JP7396932B2 - Resin composition and its solution - Google Patents

Description

The present invention relates to a resin composition with excellent low dielectric properties, a cured resin composition using the same with excellent low dielectric properties, and a laminate for electric/electronic circuits.

In general, electrical/electronic circuit boards are made by stacking sheets (prepreg) made of resin-impregnated base materials such as paper or glass, called copper clad laminates (CCL), and applying pressure and heat treatment. The main types are those with copper foil applied to the surface of an insulating board, and those with an insulating adhesive layer formed on a base film, called flexible printed circuit boards (FPC), on which conductive foil such as copper is laminated. used.

Here, thermosetting resins such as epoxy resins, acrylic resins, phenolic resins, polyphenylene ether resins, polyimide resins, and bismaleimide resins are used as prepreg resins and insulating adhesive layers, and are thermally cured by heating and pressure after lamination. This results in a circuit board with excellent heat resistance, adhesiveness, water resistance, mechanical strength, and electrical properties.
In recent years, multilayer circuit boards used in electrical and electronic equipment have become smaller, lighter, and more highly functional. Improvements in workability, etc. are required.

Low dielectric properties are an important performance required of materials and resin materials for electrical and electronic components such as laminates for electrical and electronic circuits. In recent years, communication frequencies have been increasing in order to improve the amount and speed of information transmission, and the increase in transmission loss (α) has become a major issue. The lower the value of the transmission loss (α), the less attenuation of the information signal, which means that high communication reliability can be ensured.
Since transmission loss (α) is proportional to frequency (f), α increases in communication in a high frequency region, leading to a decrease in reliability. One method for suppressing transmission loss (α) is to reduce the dielectric loss tangent (tan δ), which is proportional to α, like the frequency (f). For high-speed transmission of communication signals, materials with a low dielectric loss tangent (tan δ), that is, materials with low dielectric properties are required.

For example, epoxy resin is widely used as a resin for circuit boards because of its excellent adhesiveness and heat resistance, but various improvements and inventions have been made because of its large tan δ.
For example, Patent Document 1 discloses an epoxy resin in which a third component is introduced into a polyphenylene ether-modified epoxy resin, and Patent Document 2 discloses an ester-modified epoxy resin.

JP2019-052278A Japanese Patent Application Publication No. 2017-193649

However, the tan δ of any of the resins described in Patent Document 1 and Patent Document 2 was still insufficient in the high frequency region.
SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide a thermosetting resin composition that is easy to operate and has excellent low dielectric properties in a high frequency range, a cured product thereof, and a laminate for electric/electronic circuits made of the composition. It is in.

As a result of intensive studies aimed at solving the above problems, the present inventor found that the above problems could be solved by using a specific modified cyclic polyolefin and creating a resin composition by blending this with a thermosetting resin. .
That is, the present invention has the following features.

[1] A resin composition comprising a modified cyclic polyolefin, at least one thermosetting resin selected from epoxy resins, acrylic resins, phenolic resins, polyphenylene ether resins, polyimide resins and bismaleimide resins, and a curing agent. , the weight average molecular weight (Mw) of the modified cyclic polyolefin is 60,000 or less, the modified cyclic polyolefin is a cyclic polyolefin modified with an unsaturated carboxylic acid and/or an anhydride thereof, and the cyclic polyolefin is A resin composition comprising a hydrogenated block copolymer which is a hydrogenated block copolymer containing at least one aromatic vinyl monomer unit and at least one conjugated diene monomer unit.

[2] The hydrogenated block copolymer is a hydrogenated aromatic vinyl polymer block unit which is a hydrogenated product of a polymer block made of the aromatic vinyl monomer unit, and a hydrogenated product of a polymer block made of the conjugated diene monomer unit. [ 1].
[3] The hydrogenated aromatic vinyl polymer block unit has a hydrogenation level of 90% or more, and the hydrogenated conjugated diene polymer block unit has a hydrogenation level of 95% or more. Resin composition.

[4] The resin composition according to any one of [1] to [3], wherein the modified cyclic polyolefin has a modification rate of 0.1 to 2% by mass with an unsaturated carboxylic acid and/or its anhydride. thing.
[5] The resin composition according to any one of [1] to [4], wherein the modified cyclic polyolefin has a dielectric loss of less than 0.001 at a measurement frequency of 10 GHz.
[6] The content of the modified cyclic polyolefin is 10 to 60% by mass (based on the entire resin composition), and the total content of the thermosetting resin and curing agent is 40 to 90% by mass (based on the entire resin composition). The resin composition according to any one of [1] to [5], which is (with respect to the entire product).

[7] A resin composition solution in which the resin composition according to any one of [1] to [6] is dissolved in an organic solvent at a solid content concentration of 10 to 90% by mass.
[8] A cured resin composition obtained by curing the resin composition according to any one of [1] to [6].
[9] A laminate for electric/electronic circuits, comprising the resin composition according to any one of [1] to [6].
[10] The cured resin composition according to [8], which has a dielectric loss of less than 0.01 at a measurement frequency of 10 GHz.
[11] The laminate for electric/electronic circuits according to [9], which has a dielectric loss of less than 0.01 at a measurement frequency of 10 GHz.

[12] A method for producing a cured resin composition by curing after removing the solvent from the resin composition solution according to [7].
[13] A method for producing a laminate for electric/electronic circuits by curing the resin composition of the solution described in [7] after removing the solvent.
[14] The method for producing the cured resin composition according to [12], wherein the dielectric loss at a measurement frequency of 10 GHz is less than 0.01.
[15] The method for manufacturing the laminate for electric/electronic circuits according to [13], wherein the dielectric loss at a measurement frequency of 10 GHz is less than 0.01.

By using the resin composition of the present invention, a cured film with an extremely low tan δ can be provided, and is suitable for a circuit board laminate with little transmission loss and suitable for high-speed, high-density communication.

The present invention will be described in detail below, but the following explanation is an example of an embodiment of the present invention, and the present invention is not limited to the following description unless it exceeds the gist thereof.
When the expression "~" is used below, it is used as an expression that includes numerical values or physical property values before and after it.

<Resin composition>
The present invention relates to a resin composition containing a modified cyclic polyolefin, a specific thermosetting resin, and a curing agent.

[Thermosetting resin]
The thermosetting resin used in the present invention is at least one thermosetting resin selected from epoxy resins, acrylic resins, phenol resins, polyphenylene ether resins, polyimide resins, and bismaleimide resins.
All of these thermosetting resins can be obtained using known techniques.

Epoxy resin is the most widely used resin, and various structures and techniques have been disclosed. For example, these are disclosed in JP-A-8-333437, JP-A-2005-97473, and JP-A-2019-172996.

As the phenol resin, a vinylbenzylated phenol compound as described in Japanese Patent No. 6025952 can be used.
As the polyphenylene ether resin, one to which a reactive functional group is added at the end as described in JP-A No. 2017-47648 can be used.

As the polyimide resin, one obtained from a tetracarboxylic acid component and a diamine component as described in 2018/079707 can be used.
As the bismaleimide resin, bismaleimide as described in JP-A-2001-028367 can be used.

[Curing agent]
The curing agent used in the present invention is, for example, a substance that contributes to a crosslinking reaction and/or a chain lengthening reaction between epoxy groups of an epoxy resin.
In addition, in the present invention, even if it is normally called a "curing accelerator", it is considered to be a curing agent if it contributes to the crosslinking reaction and/or chain lengthening reaction between the epoxy groups of the epoxy resin. .

There are no particular restrictions on the curing agent used for the epoxy resin, and any curing agent generally known as an epoxy resin curing agent can be used.
Preferred curing agents for use in acrylic resins, phenolic resins, and bismaleimide resins include phenolic curing agents, amide curing agents, imidazoles, and active ester curing agents from the viewpoint of increasing heat resistance.
These curing agents may be used alone or in combination of two or more.

As the curing agent used for the polyphenylene ether resin, a curing agent that three-dimensionally crosslinks polyphenylene ether can be used. Specifically, a polyfunctional vinyl compound, a vinylbenzyl ether compound, an allyl ether compound, or a trialkenyl isocyanurate can be used as the crosslinked curing agent.

Polyfunctional vinyl compounds include divinylbenzene, divinylnaphthalene, and divinylbiphenyl. Vinylbenzyl ether compounds are synthesized by the reaction of phenol and vinylbenzyl chloride. Allyl ether compounds are synthesized by the reaction of styrene monomer, phenol, and allyl chloride. Trialkenyl isocyanurate has good compatibility, and triallyl isocyanurate or triallyl cyanurate can be used.

Examples of curing agents used for polyimide resins include imidazole compounds such as 1,2-dimethylimidazole, nitrogen atom-containing heterocyclic compounds such as isoquinoline, and basic compounds such as triethylamine and triethanolamine.

[Other ingredients]
Other components that can be added to the resin composition of the present invention include a thermosetting resin catalyst. The catalyst may be any compound having a catalytic ability to promote the reaction between the thermosetting resin alone or the thermosetting resin and the curing agent.

For example, for epoxy resins, tertiary amines, cyclic amines, imidazoles, organic phosphorus compounds, quaternary ammonium salts, etc. may be used. For polyphenylene ether resins, α,α'-bis(t-butylperoxy-m-isopropyl)benzene, 2,5-dimethyl-2,5-di(t-butylperoxy)-3-hexyne, Benzoyl oxide, 3,3',5,5'-tetramethyl-1,4-diphenoquinone, chloranil, 2,4,6-tri-t-butylphenoxyl, t-butylperoxyisopropyl monocarbonate, azobisisobutyl Oxidizing agents such as lonitrile can be used. Here, a carboxylic acid metal salt or the like may be added as necessary to further accelerate the curing reaction.

The resin composition of the present invention may contain components other than those listed above for the purpose of further improving its functionality. For example, thermosetting resins, photocurable resins, curing accelerators (excluding those included in "curing agents"), ultraviolet inhibitors, antioxidants, coupling agents, plasticizers, fluxes, flame retardants, Colorants, dispersants, emulsifiers, elasticity reducing agents, diluents, antifoaming agents, ion trapping agents, inorganic fillers, and organic fillers are included.

[Content of each component]
The content of the modified cyclic polyolefin in the resin composition is preferably 10 to 60% by mass, more preferably 30 to 50% by mass, based on the entire resin composition (100% by mass).
It is preferable that the content of the modified cyclic polyolefin is equal to or higher than the above lower limit because a sufficient dielectric loss reduction effect is exhibited. Moreover, if it is below the said upper limit, since heat resistance and mechanical strength of a cured|cured material can be fully obtained, it is preferable.

The total content of the thermosetting resin and the curing agent in the resin composition is preferably 40 to 90% by mass, and 50 to 70% by mass, based on the entire resin composition (100% by mass). More preferred.
It is preferable that the content of the thermosetting resin and the curing agent be equal to or higher than the lower limit, since various properties of the thermosetting resin are not impaired. Moreover, if it is below the above upper limit, the dielectric loss will not deteriorate, so it is preferable.

The content of the curing agent is preferably 0.1 to 100 parts by mass based on 100 parts by mass of the thermosetting resin. More preferably it is 90 parts by mass or less, and still more preferably 80 parts by mass or less.
When the thermosetting resin is an epoxy resin, the content of the curing agent is preferably 10 to 100 parts by mass based on 100 parts by mass of the epoxy resin. The lower limit is more preferably 20 parts by mass or more. Further, the upper limit thereof is more preferably 90 parts by mass or less, and even more preferably 80 parts by mass or less.
If the content of the curing agent is within the above range, crosslinking of the epoxy resin will be sufficient, and the desired heat resistance and mechanical strength will be exhibited.

<Modified cyclic polyolefin>
The modified cyclic polyolefin of the present invention is a modified product of the cyclic polyolefin described below with an unsaturated carboxylic acid and/or an anhydride thereof. The modification operation of this cyclic polyolefin will be described later.

The lower limit of the weight average molecular weight (hereinafter abbreviated as "Mw") of the modified cyclic polyolefin is preferably 10,000 or more, more preferably 15,000 or more. Moreover, the upper limit of Mw becomes like this. Preferably it is 60,000 or less, Preferably it is 30,000 or less.
It is preferable that the Mw of the modified cyclic polyolefin is equal to or higher than the above lower limit because heat resistance and dielectric properties are improved. Moreover, if Mw is below the above upper limit, the solubility in organic solvents will be good, so it is preferable.
The Mw of the modified cyclic polyolefin is determined by gel permeation chromatography (GPC), and the specific measuring method is as described in the Examples section.

The Mw of the modified cyclic polyolefin can be controlled by the amount of organic peroxide used when modifying the cyclic polyolefin.
The modification operation of the cyclic polyolefin will be described later. In addition, similar to the modification operation of cyclic polyolefin, Mw was changed by blending an organic peroxide with modified cyclic polyolefin, blending it, feeding it into a kneader or extruder, and performing extrusion while heating, melting, and kneading. A modified cyclic polyolefin can be obtained.

By treating cyclic polyolefins and modified cyclic polyolefins with organic peroxides, the carbon-hydrogen bonds of the hydrogenated conjugated diene polymer block unit, which is one of the block units constituting the cyclic polyolefins and modified cyclic polyolefins, are once cleaved. From the resulting carbon radical structure, carbon-carbon bond cleavage accompanied by β-hydrogen elimination occurs, causing a reduction in molecular weight, and a low molecular weight modified cyclic polyolefin can be obtained from a high molecular weight cyclic polyolefin or a modified cyclic polyolefin. .
This operation may be performed after denaturation or simultaneously with denaturation. That is, since molecular weight reduction is carried out simultaneously with modification, by blending a large amount of organic peroxide, molecular weight reduction can be caused simultaneously with modification.

<Characteristics of modified cyclic polyolefin>
The modified cyclic polyolefin used in the present invention is characterized by sufficiently low dielectric loss.
By adding a small amount of modified cyclic polyolefin, it is possible to suppress the dielectric loss of the entire resin composition, and it is expected that the signal transmission efficiency will be improved when used as a laminate for electric/electronic circuits.

The dielectric loss of the modified cyclic polyolefin at a measurement frequency of 10 GHz is preferably less than 0.001, more preferably less than 0.0005.
The dielectric loss of cyclic polyolefins tends to be slightly worsened by modification with unsaturated carboxylic acids and/or their anhydrides. Therefore, in order to keep the dielectric loss low, it is necessary to control the denaturation rate as described below.

<Modification operation of cyclic polyolefin>
Next, the modification operation of the cyclic polyolefin will be explained. This modification operation is carried out by adding an unsaturated carboxylic acid and/or its anhydride as a modifying agent to the cyclic polyolefin and causing the mixture to react.

Examples of the unsaturated carboxylic acid and/or its anhydride as the modifier include acrylic acid, methacrylic acid, α-ethyl acrylic acid, maleic acid, fumaric acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, itaconic acid, Examples include unsaturated carboxylic acids such as citraconic acid, crotonic acid, isocrotonic acid, and nadic acids, and anhydrides thereof.
Further, specific examples of the acid anhydride include maleic anhydride, citraconic anhydride, and nadic anhydride.
In addition, examples of nadic acids or anhydrides thereof include endocys-bicyclo[2.2.1]hept-2,3-dicarboxylic acid (nadic acid (trademark)), methyl-endocys-bicyclo[2.2.1]hept Examples thereof include -5-ene-2,3-dicarboxylic acid (methylnadic acid (trademark)) and its anhydride.

Among these unsaturated carboxylic acids and/or anhydrides thereof, acrylic acid, maleic acid, nadic acid, maleic anhydride, and nadic anhydride are preferred.
One type of unsaturated carboxylic acid and/or its anhydride may be used alone, or two or more types may be used in combination.

A modified cyclic polyolefin can be obtained by modifying the above cyclic polyolefin with the above unsaturated carboxylic acid and/or its anhydride. Suitable methods for modification include solution modification, melt modification, solid phase modification by irradiation with electron beams or ionizing radiation, and modification in a supercritical fluid.
Among these, melt modification with excellent equipment and cost competitiveness is preferred, and melt kneading modification using an extruder with excellent continuous productivity is more preferred.
Examples of devices used at this time include a single screw extruder, a twin screw extruder, a Banbury mixer, and a roll mixer. Among these, single-screw extruders and twin-screw extruders are preferred because of their excellent continuous productivity.

In general, modification of a cyclic polyolefin with an unsaturated carboxylic acid and/or its anhydride cleaves a carbon-hydrogen bond in a hydrogenated conjugated diene polymer block unit, which is one of the block units constituting the cyclic polyolefin, to generate carbon radicals. This is carried out by a graft reaction in which an unsaturated functional group is added to the unsaturated functional group.
As the source of carbon radicals, in addition to the above-mentioned electron beams and ionizing radiation, methods using high temperatures, and radical generators such as organic peroxides, inorganic peroxides, and azo compounds can also be used. As the radical generator, it is preferable to use an organic peroxide from the viewpoint of cost and operability.

Examples of the azo compound include azobisisobutyronitrile, azobisdimethylvaleronitrile, azobis(2-methylbutyronitrile), and diazonitrophenol.
Examples of the inorganic peroxide include hydrogen peroxide, potassium peroxide, sodium peroxide, calcium peroxide, magnesium peroxide, and barium peroxide.

Examples of the organic peroxide include those included in the group of hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxy esters, and ketone peroxides.
Specifically, hydroperoxides such as cumene hydroperoxide and t-butyl hydroperoxide; dicumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-di(t-butyl peroxide); dialkyl peroxides such as oxy)hexane and 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3; diacyl peroxides such as lauryl peroxide and benzoyl peroxide; t-butyl peroxyacetate , t-butylperoxybenzoate, t-butylperoxyisopropyl carbonate, and other peroxyesters; and cyclohexanone peroxide and other ketone peroxides.
These radical generators may be used alone or in combination of two or more.

[Melt-kneading modification]
A commonly used melt-kneading modification operation involves blending a cyclic polyolefin, an unsaturated carboxylic acid and/or its anhydride, and an organic peroxide, charging the mixture into a kneader or extruder, and extruding it while heating, melt-kneading, and extruding the mixture. The molten resin coming out of the tip die is cooled in a water tank or the like to obtain a modified cyclic polyolefin.

The blending ratio of the cyclic polyolefin and the unsaturated carboxylic acid and/or its anhydride is 0.2 to 5 parts by mass of the unsaturated carboxylic acid and/or its anhydride per 100 parts by mass of the cyclic polyolefin.
If the blending ratio of the unsaturated carboxylic acid and/or its anhydride to the cyclic polyolefin is at least the above-mentioned lower limit, a predetermined modification rate necessary for achieving the effects of the present invention can be obtained. Moreover, if it is below the above upper limit, unreacted unsaturated carboxylic acid and/or its anhydride will not remain, which is preferable in terms of dielectric properties.

The blending ratio of the unsaturated carboxylic acid and/or its anhydride to the organic peroxide is 20 to 100 parts by mass of the organic peroxide per 100 parts by mass of the unsaturated carboxylic acid and/or its anhydride. Department.
When the blending ratio of the organic peroxide to the unsaturated carboxylic acid and/or its anhydride is equal to or higher than the lower limit, a predetermined modification rate necessary for achieving the effects of the present invention can be obtained. Moreover, if it is below the said upper limit, deterioration of a cyclic polyolefin will not occur and a hue will not deteriorate.

Further, as the melt-kneading modification conditions, for example, extrusion is preferably carried out at a temperature of 150 to 300°C in a single-screw extruder or a twin-screw extruder.

[Reduction in molecular weight of modified cyclic polyolefin]
When reducing the molecular weight of the modified cyclic polyolefin, the blending ratio of the modified cyclic polyolefin and the organic peroxide is such that the organic peroxide is 0.01 to 2 parts by mass per 100 parts by mass of the modified cyclic polyolefin. .
Further, as the melt-kneading modification conditions, for example, extrusion is preferably carried out at a temperature of 150 to 300° C. in a single screw extruder or a twin screw extruder.

[Denaturation rate]
The modification rate of the modified cyclic polyolefin with the unsaturated carboxylic acid and/or its anhydride is preferably 0.1 to 2% by mass.
If the modification rate is at least the above lower limit, the compatibility with thermosetting resins such as epoxy will be good, resulting in improved coating film strength, which is preferable. Moreover, if it is below the above upper limit, there will be no generation of odor or deterioration of color, and the solubility in organic solvents will be good.
The modification rate of the modified cyclic polyolefin can be measured by ¹ HNMR after subjecting the modified cyclic polyolefin to methyl esterification.

<Cyclic polyolefin>
The cyclic polyolefin used as a raw material for the modified cyclic polyolefin used in the present invention consists of a hydrogenated block copolymer that is a hydrogenated product of a block copolymer containing at least one type of aromatic vinyl monomer unit and at least one type of conjugated diene monomer unit.
The hydrogenated block copolymer comprises a hydrogenated aromatic vinyl polymer block unit which is a hydrogenated product of a polymer block made of the aromatic vinyl monomer unit, and hydrogen which is a hydrogenated product of a polymer block made of the conjugated diene monomer unit. It has a conjugated diene polymer block unit.
Further, the hydrogenated block copolymer has at least two of the hydrogenated aromatic vinyl polymer block units and at least one of the hydrogenated conjugated diene polymer block units.

The cyclic polyolefin used in the present invention is preferably made of the hydrogenated block copolymer described above from the viewpoint of transparency and dielectric properties, specifically low dielectric loss (tangent).
As described later, the term "block" as used herein refers to a polymerized segment of a copolymer that represents microlayer separation from structurally or compositionally different polymerized segments of the copolymer. Thus, for example, "having at least two block units" means that the hydrogenated block copolymer has at least two polymerized segments of the copolymer that represent microlayer separation from structurally or compositionally different polymerized segments. Say something.

The aromatic vinyl monomer serving as the raw material for the aromatic vinyl monomer unit is a monomer represented by general formula (1).

ここでＲは、水素又はアルキル基、Ａｒはフェニル基、ハロフェニル基、アルキルフェニル基、アルキルハロフェニル基、ナフチル基、ピリジニル基又はアントラセニル基である。

Here, R is hydrogen or an alkyl group, and Ar is a phenyl group, a halophenyl group, an alkylphenyl group, an alkylhalophenyl group, a naphthyl group, a pyridinyl group, or an anthracenyl group.

The alkyl group may be mono- or multi-substituted with a functional group such as a halo group, a nitro group, an amino group, a hydroxy group, a cyano group, a carbonyl group, and a carboxyl group. The alkyl group preferably has 1 to 6 carbon atoms.
The above Ar is preferably a phenyl group or an alkylphenyl group, and more preferably a phenyl group.

Aromatic vinyl monomers include, for example, styrene, α-methylstyrene, vinyltoluene (including all isomers, but especially p-vinyltoluene), ethylstyrene, propylstyrene, butylstyrene, vinylbiphenyl, vinylnaphthalene, vinylanthracene. (all isomers), and mixtures thereof.

The conjugated diene monomer described above is not particularly limited as long as it is a monomer having two conjugated double bonds.
Examples of the conjugated diene monomer include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2-methyl-1,3-pentadiene and similar compounds thereof, and mixtures thereof.

Polybutadiene, which is a polymer of 1,3-butadiene, has either a 1,2 configuration that gives an equivalent of a 1-butene repeating unit when hydrogenated, or a 1,4 configuration that gives an equivalent of an ethylene repeating unit when hydrogenated. It can include

The hydrogenated product of the polymerizable block composed of the aromatic vinyl monomer and the conjugated diene monomer containing 1,3-butadiene is included in the hydrogenated block copolymer used in the present invention. Preferably, the hydrogenated block copolymer is a block copolymer without functional groups.
Note that "no functional group" means that the block copolymer does not contain any functional group, ie, a group containing elements other than carbon and hydrogen.

A preferred example of the hydrogenated aromatic vinyl polymer block unit is hydrogenated polystyrene, and a preferred example of the hydrogenated conjugated diene polymer block unit is hydrogenated polybutadiene.
A preferred embodiment of the hydrogenated block copolymer is a hydrogenated triblock or pentablock copolymer of styrene and butadiene, which preferably does not contain any other functional group or structural modifier.

A "block" is defined as a polymerized segment of a copolymer that represents a microlayer separation from structurally or compositionally distinct polymerized segments of the copolymer. Microlayer separation occurs due to the immiscibility of polymerized segments in block copolymers.
Note that microlayer separation and block copolymers are extensively discussed in "Block Copolymers-Designer Soft Materials" in PHYSICS TODAY, February 1999 issue, pages 32-38.

The content of hydrogenated aromatic vinyl polymer block units is preferably 50 to 99 mol%, more preferably 60 to 90 mol%, based on the cyclic polyolefin.
If the ratio of hydrogenated aromatic vinyl polymer block units is at least the above-mentioned lower limit, the rigidity will not decrease, and if it is below the above-mentioned upper limit, the brittleness will not deteriorate.

Further, the content of hydrogenated conjugated diene polymer block units is preferably 1 to 50 mol%, more preferably 10 to 40 mol%, based on the cyclic polyolefin.
If the ratio of hydrogenated conjugated diene polymer block units is at least the above-mentioned lower limit, brittleness will not deteriorate, and if it is below the above-mentioned upper limit, rigidity will not decrease.

As mentioned above, the polyolefin according to the present invention is a "cyclic polyolefin," and the term "cyclic" refers to an alicyclic ring produced by hydrogenation of an aromatic ring contained in the hydrogenated aromatic vinyl polymer block unit. Refers to the formula structure.

Hydrogenated block copolymers of the present invention include triblock, multiblock, tapered block copolymers such as SBS, SBSBS, SIS, SISIS, and SISBS (where S means polystyrene, B means polybutadiene, and I means polyisoprene). and by hydrogenation of block copolymers, including star block copolymers.

The hydrogenated block copolymers of the present invention contain segments of aromatic vinyl polymer at each end. Therefore, the hydrogenated block copolymer of the present invention will have at least two hydrogenated aromatic vinyl polymer block units. And, between these two hydrogenated aromatic vinyl polymer block units, there is at least one hydrogenated conjugated diene polymer block unit.

The pre-hydrogenated block copolymer constituting the hydrogenated block may contain several additional blocks, and these blocks may be bonded at any position on the triblock polymer backbone. Thus, linear blocks include, for example, SBS, SBSB, SBSBS, and SBSBSB. The copolymer may be branched and the polymeric chains may be attached anywhere along the backbone of the copolymer.

The lower limit of Mw of the hydrogenated block copolymer is preferably 10,000 or more, more preferably 20,000 or more. Further, the upper limit of Mw is preferably 120,000 or less, more preferably 100,000 or less, even more preferably 95,000 or less, particularly preferably 90,000 or less, most preferably 85,000 or less, and extremely preferably 80,000 or less. ,000 or less.
If Mw is at least the above-mentioned lower limit, mechanical strength will not decrease, and if it is below the above-mentioned upper limit, the solvent solubility of the obtained modified cyclic polyolefin will improve.
Mw in this specification is determined by GPC measurement.

The hydrogenation level of the block copolymer is preferably at least 90% hydrogenated aromatic vinyl polymer block units and at least 95% hydrogenated conjugated diene polymer block units; more preferably at least 95% hydrogenated aromatic vinyl polymer block units. , 99% or more hydrogenated conjugated diene polymer block units; more preferably 98% or more hydrogenated aromatic vinyl polymer block units; 99.5% or more hydrogenated conjugated diene polymer block units; particularly preferably hydrogenated aromatic vinyl polymer block units; The vinyl polymer block units are 99.5% or more, and the hydrogenated conjugated diene polymer block units are 99.5% or more.
Such high levels of hydrogenation are preferred to reduce dielectric losses.
The hydrogenation level of the hydrogenated aromatic vinyl polymer block unit refers to the rate at which the aromatic vinyl polymer block unit is saturated by hydrogenation, and the hydrogenation level of the hydrogenated conjugated diene polymer block unit refers to the rate at which the aromatic vinyl polymer block unit is saturated by hydrogenation. Indicates the percentage of polymer block units saturated by hydrogenation.

The hydrogenation level of the hydrogenated aromatic vinyl polymer block units and the hydrogenation level of the hydrogenated conjugated diene polymer block units are determined using proton NMR.

The melt flow rate (MFR) of the cyclic polyolefin of the present invention is not particularly limited, but is usually 0.1 g/10 minutes or more, and preferably 0.5 g/10 minutes or more from the viewpoint of the molding method and the appearance of the molded product. be. Further, it is usually 200 g/10 minutes or less, and from the viewpoint of material strength, preferably 100 g/10 minutes or less, more preferably 50 g/10 minutes or less.
MFR was measured in accordance with ISO R1133 at a measurement temperature of 230° C. and a measurement load of 2.16 kg.

One type of cyclic polyolefin may be used alone, or two or more types may be used in combination.
Commercially available cyclic polyolefins can be used as the cyclic polyolefin of the present invention, and specific examples include Zelas (registered trademark) manufactured by Mitsubishi Chemical Corporation.

<Resin composition solution>
The resin composition of the present invention can be dissolved in an organic solvent to form a resin composition solution.
In the present invention, it is possible to use an organic solvent in the process of manufacturing the resin composition, and when a highly viscous product is generated during the reaction of the resin composition, an organic solvent can be added to continue the reaction. You can also.
When an organic solvent is added during the reaction, the organic solvent may be removed or added after the reaction is completed.

When the resin composition is made into a solution, the solid content concentration is preferably 10 to 90% by mass.
Here, the term "solid content" refers to components excluding organic solvents, and includes not only solid resin components but also semi-solid and viscous liquid components.

Examples of the organic solvent used here include ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate; ethers such as ethylene glycol monomethyl ether; N,N-dimethylformamide, Examples include amides such as N,N-dimethylacetamide; alcohols such as methanol and ethanol; alkanes such as hexane and cyclohexane; and aromatics such as toluene and xylene.
These organic solvents may be used alone or in combination of two or more.

<Cured resin composition>
A cured resin composition obtained by curing the resin composition of the present invention has an excellent balance of heat resistance, low water absorption, and low dielectric properties, and exhibits good cured physical properties.
"Curing" here means intentionally curing the resin composition by heat and/or light, and the degree of curing may be controlled depending on desired physical properties and intended use.
The degree of curing may be either complete or semi-cured, but for example, the reaction rate of the thermosetting resin portion is usually 5 to 95%.

The curing method for curing the resin composition of the present invention to form a cured product varies depending on the components and amounts blended in the resin composition, but can be carried out in accordance with the conditions described in each of the above-mentioned prior art techniques.
For example, when the thermosetting resin is an epoxy resin, the heating conditions are usually 80 to 280° C. for 60 to 360 minutes. This heating is preferably carried out in two stages: primary heating at 80-160°C for 10-90 minutes and secondary heating at 120-200°C for 60-150 minutes. In a compound system that exceeds the temperature of the secondary heating, it is preferable to further perform a tertiary heating at 150 to 280° C. for 60 to 120 minutes.
It is preferable to perform secondary heating and tertiary heating in this manner from the viewpoint of reducing curing failure and residual solvent.

Further, when the thermosetting resin is polyphenylene ether, it is preferable to heat it at 170 to 230° C. for an appropriate period of time.
Further, when the thermosetting resin is a bismaleimide resin, it is preferable to perform primary curing at 200 to 400°C and then completely cure at 400 to 500°C.

When producing a semi-cured product, it is preferable to allow the curing reaction of the resin composition to proceed to such an extent that the shape can be maintained by heating or the like. If the resin composition contains a solvent, most of the solvent is usually removed by heating, reduced pressure, air drying, etc., but 5% by mass or less of the solvent may remain in the semi-cured product. .

[Characteristics of cured resin composition]
The cured resin composition of the present invention is characterized by sufficiently low dielectric loss.
The dielectric loss of the cured resin composition at a measurement frequency of 10 GHz is preferably less than 0.01, more preferably less than 0.008. The lower the dielectric loss, the better the electrical signal transmission efficiency and speed when used as a circuit board.

[Manufacture of cured resin composition]
The cured resin composition can be produced by removing the solvent from the resin composition solution and then curing it by the method described above.
In addition, by using the resin composition of the present invention, the dielectric loss of the resin composition cured product obtained by this method can satisfy the above range.

<Application>
The resin composition of the present invention has excellent film forming properties. Further, it has the effect of providing a cured product that has excellent heat resistance and low dielectric properties, and further has excellent low water absorption. Therefore, it can be applied to various fields such as adhesives, paints, materials for civil engineering and construction, and insulating materials for electrical and electronic parts.In particular, it can be used as insulation casting, laminated materials, sealing materials, etc. in the electrical and electronic fields. Useful.

Examples of uses of the resin composition of the present invention include copper foil laminates, flexible printed circuit boards, multilayer printed wiring boards, laminates for electrical and electronic circuits such as capacitors, adhesives such as film adhesives, and liquid adhesives. Examples include, but are not limited to, semiconductor sealing materials, underfill materials, interchip fills for 3D-LSI, insulating sheets, prepregs, and heat sinks.

<Laminated body containing conductive metal layer>
The resin composition of the present invention can be made into a conductive metal layer-containing laminate by forming a layer made of the resin composition on the conductive metal layer.
This conductive metal layer-containing laminate is a laminate of a resin composition film layer of the present invention and a conductive metal layer, and a laminate of a resin composition film layer of the present invention and a conductive metal layer. If so, it can be used for electrical/electronic circuits, circuits with capacitors, etc.
Note that layers made of two or more types of resin compositions may be formed in the conductive metal layer-containing laminate, and the resin composition of the present invention may be used in at least one layer. Moreover, two or more types of conductive metal layers may be formed.

The conductive metal layer-containing laminate can be produced by a coating method such as directly applying a resin composition solution onto the conductive metal or by dipping the conductive metal in a resin composition solution, or by applying a coating method such as applying a resin composition solution directly onto the conductive metal or by dipping the conductive metal in a resin composition solution. A resin composition-containing material obtained by a coating method such as applying a resin composition solution to the core material, or dipping the core material in a resin composition solution, is laminated onto a conductive metal. This can be produced by obtaining a laminate, removing the solvent during or after lamination, and then curing in the manner described above.

Examples of the core material include nonwoven fabrics and cloths made of inorganic and/or organic fiber materials such as glass fibers, polyester fibers, aramid fibers, cellulose, and nanofiber cellulose.

Note that by using the resin composition of the present invention, the dielectric loss of the conductive metal layer-containing laminate obtained by this method can satisfy the above range.

[Electrical/electronic circuit laminate]
When the conductive metal layer-containing laminate is a laminate for electric/electronic circuits, the thickness of the layer made of the resin composition in the laminate for electric/electronic circuits is usually about 10 to 200 μm. Further, the thickness of the conductive metal layer is usually about 0.2 to 70 μm.

The electrical/electronic circuit laminate of the present invention is characterized by sufficiently low dielectric loss.
The dielectric loss of the laminate for electric/electronic circuits at a measurement frequency of 10 GHz is preferably less than 0.01, more preferably less than 0.008. The lower the dielectric loss, the better the electrical signal transmission efficiency and speed when used as a circuit board.

[Conductive metal]
Examples of the conductive metal in the laminate for electric/electronic circuits include metals such as copper and aluminum, and alloys containing these metals. In the present invention, a metal foil of these metals or a metal layer formed by plating or sputtering can be used as the conductive metal layer of the laminate for electric/electronic circuits.

[Method for manufacturing laminates for electrical/electronic circuits]
As a specific method for manufacturing the laminate for electric/electronic circuits in the present invention, the following method may be mentioned, for example.
(1) A nonwoven fabric or cloth made of inorganic and/or organic fiber materials such as glass fiber, polyester fiber, aramid fiber, cellulose, nanofiber cellulose, etc. is impregnated with the resin composition of the present invention or a solution containing the same. If a solution is used, remove the solvent appropriately, provide a conductive metal layer using conductive metal foil and/or plating, and then form a circuit using photoresist etc. Stack several layers to form a laminate.

(2) The prepreg in (1) above is used as the core material, and a layer made of a resin composition or a solution containing the resin composition (the solvent is appropriately removed) and a conductive metal layer are laminated (on one side or both sides) (build). up method). The layer made of this resin composition may contain organic and/or inorganic fillers.
(3) A laminate for electric/electronic circuits is produced by alternately laminating only layers made of a resin composition or a solution containing the resin composition (the solvent is removed as appropriate) and a conductive metal layer without using a core material.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way. In addition, in the following examples and comparative examples, various physical properties were measured by the following methods.

<Molecular weight>
・Equipment: GPC HLC-832GPC/HT manufactured by Tosoh Corporation
・Detector: MIRAN 1A infrared spectrophotometer (measurement wavelength, 3.42 μm)
・Column: 3 AD806M/S manufactured by Showa Denko Co., Ltd. (Column calibration was performed using monodispersed polystyrene manufactured by Tosoh (0.5 mg/ml each of A500, A2500, F1, F2, F4, F10, F20, F40, F288) solution) was measured, and the logarithm of the elution volume and molecular weight was approximated by a cubic equation.
・Measurement temperature: 135℃
・Concentration: 20mg/10mL
・Injection amount: 0.2ml
・Solvent: o-dichlorobenzene ・Flow rate: 1.0ml/min

<Polymer block ratio>
[Measurement by carbon NMR]
・Device: Bruker “AVANCE 400 spectrometer”
・Solvent: o-dichlorobenzene-h ₄ /p-dichlorobenzene-d ₄ mixed solvent ・Concentration: 0.3g/2.5mL
・Measurement: ^13C -NMR
・Resonance frequency: 400MHz
・Accumulation count: 3600
・Flip angle: 45 degrees ・Data acquisition time: 1.5 seconds ・Pulse repetition time: 15 seconds ・Measurement temperature: 100℃
・^1H irradiation: complete decoupling

<Hydrogenation level of hydrogenated aromatic vinyl polymer block unit and hydrogenated conjugated diene polymer block unit>
[Measurement by proton NMR]
・Device: Bruker “AVANCE 400 spectrometer”
・Solvent: Tetrachloroethane ・Concentration: 0.045g/1.0mL
・Measurement: ^1H -NMR
・Resonance frequency: 400MHz
・Flip angle: 45 degrees ・Data acquisition time: 4 seconds ・Pulse repetition time: 10 seconds ・Number of integration: 64
・Measurement temperature: 80℃
・Hydrogenation level of hydrogenated aromatic vinyl polymer block unit: Integral value reduction rate of 6.8 to 7.5 ppm ・Hydrogenation level of hydrogenated conjugated diene polymer block unit: Integral value reduction of 5.7 to 6.4 ppm rate

<Modification rate of modified cyclic polyolefin>
[Measurement by proton NMR]
・Device: BRUKER “AVANCE 400 Spectrometer”
・Solvent: Heavy orthodichlorobenzene ・Concentration: 20mg/0.62mL
・Measurement: ^1H -NMR
・Resonance frequency: 400MHz
・Flip angle: 45 degrees ・Data acquisition time: 4 seconds ・Pulse repetition time: 10 seconds ・Number of integration: 64
・Measurement temperature: 120℃
・Modification rate of acid-modified cyclic polyolefin: Integral value reduction rate of 3.42 to 3.94 ppm

<Permittivity and dielectric loss measurement>
Measurements were performed using a transmission attenuation measurement jig equipped with a dielectric lens.
・Device: KEYSIGHT “Vector Network Analyzer N5227A”
"Millimeter wave module WR10-VNAX" manufactured by VIRGINIA DIODES
"Network Analyzer E8361A" manufactured by KEYSIGHT
・Measurement environment: 26℃, humidity 40%
・Measurement frequency: 10GHz

The modified cyclic polyolefin was heat-pressed at 200°C to form a sheet with a thickness of 1 mm and a size of 10 cm x 10 cm, and this sheet was used for measurement.
The cured product was peeled off from the release PET film using the method described in Example 1, cut into a size of 10 cm x 10 cm, and used for measurement.

<Solution state>
The uniformity and fluidity of the liquid were determined by visual observation.
○: The liquid state is uniform, and the liquid surface flows quickly when the container is tilted. △: The liquid state is not uniform, but when the container is tilted, the liquid surface flows quickly. ×: The liquid state is uniform. The liquid does not flow even when the container is tilted.

<Coating film condition>
Judgment was made by visual observation based on the presence or absence of bubbles, clumps, unpainted areas, and flickering.
○: No air bubbles, clumps, unpainted areas, or repellents △: Slight bubbles, clumps, unpainted areas, or repellents ×: Many air bubbles, clumps, unpainted areas, or repellents

<Cured film condition>
Judgment was made by visual observation based on the presence or absence of bubbles, clumps, unpainted areas, and flickering.
○: No air bubbles, clumps, unpainted areas, or repellents △: Slight bubbles, clumps, unpainted areas, or repellents ×: Many air bubbles, clumps, unpainted areas, or repellents

<Raw materials>
[Cyclic polyolefin]
・a-1:
As the cyclic polyolefin, Zelas MC930 manufactured by Mitsubishi Chemical Co., Ltd. was used, and maleic anhydride and organic peroxide (manufactured by NOF Corporation: Perhexa 25B (2,5?dimethyl?2,5?di(t?)) were used as the cyclic polyolefin. Butylperoxy)hexane)) was stirred well at a mixing ratio of 1.3 parts by mass of maleic anhydride and 0.0065 parts by mass of organic peroxide per 100 parts by mass of cyclic polyolefin, and then twin-screw extruded. Using a machine (manufactured by Nippon Steel Corporation, TEX25αIII), the cylinder temperature was 280°C, the screw rotation speed was 400 rpm, and the discharge rate was 10 kg/h, and the extruded molten strand was water-cooled and cut to form a modified ring shape. Polyolefin a-1 was obtained. Table 1 shows the physical properties of the obtained a-1.

[Modified cyclic polyolefin]
・A-1:
Modified cyclic polyolefin A-1 was obtained in the same manner as a-1 except that the amount of maleic anhydride was 1.0 parts by mass and the amount of organic peroxide was 2 parts by mass. The physical properties of A-1 are shown in Table 1.

・A-2:
After stirring thoroughly at a blending ratio of 100 parts by mass of a-1 and 1 part by mass of Perhexa 25B, modified cyclic polyolefin A-2 was obtained in the same manner as a-1. The physical properties of A-2 are shown in Table 1.

・a-2:
As the cyclic polyolefin, Zelas MC930 manufactured by Mitsubishi Chemical Corporation was used as it was without any modification treatment. The physical properties of a-2 are shown in Table 1.

・a-3:
As a maleic acid modified product of a hydrogenated styrene-butadiene block copolymer, Tuftec M1943 manufactured by Asahi Kasei Corporation was used.
A-3 is a polyolefin modified with maleic acid, but the aromatic vinyl polymer block unit of the raw material polyolefin is not hydrogenated. Table 1 shows the physical properties of a-3.

[Thermosetting resin]
・B-1:
Manufactured by Mitsubishi Chemical Corporation: Product name "jER YX7700" (xylenol skeleton-containing novolac type epoxy resin, epoxy equivalent: 271 g/equivalent, Mn: 660, average number of epoxy groups in 1 molecule: 2.4); 85 g, benzoic 38.41 g of 2-naphthyl acid (active equivalent: 248 g/equivalent) and 0.01 g of 4-(dimethylamino)pyridine were placed in a reaction vessel equipped with a stirrer, and the reaction was carried out at a reaction temperature of 140° C. under a nitrogen gas atmosphere. The reaction was carried out for 6 hours to obtain a solid epoxy resin. The obtained epoxy resin was used.

・B-2:
Mitsubishi Chemical Corporation's product name "jER1007" (bisphenol-A type epoxy resin, epoxy equivalent: 2000 g/equivalent, Mn: 2900) was used.

[Curing agent]
・C-1:
The product manufactured by Sumitomo Chemical Co., Ltd. under the trade name "Unifire W575" (functional group equivalent: 220 g/equivalent, number average molecular weight: 3500) was used.

・C-2:
"PSM-4261" (phenol resin) manufactured by Gun-ei Chemical Industry Co., Ltd. was used.

[catalyst]
The product manufactured by Shikoku Kasei Kogyo Co., Ltd. under the trade name "Curezol 2E4MZ" (imidazole-based epoxy resin curing accelerator) was used.

<Example 1>
According to Table 2, 5 g of modified cyclic polyolefin A-1, 9 g of thermosetting resin B-1, 68 mL of toluene as a solvent, and 16.3 g of methyl ethyl ketone (MEK) were placed in a 200 mL separable flask and heated to 60°C while stirring. It was heated to form a solution. Next, the liquid temperature was lowered to 40° C., 1.65 g of curing agent C-2 was added, and when it was completely dissolved with stirring, 0.05 g of catalyst was added, and the mixture was further stirred and dissolved for 20 minutes.
The obtained solution was coated on the release surface of a release PET film (Toray Film Processing Co., Ltd., Therapel PJ271) at a coating thickness of 10 mils, and after removing the solvent with a dryer, it was heated in an oven at 160°C. A heat treatment was performed for 2 hours to perform a hardening treatment.
The obtained film was peeled off from the release PET film, and the dielectric loss tangent was measured. The results are shown in Table 2.

<Example 2>
The procedure was the same as in Example 1 except that C-1 was used as the curing agent and only toluene was used as the solvent, except that solutions were prepared at the ratios shown in Table 2, and the dielectric loss tangent was measured in the same manner.

<Example 3>
The procedure was the same as in Example 2 except that A-2 was used as the modified cyclic polyolefin, except that solutions were prepared at the ratios shown in Table 2, and the dielectric loss tangent was measured in the same manner.

<Comparative example 1>
A solution was prepared at the ratio shown in Table 2 without using the modified cyclic polyolefin, and the dielectric loss tangent was measured in the same manner as in Example 1.

<Comparative example 2>
The procedure was the same as in Comparative Example 1 except that B-2 was used as the thermosetting resin and C-2 was used as the curing agent, except that solutions were prepared at the ratios listed in Table 2, and the dielectric loss tangent was measured in the same manner.

<Comparative example 3>
A solution was prepared and a cured film was prepared in the same manner as in Example 2 except that a-1 was used as the modified cyclic polyolefin. The resulting cured film was brittle and broke into pieces when it was peeled off from the release PET film, making it impossible to measure the dielectric loss tangent.

<Comparative example 4>
A solution was prepared and a cured film was prepared in the same manner as in Example 2, except that a-2 was used instead of A-1 as the modified cyclic polyolefin. The resulting cured film was brittle and broke into pieces when it was peeled off from the release PET film, making it impossible to measure the dielectric loss tangent.

<Comparative example 5>
A solution was prepared in the same manner as in Example 2 except that a-3 was used instead of A-1 as the modified cyclic polyolefin. An attempt was made to coat the solution onto a release PET film, but the solution gelled and became non-uniform, making it impossible to coat.

<Results>
From these results, a block copolymer having an aromatic vinyl polymer block unit that is insufficiently hydrogenated (a-3: Comparative Example 5), a cyclic polyolefin that is sufficiently hydrogenated but not acid-modified ( a-2: Comparative Example 4) and acid-modified cyclic polyolefin with too large Mw (a-1: Comparative Example 3), the composition with thermosetting resin showed a good cured film. I found out that I can't get it.

On the other hand, it was found that the thermosetting resin compositions (Examples 1 and 2) using modified cyclic polyolefins with controlled Mw provided thermosetting films with significantly improved dielectric loss.

Claims (15)

A resin composition comprising a modified cyclic polyolefin, at least one thermosetting resin selected from epoxy resins, acrylic resins, phenolic resins, polyphenylene ether resins, polyimide resins and bismaleimide resins, and a curing agent,
The weight average molecular weight (Mw) of the modified cyclic polyolefin is 60,000 or less,
The modified cyclic polyolefin is a cyclic polyolefin modified with an unsaturated carboxylic acid and/or an anhydride thereof,
The cyclic polyolefin consists of a hydrogenated block copolymer that is a hydrogenated product of a block copolymer containing at least one aromatic vinyl monomer unit and at least one conjugated diene monomer unit,
The hydrogenated block copolymer is a hydrogenated aromatic vinyl polymer block unit which is a hydrogenated product of a polymer block made of the aromatic vinyl monomer unit, and a hydrogenated product which is a hydrogenated product of a polymer block made of the conjugated diene monomer unit. A resin composition having a conjugated diene polymer block unit . The resin composition according to claim 1 , wherein the hydrogenated block copolymer has at least two of the hydrogenated aromatic vinyl polymer block units and at least one of the hydrogenated conjugated diene polymer block units. The resin composition of claim 2, wherein the hydrogenated aromatic vinyl polymer block units have a hydrogenation level of 90% or more, and the hydrogenated conjugated diene polymer block units have a hydrogenation level of 95% or more. . The resin composition according to any one of claims 1 to 3, wherein the modified cyclic polyolefin has a modification rate of 0.1 to 2% by mass with an unsaturated carboxylic acid and/or its anhydride. The resin composition according to any one of claims 1 to 4, wherein the modified cyclic polyolefin has a dielectric loss of less than 0.001 at a measurement frequency of 10 GHz. The content of the modified cyclic polyolefin is 10 to 60% by mass (based on the entire resin composition), and the total content of the thermosetting resin and curing agent is 40 to 90% by mass (based on the entire resin composition). The resin composition according to any one of claims 1 to 5, which is (as opposed to). A resin composition solution in which the resin composition according to any one of claims 1 to 6 is dissolved in an organic solvent at a solid content concentration of 10 to 90% by mass. A cured resin composition obtained by curing the resin composition according to any one of claims 1 to 6. A laminate for electric/electronic circuits, comprising the resin composition according to any one of claims 1 to 6. The cured resin composition according to claim 8, having a dielectric loss of less than 0.01 at a measurement frequency of 10 GHz. The laminate for electric/electronic circuits according to claim 9, wherein the dielectric loss at a measurement frequency of 10 GHz is less than 0.01. A method for producing a cured resin composition by curing the resin composition solution according to claim 7 after removing the solvent. A method for producing a laminate for electric/electronic circuits by curing the resin composition of the solution according to claim 7 after removing the solvent. The method for producing a cured resin composition according to claim 12, wherein the dielectric loss at a measurement frequency of 10 GHz is less than 0.01. The method for manufacturing a laminate for electric/electronic circuits according to claim 13, wherein the dielectric loss at a measurement frequency of 10 GHz is less than 0.01.