Resin composition

Abstract

To provide a resin composition that achieves a lower dielectric tangent even in high-temperature conditions, and affords a cured product with superior crack resistance after desmear processing.SOLUTION: A resin composition comprises (A) an organic filler with liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a resin composition containing an epoxy resin, and further to a cured product, a sheet-like laminate material, a resin sheet, a printed wiring board, and a semiconductor device obtained by using the resin composition. [Background technology]

[0002] A known manufacturing technique for printed wiring boards is a build-up method in which insulating layers and conductor layers are alternately stacked. In the build-up method, the insulating layer is generally formed by curing a resin composition. The insulating layer of the printed wiring board of a semiconductor device is required to exhibit good dielectric properties (low dielectric constant, low dielectric loss tangent) in order to suppress transmission loss when the device is operated in a high-frequency environment.

[0003] As a resin composition that provides a cured product exhibiting good dielectric properties, for example, Patent Document 1 reports a resin composition that contains an active ester compound as a curing agent for an epoxy resin. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2009-235165 A Summary of the Invention [Problem to be solved by the invention]

[0005] A resin composition containing an active ester compound as a curing agent as described in Patent Document 1 produces a cured product with superior dielectric properties compared to a resin composition using a general phenol-based curing agent, but cracks tend to occur easily after desmearing. In addition, semiconductor devices may be exposed to high-temperature environments, such as when operating in a high-frequency environment, and it has been found that even materials that exhibit good dielectric properties in a room-temperature environment may have deteriorated dielectric properties (particularly dielectric tangent) in a high-temperature environment, and may not achieve the desired dielectric properties in an actual usage environment.

[0006] An object of the present invention is to provide a resin composition that can maintain a low dielectric tangent even in a high-temperature environment and can give a cured product that has excellent crack resistance after a desmear treatment, as well as a cured product, a sheet-like laminate material, a resin sheet, a printed wiring board, and a semiconductor device obtained using the resin composition. [Means for solving the problem]

[0007] Means for Solving the Problems of the Invention The present inventors conducted intensive studies in order to achieve the objects of the present invention, and as a result, unexpectedly found that by using an epoxy resin and an active ester compound as components of a resin composition, and further containing an organic filler having liquid crystallinity, it is possible to obtain a cured product which can keep the dielectric tangent low even in a high temperature environment and which can suppress the occurrence of cracks after a desmear treatment, and thus completed the present invention.

[0008] That is, the present invention includes the following. [1] A resin composition comprising (A) an organic filler having liquid crystal properties, (B) an epoxy resin, and (C) an active ester compound. [2] The resin composition according to the above-mentioned [1], wherein the content of the component (A) is 0.1 mass % or more and 10 mass % or less, when the resin component in the resin composition is 100 mass %. [3] (A) The resin composition according to the above [1] or [2], wherein the melting point of the organic filler having liquid crystallinity is 270° C. or higher. [4] The resin composition according to any one of the above [1] to [3], further comprising (D) an inorganic filler. [5] The resin composition according to any one of the above [1] to [4], further comprising (E) a radically polymerizable compound. [6] The resin composition according to any one of the above [1] to [5], which is for forming an interlayer insulating layer of a printed wiring board. [7] A cured product of the resin composition according to any one of the above items [1] to [6]. [8] A sheet-like laminate material comprising the resin composition according to any one of the above items [1] to [6]. [9] A resin sheet comprising: a support; and a resin composition layer formed on the support from the resin composition according to any one of the above items [1] to [6].

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

[11] A semiconductor device comprising the printed wiring board according to

[10] above. Effect of the Invention

[0009] According to the present invention, it is possible to provide a resin composition that can maintain a low dielectric tangent even in a high-temperature environment and can give a cured product that has excellent crack resistance after a desmear treatment; a cured product of the resin composition; a sheet-like laminate material and a resin sheet that include the resin composition; and a printed wiring board and a semiconductor device that include the cured product of the resin composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Hereinafter, the present invention will be described in detail with reference to embodiments and examples. However, the present invention is not limited to the following embodiments and examples, and may be modified and implemented as desired without departing from the scope of the claims of the present invention and their equivalents.

[0011] In the following description, the amount of each component is the amount of non-volatile component, unless otherwise specified. In the following description, unless otherwise specified, the "non-volatile components in the resin composition" may include the inorganic filler (D), while the "resin components" refers to the non-volatile components contained in the resin composition excluding the inorganic filler (D), unless otherwise specified.

[0012] <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, it is possible to keep the dielectric tangent low even in a high temperature environment such as 90°C, and to obtain a cured product having excellent crack resistance after desmearing. In addition, in the present invention, it is also possible to obtain a cured product having a low dielectric tangent even at room temperature such as 23°C or at normal temperature.

[0013] The resin composition of the present invention may further contain optional components in addition to (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound. Examples of the optional components include (D) an inorganic filler, (E) a radical polymerizable compound, (F) other curing agents, (G) a curing accelerator, (H) other additives, and (K) an organic solvent. In this specification, each of the above components (A) to (K) may also be referred to as "component (A)", "component (B)", etc. Each component contained in the resin composition will be described in detail below.

[0014] <(A) Organic filler having liquid crystal properties> The (A) organic filler having liquid crystallinity is specifically a filler containing an organic polymer having liquid crystallinity, and may be a filler made of an organic polymer having liquid crystallinity. The (A) component may be used alone or in combination of two or more types. In this specification, "having liquid crystallinity" means that anisotropy is observed by polarizing microscope observation when heated to the melting point or higher.

[0015] Examples of organic polymers having liquid crystallinity include general liquid crystal polymers, such as wholly aromatic polyesters synthesized from parahydroxybenzoic acid, biphenol, terephthalic acid, etc., and more specifically, those having a structural unit derived from parahydroxybenzoic acid ([-OC 6 H 4 -CO-]), and structural units derived from biphenol ([-OC 6 H 4 -C 6 H 4 -O-]), and structural units derived from terephthalic acid ([-OC-C 6 H 4 Examples of the structural unit include a polymer having at least one structural unit selected from the group consisting of: -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 at the end or side chain. As the liquid crystal polymer, for example, the liquid crystal polymer particles described in JP-A-2022-79336 can be preferably used.

[0016] The melting point of the liquid crystalline organic polymer is preferably 270° C. or higher, more preferably 280° C. or higher, and even more preferably 290° C. or higher, with the upper limit being preferably 370° C. or lower, preferably 360° C. or lower, and even more preferably 350° C. or lower. In this specification, the melting point of the liquid crystalline polymer complies with the test methods of ISO11357 and ASTM D3418, and can be measured using a differential scanning calorimeter (DSC) manufactured by Hitachi High-Tech Science Corporation, or the like.

[0017] When the organic polymer having liquid crystallinity has the above melting point, in the resin composition of the present invention, even under general curing conditions, it is poorly compatible with the epoxy resin (B) and the active ester compound (C), which generally have a relatively small average molecular weight, and is likely to contribute to stress relaxation of the cured product obtained using the resin composition, and tends to improve the crack resistance after a desmear treatment.

[0018] The filler, which is the component (A), is preferably a particle, powder or powder, and the particle size distribution of the powder is, for example, 0.1 μm or more, preferably 0.3 μm or more, more preferably 0.4 μm or more, even more preferably 0.5 μm or more, even more preferably 1 μm or more, particularly preferably 3 μm or more, and for example, 12 μm or less, 10 μm or less, preferably 8 μm or less, more preferably 6 μm or less, even more preferably 5.5 μm or less, and particularly preferably 5 μm. The particle size can be measured by a laser diffraction / scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is prepared on a volume basis using a laser diffraction / scattering type particle size distribution measuring device, and the median diameter is used as the average particle size.

[0019] The amount of acetic acid generated in the outgassing of the organic polymer having liquid crystallinity 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 generated in the outgassing of the organic polymer having liquid crystallinity can be controlled by adjusting the conditions in the synthesis process of the liquid crystal polymer, which is the raw material, such as the heating temperature and time of solid-phase polymerization. If the amount of acetic acid in the outgassing is small as described above, it is easy to reduce the increase in the dielectric tangent in the cured product obtained using the resin composition even in a situation where molecular motion generally increases in a high-temperature environment.

[0020] The dielectric loss tangent (measurement frequency: 10 GHz) of the liquid crystal organic polymer is 0.001 or less, preferably 0.0009 or less, more preferably 0.0008 or less, and even more preferably 0.0007 or less. This value is the measured value of the dielectric loss tangent in the in-plane direction of an injection molded product of the liquid crystal organic polymer. The injection molded product is a flat plate-shaped test piece of 30 mm x 30 mm x 0.4 mm (thickness).

[0021] Although the mechanism of the resin composition of the present invention is not entirely clear, it is presumed that the inclusion of component (A) that has liquid crystallinity, i.e., a rigid portion in the molecule, reduces the increase in dielectric tangent in the cured product obtained using the resin composition even in a high-temperature environment where molecular motion generally increases, and that the component (A) does not react with the active ester compound (C), contributing to stress relaxation in the cured product and improving crack resistance after desmearing. The component (A) is preferably insoluble in the epoxy resin (B), more preferably insoluble in the resin in the resin composition of the present invention even if the resin composition of the present invention contains a resin other than the component (B), and even more preferably insoluble in the resin and organic solvent in the resin composition of the present invention even if the resin composition of the present invention further contains an organic solvent (K).

[0022] The content of component (A) is, relative to 100 mass% of nonvolatile components in the resin composition, for example, 0.1 mass% or more, preferably 0.3 mass% or more, more preferably 0.4 mass% or more, even more preferably 0.5 mass% or more, even 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 mass% or less, and even more preferably 2.5 mass% or less.

[0023] The content of the (A) component, relative to 100 mass% of the resin components in the resin composition, is, for example, 0.1 mass% or more, preferably 0.5 mass% or more, more preferably 1 mass% or more, even more preferably 1.5 mass% or more, even more preferably 2 mass% or more, and is, for example, 12 mass% or less, preferably 10 mass% or less, more preferably 9.5 mass% or less, even more preferably 9 mass% or less, and even more preferably 8.5 mass% or less.

[0024] <(B) Epoxy resin> The resin composition of the present invention contains an epoxy resin (B). The epoxy resin (B) means a curable resin having an epoxy group.

[0025] (B) Epoxy resins include, for example, bixylenol type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol AF type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, naphthol novolac type epoxy resins, phenol novolac type epoxy resins, tert-butyl-catechol type epoxy resins, naphthalene type epoxy resins, naphthol type epoxy resins, anthracene type epoxy resins, glycidylamine type epoxy resins, glycidyl ester type epoxy resins, and the like. Examples of the epoxy resins include cresol novolac type epoxy resins, phenol aralkyl type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane type epoxy resins, cyclohexane dimethanol type epoxy resins, naphthylene ether type epoxy resins, trimethylol type epoxy resins, tetraphenylethane type epoxy resins, isocyanurate type epoxy resins, phenolphthalimidine type epoxy resins, phenolphthalein type epoxy resins, etc. (B) The epoxy resins may be used alone or in combination of two or more.

[0026] The resin composition preferably contains, as the (B) epoxy resin, an epoxy resin having two or more epoxy groups in one molecule. The proportion of the epoxy resin having two or more epoxy groups in one molecule relative to 100% by mass of the non-volatile components of the (B) epoxy resin is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0027] 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"). The resin composition of the present invention may contain only liquid epoxy resins as epoxy resins, or may contain only solid epoxy resins, or may contain a combination of liquid epoxy resins and solid epoxy resins. 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.

[0028] The liquid epoxy resin is preferably a liquid epoxy resin having two or more epoxy groups in one molecule.

[0029] As the liquid epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin having an ester skeleton, cyclohexane type epoxy resin, cyclohexane dimethanol type epoxy resin, and epoxy resin having a butadiene structure are preferred.

[0030] Specific examples of liquid epoxy resins include "HP4032", "HP4032D", and "HP4032SS" (naphthalene type epoxy resins) manufactured by DIC Corporation; "828US", "828EL", "jER828EL", "825", and "Epicoat 828EL" (bisphenol A type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER807" and "1750" (bisphenol F type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", and "604" (glycidylamine type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (glycirol type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L" and "EP-3 980S" (glycidylamine type epoxy resin); ADEKA's "EP-4088S" (dicyclopentadiene type epoxy resin); Nippon Steel & Sumitomo Metal Chemical's "ZX1059" (mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin); Nagase ChemteX's "EX-721" (glycidyl ester type epoxy resin); Daicel's "Celloxide 2021P" (alicyclic epoxy resin having an ester skeleton); Daicel's "PB-3600", Nippon Soda's "JP-100" and "JP-200" (epoxy resin having a butadiene structure); Nippon Steel & Sumitomo Metal Chemical's "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin). These may be used alone or in combination of two or more.

[0031] As the solid epoxy resin, a solid epoxy resin having three or more epoxy groups in one molecule is preferable, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferable.

[0032] Preferred solid epoxy resins include bixylenol type epoxy resins, naphthalene type epoxy resins, naphthalene type tetrafunctional epoxy resins, naphthol novolac type epoxy resins, cresol novolac type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, naphthol type epoxy resins, biphenyl type epoxy resins, naphthylene ether type epoxy resins, anthracene type epoxy resins, bisphenol A type epoxy resins, bisphenol AF type epoxy resins, phenol aralkyl type epoxy resins, tetraphenylethane type epoxy resins, phenolphthalimidine type epoxy resins, and phenolphthalein type epoxy resins.

[0033] Specific examples of solid epoxy resins include "HP4032H" (naphthalene type epoxy resin) manufactured by DIC Corporation; "HP-4700" and "HP-4710" (naphthalene type tetrafunctional epoxy resins) 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 resins) manufactured by DIC Corporation; and "EXA-73" manufactured by DIC Corporation. 11", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP6000" (naphthylene ether type epoxy resin); "EPPN-502H" (trisphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN475V" manufactured by Nippon Steel Chemical & Material Co., Ltd. (Naphthalene type epoxy resin); "ESN485" (Naphthol type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN375" (Dihydroxynaphthalene type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", "YL7890" (Bixylenol type epoxy resin) manufactured by Mitsubishi Chemical Co., Ltd.; "YL6121" (Biphenyl type epoxy resin) manufactured by Mitsubishi Chemical Co., Ltd.; "YX8800" (Anthracene type epoxy resin) manufactured by Mitsubishi Chemical Co., Ltd.; "YX77" manufactured by Mitsubishi Chemical Co., Ltd. Examples of epoxy resins include "PG-100" (phenol aralkyl type epoxy resin), "PG-100" and "CG-500" manufactured by Osaka Gas Chemicals, "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical, "YL7800" (fluorene type epoxy resin) manufactured by Mitsubishi Chemical, "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical, "jER1031S" (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical, and "WHR991S" (phenolphthalimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. These may be used alone or in combination of two or more types.

[0034] When a liquid epoxy resin and a solid epoxy resin are used in combination as the (B) 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, and even more preferably 1 or less.

[0035] The epoxy equivalent of the (B) epoxy resin is preferably 50 g / eq. to 5,000 g / eq., more preferably 60 g / eq. to 2,000 g / eq., even more preferably 70 g / eq. to 1,000 g / eq., and even more preferably 80 g / eq. to 500 g / eq. The epoxy equivalent is the mass of the resin per equivalent of epoxy group. This epoxy equivalent can be measured according to JIS K7236.

[0036] The weight average molecular weight (Mw) of the epoxy resin (B) is preferably from 100 to 5,000, more preferably from 250 to 3,000, and further preferably from 400 to 1500. The weight average molecular weight of the resin can be measured by gel permeation chromatography (GPC) as a polystyrene-equivalent value.

[0037] The content of the (B) component, relative to 100 mass% of the non-volatile components in the resin composition, is, for example, 1 mass% or more, preferably 3 mass% or more, more preferably 5 mass% or more, even more preferably 8 mass% or more, even more preferably 8.5 mass% or more, and is, for example, 30 mass% or less, preferably 20 mass% or less, more preferably 15 mass% or less, even more preferably 13 mass% or less, and even more preferably 10 mass% or less.

[0038] The content of the (B) component, relative to 100 mass% of the resin components in the resin composition, is, for example, 10 mass% or more, preferably 15 mass% or more, more preferably 20 mass% or more, even more preferably 25 mass% or more, even more preferably 28 mass% or more, particularly preferably 30 mass% or more, and is, for example, 60 mass% or less, preferably 55 mass% or less, more preferably 50 mass% or less, even more preferably 45 mass% or less, even more preferably 40 mass% or less, and particularly preferably 35 mass% or less.

[0039] <(C) Active ester compound> The resin composition of the present invention contains an active ester compound (C). The active ester compound (C) may be used alone or in any combination of two or more kinds at any ratio. The active ester compound (C) may have a function of reacting with the epoxy resin (B) to crosslink the epoxy resin (B). The active ester compound (C) may have a carbon-carbon unsaturated bond, and this unsaturated bond is preferably a carbon-carbon double bond, and may be, for example, the same as the carbon-carbon unsaturated bond of the component (C1) described below.

[0040] As the (C) active ester compound, generally, compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are preferably used. The active ester compound is preferably one obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester compound obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester compound obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is more preferred. Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenol compounds or naphthol compounds include 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, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, phenol novolac, etc. Here, the term "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing one molecule of dicyclopentadiene with two molecules of phenol.

[0041] Specifically, the (C) active ester compound is preferably 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 novolac, or an active ester compound containing a benzoylated product of phenol novolac, and more preferably at least one selected from a dicyclopentadiene type active ester compound and a naphthalene type active ester compound, and even more preferably a dicyclopentadiene type active ester compound. The dicyclopentadiene type active ester compound is preferably an active ester compound containing a dicyclopentadiene type diphenol structure. The "dicyclopentadiene type diphenol structure" refers to a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.

[0042] (C) Commercially available active ester compounds include, as active ester compounds containing a dicyclopentadiene-type diphenol structure, "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000", "HPC-8000-65T", "HPC-8000H", "HPC-8000H-65TM" (manufactured by DIC Corporation); as active ester compounds containing a naphthalene structure, "EXB-8100L-65T", "EXB-8150-60T", and "EXB-8150-62T" ", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T" (manufactured by DIC Corporation); an active ester compound containing phosphorus, "EXB9401" (manufactured by DIC Corporation); an active ester compound which is an acetylated product of phenol novolac, "DC808" (manufactured by Mitsubishi Chemical Corporation); active ester compounds which are benzoylated products of phenol novolac, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); an active ester compound containing a styryl group and a naphthalene structure, "PC1300-02-65MA" (manufactured by Air Water Inc.), and the like.

[0043] The active ester group equivalent of the (C) active ester compound is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., and further 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.

[0044] The ratio of the amounts of the (B) component and the (C) component is preferably 1.0 or more, more preferably 1.01 or more, even more preferably 1.03 or more, even more preferably 1.05 or more, and particularly preferably 1.1 or more, and is preferably 2.0 or less, more preferably 1.75 or less, even more preferably 1.5 or less, even more preferably 1.3 or less, and particularly preferably 1.2 or less, when the ratio of the amounts of the (B) component and the (C) component is within this range, the effects of the present invention can be easily obtained.

[0045] The content of component (C) is, relative to 100 mass% of non-volatile components in the resin composition, for example, 3 mass% or more, preferably 5 mass% or more, more preferably 10 mass% or more, even more preferably 13 mass% or more, even more preferably 15 mass% or more, and is, for example, 30 mass% or less, preferably 25 mass% or less, more preferably 20 mass% or less, and even more preferably 16 mass% or less.

[0046] The content of the (C) component, relative to 100 mass% of the resin components in the resin composition, is, for example, 30 mass% or more, preferably 40 mass% or more, more preferably 45 mass% or more, even more preferably 50 mass% or more, even more preferably 54 mass% or more, and is, for example, 70 mass% or less, preferably 65 mass% or less, more preferably 63 mass% or less, and even more preferably 60 mass% or less.

[0047] <(D) Inorganic filler> The resin composition of the present invention may contain an inorganic filler (D) as an optional component. The inorganic filler (D) is contained in the resin composition in the form of particles. The inorganic filler (D) may be used alone or in any combination of two or more kinds.

[0048] (D) An inorganic compound is used as the material of the inorganic filler. (D) Examples of the material of the inorganic filler include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, 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, 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. In addition, spherical silica is preferable as the silica. The (D) inorganic filler may be used alone or in combination of two or more kinds in any ratio.

[0049] (D) Commercially available inorganic fillers include, for example, "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", "YC100C", "YA050C", "YA050C-MJE", and "YA010C" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" manufactured by Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" manufactured by Tokuyama Corporation; "MGH-005" manufactured by Taiheiyo Cement Corporation; and "BA-S" manufactured by JGC Catalysts and Chemicals Co., Ltd.

[0050] The average particle size of the (D) inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, even more preferably 2 μm or less, even more preferably 1 μm or less, and particularly preferably 0.7 μm or less. The lower limit of the average particle size of the (D) inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, and particularly preferably 0.2 μm or more. The average particle size of the (D) inorganic filler can be measured by a laser diffraction / scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is created on a volume basis using a laser diffraction / scattering type particle size distribution measuring device, and the median diameter is taken as the average particle size. The measurement sample can be prepared by weighing 100 mg of the inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing it by ultrasonic waves for 10 minutes. The measurement sample was measured using a laser diffraction type particle size distribution measuring device with blue and red light source wavelengths, and the particle size distribution of the inorganic filler on a volume basis was measured using a flow cell method, and the average particle size was calculated as the median diameter from the particle size distribution obtained. An example of a laser diffraction type particle size distribution measuring device is the "LA-960" manufactured by Horiba, Ltd.

[0051] The specific surface area of ​​the (D) inorganic filler is not particularly limited, but is preferably 0.1 m 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more, particularly preferably 3m 2 The upper limit of the specific surface area of ​​the inorganic filler (D) is not particularly limited, but is preferably 100 m 2 / g or less, more preferably 70m 2 / g or less, more preferably 50m 2 / g or less, particularly preferably 40m 2 The specific surface area of ​​the inorganic filler is obtained by adsorbing nitrogen gas onto the surface of a sample using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) according to the BET method, and calculating the specific surface area using the BET multipoint method.

[0052] The inorganic filler (D) is preferably surface-treated with an appropriate surface treatment agent, which can enhance the moisture resistance and dispersibility of the inorganic filler (D). Examples of the surface treatment agent include vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy-based silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; styryl-based silane coupling agents such as p-styryltrimethoxysilane; methacryl-based silane coupling agents such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane; acrylic-based silane coupling agents such as 3-acryloxypropyltrimethoxysilane; N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltriethoxysilane, and N-2-(aminoethyl)-3-aminopropyltriethoxysilane; Amino-based silane coupling agents such as trimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, 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-isocyanatepropyltriethoxysilane; acid anhydride-based silane coupling agents such as 3-trimethoxysilylpropylsuccinic anhydride; and other silane coupling agents;Examples of the non-silane coupling alkoxysilane compounds include methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, 1,6-bis(trimethoxysilyl)hexane, and trifluoropropyltrimethoxysilane. The surface treatment agent may be used alone or in combination of two or more in any ratio.

[0053] Commercially available surface treatment agents include, for example, "KBM-1003" and "KBE-1003" (vinyl-based silane coupling agents) manufactured by Shin-Etsu Chemical Co., Ltd.; "KBM-303", "KBM-402", "KBM-403", "KBE-402", and "KBE-403" (epoxy-based silane coupling agents); "KBM-1403" (styryl-based silane coupling agents); "KBM-502", "KBM-503", "KBE-502", and "KBE-503" (methacrylic-based silane coupling agents); "KBM-5103" (acrylic-based silane coupling agents); "KBM-602", "KBM-603", "KBM-903", "KBE-903", "KBE-9103P", "KBM-573", and "KBM-575" (amino-based silane coupling agents); Examples include "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", and "KBM-7103" (non-silane coupling alkoxysilane compound).

[0054] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment with the surface treatment agent is preferably within a predetermined range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2% to 5% by mass of the surface treatment agent, more preferably 0.2% to 3% by mass, and even more preferably 0.3% to 2% by mass.

[0055] The degree of surface treatment with the 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 set to 0.02 mg / m 2 More than 0.1 mg / m is preferable. 2 More preferably, 0.2 mg / m or more 2 On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity in the form of a sheet, it is more preferable that the melt viscosity is 1.0 mg / m 2 Less than 0.8 mg / m is preferred. 2 Less than 0.5 mg / m is more preferable. 2 The following is even more preferred:

[0056] (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 (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been 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 solid content, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. As the carbon analyzer, the "EMIA-320V" manufactured by Horiba, Ltd., or the like can be used.

[0057] The content of the (D) inorganic filler in the resin composition is not particularly limited, but when the non-volatile components in the resin composition are taken as 100 mass%, it may be preferably 95 mass% or less, more preferably 90 mass% or less, even more preferably 85 mass% or less, even 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 components in the resin composition are taken as 100 mass%, it may be, for example, 0 mass% or more, 1 mass% or more, 10 mass% or more, 20 mass% or more, 30 mass% or more, etc., preferably 40 mass% or more, more preferably 50 mass% or more, even more preferably 60 mass% or more, even more preferably 65 mass% or more, and particularly preferably 70 mass% or more.

[0058] <(E) Radical Polymerizable Compound> The resin composition of the present invention may contain a radically polymerizable compound (E) as an optional component. The radically polymerizable compound (E) may be used alone or in any combination of two or more kinds.

[0059] The type of the radical polymerizable compound is not particularly limited as long as it has one or more (preferably two or more) radical polymerizable unsaturated groups in one molecule. Examples of the radical polymerizable compound include compounds having one or more radical polymerizable unsaturated groups selected from maleimide group, vinyl group, allyl group, styryl group, vinylphenyl group, acryloyl group, methacryloyl group, fumaroyl group, and maleoyl group. Among them, from the viewpoint of easily obtaining a cured product with excellent dielectric properties, it is preferable to contain (E1) a maleimide compound and / or (E2) other radical polymerizable compounds. (E2) Other radical polymerizable compounds are compounds that do not have a maleimide group and have a radical polymerizable unsaturated group other than a maleimide group, and among them, it is preferable to contain one or more selected from (meth)acrylic resins and styryl resins.

[0060] The type of the maleimide compound (E1) is not particularly limited, so long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups) in one molecule. Examples of maleimide compounds include maleimide resins containing an aliphatic skeleton having 36 carbon atoms derived from dimer diamine, such as "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all manufactured by DigiCner Molecules); maleimide resins containing an indane skeleton, as described in the Japan Institute of Invention and Innovation Disclosure Technical Bulletin No. 2020-500211; and maleimide resins containing an aromatic ring skeleton directly bonded to the nitrogen atom of the maleimide group, such as "MIR-3000-70MT", "MIR-5000-60T" (both manufactured by Nippon Kayaku Co., Ltd.), "BMI-4000" (manufactured by Daiwa Kasei Co., Ltd.), and "BMI-80" (manufactured by Keiai Kasei Co., Ltd.).

[0061] 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 groups and methacryloyl groups. Examples of methacrylic resins include (meth)acrylic resins such as "A-DOG" (manufactured by Shin-Nakamura Chemical Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Co., Ltd.), "NPDGA", "FM-400", "R-687", "THE-330", "PET-30", and "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.).

[0062] 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 in one 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 Company, Inc.).

[0063] The content of the (E) radically polymerizable compound in the resin composition may be 0% by mass or more than 0% by mass, and is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and particularly preferably 0.5% by mass or more, and is, for example, 10% by mass or less, preferably 5% by mass or less, more preferably 3% by mass or less, and particularly preferably 1.5% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0064] The content of the (E) radically polymerizable compound in the resin composition may be 0% by mass or more than 0% by mass, and is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, particularly preferably 2.5% by mass or more, and is, for example, 20% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, and particularly preferably 5% by mass or less, when the resin component in the resin composition is 100% by mass.

[0065] <(F) Other hardeners] The resin composition of the present invention may contain (F) other curing agents as optional components. The (F) other curing agents do not include those corresponding to the above-mentioned (A) to (C) and (E) components. The (F) other curing agents, like the above-mentioned (C) active ester compound, can function as an epoxy resin curing agent that reacts with the (B) epoxy resin to cure the resin composition. The (F) other curing agents may be used alone or in combination of two or more.

[0066] (F) Examples of other curing agents include 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 these, it is preferable to use one or more curing agents selected from the group consisting of phenol-based curing agents and carbodiimide-based curing agents.

[0067] As the phenol-based curing agent, a curing agent having one or more, preferably two or more, hydroxyl groups bonded to an aromatic ring such as a benzene ring or a naphthalene ring in one molecule can be used. From the viewpoint of heat resistance and water resistance, a phenol-based curing agent having a novolac structure is preferred. From the viewpoint of adhesion, a nitrogen-containing phenol-based curing agent is preferred, and a triazine skeleton-containing phenol-based curing agent is more preferred. Among them, from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion, a triazine skeleton-containing phenol novolac resin is preferred. Specific examples of phenol-based curing agents include "MEH-7700", "MEH-7810", and "MEH-7851" manufactured by Meiwa Kasei Co., Ltd.; "NHN", "CBN", and "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", and "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "LA-7052", "LA-7054", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", and "TD-2090-60M" manufactured by DIC Corporation.

[0068] 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 the carbodiimide-based curing agent include aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane bis(methylene-t-butylcarbodiimide); aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide); poly(phenylenecarbodiimide), poly( Examples of polycarbodiimides include aromatic polycarbodiimides such as poly(naphthylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and poly[methylenebis(methylphenylene)carbodiimide]. Commercially available carbodiimide curing agents include, for example, "Carbodilite V-02B", "Carbodilite V-03", "Carbodilite V-04K", "Carbodilite V-07", and "Carbodilite V-09" manufactured by Nisshinbo Chemical Inc.; and "Stavaxol P", "Stavaxol P400", and "Hi-Kasil 510" manufactured by Rhein Chemie.

[0069] As the acid anhydride 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 preferable. Specific examples of the acid anhydride curing agent include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic dianhydride, and benzophenonetetracarboxylic dianhydride. Examples of acid anhydrides include anhydrides, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic 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 copolymer of styrene and maleic acid. Commercially available acid anhydride curing agents include, for example, "HNA-100", "MH-700", "MTA-15", "DDSA", and "OSA" manufactured by New Japan Chemical Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200" and "HN-5500" manufactured by Hitachi Chemical Co., Ltd.; and "EF-30", "EF-40", "EF-60", and "EF-80" manufactured by Clay Valley.

[0070] As the amine-based curing agent, a curing agent having one or more, preferably two or more, amino groups in one molecule can be used. As the amine-based curing agent, for example, aliphatic amines, polyether amines, alicyclic amines, aromatic amines, etc. can be mentioned, among which aromatic amines are preferred. As the amine-based curing agent, primary amines or secondary amines are preferred, and primary amines are more preferred. Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxyphenyl)propane. 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(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, and the like. Commercially available amine-based curing agents include, for example, "SEIKACURE-S" manufactured by Seika Corporation; "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD AA", "KAYAHARD AB", and "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd.; "Epicure W" manufactured by Mitsubishi Chemical Corporation; and "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd.

[0071] Specific examples of benzoxazine-based curing agents include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation; "HFB2006M" manufactured by Showa Polymer Co., Ltd.; and "Pd" and "Fa" manufactured by Shikoku Chemical Industry Co., Ltd.

[0072] Examples of the cyanate ester curing agent include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanate phenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanate phenyl-1-(methylethylidene))benzene, bis(4-cyanate phenyl)thioether, and bis(4-cyanate phenyl)ether; polyfunctional cyanate resins derived from phenol novolac and cresol novolac; and prepolymers in which these cyanate resins are partially converted to triazine. Specific examples of cyanate ester-based curing agents include "PT30" and "PT60" (both of which are phenol novolac-type multifunctional cyanate ester resins), "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate has been converted to triazine to form a trimer), all of which are manufactured by Lonza Japan.

[0073] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate.

[0074] The active group equivalent of the (F) other curing agent is preferably 50 g / eq. to 3000 g / eq., more preferably 100 g / eq. to 1000 g / eq., further preferably 100 g / eq. to 500 g / eq., and 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.

[0075] The ratio of the amount of epoxy resin to the curing agent, that is, the ratio of the amount of the (B) component to the (C) component and the (F) component, is preferably 1.0 or more, more preferably 1.01 or more, more preferably 1.1 to 1.10 or more, even more preferably 1.15 or more, particularly preferably 1.2 or more, and is preferably 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 particularly preferably 1.3 or less, when the total value of the mass of the non-volatile component of the (B) component divided by the epoxy equivalent is a, the total value of the mass of the non-volatile component of the (C) component divided by the active ester group equivalent is b, and the total value of the mass of the non-volatile component of the (F) component divided by the active group equivalent is c, (b+c) / a is preferably 1.0 or more, more preferably 1.01 or more, even more preferably 1.1 to 1.10 or more, even more preferably 1.15 or more, and particularly preferably 1.2 or more, and is preferably 2.0 or less, more preferably 1.75 or less, even more preferably 1.5 or less, even more preferably 1.4 to 1.40 or less, and particularly preferably 1.3 or less. By setting the ratio of the amount of the epoxy resin to the curing agent within this range, the effects of the present invention can be easily obtained.

[0076] The content of (F) other curing agents in the resin composition may be 0% by mass or more, and is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and particularly preferably 1.0% by mass or more, and is preferably 20% by mass or less, more preferably 10% by mass or less, and particularly preferably 5% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0077] The content of (F) other curing agent in the resin composition may be 0% by mass or may be more than 0% by mass, and is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, particularly preferably 5.0% by mass or more, and is preferably 50% by mass or less, more preferably 20% by mass or less, and particularly preferably 10% by mass or less, when the resin component in the resin composition is 100% by mass.

[0078] <(G) Curing accelerator> The resin composition of the present invention may contain a curing accelerator (G) as an optional component.

[0079] 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, amine-based curing accelerators, etc. The (G) curing accelerator may be used alone or in combination of two or more kinds.

[0080] Examples of the phosphorus-based curing accelerator include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitate, tetrabutylphosphonium hydrogenhexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butylmethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate ... aromatic phosphonium salts such as tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone adducts such as triphenylphosphine-p-benzoquinone adduct; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine;Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, 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 Examples of aromatic phosphines include 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-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether.

[0081] Examples of the urea-based curing accelerator 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, and 3-(3,4-dimethylphenyl)-1,1-dimethylurea. aromatic dimethylureas such as butylurea, 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 N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluene bisdimethylurea].

[0082] Examples of the guanidine curing accelerator include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide.

[0083] Examples of the imidazole-based curing accelerator include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl-2-methylimidazole. 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-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl -(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(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-phenylimidazole isocyanuric acid adduct imidazole compounds such as 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of imidazole compounds and epoxy resins.

[0084] As the imidazole-based curing accelerator, commercially available products may be used, for example, "1B2PZ", "2MZA-PW", and "2PHZ-PW" manufactured by Shikoku Chemical Industry Co., Ltd., and "P200-H50" manufactured by Mitsubishi Chemical Corporation.

[0085] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, and organomanganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0086] Examples of the amine curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene.

[0087] As the amine-based curing accelerator, a commercially available product may be used, for example, "MY-25" manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0088] The content of the (G) curing accelerator in the resin composition is not particularly limited, but is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 3% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass. The lower limit of the content of the (E) curing accelerator in the resin composition is not particularly limited, but may be, for example, 0% by mass or more, 0.001% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, when the non-volatile components in the resin composition are taken as 100% by mass.

[0089] <(H) Other Additives> The resin composition of the present invention may further contain any additive as a non-volatile component. Examples of such additives include radical polymerization initiators such as peroxide radical polymerization initiators and azo radical polymerization initiators; epoxy curing agents other than active ester compounds such as phenolic curing agents, naphthol curing agents, acid anhydride curing agents, thiol curing agents, benzoxazine curing agents, cyanate ester curing agents, carbodiimide curing agents, and imidazole curing agents; phenoxy resins, polyvinyl acetal resins, polyolefin resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, and the like. thermoplastic resins such as polyether ether ketone resin, polyether ether ketone resin, polyester resin, etc.; organic fillers such as rubber particles; organometallic compounds such as organocopper compounds, organozinc compounds, organocobalt compounds, etc.; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black, etc.; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, phenothiazine, etc.; leveling agents such as silicone-based leveling agents, acrylic polymer-based leveling agents, etc.; bentone, montmorillonite, etc. thickeners such as nitrite; defoamers such as silicone-based defoamers, acrylic-based defoamers, fluorine-based defoamers, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silane; adhesion imparters such as triazole-based adhesion imparters, tetrazole-based adhesion imparters, and triazine-based adhesion imparters; antioxidants such as hindered phenol-based antioxidants and hindered amine-based antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; phosphorus-based flame retardants (for example, phosphate esters Examples of suitable flame retardants include flame retardants such as butyl compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus, nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; and stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers.The other additives (F) may be used alone or in any combination of two or more at any ratio. The content of the other additives (H) can be appropriately determined by a person skilled in the art.

[0090] <(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 components described above. As the (K) organic solvent, a known one may be appropriately used, and the type is not particularly limited. As the (K) organic solvent, for example, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.; ester-based solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, γ-butyrolactone, etc.; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, etc.; alcohol-based solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, etc.; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, methyl methoxypropionate, etc. Examples of the organic solvent include ether ester 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 solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The organic solvent (K) may be used alone or in combination of two or more in any ratio.

[0091] In one embodiment, the content of the (K) organic solvent is not particularly limited, but when all components in the resin composition are taken as 100 mass%, it can be, for example, 60 mass% or less, 40 mass% or less, 30 mass% or less, 20 mass% or less, 15 mass% or less, 10 mass% or less, etc.

[0092] <Method of producing resin composition> The resin composition of the present invention can be produced, for example, by adding (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (C) an active ester compound, if necessary (D) an inorganic filler, if necessary (E) a radically polymerizable compound, if necessary (F) other curing agents, if necessary (G) a curing accelerator, if necessary (H) other additives, if necessary, and if necessary (K) an organic solvent in any order and / or all at once and mixing them in any preparation vessel. In addition, the temperature can be appropriately set during the process of adding and mixing each component, and heating and / or cooling may be performed temporarily or throughout. In addition, during or after the process of adding and mixing, the resin composition may be stirred or shaken using a stirring device or shaking device such as a mixer to disperse uniformly. In addition, degassing may be performed under low pressure conditions such as under vacuum at the same time as stirring or shaking.

[0093] <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, it is possible to keep the dielectric tangent low even in a high temperature environment such as 90° C., and to obtain a cured product having excellent crack resistance after desmearing, and preferably, to obtain a cured product having a low dielectric tangent even at room temperature such as 23° C.

[0094] The cured product of the resin composition of the present invention may have a feature that it can suppress the occurrence of cracks after desmear treatment (roughening treatment). Thus, in one embodiment, after producing a circuit board and subjecting it to desmear treatment as in the following Test Example 2, when 100 copper pads of the circuit board are observed, the number of cracks may be preferably 10 or less (10% or less).

[0095] The cured product of the resin composition of the present invention may be characterized by a low dielectric loss tangent (Df) even in a high temperature environment such as 90° C. Thus, 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 may be preferably 0.020 or less, 0.010 or less, more preferably 0.009 or less, 0.008 or less, even more preferably 0.007 or less, 0.006 or less, and particularly preferably 0.005 or less, 0.004 or less, or 0.003 or less.

[0096] The cured product of the resin composition of the present invention may be characterized by a low dielectric loss tangent (Df) even at room temperature or normal temperature, such as 23° C. Thus, 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 may be preferably 0.020 or less, 0.010 or less, more preferably 0.009 or less, 0.008 or less, even more preferably 0.007 or less, 0.006 or less, still more preferably 0.005 or less, 0.004 or less, and particularly preferably 0.003 or less, 0.002 or less.

[0097] <Applications of resin composition> The resin composition of the present invention can be suitably used as a resin composition for insulating purposes, particularly as a resin composition for forming an insulating layer. Specifically, it can be suitably used as a resin composition for forming an 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 an insulating layer. In addition, in a 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 can also be used in a wide range of applications requiring a resin composition, such as a resin sheet, a sheet-like laminate material such as a prepreg, a solder resist, an underfill material, a die bonding material, a semiconductor encapsulant, a hole filling resin, and a component embedding resin.

[0098] In addition, for example, when a semiconductor chip package is manufactured through the following steps (1) to (6), the resin composition of the present invention can be suitably used as a resin composition for a rewiring formation layer (resin composition for forming a rewiring formation layer) as an insulating layer for forming a rewiring layer, and as a resin composition for sealing a semiconductor chip (resin composition for sealing a semiconductor chip). When a semiconductor chip package is manufactured, a rewiring layer may be further formed on the sealing layer. (1) A step of laminating a temporary fixing film onto a substrate; (2) a step of temporarily fixing a semiconductor chip on a temporary fixing film; (3) forming an encapsulation layer on the semiconductor chip; (4) peeling the substrate and the temporary fixing film from the semiconductor chip; (5) forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled off; and (6) A process of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0099] Furthermore, the resin composition of the present invention provides an insulating layer with good component embedding properties, and therefore can be suitably used when the printed wiring board is a circuit board with built-in components.

[0100] <Sheet-type laminated material> The resin composition of the present invention can be used by coating in the form of a varnish, but from an industrial perspective, it is generally preferred to use the resin composition in the form of a sheet-like laminate material containing the resin composition.

[0101] As the sheet-like laminate material, the following resin sheets and prepregs are preferred.

[0102] 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.

[0103] The thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less, from the viewpoint of making the printed wiring board thinner and being able to provide a cured product with excellent insulation 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.

[0104] Examples of the support include films made of plastic materials, metal foils, and release papers, with films made of plastic materials and metal foils being preferred.

[0105] When a film made of a plastic material is used as the support, examples of the plastic material include polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), polycarbonate (hereinafter sometimes abbreviated as "PC"), acrylics such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0106] When a metal foil is used as the support, examples of the metal foil include copper foil, aluminum foil, etc., and copper foil is preferred. As the copper foil, a foil made of a single metal, copper, or an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0107] The surface of the support to be bonded to the resin composition layer may be subjected to a matte treatment, a corona treatment, or an antistatic treatment.

[0108] In addition, as the support, a support with a release layer having a release layer on the surface to be bonded to the resin composition layer may be used. The release agent used in the release layer of the support with a release layer may be, for example, one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. The support with a release layer may be a commercially available product, for example, "SK-1", "AL-5", and "AL-7" manufactured by Lintec Corporation, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, and "Unipeel" manufactured by Unitika Limited, which are PET films having a release layer mainly composed of an alkyd resin-based release agent.

[0109] 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. When a support with a release layer is used, it is preferable that the total thickness of the support with a release layer is in the above range.

[0110] In one embodiment, the resin sheet may further include an optional layer as necessary. For example, such an optional layer may be a protective film equivalent to the support provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface 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 the protective film, adhesion of dirt and the like to the surface of the resin composition layer and scratches can be suppressed.

[0111] The resin sheet can be produced, for example, by preparing a liquid resin composition as is or a resin varnish by dissolving the resin composition in an organic solvent, applying this onto a support using a die coater or the like, and then drying to form a resin composition layer.

[0112] The organic solvent may be the same as the organic solvent described as a component of the resin composition. The organic solvent may be used alone or in combination of two or more kinds.

[0113] Drying may be performed by a known method such as heating or hot air blowing. Drying conditions are not particularly limited, but drying is performed so that the content of the organic solvent in the resin composition layer becomes 10% by mass or less, preferably 5% by mass or less. Although it varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when a resin composition or resin varnish containing 30% by mass to 60% by mass of the organic solvent is used, the resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0114] The resin sheet can be stored in a rolled state. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0115] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber substrate with the resin composition of the present invention.

[0116] The sheet-like fiber substrate used for the prepreg is not particularly limited, and can be a substrate commonly used for prepreg, such as glass cloth, aramid nonwoven fabric, liquid crystal polymer nonwoven fabric, etc. From the viewpoint of thinning the printed wiring board, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber substrate is not particularly limited. It is usually 10 μm or more.

[0117] The prepreg can be produced by a known method such as a hot melt method or a solvent method.

[0118] The thickness of the prepreg may be in the same range as that of the resin composition layer in the above-mentioned resin sheet.

[0119] The sheet-like laminate material of the present invention can be suitably used for forming an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board).

[0120] <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.

[0121] The printed wiring board can be produced, for example, by using the above-mentioned resin sheet by a method including the following steps (I) and (II). (I) A step of laminating a resin sheet on an inner layer substrate such that a resin composition layer of the resin sheet is bonded to the inner layer substrate. (II) A step of curing (e.g., heat curing) the resin composition layer to form an insulating layer.

[0122] The "inner layer substrate" used in step (I) is a member that becomes the substrate of a printed wiring board, and examples thereof include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, and a thermosetting polyphenylene ether substrate. The substrate may have a conductor layer on one or both sides, and the conductor layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate may be called an "inner layer circuit substrate". In addition, an intermediate product on which an insulating layer and / or a conductor layer is to be further formed during the manufacture of a printed wiring board is also included in the "inner layer substrate" of the present invention. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

[0123] The lamination of the inner layer substrate and the resin sheet can be carried out, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of the member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as the "thermocompression bonding member") include a heated metal plate (such as a SUS plate) or a metal roll (SUS roll). It is preferable to press the thermocompression member not directly onto the resin sheet, but via an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently follow the surface irregularities of the inner layer substrate.

[0124] The lamination of the inner layer substrate and the resin sheet may be performed by a vacuum lamination method. In the vacuum lamination method, the thermocompression temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the thermocompression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably in the range of 0.29MPa to 1.47MPa, and the thermocompression time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. The lamination may be performed under reduced pressure conditions, preferably at a pressure of 26.7hPa or less.

[0125] The lamination can be performed by a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch type vacuum pressure laminator.

[0126] After lamination, the laminated resin sheet may be smoothed under normal pressure (atmospheric pressure), for example, by pressing a thermocompression member from the support side. The pressing conditions for the smoothing treatment may be the same as the thermocompression conditions for the lamination. The smoothing treatment may be performed using a commercially available laminator. The lamination and smoothing treatment may be performed consecutively using the commercially available vacuum laminator.

[0127] The support may be removed between step (I) and step (II) or after step (II).

[0128] In step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer made of a cured product of the resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions that are usually adopted when forming an insulating layer for a printed wiring board may be used.

[0129] For example, the heat curing conditions of the resin composition layer vary depending on the type of resin composition, but in one embodiment, the curing temperature is, for example, 120° C. or higher, 130° C. or higher, more than 130° C., 135° C. or higher, more preferably 140° C. or higher, more preferably 150° C. or higher, and even more preferably 170° C. or higher, and is, for example, 240° C. or lower, preferably 220° C. or lower, and more preferably 210° C. or lower. The curing time can be preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0130] Before the resin composition layer is thermally cured, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated 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, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0131] In manufacturing a printed wiring board, the steps of (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming a conductor layer may be further carried out. These steps (III) to (V) may be carried out according to various methods known to those skilled in the art for use in manufacturing printed wiring boards. When the support is removed after step (II), the support may be removed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). In addition, the formation of the insulating layer and the conductor layer in steps (II) to (V) may be repeated to form a multilayer wiring board, as necessary.

[0132] In another embodiment, the printed wiring board of the present invention can be manufactured using the above-mentioned prepreg. The manufacturing method is basically the same as when a resin sheet is used.

[0133] Step (III) is a step of drilling holes in the insulating layer, which allows holes such as via holes and through holes to be formed in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, etc., depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be appropriately determined depending on the design of the printed wiring board.

[0134] Step (IV) is a step of roughening the insulating layer. Usually, smears are also removed in this step (IV). The procedure and conditions of the roughening treatment are not particularly limited, and known procedures and conditions that are usually used when forming an insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by carrying out a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid in this order.

[0135] The swelling liquid used in the roughening treatment is not particularly limited, but includes an alkaline solution, a surfactant solution, etc., and is preferably an alkaline solution, and more preferably a sodium hydroxide solution or a potassium hydroxide solution. Examples of commercially available swelling liquids include "Swelling Dip Securigans P" and "Swelling Dip Securigans SBU" manufactured by Atotech Japan. The swelling treatment using the swelling liquid is not particularly limited, but can be performed by immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes, for example. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0136] The oxidizing agent used in the roughening treatment is not particularly limited, but may be, for example, an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The roughening treatment using an oxidizing agent such as an alkaline permanganate solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include, for example, alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigans P" manufactured by Atotech Japan.

[0137] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and a commercially available product such as "Reduction Solution Securigant P" manufactured by Atotech Japan can be mentioned.

[0138] The treatment with the neutralizing solution can be carried out by immersing the surface that has been roughened with an oxidizing agent in a neutralizing solution at 30° C. to 80° C. for 5 to 30 minutes. From the viewpoint of workability, etc., a method in which the object that has been roughened with an oxidizing agent is immersed in a neutralizing solution at 40° C. to 70° C. for 5 to 20 minutes is preferred.

[0139] In the step (V), a conductor layer is formed on the insulating layer. There is no particular limitation on the conductor material used for the conductor layer.

[0140] In a preferred embodiment, the conductor layer contains 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. The conductor layer may be a single metal layer or an alloy layer, and examples of the alloy layer include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy and copper-titanium alloy). Among them, from the viewpoints of versatility, cost, ease of patterning, etc. of the conductor layer formation, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or an alloy layer of a nickel-chromium alloy, a copper-nickel alloy or a copper-titanium alloy is preferred, 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 preferred, and a single metal layer of copper is even more preferred.

[0141] The conductor layer may be a single-layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different kinds 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 a nickel-chromium alloy.

[0142] The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, and preferably 5 μm to 30 μm.

[0143] In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer by a conventionally known technique such as a semi-additive method or a full-additive method, and from the viewpoint of ease of production, it is preferable to form the conductor layer by the semi-additive method. An example of forming the conductor layer by the semi-additive method will be described below.

[0144] First, a plating seed layer is formed on the surface of an insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer to expose a part of the plating seed layer corresponding to a desired wiring pattern. After a metal layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, unnecessary plating seed layer is removed by etching or the like to form a conductor layer having a desired wiring pattern.

[0145] In another embodiment, the conductor layer may be formed using a metal foil. When the conductor layer is formed using a metal foil, it is preferable to carry out step (V) between steps (I) and (II). For example, after step (I), the support is removed, and a metal foil is laminated on the exposed surface of the resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is carried out to form an insulating layer. Thereafter, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as a subtractive method or a modified semi-additive method, using the metal foil on the insulating layer.

[0146] The metal foil can be produced by a known method such as an electrolytic method, a rolling method, etc. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Nippon Mining & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0147] <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 by using the printed wiring board of the present invention.

[0148] Examples of the semiconductor device include various semiconductor devices used in electric appliances (for example, computers, mobile phones, digital cameras, and televisions) and vehicles (for example, motorcycles, automobiles, trains, ships, and aircraft). EXAMPLES

[0149] The present invention will be specifically described below with reference to examples. The present invention is not limited to these examples. In the following, "parts" and "%" representing amounts mean "parts by mass" and "% by mass", respectively, unless otherwise specified. Unless otherwise specified, the temperature condition is room temperature (25°C).

[0150] <Synthesis Example 1: Synthesis of Liquid Crystal Polymer> A polymerization vessel equipped with a stirring blade was charged with 60 mol% of 6-hydroxy-2-naphthoic acid (HNA), 20 mol% of 4,4-dihydroxybiphenyl (BP), 15.5 mol% of terephthalic acid (TPA), and 4.5 mol% of 2,6-naphthalenedicarboxylic acid (NADA). Potassium acetate and magnesium acetate were also charged as catalysts. The vessel was depressurized and nitrogen was injected three times to replace the atmosphere with nitrogen. Then, acetic anhydride (1.08 molar equivalents relative to the hydroxyl groups) was further added, and the temperature was raised to 150°C. The acetylation reaction was carried out under reflux for 2 hours.

[0151] After the acetylation was completed, the polymerization vessel in which acetic acid was distilled was heated at a rate of 0.5°C / min, and when the melt temperature in the vessel reached 310°C, the polymer was taken out and cooled to solidify. The obtained polymer was pulverized to a size that could pass through a sieve with 2.0 mm openings to obtain a prepolymer.

[0152] Next, the prepolymer obtained above was heated from room temperature to 310°C over 14 hours using a heater in an oven manufactured by Yamato Scientific Co., Ltd., and then the temperature was maintained at 310°C for 1 hour to carry out solid-phase polymerization. The prepolymer was then allowed to naturally dissipate heat at room temperature to obtain liquid crystal polymer A. Using a polarizing microscope manufactured by Olympus Co., Ltd. (product name: BH-2) equipped with a hot stage for microscope manufactured by Mettler (product name: FP82HT), the liquid crystal polymer A was heated and melted on the microscope heating stage, and it was confirmed that the polymer exhibited liquid crystallinity based on the presence or absence of optical anisotropy.

[0153] <Preparation Example 1: Production of Liquid Crystal Polymer Particles> The powder of liquid crystal polymer A synthesized above was continuously pulverized using an apparatus consisting of a Nippon Pneumatic Mfg. Co., Ltd. SPK-12 jet mill combined with a Nippon Pneumatic Mfg. Co., Ltd. DSF-10 classifier under conditions of a pulverization pressure of 0.65 MPa and a resin supply rate of 5 kg / h to obtain liquid crystal polymer particles A.

[0154] <Evaluation of Liquid Crystal Polymer Particles> (Melt point measurement) 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 was raised from room temperature to 360 to 380°C at a rate of 10°C / min to completely melt the polymer, then the temperature was lowered to 30°C at a rate of 10°C / min, and the apex of the endothermic peak obtained when the temperature was further raised to 380°C at a rate of 10°C / min was taken as the melting point. The measured melting point was 319°C.

[0155] (Measurement of particle size distribution) The particle size distribution of the liquid crystal polymer particles A obtained above was measured using a laser diffraction / scattering particle size distribution measurement device (Beckman Coulter, LS 13 320 dry system, equipped with a Tornado dry powder module). The parameters D50, D90 and Dp, which indicate the particle size distribution, were obtained as calculation results from the measurement data. As a result, D50 was 4.8 μm and D90 / D50 was 1.7.

[0156] (Measurement of dielectric tangent (10GHz)) The liquid crystal polymer particles A obtained above were heated and melted under conditions of melting point to melting point + 30°C, and injection molded using a mold of 30mm x 30mm x 0.4mm (thickness) to prepare a flat test piece. Next, the dielectric loss tangent at a frequency of 10GHz was measured using the Keysight Technologies' network analyzer N5247A by split post dielectric resonator method (SPDR method). Each type of sample was measured by N=4, and the dielectric loss tangent calculated as the average value of the four measurements was 0.0007.

[0157] (Outgassing Measurement) The liquid crystal polymer particles A obtained above were placed in a 20 ml vial and sealed, and then heat-treated at 190°C for 1 hour. The acetic acid and other gases (phenol, phenyl acetate, etc.) generated during the heat treatment were quantified using a gas chromatograph (HP7820A) connected to a headspace sampler (HP7697A) manufactured by Hewlett-Packard. The column used was G-100 (40 m) manufactured by Chemical Inspection Association, and other conditions were an initial temperature of 45°C, a heating rate of 20°C / min, a final temperature of 280°C, a helium pressure of 8.3 psi, and a split ratio of 2.0, and measurements were performed using an FID detector. The measured outgassing amount was 0.4 ppm for acetic acid, and 5.8 ppm for other outgases.

[0158] <Examples 1 to 8 and Comparative Example 1: Preparation of Resin Varnish> [Example 1] Naphthalene-type epoxy resin (DIC Corporation "HP-4032-SS", epoxy equivalent 144 g / eq.) 15 parts, active ester-based curing agent ("HPC-8150-62T", active group equivalent 229 g / eq., toluene solution with non-volatile content of 61.5% by mass) 43 parts, other curing agent (phenol-based curing agent, DIC Corporation "LA-3018-50P", hydroxyl group equivalent 151 g / eq., 1-methoxy-2-propanol solution with non-volatile content of 50% by mass) 5 parts, liquid crystal polymer powder A as component (A) 2 parts, inorganic filler (spherical silica surface-treated with an amine-based alkoxysilane compound (Shin-Etsu Chemical Co., Ltd. "KBM573") (Admatechs Co., Ltd., "SO-C2", average particle size 0.5 μm, specific surface area 5.8 m 2 A resin varnish was obtained by mixing 125 parts of ethyl acetate / g, 0.5 parts of a curing accelerator (manufactured by Shikoku Chemical Industry Co., Ltd., "1B2PZ"), 10 parts of MEK, and 10 parts of cyclohexanone and dispersing the mixture uniformly using a high-speed rotating mixer.

[0159] [Example 2] In Example 1, 2 parts of an MEK solution (62% by mass of non-volatile components) of maleimide compound A (Mw / Mn=1.81, t''=1.47 (mainly 1, 2 or 3)) represented by the following formula (M) synthesized by the method described in Synthesis Example 1 of Japan Institute of Invention and Innovation Disclosure Technical Journal Publication No. 2020-500211 was used. A resin varnish was obtained in the same manner as in Example 1, except for the above points. [ka]

[0160] [Example 3] A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of another maleimide compound ("MIR-5000-60T" manufactured by Nippon Kayaku Co., Ltd., a toluene solution with a non-volatile content of 60% by mass) was added.

[0161] [Example 4] A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of another maleimide compound ("MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd., a mixed solution of toluene and MEK with a non-volatile content of 70% by mass) was added.

[0162] [Example 5] A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of another maleimide compound ("BMI-689" manufactured by Designor Molecules, Inc.) was added.

[0163] [Example 6] A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of another compound having a double bond ("OPE-2St-1200" manufactured by Mitsubishi Gas Chemical Co., Ltd., a toluene solution with a non-volatile content of 65% by mass) was added.

[0164] [Example 7] A resin varnish was obtained in the same manner as in Example 1, except that the amount of liquid crystal polymer powder A as component (A) was changed from 2 parts to 1 part.

[0165] [Example 8] A resin varnish was obtained in the same manner as in Example 1, except that the amount of liquid crystal polymer powder A as component (A) was changed from 2 parts to 4 parts.

[0166] [Comparative Example 1] A resin varnish was obtained in the same manner as in Example 1, except that 2 parts of the liquid crystal polymer powder A as the component (A) was not added.

[0167] <Production Example 1: Production of resin sheet A having a resin composition layer thickness of 40 μm> A polyethylene terephthalate film with a release layer ("AL5" manufactured by Lintec Corporation, thickness 38 μm) was prepared as a support. On the release layer of this support, the resin varnish obtained in the examples and comparative examples was uniformly applied so that the thickness of the resin composition layer after drying 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 including a support and a resin composition layer.

[0168] <Test Example 1: Measurement of dielectric tangent> The resin sheet A obtained in Production Example 1 was cured in an oven at 190° C. for 90 minutes using the resin varnish obtained in the Examples and Comparative Examples. The support was peeled off from the resin sheet A taken out of the oven to obtain a cured product of the resin composition layer. The cured product was cut into a length of 80 mm and a width of 2 mm to be used as a cured product for evaluation.

[0169] For each evaluation cured product, the dielectric tangent value (Df value) was measured by the cavity resonance perturbation method using an Agilent Technologies HP8362B at a measurement frequency of 5.8 GHz and measurement temperatures of 23° C. and 90° C. Measurements were performed on two test pieces, and the average was calculated.

[0170] <Production Example 2: Production of resin sheet B having a resin composition layer thickness of 25 μm> A polyethylene terephthalate film with a release layer ("AL5" manufactured by Lintec Corporation, thickness 38 μm) was prepared as a support. On the release layer of this support, the resin varnish obtained in the examples and comparative examples was uniformly applied so that the thickness of the resin composition layer after drying was 25 μm, and dried at 70°C to 80°C (average 75°C) for 2.5 minutes to obtain a resin sheet B including a support and a resin composition layer.

[0171] <Test Example 2: Evaluation of crack resistance after desmear treatment> The 25 μm thick resin sheet B produced in Production Example 2 was laminated on both sides of a core material (Hitachi Chemical Co., Ltd. "E705GR", thickness 400 μm) in which circular copper pads (copper thickness 35 μm) with a diameter of 350 μm were formed in a grid pattern at intervals of 400 μm so that the residual copper rate was 60%. Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd. 2-stage build-up laminator "CVP700"), the resin composition layer was bonded to the inner layer substrate. This lamination was performed by decompressing for 30 seconds to an atmospheric pressure of 13 hPa or less, and then pressing for 30 seconds at a temperature of 100 ° C and a pressure of 0.74 MPa. This was placed in a 130 ° C oven and heated for 30 minutes, and then transferred to a 170 ° C oven and heated for 30 minutes. The support was then peeled off, and the resulting circuit board was immersed in a swelling liquid, Swelling Dip Securigant P (Atotech Japan Co., Ltd.), at 60°C for 10 minutes. Next, a roughening liquid, Concentrate Compact P (KMnO 4 The substrate was immersed in a neutralizing solution (aqueous solution of NaOH: 60 g / L, NaOH: 40 g / L) at 80°C for 30 minutes. Finally, the substrate was immersed in a neutralizing solution, Reduction Solution Securigant P, manufactured by Atotech Japan Co., Ltd., at 40°C for 5 minutes. After the roughening treatment, 100 copper pads of the circuit board were observed to check for the presence or absence of cracks in the resin composition layer. If there were 10 or fewer cracks, the result was marked as "Good", and if there were more than 10 cracks, the result was marked as "Poor".

[0172] The amounts (parts by mass) of components (A) to (G) used, including volatile components, in the resin compositions of the Examples and Comparative Examples, and the measurement results of the Test Examples, are shown in the following Table 1. In Table 1, the non-volatile content (mass%) of each component is shown in the "NV" column.

[0173] [Table 1]

[0174] From the above, it was found that by using a resin composition containing (A) an organic filler having liquid crystallinity, (B) an epoxy resin, and (B) an active ester compound, it is possible to obtain a cured product that has a low dielectric tangent (Df) even in a high-temperature environment such as 90° C. and has excellent crack resistance after desmearing. It was also found that this cured product has a low dielectric tangent (Df) even at room temperature such as 23° C. or in the normal temperature range.

Claims

1. A resin composition comprising (A) an organic filler having liquid crystallinity, (B) an epoxy resin, (C) an active ester compound, (D) an inorganic filler, (F) a curing agent (provided that it does not include those corresponding to component (A), those corresponding to component (B), and those corresponding to component (C)), and (G) a curing accelerator, wherein the content of component (A) is 0.1% by mass or more and 5% by mass or less based on 100% by mass of the non-volatile components in the resin composition; the content of component (B) is 3% by mass or more and 15% by mass or less based on 100% by mass of the non-volatile components in the resin composition; the content of component (C) is 5% by mass or more and 25% by mass or less based on 100% by mass of the non-volatile components in the resin composition; the content of component (D) is 60% by mass or more and 80% by mass or less when the non-volatile components in the resin composition are taken as 100% by mass.

2. The resin composition according to claim 1, wherein the melting point of the organic filler (A) having liquid crystallinity is 270°C or higher.

3. The resin composition according to claim 1, further comprising (E) a radically polymerizable compound.

4. The resin composition according to claim 1, which is used for forming an interlayer insulating layer of a printed wiring board.

5. A cured product of the resin composition according to any one of claims 1 to 4.

6. A sheet-like laminated material containing the resin composition according to any one of claims 1 to 4.

7. A resin sheet having a support and a resin composition layer formed from the resin composition according to any one of claims 1 to 4 provided on the support.

8. A printed wiring board provided with an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 4.

9. A semiconductor device including the printed wiring board according to claim 8.

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