Polyether compound, resin composition, cured product, laminated film, copper-clad laminate, laminate, electrical / electronic component, use of resin composition as raw material for electrical / electronic component, and method for producing polyether compound

Abstract

Provided is a polyether compound having excellent solvent solubility, capable of providing a cured product having low dielectric properties in a higher frequency environment and excellent metal adhesion. The polyether compound of the present invention is represented by the following formula (1).

Description

Technical Field

[0001] This invention relates to a polyether compound, a resin composition, a cured product, a laminated film, a copper-clad laminate, a laminate, an electrical and electronic component, the use of the resin composition as a raw material for electrical and electronic components, and a method for manufacturing the polyether compound.

[0002] This application claims priority based on Japanese Patent Application No. 2024-048509, filed in Japan on March 25, 2024, the contents of which are incorporated herein by reference. Background Technology

[0003] In recent years, the use of multilayer circuit boards in electrical and electronic equipment has been driving the miniaturization, weight reduction, and high functionality of devices, requiring further multilayering, high density, thinness, lightweighting, as well as improvements in reliability and manufacturability.

[0004] The properties required for curable resins used as materials for electrical and electronic components such as laminates for electrical and electronic circuits involve many aspects, and low dielectric properties can be listed as one of the important properties.

[0005] In recent years, to improve information transmission volume and speed, communication frequencies have been increasing, and the increase in transmission loss (α) has become a major challenge. A lower value of α means less signal attenuation, ensuring higher communication reliability. One method to suppress α is to suppress dielectric loss, a key component of communication. Since dielectric loss is proportional to frequency, it increases in high-frequency communication, leading to decreased reliability. However, by reducing the dielectric loss tangent (tanδ), which is also proportional to frequency, both dielectric loss and α can be suppressed. Therefore, for high-speed communication signal transmission, materials with low dielectric loss tangent (tanδ), i.e., materials with low dielectric properties, are sought.

[0006] Another method to suppress transmission loss (α) is to suppress scattering loss. The higher the frequency, the greater the skin effect. In the roughened areas near the conductor surface, the signal is scattered and lost as heat. Therefore, reducing the roughness of the conductor surface is effective in suppressing scattering loss. On the other hand, if the conductor surface is made less rough, the adhesion to the thermosetting resin used as the material decreases, leading to a reduction in reliability. That is, in addition to low dielectric properties, the curing resin used as the material requires high adhesion to the metal used as the conductor.

[0007] Furthermore, when curing curable resin compositions on an industrial scale and applying them to electrical and electronic components, they are sometimes dissolved in solvents as varnishes to adjust the viscosity of the material. Therefore, the material needs to have excellent solvent solubility.

[0008] Patent document 1 discloses a polyether compound containing an olefinic unsaturated double bond at the end of the reaction product of a bisphenol compound and p-xylene dichloro.

[0009] Patent document 2 discloses a polyether compound that contains an olefinic unsaturated double bond at the end of the reaction product of a phenolic compound having a diphenylphosphine oxide skeleton and m-xylene dichloro.

[0010] Existing technical documents

[0011] Patent documents

[0012] Patent Document 1: International Publication No. 2014 / 156778

[0013] Patent Document 2: Japanese Patent Application Publication No. 2011-84697 Summary of the Invention

[0014] The problem that the invention aims to solve

[0015] The cured product using a curable resin composition containing the compound described in Patent Document 1 has excellent low dielectric properties at 2 GHz, but according to the research of the inventors, it has been determined that the cured product is insufficient from the viewpoint of low dielectric properties or metallic adhesion at higher frequency environments (10 GHz).

[0016] According to the research of the inventors, it has been determined that the solvent solubility of the curable resin composition containing the compound described in Patent Document 2 is insufficient.

[0017] The present invention was made in view of the above-mentioned problems, and its objective is to provide a polyether compound having excellent solvent solubility and capable of providing a cured product with low dielectric properties and excellent metal adhesion at higher frequency environments. Furthermore, the present invention aims to provide a resin composition having excellent solvent solubility and capable of providing a cured product with low dielectric properties and excellent metal adhesion at higher frequency environments, a cured product with low dielectric properties and excellent metal adhesion at higher frequency environments, a laminate containing the cured product, an electrical and electronic component containing the cured product, and an electrical and electronic component containing the laminate.

[0018] Solution for solving the problem

[0019] The inventors conducted in-depth research to solve the aforementioned problems and discovered that polyether compounds with a specific structure can solve these problems, thus completing this invention.

[0020] That is, the main idea of ​​this invention is as follows.

[0021] [1] A polyether compound represented by the following formula (1).

[0022] [Chemical Formula 1]

[0023]

[0024] In formula (1), l and n represent 0 or 1, m represents an integer from 1 to 50, Ar1 independently represents an aromatic hydrocarbon group with 6 to 100 carbon atoms that does not have the structure shown in formula (2), Ar2 represents the structure shown in formula (3) or the structure shown in formula (4) when m is 1 and n is 0, and independently represents at least one structure selected from the group consisting of the structure shown in formula (3) and the structure shown in formula (4) when m is 2 to 50 or n is 1, and Y independently represents a group containing an olefinic unsaturated double bond with 3 to 50 carbon atoms.

[0025] [Chemical Formula 2]

[0026]

[0027] In equations (2) to (4), the symbol "*" represents a bond, A1 to A 10 Each is independently selected from any one of the group consisting of hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, phenyl groups, and naphthyl groups, R 1 ~R 8 Each is independently selected from any one of the groups consisting of hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms, and alkoxy groups with 1 to 20 carbon atoms.

[0028] [2] According to the polyether compound of [1], wherein Y in the formula (1) comprises at least one group selected from the group consisting of 2-vinylbenzyl, 3-vinylbenzyl, 4-vinylbenzyl, allyl, methylallyl, cinnamyl, acryloyl, methacryloyl, 2-allylphenyl, 2-propenylphenyl, 4-vinylphenyl, 4-isopropenylphenyl, 2-methoxy-4-allylphenyl and 2-methoxy-4-propenylphenyl.

[0029] [3] According to the polyether compound of [1] or [2], wherein Ar1 in the formula (1) is at least one group selected from the group consisting of the groups shown in formulas (5) to (8).

[0030] [Chemical Formula 3]

[0031]

[0032] In equations (5) to (8), the symbol "*" represents a bond, X4 is any one of the following groups consisting of directly bonded divalent hydrocarbon groups with 1 to 20 carbon atoms, -O-, -S-, -CO-, -C(O)-O-, -C(O)-NH-, -SO-, -SO2-, -C(CF3)2-, and -P(O)-, X5 is a trivalent hydrocarbon group with 1 to 20 carbon atoms, X6 is a tetravalent hydrocarbon group with 1 to 20 carbon atoms, and R 9 ~R 50 Each of the following groups is independently selected from hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms, and alkoxy groups with 1 to 20 carbon atoms. Z represents the structure shown in the following formula (9).

[0033] [Chemical Formula 4]

[0034]

[0035] In equation (9), the symbol “*” represents a bonding bond, M represents an integer from 1 to 50, N represents 0 or 1, Ar1 and Y have the same meaning as Ar1 and Y in equation (1), Ar2 represents the structure shown in equation (3) or the structure shown in equation (4) when M is 1 and N is 0, or when M is 0 and N is 1, and when M is 2 to 50, or when M is 1 and N is 1, each independently represents at least one structure selected from the group consisting of the structure shown in equation (3) and the structure shown in equation (4).

[0036] [4] The polyether compound according to any one of [1] to [3], wherein the polyether compound has a polystyrene equivalent weight-average molecular weight of 1,000 to 100,000.

[0037] [5] A resin composition comprising a polyether compound of any one of [1] to [4] and a curable compound having a structure different from that of the polyether compound of any one of [1] to [4].

[0038] [6] According to the resin composition of [5], wherein the curable compound is the compound shown in the formula (1) when l is 1 and m and n are 0.

[0039] [7] The resin composition according to [5] or [6], wherein the resin composition further comprises a curing accelerator.

[0040] [8] A resin composition according to any one of [5] to [7], wherein the curable compound has at least one substituent selected from the group consisting of epoxy, ester, oxazinyl, cyanate ester, maleimide, acryloyl, methacryloyl, styrene, allyl, vinyl, propylene and benzoxazinyl.

[0041] [9] A resin composition according to any one of [5] to [8], wherein the resin composition further comprises an antioxidant.

[0042]

[10] A cured product, which is a cured product of a resin composition of any one of [5] to [9].

[0043]

[11] A laminated film comprising a cured product of

[10] .

[0044]

[12] A copper-clad laminate comprising a cured product of

[10] .

[0045]

[13] A laminate comprising a cured form of

[10] .

[0046]

[14] An electrical and electronic component comprising a cured form of

[10] .

[0047]

[15] An electrical and electronic component having a stack of

[13] .

[0048]

[16] Use of a resin composition as a raw material for electrical and electronic components, said resin composition being any one of [5] to [9].

[0049]

[17] A method for manufacturing a polyether compound, wherein the polyether compound is any one of [1] to [4], the method comprising a step of reacting a phenolic compound, a divalent aromatic halomethyl compound and a monovalent compound containing an olefinic unsaturated double bond in the presence of an alkaline compound.

[0050] Invention Effects

[0051] According to the present invention, polyether compounds exhibiting excellent solvent solubility, providing low dielectric properties and excellent metal adhesion in cured products at higher frequency environments, can be obtained. Additionally, resin compositions providing low dielectric properties and excellent metal adhesion in cured products at higher frequency environments, cured products exhibiting low dielectric properties and excellent metal adhesion in higher frequency environments, laminates containing the cured products, electrical and electronic components containing the cured products, and electrical and electronic components having the laminates can be obtained.

[0052] In addition, the resin composition of the present invention can be suitably used in (multilayer) printed circuit boards, laminates for electrical and electronic circuits such as capacitors, adhesives such as thin film adhesives and liquid adhesives, semiconductor sealing materials, underfill materials, inter-chip fillers for 3D-LSI, insulating sheets, prepregs, heat dissipation substrates, etc. Detailed Implementation

[0053] The embodiments of the present invention will be described in detail below. However, the following description is only one example of the embodiments of the present invention, and the present invention is not limited to the following description without departing from its spirit.

[0054] In this specification, the use of expressions such as “~” is used to indicate the numerical or physical property values ​​that come before or after it.

[0055] In this invention, for example, the statement "selected from at least one of the groups consisting of XX, YY and ZZ" means any one of XX, YY, ZZ, the combination of XX and YY, the combination of XX and ZZ, the combination of YY and ZZ, or the combination of XX, YY and ZZ.

[0056] [Polyether compounds]

[0057] The polyether compound in this embodiment is the polyether compound shown in the following formula (1) (hereinafter, sometimes referred to as "compound (1)").

[0058] [Chemical Formula 5]

[0059]

[0060] In equation (1), l and n represent 0 or 1, m represents an integer from 1 to 50, and Ar 1 Each of the following independently represents an aromatic hydrocarbon group with 6 to 100 carbon atoms that does not have the structure shown in formula (2), Ar 2 When m is 1 and n is 0, it represents the structure shown in formula (3) or the structure shown in formula (4). When m is 2 to 50 or n is 1, it independently represents at least one structure selected from the group consisting of the structure shown in formula (3) and the structure shown in formula (4). Y independently represents a group containing an olefinic unsaturated double bond with 3 to 50 carbon atoms.

[0061] [Chemical Formula 6]

[0062]

[0063] In equations (2) to (4), the symbol "*" represents a bond, A1 to A 10 Each is independently selected from any one of the group consisting of hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, phenyl groups, and naphthyl groups, R 1 ~R 8 Each is independently selected from any one of the groups consisting of hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms, and alkoxy groups with 1 to 20 carbon atoms.

[0064] The cured resin composition containing the polyether compound of this embodiment exhibits the effect of low dielectric properties and excellent metal adhesion. As a reason, it can be presumed that this is due to the presence of ortho-xylene and / or meta-xylene sites with small dipole moments and moderate flexibility in formula (1), that is, the two oxymethylene (-CH2-O-) chains in Ar2 are in ortho and / or meta positions relative to the bonding positions of the benzene ring.

[0065] In the polyether compound of this embodiment, from the viewpoint of obtaining a cured product that can better exhibit the above-mentioned effects, Ar2 is particularly preferred to have the structure shown in the above formula (3), that is, the structure in which the two oxymethylene chains in Ar2 are in a meta-position relative to the bonding position of the benzene ring.

[0066] As R 1 ~R 8 Hydrocarbon groups with 1 to 20 carbon atoms include, for example, monovalent chain aliphatic hydrocarbon groups, monovalent cyclic aliphatic hydrocarbon groups, and monovalent aromatic hydrocarbon groups.

[0067] Examples of monovalent chain aliphatic hydrocarbon groups include: alkyl groups (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, n-hexyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc.), alkenyl groups (e.g., vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, cyclohexenyl, cyclohexadienyl, cinnamyl, naphthylvinyl, etc.), and alkynyl groups (e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1,3-butadienyl, phenylethynyl, naphthylethynyl, etc.).

[0068] Examples of monovalent cyclic aliphatic hydrocarbon groups include: cyclohexyl, cycloheptyl, methylcyclohexyl, cyclooctyl, 3,3,5-trimethylcyclohexyl, cyclodecyl, cyclododecyl, norbornyl, adamantyl, and norbornyl.

[0069] Examples of monovalent aromatic hydrocarbon groups include: phenyl, o-tolyl, m-tolyl, p-tolyl, ethylphenyl, styryl, xylyl, n-propylphenyl, isopropylphenyl, mesitylene, ethynylphenyl, naphthyl, vinylnaphthyl, benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, naphthylmethyl, phenethyl, and 2-phenylisopropyl.

[0070] As R 1 ~R 8Alkoxy groups, for example, include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy, tert-pentoxy, cyclopentoxy, n-hexoxy, isohexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, methylcyclohexoxy, n-octoxy, cyclooctoxy, n-nonoxy, 3,3,5-trimethylcyclohexoxy, n-decoxy, cyclodecoxy, n-undecoxy, n-dodecoxy, cyclododecoxy, benzyloxy, methylbenzyloxy, dimethylbenzyloxy, trimethylbenzyloxy, naphthylmethoxy, phenylethoxy, and 2-phenylisopropoxy.

[0071] Based on the reasons of readily available raw materials and industrial advantages, R 1 ~R 8 Preferably, each is independently composed of any one of the groups consisting of hydrogen atoms and hydrocarbon groups having 1 to 12 carbon atoms; more preferably, each is independently composed of any one of the groups consisting ...

[0072] In formula (1), the aromatic hydrocarbon group in Ar1 is preferably at least one group selected from the group consisting of the groups shown in formulas (5) to (8). In particular, from the viewpoint of obtaining a cured product that can better exhibit excellent metal adhesion, Ar1 is more preferably the structure shown in formula (5) or formula (6), and from the viewpoint of obtaining a cured product that can better exhibit effects such as low dielectric properties and excellent metal adhesion, Ar1 is particularly preferably the structure shown in formula (5).

[0073] Therefore, in the polyether compounds of the present invention having the structure shown in formula (1), Ar1 is particularly preferred to have the structure shown in formula (5), and Ar2 is preferred to have the structure shown in formula (3).

[0074] [Chemical Formula 7]

[0075]

[0076] In equations (5) to (8), the symbol "*" represents a bond, X4 is any one of the following groups consisting of directly bonded divalent hydrocarbon groups with 1 to 20 carbon atoms, -O-, -S-, -CO-, -C(O)-O-, -C(O)-NH-, -SO-, -SO2-, -C(CF3)2-, and -P(O)-, X5 is a trivalent hydrocarbon group with 1 to 20 carbon atoms, X6 is a tetravalent hydrocarbon group with 1 to 20 carbon atoms, and R 9 ~R 50Each of the following groups is independently selected from hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms, and alkoxy groups with 1 to 20 carbon atoms. Z represents the structure shown in the following formula (9).

[0077] [Chemical Formula 8]

[0078]

[0079] In equation (9), the symbol “*” represents a bonding bond, M represents an integer from 1 to 50, N represents 0 or 1, Ar1 and Y have the same meaning as Ar1 and Y in equation (1), Ar2 represents the structure shown in equation (3) or the structure shown in equation (4) when M is 1 and N is 0, or when M is 0 and N is 1, and when M is 2 to 50, or when M is 1 and N is 1, each independently represents at least one structure selected from the group consisting of the structure shown in equation (3) and the structure shown in equation (4).

[0080] In equation (5), R 9 ~R 16 R in equations (3) and (4) respectively 1 ~R 8 The meaning is the same. From the viewpoints of readily available raw materials, industrial advantages, and obtaining cured products that can better exhibit low dielectric properties and excellent metallic adhesion, it is preferable that each component is independently composed of any one of the group consisting of hydrogen atoms and hydrocarbon groups having 1 to 12 carbon atoms; more preferably, it is preferable that each component is independently composed of any one of the group consisting of hydrogen atoms and aliphatic hydrocarbon groups having 1 to 12 carbon atoms; even more preferably, it is preferable that each component is independently composed of any one of the group consisting of hydrogen atoms and aliphatic hydrocarbon groups having 1 to 6 carbon atoms; and particularly preferably, R... 9 ~R 16 At least two of the groups are aliphatic hydrocarbon groups with 1 to 6 carbon atoms.

[0081] In equations (6) to (8), R 17 ~R 50 R in equations (3) and (4) respectively 1 ~R 8 The meanings are the same. It should be noted that the same applies to their respective preferred ranges.

[0082] In formula (5), divalent hydrocarbon groups with 1 to 20 carbon atoms can be listed as divalent chain aliphatic hydrocarbon groups, divalent cyclic aliphatic hydrocarbon groups, and divalent cyclic aromatic hydrocarbon groups.

[0083] Examples of divalent chain aliphatic hydrocarbon groups include: methylene, 1,1-ethylene, isopropylidene, 1,2-ethylene, 1,3-propylene, 1,1-butylene, 1,4-butylene, and 1,3-dimethylbutylidene.

[0084] Examples of divalent cyclic aliphatic hydrocarbon groups include: 1,1-cyclopentylene, 1,1-cyclohexylene, 3-methyl-1,1-cyclohexylene, 3,3,5-trimethyl-1,1-cyclohexylene, 1,1-cyclododecylene, 1,2-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclopentylene, 1,3-cyclohexylene, and 1,4-cyclohexylene.

[0085] Examples of divalent cyclic aromatic hydrocarbon groups include: -CH(Ph)-, -C(CH3)(Ph)-, -C(Ph)2-, 9,9-fluoreneyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,3-phenylene diisopropylidene, 1,4-phenylene diisopropylidene, and groups represented by formula (10) below. In formula (10), the symbol "*" represents a bonded bond. The "Ph" above represents phenyl.

[0086] [Chemical Formula 9]

[0087]

[0088] From the viewpoint of low dielectric properties and heat resistance when the product is cured, X4 is preferably any one selected from the group consisting of directly bonded, -O-, and divalent hydrocarbon groups having 1 to 13 carbon atoms. More preferably, it is any one selected from the group consisting of methylene, 1,1-ethylene, isopropylidene, 1,1-butylene, 1,3-dimethylbutylidene, 9,9-fluorene, 1,1-cyclohexylene, 3,3,5-trimethyl-1,1-cyclohexylene, 1,1-cyclododecylene, and 1,3-phenylene diisopropylidene. Particularly preferably, it is any one selected from the group consisting of methylene, isopropylidene, 1,1-butylene, 9,9-fluorene, and 1,3-phenylene diisopropylidene.

[0089] Then, from the viewpoint of obtaining a cured product that can better exhibit effects such as low dielectric properties and excellent metallic adhesion, Ar is preferred in compound (1). 1 The structure is shown in formula (5), and X4 in formula (5) is a structure selected from any group in the group consisting of isopropylidene, 1,1-butylene and 9,9-fluorene.

[0090] Therefore, in compound (1), Ar is particularly preferred. 1X4 is a group represented by formula (5), where X4 is any group selected from the group consisting of isopropylidene, 1,1-butylene, and 9,9-fluorene, and Ar 2 The structure is shown in equation (3).

[0091] As trivalent hydrocarbon groups with 1 to 20 carbon atoms in X5, the structures shown in formulas (11) to (16) below can be listed for example. The symbol "*" represents a bond.

[0092] [Chemical Formula 10]

[0093]

[0094] As a tetravalent hydrocarbon group with 1 to 20 carbon atoms in X6, the structure shown in the following formula (17) can be listed as an example.

[0095] [Chemical Formula 11]

[0096]

[0097] In equation (9), Ar1, Ar2, and Y have the same meanings as Ar1, Ar2, and Y in equation (1). It should be noted that the preferred cases for Ar1, Ar2, and Y are also the same.

[0098] In formula (1), l and n represent 0 or 1. From the viewpoint of obtaining a cured product that can better exhibit low dielectric properties and excellent metal adhesion, l is preferably 1 and n is 0. m represents an integer from 1 to 50. From the viewpoint of solvent solubility, m is preferably 1 to 30, and more preferably 1 to 10.

[0099] In formula (9), N represents 0 or 1, and from the viewpoint of obtaining a cured product that can better exhibit low dielectric properties and excellent metal adhesion, it is preferably 0. M represents an integer from 1 to 50, and from the viewpoint of solvent solubility, it is preferably 1 to 30, and more preferably 1 to 10.

[0100] In formula (1), the group containing an olefinic unsaturated double bond with 3 to 50 carbon atoms represented by Y can be exemplified by, for example, 2-vinylbenzyl, 3-vinylbenzyl, 4-vinylbenzyl, allyl, methylallyl, cinnamyl, acryloyl, methacryloyl, 2-allylphenyl, 2-propenylphenyl, 4-vinylphenyl, 4-isopropenylphenyl, 2-methoxy-4-allylphenyl, and 2-methoxy-4-propenylphenyl. Preferably, it includes at least one group selected from the group consisting of 2-vinylbenzyl, 3-vinylbenzyl, 4-vinylbenzyl, allyl, methylallyl, cinnamyl, acryloyl, and methacryloyl. Among these, based on the reasons that raw materials are readily available and industrially advantageous, Y is preferably selected independently from any group selected from the group consisting of 3-vinylbenzyl, 4-vinylbenzyl, allyl, cinnamyl, acryloyl and methacryloyl, more preferably from any group selected from the group consisting of 3-vinylbenzyl, 4-vinylbenzyl, allyl and methacryloyl, and even more preferably from any group selected from the group consisting of 3-vinylbenzyl, 4-vinylbenzyl and methacryloyl.

[0101] <Method for manufacturing compound (1)>

[0102] There are no particular restrictions on the method of manufacturing compound (1). For example, it can be manufactured by a method having the following steps: using any phenolic compound, a divalent aromatic halomethyl compound, and a monovalent compound containing an olefinic unsaturated double bond as raw materials, and reacting them in an organic solvent in the presence of a basic compound. The monovalent compound containing an olefinic unsaturated double bond can be reacted after polymerizing any phenolic compound with a divalent aromatic halomethyl compound.

[0103] The phenolic compound used as a raw material is not particularly limited as long as it has two or more aromatic rings, but is preferably a phenolic compound having at least one structure selected from the group consisting of the structures shown in formulas (18) to (21).

[0104] [Chemical Formula 12]

[0105]

[0106] In equations (18) to (21), X4 to X6, R 9 ~R 50 respectively with X4~X6, R in equations (5)~(8) 9 ~R 50 The meanings are the same. It should be noted that for X4~X6, R... 9 ~R 50 The same applies to their respective preferred scenarios.

[0107] Phenolic compounds can be used alone or in combination with two or more.

[0108] As a divalent aromatic halomethyl compound that can be used as a raw material, as long as Ar can be introduced into compound (1) 2 The compound having the structure is not particularly limited, but is preferably selected from at least one compound of the group consisting of the compound shown in formula (22) and the compound shown in formula (23).

[0109] [Chemical Formula 13]

[0110]

[0111] In equations (22) and (23), R 1 ~R 8 R in equations (3) and (4) respectively 1 ~R 8 The meanings are the same. It should be noted that for R... 1 ~R 8 The preferred options are also the same. In addition, in the above formulas (22) and (23), Z independently represents a halogen atom. Based on the reasons that raw materials are readily available and industrially advantageous, chlorine or bromine atoms are preferred.

[0112] From the viewpoint of solvent solubility of the manufactured compound, the amount of divalent aromatic halomethyl compound can be 0.5 to 4.0 times molar, preferably 0.7 to 3.0 times molar, relative to 1 mole of hydroxyl group of the raw phenolic compound.

[0113] Divalent aromatic halomethyl compounds can be used alone or in combination with two or more.

[0114] Examples of monovalent compounds containing olefinic unsaturated double bonds that can be used as raw materials include halogenated compounds containing olefinic unsaturated double bonds and phenolic compounds containing olefinic unsaturated double bonds.

[0115] As halogenated compounds containing olefinic unsaturated double bonds, there are no particular limitations. Based on the reasons that raw materials are readily available and industrially advantageous, the following are preferred: 2-(chloromethyl)styrene, 3-(chloromethyl)styrene, 4-(chloromethyl)styrene, allyl chloride, allyl bromide, 2-methylallyl chloride, cinnamyl chloride, cinnamyl bromide, acryloyl chloride, and methacryloyl chloride.

[0116] As phenolic compounds containing olefinic unsaturated double bonds, there are no particular limitations. Based on the reasons that raw materials are readily available and industrially advantageous, the following are preferred: 2-allylphenol, 2-propenylphenol, 4-vinylphenol, 4-isopropenylphenol, 2-methoxy-4-allylphenol, and 2-methoxy-4-propenylphenol.

[0117] From the viewpoint of suppressing production costs while carrying out the reaction efficiently, the amount of a monovalent phenolic compound containing an olefinic unsaturated double bond can be 0.05 to 1.0 times molar, preferably 0.1 to 0.8 times molar, relative to 1 mole of the hydroxyl group of the phenolic compound used as a raw material.

[0118] From the viewpoint of suppressing production costs while carrying out the reaction efficiently, the amount of monovalent alkyl halogenated compound containing alkene unsaturated double bonds can be 0.05 to 1.0 times the molar amount, preferably 0.1 to 0.8 times the molar amount, relative to 1 molar amount of halogen atoms in divalent aromatic alkyl halogenated compound that becomes a raw material.

[0119] This reaction is preferably carried out in the presence of a basic compound. Examples of basic compounds include: alkali metal hydroxides and salts such as sodium hydroxide, potassium hydroxide, and potassium carbonate; amines such as diazabicyclononene, diazabicycloundecene, and triethylamine; sodium tert-butoxide, potassium tert-butoxide, lithium diisopropylamino, silicon-basic amines, and lithium tetramethylpiperidine.

[0120] In terms of being relatively inexpensive and less prone to side reactions, alkali metals, diazabicycloundecene, and potassium tert-butoxide are preferred, with sodium hydroxide, potassium hydroxide, and potassium carbonate being particularly preferred.

[0121] These basic compounds can be used alone or in combination of two or more. Furthermore, these basic compounds can be used in the form of aqueous or alcoholic solutions.

[0122] From the viewpoint that it can accelerate the reaction rate and eliminate the need to remove the residual alkali, thereby increasing productivity, the amount of basic compound used is preferably 0.7 to 3.0 times the molar amount of hydroxyl group of the raw phenolic compound, more preferably 0.8 to 2 times the molar amount of hydroxyl group of phenolic compound.

[0123] This reaction is preferably carried out in the presence of an organic solvent, such as a polar solvent.

[0124] Examples of polar solvents include: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, N,N-dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol, butanol, ethyl acetate, butyl acetate, methyl cellosolve, diethylene glycol ethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran.

[0125] In terms of relatively low cost and good reactivity, acetone, N,N-dimethylformamide, N-methyl-2-pyrrolidone, and diethylene glycol dimethyl ether are preferred.

[0126] As an organic solvent, it can be used alone or in combination with two or more. Additionally, it can be used with low-polarity solvents such as toluene and xylene. Furthermore, the reaction can also be carried out in the presence of water.

[0127] In this reaction, a phase transfer catalyst can coexist to promote the reaction.

[0128] Quaternary ammonium salts can be cited as examples of phase transfer catalysts.

[0129] Examples of quaternary ammonium salts include: tetramethylammonium, trimethylethylammonium, dimethyldiethylammonium, triethylmethylammonium, tripropylmethylammonium, tributylmethylammonium, trioctylmethylammonium, tetraethylammonium, trimethylpropylammonium, trimethylphenylammonium, benzyltrimethylammonium, benzyltriethylammonium, diallyldimethylammonium, n-octyltrimethylammonium, stearyltrimethylammonium, cetyldimethylethylammonium, tetrapropylammonium, tetra-n-butylammonium, bromide, chloride, iodide, hydrogen sulfate, and hydroxide of β-methylcholine and phenyltrimethylammonium.

[0130] In terms of being relatively inexpensive and having good reactivity, tetra-n-butylammonium salt is preferred.

[0131] More specifically, regarding this reaction, the phenolic compound is dissolved in an organic solvent along with a divalent aromatic halomethyl compound and a basic compound, and the reaction is carried out for 0.5 to 20 hours. Then, a monovalent compound containing an olefinic unsaturated double bond is added, and the reaction is carried out for another 0.5 to 20 hours. The reaction temperature is not particularly limited as long as it is the temperature at which the phenolic compound reacts with the divalent aromatic halomethyl compound and the monovalent compound containing the olefinic unsaturated double bond; preferably, it is 10 to 150°C, more preferably 40 to 130°C.

[0132] After the reaction, inorganic components are removed by methods such as washing with water and filtration. Unreacted raw materials are then removed, concentrated, and purified (recrystallized, reprecipitated, washed, column chromatography, etc.) through distillation or other processes to obtain the polyether compound of this embodiment. The number of water washes is not particularly limited, but is preferably 1 to 6 times, more preferably 1 to 4 times.

[0133] <Properties of Polyether Compounds>

[0134] The polyether compound of this embodiment has a polystyrene-converted weight-average molecular weight (Mw) preferably of 1,000 to 100,000, more preferably of 1,500 to 50,000, and even more preferably of 2,000 to 30,000.

[0135] The number-average molecular weight (Mn) of the polystyrene-based polyether compound used in this embodiment is preferably 500 to 50,000, more preferably 750 to 10,000, and even more preferably 1,000 to 5,000.

[0136] By setting Mw and Mn to values ​​above the lower limit mentioned above, a cured product with superior low dielectric properties and metal adhesion can be obtained, which is therefore preferred. By setting Mw and Mn to values ​​below the upper limit mentioned above, the solubility in solvents is improved, and a polyether compound with better workability can be obtained, which is also preferred.

[0137] In this invention, Mw and Mn are values ​​determined by gel permeation chromatography (GPC) under the conditions described in the following examples.

[0138] [Resin Composition]

[0139] One embodiment of the resin composition is that it contains at least the polyether compound of this embodiment.

[0140] The polyether compound contained in the resin composition of this embodiment may be used alone or in combination with two or more.

[0141] Another preferred embodiment of the resin composition of this embodiment also preferably contains a curing compound (hereinafter also referred to as "curing compound (2)") with a structure different from that of the polyether compound of this embodiment. It may also contain a curing accelerator.

[0142] The resin composition of this embodiment may be based on the polyether compound and curing compound (2) of this embodiment, or on the polyether compound, curing compound (2) and curing accelerator of this embodiment, and may also contain other components.

[0143] <Cureable Compounds (2)>

[0144] As a curable compound (2), there are no particular limitations. It can be a compound that is cured by irradiation of heat or light (visible light, ultraviolet light, infrared light, etc.) or a compound that requires a curing accelerator as described later during curing.

[0145] As a curable compound (2), for example, it is preferred to use a compound represented by l being 1 and m and n being 0 in formula (1) (hereinafter also referred to as "compound (3)"); or a compound having at least one substituent selected from the group consisting of epoxy, ester, oxazinyl, cyanate ester, maleimide, acryloyl, methacryloyl, styryl, allyl, vinyl, propenyl and benzoxazinyl.

[0146] As a curable compound (2), it may be, for example, at least one compound selected from the group consisting of compound (3), maleimide compound, styrene compound, acrylic compound, methacrylic compound, vinyl compound, allyl compound, propylene compound, cyanate compound, oxazine compound, benzocyclobutene compound, epoxy compound, phenolic compound, amine compound, acid anhydride compound and active ester compound.

[0147] Based on the balance of dielectric properties, curability, and other physical properties, it is preferred to select at least one compound from the group consisting of compound (3), maleimide compound, styrene compound, acrylic compound, methacrylic compound, vinyl compound and allyl compound.

[0148] Curable compound (2) can be used alone or in combination with two or more.

[0149] In the resin composition of this embodiment, the content ratio of the curable compound (2) relative to 100 parts by weight of compound (1) is preferably 0.01 to 10,000 parts by weight, more preferably 0.05 to 5,000 parts by weight, and even more preferably 0.1 to 1,000 parts by weight. By making the content ratio of the curable compound (2) in the resin composition at or above the above-mentioned lower limit, it is easier to obtain a cured product with excellent dielectric properties. In addition, by making the content ratio of the curable compound (2) in the resin composition at or below the above-mentioned upper limit, it is easier to obtain a resin composition with uniformity and excellent curability.

[0150] <Compound (3)>

[0151] Compound (3) is the compound shown in the following formula (24a).

[0152] [Chemical Formula 14]

[0153]

[0154] In equation (24a), Ar 1 And Y are respectively related to Ar in equation (1) 1 The meaning is the same as Y. It should be noted that for Ar... 1 The optimal choices for Y and Y are the same.

[0155] In the resin composition of this embodiment, the content ratio of compound (3) relative to 100 parts by weight of compound (1) is preferably 0.01 to 50 parts by weight, more preferably 0.05 to 30 parts by weight, and even more preferably 0.1 to 20 parts by weight. By making the content ratio of compound (3) in the resin composition at or above the above-mentioned lower limit, a cured product that can better exhibit excellent metal adhesion and other effects can be obtained. In addition, by making the content ratio of curable compound (2) in the resin composition at or below the above-mentioned upper limit, a cured product with excellent heat resistance can be obtained.

[0156] <Maleimide compounds>

[0157] Maleimide compounds are compounds having at least one maleimide group in their molecule. Preferably, each maleimide compound has one or more maleimide groups, and more preferably has two or more maleimide groups.

[0158] You can use only one of these, or you can use two or more together.

[0159] Examples of maleimide compounds include, for example, compounds shown in: "BMI-1100" (Formula 24-1 below), "BMI-2300" (Formula 24-2 below), "BMI-TMH" (Formula 24-3 below) manufactured by Yamato Chemical Industries Co., Ltd.; "BMI-70" (Formula 24-4 below), "BMI-80" (Formula 24-5 below) manufactured by K・I CHEMICAL INDUSTRY CO., LTD.; "MIR-3000" (Formula 24-6 below), "MIR-5000" (Formula 24-7 below) manufactured by Nippon Kayaku Co., Ltd.; and "BMI-689" (Formula 24-8 below), "BMI-1500" (Formula 24-9 below), "BMI-1700" (Formula 24-10 below), "BMI-3000", "BMI-5000" (Formula 24-11 below), and (Formula 24-12 below) manufactured by Designer Molecules Co., Ltd.

[0160] [Chemical Formula 15]

[0161]

[0162] [Chemical Formula 16]

[0163]

[0164] [Chemical Formula 17]

[0165]

[0166] In equations (24-2), (24-6), (24-9), (24-10), (24-11), and (24-12), n is an integer from 1 to 50.

[0167] <Styrene-based compounds>

[0168] A styryl compound is a compound having at least one styryl group in its molecule. Preferably, each styryl compound has one or more styryl groups, and more preferably has two or more styryl groups.

[0169] You can use only one of these, or you can use two or more together.

[0170] There are no particular limitations on what constitutes a styrene-based compound; for example, condensates of phenolic compounds and chloromethylstyrene described later can be cited.

[0171] Examples of styrene-based compounds include, for instance, the compounds shown in formulas (25-2) to (25-4) of "OPE-2st" manufactured by Mitsubishi Gas Chemical Co., Ltd.

[0172] [Chemical Formula 18]

[0173]

[0174] In equations (25-1) and (25-4) above, n is an integer from 0 to 300. In equation (25-3) above, n is an integer from 0 to 10.

[0175] <Acrylic compounds and methacrylic compounds>

[0176] Acrylic acid compounds and methacrylic acid compounds refer to compounds containing acryloyl and methacryloyl groups. Preferably, each molecule of acrylic acid compounds and methacrylic acid compounds has one or more acryloyl and methacryloyl groups, more preferably two or more acryloyl and methacryloyl groups.

[0177] You can use only one of these, or you can use two or more together.

[0178] Examples of acrylic and methacrylic acid compounds include: SA9000 (Formula 26-1 below) manufactured by SABIC Corporation; NK Ester DCP (Formula 26-2 below) manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; DCP-A manufactured by Kyoeisha Chemical Co., Ltd.; and Nippon Kayaku Co., Ltd., including NPDGA, FM-400, R-687, THE-330, PET-30, and DPHA.

[0179] [Chemical Formula 19]

[0180]

[0181] In the above formula (26-1), n ​​is an integer from 0 to 300.

[0182] Vinyl compounds

[0183] A vinyl compound is a compound containing vinyl groups. Preferably, each molecule of a vinyl compound has one or more vinyl groups, more preferably two or more vinyl groups.

[0184] You can use only one of these, or you can use two or more together.

[0185] Examples of vinyl compounds include: “Ricon100”, “Ricon181”, and “Ricon184” (Formula 27-1 below) manufactured by CRAYVALLEY Co., Ltd., and “B-1000” (Formula 27-2 below) and “JP-100” (Formula 27-3 below) manufactured by Nippon Soda Co., Ltd.

[0186] [Chemical Formula 20]

[0187]

[0188] In the above equations (27-1) to (27-3), l, m, and n are each an integer from 0 to 5000.

[0189] <Allyl compounds>

[0190] Allyl compounds are compounds containing an allyl group (CH2=CH-CH2-). Preferably, each molecule of an allyl compound has one or more allyl groups, more preferably two or more allyl groups.

[0191] You can use only one of these, or you can use two or more together.

[0192] Examples of allyl compounds include: "DABPA" (Formula 28-1 below) manufactured by Daiwa Chemical Co., Ltd.; "MEH-8000H" and "MEH-8005" manufactured by Meiwa Chemical Co., Ltd.; "SBA", "APG", "LVA", and "FATC" and other allylphenol compounds manufactured by Gunei Chemical Industry Co., Ltd.; "TAIC" (Formula 28-2 below) manufactured by Mitsubishi Chemical Co., Ltd.; "L-DAIC", "DD-1", "TA-G", and "P-DAIC" and other allyl compounds containing isocyanurate rings manufactured by Shikoku Chemical Industry Co., Ltd.; "DAD" (Formula 28-3 below) and other allyl ester compounds manufactured by Nisshoku Techno Fine Chemical Co., Ltd.; "FTC-AE" and other allyl ether compounds manufactured by Gunei Chemical Industry Co., Ltd.; and "BANI-M" (Formula 28-4 below) and "BANI-X" (Formula 28-5 below) and other dielyl nadicimide compounds manufactured by Maruzen Petrochemical Co., Ltd.

[0193] [Chemical Formula 21]

[0194]

[0195] <Propylene-based compounds>

[0196] A propenyl compound is a compound containing a propenyl group. Preferably, each molecule of a propenyl compound has one or more propenyl groups, and more preferably, it has two or more propenyl groups.

[0197] You can use only one of these, or you can use two or more together.

[0198] Examples of propylene-based compounds include, for example, “BPN” manufactured by Chung-Yong Chemical Co., Ltd., and “Compimide™ 123” manufactured by Evonik Co., Ltd. (Formula 29 below).

[0199] [Chemical Formula 22]

[0200]

[0201] <Benzocyclobutene compounds>

[0202] Examples of benzocyclobutene compounds include, for instance, "CYCLOTENE" (Formula 30 below) manufactured by Dow Chemical Company.

[0203] [Chemical Formula 23]

[0204]

[0205] <Oxazine compounds>

[0206] Examples of oxazine compounds include: "Pd" (Formula 31-1 below), "ALP-d" (Formula 31-2 below), and "Fa" (Formula 31-3 below) manufactured by Shikoku Chemical Co., Ltd.; and "BTBz" (Formula 31-4 below) manufactured by Nippon Materials Technology Co., Ltd.

[0207] You can use only one of these, or you can use two or more together.

[0208] [Chemical Formula 24]

[0209]

[0210] [Chemical Formula 25]

[0211]

[0212] <Cyanate compounds>

[0213] Examples of cyanate ester compounds include those shown in formulas (32-1) to (32-7).

[0214] You can use only one of these, or you can use two or more together.

[0215] [Chemical Formula 26]

[0216]

[0217] [Chemical Formula 27]

[0218]

[0219] In equations (32-5) to (32-7), n independently represents an integer from 1 to 50.

[0220] <Epoxy Compounds>

[0221] Examples of epoxy compounds include: bisphenol A type epoxy resin, bisphenol C type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, phenolic varnish type epoxy resin, tert-butylcatechol type epoxy resin, naphthol type epoxy resin, naphthalene type epoxy resin, naphthylene ether type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, cresolic varnish type epoxy resin, biphenyl type epoxy resin, anthracene type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spirocyclic epoxy resin, cyclohexanediol type epoxy resin, tris(hydroxymethyl) type epoxy resin, and halogenated epoxy resin. Epoxy resins may contain high molecular weight epoxy resins or phenoxy resins.

[0222] You can use only one of these, or you can use two or more together.

[0223] <Phenolic compounds>

[0224] Examples of phenolic compounds include: bisphenols, biphenyls, hydroquinones, dihydroxynaphthalenes, phenol-formaldehyde varnish resins, cresol-formaldehyde varnish resins, phenol-aralkyl resins, biphenyl-aralkyl resins, naphthol-aralkyl resins, terpene phenol resins, dicyclopentadienol resins, bisphenol A phenol-formaldehyde varnish resins, triphenol-methane type resins, naphthol-formaldehyde varnish resins, and various other polyphenols; polyphenolic resins obtained through the condensation reaction of various phenols and aldehydes; and polyphenolic resins obtained through the condensation reaction of xylene resin and phenol.

[0225] You can use only one of these, or you can use two or more together.

[0226] <Amine compounds>

[0227] Examples of amine compounds include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines. Only one type of these may be used, or two or more may be used in combination.

[0228] <Acid anhydride compounds>

[0229] Examples of acid anhydride compounds include, for example, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, and hexahydrophthalic anhydride.

[0230] You can use only one of these, or you can use two or more together.

[0231] <Active Ester Compounds>

[0232] There are no particular limitations on the reactive ester compounds used, but compounds with two or more highly reactive ester groups in one molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, and heterocyclic hydroxyl compounds, are generally preferred. Reactive ester resins are preferably obtained through the condensation reaction of carboxylic acid compounds and / or thiocarboxylic acid compounds with hydroxyl compounds and / or thiols. Particularly from the viewpoint of improving heat resistance, reactive ester resins obtained from carboxylic acid compounds and hydroxyl compounds are preferred, and reactive ester resins obtained from carboxylic acid compounds and phenolic compounds and / or naphthol compounds are more preferred.

[0233] You can use only one of these, or you can use two or more together.

[0234] Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.

[0235] Examples of phenolic or naphthol compounds include: hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyroglucinol, dicyclopentadiene-type diphenol compounds, and phenolic varnishes. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by the condensation of one molecule of dicyclopentadiene with two molecules of phenol.

[0236] Specifically, preferred active ester resins include those containing a dicyclopentadiene-type diphenol structure, those containing a naphthalene structure, those containing an acetylated form of phenolic varnish, and those containing a benzoylated form of phenolic varnish. More preferred are active ester resins containing a naphthalene structure and active ester resins containing a dicyclopentadiene-type diphenol structure. Here, "dicyclopentadiene-type diphenol structure" refers to a divalent structural unit composed of phenylene-dicyclopentene-phenylene.

[0237] <Other Ingredients>

[0238] In the resin composition of this embodiment, for the purpose of further improving its functionality, it may contain components other than those listed above (sometimes referred to as "other components" in this invention).

[0239] Other components include, for example: elastomers, curing accelerators, antioxidants, polymerization inhibitors, inorganic fillers, organic fillers, UV stabilizers, coupling agents, plasticizers, fluxes, flame retardants, colorants, dispersants, emulsifiers, low-elasticity agents, diluents, defoamers, and ion traps.

[0240] <Elastomers>

[0241] The resin composition of this embodiment may contain an elastomer in order to achieve low dielectric properties and further improvement in metal adhesion as a cured product.

[0242] Examples of elastomers include: styrene-based elastomers, olefin-based elastomers, urethane-based elastomers, polyester-based elastomers, polyamide-based elastomers, acrylic-based elastomers, and silicone-based elastomers.

[0243] These elastomers are composed of hard segment components and soft segment components. Generally, the hard segment components contribute to heat resistance and strength, while the soft segment components contribute to flexibility and toughness.

[0244] Elastomers can be used alone or in combination with two or more.

[0245] From the viewpoint of dielectric loss tangent (tanδ), styrene-based elastomers are preferred as elastomers, and styrene-based thermoplastic elastomers are more preferred. As a styrene-based elastomer, it is acceptable as long as it has a structural unit derived from a styrene-based compound. From the viewpoint of dielectric loss tangent (tanδ), metal adhesion, heat resistance, and low thermal expansion, it is preferred to be one or more selected from the group consisting of styrene-butadiene-styrene block copolymers (SEBS, SBBS), styrene-isoprene-styrene block copolymers (SEPS), and styrene-maleic anhydride copolymers (SMA). More preferably, it is one or more selected from the group consisting of SEBS and SEPS, and even more preferably, it is SEBS.

[0246] Elastomers can be used in combination with one type or two or more types.

[0247] <Curing Accelerator>

[0248] The resin composition of this embodiment preferably contains a curing accelerator. By including a curing accelerator, the curing time can be shortened, the curing temperature can be lowered, and the desired cured product can be easily obtained.

[0249] There are no particular limitations on what can be used as a curing accelerator. Examples include: thermal free radical curing accelerators or photofree radical curing accelerators, cationic curing accelerators, anionic curing accelerators, and transition metal compounds.

[0250] Examples of thermal free radical curing accelerators include: dicumyl peroxide, di(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyn-3, di-tert-pentyl peroxide, di-tert-hexyl peroxide, benzoyl peroxide, and other organic peroxides; azobisisobutyronitrile, 1,1'-azobis(1-acetoxy-1-phenylethane), 2,2'-azobis(2,4-dimethylpentanonitrile), 1,1'-azobis(cyclohexane-1-formonitrile), dimethyl-2,2'-azobis(isobutyrate), 2,2'-azobis(2-methylbutyronitrile), and other azo compounds.

[0251] Examples of cationic curing accelerators include: diallyl iodonium salts, trialkyl phosphonium salts, phosphonium salts such as butyltriphenylthiocyanate, and boron trifluoride, which use BF4, PF6, and SbF6 as counterions for anions.

[0252] Examples of anionic curing accelerators include: 2-ethyl-4-methylimidazolium, 2-methylimidazolium, 2-ethylimidazolium, 2,4-dimethylimidazolium, 2-undecylimidazolium, 2-heptadecanylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 1-vinyl-2-methylimidazolium, 1-propyl-2- Imidazole compounds such as methylimidazole, 2-isopropylimidazole, 1-cyanomethyl-2-methyl-imidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, and 1-cyanoethyl-2-phenylimidazole; amine compounds such as 1,8-diaza-bicyclo(5,4,0)undecene-7 and 4-dimethylaminopyridine; phosphine compounds such as triphenylphosphine; and quaternary phosphine salts such as triphenylbenzylphosphine, triphenylethylphosphine, and tetrabutylphosphine.

[0253] Transition metal compounds include, for example, zinc compounds such as tin octoate, zinc carboxylate (zinc 2-ethylhexanoate, zinc stearate, zinc benzylate, zinc myristate), zinc phosphate (zinc octyl phosphate, zinc stearyl phosphate, etc.) and other zinc compounds (transition metal salts).

[0254] As a curing accelerator, thermal free radical curing accelerators and anionic curing accelerators are preferred, and thermal free radical curing accelerators are more preferred.

[0255] A curing accelerator can be used alone or in combination with two or more.

[0256] The curing accelerator is preferably 0.0001 parts by weight or more, more preferably 0.001 parts by weight or more, and even more preferably 0.005 parts by weight or more, relative to 100 parts by weight of the resin composition. On the other hand, it is preferably 20 parts by weight or less, more preferably 10 parts by weight or less, and even more preferably 5 parts by weight or less. The above-mentioned upper and lower limits can be combined arbitrarily. For example, it can be 0.0001 parts by weight or more and 20 parts by weight or less, or 0.001 parts by weight or more and 10 parts by weight or less, or 0.005 parts by weight or more and 5 parts by weight or less. If the content of the curing accelerator is above or below the above-mentioned lower limit, a good curing promotion effect can be obtained. On the other hand, if it is below the above-mentioned upper limit, the desired cured properties are easily obtained, which is preferred.

[0257] Solvent

[0258] In the resin composition of this embodiment, any solvent can be added for dilution in order to moderately adjust the viscosity.

[0259] In the resin composition of this embodiment, the solvent is used to ensure the processability and operability of the resin composition during molding, and its amount is not particularly limited.

[0260] In this invention, although the term "solvent" and the term "solvent medium" are used to distinguish them according to their usage, they can be used independently of the same substance or different substances.

[0261] Examples of solvents include: ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; esters such as γ-butyrolactone and ethyl acetate; ethers such as ethylene glycol monomethyl ether; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; alcohols such as methanol and ethanol; alkanes such as hexane and cyclohexane; and aromatics such as toluene, xylene, and anisole.

[0262] Solvents can be used in combination, or in combination of two or more.

[0263] The amount of solvent relative to the resin composition is not particularly limited, but it is preferably used in the range of 0 parts by weight or more and 2000 parts by weight or less relative to 100 parts by weight of the resin composition. More preferably, it is 1000 parts by weight or less.

[0264] Antioxidants

[0265] Examples of antioxidants include hindered phenolic compounds, phosphorus compounds, sulfur compounds, metal compounds, and hindered amine compounds, with hindered phenolic compounds being preferred.

[0266] As hindered phenolic compounds, compounds with a molecular weight of 500 or higher are preferred. Examples of hindered phenolic compounds with a molecular weight of 500 or higher include: triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylaniline)-3,5-triazine, pentaerythritol tetra[3-(3,5-tert-butyl-4-hydroxyphenyl)propionate], 1,1,3-triazine... [2-Methyl-4-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-5-tert-butylphenyl]butane, 2,2-thio-diethylidene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamoamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenyl) (Benyl)benzene, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 3,9-bis[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8,10-tetraoxazolo[5.5]undecane, 2,6-di-tert-butyl-p-cresol (BHT), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione [Company Name] [AO-020 manufactured by ADEKA Co., Ltd.], 4,4',4''-(1-methylpropyl-3-ylidene)tris(6-tert-butyl-m-cresol) [AO-030 manufactured by ADEKA Co., Ltd.], 6,6'-di-tert-butyl-4,4'-butylidene di-m-cresol [AO-040 manufactured by ADEKA Co., Ltd.], 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene [AO-330 manufactured by ADEKA Co., Ltd.]

[0267] Examples of hindered amine compounds include: 2,2,6,6-tetramethyl-4-hydroxypiperidin-1-oxy [ADK STAB LA-7RD manufactured by ADEKA Co., Ltd.], IRGASTAB UV 10 (4,4'-[1,10-dioxo-1,10-decanediyl)bis(oxy)]bis[2,2,6,6-tetramethyl]-1-piperidinyloxy (CAS. 2516-92-9), TINUVIN 123 (4-hydroxy-2,2,6,6-tetramethylpiperidin-N-oxy) (all manufactured by BASF), FA-711HM, FA-712HM (2,2,6,6-tetramethylpiperidinyl methacrylate, manufactured by Showa Denko Materials Co., Ltd.), TINUVIN 111FDL, TINUVIN144, TINUVIN 152, and TINUVIN. 292, TINUVIN 765, TINUVIN 770DF, TINUVIN 5100, SANOL LS-2626, CHIMASSORB 119FL, CHIMASSORB 2020 FDL, CHIMASSORB 944 FDL, TINUVIN 622 LD (all manufactured by BASF), LA-52, LA-57, LA-62, LA-63P, LA-68LD, LA-77Y, LA-77G, LA-81, LA-82 (1,2,2,6,6-pentamethyl-4-piperidinyl methacrylate), LA-87 (all manufactured by ADEKA Corporation).

[0268] The content of antioxidant relative to the resin composition is not particularly limited, but it is preferred to use it in the range of 0.001 parts by weight or more and 10 parts by weight or less relative to 100 parts by weight of the resin composition.

[0269] <Polymerization inhibitors>

[0270] Examples of polymerization inhibitors include quinones such as hydroquinone, methylhydroquinone, p-benzoquinone, chloroquinone, and trimethylquinone, and phenols such as 4-tert-butylpyrocatechol, p-methoxyphenol, and 2,6-di-tert-4-methylphenol.

[0271] [Cured product]

[0272] The cured product obtained by curing the resin composition of this embodiment exhibits an excellent balance between low dielectric properties and high metal adhesion, displaying good cured product properties. Here, "curing" refers to the intentional curing of the resin composition by heat and / or light, and the degree of curing can be controlled according to the desired properties and application. The degree of curing can be complete curing or a semi-cured state.

[0273] The curing method of the resin composition in this embodiment varies depending on the formulation and amount of the resin composition. Preferably, curing is based on heating conditions of 60–280°C for 1–600 minutes. Regarding the heating temperature, 100–250°C is more preferred, and 120–230°C is even more preferred. Regarding the heating time, 5–450 minutes is more preferred, and 30–300 minutes is even more preferred.

[0274] When producing a resin semi-cured product, it is preferable to allow the resin composition to cure to a degree that allows it to maintain its shape by means of heating or the like. If the resin composition contains a solvent, most of the solvent is usually removed by methods such as heating, depressurization, or air drying, but it is also possible to leave less than 5 parts by weight of solvent remaining in the resin semi-cured product.

[0275] [Layered structure]

[0276] The laminate of this embodiment can be a laminate obtained by laminating a layer containing the resin composition of this embodiment with a substrate. It should be noted that in the laminate of this embodiment, it is sufficient to use the resin composition of this embodiment in at least one layer, or a layer composed of two or more resin compositions may be formed. Furthermore, when a substrate is used in the laminate, two or more substrates may be used. The thickness of the layer formed by the resin composition in the laminate is typically, for example, 1 μm to 3 mm.

[0277] The layer comprising the resin composition of this embodiment can be a prepreg obtained by impregnating the resin composition of the present invention into a nonwoven fabric or cloth using inorganic and / or organic fibrous materials such as glass fiber, polyester fiber, aramid fiber, cellulose, or nanofiber cellulose, and then curing it. Alternatively, it can be a cured film obtained by melt molding or casting the resin composition.

[0278] From the perspective of adhesion and practicality, substrates can be categorized as follows: inorganic substrates, metal substrates, resin substrates, and prepregs.

[0279] Examples of inorganic substrates include substrates containing at least one selected from the group consisting of glass, silicon, aluminum oxide, silicon carbide, gallium nitride, and silicon nitride.

[0280] Examples of metal substrates include substrates containing at least one selected from the group consisting of copper, aluminum, gold, silver, nickel, palladium, etc. Alternatively, metal foils of these metals, or metal layers formed by plating or sputtering, can be used as metal substrates.

[0281] Examples of resin substrates include substrates comprising at least one selected from the group consisting of liquid crystal polymers, polyimide, polyphenylene sulfide, polyether ether ketone, polyamide, polyethylene terephthalate, polyethylene naphthalate, cyclic olefin polymers, and polyolefins.

[0282] [use]

[0283] The compounds, resin compositions, cured products, and laminates of this embodiment can be applied to various fields such as adhesives, coatings, civil engineering materials, various composite materials, primarily carbon fiber reinforced plastics (CFRP), and insulating materials for electrical and electronic components. In particular, they are useful as insulating casting, laminate materials, and sealing materials for electrical and electronic components. Specifically, examples include (multilayer) printed circuit boards, copper-clad laminates, laminated films, capacitors, and other electrical and electronic circuit laminates; adhesives such as film adhesives and liquid adhesives; semiconductor sealing materials; underfill materials; inter-chip fill materials for 3D-LSI; insulating sheets; prepregs; and heat dissipation substrates, but are not limited to any of them.

[0284] Example

[0285] The present invention will now be described in more detail based on embodiments, but the present invention is not limited to any of the following embodiments. It should be noted that the various manufacturing conditions and evaluation results in the following embodiments have the meaning of preferred values ​​as upper or lower limits in the implementation of the present invention, and the preferred range can be the range defined by the above-mentioned upper or lower limit values ​​and the values ​​of the following embodiments or the values ​​of the embodiments.

[0286] [Methods for evaluating physical properties and characteristics]

[0287] In the following synthesis examples, embodiments, and comparative examples, the evaluation of physical properties and characteristics was carried out according to the methods described below.

[0288] <1> The weight-average molecular weight (Mw), number-average molecular weight (Mn), and weight ratio of compound (1) to compound (3) (curing compound (2)) of the polyether compounds.

[0289] Using the HLC-8320GPC apparatus manufactured by Tosoh Corporation, the following test conditions were met: TSK Standard Polystyrene: F-128 (Mw: 1,090,000, Mn: 1,030,000), F-10 (Mw: 106,000, Mn: 103,000), F-4 (Mw: 43,000, Mn: 42,700), and F-2 (Mw: 17,200, Mn: 16,900). A-5000 (Mw: 6,400, Mn: 6,100), A-2500 (Mw: 2,800, Mn: 2,700), A-1000 (Mw: 1,100, Mn: 871), and A-300 (Mw: 453, Mn: 387) were used as standard curves for standard polystyrene. The weight-average molecular weight (Mw), number-average molecular weight (Mn), and weight ratio of compound (1) to compound (3) (curing compound (2)) were determined in the form of polystyrene conversion values.

[0290] Pillar: "TSKGEL SuperHM-H+H5000+H4000+H3000+H2000" manufactured by Tosoh Corporation

[0291] Eluent: Tetrahydrofuran

[0292] Flow rate: 0.5 ml / min

[0293] Detection: UV (wavelength 254nm)

[0294] Temperature: 40℃

[0295] Sample concentration: 0.1% by weight

[0296] Injection volume: 10 μL

[0297] <2> Dielectric loss tangent of cured material

[0298] The thin-film cured material was cut into test pieces with a width of 2 mm and a length of 90 mm, and the dielectric loss tangent at 10 GHz was measured using the split cylinder method. As a measuring device, a network analyzer (N5224B, manufactured by Keysight Technologies) and a cavity resonator (CP531, manufactured by Kanto Electronics Application Development Co., Ltd.) were used for the measurement.

[0299] <3> Copper foil peel strength

[0300] To evaluate the metallic adhesion of the cured product, the copper foil peel strength was determined according to the following steps.

[0301] Specifically, a varnish-like resin composition is applied to copper foil (trade name "3EC-M3-VLP" manufactured by Mitsui Metals & Mining Co., Ltd.) using a coater and dried at 130°C for 5 minutes to form a resin composition coating. Copper foil (trade name "3EC-M3-VLP" manufactured by Mitsui Metals & Mining Co., Ltd.) is then overlapped on the resulting coating and vacuum-pressed at 200°C and 0.2 MPa for 2 hours to produce a cured film with copper foil. The resulting cured film with copper foil is cut into pieces 2.5 cm wide and 20 cm long, and subjected to a 180° peel test using an Instron tensile testing machine at a tensile speed of 50 mm / min under an atmosphere of 23°C and 50% relative humidity. The center value is taken as the adhesion strength of the cured film to the copper foil (copper foil peel strength) (N / cm).

[0302] [Synthesis example 1]

[0303] 15 g (0.059 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 6.8 g (0.039 mol) of m-xylene dichloro, 9.3 g (0.14 mol) of potassium hydroxide (85% purity), 0.63 g of tetrabutylammonium bromide, and 30 g of diethylene glycol dimethyl ether were added to a 500 mL four-necked flask equipped with a thermometer, stirrer, and condenser. The reaction was heated to 75 °C and carried out for 3 hours. Then, 7.14 g (0.047 mol) of 4-(chloromethyl)styrene (product name "CMS-14" manufactured by AGC Seimei Chemical Co., Ltd.) was added, and the reaction was carried out for another 3 hours at 75 °C. After the reaction was completed, 30 g of toluene was added, and the mixture was washed four times with 100 g of water. Then, 300 g of isopropanol was added, and the precipitated solid was separated by filtration. The obtained solid was washed three times with 100g of isopropanol and dried to obtain 16g of a resin composition of compound (1-1) as shown in formula (33) and compound (3-1) as shown in formula (34). The weight-average molecular weight of compound (1-1) is 7876 and the number-average molecular weight is 1236. In the obtained resin composition, the content of compound (3-1) is 26% by weight.

[0304] [Chemical Formula 28]

[0305]

[0306] [Chemical Formula 29]

[0307]

[0308] [Synthesis example 2]

[0309] 15 g (0.059 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 9.3 g (0.14 mol) of potassium hydroxide (85% purity), 0.63 g of tetrabutylammonium bromide, and 45 g of diethylene glycol dimethyl ether were added to a 500 mL four-necked flask equipped with a thermometer, stirrer, and condenser. The mixture was stirred at room temperature for 1 hour. 6.8 g (0.039 mol) of m-xylene dichloro was added, and the reaction temperature was raised to 75°C, and the reaction was carried out for 3 hours. Then, 7.14 g (0.047 mol) of 4-(chloromethyl)styrene (product name "CMS-14" manufactured by AGC Seimei Chemical Co., Ltd.) was added, and the reaction was further carried out at 75°C for 3 hours. After the reaction was completed, 30 g of toluene was added, and the mixture was washed four times with 100 g of water. Then, 300 g of isopropanol was added, and the precipitated solid was separated by filtration. The obtained solid was washed three times with 100g of isopropanol and dried to obtain 16g of a resin composition of compound (1-2) of formula (33) and compound (3-1) of formula (34). The weight-average molecular weight of compound (1-2) is 2766 and the number-average molecular weight is 1375. In the obtained resin composition, the content of compound (3-1) is 15% by weight.

[0310] [Synthesis example 3]

[0311] 25 g (0.098 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 14.23 g (0.081 mol) of m-xylene dichloro, 1.57 g of tetrabutylammonium bromide, and 75 g of DMF were added to a 500 mL four-necked flask equipped with a thermometer, stirrer, and condenser. The reaction temperature was raised to 80 °C and the reaction was carried out for 4 hours. Then, 5.95 g (0.039 mol) of 4-(chloromethyl)styrene (product name "CMS-14" manufactured by AGC Seimei Chemical Co., Ltd.) was added, and the reaction was carried out again at 80 °C for 4 hours. After the reaction was completed, 25 g of DMF was added to the resulting reaction solution for dilution. After removing residual salts by filtration, the resulting solution was added to 250 g of methanol. The precipitated solid was separated by filtration, washed three times with 250 g of methanol, and then separated by filtration again. The obtained solid was dried in a vacuum dryer at 80°C under reduced pressure for 12 hours to obtain 23 g of a resin composition of compound (1-3) of formula (33) and compound (3-1) of formula (34). The weight-average molecular weight of compound (1-3) is 5651, and the number-average molecular weight is 2396. The content of compound (3-1) in the obtained resin composition is 6% by weight.

[0312] [Synthesis example 4]

[0313] The raw materials used in Synthesis Example 3 were changed to 20 g (0.078 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 10.93 g (0.062 mol) of o-xylene dichloro, 25.88 g (0.187 mol) of potassium carbonate, 2.52 g of tetrabutylammonium bromide, 60 g of DMF, and 5.72 g (0.037 mol) of 4-(chloromethyl)styrene (product name "CMS-14" manufactured by AGC Seimei Chemical Co., Ltd.). The reaction temperature was changed to 90 °C. Otherwise, the same method was used to synthesize 21 g of a resin composition of compound (1-4) shown in formula (35) and compound (3-1) shown in formula (34). The weight-average molecular weight of compound (1-4) is 8649, and the number-average molecular weight is 1577. The content of compound (3-1) in the obtained resin composition is 11% by weight.

[0314] [Chemical Formula 30]

[0315]

[0316] [Synthesis example 5]

[0317] The raw materials used in Synthesis Example 3 were changed to 25 g (0.065 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Co., Ltd. under the product name "YOSHINOX BB"), 9.15 g (0.052 mol) of m-xylene dichloro, 19.87 g (0.144 mol) of potassium carbonate, 2.10 g of tetrabutylammonium bromide, 75 g of DMF, and 4.79 g (0.048 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (manufactured by AGC Seimei Chemical Co., Ltd. under the product name "CMS-P"). The reaction temperature was changed to 105 °C. Otherwise, the same method was used to synthesize 33 g of a resin composition of compound (1-5) shown in formula (36) and compound (3-2) shown in formula (37). The weight-average molecular weight of compound (1-5) was 6209, and the number-average molecular weight was 3066. The resin composition obtained contains 5% by weight of compound (3-2).

[0318] [Chemical Formula 31]

[0319]

[0320] [Chemical Formula 32]

[0321]

[0322] [Synthesis example 6]

[0323] The raw materials used in Synthesis Example 3 were changed to 25 g (0.065 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Co., Ltd. under the product name "YOSHINOX BB"), 10.61 g (0.061 mol) of m-xylene dichloro, 21.62 g (0.156 mol) of potassium carbonate, 2.10 g of tetrabutylammonium bromide, 75 g of DMF, and 2.78 g (0.018 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (manufactured by AGC Seimei Chemical Co., Ltd. under the product name "CMS-P"). The reaction temperature was changed to 105 °C. Otherwise, the same method was used to synthesize 20 g of a resin composition of compound (1-6) of formula (36) and compound (3-2) of formula (37). The weight-average molecular weight of compound (1-6) was 10390 and the number-average molecular weight was 3774. The obtained resin composition contains 4% by weight of compound (3-2).

[0324] [Synthesis Example 7]

[0325] The raw materials used in Synthesis Example 3 were changed to 25 g (0.065 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Co., Ltd. under the product name "YOSHINOX BB"), 10.89 g (0.062 mol) of m-xylene dichloro, 21.67 g (0.157 mol) of potassium carbonate, 2.10 g of tetrabutylammonium bromide, 75 g of DMF, and 1.42 g (0.009 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (manufactured by AGC Seimei Chemical Co., Ltd. under the product name "CMS-P"). The reaction temperature was changed to 105 °C. Otherwise, the same method was used to synthesize 22 g of resin compositions of compounds (1-7) of formula (36) and compounds (3-2) of formula (37). The weight-average molecular weight of compounds (1-7) was 17004, and the number-average molecular weight was 6036. The resin composition obtained contains 2% by weight of compound (3-2).

[0326] [Synthesis example 8]

[0327] The starting materials used in Synthesis Example 3 were changed to 20 g (0.052 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Corporation under the product name "YOSHINOX BB"), 11.41 g (0.065 mol) of m-xylene dichloro, 21.62 g (0.156 mol) of potassium carbonate, 2.52 g of tetrabutylammonium bromide, 75 g of DMF, and 4.20 g (0.031 mol) of o-allylphenol. The reaction temperature was changed to 105 °C. Otherwise, the same method was used to synthesize 16 g of compound (1-8) as shown in formula (38). The weight-average molecular weight of compound (1-8) was 7255, and the number-average molecular weight was 2923. No compound equivalent to compound (3) was detected.

[0328] [Chemical Formula 33]

[0329]

[0330] [Synthesis example 9]

[0331] 25 g (0.065 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Corporation under the product name "YOSHINOX BB"), 9.15 g (0.052 mol) of m-xylene dichloro, 19.87 g (0.144 mol) of potassium carbonate, 2.10 g of tetrabutylammonium bromide, and 75 g of DMF were added to a 500 mL four-necked flask equipped with a thermometer, stirrer, and condenser. The reaction temperature was raised to 105 °C and the reaction was carried out for 4 hours. After removing residual salts by filtration, the resulting solution was added to 250 g of water. The precipitated solid was separated by filtration, washed three times with 250 g of water, and then separated by filtration again. The obtained solid was dried in a vacuum dryer at 100 °C under reduced pressure for 12 hours.

[0332] The solid obtained above, 4.08 g (0.039 mol) of methacryloyl chloride, and 75 g of dichloromethane were added to a 500 mL four-necked flask equipped with a thermometer, a stirrer, and a condenser. The mixture was stirred at room temperature until dissolved. Then, 5.26 g (0.052 mol) of triethylamine was added dropwise over 15 minutes, and the reaction was carried out at room temperature for 1 hour. After the reaction was completed, the resulting reaction solution was added to 250 g of methanol. The precipitated solid was filtered and separated, washed three times with 250 g of methanol, and then filtered again. The obtained solid was dried in a vacuum dryer at 80 °C under reduced pressure for 12 hours to obtain 20 g of a resin composition of compound (1-9) shown in formula (39) and compound (3-3) shown in formula (40). The weight-average molecular weight of compound (1-9) is 6109, and the number-average molecular weight is 2871. The content of compound (3-3) in the obtained resin composition is 6% by weight.

[0333] [Chemical Formula 34]

[0334]

[0335] [Chemical Formula 35]

[0336]

[0337] [Synthesis Example 10]

[0338] The raw materials used in Synthesis Example 3 were changed to 25 g (0.081 mol) of 2,2'-diallylbisphenol A (product name "DABPA" manufactured by Yamato Chemical Co., Ltd.), 11.75 g (0.067 mol) of m-xylene dichloro, 24.65 g (0.178 mol) of potassium carbonate, 1.31 g of tetrabutylammonium bromide, 75 g of DMF, and 4.95 g (0.032 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Seimei Chemical Co., Ltd.). The reaction temperature was changed to 90 °C. Otherwise, the same method was used to synthesize 24 g of a resin composition of compounds (1-10) shown in formula (41) and compounds (3-4) shown in formula (42). The weight average molecular weight of compounds (1-10) was 6109, and the number average molecular weight was 2871. The resin composition obtained contains 5% by weight of compounds (3-4).

[0339] [Chemical Formula 36]

[0340]

[0341] [Chemical Formula 37]

[0342]

[0343] [Synthesis Example 11]

[0344] The raw materials used in Synthesis Example 3 were changed to 25 g (0.081 mol) of 4,4'-(3,3,5-trimethylcyclohexane-1,1-diyl)diphenol (product name "BisP-HTG" manufactured by Honshu Chemical Co., Ltd.), 11.82 g (0.067 mol) of m-xylene dichloro, 26.71 g (0.193 mol) of potassium carbonate, 2.60 g of tetrabutylammonium bromide, 75 g of DMF, and 6.15 g (0.040 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Seimei Chemical Co., Ltd.). The reaction temperature was changed to 70 °C. Otherwise, the same method was used to synthesize 19 g of a resin composition of compound (1-11) shown in formula (43) and compound (3-5) shown in formula (44). The weight-average molecular weight of compounds (1-11) is 6226, and the number-average molecular weight is 2561. The content of compounds (3-5) in the obtained resin composition is 6% by weight.

[0345] [Chemical Formula 38]

[0346]

[0347] [Chemical Formula 39]

[0348]

[0349] [Synthesis Example 12]

[0350] The starting materials used in Synthesis Example 3 were changed to 25 g (0.066 mol) of 9,9'-bis(4-hydroxy-3-methylphenyl)fluorene (product name "BisOC-FL" manufactured by Honshu Chemical), 9.25 g (0.053 mol) of m-xylene dichloro, 21.91 g (0.159 mol) of potassium carbonate, 2.13 g of tetrabutylammonium bromide, 75 g of DMF, and 6.05 g (0.040 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Seimei Chemical Co., Ltd.). The reaction temperature was changed to 90 °C. Otherwise, the same method was used to synthesize 21 g of a resin composition of compounds (1-12) shown in formula (45) and compounds (3-6) shown in formula (46). The weight-average molecular weight of compounds (1-12) was 6288, and the number-average molecular weight was 2442. The resin composition obtained contains 5% by weight of compounds (3-6).

[0351] [Chemical Formula 40]

[0352]

[0353] [Chemical Formula 41]

[0354]

[0355] [Synthesis Example 13]

[0356] The raw materials used in Synthesis Example 3 were changed to 12.0 g (0.032 mol) of 9,9'-bis(4-hydroxy-3-methylphenyl)fluorene (product name "BisOC-FL" manufactured by Honshu Chemical), 12.2 g (0.048 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical), 11.6 g (0.066 mol) of m-xylene dichloro, 26.29 g (0.190 mol) of potassium carbonate, 2.56 g of tetrabutylammonium bromide, and DMF. 75 g of a mixture of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene isomers (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 5.24 g (0.034 mol) were used. The reaction temperature was changed to 90 °C. Otherwise, the same method was used to synthesize 20 g of a resin composition of compound (1-13) shown in formula (47), compound (3-7) shown in formula (50), and compound (3-6) shown in formula (46). The weight-average molecular weight of compound (1-13) is 6288, and the number-average molecular weight is 2442. The total content of compounds (3-7) and (3-6) in the obtained resin composition is 5% by weight.

[0357] [Chemical Formula 42]

[0358]

[0359] In equation (46) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (48) and equation (49) below. In equations (48) and (49), the symbol "*" represents a bonding bond.

[0360] [Chemical Formula 43]

[0361]

[0362] [Chemical Formula 44]

[0363]

[0364] [Synthesis Example 14]

[0365] The raw materials used in Synthesis Example 3 were changed to 20.0 g (0.053 mol) of 9,9'-bis(4-hydroxy-3-methylphenyl)fluorene (product name "BisOC-FL" manufactured by Honshu Chemical), 3.40 g (0.013 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical), 9.25 g (0.053 mol) of m-xylene dichloro, 21.91 g (0.190 mol) of potassium carbonate, 2.13 g of tetrabutylammonium bromide, and DMF. 75 g of a mixture of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene isomers (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 4.84 g (0.032 mol) were used. The reaction temperature was changed to 90 °C. Otherwise, the same method was used to synthesize 18 g of a resin composition of compounds (1-14) of formula (47), compounds (3-7) of formula (50), and compounds (3-6) of formula (46). The weight-average molecular weight of compound (1-14) is 5608, and the number-average molecular weight is 2649. The total content of compounds (3-7) and (3-6) in the obtained resin composition is 4% by weight.

[0366] [Synthesis Example 15]

[0367] The raw materials used in Synthesis Example 3 were changed to 21.0 g (0.055 mol) of 9,9'-bis(4-hydroxy-3-methylphenyl)fluorene (product name "BisOC-FL" manufactured by Honshu Chemical), 3.56 g (0.014 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical), 11.0 g (0.063 mol) of m-xylene dichloro, 23.0 g (0.190 mol) of potassium carbonate, 2.24 g of tetrabutylammonium bromide, and DMF. 75.0 g of a mixture of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene isomers (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 2.89 g (0.019 mol) were used to synthesize a resin composition of compounds (1-15) of formula (47), compounds (3-7) of formula (50), and compounds (3-6) of formula (46) by changing the reaction temperature to 90 °C. The weight-average molecular weight of compound (1-15) was 13015, and the number-average molecular weight was 4000. The total content of compounds (3-7) and (3-6) in the obtained resin composition was 3% by weight.

[0368] [Synthesis Example 16]

[0369] The raw materials used in Synthesis Example 3 were changed to 20.0 g (0.053 mol) of 9,9'-bis(4-hydroxy-3-methylphenyl)fluorene (manufactured by Honshu Chemical under the product name "BisOC-FL"), 5.11 g (0.018 mol) of 4,4'-(α-methylbenzyl)bisphenol (manufactured by Honshu Chemical under the product name "BisP-AP"), 10.3 g (0.059 mol) of m-xylene dichloro, 23.4 g (0.169 mol) of potassium carbonate, 2.27 g of tetrabutylammonium bromide, and DMF. 75.0 g of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 5.38 g (0.035 mol) were used, and 24 g of a resin composition of compounds (1-16) of formula (51), compounds (3-6) of formula (46), and compounds (3-8) of formula (53) were synthesized by the same method. The weight-average molecular weight of compound (1-16) was 5740, and the number-average molecular weight was 2358. The total content of compounds (3-6) and (3-8) in the obtained resin composition was 6% by weight.

[0370] [Chemical Formula 45]

[0371]

[0372] In equation (50) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (48) and equation (52) below. In equations (48) and (52), the symbol "*" represents a bonding bond.

[0373] [Chemical Formula 46]

[0374]

[0375] [Chemical Formula 47]

[0376]

[0377] [Synthesis Example 17]

[0378] The starting materials used in Synthesis Example 3 were changed to 10.6 g (0.041 mol) of 4,4'-methylenebis(2,6-dimethylphenol) (manufactured by Deepak under the product name "Tetramethylbisphenol F"), 5.11 g (0.018 mol) of 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl, 14.5 g (0.083 mol) of m-xylenedichloro, 34.2 g (0.248 mol) of potassium carbonate, 3.33 g of tetrabutylammonium bromide, and DMF. 75.0 g of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 7.56 g (0.050 mol) were used, and 23 g of a resin composition of compounds (1-17) of formula (54), compounds (3-9) of formula (57), and compounds (3-10) of formula (58) were synthesized by the same method. The weight-average molecular weight of compound (1-17) was 5740, and the number-average molecular weight was 2358. The total content of compounds (3-9) and (3-10) in the obtained resin composition was 19% by weight.

[0379] [Chemical Formula 48]

[0380]

[0381] In equation (54) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (55) and equation (56) below. In equations (55) and (56), the symbol "*" represents a bonding bond.

[0382] [Chemical Formula 49]

[0383]

[0384] [Chemical Formula 50]

[0385]

[0386] [Chemical Formula 51]

[0387]

[0388] [Synthesis Example 18]

[0389] The starting materials used in Synthesis Example 3 were changed to 7.28 g (0.028 mol) of 4,4'-methylenebis(2,6-dimethylphenol) (manufactured by Deepak under the product name "Tetramethylbisphenol F"), 18.0 g (0.043 mol) of the phenolic compound shown in formula (59) (manufactured by Chung-Ying Chemical Co., Ltd. under the product name "XB26H"), 9.94 g (0.057 mol) of m-xylene dichloro, 23.6 g (0.170 mol) of potassium carbonate, 2.29 g of tetrabutylammonium bromide, and DMF. 75.0 g of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 5.20 g (0.050 mol), and 24 g of a resin composition of compounds (1-18) of formula (60), compounds (3-9) of formula (57), and compounds (3-11) of formula (62) were synthesized by the same method. The weight-average molecular weight of compound (1-18) is 10773, and the number-average molecular weight is 2298. The total content of compounds (3-9) and (3-11) in the obtained resin composition is 9% by weight.

[0390] [Chemical Formula 52]

[0391]

[0392] [Chemical Formula 53]

[0393]

[0394] In equation (58) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (55) and equation (61) below. In equations (55) and (61), the symbol "*" represents a bonding bond.

[0395] [Chemical Formula 54]

[0396]

[0397] [Chemical Formula 55]

[0398]

[0399] [Synthesis Example 19]

[0400] The raw materials used in Synthesis Example 3 were changed to 18.0 g (0.070 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 7.50 g (0.047 mol) of 2,7-dihydroxynaphthalene, 16.39 g (0.094 mol) of m-xylene dichloro, 38.8 g (0.281 mol) of potassium carbonate, 3.77 g of tetrabutylammonium bromide, 75.0 g of DMF, and 8.57 g (0.050 mol) of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Seimei Chemical Co., Ltd.). Otherwise, the same method was used to synthesize 19 g of resin compositions of compounds (1-19) shown in Formula (63), compounds (3-7) shown in Formula (50), and compounds (3-12) shown in Formula (65). The weight-average molecular weight of compounds (1-19) is 5482, and the number-average molecular weight is 1673. The total content of compounds (3-7) and (3-12) in the obtained resin composition is 12% by weight.

[0401] [Chemical Formula 56]

[0402]

[0403] In equation (63) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (49) and equation (64) below. In equations (49) and (64), the symbol "*" represents a bonding bond.

[0404] [Chemical Formula 57]

[0405]

[0406] [Chemical Formula 58]

[0407]

[0408] [Synthesis Example 20]

[0409] The starting materials used in Synthesis Example 3 were changed to 20.0 g (0.052 mol) of 4,4'-butylidene bis-(6-tert-butyl-3-methylphenol) (manufactured by Mitsubishi Chemical Corporation, product name "YOSHINOX BB"), 7.12 g (0.013 mol) of 4,4',4''-(1-methylpropyl-3-ylidene)tris(6-tert-butyl-m-cresol) (manufactured by ADEKA Corporation, product name "ADK STAB AO-30"), 9.15 g (0.052 mol) of m-xylene dichloro, 28.8 g (0.173 mol) of potassium carbonate, 3.77 g of tetrabutylammonium bromide, and DMF. 75.0 g of a mixture of isomers of 3-(chloromethyl)styrene and 4-(chloromethyl)styrene (product name "CMS-P" manufactured by AGC Chingmy Chemical Co., Ltd.) 8.98 g (0.059 mol) were used, and 18 g of a resin composition of compounds (1-20) of formula (66), compound (3-2) of formula (37), and compound (3-13) of formula (70) were synthesized by the same method. The weight-average molecular weight of compound (1-20) was 7807, and the number-average molecular weight was 2311. The total content of compounds (3-2) and (3-13) in the obtained resin composition was 13% by weight.

[0410] [Chemical Formula 59]

[0411]

[0412] In equation (66) above, Ar independently represents one of the structures selected from the group consisting of the structures shown in equation (67) and equation (68) below. In equation (68), Z represents the structure shown in equation (69) below, and in equation (69), Ar is the same as Ar in equation (66). In equations (66) and (67), the symbol "*" represents a bonding bond.

[0413] [Chemical Formula 60]

[0414]

[0415] [Chemical Formula 61]

[0416]

[0417] [Synthesis Example 21]

[0418] In Synthesis Example 1, 6.8 g of p-xylene dichloro was used instead of 6.8 g of m-xylene dichloro. Otherwise, 17 g of a resin composition of compound (1-21) of formula (71) and compound (3-1) of formula (34) was obtained by the same method. The weight-average molecular weight of compound (1-21) was 8416, and the number-average molecular weight was 1203. The content of compound (3-1) in the obtained resin composition was 26% by weight.

[0419] [Chemical Formula 62]

[0420]

[0421] [Synthesis Example 22]

[0422] The raw materials used in Synthesis Example 3 were changed to 25.0 g (0.081 mol) of 2,5-dihydroxy(diphenyl)phosphine oxide, 11.8 g (0.067 mol) of m-xylene dichloro, 26.7 g (0.193 mol) of potassium carbonate, 2.60 g of tetrabutylammonium bromide, 75.0 g of DMF, and 6.15 g (0.040 mol) of 4-(chloromethyl)styrene (product name "CMS-14" manufactured by AGC Chingmy Chemical Co., Ltd.). Otherwise, the same method was used to synthesize 17 g of a resin composition of compounds (1-22) shown in formula (72) and compounds (3-14) shown in formula (73). The weight-average molecular weight of compounds (1-22) was 5784, and the number-average molecular weight was 2215. The content of compound (3-14) in the obtained resin composition was 5% by weight.

[0423] [Chemical Formula 63]

[0424]

[0425] [Chemical Formula 64]

[0426]

[0427] [Synthesis example 23]

[0428] 25 g (0.098 mol) of bisphenol C (product name "S-BOC" manufactured by Honshu Chemical Co., Ltd.), 14.23 g (0.081 mol) of m-xylene dichloro, 0.215 mol of potassium carbonate, 1.57 g of tetrabutylammonium bromide, and 75 g of DMF were added to a 500 mL four-necked flask equipped with a thermometer, a stirrer, and a condenser. The reaction temperature was raised to 80 °C and the reaction was carried out for 4 hours. After removing the residual salt by filtration, the resulting solution was added to 250 g of water. The precipitated solid was filtered and separated, washed three times with 250 g of water, filtered and separated again, and the obtained solid was dried in a vacuum dryer at 100 °C under reduced pressure for 12 hours to obtain 16 g of compound (1-23) as shown in formula (74). The weight average molecular weight is 5868 and the number average molecular weight is 1976.

[0429] [Chemical Formula 65]

[0430]

[0431] [Examples 1-27, Comparative Examples 1-3]

[0432] Solvent solubility

[0433] Weigh the following components according to the mixing ratios listed in Table 1: resin composition containing polyether compound, vinyl compound (product name "OPE-2st2200" manufactured by Mitsubishi Gas Chemical Co., Ltd.), maleimide compound (product name "BMI-80" manufactured by K・I CHEMICAL INDUSTRY CO., LTD.), maleimide compound (product name "Designer Molecules" manufactured by Mitsubishi Chemical Co., Ltd.), allyl compound (product name "TAIC" manufactured by Mitsubishi Chemical Co., Ltd.), and elastomer (product name "SEPTON" manufactured by Kuraray Co., Ltd.). The mixture consisted of 8007”, an antioxidant (product name “AO-60” manufactured by ADEKA), and dicumyl peroxide (DCP) as a curing accelerator. Toluene was then added at a solids concentration of 50% by weight, and the mixture was stirred at room temperature for 1 hour to obtain a varnish-like resin composition. Visual confirmation was used to classify the solubility of toluene as “A” (no residual solids) and “B” (residual solids). The results are shown in Table 1.

[0434] <Film-forming properties>

[0435] The obtained varnish-like resin composition was applied to an isolation layer (a silicone-treated polyethylene terephthalate film) using a coater to form a 10cm × 15cm film, which was then dried at 130°C for 15 minutes. The film was then vacuum-pressed at 160°C for 15 minutes and then vacuum-pressed at 200°C for 2 hours to obtain a cured product. The case where the cured product could be removed as a film larger than 2cm × 10cm was evaluated as film-forming property "A", and the case where it could not be removed was evaluated as film-forming property "B". The results are shown in Table 1. Comparative Example 2 could not be evaluated.

[0436] <Dielectric loss tangent>

[0437] The dielectric loss tangent at 10 GHz was measured for the obtained cured products using the method described above. The results are shown in Table 1. For Comparative Examples 2 and 3, no cured films were obtained for evaluation and therefore evaluation was not possible.

[0438] <Copper Foil Peel Strength>

[0439] Using the obtained varnish-like resin composition, a cured film with copper foil was prepared by the method described above. The copper foil peel strength of the obtained cured film with copper foil was measured by the method described above. The results are shown in Table 1. For Comparative Examples 2 and 3, no cured films were obtained for evaluation and therefore evaluation was not possible.

[0440] [Table 1]

[0441]

[0442] [Table 2]

[0443]

[0444] [Table 3]

[0445]

[0446] [Evaluation of Results]

[0447] As shown in Tables 1 to 3, the resin compositions containing the polyether compounds of the present invention exhibit excellent solvent solubility and excellent film-forming properties during curing. Furthermore, it is evident that the cured resin compositions containing the polyether compounds of the present invention possess low dielectric properties even under high-frequency environments and exhibit excellent metal adhesion.

[0448] Industrial availability

[0449] The resin composition of the present invention can be applied to various fields such as adhesives, coatings, civil engineering building materials, various composite materials, primarily carbon fiber reinforced plastics (CFRP), and insulating materials for electrical and electronic components. In particular, it is useful as an insulating casting, laminating material, and sealing material in the electrical and electronic field.

Claims

1. A polyether compound, represented by the following formula (1), [Chemical Formula 1] In formula (1), l and n represent 0 or 1, m represents an integer from 1 to 50, Ar1 independently represents an aromatic hydrocarbon group with 6 to 100 carbon atoms that does not have the structure shown in formula (2), Ar2 represents the structure shown in formula (3) or the structure shown in formula (4) when m is 1 and n is 0, and independently represents at least one structure selected from the group consisting of the structure shown in formula (3) and the structure shown in formula (4) when m is 2 to 50 or n is 1, and Y independently represents a group containing an olefinic unsaturated double bond with 3 to 50 carbon atoms. [Chemical Formula 2] In equations (2) to (4), the symbol "*" represents a bond, A1 to A 10 Each is independently selected from any one of the group consisting of hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, phenyl groups, and naphthyl groups, R 1 ~R 8 Each is independently selected from any one of the groups consisting of hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms, and alkoxy groups with 1 to 20 carbon atoms.

2. The polyether compound according to claim 1, wherein, In formula (1), Y comprises at least one group selected from the group consisting of 2-vinylbenzyl, 3-vinylbenzyl, 4-vinylbenzyl, allyl, methylallyl, cinnamyl, acryloyl, methacryloyl, 2-allylphenyl, 2-propenylphenyl, 4-vinylphenyl, 4-isopropenylphenyl, 2-methoxy-4-allylphenyl, and 2-methoxy-4-propenylphenyl.

3. The polyether compound according to claim 1, wherein, Ar1 in formula (1) is at least one group selected from the group consisting of the groups shown in formulas (5) to (8). [Chemical Formula 3] In equations (5) to (8), the symbol "*" represents a bond, X4 is any one of the following groups consisting of directly bonded divalent hydrocarbon groups with 1 to 20 carbon atoms, -O-, -S-, -CO-, -C(O)-O-, -C(O)-NH-, -SO-, -SO2-, -C(CF3)2-, and -P(O)-, X5 is a trivalent hydrocarbon group with 1 to 20 carbon atoms, X6 is a tetravalent hydrocarbon group with 1 to 20 carbon atoms, and R 9 ~R 50 Each of the following groups is independently selected from hydrogen atoms, halogen atoms, hydrocarbon groups with 1 to 20 carbon atoms and alkoxy groups with 1 to 20 carbon atoms, and Z represents the structure shown in the following formula (9); [Chemical Formula 4] In equation (9), the symbol "*" represents a bonding bond, M represents an integer from 1 to 50, N represents 0 or 1, Ar1 and Y have the same meaning as Ar1 and Y in equation (1), Ar2 represents the structure shown in equation (3) or the structure shown in equation (4) when M is 1 and N is 0, or when M is 0 and N is 1, and when M is 2 to 50, or when M is 1 and N is 1, each independently represents at least one structure selected from the group consisting of the structure shown in equation (3) and the structure shown in equation (4).

4. The polyether compound according to claim 1, wherein, The polyether compound has a polystyrene equivalent weight-average molecular weight of 1,000 to 100,000.

5. A resin composition comprising the polyether compound according to claim 1 and a curable compound having a different structure from the polyether compound according to claim 1.

6. The resin composition according to claim 5, wherein, The curable compound is the compound represented by the formula (1) where l is 1 and m and n are 0.

7. The resin composition according to claim 5, wherein, The resin composition also includes a curing accelerator.

8. The resin composition according to claim 5, wherein, The curable compound has at least one substituent selected from the group consisting of epoxy, ester, oxazinyl, cyanate ester, maleimide, acryloyl, methacryloyl, styryl, allyl, vinyl, propenyl and benzoxazinyl.

9. The resin composition according to claim 5, wherein, The resin composition also contains an antioxidant.

10. A cured product, said cured product being a cured product of the resin composition according to any one of claims 5 to 9.

11. A laminated film comprising the cured material according to claim 10.

12. A copper-clad laminate comprising the cured material according to claim 10.

13. A laminate comprising the cured material according to claim 10.

14. An electrical and electronic component comprising the cured material according to claim 10.

15. An electrical and electronic component having a laminate according to claim 13.

16. Use of a resin composition as a raw material for electrical and electronic components, said resin composition being the resin composition according to any one of claims 5 to 9.

17. A method for manufacturing a polyether compound, said polyether compound being a polyether compound according to any one of claims 1 to 4, said manufacturing method comprising a step of reacting a phenolic compound, a divalent aromatic halomethyl compound, and a monovalent compound containing an olefinic unsaturated double bond in the presence of a basic compound.

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