KR20240052681A - Resin composition - Google Patents

Abstract

[Problem] To provide a resin composition that can suppress the dielectric loss tangent to a lower level even in a high-temperature environment and at the same time obtain a cured product with excellent crack resistance after desmear treatment.
[Solution] A resin composition comprising (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound.

Description

Resin composition {RESIN COMPOSITION}

The present invention relates to a resin composition containing an epoxy resin. It also relates to a cured product, a sheet-like laminated material, a resin sheet, a printed wiring board, and a semiconductor device obtained by using the resin composition.

As a manufacturing technology for printed wiring boards, a manufacturing method using a build-up method is known in which insulating layers and conductor layers are stacked alternately. In the manufacturing method using the build-up method, generally, the insulating layer is formed by curing the resin composition. As an insulating layer of a printed wiring board of a semiconductor device, it is required to exhibit good dielectric properties (low dielectric constant, low dielectric loss tangent) to suppress transmission loss when operating in a high frequency environment.

As a resin composition that forms a cured product showing good dielectric properties, for example, Patent Document 1 reports a resin composition containing an active ester compound as a curing agent for an epoxy resin.

Japanese Patent Publication No. 2009-235165

A resin composition containing an active ester compound as a curing agent, as described in Patent Document 1, forms a cured product with excellent dielectric properties compared to the case of using a general phenol-based curing agent, but cracks are less likely to occur after desmear treatment. It tends to get easier. In addition, semiconductor devices may be exposed to high-temperature environments, such as when operating in a high-frequency environment. Even if the material exhibits good dielectric properties under a room temperature environment, the dielectric properties (especially dielectric loss tangent) may deteriorate under a high-temperature environment. It was discovered that there are cases where the desired dielectric properties cannot be achieved under actual use environments.

The object of the present invention is to provide a resin composition that can suppress the dielectric loss tangent to a low level even in a high temperature environment and at the same time obtain a cured product with excellent crack resistance after desmear treatment, a cured product obtained using the resin composition, and a sheet-like laminate material. , resin sheets, printed wiring boards, and semiconductor devices.

In order to achieve the object of the present invention, the present inventors have carefully studied and found that by using an epoxy resin and an active ester compound as components of the resin composition and also containing an organic filler having liquid crystallinity, surprisingly, even in a high temperature environment. It was discovered that a cured product could be obtained that could suppress the dielectric loss tangent to a low level and suppress the occurrence of cracks after desmear treatment, leading to the completion of the present invention.

That is, the present invention includes the following contents.

[One]

A resin composition comprising (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound.

[2]

The resin composition according to [1] above, wherein the content of component (A) is 0.1% by mass or more and 10% by mass or less when the resin component in the resin composition is 100% by mass.

[3]

(A) The resin composition according to [1] or [2] above, wherein the organic filler having liquid crystallinity has a melting point of 270°C or higher.

[4]

(D) The resin composition according to any one of [1] to [3] above, further comprising an inorganic filler.

[5]

(E) The resin composition according to any one of [1] to [4] above, further comprising a radically polymerizable compound.

[6]

The resin composition according to any one of [1] to [5] above, for forming an interlayer insulating layer of a printed wiring board.

[7]

A cured product of the resin composition according to any one of [1] to [6] above.

[8]

A sheet-like laminated material containing the resin composition according to any one of [1] to [6] above.

[9]

A resin sheet comprising a support and a resin composition layer formed of the resin composition according to any one of [1] to [6] provided on the support.

[10]

A printed wiring board comprising an insulating layer made of a cured product of the resin composition according to any one of [1] to [6] above.

[11]

A semiconductor device comprising the printed wiring board according to [10] above.

According to the present invention, a resin composition that can suppress the dielectric loss tangent to a lower level even in a high temperature environment and at the same time obtain a cured product with excellent crack resistance after desmear treatment; A cured product of the resin composition; Sheet-like laminated materials and resin sheets containing the above resin composition; And a printed wiring board and a semiconductor device containing a cured product of the resin composition can be provided.

Hereinafter, the present invention will be described in detail by showing embodiments and examples. However, the present invention is not limited to the following embodiments and examples, and may be implemented with arbitrary changes without departing from the scope of the claims and equivalents thereof.

In the following description, the amount of each component is the amount of the non-volatile component, unless otherwise specified.

In the following description, “non-volatile components in the resin composition” may include (D) inorganic fillers, unless otherwise specified, and “resin components” may include the non-volatile components contained in the resin composition, unless otherwise specified. Among non-volatile components, it refers to components excluding (D) inorganic fillers.

<Resin composition>

The resin composition of the present invention contains (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound. By using such a resin composition, the dielectric loss tangent can be kept low even in a high temperature environment such as 90°C, and a cured product with excellent crack resistance after desmear treatment can be obtained. In addition, in the present invention, a cured product with a low dielectric loss tangent can be obtained even in the room temperature range, such as 23°C.

The resin composition of the present invention may further contain arbitrary components in addition to (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound. Optional components include, for example, (D) inorganic filler, (E) radically polymerizable compound, (F) other curing agent, (G) curing accelerator, (H) other additive, and (K) organic solvent. . In this specification, each component (A) to (K) above may be referred to as “component (A)”, “component (B)”, etc., respectively. Hereinafter, each component included in the resin composition will be described in detail.

<(A) Organic filler with liquid crystallinity>

(A) The organic filler having liquid crystallinity is specifically a filler containing an organic polymer having liquid crystallinity, and may be a filler consisting of an organic polymer having liquid crystallinity. (A) Component may be used individually, or may be used in combination of two or more types. In the present specification, “having liquid crystallinity” means that anisotropy is observed by polarizing microscope observation when heated above the melting point.

Examples of organic polymers having liquid crystallinity include general liquid crystal polymers, for example, parahydroxybenzoic acid, biphenol, wholly aromatic polyester synthesized from terephthalic acid, etc., and specifically, parahydroxybenzoic acid, biphenol, terephthalic acid, etc. Structural units derived from benzoic acid ([-OC ₆ H ₄ -CO-]), structural units derived from biphenol ([-OC ₆ H ₄ -C ₆ H ₄ -O-]) and structural units derived from terephthalic acid. and polymers having at least one structural unit selected from the group consisting of ([-OC-C ₆ H ₄ -CO-]). The structural unit referred to in this specification includes a repeating unit present in the main chain of the polymer and a unit or terminal group present in the terminal or side chain. As the liquid crystal polymer, for example, liquid crystal polymer particles described in Japanese Patent Application Laid-Open No. 2022-79336 can be preferably used.

The melting point of the organic polymer having liquid crystallinity is preferably 270°C or higher, more preferably 280°C or higher, and still more preferably 290°C or higher. The upper limit is preferably 370°C or lower, and preferably 360°C. or less, and more preferably 350°C or less. In this specification, the melting point of the liquid crystal polymer is based on the test method of ISO11357 and ASTM D3418, and can be measured using a differential scanning calorimeter (DSC) manufactured by Hitachi High-Tech Science Co., Ltd., etc.

When the organic polymer having liquid crystallinity has the above melting point, it fuses well with the epoxy resin (B) and the active ester compound (C), which generally have relatively small average molecular weights, even under general curing conditions in the resin composition of the present invention. It is difficult to achieve this, and it tends to contribute to stress relaxation of the cured product obtained using the resin composition, and tends to improve crack resistance after desmear treatment.

As the filler that is component (A), particles, powders or powders are preferable, and the particle size distribution of the powder is, for example, D50 (median diameter), which represents the particle diameter accumulated by 50% from the smaller particle diameter. , 0.1 μm or more, preferably 0.3 μm or more, more preferably 0.4 μm or more, further preferably 0.5 μm or more, even more preferably 1 μm or more, particularly preferably 3 μm or more, for example, It is desirable that it is 12㎛ or less, 10㎛ or less, preferably 8㎛ or less, more preferably 6㎛ or less, further preferably 5.5㎛ or less, and particularly preferably 5㎛. The particle diameter can be measured by a laser diffraction/scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be prepared on a volume basis using a laser diffraction scattering type particle size distribution measuring device, and the intermediate diameter can be measured as the average particle size.

For organic polymers having liquid crystallinity, the amount of acetic acid in outgas generated when heat-treated at 190°C for 1 hour is, for example, 10 ppm or less, preferably 5 ppm or less, and more preferably 1 ppm or less. The amount of acetic acid in the outgas of the liquid crystalline organic polymer can be controlled by adjusting the conditions in the synthesis process of the liquid crystal polymer as a raw material, for example, the heating temperature and time of solid phase polymerization. If the amount of acetic acid in the outgas is small as described above, it is easy to reduce the increase in dielectric loss tangent in the cured product obtained using the resin composition even in a situation where molecular motion generally increases under a high temperature environment.

The dielectric loss tangent (measurement frequency: 10 GHz) of an organic polymer having liquid crystallinity is 0.001 or less, preferably 0.0009 or less, more preferably 0.0008 or less, and still more preferably 0.0007 or less. The above value is a measured value of the dielectric loss tangent in the in-plane direction of an injection molded product of an organic polymer having liquid crystallinity. Meanwhile, the injection molded product is a flat test piece of 30 mm x 30 mm x 0.4 mm (thickness).

The resin composition of the present invention is not necessarily clear in terms of mechanism, etc., but it is liquid crystalline, that is, it contains component (A) with a rigid portion in the molecule, so that the cured product obtained by using the resin composition is generally used in a high temperature environment. This can reduce the increase in dielectric loss tangent even in situations where molecular motion increases, and at the same time, since component (A) does not react with the active ester compound (C), it contributes to stress relief in the cured product and desmear treatment. It is presumed that this may improve crack resistance later. Component (A) is preferably insoluble in the epoxy resin (B), and more preferably, even if the resin composition of the present invention contains a resin other than component (B), it is insoluble in the resin in the resin composition, More preferably, even if the resin composition of the present invention further contains (K) an organic solvent, it is insoluble in the resin and organic solvent in the resin composition.

The content of component (A) is, for example, 0.1 mass% or more, preferably 0.3 mass% or more, more preferably 0.4 mass% or more, with respect to 100 mass% of non-volatile components in the resin composition. It is 0.5 mass% or more, more preferably 0.55 mass% or more, and for example, 5 mass% or less, preferably 4 mass% or less, more preferably 3.5 mass% or less, even more preferably 3. It is mass % or less, more preferably 2.5 mass % or less.

The content of component (A) is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, and still more preferably 1.5% by mass, based on 100% by mass of the resin component in the resin composition. It is % by mass or more, more preferably 2% by mass or more, and for example, 12% by mass or less, preferably 10% by mass or less, more preferably 9.5% by mass or less, even more preferably 9% by mass. % or less, more preferably 8.5 mass% or less.

<(B) Epoxy resin>

The resin composition of the present invention contains (B) an epoxy resin. (B) Epoxy resin means a curable resin having an epoxy group.

(B) As the epoxy resin, for example, bixylenol type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, and tris. Phenol type epoxy resin, naphthol novolac type epoxy resin, phenol novolak type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin. , glycidyl ester type epoxy resin, cresol novolak type epoxy resin, phenol aralkyl type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin. , spiro ring-containing epoxy resin, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, naphthylene ether type epoxy resin, trimethylol type epoxy resin, tetraphenylethane type epoxy resin, isocyanurate type epoxy resin, phenolphthalate. Imidine type epoxy resin, phenolphthalein type epoxy resin, etc. are mentioned. (B) Epoxy resins may be used individually or in combination of two or more types.

The resin composition preferably contains an epoxy resin (B) having two or more epoxy groups in one molecule. (B) The proportion of the epoxy resin having two or more epoxy groups in one molecule relative to 100% by mass of the non-volatile component of the epoxy resin is preferably 50% by mass or more, more preferably 60% by mass or more, especially preferably is 70% by mass or more.

Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter sometimes referred to as “liquid epoxy resins”) and epoxy resins that are solid at a temperature of 20°C (hereinafter sometimes referred to as “solid epoxy resins”). There is. The resin composition of the present invention may contain only a liquid epoxy resin as an epoxy resin, may contain only a solid epoxy resin, or may contain a combination of a liquid epoxy resin and a solid epoxy resin. The epoxy resin in the resin composition of the present invention is preferably a solid epoxy resin or a combination of a liquid epoxy resin and a solid epoxy resin, and more preferably a solid epoxy resin.

As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferable.

Liquid epoxy resins include bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, bisphenol AF-type epoxy resin, naphthalene-type epoxy resin, glycidyl ester-type epoxy resin, glycidylamine-type epoxy resin, and phenol novolak-type epoxy resin. , alicyclic epoxy resins having an ester skeleton, cyclohexane-type epoxy resins, cyclohexanedimethanol-type epoxy resins, and epoxy resins having a butadiene structure are preferable.

Specific examples of the liquid epoxy resin include "HP4032", "HP4032D", and "HP4032SS" (naphthalene type epoxy resin) manufactured by DIC Corporation; "828US", "828EL", "jER828EL", "825", "Epicoat 828EL" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F type) manufactured by Mitsubishi Chemical Corporation epoxy resin); "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “630”, “630LSD”, and “604” (glycidylamine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “ED-523T” manufactured by ADEKA (glycirol type epoxy resin); “EP-3950L” and “EP-3980S” (glycidylamine type epoxy resin) manufactured by ADEKA; “EP-4088S” manufactured by ADEKA (dicyclopentadiene type epoxy resin); “ZX1059” manufactured by Shin-Nittetsu Sumikin Chemical Co., Ltd. (mixture of bisphenol A-type epoxy resin and bisphenol F-type epoxy resin); “EX-721” (glycidyl ester type epoxy resin) manufactured by Nagase Chemtex Corporation; “Celoxide 2021P” manufactured by Daicel Corporation (alicyclic epoxy resin with an ester skeleton); “PB-3600” manufactured by Daicel Corporation, “JP-100” and “JP-200” manufactured by Nippon Soda Corporation (epoxy resin with a butadiene structure); “ZX1658” and “ZX1658GS” (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon-Steel Sumikin Chemical Co., Ltd., and the like. These may be used individually or in combination of two or more types.

As the solid epoxy resin, a solid epoxy resin having 3 or more epoxy groups per molecule is preferable, and an aromatic solid epoxy resin having 3 or more epoxy groups per molecule is more preferable.

As solid epoxy resins, xylenol-type epoxy resin, naphthalene-type epoxy resin, naphthalene-type tetrafunctional epoxy resin, naphthol novolak-type epoxy resin, cresol novolak-type epoxy resin, dicyclopentadiene-type epoxy resin, and trisphenol-type epoxy resin. , naphthol type epoxy resin, biphenyl type epoxy resin, naphthylene ether type epoxy resin, anthracene type epoxy resin, bisphenol A type epoxy resin, bisphenol AF type epoxy resin, phenol aralkyl type epoxy resin, tetraphenylethane type epoxy resin, Phenolphthalimidine type epoxy resin and phenolphthalein type epoxy resin are preferred.

Specific examples of the solid epoxy resin include "HP4032H" (naphthalene type epoxy resin) manufactured by DIC Corporation; “HP-4700” and “HP-4710” (naphthalene type tetrafunctional epoxy resin) manufactured by DIC Corporation; "N-690" (cresol novolac type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolac type epoxy resin) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", and "HP-7200L" (dicyclopentadiene type epoxy resin) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", and "HP6000" (naphthylene ether type epoxy resin) manufactured by DIC Corporation; “EPPN-502H” manufactured by Nippon Kayaku Co., Ltd. (trisphenol type epoxy resin); “NC7000L” manufactured by Nippon Kayaku Co., Ltd. (naphthol novolac type epoxy resin); "NC3000H", "NC3000", "NC3000L", "NC3000FH", and "NC3100" (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; “ESN475V” (naphthalene type epoxy resin) manufactured by Nittetsu Chemical &Materials; “ESN485” (naphthol type epoxy resin) manufactured by Nittetsu Chemical &Materials; “ESN375” (dihydroxynaphthalene type epoxy resin) manufactured by Nittetsu Chemical &Materials; "YX4000H", "YX4000", "YX4000HK", and "YL7890" (bixylenol type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “YL6121” (biphenyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “YX8800” (anthracene type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “YX7700” (phenol aralkyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “PG-100” and “CG-500” manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “YL7800” (fluorene type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; “jER1031S” (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "WHR991S" (phenolphthalimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., etc. are mentioned. These may be used individually or in combination of two or more types.

(B) When using a liquid epoxy resin and a solid epoxy resin together as the epoxy resin, the mass ratio of the liquid epoxy resin to the solid epoxy resin (liquid epoxy resin/solid epoxy resin) is not particularly limited, but is preferably 10. or less, more preferably 5 or less, even more preferably 1 or less.

(B) The epoxy equivalent of the epoxy resin is preferably 50 g/eq. to 5,000 g/eq., more preferably 60 g/eq. to 2,000 g/eq., more preferably 70 g/eq. to 1,000 g/eq., more preferably 80 g/eq. to 500 g/eq. Epoxy equivalent is the mass of resin per equivalent of epoxy group. The epoxy equivalent can be measured according to JIS K7236.

(B) The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and still more preferably 400 to 1,500. The weight average molecular weight of the resin can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC).

The content of component (B) is, for example, 1% by mass or more, preferably 3% by mass or more, more preferably 5% by mass or more, with respect to 100% by mass of non-volatile components in the resin composition. 8 mass% or more, more preferably 8.5 mass% or more, for example, 30 mass% or less, preferably 20 mass% or less, more preferably 15 mass% or less, even more preferably 13 It is % by mass or less, more preferably 10% by mass or less.

The content of component (B) is, for example, 10% by mass or more, preferably 15% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass, based on 100% by mass of the resin component in the resin composition. It is % by mass or more, more preferably 28 mass % or more, particularly preferably 30 mass % or more, and for example, 60 mass % or less, preferably 55 mass % or less, more preferably 50 mass % or more. % or less, more preferably 45 mass% or less, even more preferably 40 mass% or less, particularly preferably 35 mass% or less.

<(C) Active ester compound>

The resin composition of the present invention contains (C) an active ester compound. (C) The active ester compound may be used individually, or two or more types may be used in combination in any ratio. (C) The active ester compound may react with the epoxy resin (B) and have the function of crosslinking the epoxy resin (B). (C) The active ester compound may have a carbon-carbon unsaturated bond, and the unsaturated bond is preferably a carbon-carbon double bond, for example, the carbon-carbon of the (C1) component described later. It may be the same as the unsaturated bond.

(C) The active ester compound generally contains two or more highly reactive ester groups per molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds. Compounds having these are preferably used. The active ester compound is preferably obtained by condensation reaction of a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxy compound and/or a thiol compound. Particularly from the viewpoint of improving heat resistance, active ester compounds obtained from a carboxylic acid compound and a hydroxy compound are preferable, and active ester compounds obtained from a carboxylic acid compound and a phenol compound and/or a naphthol compound are more preferable. Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. As phenol compounds or naphthol compounds, for example, hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, phenolphthaline, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m- Cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, Trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucine, benzenetriol, dicyclopentadiene type diphenol compound, phenol novolac, etc. are mentioned. Here, “dicyclopentadiene-type diphenol compound” refers to a diphenol compound obtained by condensing two molecules of phenol with one molecule of dicyclopentadiene.

Specifically, (C) the active ester compound includes a dicyclopentadiene-type active ester compound, a naphthalene-type active ester compound containing a naphthalene structure, an active ester compound containing an acetylated product of phenol novolak, and benzoyl phenol novolac. An active ester compound containing a cargo is preferable, and among these, it is more preferable that it is at least one type selected from a dicyclopentadiene type active ester compound and a naphthalene type active ester compound, and a dicyclopentadiene type active ester compound is more preferable. . As the dicyclopentadiene type active ester compound, an active ester compound containing a dicyclopentadiene type diphenol structure is preferable. “Dicyclopentadiene type diphenol structure” refers to a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.

(C) Commercially available active ester compounds include dicyclopentadiene-type diphenol structures, such as “EXB9451,” “EXB9460,” “EXB9460S,” “EXB-8000L,” and “EXB-8000L-65M.” ”, “EXB-8000L-65TM”, “HPC-8000L-65TM”, “HPC-8000”, “HPC-8000-65T”, “HPC-8000H”, “HPC-8000H-65TM” (manufactured by DIC) ; As an active ester compound containing a naphthalene structure, “EXB-8100L-65T”, “EXB-8150-60T”, “EXB-8150-62T”, “EXB-9416-70BK”, “HPC-8150-60T”, “ “HPC-8150-62T” (manufactured by DIC); As a phosphorus-containing active ester compound, “EXB9401” (manufactured by DIC), as an active ester compound that is an acetylate of phenol novolac, “DC808” (manufactured by Mitsubishi Chemical Corporation), and as an active ester compound that is a benzoylate of phenol novolac, “YLH1026.” ", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation), and "PC1300-02-65MA" (manufactured by Airwater Corporation) as an active ester compound containing a styryl group and a naphthalene structure.

(C) The active ester group equivalent of the active ester compound is preferably 50 g/eq. to 500 g/eq., more preferably 50 g/eq. to 400 g/eq., more preferably 100 g/eq. to 300 g/eq. The active ester group equivalent is the mass of the active ester compound per equivalent of the active ester group.

The amount ratio of component (B) and component (C) is the sum of the mass of the non-volatile component of component (B) divided by the epoxy equivalent, and the mass of the non-volatile component of component (C) is set to a. When b is the sum of all the values divided by the active ester group equivalent, b/a is preferably 1.0 or more, more preferably 1.01 or more, more preferably 1.03 or more, and even more preferably 1.05 or more, 1.1 or more is particularly preferable, 2.0 or less is preferable, 1.75 or less is more preferable, 1.5 or less is still more preferable, 1.3 or less is still more preferable, and 1.2 or less is especially preferable. By keeping the amount ratio of component (B) and component (C) within this range, the effect of the present invention can be easily obtained.

The content of component (C) is, for example, 3% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, with respect to 100% by mass of non-volatile components in the resin composition. 13% by mass or more, more preferably 15% by mass or more, for example, 30% by mass or less, preferably 25% by mass or less, more preferably 20% by mass or less, even more preferably 16% by mass. It is less than mass%.

The content of component (C) is, for example, 30% by mass or more, preferably 40% by mass or more, more preferably 45% by mass or more, and still more preferably 50% by mass or more, based on 100% by mass of the resin component in the resin composition. mass% or more, more preferably 54 mass% or more, and for example, 70 mass% or less, preferably 65 mass% or less, more preferably 63 mass% or less, even more preferably 60 mass%. % or less.

<(D) Inorganic filler>

The resin composition of the present invention may contain (D) an inorganic filler as an optional component. (D) The inorganic filler is contained in the resin composition in the form of particles. (D) Inorganic fillers may be used individually or in combination of two or more types.

(D) An inorganic compound is used as the material for the inorganic filler. (D) Inorganic filler materials include, for example, silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, and hydroxide. Aluminum, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, Examples include barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly suitable. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Additionally, spherical silica is preferred as the silica. (D) Inorganic fillers may be used individually, or two or more types may be used in combination at any ratio.

(D) Commercially available inorganic fillers include, for example, “SP60-05” and “SP507-05” manufactured by Nittetsu Chemical &Materials; "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", "YC100C", "YA050C", "YA050C-MJE", "YA010C" manufactured by Adomatex Corporation; manufactured by Denka Corporation “UFP-30”, “DAW-03”, “FB-105FD”; “Actual writing NSS-3N”, “Actual writing NSS-4N”, and “Actual writing NSS-5N” manufactured by Tokuyama Corporation; “MGH-005” manufactured by Taiheyo Cement Co., Ltd.; and "BA-S" manufactured by Nikki Shokubai Kasei.

(D) The average particle diameter of the inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, further preferably 2 μm or less, even more preferably 1 μm or less, especially Preferably it is 0.7㎛ or less. (D) The lower limit of the average particle diameter of the inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.1 μm or more, particularly preferably 0.2 μm or more. . (D) The average particle diameter of the inorganic filler can be measured by a laser diffraction/scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be prepared on a volume basis using a laser diffraction scattering type particle size distribution measuring device, and the intermediate diameter can be measured as the average particle size. The measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial bottle and dispersing them by ultrasonic waves for 10 minutes. For the measurement sample, a laser diffraction type particle size distribution measuring device is used, the light source wavelength used is blue and red, the volume-based particle size distribution of the inorganic filler is measured using a flow cell method, and the median diameter is calculated from the obtained particle size distribution. The average particle diameter was calculated as . Examples of the laser diffraction type particle size distribution measuring device include "LA-960" manufactured by Horiba Sesakusho Co., Ltd.

(D) The specific surface area of the inorganic filler is not particularly limited, but is preferably 0.1 m2/g or more, more preferably 0.5 m2/g or more, further preferably 1 m2/g or more, especially preferably 3. It is more than ㎡/g. (D) The upper limit of the specific surface area of the inorganic filler is not particularly limited, but is preferably 100 m2/g or less, more preferably 70 m2/g or less, further preferably 50 m2/g or less, especially preferably is less than 40㎡/g. The specific surface area of the inorganic filler can be obtained by adsorbing nitrogen gas to the surface of the sample using a specific surface area measuring device (Macsorb HM-1210, manufactured by Mountec) according to the BET method, and calculating the specific surface area using the BET multipoint method. there is.

(D) The inorganic filler is preferably surface treated with an appropriate surface treatment agent. By surface treatment, the moisture resistance and dispersibility of the (D) inorganic filler can be improved. Examples of the surface treatment agent include vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, Epoxy-based silane coupling agents such as 3-glycidoxypropyltriethoxysilane; Styryl-based silane coupling agents such as p-styryltrimethoxysilane; Methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane. Ringje; Acrylic silane coupling agents such as 3-acryloxypropyltrimethoxysilane; N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltri Ethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrime Amino silane coupling agents such as oxysilane and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; Isocyanurate-based silane coupling agents such as tris-(trimethoxysilylpropyl)isocyanurate; Ureido-based silane coupling agents such as 3-ureidopropyltrialkoxysilane; Mercapto-based silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; Isocyanate-based silane coupling agents such as 3-isocyanate propyltriethoxysilane; Silane coupling agents such as acid anhydride-based silane coupling agents such as 3-trimethoxysilylpropylsuccinic acid anhydride; Methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, Non-silane coupling such as hexyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, 1,6-bis(trimethoxysilyl)hexane, and trifluoropropyltrimethoxysilane. -Alkoxysilane compounds, etc. can be mentioned. In addition, the surface treatment agent may be used individually, or two or more types may be used in combination in an arbitrary ratio.

Examples of commercially available surface treatment agents include "KBM-1003" and "KBE-1003" (vinyl-based silane coupling agent) manufactured by Shin-Etsu Chemical Co., Ltd.; “KBM-303”, “KBM-402”, “KBM-403”, “KBE-402”, “KBE-403” (epoxy-based silane coupling agent); “KBM-1403” (styryl-based silane coupling agent); “KBM-502”, “KBM-503”, “KBE-502”, “KBE-503” (methacrylic silane coupling agent); “KBM-5103” (acrylic silane coupling agent); “KBM-602”, “KBM-603”, “KBM-903”, “KBE-903”, “KBE-9103P”, “KBM-573”, “KBM-575” (amino silane coupling agent); “KBM-9659” (isocyanurate-based silane coupling agent); “KBE-585” (ureido-based silane coupling agent); “KBM-802”, “KBM-803” (mercapto-based silane coupling agent); “KBE-9007N” (isocyanate-based silane coupling agent); “X-12-967C” (acid anhydride-based silane coupling agent); 「KBM-13」, 「KBM-22」, 「KBM-103」, 「KBE-13」, 「KBE-22」, 「KBE-103」, 「KBM-3033」, 「KBE-3033」, 「KBM -3063", "KBE-3063", "KBE-3083", "KBM-3103C", "KBM-3066", "KBM-7103" (non-silane coupling-alkoxysilane compound), etc.

The degree of surface treatment with the surface treatment agent is preferably within a predetermined range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, 100% by mass of the inorganic filler is preferably surface treated with 0.2% by mass to 5% by mass of a surface treatment agent, more preferably 0.3% by mass by 0.3% by mass. It is more preferable that the surface is treated in an amount of 2 to 2% by mass.

The degree of surface treatment by a surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of the inorganic filler is preferably 0.02 mg/m 2 or more, more preferably 0.1 mg/m 2 or more, and even more preferably 0.2 mg/m 2 or more. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity in sheet form, 1.0 mg/m2 or less is preferable, 0.8 mg/m2 or less is more preferable, and 0.5 mg/m2 or less is still more preferable. .

(D) The amount of carbon per unit surface area of the inorganic filler can be measured after the surface-treated inorganic filler is washed with a solvent (for example, methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solids, the amount of carbon per unit surface area of the inorganic filler can be measured using a carbon analyzer. As a carbon analyzer, "EMIA-320V" manufactured by Horiba Sesakusho, etc. can be used.

The content of the (D) inorganic filler in the resin composition is not particularly limited, but when the non-volatile component in the resin composition is 100% by mass, it is preferably 95% by mass or less, more preferably 90% by mass or less, and further. It may be preferably 85 mass% or less, more preferably 80 mass% or less, and particularly preferably 75 mass% or less. The lower limit of the content of the (D) inorganic filler in the resin composition is not particularly limited, but when the non-volatile component in the resin composition is 100% by mass, for example, 0% by mass or more, 1% by mass or more, 10% by mass. % or more, 20% by mass or more, 30% by mass or more, etc., preferably 40% by mass or more, more preferably 50% by mass or more, further preferably 60% by mass or more, even more preferably 65% by mass. It may be more than 70% by mass, especially preferably 70% by mass or more.

<(E) Radically polymerizable compound>

The resin composition of the present invention may contain (E) a radically polymerizable compound as an optional component. (E) The radically polymerizable compound may be used individually or in combination of two or more types.

The type of radically polymerizable compound is not particularly limited as long as it has one or more (preferably two or more) radically polymerizable unsaturated groups in one molecule. Examples of radically polymerizable compounds include radically polymerizable unsaturated groups, such as maleimide group, vinyl group, allyl group, styryl group, vinylphenyl group, acryloyl group, methacryloyl group, fumaroyl group, and maleoyl group. Compounds having one or more selected types can be mentioned. Among these, it is preferable to include (E1) a maleimide compound and/or (E2) other radically polymerizable compounds from the viewpoint of easily obtaining a cured product with excellent dielectric properties. (E2) Other radically polymerizable compounds are compounds that do not have a maleimide group and have a radically polymerizable unsaturated group other than the maleimide group, and include, among others, at least one selected from (meth)acrylic resin and styryl resin. It is desirable to do so.

(E1) As a maleimide compound, one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups) are contained in one molecule. As long as it has it, its type is not particularly limited. As maleimide compounds, for example, "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all designer Molecules) maleimide resins containing an aliphatic skeleton with 36 carbon atoms derived from dimerdiamine, such as those produced by the company; A maleimide resin containing an indan skeleton, described in Invention Association Public Notice No. 2020-500211; “MIR-3000-70MT”, “MIR-5000-60T” (all manufactured by Nippon Kayaku), “BMI-4000” (manufactured by Yamato Kasei), “BMI-80” (manufactured by Keai Kasei), etc. and a maleimide resin containing an aromatic ring skeleton directly bonded to the nitrogen atom of the maleimide group.

The type of (meth)acrylic resin is not particularly limited as long as it has one or more (preferably two or more) (meth)acryloyl groups in one molecule. Here, the term “(meth)acryloyl group” is a general term for acryloyl group and methacryloyl group. As methacrylic resin, for example, "A-DOG" (manufactured by Shinnakamura Chemical Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Company), "NPDGA", "FM-400", and "R" (meth)acrylic resins such as "-687", "THE-330", "PET-30", and "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.).

The type of styryl resin is not particularly limited as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups per molecule. Examples of the styryl resin include styryl resins such as "OPE-2St", "OPE-2St 1200", and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Co., Ltd.).

The content of the radically polymerizable compound (E) in the resin composition may be 0 mass% or greater than 0 mass% when the non-volatile component in the resin composition is 100 mass%, and is preferably 0.01 mass% or more. Preferably it is 0.1 mass% or more, especially preferably 0.5 mass% or more, and for example, 10 mass% or less, preferably 5 mass% or less, more preferably 3 mass% or less, especially preferably It is 1.5% by mass or less.

The content of the radically polymerizable compound (E) in the resin composition may be 0% by mass, may be greater than 0% by mass, and is preferably 0.1% by mass or more, more preferably 0.1% by mass or more, when the resin component in the resin composition is 100% by mass. Preferably it is 1% by mass or more, more preferably 2% by mass or more, especially preferably 2.5% by mass or more, and further, for example, 20% by mass or less, preferably 10% by mass or less, more preferably 7% by mass. It is 5 mass % or less, especially preferably 5 mass % or less.

<(F) Other hardeners>

The resin composition of the present invention may contain (F) other curing agents as optional components. The other curing agents of (F) do not include those corresponding to the components (A) to (C) and (E). (F) Other curing agents, like the active ester compound (C) above, may have a function as an epoxy resin curing agent that reacts with the epoxy resin (B) to cure the resin composition. (F) Other hardening agents may be used individually or in combination of two or more types.

(F) Other curing agents include, for example, phenol-based curing agents, carbodiimide-based curing agents, acid anhydride-based curing agents, amine-based curing agents, benzoxazine-based curing agents, cyanate ester-based curing agents, and thiol-based curing agents. Among them, it is preferable to use at least one type of curing agent selected from the group consisting of phenol-based curing agents and carbodiimide-based curing agents.

As a phenol-based curing agent, a curing agent having one or more, preferably two or more hydroxyl groups per molecule bonded to an aromatic ring such as a benzene ring or naphthalene ring can be used. From the viewpoint of heat resistance and water resistance, a phenol-based curing agent having a novolak structure is preferable. Furthermore, from the viewpoint of adhesion, a nitrogen-containing phenol-based curing agent is preferable, and a triazine skeleton-containing phenol-based curing agent is more preferable. Among them, a phenol novolak resin containing a triazine skeleton is preferable from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion. Specific examples of phenol-based curing agents include, for example, "MEH-7700", "MEH-7810", and "MEH-7851" manufactured by Meiwa Kasei Co., Ltd., and "NHN", "CBN", and "GPH" manufactured by Nippon Kayaku Co., Ltd. ", "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375" manufactured by Nittetsu Chemical & Materials Co., Ltd. ”, “SN-395”, “LA-7052”, “LA-7054”, “LA-3018”, “LA-3018-50P”, “LA-1356”, “TD2090”, “TD” manufactured by DIC Corporation -2090-60M” and the like.

As the carbodiimide-based curing agent, a curing agent having one or more, preferably two or more, carbodiimide structures in one molecule can be used. Specific examples of carbodiimide-based curing agents include aliphatic biscabodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane bis(methylene-t-butylcarbodiimide); Biscabodiimides such as aromatic biscabodiimides such as phenylene-bis(xylylcarbodiimide); Aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide). ; Poly(phenylenecarbodiimide), poly(naphthylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(di Ethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly (methylenediphenylenecarbodiimide), and aromatic polycarbodiimide such as poly[methylenebis(methylphenylene)carbodiimide]. Commercially available carbodiimide-based curing agents include, for example, “CarbodiLite V-02B,” “CarbodyLite V-03,” “CarbodyLite V-04K,” and “CarbodyLite” manufactured by Nisshinbo Chemical Co., Ltd. V-07” and “Carbody Light V-09”; “Stabakusol P”, “Starvacuzol P400”, and “Hycadyl 510” manufactured by Line Chemistry, etc. can be mentioned.

As the acid anhydride-based curing agent, a curing agent having one or more acid anhydride groups in one molecule can be used, and a curing agent having two or more acid anhydride groups in one molecule is preferred. Specific examples of acid anhydride-based curing agents include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, and trialkyltetrahydrophthalic anhydride. , dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, trimellitic anhydride, pyromelli anhydride. Triacic acid, benzophenone tetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, naphthalenetetracarboxylic acid dianhydride, oxydiphthalic acid dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic acid dianhydride, 1,3, 3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis (anhydrotrimellitate), and polymeric acid anhydrides such as styrene/maleic acid resin, which is a copolymerization of styrene and maleic acid. Commercially available acid anhydride-based curing agents include, for example, "HNA-100", "MH-700", "MTA-15", "DDSA", and "OSA" manufactured by Nippon Rika Corporation; “YH-306” and “YH-307” manufactured by Mitsubishi Chemical Corporation; “HN-2200” and “HN-5500” manufactured by Hitachi Kasei Corporation; “EF-30,” “EF-40,” “EF-60,” and “EF-80” manufactured by Cray Vale Co., Ltd. can be mentioned.

As an amine-based curing agent, a curing agent having at least one amino group, preferably at least two amino groups, in one molecule can be used. Examples of amine-based curing agents include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines. Among these, aromatic amines are preferable. The amine-based curing agent is preferably a primary amine or a secondary amine, and a primary amine is more preferable. Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'- Diaminodiphenyl sulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobi Phenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3 -Dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane , 1,3-bis (3-aminophenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 1,4-bis (4-aminophenoxy) benzene, 4,4'-bis ( Examples include 4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, and bis(4-(3-aminophenoxy)phenyl)sulfone. Examples of commercially available amine-based curing agents include “SEIKACURE-S” manufactured by Seika Corporation; "KAYABOND C-200S", "KAYABOND C-100", "Kayahard A-A", "Kayahard A-B", and "Kayahard A-S" manufactured by Nippon Kayaku Corporation; “Epicure W” manufactured by Mitsubishi Chemical Corporation; "DTDA" manufactured by Sumitomo Seika Co., Ltd., etc. are mentioned.

Specific examples of benzoxazine-based curing agents include “JBZ-OP100D” and “ODA-BOZ” manufactured by JFE Chemicals; “HFB2006M” manufactured by Showa Kobunshi Corporation; “P-d” and “F-a” manufactured by Shikoku Kaseiko Kogyo Co., Ltd. can be mentioned.

Examples of cyanate ester-based curing agents include bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylenecyanate)), and 4,4'-methylenebis(2,6). -dimethylphenylcyanate), 4,4'-ethylidenediphenyldicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4) -cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4- Bifunctional cyanate resins such as cyanatephenyl)thioether and bis(4-cyanatephenyl)ether, polyfunctional cyanate resins derived from phenol novolak and cresol novolac, etc., some of these cyanate resins are triazinated. Prepolymers, etc. can be mentioned. Specific examples of cyanate ester-based curing agents include "PT30" and "PT60" (both phenol novolak-type polyfunctional cyanate ester resins), "BA230", and "BA230S75" (part of bisphenol A dicyanate) manufactured by Lonza Japan Co., Ltd. or a prepolymer in which the entire polymer is triazylated to form a trimer).

Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate. You can.

(F) The active group equivalent of other curing agents is preferably 50 g/eq. to 3,000 g/eq., more preferably 100 g/eq. to 1,000 g/eq., more preferably 100 g/eq. to 500 g/eq., particularly preferably 100 g/eq. to 300 g/eq. The active group equivalent represents the mass of the curing agent per equivalent of the active group.

The amount ratio of the epoxy resin and the curing agent, that is, the amount ratio of component (B), component (C), and component (F) is the sum of the mass of the non-volatile component of component (B) divided by the epoxy equivalent. Let a be, let b be the sum of the mass of the non-volatile component of component (C) divided by the equivalent of the active ester group, and let b be the mass of the non-volatile component of component (F) divided by the equivalent of the active ester group. When the total value is c, (b+c)/a is preferably 1.0 or more, more preferably 1.01 or more, more preferably 1.1 to 1.10 or more, still more preferably 1.15 or more, and 1.2 or more. This is particularly preferable, and it is preferable that it is 2.0 or less, more preferably 1.75 or less, more preferably 1.5 or less, even more preferably 1.4 to 1.40 or less, and especially preferably 1.3 or less. By keeping the amount ratio of the epoxy resin and the curing agent within this range, the effects of the present invention can be easily obtained.

The content of (F) other curing agents in the resin composition may be 0 mass% or greater than 0 mass% when the non-volatile component in the resin composition is 100 mass%, and is preferably 0.01 mass% or more, more preferably is 0.1 mass% or more, particularly preferably 1.0 mass% or more, preferably 20 mass% or less, more preferably 10 mass% or less, particularly preferably 5 mass% or less.

The content of (F) other curing agents in the resin composition may be 0% by mass or may be greater than 0% by mass when the resin component in the resin composition is 100% by mass, and is preferably 0.1% by mass or more, more preferably It is 1.0 mass% or more, especially preferably 5.0 mass% or more, preferably 50 mass% or less, more preferably 20 mass% or less, and particularly preferably 10 mass% or less.

<(G) Curing accelerator>

The resin composition of the present invention may contain (G) a curing accelerator as an optional component.

Examples of the curing accelerator include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. (G) A hardening accelerator may be used individually by 1 type, or may be used in combination of 2 or more types.

Examples of phosphorus-based curing accelerators include tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, and bis(tetrabutylphosphonium)pyrro. Mellitate, tetrabutylphosphonium hydrogenhexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, di-tert-butylmethylphosphonium Aliphatic phosphonium salts such as tetraphenyl borate; Methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra- p-tolyl borate, tetraphenylphosphonium tetraphenyl borate, tetraphenylphosphonium tetrap-tolyl borate, triphenylethylphosphonium tetraphenyl borate, tris (3-methylphenyl) ethylphosphonium tetraphenyl borate, tris (2-methyl aromatic phosphonium salts such as toxyphenyl)ethylphosphonium tetraphenyl borate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; Aromatic phosphine/borane complexes such as triphenylphosphine/triphenylborane; Aromatic phosphine/quinone addition reactants such as triphenylphosphine/p-benzoquinone addition reactants; Tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, Aliphatic phosphines such as tricyclohexylphosphine; Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolyl Phosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, Tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2, 6-dimethylphenyl)phosphine, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine , tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl- 2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2- and aromatic phosphines such as bis(diphenylphosphino)acetylene and 2,2'-bis(diphenylphosphino)diphenyl ether.

Examples of urea-based curing accelerators include 1,1-dimethylurea; Aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3- Chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, 3-(3,4 -dimethylphenyl)-1,1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4 -nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]- 1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea ), and aromatic dimethyl ureas such as N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluene bisdimethylurea].

Examples of guanidine-based curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, and diphenylguanidine. , trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]deca-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0] Deca-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1, Examples include 1-diethyl biguanide, 1-cyclohexyl biguanide, 1-allyl biguanide, 1-phenyl biguanide, and 1-(o-tolyl) biguanide.

Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, and 2-ethyl-4-methyl. Imidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methyl Imidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2- Ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimida Zolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-unde Cylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s -Triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazolisocyanuric acid Adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1, 2-a] Imidazole compounds such as benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, and imidazole compounds and epoxy resins Adduct forms of .

As the imidazole-based curing accelerator, you may use a commercial product, for example, "1B2PZ", "2MZA-PW", "2PHZ-PW" manufactured by Shikoku Chemical Company, "P200-H50" manufactured by Mitsubishi Chemical Corporation, etc. can be mentioned.

Examples of the metal-based curing accelerator include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organic cobalt complexes such as cobalt (II) acetylacetonate and cobalt (III) acetylacetonate, organic copper complexes such as copper (II) acetylacetonate, and zinc (II) acetylacetonate. Examples include organic zinc complexes, organic iron complexes such as iron(III) acetylacetonate, organic nickel complexes such as nickel(II) acetylacetonate, and organic manganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8. -Diazabicyclo(5,4,0)-undecene, etc. can be mentioned.

As an amine-type hardening accelerator, a commercial item may be used, for example, "MY-25" manufactured by Ajinomoto Fine Techno Co., Ltd., etc.

The content of the (G) curing accelerator in the resin composition is not particularly limited, but when the non-volatile component in the resin composition is 100% by mass, it is preferably 15% by mass or less, more preferably 10% by mass or less, and further. Preferably it is 5 mass% or less, especially preferably 3 mass% or less. The lower limit of the content of the (E) curing accelerator in the resin composition is not particularly limited, but when the nonvolatile component in the resin composition is 100% by mass, for example, 0% by mass or more, 0.001% by mass or more, or 0.01% by mass. It may be % or more, 0.1 mass% or more, or 0.5 mass% or more.

<(H) Other additives>

The resin composition of the present invention may further contain arbitrary additives as non-volatile components. Examples of such additives include radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; Epoxy curing agents other than active ester compounds such as phenol-based curing agents, naphthol-based curing agents, acid anhydride curing agents, thiol-based curing agents, benzoxazine-based curing agents, cyanate ester-based curing agents, carbodiimide-based curing agents, and imidazole-based curing agents; Thermoplastic resins such as phenoxy resin, polyvinyl acetal resin, polyolefin resin, polysulfone resin, polyether sulfone resin, polyphenylene ether resin, polycarbonate resin, polyether ether ketone resin, and polyester resin; Organic fillers such as rubber particles; Organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; Colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; Polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; Leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; Thickeners such as bentone and montmorillonite; Antifoaming agents such as silicone-based defoaming agents, acrylic-based defoaming agents, fluorine-based defoaming agents, and vinyl resin-based defoaming agents; UV absorbers such as benzotriazole-based UV absorbers; Adhesion improvers such as urea silane; Adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; Antioxidants such as hindered phenol-based antioxidants and hindered amine-based antioxidants; Fluorescent whitening agents such as stilbene derivatives; Surfactants such as fluorine-based surfactants and silicone-based surfactants; Phosphorus-based flame retardants (e.g., phosphoric acid ester compounds, phosphazene compounds, phosphinic acid compounds, red), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, inorganic flame retardants (e.g., antimony trioxide), etc. flame retardant; Dispersants such as phosphoric acid ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; Stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers can be mentioned. (F) Other additives may be used individually, or two or more types may be used in combination at any ratio. (H) The content of other additives can be appropriately set by those skilled in the art.

<(K) Organic Solvent>

The resin composition of the present invention may further contain an arbitrary organic solvent as a volatile component in addition to the non-volatile component described above. (K) As the organic solvent, known solvents can be appropriately used, and the type is not particularly limited. (K) Examples of the organic solvent include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; Ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; Alcohol-based solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; Ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; Ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; Sulfoxide-based solvents such as dimethyl sulfoxide; Nitrile-based solvents such as acetonitrile and propionitoryl; Aliphatic hydrocarbon-based solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon-based solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (K) Organic solvents may be used individually, or two or more types may be used in combination at any ratio.

In one embodiment, the content of the organic solvent (K) is not particularly limited, but when all components in the resin composition are 100% by mass, for example, 60% by mass or less, 40% by mass or less, and 30% by mass. % or less, 20 mass% or less, 15 mass% or less, 10 mass% or less, etc.

<Method for producing resin composition>

The resin composition of the present invention is, for example, in an optional preparation container, (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound, (D) an inorganic filler, if necessary, Accordingly, (E) a radically polymerizable compound, if necessary (F) other curing agent, if necessary (G) curing accelerator, if necessary (H) other additives, and if necessary (K) organic solvent, in any order. And/or it can be prepared by adding and mixing some or all of them at the same time. Additionally, in the process of adding and mixing each component, the temperature may be appropriately set, and may be heated and/or cooled temporarily or over time. In addition, during or after the addition and mixing process, the resin composition may be uniformly dispersed by stirring or shaking using, for example, a stirring device such as a mixer or a shaking device. Additionally, degassing may be performed simultaneously with stirring or shaking under low pressure conditions such as under vacuum.

<Characteristics of resin composition>

The resin composition of the present invention contains (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound. By using such a resin composition, the dielectric loss tangent can be kept low even in a high temperature environment such as 90°C, and a cured product with excellent crack resistance after desmear treatment can be obtained, preferably at room temperature such as 23°C. A cured product with a low dielectric loss tangent can be obtained even in the to room temperature range.

The cured product of the resin composition of the present invention can have the characteristic of suppressing the occurrence of cracks after desmear treatment (roughening treatment). Therefore, in one embodiment, after manufacturing and desmearing a circuit board as in Test Example 2 below, when 100 copper pad portions of the circuit board are observed, the number of cracks is preferably 10 or less (10% or less). It can be.

The cured product of the resin composition of the present invention can have the characteristic of low dielectric loss tangent (Df) even in a high temperature environment such as 90°C. Therefore, in one embodiment, the dielectric loss tangent (Df) of the cured product of the resin composition when measured at 5.8 GHz and 90°C as in Test Example 1 below is preferably 0.020 or less, 0.010 or less, and more preferably 0.009. It may be 0.008 or less, more preferably 0.007 or less, 0.006 or less, particularly preferably 0.005 or less, 0.004 or less, and 0.003 or less.

The cured product of the resin composition of the present invention can have the characteristic of low dielectric loss tangent (Df) even at room temperature such as 23°C. Therefore, in one embodiment, the dielectric loss tangent (Df) of the cured product of the resin composition when measured at 5.8 GHz and 23°C as in Test Example 1 below is preferably 0.020 or less, 0.010 or less, and more preferably 0.009. It may be 0.008 or less, more preferably 0.007 or less, 0.006 or less, even more preferably 0.005 or less, 0.004 or less, particularly preferably 0.003 or less, 0.002 or less.

<Use of resin composition>

The resin composition of the present invention can be suitably used as a resin composition for insulation purposes, particularly as a resin composition for forming an insulating layer. Specifically, it is suitably used as a resin composition for forming the insulating layer (resin composition for forming an insulating layer for forming a conductor layer) for forming a conductor layer (including a rewiring layer) formed on the insulating layer. You can. In addition, in the printed wiring board described later, it can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for forming an insulating layer of a printed wiring board). The resin composition of the present invention is also widely used in applications requiring a resin composition, such as sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, semiconductor sealants, hole filling resins, and component filling resins. It can be used easily.

In addition, for example, when a semiconductor chip package is manufactured through the following processes (1) to (6), the resin composition of the present invention is used as a resin composition for a redistribution formation layer (cultivation layer) as an insulating layer for forming a redistribution layer. It can also be suitably used as a resin composition for forming a line forming layer) and a resin composition for sealing a semiconductor chip (a resin composition for sealing a semiconductor chip). When a semiconductor chip package is manufactured, a redistribution layer may be additionally formed on the sealing layer.

(1) A process of laminating a temporarily fixed film on a substrate,

(2) A process of temporarily fixing a semiconductor chip on a temporarily fixing film,

(3) Process of forming a sealing layer on the semiconductor chip,

(4) A process of peeling the base material and temporarily fixed film from the semiconductor chip,

(5) A process of forming a redistribution layer as an insulating layer on the surface of the semiconductor chip from which the substrate and temporarily fixed film are peeled, and

(6) A process of forming a redistribution layer as a conductor layer on the redistribution forming layer.

Additionally, since the resin composition of the present invention forms an insulating layer with good component embedding properties, it can be suitably used even when the printed wiring board is a component-embedded circuit board.

<Sheet-like laminated material>

Although the resin composition of the present invention can be used by applying it in a varnish state, it is generally suitable industrially to use it in the form of a sheet-like laminated material containing the resin composition.

As the sheet-like laminated material, the resin sheets and prepregs shown below are preferable.

In one embodiment, the resin sheet includes a support and a resin composition layer provided on the support, and the resin composition layer is formed from the resin composition of the present invention.

The thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less, from the viewpoint of reducing the thickness of the printed wiring board and providing a cured product with excellent insulating properties even if the cured product of the resin composition is a thin film. The lower limit of the thickness of the resin composition layer is not particularly limited, but can usually be 5 μm or more, 10 μm or more, etc.

Examples of the support include films, metal foils, and release papers made of plastic materials, and films and metal foils made of plastic materials are preferred.

When using a film made of a plastic material as a support, examples of the plastic material include polyethylene terephthalate (hereinafter sometimes abbreviated as “PET”), polyethylene naphthalate (hereinafter abbreviated as “PEN”) ), polyester such as polycarbonate (hereinafter sometimes abbreviated as “PC”), acrylic such as polymethyl methacrylate (PMMA), cyclic polyolefin, triacetyl cellulose (TAC), and polyether sulfide ( PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is especially preferable.

When using a metal foil as a support, examples of the metal foil include copper foil, aluminum foil, etc., and copper foil is preferable. As the copper foil, a foil made of the simple metal of copper may be used, or a foil made of an alloy of copper and other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used. good night.

The support may be subjected to mat treatment, corona treatment, or antistatic treatment on the surface joined to the resin composition layer.

Additionally, as the support, you may use a support with a mold release layer that has a mold release layer on the surface bonded to the resin composition layer. Examples of the release agent used in the release layer of the support with a release layer include one or more types of release agents selected from the group consisting of alkyd resin, polyolefin resin, urethane resin, and silicone resin. The support with the release layer may be a commercially available product, for example, "SK-1", "AL-5", and "AL-" manufactured by Lintech, which are PET films with a release layer containing an alkyd resin-based release agent as a main component. 7”, “Lumira T60” manufactured by Torres, “Purex” manufactured by Teijin, and “Unifill” manufactured by Unichika.

The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. On the other hand, when using a support body with a release layer, it is preferable that the entire thickness of the support body with a release layer is within the above range.

In one embodiment, the resin sheet may further include arbitrary layers as needed. Examples of such an optional layer include a protective film similar to the support provided on the side of the resin composition layer that is not bonded to the support (that is, the side opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating a protective film, adhesion of dust or the like to the surface of the resin composition layer and scratches can be suppressed.

The resin sheet is, for example, prepared by preparing a resin varnish from the liquid resin composition as is or by dissolving the resin composition in an organic solvent, applying this to a support using a die coater, etc., and further drying to form a resin composition layer. can do.

Examples of the organic solvent include the same organic solvents described as components of the resin composition. Organic solvents may be used individually, or two or more types may be used in combination.

Drying may be performed by known methods such as heating or hot air spraying. Drying conditions are not particularly limited, but the resin composition layer is dried so that the content of the organic solvent is 10% by mass or less, preferably 5% by mass or less. It also varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, but for example, when using a resin composition or resin varnish containing 30% by mass to 60% by mass of an organic solvent, the boiling point is heated at 50°C to 150°C for 3 minutes. A resin composition layer can be formed by drying for 10 minutes.

The resin sheet can be wound into a roll and stored. When the resin sheet has a protective film, it becomes usable by peeling the protective film.

In one embodiment, the prepreg is formed by impregnating a sheet-like fiber base material with the resin composition of the present invention.

The sheeting fiber base material used for the prepreg is not particularly limited, and commonly used prepreg base materials such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of reducing the thickness of the printed wiring board, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber base material is not particularly limited. Usually, it is 10㎛ or more.

Prepreg can be manufactured by known methods such as hot melt method and solvent method.

The thickness of the prepreg can be within the same range as that of the resin composition layer in the resin sheet.

The sheet-like laminated material of the present invention can be suitably used to form an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and to form an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board). It can be used appropriately.

<Printed wiring board>

The printed wiring board of the present invention includes an insulating layer made of a cured product obtained by curing the resin composition of the present invention.

A printed wiring board can be manufactured, for example, by a method including the following steps (I) and (II) using the above resin sheet.

(I) A process of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is bonded to the inner layer substrate.

(II) Process of curing (e.g., heat curing) the resin composition layer to form an insulating layer

The “inner layer substrate” used in step (I) is a member that becomes the substrate of the printed wiring board, for example, glass epoxy substrate, metal substrate, polyester substrate, polyimide substrate, BT resin substrate, and thermosetting polyphenylene. Ether substrates, etc. can be mentioned. Additionally, the substrate may have a conductor layer on one or both sides, and the conductor layer may be pattern-processed. An inner layer substrate on which a conductor layer (circuit) is formed on one or both sides of the substrate is sometimes referred to as an “inner layer circuit board.” In addition, when manufacturing a printed wiring board, intermediate products on which an insulating layer and/or a conductor layer must be additionally formed are also included in the "inner layer substrate" referred to in the present invention. If the printed wiring board is a circuit board with embedded components, an inner layer board with embedded components may be used.

Lamination of the inner layer substrate and the resin sheet can be performed, for example, by heat-pressing the resin sheet to the inner layer substrate from the support side. Examples of members for heat-pressing the resin sheet to the inner layer substrate (hereinafter also referred to as “heat-pressing members”) include heated metal plates (SUS head plates, etc.) or metal rolls (SUS rolls). On the other hand, it is preferable not to press the heat-compression member directly on the resin sheet, but to press it through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the inner layer substrate.

Lamination of the inner layer substrate and the resin sheet may be performed by a vacuum lamination method. In the vacuum lamination method, the heat-pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, and the heat-compression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably is in the range of 0.29 MPa to 1.47 MPa, and the heat compression time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination can be preferably carried out under reduced pressure conditions of 26.7 hPa or less.

Lamination can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressurization laminator manufactured by Meiki Sesakusho, a vacuum applicator manufactured by Nikko Materials, and a batch vacuum pressurized laminator.

After lamination, the laminated resin sheets may be smoothed under normal pressure (under atmospheric pressure), for example, by pressing a heat-pressing member from the support side. The press conditions for the smoothing treatment can be the same as the heat-pressing conditions for the above-mentioned lamination. Smoothing treatment can be performed using a commercially available laminator. Meanwhile, the lamination and smoothing treatment may be performed continuously using the commercially available vacuum laminator.

The support may be removed between step (I) and step (II), or may be removed after step (II).

In step (II), the resin composition layer is cured (for example, heat cured) to form an insulating layer made of a cured resin composition. The curing conditions of the resin composition layer are not particularly limited, and conditions normally employed when forming the insulating layer of a printed wiring board may be used.

For example, the heat curing conditions of the resin composition layer vary depending on the type of the resin composition, etc., but in one embodiment, the curing temperature is, for example, 120°C or higher, 130°C or higher, higher than 130°C, 135°C or higher, It is more than 135°C, preferably 140°C or more, more than 140°C, more preferably 150°C or more, more preferably 170°C or more, and also, for example, 240°C or less, preferably 220°C or less. Preferably it is 210°C or lower. The curing time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to heat curing the resin composition layer, the resin composition layer is cured at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more. Preheating may be performed preferably for 5 minutes to 150 minutes, more preferably for 15 minutes to 120 minutes, and even more preferably for 15 minutes to 100 minutes.

When manufacturing a printed wiring board, (III) a step of perforating the insulating layer, (IV) a step of roughening the insulating layer, and (V) a step of forming a conductor layer may be additionally performed. These steps (III) to (V) may be carried out according to various methods known to those skilled in the art that are used in the manufacture of printed wiring boards. On the other hand, when the support is removed after step (II), the support is removed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). It can be done in between. Additionally, if necessary, the formation of the insulating layer and the conductor layer in steps (II) to (V) may be repeated to form a multilayer wiring board.

In another embodiment, the printed wiring board of the present invention can be manufactured using the prepreg. The manufacturing method is basically the same as when using a resin sheet.

Process (III) is a process of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, laser, plasma, etc., depending on the composition of the resin composition used to form the insulating layer. The size and shape of the hole may be determined appropriately according to the design of the printed wiring board.

Process (IV) is a process of roughening the insulating layer. Usually, smear is also removed in this step (IV). The procedures and conditions of the roughening process are not particularly limited, and known procedures and conditions usually used when forming the insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by performing swelling treatment with a swelling liquid, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing liquid in this order.

The swelling liquid used in the roughening treatment is not particularly limited, and includes an alkaline solution and a surfactant solution, and is preferably an alkaline solution. As the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferable. Examples of commercially available swelling liquids include "Swelling Deep Securiganth P" and "Swelling Deep Securiganth SBU" manufactured by Atotech Japan. The swelling treatment using the swelling liquid is not particularly limited, but can be performed, for example, by immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid of 40°C to 80°C for 5 to 15 minutes.

The oxidizing agent used in the roughening treatment is not particularly limited, and examples include an alkaline permanganate solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganic acid solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. Additionally, the concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as “Concentrate Compact CP” and “Dosing Solution Securiganth P” manufactured by Atotech Japan.

In addition, as the neutralizing liquid used in the roughening treatment, an acidic aqueous solution is preferable, and examples of commercial products include "Reduction Solution Securigant P" manufactured by Atotech Japan.

Treatment with a neutralizing liquid can be performed by immersing the treated surface that has been roughened with an oxidizing agent in a neutralizing liquid at 30°C to 80°C for 5 to 30 minutes. In terms of workability, etc., a method of immersing the object that has been roughened with an oxidizing agent in a neutralizing liquid at 40°C to 70°C for 5 to 20 minutes is preferable.

Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used in the conductor layer is not particularly limited.

In a suitable embodiment, the conductor layer includes one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. do. The conductor layer may be a single metal layer or an alloy layer, and the alloy layer may be, for example, an alloy of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy) ) can include a layer formed of. Among them, from the viewpoint of versatility of forming the conductor layer, cost, ease of patterning, etc., a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or a nickel-chromium alloy, copper-nickel alloy, An alloy layer of a copper/titanium alloy is preferable, and a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper or an alloy layer of a nickel/chromium alloy is more preferable, and a single metal layer of copper is even more preferable. desirable.

The conductor layer may have a single-layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer with a desired wiring pattern can be formed by plating on the surface of the insulating layer using a conventionally known technique such as a semi-additive method or a full additive method, and from the viewpoint of ease of manufacturing, the semi-additive method can be used. It is preferable to form it by the additive method. Hereinafter, an example of forming a conductor layer by a semi-additive method will be shown.

First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, on the formed plating seed layer, a mask pattern is formed to expose a portion of the plating seed layer corresponding to the desired wiring pattern. After forming a metal layer on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, the unnecessary plating seed layer can be removed by etching or the like to form a conductor layer with a desired wiring pattern.

In another embodiment, the conductor layer may be formed using metal foil. When forming a conductor layer using metal foil, step (V) is preferably performed between step (I) and step (II). For example, after step (I), the support is removed and a metal foil is laminated on the surface of the exposed resin composition layer. Lamination of the resin composition layer and the metal foil may be performed by a vacuum lamination method. The conditions for lamination may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Thereafter, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by conventionally known techniques such as the subtractive method and the modified semiadditive method.

Metal foil can be manufactured by known methods such as electrolysis and rolling, for example. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Nikko Nisseki Kinzoku Corporation, 3EC-III foil and TP-III foil manufactured by Mitsui Kinzoku Kozan Corporation.

<Semiconductor device>

The semiconductor device of the present invention includes the printed wiring board of the present invention. The semiconductor device of the present invention can be manufactured using the printed wiring board of the present invention.

Semiconductor devices include various semiconductor devices used in electrical appliances (e.g., computers, mobile phones, digital cameras, televisions, etc.) and vehicles (e.g., motorcycles, automobiles, trains, ships, aircraft, etc.). there is.

[Example]

Hereinafter, the present invention will be specifically explained by examples. The present invention is not limited to these examples. Meanwhile, in the following, “part” and “%” indicating quantity mean “part by mass” and “% by mass”, respectively, unless otherwise specified. In particular, when the temperature is not specified, the temperature condition is room temperature (25°C).

<Synthesis Example 1: Synthesis of liquid crystal polymer>

In a polymerization vessel with a stirring blade, 60 mol% 6-hydroxy-2-naphthoic acid (HNA), 20 mol% 4,4-dihydroxybiphenyl (BP), 15.5 mol% terephthalic acid (TPA), 4.5 mol% of 2,6-naphthalenedicarboxylic acid (NADA) was added, potassium acetate and magnesium acetate were injected as catalysts, and the polymerization vessel was reduced in pressure and nitrogen was injected three times to perform nitrogen substitution, and then acetic anhydride (hydroxyl group) was added. 1.08 molar equivalent) was additionally added, the temperature was raised to 150°C, and the acetylation reaction was performed under reflux for 2 hours.

After completion of acetylation, the temperature of the polymerization vessel with acetic acid flowing was raised at 0.5°C/min, and when the temperature of the melt in the tank reached 310°C, the polymer was extracted and cooled and solidified. The obtained polymer was pulverized to a size that passes through a sieve with a mesh size of 2.0 mm to obtain a prepolymer.

Next, the temperature of the prepolymer obtained above was raised from room temperature to 310°C over 14 hours using a heater in an oven manufactured by Yamato Chemical Co., Ltd., and then maintained at 310°C for 1 hour to perform solid-state polymerization. did. Afterwards, heat was naturally dissipated at room temperature to obtain liquid crystal polymer A. Using a polarizing microscope (product name: BH-2) manufactured by Olympus Corporation equipped with a hot stage for microscopy (product name: FP82HT) manufactured by Mettler, liquid crystal polymer A was heated and melted on the microscope heating stage, and the presence or absence of optical anisotropy was determined. It was confirmed that liquid crystallinity was exhibited.

<Preparation Example 1: Preparation of liquid crystal polymer particles>

The liquid crystal polymer A powder synthesized above was used in a device combining an SPK-12 type jet mill manufactured by Nippon Pneumatic Kogyo Company and a DSF-10 type classifier manufactured by Nippon Pneumatic Kogyo Company, grinding pressure of 0.65 MPa, and resin supply amount. The pulverization was continuously performed under the conditions of 5 kg/h, and liquid crystal polymer particles A were obtained.

<Evaluation of liquid crystal polymer particles>

(Measurement of melting point)

The melting point of the liquid crystal polymer particles A obtained above was measured by a differential scanning calorimeter (DSC) manufactured by Hitachi High-Tech Science Co., Ltd. in accordance with the test methods of ISO11357 and ASTM D3418. At this time, the temperature is raised from room temperature to 360 to 380°C at a temperature increase rate of 10°C/min to completely melt the polymer, then lowered to 30°C at a rate of 10°C/min, and then further lowered to 380°C at a rate of 10°C/min. The peak of the endothermic peak obtained when the temperature was raised was taken as the melting point. The measured melting point was 319°C.

(Measurement of particle diameter distribution)

The particle diameter distribution of the liquid crystal polymer particles A obtained above was measured using a laser diffraction/scattering method particle diameter distribution measuring device (manufactured by Beckman Coulter, LS 13 320 dry system, equipped with a tornado dry powder module). D50, D90, and Dp, which are parameters representing particle diameter distribution, were obtained as calculation results from measurement data. As a result, D50 was 4.8㎛, and D90/D50 was 1.7.

(Measurement of dielectric loss tangent (10 GHz))

The liquid crystal polymer particles A obtained above were heated and melted under the conditions of melting point to melting point +30°C, injection molded using a mold of 30 mm x 30 mm x 0.4 mm (thickness), and a flat test piece was produced. Subsequently, using the above flat test piece, the dielectric loss tangent at a frequency of 10 GHz was measured by the split post dielectric resonance technique (SPDR method) using a network analyzer N5247A from Keysight Technologies. Meanwhile, N = 4 samples of each type were measured, and the dielectric loss tangent obtained as the average value of 4 times was 0.0007.

(Measurement of outgassing)

The liquid crystal polymer particles A obtained above were placed in a 20 ml vial bottle and sealed, followed by heat treatment at 190°C for 1 hour. Acetic acid and other (phenol, phenyl acetate, etc.) gases generated during the heat treatment were quantified by gas chromatography (HP7820A) connected to a head space sampler (HP7697A) manufactured by Hewlett-Peckard. The column used was G-100 (40m) manufactured by the Chemical Products Inspection Association, and other conditions were initial temperature 45°C, temperature increase rate 20°C/min, final temperature 280°C, helium pressure 8.3 psi, and split ratio 2.0. Measurements were made using an FID detector. Acetic acid as the measured out gas was 0.4 ppm, and other out gases were 5.8 ppm.

<Examples 1 to 8, Comparative Example 1: Preparation of resin varnish>

[Example 1]

15 parts of naphthalene type epoxy resin (“HP-4032-SS” manufactured by DIC, epoxy equivalent 144 g/eq.), activated ester curing agent (“HPC-8150-62T”, active group equivalent 229 g/eq., non-volatile matter 61.5 mass) % toluene solution) 43 parts, other curing agent (phenol-based curing agent, “LA-3018-50P” manufactured by DIC, hydroxyl equivalent 151 g/eq., 1-methoxy 2-propanol solution with 50 mass% non-volatile matter) 5 parts , (A) 2 parts of liquid crystal polymer powder A as component, spherical silica surface-treated with an inorganic filler (amine-based alkoxysilane compound (“KBM573” manufactured by Shin-Etsu Chemical Co., Ltd.) (“SO-C2” manufactured by Adomatex Corporation) , 125 parts (average particle diameter: 0.5 μm, specific surface area: 5.8 m2/g), 0.5 parts of curing accelerator (“1B2PZ”, manufactured by Shikoku Kaseikogyo Co., Ltd.), 10 parts of MEK, and 10 parts of cyclohexanone were mixed, using a high-speed rotating mixer. It was dispersed uniformly to obtain a resin varnish.

[Example 2]

In Example 1, maleimide compound A (Mw/Mn = 1.81, t" = 1.47 (Mw/Mn = 1.81, t" = 1.47 ( Mainly, 2 parts of the MEK solution (62% by mass of non-volatile component) of 1, 2 or 3)) was used in the same manner as in Example 1 except for the above points, to obtain a resin varnish.

[Formula (M)]

[Example 3]

A resin varnish was prepared in the same manner as in Example 1, except that 2 parts of the other maleimide compound (“MIR-5000-60T” manufactured by Nippon Kayaku Co., Ltd., toluene solution with 60% by mass of non-volatile matter) was added. got it

[Example 4]

In the same manner as in Example 1, except that 2 parts of the other maleimide compound (“MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd., toluene/MEK mixed solution with 70% by mass of non-volatile matter) was added. Got a resin varnish.

[Example 5]

A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of the other maleimide compound (“BMI-689” manufactured by Designer Molecular Ink Co., Ltd.) was added.

[Example 6]

In the same manner as in Example 1, except that 2 parts of a compound having another double bond (“OPE-2St-1200” manufactured by Mitsubishi Gas Chemical Co., Ltd., a toluene solution containing 65% by mass of non-volatile matter) was added. Got a resin varnish.

[Example 7]

A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of liquid crystal polymer powder A as component (A) was changed to 1 part.

[Example 8]

A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of liquid crystal polymer powder A as component (A) was changed to 4 parts.

[Comparative Example 1]

A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of liquid crystal polymer powder A as component (A) was not added.

<Production Example 1: Production of resin sheet A with a resin composition layer thickness of 40㎛>

As a support, a polyethylene terephthalate film (“AL5” manufactured by Lintech, thickness 38 μm) provided with a release layer was prepared. On the release layer of the support, the resin varnish obtained in Examples and Comparative Examples was uniformly applied so that the thickness of the dried resin composition layer was 40 μm. Thereafter, the resin composition was dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet A containing a support and a resin composition layer.

<Test Example 1: Measurement of dielectric loss tangent>

Resin sheet A obtained in Production Example 1 using the resin varnish obtained in Examples and Comparative Examples was cured in an oven at 190°C for 90 minutes. By peeling the support from the resin sheet A taken out from the oven, a cured product of the resin composition layer was obtained. The cured product was cut into 80 mm in length and 2 mm in width and referred to as the cured product for evaluation.

For each cured product for evaluation, the value of dielectric loss tangent (Df) was measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C and 90°C by the cavity resonance perturbation method using “HP8362B” manufactured by Agilent Technologies. value) was measured. Measurements were performed on two test pieces, and the average was calculated.

<Production Example 2: Production of resin sheet B with a resin composition layer thickness of 25㎛>

As a support, a polyethylene terephthalate film (“AL5” manufactured by Lintech, thickness 38 μm) provided with a release layer was prepared. On the release layer of the support, the resin varnish obtained in Examples and Comparative Examples was uniformly applied so that the thickness of the dried resin composition layer was 25 μm, and dried at 70°C to 80°C (average 75°C) for 2.5 minutes. As a result, resin sheet B containing a support and a resin composition layer was obtained.

<Test Example 2: Evaluation of crack resistance after desmear treatment>

Resin sheet B with a thickness of 25 ㎛ produced in Production Example 2 was made into a core material (Hitachi Kaseiko) in which circular copper pads (copper thickness 35 ㎛) with a diameter of 350 ㎛ were formed in a lattice shape at 400 ㎛ intervals so that the floating rate was 60%. Using a batch type vacuum pressurized laminator (two-stage build-up laminator "CVP700" manufactured by Nikko Materials) on both sides of the "E705GR" manufactured by Kyoto, thickness 400㎛, the inner layer substrate is bonded to the inner layer substrate so that the resin composition layer is bonded to the inner layer substrate. Laminated on both sides. The laminate was performed by reducing the pressure for 30 seconds to bring the atmospheric pressure to 13 hPa or less, and then compressing it at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds. This was placed in an oven at 130°C and heated for 30 minutes, and then transferred to an oven at 170°C and heated for 30 minutes. Additionally, the support was peeled off, and the obtained circuit board was immersed in Swelling Deep Securigant P from Atotech Japan Co., Ltd., a swelling liquid, at 60°C for 10 minutes. Next, it was immersed in Atotech Japan Co., Ltd.'s Concentrate Compact P (aqueous solution of KMnO ₄ : 60 g/L and NaOH: 40 g/L), which is a roughening solution, at 80°C for 30 minutes. Finally, it was immersed in Atotech Japan Co., Ltd.'s reduction solution Securigant P, a neutralizing liquid, at 40°C for 5 minutes. 100 copper pad portions of the circuit board after the roughening treatment were observed to confirm the presence or absence of cracks in the resin composition layer. If there were 10 or less cracks, it was designated as “○,” and if there were more than 10, it was designated as “×.”

The usage amounts (parts by mass) of components (A) to (G) including volatile components of the resin compositions of Examples and Comparative Examples and the measurement results of Test Examples are shown in Table 1 below. In Table 1, the non-volatile content (% by mass) of each component is shown in the “N.V.” column.

As described above, by using a resin composition containing (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (B) an active ester compound, the dielectric loss tangent (Df) is low even in a high temperature environment such as 90°C, It was found that a cured product with excellent crack resistance after desmear treatment could be obtained. It was also found that the cured product had a low dielectric loss tangent (Df) even in the room temperature to room temperature range, such as 23°C.

Claims (11)

A resin composition comprising (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound. The resin composition according to claim 1, wherein when the resin component in the resin composition is 100% by mass, the content of component (A) is 0.1% by mass or more and 10% by mass or less. The resin composition according to claim 1, wherein (A) the organic filler having liquid crystallinity has a melting point of 270°C or higher. The resin composition according to claim 1, further comprising (D) an inorganic filler. The resin composition according to claim 1, further comprising (E) a radically polymerizable compound. The resin composition according to claim 1, which is used for forming an interlayer insulating layer of a printed wiring board. A cured product of the resin composition according to any one of claims 1 to 6. A sheet-like laminated material containing the resin composition according to any one of claims 1 to 6. A resin sheet comprising a support and a resin composition layer formed of the resin composition according to any one of claims 1 to 6 provided on the support. A printed wiring board comprising an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 6. A semiconductor device comprising the printed wiring board according to claim 10.