Resin composition

Abstract

The present invention aims to provide a resin composition that can reduce the dielectric properties of a cured product and suppress the generation of flow marks. The solution of the present invention is a resin composition comprising (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, wherein component (B) comprises (B-1) an active ester resin having a softening point of 100°C or less, (B-2) a difunctional active ester resin, or (B-3) an active ester resin having a molecular weight of 1000 or less.

Description

Technical Field

[0001] The present invention relates to a resin composition comprising an epoxy resin and a curing agent, a cured product of the resin composition, a resin sheet comprising the resin composition, a circuit substrate comprising the cured product, a semiconductor chip package comprising the cured product, and a semiconductor device comprising the semiconductor chip package. Background Art

[0002] In recent years, with the increasing demand for small, high-performance electronic devices such as smartphones and tablets, the insulating materials used to encapsulate semiconductor chips in these small electronic devices are also required to be more functional. Such insulating layers are known to be formed by curing resin compositions (see, for example, Patent Document 1).

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Laid-Open No. 2017-008312. Summary of the Invention

[0006] Technical problem to be solved by the invention

[0007] As the demand for miniaturization and thinner films continues to increase, insulating materials used in semiconductor chip packaging are required to have lower dielectric properties. However, conventional insulating materials with low dielectric properties are prone to flow marks.

[0008] An object of the present invention is to provide a resin composition that can reduce the dielectric properties of a cured product and suppress the generation of flow marks.

[0009] Technical solutions used to solve technical problems

[0010] To achieve the objectives of the present invention, the present inventors conducted intensive research and found that the aforementioned issues can be resolved by using (B-1) an active ester resin having a softening point of 100°C or less, (B-2) a difunctional active ester resin, or (B-3) an active ester resin having a molecular weight of 1000 or less as the curing agent (B), thereby completing the present invention.

[0011] That is, the present invention includes the following contents,

[0012] [1] A resin composition comprising (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, wherein the component (B) comprises (B-1) an active ester resin having a softening point of 100°C or less;

[0013] [2] The resin composition according to [1] above, wherein the content of the component (B-1) is 1% by mass to 50% by mass, based on 100% by mass of the non-volatile component in the resin composition;

[0014] [3] A resin composition comprising (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, wherein component (B) comprises (B-2) a difunctional active ester resin;

[0015] [4] The resin composition according to [3] above, wherein the component (B-2) is a compound represented by formula (1);

[0016] [Chemical Formula 1]

[0017]

[0018] In the formula, rings X, Y and Z each independently represent an aromatic ring which may further have a substituent;

[0019] [5] The resin composition according to any one of [1] to [4] above, wherein the component (B) further comprises one or more curing agents selected from the group consisting of phenolic curing agents, naphthol curing agents, amine curing agents, and acid anhydride curing agents;

[0020] [6] The resin composition according to any one of [1] to [5] above, wherein component (A) is a liquid epoxy resin;

[0021] [7] The resin composition according to any one of [1] to [6] above, wherein the average particle size of component (C) is 1 μm to 40 μm;

[0022] [8] The resin composition according to any one of [1] to [7] above, wherein the content of component (C) is 80% by mass or more, based on 100% by mass of the non-volatile component in the resin composition;

[0023] [9] The resin composition according to any one of [1] to [8] above, which is liquid at 25°C;

[0024]

[10] The resin composition according to any one of [1] to [9] above, which is used to form an insulating layer of a semiconductor chip package;

[0025]

[11] The resin composition according to any one of [1] to [9], which is used to form an insulating layer of a circuit board;

[0026]

[12] The resin composition according to any one of [1] to [9] above, which is used for sealing a semiconductor chip in a semiconductor chip package;

[0027]

[13] A cured product, which is a cured product of the resin composition described in any one of [1] to

[12] above;

[0028]

[14] A resin sheet comprising: a support; and a resin composition layer provided on the support and comprising the resin composition described in any one of [1] to

[12] above;

[0029]

[15] A circuit board comprising an insulating layer formed from a cured product of the resin composition described in any one of [1] to

[12] above;

[0030]

[16] A semiconductor chip package comprising: the circuit substrate described in

[15] above, and a semiconductor chip mounted on the circuit substrate;

[0031]

[17] A semiconductor chip package comprising: a semiconductor chip; and a cured product of the resin composition described in any one of [1] to

[12] above, which seals the semiconductor chip;

[0032]

[18] A semiconductor device comprising the semiconductor chip package described in

[16] or

[17] above;

[0033]

[19] A resin composition comprising (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, wherein the component (B) comprises (B-3) an active ester resin having a molecular weight of 1000 or less.

[0034] Effects of the Invention

[0035] According to the present invention, it is possible to provide a resin composition that can reduce the dielectric properties of a cured product and suppress the generation of flow marks, a cured product of the resin composition, a resin sheet comprising the resin composition, a circuit substrate comprising the cured product, a semiconductor chip package comprising the cured product, and a semiconductor device having the semiconductor chip package. DETAILED DESCRIPTION

[0036] Hereinafter, the present invention will be described in detail with reference to its preferred embodiments. However, the present invention is not limited to the following embodiments and examples, and can be arbitrarily modified and implemented without departing from the scope of the claims and their equivalents.

[0037] <Resin composition>

[0038] The resin composition of the present invention comprises (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler. In a first embodiment, component (B) comprises (B-1) an active ester resin having a softening point of 100°C or less. In a second embodiment, component (B) comprises (B-2) a difunctional active ester resin. In a third embodiment, component (B) comprises (B-3) an active ester resin having a molecular weight of 1000 or less.

[0039] By using such a resin composition, both the reduction of dielectric properties of the cured product and the suppression of flow mark generation can be achieved. In addition, according to such a resin composition, in one embodiment, a cured product having long-term adhesion to a semiconductor chip and excellent storage elastic modulus can be obtained.

[0040] The resin composition of the present invention may further include, in addition to (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, any additional components. Examples of such optional components include (D) a curing accelerator, (E) an organic solvent, and (F) other additives. The components of the resin composition are described in detail below.

[0041] <(A) Epoxy resin>

[0042] The resin composition of the present invention contains (A) an epoxy resin.

[0043] Examples of the epoxy resin (A) include bixylene-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-butylcatechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins, glycidyl ester-type epoxy resins, cresol novolac-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, cyclohexanedimethanol-type epoxy resins, naphthylene ether-type epoxy resins, trimethylol-type epoxy resins, and tetraphenylethane-type epoxy resins. The epoxy resins may be used alone or in combination of two or more.

[0044] Regarding the resin composition, it is preferred that the epoxy resin (A) contain an epoxy resin having two or more epoxy groups in one molecule. From the viewpoint of significantly obtaining the desired effect of the present invention, relative to 100% by mass of the non-volatile component of the epoxy resin (A), the ratio of the epoxy resin having two or more epoxy groups in one molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0045] Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter also referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter also referred to as "solid epoxy resins"). In one embodiment, the resin composition of the present invention contains a liquid epoxy resin as the epoxy resin. In one embodiment, the resin composition of the present invention contains a solid epoxy resin as the epoxy resin. Liquid epoxy resins and solid epoxy resins can be used in combination. The resin composition of the present invention preferably contains only liquid epoxy resin as the epoxy resin.

[0046] The liquid epoxy resin is preferably one having two or more epoxy groups in one molecule.

[0047] As liquid epoxy resins, preferred are bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidyl amine type epoxy resins, phenol novolac type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, and epoxy resins having a butadiene structure.

[0048] Specific examples of liquid epoxy resins include: "HP4032", "HP4032D", and "HP4032SS" (naphthalene-type epoxy resins) manufactured by DIC Corporation; "828US", "828EL", "jER828EL", "825", and "EPIKOTE" manufactured by Mitsubishi Chemical Corporation; "828EL" (bisphenol A type epoxy resin); "jER807" and "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630" and "630LSD" (glycidylamine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "EP-3950S", "EP-3950L" and "EP-3980S" (glycidylamine type epoxy resin) manufactured by ADEKA Corporation; "ZX1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel & Sumitomo Metal Chemical Corporation; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; "CELLOXIDE 2021P (CEL2021P)" (alicyclic epoxy resin with an ester skeleton); "PB-3600" manufactured by Daicel Corporation, "JP-100" and "JP-200" manufactured by Nippon Soda Co., Ltd. (epoxy resins with a butadiene structure); "ZX1658" and "ZX1658GS" manufactured by Nippon Steel & Sumikin Chemical Corporation (liquid 1,4-glycidylcyclohexane type epoxy resins), etc. These can be used alone or in combination of two or more.

[0049] The solid epoxy resin is preferably a solid epoxy resin having three or more epoxy groups in one molecule, more preferably an aromatic solid epoxy resin having three or more epoxy groups in one molecule.

[0050] As solid epoxy resins, preferred are biphenylol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional 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, and tetraphenylethane-type epoxy resins.

[0051] Specific examples of solid epoxy resins include: "HP4032H" manufactured by DIC Corporation (naphthalene-type epoxy resin); "HP-4700" and "HP-4710" manufactured by DIC Corporation (naphthalene-type tetrafunctional epoxy resin); "N-690" manufactured by DIC Corporation (cresol novolac-type epoxy resin); "N-695" manufactured by DIC Corporation (cresol novolac-type epoxy resin); "HP-7200" manufactured by DIC Corporation (dicyclopentadiene ... 00HH", "HP-7200H", "EXA-7311", "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" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. ", "NC3100" (biphenyl type epoxy resin); "ESN475V" (naphthol type epoxy resin) manufactured by Nippon Steel & Sumitomo Metal Chemical Corporation; "ESN485" (naphthol novolac type epoxy resin) manufactured by Nippon Steel & Sumitomo Metal Chemical Corporation; "YX4000H", "YX4000", "YL6121" (biphenyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX4000HK" (dimethylphenol type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene type epoxy resin) manufactured by Mitsubishi Chemical Corporation ); "YX7700" manufactured by Mitsubishi Chemical Corporation (a novolac-type epoxy resin containing a xylene structure); "PG-100" and "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" manufactured by Mitsubishi Chemical Corporation (a bisphenol AF-type epoxy resin); "YL7800" manufactured by Mitsubishi Chemical Corporation (a fluorene-type epoxy resin); "jER1010" manufactured by Mitsubishi Chemical Corporation (a solid bisphenol A-type epoxy resin); "jER1031S" manufactured by Mitsubishi Chemical Corporation (a tetraphenylethane-type epoxy resin). These may be used alone or in combination of two or more.

[0052] When a liquid epoxy resin and a solid epoxy resin are used in combination as the epoxy resin (A), the mass ratio of the liquid epoxy resin to the solid epoxy resin (liquid epoxy resin / solid epoxy resin) is preferably at least 1, more preferably at least 10, particularly preferably at least 50. By setting the mass ratio of the liquid epoxy resin to the solid epoxy resin within the above range, the desired effects of the present invention can be significantly achieved.

[0053] The epoxy equivalent weight of the epoxy resin (A) is preferably 50 g / eq. to 5000 g / eq., more preferably 50 g / eq. to 3000 g / eq., further preferably 80 g / eq. to 2000 g / eq., and even more preferably 110 g / eq. to 1000 g / eq. Within this range, the cured resin sheet has a sufficient crosslinking density, resulting in an insulating layer with minimal surface roughness. The epoxy equivalent weight is the mass of the resin containing one equivalent of epoxy groups. This epoxy equivalent weight can be measured in accordance with JIS K7236.

[0054] From the viewpoint of significantly achieving the desired effects of the present invention, the weight average molecular weight (Mw) of the epoxy resin (A) is preferably from 100 to 5000, more preferably from 100 to 3000, and even more preferably from 100 to 1500. The weight average molecular weight of the resin can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC).

[0055] When " non-volatile component " in resin combination is set to 100 mass %, the content of (A) epoxy resin is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 1 mass %, more preferably more than 2 mass %, further more preferably more than 3 mass %, particularly preferably more than 4 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 50 mass %, more preferably below 30 mass %, further more preferably below 20 mass %, particularly preferably below 10 mass %.

[0056] When " resin component " in resin combination is set to 100 mass %, the content of (A) epoxy resin is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 20 mass %, more preferably more than 30 mass %, further more preferably more than 40 mass %, especially preferably more than 45 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 90 mass %, more preferably below 70 mass %, further more preferably below 60 mass %, especially preferably below 50 mass %.

[0057] In this specification, the "resin component" refers to all non-volatile components remaining after removing the (C) inorganic filler from the resin composition. Therefore, the "resin component" may also include low molecular weight compounds.

[0058] (B) Curing agent

[0059] The resin composition of the present invention contains (B) a curing agent. The (B) curing agent has a function of curing the (A) epoxy resin.

[0060] When " non-volatile component " in resin combination is set to 100 mass %, the content of (B) curing agent is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 1 mass %, more preferably more than 3 mass %, further more preferably more than 4 mass %, particularly preferably more than 5 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 50 mass %, more preferably below 30 mass %, further more preferably below 20 mass %, particularly preferably below 10 mass %.

[0061] When " resin component " in resin combination is set to 100 mass %, the content of (B) curing agent is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 20 mass %, more preferably more than 30 mass %, further more preferably more than 40 mass %, particularly preferably more than 50 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 90 mass %, more preferably below 70 mass %, further more preferably below 60 mass %, particularly preferably below 55 mass %.

[0062] In a first embodiment, the curing agent (B) comprises (B-1) an active ester resin having a softening point of 100°C or less. In a second embodiment, the component (B) comprises (B-2) a difunctional active ester resin. In a third embodiment, the component (B) comprises (B-3) an active ester resin having a molecular weight of 1000 or less.

[0063] Active ester resins are ester compounds that react with epoxy groups in epoxy resins. Active ester resins are characterized by not generating hydroxyl groups during the addition reaction with epoxy groups in epoxy resins. Therefore, using active ester resins as curing agents can reduce the concentration of polar groups in the resulting cured product, thereby achieving low dielectric properties.

[0064] <(B-1) Active ester resin having a softening point of 100°C or less>

[0065] The active ester resin of component (B-1) is not particularly limited as long as it has a softening point of 100°C or less. The softening point can be measured, for example, by the ring and ball method based on JIS K2351. By using component (B-1), the uniformity of the composition of the resin composition can be improved, so the generation of flow marks can be suppressed. As component (B-1), preferably, a difunctional active ester resin having a softening point of 100°C or less (the "difunctional active ester resin" is described below); more preferably, it is a resin of formula (1):

[0066] [Chemical Formula 2]

[0067]

[0068] [In the formula, rings X, Y, and Z each independently represent an aromatic ring which may further have a substituent.]

[0069] The difunctional active ester resin represented by the present invention has a softening point of 100°C or less; further preferably, it is a resin represented by formula (2):

[0070] [Chemical Formula 3]

[0071]

[0072] [In the formula, rings A, B, C, D, and E each independently represent a benzene ring which may further have a substituent.]

[0073] Among the bifunctional active ester resins shown, the resin has a softening point of 100° C. or less.

[0074] In the present specification, the "aromatic ring" refers to a ring that complies with Hückel's rule and has 4n+2 electrons (n ​​is a natural number) in the π-electron system on the ring, and includes aromatic hydrocarbon rings and aromatic heterocycles.

[0075] In this specification, an "aromatic hydrocarbon ring" refers to an aromatic ring having carbon atoms as ring atoms. An "aromatic hydrocarbon ring" is preferably an aromatic hydrocarbon ring having 6 to 14 carbon atoms, more preferably an aromatic hydrocarbon ring having 6 to 10 carbon atoms. Examples of the "aromatic hydrocarbon ring" include a benzene ring, a naphthalene ring, and an anthracene ring.

[0076] In this specification, "aromatic heterocycle" refers to an aromatic ring containing, in addition to carbon atoms, heteroatoms such as nitrogen atoms, sulfur atoms, and oxygen atoms (preferably 1 to 4 atoms) as ring atoms. The "aromatic heterocycle" is preferably a 5- to 14-membered aromatic heterocycle, more preferably a 5- to 10-membered aromatic heterocycle. Examples of the “aromatic heterocycle” include 5- or 6-membered monocyclic aromatic heterocycles such as a thiophene ring, a furan ring, a pyrrole ring, a imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a 1,2,4-oxadiazole ring, a 1,3,4-oxadiazole ring, a 1,2,4-thiadiazole ring, a 1,3,4-thiadiazole ring, a triazole ring, a tetrazole ring, and a triazine ring; and 8- to 14-membered condensed aromatic heterocycles such as a benzothiophene ring, a benzofuran ring, a benzimidazole ring, a benzoxazole ring, a benzisoxazole ring, a benzothiazole ring, a benzisothiazole ring, and a benzotriazole ring.

[0077] The further substituents of the "aromatic ring optionally further having a substituent" in formula (1) and the "phenyl ring optionally further having a substituent" in formula (2) are not particularly limited, and examples thereof include halogen atoms, alkyl groups, alkenyl groups, alkoxy groups, alkylcarbonyl groups, aryl groups, aryloxy groups, arylcarbonyl groups, aralkyl groups, aromatic heterocyclic groups, and non-aromatic heterocyclic groups.

[0078] In the present specification, examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0079] In this specification, "alkyl" refers to a linear, branched or cyclic monovalent aliphatic saturated hydrocarbon group. The number of carbon atoms in the "alkyl" is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the "alkyl" group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0080] In this specification, "alkenyl" refers to a linear, branched or cyclic monovalent unsaturated aliphatic hydrocarbon group having at least one carbon-carbon double bond. The number of carbon atoms in the "alkenyl" is preferably 2 to 6, more preferably 2 to 4, and further preferably 2 or 3. Examples of the "alkenyl" include ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 3-hexenyl, 5-hexenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl.

[0081] In this specification, "alkoxy" refers to a monovalent group formed by bonding an alkyl group to an oxygen atom (alkyl-O-). The number of carbon atoms in the "alkoxy" is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, and hexyloxy.

[0082] In this specification, "alkylcarbonyl" refers to a monovalent group (alkyl-CO-) formed by bonding an alkyl group to a carbonyl group. The number of carbon atoms in the "alkylcarbonyl" is preferably 2 to 7, more preferably 2 to 5, and even more preferably 2 to 4. Examples of the "alkylcarbonyl" group include acetyl, propionyl, butyryl, 2-methylpropionyl, valeryl, 3-methylbutyryl, 2-methylbutyryl, 2,2-dimethylpropionyl, hexanoyl, and heptanoyl.

[0083] In this specification, "aryl" refers to a monovalent aromatic hydrocarbon group. The number of carbon atoms in the "aryl" is preferably 6 to 14, more preferably 6 to 10. Examples of the "aryl" group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, and 9-anthryl.

[0084] In the present specification, "aryloxy" refers to a monovalent group formed by bonding an aryl group to an oxygen atom (aryl-O-). The number of carbon atoms in "aryloxy" is preferably 6 to 14, more preferably 6 to 10. Examples of "aryloxy" include phenoxy and naphthoxy.

[0085] In this specification, "arylcarbonyl" refers to a monovalent group formed by bonding an aryl group to a carbonyl group (aryl-CO-). The number of carbon atoms in the "arylcarbonyl" is preferably 7 to 15, more preferably 7 to 11. Examples of the "arylcarbonyl" include benzoyl, 1-naphthoyl, and 2-naphthoyl.

[0086] In this specification, "aralkyl" refers to an alkyl group substituted with one or more aryl groups. The number of carbon atoms in the "aralkyl" is preferably 7 to 15, more preferably 7 to 11. Examples of the "aralkyl" include benzyl, phenethyl, and 2-naphthylmethyl.

[0087] In this specification, an "aromatic heterocyclic group" refers to an aromatic ring group containing, in addition to carbon atoms, heteroatoms such as nitrogen atoms, sulfur atoms, and oxygen atoms (preferably 1 to 4 atoms) as ring atoms. The "aromatic heterocyclic group" is preferably a 5- to 14-membered aromatic heterocyclic group, more preferably a 5- to 10-membered aromatic heterocyclic group. Examples of the “aromatic heterocyclic group” include 5- or 6-membered monocyclic aromatic heterocyclic groups such as thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, triazolyl, tetrazolyl, and triazinyl; and 8- to 14-membered condensed aromatic heterocyclic groups such as benzothienyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, and benzotriazolyl.

[0088] In this specification, a "non-aromatic heterocyclic group" refers to a non-aromatic ring group containing, in addition to carbon atoms, heteroatoms such as nitrogen atoms, sulfur atoms, and oxygen atoms (preferably 1 to 4 atoms) as ring atoms. The "non-aromatic heterocyclic group" is preferably a 3- to 14-membered non-aromatic heterocyclic group, more preferably a 4- to 10-membered non-aromatic heterocyclic group. Examples of the “non-aromatic heterocyclic group” include 3- to 8-membered monocyclic non-aromatic heterocyclic groups such as aziridinyl, oxirane, thiirane, azetidinyl, oxetanyl, thietanyl, tetrahydrothienyl, tetrahydrofuranyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, oxazolidinyl, pyrazolinyl, pyrazolidinyl, thiazolinyl, thiazolidinyl, tetrahydroisothiazolyl, tetrahydrooxazolyl, tetrahydroisoxazolyl, piperidinyl, and pyrazinyl; and 9- to 14-membered condensed non-aromatic heterocyclic groups such as dihydrobenzofuranyl, dihydrobenzimidazolyl, dihydrobenzoxazolyl, dihydrobenzothiazolyl, dihydrobenzisothiazolyl, dihydronaphtho[2,3-b]thienyl, and tetrahydroisoquinolinyl.

[0089] In formula (1), rings X, Y and Z are each independently preferably an aromatic hydrocarbon ring which may further have a substituent, more preferably a benzene ring or a naphthalene ring which may further have a substituent, and still more preferably an unsubstituted benzene ring or a naphthalene ring.

[0090] In the formula (2), the rings A, B, C, D and E are preferably unsubstituted benzene rings.

[0091] The softening point of the component (B-1) is preferably at most 90°C, more preferably at most 85°C, further preferably at most 80°C.

[0092] The molecular weight of the component (B-1) is preferably at most 1000, more preferably at most 700, further preferably at most 600, further preferably at most 500, particularly preferably at most 450. The lower limit is not particularly limited and may be 200 or the like.

[0093] Specific examples of the component (B-1) include the following:

[0094] [Chemical Formula 4]

[0095]

[0096] Representing compounds, etc.

[0097] As the component (B-1), a commercially available compound or a compound synthesized by a known method may be used. The component (B-1) may be used alone or in combination of two or more.

[0098] <(B-2) Difunctional active ester resin>

[0099] The active ester resin of component (B-2) is not particularly limited as long as it is difunctional. A difunctional active ester resin refers to a compound having two ester structures that can undergo addition reaction with the epoxy groups of the epoxy resin. By using component (B-2), the uniformity of the composition of the resin composition can be improved, so the generation of flow marks can be suppressed. As component (B-2), it is preferably represented by formula (1):

[0100] [Chemical Formula 5]

[0101]

[0102] [In the formula, rings X, Y, and Z each independently represent an aromatic ring which may further have a substituent.]

[0103] A difunctional active ester resin represented by formula (2):

[0104] [Chemical Formula 6]

[0105]

[0106] [In the formula, rings A, B, C, D, and E each independently represent a benzene ring which may further have a substituent.]

[0107] Represents a difunctional active ester resin.

[0108] The softening point of the component (B-2) is preferably at most 100°C, more preferably at most 90°C, further preferably at most 85°C, particularly preferably at most 80°C.

[0109] The molecular weight of the component (B-2) is preferably at most 1000, more preferably at most 700, further preferably at most 600, further preferably at most 500, particularly preferably at most 450. The lower limit of the molecular weight of the component (B-2) is not particularly limited and may be at least 200.

[0110] Specific examples of the component (B-2) include the following:

[0111] [Chemical Formula 7]

[0112]

[0113] Representing compounds, etc.

[0114] As the component (B-2), a commercially available compound or a compound synthesized by a known method may be used. The component (B-2) may be used alone or in combination of two or more.

[0115] <(B-3) Active ester resin having a molecular weight of 1000 or less>

[0116] The active ester resin of component (B-3) is not particularly limited as long as its molecular weight is 1000 or less. By using component (B-3), the uniformity of the composition of the resin composition can be improved, thereby suppressing the occurrence of flow marks. As component (B-3), a difunctional active ester resin having a molecular weight of 1000 or less is preferred (the "difunctional active ester resin" is as described above); more preferably, it is a difunctional active ester resin having a molecular weight of 1000 or less;

[0117] [Chemical Formula 8]

[0118]

[0119] [In the formula, rings X, Y, and Z each independently represent an aromatic ring which may further have a substituent.]

[0120] The difunctional active ester resin represented by the present invention has a molecular weight of 1000 or less; more preferably, it is a resin represented by formula (2):

[0121] [Chemical Formula 9]

[0122]

[0123] [In the formula, rings A, B, C, D, and E each independently represent a benzene ring which may further have a substituent.]

[0124] Among the difunctional active ester resins represented, those having a molecular weight of 1000 or less.

[0125] The softening point of the component (B-3) is preferably at most 100°C, more preferably at most 90°C, further preferably at most 85°C, particularly preferably at most 80°C.

[0126] The molecular weight of the component (B-3) is preferably at most 700, more preferably at most 600, further preferably at most 500, particularly preferably at most 450. The lower limit of the molecular weight of the component (B-3) is not particularly limited, and may be at least 200.

[0127] Specific examples of the component (B-3) include the following:

[0128] [Chemical Formula 10]

[0129]

[0130] Representing compounds, etc.

[0131] As the component (B-3), a commercially available compound may be used, or a compound synthesized by a known method may be used. The component (B-3) may be used alone or in combination of two or more.

[0132] When " non-volatile component " in resin combination is set to 100 mass %, the content of (B-1) component, (B-2) component or (B-3) component is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 1 mass %, more preferably more than 1.5 mass %, further more preferably more than 2 mass %, more preferably more than 2.5 mass %, particularly preferably more than 3 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 50 mass %, more preferably below 20 mass %, further more preferably below 10 mass %, particularly preferably below 5 mass %.

[0133] When " resin component " in resin combination is set to 100 mass %, the content of (B-1) component, (B-2) component or (B-3) component is not particularly limited, from the viewpoint of significantly obtaining the desired effect of the present invention, preferably more than 10 mass %, more preferably more than 15 mass %, further more preferably more than 20 mass %, especially preferably more than 25 mass %.From the viewpoint of significantly obtaining the desired effect of the present invention, its upper limit is preferably below 60 mass %, more preferably below 50 mass %, further more preferably below 45 mass %, especially preferably below 40 mass %.

[0134] (B-1) component, (B-2) component or (B-3) component are not particularly limited relative to the mass ratio of (B) curing agent, from the viewpoint of significantly obtaining the desired effect of the present invention, when (B) curing agent in resin combination is set to 100 mass %, preferably more than 5 mass %, more preferably more than 15 mass %, further more preferably more than 25 mass %, especially preferably more than 35 mass %.Its upper limit is preferably below 100 mass %, more preferably below 90 mass %, further more preferably below 80 mass %, especially preferably below 75 mass %.

[0135] <Optional curing agent other than components (B-1) to (B-3)>

[0136] In addition to comprising (B-1) component, (B-2) component or (B-3) component, (B) curing agent may also include other arbitrary curing agents. As any curing agent other than (B-1) component, (B-2) component or (B-3) component, it is not particularly limited as long as it has the function of curing epoxy resin. For example, phenol curing agent, naphthol curing agent, acid anhydride curing agent, active ester curing agent other than (B-1) component, (B-2) component or (B-3) component, benzoxazine curing agent, cyanate curing agent, carbodiimide curing agent and amine curing agent can be listed. Among them, preferably phenol curing agent, naphthol curing agent, amine curing agent and acid anhydride curing agent, more preferably acid anhydride curing agent. Such curing agent can be used alone or in combination of two or more.

[0137] As phenolic curing agents and naphthol curing agents, from the viewpoint of heat resistance and water resistance, preferably a phenolic curing agent having a novolac structure or a naphthol curing agent having a novolac structure. In addition, from the viewpoint of adhesion to the adherend, preferably a nitrogen-containing phenolic curing agent or a nitrogen-containing naphthol curing agent, more preferably a phenolic curing agent containing a triazine skeleton or a naphthol curing agent containing a triazine skeleton. Among them, from the viewpoint of highly satisfying heat resistance, water resistance and adhesion, preferably a phenolic novolac resin containing a triazine skeleton. Specific examples of phenol-based curing agents and naphthol-based curing agents include "MEH-7700", "MEH-7810", and "MEH-7851" manufactured by Meiwa Chemicals 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 & Sumitomo Metal Chemicals Corporation; and "LA-7052", "LA-7054", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", and "TD-2090-60M" manufactured by DIC Corporation.

[0138] Examples of the acid anhydride curing agent include curing agents having one or more acid anhydride groups in one molecule. 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, dodecenylsuccinic anhydride, 5-(2,5-dioxotetrahydro-3-furyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and the like. Acid anhydrides of the polymer type, such as acid anhydrides, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, oxydiphthalic anhydride, 3,3'-4,4'-diphenylsulfone tetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furyl)-naphtho[1,2-c]furan-1,3-dione, ethylene glycol bis(trimellitic anhydride), styrene-maleic acid resin obtained by copolymerization of styrene and maleic acid, etc. Commercially available products of anhydride curing agents include "HNA-100", "MH-700", "MTA-15", "DDSA", "HF-08", and "OSA" manufactured by Shin Nippon Chemical Co., Ltd., "YH306" and "YH307" manufactured by Mitsubishi Chemical Corporation, "H-TMAn" manufactured by Mitsubishi Gas Chemical Co., Ltd., and "HN-2200", "HN-2000", "HN-5500", and "MHAC-P" manufactured by Hitachi Chemical Co., Ltd.

[0139] As active ester curing agent except (B-1) component, (B-2) component or (B-3) component, it is not particularly limited, generally preferably use the compound with ester group with more than 3 reactive high reaction activity in 1 molecule of ester of phenolic ester, thiophenolic ester, N-hydroxylamine ester, heterocyclic hydroxy compound etc. The active ester curing agent is preferably the compound obtained by the condensation reaction of carboxylic acid compound and / or thiocarboxylic acid compound and hydroxy compound and / or thiol compound. Particularly from the viewpoint that heat resistance improves, it is preferably the active ester compound obtained by carboxylic acid compound and hydroxy compound, more preferably the active ester compound obtained by carboxylic acid compound and phenol compound and / or naphthol compound. As carboxylic acid compound, the compound with more than 3 carboxyl groups can be enumerated. Examples of the phenolic compound or naphthol compound include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyrogallol, dicyclopentadiene-type diphenolic compounds, and phenol novolacs. Here, the term "dicyclopentadiene-type diphenolic compound" refers to a diphenolic compound obtained by condensing two molecules of phenol with one molecule of dicyclopentadiene.

[0140] Specifically, preferred are active ester compounds containing a dicyclopentadiene-type diphenol structure, active ester compounds containing a naphthalene structure, active ester compounds containing acetylated phenol novolacs, and active ester compounds containing benzoylated phenol novolacs. Among these, more preferred are active ester compounds containing a naphthalene structure and active ester compounds containing a dicyclopentadiene-type diphenol structure. "Dicyclopentadiene-type diphenol structure" refers to a divalent structural unit composed of phenylene-dicyclopentylene-phenylene.

[0141] As commercially available active ester curing agents other than component (B-1), component (B-2) or component (B-3), active ester compounds containing a dicyclopentadiene-type diphenol structure include "EXB9451", "EXB9460", "EXB9460S", "HPC-8000", "HPC-8000H", "HPC-8000-65T", "HPC-8000H-65TM", "EXB-8000L", "EXB-8000L-65TM" (manufactured by DIC Corporation); active ester compounds containing a naphthalene structure include "EXB9416-70BK", "EXB-8150-65T" (manufactured by DIC Corporation); IC Co., Ltd.); examples of active ester compounds of acetylated phenol novolacs include "DC808" (manufactured by Mitsubishi Chemical Corporation); examples of active ester compounds of benzoylated phenol novolacs include "YLH1026" (manufactured by Mitsubishi Chemical Corporation); examples of active ester curing agents for acetylated phenol novolacs include "DC808" (manufactured by Mitsubishi Chemical Corporation); examples of active ester curing agents for benzoylated phenol novolacs include "YLH1026" (manufactured by Mitsubishi Chemical Corporation), "YLH1030" (manufactured by Mitsubishi Chemical Corporation), and "YLH1048" (manufactured by Mitsubishi Chemical Corporation).

[0142] Specific examples of benzoxazine curing agents include “JBZ-OP100D” and “ODA-BOZ” manufactured by JFE Chemical Corporation, “HFB2006M” manufactured by Showa Highpolymer Co., Ltd., and “Pd” and “Fa” manufactured by Shikoku Chemicals Co., Ltd.

[0143] Examples of cyanate curing agents include difunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenylcyanate), 4,4'-ethylenediphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylene))benzene, bis(4-cyanatephenyl)sulfide, and bis(4-cyanatephenyl)ether; polyfunctional cyanate resins derived from phenol novolac and cresol novolac; and prepolymers obtained by triazinization of a portion of these cyanate resins. Specific examples of cyanate curing agents include "PT30" and "PT60" manufactured by Lonza Japan Co., Ltd. (both are phenol novolac-type multifunctional cyanate resins), "BA230", and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate is triazinized to form a trimer).

[0144] Specific examples of the carbodiimide-based curing agent include "V-03" and "V-07" manufactured by Nisshinbo Chemical Co., Ltd.

[0145] As the amine curing agent, there can be mentioned a curing agent having more than one amino group in one molecule, for example, aliphatic amines, polyetheramines, alicyclic amines, aromatic amines, etc., wherein, from the viewpoint of exerting the desired effect of the present invention, aromatic amines are preferred. The amine curing agent is preferably a primary amine or a secondary amine, more preferably a primary amine. As a specific example of the amine curing agent, 4,4'-methylenebis(2,6-dimethylaniline), diphenyldiaminosulfone, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, metaphenylenediamine, metaxylene diamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino 4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. As the amine curing agent, commercially available products can be used, for example, "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD AA", "KAYAHARD AB", "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd., and "EPICURE W" manufactured by Mitsubishi Chemical Corporation.

[0146] In the case where resin combination includes any curing agent except (B-1) component, (B-2) component or (B-3) component, when " non-volatile component " in resin combination is set to 100 mass %, the content of any curing agent except (B-1) component, (B-2) component or (B-3) component is not particularly limited, preferably more than 0.1 mass %, more preferably more than 0.5 mass %, further more preferably more than 1 mass %, especially preferably more than 1.5 mass %.Its upper limit is preferably below 50 mass %, more preferably below 20 mass %, further more preferably below 10 mass %, especially preferably below 5 mass %.

[0147] In the case where resin combination includes any curing agent except (B-1) component, (B-2) component or (B-3) component, when " resin composition " in resin combination is set to 100 mass %, the content of any curing agent except (B-1) component, (B-2) component or (B-3) component is not particularly limited, preferably more than 1 mass %, more preferably more than 5 mass %, further more preferably more than 10 mass %, especially preferably more than 15 mass %.Its upper limit is preferably below 60 mass %, more preferably below 50 mass %, further more preferably below 40 mass %, especially preferably below 30 mass %.

[0148] The amount ratio of (A) epoxy resin to (B) curing agent is preferably in the range of 1:0.2 to 1:2, more preferably in the range of 1:0.3 to 1:1.5, and further preferably in the range of 1:0.4 to 1:1.2, based on the ratio of [the total number of epoxy groups of the epoxy resin]: [the total number of reactive groups of the curing agent]. Here, the reactive group of the curing agent refers to an active hydroxyl group, an active ester group, etc., which varies depending on the type of curing agent. In addition, the total number of epoxy groups of the epoxy resin refers to the value obtained by summing up the values ​​obtained by dividing the non-volatile component mass of each epoxy resin by the epoxy equivalent for all epoxy resins, and the total number of reactive groups of the curing agent refers to the value obtained by summing up the values ​​obtained by dividing the non-volatile component mass of each curing agent by the reactive group equivalent for all curing agents. By making the amount ratio of epoxy resin to curing agent within such a range, the heat resistance of the resulting cured product is further improved.

[0149] <(C) Inorganic fillers>

[0150] The resin composition of the present invention contains (C) an inorganic filler.

[0151] (C) The material of the inorganic filler is not particularly limited, and examples thereof include silica, aluminum oxide, 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, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate, and particularly preferably silica and aluminum oxide. As silica, amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, etc. can be listed. In addition, as silica, spherical silica is preferably used. (C) The inorganic filler can be used alone or in combination of two or more.

[0152] Examples of commercially available inorganic fillers (C) include "UFP-30" manufactured by Denki Kagaku Kogyo Co., Ltd., "SP60-05" and "SP507-05" manufactured by Nippon Steel & Sumitomo Metal Materials Corporation, "YC100C," "YA050C," "YA050C-MJE," "YA010C," "FE9 series," "FEB series," and "FED series" manufactured by Yaduma Co., Ltd., "UFP-30" manufactured by Denka Co., Ltd., "SILFIL NSS-3N," "SILFIL NSS-4N," and "SILFIL NSS-5N" manufactured by Tokuyama Co., Ltd., and "SC2500SQ," "SO-C4," "SO-C2," and "SO-C1" manufactured by Yaduma Co., Ltd.

[0153] (C) The average particle size of the inorganic filler is not particularly limited. From the perspective of suppressing the generation of flow marks, it is preferably 40 μm or less, more preferably 30 μm or less, further preferably 25 μm or less, further preferably 20 μm or less, and particularly preferably 15 μm or less. The lower limit of the average particle size of the inorganic filler is not particularly limited. It is preferably 0.1 μm or more, more preferably 1 μm or more, further preferably 3 μm or more, further preferably 5 μm or more, further preferably 7 μm or more, and particularly preferably 8 μm or more. The average particle size of the inorganic filler can be measured by a laser diffraction scattering method based on Mie scattering theory. Specifically, a particle size distribution of the inorganic filler can be prepared based on a volume basis using a laser diffraction scattering particle size distribution measuring device, and the median particle size can be measured as the average particle size. The measurement sample can be a sample obtained 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. For the measurement sample, a laser diffraction particle size distribution measuring apparatus is used. The wavelength of the light source used is set to blue and red. The volume-based particle size distribution of the inorganic filler is measured by a flow cell method. The average particle size is calculated based on the obtained particle size distribution as the median particle size. Examples of laser diffraction particle size distribution measuring apparatuses include the "LA-960" manufactured by Horiba, Ltd.

[0154] From the viewpoint of improving moisture resistance and dispersibility, (C) inorganic filler is preferably treated with one or more surface treatment agents such as aminosilane coupling agent, epoxysilane coupling agent, mercaptosilane coupling agent, alkoxysilane compound, organosilazane compound, titanate coupling agent, etc. Commercially available products of surface treatment agents include, for example, "KBM403" (3-glycidoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM803" (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBE903" (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Co., Ltd. alkane), Shin-Etsu Chemical Co., Ltd. “KBM103” (phenyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd. “KBM-4803” (long-chain epoxy-type silane coupling agent), Shin-Etsu Chemical Co., Ltd. “KBM-7103” (3,3,3-trifluoropropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd. “KBM503” (3-methacryloyloxypropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd. “KBM5783” (N-phenyl-3-aminooctyltrimethoxysilane), etc.

[0155] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment performed by the surface treatment agent is preferably within a specified range. Specifically, 100% by mass of the inorganic filler is preferably surface treated by a surface treatment agent of 0.2% by mass to 5% by mass, more preferably surface treated by a surface treatment agent of 0.2% by mass to 3% by mass, and further preferably surface treated by a surface treatment agent of 0.3% by mass to 2% by mass.

[0156] The degree of surface treatment by the surface treatment agent can be evaluated by the carbon content per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon content per unit surface area of ​​the inorganic filler is preferably 0.02 mg / m 2 More than 0.1 mg / m 2 More than 0.2 mg / m 2 On the other hand, from the viewpoint of preventing the increase of the melt viscosity of the resin varnish or the melt viscosity in the sheet form, 1 mg / m 2 Below, more preferably 0.8mg / m 2 Below, more preferably 0.5 mg / m 2 the following.

[0157] (C) The amount of carbon per unit surface area of ​​the inorganic filler can be measured after the surface-treated inorganic filler is cleaned with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent can be added to the inorganic filler surface-treated with a surface treatment agent, and ultrasonic cleaning can be performed at 25°C for 5 minutes. After removing the supernatant and drying the solid component, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. As a carbon analyzer, "EMIA-320V" manufactured by Horiba, Ltd. can be used.

[0158] From the viewpoint of further enhancing the effects of the present invention, the specific surface area of ​​the inorganic filler (C) is preferably 0.01 m 2 / g or more, more preferably 0.1m 2 / g or more, particularly preferably 0.2m 2 There is no particular upper limit, but it is preferably 50 m 2 / g or less, preferably 20m 2 / g or less, 10m 2 / g or less or 5m 2 The specific surface area of ​​the inorganic filler can be obtained by adsorbing nitrogen gas on the sample surface using a specific surface area measuring apparatus (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) according to the BET method and calculating the specific surface area by the BET multipoint method.

[0159] (C) the content of inorganic filler is not particularly limited. When the " non-volatile component " in the resin combination is set to 100 mass %, it is preferably more than 20 mass %, more preferably more than 50 mass %, further more preferably more than 70 mass %, and particularly preferably more than 80 mass %. Its upper limit is not particularly limited, and can be set to, for example, below 98 mass %, below 95 mass %, below 92 mass %, below 90 mass %, etc.

[0160] <(D) Curing accelerator>

[0161] The resin composition of the present invention may contain (D) a curing accelerator as an optional component.

[0162] (D) Curing accelerators include, for example, phosphorus curing accelerators, amine curing accelerators, imidazole curing accelerators, guanidine curing accelerators, and metal curing accelerators. Among them, phosphorus curing accelerators, amine curing accelerators, imidazole curing accelerators, and metal curing accelerators are preferred, amine curing accelerators, imidazole curing accelerators, and metal curing accelerators are more preferred, and imidazole curing accelerators are particularly preferred. One curing accelerator may be used alone, or two or more may be used in combination.

[0163] Examples of the phosphorus-based curing accelerator include triphenylphosphine, phosphonium borate compounds, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate.

[0164] Examples of the amine curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine (DMAP), benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo[5.4.0]undecene, and 4-dimethylaminopyridine is preferred.

[0165] Examples of the imidazole 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, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 2,4-diamino-6-[2'-methylimidazolyl-(1')] imidazole compounds such as 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, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 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, and adducts of imidazole compounds with epoxy resins.

[0166] As the imidazole-based curing accelerator, a commercially available item can be used, and examples thereof include "P200-H50" manufactured by Mitsubishi Chemical Corporation.

[0167] 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-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, and 1-(o-tolyl)biguanidine.

[0168] Examples of metal 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, organoferric 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 octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0169] When resin combination contains (D) curing accelerator, when " non-volatile component " in resin combination is set to 100 mass %, the content of (D) curing accelerator is not particularly limited, preferably more than 0.001 mass %, more preferably more than 0.01 mass %, further more preferably more than 0.05 mass %, especially preferably more than 0.1 mass %.Its upper limit is preferably below 2 mass %, more preferably below 1 mass %, further more preferably below 0.5 mass %, especially preferably below 0.2 mass %.

[0170] When resin combination contains (D) curing accelerator, when " resin component " in resin combination is set to 100 mass %, the content of (D) curing accelerator is not particularly limited, preferably more than 0.001 mass %, more preferably more than 0.01 mass %, further more preferably more than 0.1 mass %, especially preferably more than 0.5 mass %.Its upper limit is preferably below 5 mass %, more preferably below 2 mass %, further more preferably below 1 mass %, especially preferably below 0.6 mass %.

[0171] <(E) Organic solvents>

[0172] The resin composition of the present invention may further contain (E) an organic solvent as an optional volatile component.

[0173] Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethylene glycol monoethyl ether acetate, and γ-butyrolactone; carbitol solvents such as cellosolve and butyl carbitol; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene; amide solvents such as dimethylformamide, dimethylacetamide (DMAc), and N-methylpyrrolidone; alcohol solvents such as methanol, ethanol, and 2-methoxypropanol; and hydrocarbon solvents such as cyclohexane and methylcyclohexane. The organic solvent may be used alone or in combination of two or more in any proportions.

[0174] <(F) Other additives>

[0175] Except above-mentioned composition, resin combination can further comprise other additives as arbitrary composition.As such additive, can enumerate for example organic filler, thickener, defoamer, leveler, adhesion imparting agent, polymerization initiator, flame retardant etc. These additives can use 1 kind alone, also can use in combination of 2 or more kinds.If those skilled in the art, then can suitably set the content of each additive.

[0176] <Method for producing resin composition>

[0177] In one embodiment, the resin composition of the present invention can be manufactured, for example, by a method comprising the following steps: (A) epoxy resin, (B) curing agent, (C) inorganic filler, (D) curing accelerator used as needed, (E) organic solvent used as needed, and (F) other additives used as needed are added to a reaction vessel in any order and / or partially or all at the same time and mixed to obtain a resin composition.

[0178] In the above-mentioned process, the temperature of the process of adding each component can be appropriately set, and heating and / or cooling can be temporarily or always performed during the process of adding each component. In the process of adding each component, stirring or vibration can be performed. In addition, it is preferred that after the above-mentioned process, the resin combination is further stirred with a stirring device such as a mixer to make it uniformly dispersed.

[0179] <Characteristics of the resin composition>

[0180] The resin composition of the present invention comprises (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler. Component (B) comprises (B-1) an active ester resin having a softening point of 100°C or less, (B-2) a difunctional active ester resin, or (B-3) an active ester resin having a molecular weight of 1000 or less. This allows for the production of a cured product having reduced dielectric properties and suppressed flow marks. Furthermore, the resin composition of the present invention, in one embodiment, allows for the production of a cured product having long-term, maintainable adhesion to semiconductor chips and excellent storage modulus.

[0181] About the low dielectric properties of one of the features of the cured product of the resin composition of the present invention, in one embodiment, the dielectric loss tangent (tan δ) measured by the Fabry-Perot method (measurement frequency 79 GHz) of the cured product obtained by thermosetting the resin composition is preferably less than 0.01, more preferably less than 0.005, further more preferably less than 0.004, and particularly preferably less than 0.003. The lower limit of dielectric loss tangent is not particularly limited and can be set to more than 0.001, more than 0.0001, more than 0.00001, etc.

[0182] Regarding the ability to maintain long-term adhesion to a semiconductor chip, which is one of the characteristics of the cured product of the resin composition of the present invention in one embodiment, for example, after a resin composition layer formed by the resin composition is compression-molded on a silicon wafer and heat-cured, a high temperature and high humidity environment test (HAST) is performed at 130°C and 85% RH for 100 hours, no peeling will occur at the interface between the cured product of the resin composition layer and the silicon wafer serving as the substrate.

[0183] Regarding the excellent storage modulus, which is one of the characteristics of the cured product of the resin composition of the present invention in one embodiment, for example, the storage modulus of a layered cured product obtained by thermally curing the resin composition at 25°C, measured under the conditions of a frequency of 1 Hz and a heating rate of 5°C / min, is preferably 40 GPa or less, more preferably 30 GPa or less, and further preferably 25 GPa or less. The lower limit of the storage modulus is not particularly limited and can be set to 10 GPa or more, 1 GPa or more, 0.1 GPa or more, etc.

[0184] Furthermore, in one embodiment, even after the resin composition of the present invention is compression molded to form a resin composition layer and then heated at 150°C for 60 minutes, no flow marks are formed on the surface of the resin composition layer. Furthermore, in one embodiment, the resin composition of the present invention is in a fluid liquid state at 25°C.

[0185] <Applications of the resin composition>

[0186] Based on the above advantages, the cured product of the resin composition of the present invention can be used as a sealing layer and an insulating layer of a semiconductor. Therefore, the resin composition can be used as a resin composition for semiconductor sealing or insulating layer.

[0187] For example, the resin composition of the present invention can be suitably used as: a resin composition for forming an insulating layer of a semiconductor chip package (resin composition for an insulating layer of a semiconductor chip package), and a resin composition for forming an insulating layer of a circuit substrate (including a printed wiring board) (resin composition for an insulating layer of a circuit substrate).

[0188] Furthermore, for example, the resin composition of the present invention can be suitably used as a resin composition for sealing a semiconductor chip for semiconductor chip packaging (resin composition for semiconductor chip sealing).

[0189] As semiconductor chip packages that can be used with a sealing layer or an insulating layer formed by the cured product of the resin composition of the present invention, for example, FC-CSP, MIS-BGA package, ETS-BGA package, fan-out (Fan-out) type WLP (Wafer Level Package), fan-in (Fan-in) type WLP, fan-out type PLP (Panel Level Package), and fan-in type PLP.

[0190] Furthermore, the resin composition of the present invention can be used as an underfill material, for example, a material for MUF (Molding Under Filling) used after a semiconductor chip is connected to a substrate.

[0191] Furthermore, the resin composition of the present invention can be used in a wide range of applications using resin compositions, including resin sheets, sheet-like laminated materials such as prepregs, liquid materials such as resin inks for solder resists, die bonding materials, hole-filling resins, and component embedding resins.

[0192] <Resin Sheet>

[0193] The resin sheet of the present invention comprises a support and a resin composition layer provided on the support. The resin composition layer is a layer containing the resin composition of the present invention and is usually formed of the resin composition.

[0194] From the viewpoint of thinning, the thickness of the resin composition layer is preferably 600 μm or less, more preferably 500 μm or less. The lower limit of the thickness of the resin composition layer is preferably 1 μm or more, 5 μm or more, more preferably 10 μm or more, further preferably 50 μm or more, and particularly preferably 100 μm or more.

[0195] The thickness of the cured product obtained by curing the resin composition layer is preferably at least 1 μm, at least 5 μm, more preferably at least 10 μm, further preferably at least 50 μm, particularly preferably at least 100 μm.

[0196] Examples of the support include films formed of plastic materials, metal foils, and release papers, and films formed of plastic materials and metal foils are preferred.

[0197] When a film formed of a plastic material is used as the support, examples of the plastic material include polyesters such as polyethylene terephthalate (hereinafter sometimes referred to as "PET") and polyethylene naphthalate (hereinafter sometimes referred to as "PEN"); polycarbonate (hereinafter sometimes referred to as "PC"); acrylic polymers such as polymethyl methacrylate (hereinafter sometimes referred to as "PMMA"); cyclic polyolefins; triacetyl cellulose (hereinafter sometimes referred to as "TAC"); polyether sulfide (hereinafter sometimes referred to as "PES"); polyether ketone; and polyimide. Among them, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0198] When a metal foil is used as a support, examples of the metal foil include copper foil and aluminum foil. Among them, copper foil is preferred. As the copper foil, a foil made of a single metal of copper can be used, or a foil made of an alloy of copper and other metals (such as tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can also be used.

[0199] The surface of the support that contacts the resin composition layer may be subjected to treatment such as matte treatment, corona treatment, and antistatic treatment.

[0200] In addition, as a support, a support with a release layer having a release layer on the surface bonded to the resin composition layer can be used. As a release agent for the release layer of a support with a release layer, for example, one or more release agents selected from alkyd resins, polyolefin resins, polyurethane resins and silicone resins can be mentioned. As commercially available products of release agents, for example, "SK-1", "AL-5", "AL-7" manufactured by Lintec Co., Ltd., which are alkyd resin release agents, can be mentioned. In addition, as a support with a release layer, for example, "LUMIRROR T60" manufactured by Toray Industries, Ltd., "Purex" manufactured by Teijin Limited, "Unipeel" manufactured by Unitika Co., Ltd., etc. can be mentioned.

[0201] The thickness of the support is preferably in the range of 5 μm to 75 μm, more preferably in the range of 10 μm to 60 μm. When a support with a release layer is used, the thickness of the entire support with a release layer is preferably within the above range.

[0202] The resin sheet can be manufactured by applying a resin composition to a support using a coating device such as a die coater. In addition, the resin composition can be dissolved in an organic solvent as needed to form a resin varnish, and the resin sheet can be manufactured by applying the resin varnish. By using a solvent, the viscosity can be adjusted and the coating property can be improved. When using a resin varnish, the resin varnish is usually dried after application to form a resin composition layer.

[0203] Drying can be carried out by known methods such as heating and blowing hot air. Regarding drying conditions, drying is performed so that the organic solvent content in the resin composition layer is generally 10% by mass or less, preferably 5% by mass or less. This varies depending on the boiling point of the organic solvent in the resin varnish. For example, when using a resin varnish containing 30% to 60% by mass of an organic solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0204] The resin sheet may include any layer other than the support and the resin composition layer as needed. For example, in the resin sheet, a protective film selected according to the support may be provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface on the side opposite to the support). The thickness of the protective film is, for example, 1 μm to 40 μm. The protective film can prevent the surface of the resin composition layer from being attached to garbage or being damaged. In the case where the resin sheet has a protective film, the resin sheet can be used by peeling off the protective film. In addition, the resin sheet can be rolled up and stored.

[0205] Resin sheets can be suitably used to form insulating layers in the manufacture of semiconductor chip packages (resin sheets for insulating layers of semiconductor chip packages). For example, resin sheets can be used to form insulating layers of circuit boards (resin sheets for insulating layers of circuit boards). Examples of packages using such substrates include FC-CSP, MIS-BGA packages, and ETS-BGA packages.

[0206] Furthermore, the resin sheet can be suitably used for sealing semiconductor chips (resin sheet for semiconductor chip sealing). Examples of applicable semiconductor chip packages include fan-out WLP, fan-in WLP, fan-out PLP, and fan-in PLP.

[0207] Furthermore, the resin sheet can be used as a material for MUF used after the semiconductor chip is connected to the substrate.

[0208] In addition, the resin sheet can be used in a wide range of other applications requiring high insulation reliability. For example, the resin sheet can be suitably used to form an insulating layer of a circuit board such as a printed circuit board.

[0209] <Circuit board>

[0210] The circuit board of the present invention includes an insulating layer formed by a cured product of the resin composition of the present invention. The circuit board can be produced, for example, by a production method comprising the following steps (1) and (2):

[0211] (1) forming a resin composition layer on a substrate;

[0212] (2) A step of thermally curing the resin composition layer to form an insulating layer.

[0213] In step (1), a substrate is prepared. Examples of the substrate include glass epoxy substrates, metal substrates (stainless steel or cold-rolled steel (SPCC) etc.), polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. In addition, as for the substrate, a metal layer such as copper foil may be provided on the surface as part of the substrate. For example, a substrate having a first metal layer and a second metal layer that can be peeled off on both surfaces may be used. When such a substrate is used, a conductor layer that is usually a wiring layer that can play the role of circuit wiring is formed on the surface of the second metal layer on the opposite side of the first metal layer. Examples of such a substrate having a metal layer include, for example, the ultra-thin copper foil "Micro Thin" with a carrier copper foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0214] In addition, a conductor layer may be formed on one or both surfaces of the substrate. In the following description, a member comprising a substrate and a conductor layer formed on the surface of the substrate is sometimes appropriately referred to as a "substrate with a wiring layer". Examples of the conductor material contained in the conductor layer include materials comprising one or more metals selected from gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin and indium. As the conductor material, a single metal may be used, or an alloy may be used. Examples of the alloy include alloys of two or more metals selected from the above metals (e.g., nickel-chromium alloys, copper-nickel alloys and copper-titanium alloys). Among them, from the perspective of versatility, cost and ease of pattern formation in forming the conductor layer, preferred are single metals such as chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper; and alloys of nickel-chromium alloys, copper-nickel alloys and copper-titanium alloys. Among them, more preferred are single metals such as chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper; and nickel-chromium alloys; and particularly preferred is single metal such as copper.

[0215] About the conductor layer, pattern processing can be performed in order to function as a wiring layer, for example. At this time, the line width (circuit width) / line spacing (width between circuits) ratio of the conductor layer is not particularly limited, preferably 20 / 20 μm or less (i.e., a spacing of 40 μm or less), more preferably 10 / 10 μm or less, further preferably 5 / 5 μm or less, further preferably 1 / 1 μm or less, and particularly preferably 0.5 / 0.5 μm or more. The spacing does not need to be the same throughout the conductor layer. The minimum spacing of the conductor layer can be, for example, 40 μm or less, 36 μm or less, or 30 μm or less.

[0216] The thickness of the conductor layer varies depending on the design of the circuit board, but is preferably from 3 μm to 35 μm, more preferably from 5 μm to 30 μm, further preferably from 10 μm to 20 μm, particularly preferably from 15 μm to 20 μm.

[0217] The conductor layer can be formed, for example, by a method comprising the following steps: laminating a dry film (photosensitive resist film) on a substrate; exposing and developing the dry film under predetermined conditions using a photomask to form a pattern, thereby obtaining a patterned dry film; forming a conductor layer by a plating method such as electroplating using the developed patterned dry film as a plating mask; and stripping the patterned dry film. A photosensitive dry film formed from a photoresist composition can be used as the dry film, for example, a dry film formed from a resin such as a novolac resin or an acrylic resin. The conditions for laminating the substrate and the dry film can be the same as the conditions for laminating the substrate and the resin sheet described below. Stripping the dry film can be performed, for example, using an alkaline stripping solution such as a sodium hydroxide solution.

[0218] After preparing a substrate, a resin composition layer is formed on the substrate. When a conductor layer is formed on the surface of the substrate, the resin composition layer is preferably formed so that the conductor layer is embedded in the resin composition layer.

[0219] The formation of the resin composition layer is carried out, for example, by laminating a resin sheet with a substrate. The lamination can be carried out, for example, by the following manner: the resin sheet is heat-pressed to the substrate from the support side, thereby the resin composition layer is attached to the substrate. As a component for heat-pressing the resin sheet to the substrate (hereinafter sometimes referred to as "heat-pressing component"), for example, a heated metal plate (SUS end plate, etc.) or a metal roller (SUS roller, etc.) can be cited. It should be noted that it is better not to directly press the heat-pressing component to the resin sheet, but to press it across an elastic material such as heat-resistant rubber in order to make the resin sheet fully conform to the surface unevenness of the substrate.

[0220] The lamination of the substrate and the resin sheet can be performed, for example, by vacuum lamination. In the vacuum lamination method, the heat pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C. The heat pressing pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa. The heat pressing time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination is preferably performed under reduced pressure conditions of 13 hPa or less.

[0221] After lamination, the laminated resin sheets can be smoothed by, for example, applying a heat-pressing member to the support under normal pressure (atmospheric pressure). The smoothing pressing conditions can be the same as those for the heat-pressing lamination described above. Lamination and smoothing can be performed continuously using a vacuum laminator.

[0222] The resin composition layer can be formed by compression molding, for example. The molding conditions can be the same as those for the resin composition layer formation method in the step of forming the sealing layer of the semiconductor chip package described later.

[0223] After forming a resin composition layer on a substrate, the resin composition layer is thermally cured to form an insulating layer. The thermal curing conditions for the resin composition layer vary depending on the type of resin composition, but the curing temperature is generally in the range of 120°C to 240°C (preferably 150°C to 220°C, more preferably 170°C to 200°C), and the curing time is in the range of 5 minutes to 120 minutes (preferably 10 minutes to 100 minutes, more preferably 15 minutes to 90 minutes).

[0224] Before thermally curing the resin composition layer, the resin composition layer may be subjected to a preheating treatment in which the resin composition layer is heated at a temperature lower than the curing temperature. For example, before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature generally of 50°C or higher and lower than 120°C (preferably 60°C or higher and 110°C or lower, more preferably 70°C or higher and 100°C or lower) for generally 5 minutes or more (preferably 5 to 150 minutes, more preferably 15 to 120 minutes).

[0225] By performing the above operation, a circuit board having an insulating layer can be manufactured. In addition, the method for manufacturing a circuit board may further include an optional step.

[0226] For example, when a circuit board is produced using a resin sheet, the method for producing the circuit board may include a step of peeling off the support of the resin sheet. The support may be peeled off before or after the resin composition layer is thermally cured.

[0227] The method for manufacturing a circuit board may include, for example, a step of grinding the surface of the insulating layer after forming the insulating layer. The grinding method is not particularly limited. For example, the surface of the insulating layer may be ground using a surface grinding disc.

[0228] The method for manufacturing a circuit substrate may include, for example, a step (3) of connecting the conductor layers between layers, and a step of forming a hole in the insulating layer. This allows holes such as through holes and through holes to be formed in the insulating layer. Examples of methods for forming through holes include laser irradiation, etching, and mechanical drilling. The size and shape of the through holes can be appropriately determined based on the design of the circuit substrate. It should be noted that, in step (3), interlayer connection can be achieved by grinding or polishing the insulating layer.

[0229] After forming the through hole, it is better to remove the smear in the through hole. This operation is sometimes referred to as a desmearing process. For example, when a conductive layer is formed on an insulating layer by a plating process, a wet desmearing process can be performed on the through hole. In addition, when a conductive layer is formed on an insulating layer by a sputtering process, a dry desmearing process such as a plasma treatment process can be performed. And then, the insulating layer can also be roughened by the desmearing process.

[0230] Furthermore, the insulating layer may be subjected to a roughening treatment before forming the conductive layer thereon. This roughening treatment typically roughens the surface of the insulating layer, including the interior of the through-holes. The roughening treatment may be either dry or wet. Examples of dry roughening treatments include plasma treatment. Examples of wet roughening treatments include a method in which swelling treatment using a swelling solution, roughening treatment using an oxidizing agent, and neutralization treatment using a neutralizing solution are sequentially performed.

[0231] After the through-hole is formed, a conductor layer can be formed on the insulating layer. By forming a conductor layer at the position where the through-hole is formed, the newly formed conductor layer is connected to the conductor layer on the surface of the substrate to perform interlayer connection. The method for forming the conductor layer can include, for example, plating, sputtering, evaporation, etc., among which plating is preferred. In a preferred embodiment, plating is performed on the surface of the insulating layer by an appropriate method such as a semi-additive method and a full-additive method to form a conductor layer with a desired wiring pattern. In addition, when the support in the resin sheet is a metal foil, a conductor layer with a desired wiring pattern can be formed by a subtractive method. The material of the conductor layer formed can be a single metal or an alloy. In addition, the conductor layer can have a single-layer structure or a multilayer structure comprising two or more layers of different types of materials.

[0232] Here, an example of an embodiment of forming a conductor layer on an insulating layer is described in detail. A plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer to expose a portion of the plating seed layer corresponding to the desired wiring pattern. After an electrolytic plating layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or other processes, thereby forming a conductor layer having the desired wiring pattern. It should be noted that when forming the conductor layer, the dry film used to form the mask pattern is the same as the dry film described above.

[0233] The method for producing a circuit board may include a step (4) of removing the substrate. By removing the substrate, a circuit board having an insulating layer and a conductive layer embedded in the insulating layer is obtained. This step (4) can be performed, for example, when using a substrate having a removable metal layer.

[0234] Semiconductor chip packaging

[0235] A semiconductor chip package according to a first embodiment of the present invention includes the circuit substrate described above and a semiconductor chip mounted on the circuit substrate. The semiconductor chip package can be manufactured by bonding the semiconductor chip to the circuit substrate.

[0236] The circuit substrate and the semiconductor chip can be bonded under any conditions that allow for conductive connection between the terminal electrodes of the semiconductor chip and the circuit wiring of the circuit substrate. For example, conditions used in flip-chip mounting of semiconductor chips can be employed. Alternatively, for example, the semiconductor chip and the circuit substrate can be bonded via an insulating adhesive.

[0237] An example of a bonding method is to press-bond a semiconductor chip to a circuit board. The pressing conditions are typically a temperature in the range of 120°C to 240°C (preferably 130°C to 200°C, more preferably 140°C to 180°C), and a time in the range of 1 second to 60 seconds (preferably 5 seconds to 30 seconds).

[0238] Another example of the bonding method is a method of bonding a semiconductor chip to a circuit board by reflow soldering. The reflow soldering conditions can be set to a range of 120°C to 300°C.

[0239] After the semiconductor chip is bonded to the circuit board, the semiconductor chip may be filled with a mold underfill material. As the mold underfill material, the above-mentioned resin composition may be used, or the above-mentioned resin sheet may be used.

[0240] The semiconductor chip package according to the second embodiment of the present invention includes a semiconductor chip and a cured product of the resin composition described above that seals the semiconductor chip. In such a semiconductor chip package, the cured product of the resin composition typically functions as a sealing layer. Examples of the semiconductor chip package according to the second embodiment include fan-out WLPs.

[0241] The method for manufacturing such a semiconductor chip package comprises:

[0242] (A) a step of laminating a temporary fixing film on a substrate;

[0243] (B) a step of temporarily fixing the semiconductor chip on a temporary fixing film;

[0244] (C) forming a sealing layer on the semiconductor chip;

[0245] (D) a step of peeling the substrate and the temporary fixing film from the semiconductor chip;

[0246] (E) forming a rewiring forming layer as an insulating layer on the surface of the semiconductor chip from which the substrate and the temporary fixing film have been peeled off;

[0247] (F) forming a rewiring layer as a conductor layer on the rewiring formation layer; and

[0248] (G) A step of forming a solder resist layer on the redistribution layer.

[0249] Furthermore, the manufacturing method of the semiconductor chip package may include:

[0250] (H) A step of cutting a plurality of semiconductor chip packages into individual semiconductor chip packages.

[0251] (Process (A))

[0252] Step (A) is a step of laminating a temporary fixing film on a substrate. The lamination conditions of the substrate and the temporary fixing film can be the same as the lamination conditions of the substrate and the resin sheet in the method for producing a circuit board.

[0253] Examples of the substrate include silicon wafers, glass wafers, glass substrates, metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC), FR-4 substrates, and other substrates obtained by impregnating glass fibers with epoxy resins and then thermally curing the glass fibers, and substrates formed from bismaleimide triazine resins such as BT resin, and the like.

[0254] Any material that can be peeled from the semiconductor chip and can temporarily fix the semiconductor chip can be used as the temporary fixing film. Examples of commercially available products include "REVALPHA" manufactured by Nitto Denko Corporation.

[0255] (Process (B))

[0256] Step (B) is a step of temporarily securing the semiconductor chip to the temporary securing film. Temporary securing of the semiconductor chip can be performed using, for example, a flip chip bonder or a die bonder. The layout and number of semiconductor chips can be appropriately determined based on the shape and size of the temporary securing film, the target production volume of semiconductor chip packages, and the like. For example, the semiconductor chips can be arranged in a matrix of multiple rows and columns for temporary securing.

[0257] (Process (C))

[0258] Step (C) is a step of forming a sealing layer on the semiconductor chip. The sealing layer is formed from a cured product of the resin composition. The sealing layer is typically formed by a method comprising the steps of forming a resin composition layer on the semiconductor chip and thermally curing the resin composition layer to form the sealing layer.

[0259] It is preferred to utilize the excellent compression moldability of the resin composition to form the resin composition layer by a compression molding method. In the compression molding method, a semiconductor chip and a resin composition are usually arranged in a mold, and pressure is applied to the resin composition in the mold and heated as needed to form a resin composition layer covering the semiconductor chip.

[0260] The specific operation of the compression molding method can be carried out as follows. As the mold used for compression molding, an upper mold and a lower mold are prepared. In addition, the semiconductor chip temporarily fixed on the temporary fixing film as mentioned above is coated with a resin composition. The semiconductor chip coated with the resin composition is installed on the lower mold together with the substrate and the temporary fixing film. Then, the upper mold and the lower mold are matched, and heat and pressure are applied to the resin composition to carry out compression molding.

[0261] In addition, the specific operation of the compression molding method can also be carried out as follows. As a mold for compression molding, an upper mold and a lower mold are prepared. A resin composition is carried on the lower mold. In addition, a semiconductor chip is installed in the upper mold together with a substrate and a temporary fixing film. Then, the upper mold and the lower mold are clamped in a manner such that the resin composition carried on the lower mold and the semiconductor chip installed on the upper mold are connected, and heat and pressure are applied to perform compression molding.

[0262] The molding conditions vary according to the composition of the resin composition, and suitable conditions can be used to achieve good sealing. For example, the temperature of the mold during molding is preferably a temperature at which the resin composition can exert excellent compression moldability, preferably more than 80°C, more preferably more than 100°C, particularly preferably more than 120°C, preferably less than 200°C, more preferably less than 170°C, and particularly preferably less than 150°C. In addition, the pressure applied during molding is preferably more than 1MPa, more preferably more than 3MPa, particularly preferably more than 5MPa, preferably less than 50MPa, more preferably less than 30MPa, and particularly preferably less than 20MPa. The curing time is preferably more than 1 minute, more preferably more than 2 minutes, particularly preferably more than 5 minutes, preferably less than 60 minutes, more preferably less than 30 minutes, and particularly preferably less than 20 minutes. Typically, after forming the resin composition layer, the mold is unloaded. The unloading of the mold can be carried out before the thermal curing of the resin composition layer, or after thermal curing.

[0263] The resin composition layer is formed, for example, by laminating a resin sheet with a semiconductor chip. For example, the resin composition layer of the resin sheet and the semiconductor chip are heat-pressed to form the resin composition layer on the semiconductor chip. The lamination of the resin sheet and the semiconductor chip can generally be performed in the same manner as the lamination of the resin sheet and the substrate in the circuit board manufacturing method, using the semiconductor chip instead of the substrate.

[0264] After forming the resin composition layer on the semiconductor chip, the resin composition layer is heat-cured to obtain a sealing layer covering the semiconductor chip. Thus, the semiconductor chip is sealed based on the cured product of the resin composition. The heat curing conditions of the resin composition layer can adopt the same conditions as the heat curing conditions of the resin composition layer in the manufacture method of the circuit substrate. And then, before the resin composition layer is heat-cured, a preheating treatment of heating at a temperature lower than the curing temperature can be implemented for the resin composition layer. The processing conditions of the preheating treatment can adopt the same conditions as the preheating treatment in the manufacture method of the circuit substrate.

[0265] (Process (D))

[0266] Step (D) is a step of peeling the substrate and temporary fixing film from the semiconductor chip. The peeling method is preferably a method suitable for the material of the temporary fixing film. Examples of peeling methods include methods of heating, foaming, or expanding the temporary fixing film. Other examples of peeling methods include methods of irradiating the temporary fixing film with ultraviolet light through the substrate to reduce the adhesive strength of the temporary fixing film.

[0267] In the method of heating, foaming or expanding the temporary fixing film, the heating conditions are generally 100°C to 250°C for 1 second to 90 seconds or 5 minutes to 15 minutes. In the method of irradiating the temporary fixing film with ultraviolet light to reduce the adhesive strength and then peeling it off, the ultraviolet light irradiation dose is generally 10 mJ / cm 2 ~1000mJ / cm 2 .

[0268] (Process (E))

[0269] Step (E) is a step of 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.

[0270] The material of the rewiring forming layer can be any material having insulating properties. Among them, from the viewpoint of the manufacturing difficulty of the semiconductor chip package, photosensitive resins and thermosetting resins are preferred. In addition, as the thermosetting resin, the resin composition of the present invention can be used.

[0271] After the rewiring formation layer is formed, a through hole may be formed in the rewiring formation layer in order to establish an interlayer connection between the semiconductor chip and the rewiring layer.

[0272] In the formation method of the through hole in the case where the material of the rewiring forming layer is a photosensitive resin, the surface of the rewiring forming layer is usually irradiated with active energy rays through the mask pattern to photocure the rewiring forming layer of the irradiated portion. As active energy rays, for example, ultraviolet rays, visible light, electron beams, X-rays, etc. can be listed, and ultraviolet rays are particularly preferred. The irradiation amount and irradiation time of ultraviolet rays can be appropriately set according to the photosensitive resin. As exposure methods, for example, a contact exposure method in which a mask pattern is closely attached to the rewiring forming layer and exposed, a non-contact exposure method in which a mask pattern is not closely attached to the rewiring forming layer and exposed using parallel light, etc. can be listed.

[0273] After the rewiring forming layer is photocured, it is developed to remove the unexposed portion and form a through hole. Development can be performed by either wet or dry methods. Examples of development methods include immersion, puddle coating, spraying, brushing, and scraping. From the perspective of resolution, puddle coating is preferred.

[0274] As the formation method of the through hole when the material of the rewiring forming layer is a thermosetting resin, for example, laser irradiation, etching, mechanical drilling, etc. can be enumerated. Wherein laser irradiation is preferably. Laser irradiation can be carried out using a suitable laser processing machine using light sources such as carbon dioxide laser, UV-YAG laser, excimer laser, etc.

[0275] The shape of the through hole is not particularly limited, but a circular (substantially circular) shape is generally adopted. The top diameter of the through hole is preferably 50 μm or less, more preferably 30 μm or less, further preferably 20 μm or less, preferably 3 μm or more, more preferably 10 μm or more, further preferably 15 μm or more. Here, the top diameter of the through hole refers to the opening diameter of the through hole on the surface of the rewiring formation layer.

[0276] (Process (F))

[0277] Step (F) is a step of forming a rewiring layer as a conductive layer on the rewiring-forming layer. The method for forming the rewiring layer on the rewiring-forming layer can be the same as the method for forming a conductive layer on the insulating layer in the circuit board manufacturing method. Alternatively, steps (E) and (F) can be repeated to alternately deposit (stack) the rewiring layer and the rewiring-forming layer.

[0278] (Process (G))

[0279] Operation (G) is the operation of forming a solder mask on the redistribution layer. The material of the solder mask can use any material with insulating properties. Wherein, from the viewpoint of the manufacturing difficulty of semiconductor chip packaging, preferably a photosensitive resin and a thermosetting resin. In addition, as a thermosetting resin, the resin composition of the present invention can be used.

[0280] In addition, in step (G), bump processing can be performed as needed to form bumps. Bump processing can be performed using methods such as solder balls and solder plating. In addition, through-hole formation in bump processing can be performed in the same manner as in step (E).

[0281] (Process (H))

[0282] In addition to steps (A) to (G), the method for manufacturing a semiconductor chip package may further include step (H). Step (H) is a step of singulating the plurality of semiconductor chip packages into individual semiconductor chip packages. The method for singulating the semiconductor chip packages into individual semiconductor chip packages is not particularly limited.

[0283] Semiconductor devices

[0284] Semiconductor devices include semiconductor chip packages. Examples of semiconductor devices include various semiconductor devices used in electrical products (such as computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical equipment, and televisions) and vehicles (such as motorcycles, automobiles, trains, ships, and airplanes). Example

[0285] The present invention will be described in detail below by way of examples. The present invention is not limited to these examples. It should be noted that, unless otherwise indicated, "parts" and "%" indicating amounts herein represent "parts by mass" and "% by mass," respectively.

[0286] <Synthesis Example 1: Synthesis of Active Ester Resin>

[0287] Add 288 parts by mass of 1-naphthol and 1400 parts by mass of toluene to the reaction vessel, and dissolve the above components while replacing the container with nitrogen under reduced pressure. Next, add 203 parts by mass of isophthaloyl chloride and dissolve it. While purging the container with nitrogen, add 400 g of a 20% aqueous sodium hydroxide solution dropwise over 3 hours. At this time, the temperature in the system is controlled below 60°C. Then, stir the reaction for 1 hour. After the reaction is completed, separate the reactants and remove the water layer. Repeat this operation until the pH of the water layer reaches 7, and distill off the toluene and the like under heating and reduced pressure conditions to obtain an active ester resin (the compound of the above formula (3), molecular weight 418.4). The functional group equivalent of the active ester resin is 209 g / equivalent, and the softening point is 78°C.

[0288] <Example 1>

[0289] 2 parts of a glycidylamine epoxy resin ("EP-3980S" manufactured by ADEKA Co., Ltd., epoxy equivalent 115 g / eq.), 7 parts of an alicyclic epoxy resin ("CELLOXIDE 2021P" manufactured by Daicel Corporation, epoxy equivalent 136 g / eq.), 5 parts of the active ester resin obtained in Synthesis Example 1 (softening point 78° C.), 5 parts of an acid anhydride curing agent ("MH-700" manufactured by Shin Nippon Rika Co., Ltd.), and silica A (average particle size 9 μm, specific surface area 5.0 m 2 / g, surface-treated with KBM573 (manufactured by Shin-Etsu Chemical Co., Ltd.) and 0.1 part of a curing accelerator ("1B2PZ" manufactured by Shikoku Chemicals Co., Ltd., 1-benzyl-2-phenylimidazole) were uniformly dispersed to obtain a resin composition.

[0290] <Example 2>

[0291] In addition to using alumina A (average particle size 10 μm, specific surface area 0.3 m 2 / g, and 170 parts of KBM5783 (manufactured by Shin-Etsu Chemical Co., Ltd., surface-treated) were used instead of 140 parts of silica A. The same operation as in Example 1 was carried out to obtain a resin composition.

[0292] <Example 3>

[0293] In addition to using silica B (average particle size 9 μm, specific surface area 5.0 m 2 / g, and 140 parts of KBM503 (manufactured by Shin-Etsu Chemical Co., Ltd., surface-treated) were used instead of 140 parts of silica A. The same operation as in Example 1 was carried out to obtain a resin composition.

[0294] <Example 4>

[0295] A resin composition was obtained by performing the same operation as in Example 1, except that the amount of the active ester resin (softening point 78° C.) obtained in Synthesis Example 1 was changed from 5 parts to 3 parts, and the amount of the acid anhydride curing agent (“MH-700” manufactured by Shin Nippon Rika Co., Ltd.) was changed from 5 parts to 7 parts.

[0296] <Example 5>

[0297] A resin composition was obtained by performing the same operation as in Example 1, except that the amount of the active ester resin (softening point 78° C.) obtained in Synthesis Example 1 was changed from 5 parts to 7 parts, and the amount of the acid anhydride curing agent (“MH-700” manufactured by Shin Nippon Rika Co., Ltd.) was changed from 5 parts to 3 parts.

[0298] <Comparative Example 1>

[0299] A resin composition was obtained by performing the same operation as in Example 1, except that the active ester resin (softening point 78° C.) obtained in Synthesis Example 1 was not used and the amount of the acid anhydride curing agent (“MH-700” manufactured by Shin Nippon Rika Co., Ltd.) used was changed from 5 parts to 10 parts.

[0300] Comparative Example 2

[0301] A resin composition was obtained by the same operation as in Example 1 except that 5 parts of a commercially available active ester resin ("HPC-8000" manufactured by DIC Corporation, softening point 152°C) was used instead of 5 parts of the active ester resin (softening point 78°C) obtained in Synthesis Example 1.

[0302] <Test Example 1: Evaluation of Adhesion to Silicon Wafer after High-Temperature and High-Humidity Environment Test (HAST)>

[0303] On a 12-inch silicon wafer, the resin composition prepared in the embodiment and the comparative example was compression molded using a compression molding device (mold temperature: 130°C, pressure: 6MPa, curing time: 10 minutes) to form a resin composition layer 300 μm thick. Then, the resin composition layer was thermally cured at 180°C for 90 minutes to prepare a sample. For the sample prepared, a high-temperature, high-humidity environmental test of 100 hours was carried out at 130°C, 85%RH using a highly accelerated life tester ("PM422" manufactured by Kusunoki Chemicals, Ltd.). For the sample after the test, it was confirmed whether there was peeling between the interface of the cured product and the silicon wafer of the substrate. The situation where there was no peeling between the interface of the cured product and the silicon wafer of the substrate was evaluated as "○", and the situation where there was peeling between the interface of the cured product and the silicon wafer of the substrate was evaluated as "×".

[0304] <Test Example 2: Measurement of Dielectric Loss Tangent>

[0305] On a 12-inch silicon wafer that has been subjected to a demolding treatment, the resin composition prepared in the embodiment and the comparative example was compression molded using a compression molding device (mold temperature: 130°C, pressure: 6MPa, curing time: 10 minutes) to form a resin composition layer with a thickness of 300μm. Then, the resin composition was peeled off from the demolded silicon wafer and heated at 180°C for 90 minutes to thermally cure the resin composition to prepare a sample. The dielectric loss tangent at 79GHz was measured by the Fabry-Perot method. Three test pieces were measured and the average value was calculated.

[0306] <Test Example 3: Measurement of Storage Modulus>

[0307] On a 12-inch silicon wafer subjected to demoulding, a compression molding device (mold temperature: 130°C, pressure: 6MPa, curing time: 10 minutes) was used to compression mold the resin composition prepared in the embodiment and the comparative example to form a resin composition layer 300 μm thick. Then, the resin composition was peeled off from the silicon wafer subjected to demoulding, and the resin composition was heat-cured at 180°C for 90 minutes to prepare a cured product sample. The cured product was cut into test pieces of 7 mm wide and 40 mm long, and dynamic mechanical analysis was performed in a tensile mode using a dynamic mechanical analyzer DMS-6100 (manufactured by Seiko Instruments Inc.). After the test piece was loaded into the device, it was measured under the measuring conditions of a frequency of 1 Hz and a heating rate of 5°C / minute. The value of the storage modulus (E') GPa at 25°C in the measurement was read.

[0308] <Test Example 4: Evaluation of Flow Marks>

[0309] The resin compositions prepared in the Examples and Comparative Examples were compression-molded onto a 12-inch silicon wafer using a compression molding apparatus (mold temperature: 130°C, pressure: 6 MPa, curing time: 10 minutes) to form a 300 μm thick resin composition layer. The layers were then heated at 150°C for 60 minutes, and the presence of flow marks on the surface of the resin composition layer was visually inspected. Samples with flow marks were rated "×"; samples without flow marks were rated "○."

[0310] <Test Example 5: Evaluation of Properties of Resin Composition>

[0311] The properties of the resin compositions prepared in Examples and Comparative Examples were evaluated: a resin composition that was in a fluid liquid state at 25° C. was evaluated as "liquid," and a resin composition that was in a clay-like state without fluidity was evaluated as "clay-like."

[0312] The non-volatile components of the resin compositions of Examples and Comparative Examples and their usage amounts, as well as the measurement results and evaluation results of the test examples are shown in Table 1 below.

[0313] [Table 1]

[0314] .

[0315] The above results show that when the components (B-1) to (B-3) are used as the (B) curing agent, a cured product can be obtained in which the dielectric properties are reduced and the generation of flow marks is suppressed.

Claims

1. A resin composition comprising (A) an epoxy resin, (B) a curing agent, and (C) an inorganic filler, wherein: Component (A) comprises a liquid epoxy resin, The liquid epoxy resin comprises an alicyclic epoxy resin having an ester skeleton, Component (A) contains a glycidylamine type epoxy resin, The component (B) comprises (B-1) an active ester resin having a softening point of 100° C. or lower among the bifunctional active ester resins represented by formula (1). In the formula, rings X, Y and Z each independently represent an unsubstituted benzene ring or a naphthalene ring, When the nonvolatile matter in the resin composition is 100% by mass, the content of the component (A) is 1% by mass to 50% by mass. When the non-volatile components in the resin composition are taken as 100% by mass, the content of the component (B-1) is 1% to 10% by mass, and when the non-volatile components in the resin composition are taken as 100% by mass, the content of the component (C) is 50% by mass or more. The cured product obtained by thermally curing the resin composition at 180° C. for 90 minutes had a dielectric loss tangent of 0.004 or less as measured by the Fabry-Perot method at a measurement frequency of 79 GHz.

2. The resin composition according to claim 1, wherein The component (B-1) is an active ester resin having a softening point of 100° C. or less among the bifunctional active ester resins represented by formula (2). In the formula, rings A, B, C, D and E each independently represent an unsubstituted benzene ring.

3. The resin composition according to claim 1, wherein The softening point of the component (B-1) is 80°C or lower.

4. The resin composition according to claim 1, wherein The molecular weight of the component (B-1) is 1,000 or less.

5. The resin composition according to claim 1, wherein The molecular weight of the component (B-1) is 500 or less. The resin composition according to claim 1 , wherein The component (B) further contains one or more curing agents selected from the group consisting of phenol-based curing agents, naphthol-based curing agents, amine-based curing agents, and acid anhydride-based curing agents.

7. The resin composition according to claim 1, wherein The component (B) further contains an acid anhydride curing agent.

8. The resin composition according to claim 1, wherein When the nonvolatile matter in the resin composition is 100% by mass, the content of the component (B) is 1% by mass to 50% by mass.

9. The resin composition according to claim 1, wherein When the nonvolatile matter in the resin composition is 100 mass %, the content of the component (B) is 4 mass % to 20 mass %.

10. The resin composition according to claim 1, wherein The epoxy equivalent of the component (A) is 50 g / eq. to 5000 g / eq.

11. The resin composition according to claim 1, wherein The weight average molecular weight (Mw) of the component (A) is 100 to 5,000.

12. The resin composition according to claim 1, wherein When the nonvolatile matter in the resin composition is 100 mass %, content of the component (A) is 3 mass % to 20 mass %.

13. The resin composition according to claim 1, wherein The component (C) contains an inorganic filler selected from silica and alumina.

14. The resin composition according to claim 1, wherein The average particle size of the component (C) is 1 μm to 40 μm.

15. The resin composition according to claim 1, wherein When the nonvolatile matter in the resin composition is 100% by mass, the content of the component (C) is 80% by mass or more.

16. The resin composition according to claim 1, wherein When the nonvolatile matter in the resin composition is 100% by mass, the content of the component (C) is 98% by mass or less. The resin composition according to claim 1 , which is liquid at 25° C. The resin composition according to claim 1 , which is used to form an insulating layer of a semiconductor chip package. The resin composition according to claim 1 , which is used to form an insulating layer of a circuit board. 20 . The resin composition according to claim 1 , which is used for sealing a semiconductor chip of a semiconductor chip package. 21 . A cured product, which is a cured product of the resin composition according to claim 1 .

22. A resin sheet comprising: Support body, and A resin composition layer provided on the support and comprising the resin composition according to any one of claims 1 to 20. 23 . A circuit board comprising an insulating layer formed from a cured product of the resin composition according to claim 1 .

24. A semiconductor chip package, comprising: The circuit substrate according to claim 23, and A semiconductor chip is mounted on the circuit substrate. A semiconductor device comprising the semiconductor chip package according to claim 24 .

26. A semiconductor chip package, comprising: semiconductor chips, and A cured product of the resin composition according to any one of claims 1 to 20 for sealing the semiconductor chip. A semiconductor device comprising the semiconductor chip package according to claim 26 .

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