Epoxy resin composition, insulating layer, electric / electronic component, printed wiring board, use of epoxy resin composition as raw material for insulator, and method for producing polymer

Abstract

Provided is an epoxy resin composition capable of suppressing viscosity increase even during long-term storage. An epoxy resin composition according to the present invention contains a polymer component, wherein: the weight-average molecular weight of the polymer component is 10,000 or more; the polymer component contains a polymer represented by formula (1); and at least a part of the polymer component is a polymer having a specific group.

Description

Epoxy resin composition, insulating layer, electric / electronic component, printed wiring board, use of epoxy resin composition as raw material for insulator, and method for producing polymer

[0001] The present invention relates to an epoxy resin composition, an insulating layer, an electric / electronic component, a printed wiring board, use of the epoxy resin composition as a raw material for an insulator, and a method for producing a polymer. This application claims priority based on Japanese Patent Application No. 2024-053146, filed on March 28, 2024, the contents of which are incorporated herein by reference.

[0002] In recent years, multilayer circuit boards used in electrical and electronic devices have become smaller, lighter, and more functional, and as a result, there is a demand for improved moldability, such as greater multilayering, higher density, thinner size, and lighter weight, as well as reliability in harsh environments such as automotive applications. In addition, as signals in various electronic devices become faster and higher in frequency, there is a demand for substrates with low transmission loss. Therefore, there is a demand for technologies that can balance and improve various properties of resin compositions used in substrates, such as heat resistance, adhesion, water resistance, low dielectric constant (low dielectric dissipation factor), mechanical strength, film formability, low linear expansion, and flame retardancy.

[0003] Patent Documents 1 and 2 disclose that a resin composition containing a polymer epoxy resin having a weight-average molecular weight of 10,000 to 200,000 is known as a resin composition for use in a multilayer circuit board, and that the resin composition is a resin composition for use in an electrical laminate that has excellent properties such as heat resistance, low water absorption, low dielectric constant, and low dielectric loss.

[0004] Japanese Patent Publication No. 2003-252951 Japanese Patent Publication No. 2003-342350

[0005] The polymeric epoxy resins disclosed in Patent Documents 1 and 2, which are polymers of a difunctional epoxy resin and a difunctional bisphenol, are excellent in heat resistance, low water absorption, etc., but their viscosity increases upon long-term storage, leaving room for improvement in long-term storage stability. An object of the present invention is to improve the long-term storage stability of compositions containing epoxy resins.

[0006] As a result of extensive research aimed at solving the above-mentioned problems, the present inventors have found that the long-term storage stability of an epoxy resin composition can be improved by preparing an epoxy resin composition containing a polymer having a specific structure at its terminal.

[0007] [1] An epoxy resin composition containing a polymer component having a weight average molecular weight of 10,000 or more, wherein the polymer component contains a polymer represented by the following formula (1):

[0008]

[0009] (In formula (1), A includes a chemical structure represented by formula (2); R １ and R ２ may be the same or different and are selected from the group consisting of a hydrogen atom, a group represented by formula (3), and a group represented by formula (4); R ３ represents a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms; and n represents the average number of repeating groups and is 5 to 120.

[0010]

[0011] (In formula (2), S １ , and S ２ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k1 and k2 are each independently an integer of 0 to 4; X １ is a direct bond. In formula (4), S ３ is a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k3 is an integer of 0 to 4; R ３ is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms), and at least a part of the polymer component is １ and R ２is a polymer in which at least one of the R １ and R ２ [2] The epoxy resin composition of [1], wherein the molar ratio of the group represented by formula (4) to the group represented by formula (3) in the polymer component (molar ratio of the group represented by formula (4) / molar ratio of the group represented by formula (3)) is 0.0001 or more and 0.50 or less. [3] The epoxy resin composition of [1] or [2], wherein k3 in formula (4) is 2. [4] The epoxy resin composition of [1], wherein k3 in formula (4) is 2. ３ The epoxy resin composition according to any one of [1] to [3], wherein S is an alkyl group having 1 to 12 carbon atoms. ３ is a methyl group. [6] The epoxy resin composition of any of [1] to [5], further comprising a curing agent. [7] An insulating layer obtained by curing the epoxy resin composition of [6]. [8] An electric / electronic component having the insulating layer of [7]. [9] A printed wiring board having the insulating layer of [7].

[10] Use of the epoxy resin composition of any of [1] to [6] as a raw material for an insulating layer.

[11] A method for producing a polymer, comprising reacting a bifunctional epoxy resin represented by formula (6), a bifunctional phenol compound represented by formula (7), and a monofunctional epoxy compound represented by formula (8) in a solvent in the presence of a catalyst.

[0012]

[0013] (In formula (6), each A independently contains a chemical structure represented by formula (2); m is an integer of 0 to 5. In formula (7), S ４ , and S ５ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k4 and k5 are each independently an integer of 0 to 4; R ３is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms; X ２ represents a direct bond, a divalent hydrocarbon group having 1 to 30 carbon atoms, —O—, —S—, or —SO ２ -, -C(CF ３ ) ２ In formula (8), S is a group selected from - and -CO-. ３ is a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; and k3 is an integer of 0 to 4.

[0014]

[0015] (In formula (2), S １ and S ２ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k1 and k2 are each independently an integer of 0 to 4; X １ is a direct bond.)

[0016] According to the present invention, an epoxy resin composition can be provided that can suppress an increase in viscosity even during long-term storage.

[0017] The following describes in detail an embodiment of the present invention, but the following description is merely an example of an embodiment of the present invention, and the present invention is not limited to the following description as long as it does not deviate from the gist of the present invention. Note that when the expression "to" is used in this specification, it is used as an expression that includes the numerical values ​​or physical property values ​​before and after it.

[0018] [Polymer] The epoxy resin composition of one embodiment of the present invention contains a polymer component having a weight average molecular weight of 10,000 or more, and the polymer component contains a polymer represented by the following formula (1).

[0019]

[0020] In formula (1), A contains a chemical structure represented by formula (2); １and R ２ may be the same or different and are selected from the group consisting of a hydrogen atom, a group represented by formula (3), and a group represented by formula (4); R ３ represents a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms; and n represents the average number of repeating groups and is 5 or more and 120 or less.

[0021]

[0022] In formula (2), S １ , and S ２ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k1 and k2 are each independently an integer of 0 to 4; X １ is a direct bond. In formula (4), S ３ is a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k3 is an integer of 0 to 4; R ３ is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms.

[0023] At least a part of the polymer component contained in the epoxy resin composition of the present invention is R １ and R ２ is a polymer in which at least one of the following is a group represented by formula (3), and at least a part of the polymer component is a polymer in which at least one of the following is a group represented by formula (1): １ and R ２ In other words, the polymer component contained in the epoxy resin composition of the present invention is a polymer in which at least one of R in formula (1) is a group represented by formula (4). １ and R ２ a polymer in which at least one of R in formula (1) is a group represented by formula (3), １ and R ２ and at least one of the groups represented by formula (4) is a polymer.

[0024] The reason why an epoxy resin composition containing a polymer component containing a polymer represented by formula (1) exhibits good long-term storage stability is unclear, but the present inventors speculate as follows. One factor that may worsen long-term storage stability is that the remaining epoxy groups react with moisture, etc., causing the epoxy groups to open, resulting in an increase in hydroxyl groups, which then form hydrogen bonds with the solvent, resulting in increased viscosity. In the epoxy resin composition of the present invention, the inclusion of a polymer component containing a polymer having a structure represented by formula (4) at its terminal reduces reactivity with moisture, suppressing the increase in hydroxyl groups during storage and presumably allowing stability to be maintained even during long-term storage. Furthermore, the weight-average molecular weight of the entire polymer component being at a certain level or higher suppresses molecular motion, inhibiting the formation of new hydrogen bonds, and presumably allowing stability to be maintained even during long-term storage. Furthermore, in formula (2), X １ It is believed that the inclusion of a polymer component containing a polymer in which the bond is direct increases the cohesive strength of the resin, suppressing molecular movement and inhibiting the formation of new hydrogen bonds, allowing the resin to maintain stability even during long-term storage.

[0025] In the polymer component, the molar ratio of the group represented by formula (4) to the group represented by formula (3) (molar ratio of the group represented by formula (4) / molar ratio of the group represented by formula (3)) is preferably 0.0001 or more and 0.50 or less, more preferably 0.001 or more and 0.40 or less, even more preferably 0.01 or more and 0.35 or less, and particularly preferably 0.1 or more and 0.3 or less. When the molar ratio of the group represented by formula (4) to the group represented by formula (3) in the polymer component is within the above range, the polymer component contains a polymer having an epoxy group terminal, thereby maintaining the physical properties of a high molecular weight epoxy resin, and the polymer component contains a polymer having a group represented by formula (4), thereby exhibiting the effect of suppressing an increase in viscosity.

[0026] In formula (1), formula (4), and formula (7), R ３is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms. Examples of the aliphatic acyl group having 2 to 10 carbon atoms include an acetyl group, a propanoyl group, an isopropanoyl group, a butanoyl group, an isobutanoyl group, a sec-butanoyl group, a tert-butanoyl group, a pentanoyl group, an isopentanoyl group, a hexanoyl group, a heptanoyl group, a cyclohexylcarbonyl group, an octanoyl group, a decanoyl group, and a phenylpropanoyl group. An aliphatic acyl group having 2 to 4 carbon atoms is preferred, and an acetyl group, a propanoyl group, or a butanoyl group is more preferred.

[0027] Examples of aromatic acyl groups having 2 to 10 carbon atoms include benzoyl, methylbenzoyl, methoxybenzoyl, and furylcarbonyl groups, with benzoyl being preferred.

[0028] In formula (2) and formula (4), S １ ~S ３ The alkyl group, alkoxy group, aryl group, alkenyl group, and alkynyl group represented by the formula (I) are not limited to linear groups, and may have a branched structure or a cyclic structure. The positions and numbers of double bonds in the alkenyl group and triple bonds in the alkynyl group are not particularly limited.

[0029] Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a cyclopentyl group, an n-hexyl group, an isohexyl group, a cyclohexyl group, an n-heptyl group, a cycloheptyl group, a methylcyclohexyl group, an n-octyl group, a cyclooctyl group, an n-nonyl group, a 3,3,5-trimethylcyclohexyl group, an n-decyl group, a cyclodecyl group, an n-undecyl group, an n-dodecyl group, a cyclododecyl group, a benzyl group, a methylbenzyl group, a dimethylbenzyl group, a trimethylbenzyl group, a naphthylmethyl group, a phenethyl group, and a 2-phenylisopropyl group.

[0030] Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group, an isopentoxy group, a neopentoxy group, a tert-pentoxy group, a cyclopentoxy group, an n-hexyloxy group, an isohexyloxy group, a cyclohexyloxy group, an n-heptoxy group, a cycloheptoxy group, and a methylcyclohexyloxy group. Examples of the alkyl group include an alkoxy group, an n-octyloxy group, a cyclooctyloxy group, an n-nonyloxy group, a 3,3,5-trimethylcyclohexyloxy group, an n-decyloxy group, a cyclodecyloxy group, an n-undecyloxy group, an n-dodecyloxy group, a cyclododecyloxy group, a benzyloxy group, a methylbenzyloxy group, a dimethylbenzyloxy group, a trimethylbenzyloxy group, a naphthylmethoxy group, a phenethyloxy group, and a 2-phenylisopropoxy group.

[0031] Examples of the aryl group having 6 to 12 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, an ethylphenyl group, a styryl group, a xylyl group, an n-propylphenyl group, an isopropylphenyl group, a mesityl group, an ethynylphenyl group, a naphthyl group, and a vinylnaphthyl group.

[0032] Examples of alkenyl groups having 2 to 12 carbon atoms include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, cyclohexenyl, cyclohexadienyl, cinnamyl, and naphthylvinyl groups.

[0033] Examples of the alkynyl group having 2 to 12 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1,3-butadienyl group, a phenylethynyl group, and a naphthylethynyl group.

[0034] S in formula (2) １ and S ２ are each independently preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group. ３As the substituent, an alkyl group having 1 to 12 carbon atoms is preferred, and a methyl group is more preferred, because if the substituent is not sterically bulky, it is possible to prevent intermolecular aggregation from being hindered and improve flexibility and heat resistance during film formation.

[0035] In formula (2), k1 and k2 each independently represent an integer of 0 to 4, preferably 0 to 2, and more preferably 1 or 2. When both k1 and k2 are 1, the substitution positions are preferably the 2-position and 2'-position. When both k1 and k2 are 2, the substitution positions are preferably the 2-position, 2'-position, 6-position, and 6'-position.

[0036] In formula (4), k3 is an integer of 0 to 4, and preferably 0 to 2. When k3 is 1, the substitution position is preferably the 2-position. When k3 is 2, the substitution positions are preferably the 2-position and the 6-position.

[0037] X in formula (2) １ is a direct bond. １ is a direct bond, the biphenylene skeleton represented by formula (2) may be any one of a 2,2'-biphenylene skeleton, a 2,3'-biphenylene skeleton, a 2,4'-biphenylene skeleton, a 3,3'-biphenylene skeleton, a 3,4'-biphenylene skeleton, and a 4,4'-biphenylene skeleton. A 4,4'-biphenylene skeleton is preferred.

[0038] The polymer component contained in the epoxy resin composition of the present invention may contain a polymer in which A in formula (1) does not contain a chemical structure represented by formula (2) (hereinafter also referred to as "polymer α"). When the polymer component contained in the epoxy resin composition of the present invention contains polymer α, the content of the polymer in which A in formula (1) contains a chemical structure represented by formula (2) is not particularly limited. However, relative to the total amount (100 mol %) of polymer α and the polymer in which A in formula (1) contains a chemical structure represented by formula (2), the content of the polymer in which A in formula (1) contains a chemical structure represented by formula (2) is preferably 10 mol % or more, more preferably 30 mol % or more, and even more preferably 50 mol % or more. The higher the content of the polymer in which A in formula (1) contains a chemical structure represented by formula (2), the higher the Tg, lower the dielectric constant, and lower the dielectric loss tangent. Furthermore, when polymer α is contained, the content of the polymer in which A in formula (1) contains a chemical structure represented by formula (2) is preferably 99 mol% or less, more preferably 95 mol% or less, and even more preferably 90 mol% or less, relative to the total amount (100 mol%) of polymer α and the polymer in which A in formula (1) contains a chemical structure represented by formula (2). If the content of the polymer represented by formula (1) is below the above upper limit, crystallization is easily suppressed. The above upper and lower limits can be arbitrarily combined. For example, it may be 10 mol% or more and 99 mol% or less, 30 mol% or more and 90 mol% or less, or 50 mol% or more and 95 mol% or less.

[0039] In formula (1), n ​​is the average number of repeating units and is 5 or more and 120 or less. From the viewpoint of improving the mechanical strength of the polymer, it is preferably 10 or more, more preferably 15 or more. On the other hand, from the viewpoint of further improving the solvent solubility of the polymer compound and the viscosity of the solution, it is preferably 100 or less, more preferably 80 or less. The above upper and lower limits can be combined arbitrarily. For example, it may be 10 or more and 100 or 15 or more and 80 or less. The number n can be calculated from the number average molecular weight Mn obtained by gel permeation chromatography (GPC). Specific examples of the GPC method will be described in the Examples below.

[0040] <Weight Average Molecular Weight (Mw)> The weight average molecular weight (Mw) of the entire polymer component contained in the epoxy resin composition is preferably 10,000 or more and 100,000. When the weight average molecular weight is equal to or more than the above-mentioned lower limit, mechanical strength tends to be less likely to decrease, and when it is equal to or less than the above-mentioned upper limit, solvent solubility tends to be less likely to decrease, and the solution viscosity is less likely to increase, making it easier to suppress a significant decrease in processability. From the viewpoint of improving mechanical strength, the weight average molecular weight of the polymer is preferably 20,000 or more, more preferably 30,000 or more. On the other hand, from the viewpoint of improving processability, it is preferably 80,000 or less, more preferably 60,000 or less. The above upper and lower limits can be arbitrarily combined. For example, it may be 20,000 or more and 80,000 or less, or 30,000 or more and 60,000 or less. The weight average molecular weight and number average molecular weight of the polymer can be measured by the aforementioned gel permeation chromatography method (GPC method).

[0041] <Epoxy Equivalent> The epoxy equivalent of the entire polymer components contained in the epoxy resin composition is preferably 2,000 to 100,000 g / equivalent. The epoxy equivalent can be measured in accordance with JIS K7236 and is the mass of a resin containing one equivalent of epoxy groups.

[0042] <Method for Producing Polymer> The polymer can be obtained, for example, by reacting a bifunctional epoxy resin represented by the following formula (6), a bifunctional phenol compound represented by the following formula (7), and a monofunctional epoxy compound represented by the following formula (8) in a solvent. The reaction may be carried out in the presence of a catalyst.

[0043]

[0044] In formula (6), A has the same meaning as A in formula (1), and m is an integer of 0 to 5.

[0045]

[0046] In formula (7), S 4 and S 5are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms. k4 and k5 are each independently an integer of 0 to 4. k4 and k5 are preferably 0 to 2, more preferably 0 or 1. When k4 and k5 are both 1, the substitution positions are preferably the 2-position and 2'-position. When k4 and k5 are both 2, the substitution positions are preferably the 2-position, 2'-position, 6-position, and 6'-position. X ２ represents a direct bond, a divalent hydrocarbon group having 1 to 30 carbon atoms, —O—, —S—, or —SO ２ -, -C(CF ３ ) ２ - and -CO-. ３ is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms.

[0047] X ２ Examples of the divalent hydrocarbon group having 1 to 30 carbon atoms in ２ -, -CH(CH ３ ) -, -C(CH ３ ) ２ -, -C(CF ３ ) ２ -, -CHPh-, -C(CH ３ ) Ph-, -CPh ２ 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclohexylene, 1,3-phenylene, 1,4-butylene, 1,4-cyclohexylene, and 1,4-phenylene groups. ２As long as the carbon number is 1 to 30, the alkyl group, arylalkyl group, alkoxy group, arylalkoxy group, aryl group, alkenyl group, arylalkenyl group, alkynyl group, arylalkynyl group, halogen atom, hydroxyl group, carboxy group, sulfone group, amino group, cyano group, nitro group, or the like may have a substituent. Note that the alkyl group, alkoxy group, alkenyl group, and alkynyl group are not limited to linear groups, and may have a branched structure or a cyclic structure. Furthermore, the positions and numbers of double bonds in the alkenyl group and triple bonds in the alkynyl group are not particularly limited.

[0048]

[0049] In formula (8), S ３ and k3 is S in Equation (4). ３ and k3.

[0050] In producing the polymer, it is preferable to carry out the reaction in the presence of a catalyst. As the catalyst, a compound having catalytic ability to promote the reaction between an epoxy group and a phenol can be used. Examples of such catalysts include alkali metal compounds, organic phosphorus compounds, tertiary amines, quaternary ammonium salts, cyclic amines, and imidazoles. The catalyst used in producing the polymer may be used alone or in combination of two or more types.

[0051] Examples of alkali metal compounds include alkali metal hydroxides such as sodium hydroxide, lithium hydroxide, and potassium hydroxide; alkali metal salts such as sodium carbonate, sodium bicarbonate, sodium chloride, lithium chloride, and potassium chloride; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal phenoxides; lithium hydride; and alkali metal salts of organic acids such as sodium acetate and sodium stearate.

[0052] Examples of organic phosphorus compounds include tri-n-propylphosphine, tri-n-butylphosphine, triphenylphosphine, tetramethylphosphonium bromide, tetramethylphosphonium iodide, tetramethylphosphonium hydroxide, trimethylcyclohexylphosphonium chloride, trimethylcyclohexylphosphonium bromide, trimethylbenzylphosphonium chloride, trimethylbenzylphosphonium bromide, tetraphenylphosphonium bromide, triphenylmethylphosphonium bromide, triphenylmethylphosphonium iodide, triphenylethylphosphonium chloride, triphenylethylphosphonium bromide, triphenylethylphosphonium iodide, triphenylbenzylphosphonium chloride, and triphenylbenzylphosphonium bromide.

[0053] Examples of tertiary amines include triethylamine, tri-n-propylamine, tri-n-butylamine, triethanolamine, and benzyldimethylamine.

[0054] Examples of quaternary ammonium salts include tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium hydroxide, triethylmethylammonium chloride, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium iodide, tetrapropylammonium bromide, tetrapropylammonium hydroxide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium hydroxide, benzyltributylammonium chloride, and phenyltrimethylammonium chloride.

[0055] Examples of imidazoles include 2-methylimidazole, 2-ethyl-4-methylimidazole, and 2-phenylimidazole.

[0056] Examples of cyclic amines include 1,8-diazabicyclo(5,4,0)undecene-7 and 1,5-diazabicyclo(4,3,0)nonene-5.

[0057] The amount of catalyst used can be 0.001 to 1% by weight based on the reaction solid content. For example, when an alkali metal compound is used as the catalyst, the amount of alkali metal compound used is preferably 0.5% by weight or less based on the reaction solid content, since this can prevent deterioration of insulating properties due to alkali metal content remaining in the epoxy resin composition.

[0058] A solvent may be used in producing the polymer. The solvent is not limited as long as it dissolves the epoxy resin. Examples of the solvent include aromatic solvents, ketone solvents, amide solvents, and glycol ether solvents. The solvent used in producing the polymer may be a single solvent or a combination of two or more solvents.

[0059] Examples of aromatic solvents include benzene, toluene, and xylene. Examples of ketone solvents include acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, 2-heptanone, 4-heptanone, 2-octanone, cyclohexanone, and acetylacetone. Examples of amide solvents include formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, 2-pyrrolidone, and N-methylpyrrolidone.

[0060] Examples of glycol ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether, propylene glycol mono-n-butyl ether, and propylene glycol monomethyl ether acetate.

[0061] The solvent used in the production of the polymer is preferably toluene, xylene, MEK, or cyclohexanone from the viewpoints of toxicity, solubility, and availability, and more preferably toluene, MEK, or cyclohexanone from the viewpoint of solubility. The solids concentration in the synthesis reaction during the production of the polymer is preferably 35 to 95% by weight. Furthermore, if a highly viscous product is produced during the reaction, the reaction can be continued by adding additional solvent. After the reaction is completed, the solvent can be removed or further added as necessary.

[0062] When producing a polymer using a catalyst, the reaction is carried out at a temperature that does not decompose the catalyst used. If the reaction temperature is not too high, the risk of the catalyst decomposing and stopping the reaction, or the resulting epoxy resin deteriorating, is suppressed. If the reaction temperature is not too low, the reaction can proceed sufficiently. For these reasons, the reaction temperature is preferably 50 to 230°C, more preferably 120 to 200°C. The reaction time can be 1 to 12 hours, preferably 3 to 10 hours. When a low-boiling solvent such as acetone or methyl ethyl ketone is used, the reaction temperature can be ensured by carrying out the reaction under high pressure using an autoclave.

[0063] The epoxy resin composition may further contain a curing agent. Any known curing agent capable of curing an epoxy resin can be used as the curing agent. When a curing agent is contained, it is preferable that the amount of the curing agent is 10 parts by weight or more and 1,000 parts by weight or less per 100 parts by weight of the polymer in the epoxy resin composition.

[0064] The epoxy resin composition may contain a low-molecular-weight epoxy resin. Known epoxy resins that react with a curing agent can be used as the low-molecular-weight epoxy resin. In this specification, an epoxy resin having a number-average molecular weight of 2,000 or less is defined as a low-molecular-weight epoxy resin. When the epoxy resin composition of the present invention contains a low-molecular-weight epoxy resin, the amount of the low-molecular-weight epoxy resin is preferably 10 parts by weight or more and 1,000 parts by weight or less per 100 parts by weight of the polymer component in the epoxy resin composition.

[0065] The epoxy resin composition functions as an insulating layer when cured, and is suitable for use in, for example, electric and electronic components and printed wiring boards.

[0066] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Note that the values ​​of various production conditions and evaluation results in the following examples represent preferred upper or lower limit values ​​in the embodiments of the present invention, and a preferred range may be defined by a combination of the above-mentioned upper or lower limit values ​​and the values ​​in the following examples or values ​​between the examples.

[0067] Analysis Method (1) Weight-average molecular weight (Mw) Using a Tosoh Corporation "HLC-8320 GPC apparatus," the weight-average molecular weight (Mw) was measured under the following measurement conditions using standard polystyrenes: 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). ), F-2 (Mw: 17,200, Mn: 16,900), A-5000 (Mw: 6,400, Mn: 6,100), A-2500 (Mw: 2,800, Mn: 2,700), and A-300 (Mw: 453, Mn: 387). A calibration curve was created using these copolymers, and the weight average molecular weight (Mw) and number average molecular weight (Mn) were measured as polystyrene equivalent values.

[0068] Column: "TSK-GEL SUPER HZ-H + HZ4000 + HZ3000 + HZ2000" manufactured by Tosoh Corporation Eluent: tetrahydrofuran Flow rate: 0.5 ml / min Detection: UV (wavelength 254 nm) Temperature: 40°C Sample concentration: 0.1 wt% Injection amount: 10 μl

[0069] (2) Epoxy Equivalent: Measured in accordance with JIS K7236 and expressed as a value converted into solid content.

[0070] (3) Viscosity The viscosity was measured using a Cannon-Fenske opaque liquid viscometer in accordance with JIS Z8803.

[0071] (4) NMR of the sample was measured using a Bruker AVANCE NEO600 spectrometer. １ H NMR, １３ C NMR was measured. １ The measurement conditions for the H NMR spectrum were a resonance frequency of 600.1 MHz, a flip angle of 45°, a data acquisition time of 3 s, a pulse repetition time of 10 s, an accumulation number of 16, and a temperature of 25°C. １３ The measurement conditions for the C NMR spectrum were a resonance frequency of 150.9 MHz, a flip angle of 45°, a data acquisition time of 2 s, a pulse repetition time of 5 s, an accumulation number of 15,600, and a temperature of 25°C.

[0072] Raw materials, etc. [Bifunctional epoxy resins] (A-1) (3,3',5,5'-tetramethyl-)4,4'-biphenol diglycidyl ether (epoxy equivalent: 186 g / eq) (A-2) 1,6-hexanediol diglycidyl ether (epoxy equivalent: 118 g / eq) (A-3) 1:1 weight ratio mixture of 3,3',5,5'-tetramethyl-4,4'-biphenol diglycidyl ether and 4,4'-biphenol diglycidyl ether (epoxy equivalent: 172 g / eq)

[0073] [Bifunctional phenol compounds] (B-1) bisphenolacetophenone (phenolic hydroxyl group: 145 g / eq) (B-2) bisphenol F (phenolic hydroxyl group: 82 g / eq) (B-3) bisphenolfluorene (phenolic hydroxyl group: 175 g / eq) (B-4) bis-o-cresolfluorene (phenolic hydroxyl group: 189 g / eq) (B-5) bisphenol S (phenolic hydroxyl group: 125 g / eq) (B-6) bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (phenolic hydroxyl group: 155 g / eq) (B-7) 4,4'-dihydroxybiphenyl diacetate (ester group equivalent 135 g / eq) Note that (B-7) does not have a phenolic hydroxyl group, but for convenience it is classified as a bifunctional phenol compound.

[0074] [Catalyst] (C-1) 27% tetramethylammonium hydroxide aqueous solution (C-2) 4-dimethylaminopyridine

[0075] [Solvent] (D-1) Cyclohexanone (D-2) Methyl ethyl ketone (D-3) Toluene

[0076] [Monofunctional epoxy compounds] (E-1) 2,6-dimethylphenol glycidyl ether

[0077] Example 1: A reaction vessel was charged with 29.5 parts of a difunctional epoxy resin (A-1), 23 parts of a difunctional phenol compound (B-1), 0.15 parts of a catalyst (C-1), 28 parts of a solvent (D-1), and 0.46 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 130°C for 7 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-1) (a solution of 35% by weight of cyclohexanone and 35% by weight of methyl ethyl ketone with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-1) were measured, revealing that the Mw was 39,411, the Mn was 15,446, the n number calculated from the number average molecular weight was 23, the viscosity was 14.8 St, and the epoxy equivalent was 13,200. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.30. When the viscosity of polymer (J-1) was measured after storage at room temperature for one year, the viscosity was 17.2 St, and the viscosity deterioration rate was 16%.

[0078]

[0079] Comparative Example 1: A reaction vessel was charged with 36 parts of a bifunctional epoxy resin (A-2), 30 parts of a bifunctional phenol compound (B-2), 0.17 parts of a catalyst (C-1), and 16 parts of a solvent (D-2), and the mixture was stirred to dissolve. The mixture was allowed to react under a nitrogen atmosphere at 145°C for 6 hours. After the reaction was completed, the mixture was diluted with solvent (D-2) to obtain polymer (J-2) (a methyl ethyl ketone solution with a solids content of 40% by mass). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-2) were measured, and the Mw was 50235, Mn was 7502, the n number calculated from the number average molecular weight was 17, the viscosity was 6.5 St, and the epoxy equivalent was 6996. Furthermore, NMR analysis revealed that the polymer did not have a structure corresponding to formula (4). When the viscosity of polymer (J-2) was measured after storage at room temperature for one year, the viscosity was 13.2 St, and the deterioration rate was 103%. Furthermore, when the polymer compound (J-2) was stored at 5° C. for one year and then the viscosity was measured, the viscosity was 8.9 St, and the deterioration rate was 37%.

[0080] Example 2: A reaction vessel was charged with 24 parts of a bifunctional epoxy resin (A-1), 2 parts of bifunctional phenolic compounds (B-1) and (B-3), 0.13 parts of a catalyst (C-1), 25 parts of a solvent (D-1), and 0.37 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 145°C for 5 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-3) (a 35% by weight cyclohexanone-35% by weight methyl ethyl ketone solution with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-3) were measured, revealing that the Mw was 41,256, the Mn was 15,019, the n number calculated from the number average molecular weight was 21, the viscosity was 19.9 St, and the epoxy equivalent was 13,501. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.27. When the polymer (J-3) was stored at room temperature for one year and then its viscosity was measured, it was found to be 28.3 St, and the deterioration rate was 42%.

[0081] Example 3: A reaction vessel was charged with 23 parts of a bifunctional epoxy resin (A-1), 2 parts of bifunctional phenolic compounds (B-1) and (B-4), 0.19 parts of a catalyst (C-1), 25 parts of a solvent (D-1), and 0.36 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 145°C for 5 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-4) (a 35% by weight cyclohexanone-35% by weight methyl ethyl ketone solution with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-4) were measured, revealing that the Mw was 35,813, the Mn was 13,573, the n number calculated from the number average molecular weight was 18, the viscosity was 10.7 St, and the epoxy equivalent was 11,306. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.15. When the polymer (J-4) was stored at room temperature for one year and then its viscosity was measured, it was found to be 13.6 St, and the deterioration rate was 27%.

[0082] Example 4: A reaction vessel was charged with 20 parts of a bifunctional epoxy resin (A-1), 2 parts of bifunctional phenolic compounds (B-1) and (B-4), 18 parts of a catalyst (C-1), 0.23 parts of a catalyst, 24 parts of a solvent (D-1), and 0.32 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 145°C for 6 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-5) (a solution of 35% by weight of cyclohexanone and 35% by weight of methyl ethyl ketone with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-5) were measured, revealing that the Mw was 45,436, the Mn was 16,156, the n number calculated from the number average molecular weight was 22, the viscosity was 21.6 St, and the epoxy equivalent was 16,997. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.28. When the polymer (J-5) was stored at room temperature for one year and then its viscosity was measured, it was found to be 31.0 St, and the deterioration rate was 43%.

[0083] Example 5: A reaction vessel was charged with 33 parts of a bifunctional epoxy resin (A-1), 2.5 parts of bifunctional phenolic compounds (B-1) and (B-4), 27 parts of a catalyst (C-1), 0.1 parts of a catalyst, 21 parts of a solvent (D-1), and 0.51 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 145°C for 7 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-6) (a 30% by weight cyclohexanone-30% by weight methyl ethyl ketone solution with a solids content of 40% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-6) were measured, revealing that the Mw was 20,974, the Mn was 7,660, the number n calculated from the number average molecular weight was 10, the viscosity was 21.9 St, and the epoxy equivalent was 4,134. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.01. When the polymer (J-6) was stored at room temperature for one year and then its viscosity was measured, it was found to be 28.0 St, and the deterioration rate was 28%.

[0084] Example 6: A reaction vessel was charged with 32 parts of a bifunctional epoxy resin (A-1), 21 parts of a bifunctional phenol compound (B-5), 0.27 parts of a catalyst (C-1), 43 parts of a solvent (D-1), and 0.51 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react under a nitrogen atmosphere at 145°C for 3 hours and 155°C for 3 hours. After the reaction was completed, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-7) (a solution of 35% by weight of cyclohexanone and 35% by weight of methyl ethyl ketone with a solids content of 30% by weight). The Mw, Mn, and viscosity of polymer (J-7) were measured, revealing that the Mw was 37,019, the Mn was 15,048, the n number calculated from the number average molecular weight was 24, and the viscosity was 12.1 St. Furthermore, NMR analysis revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.35. When the polymer (J-7) was stored at 5° C. for one year and then the viscosity was measured, it was found to be 12.5 St and the deterioration rate was 3.3%.

[0085] Example 7: A reaction vessel was charged with 30 parts of a bifunctional epoxy resin (A-1), 24 parts of a bifunctional phenol compound (B-6), 0.14 parts of a catalyst (C-1), 28 parts of a solvent (D-2), and 0.46 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react under a nitrogen atmosphere at 135°C for 7 hours. After the reaction was completed, the mixture was diluted with solvent (D-2) to obtain polymer (J-8) (a methyl ethyl ketone solution with a solids content of 35% by mass). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-8) were measured, revealing that the Mw was 33,479, the Mn was 11,755, the number n calculated from the number average molecular weight was 17, the viscosity was 10.0 St, and the epoxy equivalent was 9,621. Furthermore, NMR analysis revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.16. When the viscosity of polymer (J-8) was measured after storage at 5° C. for one year, it was found to be 11.3 St, and the deterioration rate was 13%.

[0086] Example 8: A reaction vessel was charged with 32 parts of a bifunctional epoxy resin (A-1), 22 parts of a bifunctional phenol compound (B-7), 0.06 parts of a catalyst (C-2), 18 parts of a solvent (D-3), and 0.51 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The reaction was carried out under a nitrogen atmosphere at 140°C for 7 hours. After completion of the reaction, the mixture was diluted with solvent (D-3) to obtain polymer (J-9) (a toluene solution with a solids content of 30% by mass). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-9) were measured, revealing that the Mw was 30,400, the Mn was 10,116, the number n calculated from the number average molecular weight was 16, the viscosity was 11.6 St, and the epoxy equivalent was 6,775. Furthermore, NMR analysis revealed that the molar ratio of the structure of formula (10) to the structure of formula (3) was 0.15. When the polymer (J-7) was stored at 5° C. for one year and then the viscosity was measured, it was found to be 13.5 St, and the deterioration rate was 16%.

[0087]

[0088] Example 9: A reaction vessel was charged with 32 parts of a bifunctional epoxy resin (A-3), 24 parts of a bifunctional phenolic compound (B-7), 0.05 parts of a catalyst (C-2), 21 parts of a solvent (D-1), and 0.13 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react under a nitrogen atmosphere at 140°C for 7 hours. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-10) (a 35% by weight cyclohexanone-35% by weight methyl ethyl ketone solution with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-10) were measured, revealing that the Mw was 23,862, the Mn was 8,363, the n number calculated from the number average molecular weight was 13, the viscosity was 6.7 St, and the epoxy equivalent was 6,744. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (10) to the structure of formula (3) was 0.04. When the polymer (J-10) was stored at 5°C for 1 year and then its viscosity was measured, it was found to be 6.8 St, and the deterioration rate was 1.5%.

[0089] Comparative Example 2: A reaction vessel was charged with 33 parts of a bifunctional epoxy resin (A-1), 4 parts of a bifunctional phenolic compound (B-1), 40 parts of a bifunctional phenolic compound (B-4), 0.1 parts of a catalyst (C-1), 22 parts of a solvent (D-1), and 0.51 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 140°C for 6 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-11) (a 30% by weight cyclohexanone-30% by weight methyl ethyl ketone solution with a solids content of 40% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-11) were measured, revealing that the Mw was 8650, the Mn was 3890, the n number calculated from the number average molecular weight was 5, the viscosity was 6.9 St, and the epoxy equivalent was 2134. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.17. When the polymer (J-11) was stored at room temperature for one year and then its viscosity was measured, it was 11.5 St, and the deterioration rate was 67%. When the polymer compound (J-11) was stored at 5°C for one year and then its viscosity was measured, it was 9.1 St, and the deterioration rate was 32%.

[0090] Comparative Example 3: A reaction vessel was charged with 40 parts of a bifunctional epoxy resin (A-3), 24 parts of a bifunctional phenolic compound (B-7), 0.2 parts of a catalyst (C-1), 22 parts of a solvent (D-1), and 0.40 parts of a monofunctional epoxy resin (E-1), and the mixture was stirred to dissolve. The mixture was allowed to react at 145°C for 6 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was diluted with solvents (D-1) and (D-2) to obtain polymer (J-12) (a solution of 35% by weight of cyclohexanone and 35% by weight of methyl ethyl ketone with a solids content of 30% by weight). The Mw, Mn, viscosity, and epoxy equivalent of polymer (J-12) were measured, revealing that the Mw was 33,507, the Mn was 11,470, the n number calculated from the number average molecular weight was 22, the viscosity was 18.9 St, and the epoxy equivalent was 8,770. Furthermore, NMR measurement revealed that the molar ratio of the structure of formula (9) to the structure of formula (3) was 0.11. When the polymer (J-12) was stored at room temperature for one year and then its viscosity was measured, it was found to be 32.2 St, with a deterioration rate of 70%.

[0091]

[0092] In Table 1, items that satisfy each requirement are marked with a circle, and items that do not satisfy each requirement are marked with an x.

[0093] The epoxy resin composition of the present invention can suppress an increase in viscosity even during long-term storage.

Claims

1. An epoxy resin composition comprising a polymer component having a weight average molecular weight of 10,000 or more, wherein the polymer component comprises a polymer represented by the following formula (1): (In formula (1), A includes a chemical structure represented by formula (2); R １ and R ２ may be the same or different and are selected from the group consisting of a hydrogen atom, a group represented by formula (3), and a group represented by formula (4); R ３ represents a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms; and n represents the average number of repeating groups and is 5 to 120. (In formula (2), S １ , and S ２ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k1 and k2 are each independently an integer of 0 to 4; X １ is a direct bond. In formula (4), S ３ is a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k3 is an integer of 0 to 4; R ３ is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms), and at least a part of the polymer component is １ and R ２ is a polymer in which at least one of the R １ and R ２ an epoxy resin composition, wherein at least one of the above is a group represented by formula (4):

2. The epoxy resin composition according to claim 1, wherein the molar ratio of the group represented by formula (4) to the group represented by formula (3) in the polymer component (molar ratio of the group represented by formula (4) / molar ratio of the group represented by formula (3)) is 0.0001 or more and 0.50 or less.

3. The epoxy resin composition according to claim 1, wherein k3 in formula (4) is 2.

4. In the formula (4), S ３ The epoxy resin composition according to claim 1, wherein is an alkyl group having 1 to 12 carbon atoms.

5. In the formula (4), S ３ The epoxy resin composition according to claim 1, wherein is a methyl group.

6. The epoxy resin composition according to any one of claims 1 to 5, further comprising a curing agent.

7. An insulating layer obtained by curing the epoxy resin composition according to claim 6.

8. An electric or electronic part having the insulating layer according to claim 7.

9. A printed wiring board having the insulating layer according to claim 7.

10. Use of the epoxy resin composition according to any one of claims 1 to 5 as a raw material for an insulating layer.

11. A method for producing a polymer, comprising reacting a difunctional epoxy resin represented by formula (6), a difunctional phenol compound represented by formula (7), and a monofunctional epoxy compound represented by formula (8) in a solvent in the presence of a catalyst. (In formula (6), each A independently contains a chemical structure represented by formula (2); m is an integer of 0 to 5. In formula (7), S ４ , and S ５ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k4 and k5 are each independently an integer of 0 to 4; R ３ is a hydrogen atom, an aliphatic acyl group having 2 to 10 carbon atoms, or an aromatic acyl group having 2 to 10 carbon atoms; X ２ represents a direct bond, a divalent hydrocarbon group having 1 to 30 carbon atoms, —O—, —S—, or —SO ２ -, -C(CF ３ ) ２ In formula (8), S is a group selected from - and -CO-. ３ is a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; and k3 is an integer of 0 to 4. (In formula (2), S １ and S ２ are each independently a group selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms; k1 and k2 are each independently an integer of 0 to 4; X １ is a direct bond.)

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