Resin composition, prepreg, metal-clad laminate, and method for producing same

Abstract

Provided are a resin composition having excellent electrical characteristics and flame retardancy, a prepreg, a metal-clad laminate, and a method for producing the same. The resin composition contains at least a resin having an α-olefin structure represented by formula (1), an organophosphorus compound, and a compound having at least one of an oxygen atom and a nitrogen atom. Also provided are a prepreg, a metal-clad laminate, and a method for producing the metal-clad laminate using the resin composition. In formula (1), each R1 independently represents a hydrocarbon group having 1-10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0-4, and each * represents a bonding position.

Description

Resin composition, prepreg, metal-clad laminate, and method for producing same

[0001] The present disclosure relates to a resin composition, a prepreg, a metal-clad laminate, and a method for producing the same.

[0002] Laminates used in printed circuit boards for high-speed communications are required to have higher performance, and the resin compositions used in laminates are required to have various practical properties, including electrical properties.

[0003] Patent Document 1 discloses polymers containing indane structures based on specific diisoalkenylarenes, which have satisfactory electronic properties.

[0004] Japanese Patent Application Laid-Open No. 2022-100270

[0005] When the polymer containing a large amount of indane structures described in Patent Document 1 is used in a metal-clad laminate, it may be difficult to achieve both electrical properties and flame retardancy.

[0006] The present disclosure has been made in view of the above-mentioned problems, and aims to provide a resin composition, a prepreg, and a metal-clad laminate having excellent electrical properties and flame retardancy, and methods for producing the same.

[0007] The resin composition, prepreg, metal-clad laminate, and manufacturing method thereof according to the present disclosure are shown in the following [1] to

[23] . [1] A resin composition containing at least a resin having an α-olefin structure shown in the following formula (1), an organic phosphorus compound, and a compound having at least one atom of an oxygen atom and a nitrogen atom: (In formula (1), R １each independently represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p1 represents a real number of 0 to 4, and * represents a bonding position.) [2] The resin composition according to [1], wherein the resin has an iodine value of 70 or more and 200 or less. [3] The resin composition according to [1] or [2], wherein the resin has a weight-average molecular weight Mw of 2,500 or more and 500,000 or less. [4] The resin composition according to any one of [1] to [3], wherein the content of the α-olefin structure represented by formula (1) in the resin is 1.0 mmol / g or more and 6.3 mmol / g or less. [5] The resin composition according to any one of [1] to [4], wherein the following parameter FA, represented by the content of the α-olefin structure represented by formula (1), the content of the indane structure represented by formula (2), and the content of the inner olefin structure represented by formula (3), in the resin, is 0.39 or more. FA = [α-olefin structure content] / ([inner olefin structure content] + [indan structure content] + [α-olefin structure content]) (In formula (2), R ２ each independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number from 0 to 4, q1 represents a real number from 0 to 3, and * represents a bonding position. (In formula (3), R ３each independently represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p3 represents a real number of 0 to 4, and * represents a bonding position.) [6] The resin composition according to any one of [1] to [5], wherein the following parameter FI, represented by the content of the α-olefin structure represented by the formula (1), the content of the indane structure represented by the formula (2), and the content of the inner olefin structure represented by the formula (3), in the resin is less than 0.58. FI = [Content of indane structure] / ([Content of inner olefin structure] + [Content of indane structure] + [Content of α-olefin structure] / 2) [7] The resin composition according to any one of [1] to [6], wherein the content of heteroatoms other than carbon atoms and hydrogen atoms in the resin is 3 mass% or less. [8] The resin composition according to [7], wherein the resin does not contain any heteroatoms. [9] The resin composition according to any one of [1] to [8], wherein the resin has an olefin structure at a terminal.

[10] The resin composition according to any one of [1] to [9], wherein the resin further has a side-chain olefin structure having an olefin structure in a side chain portion.

[11] The resin composition according to any one of [1] to

[10] , wherein the total content of the α-olefin structure, the terminal olefin structure, and the side-chain olefin structure having an olefin structure in a side chain portion in the resin is 1.8 mmol / g or more.

[12] The resin composition according to any one of [1] to

[11] , wherein the content of the indane structure represented by the above formula (2) in the resin is 3.0 mmol / g or less.

[13] The resin composition according to any one of [1] to

[12] , wherein the organophosphorus compound has a solubility of 5 g or less in 100 g of toluene at 25°C.

[14] The resin composition according to any one of [1] to

[13] , wherein the organophosphorus compound is incompatible with the resin.

[15] The resin composition according to any one of [1] to

[14] , wherein the organophosphorus compound has a melting point of 240°C or higher.

[16] The resin composition according to any one of [1] to

[15] , wherein the organic phosphorus compound has a phosphine oxide structure or a phosphinic acid structure.

[17] The resin composition according to any one of [1] to

[16] , wherein the compound having at least one of an oxygen atom and a nitrogen atom has a number-average molecular weight Mn of 300 to 50,000.

[18] The resin composition according to any one of [1] to

[17] , wherein the compound having at least one of an oxygen atom and a nitrogen atom contains a radically polymerizable group.

[19] The resin composition according to any one of [1] to

[18] , wherein the total content of oxygen atoms and nitrogen atoms is 0.01 to 10 mass%.

[20] The resin composition according to any one of [1] to

[19] , wherein the contents of the resin, the organophosphorus compound, and the compound having at least one of an oxygen atom and a nitrogen atom, in the solid content of the resin composition, are 1 to 80 mass%.

[21] A prepreg comprising the resin composition according to any one of [1] to

[20] .

[22] A metal-clad laminate comprising a cured product of the resin composition according to any one of [1] to

[20] , and a metal foil.

[23] A method for producing a metal-clad laminate, comprising laminating a prepreg containing the resin composition according to any one of [1] to

[20] and a metal foil.

[0008] According to the present disclosure, a resin composition, a prepreg, a metal-clad laminate, and methods for producing the same, each having excellent electrical properties and flame retardancy, are provided.

[0009] In this specification, a numerical range indicated using "to" includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in numerical ranges described in this specification, the upper or lower limit value of that numerical range may be replaced with a value shown in the examples. Note that when the same symbol exists in a chemical formula, the same symbol may represent the same structure as each other, or may represent different structures within the specified range.

[0010] As described above, compositions (resin compositions) used in laminates mounted in electrical and electronic components are required to have various practical performance characteristics, including electrical properties. In particular, for laminates used in high-speed communications, it is desirable to use resins with extremely low loss, having a dielectric loss tangent of 0.004 or less (more preferably 0.0015 or less) at a frequency of 10 GHz.

[0011] To date, hydrocarbon resins and fluororesins composed of carbon and hydrogen atoms have been used as such resins. More specifically, examples of the hydrocarbon resins include polyfunctional vinyl aromatic polymers, cyclic polyolefin resins, and vinyl aromatic compound-conjugated diene compound copolymers. Examples of the fluororesins include polytetrafluoroethylene.

[0012] Patent Document 1 discloses a polymer based on a specific diisoalkenyl allene, which is considered to contain a large amount of the indane structure described below, as a resin having sufficient electronic properties.

[0013] However, when the polymer described in Patent Document 1 is used in a laminate, it may be difficult to achieve both electrical properties and flame retardancy. The present inventors have discovered that excellent electrical properties and flame retardancy can be imparted to a metal-clad laminate by using a resin composition containing a resin having an α-olefin structure represented by the following formula (1), an organic phosphorus compound, and a compound having at least one of an oxygen atom and a nitrogen atom. In recent years, there has been a demand for metal-clad laminates using halogen-free resin compositions that do not contain halogen materials in order to address environmental issues related to the production and disposal of printed wiring boards using metal-clad laminates. The resin composition according to the present disclosure may also be a halogen-free resin composition that can easily achieve both electrical properties and flame retardancy without using halogen materials.

[0014] Hereinafter, an embodiment of the resin composition according to the present disclosure (hereinafter also referred to as "the composition") will be described in detail, but the present disclosure is not limited to this embodiment. In addition, any modifications can be made without departing from the gist of the present disclosure.

[0015] <Resin Composition> This composition contains at least a resin having an α-olefin structure represented by the above formula (1) (hereinafter also referred to as resin A), an organic phosphorus compound (hereinafter also referred to as compound B), and a compound having at least one of an oxygen atom and a nitrogen atom (hereinafter also referred to as compound C). By using these resins and compounds in combination, this composition can keep the dielectric loss tangent Df low and can also impart excellent flame retardancy. The molecular structures of the resins and compounds contained in the composition are as follows: １ H-NMR and １３ The components of the composition are described in detail below.

[0016] (Resin having an α-olefin structure represented by formula (1)) Resin A has at least an α-olefin structure represented by the following formula (1) as a unit structure. By containing Resin A, the present composition can be imparted with excellent electrical properties, and furthermore, can improve heat resistance and adhesion to metal foil. One type of Resin A may be used alone, or two or more types may be used in combination. Furthermore, Resin A may be a curable resin.

[0017] Here, in formula (1), R １ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0 to 4, and * represents a bonding position.

[0018] In formula (1), R １ is a hydrocarbon group or halogenated alkyl group having 1 to 10 carbon atoms, and from the viewpoint of imparting excellent electrical properties and being halogen-free, is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isopropenyl group, a t-butyl group, and an n-butyl group. The halogenated alkyl group is an alkyl group in which a hydrogen atom has been substituted with a halogen atom, and examples of the halogen atom include F, Cl, Br, and I. The alkyl group has, for example, 1 to 10 carbon atoms.

[0019] In formula (1), p1 is a real number of 0 to 4, preferably 0 to 3, and more preferably 0.

[0020] Resin A, as will be described in detail below, can be a resin obtained by polymerizing a compound having multiple isopropenyl groups (e.g., a diisopropenyl compound) at a specific reaction temperature in the presence of an acid catalyst. Examples of compounds having multiple isopropenyl groups that can be used include 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene. These diisopropenyl compounds can be produced by known methods. For example, a diisopropenyl compound can be synthesized by intramolecular dehydration of a diol compound obtained by oxidizing a cumyl group and reducing it with hydrogen. Furthermore, a diisopropenyl compound can also be produced by adding propylene to an aromatic compound and subjecting it to a dehydrogenation reaction. The raw material monomer for producing Resin A may also be a precursor of a compound having multiple isopropenyl groups (e.g., a diisopropenyl compound precursor).

[0021] From the viewpoints of flexibility, adhesion to metal foil, and curability, the iodine value of the resin A is preferably, for example, the following values: That is, the iodine value of the resin A is preferably, for example, 70 or more, 71 or more, 72 or more, 73 or more, 74 or more, 75 or more, 76 or more, 77 or more, 78 or more, 79 or more, 80 or more, 81 or more, 82 or more, 83 or more, 84 or more, 85 or more, 86 or more, 87 or more, 88 or more, 89 or more, 90 or more, 91 or more, 92 or more, 93 or more, more than 93, 94 or more, or 95 or more. Furthermore, from the viewpoints of adjustability of the degree of polymerization, heat resistance, and curability, the iodine value of the resin A is preferably, for example, the following values: That is, the iodine value of the resin A is preferably, for example, 200 or less, 195 or less, 190 or less, 185 or less, 180 or less, 175 or less, 170 or less, 165 or less, 160 or less, 155 or less, or 150 or less.

[0022] Here, the iodine value is the amount of iodine (I) that can be added (reacted) to 100 grams of the target sample (here, Resin A). ２) in grams. Therefore, the larger this value, the higher the degree of unsaturation in the sample, i.e., the greater the number of unsaturated bonds (double bonds) in the structure. Since the above α-olefin structure has double bonds in the structure, the iodine value can be used as a guide to know the content of α-olefin structure in resin A. The iodine value can be determined by the Wiess method.

[0023] From the viewpoint of curability and heat resistance, the weight average molecular weight Mw of the resin A is preferably, for example, the following values: 2,500 or more, 2,550 or more, 2,600 or more, 2,650 or more, 2,700 or more, 2,750 or more, 2,800 or more, 2,850 or more, 2,900 or more, 2,950 or more, 3,000 or more, 3,100 or more, 3,200 or more, 3,300 or more, 3,400 or more, 3,500 or more, 3,600 or more, 3,700 or more, 3,800 or more, 3,900 or more, 4,000 or more, 4,100 or more, 4,200 or more, 4,300 or more, 4400 or more, 4,500 or more, 4,600 or more, 4,700 or more, Preferably, the weight average molecular weight Mw of the resin A is 4,800 or more, 4,900 or more, 5,000 or more, 5,100 or more, 5,200 or more, 5,300 or more, 5,400 or more, 5,500 or more, 5,600 or more, 5,700 or more, 5,800 or more, 5,900 or more, 6,000 or more, more than 6,000, 6,100 or more, 6,200 or more, 6,300 or more, 6,400 or more, 6,500 or more, 6,600 or more, 6,700 or more, 6,800 or more, 6,900 or more, 7,000 or more, 7,500 or more, 8,000 or more, 8,500 or more, 9,000 or more, 9,500 or more, or 10,000 or more. From the viewpoint of solvent solubility, the weight average molecular weight Mw of the resin A is, for example, preferably the following value. That is, the weight average molecular weight Mw of the resin A is preferably, for example, 500,000 or less, 450,000 or less, 400,000 or less, 350,000 or less, 300,000 or less, 250,000 or less, 200,000 or less, 190,000 or less, 180,000 or less, 170,000 or less, 160,000 or less, 150,000 or less, 140,000 or less, 130,000 or less, 120,000 or less, 110,000 or less, or 100,000 or less. A method for measuring the weight average molecular weight will be described later.

[0024] The number average molecular weight Mn of the resin A is preferably 700 or more, more preferably 1,000 or more. The number average molecular weight Mn of the resin A is preferably 5,000 or less. The method for measuring the number average molecular weight will be described later.

[0025] The content of the α-olefin structure represented by the formula (1) in the resin A (hereinafter also referred to as the α-olefin content) is preferably, for example, the following value from the viewpoints of electrical properties, heat resistance, and metal foil adhesion. That is, the α-olefin content (content ratio) is, for example, 1.0 mmol / g or more, 1.1 mmol / g or more, 1.2 mmol / g or more, 1.3 mmol / g or more, 1.4 mmol / g or more, 1.5 mmol / g or more, 1.6 mmol / g or more, 1.7 mmol / g or more, 1.8 mmol / g or more, 1.9 mmol / g or more, 2.0 mmol / g or more, 2.1 mmol / g or more, 2.2 mmol / g or more, 2.3 mmol / g or more, or 2.35 mmol / g or more. Furthermore, from the viewpoints of heat resistance and curability, the content of the α-olefin structure in the resin A is preferably, for example, the following value. That is, the α-olefin content is preferably, for example, 6.3 mmol / g or less, 6.2 mmol / g or less, 6.1 mmol / g or less, 6.0 mmol / g or less, 5.9 mmol / g or less, 5.8 mmol / g or less, 5.7 mmol / g or less, 5.6 mmol / g or less, 5.5 mmol / g or less, 5.4 mmol / g or less, 5.3 mmol / g or less, 5.2 mmol / g or less, 5.1 mmol / g or less, or 5.0 mmol / g or less.

[0026] From the viewpoint of electrical properties, the content of heteroatoms other than carbon and hydrogen atoms in Resin A is preferably 3 mass% or less, and more preferably contains no heteroatoms. The content of heteroatoms in Resin A can be determined by elemental analysis using a combustion method, for example.

[0027] As described above, resin A can be a polymer of a diisopropenyl compound, as will be described in detail later. In addition to the α-olefin structure shown in formula (1) above, resin A can contain, as unit structures, an olefin structure located at the end of the molecular structure (terminal olefin structure), a side-chain olefin structure having an olefin structure in the side chain portion, an indane structure shown in formula (2) below, an inner olefin structure shown in formula (3) below, and other structures.

[0028] In addition to the α-olefin structure, Resin A preferably has either or both of the terminal olefin structure and the side chain olefin structure, which improves adhesion to metal foil and provides high metal peel strength.

[0029] More specifically, the total content of the α-olefin structure, the olefin structure at the terminal of the molecular structure (terminal olefin structure), and the side-chain olefin structure having an olefin structure in the side chain portion in Resin A is preferably as follows: That is, from the viewpoint of peel strength, the total content of these three structures (hereinafter also referred to as the three-structure content) is preferably, for example, the following value: That is, the three-structure content is preferably, for example, 1.8 mmol / g or more, 1.9 mmol / g or more, 2.0 mmol / g or more, 2.1 mmol / g or more, 2.2 mmol / g or more, 2.3 mmol / g or more. Furthermore, from the viewpoint of heat resistance and curability, the total content of these three structures in Resin A is preferably, for example, the following value: That is, the content of the three structures is preferably, for example, 6.5 mmol / g or less, 6.4 mmol / g or less, 6.3 mmol / g or less, 6.2 mmol / g or less, 6.1 mmol / g or less, 6.0 mmol / g or less, 5.9 mmol / g or less, 5.8 mmol / g or less, 5.7 mmol / g or less, 5.6 mmol / g or less, 5.5 mmol / g or less, 5.4 mmol / g or less, 5.3 mmol / g or less, 5.2 mmol / g or less, 5.1 mmol / g or less, or 5.0 mmol / g or less.

[0030] Furthermore, from the viewpoint of peel strength, the total content of terminal olefin structures and side-chain olefin structures in resin A (hereinafter also referred to as the "two-structure content") is preferably, for example, the following value. That is, the two-structure content is preferably, for example, 0.1 mmol / g or more, 0.11 mmol / g or more, 0.12 mmol / g or more, 0.13 mmol / g or more, 0.14 mmol / g or more, 0.15 mmol / g or more, 0.16 mmol / g or more, 0.17 mmol / g or more, 0.18 mmol / g or more, 0.19 mmol / g or more, 0.2 mmol / g or more, 0.25 mmol / g or more, or 0.3 mmol / g or more. Furthermore, from the viewpoint of heat resistance and curability, the total content of terminal olefin structures and side-chain olefin structures in resin A is preferably, for example, the following value. That is, the content of the two structures is preferably, for example, 6.0 mmol / g or less, 5.9 mmol / g or less, 5.8 mmol / g or less, 5.7 mmol / g or less, 5.6 mmol / g or less, 5.5 mmol / g or less, 5.4 mmol / g or less, 5.3 mmol / g or less, 5.2 mmol / g or less, 5.1 mmol / g or less, 5.0 mmol / g or less, 4.9 mmol / g or less, 4.8 mmol / g or less, 4.7 mmol / g or less, 4.6 mmol / g or less, 4.5 mmol / g or less, 4.4 mmol / g or less, 4.3 mmol / g or less, 4.2 mmol / g or less, 4.1 mmol / g or less, or 4.0 mmol / g or less.

[0031] The total content of these three structures in resin A may consist of two of the three structures, or may consist of one (for example, an α-olefin structure). That is, resin A may have only one of the three structures (for example, an α-olefin structure), only two of the structures, or all three of the structures.

[0032] From the above, the resin A can be a polymer having an α-olefin structure, a terminal olefin structure, a side chain olefin structure, and, if necessary, an indane structure, an inner olefin structure, and other structures as repeating units.

[0033] The terminal olefin structure is an olefin structure located at the end of a molecular structure, and is not particularly limited in structure, but can be represented, for example, by the following formula (4). In formula (4), A represents a polymer chain and may contain at least one structure selected from the group consisting of the α-olefin structure shown in formula (1) above, the side chain olefin structure shown in formula (5) below, the indane structure shown in formula (2) below, and the inner olefin structure shown in formula (3) below. In this embodiment, A contains at least the α-olefin structure shown in formula (1) above.

[0034] The terminal olefin structure may be a structure represented by the following formula (4-1): Here, in formula (4-1), A １ represents a polymer chain, and may contain at least one structure selected from the group consisting of the α-olefin structure shown in the above formula (1), the side chain olefin structure shown in the following formula (5), the indane structure shown in the following formula (2), and the inner olefin structure shown in the following formula (3). In this embodiment, A contains at least the α-olefin structure shown in the above formula (1). In addition, in formula (4-1), R ４ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group; and p4 represents a real number of 0 to 4.

[0035] In formula (4-1), R ４ is a hydrocarbon group or halogenated alkyl group having 1 to 10 carbon atoms, and from the viewpoints of electrical properties and halogen-free properties, is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isopropenyl group, a t-butyl group, and an n-butyl group. The halogenated alkyl group is an alkyl group in which a hydrogen atom has been substituted with a halogen atom, and examples of the halogen atom include F, Cl, Br, and I. The number of carbon atoms in the alkyl group is, for example, 1 to 10. In addition, in formula (4-1), p4 is a real number of 0 to 4, preferably 0 to 3, and more preferably 0.

[0036] The above-mentioned side chain olefin structure is not particularly limited as long as it has an olefin structure in the side chain portion, but may be, for example, a structure shown in the following formula (5). Here, in formula (5), R ５ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p5 represents a real number of 0 to 4, and * represents a bonding position.

[0037] In formula (5), R ５ is a hydrocarbon group or halogenated alkyl group having 1 to 10 carbon atoms, and from the viewpoints of electrical properties and halogen-free properties, is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isopropenyl group, a t-butyl group, and an n-butyl group. The halogenated alkyl group is an alkyl group in which a hydrogen atom has been substituted with a halogen atom, and examples of the halogen atom include F, Cl, Br, and I. The number of carbon atoms in the alkyl group is, for example, 1 to 10. Furthermore, in formula (5), p5 is a real number of 0 to 4, preferably 0 to 3, and more preferably 0.

[0038] The indane structure described above is represented by the following formula (2): Here, in formula (2), R ２ each independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and * represents a bonding position.

[0039] In formula (2), R ２is a hydrocarbon group or halogenated alkyl group having 1 to 10 carbon atoms. From the viewpoints of electrical properties and halogen-free properties, it is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isopropenyl group, a t-butyl group, and an n-butyl group. The halogenated alkyl group is an alkyl group in which a hydrogen atom is substituted with a halogen atom. Examples of the halogen atom include F, Cl, Br, and I. The alkyl group has, for example, 1 to 10 carbon atoms. In formula (2), p2 is a real number of 0 to 4, preferably 0 to 3, and more preferably 0. Furthermore, q1 is a real number of 0 to 3, preferably 0 to 2, and more preferably 0.

[0040] The inner olefin structure described above is represented by the following formula (3). Here, in formula (3), R ３ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p3 represents a real number of 0 to 4, and * represents a bonding position.

[0041] In formula (3), R ３ is a hydrocarbon group or halogenated alkyl group having 1 to 10 carbon atoms, and from the viewpoints of electrical properties and halogen-free properties, is preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isopropenyl group, a t-butyl group, and an n-butyl group. The halogenated alkyl group is an alkyl group in which a hydrogen atom has been substituted with a halogen atom, and examples of the halogen atom include F, Cl, Br, and I. The number of carbon atoms in the alkyl group is, for example, 1 to 10. Furthermore, in formula (3), p3 is a real number of 0 to 4, preferably 0 to 3, and more preferably 0.

[0042] Here, the indane structure has a good balance of aromaticity and aliphaticity, improving solvent solubility and compatibility with other polymers and imparting excellent heat resistance. However, if the content of the indane structure in resin A is high, adhesion to metal foil tends to decrease, so the content of the indane structure in resin A (hereinafter also referred to as the indane content) is preferably lower than that of the α-olefin structure. The content of the indane structure in resin A is preferably, for example, the following value. That is, the content of the indane structure in Resin A is preferably, for example, 4.2 mmol / g or less, 4.1 mmol / g or less, 4.0 mmol / g or less, 3.9 mmol / g or less, 3.8 mmol / g or less, 3.7 mmol / g or less, 3.6 mmol / g or less, 3.5 mmol / g or less, 3.4 mmol / g or less, 3.3 mmol / g or less, 3.2 mmol / g or less, 3.1 mmol / g or less, 3.0 mmol / g or less, 2.9 mmol / g or less, 2.8 mmol / g or less, 2.7 mmol / g or less, 2.6 mmol / g or less, 2.5 mmol / g or less, 2.4 mmol / g or less, 2.3 mmol / g or less, 2.2 mmol / g or less, 2.1 mmol / g or less, 2.0 mmol / g or less, 1.9 mmol / g or less, 1.8 mmol / g or less, 1.7 mmol / g or less, 1.6 mmol / g or less, or 1.5 mmol / g or less. From the viewpoint of ease of production, the content of the indane structure in Resin A is preferably, for example, one of the following values: That is, the content of indane in Resin A is preferably, for example, 0.01 mmol / g or more, 0.02 mmol / g or more, 0.03 mmol / g or more, 0.04 mmol / g or more, or 0.05 mmol / g or more.

[0043] For example, when Resin A (diisopropenyl compound homopolymer) is produced using a diisopropenyl compound as a raw material monomer, if the iodine value is small, it is considered that the content of the indane structure is high.

[0044] The inner olefin structure improves electrical properties and heat resistance and imparts good curability, but the α-olefin structure contributes more to curability. Therefore, the content of the α-olefin structure (α-olefin content) in Resin A is preferably greater than the content of the inner olefin structure (hereinafter also referred to as the inner olefin content).

[0045] Furthermore, in Resin A, the following parameter FA, which is expressed by the above-mentioned contents of the α-olefin structure, the inner olefin structure, and the indane structure, is preferably 0.39 or more: FA = [α-olefin structure content] / ([inner olefin structure content] + [indane structure content] + [α-olefin structure content]) Here, if the FA is 0.39 or more, a resin having excellent adhesion to metal foil and good electrical properties and heat resistance can be easily produced. From the same viewpoint, it is preferable that FA is, for example, 0.40 or more, 0.41 or more, 0.42 or more, 0.43 or more, 0.44 or more, 0.45 or more, 0.46 or more, 0.47 or more, 0.48 or more, 0.49 or more, 0.50 or more, 0.51 or more, 0.52 or more, 0.53 or more, 0.54 or more, 0.55 or more, 0.56 or more, 0.57 or more, 0.58 or more, 0.59 or more, 0.60 or more, 0.61 or more, 0.62 or more, 0.63 or more, 0.64 or more, 0.65 or more, 0.66 or more, 0.67 or more, 0.68 or more, 0.69 or more, 0.70 or more, 0.71 or more, 0.72 or more, 0.73 or more, 0.74 or more, or 0.75 or more. From the same viewpoint, the FA is preferably, for example, 0.95 or less.

[0046] Furthermore, in Resin A, the following parameter FI, which is expressed by the above-mentioned content of α-olefin structures, content of inner olefin structures, and content of indane structures, is preferably less than 0.58: FI = [content of indane structures] / ([content of inner olefin structures] + [content of indane structures] + [content of α-olefin structures] / 2) Here, if the FI is less than 0.58, a resin with excellent adhesion to metal foil can be easily produced. From the same viewpoint, the FI is, for example, 0.579 or less, 0.575 or less, 0.57 or less, 0.56 or less, 0.55 or less, 0.54 or less, 0.53 or less, 0.52 or less, 0.51 or less, 0.50 or less, 0.49 or less, 0.48 or less, 0.47 or less, 0.46 or less, 0.45 or less, 0.44 or less, 0.43 or less, 0.42 or less, 0.41 or less, 0.40 or less, 0.39 or less, 0.38 or less, 0.37 or less, 0.36 or less, 0.35 or less, 0.34 or less, 0.33 or less, 0.32 or less, 0.31 or less, 0.30 or less, 0.29 or less, 0.28 or less, 0.27 or less, 0.26 or less, or 0.25 or less. From the same viewpoint, the FI is preferably, for example, 0.15 or more.

[0047] In order to maintain a desirable state as a resin varnish, when Resin A is dissolved in a solvent at a concentration of 60 mass %, the blending ratio of insoluble components is preferably 5 mass % or less, more preferably 4 mass % or less, and even more preferably 3 mass % or less. Examples of solvents include methyl ethyl ketone and toluene.

[0048] From the viewpoint of practical application, the dielectric loss tangent of Resin A at a frequency of 10 GHz is preferably 0.004 or less, more preferably 0.0015 or less, even more preferably 0.001 or less, and particularly preferably 0.0008 or less. The method for measuring the dielectric loss tangent will be described later.

[0049] As used herein, the glass transition temperature (Tg) of a (cured product) refers to the glass transition temperature of a cured product obtained by curing Resin A according to the present disclosure or a resin composition according to the present disclosure. The cured product exhibits a favorable glass transition temperature and can exhibit favorable heat resistance. The glass transition temperature of the cured product is preferably 125°C or higher, more preferably 150°C or higher, even more preferably 175°C or higher, and particularly preferably 200°C or higher. The method for measuring glass transition temperature will be described later. Resin A exhibits the above-mentioned glass transition temperature even when thermally cured at the thermal curing temperature used in producing substrate materials such as prepregs. The thermal curing temperature is at least 250°C or lower, for example, 150 to 230°C. Furthermore, a cured product exhibiting the above-mentioned heat resistance may be obtained by curing a resin composition according to the present disclosure, as described above. Resin A may be composed of one type of polymer or multiple polymers. When resin A is composed of a plurality of polymers, the various physical properties such as the content ratio of insoluble components in the solvent, the glass transition temperature, and the dielectric loss tangent described above are values ​​for a mixture (resin) of these plurality of polymers.

[0050] From the viewpoints of electrical properties, heat resistance, and adhesion to metal foil, the content of resin A in the solid content of the composition is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more. From the viewpoint of flame retardancy, the content of resin A in the solid content of the composition is preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 50% by mass or less, still more preferably 40% by mass or less, and particularly preferably 30% by mass or less.

[0051] (Organophosphorus Compound) The organophosphorus compound (compound B) is not particularly limited and may be any conventionally known organic compound containing a carbon atom and a phosphorus atom (for example, as a carbon-phosphorus bond). The organophosphorus compound may act as a flame retardant. One type of the organophosphorus compound may be used alone, or two or more types may be used in combination.

[0052] From the viewpoint of improving flame retardancy, the solubility of the organophosphorus compound in 100 g of toluene at 25° C. is preferably 5 g or less, more preferably 4 g or less, and even more preferably 3 g or less. In other words, from the viewpoint of heat resistance and chemical resistance, the organophosphorus compound is preferably incompatible with toluene.

[0053] Furthermore, from the viewpoint of heat resistance and chemical resistance, the organic phosphorus compound is preferably incompatible with the above-mentioned resin A.

[0054] Furthermore, from the viewpoint of heat resistance, the melting point of the organic phosphorus compound is preferably 240° C. or higher, more preferably 250° C. or higher, and even more preferably 260° C. or higher. If the melting point of the organic phosphorus compound is 240° C. or higher, volume change at high temperatures can be easily suppressed, which tends to have a favorable effect on improving reliability and reducing warpage of the substrate when used in a printed wiring board.

[0055] From the viewpoint of improving flame retardancy, the organic phosphorus compound is preferably a pentavalent organic phosphorus compound having a P═O bond in its molecular structure. Examples of such pentavalent organic phosphorus compounds include organic phosphorus compounds having a phosphine oxide structure shown in the following formula (6), organic phosphorus compounds having a phosphinic acid structure shown in the following formula (7), organic phosphorus compounds having a phosphonic acid structure shown in the following formula (8), and organic phosphorus compounds having a phosphoric acid structure shown in the following formula (9). Among these, from the viewpoint of electrical properties, the organic phosphorus compound used in the present composition preferably has a phosphine oxide structure, a phosphinic acid structure, or a phosphoric acid structure, and more preferably has a phosphine oxide structure or a phosphinic acid structure. Note that compounds in which these organic phosphorus compounds are coordinated via a metal (e.g., Al, Mg, or Ca) can also be used as compound B. Furthermore, these organic phosphorus compounds may form dimers or trimers as shown in the following formulas (10) and (11).

[0056] In formulas (6) to (11), R each independently represents a substituted or unsubstituted hydrocarbon group, and R may be bonded to each other to form a ring structure. In formulas (10) and (11), Ra each independently represents a substituted or unsubstituted divalent hydrocarbon group. Note that multiple R may be the same or different from each other.

[0057] Examples of the hydrocarbon group represented by R include saturated hydrocarbon groups, unsaturated hydrocarbon groups, and aromatic hydrocarbon groups, and may be combinations thereof. The saturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include alkyl groups. The saturated hydrocarbon group preferably has 1 to 20 carbon atoms. The unsaturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include alkenyl groups. The saturated hydrocarbon group preferably has 1 to 20 carbon atoms. The aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, and examples thereof include aryl groups such as phenyl groups and monovalent biphenyl groups. These hydrocarbon groups may contain heteroatoms (e.g., oxygen atoms, nitrogen atoms) in their structures. Furthermore, these hydrocarbon groups may or may not have a substituent, and the number of such substituents is not particularly limited. Examples of such substituents include alkyl groups, halogen groups, and alkoxy groups. However, from the perspective of environmental issues, the substituent is preferably an alkyl group or an alkoxy group.

[0058] Examples of the divalent hydrocarbon group represented by Ra include a divalent saturated hydrocarbon group, a divalent unsaturated hydrocarbon group, a divalent aromatic hydrocarbon group, and the like, and may be a group formed by combining these. The divalent saturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include an alkylene group. The divalent saturated hydrocarbon group preferably has 1 to 20 carbon atoms. The divalent aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, and examples thereof include a phenylene group and a divalent biphenyl group (-C ６ H ５ -C ６ H ５-). The divalent unsaturated hydrocarbon group preferably has 2 to 20 carbon atoms, and examples thereof include an alkenylene group and an alkynylene group. These divalent hydrocarbon groups may contain a heteroatom (e.g., an oxygen atom or a nitrogen atom) in the structure. Examples of the substituents on these divalent hydrocarbon groups include an alkyl group, a halogen group, an alkoxy group, and a heterocyclic group. However, from the viewpoint of environmental issues, the substituent is preferably an alkyl group, an alkoxy group, or a heterocyclic group. Examples of the heterocyclic ring in the heterocyclic group include a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.

[0059] The organic phosphorus compounds contained in the composition may be, for example, the following compounds. These compounds can be produced by conventionally known methods. Commercially available organic phosphorus compounds may also be used. Compounds P-1 to P-15 are as follows: Compound P-1: aluminum tris(diethylphosphinate) Compound P-2: diphenylvinylphosphine oxide Compound P-3: compound described in Japanese Patent No. 6635415 Compound P-4: compound described in WO 2020-031495 and WO 2022-259851 Compound P-5: compound described in U.S. Patent No. 10,626,250 Compound P-6: compound described in Japanese Patent No. 3897138 Compound P-7: compound described in Chinese Patent Application Publication No. 115710424 Compound P-8: MC-4 (trade name, manufactured by Katayama Chemical Industry Co., Ltd.) Compound P-9: compound described in Japanese Patent No. 6635415 Compound P-10: S-4 (trade name, manufactured by Katayama Chemical Industry Co., Ltd.) Compound P-11: compound described in Japanese Patent No. 6757215 Compound P-12: PX-200 (trade name, manufactured by Daihachi Scientific Industry Co., Ltd.) Compound P-13: SPV-100 (trade name, manufactured by Otsuka Chemical Co., Ltd.) Compound P-14: SPB-100 (trade name, manufactured by Otsuka Chemical Co., Ltd.) Compound P-15: FP-700TP (trade name, manufactured by Fushimi Pharmaceutical Co., Ltd.)

[0060] From the viewpoint of flame retardancy, the content of the organic phosphorus compound in the solid content of the composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, and even more preferably 10% by mass or more. From the viewpoint of electrical properties, the content of the organic phosphorus compound in the solid content of the composition is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less.

[0061] (Compound Having At Least One of an Oxygen Atom and a Nitrogen Atom) The compound C may have at least one of an oxygen atom and a nitrogen atom, and its structure is not particularly limited. The compound C may be, for example, a polymer or an elastomer. Note that compounds corresponding to the above-mentioned resin A and organic phosphorus compound (compound B) are not included in the compound C. Furthermore, one type of compound C may be used alone, or two or more types may be used in combination.

[0062] From the viewpoint of heat resistance, the number average molecular weight Mn of compound C is preferably 300 or more, more preferably 500 or more, and even more preferably 1000 or more. From the viewpoint of resin fluidity, the number average molecular weight Mn of compound C is preferably 50,000 or less, more preferably 35,000 or less, and even more preferably 20,000 or less.

[0063] The weight-average molecular weight Mw of compound C is preferably 1,000 or more from the viewpoints of electrical properties, heat resistance, polymerizability, etc. Furthermore, the weight-average molecular weight Mw of compound C is preferably 500,000 or less, more preferably 100,000 or less, even more preferably 50,000 or less, and particularly preferably 10,000 or less from the viewpoints of solubility in solvents, etc.

[0064] Compound C preferably has a radically polymerizable group in its molecular structure. The radically polymerizable group may be any group that allows radical polymerization, and may be any group containing an unsaturated double bond or an unsaturated triple bond. Examples of the radically polymerizable group include a vinyl group, a vinylidene group, a vinylene group, an ethynyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, an acryloyl group, a methacryloyl group, a fumaroyl group, a maleoyl group, an acryloyloxy group, a methacryloyloxy group, a vinylphenyl group, a fluorovinyl group, a vinyl ether group, an allyl ether group, a styryl group, a vinylnaphthyl group, a norbornyl group, a cinnamoyl group, and a maleimide group (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl group). Of these, the radical polymerizable group is preferably a vinyl group, a vinylidene group, an isopropenyl group, an acryloyl group, a methacryloyl group, or a styryl group.

[0065] For example, a radical polymerizable compound having at least one atom of an oxygen atom and a nitrogen atom can be used as compound C. More specifically, compound C includes (meth)acrylic radical polymerizable compounds having one or two or more acryloyl groups and / or methacryloyl groups; styrene radical polymerizable compounds having one or two or more vinyl groups or vinylidene groups directly bonded to an aromatic carbon atom and at least one atom of an oxygen atom and a nitrogen atom; allyl radical polymerizable compounds having one or two or more allyl groups and at least one atom of an oxygen atom and a nitrogen atom; and maleimide radical polymerizable compounds having one or two or more maleimide groups.

[0066] Examples of compound C include maleimide compounds, bismaleimide compounds, and compounds having two or more structures (ether structures) represented by the following formula (A) in the molecule and a heterocyclic structure. The maleimide compounds and bismaleimide compounds may be polymerized products or may contain other structures (e.g., an indane skeleton) in the structure. In formula (A), R ａare each independently a hydroxyl group, a halogen group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, n1 represents a real number of 0 to 4, and * and ** each represent a bonding position. Note that in a compound having the structure shown in formula (A) above and a heterocyclic structure, R bonded to the benzene ring of formula (A) above ａ The bonding position of the bonding group such as above is not particularly limited as long as it has the above ether structure.

[0067] R ａ Examples of the halogen group represented by include —F, —Cl, —Br and —I.

[0068] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms (the total number of carbon atoms including the carbon atoms of the substituent) which may have a substituent include monovalent aromatic hydrocarbon groups such as a phenyl group, a naphthyl group, a biphenyl group, etc. Examples of the substituent which the aromatic hydrocarbon group may have include, but are not limited to, alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, etc., a hydroxyl group, a halogen group, etc.

[0069] Examples of the alkyl group having 1 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include linear and branched groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc. Examples of the substituent which the alkyl group has include, but are not limited to, a hydroxyl group, a halogen group, etc.

[0070] Examples of the cycloalkyl group having 5 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include a cyclopentyl group, a cyclohexyl group, etc. Examples of the substituent which the cycloalkyl group may have include alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group, a hydroxyl group, a halogen group, etc., but are not limited to these.

[0071] Examples of the aralkyl group having 7 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a diphenylmethyl group, etc. Examples of the substituent which the aralkyl group has include, but are not limited to, a hydroxyl group, a halogen group, etc.

[0072] In formula (A), n1 is a real number of 0 to 4, and is preferably 0 to 3, more preferably 0 or 1, from the viewpoint of achieving both polymerizability and heat resistance.

[0073] Compound C preferably has a structure shown in the following formula (B) as the structure shown in the above formula (A). From the viewpoint of environmental issues, it is preferable that the structure shown in the above formula (A) and the structure shown in the following formula (B) do not contain a halogen atom. In formula (B), R ｂ and R ｃ are each independently a hydroxyl group, a halogen group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms; n3 and n4 are each independently a real number of 0 to 4; X is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 20 carbon atoms, a substituted or unsubstituted alkylidene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylidene group having 5 to 20 carbon atoms, a substituted or unsubstituted aralkylene group having 8 to 20 carbon atoms, or a substituted or unsubstituted aralkylidene group having 7 to 20 carbon atoms, or a group combining these; * and ** represent the bond positions.

[0074] R ｂ and R ｃThe halogen group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, and substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, including their preferred forms, are the same as those in the above formula (A), and therefore further explanation will be omitted. In formula (3), n3 and n4 are real numbers of 0 to 4, and from the viewpoint of heat resistance, are preferably 0 to 3, and more preferably 0 or 1. In addition, in the above formula (B), R bonded to the benzene ring ｂ and R ｃ The bonding position of the bonding group such as is not particularly limited.

[0075] Examples of the aromatic hydrocarbon group represented by X having 6 to 20 carbon atoms (the total number of carbon atoms including the carbon atoms of the substituent) and which may have a substituent include divalent aromatic hydrocarbon groups such as a phenylene group, a naphthylene group, a biphenylene group, a divalent fluorene group (e.g., a 9,9-fluorene group), and a divalent anthracene group. The aromatic hydrocarbon group may be a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group. Examples of the substituent on the aromatic hydrocarbon group include alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group, a hydroxyl group, and a halogen group, but are not limited to these.

[0076] Examples of the alkylene group having 1 to 20 carbon atoms (total carbon number including the number of carbon atoms of the substituent) which may have a substituent include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, an isobutylene group, etc. Examples of the substituent which the alkylene group has include, but are not limited to, a hydroxyl group, a halogen group, etc.

[0077] Examples of cycloalkylene groups having 5 to 20 carbon atoms (the total number of carbon atoms including the carbon atoms of the substituent) that may have a substituent include a cyclopentylene group and a cyclohexylene group. Examples of substituents that the cycloalkylene group may have include alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group, a hydroxyl group, and a halogen group, but are not limited to these. For example, an example of a cycloalkylene group having a substituent is a 3,3,5-trimethylcyclohexylene group.

[0078] Examples of the alkylidene group having 1 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include an ethylidene group, a hexylidene group, etc. Examples of the substituent which the alkylidene group has include, but are not limited to, a hydroxyl group, a halogen group, etc.

[0079] Examples of the cycloalkylidene group having 5 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include a cyclopentylidene group, a cyclohexylidene group, etc. Examples of the substituent which the cycloalkylidene group has include alkyl groups such as a methyl group, an ethyl group, a propyl group, and a butyl group, a hydroxyl group, a halogen group, etc., but are not limited to these.

[0080] Examples of the aralkylene group having 8 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include a phenyldimethylene group, a naphthyldimethylene group, a biphenyldimethylene group, etc. Examples of the substituent which the aralkylene group has include alkyl groups such as methyl groups, ethyl groups, propyl groups, and butyl groups, hydroxyl groups, halogen groups, etc., but are not limited to these.

[0081] Examples of the aralkylidene group having 7 to 20 carbon atoms (the total number of carbon atoms including the number of carbon atoms of the substituent) which may have a substituent include a phenylmethylidene group, a phenylethylidene group, a phenylpropylidene group, etc. Examples of the substituent which the aralkylidene group has include, but are not limited to, alkyl groups such as methyl groups, ethyl groups, propyl groups, and butyl groups, hydroxyl groups, halogen groups, etc.

[0082] Examples of the group represented by X that is a combination of these groups include a divalent group that is a combination of at least two of the above-mentioned aromatic hydrocarbon groups, alkylene groups, cycloalkylene groups, alkylidene groups, cycloalkylidene groups, aralkylene groups, and aralkylidene groups. The bonding positions and arrangements of each group are not particularly limited and can be set appropriately.

[0083] The heterocyclic structure of compound C is not particularly limited, but is preferably a heterocyclic structure containing at least one of a nitrogen atom and an oxygen atom, which may have a substituent, i.e., a substituted or unsubstituted nitrogen-containing heterocyclic structure, an oxygen-containing heterocyclic structure, or an oxygen-containing nitrogen-containing heterocyclic structure, and more preferably a substituted or unsubstituted nitrogen-containing heteroaromatic ring structure.

[0084] Examples of the heterocyclic ring contained in the compound C include a pyrrole ring, a pyrrolidine ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, a carbazole ring, an acridine ring, a phenazine ring, a piperidine ring, a tetrahydropyran ring, a morpholine ring, a tetrahydrofuran ring, a furan ring, an oxazole ring, an oxazolidine ring, an oxazine ring, and an oxetane ring. From the viewpoints of reactivity and solubility in various organic solvents, the heterocyclic ring is preferably a pyrimidine ring or a triazine ring.

[0085] The bonding position of the heterocycle to another structure (for example, the structure represented by the above formula (A)) is not particularly limited. However, when the heterocycle is bonded to two other structures, i.e., when two bond positions are present, the bonding position is preferably the meta position from the viewpoint of reactivity.

[0086] Examples of the substituent on the heterocyclic structure include a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, a halogenated hydrocarbon group having 1 to 20 carbon atoms, a group in which a portion of these hydrocarbon groups or halogenated hydrocarbon groups is substituted with at least one atom selected from an oxygen atom and a sulfur atom, a nitro group, a cyano group, an amino group, and a salt of an amino group.

[0087] Examples of the halogen group in the above substituent include —F, —Cl, —Br and —I.

[0088] Examples of the hydrocarbon group having 1 to 20 carbon atoms in the above substituent include a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.

[0089] Examples of the chain hydrocarbon group include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and an n-pentyl group; alkenyl groups such as an ethenyl group, a propenyl group, a butenyl group, and a pentenyl group; and alkynyl groups such as an ethynyl group, a propynyl group, a butynyl group, and a pentynyl group.

[0090] Examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group; monocyclic cycloalkenyl groups such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group; and polycyclic cycloalkenyl groups such as a norbornenyl group.

[0091] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl, tolyl, xylyl, naphthyl and anthryl groups; and aralkyl groups such as benzyl, phenethyl, phenylpropyl and naphthylmethyl groups.

[0092] Examples of the halogenated hydrocarbon group having 1 to 20 carbon atoms in the above-mentioned substituent include groups in which some or all of the hydrogen atoms in the hydrocarbon group having 1 to 20 carbon atoms have been substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0093] Examples of the substituent in which a hydrocarbon group having 1 to 20 carbon atoms or a halogenated hydrocarbon group having 1 to 20 carbon atoms is partially substituted with at least one atom selected from an oxygen atom and a sulfur atom include groups in which the hydrocarbon group or halogenated hydrocarbon group is partially substituted with —O—, —S—, an ester group or a sulfonyl group.

[0094] The amino group in the above substituent is not particularly limited, and may be a primary amino group (—NH ２ ), a secondary amino group (—NHR), or a tertiary amino group (—NR ２ The substituent (R) in the secondary amino group and the tertiary amino group is not particularly limited, and examples thereof include the above-mentioned hydrocarbon groups having 1 to 20 carbon atoms. The anion constituting the anion moiety in the salt of the amino group is not particularly limited, and may be Cl. － Examples of known anions include:

[0095] From the viewpoints of reactivity and solubility, the substituent in the heterocyclic structure is preferably a halogen group, a hydrocarbon group having 1 to 6 carbon atoms, a halogenated hydrocarbon group having 1 to 6 carbon atoms, a nitro group, a cyano group, an amino group, or a salt of an amino group, and more preferably a fluorine atom, a chlorine atom, a methyl group, a nitro group, a cyano group, a tert-butyl group, a phenyl group, or a primary amino group.

[0096] From the viewpoint of heat resistance and electrical properties, the heterocyclic structure is preferably a structure selected from the structures shown in the following formulas (C) to (E), and more preferably the structure shown in formula (C). In formulas (C) to (E), R ｄ ~R ｈ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms; n5 represents a real number of 0 to 4; n6, n8, and n9 each independently represent a real number of 0 to 3; n7 represents a real number of 0 to 2; Q １ ~Q ２５ are each independently a nitrogen atom or a carbon atom, provided that Q １ ~Q ６ At least one of Q is a nitrogen atom; ７ ~Q １５ At least one of Q is a nitrogen atom; １６ ~Q ２５ At least one of Q is a nitrogen atom; １１ and Q １２ When at least one of the groups is a nitrogen atom, Q １１and Q １２ and Q ７ and Q １２ and Q １２ and Q １３ Bond with, or Q １０ and Q １１ and Q １１ and Q １５ The bond with Q is a single bond, ２０ and Q ２１ When at least one of the groups is a nitrogen atom, Q ２０ and Q ２１ and Q １６ and Q ２１ and Q ２１ and Q ２２ Bond with, or Q １９ and Q ２０ and Q ２０ and Q ２５ The bond to is a single bond, and * and ** indicate the bond positions.

[0097] R ｄ ~R ｈ Examples of the alkyl group having 1 to 20 carbon atoms represented by include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and an n-pentyl group.

[0098] R ｄ ~R ｈ Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R include aryl groups such as phenyl, tolyl, xylyl, naphthyl, and anthryl; and aralkyl groups such as benzyl, phenethyl, phenylpropyl, and naphthylmethyl. ｄ ~R ｈ Examples of the substituent that the alkyl group and aromatic hydrocarbon group represented by the formula (I) may have include the same substituents that the heterocyclic structure described above may have.

[0099] n5 is a real number of 0 to 4, and from the viewpoint of polymerizability, preferably 0 to 3, more preferably 0 to 2. n6, n8, and n9 are each independently a real number of 0 to 3, and from the viewpoint of polymerizability, preferably 0 to 2, more preferably 0 or 1. n7 is a real number of 0 to 2, and from the viewpoint of polymerizability, preferably 0 or 1. In the above formulae (C) to (E), R bonded to the cyclic structure ｄ ~R ｈ The bonding position of the bonding group such as is not particularly limited.

[0100] As described above, in the heterocyclic structures represented by formulae (C) to (E), the arrangement of the nitrogen atoms is not particularly limited, and accordingly, the position of the double bond in the ring structure can be appropriately selected and is not particularly limited.

[0101] Compound C can be represented by, for example, the structures shown in the following formulas (F) and (Z): １ -O-(A １ -B-O-) ｎ２ - (A ２ ) ｑ１ -R ２ (F) R １ -O-(B-O-A １ -) ｎ２ -(B-O) ｑ２ -R ２ (Z) In formula (F) and formula (Z), R １ and R ２ are each independently a group containing an ethylenically unsaturated double bond having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted nitrogen-containing heteroaromatic ring, １ and A ２ are each independently a group having the structure shown in formula (A) or a group having the structure shown in formula (B), provided that in formula (F), in formula (A) and formula (B), ** represents B or R ２ In the formula (Z), in the formulas (A) and (B), ** represents B or R ２Each B is independently a group having a divalent nitrogen-containing heterocyclic structure; each n2 is independently a real number of 1 or more; q1 is 0 or 1, and when q1 is 0, (A ２ ) ｑ１ represents a single bond, q2 is 0 or 1, and when q2 is 0, (B—O) ｑ２ represents a single bond.

[0102] R １ and R ２ Examples of the group having 2 to 50 carbon atoms and containing an ethylenically unsaturated double bond represented by the formula (I) include aromatic ring-containing groups such as a 3-isopropenylphenyl group, a 4-isopropenylphenyl group, a 2-allylphenyl group, a 2-methoxy-4-allylphenyl group, a 4-(1-propenyl)-2-methoxyphenyl group, a 3-isopropenylbenzyl group, a 4-isopropenylbenzyl group, a 4-vinylbenzyl group, a 3-vinylbenzyl group, and a 2-vinylbenzyl group, an allyl group, an acrylic group, and a methacrylic group.

[0103] Examples of the aromatic hydrocarbon group having 6 to 50 carbon atoms include aryl groups such as a phenyl group, a biphenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group; and aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, and a naphthylmethyl group.

[0104] Examples of the aliphatic hydrocarbon group having 6 to 50 carbon atoms include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group; monocyclic cycloalkenyl groups such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group; and polycyclic cycloalkenyl groups such as a norbornenyl group.

[0105] Examples of the nitrogen-containing heteroaromatic ring include the same rings as those exemplified in the heterocyclic structure described above.

[0106] R １ and R ２Examples of the substituent that may be possessed by include groups other than a hydroxy group, and specific examples include an allyl group, a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, a halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphate group, a hydroxy group, a primary to tertiary amino group, a salt of a carboxy group, a salt of a sulfonic acid group, a salt of a phosphonic acid group, a salt of a phosphate group, a salt of a hydroxy group, or a salt of a primary to tertiary amino group. Of these, an allyl group is preferred.

[0107] Examples of the halogen group, hydrocarbon group having 1 to 20 carbon atoms, and halogenated hydrocarbon group having 1 to 20 carbon atoms in the above substituents include the same as those in the substituents of the heterocyclic structure described above.

[0108] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, and an octyloxy group.

[0109] Examples of the alkylthio group having 1 to 20 carbon atoms include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a butylthio group, a pentylthio group, a hexylthio group, and an octylthio group.

[0110] Secondary amino group (-NHR) and tertiary amino group (-NR ２ The substituent (R) in the heterocyclic structure (R) is not particularly limited, and examples thereof include hydrocarbon groups having 1 to 20 carbon atoms. Specific examples thereof include the same groups exemplified as the substituent in the heterocyclic structure described above.

[0111] The cations constituting the cationic moieties in the salts of the carboxyl group, the salts of the sulfonic acid group, the salts of the phosphonic acid group, the salts of the phosphoric acid group, and the salts of the hydroxyl group are not particularly limited, and include Na ＋ Examples of known cations include:

[0112] The anion constituting the anion moiety in the salt of the amino group is not particularly limited, and may be Cl － Examples of known anions include:

[0113] In addition, A １ and A ２ The group having the structure represented by formula (A) is preferably the group represented by formula (B) above. In this case, in the case of formula (F), * in formula (B) represents the bonding position with O, and ** represents B or R ２ Similarly, in the case of formula (Z), * in formula (B) represents the bonding position with O, and ** represents the bonding position with B or R ２ represents the bonding position with

[0114] The group having a divalent nitrogen-containing heterocyclic structure represented by B is preferably a group selected from the structures shown in the above formulas (C) to (E). In this case, * and ** in formulas (C) to (E) respectively represent A in formula (F). １ or O, and O, A in formula (Z) １ or R ２ represents the bonding position with

[0115] n2 is a real number equal to or greater than 1, for example, a real number between 1 and 100.

[0116] Compound C is preferably a compound represented by the following formula (G): In formula (G), R １０ and R １６ are each independently a group containing an ethylenically unsaturated double bond having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted nitrogen-containing heteroaromatic ring, and R １１ , R １２ , R １４ and R １５ are each independently a hydroxyl group, a halogen group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms; R １３ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms; １ and X２ are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 20 carbon atoms, a substituted or unsubstituted alkylidene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylidene group having 5 to 20 carbon atoms, a substituted or unsubstituted aralkylene group having 8 to 20 carbon atoms, or a substituted or unsubstituted aralkylidene group having 7 to 20 carbon atoms, or a combination thereof; each Q is independently a nitrogen atom or a carbon atom, with the proviso that at least two of the Qs are nitrogen atoms; m1, m2, m4, and m5 are real numbers of 0 to 4, and from the viewpoint of polymerizability and heat resistance, are preferably 0 to 2, and more preferably 0 or 1; m3 is a real number of 0 to 2, and from the viewpoint of polymerizability and heat resistance, are preferably 0 or 1. p1 is a real number equal to or greater than 1, for example, a real number between 1 and 100.

[0117] In addition, R １０ and R １６ Each structure represented by is R in the above formula (F). １ and R ２ The preferred embodiments are also the same as those of the above. １１ , R １２ , R １４ and R １５ Each structure represented by is R in the above formula (B). ｂ and R ｃ The preferred embodiments are also the same as those of the above. １３ Each structure represented by is R in the above formulas (C) to (E). ｄ ~R ｈ The preferred embodiments are also the same as those of the above. １ and X ２ Each structure represented by is the same as X in the above formula (B), and the preferred forms are also the same.

[0118] Compound C is particularly preferably a compound represented by the following formula (G-1). In formula (G-1), R １０ ~R １６ , X１ and X ２ , m1 to m5, and p1 are all the same as those shown in the above formula (G), and the preferred embodiments are also the same.

[0119] For example, the following compounds can also be used as compound C. Modified polyphenylene ether (PPE) resins, vinylbenzyl ether resins, curable resins having a heterocyclic ether bond in the main chain such as triazine ether, polyfunctional methacrylate compounds having two or more methacrylic groups in the molecule, polyfunctional acrylate compounds having two or more acrylic groups in the molecule, trialkenyl isocyanurate compounds such as triallyl isocyanurate (TAIC), polyfunctional acrylate compounds, polyfunctional methacrylate compounds, and the like can also be used as compound C. The vinylbenzyl ether resin (a compound having a vinylbenzyl ether group) can be synthesized by reacting a phenolic resin such as a biphenylaralkyl phenol, an aralkyl phenol, or a naphthol aralkyl resin with chloromethylstyrene in the presence of an alkaline catalyst. As the modified PPE resin, for example, Noryl (registered trademark) SA-9000, manufactured by SABIC Innovative Plastics, can be used.

[0120] From the viewpoint of heat resistance, the content of Compound C in the solid content of the composition is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. From the viewpoint of electrical properties, the content of Compound C in the solid content of the composition is preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 50% by mass or less, still more preferably 40% by mass or less, and particularly preferably 30% by mass or less.

[0121] (Other Components) The composition may further contain other curable resins besides the resin A, and additives such as flame retardants other than the above-mentioned organophosphorus compounds, crosslinking agents, fillers, elastomers, etc. The composition may also contain a polymerization initiator such as dicumyl peroxide, 2,3-dimethyl-2,3-diphenylbutane (CCDFB), or an azo initiator. Note that the other components do not include those corresponding to the above-mentioned resin A, compound B, and compound C. Furthermore, from the viewpoint of environmental concerns, it is preferable that the other components do not contain halogen materials.

[0122] The composition may contain other curable resins as needed. Known curable resins may be used as appropriate, such as ODV and soluble divinylbenzene polymers.

[0123] Adding a crosslinking agent to the present composition and curing it results in a cured composition with excellent properties. Examples of the crosslinking agent include compounds having a reactive functional group, such as a styryl group (St group) or an allyl group, in the molecule. From the viewpoint of reactivity with the present composition, the reactive functional group is preferably a styryl group. More specifically, from the viewpoint of electrical properties, the crosslinking agent is preferably a vinyl compound such as 1,2-bis(vinylphenyl)ethane (BVPE), a fluorene compound having a vinylbenzyl group, an indene compound having a vinylbenzyl group, or divinylbenzene, as described in Japanese Patent No. 3681170, with BVPE being more preferred. The crosslinking agent may be a mixture of two or more types or a compound (polymer) having a repeating unit. For example, a vinyl compound represented by the following formula (H) or a vinyl compound represented by the following formula (I) may be used.

[0124] In formula (H), X ａ represents a hydrocarbon group having 6 or more carbon atoms, including at least one selected from an aromatic cyclic group and an aliphatic cyclic group; n ａ represents an integer of 1 to 10.

[0125] In formula (I), X ｂ represents one or more of (a) to (h) shown in the following formula (J).ｂ If there are multiple X ｂ may be the same as or different from each other. ２ represents a methylene group or an oxygen atom, and Q represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group. Multiple Qs may be the same or different. R represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group. When there are multiple Rs, the multiple Rs may be the same or different. l and m each represent an integer of 0 to 3, and n ｂ is a repeating unit, and l≦n ｂ ≦20, p is a repeating unit, and 1.1≦p≦20.

[0126] In formula (11), * indicates each bonding position.

[0127] The crosslinking agent may be, for example, a compound obtained by reacting a compound having fluorene or indene in its partial skeleton with a halogenated compound having an St group, such as chloromethylstyrene, in the presence of an alkali catalyst. A phase transfer catalyst may be used during the reaction, and the solvent is preferably an aprotic organic solvent containing an aprotic organic catalyst. More specifically, the crosslinking agent may be a compound represented by the following formula (K), obtained by reacting a compound having fluorene in its partial skeleton with chloromethylstyrene. In formula (K), R ３０ represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a halogenated alkyl group; X １０ represents an integer of 0 to 4.

[0128] The crosslinking agent may also be a vinyl compound (polyfunctional vinyl compound) having two or more vinyl groups in the molecule, such as polybutadiene or a styrene-butadiene copolymer; a polyfunctional aromatic copolymer obtained by copolymerizing divinylbenzene with a styrene derivative; or a vinylbenzyl compound such as styrene or divinylbenzene, which has a vinylbenzyl group in the molecule. Among these, those having two or more carbon-carbon double bonds in the molecule are preferred. Specific examples include polyfunctional aromatic copolymers and divinylbenzene compounds. The use of these crosslinking agents is believed to more effectively form crosslinks during the curing reaction, thereby further enhancing the heat resistance of the cured product of the present composition. The exemplified crosslinking agents may be used alone or in combination of two or more. Furthermore, as the crosslinking agent, a compound having two or more carbon-carbon unsaturated double bonds in the molecule may be used in combination with a compound having one carbon-carbon unsaturated double bond in the molecule. Specific examples of compounds having one carbon-carbon unsaturated double bond in the molecule include compounds having one vinyl group in the molecule (monovinyl compounds).

[0129] The average number of carbon-carbon unsaturated double bonds (number of terminal double bonds) per molecule of the crosslinking agent varies depending on the weight-average molecular weight of the crosslinking agent, but from the viewpoint of the heat resistance of the cured product, it is preferably 1 or more, more preferably 2 or more. From the viewpoints of reactivity, storage stability, and flowability of the composition, the number of terminal double bonds per molecule of the crosslinking agent is preferably 20 or less, more preferably 18 or less.

[0130] Considering the weight-average molecular weight of the crosslinking agent, the number of terminal double bonds of the crosslinking agent is preferably 1 to 4 when the weight-average molecular weight of the crosslinking agent is less than 500 (e.g., 100 or more and less than 500). Furthermore, the number of terminal double bonds of the crosslinking agent is preferably 3 to 20 when the weight-average molecular weight of the crosslinking agent is 500 or more (e.g., 500 or more and 5,000 or less). In each case, if the number of terminal double bonds is equal to or greater than the lower limit of the above range, the crosslinking agent is likely to have good reactivity, and it is easy to impart an appropriate crosslink density to the cured product of the resin composition, and it is easy to improve heat resistance and Tg. On the other hand, if the number of terminal double bonds is equal to or less than the upper limit of the above range, gelation of the composition can be easily prevented.

[0131] The number of terminal double bonds of the crosslinking agent can be determined from the specifications of the product of the crosslinking agent used. The number of terminal double bonds here refers to a value representing the average number of double bonds per molecule of all crosslinking agents present in 1 mole of the crosslinking agent.

[0132] Examples of the other flame retardants include halogen-based flame retardants such as bromine-based flame retardants. Each flame retardant may be used alone or in combination of two or more. However, from the viewpoint of environmental issues, it is preferable that the composition does not contain halogen materials. When a halogen-based flame retardant is used as the flame retardant, for example, SAYTEX 8010 (trade name, manufactured by Albemarle Corporation) can be used. These compounds can be produced by conventionally known methods. Commercially available halogen-based flame retardants may also be used. The structure of SAYTEX 8010 is as follows:

[0133] As the filler, silica, hollow silica, etc. can be used. From the viewpoint of dielectric properties, fillers with a small number of silanol groups are preferred. Furthermore, hollow silica allows for the production of compositions with a low dielectric constant. Silica whose surface has been modified can also be used. Specifically, silica that has been treated with a functional group containing a carbon-carbon unsaturated double bond and / or trimethylsilylation can be used.

[0134] Examples of the elastomer include styrene-based elastomers, such as styrene-butadiene-styrene copolymers, hydrogenated styrene-butadiene-styrene copolymers, styrene-isoprene-styrene copolymers, hydrogenated styrene-isoprene-styrene copolymers, and hydrogenated styrene (butadiene / isoprene)-styrene copolymers.

[0135] In addition, the present composition may contain acenaphthylene, indene, or derivatives thereof, if necessary. The blending ratio of these may be 75 mass% or less based on the present composition. Furthermore, the present composition may contain a fluororesin. The fluororesin may have a functional group to improve adhesion.

[0136] The total content of oxygen atoms and nitrogen atoms contained in the organic matter, excluding the inorganic filler, in the composition can be, for example, 0.01 to 10 mass %. This content can be measured using elemental analysis by a combustion method or calculated when raw materials with known structures are used.

[0137] <Method for Producing Resin Composition> The present composition can be prepared by mixing the above-mentioned resin A, organic phosphorus compound (compound B), compound C, and various additives as required.

[0138] (Method for Producing Resin A) The resin A can be obtained, for example, by polymerizing a compound having multiple isopropenyl groups (for example, a diisopropenyl compound) in the presence of an acid catalyst at a reaction temperature of 10 to 75°C.

[0139] As mentioned above, in addition to the α-olefin structure shown in formula (1), resin A may also have the terminal olefin structure, side chain olefin structure, indane structure shown in formula (2), and inner olefin structure shown in formula (3). Each of these structures is produced by a reaction between molecules having an isopropenyl group in the raw material, with the indane structure being dominant in terms of equilibrium (thermodynamics) and the α-olefin structure being dominant kinetically. Therefore, the blending ratio of each structure contained in resin A can be controlled by reaction conditions such as the type of catalyst and temperature conditions.

[0140] Here, the compound having multiple isopropenyl groups is a compound having two or more isopropenyl groups in one molecule. As described above, the compound can be one produced by a conventionally known method, and for example, diisopropenylbenzenes such as 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene can be used. Furthermore, as the compound, a precursor thereof (for example, α,α,α',α'-tetramethyl-1,3-benzenedimethanol) can also be used.

[0141] In the method for producing resin A, other compounds may be copolymerized together with the compound having multiple isopropenyl groups. That is, resin A may be a homopolymer of a compound having multiple isopropenyl groups, or a copolymer using multiple compounds including the compound. Examples of the other compounds include monovinyl compounds and divinyl compounds. More specifically, examples of the other compounds that can be used include alpha-olefin compounds such as alpha-methylstyrene, alpha-methylstyrene dimer, and diphenylethylene, monoisopropenyl compounds, and cyclic dienes. For example, the monoisopropenyl compound can be used as a terminator to stop the propagation reaction.

[0142] Furthermore, from the viewpoint of adjusting physical properties and molecular weight by introducing functional groups, structures such as a phenol structure, an aromatic amine structure, an aromatic ether structure, and a maleimide structure may be introduced into the resin A. When introducing such a structure, it is preferably introduced into the structure by utilizing an electrophilic substitution reaction with a cation generated from an isopropenyl group of the raw material during the polymerization reaction. However, as described above, the resin A does not need to contain heteroatoms other than carbon atoms and hydrogen atoms.

[0143] From the viewpoint of reactivity, the moisture content in the raw materials for obtaining Resin A, such as monomers, is preferably 500 ppm or less. If necessary, the raw materials can be dehydrated using a molecular sieve, alumina, or the like.

[0144] Examples of the acid catalyst used in the polymerization reaction include the following inorganic acids, solid acids, organic sulfonic acids, Lewis acids, and Bronsted acids. Note that one acid may correspond to multiple types of inorganic acids, solid acids, organic sulfonic acids, Lewis acids, and Bronsted acids. Inorganic acids: for example, sulfuric acid, nitric acid, hydrochloric acid, and phosphoric acid; Solid acids: for example, activated clay, acid clay, silica alumina, zeolite, sulfonated carbon, strongly acidic ion exchange resins, heteropolyhydrochloric acid, and tungstic acid; Organic sulfonic acids: for example, benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, methanesulfonic acid, fluoromethanesulfonic acid, and CF ３ SO ３ H, C ２ F ５ SO ３ H and C ６ F ５ SO ３ perfluoroalkanesulfonic acids such as H; Lewis acids such as AlCl ３ , TiCl ４ , SnCl ４ , B(C ６ F ５ ) ３ , B.F. ３ and Lewis bases and their complexes, methylalumoxanes, metallocene halides and methylalumoxanes and combinations thereof, and combinations thereof; Bronsted acids: for example, boric acid, acetic acid, benzoic acid.

[0145] As the Lewis base acting as a promoter component, for example, one or more compounds selected from the group consisting of ester compounds, thioester compounds, ketone compounds, amine compounds, ether compounds, thioether compounds, and phosphine compounds shown below can be used. Ester compounds: for example, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, phenyl acetate, methyl propionate, dimethyl carbonate, diethyl carbonate, ethylene carbonate; Thioester compounds: for example, methyl mercaptopropionic acid, ethyl mercaptopropionic acid; Ketone compounds: for example, methyl ethyl ketone, methyl isobutyl ketone, benzophenone; Amine compounds: for example, methylamine, ethylamine, propylamine, butylamine, cyclohexylamine, methylethylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine; Ether compounds: for example, diethyl ether, methyl tert-butyl ether, diethylene glycol dimethyl ether, propylene glycol dimethyl ether, tetrahydrorane, cyclopentyl methyl ether; Thioether compounds: for example, diethyl sulfide, diphenyl sulfide; Phosphine compounds: for example, tripropylphosphine, tributylphosphine, trihexylphosphine, tricyclohexylphosphine, trioctylphosphine, vinylphosphine, propenylphosphine, cyclohexenylphosphine, dialkenylphosphine, trialkenylphosphine.

[0146] In the method for producing Resin A, from the viewpoint of facilitating the production of an α-olefin structure (and terminal olefin structure, side chain olefin structure) and facilitating the control of molecular weight, it is preferable to use a combination (mixture) of one or more of the above-mentioned ester compounds, ketone compounds, and ether compounds with one or more of the above-mentioned acid catalysts. Here, examples of the acid catalyst include the above-mentioned Bronsted acids, Lewis acids, organic sulfonic acids, and inorganic acids. From the same viewpoint, it is also preferable to use one selected from the group consisting of methanesulfonic acid, BF3 complex, tin chloride, and toluenesulfonic acid as the acid catalyst. The amount of the co-catalyst relative to the acid catalyst is not particularly limited as it may vary depending on the reaction conditions, but it is preferable that the co-catalyst is 1 mole or more per 1 mole of the acid catalyst. For example, a Lewis acid (e.g., BF ３ ・O(C ２ H ５ ) ２ A catalytic mixture of methyl methyl acrylate and a Lewis base (e.g., isopropyl acetate) can be used.

[0147] The polymerization reaction can be carried out in a solvent. Examples of such solvents include: nonpolar organic solvents such as hexane, decane, dodecane, cyclohexane, benzene, toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, and trimethylbenzene; chlorine-based organic solvents such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, trichloroethane, and perchloroethane; and aromatic compounds such as halogenated benzenes, nitrobenzene, and trifluoromethylbenzene. In addition to the above solvents, the above-mentioned ester-based compounds, ketone-based compounds, and ether-based compounds can also be used as solvents.

[0148] In the method for producing Resin A, the reaction temperature in the polymerization reaction is preferably 10 to 75°C. When the reaction temperature is 10°C or higher, the reaction can be easily completed within an appropriate time. On the other hand, when the reaction temperature is 75°C or lower, the formation of indane structures and inner olefin structures is easily suppressed, and α-olefin structures, terminal olefin structures, and side chain olefin structures are easily formed.

[0149] Here, in the method for producing resin A, it is preferable to add raw materials (e.g., a diisopropenyl compound) to a reaction solution containing an acid catalyst and then carry out an aging reaction. Here, the reaction temperature and reaction time in the polymerization reaction refer to the temperature and time, respectively, from the start of the addition of raw materials to the reaction system and the start of the polymerization reaction of the added raw materials until the end of the polymerization reaction. In other words, the reaction time begins when the polymerization reaction of some of the raw materials starts. On the other hand, the aging temperature and aging time in the polymerization reaction refer to the temperature and time (in the aging reaction), respectively, from the end of the addition of all raw materials to the reaction system (after the entire amount is added dropwise, if the raw materials are added dropwise to the reaction system) until the end of the reaction. In other words, the end points of the reaction time and the aging time are the same. Note that the polymerization reaction in the method for producing resin A can be stopped by quenching the reaction by adding an alkaline raw material to the reaction system, lowering the temperature in the reaction system, or removing the catalyst by washing with water, etc. In this case, the reaction can be stopped when the desired compounding ratio of each structure is obtained, even if raw materials remain. When the polymerization reaction is stopped by such a method, the time at which the reaction reaction is stopped is regarded as the end time of the reaction time and the aging time.

[0150] The aging time is preferably 72 hours or less, more preferably 32 hours or less, even more preferably 24 hours or less, and particularly preferably 12 hours or less, from the viewpoint of controlling the blending ratio of the α-olefin structure (and terminal olefin structure and side chain olefin structure), control of the molecular weight, and control of the formation of insoluble components. Also, from the viewpoint of controlling the molecular weight, the aging time is preferably 5 minutes or more, more preferably 10 minutes or more, and even more preferably 15 minutes or more.

[0151] The aging temperature is preferably 10 to 75° C. from the viewpoint of molecular weight control and structure control.

[0152] In the method for producing Resin A, the solution containing the polymer (polymer) after the polymerization reaction has been stopped can be purified by a known method to obtain the target product (Resin A). Examples of purification methods include washing with water to remove water-soluble compounds by liquid separation, distilling off low-boiling compounds such as solvents under reduced pressure, and reprecipitation by mixing with a poor solvent. The obtained polymer can be further purified by a known method to achieve a high purity. Examples of purification methods include repeated redissolution and reprecipitation, washing with a poor solvent, drying under reduced pressure, and adsorption treatment using a cation exchange adsorbent or an anion exchange adsorbent.

[0153] Through the above operations, Resin A can be obtained. Note that different curable functional groups such as hydroxyl groups and amino groups can be introduced into Resin A to produce cured products with phenolic resins, epoxy resins, polyimide resins, etc., or this resin can be modified to be used as a maleimide resin or benzoxazine resin.

[0154] (Method for Producing Organophosphorus Compound (Compound B)) The organophosphorus compound may be a commercially available product, or may be produced by a conventionally known method. For example, the organophosphorus compound shown below can be produced by the following method.

[0155] First, phosphorus oxychloride, 2,6-xylenol, xylene as a solvent, and magnesium chloride as a catalyst are reacted under heating conditions (for example, at a temperature of 160°C) to synthesize the following dixylyl phosphorochloridate. During the reaction, the hydrogen chloride (hydrochloric acid gas) generated is recovered, and xylene, unreacted phosphorus oxychloride and 2,6-xylenol, and by-product hydrogen chloride are removed under reduced pressure. Next, the obtained dixylyl phosphorochloridate and bisphenol are added to a solvent of toluene and tetrahydrofuran, and triethylamine is added dropwise under heating conditions (for example, at a temperature of 65° C.) while stirring. Then, purification by distillation or the like is carried out as necessary to obtain the above-mentioned organophosphorus compound.

[0156] (Method for producing compound C) The method for producing compound C is not particularly limited, and a known method can be used as appropriate. For example, when compound C is represented by the structure shown in formula (F) above, A １ A monomer serving as a raw material for the portion containing A ２ a monomer serving as a raw material for the portion containing B; and a monomer serving as a raw material for the portion containing R １ and a monomer serving as a raw material for the portion containing R ２ The monomers that are raw materials for the moiety containing A and, if necessary, other monomers are heated together with an alkali metal or an alkali metal compound in an organic solvent. １ A monomer serving as a raw material for the portion containing A ２ The monomers that are raw materials for the portion containing R may be the same monomer or different monomers. １ and a monomer serving as a raw material for the portion containing R ２ The monomers that are raw materials for the moiety containing A may be the same monomer or different monomers. １ After polymerizing the monomer that is the raw material for the portion containing R and the monomer that is the raw material for the portion containing B, １ or R ２ The monomers that are the raw materials for the portion containing the monomer and other monomers may be heated and mixed to react with each other.

[0157] The above A １ Or A ２Examples of the monomers that can be used as raw materials for the portion containing the formula (I) include dihydroxyphenyl compounds such as hydroquinone, resorcinol, catechol, and phenylhydroquinone; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-allylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-phenylphenyl)propane, 4,4'-(1,3-dimethylbutylidene)bisphenol, and 1,1-bis(4-hydroxyphenyl)-nonane. bisphenol compounds such as bisphenol, bis(4-hydroxyphenyl)sulfone, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-methyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 4,4'-cyclododecylidenebisphenol, and 4,4'-decylidenebisphenol; and diol compounds such as Priplast 1901, 1838, 3186, 3192, 3197, and 3199 (all trade names, manufactured by Croda Japan Ltd.). These monomers may be used alone or in combination of two or more.

[0158] Examples of the monomer that serves as a raw material for the portion containing B include 4,6-dichloropyrimidine, 4,6-dibromopyrimidine, 2,4-dichloropyrimidine, 2,5-dichloropyrimidine, 2,5-dibromopyrimidine, 5-bromo-2-chloropyrimidine, 5-bromo-2-fluoropyrimidine, 5-bromo-2-iodopyrimidine, 2-chloro-5-fluoropyrimidine, and 2-chloro-5-iodopyrimidine. 2-phenyl-4,6-dichloropyrimidine, 2-methylthio-4,6-dichloropyrimidine, 2-methylsulfonyl-4,6-dichloropyrimidine, 5-methyl-4,6-dichloropyrimidine, 2-amino-4,6-dichloropyrimidine, 5-amino-4,6-dichloropyrimidine, 2,5-diamino-4,6-dichloropyrimidine, 4-amino-2,6-dichloropyrimidine, 5-methoxy-4, 6-Dichloropyrimidine, 5-methoxy-2,4-dichloropyrimidine, 2-methyl-4,6-dichloropyrimidine, 6-methyl-2,4-dichloropyrimidine, 5-methyl-2,4-dichloropyrimidine, 5-nitro-2,4-dichloropyrimidine, 4-amino-2-chloro-5-fluoropyrimidine, 2-methyl-5-amino-4,6-dichloropyrimidine, 5-bromo-4-chloro-2-methylthio pyrimidine compounds such as pyrimidine; pyridazine compounds such as 3,6-dichloropyridazine, 3,5-dichloropyridazine, and 4-methyl-3,6-dichloropyridazine; and pyrazine compounds such as 2,3-dichloropyrazine, 2,6-dichloropyrazine, 2,5-dibromopyrazine, 2,6-dibromopyrazine, 2-amino-3,5-dibromopyrazine, and 5,6-dicyano-2,3-dichloropyrazine. These monomers may be used alone or in combination of two or more.

[0159] The R １ or R ２Examples of monomers that can be used as raw materials for the moiety containing include monohydric phenol compounds such as t-butylphenol, nonylphenol, 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, tocotrienol, α-tocophenol, 4-hydroxyphenylmaleimide, and 2-phenylphenol; monovalent amine compounds such as 4-hexylaniline and diallylamine; monovalent thiol compounds such as 1-octanethiol; monovalent aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, and 3-(chloromethyl)styrene; monovalent acid halides such as acryl chloride, methacryl chloride, crotonoyl chloride, and cinnamoyl chloride; and monovalent acid anhydrides such as acrylic anhydride, crotonic anhydride, and methacrylic anhydride. These monomers may be used alone or in combination of two or more.

[0160] Examples of other monomers include compounds that derive structural units containing a carbonate bond, a thiocarbonate bond, or a selenocarbonate bond, such as diphenyl carbonate, diphenyl thiocarbonate, diphenyl selenocarbonate, phosgene, thiophosgene, and selenophosgene; dihydroxy compounds such as benzene dimethanol and cyclohexane dimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthrylphosphine oxide; and dihalides of dicarboxylic acids such as phthalic acid dichloride, isophthalic acid dichloride, and terephthalic acid dichloride. These monomers may be used alone or in combination of two or more.

[0161] When a compound having a hydroxy group, such as a phenol compound, is used as a raw material in the synthesis of Compound C, the alkali metal and alkali metal compound react with the compound having a hydroxy group to form an alkali metal salt. Examples of such alkali metal and alkali metal compounds include: alkali metals such as lithium, sodium, and potassium; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal bicarbonates such as lithium bicarbonate, sodium bicarbonate, and potassium bicarbonate. Among these, alkali metal carbonates are preferred, and potassium carbonate is more preferred.

[0162] When a compound having a hydroxy group is used in the synthesis of compound C, the amounts of alkali metal and alkali metal compound used are such that the lower limit of the ratio of the number of moles of alkali metal atoms to the number of moles of hydroxy groups in all compounds used in the synthesis of compound C is preferably 1, more preferably 1.1, and even more preferably 1.2, and the upper limit of said ratio is preferably 3, more preferably 2, and even more preferably 1.8.

[0163] Examples of the organic solvent include: ether-based solvents such as tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, anisole, phenetole, diphenyl ether, dialkoxybenzene, and trialkoxybenzene; nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; ester-based solvents such as γ-butyrolactone; sulfur-containing solvents such as sulfolane, dimethyl sulfoxide, diethyl sulfoxide, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, and diphenyl sulfone; ketone-based solvents such as benzophenone, 2-heptanone, cyclohexanone, and methyl ethyl ketone; halogen-based solvents such as methylene chloride, chloroform, and chlorobenzene; and aromatic hydrocarbon-based solvents such as benzene, toluene, and xylene.

[0164] Of these organic solvents, 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, and xylene are preferred, and N-methyl-2-pyrrolidone, 2-heptanone, and cyclohexanone are more preferred.

[0165] The reaction temperature during the synthesis is preferably 50° C. or higher, more preferably 80° C. or higher, and preferably 300° C. or lower, more preferably 200° C. or lower. The reaction time during the synthesis is preferably 1 hour or longer, more preferably 2 hours or longer, even more preferably 3 hours or longer, and preferably 100 hours or shorter, more preferably 50 hours or shorter, even more preferably 24 hours or shorter.

[0166] From the viewpoint of suppressing gelation of the polymerization reaction solution, R １ or R ２ The reaction temperature when the monomer serving as the raw material for the portion containing is added after polymerization is preferably 0°C or higher, more preferably 10°C or higher, and is preferably 130°C or lower, more preferably 110°C or lower.

[0167] The R １ or R ２The reaction time when a monomer serving as a raw material for the portion containing (a) is added after polymerization and reacted is preferably 1 hour or more, more preferably 2 hours or more, even more preferably 3 hours or more, and is preferably 48 hours or less, more preferably 24 hours or less, even more preferably 10 hours or less.

[0168] <Prepreg> The prepreg according to the present disclosure (hereinafter also referred to as the present prepreg) includes the present composition described above. The present prepreg can be produced, for example, by the following method. Specifically, first, the present composition, to which the other additives described above (elastomer, curing agent such as a crosslinking agent, etc.) have been added as necessary, is mixed and stirred to produce a resin varnish. Next, a fibrous material is immersed in the resin varnish and dried to obtain a prepreg.

[0169] Here, as the fibrous material to be immersed in the resin varnish, it is preferable to use glass cloth of any composition from the viewpoints of processability and electrical properties, and it is more preferable to use quartz cloth from the viewpoint of electrical properties.

[0170] <Metal-clad laminate and manufacturing method thereof> The metal-clad laminate according to the present disclosure (hereinafter referred to as the present laminate) includes a cured product of the present composition described above and a metal foil. The present laminate is obtained by bonding a prepreg containing the present composition described above to a metal foil. More specifically, the present laminate can be manufactured by bonding a metal foil (e.g., copper foil) to both sides of a prepreg impregnated with the present composition described above by laminating, for example, under heat and pressure.

[0171] From the viewpoint of practical application, the metal foil peel strength (peel strength) of a metal-clad laminate obtained by laminating a prepreg obtained using the present composition and a metal foil under heat and pressure is preferably 2.0 N / cm or more, and more preferably 2.5 N / cm or more.

[0172] The present disclosure will be described in more detail below using several examples, but the present disclosure is not limited to these examples. Examples 1 to 23 are working examples according to the present disclosure, and Examples 24 to 27 are comparative examples.

[0173] <Structural analysis method> The blending ratio of each structure in the resin A, compound B, and compound C used in each example was calculated as follows: １ H-NMR and １３ Identification was carried out using C-NMR.

[0174] ( １ H-NMR) The object to be measured (for example, resin A) is dissolved in chloroform-d １ Dissolved in １ Measurement was carried out by H-NMR (Bruker, product name: Avance NEO400). Tetramethylsilane was used as an internal standard. Peaks of hydrogen atoms derived from the α-olefin structure, inner olefin structure, terminal olefin, and side chain olefin in the present invention can be confirmed at 4.70-5.40 ppm.

[0175] ( １３ C-NMR) The object to be measured (for example, resin A) is dissolved in chloroform-d １ to a concentration of 20% by mass, １３ Measurements were performed using a C-NMR (manufactured by JEOL, trade name: ECZ600). Hexamethyldisiloxane was used as an internal standard substance. Spectral analysis was performed using Delta v6.0 (analysis software manufactured by JEOL Ltd.).

[0176] (Calculation of the content of each structure in Resin A) Peaks were assigned by two-dimensional NMR and DEPT method. １３A baseline was drawn for each peak in C-NMR, and the content (mmol / g) of each structure in 1 g of the target substance (resin A) was calculated from the amount (g) of the measurement target (resin A) using the following formula: area a (area from 16.8 to 18.2 ppm) assigned to carbon in the inner olefin structure; area b (area from 59.1 to 60.2 ppm) assigned to carbon in the indane structure; area c (area from 114.3 to 118.1 ppm) assigned to carbon in the α-olefin structure, terminal olefin structure, and side-chain olefin structure; area d (area from 21.6 ppm to 22.3 ppm) assigned to carbon in the terminal olefin structure and side-chain olefin structure; area e (area from 1.4 to 2.5 ppm) of the internal standard substance; and the amount f (grams) of hexamethyldisiloxane added. Inner olefin content: a / (e / 6) x f / 162.38 / g x 1000 Indane content: b / (e / 6) x f / 162.38 / g x 1000 α-olefin content: (c-d) / (e / 6) x f / 162.38 / g x 1000 Terminal olefin and side chain olefin content: d / (e / 6) x f / 162.38 / g x 1000. FA = [α-olefin structure content] / ([inner olefin structure content] + [indane structure content] + [α-olefin structure content]) FI = [indane structure content] / ([inner olefin structure content] + [indane structure content] + [α-olefin structure content] / 2)

[0177] <Iodine Value Measurement Method> The iodine value of the object to be measured (resin A) was measured by a method in accordance with JIS K 0070. Specifically, the object to be measured was reacted with Wiess's reagent (iodine monochloride / acetic acid solution) and allowed to stand in a dark place, and then the excess iodine monochloride was titrated with sodium thiosulfate to calculate the iodine value.

[0178] <Molecular Weight Measurement Method> The weight average molecular weight Mw, number average molecular weight Mn, and molecular weight distribution (Mw / Mn) were measured using gel permeation chromatography (GPC) (manufactured by Tosoh Corporation, trade name: HLC-8420 GPC). The column used was a combination of guard columns manufactured by Tosoh Corporation: "HXL-L" (trade name), "SuperH-RC" (trade name), "TSKgel SuperHZ2000" (trade name), "TSKgel SuperHZ2500" (trade name), "TSKgel SuperHZ3000" (trade name), and "TSKgel SuperHZ4000" (trade name). The measurement was performed using a developing solvent of tetrahydrofuran, a flow rate of 1.0 ml / min, a column temperature of 40°C, a detector of RI (differential refractometer), and a calibration curve based on monodisperse polystyrene. Data processing was performed using a "GPC Workstation EcoSEC-WorkStation" (product name) manufactured by Tosoh Corporation.

[0179] <Measurement of Dielectric Loss Tangent (Df)> The film-like cured product described below and a substrate obtained by etching the copper foil from a copper-clad laminate for evaluation described below were used as test specimens, and the dielectric loss tangent (Df) at a frequency of 10 GHz was measured at room temperature (25°C) using a vector network analyzer ("E8361C" (trade name) manufactured by Agilent Technologies) by the SPDR method. For measurements without glass cloth, a film-like cured product described below was used, and for measurements with glass cloth, a substrate obtained by etching the copper foil from a copper-clad laminate for evaluation described below was used. The dielectric loss tangent (Df) of the copper-clad laminate for evaluation was evaluated based on the following criteria. (Evaluation Criteria) A+: 0.0015 or less A: More than 0.0015 and 0.0025 or less B: More than 0.0025 and 0.004 or less C: More than 0.004

[0180] <Preparation of Film-Like Cured Product> The film-like cured product was prepared as follows. 10 parts by mass of each resin obtained in Production Examples A1 to A8 described below and 2 parts by mass of BVPE were dissolved in 12 parts by mass of toluene. The resulting toluene solution was then poured between PTFE spacers, sandwiched between polyimide films, held between SUS plates, and cured in a vacuum press at a pressure of 2 MPa and 200°C for 2 hours to obtain a film-like cured product.

[0181] (Production of Resin A) [Production Example A1] N ２ Under flow, 480 g of paraxylene, 4.80 g (33.8 mmol) of boron trifluoride / diethyl ether complex (manufactured by Tokyo Chemical Industry Co., Ltd.) as an acid catalyst, and 6.91 g (67.6 mmol) of propyl acetate as a co-catalyst were added to a 1 L glass reaction vessel equipped with a stirring blade and a fluororesin-coated thermocouple, and the mixture was maintained at 25 ° C for 2 hours. Then, while maintaining the reaction temperature at 50 ° C, 120.0 g of 1,3-diisopropenylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the reaction vessel over 2 hours using a syringe pump. Furthermore, after the dropwise addition, the reaction was continued for 15 minutes (aging time) while maintaining the temperature at 50 ° C (aging temperature) as an aging step. Then, 100 g of a 5% by mass aqueous sodium bicarbonate solution was added to the reaction vessel to terminate the reaction. Subsequently, the aqueous phase in the reaction vessel was discarded, and the mixture was washed three times with 300 ml of ion-exchanged water to obtain a resin solution. Next, 2200 g of methanol was added to another 6 L flask, and the resin solution was gradually added to reprecipitate the resin. Thereafter, a resin cake was obtained by filtration. The resin cake was redispersed in 2200 g of methanol, washed, and filtered twice, and the resulting resin was then vacuum dried at 60°C to obtain 107.9 g of resin A-1. The structural analysis, iodine value measurement, and molecular weight measurement of the resulting resin A-1 were performed according to the methods described above. As a result, the molecular weight of the resulting resin A-1 was Mn: 1,770, Mw: 7,090. The iodine value of the resin A-1 was 131. When the resin A-1 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. It was confirmed that the resulting resin A-1 contained an α-olefin structure. １３ This was confirmed by C-NMR.

[0182] [Production Example A2] Production Example A1 was repeated except that 0.96 g (6.76 mmol) of boron trifluoride / diethyl ether complex was used, 1.38 g (13.5 mmol) of propyl acetate was used, the reaction temperature and aging temperature were set to 37.5°C, and the aging time was set to 25 minutes, to obtain 112.7 g of resin A-2. Structural analysis, iodine value measurement, and molecular weight measurement of the obtained resin A-2 were performed according to the methods described above. As a result, the molecular weight of the obtained resin A-2 was Mn: 2,260, Mw: 19,130. The iodine value of the resin A-2 was also 124. The content of each structure in the obtained resin A-2 is as follows. When the resin A-2 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. Content of each structure: α-olefin structure: 1.97 mmol / g, indane structure: 0.53 mmol / g, inner olefin structure: 0.16 mmol / g, terminal and side chain olefin structures: 0.96 mmol / g.

[0183] [Production Example A3] Production Example A1 was repeated except that 0.96 g (6.76 mmol) of boron trifluoride / diethyl ether complex was used, 1.38 g (13.5 mmol) of propyl acetate was used, the reaction temperature and aging temperature were set to 37.5°C, and the aging time was set to 45 minutes, yielding 110.3 g of Resin A-3. The structural analysis, iodine value measurement, and molecular weight measurement of the obtained Resin A-3 were performed according to the methods described above. The results are as follows. When Resin A-3 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. Molecular weight: Mn: 2,680, Mw: 40,683, Iodine value: 119, Content of each structure: α-olefin structure: 2.18 mmol / g, indane structure: 0.53 mmol / g, inner olefin structure: 0.14 mmol / g, terminal and side chain olefin structure: 0.62 mmol / g.

[0184] [Production Example A4] 98.1 g of Resin A-4 was obtained by the same procedure as in Production Example A1, except that 2.0 g (14.1 mmol) of boron trifluoride / diethyl ether complex, 2.87 g (28.1 mmol) of propyl acetate, and the aging time were changed to 60 minutes. The structural analysis, iodine value measurement, and molecular weight measurement of the obtained Resin A-4 were performed according to the methods described above. The results are as follows. When Resin A-4 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. Molecular weight: Mn: 2,460, Mw: 23,800, Iodine value: 114, Content of each structure: α-olefin structure: 3.55 mmol / g, indane structure: 1.37 mmol / g, inner olefin structure: 0.14 mmol / g, terminal and side chain olefin structure: 0.27 mmol / g.

[0185] [Production Example A5] 99.1 g of Resin A-5 was obtained in the same manner as in Production Example A1, except that the aging time was changed to 120 minutes. The structural analysis, iodine value measurement, and molecular weight measurement of the obtained Resin A-5 were performed according to the methods described above. The results are as follows. When Resin A-5 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. Molecular weight: Mn: 3,040, Mw: 35,720, Iodine value: 96, Content of each structure: α-olefin structure: 2.25 mmol / g, indane structure: 1.03 mmol / g, inner olefin structure: 0.47 mmol / g, terminal and side chain olefin structure: 0.07 mmol / g.

[0186] [Production Example A6] Production Example A1 was repeated except that the reaction temperature and aging temperature were changed to 55°C and the aging time to 90 minutes, yielding 111.0 g of Resin A-6. The structural analysis, iodine value measurement, and molecular weight measurement of the obtained Resin A-6 were performed according to the methods described above. The results are as follows. When Resin A-6 was dissolved in toluene to a concentration of 60% by mass, no insoluble matter was generated. Molecular weight: Mn: 2,640, Mw: 20,900, Iodine value: 110, Content of each structure: α-olefin structure: 2.50 mmol / g, indane structure: 0.89 mmol / g, inner olefin structure: 0.73 mmol / g, terminal and side chain olefin structure: 0.15 mmol / g.

[0187] [Production Example A7] Production Example A1 was repeated except that the reaction temperature and aging temperature were changed to 75°C and the aging time to 60 minutes, yielding 109.1 g of Resin A-7. The structural analysis, iodine value measurement, and molecular weight measurement of the obtained Resin A-7 were carried out according to the methods described above. The results are as follows: Molecular weight: Mn: 2,700, Mw: 15,530, Iodine value: 65, Content of each structure: α-olefin structure: 1.61 mmol / g, indane structure: 2.00 mmol / g, inner olefin structure: 0.65 mmol / g, terminal and side chain olefin structure: 0.07 mmol / g

[0188] [Manufacture example A8] N ２ Under flow conditions, 500 g of paraxylene and 17.5 g of paratoluenesulfonic acid monohydrate were added to a 1 L glass flask equipped with a thermometer and a stirrer, and the temperature was raised to 60°C. While maintaining the reaction temperature at 60°C, 250 g of 1,3-diisopropenylbenzene (manufactured by TCI) was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was allowed to mature for one hour at a ripening temperature of 60°C. After cooling, 160 g of water was added to dissolve the catalyst and then removed. The mixture was repeatedly washed with 160 g of water until neutral. The solvent and monomer were then distilled off under reduced pressure, yielding 136 g of viscous resin A-8. The structural analysis, iodine value measurement, and molecular weight measurement of the resulting resin A-8 were performed according to the methods described above. The molecular weight of the resulting resin A-8 was Mn: 390, Mw: 570, and the iodine value was 210. When the obtained resin A-8 was analyzed by NMR, a peak of an isopropenyl group was confirmed in the 4.70-5.40 ppm region in the 1H-NMR chart.

[0189] The reaction conditions, molecular weight, content of each structure, etc. of each resin obtained in Production Examples A1 to A8 are shown in Table 1. In addition, the Df of the film-like cured product using each resin was measured according to the method described above, and is shown in Table 1.

[0190]

[0191] (Production of Compound C) [Production Example C1] 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.65 g), and potassium carbonate (18.65 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (50.50 g) was added. The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, m,p-(chloromethyl)styrene (11.53 g) was added dropwise with the vessel cooled to 10°C, and the mixture was reacted at 100°C for 4 hours. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (55.0 g), and the salt was removed from the diluted solution by filtration. The resulting solution was then poured into methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, and collected by filtration again. The solid was then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain polymer C-1 (compound C-1) represented by the following formula (C-1). The number-average molecular weight (Mn) of the polymer was 1,800 and the weight-average molecular weight (Mw) was 4,000.

[0192] [Production Example C2] 2,2-bis(4-hydroxy-3-methylphenyl)propane (26.43 g), 4,6-dichloro-2-phenylpyrimidine (17.08 g), and potassium carbonate (19.23 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (42.50 g) was added. The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, m,p-(chloromethyl)styrene (11.53 g) was added dropwise with the vessel cooled to 10°C, and the mixture was reacted at 100°C for 4 hours. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (55.0 g), and the salt was removed from the diluted solution by filtration. The resulting solution was then poured into methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, and collected by filtration again. The solid was then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain polymer C-2 (compound C-2) represented by the following formula (C-2). The number-average molecular weight (Mn) of the polymer was 1,600 and the weight-average molecular weight (Mw) was 3,200.

[0193] [Production Example C3] 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (57.95 g), 4,6-dichloropyrimidine (31.72 g), isopropenylphenol (7.11 g), and potassium carbonate (33.77 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (42.67 g) was added. The mixture was reacted at 130°C for 6 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with N-methyl-2-pyrrolidone (240.0 g). After removing the salt by filtration, the resulting solution was poured into methanol (12.9 kg). The precipitated solid was separated by filtration, washed with a small amount of methanol, and recovered by filtration again. The solid was then dried under reduced pressure at 120°C for 12 hours using a vacuum dryer to obtain polymer C-3 (compound C-3) represented by the following formula (C-3). The polymer had a number average molecular weight (Mn) of 1,500 and a weight average molecular weight (Mw) of 3,100.

[0194] [Preparation Example C4] Polymer C-4 (compound C-4) represented by the following formula (C-4) was obtained by synthesis in the same manner as in Preparation Example C3, except that the raw materials and alkali metal compound used were changed to 2,2-bis(4-hydroxyphenyl)propane (30.4 g), isopropenylphenol (5.2 g), 4,6-dichloro-2-phenylpyrimidine (34.3 g), and potassium carbonate (24.0 g). The number-average molecular weight (Mn) of the polymer was 1500, and the weight-average molecular weight (Mw) was 3100.

[0195] [Preparation Example C5] Polymer C-5 (Compound C-5) represented by the following formula (C-5) was obtained by synthesizing the polymer in the same manner as in Preparation Example C3, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (36.1 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (10.1 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (34.5 g), isopropenylphenol (5.2 g), potassium carbonate (24.0 g), and N-methyl-2-pyrrolidone (69.1 g). The number-average molecular weight (Mn) of the polymer was 1900, and the weight-average molecular weight (Mw) was 4100.

[0196] [Production Example C6] 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (41.52 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (11.61 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (30.14 g), and potassium carbonate (26.18 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (42.67 g) was added, followed by reaction for 6 hours at 130°C under a nitrogen atmosphere. After the reaction, the vessel was cooled to 10°C, and methacryloyl chloride (4.06 g) was added dropwise, followed by reaction for 6 hours at 50°C. The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (240.0 g), and the salt was removed by filtration. The resulting solution was then poured into methanol (12.90 kg). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtration again. The solid was then dried under reduced pressure at 120°C for 12 hours using a vacuum dryer to obtain Polymer C-6 (Compound C-6) represented by the following formula (C-6). The number-average molecular weight (Mn) of the polymer was 1900, and the weight-average molecular weight (Mw) was 4100.

[0197] [Preparation Example C7] Polymer C-7 (Compound C-7) represented by the following formula (C-7) was obtained by synthesizing the polymer in the same manner as in Preparation Example C1, except that the raw materials and alkali metal compound used were changed to 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (30.78 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (8.58 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (20.18 g), m,p-chloromethylstyrene (10.0 g), potassium carbonate (22.1 g), and N-methyl-2-pyrrolidone (69.1 g). The number-average molecular weight (Mn) of the polymer was 1800, and the weight-average molecular weight (Mw) was 4000.

[0198] Next, compositions (resin varnishes) and metal-clad laminates were prepared using the resin A, the compound B described below, the compound C described above, and the like, according to the following procedure, and the laminates were evaluated.

[0199] <Preparation of Resin Varnish> Resin A, Compound C, elastomer, crosslinking agent, and initiator (described later) were dissolved in toluene to a solid content of 50% by mass. Further, an organic phosphorus compound (Compound B) and an inorganic filler (filler) (described later) were added to the obtained toluene solution, and the mixture was mixed and dispersed using a rotor / stator mixer to obtain a resin varnish. Resin A: each resin obtained in Production Examples A1 to A8, Compound C: each compound obtained in Production Examples C1 to C7, modified polyphenylene ether (trade name: SA-9000, manufactured by SABIC Innovative Plastics), maleimide resin (trade name: NE-X 9470S, manufactured by DIC Corporation), elastomer: Tuftec H1043 (trade name, manufactured by Asahi Kasei), crosslinking agent: 1,2-bis(vinylphenyl)ethane (BVPE), initiator: CUROX (registered trademark) CC-DC (trade name, manufactured by United Initiators GmbH), inorganic filler: spherical silica EQ2410-SCM (trade name, manufactured by Zhejiang Third Age Material Technology Co. Ltd.), Organic phosphorus compound (compound B): ((1,4-phenylenedimethylene)bis(diphenylphosphane oxide) (trade name: BES5-1150P, manufactured by Regina Electronics), [2-(diphenylphosphoryl)ethyl](diphenyl)phosphorine oxide (trade name: VHP-4 dimer, manufactured by Osaka Gas Industries, Ltd.), SPV-100 (trade name, manufactured by Otsuka Chemical Co., Ltd.)

[0200] <Preparation of Evaluation Substrates> Glass cloth (E-glass, #2116) was immersed in the resulting resin varnish, sandwiched between metal bars, and pulled out. After removing excess varnish, the cloth was dried at room temperature (25°C) for 10 minutes. This was then dried in an air oven at 130°C for 4 minutes to prepare a prepreg. The resin content (R.C) of the resin composition relative to the prepreg was adjusted to 55% by mass. Two sheets of this prepreg were stacked, and copper foil: HS1-M2-VSP (trade name, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides. The resulting prepreg was molded and cured using a vacuum press molding machine to obtain evaluation substrates (copper-clad laminates) for Examples 1 to 22. The curing conditions were a pressure of 3 MPa and a temperature of 200°C for 90 minutes.

[0201] <Evaluation of Flame Retardancy> Copper-clad laminates for evaluation were obtained in the same manner as in Examples 1 to 27, except that 12 sheets of prepreg were stacked. The copper foil was removed from the obtained copper-clad laminate for evaluation by etching. Five samples of 125 mm x 13 mm were prepared from this substrate. Each of these five samples was exposed to a flame for 10 seconds to check their burning behavior. Flame retardancy was evaluated according to the following criteria. (Evaluation Criteria) A+: The total burning time of the five samples was 30 seconds or less, and all five samples were less than 10 seconds. A: The total burning time of the five samples was more than 30 seconds but less than 50 seconds, and all five samples were less than 10 seconds. B: The total burning time of the five samples was 50 seconds or less, and one or more samples had a burning time of 10 seconds or more. C: The total burning time of the five samples was more than 50 seconds.

[0202] <Measurement of Glass Transition Temperature Tg> The copper foil was removed by etching from the copper-clad laminates for evaluation shown in Examples 1 to 27, and the resulting substrates were used as test specimens. Dynamic viscoelasticity measurement (DMA) was performed using a dynamic viscoelasticity measuring device ("DVA-200" (trade name) manufactured by IT Measurement Control Co., Ltd.) to measure the glass transition temperature (Tg) (°C). The measurement was performed under conditions of a frequency of 10 Hz, a heating rate of 2°C / min, and a temperature range of 25 to 300°C. Tg was evaluated based on the following criteria. (Evaluation Criteria) A+: 200°C or higher A: 175°C or higher, but less than 200°C B: 150°C or higher, but less than 175°C C: Less than 150°C The measurement results are shown in Tables 2 to 4 below.

[0203] <Copper Foil Peel Strength: Measurement of Peel Strength> Test pieces measuring 20 mm wide and 100 mm long were cut from the copper-clad laminates prepared in Examples 1 to 27 for evaluation, and 10 mm-wide parallel cuts were made on the copper foil surface. The copper foil was then continuously peeled off in a direction 90° relative to the copper foil surface at a rate of 50 mm / min. The stress at this time was measured using a tensile tester, and the minimum stress value was recorded as the copper foil peel strength (in accordance with JIS C 6481). The copper peel strength was evaluated based on the following criteria. (Evaluation Criteria) A+: 4 N / cm or more A: 3 N / cm or more, less than 4 N / cm B: 2 N / cm or more, less than 3 N / cm C: Less than 2 N / cm The measurement results are shown in Tables 2 to 4 below.

[0204]

[0205] From the above, it was found that the composition has a low dielectric tangent and excellent flame retardancy, and satisfies a good balance of practical properties, making it an excellent substrate material.

[0206] From the above, it can be seen that the present composition containing the above-mentioned Resin A, Compound B, and Compound C has excellent electrical properties and flame retardancy. Furthermore, the present disclosure can provide electronic materials that are excellent in electrical properties, flame retardancy, etc., such as the present composition, a cured product using the present composition, a prepreg, and a metal-clad laminate.

[0207] The present disclosure is not limited to the above-described embodiment, and can be appropriately modified without departing from the spirit and scope of the present disclosure. Furthermore, the present disclosure may be implemented by appropriately combining the above-described embodiment and examples thereof.

[0208] This application claims priority based on Japanese Patent Application No. 2023-178264, filed October 16, 2023, and Japanese Patent Application No. 2024-070640, filed April 24, 2024, the disclosures of which are incorporated herein in their entireties.

Claims

1. A resin composition comprising at least a resin having an α-olefin structure represented by the following formula (1), an organic phosphorus compound, and a compound having at least one of an oxygen atom and a nitrogen atom: In formula (1), R １ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0 to 4, and * represents a bonding position.

2. The resin composition according to claim 1, wherein the resin has an iodine value of 70 or more and 200 or less.

3. The resin composition according to claim 1, wherein the weight average molecular weight Mw of the resin is 2,500 or more and 500,000 or less.

4. The resin composition according to claim 1, wherein the content of the α-olefin structure represented by formula (1) in the resin is 1.0 mmol / g or more and 6.3 mmol / g or less.

5. The resin composition according to claim 1, wherein the following parameter FA, which is represented by the content of the α-olefin structure shown in the formula (1), the content of the indane structure shown in the following formula (2), and the content of the inner olefin structure shown in the following formula (3), in the resin, is 0.39 or more: FA = [content of α-olefin structure] / ([content of inner olefin structure] + [content of indane structure] + [content of α-olefin structure]). In formula (2), R ２ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and * represents a bonding position. In formula (3), R ３ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p3 represents a real number of 0 to 4, and * represents a bonding position.

6. The resin composition according to claim 1, wherein the following parameter FI, which is represented by the content of the α-olefin structure shown in the formula (1), the content of the indane structure shown in the following formula (2), and the content of the inner olefin structure shown in the following formula (3), in the resin, is less than 0.58: FI = [content of indane structure] / ([content of inner olefin structure] + [content of indane structure] + [content of α-olefin structure] / 2). In formula (2), R ２ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and * represents a bonding position. In formula (3), R ３ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p3 represents a real number of 0 to 4, and * represents a bonding position.

7. The resin composition according to claim 1, wherein the content of heteroatoms other than carbon and hydrogen atoms in the resin is 3 mass % or less.

8. The resin composition according to claim 7, wherein the resin does not contain any heteroatoms.

9. The resin composition according to claim 1, wherein the resin has an olefin structure at a terminal thereof.

10. The resin composition according to claim 1, wherein the resin further has a side chain olefin structure having an olefin structure in the side chain portion.

11. The resin composition according to claim 1, wherein the total content of the α-olefin structure, the olefin structure at the terminal, and the side chain olefin structure having an olefin structure in the side chain portion in the resin is 1.8 mmol / g or more.

12. The resin composition according to claim 1, wherein the content of the indane structure represented by the following formula (2) in the resin is 3.0 mmol / g or less. In formula (2), R ２ each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and * represents a bonding position.

13. The resin composition according to claim 1, wherein the organophosphorus compound has a solubility of 5 g or less in 100 g of toluene at 25°C.

14. The resin composition according to claim 1, wherein the organophosphorus compound is incompatible with the resin.

15. The resin composition according to claim 1, wherein the organic phosphorus compound has a melting point of 240° C. or higher.

16. The resin composition according to claim 1, wherein the organic phosphorus compound has a phosphine oxide structure or a phosphinic acid structure.

17. The resin composition according to claim 1, wherein the compound having at least one of an oxygen atom and a nitrogen atom has a number average molecular weight Mn of 300 to 50,000.

18. The resin composition according to claim 1, wherein the compound having at least one of an oxygen atom and a nitrogen atom contains a radically polymerizable group.

19. The resin composition according to claim 1, wherein the total content of oxygen atoms and nitrogen atoms is 0.01 to 10 mass %.

20. A resin composition according to claim 1, wherein the contents of the resin in the solid content of the resin composition are 1 to 80 mass % of the resin, 0.1 to 30 mass % of the organophosphorus compound, and 1 to 80 mass % of the compound having at least one of an oxygen atom and a nitrogen atom.

21. A prepreg comprising the resin composition according to any one of claims 1 to 20.

22. A metal-clad laminate comprising a cured product of the resin composition according to any one of claims 1 to 20 and a metal foil.

23. A method for producing a metal-clad laminate, comprising laminating a prepreg containing the resin composition according to any one of claims 1 to 20 with a metal foil.

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