Prepreg, metal foil-clad laminate, printed wiring board, and semiconductor device

Abstract

To provide a prepreg, a metal foil-clad laminate, a printed wiring board, and a semiconductor device. A prepreg according to the present disclosure comprises: a resin composition and / or a semi-cured product thereof; and a glass cloth, wherein the resin composition contains a thermosetting compound, the glass cloth has a dielectric constant of 4.4 or less at the frequency of 10 GHz as measured by a cavity perturbation method in accordance with JIS C218:2007, and the proportion of SiO2 in the glass cloth is 61-85 mass%.

Description

Prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices

[0001] The present invention relates to prepregs, metal foil-clad laminates, printed circuit boards, and semiconductor devices.

[0002] In recent years, the integration and miniaturization of semiconductor elements used in mobile devices, electronic equipment, and communication devices has accelerated. Consequently, technologies that enable high-density mounting of semiconductor elements are required, and improvements are needed in printed circuit boards, such as substrates for mounting semiconductor elements, which play a crucial role in this process. Meanwhile, the applications of electronic equipment are diversifying and expanding. As a result, the various characteristics required of printed circuit boards, such as substrates for mounting semiconductor elements, and the metal foil laminates and prepregs used therein, have become more diverse and stringent. To obtain improved printed circuit boards while considering these required characteristics, various materials and processing methods have been proposed. One example is the development of improved prepregs. Such materials are described in Patent Documents 1 and 2.

[0003] International Publication No. 2019 / 065940, International Publication No. 2019 / 230945

[0004] As mentioned above, improvements to prepregs are being considered, but as the applications of electronic devices and other equipment diversify and expand, there is a demand for new materials. Under these circumstances, the present invention aims to provide a prepreg that maintains low dielectric properties while also having excellent drillability, as well as a metal foil-clad laminate, printed circuit board, and semiconductor device.

[0005] Under the above problems, the inventors have conducted studies and found that in a prepreg having glass cloth, the dielectric constant is low and SiO ２It has been found that the above problems can be solved by using a glass cloth in which the ratio is within a predetermined range. Specifically, the above problems have been solved by the following means. [1] A prepreg having a resin composition and / or a semi-cured product of the resin composition and a glass substrate, the resin composition containing a thermosetting compound, and according to JIS C218: 2007 of the glass substrate, the dielectric constant at a frequency of 10 GHz measured by the cavity resonator perturbation method is 4.4 or less, and SiO in the glass substrate ２ A prepreg in which the ratio is 61 to 85% by mass. [2] The prepreg according to [1], wherein the dielectric tangent at a frequency of 10 GHz measured by the cavity resonator perturbation method according to JIS C218: 2007 of the glass substrate is less than 0.002. [3] The thermosetting compound is at least one selected from the group consisting of a maleimide compound, an aromatic-containing resin having a carbon-carbon double bond at the terminal, a cyanate ester compound, a (meth) allyl compound, a (meth) acrylate compound, an epoxy compound, a phenol compound, an oxetane compound, a benzoxazine compound, an arylcyclobutene compound, a perfluorovinyl ether resin, a polyimide compound, and a compound having a vinylene group. The prepreg according to [1] or [2]. [4] The thermosetting compound is a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), a maleimide compound (M6), a maleimide compound (M7) and a maleimide compound (M8). The prepreg according to any one of [1] to [3], which contains one or more selected from the group consisting of. (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group, and R ５２ each independently represents a hydrogen atom or a methyl group, and n １ represents an integer of 1 or more.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ each independently represents a hydrogen atom or an organic group. RＭ５ and R Ｍ６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4-6 membered alicyclic group. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. Ｍ９ and R Ｍ１０ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. Ｍ１５ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20. (In formula (M2), R ５４ Each of these independently represents a hydrogen atom or a methyl group, n ４ (This represents an integer greater than or equal to 1.) (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10, inclusive.) (In formula (M4), R ５６ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and R ５７ (Each of these independently represents either a hydrogen atom or a methyl group.) (In formula (M5), R ５８ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５９ Each of these independently represents a hydrogen atom or a methyl group, n ６ (This represents an integer greater than or equal to 1.) (In formula (M6), R ６１R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６２ R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６３ Each of these 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 of these independently represents an integer from 0 to 10. (In formula (M7), R １ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, and R ２ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group. ３ , R ４ , R ５ and R ６ Each of these independently represents a hydrogen atom or a methyl group, and R ３ and R ４ One side is a hydrogen atom, and the other side is a methyl group, R ５ and R ６ One side is a hydrogen atom, and the other side is a methyl group, X １ These are expressed independently as follows (x): (In formula (x), R ７ and R ８ Each of these independently represents a hydrogen atom or a methyl group, and R ７ and R ８ One side is a hydrogen atom, and the other side is a methyl group, R ９ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, where t represents an integer from 0 to 4. ) represents a substituent represented by X１ X per benzene ring to which is bonded １ (This is the average number of substitutions, representing numbers from 0 to 4, where p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.) (In formula (M8), R １ and R ３ Each of these independently represents a hydrocarbon group in which eight or more atoms are linked in a linear chain, and R ２ Each independently represents a substituted or unsubstituted cyclic hydrocarbon group which may contain 4 to 10 heteroatoms constituting the ring, and n represents a number from 1 to 10.) [5] The prepreg according to any one of [1] to [4], wherein the thermosetting compound comprises a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, and -(Y-O) ｎ１ The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Each independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.) [6] A prepreg according to any one of [1] to [5], wherein the thermosetting compound comprises a compound represented by formula (M1), a compound represented by formula (M3), and a polyphenylene ether compound represented by formula (OP). (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4-6 membered alicyclic group. R Ｍ７ and RＭ８ Each of these is independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. Ｍ９ and R Ｍ１０ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. Ｍ１５ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20. (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10, inclusive.) [7] A prepreg according to any one of [1] to [6], further comprising a filler other than the glass substrate. [8] A prepreg according to any one of [1] to [7], further comprising a flame retardant. [9] A prepreg according to any one of [1] to [8], for use in printed circuit boards.

[10] A prepreg according to any one of [1] to [9], wherein the dielectric loss tangent of the glass substrate at a frequency of 10 GHz measured by the cavity resonator perturbation method in accordance with JIS C218:2007 is less than 0.002, the thermosetting compound comprises a compound represented by formula (M1), a compound represented by formula (M3), and a polyphenylene ether compound represented by formula (OP), further comprising a filler other than the glass substrate, further comprising a flame retardant, for use in printed circuit boards. (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６Each independently represents a hydrogen atom or an alkyl group. Ar Ｍ represents a divalent aromatic group. A is an alicyclic group having 4 to 6 members. 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 each independently represents a hydrogen atom or an alkyl group. R Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ each independently represents a hydrogen atom or an organic group; 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. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) (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 n ５ represents an integer of 1 or more and 10 or less.)

[11] A metal foil-clad laminate including at least one prepreg according to any one of [1] to

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

[12] A printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes a layer formed from the prepreg according to any one of [1] to

[10] .

[13] A semiconductor device including the printed wiring board according to

[12] .

[0006] According to the present invention, it is possible to provide a prepreg that maintains low dielectric characteristics and is also excellent in drillability, as well as a metal foil-clad laminate, a printed wiring board, and a semiconductor device.

[0007] Hereinafter, embodiments for carrying out the present invention (hereinafter simply referred to as "this embodiment") will be described in detail. Note that the following embodiments are illustrative examples for explaining the present invention, and the present invention is not limited to these embodiments. In this specification, "~" is used to mean that the numerical values ​​before and after it include the lower and upper limits. "A~B" means A or greater and B or less. Furthermore, any combination of the upper and lower limits of numerical values ​​in this specification is given as an example of this embodiment. In this specification, various physical properties and characteristic values ​​are given at 23°C unless otherwise specified. In the notation of groups (atomic groups) in this specification, notations that do not specify substitution and unsubstituted include both groups (atomic groups) with substituents and groups (atomic groups) without substituents. For example, "alkyl group" includes not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups). In this specification, when notations that do not specify substitution and unsubstituted are used, unsubstituted is preferred. Examples of substituents in this specification are preferably halogen atoms, cyano groups, nitro groups, hydroxyl groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclic oxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, acyl groups, or amino groups; more preferably halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, alkenyl groups, or acyl groups; even more preferably alkyl groups, aryl groups, aryloxy groups, or alkenyl groups; and even more preferably alkyl groups. The formula weight of these substituents is preferably 15 or more, and preferably 200 or less. Formula weight refers to, for example, a methyl group (-CH ３ If so, the result is 15. These substituents may have further substituents, but it is preferable that they do not have substituents.

[0008] In this specification, "(meth)allyl" represents both allyl and methallyl, or either of them; "(meth)acrylate" represents both acrylate and methacrylate, or either of them; "(meth)acrylic" represents both acrylic and methacrylic, or either of them; and "(meth)acryloyl" represents both acryloyl and methacryloyl, or either of them.

[0009] In this specification, the relative dielectric constant indicates the ratio of the dielectric constant of a substance to the dielectric constant of vacuum. Also, in this specification, the relative dielectric constant may sometimes be simply referred to as "dielectric constant". Furthermore, unless otherwise specified, the relative dielectric constant in this specification means the relative dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method. In this specification, the weight average molecular weight and the number average molecular weight are measured according to the description in paragraph 0259 of International Publication No. 2024 / 101237, unless otherwise specified. When the standards shown in this specification vary depending on the year and the measurement method, etc., unless otherwise specified, they shall be based on the standards as of January 1, 2024.

[0010] In this specification, the resin solid content refers to the components excluding the filler and the solvent, and is intended to include thermosetting compounds and, if necessary, resin additive components (additives such as flame retardants).

[0011] The prepreg of this embodiment is a prepreg having a resin composition and / or a semi-cured product of the resin composition and a glass base material, the resin composition contains a thermosetting compound, and according to JIS C218:2007 of the glass base material, the dielectric constant at a frequency of 10 GHz measured by the cavity resonator perturbation method is 4.4 or less, and the proportion of SiO ２ in the glass base material is 61 to 85% by mass. By adopting such a configuration, a prepreg with excellent drillability while maintaining low dielectric characteristics can be obtained. That is, conventionally, Q glass has been used as the glass used for the glass base material. However, Q glass has SiO ２Due to the high content of SiO, the cured prepreg using Q glass substrates was prone to drill wear. As a result of the inventors' investigation, the SiO used in the glass substrates was found to be ２ It was found that reducing the content of [the substance] effectively suppresses drill wear. Furthermore, it was found that sufficient low dielectric properties can be maintained.

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

[0013] <Resin Composition> The resin composition used in this embodiment contains a thermosetting compound, and more preferably contains a thermosetting resin. The thermosetting compound preferably contains at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group, and consists of a compound having a maleimide compound, an aromatic resin having a carbon-carbon double bond at the terminal, a cyanate ester compound, a (meth)allyl compound, a (meth)acrylate compound, an epoxy compound, and a phenol compound. It is more preferable to include at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, and cyanate ester compounds; it is even more preferable to include at least one selected from the group consisting of maleimide compounds and aromatic resins having a carbon-carbon double bond at the terminal, and it is even more preferable to include maleimide compounds and / or aromatic resins having a carbon-carbon double bond at the terminal, and it is even more preferable to include compounds represented by formula (M1), compounds represented by formula (M3), and polyphenylene ether compounds represented by formula (OP), which will be described later.

[0014] Among the thermosetting compounds contained in the resin composition of this embodiment, compounds that fall under two or more of the compounds listed above shall be considered as examples of specific compounds, as specified herein. On the other hand, among the thermosetting compounds contained in the resin composition of this embodiment, compounds that fall under two or more of the compounds listed above but are not specified herein shall be classified as the compounds listed above, unless otherwise specified. For example, a compound that falls under both maleimide compounds and epoxy compounds shall be considered a maleimide compound.

[0015] The content of the thermosetting compound in the resin composition in this embodiment is preferably 1 part by mass or more, more preferably 10 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, and may be 60 parts by mass or more, 65 parts by mass or more, and also preferably 99 parts by mass or less, more preferably 95 parts by mass or less, even more preferably 90 parts by mass or less, even more preferably 85 parts by mass or less, and may be less than 80 parts by mass. Setting the content above the lower limit tends to further improve the heat resistance and peel strength of the resulting cured product. Setting the content below the upper limit tends to further improve the low dielectric properties (Dk and / or Df) of the resulting cured product. The resin composition in this embodiment may contain only one type of thermosetting compound or two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0016] In this embodiment, the total amount of the thermosetting compound contained in the resin composition is preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 99% by mass or more, of the maleimide compound, aromatic-containing resin having a carbon-carbon double bond at the end, and cyanate ester compound (preferably the maleimide compound and the aromatic-containing resin having a carbon-carbon double bond at the end). The maleimide compound here is preferably one or more selected from the group consisting of the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M2), the compound represented by formula (M3), the compound represented by formula (M4), the compound represented by formula (M5), maleimide compound (M6), maleimide compound (M7), and maleimide compound (M8), and is more preferably the compound represented by formula (M1) and / or the compound represented by formula (M3). The aromatic-containing resin having a carbon-carbon double bond at the end is preferably a polyphenylene ether compound represented by formula (OP), which will be described later.

[0017] <<Maleimide Compound>> The resin composition in this embodiment preferably contains a maleimide compound. In this embodiment, the maleimide compound is preferably a compound having one or more (preferably two or more, more preferably two to twelve, even more preferably two to six, even more preferably two to four, even more preferably two or three, and even more preferably two) maleimide groups per molecule. In this embodiment, the maleimide compound preferably contains one or more selected from the group consisting of the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M2), the compound represented by formula (M3), the compound represented by formula (M4), the compound represented by formula (M5), maleimide compound (M6), maleimide compound (M7), and maleimide compound (M8), and more preferably contains one or more selected from the group consisting of the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula (M2), the compound represented by formula (M3), the compound represented by formula (M4), and the compound represented by formula (M5). Furthermore, it is more preferable to include one or more compounds selected from the group consisting of compounds represented by formula (M0), compounds represented by formula (M1), compounds represented by formula (M3), compounds represented by formula (M4), and compounds represented by formula (M5); it is even more preferable to include one or more compounds selected from the group consisting of compounds represented by formula (M1), compounds represented by formula (M3), and compounds represented by formula (M5); and it is even more preferable to include the compound represented by formula (M1) and / or the compound represented by formula (M3). When these maleimide compounds are used in printed circuit board materials (e.g., metal foil laminates), excellent heat resistance can be imparted.

[0018] (In formula (M0), R ５１ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５２ Each of these independently represents a hydrogen atom or a methyl group, n １ (This represents an integer greater than or equal to 1.) R ５１Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５２ It is preferable that it is a methyl group. １ The integer is preferably between 1 and 10, more preferably between 1 and 5, even more preferably between 1 and 3, even more preferably 1 or 2, and even more preferably 1. Specifically, the following compounds are examples of preferred values ​​of formula (M0). In the above formula, R ８ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and a methyl group is preferred.

[0019] The compound represented by formula (M0) may be a single compound or a mixture of two or more compounds. An example of a mixture is n １ A mixture of different compounds, R ５１ and / or R ５２ Examples include mixtures of compounds with different types of substituents, mixtures of compounds with different bonding positions (meta, para, ortho) between the maleimide group and the oxygen atom on the benzene ring, and mixtures of compounds in which two or more of the above differences are combined. The same applies to compounds represented by formulas (M1) to (M8) below.

[0020] (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4-6 membered alicyclic group. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. Ｍ９ and R Ｍ１０Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. Ｍ１５ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20.

[0021] R in the formula Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, ethyl group, propyl group, or butyl group, with the methyl group being particularly preferred. Ｍ１ and R Ｍ３ Each of these is independently preferably an alkyl group, R Ｍ２ and R Ｍ４ A hydrogen atom is preferred. Ｍ５ and R Ｍ６ Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ Ar represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or anthracenediyl group, more preferably a phenylene group, and even more preferably an m-phenylene group. ＭAr may have substituents, preferably alkyl groups, more preferably alkyl groups having 1 to 12 carbon atoms, even more preferably alkyl groups having 1 to 6 carbon atoms, even more preferably methyl groups, ethyl groups, propyl groups, and butyl groups, with methyl groups being particularly preferred. However, Ar Ｍ It is preferable that it is unsubstituted. A is a 4- to 6-membered alicyclic group, and a 5-membered alicyclic group (preferably a group that combines with a benzene ring to form an indan ring) is more preferable. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R Ｍ９ and R Ｍ１０ Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being more preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, ethyl group, propyl group, or butyl group, with the methyl group being particularly preferred. Ｍ１２ and R Ｍ１３ Each of these is independently preferably an alkyl group, R Ｍ１１ and R Ｍ１４ A hydrogen atom is preferred. Ｍ１５Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and is preferably an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms. px represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0. nx represents an integer from 1 to 20. nx may be an integer of 10 or less. The resin composition in this embodiment may contain only one compound represented by formula (M1) with at least two or more compounds having different nx values. When two or more types are included, the average value of nx (average number of repeating units) in the compound represented by formula (M1) in the resin composition is preferably 0.92 or higher, more preferably 0.95 or higher, even more preferably 1.0 or higher, and even more preferably 1.1 or higher, in order to obtain a low melting point (low softening point), low melt viscosity, and excellent handling properties. Furthermore, n is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 7.0 or less, even more preferably 6.0 or less, and may also be 5.0 or less. The same applies to formula (M1-1), etc., which will be described later.

[0022] The compound represented by formula (M1) is preferably the compound represented by the following formula (M1-1). (In formula (M1-1), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ Each of these independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ Each of these independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ Each of these independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ Each of these independently represents either a hydrogen atom or an alkyl group. nx represents an integer between 1 and 20.

[0023] R in the formula Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ Each of these independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, even more preferably a methyl group, ethyl group, propyl group, or butyl group, and particularly preferably a methyl group. Ｍ２１ and R Ｍ２３ The alkyl group is preferred, R Ｍ２２ and R Ｍ２４ A hydrogen atom is preferred. Ｍ２５ and R Ｍ２６ Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ Each of these independently represents a hydrogen atom or an organic group, with hydrogen atoms being preferred. 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, even more preferably a methyl group, ethyl group, propyl group, or butyl group, and particularly preferably a methyl group. Ｍ３１ and R Ｍ３２Each of these independently represents a hydrogen atom or an alkyl group, with alkyl groups being preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, and methyl, ethyl, propyl, and butyl groups are even more preferred, with methyl groups being particularly preferred. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ Each of these independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, even more preferably a methyl group, ethyl group, propyl group, or butyl group, and particularly preferably a methyl group. Ｍ３３ and R Ｍ３６ A hydrogen atom is preferred, R Ｍ３４ and R Ｍ３５ A alkyl group is preferred. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ Each of these independently represents either a hydrogen atom or an alkyl group, with alkyl groups being preferred. Here, alkyl groups having 1 to 12 carbon atoms are preferred, alkyl groups having 1 to 6 carbon atoms are more preferred, methyl groups, ethyl groups, propyl groups, and butyl groups are even more preferred, and among these, methyl groups are particularly preferred. nx represents an integer between 1 and 20. nx may also be an integer less than or equal to 10.

[0024] The compound represented by formula (M1-1) is preferably the compound represented by the following formula (M1-2). (In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ Each of these independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ Each of these independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ Each of these independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ Each of these independently represents either a hydrogen atom or an alkyl group. nx represents an integer between 1 and 20.

[0025] In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and nx are R in equation (M1-1), respectively. Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and are synonymous with nx, and the preferred range is also similar.

[0026] The compound represented by formula (M1-1) is preferably the compound represented by the following formula (M1-3), and more preferably the compound represented by the following formula (M1-4). (In equation (M1-3), nx represents an integer between 1 and 20.) nx may also be an integer less than or equal to 10. (In equation (M1-4), nx represents an integer between 1 and 20.) nx may also be an integer less than or equal to 10.

[0027] The molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. Setting it above the lower limit tends to further improve the low dielectric properties (Dk and / or Df) and low water absorption of the resulting cured product. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, even more preferably 5,000 or less, and even more preferably 4,000 or less. Setting it below the upper limit tends to further improve the heat resistance and handling properties of the resulting cured product.

[0028] Further details of the compound represented by formula (M1) can be found in International Publication No. 2020-217679, which is incorporated herein by reference.

[0029] (In formula (M2), R ５４ Each of these independently represents a hydrogen atom or a methyl group, n ４ n represents an integer greater than or equal to 1. ４ n is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and may be 1. The compound represented by formula (M2) is n ４ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0030] (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10.) ５５Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５ n is preferably an integer between 1 and 5, more preferably an integer between 1 and 3, and even more preferably 1 or 2. The compound represented by formula (M3) is n ５ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0031] (In formula (M4), R ５６ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and R ５７ Each of these independently represents either a hydrogen atom or a methyl group.) An example of a compound represented by formula (M4) is R ５６ Each is independently a methyl group or an ethyl group, R ５７ The R is a methyl group. ５６ It is more preferable that the two benzene rings are a methyl group and an ethyl group, respectively. Another example of a compound represented by formula (M4) is R ５６ and R ５７ The fact is that it is a hydrogen atom.

[0032] (In formula (M5), R ５８ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５９ Each of these independently represents a hydrogen atom or a methyl group, n ６ (This represents an integer greater than or equal to 1.) R ５８Each of these is preferably independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and a phenyl group, more preferably a hydrogen atom and / or a methyl group, and even more preferably a hydrogen atom. ５９ It is preferable that it is a methyl group. ６ n is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and may be 1. The compound represented by formula (M5) is n ６ It may be a mixture of different compounds, and is preferable. Also, as mentioned in the section on the compound represented by formula (M0), it may be a mixture of compounds with other parts that are different.

[0033] Maleimide compounds (M6) are compounds having the structure represented by formula (M6) and maleimide groups at both ends of the molecular chain. (In formula (M6), R ６１ R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６２ R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６３ Each independently represents a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. Each independently represents an integer from 0 to 10.) Details of the maleimide compound (M6) and its preparation method can be found in paragraphs 0061 to 0066 of International Publication No. 2020 / 262577, which are incorporated herein by reference.

[0034] Maleimide compound (M7) is a maleimide compound obtained by using as reaction raw materials (1) an aromatic amine compound (a1) having 1 to 3 alkyl groups on the aromatic ring, an aromatic divinyl compound (a2) having 2 ethenyl groups, and maleic anhydride. Preferably, maleimide compound (M7) is a compound having the structure represented by formula (M7). (In the above formula (M7), R １ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, and R ２ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group. ３ , R ４ , R ５ and R ６ Each of these independently represents a hydrogen atom or a methyl group, and R ３ and R ４ One side is a hydrogen atom, and the other side is a methyl group, R ５ and R ６ One side is a hydrogen atom, and the other side is a methyl group, X １ These are expressed independently as follows (x): (In formula (x), R ７ and R ８ Each of these independently represents a hydrogen atom or a methyl group, and R ７ and R ８ One side is a hydrogen atom, and the other side is a methyl group, R ９ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, where t represents an integer from 0 to 4. ) represents a substituent represented by X １ X per benzene ring to which is bonded １ (This is the average number of substitutions, representing numbers from 0 to 4, where p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.)

[0035] Details of the maleimide compound (M7) used in this embodiment can be found in Japanese Patent No. 7160151, which is incorporated herein by reference.

[0036] The maleimide compound (M8) is a bismaleimide compound having a hydrocarbon group in which 8 or more atoms are linearly connected, and is preferably a compound represented by the formula (M8). Such a maleimide compound (M8) tends to have a higher stress relaxation ability. As a result, the thermal expansion coefficient of the obtained cured product tends to be further reduced, and the electrical properties such as the dielectric constant and the dielectric tangent tend to be more excellent. (In the formula (M8), R １ and R ３ each independently represent a hydrocarbon group in which 8 or more atoms are linearly connected, and R ２ each independently represents a cyclic hydrocarbon group which may contain a hetero atom having 4 to 10 ring-constituting atoms, either substituted or unsubstituted, and n represents a number from 1 to 10.)

[0037] In the formula (M8), R １ and R ３ are each preferably an octylene group, and R ２ is preferably a cycloalkylene group having an alkyl group having 6 to 8 carbon atoms as a substituent.

[0038] As the maleimide compound (M8), the descriptions in paragraphs 0014 to 0022 of JP-A-2018-083893 and the descriptions in 0012 to 0022 of JP-A-2018-090728 can be referred to, and these contents are incorporated herein.

[0039] Maleimide compounds may be manufactured by known methods or commercially available products may be used. Examples of commercially available products include "BMI-80" manufactured by K.I. Chemicals Co., Ltd. as a compound represented by formula (M0), "NE-X-9470S" and "NE-X-9480S" manufactured by DIC Corporation as compounds represented by formula (M1), "BMI-2300" manufactured by Yamato Chemical Industries Co., Ltd. as a compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M3), and a compound represented by formula (M4) Examples of compounds include "BMI-70" manufactured by Kei-I Kasei Co., Ltd., "BMI-5100" manufactured by Yamato Kasei Kogyo Co., Ltd., "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M5), "MIZ-001" manufactured by Nippon Kayaku Co., Ltd. as a maleimide compound (M6), "NE-X-9500" manufactured by DIC Corporation as a maleimide compound (M7), "SFR" manufactured by Resonac Corporation, and "BMI-689", "BMI-1500", "BMI-2500", "BMI-3000", and "BMI-5000" manufactured by Designer Molecules Inc.

[0040] Other maleimide compounds include, for example, N-phenylmaleimide, N-cyclohexylmaleimide, oligomers of phenylmethanemaleimide, m-phenylenebismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane, 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, and their prepolymers, as well as prepolymers of these maleimides and amines. In addition to the above, the compounds described in paragraphs 0051 to 0068 of International Publication No. 2020 / 262577 can also be referenced, and this content is incorporated herein.

[0041] The maleimide group equivalent of the maleimide compound is preferably 130 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 170 g / eq. or more, even more preferably 180 g / eq. or more, even more preferably 200 g / eq. or more, even more preferably 290 g / eq. or more, and also preferably 1000 g / eq. or less, more preferably 800 g / eq. or less, even more preferably 700 g / eq. or less, even more preferably 600 g / eq. or less, and even more preferably 500 g / eq. or less. Setting it above the lower limit tends to result in better low dielectric properties (Dk and / or Df, particularly Df) of the resulting cured product. Setting it below the upper limit tends to result in better peel strength of the resulting cured product.

[0042] In this embodiment, if the resin composition contains a maleimide compound, the lower limit of its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more, depending on the application, etc., it may be 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more. A maleimide compound content of 1 part by mass or more tends to improve the flame resistance of the resulting cured product. Furthermore, the upper limit of the maleimide compound content is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and even more preferably 55 parts by mass or less, depending on the application, etc., it may be 50 parts by mass or less, or 45 parts by mass or less, depending on the application, etc. A maleimide compound content of 90 parts by mass or less tends to improve peel strength and low water absorption. The resin composition in this embodiment may contain only one maleimide compound or two or more. When two or more are included, it is preferable that the total amount is within the above range.

[0043] <<Aromatic Resins Having Carbon-Carbon Double Bonds at the Terminals>> Aromatic resins having carbon-carbon double bonds at the terminals are, for example, compounds that have carbon-carbon double bonds at the terminals and contain aromatic rings, and are compounds that harden with heat. Aromatic resins having carbon-carbon double bonds at the terminals tend to have low dielectric constant and low dielectric loss tangent due to their low polarity skeleton. Specifically, aromatic resins having carbon-carbon double bonds at the terminals preferably include one or more selected from the group consisting of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals, polymers having structural units represented by formula (V), and resins having terminal groups represented by formula (T1) and having an indan skeleton. It is more preferable to include polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals and / or resins having terminal groups represented by formula (T1) and having an indan skeleton, and it is even more preferable to include polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals.

[0044] In this embodiment, if the resin composition contains an aromatic resin having carbon-carbon double bonds at its ends, the content is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more depending on the application, and also preferably 95 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, even more preferably 55 parts by mass or less depending on the application, even more preferably 50 parts by mass or less, and may also be 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less. By setting the content of the aromatic resin having carbon-carbon double bonds at its ends to above the lower limit, compatibility and heat resistance tend to improve further. Furthermore, by setting the content of the aromatic resin having carbon-carbon double bonds at its ends to below the upper limit, low thermal expansion tend to improve further. The resin composition in this embodiment may contain only one aromatic resin having a carbon-carbon double bond at its terminus, or it may contain two or more aromatic resins. When two or more aromatic resins are included, it is preferable that the total amount is within the above range.

[0045] <<<Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals>>> The resin composition in this embodiment preferably contains a polyphenylene ether compound having carbon-carbon unsaturated double bonds at the terminals, and more preferably contains a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminals. The polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the terminals preferably contains a polyphenylene ether compound having two or more groups represented by the formula (Rx-1) described later (preferably vinylbenzyl groups) at the terminals. By using these polyphenylene ether compounds, it is possible to more effectively improve the low dielectric properties (Dk and / or Df) and low water absorption of printed circuit boards and the like. The details of these will be explained below.

[0046] Examples of polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal include compounds having a phenylene ether skeleton represented by the following formula (X1).

[0047] (In formula (X1), R ２４ , R ２５ , R ２６ , and, R ２７ (These may be the same or different characters, and represent an alkyl group, aryl group, halogen atom, or hydrogen atom having six or fewer carbon atoms.)

[0048] A polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus is given by formula (X2): (In formula (X2), R ２８ , R ２９ , R ３０ , R ３４ , and, R ３５ R may be the same or different, and represents an alkyl group or phenyl group having 6 or fewer carbon atoms. ３１ , R ３２ , and, R ３３ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) A repeating unit represented by formula (X3): (In formula (X3), R ３６ , R ３７ , R ３８ , R ３９ , R ４０ , R ４１ , R ４２ , and, R ４３ ) may be the same or different, and is a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. -A- is a straight, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms. ) may further contain repeating units represented by ).

[0049] The polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus is preferably a modified polyphenylene ether compound (hereinafter sometimes referred to as "modified polyphenylene ether compound (g)") in which part or all of the terminus is functionalized with an ethylenically unsaturated group, and more preferably a modified polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acryloyl groups and vinylbenzyl groups at its terminus. By employing such a modified polyphenylene ether compound (g), it is possible to further reduce the dielectric loss tangent (Df) of the cured resin composition and to improve water absorption and peel strength. These modified polyphenylene ether compounds (g) may be used individually or in combination of two or more.

[0050] Examples of modified polyphenylene ether compounds (g) include polyphenylene ether compounds represented by formula (OP). (In formula (OP), X represents an aromatic group, and -(Y-O) ｎ１ The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bonding site with the oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0051] The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described later can be an example, but it is preferable that it is at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Also, the -(Y-O)n １The polyphenylene ether structure represented by - may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. １ and / or n ２ If n is an integer greater than or equal to 2, １ individual constituent units (Y-O) and / or n ２ Each constituent unit may be identical or different. ２ The number is preferably 2 or more, and more preferably 2.

[0052] In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. １ A hydrogen atom or an alkyl group is preferred, a hydrogen atom or a methyl group is more preferred, and a hydrogen atom is even more preferred. ２ and R ３ Each of these is independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. １ , R ２ , and, R ３ The number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0053] In formula (Rx-1), r represents an integer from 0 to 6, and may be an integer of 1 or more, preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, even more preferably 1 or 2, and even more preferably 1.

[0054] In formula (Rx-1), Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In formula (Rx-1), z represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0055] A specific example of the group represented by formula (Rx-1) is the vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is the (meth)acryloyl group.

[0056] The resin composition in this embodiment is a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus, and is preferably a compound represented by formula (OP), which may include both a polyphenylene ether compound having a group represented by formula (Rx-1) and a polyphenylene ether compound having a group represented by formula (Rx-2).

[0057] Examples of modified polyphenylene ether compounds (g) include the compound represented by formula (OP-1). (In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents the polyphenylene ether structure, R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, and n １ n represents an integer from 0 to 6, and n ２ n represents an integer between 1 and 100, and n ３(where represents an integer from 1 to 4.) The aromatic group represented by X may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferable that it be at least one selected from the group consisting of alkyl groups, aryl groups, and halogen atoms having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. Also, the -(Y-O)n ２ The polyphenylene ether structure represented by - may or may not have substituents on the benzene ring, but it is preferable that it does. If substituents are present, the substituent Z described above can be exemplified, but it is preferably an alkyl group or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group. ２ and / or n ３ If n is an integer greater than or equal to 2, ２ individual constituent units (Y-O) and / or n ３ Each constituent unit may be identical or different. ３ The number is preferably 2 or more, and more preferably 2.

[0058] In this embodiment, the modified polyphenylene ether compound (g) is preferably a compound represented by formula (OP-2). Here, -(O-X-O)- is equation (OP-3): (In formula (OP-3), R ４ , R ５ , R ６ , R ９ , R １０ , and, R １１ These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. ７ , and, R ８ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) and / or formula (OP-4): (In formula (OP-4), R １２ , R １３ , R １４ , R１５ , R １６ , R １７ , R １８ , and, R １９ (These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group.) -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.

[0059] Also, -(Y-O)- is given by equation (OP-5): (In formula (OP-5), R ２０ , R ２１ These may be the same or different alkyl groups or phenyl groups having 6 or fewer carbon atoms. ２２ , R ２３ These may be the same or different, and are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group. It is preferable that it be represented as ). In particular, R ２０ and R ２１ Each of these groups independently has one or more methyl and / or cyclohexyl groups. This increases the rigidity of the resulting resin molecule. Since molecules with high rigidity have lower mobility than molecules with low rigidity, the relaxation time during dielectric relaxation is longer, resulting in excellent low dielectric properties (Dk and / or Df, especially Dk), which is therefore preferable. An example of formula (OP-5) is shown below. For polyphenylene ether compounds having the above structure, please refer to the description in Japanese Patent Application Publication No. 2019-194312, which is incorporated herein by reference.

[0060] In formula (OP-2), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are integers from 0 to 50, more preferably from 1 to 30, and preferably from 1 to 10. When a and / or b are integers of 2 or more, the 2 or more -(Y-O)- may each independently consist of one type of structure, or two or more structures may be arranged in a block or randomly. Furthermore, when multiple compounds represented by formula (OP-2) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0061] Examples of the -A- in formula (OP-4) include, but are not limited to, divalent organic groups such as methylene group, ethylidene group, 1-methylethylidene group, 1,1-propyridene group, 1,4-phenylenebis(1-methylethylidene) group, 1,3-phenylenebis(1-methylethylidene) group, cyclohexylidene group, phenylmethylene group, naphthylmethylene group, and 1-phenylethylidene group.

[0062] Among the compounds represented by the above formula (OP-2), R ４ , R ５ , R ６ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , R １８ , R １９ , R ２０ , and, R ２１ is an alkyl group having 3 or fewer carbon atoms, R ７ , R ８ , R ２２ , and, R ２３A polyphenylene ether compound in which is a hydrogen atom or an alkyl group having 3 or fewer carbon atoms is preferred, and in particular, the -(O-X-O)- represented by formula (OP-3) or formula (OP-4) is preferably formula (OP-9), formula (OP-10), and / or formula (OP-11), and the -(Y-O)- represented by formula (OP-5) is preferably formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the 2 or more -(Y-O)- may each independently be a structure in which two or more of formula (OP-12) and / or formula (OP-13) are arranged, or a structure in which formula (OP-12) and formula (OP-13) are arranged in a block or randomly.

[0063] (In formula (OP-10), R ４４ , R ４５ , R ４６ , and, R ４７ A is a hydrogen atom or a methyl group, and may be the same or different. B is a straight, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms. Specific examples of B are the same as the specific examples of A in formula (OP-4). (In formula (OP-11), -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.) Specific examples of -B- are the same as the specific examples of -A- in formula (OP-4).

[0064] The modified polyphenylene ether compound (g) is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and even more preferably a compound represented by formula (OP-15). (In formula (OP-14), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.) In formula (OP-14), a and b are each independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same. (In formula (OP-15), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.) In formula (OP-15), a and b are each independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same.

[0065] Furthermore, the polyphenylene ether compound used in this embodiment may also be a compound represented by formula (OP-16). (In formula (OP-16), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.) In formula (OP-16), a and b are each independently equivalent to a and b in formula (OP-2), and the preferred ranges are also the same.

[0066] Polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal may be produced by known methods or commercially available products may be used. Examples of commercially available products include SA9000 from SABIC Innovative Plastics, which is a modified polyphenylene ether compound with a methacryloyl group at the terminal. Examples of modified polyphenylene ether compounds with a vinylbenzyl group at the terminal include OPE-2St1200 and OPE-2St2200 from Mitsubishi Gas Chemical Company. Furthermore, as a modified polyphenylene ether compound with a vinylbenzyl group at the terminal, it is also possible to use a polyphenylene ether compound with a hydroxyl group at the terminal, such as SA90 from SABIC Innovative Plastics, which has been modified to have a vinylbenzyl group using vinylbenzyl chloride or the like.

[0067] Further details regarding polyphenylene ether compounds having a terminal carbon-carbon unsaturated double bond can be found in Japanese Patent Publication No. 2006-028111, Japanese Patent Publication No. 2018-131519, International Publication No. 2019-138992, and International Publication No. 2022-054303, the contents of which are incorporated herein by reference.

[0068] The number-average molecular weight in polystyrene terms of a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus (preferably a modified polyphenylene ether compound (g)) is preferably 500 to 3,000, as determined by GPC (gel permeation chromatography). A number-average molecular weight of 500 or more tends to further suppress stickiness when the resin composition in this embodiment is formed into a coating film. Furthermore, a number-average molecular weight of 3,000 or less tends to further improve solubility in solvents. In addition, the weight-average molecular weight in polystyrene terms of a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus (preferably a modified polyphenylene ether compound (g)) as determined by GPC is preferably 800 to 10,000, and more preferably 800 to 5,000. When the weight-average molecular weight is above the lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, low viscosity, and moldability of the resin composition when producing varnishes, etc., as described later tend to be improved. Furthermore, for polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals (preferably modified polyphenylene ether compounds (g)), the equivalent amount of the terminal carbon-carbon unsaturated double bonds is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, and more preferably 400 to 2500 g. When the equivalent amount of the terminal carbon-carbon unsaturated double bonds is above the lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to be lower, and when it is below the upper limit, the solubility in solvents, low viscosity, and moldability of the resin composition tend to be improved.

[0069] The functional group equivalent (equivalent of carbon-carbon unsaturated double bond) in polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the terminal is calculated by determining the amount of double bond from the measurement results using an infrared spectrometer and then calculating the reciprocal. The double bond equivalent [g / eq.] was determined as follows: The weight of the polyphenylene ether powder was weighed and recorded. After placing this powder in a volumetric flask, the measurement sample was prepared by making up the volume with carbon disulfide to a predetermined amount. This sample solution was placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Subsequently, infrared spectroscopic measurement of the sample solution was performed. In the case of vinyl groups in polyphenylene ether compounds, the value was 905 cm⁻¹. －１ Record the peak area of ​​the spectrum in the vicinity. When the carbon-carbon unsaturated double bond is a methacrylic group, the peak area is 1640 cm⁻¹. －１ The peak area of ​​the spectrum in the vicinity is recorded. From this area value and the calibration curve, the double bond concentration [mol / L] is determined as a measured value. Next, the double bond equivalent is calculated using the following formula: Double bond equivalent [g / eq.] = Powder weight in the measurement sample [g] / Double bond concentration [mol / L] × Volume of measurement sample liquid [L] The functional group equivalent of other thermosetting compounds other than polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the terminals can also be measured following the above method. However, for compounds (monomers) that can be expressed by a single molecular weight, the value obtained by (theoretical molecular weight ÷ number of functional groups) shall be used preferentially. If two or more other thermosetting compounds are included, the functional group equivalent of the other thermosetting compounds shall be the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each other thermosetting compound by its mass fraction.

[0070] In this embodiment, if the resin composition contains a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus, the lower limit of its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, and may be 25 parts by mass or more depending on the application. By setting the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminus to be above the lower limit, the moldability of the resin composition, the heat resistance, low water absorption, and low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. Furthermore, the upper limit of the content of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. Depending on the application, it may also be 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less. By keeping the content of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends below the above upper limit, the low dielectric properties (especially low dielectric loss tangent) and chemical resistance of the resulting cured product tend to improve. The resin composition in this embodiment may contain only one type of polyphenylene ether compound having carbon-carbon unsaturated double bonds at the ends, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0071] <<<Polymer having a constituent unit represented by formula (V)>>> The resin composition in this embodiment may contain a polymer having a constituent unit represented by formula (V). By including a polymer having a constituent unit represented by formula (V), a resin composition with excellent low dielectric properties (low relative permittivity, low dielectric loss tangent) can be obtained. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents the bond position.) An aromatic hydrocarbon linking group may consist only of an aromatic hydrocarbon which may have substituents, or it may consist of a combination of an aromatic hydrocarbon which may have substituents and another linking group, and it is preferable that it consists only of an aromatic hydrocarbon which may have substituents. The substituents that the aromatic hydrocarbon may have include substituent Z (for example, alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxyl groups, amino groups, carboxyl groups, halogen atoms, etc.). Furthermore, it is preferable that the above aromatic hydrocarbon does not have substituents. The aromatic hydrocarbon linking group is usually a divalent linking group.

[0072] Aromatic hydrocarbon linking groups specifically include phenylene groups, naphthalenediyl groups, anthracenediyl groups, phenanthrenediyl groups, biphenyldiyl groups, and fluoroorangeyl groups, which may have substituents, with the phenylene group being preferred among them, which may have substituents. The substituent Z mentioned above is an example of a substituent, but it is preferable that groups such as the phenylene group mentioned above do not have substituents.

[0073] A polymer having a structural unit represented by formula (V) more preferably contains at least one of the structural units represented by formula (V1), formula (V2), and formula (V3). * in the following formulas represents a bond position. Furthermore, the structural units represented by formulas (V1) to (V3) are sometimes collectively referred to as "structural unit (a)".

[0074] In formulas (V1) to (V3), L １The is an aromatic hydrocarbon linking group (preferably with 6 to 22 carbon atoms, more preferably with 6 to 18 carbon atoms, and even more preferably with 6 to 10 carbon atoms). Specifically, examples include phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrenediyl group, biphenyldiyl group, and fluoradiyl group, which may have substituents, and among these, the phenylene group, which may have substituents, is preferred. The substituent is exemplified by the substituent Z mentioned above, but it is preferable that groups such as the phenylene group mentioned above do not have substituents. The compound that forms the constituent 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. One of these divinyl aromatic compounds may be used, or two or more may be used as needed. That is, it is preferable that the constituent unit (a) is a constituent unit derived from a divinyl aromatic compound.

[0075] As described above, the polymer having the constituent unit represented by formula (V) may be a homopolymer of the compound forming the constituent unit (a), or it may be a copolymer with a constituent unit derived from another monomer. When the polymer having the constituent unit represented by formula (V) is a copolymer, the copolymerization ratio is preferably 3 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, and may be 15 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, even more preferably 30 mol% or less, and may also be 25 mol% or less or 20 mol% or less.

[0076] Other monomer-derived structural units include structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0077] The constituent unit (b) derived from the monovinyl aromatic compound is preferably a constituent unit represented by the following formula (V4).

[0078] In formula (V4), L ２ is an aromatic hydrocarbon linking group, and a specific example of a preferred one is the above L １ Examples include the following. * indicates the bonding position. R Ｖ１ R is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). Ｖ１ When it is a hydrocarbon group, its number of carbon atoms is preferably 1 to 6, and more preferably 1 to 3. Ｖ１ and L ２ It may have the substituent Z described above.

[0079] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (b) derived from a monovinyl aromatic compound, examples of monovinyl aromatic compounds include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinylbiphenyl; and nuclear alkyl-substituted vinyl aromatic compounds such as o-methylstyrene, m-methylstyrene, p-methylstyrene, o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, and ethylvinylbiphenyl. The monovinyl aromatic compounds exemplified here may optionally have the above-mentioned substituent Z. Furthermore, one or more of these monovinyl aromatic compounds may be used. Among these, structural unit (b) preferably contains structural units derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene, and more preferably further contains structural units derived from styrene in addition to structural units derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene.

[0080] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (b), the copolymerization ratio of structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may be 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, or 75 mol% or more. The upper limit is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.

[0081] A polymer having a structural unit represented by formula (V) may have other structural units besides structural units (a) and (b). Examples of other structural units include structural unit (c) derived from a cycloolefin compound. Examples of cycloolefin compounds include hydrocarbons having a double bond in the ring structure. Specifically, examples include monocyclic cyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, as well as compounds having a norbornene ring structure such as norbornene and dicyclopentadiene, and cycloolefin compounds in which aromatic rings are fused, such as indene and acenaphthylene. Examples of norbornene compounds are those described in paragraphs 0037 to 0043 of Japanese Patent Application Publication No. 2018-039995, the contents of which are incorporated herein by reference. The cycloolefin compounds exemplified herein may further have the substituent Z described above.

[0082] When a polymer having a structural unit represented by formula (V) is a copolymer containing structural unit (c), the copolymerization ratio of structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, even more preferably 70 mol% or less, and may also be 50 mol% or less, or 30 mol% or less.

[0083] A polymer having a structural unit represented by formula (V) may also incorporate structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as "other polymerizable compound"). Examples of other polymerizable compounds (monomers) include compounds containing three vinyl groups. Specifically, examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate, butadiene (e.g., 1,3-butadiene), isoprene, etc. The copolymerization ratio of structural unit (d) derived from the other polymerizable compound is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0084] As one embodiment of a polymer having a structural unit represented by formula (V), a polymer is provided in which structural unit (a) is essential and at least one of structural units (b) and (c) is included. Furthermore, an embodiment is provided in which the sum of structural units (a) to (c) accounts for 90 mol% or more, more preferably 95 mol% or more, and particularly preferably 98 mol% or more of the total structural units. As another embodiment of a polymer having a structural unit represented by formula (V), a polymer is provided in which structural unit (a) is essential and at least one of structural units (b) to (d) is included. Furthermore, an embodiment is provided in which the sum of structural units (a) to (d) accounts for 95 mol% or more, more preferably 98 mol% or more of the total structural units. As yet another embodiment of a polymer having a structural unit represented by formula (V), structural unit (a) is essential, and it is preferable that the polymer contains 90 mol% or more of structural units including aromatic rings among all structural units excluding the terminals, more preferably 95 mol% or more, and may also be a polymer of 100 mol%. In calculating the mole percentage per total constituent unit, one constituent unit is defined as one molecule of the monomer (e.g., divinyl aromatic compound, monovinyl aromatic compound, etc.) used in the production of a polymer having a constituent unit represented by formula (V).

[0085] The method for producing a polymer having a constituent unit represented by formula (V) is not particularly limited and can be carried out by conventional methods. For example, a raw material containing a divinyl aromatic compound (and, if necessary, a monovinyl aromatic compound, a cycloolefin compound, etc.) can be polymerized in the presence of a Lewis acid catalyst. As the Lewis acid catalyst, a metal fluoride such as boron trifluoride or a complex thereof can be used.

[0086] The structure of the chain ends of a polymer having a constituent unit represented by formula (V) is not particularly limited, but with respect to the group derived from the above-mentioned divinyl aromatic compound, it can take the structure of formula (E1) below. Note that L in formula (E1) １ This is the same as defined in formula (V1) above. * indicates the bond position. *-CH=CH-L １ -CH=CH ２ (E1)

[0087] When a group derived from a monovinyl aromatic compound becomes the chain terminus, it can take the structure shown in formula (E2) below. ２ and R Ｖ１ These have the same meaning as defined in equation (V4) above. * represents the bond position. *-CH=CH-L ２ -R Ｖ１ (E2)

[0088] The molecular weight of the polymer having the constituent unit represented by formula (V) is preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and even more preferably 1,500 or more, in terms of number average molecular weight (Mn). The upper limit of the number average molecular weight is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, even more preferably 100,000 or less, and may also be 30,000 or less, 10,000 or less, or 5,000 or less. The molecular weight of the polymer having the constituent unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 10,000 or more, in terms of weight average molecular weight Mw. By setting the weight average molecular weight to be above the lower limit, the excellent low dielectric properties (Dk and / or Df), particularly Df and dielectric properties after moisture absorption, of the polymer having the constituent unit represented by formula (V) can be effectively exhibited in the cured product of the resin composition. The upper limit of the weight-average molecular weight Mw is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less. By keeping the weight-average molecular weight below the above upper limit, when the prepreg or resin sheet is laminated onto a circuit forming substrate, embedding defects tend to be less likely to occur. The monodispersity (Mw / Mn), expressed as the ratio of the weight-average molecular weight (Mw) to the number-average molecular weight (Mn), is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and may also be 15 or less or 12 or less. As a lower limit, it is practical to be 1.1 or more, preferably 2.0 or more, more preferably 4 or more, even more preferably 5 or more, even more preferably 7 or more, and even more preferably 8 or more. When the resin composition in this embodiment contains two or more polymers having a constituent unit represented by formula (V), it is preferable that the Mw, Mn, and Mw / Mn of the mixture satisfy the above ranges.

[0089] The equivalent amount of vinyl groups in a polymer having a constituent unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, even more preferably 250 g / eq. or more, and may be 300 g / eq. or more, or 350 g / eq. or more. Furthermore, the equivalent amount of vinyl groups is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and may be 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 350 g / eq. or less. When the equivalent amount of vinyl groups is above the above lower limit, the storage stability of the resin composition is improved and the fluidity of the resin composition tends to improve. As a result, moldability is improved, voids are less likely to occur when forming prepregs, etc., and a more reliable printed circuit board tends to be obtained. On the other hand, when the vinyl group equivalent is below the aforementioned upper limit, the heat resistance of the resulting cured product tends to improve.

[0090] Polymers having a constituent unit represented by formula (V) preferably have cured products with excellent low dielectric properties (Dk and / or Df). For example, the cured product of a polymer having a constituent unit represented by formula (V) used in this embodiment preferably has a relative permittivity (Dk) at 10 GHz measured according to the cavity resonator perturbation method of 2.80 or less, more preferably 2.60 or less, even more preferably 2.50 or less, and even more preferably 2.40 or less. Furthermore, a practical lower limit for the relative permittivity is, for example, 1.80 or more. Furthermore, the cured product of a polymer having a constituent unit represented by formula (V) preferably has a dielectric loss tangent (Df) at 10 GHz measured according to the cavity resonator perturbation method of 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less. Furthermore, a practical lower limit for the dielectric loss tangent is, for example, 0.0001 or more. The relative permittivity (Dk) and dielectric loss tangent (Df) are measured by the following method. 4.5 g of resin powder is spread into a stainless steel mold measuring 100 mm x 30 mm x 1.0 mm high, and placed in a vacuum press (manufactured by Kitagawa Seiki Co., Ltd.). The mold is held at 200°C for 2 hours and pressed at a surface pressure of 3.0 MPa to produce a cured plate. After downsizing the cured plate to a width of 1.0 mm, it is dried at 120°C for 60 minutes. The relative permittivity (Dk) and dielectric loss tangent (Df) after drying are then measured at 10 GHz using a perturbation cavity resonator. The measurement temperature is 23°C.

[0091] With respect to polymers having a constituent unit represented by formula (V) in this specification, reference can be made to and incorporated herein to the compounds and their synthesis reaction conditions described in paragraphs 0029 to 0058 of International Publication No. 2017 / 115813, the compounds and their synthesis reaction conditions described in paragraphs 0013 to 0058 of Japanese Patent Application Publication No. 2018-039995, the compounds and their synthesis reaction conditions described in paragraphs 0008 to 0043 of Japanese Patent Application Publication No. 2018-168347, the compounds and their synthesis reaction conditions described in paragraphs 0014 to 0042 of Japanese Patent Application Publication No. 2006-070136, the compounds and their synthesis reaction conditions described in paragraphs 0014 to 0061 of Japanese Patent Application Publication No. 2006-089683, and the compounds and their synthesis reaction conditions described in paragraphs 0008 to 0036 of Japanese Patent Application Publication No. 2008-248001. A polymer having the constituent unit represented by formula (V) can be a commercially available product, such as LF-310T50 manufactured by Nippon Steel Chemical & Material Co., Ltd.

[0092] In this embodiment, if the resin composition contains a polymer having a structural unit represented by formula (V), the lower limit of its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and depending on the application, it may be 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. By setting the content of the polymer having a structural unit represented by formula (V) to the above lower limit, it tends to be possible to effectively achieve low dielectric properties, in particular, a low relative permittivity. Furthermore, the upper limit of the content of the polymer having a structural unit represented by formula (V) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, and may be 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, 35 parts by mass or less, or 30 parts by mass or less, based on 100 parts by mass of resin solids in the resin composition. By keeping the content of polymers having the structural unit represented by formula (V) below the above upper limit, the metal foil peel strength and low water absorption tend to improve. The resin composition in this embodiment may contain only one type of polymer having the structural unit represented by formula (V), or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range. Furthermore, the resin composition in this embodiment may also be configured to substantially not contain polymers having the structural unit represented by formula (V). Substantially not containing polymers means that the content of polymers having the structural unit represented by formula (V) is less than 1 part by mass per 100 parts by mass of resin solids in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0093] << (In formula (T1), Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may be independently substituted with a halogen atom, and x represents an integer from 0 to 4. * represents the bonding position with other sites.)

[0094] In formula (T1), Ma is preferably, independently, a C1-C10 hydrocarbon group which may be substituted with a halogen atom, more preferably a C1-C5 hydrocarbon group which may be substituted with a halogen atom, and even more preferably a C1-C3 hydrocarbon group which may be substituted with a halogen atom. Examples of halogen atoms include fluorine, chlorine, and bromine atoms, with fluorine or chlorine atoms being preferred. Ma is preferably, independently, a C1-C12 hydrocarbon group which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. Methyl and ethyl groups are particularly preferred for Ma.

[0095] x is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, even more preferably 0 or 1, and even more preferably 0.

[0096] Resin (A) may have terminal groups represented by formula (T1) at all of its ends, or at only some of its ends, for each resin molecule. Preferably, the resin molecule of resin (A) contains two terminal groups represented by formula (T1).

[0097] Resin (A) has an indan skeleton. While it is not particularly limited as long as at least one of the resin molecules contained in resin (A) has at least one indan skeleton, the number of indan skeletons in the resin molecules of resin (A) is preferably one or more per molecule, and more preferably 1 to 20. This configuration tends to more effectively exhibit the effects of the present invention.

[0098] The resin (A) preferably contains a constituent unit represented by formula (Txn). (In formula (T x n), n is the average number of repeating units, representing a number greater than 0 and less than or equal to 20. Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may be independently substituted with halogen atoms. x represents an integer from 0 to 4.)

[0099] In formula (Txn), Ma is preferably, independently, a C1-C10 hydrocarbon group which may be substituted with a halogen atom, more preferably a C1-C5 hydrocarbon group which may be substituted with a halogen atom, and even more preferably a C1-C3 hydrocarbon group which may be substituted with a halogen atom. Examples of halogen atoms include fluorine, chlorine, and bromine atoms, with fluorine or chlorine atoms being preferred. Ma is preferably, independently, a C1-C12 hydrocarbon group which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. Methyl and ethyl groups are particularly preferred for Ma.

[0100] x is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, even more preferably 0 or 1, and even more preferably 0.

[0101] The proportion of the constituent unit represented by formula (Txn) in 100 parts by mass of resin (A) is preferably 20 parts by mass or more, more preferably 25 parts by mass or more, even more preferably 34 parts by mass or more, even more preferably 45 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, and even more preferably 60 parts by mass or more, 65 parts by mass or more, and may also be 70 parts by mass or more, 75 parts by mass or more, and also preferably 100 parts by mass or less, and may be 95 parts by mass or less, 90 parts by mass or less, 85 parts by mass or less, 82 parts by mass or less, or 80 parts by mass or less.

[0102] Resin (A) more preferably contains a resin represented by formula (T1-1), and more preferably contains a resin represented by formula (T1-1-2). (In formula (T1-1), R is a group containing the constituent unit represented by formula (Tx). Ma represents a hydrocarbon group having 1 to 12 carbon atoms, which may each be independently substituted with a halogen atom. x is an integer from 0 to 4.) In formula (T1-1), Ma and x are the same as Ma and x in formula (T1), and the preferred ranges are also the same. (In formula (T1-1-2), R is a group containing the constituent unit represented by formula (Tx).) (In formula (Tx), n, o, and p are the average number of repeating units, where n is a number greater than 0 and less than or equal to 20, and o and p each independently represent numbers from 0 to 20, with 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms, which may be substituted with halogen atoms. x represents an integer from 0 to 4. Constituent units (a), (b), and (c) are each bonded to constituent units (a), (b), (c), or other groups by *, and each constituent unit may be bonded randomly.)

[0103] In formula (Tx), n, o, and p each represent the average number of repeating units in all molecules in the resin. In formula (Tx), the sum of n, o, and p is preferably 1.1 ≤ n + o + p, more preferably 1.2 ≤ n + o + p, even more preferably 1.5 ≤ n + o + p, even more preferably 2.0 ≤ n + o + p, even more preferably 2.5 ≤ n + o + p, even more preferably 3.0 ≤ n + o + p, and especially even more preferably 3.3 ≤ n + o + p. Furthermore, in formula (Tx), the sum of n, o, and p is preferably n + o + p ≤ 20.0, more preferably n + o + p ≤ 10.0, even more preferably n + o + p ≤ 8.0, even more preferably n + o + p ≤ 7.0, and even more preferably n + o + p ≤ 6.4. The sum of n, o, and p can be calculated by the method described in the examples of International Publication No. 2024 / 101237.

[0104] In formula (Tx), n is preferably 0.2 or greater, more preferably 0.6 or greater, even more preferably 1.0 or greater, even more preferably 1.2 or greater, even more preferably 1.6 or greater, and may also be 2.2 or greater, 2.4 or greater, and may also be 18.0 or less, more preferably 12.0 or less, even more preferably 9.0 or less, even more preferably 7.0 or less, even more preferably 6 or less, and may also be 5.0 or less, 4.0 or less, or 3.0 or less. In formula (Tx), o is preferably 0 or greater, more preferably 0.01 or greater, even more preferably 0.03 or greater, even more preferably 0.05 or greater, even more preferably 0.07 or greater, and also preferably 10.0 or less, more preferably 5.0 or less, even more preferably 4.0 or less, even more preferably 2.0 or less, even more preferably 1.0 or less, and may be 0.8 or less, 0.5 or less, 0.3 or less, 0.2 parts or less, or 0.1 parts or less. In formula (Tx), p is preferably 0 or greater, more preferably 0.01 or greater, even more preferably 0.1 or greater, even more preferably 0.2 or greater, even more preferably 0.3 or greater, and also preferably 18.0 or less, more preferably 10.0 or less, even more preferably 5.0 or less, even more preferably 4.0 or less, even more preferably 3.0 or less, and may be 2.5 or less, 2.0 or less, 1.0 or less, or 0.5 or less.

[0105] Furthermore, in formula (Tx), n / (n+o+p) is, for example, 0.2 or more, 0.25 or more, 0.3 or more, 0.34 or more, 0.4 or more, 0.45 or more, 0.5 or more, 0.55 or more, 0.6 or more, or 0.7 or more, and is also 1.0 or less. Among the constituent units (a) to (c) included in formula (Tx), constituent unit (a) which has the smallest activation energy and the largest free energy change is preferentially produced. In formula (T1-1), the proportion (total amount) of the constituent unit represented by formula (Tx) (i.e., any of the constituent units (a), (b), or (c)) in 100 parts by mass of R is preferably 80 parts by mass or more, more preferably 90 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 97 parts by mass or more, even more preferably 99 parts by mass or more, and also 100 parts by mass or less.

[0106] In equation (Tx), Ma and x are equivalent to Ma and x in equation (Txn), respectively, and the preferred ranges are also the same.

[0107] Furthermore, resin (A) may contain constituent units represented by formula (Ty). Formula (Ty)

[0108] The number-average molecular weight (Mn) of resin (A) as polystyrene equivalent, measured by GPC (gel permeation chromatography), is preferably 400 or more, more preferably 500 or more, even more preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By setting the number-average molecular weight above the lower limit, the heat resistance of the resulting cured product is improved, and the Df tends to decrease. Furthermore, the upper limit of the number-average molecular weight (Mn) of resin (A) as polystyrene equivalent, measured by GPC (gel permeation chromatography), is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, and even more preferably 1250 or less. Depending on the application, it may also be 1000 or less, or 800 or less. By setting the number-average molecular weight below the upper limit, the heat resistance of the resulting cured product is improved, and the relative permittivity (Dk) and dielectric loss tangent (Df) tend to decrease. Furthermore, the weight-average molecular weight (Mw) of resin (A) in polystyrene equivalent by GPC (details are as described in the examples below) is preferably 500 or more, more preferably 800 or more, even more preferably 900 or more, and even more preferably 1000 or more. By setting the weight-average molecular weight above the lower limit, the heat resistance of the resulting cured product is improved and the Df tends to decrease. The upper limit of the weight-average molecular weight (Mw) of resin (A) in polystyrene equivalent by GPC is preferably 6000 or less, more preferably 5000 or less, even more preferably 4000 or less, even more preferably 3000 or less, and even more preferably 2800 or less. Depending on the application, it may also be 2500 or less, 2000 or less, or 1500 or less. By setting the weight-average molecular weight below the upper limit, the heat resistance of the resulting cured product is improved and the relative permittivity (Dk) and dielectric loss tangent (Df) tend to decrease.

[0109] The resin (A) preferably has a Mw / Mn ratio, which is the ratio of weight-average molecular weight to number-average molecular weight, of 1.1 to 3.0. More preferably, the Mw / Mn of resin (A) is 1.2 or higher, even more preferably 1.3 or higher, even more preferably 1.4 or higher, even more preferably 1.5 or higher, and even more preferably 1.6 or higher. Furthermore, the Mw / Mn of resin (A) is more preferably 2.5 or lower, even more preferably 2.4 or lower, and may be 2.3 or lower, 2.0 or lower, or 1.8 or lower.

[0110] In this embodiment, the functional group equivalent (isopropenyl group equivalent) of resin (A) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, even more preferably 250 g / eq. or more, even more preferably 275 g / eq. or more, even more preferably 300 g / eq. or more, and also preferably 7500 g / eq. or less, more preferably 5000 g / eq. or less, even more preferably 4000 g / eq. or less, even more preferably 3000 g / eq. or less, even more preferably 2000 g / eq. or less, even more preferably 1500 g / eq. or less, and especially even more preferably 1000 g / eq. or less. Furthermore, it may also be 800 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, or 500 g / eq. or less. By setting the functional group equivalent of resin (A) to above the lower limit, the low dielectric properties (Dk and / or Df, especially Df) of the resulting cured product are improved, and the heat resistance over time (low dielectric properties after heating (Dk and / or Df, especially Df)) of the resulting cured product can be maintained more effectively. Furthermore, by setting the functional group equivalent of resin (A) to below the upper limit, the low dielectric properties (Dk and / or Df, especially Df) of the resulting cured product tend to be improved, and the heat resistance (especially the glass transition temperature) tends to be improved. The isopropenyl group equivalent is measured in accordance with the description of the examples in International Publication No. 2024 / 101237.

[0111] The method for producing resin (A) in this embodiment is not particularly limited, and resins obtained by known production methods can be used. Furthermore, the raw materials, reaction temperature, catalyst type, catalyst amount, reaction solvent, raw material concentration, etc., used in the synthesis of resin (A) are not particularly limited and can be appropriately selected or controlled according to the desired physical properties described above.

[0112] In this embodiment, examples of raw materials used when synthesizing resin (A) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0113] In addition to the above, as aromatic resins having a carbon-carbon double bond at the terminal, the compounds described in paragraphs 0011 to 0025 of International Publication No. 2023 / 176766, paragraphs 0012 to 0033 of International Publication No. 2023 / 176764, paragraphs 0012 to 0033 of International Publication No. 2023 / 176763, paragraphs 0026 to 0043 of International Publication No. 2023 / 176765, and Japanese Patent Application Publication No. 2023-104785 can be considered, and this information is incorporated herein by reference.

[0114] <<<Other compounds having carbon-carbon unsaturated double bonds at the terminals (compound (XC))>>> The resin composition in this embodiment may also contain other compounds having carbon-carbon unsaturated double bonds at the terminals other than those mentioned above (compound (XC)). An example of compound (XC) is a low molecular weight aromatic vinyl compound (excluding those that fall under the category of other low molecular weight compounds having cyclic compounds as described above). Examples of aromatic vinyl compounds include methylstyrene (e.g., 4-methylstyrene), ethyl vinylbenzene, diethyl 4-vinylbenzylphosphonate, 4-vinylbenzylglycidyl ether, α-methylstyrene, 4-tert-butylstyrene, vinylbenzyl ether, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene, with 4-methylstyrene, 4-tert-butylstyrene, divinylbenzene, and 1,2-bis(4-vinylphenyl)ethane being preferred. Furthermore, resins having isopropenyl groups as described in International Publication No. 2022 / 210095 (for example, the compounds described in Synthesis Examples 1, 2, 7, and 8 of the same publication) are exemplified and incorporated herein.

[0115] Another example of a compound (compound (XC)) having a carbon-carbon unsaturated double bond at its terminus is vinylbenzyl ether. Examples of vinylbenzyl ethers include reaction products produced from the reaction of 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), hexamethylbiphenol (2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol), 2,6-dihydroxynaphthalene, etc., with vinylbenzyl chloride and / or vinylbenzyl bromide. Furthermore, resorcinol, catechol, hydroquinone, 2,7-dihydroxynaphthalene, 2-(diphenylphosphoryl)hydroquinone, bis(2,6-dimethylphenol), 2,2'-biphenol, 4,4-biphenol, 2,2',6,6'-tetramethylbiphenol, 3,3',5,5'-tetrabromo-2,2'6,6'-tetramethylbiphenol, 3,3'-dibromo-2,2',6,6'-tetramethylbiphenol, 4,4'-isopropylidenebis(2,6-dibromophenol) (tetrabromobisphenol A), 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), 4,4'-isopropylidenebis(2-methylphenol), 4,4'-isopropylidenebis(2-allylphenol), 4 ,4'(1,3-phenylenediisopropylidene)bisphenol (bisphenol M), 4,4'-isopropylidenebis(3-phenylphenol), 4,4'-(1,4-phenylenediisopropylidene)bisphenol (bisphenol P), 4,4'-ethylidenediphenol (bisphenol E), 4,4'-oxydiphenol, 4,4'-thiodiphenol, 4,4'-thiobis(2,6-dimethylphenol), 4,4'-sulfonyldiphenol, 4,4'-sulfonylbis(2,6-dimethylphenol), 4,4'-sulfinyldiphenol, 4,4'-hexafluoroisopropylidene)bisphenol (bisphenol AF), 4,4'(1-phenylethylidene)bisphenol (bisphenol AP), bis(4-hydroxyphenyl)-2,2-Dichloroethylene (bisphenol C), bis(4-hydroxyphenyl)methane (bisphenol-F), bis(2,6-dimethyl-4-hydroxyphenyl)methane, 4,4'-(cyclopentylidene)diphenol, 4,4'-(cyclohexylidene)diphenol (bisphenol Z), 4,4'-(cyclododecylidene)diphenol, 4,4'-(bicyclo[2.2.1]heptylidene)diphenol, 4,4'-(9H-fluoren-9,9-diyl)diphenol, 3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one, 1-(4-hydroxyphenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol, 1-(4-hydroxy-3,5-dimethylphenyl)-1,3,3,4,6-pentamethyl-2, 3-dihydro-1H-inden-5-ol, 3,3,3',3'-tetramethyl-2,2',3,3'-tetrahydro-1,1'-spirobi[inden]-5,6'-diol (spirobindan), dihydroxybenzophenone (bisphenol K), tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)propane, tris(4-hydroxyphenyl)butane, tris(3-methyl-4-hydroxyphenyl)methane, tris(3,5-dimethyl-4-hydroxyphenyl)methane, tetrakis(4-hydroxyphenyl)ethane, tetrakis(3,5-dimethyl-4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)phenylphosphine oxide, dicyclopentadienylbis(2,Examples of vinyl benzyl ethers produced by the reaction of 6-dimethylphenol, dicyclopentadienylbis(o-cresol), dicyclopentadienylbisphenol, etc., with vinyl benzyl chloride or vinyl benzyl bromide include vinyl benzyl ethers. In addition to the above, vinyl benzyl compounds also include vinyl benzyl ether compounds described in paragraph 0041 of Japanese Patent Publication No. 2019-194312, resins having a styryl group described in International Publication No. 2022 / 210095 (for example, compounds described in Synthesis Examples 12 to 16 of the same publication), resins having a styryl group described in International Publication No. 2024 / 101237, resins having a styryl group described in International Publication No. 2024 / 101238, copolymers described in Japanese Patent Publication No. 2024-007493, compounds described in International Publication No. 2021 / 100658, and compounds described in Japanese Patent Publication No. 2024-086554, the contents of which are incorporated herein by reference. ,

[0116] In this embodiment, the content of other compounds having a carbon-carbon unsaturated double bond at the end (compound (XC)) in the resin composition is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and may be 15 parts by mass or more, depending on the application, etc., and may be 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, 35 parts by mass or more, 40 parts by mass or more, or 45 parts by mass or more. By setting the content of other compounds having a carbon-carbon unsaturated double bond at the end (compound (XC))) to be above the lower limit, the Df of the resulting cured product tends to be lower. Furthermore, the upper limit of the content of other compounds having a carbon-carbon unsaturated double bond at the end (compound (XC)) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, depending on the application, etc., and may be 70 parts by mass or less, 65 parts by mass or less, or 55 parts by mass or less, depending on the application, etc. By keeping the content of other compounds (compound (XC)) having a carbon-carbon unsaturated double bond at the terminal below the upper limit, the moldability of the resin composition and the heat resistance of the resulting cured product tend to improve. The resin composition in this embodiment may contain only one other compound (compound (XC)) having a carbon-carbon unsaturated double bond at the terminal, or it may contain two or more. When two or more are included, it is preferable that the total amount is within the above range.

[0117] <<Cyanate Ester Compounds>> The resin composition in this embodiment may contain cyanate ester compounds. The cyanate ester compound in this embodiment is not particularly limited as long as it contains one or more cyanate groups (preferably two or more, more preferably two to twelve, even more preferably two to six, even more preferably two to four, even more preferably two or three, and even more preferably two) in one molecule, and compounds commonly used in the field of printed circuit boards can be widely used. Furthermore, it is preferable that the cyanate ester compound is a compound in which the cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Preferred cyanate ester compounds in this embodiment include, for example, at least one selected from the group consisting of phenol novolac type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds (naphthol aralkyl type cyanates), naphthylene ether type cyanate ester compounds, biphenyl aralkyl type cyanate ester compounds, xylene resin type cyanate ester compounds, trisphenolmethane type cyanate ester compounds, adamantane skeleton type cyanate ester compounds, bisphenol M type cyanate ester compounds, bisphenol A type cyanate ester compounds, bisphenol E type cyanate ester compounds, diallylbisphenol A type cyanate ester compounds, and indancyanate compounds. Among these, from the viewpoint of further improving the low water absorption of the resulting cured product, it is more preferable to use at least one selected from the group consisting of phenol novolac type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds, naphthylene ether type cyanate ester compounds, xylene resin type cyanate ester compounds, bisphenol M type cyanate ester compounds, bisphenol A type cyanate ester compounds, and diallylbisphenol A type cyanate ester compounds; it is even more preferable to use at least one selected from the group consisting of phenol novolac type cyanate ester compounds and naphthol aralkyl type cyanate ester compounds; and it is even more preferable to use a naphthol aralkyl type cyanate ester compound.These cyanate ester compounds may be prepared by known methods or commercially available products may be used. Cyanate ester compounds having a naphthol aralkyl skeleton, naphthylene ether skeleton, xylene skeleton, trisphenolmethane skeleton, or adamantane skeleton tend to have a relatively large number of functional group equivalents and fewer unreacted cyanate ester groups, resulting in cured resin compositions using these compounds exhibiting even greater low water absorption. Furthermore, due primarily to the presence of an aromatic or adamantane skeleton, plating adhesion tends to be even more improved.

[0118] As naphthol aralkyl type cyanate ester compounds, compounds represented by the following formula (1) are more preferred. (In formula (1), R ３ Each of these independently represents either a hydrogen atom or a methyl group, and n3 represents an integer greater than or equal to 1.

[0119] In formula (1), R ３ Each of these independently represents either a hydrogen atom or a methyl group, with hydrogen atoms being preferred. In formula (1), n3 is an integer of 1 or more, preferably an integer between 1 and 20, more preferably an integer between 1 and 10, and even more preferably an integer between 1 and 6.

[0120] Furthermore, while the novolac-type cyanate ester compound is not particularly limited, for example, a compound represented by the following formula (VII) is preferred. (In formula (VII), R ６ Each of these independently represents either a hydrogen atom or a methyl group, and n7 represents an integer greater than or equal to 1.

[0121] In formula (VII), R ６ Each of these independently represents either a hydrogen atom or a methyl group, with hydrogen atoms being preferred. In formula (VII), n7 is an integer of 1 or more, preferably an integer between 1 and 20, more preferably an integer between 1 and 10, and even more preferably an integer between 1 and 6.

[0122] As the bisphenol A type cyanate ester compound, one or more compounds selected from the group consisting of 2,2-bis(4-cyanatophenyl)propane and 2,2-bis(4-cyanatophenyl)propane prepolymers may be used.

[0123] Examples of indanthyanate compounds include those represented by the following formula (a): Formula (a) (In equation (a), n is the average number of repetitions, and is a number between 3.0 and 15.0.)

[0124] In addition to the above, the compounds described in paragraphs 0035 to 0061 of Japanese Patent Application No. 2024-110099 can also be used as cyanate ester compounds, and this is incorporated herein by reference.

[0125] The resin composition in this embodiment preferably contains a cyanate ester compound in a range that does not impair the effects of the present invention. When the resin composition in this embodiment contains a cyanate ester compound, the lower limit of its content is preferably 0.1 parts by mass or more, more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. When the cyanate ester compound content is 0.1 parts by mass or more, the heat resistance, flame resistance, chemical resistance, low dielectric properties (low relative permittivity, low dielectric loss tangent), and insulation properties of the resulting cured product tend to improve. When the resin composition in this embodiment contains a cyanate ester compound, the upper limit of its content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. The resin composition in this embodiment may contain only one type of cyanate ester compound, or it may contain two or more types. If two or more types are included, it is preferable that the total amount falls within the above range.

[0126] Details of (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having vinylene groups can be found in paragraphs 0173 to 0225 of International Publication No. 2024 / 101238, which are incorporated herein by reference. The resin composition of this embodiment may contain, for example, less than 40 parts by mass of (meth)allyl compounds and / or (meth)acrylate compounds, preferably less than 30 parts by mass, more preferably less than 20 parts by mass, even more preferably less than 10 parts by mass, even more preferably less than 5 parts by mass, even more preferably 3 parts by mass or less, even more preferably 1 part by mass or less, or may not contain any at all, based on 100 parts by mass of resin solids contained in the resin composition. The (meth)allyl compound and / or (meth)acrylate compound mentioned above are exemplified by being a (meth)allyl compound and / or (meth)acrylate compound other than a compound that corresponds to a polyphenylene ether compound. The (meth)allyl compound and / or (meth)acrylate compound are exemplified by having a weight-average molecular weight of less than 5000, more specifically less than 3000, and particularly less than 1000. An example of the resin composition of this embodiment is a (meth)allyl compound (excluding compounds that correspond to polyphenylene ether compounds) in which the content of a compound with a weight-average molecular weight of less than 3000 is 1 part by mass or less per 100 parts by mass of resin solids contained in the resin composition. Another example of the resin composition of this embodiment is a (meth)acrylate compound (excluding compounds that correspond to polyphenylene ether compounds) in which the content of a compound with a weight-average molecular weight of less than 3000 is 1 part by mass or less per 100 parts by mass of resin solids contained in the resin composition.

[0127] <Flame Retardant> The resin composition in this embodiment may contain a flame retardant. Examples of flame retardants include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, with phosphorus-based flame retardants being preferred. As flame retardants, known substances can be used, for example, halogenated flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromopentane, chlorinated polystyrene, chlorinated paraffin, red phosphorus, tricresyl phosphate, triphenyl phosphate, 2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, cresyldiphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, Examples of suitable flame retardants include monomeric phosphate esters such as tris(chloroethyl) phosphate, phosphazenes, phenoxyphosphazenes, 1,3-phenylenebis(2,6-dixylenyl phosphate), xylenebisdiphenylphosphine oxides of the bisdiphenylphosphine oxide type, condensed phosphate esters of dixylenyl phosphate of the phosphate ester type, 6H-dibenz[c,e][1,2]oxaphosphorine, 6,6'-[1,4-phenylenebis(methylene)]bis-,6,6'-dioxide, and phosphinate metal salts; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, partial boehmite, boehmite, zinc borate, and antimony trioxide; and silicone-based flame retardants such as silicone rubber and silicone resin, with phosphinate metal salts being preferred.

[0128] The metal salt of phosphinic acid is preferably a salt of at least one metal selected from the group consisting of Mg, Ca, Al, Zn, Ti, Sn, Zr, and Fe, more preferably at least one metal selected from the group consisting of Mg, Ca, and Al, and even more preferably Al.

[0129] The flame retardant is more preferably a compound represented by formula (i). (R' and R'' are each independently hydrocarbon groups having 1 to 12 carbon atoms, and M is a metal atom. p is the valence of the metal atom represented by M.)

[0130] In formula (i) above, R' and R'' each independently represent a hydrocarbon group having 1 to 12 carbon atoms. Examples of such hydrocarbon groups include alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, and aralkyl groups. Examples of the alkyl groups include alkyl groups having 1 to 12 carbon atoms, such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, lauryl group, isopropyl group, isobutyl group, sec-butyl group, t-butyl group, isopentyl group, neopentyl group, 2-methylpentyl group, 2-methylhexyl group, 2-ethylpentyl group, 3-ethylpentyl group, isooctyl group, 2-ethylhexyl group, 3-ethylhexyl group, isononyl group, 2-ethyloctyl group, isodecyl group, and isododecyl group. Examples of the above cycloalkyl groups include cyclopentyl, cyclohexyl, cyclooctyl, and cyclodecanyl groups, which have 5 to 12 carbon atoms. Examples of the above alkenyl groups include vinyl, allyl, butenyl, 1-pentenyl, 2-pentenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, nonenyl, decenyl, and dodecenyl groups, which have 2 to 12 carbon atoms. Examples of the above aryl groups include phenyl, toluyl, biphenyl, and naphthyl groups, which have 6 to 12 carbon atoms. Examples of the above aralkyl groups include benzyl, phenylethyl, and phenylpropyl groups, which have 7 to 12 carbon atoms. Among the above, R' and R'' are preferably alkyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 8, more preferably 1 to 6, and even more preferably 1 to 3. R' and R'' may be the same or different, but it is preferable that they be the same.

[0131] In formula (i) above, M is a metal atom, preferably a salt of at least one metal selected from the group consisting of Mg, Ca, Al, Zn, Ti, Sn, Zr, and Fe, more preferably at least one metal selected from the group consisting of Mg, Ca, and Al, and even more preferably Al.

[0132] The resin composition used in this embodiment may contain commercially available metal phosphinate flame retardants, such as "EXOLIT OP1230", "EXOLIT OP1240", "EXOLIT OP1400", "EXOLIT OP930", "EXOLIT OP935", and "EXOLIT OP945TP" manufactured by Clariant Chemicals Co., Ltd.

[0133] If the resin composition in this embodiment contains a flame retardant, its content is preferably 1 part by mass or more, more preferably 3 parts by mass or more, 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, based on 100 parts by mass of the resin solids in the resin composition. The flame retardant can be used alone or in combination of two or more types. When two or more types are used, the total amount will be within the above range.

[0134] <Activated Ester Compounds> The resin composition in this embodiment may contain activated ester compounds to the extent that it does not impair the effects of the present invention. The activated ester compounds are not particularly limited, and for example, the description in paragraphs 0064 to 0066 of International Publication No. 2021 / 172317 can be given reference, and this content is incorporated herein.

[0135] In this embodiment, if the resin composition contains an active ester compound, it is preferable that the amount is 1 part by mass or more, and more preferably 50 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. The resin composition in this embodiment may contain only one type of active ester compound, or it may contain two or more types. If it contains two or more types, it is preferable that the total amount is within the above range. Furthermore, the resin composition in this embodiment may also be configured to be substantially free of active ester compounds. Substantially free means that the content of the active ester compound is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass, per 100 parts by mass of resin solids in the resin composition.

[0136] <Dispersant> The resin composition in this embodiment may contain a dispersant. Suitable dispersants are those commonly used for paints, and the type is not particularly limited. Preferably, copolymer-based wetting dispersants are used, and specific examples include DISPERBYK®-110, 111, 161, 180, 2009, 2152, 2155, BYK®-W996, W9010, W903, and W940, all manufactured by BIC-Chemie Japan Co., Ltd.

[0137] If the resin composition in this embodiment contains a dispersant, the lower limit of its content is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and may be 0.3 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. The upper limit of the dispersant content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and may be even 3 parts by mass or less, per 100 parts by mass of resin solids in the resin composition. One type of dispersant can be used alone, or two or more types can be used in combination. When two or more types are used, the total amount will be within the above range.

[0138] <Solvent> The resin composition in this embodiment may contain a solvent, and preferably an organic solvent. When a solvent is included, the resin composition in this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the above-mentioned resin solids are dissolved or miscible with the solvent. The solvent is not particularly limited as long as it is a polar or nonpolar organic solvent capable of dissolving or miscible at least a portion, preferably all, of the above-mentioned resin solids. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), cellosolves (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and amides (e.g., dimethoxyacetamide, dimethylformamides, etc.). Examples of nonpolar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). Solvents can be used individually or in combination of two or more. When using two or more solvents, the total amount must be within the above range.

[0139] <Curing accelerator> The resin composition in this embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, but examples include imidazoles such as 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, and triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, α,α'-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexine-3; azo compounds such as azobisnitrile (e.g., azobisisobutyronitrile) and 2,2-azobis(2,4,4-trimethylpentane); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, and 2-N-ethylanilinoethanol Examples include tertiary amines such as tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organometallic salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octoate, manganese octoate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetone; compounds obtained by dissolving these organometallic salts in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organotin compounds such as dioctyl tin oxide, other alkyltins, and alkyltin oxides. Among these, preferred curing accelerators are at least one selected from the group consisting of imidazoles, organometallic salts, and organic peroxides, with at least one selected from the group consisting of organometallic salts and organic peroxides being more preferred, and organic peroxides being even more preferred.

[0140] If the resin composition in this embodiment contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.05 parts by mass or more, and even more preferably 0.08 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. The upper limit of the curing accelerator content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, even more preferably 2 parts by mass or less, even more preferably 1.0 part by mass or less, even more preferably 0.8 parts by mass or less, even more preferably 0.5 parts by mass or less, and especially most preferably 0.3 parts by mass or less, and depending on the application, it may be 0.2 parts by mass or less, or 0.15 parts by mass or less. The resin composition in this embodiment is preferable in that it can sufficiently cure even if the curing accelerator content is below the above upper limit. The curing accelerator can be used alone or in combination of two or more types. If two or more types are used, the total amount will be within the above range.

[0141] <Filler> The resin composition in this embodiment may contain fillers other than the glass substrate. By including a filler, the physical properties of the resin composition and its cured product, such as dielectric properties (relative permittivity and / or dielectric loss tangent), flame resistance, and low thermal expansion, can be further improved. Furthermore, it is more preferable that the filler used in this embodiment has excellent low dielectric properties (Dk and / or Df). For example, the filler used in this embodiment preferably has a relative permittivity (Dk) of 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less at a frequency of 10 GHz measured according to the cavity resonator perturbation method. Furthermore, the lower limit of the relative permittivity is practically 2.0 or more. Furthermore, the filler used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, at a frequency of 10 GHz measured according to the cavity resonator perturbation method. Furthermore, the lower limit of the dielectric loss tangent is practically 0.0001 or more.

[0142] The type of filler used in this embodiment is not particularly limited, and those commonly used in the industry can be suitably used. Specifically, silica such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, etc.; metal oxides such as alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, etc.; composite oxides such as zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, etc.; nitrides such as boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, etc.; aluminum hydroxide, heat-treated aluminum hydroxide (aluminum hydroxide that has been heat-treated to reduce some of the crystal water), boehmite, magnesium hydroxide, etc. (including hydrates); acid Examples of inorganic fillers include molybdenum compounds such as molybdenum molasses and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (including glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, and spherical glass, as well as organic fillers such as styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell-type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders. In this embodiment, inorganic fillers are preferred, and more preferably include one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. From the viewpoint of low dielectric properties (Dk and / or Df), it is more preferable to include one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferable to include silica. By using these inorganic fillers, the properties of the cured resin composition, such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy, are further improved.

[0143] The filler content in the resin composition in this embodiment can be appropriately set according to the desired properties and is not particularly limited, but is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and may be 30 parts by mass or more, 50 parts by mass or more, or 90 parts by mass or more, depending on the application, etc. Setting it above the lower limit tends to result in better low thermal expansion and low dielectric loss tangent of the resulting cured product. Furthermore, the upper limit of the filler content is preferably 300 parts by mass or less, more preferably 250 parts by mass or less, even more preferably 200 parts by mass or less, and even more preferably 180 parts by mass or less, and may be 150 parts by mass or less, or 110 parts by mass or less, depending on the application, etc. Setting it below the upper limit tends to result in better moldability of the resin composition. In the resin composition of this embodiment, as an example of a preferred embodiment, there is an example in which the filler content is 1 to 95% by mass of the components excluding the solvent, and an embodiment in which it is 10% to 60% by mass is preferred. The resin composition of this embodiment may contain only one type of filler, or it may contain two or more types. When it contains two or more types, it is preferable that the total amount is within the above range.

[0144] In the resin composition of this embodiment, when a filler, particularly an inorganic filler, is used, a silane coupling agent may be further included. Including a silane coupling agent tends to further improve the dispersibility of the filler and the adhesive strength between the resin component and the filler and glass substrate. Silane coupling agents are not particularly limited and generally include silane coupling agents used for surface treatment of inorganic materials, such as aminosilane compounds (e.g., γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, etc.), epoxysilane compounds (e.g., γ-glycidoxypropyltrimethoxysilane, etc.), vinylsilane compounds (e.g., vinyltrimethoxysilane, vinyltriethoxysilane, tetravinylsilane, triethylvinylsilane, 1,3-vinyltetramethylsiloxane, etc.), styrylsilane compounds (e.g., 4-vinylphenyltrimethoxysilane, etc.), acrylicsilane compounds (e.g., γ-acryloxypropyltrimethoxysilane, etc.), cationicsilane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds. Among these, it is preferable to include at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylicsilane compounds, with vinylsilane compounds being more preferable. The silane coupling agent can be used alone or in combination of two or more. The content of the silane coupling agent is not particularly limited, but may be 0.1 to 5.0 parts by mass per 100 parts by mass of resin solids in the resin composition.

[0145] <Elastomer> The resin composition in this embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but it is preferably thermoplastic. The elastomer in this embodiment is preferably a styrene-based elastomer. Details of the elastomer can be found in paragraphs 0230-0247 of International Publication No. 2024 / 101238, which are incorporated herein by reference.

[0146] When the resin composition in this embodiment contains a thermoplastic elastomer, its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 12 parts by mass or more, per 100 parts by mass of resin solids in the resin composition. Setting it above the lower limit tends to further improve dielectric properties (low dielectric loss tangent). Furthermore, the upper limit of the thermoplastic 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 resin solids in the resin composition. Setting it below the upper limit tends to further improve heat resistance. The resin composition in this embodiment may contain only one type of thermoplastic elastomer, or it may contain two or more types. When two or more types are included, it is preferable that the total amount is within the above range.

[0147] <Other Components> In addition to the components described above, the resin composition in this embodiment may also contain various polymer compounds (such as petroleum resins) such as thermoplastic resins and their oligomers, and various additives. Examples of additives include at least one selected from the group consisting of ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, glossing agents, and polymerization inhibitors. The content of other components in the resin composition in this embodiment (various polymer compounds such as thermoplastic resins and their oligomers, various additives, etc.) other than the components described above is preferably 0 parts by mass or more and less than 10 parts by mass, more preferably 0 parts by mass or more and less than 5 parts by mass, even more preferably 0 parts by mass or more and less than 3 parts by mass, and may be 0 parts by mass or more and less than 1 part by mass, per 100 parts by mass of resin solids. The total amount of additives is preferably 0 parts by mass or more and less than 5 parts by mass, more preferably 0 parts by mass or more and less than 3 parts by mass, even more preferably 0 parts by mass or more and less than 1 part by mass, and may also be 0 parts by mass or more and less than 0.5 parts by mass, per 100 parts by mass of resin solids.

[0148] <Glass Substrate> The prepreg of this embodiment has a dielectric constant of 4.4 or less at a frequency of 10 GHz, as measured by the cavity resonator perturbation method in accordance with JIS C218:2007, and contains SiO ２ The material contains a glass substrate in a proportion of 61 to 85% by mass. By including such a glass substrate, a prepreg can be obtained that maintains low dielectric properties while also having excellent drillability. The glass substrate is not particularly limited in type, as long as it is a substrate made of glass, and can be glass cloth (woven fabric), nonwoven fabric, chopped strand mat, surfacing mat, etc., with glass cloth being more preferred.

[0149] The glass substrate used in this embodiment has a dielectric constant of 4.4 or less at a frequency of 10 GHz, measured by the cavity resonator perturbation method in accordance with JIS C218:2007, preferably 4.3 or less, more preferably 4.2 or less, and even more preferably 4.1 or less. By keeping it below the upper limit, the resulting cured prepreg tends to have a lower dielectric constant. Furthermore, there is no specific lower limit for the dielectric constant, but 3.0 or higher is practical, and values ​​above 3.8, and even 3.9 or higher, sufficiently satisfy the required performance.

[0150] The glass substrate used in this embodiment preferably has a dielectric loss tangent of 0.0030 or less at a frequency of 10 GHz, measured by the cavity resonator perturbation method in accordance with JIS C218:2007, more preferably less than 0.0020, even more preferably 0.0015 or less, even more preferably 0.0013 or less, even more preferably 0.0012 or less, and even more preferably 0.0011 or less. Furthermore, there is no particular lower limit for the dielectric loss tangent, but 0.0001 or more is practical, and even 0.0005 or more will sufficiently satisfy the required performance.

[0151] The glass substrate used in this embodiment is SiO ２ The glass substrate contains SiO in a proportion of 61 to 85% by mass. ２The content of is preferably 62% by mass or more, more preferably 63% by mass or more, even more preferably 64% by mass or more, even more preferably 65% ​​by mass or more, and also preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, even more preferably 68% by mass or less, and even more preferably 67% by mass or less. Setting it above the lower limit tends to improve the low dielectric properties (Dk and / or Df) of the cured prepreg. Setting it below the upper limit tends to further improve the drillability of the cured prepreg.

[0152] B in the glass substrate used in this embodiment ２ O ３ The content of is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 12% by mass or more, and also preferably 20% by mass or more, more preferably 18% by mass or less, and even more preferably 16% by mass or less.

[0153] The CaO content in the glass substrate used in this embodiment is preferably 1% by mass or more, more preferably 1.5% by mass or more, even more preferably 2.0% by mass or more, preferably 3.8% by mass or less, more preferably 3.5% by mass or less, even more preferably 3.0% by mass or less, even more preferably 2.6% by mass or less, and even more preferably 2.4% by mass or less.

[0154] In this embodiment, it is preferable to have a low MgO content in the glass substrate. Specifically, the MgO content in the glass substrate is preferably 0.7% by mass or less, more preferably 0.5% by mass or less, even more preferably 0.3% by mass or less, even more preferably 0.1% by mass or less, and may also be 0% by mass or more.

[0155] The composition of the glass substrate is measured by X-ray fluorescence analysis. In this embodiment, the glass substrate used is, in addition to the above, Al ２O ３ CO ２ , TiO ２ It may also contain F, etc. The glass substrate used in this embodiment is SiO ２ , B ２ O ３ Al ２ O ３ CaO, CO ２ , TiO ２ , F, and P ２ O ５ Preferably, the total of these components accounts for 99% or more by mass of the glass contained in the glass substrate, and more preferably 99.5% or more by mass. When the glass substrate used in this embodiment satisfies the above composition, the effects of the present invention tend to be exhibited more effectively.

[0156] The thickness of the glass cloth is preferably 1 μm or more, more preferably 5 μm or more, preferably 200 μm or less, more preferably 150 μm or less, and even more preferably 100 μm or less. Setting the thickness above the lower limit tends to increase rigidity. Setting the thickness below the upper limit tends to further improve the thinning effect.

[0157] The mass of the glass cloth is 10 g / m ２ Preferably, it is 30 g / m ２ It is more preferable that the amount be greater than or equal to 50 g / m ２ It is even more preferable that the amount be greater than or equal to 200 g / m². ２ Preferably, it is 150 g / m ２ It is more preferable that the following conditions apply: 100 g / m ２ It is even more preferable that the following conditions are met. Setting the value above the lower limit tends to increase rigidity. Setting the value below the upper limit tends to further improve the thin-leaf effect.

[0158] <Prepreg composition and manufacturing method> The prepreg of this embodiment comprises a resin composition and / or a semi-cured product of the resin composition and glass cloth. In this embodiment, it is preferable that the prepreg exists in a semi-cured state in which the resin composition is impregnated into the glass cloth. The semi-cured product includes, for example, a state referred to as the B stage.

[0159] The thickness of the prepreg in this embodiment is preferably 5 μm or more, and more preferably 10 μm or more. The upper limit of the thickness is preferably 200 μm or less, and more preferably 180 μm or less.

[0160] The prepreg of this embodiment is obtained, for example, by applying the resin composition of this embodiment to a glass cloth (e.g., impregnation and / or coating), and then partially curing it by heating (e.g., drying at 120 to 220°C for 2 to 15 minutes). In this case, the total amount of the components in the resin composition excluding the solvent relative to the glass cloth, i.e., the amount of cured resin composition relative to the total amount of prepreg after partial curing, is preferably in the range of 20% by mass or more, more preferably in the range of 30% by mass or more, preferably in the range of 99% by mass or less, and more preferably in the range of 80% by mass or less.

[0161] The relative permittivity (Dk) of the prepreg in this embodiment, measured by the cavity resonator perturbation method at a frequency of 10 GHz, is preferably less than 3.2, and more preferably less than 3.0. The lower limit of the relative permittivity is 0 or greater, and even if it is 1.0 or greater, it sufficiently satisfies the required performance. The dielectric loss tangent (Df) of the prepreg in this embodiment, measured by the cavity resonator perturbation method at a frequency of 10 GHz, is preferably less than 0.0025, and more preferably less than 0.0020. The lower limit of the dielectric loss tangent is 0 or greater, and even if it is 0.0001 or greater, it sufficiently satisfies the required performance.

[0162] <Metal Foil Clad Laminate> The metal foil clad laminate of this embodiment includes the prepreg of this embodiment and metal foil arranged on one or both sides of the prepreg. As a method for manufacturing the metal foil clad laminate of this embodiment, for example, one method is to arrange at least one sheet of the prepreg of this embodiment (preferably two or more sheets stacked) and arrange metal foil on one or both sides thereof and then laminate-form it. More specifically, it can be manufactured by arranging metal foil such as copper or aluminum on one or both sides of the prepreg and then laminating it. The number of prepreg sheets is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil is not particularly limited as long as it is used as a material for printed circuit boards, but examples include copper foil such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited and may be about 1.5 to 70 μm. Furthermore, when copper foil is used as the metal foil, it is preferable that the surface roughness Rz of the copper foil, measured according to JIS B0601:2013, is adjusted to 0.2 to 4.0 μm. Setting the surface roughness Rz of the copper foil to 0.2 μm or more results in an appropriate surface roughness, which tends to further improve the copper foil peel strength. On the other hand, setting the surface roughness Rz of the copper foil to 4.0 μm or less results in an appropriate surface roughness, which tends to further improve the dielectric loss tangent properties of the resulting cured product. From the viewpoint of the dielectric loss tangent properties of the resulting cured product and the copper foil peel strength, the surface roughness Rz of the copper foil is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, particularly preferably 0.7 μm or more, even more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0163] The lamination method includes methods commonly used when forming laminates and multilayer boards for printed circuit boards. More specifically, it includes a method using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, etc., at a temperature of approximately 180 to 350°C, a heating time of approximately 100 to 300 minutes, and a surface pressure of approximately 1 to 10 MPa. Furthermore, a multilayer board can be made by laminating the prepreg of this embodiment with a separately manufactured inner layer wiring board. As a method for manufacturing a multilayer board, for example, copper foil of approximately 35 μm is placed on both sides of one prepreg of this embodiment, and after lamination using the above molding method, an inner layer circuit is formed, and this circuit is subjected to a blackening treatment to form an inner layer circuit board. After that, this inner layer circuit board and the prepreg of this embodiment are arranged alternately one by one, and then copper foil is placed as the outermost layer, and a multilayer board can be manufactured by lamination under the above conditions, preferably under vacuum. The metal foil-clad laminate of this embodiment can be suitably used as a printed circuit board.

[0164] <Printed Wiring Board> The printed wiring board of this embodiment includes an insulating layer and a conductive layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of the layers formed from the prepreg of this embodiment. Such a printed wiring board can be manufactured according to conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is shown below. First, a metal foil laminate such as the copper foil laminate described above is prepared. Next, an etching treatment is performed on the surface of the metal foil laminate to form an inner layer circuit and produce an inner layer substrate. Surface treatment is performed on the inner layer circuit surface of this inner layer substrate to increase the adhesive strength as needed, then the required number of prepregs described above are stacked on the inner layer circuit surface, and then metal foil for the outer layer circuit is laminated on the outside thereafter, and the substrate is integrally molded by heating and pressing. In this way, a multilayer laminate is produced in which an insulating layer made of glass cloth and a cured resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, after drilling holes for through-holes and via-holes in this multilayer laminate, a plated metal film is formed on the walls of these holes to provide electrical connectivity between the inner layer circuit and the metal foil for the outer layer circuit. Furthermore, the metal foil for the outer layer circuit is etched to form the outer layer circuit, thereby manufacturing a printed circuit board.

[0165] Furthermore, it is preferable to reduce the surface roughness of the insulating layer after the roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after the roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but for example it may be 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x lens. The non-contact surface roughness meter used is the WYKONT 3300 manufactured by Bee Instruments.

[0166] Furthermore, this embodiment also relates to a semiconductor device including the printed circuit board. Details of the semiconductor device can be found in paragraphs 0200 to 0202 of Japanese Patent Application Publication No. 2021-021027, and these contents are incorporated herein by reference.

[0167] The present invention will be described in more detail below with reference to examples. The materials, amounts used, proportions, processing content, processing procedures, etc., shown in the following examples can be modified as appropriate, as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments, etc., used in the examples are difficult to obtain due to discontinuation or other reasons, measurements can be taken using other instruments with equivalent performance.

[0168] <Measurement of Weight-Average and Number-Average Molecular Weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of compounds (including resins) were measured by gel permeation chromatography (GPC). A liquid delivery pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Showa Denko Corporation, GPC KF-801, 802, 803, 804) were used. Tetrahydrofuran was used as the solvent, and the flow rate was 1.0 mL / min at a column temperature of 40°C. A calibration curve using monodisperse polystyrene was prepared and used.

[0169] <Synthesis Example 1: Synthesis of Modified Polyphenylene Ether Compounds> <<Synthesis of Bifunctional Phenylene Ether Oligomers>> The polymerization reaction was carried out according to the following procedure. In a vertical reactor equipped with a stirrer, thermometer, air inlet tube and baffle, 46.21 g (171 mmol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol, 104.4 g (855 mmol) of 2,6-dimethylphenol, and CuBr ２1.37 g (6.1 mmol) of N,N'-di-t-butylethylenediamine, 1.59 g (9.2 mmol) of n-butyldimethylamine, 9.26 g (92 mmol) of n-butyldimethylamine, 1,000 g of toluene, and 500 g of methanol were charged and stirred at a reaction temperature of 40°C until dissolved. Then, a mixture of nitrogen and air, adjusted to an oxygen concentration of 8%, was bubbling into the resulting mixed solution while stirring for 230 minutes. Next, 580 g of water in which 4.72 g (10 mmol) of tetrasodium ethylenediaminetetraacetate was dissolved was added to stop the reaction. The aqueous layer and the organic layer were separated, and the organic layer was washed with 670 g of pure water. 1,310 g of toluene solution A1 of the phenylene ether resin composition was obtained. The number-average molecular weight in polystyrene terms by the GPC method was 950, and the weight-average molecular weight in polystyrene terms by the GPC method was 1,050.

[0170] <<Synthesis of Modified Polyphenylene Ether Compound>> In a reactor equipped with a stirrer, thermometer, and reflux tubing, 833 g of toluene solution A1 of the phenylene ether resin obtained above, 76.7 g (0.50 mol) of vinyl benzyl chloride (AGC Seimi Chemical Co., Ltd., "CMS-P"), 1600 g of methylene chloride, 6.20 g (0.046 mol) of benzyldimethylamine, 200 g of pure water, and 84 g of 30.5% by mass NaOH aqueous solution were charged, and the mixture was stirred at a reaction temperature of 40°C. After stirring for 24 hours, the organic layer was washed with 1 M hydrochloric acid aqueous solution, and then with pure water. The obtained solution was concentrated and added dropwise to methanol to solidify it, and the solid was recovered by filtration and vacuum dried to obtain 450 g of a polyphenylene ether compound mainly composed of the compound represented by formula (OP-15). The number-average molecular weight in polystyrene equivalents according to the GPC method was 2250, the weight-average molecular weight in polystyrene equivalents according to the GPC method was 3920, the double bond equivalent of the vinyl group was 1189 g / eq., and the hydroxyl group equivalent was 56250 g / eq.

[0171] Example 1 A varnish was obtained by dissolving and mixing methyl ethyl ketone and toluene with 40 parts by mass of a maleimide compound (ma) having the structure shown below (manufactured by DIC Corporation, NE-X-9470S, corresponding to formula (M1)), 25 parts by mass of a biphenyl aralkyl type polymaleimide compound (manufactured by Nippon Kayaku Co., Ltd., MIR-3000, corresponding to formula (M3)), 5 parts by mass of a flame retardant (aluminium phosphorus complex, manufactured by Clariant, EXOLIT OP935), 30 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 1, 1 part by mass of a humidity dehumidifier (manufactured by BYK Corporation, BYK-2009), and 100 parts by mass of a methyl ethyl ketone (MEK) slurry of vinylsilane-treated silica (SC2050MNU (trade name), median diameter 0.5 μm, non-volatile content 70% by mass, manufactured by Admatex Co., Ltd.). The amounts of each component mentioned above are given in terms of solid content.

[0172] Maleimide compounds (MA)

[0173] <Preparation of a 0.8 mm thick cured plate test specimen> The obtained varnish was impregnated onto a 0.082 mm thick glass woven fabric (NEZ2116, manufactured by Nitto Boseki Co., Ltd.), and heated and dried at 165°C for 5 minutes to obtain a prepreg (0.1 mm thick) with a solid content of 60% by mass of the resin composition. The properties of the glass woven fabric used are as follows: IPC applicable variety: 2116 Density (threads / 25 mm) vertical: 59.7 Density (threads / 25 mm) horizontal: 56.3 Thickness (μm): 86.0 Mass (g / m²) ２ ) : 90.2 Dielectric constant: 4.0 Dielectric loss tangent: 0.0010 SiO measured by X-ray fluorescence analysis ２ Content: 66.1% by mass. B measured by X-ray fluorescence analysis. ２ O ３ Content of: 14.9 mass% CaO content measured by X-ray fluorescence analysis: 2.2 mass% MgO content measured by X-ray fluorescence analysis: 0 mass% Content of other components measured by X-ray fluorescence analysis: 16.8 mass% The above dielectric constant and dielectric loss tangent are values ​​at a frequency of 10 GHz measured by the cavity resonator perturbation method in accordance with JIS C218:2007. The X-ray fluorescence analyzer used was a Rigaku ZSX Primus IV.

[0174] Eight of the resulting prepregs were stacked, and 12 μm thick copper foil (3EC-M3-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides, and a pressure of 30 kg / cm² was applied. ２ A copper foil-clad laminate with an insulating layer thickness of 0.8 mm was obtained by vacuum pressing at a temperature of 220°C for 120 minutes. The relative permittivity (Dk), dielectric loss tangent (Df), and drillability of the obtained copper foil-clad laminate were evaluated. The evaluation results are shown in Table 1.

[0175] <Measurement Method and Evaluation Method> <Dielectric Properties> The metal foil was peeled off the obtained copper foil-clad laminate, downsized to a width of 1.0 mm, and then dried at 120°C for 60 minutes. The relative permittivity (Dk) and dielectric loss tangent (Df) of the dried sample were measured at a frequency of 10 GHz using a perturbation cavity resonator. The measurement temperature was 23°C. The measurement results were evaluated as follows. A P5005A perturbation cavity resonator manufactured by Keysight Technologies was used. <<Relative Permittivity (Dk)>> A: Less than 3.0 B: 3.0 or more and less than 3.2 C: 3.2 or more <<Dielectric Loss Tangent (Df)>> A: Less than 0.0020 B: 0.0020 or more and less than 0.0025 C: 0.0025 or more

[0176] <Drillability> The metal foil was removed from the obtained copper foil laminate, and drilling was performed using a drilling machine ND-1V211 manufactured by Via Mechanics Co., Ltd., with a drill bit KCW V103VWU manufactured by Union Tool Co., Ltd. (bit diameter 0.15 mm, blade length 35 mm) to evaluate the machinability. The processing conditions were as follows: Number of holes to be processed: 10,000 Entry sheet: LE-R12F3 manufactured by Mitsubishi Gas Chemical Co., Ltd. Backup board: SPB-W manufactured by Nippon Decorax Co., Ltd. The machinability was judged using the following indicators: A: No drill breakage occurred up to 10,000 holes processed B: Drill breakage occurred up to 10,000 holes processed

[0177] Comparative Example 1 In Example 1, the glass cloth was changed to NE2116 manufactured by Nitto Boseki Co., Ltd., and the rest of the procedure was carried out in the same manner. The characteristics of NE2116 are as follows: IPC corresponding product: 2116 Density (threads / 25mm) vertical: 59.5 Density (threads / 25mm) horizontal: 56.4 Thickness (μm): 88.0 Mass (g / m²) ２ ) : 94.9 Dielectric constant: 4.7 Dielectric loss tangent: 0.0025 SiO measured by X-ray fluorescence analysis ２ Content: 59.4% by mass. B measured by X-ray fluorescence analysis. ２ O ３ Content of: 14.8% by mass CaO content measured by X-ray fluorescence analysis: 4.0% by mass MgO content measured by X-ray fluorescence analysis: 3.6% by mass Content of other components measured by X-ray fluorescence analysis: 18.2% by mass

[0178] Comparative Example 2 In Example 1, the glass cloth was changed to Q2116 manufactured by Shin-Etsu Chemical Co., Ltd., and the rest of the procedure was carried out as before. The properties of Q2116 are as follows: IPC-eligible variety: 2116 Density (threads / 25mm) vertical: 60.0 Density (threads / 25mm) horizontal: 58.0 Thickness (μm): 89.0 Mass (g / m²) ２ ) : 88.4 Dielectric constant: 3.8 Dielectric loss tangent: 0.0005 SiO measured by X-ray fluorescence analysis ２ Content: 95.6% by mass. B measured by X-ray fluorescence analysis. ２ O ３ Content of: 1.4% by mass CaO content measured by X-ray fluorescence analysis: 0% by mass MgO content measured by X-ray fluorescence analysis: 2.9% by mass

[0179]

[0180] Although the present invention has been described in detail using specific embodiments, it will be apparent to those skilled in the art that various modifications are possible without departing from the intent and scope of the invention.

Claims

A prepreg having a resin composition and / or a semi-cured product of the resin composition and glass cloth, The resin composition contains a thermosetting compound, The dielectric constant of the aforementioned glass cloth, measured by the cavity resonator perturbation method in accordance with JIS C218:2007, is 4.4 or less at a frequency of 10 GHz. SiO in the aforementioned glass cloth ２ A prepreg in which the proportion is 61-85% by mass. The prepreg according to claim 1, wherein the dielectric loss tangent at a frequency of 10 GHz, measured by the cavity resonator perturbation method in accordance with JIS C218:2007 for the glass cloth, is less than 0.

002. The prepreg according to claim 1 or 2, wherein the thermosetting compound comprises at least one selected from the group consisting of maleimide compounds, aromatic resins having a carbon-carbon double bond at the terminal, cyanate ester compounds, (meth)allyl compounds, (meth)acrylate compounds, epoxy compounds, phenol compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene compounds, perfluorovinyl ether resins, polyimide compounds, and compounds having a vinylene group. The prepreg according to claim 1 or 2, wherein the thermosetting compound comprises one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), a maleimide compound (M6), a maleimide compound (M7), and a maleimide compound (M8). (In formula (M0), R ５１ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５２ Each of these independently represents a hydrogen atom or a methyl group, n １ (This represents an integer greater than or equal to 1.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ each independently represent a hydrogen atom or an organic group. R Ｍ５ and R Ｍ６ each independently represent a hydrogen atom or an alkyl group. Ar Ｍ represents a divalent aromatic group. A is an alicyclic group having 4 to 6 members. 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 each independently represent a hydrogen atom or an alkyl group. R Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ each independently represent a hydrogen atom or an organic group. 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. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) (In formula (M2), R ５４ Each of these independently represents a hydrogen atom or a methyl group, n ４ (This represents an integer greater than or equal to 1.) (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10, inclusive.) (In formula (M4), R ５６ Each of these independently represents a hydrogen atom, a methyl group, or an ethyl group, and R ５７ (Each of these independently represents either a hydrogen atom or a methyl group.) (In formula (M5), R ５８ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R ５９ Each of these independently represents a hydrogen atom or a methyl group, n ６ (This represents an integer greater than or equal to 1.) (In formula (M6), R ６１ R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６２ R represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６３ Each of these 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 of these independently represents an integer from 0 to 10. (In formula (M7), R １ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, and R ２ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group. R ３ , R ４ , R ５ and R ６ Each of these independently represents a hydrogen atom or a methyl group, and R ３ and R ４ One side is a hydrogen atom, and the other side is a methyl group, R ５ and R ６ One of them is a hydrogen atom, and the other is a methyl group. X １ These are expressed independently as follows (x): (In formula (x), R ７ and R ８ Each of these independently represents a hydrogen atom or a methyl group, and R ７ and R ８ One side is a hydrogen atom, and the other side is a methyl group, R ９ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms; an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, where t is an integer from 0 to 4. This represents a substituent represented by X １ X per benzene ring to which is bonded １ (This is the average number of substitutions, representing numbers from 0 to 4, where p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.) (In formula (M8), R １ and R ３ Each of these independently represents a hydrocarbon group in which eight or more atoms are linked in a linear chain, and R ２ Each of these independently represents a substituted or unsubstituted cyclic hydrocarbon group that may contain 4 to 10 heteroatoms constituting the ring, and n represents a number from 1 to 10. The prepreg according to claim 1 or 2, wherein the thermosetting compound comprises a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, and -(Y-O) ｎ１ The hyphen (-) represents a polyphenylene ether structure, where n1 is an integer from 1 to 100, and n2 is an integer from 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In equations (Rx-1) and (Rx-2), R １ , R ２ , and, R ３ Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents the bonding site with the oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6. The prepreg according to claim 1 or 2, wherein the thermosetting compound comprises a compound represented by formula (M1), a compound represented by formula (M3), and a polyphenylene ether compound represented by formula (OP). (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ Each of these independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4-6 membered alicyclic group. R Ｍ７ and R Ｍ８ Each of these is independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. Ｍ９ and R Ｍ１０ Each of these independently represents either a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ Each of these independently represents a hydrogen atom or an organic group. Ｍ１５ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20. (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10, inclusive.) Furthermore, the prepreg according to claim 1 or 2, further comprising a filler other than the glass cloth. Furthermore, the prepreg according to claim 1 or 2, comprising a flame retardant. A prepreg according to claim 1 or 2, for use in printed circuit boards. The dielectric loss tangent of the aforementioned glass cloth, measured by the cavity resonator perturbation method in accordance with JIS C218:2007, is less than 0.002 at a frequency of 10 GHz. The thermosetting compound includes a compound represented by formula (M1), a compound represented by formula (M3), and a polyphenylene ether compound represented by formula (OP). Furthermore, it includes fillers other than the aforementioned glass cloth, Furthermore, it contains a flame retardant, The prepreg according to claim 1, for use in printed circuit boards. (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ each independently represents a hydrogen atom or an organic group. R Ｍ５ and R Ｍ６ each independently represents a hydrogen atom or an alkyl group. Ar Ｍ represents a divalent aromatic group. A is an alicyclic group having 4 to 6 members. 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 each independently represents a hydrogen atom or an alkyl group. R Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ each independently represents a hydrogen atom or an organic group. 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. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) (In formula (M3), R ５５ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, n ５ (This represents an integer between 1 and 10, inclusive.) A metal foil-clad laminate comprising at least one prepreg according to claim 1, 2, or 10, and a metal foil disposed on one or both sides of the prepreg. A printed wiring board comprising an insulating layer and a conductive layer disposed on the surface of the insulating layer, A printed wiring board in which the insulating layer includes a layer formed from the prepreg described in claim 1, 2, or 10. A semiconductor device comprising a printed circuit board as described in claim 12.

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