrylic group, and a maleimide group; more preferably a polyphenylene ether compound having a group represented by formula (Rx-1), such as a vinylbenzyl group, and / or a group represented by formula (Rx-2), such as a (meth)acrylic group; and even more preferably a polyphenylene ether compound containing, at its terminal, two or more groups represented by formula (Rx-1), such as a vinylbenzyl group, and / or groups represented by formula (Rx-2), such as a (meth)acrylic group. [ka] (In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , and ,R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 1 to 6.

[0051] Use of these polyphenylene ether compounds tends to more effectively improve the low dielectric properties (Dk and / or Df) and low water absorption of printed wiring boards and the like. In this embodiment, polyphenylene ether compounds having a vinylbenzyl group at the terminal are particularly preferred. The presence of a vinylbenzyl group tends to significantly improve compatibility with the resin (A). These will be explained in detail below.

[0052] The polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond (preferably, a polyphenylene ether compound (B2) containing two or more carbon-carbon unsaturated double bonds) is exemplified by a compound having a phenylene ether skeleton represented by the following formula (X1):

[0053] [ka] (In formula (X1), R 24 , R 25 , R 26 , and ,R 27 may be the same or different and represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.

[0054] The polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond (preferably, the polyphenylene ether compound (B2) containing two or more carbon-carbon unsaturated double bonds) is represented by the formula (X2): [ka] (In formula (X2), R 28 , R 29 , R 30 , R 34 , and ,R 35 may be the same or different and represent an alkyl group having 6 or less carbon atoms or a phenyl group. 31 , R 32 , and ,R 33 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. and / or a repeating unit represented by formula (X3): [ka] (In formula (X3), R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , and ,R 43 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0055] The polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond (preferably a polyphenylene ether compound (B2) containing two or more carbon-carbon unsaturated double bonds) is preferably a modified polyphenylene ether compound in which some or all of the terminals are functionalized with ethylenically unsaturated groups (hereinafter sometimes referred to as "modified polyphenylene ether compound (g)"). It is more preferred that the modified polyphenylene ether compound has two or more terminal groups selected from the group consisting of a group represented by formula (Rx-1) such as a vinylbenzyl group, a group represented by formula (Rx-2) such as a (meth)acrylic group, and a maleimide group. The group represented by formula (Rx-1) such as a vinylbenzyl group and / or a group represented by formula (Rx-2) such as a (meth)acrylic group is even more preferred. The use of such modified polyphenylene ether compound (g) enables the resin composition to have a cured product with reduced dielectric constant (Dk and / or Df), low water absorption, and high metal foil peel strength. These may be used alone or in combination of two or more.

[0056] The modified polyphenylene ether compound (g) may be a polyphenylene ether compound represented by formula (OP). [ka] (In formula (OP), X represents an aromatic group, -(YO) n1 - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). [ka] (In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , and ,R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 1 to 6.

[0057] When n1 and / or n2 are integers of 2 or greater, the n1 structural units (YO) and / or n2 structural units may be the same or different. n2 is preferably 2 or greater, and more preferably 2.

[0058] In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , and ,R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. R 1 is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. R 2 and R 3 are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. R 1 , R 2 , and ,R 3 The number of carbon atoms in each of the alkyl group, alkenyl group, and alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0059] In formula (Rx-1), r represents an integer of 1 to 6, preferably an integer of 1 to 5, more preferably an integer of 1 to 4, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and even more preferably 1.

[0060] In formula (Rx-1), each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, still more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and still more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In formula (Rx-1), z represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and still more preferably 0.

[0061] A specific example of the group represented by formula (Rx-1) is a vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is a (meth)acryloyl group. Rx is preferably a group represented by formula (Rx-1).

[0062] The modified polyphenylene ether compound (g) may be a polyphenylene ether compound represented by formula (OP-1). [ka] (In formula (OP-1), X represents an aromatic group, -(YO)n2- represents a polyphenylene ether structure, and R 1 , R 2 , and ,R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, n1 represents an integer of 1 to 6, n2 represents an integer of 1 to 100, and n3 represents an integer of 1 to 4. When n2 and / or n3 are integers of 2 or greater, the n2 structural units (YO) and / or n3 structural units may be the same or different. n3 is preferably 2 or greater, and more preferably 2.

[0063] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2), and more preferably a compound represented by formula (OP-2-2). [ka] [ka] where -(OXO)- is a compound of formula (OP-3): [ka] (In formula (OP-3), R 4 , R 5 , R 6 , R 10 , and ,R 11 R may be the same or different and is an alkyl group or a phenyl group having 6 or less carbon atoms. 7 , R 8 , and ,R 9 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. and / or formula (OP-4): [ka] (In formula (OP-4), R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and ,R 19 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0064] Also, -(YO)- is a group represented by the formula (OP-5): [ka] (In formula (OP-5), R 20 , R 21 R may be the same or different and is an alkyl group or a phenyl group having 6 or less carbon atoms. 22 , R 23 may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. Especially R 20 and R 21By independently having one or more methyl groups and / or cyclohexyl groups, the rigidity of the resulting resin molecules increases. Since molecules with high rigidity have lower mobility compared to molecules with low rigidity, the relaxation time during dielectric relaxation becomes longer, which is preferable for improving low dielectric characteristics (Dk and / or Df). An example of formula (OP-5) has the following structure. [Chemical formula] Regarding the polyphenylene compound having the above structure, the description in JP-A-2019-194312 can be referred to, and this content is incorporated herein.

[0065] In formula (OP-2), a and b each independently represent an integer from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are each independently an integer from 0 to 50, more preferably an integer from 1 to 30, and preferably an integer from 1 to 10. When a and / or b is an integer of 2 or more, two or more -(Y-O)- may each independently be an arrangement of one kind of structure, or two or more kinds of structures may be arranged in blocks or randomly. Also, when a plurality of compounds represented by formula (OP-2) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0066] Examples of -A- in formula (OP-4) include divalent organic groups such as methylene group, ethylidene group, 1-methylethylidene group, 1,1-propylidene group, 1,4-phenylenebis(1-methylethylidene) group, 1,3-phenylenebis(1-methylethylidene) group, cyclohexylidene group, phenylmethylene group, naphthylmethylene group, 1-phenylethylidene group, etc., but are not limited thereto.

[0067] Rx is synonymous with Rx in formula (OP), and the preferred range is also the same.

[0068] Among the compounds represented by the above formula (OP-2), R 4 , R 5 , R 6 , R 10 , R 11 , R 20 , and ,R 21 is an alkyl group having 3 or less carbon atoms, and R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 22 , and ,R 23 is a hydrogen atom or an alkyl group having 3 or less carbon atoms, and it is particularly preferred that -(OXO)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and -(YO)- represented by formula (OP-5) is formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the two or more -(YO)- may each independently be a structure in which two or more formulas (OP-12) and / or formulas (OP-13) are arranged, or a structure in which formulas (OP-12) and (OP-13) are arranged in blocks or randomly.

[0069] [ka] [ka] (In formula (OP-10), R 44 , R 45 , R 46 , and ,R 47 may be the same or different and are a hydrogen atom or a methyl group. -B- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms. Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4). [ka] (In formula (OP-11), -B- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.) Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4). [ka] [ka]

[0070] The modified polyphenylene ether compound (g) used in this embodiment is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15). [ka] (In formula (OP-14), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) In formula (OP-14), a and b each independently have the same meaning as a and b in formula (OP-2), and the preferred ranges are also the same. [ka] (In formula (OP-15), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) In formula (OP-15), a and b each independently have the same meaning as a and b in formula (OP-2), and the preferred ranges are also the same.

[0071] The polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond (preferably a polyphenylene ether compound (B2) containing two or more carbon-carbon unsaturated double bonds, more preferably a modified polyphenylene ether compound (g)) has a polystyrene-equivalent number average molecular weight (Mn) measured by a GPC (gel permeation chromatography) method (details follow the method described in the Examples below) of, for example, 500 or more, preferably 800 or more, and preferably 3,000 or less. When the number average molecular weight is 500 or more, stickiness tends to be further suppressed when the resin composition of the present embodiment is formed into a coating film. When the number average molecular weight is 3,000 or less, solubility in solvents tends to be further improved. Furthermore, the polystyrene-equivalent weight average molecular weight (Mw) of the polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond (preferably a polyphenylene ether compound (B2) containing two or more carbon-carbon unsaturated double bonds, more preferably a modified polyphenylene ether compound (g)) measured by GPC (details follow the method described in the Examples below) is preferably 800 or more and 6,000 or less, and more preferably 800 or more and 5,000 or less. By setting the Mw to be equal to or more than the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower, while by setting the Mw to be equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents when preparing a varnish or the like, which will be described later, tend to be further improved. Furthermore, in the case of the modified polyphenylene ether compound (g), the terminal carbon-carbon unsaturated double bond equivalent is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, more preferably 400 to 2500 g. By setting the equivalent at or above the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower. By setting the equivalent at or below the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents tend to be further improved.

[0072] When the resin composition of this embodiment contains a polyphenylene ether compound, the lower limit of its content 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, and even more preferably 60 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content is above the lower limit, the moldability of the resin composition and 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 polyphenylene ether compound content is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and may even be 80 parts by mass or less or 75 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content is below the upper limit, the low dielectric properties (particularly low dielectric tangent) and chemical resistance of the resulting cured product tend to be improved. The resin composition of the present embodiment may contain only one type of polyphenylene ether compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0073] The resin composition of the present embodiment may also be configured to be substantially free of polyphenylene ether compounds containing two or more carbon-carbon unsaturated double bonds, or even polyphenylene ether compounds. "Substantially free" means that the content of polyphenylene ether compounds containing two or more carbon-carbon unsaturated double bonds, or even polyphenylene ether compounds, is less than 0.1 part by mass, preferably less than 0.01 part by mass, and even less than 0.001 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0074] <<Polymer Having a Constitutional Unit Represented by Formula (V)>> The resin composition of the present embodiment may contain a polymer having a structural unit represented by formula (V). By containing a polymer having a structural unit represented by formula (V), a resin composition having excellent low dielectric properties (low relative dielectric constant, low dielectric loss tangent) can be obtained. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) The aromatic hydrocarbon linking group may be a group consisting of only aromatic hydrocarbons which may have a substituent, or a group consisting of a combination of aromatic hydrocarbons which may have a substituent and other linking groups, and is preferably a group consisting of only aromatic hydrocarbons which may have a substituent. The substituent that the aromatic hydrocarbon may have includes a substituent Z (e.g., an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, an amino group, a carboxy group, a halogen atom, etc.). It is also preferable that the aromatic hydrocarbon does not have a substituent. The aromatic hydrocarbon linking group is usually a divalent linking group.

[0075] Specific examples of the aromatic hydrocarbon linking group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a biphenyldiyl group, and a fluorenediyl group, which may have a substituent, and among these, a phenylene group which may have a substituent is preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferable that the above-mentioned phenylene group and other groups have no substituent.

[0076] The structural unit represented by formula (V) more preferably includes at least one of a structural unit represented by the following formula (V1), a structural unit represented by the following formula (V2), and a structural unit represented by the following formula (V3). In the following formulae, * represents a bonding position. Furthermore, hereinafter, the structural units represented by formulas (V1) to (V3) may be collectively referred to as "structural unit (a)."

[0077] [ka] In formulas (V1) to (V3), L 1is an aromatic hydrocarbon linking group (preferably having 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 10 carbon atoms). Specific examples include phenylene groups, naphthalenediyl groups, anthracenediyl groups, phenanthrenediyl groups, biphenyldiyl groups, and fluorenediyl groups, each of which may have a substituent, and among these, phenylene groups, which may have a substituent, are preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferable that the above-mentioned phenylene groups and other groups have no substituent. The compound forming the structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene. Among these, divinylbenzene is particularly preferred. These divinyl aromatic compounds may be used alone or in combination of two or more types, as required.

[0078] As described above, the polymer having the structural unit represented by formula (V) may be a homopolymer of the structural unit (a), but it may also be a copolymer with a structural unit derived from another monomer. When the polymer having the structural unit represented by formula (V) is a copolymer, the copolymerization ratio of the structural unit (a) is preferably 3 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, and may be 15 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, particularly more preferably 30 mol% or less, and may even be 25 mol% or less, or 20 mol% or less.

[0079] An example of a structural unit derived from another monomer is a structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0080] The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[0081] [ka] In formula (V4), L 2 is an aromatic hydrocarbon linking group, and specific examples of preferred groups include the above L 1 Examples include: R V1 is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). V1 When R is a hydrocarbon group, it preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. V1 and L 2 may have the above-mentioned substituent Z.

[0082] When the polymer having a structural unit represented by formula (V) is a copolymer containing a structural unit (b) derived from a monovinyl aromatic compound, examples of the monovinyl aromatic compound include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinylbiphenyl; and nuclear alkyl-substituted vinyl aromatic compounds such as o-methylstyrene, m-methylstyrene, p-methylstyrene, o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, and ethylvinylbiphenyl. The monovinyl aromatic compounds exemplified here may optionally have the above-mentioned substituent Z. Furthermore, these monovinyl aromatic compounds may be used alone or in combination of two or more.

[0083] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (b), the copolymerization ratio of the structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may even be 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, or 75 mol% or more. The upper limit is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.

[0084] A polymer having a structural unit represented by formula (V) may have structural units other than structural unit (a) and structural unit (b). Examples of such structural units include structural unit (c) derived from a cycloolefin compound. Examples of cycloolefin compounds include hydrocarbons having a double bond within the ring structure. Specific examples include monocyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, as well as compounds having a norbornene ring structure such as norbornene and dicyclopentadiene, and cycloolefin compounds having condensed aromatic rings such as indene and acenaphthylene. Examples of norbornene compounds include those described in paragraphs 0037 to 0043 of JP 2018-039995 A, the contents of which are incorporated herein by reference. The cycloolefin compounds exemplified here may further have the aforementioned substituent Z.

[0085] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (c), the copolymerization ratio of the structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, and even more preferably 70 mol% or less, and may be 50 mol% or less, or may be 30 mol% or less.

[0086] A polymer having a structural unit represented by formula (V) may further incorporate a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as other polymerizable compound). Examples of other polymerizable compounds (monomers) include compounds containing three vinyl groups. Specific examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate and butadiene. The copolymerization ratio of the structural unit (d) derived from other polymerizable compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0087] An example of an embodiment of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains structural unit (a) and includes at least one of structural units (b) to (d). A further example is one in which the total of structural units (a) to (d) accounts for 95 mol % or more, and even 98 mol % or more, of all structural units. In another embodiment of the polymer having a structural unit represented by formula (V), the structural unit (a) is essential, and of all structural units excluding the terminals, structural units containing an aromatic ring preferably account for 90 mol % or more, more preferably 95 mol % or more, and may even account for 100 mol %. In calculating the mole percent per total structural units, one structural unit is defined as being derived from one molecule of a monomer (e.g., a divinyl aromatic compound, a monovinyl aromatic compound, etc.) used in producing a polymer having a structural unit represented by formula (V).

[0088] The method for producing a polymer having a structural unit represented by formula (V) is not particularly limited and may be a conventional method, but examples thereof include polymerizing a raw material containing a divinyl aromatic compound (optionally in the presence of a monovinyl aromatic compound, a cycloolefin compound, etc.) in the presence of a Lewis acid catalyst. The Lewis acid catalyst may be a metal fluoride such as boron trifluoride or a complex thereof.

[0089] The structure of the chain end of the polymer having the structural unit represented by formula (V) is not particularly limited, but in terms of the group derived from the above divinyl aromatic compound, it may have the structure of the following formula (E1). 1 is the same as defined in the above formula (V1). * represents the bonding position. *-CH=CH-L 1 -CH=CH2(E1)

[0090] When a group derived from a monovinyl aromatic compound is at the chain end, the structure may be that of the following formula (E2): 2 and R V1 are the same as defined in the formula (V4) above. * represents a bonding position. *-CH=CH-L 2 -R V1 (E2)

[0091] The molecular weight of the polymer having a constitutional unit represented by formula (V) is preferably a number average molecular weight Mn of 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and still more preferably 1,500 or more. The upper limit is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, and still more preferably 100,000 or less. The molecular weight of the polymer having the structural unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 10,000 or more, in terms of weight-average molecular weight Mw. By ensuring that the molecular weight is equal to or greater than the lower limit, the excellent low dielectric properties of the polymer having the structural unit represented by formula (V), particularly Df and dielectric properties after moisture absorption, can be effectively exhibited in the cured product of the resin composition. The upper limit 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 ensuring that the molecular weight is equal to or less than the upper limit, embedding defects tend to be less likely to occur when the prepreg or resin sheet is laminated on a circuit-printing substrate. The monodispersity (Mw / Mn), which is 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, and even more preferably 20 or less. A practical lower limit is 1.1 or more, preferably 5 or more, more preferably 7 or more, and even more preferably 10 or more. The Mw and Mn are measured as described in the Examples below. When the resin composition of the present embodiment contains two or more polymers having a structural unit represented by formula (V), it is preferable that the Mw, Mn and Mw / Mn of the mixture satisfy the above ranges.

[0092] The vinyl group equivalent of the polymer having a structural unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, and even more preferably 250 g / eq. or more. The vinyl group equivalent 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, 400 g / eq. or less, or 300 g / eq. or less. By setting the equivalent at or above the lower limit, the storage stability of the resin composition tends to be improved, and the flowability of the resin composition tends to be improved. Therefore, moldability is improved, voids are less likely to occur during the formation of prepregs, etc., and more reliable printed wiring boards tend to be obtained. On the other hand, by setting the equivalent at or below the upper limit, the heat resistance of the resulting cured product tends to be improved.

[0093] For polymers having a structural unit represented by formula (V) in this specification, the compounds described in paragraphs 0029 to 0058 of International Publication No. 2017 / 115813 and their synthesis reaction conditions, etc., compounds described in paragraphs 0013 to 0058 of JP-A-2018-039995 and their synthesis reaction conditions, etc., compounds described in paragraphs 0008 to 0043 of JP-A-2018-168347 and their synthesis reaction conditions, etc., compounds described in paragraphs 0014 to 0042 of JP-A-2006-070136 and their synthesis reaction conditions, etc., compounds described in paragraphs 0014 to 0061 of JP-A-2006-089683 and their synthesis reaction conditions, etc., compounds described in paragraphs 0008 to 0036 of JP-A-2008-248001 and their synthesis reaction conditions, etc. can be referenced, and are incorporated herein by reference.

[0094] 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 10 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 50 parts by mass or more, and even more preferably 60 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content of the polymer having a structural unit represented by formula (V) is 1 part by mass or more, and is above the above lower limit, low dielectric properties, particularly a low relative dielectric constant, tend to be effectively achieved. Furthermore, the upper limit of the content of the polymer having a structural unit represented by formula (V) is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and may even be 80 parts by mass or less or 75 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content of the polymer having a structural unit represented by formula (V) is 90 parts by mass or less, metal foil peel strength and low water absorbency tend to be improved. The resin composition in this embodiment may contain only one type of polymer having a structural unit represented by formula (V), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition in this embodiment may also be configured to be substantially free of a polymer having a structural unit represented by formula (V). "Substantially free" means that the content of the polymer having a structural unit represented by formula (V) is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0095] <<Cyanate ester compounds>> The resin composition of the present embodiment may contain a cyanate ester compound. The cyanate ester compound is not particularly limited as long as it contains one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) cyanate groups (cyanato groups) in the molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used.

[0096] The cyanate ester compound is preferably a cyanate ester compound having two or more aromatic moieties substituted with at least one cyanato group in the molecule, which is commonly used in printed wiring boards. Specifically, the lower limit of the number of cyanato groups in the cyanate ester compound is preferably 2 or more, more preferably 3 or more. By setting the number at or above the lower limit, heat resistance tends to be further improved. Furthermore, the upper limit of the number of cyanato groups is preferably 100 or less, more preferably 50 or less. Furthermore, it is preferable that the cured product of the cyanate ester compound has excellent low dielectric properties (Dk and / or Df). For example, the dielectric constant (Dk) of the cured product of the cyanate ester compound at a frequency of 10 GHz measured according to the cavity resonance perturbation method is preferably 4.0 or less, more preferably 3.5 or less. Furthermore, a practical lower limit of the dielectric constant is, for example, 2.0 or more. Furthermore, the dielectric loss tangent (Df) of the cured product of the cyanate ester compound (B) at a frequency of 10 GHz measured according to the cavity resonance perturbation method is preferably 0.02 or less, more preferably 0.015 or less. Furthermore, a practical lower limit of the dielectric loss tangent is, for example, 0.0001 or more. The dielectric constant and dielectric loss tangent can be measured, for example, according to the methods (curing conditions, measurement conditions) described in the Examples.

[0097] Furthermore, it is preferable that the cured product of the cyanate ester compound has high heat resistance. The cured product of the cyanate ester compound preferably has a glass transition temperature of 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher, as measured in accordance with JIS C6481 dynamic viscoelasticity measurement. By adjusting the glass transition temperature to the aforementioned lower limit or higher, a cured product with excellent heat resistance can be obtained.

[0098] The weight-average molecular weight of the cyanate ester compound, as calculated on a polystyrene basis by a GPC method, is preferably 200 or more, more preferably 300 or more, and even more preferably 400 or more. By setting the weight-average molecular weight to the above-mentioned lower limit or more, heat resistance tends to be further improved. Furthermore, the weight-average molecular weight of the cyanate ester compound is preferably 1000 or less, more preferably 900 or less, and even more preferably 800 or less. By setting the weight-average molecular weight to the above-mentioned upper limit or less, moldability and handleability tend to be further improved.

[0099] For a preferred range of the cyanate ester compound, reference can be made to paragraphs 0028 to 0033 of WO 2021 / 172317, the contents of which are incorporated herein by reference.

[0100] Preferred cyanate ester compounds include at least one selected from the group consisting of phenol novolac-type cyanate ester compounds, naphthol aralkyl-type cyanate ester compounds (naphthol aralkyl-type cyanates), naphthylene ether-type cyanate ester compounds, biphenyl aralkyl-type cyanate ester compounds, xylene resin-type cyanate ester compounds, trisphenolmethane-type cyanate ester compounds, adamantane skeleton-type cyanate ester compounds, bisphenol M-type cyanate ester compounds, and bisphenol A-type cyanate ester compounds. Among these, from the viewpoint of further improving low water absorbency, at least one selected from the group consisting of phenol novolac cyanate ester compounds, naphthol aralkyl cyanate ester compounds, naphthylene ether cyanate ester compounds, xylene resin cyanate ester compounds, bisphenol M cyanate ester compounds, and bisphenol A cyanate ester compounds is preferred, at least one selected from the group consisting of phenol novolac cyanate ester compounds, naphthol aralkyl cyanate ester compounds, naphthylene ether cyanate ester compounds, bisphenol A cyanate ester compounds, and bisphenol M cyanate ester compounds is more preferred, at least one selected from the group consisting of phenol novolac cyanate ester compounds, naphthol aralkyl cyanate ester compounds, and bisphenol A cyanate ester compounds is even more preferred, naphthol aralkyl cyanate ester compounds and / or bisphenol A cyanate ester compounds are even more preferred, and naphthol aralkyl cyanate ester compounds are even more preferred.

[0101] The naphthol aralkyl cyanate ester compound is more preferably a compound represented by formula (N1).

[0102] Formula (N1) [ka] (In formula (N1), R 3 each independently represents a hydrogen atom or a methyl group, and n3 represents an integer of 1 or greater.

[0103] In formula (N1), R 3 each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferred. In formula (N1), n3 is an integer of 1 or more, preferably an integer of 1 to 50, more preferably an integer of 1 to 20, even more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0104] The phenol novolac cyanate ester compound is not particularly limited, but is preferably, for example, a compound represented by formula (VII). [ka] (In formula (VII), R 6 each independently represents a hydrogen atom or a methyl group, and n7 represents an integer of 1 or greater.

[0105] In formula (VII), R 6 each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferred. In formula (VII), n7 is an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0106] As the bisphenol A type cyanate ester compound, one or more compounds selected from the group consisting of 2,2-bis(4-cyanatophenyl)propane and prepolymers of 2,2-bis(4-cyanatophenyl)propane may be used.

[0107] These cyanate ester compounds may be prepared by known methods, or commercially available products may be used. Cyanate ester compounds having a naphthol aralkyl skeleton, a naphthylene ether skeleton, a xylene skeleton, a trisphenolmethane skeleton, or an adamantane skeleton have a relatively large functional group equivalent weight and a small number of unreacted cyanate ester groups, so resin compositions using these compounds tend to have even better low water absorption. Furthermore, due mainly to the presence of an aromatic skeleton or an adamantane skeleton, plating adhesion tends to be even better.

[0108] When the resin composition of this embodiment contains a cyanate ester compound, the lower limit of the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and may even be 20 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Having the cyanate ester compound content at or above the above lower limit tends to improve heat resistance, flame resistance, chemical resistance, low dielectric constant, low dielectric loss tangent, and insulating properties. When the resin composition of this embodiment contains a cyanate ester compound, the upper limit of the content of the cyanate ester compound is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, and may even be 40 parts by mass or less, or 30 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of cyanate ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of cyanate ester compounds, meaning that the content of the cyanate ester compounds is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0109] <<Epoxy compounds>> The resin composition of the present embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) epoxy groups in one molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of epoxy compounds include bisphenol A epoxy resins, bisphenol E epoxy resins, bisphenol F epoxy resins, bisphenol S epoxy resins, phenol novolac epoxy resins, bisphenol A novolac epoxy resins, glycidyl ester epoxy resins, aralkyl novolac epoxy resins, biphenyl aralkyl epoxy resins, naphthylene ether epoxy resins, cresol novolac epoxy resins, multifunctional phenol epoxy resins, naphthalene epoxy resins, anthracene epoxy resins, naphthalene skeleton-modified novolac epoxy resins, phenol aralkyl epoxy resins, naphthol aralkyl epoxy resins, dicyclopentadiene epoxy resins, biphenyl epoxy resins, alicyclic epoxy resins, polyol epoxy resins, phosphorus-containing epoxy resins, glycidyl amines, glycidyl esters, compounds in which the double bond of butadiene or the like has been epoxidized, and compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin. The use of these compounds improves the moldability and adhesion of the resin composition. Among these, from the viewpoint of further improving flame retardancy and heat resistance, biphenyl aralkyl type epoxy resins, naphthylene ether type epoxy resins, polyfunctional phenol type epoxy resins, and naphthalene type epoxy resins are preferred, and biphenyl aralkyl type epoxy resins are more preferred.

[0110] The resin composition of this embodiment preferably contains an epoxy compound within a range that does not impair the effects of the present invention. From the viewpoints of moldability and adhesion, when the resin composition of this embodiment contains an epoxy compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the epoxy compound content is 0.1 parts by mass or more, the metal foil peel strength and toughness tend to be improved. When the resin composition of this embodiment contains an epoxy compound, the upper limit of the epoxy compound content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition, and may be 8 parts by mass or less, or 5 parts by mass or less. When the epoxy compound content is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition in the present embodiment may contain only one type of epoxy compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of epoxy compounds, which means that the content of the epoxy compounds is less than 0.1 parts by mass, preferably less than 0.01 parts by mass, and even less than 0.001 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0111] <<Phenol compounds>> The resin composition of the present embodiment may contain a phenol compound. For details of the phenolic resin, please refer to paragraph 0049 of International Publication No. 2021 / 172317, the contents of which are incorporated herein by reference.

[0112] The resin composition of the present embodiment preferably contains a phenolic compound within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains a phenolic compound, the content thereof is preferably 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of phenol compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of phenolic compounds, meaning that the content of phenolic compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0113] <<Compounds containing a (meth)allyl group>> The resin composition of the present embodiment preferably contains a compound containing a (meth)allyl group, and more preferably contains a compound containing an allyl group. Furthermore, the compound containing a (meth)allyl group is preferably a compound containing two or more (meth)allyl groups, and more preferably a compound containing two or more allyl groups. The compound containing a (meth)allyl group preferably contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a tri(meth)allyl cyanurate compound, a (meth)allyl group-substituted nadimide compound, a (meth)allyl compound having a glycoluril structure, and a diallyl phthalate; more preferably contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a (meth)allyl group-substituted nadimide compound, and a (meth)allyl compound having a glycoluril structure; even more preferably contains a (meth)allyl isocyanurate compound and / or a (meth)allyl group-substituted nadimide compound; and even more preferably contains a (meth)allyl group-substituted nadimide compound.

[0114] Examples of the tri(meth)allyl cyanurate compound include tri(meth)allyl cyanurate compounds (for example, triallyl cyanurate having the structure shown below). [ka] In addition, examples of compounds containing a (meth)allyl group include resins having an allyl group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 3, 4, 6, 20, and 22 of the same publication), the contents of which are incorporated herein by reference.

[0115] When the resin composition of this embodiment contains a compound containing a (meth)allyl group, the molecular weight thereof is preferably 195 or more, more preferably 300 or more, even more preferably 400 or more, and even more preferably 500 or more. By setting the molecular weight at or above the lower limit, low dielectric properties and heat resistance tend to be further improved. The molecular weight of the compound containing a (meth)allyl group is also preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight at or below the upper limit, low thermal expansion tends to be further improved.

[0116] When the resin composition of this embodiment contains a compound containing a (meth)allyl group, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the compound containing a (meth)allyl group to be equal to or greater than the above-mentioned lower limit, excellent moldability and heat resistance tend to be further improved. Furthermore, the upper limit of the content of the compound containing a (meth)allyl group is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the compound containing a (meth)allyl group to be equal to or less than the above-mentioned upper limit, low thermal expansion properties tend to be further improved. The resin composition of the present embodiment may contain only one type of compound containing a (meth)allyl group, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0117] <<<(Meth)allyl isocyanurate compounds>>> The (meth)allyl isocyanurate compound is not particularly limited as long as it has two or more (meth)allyl groups and an isocyanurate ring (nurate skeleton). Because the (meth)allyl isocyanurate compound has a large number of (meth)allyl groups that serve as crosslinking points, it tends to be strongly cured with the resin (A), the polyphenylene ether compound (B), and other resin components (e.g., other compounds (C)), resulting in a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. The (meth)allyl isocyanurate compound is preferably a compound represented by formula (TA). Formula (TA) [ka] (In formula (TA), R A represents a substituent).

[0118] In formula (TA), R A represents a substituent, and is more preferably a substituent having a formula weight of 15 to 500.

[0119] R A A first example is an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using an allyl compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, it is possible to provide a resin composition that has excellent crosslinkability and is capable of giving a cured product having high toughness. This makes it possible to prevent cracking during etching or other treatments, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 3 or more, more preferably 8 or more, and may be 12 or more and 18 or less. This improves the resin flow properties of the resin composition, and is thought to result in better circuit filling properties when a multilayer circuit board or the like is produced using the resin composition of the present embodiment.

[0120] R A A second example of R is a group containing an allyl isocyanurate group. A When contains an allyl isocyanurate group, the compound represented by formula (TA) is preferably a compound represented by formula (TA-1). Formula (TA-1) [ka] (In formula (TA-1), R A2 is a divalent linking group.

[0121] In formula (TA-1), R A2 is preferably a divalent linking group having a formula weight of 54 to 250, more preferably a divalent linking group having a formula weight of 54 to 250 and both ends of which are carbon atoms, and even more preferably an aliphatic hydrocarbon group having 2 to 20 carbon atoms (however, the aliphatic hydrocarbon group may contain an ether group or may have a hydroxyl group). More specifically, R A2 is preferably a group represented by any one of the following formulas (i) to (iii). [ka] (In formulas (i) to (iii), p c1 represents the number of repeating methylene units and is an integer of 2 to 18. c2 represents the number of repeating units of the oxyethylene group, which is either 0 or 1. * represents the bonding site. The above p c1 is preferably an integer of 2 to 10, more preferably an integer of 3 to 8, and even more preferably an integer of 3 to 5. The above p c2may be 0 or 1, but is preferably 1.

[0122] R A A third example is a phosphorus-based substituent.

[0123] R A2 is preferably the first example.

[0124] In this embodiment, the reactive group (allyl group) equivalent of the compound represented by formula (TA) is preferably 1000 g / eq or less. If the equivalent is 1000 g / eq or less, it is believed that a high Tg can be obtained more reliably.

[0125] Examples of the alkyl group having 1 to 22 carbon atoms include linear or branched alkyl groups, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl groups. Examples of the alkenyl group having 2 to 22 carbon atoms include allyl and decenyl groups.

[0126] Specific examples of the compound represented by formula (TA) include triallyl isocyanurate, 5-octyl-1,3-diallyl isocyanurate, 5-dodecyl-1,3-diallyl isocyanurate, 5-tetradecyl-1,3-diallyl isocyanurate, 5-hexadecyl-1,3-diallyl isocyanurate, 5-octadecyl-1,3-diallyl isocyanurate, 5-eicosyl-1,3-diallyl isocyanurate, 5-docosyl-1,3-diallyl isocyanurate, 5-decenyl-1,3-diallyl isocyanurate, etc. These may be used alone or in combination of two or more, and may be used as a prepolymer.

[0127] The method for producing the compound represented by formula (TA) is not particularly limited, but for example, the compound can be obtained by reacting diallyl isocyanurate with an alkyl halide in an aprotic polar solvent such as N,N'-dimethylformamide in the presence of a basic substance such as sodium hydroxide, potassium carbonate, or triethylamine at a temperature of about 60°C to 150°C.

[0128] In addition, commercially available compounds represented by formula (TA) can also be used. Commercially available compounds are not particularly limited, but examples thereof include L-DAIC manufactured by Shikoku Chemical Industries Co., Ltd. and P-DAIC having a phosphorus-based substituent manufactured by Shikoku Chemical Industries Co., Ltd. An example of triallyl isocyanurate is TAIC manufactured by Shinryo Corporation. An example of a compound represented by formula (TA-1) is DD-1 manufactured by Shikoku Chemical Industries Co., Ltd.

[0129] The molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 200 or more, more preferably 300 or more, even more preferably 400 or more, and even more preferably 500 or more. By setting the molecular weight to be equal to or greater than the above-mentioned lower limit, the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product tend to be further improved. Furthermore, the molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to be equal to or less than the above-mentioned upper limit, the low thermal expansion properties of the resulting cured product tend to be further improved.

[0130] When the resin composition of this embodiment contains a (meth)allyl isocyanurate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl isocyanurate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one type of (meth)allyl isocyanurate compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0131] <<<(Meth)allyl-substituted nadimide compounds>>> The (meth)allyl group-substituted nadimide compound is not particularly limited as long as it has two or more (meth)allyl group-substituted nadimide groups in the molecule. Specific examples thereof include compounds represented by the following formula (AN): Formula (AN) [ka] In formula (AN), each R1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by formula (AN-2) or (AN-3). Formula (AN-2) [ka] (In formula (AN-2), R3 represents a methylene group, an isopropylidene group, or a group represented by -C(=O)-, -O-, -S-, or -S(=O)2-.) Formula (AN-3) [ka] (In formula (AN-3), each R4 independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.)

[0132] Furthermore, commercially available compounds represented by formula (AN) can also be used. Examples of commercially available compounds include, but are not limited to, the compound represented by formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and the compound represented by formula (AN-5) (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). These compounds may be used alone or in combination of two or more. Formula (AN-4) [ka] Formula (AN-5) [ka]

[0133] The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 400 or more, more preferably 500 or more, and may be 550 or more. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above lower limit or more, low dielectric properties, low thermal expansion, and heat resistance tend to be further improved. The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is also preferably 1500 or less, more preferably 1000 or less, and even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above upper limit or less, moldability and peel strength tend to be further improved.

[0134] When the resin composition of the present embodiment contains a (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or greater than the above-mentioned lower limit, excellent moldability and further improved low dielectric properties, low thermal expansion, and heat resistance tend to be achieved. Furthermore, the upper limit of the content of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or less than the above-mentioned upper limit, moldability and peel strength tend to be further improved. The resin composition of the present embodiment may contain only one (meth)allyl group-substituted nadimide compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0135] <<<(Meth)allyl compounds with glycoluril structure>>> The (meth)allyl compound having a glycoluril structure is not particularly limited as long as it contains a glycoluril structure and two or more (meth)allyl groups. When a (meth)allyl compound having a glycoluril structure is blended into a resin composition, the number of (meth)allyl groups can be increased, i.e., the number of crosslinking points can be increased. Therefore, similar to the (meth)allyl isocyanurate compound, it tends to be firmly cured with the resin (A), the polyphenylene ether compound (B), and other resin components (e.g., other compounds (C)), resulting in a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. In this embodiment, the (meth)allyl compound having a glycoluril structure is preferably a compound represented by formula (GU). Formula (GU) [ka] (In formula (GU), each R is independently a hydrogen atom or a substituent, and at least two R are groups containing a (meth)allyl group.) In formula (GU), each R is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, more preferably an alkenyl group having 2 to 5 carbon atoms, more preferably a (meth)allyl group, and even more preferably an allyl group. In formula (GU), three or four of R are preferably groups containing a (meth)allyl group, and four are more preferably groups containing a (meth)allyl group.

[0136] A specific example of the compound represented by formula (GU) is 1,3,4,6-tetraallylglycoluril (a compound of formula (GU) in which all R's are allyl groups).

[0137] The compound represented by formula (GU) may also be commercially available. Examples of commercially available compounds include, but are not limited to, TA-G manufactured by Shikoku Chemicals Corporation.

[0138] The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, even more preferably 250 or more, and may be 300 or more, or even 400 or more. By adjusting the molecular weight of the (meth)allyl compound having a glycoluril structure to be equal to or greater than the above-mentioned lower limit, the heat resistance and low thermal expansion of the resulting cured product tend to be further improved. The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By adjusting the molecular weight of the (meth)allyl compound having a glycoluril structure to be equal to or less than the above-mentioned upper limit, the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product tend to be further improved.

[0139] When the resin composition of this embodiment contains a (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure at or below the above-mentioned upper limit, the low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one type of (meth)allyl compound having a glycoluril structure, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0140] <<Oxetane resin>> The resin composition of the present embodiment may contain an oxetane resin. The oxetane resin is not particularly limited as long as it is a compound having one or more oxetanyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and still more preferably 2), and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of oxetane resins include oxetane, alkyloxetane (e.g., 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3,3-di(trifluoromethyl)oxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl-type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), and OXT-121 (manufactured by Toagosei Co., Ltd.).

[0141] The resin composition of this embodiment preferably contains an oxetane resin to a degree that does not impair the effects of the present invention. When the resin composition of this embodiment contains an oxetane resin, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the oxetane resin content is 0.1 parts by mass or more, the metal foil peel strength and toughness of the resulting cured product tend to be improved. When the resin composition of this embodiment contains an oxetane resin, the upper limit of the oxetane resin 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 even more preferably 8 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. When the oxetane resin content is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition in this embodiment may contain only one type of oxetane resin, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of oxetane resin, meaning that the content of oxetane resin is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0142] <<Benzoxazine compounds>> The resin composition of the present embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it has two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings in one molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of benzoxazine compounds include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0143] The resin composition of the present embodiment preferably contains a benzoxazine compound within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains a benzoxazine compound, the content thereof is preferably 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of benzoxazine compounds, meaning that the content of the benzoxazine compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0144] <<Arylcyclobutene Resin>> The resin composition of the present embodiment may contain an arylcyclobutene resin. For details, arylcyclobutene resins and the like described in paragraph 0042 of JP 2019-194312 A are exemplified, the contents of which are incorporated herein by reference.

[0145] <<Polyamide resin>> The resin composition of the present embodiment may contain a polyamide resin, or may contain a thermosetting polyamide resin. For details, reference can be made to the polyamides described in paragraph 0065 of JP 2019-194312 A and the polyamides described in paragraph 0063 of JP 6951829 A, the contents of which are incorporated herein by reference.

[0146] <<Polyimide resin>> The resin composition of the present embodiment may contain a polyimide resin or a thermosetting polyimide resin. For details, reference can be made to the polyimides and the like described in paragraphs 0063 to 0064 of Japanese Patent No. 6951829, the contents of which are incorporated herein by reference.

[0147] <<Perfluorovinyl ether resin>> The resin composition of the present embodiment may contain a perfluorovinyl ether resin or a perfluorovinyl benzyl ether resin. For details, perfluorovinyl ether resins and the like described in paragraph 0043 of JP-A-2019-194312 are exemplified, the contents of which are incorporated herein by reference.

[0148] <<Compounds having a styrene group other than polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond>> The resin composition of the present embodiment may contain a compound having a styrene group other than the polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond. Details of these include compounds having styrene at the terminal described in WO 2022 / 210095 (for example, the compounds described in Synthesis Examples 12 to 16 of the same publication), the description in paragraphs 0029 to 0038 of JP 2022-85610 A, and the vinyl benzyl ether resin described in paragraph 0041 of JP 2019-194312 A, and the like, the contents of which are incorporated herein by reference.

[0149] <<Compounds having an isopropenyl group other than resin (A) having an indane skeleton>> The resin composition of the present embodiment may contain a compound having an isopropenyl group other than the resin (A) having an indane skeleton. Details of these are exemplified by resins having an isopropenyl group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 1, 2, 7, and 8 of the same publication), the contents of which are incorporated herein by reference.

[0150] <<Polyfunctional (meth)acrylate compounds other than the polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond>> The resin composition of this embodiment may contain a polyfunctional (meth)acrylate compound other than the polyphenylene ether compound (B) having a terminal carbon-carbon unsaturated double bond. Here, the polyfunctional (meth)acrylate compound means a compound containing two or more (meth)acryloyloxy groups in one molecule, and preferably contains three or more (meth)acryloyloxy groups in one molecule. The polyfunctional (meth)acrylate compound is preferably a compound having 3 to 5 (meth)acryloyloxy groups, more preferably a compound having 3 or 4 (meth)acryloyloxy groups, and even more preferably a compound having 3 (meth)acryloyloxy groups. The (meth)acrylate compound is preferably a compound having a methacryloyloxy group. The polyfunctional (meth)acrylate compound has a large number of (meth)acrylate groups that serve as crosslinking points, and therefore is firmly cured with the resin (A), the polyphenylene ether compound (B), and other resin components (e.g., other compounds (C)), resulting in a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. As the polyfunctional (meth)acrylate compound, a compound represented by formula (MA) is preferred. Formula (MA) [ka] (In formula (MA), R 1 represents a hydrogen atom or a substituent, and R 2 each independently represents a hydrogen atom or a methyl group.

[0151] In formula (MA), R 1 represents a hydrogen atom or a substituent, and is more preferably a substituent having a formula weight of 15 to 500, more preferably a substituent having a formula weight of 15 to 300, even more preferably a substituent having a formula weight of 15 to 100, and still more preferably a substituent having a formula weight of 15 to 50.

[0152] R 1 is preferably a hydrocarbon group or a (meth)acryloyloxy group, more preferably a hydrocarbon group having 22 or less carbon atoms, and even more preferably an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using a compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, it is possible to provide a resin composition that has excellent crosslinkability and is capable of giving a cured product having high toughness. This makes it possible to suppress cracking during etching treatments and the like, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 2 or more, and may be 8 or more, or may be 12 or more and 18 or less. This improves the resin flow properties of the resin composition, and is thought to result in better circuit filling properties when a multilayer circuit board or the like is produced using the resin composition of the present embodiment.

[0153] In this embodiment, the (meth)acrylic group equivalent of the compound represented by formula (MA) is preferably 1000 g / eq or less. If the equivalent is 1000 g / eq or less, a high Tg tends to be more reliably obtained. The lower limit of the (meth)acrylic group equivalent is, for example, 99 g / eq or more.

[0154] The alkyl group having 1 to 22 carbon atoms is preferably a linear alkyl group having 1 to 22 carbon atoms or a branched alkyl group having 3 to 22 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a docosyl group, etc. The alkenyl group having 2 to 22 carbon atoms is preferably an alkenyl group having 2 to 15 carbon atoms, such as an allyl group, a decenyl group, etc.

[0155] Specific examples of the compound represented by formula (MA) include trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetra(meth)acrylate, etc. These may be used alone or in combination of two or more, or may be used as a prepolymer.

[0156] The compound represented by formula (MA) may also be commercially available. Although there is no particular limitation on commercially available compounds, examples thereof include trimethylolpropane trimethacrylate, such as "NK Ester TMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.

[0157] The molecular weight of the polyfunctional (meth)acrylate compound is preferably 300 or more, more preferably 330 or more, and may be 400 or more, or even 500 or more. By setting the molecular weight to the above-mentioned lower limit or more, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)acrylate compound (preferably a compound represented by formula (MA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to the above-mentioned upper limit or less, the low thermal expansion properties of the obtained cured product tend to be further improved.

[0158] For details of these, examples include resins having a (meth)acrylic group described in WO 2022 / 210095 (for example, the compounds described in Synthesis Examples 5 and 21 of the same publication) and resins having a (meth)acrylic group described in Japanese Patent No. 6962507 (for example, the compounds described in Examples 1 to 9), the contents of which are incorporated herein by reference.

[0159] When the resin composition of this embodiment contains a polyfunctional (meth)acrylate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the polyfunctional (meth)acrylate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)acrylate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the polyfunctional (meth)acrylate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one type of polyfunctional (meth)acrylate compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0160] <<Elastomer>> The resin composition of the present embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but is preferably thermoplastic. The elastomer in this embodiment is not particularly limited, and examples thereof include at least one selected from the group consisting of polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. Further, examples of elastomers include oligomers or polymers having a curable vinyl functional group, and polybutadiene resins described in paragraphs 0044 and 0045 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0161] The number-average molecular weight of the elastomer (preferably a thermoplastic elastomer) used in this embodiment is preferably 1000 or more. By setting the number-average molecular weight to 1000 or more, the low dielectric properties (Dk and / or Df, particularly low dielectric dissipation factor) of the resulting cured product tend to be more excellent. The number-average molecular weight is preferably 1500 or more, more preferably 2000 or more, and may be 600,000 or more, 700,000 or more, or 800,000 or more depending on the application, etc. The upper limit of the number-average molecular weight of the elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. Setting the number-average molecular weight below the upper limit tends to improve the solubility of the elastomer component in the resin composition. When the resin composition of the present embodiment contains two or more elastomers, it is preferable that the number average molecular weight of the mixture thereof falls within the above range.

[0162] The elastomer used in this embodiment may be a resin containing a polybutadiene structure. The polybutadiene structure may be partially or completely hydrogenated. Specific examples include B-1000, B-2000, B-3000, BI-2000, and BI-3000 manufactured by Nippon Soda Co., Ltd., and Ricon 100, Ricon 130, Ricon 131, Ricon 142, Ricon 150, Ricon 181, and Ricon 184 manufactured by Cray Valley.

[0163] The elastomer used in this embodiment may be a resin containing a poly(meth)acrylate structure, such as Teisan Resin manufactured by Nagase ChemteX Corporation, and ME-2000, W-197C, KG-15, and KG-3000 manufactured by Negami Chemical Industrial Co., Ltd.

[0164] The elastomer used in this embodiment may be a resin containing a polycarbonate structure. Resins containing a polycarbonate structure are sometimes referred to as "polycarbonate resins." Examples of such resins include carbonate resins without reactive groups, hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, urethane group-containing carbonate resins, and epoxy group-containing carbonate resins. Here, the term "reactive group" refers to a functional group capable of reacting with other components, such as a hydroxy group, a phenolic hydroxyl group, a carboxy group, an acid anhydride group, an isocyanate group, a urethane group, or an epoxy group. Specific examples of polycarbonate resins include FPC0220 and FPC2136 manufactured by Mitsubishi Gas Chemical Company, Inc., and T6002 and T6001 (polycarbonate diol) manufactured by Asahi Kasei Chemicals Corporation.

[0165] The elastomer used in this embodiment is a resin containing a polysiloxane structure, such as SMP-2006, SMP-2003PGMEA, SMP-5005PGMEA, KR-510, and SMP-7014-3S manufactured by Shin-Etsu Silicones Co., Ltd.

[0166] The elastomer used in this embodiment may be a resin containing a polyalkylene structure and / or a polyalkyleneoxy structure. The polyalkyleneoxy structure is preferably a polyalkyleneoxy structure having 2 to 15 carbon atoms, more preferably a polyalkyleneoxy structure having 3 to 10 carbon atoms, and particularly preferably a polyalkyleneoxy structure having 5 to 6 carbon atoms. Specific examples of resins containing a polyalkylene structure and / or a polyalkyleneoxy structure include PTXG-1000 and PTXG-1800 manufactured by Asahi Kasei Fibers Corporation.

[0167] The elastomer used in this embodiment is a resin containing a polyisoprene structure, and specific examples include KL-610 and KL613 manufactured by Kuraray Co., Ltd.

[0168] The elastomer used in this embodiment may be a resin containing a polyisobutylene structure, such as SIBSTAR-073T (styrene-isobutylene-styrene triblock copolymer) and SIBSTAR-042D (styrene-isobutylene diblock copolymer), both manufactured by Kaneka Corporation.

[0169] In this embodiment, the elastomer is preferably an elastomer containing styrene monomer units and conjugated diene monomer units (hereinafter referred to as "elastomer (e)"). By using such elastomer (e), the low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent) of the resulting cured product are improved.

[0170] The elastomer (e) contains a styrene monomer unit. The inclusion of the styrene monomer unit improves the solubility of the elastomer (e) in the resin composition. Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Among these, styrene, α-methylstyrene, and p-methylstyrene are preferred from the viewpoints of availability and productivity. Among these, styrene is particularly preferred. The content of styrene monomer units in the elastomer (e) is preferably in the range of 10 to 50% by mass of all monomer units, more preferably in the range of 13 to 45% by mass, and even more preferably in the range of 15 to 40% by mass. If the content of styrene monomer units is 50% by mass or less, the adhesion and tackiness to substrates and the like will be better. Furthermore, if the content is 10% by mass or more, the adhesion can be suppressed, adhesive residue and stop marks are less likely to occur, and the adhesive surfaces tend to be easily peeled from each other, which is preferable. The elastomer (e) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The method for measuring the content of styrene monomer units in the elastomer (e) of this embodiment can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the content of conjugated diene monomer units, etc., described below.

[0171] The elastomer (e) contains a conjugated diene monomer unit. The inclusion of the conjugated diene monomer unit improves the solubility of the elastomer (e) in the resin composition. The conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds. Examples of the conjugated diene monomer include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene. 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. The elastomer (e) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

[0172] In the elastomer (e), the mass ratio of the styrene monomer units to the conjugated diene monomer units is preferably in the range of 5 / 95 to 80 / 20, more preferably 7 / 93 to 77 / 23, and even more preferably 10 / 90 to 70 / 30. When the mass ratio of the styrene polymer units to the conjugated diene monomer units is in the range of 5 / 95 to 80 / 20, adhesion can be suppressed, high adhesion strength can be maintained, and easy peeling of the adhesive surfaces can be improved.

[0173] The conjugated diene bonds of the elastomer (e) may be entirely hydrogenated, partially hydrogenated, or not hydrogenated at all.

[0174] The elastomer (e) may or may not contain other monomer units in addition to the styrene monomer units and conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than the styrene monomer units. In the elastomer (e), the sum of styrene monomer units and conjugated diene monomer units preferably accounts for 90% by mass or more of all monomer units, more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more. As described above, the elastomer (e) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range.

[0175] The elastomer (e) used in this embodiment may be a block polymer or a random polymer. It may also be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, an unhydrogenated elastomer in which the conjugated diene monomer units are not hydrogenated, or a partially hydrogenated elastomer in which the conjugated diene monomer units are partially hydrogenated, and is preferably an unhydrogenated elastomer or a partially hydrogenated elastomer. In one embodiment of this embodiment, the elastomer (e) is a hydrogenated elastomer. Here, the hydrogenated elastomer means, for example, an elastomer in which double bonds based on conjugated diene monomer units in the elastomer have been hydrogenated, and includes elastomers with a hydrogenation rate (hydrogenation rate) of 100% or more as well as elastomers with a hydrogenation rate of 80% or more. The hydrogenation rate in the hydrogenated elastomer is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more. In this embodiment, the hydrogenation rate is 1 It is calculated from the results of H-NMR spectroscopy. In one embodiment of this embodiment, the elastomer (e) is an unhydrogenated elastomer. Here, the unhydrogenated elastomer refers to an elastomer in which the proportion of hydrogenated double bonds based on conjugated diene monomer units in the elastomer, i.e., the hydrogenation rate (hydrogenation rate), is 20% or less. The hydrogenation rate is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less. On the other hand, a partially hydrogenated elastomer means an elastomer in which some of the double bonds based on the conjugated diene monomer units in the elastomer have been hydrogenated, and usually refers to an elastomer in which the hydrogenation rate (hydrogenation rate) is less than 80% but more than 20%.

[0176] Examples of commercially available elastomers (e) used in the present embodiment include SEPTON (registered trademark) 2104, V9461, and S8104 manufactured by Kuraray Co., Ltd., SOE (registered trademark) S1606, S1613, S1609, and S1605 manufactured by Asahi Kasei Corporation, Tuftec (registered trademark) H1041, H1043, P2000, and MP10 manufactured by Asahi Kasei Corporation, and DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Corporation.

[0177] The elastomer used in this embodiment may also be a liquid diene. Liquid diene refers to a liquid elastomer containing a conjugated diene monomer unit. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene. 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. Examples of the liquid diene used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, liquid acrylonitrile-butadiene copolymer, and liquid styrene-butadiene copolymer. The number average molecular weight of the liquid diene is not particularly limited as long as it is liquid at 20°C, but is preferably 500 or more and 10,000 or less.

[0178] When the resin composition of this embodiment contains an elastomer (preferably, elastomer (e)), the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, the content may be 10 parts by mass or more, or 12 parts by mass or more. By setting the content at or above the lower limit, the dielectric properties (low dielectric tangent) tend to be further improved. Furthermore, the upper limit of the elastomer content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 32 parts by mass or less, and even more preferably 28 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content at or below the upper limit, the heat resistance tends to be further improved. The resin composition of the present embodiment may contain only one type of elastomer, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of elastomer, meaning that the content of elastomer is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0179] <<Petroleum resin>> The resin composition of the present embodiment may contain a petroleum resin, which can reduce the melt viscosity. Petroleum resins are resins obtained by thermally cracking petroleum naphtha to extract necessary fractions, and then polymerizing the remaining components without isolating unsaturated hydrocarbons, either without a catalyst or in the presence of a catalyst. The remaining fractions are primarily fractions containing C5 fractions (isoprene, piperylene, cyclopentadiene, pentenes, pentanes, etc.) or C9 fractions (vinyltoluene, indene, dicyclopentadiene, etc.).

[0180] The catalyst used in the production of petroleum resins 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, and iron (III) bromide; solid acids such as zeolite, silica, montmorillonite, and alumina; ion exchange resins such as sulfonic acid group-containing fluororesins and sulfonic acid group-containing polystyrene resins; and protonic acids such as sulfuric acid, hydrochloric acid, acetic acid, phosphoric acid, oxalic acid, nitric acid, paratoluenesulfonic acid, and trifluoroacetic acid can be used. Among these, Lewis acids and solid acids are preferred because they are less likely to cause side reactions and have a fast reaction rate, and various boron trifluoride complexes and aluminum chloride are more preferred because of their ease of availability and high reactivity.

[0181] The weight-average molecular weight of the petroleum resin is not particularly limited, but is preferably 500 to 10,000, and more preferably 500 to 5,000. By setting it to the upper limit or less, compatibility with other resins tends to be improved and solubility in solvents also tends to be increased. By setting it to the lower limit or more, the heat resistance and mechanical strength of the resulting cured product tend to be further improved.

[0182] Although the softening point of the petroleum resin is not particularly limited, it is preferably high, preferably at least 80° C., and more preferably at least 100° C. By ensuring that the softening point is at least the above lower limit, the heat resistance of the resulting cured product tends to be improved.

[0183] 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-based petroleum resins include resins obtained by polymerizing dicyclopentadiene-based fractions such as dicyclopentadiene, isopropenylnorbornene, dimethyldicyclopentadiene, and tricyclopentadiene, and resins obtained by polymerizing dicyclopentadiene-based fractions with other monomers having unsaturated bonds, preferably unsaturated cyclic olefins.

[0184] Examples of the unsaturated cyclic olefins include cyclopentadiene; norbornene-based 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, examples of tricyclic or higher norbornene-based monomers include tricyclic monomers other than dicyclopentadiene-based fractions such as diethyldicyclopentadiene and dihydrodicyclopentadiene, tetracyclic monomers such as tetracyclododecene, pentacyclic monomers such as tricyclopentadiene, and heptacyclic monomers such as tetracyclopentadiene, and alkyl-substituted, alkylidene-substituted, and aryl-substituted products of these polycyclic monomers. Examples of the alkyl-substituted polycyclic compounds include methyl, ethyl, propyl, and butyl-substituted compounds, and examples of the alkylidene-substituted polycyclic compounds include ethylidene-substituted compounds. Examples of the aryl-substituted polycyclic compounds include phenyl, tolyl, and naphthyl-substituted compounds.

[0185] Furthermore, as a monomer having an unsaturated bond other than the unsaturated cyclic olefins, an olefin having 3 to 12 carbon atoms may be copolymerized. For example, α-olefins such as propylene, butene-1, pentene-1, 1,3-pentadiene, hexene-1, heptene-1, octene-1, diisobutene, 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.

[0186] Examples of monomers having an unsaturated bond other than those mentioned above include ethylene, tetrafluoroethylene, fluoroethylene, 1,1-difluoroethylene, trifluoroethylene; alkyl styrenes such as styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, 3,4-dimethylstyrene, 3,5-dimethylstyrene, and pt-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; maleic anhydride, maleic acid, fumaric acid, allyl alcohol, 3-buten-2-ol, methylbuten-1-ol, vinyl acetate, and vinyl chloride.

[0187] The above monomers may be used alone or in combination of two or more kinds.

[0188] 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 manufactured by Zeon Corporation, and Marucaretz T-100AS and Marucaretz R-100AS manufactured by Maruzen Petrochemical Co., Ltd.; and aromatic petroleum resins include Neopolymer L-90, Neopolymer 120, and Neopolymer 130 manufactured by JXTG Nippon Oil & Energy Corporation. Polymer 130, Neopolymer 140, Neopolymer 150, Neopolymer 170S, Neopolymer 160, Neopolymer E-100, Neopolymer E-130, Neopolymer 130S, Neopolymer S, Tosoh Corporation's Petcol LX, Petcol LX-HS, Petcol 100T, Petcol 120, Petcol 120HS, Petcol 130, Petcol 140, Petcol 140HM, Petcol 140HM5, Petcol 150, Petcol Coal 150AS, copolymer petroleum resins such as Quinton D100, Quinton N180, Quinton P195N, Quinton S100, Quinton S195, Quinton U185, Quinton G100B, Quinton G115, Quinton D200, Quinton E200SN, and Quinton N295 manufactured by Zeon Corporation, and Petrotack 60, Petrotack 70, Petrotack 90, Petrotack 90V, and Petrotack 100 manufactured by Tosoh Corporation. , Petrotack 100V, Petrotack 90HM, and DCPD (dicyclopentadiene)-based petroleum resins such as Marucaretz M-890A and Marucaretz M-845A manufactured by Maruzen Petrochemical Co., Ltd., Quinton 1325, Quinton 1345, Quinton 1500, Quinton 1525L, and Quinton 1700 manufactured by Zeon Corporation, and HA085, HA103, HA105, HA125, HB103, and HB125 manufactured by ENEOS Corporation. Furthermore, as the petroleum resin, those described in Organic Synthetic Chemistry, Vol. 25, No. 6 (1967) can also be used.

[0189] When the resin composition of this embodiment contains a 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 the resin solid content in the resin composition. By setting the content at or above the lower limit, the melt viscosity tends to decrease. Furthermore, 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 the resin solid content in the resin composition. By setting the content at or below the upper limit, the Df tends to decrease. The resin composition in the present embodiment may contain only one type of petroleum resin, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of petroleum resin, meaning that the content of petroleum resin is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0190] <Filling material (D)> The resin composition of the present embodiment preferably contains a filler (D). By containing the filler (D), the physical properties of the resin composition and its cured product, such as low dielectric properties (Dk and / or Df), flame resistance, and low thermal expansion, can be further improved. Furthermore, the filler (D) used in this embodiment preferably has excellent low dielectric properties (Dk and / or Df). For example, the filler (D) used in this embodiment preferably has a relative dielectric constant (Dk) of 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less at a frequency of 10 GHz, measured according to the cavity resonator perturbation method. Furthermore, a practical lower limit for the relative dielectric constant is, for example, 2.0 or more. Furthermore, the filler (D) used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, at a frequency of 10 GHz, measured according to the cavity resonator perturbation method. Furthermore, a practical lower limit for the dielectric loss tangent is, for example, 0.0001 or more.

[0191] The filler (D) used in this embodiment is not particularly limited in type, and those generally used in the art can be suitably used. Specific examples include silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, and hollow silica; metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, and zirconium oxide; composite oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, and calcium titanate; nitrides such as boron nitride, aggregated boron nitride, silicon nitride, and aluminum nitride; aluminum hydroxide; heat-treated aluminum hydroxide (aluminum hydroxide that has been heat-treated to remove some of the water of crystallization); boehmite; and metal hydroxides (including hydrates) such as magnesium hydroxide. Examples of fillers include inorganic fillers such as molybdenum compounds such as barium sulfate and zinc molybdate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, short glass fibers (including fine glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, and spherical glass, as well as organic fillers such as styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell-type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders. In this embodiment, inorganic fillers are preferred, and more preferably include one or more selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. From the viewpoint of low dielectric properties (Dk and / or Df), more preferably include one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferably include silica. The use of these inorganic fillers further improves the heat resistance, low dielectric properties (Dk and / or Df), thermal expansion properties, dimensional stability, flame retardancy, and other properties of the cured product of the resin composition.

[0192] The content of filler (D) in the resin composition of this embodiment can be appropriately set depending on the desired properties and is not particularly limited. However, it is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 40 parts by mass or more, even more preferably 60 parts by mass or more, and even more preferably 80 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content at or above the lower limit, the heat resistance, low thermal expansion, and low dielectric loss tangent of the resulting cured product tend to be further improved. Furthermore, the upper limit of the content of filler (D) is preferably 1,000 parts by mass or less, more preferably 500 parts by mass or less, even more preferably 300 parts by mass or less, even more preferably 250 parts by mass or less, and may be 200 parts by mass or less, or 120 parts by mass or less, per 100 parts by mass of the resin solid content. By setting the content at or below the upper limit, the moldability of the resin composition tends to be further improved. In the resin composition of the present embodiment, one preferred embodiment is one in which the content of the filler (D) is 30% by mass to 90% by mass of the components excluding the solvent. The resin composition of the present embodiment may contain only one type of filler (D), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0193] When the resin composition of this embodiment uses a filler (D), particularly an inorganic filler, it may further contain a silane coupling agent. The inclusion of a silane coupling agent tends to further improve the dispersibility of the filler (D) and the adhesive strength between the resin component and the filler (D) and the substrate described below. The silane coupling agent is not particularly limited, and examples thereof include silane coupling agents generally used for surface treatment of inorganic 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, etc.), styrylsilane compounds, acrylicsilane compounds (e.g., γ-acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), phenylsilane compounds, etc. Silane coupling agents 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 relative to 100 parts by mass of the resin solid content.

[0194] <Monomer or oligomer having an ethylenically unsaturated group> The resin composition of this embodiment can also contain a monomer or oligomer having an ethylenically unsaturated group in order to enhance the thermosetting property and curability with active energy rays (for example, photocurability with ultraviolet light). The oligomer or monomer having an ethylenically unsaturated group used in this embodiment is not particularly limited as long as it is an oligomer or monomer having one or more ethylenically unsaturated groups in one molecule. Examples include monomers or oligomers having a vinyl group, an isopropenyl group, an allyl group, a (meth)acryloyl group, etc., and a monomer or oligomer having a vinyl group is preferred. In this specification, a compound that corresponds to a monomer or oligomer having an ethylenically unsaturated group and also corresponds to a polyphenylene ether compound containing a terminal carbon-carbon unsaturated double bond is referred to as a polyphenylene ether compound containing a terminal carbon-carbon unsaturated double bond.

[0195] More specifically, the monomer having an ethylenically unsaturated group may be a compound (F1) (compound (F1)) having a molecular weight of less than 1,000 and containing one organic group containing an ethylenically unsaturated bond in the molecule. The ethylenically unsaturated bond constituting the organic group containing an ethylenically unsaturated bond does not include an ethylenically unsaturated bond contained as part of an aromatic ring. On the other hand, the ethylenically unsaturated bond is intended to include an ethylenically unsaturated bond contained as part of a non-aromatic ring. An example of an ethylenically unsaturated bond contained as part of a non-aromatic ring is a cyclohexenyl group in a molecule. The ethylenically unsaturated bond is also intended to include an ethylenically unsaturated bond contained in a portion other than the terminal of a linear or branched organic group, i.e., in a linear or branched chain. The organic group containing an ethylenically unsaturated bond is more preferably one selected from the group consisting of a vinyl group, an allyl group, an acryloyl group, and a methacryl group, and even more preferably a vinyl group. In this specification, a compound that corresponds to a monomer or oligomer having an ethylenically unsaturated group and also corresponds to a silane coupling agent is referred to as a silane coupling agent.

[0196] The compound (F1) used in the present embodiment is preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, nitrogen atoms, and silicon atoms, more preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, and silicon atoms, and even more preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, and oxygen atoms. The compound (F1) used in this embodiment may or may not have a polar group. It is preferable that the compound (F1) used in this embodiment does not have a polar group. Examples of the polar group include an amino group, a carboxyl group, a hydroxyl group, and a nitro group.

[0197] In this embodiment, the molecular weight of compound (F1) is preferably 70 or more, more preferably 80 or more, and even more preferably 90 or more. By setting the molecular weight at or above the lower limit, volatilization of compound (F1) from the resin composition of this embodiment or a cured product thereof tends to be suppressed. The upper limit of the molecular weight of compound (F1) is preferably 500 or less, more preferably 400 or less, even more preferably 300 or less, still more preferably 200 or less, and may be 150 or less. By setting the molecular weight at or below the upper limit, the effect of increasing reactivity with other resin components tends to be further improved. When the resin composition of the present embodiment contains two or more types of compound (F1), it is preferable that the average molecular weight value of the compound (F1) falls within the above range, and it is more preferable that the molecular weight of each compound falls within the above preferred range.

[0198] In this embodiment, the boiling point of compound (F1) is preferably 110°C or higher, more preferably 115°C or higher, and even more preferably 120°C or higher. By setting the boiling point at or above the lower limit, volatilization of compound (F1) during thermal curing of the resin composition is suppressed, allowing the thermosetting compound and compound (F1) to react with each other. The boiling point of compound (F1) is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower. By setting the boiling point at or below the upper limit, it is possible to reduce the likelihood of the compound (F1) remaining as a residual solvent in the cured product. When the resin composition of the present embodiment contains two or more compounds (F1), the average boiling point may be within the above range, but it is preferable that the boiling point of each compound falls within the above preferred range. Examples of the compound (F1) include (meth)acrylic acid ester compounds, aromatic vinyl compounds (preferably styrene-based compounds), isopropenyl group-containing compounds, saturated fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides, ethylenically unsaturated dicarboxylic acid monoalkyl esters, ethylenically unsaturated carboxylic acid amides, unsaturated polyester compounds based on maleic anhydride, fumaric acid, itaconic acid, and citraconic acid; unsaturated epoxy (meth)acrylate compounds containing an acryloyl group or a methacryloyl group; unsaturated epoxy (meth)acrylate compounds containing a vinyl group or a (meth)allyl group; Examples include saturated epoxy compounds, urethane (meth)acrylate compounds, polyether (meth)acrylate compounds, polyalcohol (meth)acrylate compounds, alkyd acrylate compounds, polyester acrylate compounds, spiroacetal acrylate compounds, diallyl phthalate compounds, diallyl tetrabromophthalate compounds, diethylene glycol bisallyl carbonate, and polyethylene polythiol. At least one selected from the group consisting of (meth)acrylic acid ester compounds, aromatic vinyl compounds, and saturated fatty acid vinyl compounds is preferred, and aromatic vinyl compounds are more preferred. Specific examples of compound (F1) include methylstyrene (e.g., 4-methylstyrene), ethylvinylbenzene, diethyl 4-vinylbenzylphosphonate, 4-vinylbenzyl glycidyl ether, α-methylstyrene, etc. Specific examples of compound (F1) can be found in paragraphs 0046 and 0049 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0199] On the other hand, the resin composition according to this embodiment preferably contains a styrene oligomer (F2) in order to improve the low dielectric properties (Dk and / or Df) of the resulting cured product. The styrene oligomer (F2) according to this embodiment is preferably obtained by polymerizing at least one selected from the group consisting of styrene, the styrene derivatives, and vinyltoluene. The number average molecular weight of the styrene oligomer (F2) is preferably 178 or more and 1600 or less. The styrene oligomer (F2) is preferably a compound having an average number of aromatic rings of 2 to 14, a total amount of the 2 to 14 aromatic rings of 50 mass% or more, and an unbranched structure with a boiling point of 300°C or more.

[0200] Examples of the styrene oligomer (F2) used in this embodiment include styrene polymers, vinyltoluene polymers, α-methylstyrene polymers, vinyltoluene-α-methylstyrene polymers, and styrene-α-styrene polymers. Commercially available styrene polymers may be used, including Picolastic A5 (manufactured by Eastman Chemical Co.), Picolastic A-75 (manufactured by Eastman Chemical Co.), Picotex 75 (manufactured by Eastman Chemical Co.), FTR-8100 (manufactured by Mitsui Chemicals, Inc.), and FTR-8120 (manufactured by Mitsui Chemicals, Inc.). Examples of vinyltoluene-α-methylstyrene polymers include Picotex LC (manufactured by Eastman Chemical Co.). Examples of α-methylstyrene polymers include CRYSTALEX 3070 (manufactured by Eastman Chemical Co.), CRYSTALEX 3085 (manufactured by Eastman Chemical Co.), CRYSTALEX (3100), CRYSTALEX 5140 (manufactured by Eastman Chemical Co.), FMR-0100 (manufactured by Mitsui Chemicals, Inc.), and FMR-0150 (manufactured by Mitsui Chemicals, Inc.). Examples of styrene-α-styrene polymers include FTR-2120 (manufactured by Mitsui Chemicals, Inc.). These styrene oligomers may be used alone or in combination of two or more. In the resin composition of this embodiment, α-methylstyrene oligomer is preferred because it cures well with heat, has good embedding properties for fine wiring, solder heat resistance, and low dielectric properties (Dk and / or Df).

[0201] Furthermore, the resin composition according to this embodiment preferably contains a divinyl compound (F3) as a monomer having an ethylenically unsaturated group in order to improve low dielectric constant and low dielectric loss tangent. Divinyl compounds are low-molecular-weight compounds containing two vinyl groups. The two vinyl groups result in a moderately high crosslink density, resulting in a large molecular free volume, which in turn reduces the dielectric loss tangent (Df) of the resulting cured product. Furthermore, because divinyl compound (F3) is used as a substitute for resin (A), polyphenylene ether compound (B), and part of other curable compounds, the reduced content of components containing polar groups is also thought to contribute to a reduction in the dielectric loss tangent (Df). Furthermore, because both functional groups on the divinyl compound are vinyl groups, it exhibits good reactivity with resin (A) and polyphenylene ether compound (B), which is thought to result in improved heat resistance. The divinyl compound (F3) here refers to one having a molecular weight of less than 600, preferably 300 or less, and more preferably less than 195. The lower limit of the molecular weight is practically 54. Examples of the divinyl compound (F3) include divinylbenzene, 1-ethynyl-4-[2-(4-ethynylphenyl)ethyl]benzene (BVPE), , 1,3-vinyltetramethylsiloxane, and the like.

[0202] In addition, 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene are also preferably used as the monomer or oligomer having an ethylenically unsaturated group. For details of the monomer or oligomer having an ethylenically unsaturated group, please refer to paragraphs 0069 to 0087 of WO 2017 / 135168 and paragraphs 0065 to 0067 of WO 2019 / 230945, the contents of which are incorporated herein by reference.

[0203] When the resin composition of this embodiment contains a monomer or oligomer having an ethylenically unsaturated group, the content thereof is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, even more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even optionally 5 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content is equal to or greater than the above-mentioned lower limit, the low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. Furthermore, the upper limit for the content of the monomer or oligomer having an ethylenically unsaturated group is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content is equal to or less than the above-mentioned upper limit, the heat resistance tends to be further improved. Furthermore, the low dielectric properties (Dk and / or Df) and chemical resistance of the resulting cured product tend to be further improved. The resin composition of the present embodiment may contain only one type of monomer or oligomer having an ethylenically unsaturated group, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0204] <Flame retardant> The resin composition of this embodiment may contain a flame retardant. Examples of the flame retardant include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, and phosphorus-based flame retardants are preferred. As the flame retardant, known ones can be used, for example, halogen-based flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, and chlorinated paraffin, red phosphorus, tricresyl phosphate, triphenyl phosphate, and cresyl diphenyl phosphate. Examples of flame retardants include phosphorus-based flame retardants such as phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl)phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), and 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide; 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. Among these, 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferred in this embodiment because it does not impair the low dielectric properties (Dk and / or Df) of the resulting cured product.

[0205] When the resin composition of this embodiment contains a flame retardant, the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The lower limit of the content of the flame retardant is preferably 30 parts by mass or less, more preferably 25 parts by mass or less. The flame retardants can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0206] <Active ester compounds> The resin composition of this embodiment may contain an active ester compound. The active ester compound is not particularly limited, and for example, the description in paragraphs 0064 to 0066 of WO 2021 / 172317 can be referred to, the contents of which are incorporated herein by reference.

[0207] When the resin composition of the present embodiment contains an active ester compound, the amount thereof is preferably 1 part by mass or more and 90 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of the present embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may also be configured to be substantially free of active ester compounds, which means that the content of the active ester compounds is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0208] <Dispersant> The resin composition of the present embodiment may contain a dispersant. As the dispersant, those generally used for paints can be suitably used, and the type thereof is not particularly limited. As the dispersant, a copolymer-based wetting dispersant or a fluorine-containing dispersant is preferably used. Specific examples of dispersants include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, and W940 manufactured by BYK Japan K.K., Futergent manufactured by Neos Corporation, and MPT manufactured by Mitsubishi Pencil Co., Ltd.

[0209] When the resin composition of this embodiment contains a dispersant, the lower limit of the content is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and may be 0.3 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. The upper limit of the dispersant content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 3 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. The dispersant may be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0210] <Curing accelerator> The resin composition of the present embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, and examples thereof include imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; organic peroxides such as benzoyl peroxide, bis(1-methyl-1-phenylethyl)peroxide, di-t-butyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, α,α'-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitriles (e.g., azobisisobutyronitrile); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, and thiazolinone. tertiary amines such as tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition type radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetonate; compounds obtained by dissolving these organic metal salts in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organic tin compounds such as dioctyltin oxide, other alkyltins, and alkyltin oxides. The curing accelerator is preferably at least one selected from the group consisting of imidazoles, organic peroxides, and organic metal salts, more preferably at least one selected from the group consisting of imidazoles and organic metal salts, and even more preferably an imidazole. Furthermore, in this embodiment, the resin composition may be configured to be substantially free of polymerization initiators such as organic peroxides, azo compounds, etc. "Substantially free" means that the content of the polymerization initiator is less than 0.1 part by mass, preferably less than 0.01 part by mass, and more preferably less than 0.001 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0211] When the resin composition of this embodiment contains a curing accelerator, the lower limit of the content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.1 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 2 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The curing accelerators can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0212] <Solvent> The resin composition of this embodiment may contain a solvent, preferably an organic solvent. When a solvent is contained, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the various resin solid components described above are dissolved or compatible in the solvent. The solvent is not particularly limited as long as it is a polar or non-polar organic solvent that can dissolve or compatible in at least a portion, preferably all, of the various resin solid components described above. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosolves (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and amides (e.g., dimethoxyacetamide, dimethylformamide, etc.). Examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). The solvents can be used alone or in combination of two or more. When two or more solvents are used, the total amount falls within the above range.

[0213] <Other ingredients> In addition to the above components, the resin composition of this embodiment may contain various polymeric compounds such as thermoplastic resins and their oligomers, as well as various additives. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow control agents, lubricants, antifoaming agents, leveling agents, gloss agents, and polymerization inhibitors. These additives may be used alone or in combination of two or more. The resin composition of this embodiment may also be configured to be substantially free of a polymerization inhibitor. "Substantially free" means that the resin composition does not contain a polymerization inhibitor, or the content of the polymerization inhibitor in the resin composition is, for example, less than 0.008 parts by mass, preferably 0.007 parts by mass or less, more preferably 0.001 parts by mass or less, and even more preferably 0.0001 parts by mass or less, per 100 parts by mass of the resin solid content.

[0214] <Application> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low-dielectric-constant material and / or a low-dielectric-tangent material, such as an insulating layer for a printed wiring board, a semiconductor package material, or other electronic material resin composition. The resin composition of this embodiment can be suitably used as a material for prepregs, metal foil-clad laminates using prepregs, resin composite sheets, and printed wiring boards.

[0215] The resin composition of this embodiment is used as a layered material (including film and sheet forms) such as a prepreg or resin composite sheet that serves as an insulating layer for a printed wiring board. When used as such a layered material, the thickness is preferably 5 μm or more, more preferably 10 μm or more. The upper limit of the thickness is preferably 200 μm or less, more preferably 180 μm or less. Note that the thickness of the layered material refers to the thickness including the glass cloth when, for example, the resin composition of this embodiment is impregnated into glass cloth or the like. The material formed from the resin composition of the present embodiment may be used for applications in which a pattern is formed by exposure and development, or for applications in which no exposure and development is required. It is particularly suitable for applications in which no exposure and development is required.

[0216] <<Prepreg>> The prepreg of this embodiment is formed from a substrate (prepreg substrate) and the resin composition of this embodiment. The prepreg of this embodiment can be obtained, for example, by applying the resin composition of this embodiment to the substrate (e.g., by impregnation and / or coating) and then semi-curing by heating (e.g., by drying at 120 to 220°C for 2 to 15 minutes). In this case, the amount of the resin composition attached to the substrate, i.e., the amount of the resin composition (including the filler (D)) relative to the total amount of the semi-cured prepreg, is preferably in the range of 20 to 99% by mass, more preferably in the range of 20 to 80% by mass.

[0217] The substrate is not particularly limited as long as it is a substrate used in various printed wiring board materials. Examples of the substrate material include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, NER-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited, and examples include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc. These substrates may be used alone or in combination of two or more. Among these substrates, woven fabrics that have been subjected to an ultra-opening treatment and a clogging treatment are preferred from the viewpoint of dimensional stability. From the viewpoint of strength and low water absorption, the substrate should have a thickness of 200 μm or less and a mass of 250 g / m. 2 The following glass woven fabrics are preferred, and from the viewpoint of moisture absorption and heat resistance, glass woven fabrics that have been surface-treated with a silane coupling agent such as epoxy silane or amino silane are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers exhibiting low dielectric properties (Dk and / or Df), such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. An example of a substrate with a low relative dielectric constant is a substrate with a relative dielectric constant of 5.0 or less (preferably 3.0 to 4.9). An example of a substrate with a low dielectric loss tangent is a substrate with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The relative dielectric constant and dielectric loss tangent are values ​​measured at a frequency of 10 GHz using a perturbation method cavity resonator.

[0218] <<Metal foil clad laminate>> The metal foil-clad laminate of this embodiment includes at least one layer formed from the prepreg of this embodiment and a metal foil disposed on one or both sides of the layer formed from the prepreg. Examples of methods for producing the metal foil-clad laminate of this embodiment include a method in which at least one prepreg of this embodiment (preferably two or more prepregs) is disposed, and a metal foil is disposed on one or both sides of the prepreg, followed by lamination molding. More specifically, the laminate can be produced by disposing a metal foil, such as copper or aluminum, on one or both sides of the prepreg, followed by lamination molding. The number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil may be any foil suitable for use in printed wiring boards, and examples thereof include copper foils such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited and may be approximately 1.5 to 70 μm. Furthermore, when copper foil is used as the metal foil, the copper foil preferably has a surface roughness Rz of 0.2 to 4.0 μm, as measured in accordance with JIS B0601:2013. By setting the surface roughness Rz to 0.2 μm or more, the copper foil surface roughness becomes appropriate, and copper foil peel strength tends to be further improved. On the other hand, by setting the surface roughness Rz to 4.0 μm or less, the copper foil surface roughness becomes appropriate, and conductor loss tends to be further reduced. From the viewpoint of improving peel strength, the copper foil surface roughness Rz is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, and particularly preferably 0.7 μm or more. From the viewpoint of reducing conductor loss, it is more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0219] Examples of lamination molding methods include methods commonly used for molding laminates and multilayer boards for printed wiring boards. More specifically, methods using a multistage press, multistage vacuum press, continuous molding machine, autoclave molding machine, etc. are used, at a temperature of about 180 to 350°C, for a heating time of about 100 to 300 minutes, and with a surface pressure of 20 to 100 kg / cm. 2Examples of suitable methods include lamination molding at approximately the same thickness. A multilayer board can also be produced by combining the prepreg of this embodiment with a separately prepared inner layer wiring board and laminating it together. A method for producing a multilayer board involves, for example, placing copper foil of approximately 35 μm on both sides of a single prepreg of this embodiment, laminating it using the above-described molding method, forming an inner layer circuit, and then blackening the circuit to form an inner layer circuit board. Then, the inner layer circuit board and the prepreg of this embodiment are alternately arranged one by one, and copper foil is placed on the outermost layer. The multilayer board can be produced by laminating and molding it under the above-described conditions, preferably under vacuum. The metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.

[0220] 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 provide a cured product that has excellent properties such as low dielectric properties and heat resistance, as well as moldability, crack resistance, and low thermal expansion.

[0221] <<Printed wiring boards>> The printed wiring board of this embodiment includes an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition of this embodiment and a layer formed from the prepreg of this embodiment. Such a printed wiring board can be manufactured using conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is described below. First, a metal foil-clad laminate, such as the copper foil-clad laminate described above, is prepared. Next, the surface of the metal foil-clad laminate is etched to form an inner layer circuit, thereby producing an inner layer substrate. If necessary, the surface of the inner layer circuit of this inner layer substrate is subjected to a surface treatment to enhance adhesive strength. Next, a required number of the prepregs described above are stacked on the surface of the inner layer circuit, and metal foil for an outer layer circuit is laminated on the outside of the prepreg. The resulting laminate is then integrally molded by heating and pressurizing. In this manner, a multilayer laminate is manufactured, in which an insulating layer consisting of a substrate and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, this multilayer laminate is subjected to drilling processing for through holes and via holes, and then a plated metal film is formed on the wall surface of the hole to provide electrical continuity between the inner layer circuit and the metal foil for the outer layer circuit.The metal foil for the outer layer circuit is then etched to form the outer layer circuit, thereby producing a printed wiring board.

[0222] The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of this insulating layer, and the insulating layer contains the resin composition of this embodiment described above and / or its cured product. That is, the prepreg of this embodiment described above (for example, a prepreg formed from a base material and the resin composition of this embodiment impregnated or applied thereto), or the layer formed from the resin composition of the metal foil-clad laminate of this embodiment described above, serves as the insulating layer of this embodiment. This embodiment also relates to a semiconductor device including the printed wiring board. For details of the semiconductor device, please refer to paragraphs 0200 to 0202 of Japanese Patent Application Laid-Open No. 2021-021027, the contents of which are incorporated herein by reference.

[0223] Furthermore, it is preferable that the insulating layer formed from the cured product of the resin composition of this embodiment has a small surface roughness after roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but may be, for example, 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x magnification lens. The non-contact surface roughness meter used is a WYKONT3300 manufactured by Veeco Instruments.

[0224] <<Resin composite sheet>> The resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment and disposed on the surface of the support. The resin composite sheet can be used as a build-up film or a dry film solder resist. There are no particular limitations on the method for producing the resin composite sheet, but an example of a method for obtaining the resin composite sheet includes applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent to a support and drying the applied solution.

[0225] Examples of the support used here include, but are not limited to, polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and release films obtained by applying a release agent to the surface of these films, organic film substrates such as polyimide film, conductive foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, FRP (Fiber-Reinforced Plastics), and other plate-shaped materials.

[0226] Examples of application methods (coating methods) include methods in which a solution of the resin composition of this embodiment dissolved in a solvent is applied onto a support using a bar coater, die coater, doctor blade, baker applicator, or the like. Furthermore, after drying, a single-layer sheet can be obtained by peeling or etching the support from a resin composite sheet in which the support and the resin composition are laminated. It should be noted that a single-layer sheet can also be obtained without using a support by supplying a solution of the resin composition of this embodiment dissolved in a solvent into a mold having a sheet-shaped cavity and drying it to form it into a sheet.

[0227] In the production of the monolayer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited. However, because low temperatures tend to leave the solvent in the resin composition, and high temperatures accelerate curing of the resin composition, a temperature of 20°C to 200°C for 1 to 90 minutes is preferred. The monolayer sheet or resin composite sheet can be used in an uncured state after the solvent has been dried, or it can be used in a semi-cured (B-staged) state as needed. Furthermore, the thickness of the resin layer in the monolayer sheet or resin composite sheet of this embodiment can be adjusted by the concentration and coating thickness of the solution of the resin composition of this embodiment used for coating (coating). While not particularly limited, a thickness of 0.1 to 500 μm is preferred because a thicker coating generally tends to leave the solvent during drying. [Example]

[0228] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments used in the examples are difficult to obtain due to discontinuation or the like, measurements can be made using other instruments with equivalent performance.

[0229] <Measurement of weight average molecular weight and number average molecular weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin represented by formula (T), the polyphenylene ether compound, were measured by gel permeation chromatography (GPC) using a liquid pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Showa Denko K.K., GPC KF-801, 802, 803, 804) at a flow rate of 1.0 mL / min, a column temperature of 40°C, and a calibration curve based on monodisperse polystyrene.

[0230] <Measurement of parameters α and β> The parameters α and β of the resin represented by formula (T) are: 1 The calculation was performed using H-NMR. The synthesized resin was dissolved in a mixed solvent of heptane and methanol, and the process of drying was repeated to remove the residual solvent contained in the recovered solid. The recovered solid was then dissolved in CDCl3 and 1 H-NMR measurements were performed. 1 In H-NMR, the parameters α and β of each resin were calculated using the following formula.

number

[0231] <Synthesis Example 1-1: Synthesis of Resin (1) Represented by Formula (T1)> A three-neck flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 3 g of activated clay, and a stirrer, and the mixture was heated to an internal temperature of 70°C while stirring. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise, controlling the rate of addition so that the internal temperature did not exceed 80°C. After the addition, the mixture was stirred until the internal temperature dropped to 70°C. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise in the same manner, and the mixture was allowed to react for an additional 2 hours after the addition. At the end of the reaction, 433 g of toluene was added, and the activated clay was removed by filtration. The filtrate was heated under reduced pressure to remove the solvent, yielding 231 g of solid resin. The resulting resin (1) represented by formula (T1) had an Mw of 2674, an Mn of 1153, and an Mw / Mn ratio of 2.3. In formula (Tx), the parameter α was 0.71, the parameter β was 0.50, and n+o+p was 6.3. The structures in parentheses representing structural units (a), (b), and (c) all had the same molecular weight, and n+o+p was calculated assuming that the Mn of the synthesized resin was the average molecular weight (the same applies to the following synthesis examples and synthesis comparative examples). Furthermore, GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0232] <Synthesis Example 1-2: Synthesis of Resin (2) Represented by Formula (T1)> A three-neck flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 3 g of activated clay, and a stirrer, and the mixture was heated to an internal temperature of 70°C while stirring. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise, controlling the rate of addition so that the internal temperature did not exceed 90°C. After the addition, the mixture was stirred until the internal temperature dropped to 70°C. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise in the same manner, and the mixture was allowed to react for an additional 1.5 hours after the addition. At the end of the reaction, 433 g of toluene was added, and the activated clay was removed by filtration. The filtrate was heated under reduced pressure to remove the solvent, yielding 233 g of solid resin. The resulting resin (2) represented by formula (T1) had an Mw of 2587, an Mn of 1105, and an Mw / Mn ratio of 2.3. In formula (Tx), the parameter α was 0.75, the parameter β was 0.42, and n+o+p was 6.0. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0233] <Synthesis Example 1-3: Synthesis of Resin (3) Represented by Formula (T1)> A three-neck flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 3 g of activated clay, and a stirrer, and the mixture was heated to an internal temperature of 70°C while stirring. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise, controlling the rate of addition so that the internal temperature did not exceed 80°C. After the addition, the mixture was stirred until the internal temperature dropped to 70°C. Then, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise in the same manner, and the mixture was allowed to react for an additional 1.5 hours after the addition. At the end of the reaction, 433 g of toluene was added, and the activated clay was removed by filtration. The filtrate was heated under reduced pressure to remove the solvent, yielding 246 g of solid resin. The resulting resin (3) represented by formula (T1) had an Mw of 2026, an Mn of 916, and an Mw / Mn ratio of 2.2. In formula (Tx), the parameter α was 0.66, the parameter β was 0.78, and n+o+p was 4.8. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0234] <Synthesis Example 1-4: Synthesis of Resin (4) Represented by Formula (T1)> A flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 0.75 g of activated clay, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), and a stirrer, and the mixture was heated to an internal temperature of 50°C while stirring. The mixture was then gradually heated to an internal temperature of 70°C over 5 hours and allowed to react for an additional hour at this internal temperature. After allowing the mixture to cool, the activated clay was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 129 g of a solid resin. The resulting resin (4) represented by formula (T1) had an Mw of 1193, an Mn of 693, and an Mw / Mn ratio of 1.7. In formula (Tx), the parameter α was 0.63, the parameter β was 1.07, and n+o+p was 3.4. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0235] <Synthesis Examples 1-5> A flask equipped with a thermometer and a condenser was charged with 520 g of toluene, 0.3 g of activated clay, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), and a stirrer, and the mixture was heated to an internal temperature of 50°C while stirring. The mixture was then gradually heated to an internal temperature of 80°C over 5 hours and allowed to react for an additional hour at an internal temperature of 80°C. After allowing the mixture to cool, the activated clay was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 129 g of a solid resin. The resulting resin (5) represented by formula (T1) had an Mw of 1424, an Mn of 722, and an Mw / Mn ratio of 2.0. In formula (Tx), the parameter α was 0.81, the parameter β was 0.88, and n+o+p was 3.6. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0236] <Comparative Synthesis Example 1-1> It was synthesized as follows according to Example 1 of JP 2021-143333 A. A flask equipped with a thermometer, a condenser, and a stirrer was charged with 125 parts by weight of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), 125 parts by weight of toluene, and 12.5 parts by weight of activated clay, and the internal temperature was raised to 30°C and the reaction was carried out for 2 hours, followed by reaction at 45°C for 1 hour, 60°C for 1 hour, 70°C for 1 hour, and 80°C for 10 hours. After allowing to cool, the activated clay was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 80 parts by weight of a solid resin. The resulting resin had an Mw of 2464, an Mn of 1232, an Mw / Mn ratio of 2.0, and in formula (Tx), the parameter α was 0.51, the parameter β was 0.85, and n+o+p was 6.8. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0237] <Comparative Synthesis Example 1-2> Following the preparation example of Coagent 3 in Example 1 of JP-A-02-219809, it was synthesized as follows. To 78 g of 1,3-bis(α-hydroxyisopropyl)benzene (Tokyo Chemical Industry Co., Ltd.), 330 mL of toluene and 0.633 g of p-toluenesulfonic acid were added, and then the whole was stirred at 90°C. In this process, the hydroxyisopropyl groups were dehydrated. The liberated water was distilled off by gradually increasing the temperature to 114°C. After all the water was removed, the whole was stirred at 114°C for another 3 hours. 72 g of a white solid was obtained, and the following composition (% by mass) was determined by GPC: Monomer 0.1% Dimer 2.9% Trimer-pentamer 13.8% ≧Hexamer 83.2% The resulting resin had an Mw of 2972, an Mn of 1181, an Mw / Mn ratio of 2.5, and in formula (Tx), the parameter α was 0.27, the parameter β was 5.15, and n+o+p was 6.5. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0238] <Comparative Synthesis Examples 1-3> It was synthesized as follows according to Example 3 of JP 2021-143333 A. A flask equipped with a thermometer, condenser, and stirrer was charged with 160 parts by weight of 1,3-bis(α-hydroxyisopropyl)benzene (Tokyo Chemical Industry Co., Ltd.), 80 parts by weight of toluene, 0.08 parts by weight of p-toluenesulfonic acid, and 0.19 parts by weight of water. The internal temperature was raised to 120°C and the reaction was allowed to proceed for 3 hours. 1,3-diisopropenylbenzene was generated in the system by dehydration (29.7 parts by weight of dehydrated water, nearly the theoretical amount). After cooling, 6.4 parts by weight of p-toluenesulfonic acid and 3.6 parts by weight of water were added, the internal temperature was raised to 60°C, and the reaction was allowed to proceed for 16 hours. After cooling, 150 parts by weight of toluene and 100 parts by weight of water were added, and the waste liquid was repeatedly washed with 100 parts by weight of water until it became neutral. The solvent was removed by distillation under reduced pressure with heating, yielding 122 parts by weight of resin as a white solid. The resulting resin had an Mw of 400, an Mn of 360, an Mw / Mn ratio of 1.1, and in formula (Tx), the parameter α was 0.33, the parameter β was 11.32, and n+o+p was 1.3. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0239] <Comparative Synthesis Examples 1-4> Following Example 1 of JP-A-3-252441, the compound was synthesized as follows. 50 g of chlorobenzene and 5 g of acid clay (montmorillonite K10) were placed in a three-neck flask and stirred at 100°C. While maintaining the temperature at 100°C, 50 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.) was added dropwise. Polymerization was carried out at 100°C for 1 hour, after which the acid clay (montmorillonite K10) was removed by filtration, and the polymer was precipitated in excess methanol. The polymer was filtered off and dried in a vacuum oven. The resulting resin had an Mw of 4318, an Mn of 3352, an Mw / Mn ratio of 1.3, and in formula (Tx), the parameter α was 0.88, the parameter β was 0.03, and n+o+p was 20.2. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0240] <Comparative Synthesis Examples 1-5> It was synthesized as follows, following Example 9 of U.S. Patent No. 4,205,160. 10 g (0.063 mol) of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), 115 mL of toluene, and 1.5 g of acid clay (montmorillonite K10) that had been dried in advance at 100°C were placed in a three-necked flask, heated, and refluxed for 1.5 hours. The acid clay (montmorillonite K10) was then removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 8.5 g of a solid resin. The resulting resin had an Mw of 3090, an Mn of 1350, an Mw / Mn ratio of 2.3, and in formula (Tx), the parameter α was 0.79, the parameter β was 0.07, and n+o+p was 7.5. GPC analysis confirmed that the residual monomer content was 1% by mass or less.

[0241] <Synthesis Example 2 Polyphenylene ether compound (B1)> <<Synthesis of Difunctional Phenylene Ether Oligomers>> A 12 L vertical reactor equipped with a stirrer, a thermometer, an air inlet tube, and a baffle plate was charged with 29.64 g (43.2 mmol) of CuBr, 1.86 g (10.8 mmol) of N,N'-di-t-butylethylenediamine, 69.83 g (690.1 mmol) of n-butyldimethylamine, and 2,600 g of toluene. The mixture was stirred at a reaction temperature of 40°C. 2,2',3,3',5,5'-hexamethyl-(1,1', A mixed solution of 129.3 g (0.48 mol) N,N'-di-t-butylethylenediamine, 878.4 g (7.2 mol) 2,6-dimethylphenol, 1.26 g (7.3 mmol) N,N'-di-t-butylethylenediamine, and 27.19 g (268.7 mmol) n-butyldimethylamine was added dropwise over 230 minutes while bubbling a mixed gas (nitrogen and air) adjusted to an oxygen concentration of 8% by volume at a flow rate of 5.2 L / min and stirring was continued. After the addition was completed, 1,500 g of an aqueous solution containing 48.06 g (126.4 mmol) of tetrasodium ethylenediaminetetraacetate was added to terminate the reaction. The aqueous and organic layers were separated, and the organic layer was washed with 1 N aqueous hydrochloric acid and then with pure water. The resulting solution was concentrated to 50% by mass using an evaporator to obtain 1980 g of a toluene solution of a bifunctional phenylene ether oligomer (resin "B0"). The number average molecular weight of resin "B0" measured by GPC in terms of polystyrene was 2100, the weight average molecular weight measured by GPC in terms of polystyrene was 3740, and the hydroxyl equivalent was 1070.

[0242] <<Synthesis of Polyphenylene Ether Compounds>> 792 g of a 50% by weight toluene solution of difunctional phenylene ether oligomer (B0) was evaporated to dryness using an evaporator, and then 2772 g of N,N-dimethylacetamide was added. The mixture was concentrated to a solids content of 20% by weight, yielding 1980 g of a 79.80% by weight N,N-dimethylacetamide, 0.20% by weight toluene solution of difunctional phenylene ether oligomer (B0). Next, 1980 g of the difunctional phenylene ether oligomer solution (B0) (0.37 mol in OH equivalents) and 67.78 g (0.44 mol) of chloromethylstyrene (CMS-P) were charged into a reactor equipped with a stirrer, thermometer, and reflux condenser, and heated to 50 ° C. with stirring. 84.48 g (0.44 mol) of a methanol solution of sodium methoxide (concentration: 28.4% by weight) was added dropwise while maintaining the reaction temperature at 50 ° C., and the mixture was stirred for 1 hour. Further, 9.75 g (0.05 mol) of a methanol solution of sodium methoxide (concentration: 28.4 wt%) was added dropwise, and the mixture was stirred for 2 hours. Subsequently, 5.91 g (0.05 mol) of an 85 wt% aqueous phosphoric acid solution was added, and the resulting inorganic salt was removed. The reaction solution was then added dropwise to 1975 g of water to solidify the mixture. After solid-liquid separation using a centrifuge, the solid was washed with pure water and methanol, and then dried under reduced pressure to obtain 381.87 g of the target polyphenylene ether compound (B1). The polystyrene-equivalent number average molecular weight of the polyphenylene ether compound (B1) measured by GPC was 2350, the weight average molecular weight was 3880, and the vinyl group equivalent was 1220 g / vinyl group.

[0243] <Synthesis Example 3: Synthesis of polymer (va) having a structural unit represented by formula (V)> 2.25 moles (292.9 g) of divinylbenzene, 1.32 moles (172.0 g) of ethylvinylbenzene, 11.43 moles (1190.3 g) of styrene, and 15.0 moles (1532.0 g) of n-propyl acetate were charged into a reactor, and 600 mmol of boron trifluoride diethyl ether complex was added at 70 °C. The reaction was allowed to proceed for 4 hours. After the polymerization reaction was terminated with aqueous sodium bicarbonate, the oil layer was washed three times with pure water and devolatilized under reduced pressure at 60 °C to recover polymer (va) having structural units represented by formula (V). The resulting polymer (va) having structural units represented by formula (V) was weighed, confirming that 860.8 g of polymer (va) having structural units represented by formula (V) was obtained.

[0244] The resulting polymer (va) having a structural unit represented by formula (V) had a number average molecular weight Mn of 2,060, a weight average molecular weight Mw of 30,700, and a monodispersity index Mw / Mn of 14.9. 13 C-NMR and 1 By performing H-NMR analysis, resonance lines derived from each monomer unit used as a raw material were observed in the polymer (va) having a structural unit represented by formula (V). Based on the NMR measurement results and GC analysis results, the proportion of each monomer unit (structural unit derived from each raw material) in the polymer (va) having a structural unit represented by formula (V) was calculated as follows: Divinylbenzene-derived structural units: 20.9 mol% (24.3 mass%) Structural units derived from ethylvinylbenzene: 9.1 mol% (10.7 mass%) Structural units derived from styrene: 70.0 mol% (65.0 mass%) Furthermore, the content of structural units having residual vinyl groups derived from divinylbenzene was 16.7 mol % (18.5 mass %).

[0245] Example 1 A varnish was obtained by dissolving and mixing 30 parts by mass of the resin (1) represented by formula (T1) obtained in Synthesis Example 1-1 above and 70 parts by mass of the polyphenylene ether compound (B1) obtained in Synthesis Example 2 in methyl ethyl ketone and toluene. The blending amount of each component mentioned above indicates the solid content.

[0246] <Production of 1.0 mm thick hardened plate test specimens> The solvent was evaporated and removed from the resulting varnish to obtain a resin composition powder. The resulting resin composition powder was used to prepare a cured plate as follows: 4.5 g of the resin composition powder was placed in a stainless steel mold frame measuring 100 mm x 30 mm x 1.0 mm (height), placed in a vacuum press (Kitagawa Seiki Co., Ltd.), and held at 200°C for 1.5 hours, pressing at a surface pressure of 1.9 MPa. The cured sheets were used to evaluate the glass transition temperature, dielectric constant (Dk), and dielectric loss tangent (Df). The evaluation results are shown in Table 1.

[0247] <Measurement and evaluation methods> (1) Glass transition temperature The cured plate was downsized to a size of 12.7 mm x 30 mm, and the sample was subjected to measurement by the DMA (Dynamic Mechanical Analysis) bending method using a dynamic viscoelasticity measuring device in accordance with JIS C6481 5.17.2. The peak temperature of the loss modulus obtained was taken as the glass transition temperature. The unit is °C. The dynamic viscoelasticity analyzer used was a DMA Q800 manufactured by TA Instruments.

[0248] (2) Dielectric constant (Dk) and dielectric loss tangent (Df) The cured plate was reduced in width to 1.0 mm and dried at 120°C for 60 minutes, after which the relative permittivity (Dk) and dielectric loss tangent (Df) of the dried plate were measured at a frequency of 10 GHz using a perturbation cavity resonator at 23°C. The perturbation method cavity resonator used was Agilent8722ES manufactured by Agilent Technologies.

[0249] Example 2 The same procedure was repeated in Example 1, except that the resin (1) represented by formula (T1) obtained in Synthesis Example 1-1 above was replaced with an equivalent amount of the resin (2) represented by formula (T1) obtained in Synthesis Example 1-2 above. The results are shown in Table 1.

[0250] Example 3 The same procedure was repeated in Example 1, except that the resin (1) represented by formula (T1) obtained in Synthesis Example 1-1 above was replaced with an equivalent amount of the resin (3) represented by formula (T1) obtained in Synthesis Example 1-3 above. The results are shown in Table 1.

[0251] Example 4 The same procedure was repeated in Example 1, except that the resin (1) represented by formula (T1) obtained in Synthesis Example 1-1 was replaced with an equivalent amount of the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4. The results are shown in Table 1.

[0252] Comparative Example 1 In Example 1, the resin (1) represented by formula (T1) obtained in the above Synthesis Example 1-1 was replaced with an equivalent amount of the resin obtained in the above Synthesis Comparative Example 1-1 (a resin equivalent to Example 1 of JP 2021-143333 A), and the other steps were carried out in the same manner. The results are shown in Table 1.

[0253] Comparative Example 2 In Example 1, the resin (1) represented by formula (T1) obtained in the above Synthesis Example 1-1 was replaced with an equivalent amount of the resin obtained in the above Synthesis Comparative Example 1-2 (a resin equivalent to Coagent 3 in Example 1 of JP-A-02-219809), and the other procedures were carried out in the same manner. The results are shown in Table 1.

[0254] Example 5 The same procedure was repeated in Example 1, except that the polyphenylene ether compound (B1) obtained in Synthesis Example 2 above was replaced with an equivalent amount of the maleimide compound (m1a) shown in the following structure (manufactured by DIC Corporation, "NE-X-9470S", a compound represented by formula (M1)). The results are shown in Table 2.

[0255] Maleimide compound (m1a) [ka]

[0256] Comparative Example 3 In Example 5, the resin (1) represented by formula (T1) obtained in the above Synthesis Example 1-1 was replaced with an equivalent amount of the resin obtained in the above Synthesis Comparative Example 1-3 (a resin equivalent to Example 3 of JP 2021-143333 A), and the other steps were carried out in the same manner. The results are shown in Table 2.

[0257] Comparative Example 4 In Example 5, the resin (1) represented by formula (T1) obtained in Synthesis Example 1-1 was replaced with an equivalent amount of the resin obtained in Synthesis Comparative Example 1-4 (a resin corresponding to Example 1 in JP-A-3-252441), and the other steps were carried out in the same manner. The results are shown in Table 2.

[0258] [Table 1]

[0259] [Table 2]

[0260] NMR charts and GPC charts are shown in Figures 1 to 10. NMR charts for a total of eight resins obtained in Synthesis Examples 1-1 to 1-4 and Synthesis Comparative Examples 1-1 to 1-4 are shown in order starting from Figure 1. GPC charts for the resin obtained in Synthesis Example 1-4 are shown in Figure 9, and for the resin obtained in Synthesis Comparative Example 1-2 are shown in Figure 10.

[0261] Example 6 15 parts by mass of the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 above, 85 parts by mass of polyphenylene ether compound (B2) (polyphenylene ether compound (B2): Noryl SA9000, compound shown in the structure below, manufactured by SABIC Japan, LLC, vinyl group double bond equivalent: 1011 g / eq.), and 1.5 parts by mass of Perbutyl P (1,3-bis(butylperoxyisopropyl)benzene, manufactured by NOF Corporation) as a curing accelerator were dissolved in methyl ethyl ketone and toluene and mixed to obtain a varnish. The blending amount of each component indicated above indicates the solid content. The obtained varnish was evaluated in the same manner as in Example 1. The results are shown in Table 3. [ka]

[0262] Example 7 A varnish was obtained by dissolving 30 parts by mass of the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 above and 70 parts by mass of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 in methyl ethyl ketone and toluene and mixing them. The blending amount of each component mentioned above indicates the solid content. The resulting varnish was evaluated in the same manner as in Example 1. The results are shown in Table 3.

[0263] Example 8 The same procedure was repeated in Example 4, except that the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 was replaced with an equivalent amount of the resin (5) represented by formula (T1) obtained in Synthesis Example 1-5. The results are shown in Table 3.

[0264] Example 9 A varnish was obtained by dissolving 30 parts by mass of the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 above, 70 parts by mass of a polymaleimide compound (NE-X-9500 manufactured by DIC Corporation, corresponding to a polymaleimide compound having a structural unit represented by formula (M7) above), and 1.5 parts by mass of Perbutyl P (1,3-bis(butylperoxyisopropyl)benzene manufactured by NOF Corporation) as a curing accelerator in methyl ethyl ketone and toluene and mixing them. The blending amounts of each component mentioned above indicate the solid content. The resulting varnish was evaluated in the same manner as in Example 1. The results are shown in Table 3.

[0265] Comparative Example 5 In Example 4, the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 was replaced with an equivalent amount of the resin obtained in Synthesis Comparative Example 1-5 (a resin corresponding to Example 9 in U.S. Pat. No. 4,205,160), and the other procedures were carried out in the same manner. The results are shown in Table 3.

[0266] Comparative Example 6 In Example 6, the resin (4) represented by formula (T1) obtained in the above Synthesis Example 1-4 was replaced with an equivalent amount of the resin obtained in the above Synthesis Comparison Example 1-2 (a resin equivalent to Coagent 3 in Example 1 of JP-A-02-219809), and the other procedures were carried out in the same manner.

[0267] Comparative Example 7 In Example 9, the resin (4) represented by formula (T1) obtained in Synthesis Example 1-4 was replaced with 30 parts by mass of the resin obtained in the above-mentioned Synthesis Comparison Example 1-2 (a resin equivalent to Coagent 3 in Example 1 of JP-A-02-219809), and the other procedures were carried out in the same manner.

[0268] Comparative Example 8 A varnish was obtained by dissolving 100 parts by mass of a maleimide compound (manufactured by DIC Corporation, "NE-X-9500", a compound represented by formula (M7)) and 1.5 parts by mass of Perbutyl P (1,3-bis(butylperoxyisopropyl)benzene, manufactured by NOF Corporation) as a curing accelerator in methyl ethyl ketone and toluene and mixing them. The blending amount of each component mentioned above indicates the solid content. The obtained varnish was evaluated in the same manner as in Example 1. The results are shown in Table 3. The results are shown in Table 3. [Table 3]

[0269] FIG. 11 shows the NMR chart of the resin obtained in Synthesis Example 1-5. FIG. 12 shows the NMR chart of the resin obtained in Comparative Synthesis Example 1-5.

Claims

1. A method for producing a resin represented by formula (T), The parameter α calculated from the formula (α) is 0.55 or more and 0.90 or less, The parameter β calculated from the formula (β) is 0.30 or more and 1.50 or less, The method includes using a solid acid as a catalyst when reacting raw materials, the raw material is at least one selected from the group consisting of m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene; A method for producing a resin represented by formula (T). 【number】 (In formula (T), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x1 represents 0, and R represents a group containing a structural unit represented by formula (Tx).) 【number】 (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents 0. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) [Equation 1] (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.)

2. The method for producing a resin represented by formula (T) according to claim 1 , wherein the solid acid comprises activated clay.

3. The method for producing a resin represented by formula (T) according to claim 1 or 2, wherein the solid acid is used in an amount of 0.01 to 20.0 parts by mass per 100 parts by mass of the raw material for the resin represented by formula (T).

4. The parameter α calculated from the formula (α) is 0.60 or more and 0.90 or less, The method for producing a resin represented by formula (T) according to claim 1 or 2, wherein the parameter β calculated from formula (β) is 0.40 or more and 1.50 or less.

5. The method for producing a resin represented by formula (T) according to claim 1 or 2, wherein in the constitutional unit represented by formula (Tx), 1.1≦n+o+p≦20.

0.

6. The method for producing a resin represented by formula (T) according to claim 1 or 2, wherein the resin has a number average molecular weight of 400 to 3,000.

7. The method for producing a resin represented by formula (T) according to claim 1 or 2, wherein the resin has a weight average molecular weight of 500 to 6000.

8. 3. The method for producing a resin represented by formula (T) according to claim 1, wherein Mw / Mn, which is the ratio of weight average molecular weight to number average molecular weight, is 1.1 to 3.

0.

9. The parameter α calculated from the formula (α) is 0.60 or more and 0.90 or less, The parameter β calculated from the formula (β) is 0.40 or more and 1.50 or less, In the structural unit represented by formula (Tx), 1.1≦n+o+p≦20.0; The number average molecular weight is 400 to 3000, The weight average molecular weight is 500 to 6000, 3. The method for producing a resin represented by formula (T) according to claim 1, wherein Mw / Mn, which is the ratio of weight average molecular weight to number average molecular weight, is 1.1 to 3.0.

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