Curable resin composition, adhesive, sealing material, cured product, semiconductor device and electronic component

Abstract

To provide a curable resin composition which is curable at low temperatures, for example, 50 to 100°C, preferably, 80°C, and suppresses occurrence of cracking after curing, an adhesive or sealing material containing the same, a cured product of the same, and a semiconductor device and an electronic component containing the cured product.SOLUTION: There are provided a curable resin composition which contains (A) a radical-polymerizable curable compound, (B) a radical polymerization initiator, and (C) inorganic particles, wherein a mass ratio of a component obtained by subtracting the mass of the inorganic particles from the total mass of a cured product after curing at 80°C for 60 minutes, to a mass of a component obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80°C for 60 minutes is 70 mass% or more; an adhesive or sealing material containing the same; a cured product of the same; and a semiconductor device and an electronic component containing the cured product.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a curable resin composition, an adhesive or sealing material containing the same, a cured product thereof, and a semiconductor device and an electronic component each containing the cured product. [Background technology]

[0002] As high-performance communication devices such as smartphones and tablets become more widespread, there is an increasing demand for products to be lighter, smaller, and thinner. In addition, the market for the Internet of Things (IoT), in which everything is connected to the Internet, is growing rapidly. While various devices are being developed for IoT applications, including smartphones, the inability to manufacture them at high temperatures due to issues with materials and other factors is becoming an issue. For example, joining parts with solder requires joining at high temperatures of over 180°C, which can damage the parts, so there is a demand for joining materials that can be hardened at low temperatures.

[0003] Thermal radical polymerizable resin compositions used in the manufacturing method of electronic component devices and semiconductor devices are known. Resin compositions containing conductive particles can also be used as conductive materials used for bonding electronic components. For example, Patent Document 1 discloses a conductive resin composition and a die attachment agent containing the same, characterized in that the conductive resin composition contains (A) polyethylene glycol di(meth)acrylate having a specific structure, (B) a radical generator, (C) a conductive filler, and (D) at least one selected from the group consisting of linear alkanediol di(meth)acrylate having a linear alkylene group having 5 to 14 carbon atoms, monofunctional and bifunctional polyester (meth)acrylates, and terminal-modified polybutadiene rubber. Patent Documents 2 to 4 disclose thermosetting conductive adhesives containing aromatic urethane acrylate having six acrylic groups, a monomer having one acrylic or methacrylic group, an organic peroxide, and conductive particles. On the other hand, resin compositions containing insulating particles can also be used as insulating adhesives or sealants used for bonding and protecting electronic components. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2016-117860 A [Patent Document 2] International Publication No. 2018 / 043296 [Patent Document 3] International Publication No. 2018 / 047597 [Patent Document 4] International Publication No. 2018 / 047598 Summary of the Invention [Problem to be solved by the invention]

[0005] Curable resin compositions used in IoT applications such as smartphones, for example as adhesives for camera modules, are required to be curable at low temperatures of 80° C. or less. In addition, from the viewpoint of functional expression (ensuring electrical continuity and maintaining reliability), the curable resin composition is required to be free of cracks (bulk cracks) after curing.

[0006] The conductive resin composition disclosed in Patent Document 1 requires heat curing at a temperature of about 150° C. In addition, the thermosetting conductive adhesives disclosed in Patent Documents 2 to 4 have a problem in that they shrink significantly on curing and are prone to cracking.

[0007] The present invention aims to provide a curable resin composition that can be cured at a low temperature of, for example, 50 to 100°C, preferably 80°C, and that suppresses the occurrence of cracks after curing, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product. [Means for solving the problem]

[0008] Specific means for solving the above problems are as follows. Embodiments of the present invention include a curable resin composition, an adhesive or sealant, a cured product, and a semiconductor device or electronic component having the following aspects. (1) (A) a radically polymerizable curable compound; (B) a radical polymerization initiator; (C) inorganic particles; A curable resin composition comprising: the mass ratio of the component obtained by subtracting the mass of the inorganic particles from the total mass of the cured product after curing at 80° C. for 60 minutes to the mass of the component obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80° C. for 60 minutes is 70 mass% or more; Curable resin composition. (2) The curable resin composition according to (1) above, wherein the (A) radically polymerizable curable compound contains a (meth)acrylate compound having a boiling point of 200° C. or higher. (3) The curable resin composition according to (1) or (2) above, wherein the (A) radically polymerizable curable compound comprises a monofunctional (meth)acrylate compound and a polyfunctional (meth)acrylate compound having a boiling point of 200°C or higher. (4) The curable resin composition according to any one of the above (1) to (3), wherein the content of the monofunctional (meth)acrylate compound is 0 to 45 parts by mass relative to 100 parts by mass of the component (A). (5) The curable resin composition according to any one of the above (1) to (4), wherein the (A) radically polymerizable curable compound contains a bismaleimide compound. (6) The curable resin composition according to any one of the above (1) to (5), wherein the (B) radical polymerization initiator is an organic peroxide. (7) The curable resin composition according to any one of the above (1) to (6), wherein the (B) radical polymerization initiator is an organic peroxide having a 10-hour half-life temperature of 70° C. or lower. (8) The curable resin composition according to any one of the above (1) to (7), wherein the (B) radical polymerization initiator is an organic peroxide having a dicarbonate structure. (9) The curable resin composition according to any one of the above (1) to (8), wherein the (C) inorganic particles include conductive particles. (10) The curable resin composition according to any one of the above (1) to (9), wherein the (C) inorganic particles contain silver particles. (11) The curable resin composition according to any one of (1) to (10) above, further comprising (D) a polymerization inhibitor. (12) An adhesive or sealant comprising the curable resin composition according to any one of (1) to (11) above. (13) A cured product obtained by curing the curable resin composition according to any one of (1) to (11) above, or the adhesive or sealant according to (12) above. (14) A semiconductor device or electronic part comprising the cured product described in (13) above. (15) An electronic part for a camera module, comprising the cured product according to (13) above. Effect of the Invention

[0009] According to an embodiment of the present invention, there are provided a curable resin composition that can be cured at a low temperature of, for example, 50 to 100°C, preferably 80°C, and that suppresses the occurrence of cracks after curing, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and an electronic component containing the cured product. [Brief description of the drawings]

[0010] [Figure 1] 1 shows optical microscope photographs (magnification 400x) of the resin compositions of Example 5 and Comparative Example 1 cured at 80° C. for 60 minutes. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] In this specification, following the convention in the field of synthetic resins, a name including the term "resin", which normally refers to a polymer (particularly a synthetic polymer), may be used for a component that constitutes a curable resin composition before curing, even if that component is not a polymer, for example, a prepolymer compound before curing. In this specification, the general term "pot life" refers to the time during which a resin composition remains usable after it is prepared. In this specification, the term "(meth)acryloyl group" includes both methacryloyl groups and acryloyl groups, and the term "(meth)acrylate compound" includes both acrylate compounds and methacrylate compounds. In this specification, the weight average molecular weight refers to a value obtained by gel permeation chromatography (GPC) using a calibration curve based on standard polystyrene. In this specification, the average particle size (D50) of inorganic particles including conductive particles and insulating particles refers to the particle size (median size) at a cumulative frequency of 50% in the volume-based particle size distribution measured by a laser diffraction / scattering method.

[0012] [Resin composition] The curable resin composition according to one embodiment of the present invention comprises: (A) a radically polymerizable curable compound; (B) a radical polymerization initiator; (C) inorganic particles; In this curable resin composition, the mass ratio of the components obtained by subtracting the mass of the inorganic particles from the total mass of the cured product after curing at 80° C. for 60 minutes to the mass of the components obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80° C. for 60 minutes is 70 mass% or more. According to this embodiment, it is possible to provide a curable resin composition that can be cured at a low temperature of, for example, 50 to 100° C., preferably 80° C., and that suppresses the occurrence of cracks after curing.

[0013] The present inventors have found that the occurrence of cracks can be effectively suppressed by setting the mass ratio of the components obtained by subtracting the mass of inorganic particles from the total mass of the curable resin composition before curing at 80°C for 60 minutes to 70% by mass or more. The reason for this is presumed to be, but is not limited to, the following. In particular, in a resin composition containing inorganic particles as a filler, when the resin component volatilizes from the surface of the resin composition coating film during curing, the resin component on the coating film surface decreases, and the coating film is reduced due to the curing shrinkage of the resin component, and the inorganic particle density increases especially on the coating film surface where the resin component is reduced. In this case, the resin component near the coating film surface cannot move and cannot withstand the curing shrinkage force of the resin component, resulting in cracks. In the present invention, the mass ratio of the components obtained by subtracting the mass of the inorganic particles from the total mass of the cured product after curing at 80°C for 60 minutes to the mass of the components obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80°C for 60 minutes is set to 70 mass% or more. This controls the amount of volatilization of the resin components of the resin composition during curing and controls the increase in inorganic particle density on the coating film surface, thereby effectively suppressing the occurrence of cracks.

[0014] In the resin composition of the present embodiment, the mass ratio of the components obtained by subtracting the mass of the inorganic particles from the total mass of the cured product after curing at 80°C for 60 minutes to the mass of the components obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80°C for 60 minutes (hereinafter also referred to as "mass ratio of organic matter before and after curing at 80°C for 60 minutes") is 70 mass% or more, preferably 75 mass% or more, and more preferably 79 mass% or more. When determining the mass ratio of organic matter before and after curing at 80°C for 60 minutes, the curing conditions at 80°C for 60 minutes are, for example, to attach two pieces of tape, approximately 85 to 95 μm thick, parallel to each other with an interval of 20 mm on a glass substrate, print each resin composition measuring width: 20 mm × length: 65 mm × thickness: approximately 90 μm between the two pieces of tape, and then cure at 80°C for 60 minutes in an air convention oven. The mass ratio [%] of organic matter before and after curing at 80°C for 60 minutes is calculated using the following formula. M = [{m0-m1} / {m2-m3}] x 100 M: Mass ratio of organic matter before and after curing at 80℃ for 60 minutes [%] m0: Total mass of the cured product after curing at 80℃ for 60 minutes [g] m1: Mass of inorganic particles after curing at 80℃ for 60 minutes [g] m2: Total mass [g] of the curable resin composition before curing at 80°C for 60 minutes m3: Mass of inorganic particles before hardening at 80℃ for 60 minutes [g] The cured product after curing at 80° C. for 60 minutes is a cured product of the resin composition after the curable resin composition is cured at 80° C. for 60 minutes. The mass of the inorganic particles after curing at 80°C for 60 minutes can be determined by treating the cured product in a baking oven at a high temperature of 800°C or higher for 4 hours and measuring the mass of the inorganic material obtained as a residue after the treatment. If the content of the inorganic particles in the cured product is known, the value calculated by multiplying the mass of the cured product by the content may be used as the mass of the inorganic particles. The mass ratio of the organic matter before and after curing at 80° C. for 60 minutes can be adjusted, for example, by adjusting the types and blending ratios of each component contained in the resin composition.

[0015] (A) Radical polymerizable curable compound The resin composition of the present embodiment contains (A) a radically polymerizable curable compound (hereinafter also referred to as "component (A)"). (A) The radically polymerizable curable compound imparts curability and adhesiveness to the resin composition. (A) The radically polymerizable curable compound has a relatively fast polymerization rate, and therefore can be cured quickly. Examples of (A) the radically polymerizable curable compound include, but are not limited to, (meth)acrylate compounds, bismaleimide compounds, and the like.

[0016] In this embodiment, the radically polymerizable curable compound (A) preferably contains at least one selected from the group consisting of a (meth)acrylate compound and a bismaleimide compound, and may contain two. In one embodiment, the radically polymerizable curable compound (A) preferably contains a (meth)acrylate compound. The (meth)acrylate compound includes a urethane (meth)acrylate compound, and in one embodiment, the radically polymerizable curable compound (A) preferably contains a urethane (meth)acrylate compound. In one embodiment, the radically polymerizable curable compound (A) preferably contains a bismaleimide compound. In one embodiment, the (A) radically polymerizable curable compound may, for example, contain only a (meth)acrylate compound other than a urethane (meth)acrylate compound, may contain two types of compounds, a (meth)acrylate compound other than a urethane (meth)acrylate compound and a urethane (meth)acrylate compound, may contain two types of compounds, a (meth)acrylate compound other than a urethane (meth)acrylate compound and a bismaleimide compound, or may contain three types of compounds, a (meth)acrylate compound other than a urethane (meth)acrylate compound, a bismaleimide compound, and a urethane (meth)acrylate compound.

[0017] In one embodiment, the radically polymerizable curable compound (A) is preferably liquid at 25° C. This eliminates the need for a solvent in the resin composition, making it possible to prevent the occurrence of voids when the resin composition is used. The content of the solvent in the resin composition of this embodiment is preferably less than 3% by mass, more preferably less than 1% by mass, and even more preferably 0% by mass (solvent-free), based on the total mass of the resin composition.

[0018] The content of the radically polymerizable curable compound (A) in the resin composition is preferably 4 to 90 parts by mass, more preferably 5 to 50 parts by mass, and even more preferably 7 to 30 parts by mass, relative to 100 parts by mass of the total amount of the resin composition. The content of the radically polymerizable curable compound (A) in the resin composition is preferably 75 to 99 parts by mass, more preferably 80 to 98 parts by mass, even more preferably 85 to 97 parts by mass, and particularly preferably 90 to 97 parts by mass, relative to 100 parts by mass of the total amount of all organic substances contained in the resin composition.

[0019] In this specification, the (meth)acrylate compound refers to a compound having at least one (meth)acryloyl group in the molecule, and includes a monofunctional (meth)acrylate compound having one (meth)acryloyl group and a polyfunctional (meth)acrylate compound having two or more (meth)acryloyl groups. In this embodiment, the (A) radically polymerizable curable compound preferably contains a (meth)acrylate compound having a boiling point of 200° C. or more. Since the compound has a high boiling point, the amount of volatilization of the resin component on the surface of the resin composition when cured at 80° C. for 60 minutes can be suppressed, and the increase in inorganic particle density on the coating surface can be suppressed, so that the occurrence of cracks can be effectively suppressed. In this specification, the boiling point can be measured by, for example, a method according to JIS K 2233, JIS K 2254 (corresponding to ISO 3405) or JIS K 0066, but is not limited thereto. In this embodiment, the (meth)acrylate compound having a boiling point of 200° C. or higher is preferably a polyfunctional (meth)acrylate compound having a boiling point of 200° C. or higher, and more preferably a di- to tetra-functional (meth)acrylate compound having a boiling point of 200° C. or higher. The polyfunctionality allows for improved reactivity, and the (meth)acrylate compound is incorporated into crosslinks before volatilization, thereby effectively suppressing the occurrence of cracks. In addition, when the (meth)acrylate compound is a di- to tetra-functional (meth)acrylate compound, the crosslink density does not become too dense, and curing shrinkage during curing can be suppressed.

[0020] In one embodiment, the radically polymerizable curable compound (A) contains a monofunctional (meth)acrylate compound and a polyfunctional (meth)acrylate compound having a boiling point of 200° C. or higher. Even if the compound contains a monofunctional (meth)acrylate compound having a low boiling point, it is possible to incorporate the compound into crosslinks before it volatilizes by using the compound in combination with a polyfunctional (meth)acrylate compound having a boiling point of 200° C. or higher. In one embodiment, the content of the polyfunctional (meth)acrylate compound having a boiling point of 200° C. or higher is preferably 18 parts by mass or more, for example, 18 to 100 parts by mass, relative to 100 parts by mass of the total amount of the (meth)acrylate compounds. In one embodiment, the content of the polyfunctional (meth)acrylate compound having a boiling point of 200°C or higher is preferably 10 parts by mass or more, for example, 10 to 100 parts by mass, for example, 10 to 90 parts by mass, for example, 10 to 80 parts by mass, or for example, 10 to 70 parts by mass, relative to 100 parts by mass of component (A). In one embodiment, the content of the monofunctional (meth)acrylate compound is 45 to 80 parts by mass relative to 100 parts by mass of component (A). In one embodiment, the content of the monofunctional (meth)acrylate compound is 0 to 45 parts by mass relative to 100 parts by mass of component (A).

[0021] Examples of monofunctional (meth)acrylate compounds include alkyl (meth)acrylates in which the alkyl group has a branched structure, such as isobutyl (meth)acrylate and t-butyl (meth)acrylate; esters of (meth)acrylic acid and alicyclic alcohols, such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and dicyclopentanyl (meth)acrylate; esters of (meth)acrylic acid and cyclic alcohols, such as cyclic trimethylolpropane formal (meth)acrylate; esters of (meth)acrylic acid and aromatic alcohols, such as phenoxyethyl (meth)acrylate; acid-modified mono(meth)acrylates, such as phosphoric acid-modified (meth)acrylates; and (meth)acrylamide compounds, such as hydroxyethyl (meth)acrylamide, but are not limited thereto.

[0022] Examples of polyfunctional (meth)acrylate compounds include alkyl (meth)acrylates such as 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, and neopentyl glycol di(meth)acrylate; polyalkylene glycol di(meth)acrylates such as tripropylene glycol di(meth)acrylate; bifunctional (meth)acrylates such as polyester (meth)acrylate and neopentyl glycol modified trimethylolpropane di(meth)acrylate; trifunctional (meth)acrylates such as trimethylolpropane tri(meth)acrylate; tetrafunctional (meth)acrylates such as pentaerythritol tetra(meth)acrylate and ditrimethylolpropane tetra(meth)acrylate; pentafunctional (meth)acrylates such as dipentaerythritol penta(meth)acrylate; tricyclo[5.2.1.0 2,6 ] (meth)acrylates containing a cyclic structure such as decanedimethanol di(meth)acrylate; acid-modified poly(meth)acrylates such as phosphoric acid-modified poly(meth)acrylate; urethane (meth)acrylates having a urethane bond and a (meth)acryloyl group, but are not limited to these.

[0023] Examples of polyfunctional (meth)acrylate compounds having a boiling point of 200° C. or higher include 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tripropylene glycol di(meth)acrylate, tricyclo[5.2.1.0 2,6 ] decanedimethanol, etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0024] The (meth)acrylate compounds may be used alone or in combination of two or more kinds.

[0025] The (meth)acrylate compound includes a urethane (meth)acrylate compound. Depending on the properties required for the cured product, component (A) may include a urethane (meth)acrylate compound. The urethane (meth)acrylate compound is an oligomer having a urethane bond and a (meth)acryloyl group, and is obtained by the reaction of the hydroxyl group and the isocyanate group of the three main raw materials, hydroxy (meth)acrylate, diisocyanate, and polyol. Depending on the combination of the main raw materials, various properties can be imparted to the obtained urethane (meth)acrylate compound. For example, when the main raw material polyol is an ether-based compound, it is excellent in hydrolysis resistance and flexibility. For example, when the main raw material polyol is an ester-based compound, it is excellent in heat resistance, flexibility, and toughness. For example, when the main raw material polyol is a carbonate-based compound, it is excellent in heat resistance, weather resistance, and toughness.

[0026] The weight average molecular weight of the urethane (meth)acrylate compound is preferably 1,600 to 20,000, more preferably 2,000 to 18,000, and even more preferably 3,000 to 15,000. However, from the viewpoint of workability and reactivity of the resin composition, it is preferable that the urethane (meth)acrylate compound does not substantially contain a urethane (meth)acrylate compound having a weight average molecular weight of more than 20,000. It is also preferable that the urethane (meth)acrylate compound does not substantially contain a urethane (meth)acrylate compound having a weight average molecular weight of less than 1,600. As used herein, "substantially free" means that the component is not intentionally contained, specifically, that the component is present in the curable resin composition in an amount of less than 0.1% by mass.

[0027] The urethane (meth)acrylate compounds may be used alone or in combination of two or more kinds.

[0028] When component (A) contains a urethane (meth)acrylate compound, the content of the urethane (meth)acrylate compound is preferably 5 to 75 parts by mass, more preferably 6 to 50 parts by mass, and even more preferably 7 to 30 parts by mass, per 100 parts by mass of component (A).

[0029] When reliability (heat resistance, moisture resistance) and adhesive strength are required for the cured product, it is preferable that component (A) contains a bismaleimide compound. The bismaleimide compound is not particularly limited, and any compound having a chemical structure sandwiched between two maleimide groups may be used. Examples of bismaleimide compounds include N,N'-(4,4'-diphenylmethane) bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl)methane, m-phenylene bismaleimide (N,N'-1,3-phenylene bismaleimide ), 1,6-bismaleimidohexane, 1,2-bismaleimidoethane (N,N'-ethylenedimaleimide), N,N'-(1,2-phenylene)bismaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyldi-p-phenylene)dimaleimide, N,N'-[3,3'-(1,3-phenylenedioxy)diphenyl]bismaleimide.

[0030] When a low room temperature modulus is required for the cured product of the resin composition, the bismaleimide compound is preferably a bismaleimide compound having a hydrocarbon group derived from a dimer acid. Such a bismaleimide compound is described, for example, in JP 2015-193725 A. The hydrocarbon group derived from a dimer acid does not have a crosslinkable reactive group in the molecular chain, and is therefore considered to be capable of lowering the room temperature modulus. Commercially available bismaleimide compounds having a hydrocarbon group derived from a dimer acid include, but are not limited to, products "BMI-1500" and "BMI-1700" which are liquid at 25°C, and "BMI-3000" which is solid at 25°C (both manufactured by Designer Molecules Inc.).

[0031] The bismaleimide compound may be either a liquid at 25° C. or a solid at 25° C., but is preferably a liquid at 25° C. The weight average molecular weight of the bismaleimide compound is preferably 500 to 7,000, more preferably 700 to 5,500, and further preferably 800 to 3,000.

[0032] The bismaleimide compounds may be used alone or in combination of two or more.

[0033] When component (A) contains a bismaleimide compound, the content of the bismaleimide compound is preferably from 5 to 40 parts by mass, and more preferably from 15 to 35 parts by mass, per 100 parts by mass of component (A).

[0034] (B) Radical polymerization initiator The resin composition of this embodiment contains (B) a radical polymerization initiator (hereinafter also referred to as "component (B)"). The (B) radical polymerization initiator initiates radical polymerization of the (A) radically polymerizable curable compound, and cures the compound. In this embodiment, the (B) radical polymerization initiator is a thermal radical polymerization initiator that generates an active species radical by cleavage at a predetermined temperature, and examples of such initiators include organic peroxides, inorganic peroxides, and azo compounds. In this embodiment, the (B) radical polymerization initiator is preferably an organic peroxide, from the viewpoint of being incorporated into crosslinks before the low molecular weight (meth)acrylate compound volatilizes, and thus reducing volatile components.

[0035] The 10-hour half-life temperature (T10) of the radical polymerization initiator (B) is preferably 70°C or less, more preferably 35 to 70°C, and even more preferably 40 to 70°C. The 10-hour half-life temperature (T10) refers to the temperature at which it takes 10 hours for the radical polymerization initiator to decompose and its amount to be reduced to half (1 / 2). The 10-hour half-life temperature (T10) of component (B) of 70°C or less is an index showing the radical generating ability of component (B) at a low temperature of 50 to 100°C and its stability at room temperature. By having the 10-hour half-life temperature (T10) of the radical polymerization initiator (B) within the above range, the resin composition can be cured at a relatively low temperature and a long pot life can be obtained.

[0036] In the present embodiment, the radical polymerization initiator (B) is preferably an organic peroxide having a dicarbonate structure represented by the following formula (1). [ka] In the formula (1), R1 and R2 are each independently an alkyl group. The alkyl group may be linear, branched or cyclic, or any combination thereof. R1 and R2 may be the same or different. The number of carbon atoms in the alkyl group represented by R1 and R2 is preferably 1 to 30, more preferably 2 to 20, and even more preferably 3 to 20. In one embodiment, the alkyl group is preferably linear. The organic peroxide of formula (1) is preferably a solid at 25°C. The average particle size of the organic peroxide of formula (1) is preferably 1 μm to 400 μm. Here, the average particle size refers to the value of the volume cumulative 50% particle size (D50), and is a value obtained from the volume-based particle size distribution measured using a laser diffraction particle size distribution measuring device and a measuring device using a dynamic light scattering method. Since the organic peroxide of formula (1) has a dicarbonate structure, radicals are efficiently generated at low temperatures, for example, 50 to 100°C, preferably 80°C, and a termination reaction in which the radicals are deactivated is unlikely to occur, so that the initiation reaction and propagation reaction of the radical polymerization reaction of the resin composition proceed efficiently. As a result, the volatilization of the radically polymerizable curable compound (A) during curing of the resin composition is suppressed, and the radically polymerizable curable compound (A) is efficiently incorporated into crosslinks, so that the occurrence of cracks can be effectively suppressed.

[0037] The component (B) may be used alone or in combination of two or more kinds.

[0038] The content of component (B) in the resin composition is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 3 to 10 parts by mass, relative to 100 parts by mass of the radically polymerizable curable compound (A).

[0039] (C) Inorganic particles The resin composition of the present embodiment contains (C) inorganic particles (hereinafter also referred to as "component (C)"). Examples of the inorganic particles include (C1) conductive particles and (C2) insulating particles.

[0040] The (C1) conductive particles are used to impart thermal conductivity and / or electrical conductivity to a resin composition and its cured product. The resin composition containing the (C1) conductive particles can also be used as a conductive adhesive used for bonding electronic components, etc. In this specification, the term "conductive particles" refers to particles having an average particle size in the range of 0.01 μm to 100 μm and an electrical conductivity of 10 or higher. 6 S / m or more. (C1) Conductive particles may be conductive materials molded into particles, or may be nuclei (core particles) coated with a conductive material (coated powder). The nuclei contained in the conductive particles may be made of a non-conductive material as long as they are partially coated with a conductive material. (C1) Conductive particles include metal powders and coated powders.

[0041] The conductive material in the (C1) conductive particles is not particularly limited as long as it imparts thermal conductivity and / or electrical conductivity to the resin composition, and examples thereof include, but are not limited to, gold, silver, nickel, copper, palladium, platinum, bismuth, tin, and alloys thereof (particularly, bismuth-tin alloys, solders, etc.), aluminum, indium tin oxide, silver-coated copper, silver-coated aluminum, metal-coated glass spheres, silver-coated fibers, silver-coated resins, antimony-doped tin, tin oxide, carbon fibers, graphite, carbon black, and mixtures thereof. From the viewpoint of good thermal conductivity and electrical conductivity, the conductive material in the (C1) conductive particles is preferably at least one metal selected from the group consisting of silver, nickel, copper, tin, aluminum, silver alloys, nickel alloys, copper alloys, and aluminum alloys, more preferably at least one metal selected from the group consisting of silver, copper, and nickel, even more preferably silver or copper, and particularly preferably containing silver. In one embodiment, the (C1) conductive particles are preferably silver particles. In one embodiment, the (C1) conductive particles are preferably copper particles. The silver particles or copper particles include silver powder or copper powder, and a coated powder in which at least a portion of the surface of a core (core particle) is coated with silver or copper, respectively.

[0042] The shape of the (C1) conductive particles is not particularly limited, and may be any of spherical, amorphous, flake-like (scale-like), filament-like (needle-like), dendritic, and other shapes. The flake-like shape refers to a shape with an aspect ratio of 2 or more, expressed as "long diameter / short diameter", and includes flat shapes such as plate-like and scale-like. In this specification, the long diameter and short diameter of the conductive particles refer to the average values ​​of the long diameter and short diameter of any 20 particles based on an image obtained from a scanning electron microscope (SEM). The "long diameter" refers to the longest diameter of a line segment passing through the approximate center of gravity of the particle in a particle image obtained by SEM, and the "short diameter" refers to the shortest diameter of a line segment passing through the approximate center of gravity of the particle in a particle image obtained by SEM. The (C1) conductive particles may include particles of different shapes.

[0043] (C1) When the conductive particles are silver particles, the silver particles should have a tap density of 1.5 g / cm from the viewpoint of dispersibility. 3 It is preferable that the concentration is 2.0 to 6.0 g / cm or more. 3 In this specification, the tap density is a value measured in accordance with JIS Z2512 Metal Powder-Tap Density Measurement Method.

[0044] When the (C1) conductive particles are silver particles, the average particle size (D50) is preferably 0.05 μm to 50 μm, more preferably 0.1 μm to 20 μm, and even more preferably 0.1 μm to 15 μm, from the viewpoints of the fluidity of the resin composition and the conductivity of the cured product.

[0045] When the (C1) conductive particles are silver particles, the BET specific surface area is 4.0 m from the viewpoints of the viscosity of the resin composition and the conductivity of the cured product. 2 / g or less, and 0.1 to 3.0 m 2 It is more preferable that the molecular weight is / g.

[0046] The (C1) conductive particles may be used alone or in combination of two or more kinds.

[0047] The content of the (C1) conductive particles in the resin composition is, for example, 95 parts by mass or less, for example, 92 parts by mass or less, relative to 100 parts by mass of the total amount of the resin composition. In one embodiment, the content of the (B1) conductive particles in the resin composition is, for example, 10 to 95 parts by mass, more preferably 20 to 95 parts by mass, and even more preferably 50 to 95 parts by mass, and may be 70 to 95 parts by mass, relative to 100 parts by mass of the total amount of the resin composition.

[0048] The insulating particles (C2) can reduce the linear expansion coefficient of the cured product obtained by curing the resin composition, and improve thermal cycle resistance. The resin composition containing the insulating particles (C2) can also be used as an insulating adhesive or sealant for bonding or protecting electronic components.

[0049] The (C2) insulating particles are not particularly limited as long as they are made of granular bodies formed by an insulating inorganic material and have the effect of lowering the linear expansion coefficient by addition. As the insulating inorganic material, silica, talc, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, boron nitride, etc. can be used. As the (C2) insulating particles, it is preferable to use silica particles because it is possible to increase the loading amount. As the silica, amorphous silica is preferable. The (C2) insulating particles may be surface-treated with a coupling agent such as a silane coupling agent.

[0050] The shape of the (C2) insulating particles is not particularly limited, and may be any shape, such as spherical, irregular, flake-like (scale-like), filament-like (needle-like), or dendritic.

[0051] When the (C2) insulating particles are silica particles, the average particle size (D50) is preferably 0.01 to 20 μm, more preferably 0.05 to 15 μm, and even more preferably 0.1 to 10 μm.

[0052] The insulating particles (C2) may be used alone or in combination of two or more kinds.

[0053] The content of the (C2) insulating particles is preferably 0.1 to 80 parts by mass, more preferably 1 to 75 parts by mass, and even more preferably 10 to 70 parts by mass, relative to 100 parts by mass of the total amount of the resin composition.

[0054] If desired, the resin composition of the present embodiment may contain optional components other than the above components (A) to (C), such as those described below, as necessary.

[0055] (D) Polymerization inhibitor The resin composition of the present embodiment may contain (D) a polymerization inhibitor (hereinafter also referred to as "component (D)"). (D) The polymerization inhibitor is a compound having a radical scavenging ability. By containing (D) the polymerization inhibitor, the progress of unintended radical polymerization reaction at room temperature of about 25°C is suppressed, and the stability during storage of the resin composition can be further improved.

[0056] As the (D) polymerization inhibitor, a known polymerization inhibitor can be used, and examples thereof include, but are not limited to, N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, hydroquinone, p-benzoquinone, etc. Also, known polymerization inhibitors disclosed in JP-A-2010-117545 and JP-A-2008-184514 can be used. As the (D) polymerization inhibitor, any one type may be used, or two or more types may be used in combination.

[0057] When the resin composition contains a polymerization inhibitor (D), the content of the polymerization inhibitor (D) is preferably 0.1 to 5.0 parts by mass, more preferably 0.2 to 4.0 parts by mass, and even more preferably 0.3 to 3.0 parts by mass, per 100 parts by mass of component (C).

[0058] Other additives If desired, the resin composition of the present embodiment may further contain other additives, such as carbon black, titanium black, coupling agents, ion trapping agents, leveling agents, antioxidants, defoamers, viscosity modifiers, flame retardants, colorants, plasticizers, etc., within the scope of the present embodiment. The type and amount of each additive are the same as in the conventional manner.

[0059] The method for producing the resin composition of the present embodiment is not particularly limited. For example, the components (A) to (C), and if necessary, the component (D), and other additives, etc. are simultaneously or separately introduced into an appropriate mixer, and stirred and mixed to form a uniform composition, thereby obtaining the resin composition of the present embodiment. This mixer is not particularly limited, but a Raikai mixer, Henschel mixer, three-roll mill, ball mill, planetary mixer, bead mill, etc. equipped with a stirring device and a heating device can be used. These devices may also be used in appropriate combination.

[0060] The resin composition thus obtained is thermosetting and can be cured at a low temperature, for example, 40 to 120°C, preferably 50 to 100°C, more preferably 70 to 90°C, and even more preferably 80°C. Under the condition of a temperature of 80°C, it is preferable that the composition cures within 4 hours, more preferably within 3 hours, and even more preferably within 1 hour. When the curable composition of the present embodiment is used for the manufacture of a semiconductor module including a component that deteriorates under high temperature conditions, it is preferable to thermally cure the composition at a temperature of 50 to 100°C for 15 minutes to 4 hours, preferably 30 minutes to 2 hours.

[0061] The resin composition of the present embodiment can be used, for example, as an adhesive or sealant for fixing, joining, or protecting components that constitute a semiconductor device or electronic component, or as a raw material thereof.

[0062] The application method of the resin composition of the present embodiment is not particularly limited, and can be supplied to a desired portion of a substrate or the like by a known printing method, dispensing method, or coating method. Examples of printing methods include, but are not limited to, inkjet printing, screen printing, lithographic printing, carton printing, metal printing, offset printing, gravure printing, flexographic printing, and the like. Examples of dispensing methods include, but are not limited to, methods using a jet dispenser, an air dispenser, and the like. Examples of coating methods include, but are not limited to, dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, spin coater coating, and the like.

[0063] [Adhesive or sealant] An adhesive or sealant according to one embodiment of the present invention includes the resin composition according to the above embodiment. This adhesive or sealant enables good fixing, bonding or protection of engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, and metals (e.g., copper, nickel, etc.), and can be used to fix, bond or protect components constituting a semiconductor device or electronic component. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, camera modules, semiconductor modules, and integrated circuits. The adhesive or sealant of the present embodiment can be cured under low temperature conditions, and therefore has high productivity and is suitable for use, for example, in the manufacture of semiconductor devices and electronic components.

[0064] [Cured product of resin composition, adhesive or sealant] The cured product of one embodiment of the present invention is a cured product obtained by curing the resin composition, adhesive, or sealant of the above-mentioned embodiment. Depending on the type of (C) inorganic particles, either a conductive cured product or an insulating cured product can be provided.

[0065] [Semiconductor equipment, electronic components] Since the semiconductor device or electronic component of one embodiment of the present invention includes the cured product of the third embodiment described above, the semiconductor device or electronic component has high reliability. Here, the semiconductor device refers to a device that can function by utilizing semiconductor characteristics, and includes electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc. Examples of the semiconductor device or electronic component include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, camera modules, semiconductor modules, and integrated circuits. EXAMPLES

[0066] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following examples, parts and % indicate parts by mass and % by mass unless otherwise specified.

[0067] [Examples 1 to 17, Comparative Examples 1 to 9] Resin compositions were prepared by mixing predetermined amounts of each component using a three-roll mill according to the formulation shown in Table 1. In Table 1, the amount of each component is expressed in parts by mass (unit: g). The components used in the examples and comparative examples are as follows.

[0068] (A) Radical polymerizable curable compound (component (A)) (A-1): Phenoxyethyl acrylate (product name: Light Acrylate PO-A, manufactured by Kyoeisha Chemical Co., Ltd., monofunctional, boiling point: 140°C) (A-2): Dicyclopentanyl acrylate (product name: FA-513AS, manufactured by Resonac Co., Ltd., monofunctional, boiling point: 115°C) (A-3): (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl acrylate (product name: MEDOL-10, manufactured by Osaka Organic Chemical Industry Co., Ltd., monofunctional, boiling point: 100°C) (A-4) Phenoxydiethylene glycol acrylate (product name: NK Ester AMP-20GY, manufactured by Shin-Nakamura Chemical Co., Ltd., monofunctional, boiling point: 134°C) (A-5): Cyclic trimethylolpropane formal acrylate (product name: Viscoat #200, manufactured by Osaka Organic Chemical Industry Co., Ltd., monofunctional, boiling point: 115°C) (A-6): Dipropylene glycol diacrylate (product name: DPGDA, manufactured by Daicel Allnex Corporation, bifunctional, boiling point: 119 to 121°C) (A-7): Tripropylene glycol diacrylate (product name: TPGDA, manufactured by Daicel Allnex Corporation, bifunctional, boiling point: 200°C) (A-8): 1,6-Hexanediol diacrylate (product name: HDDA, manufactured by Daicel-Allnex Corporation, bifunctional, boiling point: 295°C) (A-9): 1,9-nonanediol diacrylate (product name: NK Ester A-NOD-N, manufactured by Shin-Nakamura Chemical Co., Ltd., bifunctional, boiling point: 342°C) (A-10): Tricyclodecane dimethanol diacrylate (product name: IRR 214-K, manufactured by Daicel-Allnex Corporation, bifunctional, boiling point: 397°C) (A-11): Tripropylene glycol diacrylate (product name: TPGDA, manufactured by Daicel Allnex Corporation, bifunctional, boiling point: 310°C) (A-12): Phosphoric acid-modified methacrylate (product name: EBECRYL-168, manufactured by Daicel-Allnex Corporation, 1.5 functional) (A-13): Urethane acrylate oligomer (product name: UN-6200, manufactured by Negami Chemical Industries, Ltd., bifunctional) (A-14): Bismaleimide compound (product name: BMI-1500, manufactured by Designer Molecules Inc., bifunctional)

[0069] (B) Radical polymerization initiator (B-1): Dicetyl peroxydicarbonate (Product name: Perkadox 24L, manufactured by Kayaku Nouryon Co., Ltd., 10-hour half-life temperature (T10): 48°C) (B-2): Dimyristyl peroxydicarbonate (Product name: Perkadox26, manufactured by Kayaku Nouryon Co., Ltd., 10-hour half-life temperature (T10): 41°C) (B-3): Bis(4-tert-butylcyclohexyl) peroxydicarbonate (product name: Peroyl TCP, 10-hour half-life temperature (T10): 40.8°C) (B-4): 1,1,3,3-tetrabutyl peroxydecanoate (product name: Luperox 810, manufactured by Arkema Yoshitomi Co., Ltd., 10-hour half-life temperature (T10): 44°C) (B-5): t-amyl peroxyneodecanoate (product name: Luperox 546, manufactured by Arkema Yoshitomi Co., Ltd., 10-hour half-life temperature (T10): 46°C) (B-6): bis(1-methyl-1-phenylethyl) peroxide (product name: Percumyl D, NOF Corporation, 10-hour half-life temperature (T10): 116.4°C)

[0070] ·(C) Inorganic particles (component (C)) -(C1) Conductive particles (C1-1): Silver powder 1 (product name: EA79613, manufactured by Metalor Technologies Japan Co., Ltd., average particle size (D50): 7 μm, BET specific surface area: 0.3 m 2 / g, tap density: 5.1g / cm 3 ) (C1-2): Silver powder 2 (product name: K 79121P, manufactured by Metalor Technologies Japan Co., Ltd., average particle size (D50): 7 μm, BET specific surface area: 2.3 m 2 / g, tap density: 2.7g / cm 3 ) -(C2) Insulating particles (C2-1): Silica particles (product name: SE5200SEE, manufactured by Admatechs Co., Ltd., average particle size (D50): 2 μm)

[0071] (D) Polymerization inhibitor (ingredient (D)) (D-1): N-nitroso-N-phenylhydroxylamine aluminum (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) (D-2): p-benzoquinone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

[0072] In the examples and comparative examples, the properties of the resin composition and the cured product obtained by curing the resin composition were measured as follows.

[0073] <Viscosity> The viscosity of each resin composition was measured at a rotation speed of 10 rpm using a Brookfield RVT viscometer (spindle: SC4-14 spindle, measurement temperature: 25° C.) The results are shown in Table 1.

[0074] <Mass ratio of organic matter before and after curing at 80℃ for 60 minutes [%]> On a glass substrate, two pieces of tape with a thickness of about 85 to 95 μm were attached in parallel at an interval of 20 mm, and each resin composition with a width of 20 mm x length of 65 mm x thickness of about 90 μm was printed between the two pieces of tape, and then cured for 60 minutes at 80 ° C. in an air convention oven. The mass ratio of the component obtained by subtracting the mass of inorganic particles from the total mass of the cured product after curing at 80 ° C. for 60 minutes to the mass of the component obtained by subtracting the mass of inorganic particles from the total mass of the curable resin composition before curing at 80 ° C. for 60 minutes (mass ratio of organic matter before and after curing at 80 ° C. for 60 minutes) [%] was calculated by the following formula. The results are shown in Table 1. M = [{m0-m1} / {m2-m3}] x 100 M: Mass ratio of organic matter before and after curing at 80℃ for 60 minutes [%] m0: Total mass of the cured product after curing at 80℃ for 60 minutes [g] m1: Mass of inorganic particles after curing at 80℃ for 60 minutes [g] m2: Total mass [g] of the curable resin composition before curing at 80°C for 60 minutes m3: Mass of inorganic particles before hardening at 80℃ for 60 minutes [g]

[0075] <Non-volatile content after curing at 80℃ for 60 minutes [%]> Using the samples for which the mass ratio of organic matter was determined before and after curing at 80° C. for 60 minutes, the weights of each resin composition before and after curing were calculated according to the following formula, and the non-volatile content Nv [%] of the curable resin composition after curing at 80° C. for 60 minutes was determined. The results are shown in Table 1. Nv=[{m c -m a} / {m b -ma}]×100 Nv: Non-volatile content after curing at 80℃ for 60 minutes [%] m a : Mass of glass substrate [g] m b : Total mass of the test piece after the resin composition is printed on the glass substrate [g] m c : Total mass [g] of the test piece after printing the resin composition on a glass substrate and treating it at 80°C for 60 minutes

[0076] <Cracks after curing at 80℃ for 60 minutes> A Ni-plated copper substrate and a resin substrate (PC, LCP, etc.) were attached to a Ni-plated copper substrate with double-sided tape so that a gap of 1000 μm was formed between the two substrates to prepare a test specimen. A resin composition was applied to the 1000 μm gap of the prepared test specimen, and the specimen was cured at 80° C. for 60 minutes in an air convention oven. The cured portion of the resin composition of the test specimen was observed with an optical microscope, and a test specimen in which a crack was confirmed in the cured portion of the resin composition was evaluated as having a crack, and a test specimen in which a crack was not confirmed in the cured portion of the resin composition was evaluated as having no crack. The results are shown in Table 1. FIG. 1 is an optical microscope photograph (magnification 400 times) of the cured product obtained by curing the resin compositions of Example 5 and Comparative Example 1 at 80° C. for 60 minutes.

[0077] <Resistivity value> On a glass substrate, two tapes of about 85 to 95 μm thickness were attached in parallel at an interval of 3 mm, and each resin composition of width: 3 mm × length: 50 mm × thickness: about 90 μm was printed between the two tapes, and then cured in an air convention oven at 80 ° C. for 60 minutes. The film thickness of the obtained cured film was measured by a surface roughness shape measuring instrument (model number: Surfcom 1500SD-2) manufactured by Tokyo Seimitsu Co., Ltd., and the resistance value was measured by a four-terminal method using a digital multimeter (model number: 2001) manufactured by TFF Keithley Instruments Co., Ltd., and the volume resistivity was calculated and used as the specific resistance value. Note that the measurement was not possible for Comparative Example 8. Measurement was not performed for Examples 16 and 17, which do not contain conductive particles. The resistivity is 1.0×10 -2It is preferable that the resistivity is less than Ω·cm. The results are shown in Table 1.

[0078] [Table 1-1]

[0079] [Table 1-2]

[0080] [Table 1-3]

[0081] In each of the resin compositions of Examples 1 to 17, the mass ratio of organic matter before and after curing at 80° C. for 60 minutes was 70 mass % or more, and no cracks were generated in the cured product after curing at 80° C. for 60 minutes. In the resin compositions of Comparative Examples 1 to 7 and 9, the mass ratio of organic matter before and after curing at 80° C. for 60 minutes was less than 70 mass %, and cracks occurred in the cured products after curing at 80° C. for 60 minutes. The resin composition of Comparative Example 8 was not completely cured by heating at 80° C. for 60 minutes, and the mass ratio of the organic matter before and after curing at 80° C. for 60 minutes could not be obtained. It can be seen that the parameter of the mass ratio of the organic matter before and after curing at 80° C. for 60 minutes can also be used as a measure of low-temperature curing properties. [Industrial Applicability]

[0082] The present invention relates to a curable resin composition that can be cured under low temperature conditions and that suppresses the occurrence of cracks after curing, and is extremely useful as an adhesive or sealant suitable for use in the production of semiconductor devices and electronic components.

Claims

1. (A) a radically polymerizable curable compound; (B) a radical polymerization initiator; (C) inorganic particles; A curable resin composition comprising: the mass ratio of the components obtained by subtracting the mass of the inorganic particles from the total mass of the cured product after curing at 80°C for 60 minutes to the mass of the components obtained by subtracting the mass of the inorganic particles from the total mass of the curable resin composition before curing at 80°C for 60 minutes is 70 mass% or more; Curable resin composition.

2. The curable resin composition according to claim 1, wherein the radically polymerizable curable compound (A) comprises a (meth)acrylate compound having a boiling point of 200°C or higher.

3. 2. The curable resin composition according to claim 1, wherein the radically polymerizable curable compound (A) comprises a monofunctional (meth)acrylate compound and a polyfunctional (meth)acrylate compound having a boiling point of 200°C or higher.

4. 2. The curable resin composition according to claim 1, wherein the content of the monofunctional (meth)acrylate compound is 0 to 45 parts by mass per 100 parts by mass of the component (A).

5. The curable resin composition according to claim 1 , wherein the radically polymerizable curable compound (A) comprises a bismaleimide compound.

6. The curable resin composition according to claim 1 , wherein the radical polymerization initiator (B) is an organic peroxide.

7. The curable resin composition according to claim 1, wherein the radical polymerization initiator (B) is an organic peroxide having a 10-hour half-life temperature of 70°C or lower.

8. The curable resin composition according to claim 1 , wherein the radical polymerization initiator (B) is an organic peroxide having a dicarbonate structure.

9. The curable resin composition according to claim 1 , wherein the (C) inorganic particles include conductive particles.

10. The curable resin composition according to claim 1 , wherein the (C) inorganic particles include silver particles.

11. The curable resin composition according to claim 1 , further comprising (D) a polymerization inhibitor.

12. An adhesive or sealant comprising the curable resin composition according to any one of claims 1 to 11.

13. A cured product obtained by curing the curable resin composition according to any one of claims 1 to 11.

14. A semiconductor device or electronic part comprising the cured product according to claim 13.

15. An electronic component for a camera module, comprising the cured product according to claim 13.

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