Resin compositions and adhesives

Abstract

The present invention addresses the problem of providing a resin composition and an adhesive that have a high moisture resistance after heat curing. The present invention provides a resin composition including (A) a (meth)acrylate compound, (B) a polythiol compound, (C) a cyclic carbodiimide compound, (D) a curing catalyst, and (E) a coupling agent.

Description

[Technical Field]

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

[0002] Adhesives that are temporarily fixed by ultraviolet (UV) irradiation and then permanently cured by heat are used in many fields (for example, Patent Documents 1 and 2), and are particularly popular in image sensor module applications. Image sensor modules are used as camera modules in mobile phones and smartphones. Since the adhesives used in the manufacture of image sensor modules are also used to prevent moisture from entering the electronic components, they are also required to exhibit sufficient moisture resistance.

[0003] Patent Document 3 discloses a photocurable and thermosetting resin composition that suppresses the decrease in adhesive strength in a humidity resistance test of the cured resin composition and has a sufficiently long pot life, characterized in that it contains (A) an acrylic resin, (B) a polyfunctional nitrogen-containing heterocyclic compound having a specific formula, (C) a latent curing agent, (D) a radical polymerization inhibitor, and (E) an anionic polymerization inhibitor. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2009-51954 [Patent Document 2] International Publication No. 2005 / 052021 [Patent Document 3] International Publication No. 2016 / 143777 [Overview of the project] [Problems that the invention aims to solve]

[0005] As image sensors become larger in the future, the use of adhesives will increase in areas that are shaded by components and not exposed to ultraviolet light, such as the connection points between the support and the substrate. Therefore, improvements in moisture resistance will be required not only after UV curing and heat curing of adhesives, but also after heat curing alone. Patent document 3 describes how to suppress the decrease in adhesive strength in moisture resistance tests of resin compositions after UV curing and heat curing, but it does not describe moisture resistance after heat curing alone.

[0006] Therefore, the present invention aims to provide a resin composition and adhesive that have high moisture resistance after heat curing. [Means for solving the problem]

[0007] The specific means for solving the aforementioned problems are as follows: The first embodiment of the present invention is the following resin composition. (1)(A)(meth)acrylate compound, (B) Polythiol compounds, (C) Cyclic carbodiimide compound, (D) curing catalyst, and (E) Coupling agent A resin composition containing the following: (2)(C) The resin composition according to (1) above, wherein the content of the cyclic carbodiimide compound is 5% by mass or more with respect to the total mass of the resin composition. (3)(E) The resin composition according to (1) or (2) above, wherein the coupling agent comprises an epoxy coupling agent containing an epoxy group. (4) The resin composition according to any one of (1) to (3), further comprising (F) a photoinitiator. (5) The resin composition according to any one of the above items (1) to (4), further comprising (G) an inorganic filler and (H) a stabilizer.

[0008] A second embodiment of the present invention is (6) an adhesive comprising the resin composition described in any of (1) to (5) above. The third embodiment of the present invention is a cured product obtained by curing the resin composition according to any one of (1) to (5) above, or the adhesive according to (6) above. The fourth embodiment of the present invention is a semiconductor device including the cured product according to (7) above. The fifth embodiment of the present invention is an electronic component including the semiconductor device according to (8) above.

Advantages of the Invention

[0009] According to the first embodiment of the present invention, a resin composition having high moisture resistance after thermosetting can be obtained. Further, according to the second embodiment of the present invention, an adhesive having high moisture resistance after thermosetting can be obtained. Furthermore, according to the third embodiment of the present invention, a cured product having high moisture resistance can be obtained. According to the fourth embodiment of the present invention, a semiconductor device including a cured product having high moisture resistance can be obtained. According to the fifth embodiment of the present invention, an electronic component including a semiconductor device having high moisture resistance can be obtained.

Modes for Carrying Out the Invention

[0010] [Resin Composition] The resin composition which is the first embodiment of the present invention (A) (Meth)acrylate compound, (B) Polythiol compound, (C) Cyclic carbodiimide compound, (D) Curing catalyst, and (E) Coupling agent is included. According to this embodiment, a resin composition having high moisture resistance after thermosetting can be obtained.

[0011] (A) (Meth)acrylate compound The resin composition of this embodiment contains (A) a (meth)acrylate compound (hereinafter also referred to as "component (A)"). The (A) (meth)acrylate compound can impart transparency and appropriate hardness to the cured resin composition. The (meth)acrylate compound that is component (A) is not particularly limited as long as it has one or more (meth)acryloyl groups. Considering the need to ensure heat resistance, compounds having two or more (meth)acryloyl groups are preferred, compounds having two to six (meth)acryloyl groups are more preferred, and compounds having two (meth)acryloyl groups are even more preferred. Furthermore, in order to adjust viscosity and cured product properties (such as adhesive strength and flexibility), in addition to compounds having two (meth)acryloyl groups, compounds having one (meth)acryloyl group can also be used. Ideally, from the viewpoint of moisture resistance, component (A) should have a structure that does not contain hydrolyzable substructures such as ester bonds within the molecule. However, in this embodiment, by including the cyclic carbodiimide compound (C), hydrolysis of ester bonds and the like is suppressed, and even if the molecular chain is broken by hydrolysis, it can be recombined, so it may contain ester bonds and the like within the molecule.

[0012] (A) Examples of (meth)acrylate compounds include diacrylate and / or dimethacrylate of tris(2-hydroxyethyl)isocyanurate; tris(2-hydroxyethyl)isocyanurate ofTriacrylate and / or trimethacrylate; trimethylolpropane triacrylate and / or trimethacrylate, or their oligomers; pentaerythritol triacrylate and / or trimethacrylate, or their oligomers; polyacrylate and / or polymethacrylate of dipentaerythritol; tris(acryloxyethyl) isocyanurate; caprolactone-modified tris(acryloxyethyl) isocyanurate; caprolactone-modified tris(methacryloxyethyl) isocyanurate; alkyl-modified dipentaerythritol polyacrylate and / or polymethacrylate; polyacrylate and / or polymethacrylate of caprolactone-modified dipentaerythritol; ethoxy Examples include bisphenol A diacrylate and / or ethoxylated bisphenol A dimethacrylate; dihydrocyclopentadiethyl acrylate and / or dihydrocyclopentadiethyl methacrylate; as well as polyester acrylate and / or polyester methacrylate, dimethylol-tricyclodecane diacrylate, poly(meth)acrylate of ditrimethylolpropane, polyurethane having two or more (meth)acryloyl groups in one molecule, polyester having two or more (meth)acryloyl groups in one molecule, phenoxyethyl acrylate, isobornyl acrylate, phenoxydiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl acrylate, etc. From the viewpoint of reactivity, it is preferable that component (A) is substantially free of methacrylate compounds and is an acrylate compound. (A) The (meth)acrylate compound may be any one of the (meth)acrylate compounds described above, or two or more may be used in combination.

[0013] (A) Component (A) preferably has a viscosity of 0.01 to 80 Pa·s, from the viewpoint of resin composition preparation and dispensability. In this specification, viscosity refers to the value measured at a measurement temperature of 25°C using an appropriate viscometer depending on the viscosity range.

[0014] Examples of commercially available components (A) include polyester acrylate (product name: EBECRYL810) manufactured by Daicel Ornex Co., Ltd., polyester acrylate (product name: M7100) manufactured by Toagosei Co., Ltd., and dimethylol-tricyclodecanediaacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoeisha Chemical Co., Ltd. Component (A) may be used individually or in combination of two or more.

[0015] (A) The content of component (A) is preferably 10 to 70% by mass, and more preferably 20 to 60% by mass, relative to the total mass of the resin composition, from the viewpoint of the adhesive strength of the resin composition.

[0016] (B) Polythiol compounds The resin composition of this embodiment contains (B) a polythiol compound (hereinafter also referred to as "component (B)"). The (B) polythiol compound imparts elasticity and moisture resistance to the resin composition. Component (B) is not particularly limited as long as it has two or more thiol groups. Ideally, from the viewpoint of moisture resistance, it is preferable that component (B) has a structure that does not have hydrolyzable substructures such as ester bonds in the molecule. However, in this embodiment, by including (C) a cyclic carbodiimide compound, hydrolysis of ester bonds and the like is suppressed, and even if the molecular chain is broken by hydrolysis, it can be recombined, so it may have ester bonds and the like in the molecule.

[0017] Examples of polythiol compounds having ester bonds in their molecules include pentaerythritol tetrakis(3-mercaptopropionate), trimethylolpropanetris(3-mercaptopropionate), and dipentaerythritol hexakis(3-mercapto Examples include propionate, pentaerythritol tetrakis(3-mercaptobutyrate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropanetris(3-mercaptobutyrate), and trimethylolethanetris(3-mercaptobutyrate).

[0018] Commercially available products of component (B) having an ester bond in the molecule include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (manufactured by SC Organic Chemicals Co., Ltd.: TEMPIC), pentaerythritol tetrakis(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.: PEMP), and tetraethylene glycol bis(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.). Examples include: Chemical Co., Ltd. (EGMP-4), dipentaerythritol hexakis(3-mercaptopropionate) (SC Organic Chemicals Co., Ltd.: DPMP), pentaerythritol tetrakis(3-mercaptobutyrate) (Showa Denko K.K.: Karenz MT® PE1), and 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (Showa Denko K.K.: Karenz MT® NR1).

[0019] In this embodiment, a (B) polythiol compound that does not have an ester bond in the molecule can also be used. Examples of such (B) components include glycoluryl compounds represented by the following general formula (1).

[0020] [ka]

[0021] In general formula (1), R 6 , 2n , 4、 , n , 5 , 2n , 4 , 6 , 3 , 5 , n , and R 2 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a phenyl group. n is an integer from 0 to 10.

[0022] Also, the component (B) may be a compound represented by the following chemical formula (2) or chemical formula (3). <00​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​SH (n is 2-6). From the viewpoint of curability, n of the polythiol compound of component (B) represented by general formula (4) is preferably 2-4. Furthermore, from the viewpoint of balancing the properties of the cured product and the curing speed, it is more preferable that this polythiol compound be a mercaptopropyl group with n = 3. Component (B) represented by general formula (4) has a sufficiently flexible skeleton itself, making it effective when it is desired to lower the elastic modulus of the cured product. By adding component (B) represented by general formula (4), the elastic modulus of the cured product can be controlled, thereby increasing the adhesive strength (especially the peel strength) after curing.

[0029] Examples of commercially available components (B) that do not have ester bonds in their molecules include thiol glycol uryl derivatives manufactured by Shikoku Chemicals (product name: TS-G (corresponding to chemical formula (2), thiol equivalent: 100 g / eq), C3 TS-G (corresponding to chemical formula (3), thiol equivalent: 114 g / eq)) and thiol compounds manufactured by SC Organic Chemicals (product name: PEPT (corresponding to general formula (4), thiol equivalent: 124 g / eq)).

[0030] (B) Component may be any one type, or two or more types may be used in combination. A (B) component having an ester bond in the molecule and a (B) component not having an ester bond in the molecule may be used in combination.

[0031] When a polythiol compound having an ester bond in its molecule is used as component (B), this ester bond undergoes hydrolysis to generate carboxyl groups and hydroxyl groups. These functional groups react with the cyclic carbodiimide compound (C), creating polar groups in the resin composition, which improves the adhesive strength under high humidity. In one embodiment, the content of the polythiol compound having an ester bond in its molecule is preferably less than 60 parts by mass, more preferably less than 70 parts by mass, and even more preferably less than 80 parts by mass, per 100 parts by mass of component (B).

[0032] Furthermore, in one embodiment, from the viewpoint of long-term moisture resistance reliability, it is preferable that component (B) does not have an ester bond. From the viewpoint of maintaining the shear strength of the resin composition under high humidity after curing for a long period of time, it is preferable that the component (B) contains 70 to 100 parts by mass of a compound that does not have an ester bond per 100 parts by mass of component (B). The content of the polythiol compound that does not have an ester bond in component (B) is more preferably 80 to 100 parts by mass, and even more preferably 90 to 100 parts by mass, per 100 parts by mass of component (B).

[0033] In the resin composition, the ratio of [(B) component thiol group equivalents] / [(A) component (meth)acryloyl group equivalents] is preferably 0.5 to 2.0, and more preferably 0.5 to 1.5. In this specification, functional group equivalents such as (meth)acryloyl equivalents and thiol equivalents represent the molecular weight of the compound per functional group, and functional group equivalent numbers such as (meth)acryloyl group equivalents and thiol group equivalents represent the number of functional groups (equivalents) per mass (amount charged) of compound. Theoretically, the thiol equivalent of component (B) is the molecular weight of component (B) divided by the number of thiol groups in one molecule. The actual thiol equivalent can be determined, for example, by determining the thiol value by potentiometric measurement. (A) The (meth)acryloyl equivalent of a (meth)acrylate compound is theoretically equal to the molecular weight of the (meth)acrylate compound divided by the number of acryloyl groups (or methacryloyl groups) in one molecule. The actual (meth)acryloyl equivalent can be measured, for example, by NMR. The number of (meth)acryloyl group equivalents of component (A) is the number of (meth)acryloyl groups (equivalents) per unit mass (amount charged) of component (A), and is the quotient obtained by dividing the mass (g) of the (meth)acrylate compound by the (meth)acryloyl equivalent of that (meth)acrylate compound (if multiple (meth)acrylate compounds are included, it is the sum of such quotients for each (meth)acrylate compound). The thiol group equivalent number of component (B) is the number of thiol groups (equivalents) per unit mass (amount charged) of component (B), and is the quotient obtained by dividing the mass (g) of the thiol compound (B) by the thiol equivalent of that thiol compound (if multiple thiol compounds are included, it is the sum of such quotients for each thiol compound). Setting [(B) thiol group equivalent number] / [(A) (meth)acryloyl group equivalent number] to the range of 0.5 to 2.0 allows for sufficient reaction between acryloyl groups and thiol groups, thereby enabling the formation of molecular crosslinks and making it easier to achieve high adhesive strength.

[0034] The resin composition of this embodiment is a resin composition containing (A) a (meth)acrylate compound as the main component prepolymer compound. The resin composition of this embodiment may contain other prepolymer compounds, such as epoxy compounds, but embodiments in which the amount of epoxy compound is greater than the amount of (A) a (meth)acrylate compound are not included in this embodiment. For example, embodiments in which [(B) thiol group equivalents] / [epoxy group equivalents of epoxy compound] is 10.0 or less are not included. Conventionally, cured products of resin compositions rich in (meth)acrylate compounds as the main component prepolymer compound have had more serious problems with moisture resistance than resin compositions rich in epoxy compounds, especially when hydrolyzable ester bonds are formed in the polymer molecule. According to the resin composition of this embodiment, a cured product with high moisture resistance can be obtained even under the more stringent conditions of (meth)acrylate compound-rich resin compositions. Theoretically, the epoxy equivalent of an epoxy compound is the molecular weight of the epoxy compound divided by the number of epoxy groups in one molecule. The actual epoxy equivalent can be determined by the method described in JIS K7236. The epoxy group equivalent number of an epoxy compound is the number of epoxy groups (equivalent number) per unit mass (amount charged) of the epoxy compound, and is the quotient obtained by dividing the mass (g) of the epoxy compound by the epoxy equivalent of that epoxy compound (if multiple epoxy compounds are included, it is the sum of such quotients for each epoxy compound).

[0035] (C) Cyclic carbodiimide compound The resin composition of this embodiment contains (C) a cyclic carbodiimide compound (hereinafter also referred to as "component (C)"). The cyclic carbodiimide compound has a cyclic structure. The cyclic structure has one carbodiimide group (-N=C=N-), and its primary and secondary nitrogen atoms are bonded by a bonding group. There is only one carbodiimide group in a single cyclic structure. The number of atoms in the cyclic structure is preferably 8 to 50, more preferably 10 to 30, and even more preferably 10 to 20. The cyclic carbodiimide compound may have multiple cyclic structures.

[0036] The cyclic carbodiimide compound used in this embodiment is preferably a cyclic carbodiimide compound represented by the following general formula (5).

[0037] [ka]

[0038] In general formula (5), Ar 1 ~Ar 4 Each of these is an aromatic group independently. The aromatic group may be substituted with an alkyl or aryl group having 1 to 6 carbon atoms. Examples of aromatic groups include phenylene groups and naphthalene diyl groups.

[0039] Ar 1 ~Ar 4 A phenyl group is preferable because it results in good film-forming properties.

[0040] X is a divalent or tetravalent group. When X is divalent, q is 0, and when X is tetravalent, q is 1. Preferably, X is one of the following formulas (5-i), (5-ii), (5-iii), (5-iv), (5-v), (5-vi), or (5-vii).

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] In formula (5-i), n is an integer between 1 and 6. Examples of the group in (5-i) include the methylene group, ethylene group, 1,3-propylene group, 1,4-butylene group, 1,5-pentane group, and 1,6-hexane group.

[0046] Furthermore, in equations (5-ii) to (5-v), m and n are independent integers between 0 and 4. The methylene group with m=0 represents a single bond.

[0047] Also, in equation (5-vi), R 1 and R 2 Each of these is independently an alkyl group or aryl group having 1 to 6 carbon atoms. Examples of alkyl groups having 1 to 6 carbon atoms include methyl group, ethyl group, n-propyl group, sec-propyl group, iso-propyl group, n-butyl group, tert-butyl group, sec-butyl group, iso-butyl group, n-pentyl group, sec-pentyl group, iso-pentyl group, n-hexyl group, sec-hexyl group, iso-hexyl group, etc.

[0048] Among the cyclic carbodiimide compounds represented by formula (5), the compound represented by the following general formula (5-0) is preferred.

[0049] [ka]

[0050] In general formula (5-0), X is preferably one of the above-mentioned (5-i), (5-ii), (5-iii), (5-iv), (5-v), (5-vi), and (5-vii). Y and Z are each independently substituents other than alkyl groups having 1 to 6 carbon atoms or phenyl groups. Conventionally known substituents can be applied as alkyl groups having 1 to 6 carbon atoms or substituents other than phenyl groups. Examples include alkyl groups having 7 or more carbon atoms, aryl groups other than phenyl groups, alkoxy groups, hydroxyl groups, aldehyde groups, acyl groups, carboxyl groups, ester groups, nitro groups, amino groups, sulfo groups, sulfonyloxy groups, halogeno groups, silyl groups, vinyl groups, fluoroalkyl groups, cyano groups, isonitrile groups, amide groups, imide groups, thiol groups, etc.

[0051] In particular, compounds represented by the following chemical formula (5-1) or the following chemical formula (5-2) are preferred.

[0052] [ka]

[0053] [ka]

[0054] [Mechanism for improving moisture resistance] (C) The mechanism of moisture resistance improvement by cyclic carbodiimide compounds is not limited to the following, but is presumed to be: Hydrolyzable substructures such as ester bonds are found in some (A) (meth)acrylate compounds and some (B) polythiol compounds. For example, ester bonds hydrolyze to produce carboxylic acids and alcohols. As shown below, the carbodiimide group reacts with the carboxylic acid produced by hydrolysis and has the effect of suppressing hydrolysis by capturing the acid that acts as a catalyst for the decomposition reaction.

[0055] [ka]

[0056] However, polycarbodiimide compounds that are not (C) cyclic carbodiimide compounds have a carbodiimide group that reacts with carboxylic acid to suppress hydrolysis, but when heat is subsequently applied, decomposition occurs, generating isocyanate gas, which is known to be highly irritating and sensitizing.

[0057] [ka]

[0058] On the other hand, in (C) cyclic carbodiimide compounds, when the carbodiimide groups present in the cyclic skeleton react with carboxylic acids, the bonds do not break even when heat is applied afterward, and the resulting isocyanates remain in the polymer via the cyclic skeleton. The isocyanate groups form bonds with each other or with thiol groups. As a result, polymer chains that have been broken by hydrolysis can recombine with other polymer chains, thus maintaining or strengthening adhesive strength. Consequently, the moisture resistance improvement effect of (C) cyclic carbodiimide compounds is considered to be greater than that of polycarbodiimide compounds.

[0059] [ka]

[0060] Furthermore, (C) cyclic carbodiimide compounds do not generate isocyanate gas when heated, thus enabling the creation of void-free cured films. Voids in the cured film can lead to crack propagation and increased moisture permeability, thus degrading reliability; therefore, it is preferable to have no voids in the cured film.

[0061] (C) The content of the cyclic carbodiimide compound is preferably 5% by mass or more, more preferably 8% by mass or more, and more preferably 10% by mass or more, based on the total mass of the resin composition. (C) There is no particular upper limit to the content of the cyclic carbodiimide compound, but from the viewpoint of viscosity, for example, it is 60% by mass or less, 50% by mass or less, and 40% by mass or less.

[0062] [Method for producing cyclic carbodiimide compounds] In this embodiment, the method for producing the cyclic carbodiimide compound is not particularly limited and can be produced by conventionally known methods (for example, the methods described in International Publication No. 2010 / 071211 and Japanese Patent Application Publication No. 2011-256139). Examples include methods of production via an isocyanate from an amine, a isothiocyanate from an amine, a triphenylphosphine from an amine, a urea from an amine, a thiourea from an amine, a carboxylic acid from an isocyanate, and a lactam derivative.

[0063] Commercially available cyclic carbodiimide compounds may be used.

[0064] (D) Curing catalyst The resin composition of this embodiment includes (D) a curing catalyst (hereinafter also referred to as "component (D)"). The curing catalyst (D) used in this embodiment is not particularly limited as long as it is a curing catalyst of a (meth)acrylate compound, and known ones can be used, but it is preferable that it be a latent curing catalyst. The latent curing catalyst of component (D) is a compound that is inert at room temperature and becomes activated by heating to function as a curing catalyst, and examples include imidazole compounds that are solid at room temperature; solid-disperse amine adduct-type latent curing catalysts such as reaction products of amine compounds and epoxy compounds (amine-epoxy adduct systems); and reaction products of amine compounds and isocyanate compounds or urea compounds (urea-type adduct systems).

[0065] Examples of imidazole compounds that are solid at room temperature include 2-heptadecylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4-benzyl-5-hydroxymethylimidazole, 2,4-diamino-6-(2-methylimidazolyl-(1))-ethyl-S-triazine, and 2,4-diamino-6-(2′-methylimidazolyl-( 1)′)-ethyl-S-triazine isocyanuric acid adduct, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl-2-phenylimidazole trimellitate, N-(2-methylimidazolyl-1-ethyl)urea, N,N′-(2-methylimidazolyl-(1)-ethyl)-adductoryl Po Examples include amides, but this list is not limited to these.

[0066] Epoxy compounds used as raw materials for the production of solid-disperse amine adduct-type latent curing catalysts (amine-epoxy adduct systems) include, for example, polyglycidyl ethers obtained by reacting polyhydric phenols such as bisphenol A, bisphenol F, catechol, and resorcinol, or polyhydric alcohols such as glycerin and polyethylene glycol with epichlorohydrin; glycidyl ether esters obtained by reacting hydroxycarboxylic acids such as p-hydroxybenzoic acid and β-hydroxynaphthoic acid with epichlorohydrin; phthalic acid, terephthalate. Examples include, but are not limited to, polyglycidyl esters obtained by reacting polycarboxylic acids such as glycidyl acid with epichlorohydrin; glycidylamine compounds obtained by reacting epichlorohydrin with 4,4′-diaminodiphenylmethane or m-aminophenol; and polyfunctional epoxy compounds such as epoxidized phenol novolac resins, epoxidized cresol novolac resins, and epoxidized polyolefins, as well as monofunctional epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, and glycidyl methacrylate.

[0067] The amine compound used as another raw material for the production of solid-disperse amine adduct-type latent curing catalysts is one that has at least one active hydrogen atom capable of addition reaction with an epoxy group, and at least one functional group selected from primary, secondary, and tertiary amino groups. Examples of such amine compounds are shown below, but are not limited to these. For example, aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, and 4,4′-diamino-dicyclohexylmethane; aromatic amine compounds such as 4,4′-diaminodiphenylmethane and 2-methylaniline; heterocyclic compounds containing nitrogen atoms such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, and piperazine; etc., but are not limited to these.

[0068] Furthermore, compounds having a tertiary amino group in the molecule are particularly useful as raw materials for latent curing catalysts with excellent curing acceleration ability. Examples of such compounds include amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, and N-methylpiperazine, as well as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, and 2-phenyl Primary or secondary amines having a tertiary amino group in the molecule, such as imidazole compounds like midazole; 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy -3-butoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazole, 2-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol, N-β-hydroxyethylmorpholine, 2-dimethylaminoethanethiol, 2-mercaptopyridine, 2-benzoimi Examples include, but are not limited to, alcohols, phenols, thiols, carboxylic acids, and hydrazides having a tertiary amino group in their molecule, such as dazole, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 4-mercaptopyridine, N,N-dimethylaminobenzoic acid, N,N-dimethylglycine, nicotinic acid, isonicotinic acid, picolinic acid, N,N-dimethylglycine hydrazide, N,N-dimethylpropionic acid hydrazide, nicotinic acid hydrazide, and isonicotinic acid hydrazide.

[0069] In addition to the solid-disperse amine adduct-type latent curing catalyst, isocyanate compounds used as another raw material include, for example, monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, and benzyl isocyanate; polyfunctional isocyanate compounds such as hexamethylene diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, diphenylmethane-4,4′-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, paraphenylene diisocyanate, 1,3,6-hexamethylene triisocyanate, and bicycloheptane triisocyanate; and compounds containing terminal isocyanate groups obtained by the reaction of these polyfunctional isocyanate compounds with active hydrogen compounds. Examples of such terminal isocyanate group-containing compounds include, but are not limited to, addition compounds having terminal isocyanate groups obtained by the reaction of toluene diisocyanate and trimethylolpropane, and addition compounds having terminal isocyanate groups obtained by the reaction of toluene diisocyanate and pentaerythritol.

[0070] Examples of urea compounds include, but are not limited to, urea and thiourea.

[0071] The solid-disperse latent curing catalysts that can be used in this embodiment are, for example, (a) a two-component mixture of an amine compound and an epoxy compound, (b) a three-component mixture of these two components and an active hydrogen compound, or (c) a two- or three-component mixture of an amine compound and an isocyanate compound and / or a urea compound. These can be easily prepared by taking and mixing each component, reacting them at a temperature from room temperature to 200°C, then cooling and solidifying them before pulverizing, or by reacting them in a solvent such as methyl ethyl ketone, dioxane, or tetrahydrofuran, removing the solvent, and then pulverizing the solid component.

[0072] Representative examples of commercially available solid-disperse latent curing catalysts include, as amine-epoxy adduct systems (amine adduct systems), "Amicure PN-23" (Ajinomoto Fine Techno Co., Ltd.), "Amicure PN-40" (Ajinomoto Fine Techno Co., Ltd.), "Amicure PN-50" (Ajinomoto Fine Techno Co., Ltd.), "Hardener X-3661S" (ACR Co., Ltd.), "Hardener X-3670S" (ACR Co., Ltd.), "NovaCure HX-3742" (Asahi Kasei E-Materials Co., Ltd.), "NovaCure HX-3721" (Asahi Kasei E-Materials Co., Ltd.), "NovaCure HXA9322HP" (Asahi Kasei E-Materials Co., Ltd.), and "FXR1121" (T&K Co., Ltd.). Examples include TOKA products, and as for urea-type adduct systems, examples include "Fujicure FXE-1000" (T&K TOKA product name) and "Fujicure FXR-1030" (T&K TOKA product name), but the product is not limited to these. (D) One of the components may be used, or two or more may be used in combination.

[0073] (D) The content of the curing catalyst is preferably 0.1 to 40% by mass, and more preferably 1 to 20% by mass, relative to the total mass of the resin composition, from the viewpoint of the curing speed of the resin composition and the pot life.

[0074] (E) Coupling agent The resin composition of this embodiment contains (E) a coupling agent (hereinafter also referred to as "component (E)"). The coupling agent has two or more different functional groups in its molecule, one of which is a functional group that chemically bonds with an inorganic material, and the other is a functional group that chemically bonds with an organic material. The inclusion of the coupling agent in the resin composition improves the adhesion of the resin composition to a substrate or the like.

[0075] In this embodiment, it was found that the presence of a coupling agent (E) is also necessary for improving moisture resistance. The reasons for this are not limited to the following, but are thought to be as follows: When water, heat, ions, vibration / load, etc. are applied to the metal material bonding area, the adhesive strength decreases. In particular, water is positioned as an extremely important degradation factor, and when water molecules penetrate and accumulate at the metal-adhesive interface, the effects of other degradation factors such as heat, ions, vibration / load, etc. are further accelerated, leading to the eventual failure of the bonding area. In this embodiment, it is thought that the coupling agent (E) suppresses the penetration of water into the bonding interface, thereby improving moisture resistance.

[0076] (E) Examples of coupling agents include, but are not limited to, silane coupling agents, aluminum coupling agents, and titanium coupling agents, depending on the type of functional group that chemically bonds with the inorganic material.

[0077] Examples of coupling agents include, but are not limited to, various types of coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto-based coupling agents, depending on the type of functional group that chemically bonds with the organic material. Among these, epoxy coupling agents containing epoxy groups, methacrylic coupling agents containing methacryloyl groups, acrylic coupling agents containing acryloyl groups, and mercapto-based coupling agents containing thiol groups are preferred for reasons such as improved moisture resistance. In particular, epoxy coupling agents containing epoxy groups are more preferred from the viewpoint of achieving both heat curing and moisture resistance after UV + heat curing.

[0078] Specific examples of epoxy silane coupling agents include 3-glycidoxypropyltrimethoxysilane (product name: KBM403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropyltriethoxysilane (product name: KBE-403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldiethoxysilane (product name: KBE-402, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldimethoxysilane (product name: KBM402, manufactured by Shin-Etsu Chemical Co., Ltd.), 8-glycidoxyoctyltrimethoxysilane (product name: KBM-4803, manufactured by Shin-Etsu Chemical Co., Ltd.), and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (product name: Sylace S530, manufactured by JNC Corporation).

[0079] Specific examples of methacryl-based silane coupling agents include 3-methacryloxypropyltrimethoxysilane (product name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropylmethyldimethoxysilane (product name: KBM502, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropylmethyldiethoxysilane (product name: KBE502, manufactured by Shin-Etsu Chemical Co., Ltd.), and 3-methacryloxypropyltriethoxysilane (product name: KBE503, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0080] Specific examples of acrylic silane coupling agents include 3-acryloxypropyltrimethoxysilane (product name: KBM-5103, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0081] Specific examples of mercapto-silane coupling agents include 3-mercaptopropyltrimethoxysilane (product name KBM803, manufactured by Shin-Etsu Chemical Co., Ltd.) and 3-mercaptopropylmethyldimethoxysilane (product name KBM802, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0082] The coupling agent may be any one type, or two or more types may be used in combination.

[0083] The content of component (E) is preferably 0.1 to 10% by mass, more preferably 0.2 to 7% by mass, relative to the total mass of the resin composition. amount% More preferably, it is 0.3 to 5% by mass.

[0084] (F) Photoinitiator The resin composition of this embodiment may contain (F) a photoinitiator (hereinafter also referred to as "component (F)") to the extent that it does not impair the effects of the present invention. In this embodiment, a photoinitiator that generates radicals upon UV absorption is preferred.

[0085] Examples of photoinitiators include alkylphenone-based photoinitiators and acylphosphine oxide-based photoinitiators. body Examples include 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-one, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one. The resin composition of this embodiment is photocurable and thermocurable, but UV curing can be accelerated by using a photoinitiator.

[0086] (F) The content of component (F) is preferably 0.1 to 10 parts by mass, and more preferably 0.2 to 8 parts by mass, per 100 parts by mass of the (meth)acrylate compound, from the viewpoint of UV curability.

[0087] (G) Inorganic filler The resin composition of this embodiment may contain (G) an inorganic filler (hereinafter also referred to as "component (G)") to the extent that it does not impair the effects of the present invention. Inorganic fillers consist of granular bodies formed from inorganic materials. Suitable inorganic materials include silica, 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, and boron nitride. One or more inorganic fillers may be used. Silica fillers are preferred as the inorganic filler. Amorphous silica is preferred.

[0088] The shape of the inorganic filler is not particularly limited and can be spherical, flaky, needle-shaped, or amorphous. From the viewpoint of fluidity, a spherical shape is preferred.

[0089] The average particle size of the inorganic filler is preferably 0.01 to 15 μm, and more preferably 0.01 to 10 μm. The maximum particle size of the inorganic filler is preferably 50 μm or less, and more preferably 30 μm or less.

[0090] In this specification, the average particle size is the particle size at 50% of the cumulative value in the volume-based particle size distribution, measured by laser diffraction-scattering. The maximum particle size is the largest particle size in the volume-based particle size distribution, measured by laser diffraction-scattering.

[0091] (G) The inorganic filler content is preferably 0.5 to 80% by mass, and more preferably 1 to 70% by mass, based on the total mass of the resin composition.

[0092] (H) Stabilizer The resin composition of this embodiment may contain a (H) stabilizer (hereinafter also referred to as "(H) component") to the extent that it does not impair the effects of the present invention. The (H) stabilizer is added to enhance the stability of the resin composition during storage and to suppress the occurrence of polymerization reactions caused by unintended radicals or basic components.

[0093] (H) Stabilizers can be any known substances, such as borate ester compounds, strong acids, or radical scavengers. Specific examples of (H) stabilizers include trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, trifluoromethanesulfonic acid, maleic acid, methanesulfonic acid, difluoroacetic acid, trichloroacetic acid, phosphoric acid, dichloroacetic acid, N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, 4-methoxyphenol, and hydroquinone. Among these, the preferred (H) stabilizer is at least one selected from maleic acid, methanesulfonic acid, N-nitroso-N-phenylhydroxylamine aluminum, and 4-methoxyphenol. Alternatively, known (H) stabilizers disclosed in Japanese Patent Publication No. 2010-117545, Japanese Patent Publication No. 2008-184514, Japanese Patent Publication No. 2017-171804, etc., can also be used. (H) Stabilizers may be used individually or in combination of two or more.

[0094] The content of component (H) is preferably 0.1 to 5% by mass, more preferably 0.3 to 3% by mass, relative to the total mass of the resin composition. amount% That is the case.

[0095] In a preferred embodiment, the resin composition comprises at least one of (G) an inorganic filler and (H) a stabilizer.

[0096] The resin composition may further contain, as necessary, solvents, carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, defoaming agents, thixotropes, viscosity modifiers, flame retardants, and / or other additives, to the extent that it does not impair the purpose of this embodiment.

[0097] The resin composition can be obtained, for example, by stirring, melting, mixing, and / or dispersing components (A) to (E), optionally components (F), (G), and / or (H), and optionally other additives, simultaneously or separately, while applying heat treatment as necessary. The apparatus for these mixing, stirring, and dispersion processes is not particularly limited. As such apparatus, a Lei-Kai machine, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill, etc., equipped with stirring and heating devices, can be used. Furthermore, these apparatuses may be used in appropriate combinations.

[0098] The resin composition obtained in this manner is photocurable and thermocurable, and also cures sufficiently by thermocuring alone. The thermocuring temperature of the resin composition is preferably 70 to 90°C when the resin composition is used in an image sensor module.

[0099] The resin composition of this embodiment can be used, for example, as an adhesive for joining parts together, or as a raw material for such adhesive.

[0100] [glue] A second embodiment of the present invention is an adhesive comprising the resin composition of the first embodiment described above. This adhesive enables good bonding to engineering plastics, ceramics, and metals.

[0101] [Cured resin composition or adhesive] The cured product of the third embodiment of the present invention is a cured product obtained by curing the resin composition of the first embodiment or the adhesive of the second embodiment described above.

[0102] [Semiconductor equipment, electronic components] The semiconductor device of the fourth embodiment of the present invention has high moisture resistance because it includes the cured product of the third embodiment described above. The electronic component of the fifth embodiment of the present invention has high moisture resistance because it includes the semiconductor device of this fourth embodiment. [Examples]

[0103] 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 % refer to parts by mass and mass%, respectively, unless otherwise specified.

[0104] [Examples 1-9, Comparative Examples 1-4] Resin compositions were prepared by mixing predetermined amounts of each component using a three-roll mill according to the formulations 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.

[0105] • (A) (meth)acrylate compound (component (A)) (A1): Dimethylol-tricyclodecanediaacrylate (product name: Light Acrylate DCP-A, manufactured by Kyoeisha Chemical Co., Ltd., acryloyl equivalent: 188 g / eq) (A2): Polyester acrylate (Product name: M7100, manufactured by Toagosei Co., Ltd., acryloyl equivalent: 152g / eq) • (B) Polythiol compound (component (B)) (B1): Pentaerythritol tetrakis(3-mercaptopropionate) represented by the following formula (product name: PEMP, manufactured by SC Organic Chemicals, thiol equivalent: 122 g / eq) [ka] (B2): Glycoluryl derivative represented by formula (3) (product name: C3 TS-G, manufactured by Shikoku Chemicals, thiol equivalent: 114 g / eq) [ka] (B3): 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluryl represented by formula (2) (product name: TS-G, manufactured by Shikoku Chemicals Co., Ltd., thiol equivalent: 100 g / eq) [ka] • (C) Cyclic carbodiimide compound (component (C)) Cyclic carbodiimide compound of formula (5-1) (carbodiimide equivalent: 256 g / eq) [ka] • (C') Polycarposimide compound (Product name: CarbodiLite V-02B, manufactured by Nisshinbo Chemical Co., Ltd., Carbodiimide equivalent: 600g / eq) ·(D) Curing catalyst (component (D)) (D1): Amine-epoxy adduct type latent curing catalyst (Product name: Novacure HXA9322HP, manufactured by Asahi Kasei E-Materials Corporation) (D2): Amine-epoxy adduct type latent curing catalyst (Product name: Fujicure FXR1121, manufactured by T&K TOKA Corporation) • (E) Coupling agent (component (E)) (E1): 3-Glycidoxypropyltrimethoxysilane (Product name: KBM-403, Shin-Etsu Chemical Co., Ltd.) (E2): 8-Glycidoxyoctyltrimethoxysilane (Product name: KBM-4803, Shin-Etsu Chemical Co., Ltd.) (E3): 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (Product name: Sylace S530, JNC Corporation) • (F) Photoinitiator (Component (F)) 2-Methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (Product name: Omnirad 907, IGM Resins BV) • (G) Inorganic filler (Component (G)) Silica (Product name: SO-E2, Admatex Co., Ltd.) • (H) Stabilizer (Component (H)) Triisopropyl borate (product name: TIPB, Tokyo Chemical Industry Co., Ltd.)

[0106] In the examples and comparative examples, the properties of the cured products obtained by curing the resin compositions were measured as follows.

[0107] [Adhesive strength] A resin composition was stencil-printed onto a glass plate with a diameter of φ2 mm and a thickness of 125 μm. A 3.2 mm × 1.6 mm × 0.45 mm thick alumina chip was mounted on top of the printed resin composition, and the plate was cured under load to produce test specimens (n=10). The curing conditions were as follows: for "heat only," 80°C / 60 minutes in a forced-air dryer; for "UV + heat," UV irradiation of 2000 mJ / cm² from the opposite side (back) of the alumina chip mounting surface (front). 2 After being exposed to UV light (365nm, LED lamp), the glass plate was dried in a forced-air dryer at 80°C for 60 minutes. The alumina chips on this glass plate were then punctured from the side using an Aiko Engineering MODEL-1605HTP strength tester, and the shear strength was calculated from the value obtained when the alumina chips peeled off. Next, for Examples 1-9 and Comparative Examples 1-4, the cured specimens were subjected to a Pressure Cooker Test (PCT) (2 atm, 121°C, 100% RH, 20 hours), and the shear strength was calculated in the same manner. Table 1 shows the results (unit: N). The PCT test is a reliability test in which the cured resin composition is maintained at 121°C, 2 atmospheres, and 100% relative humidity. For both thermosetting conditions and UV + thermosetting conditions, the percentage retention of adhesive strength after the Pressure Cooker Test (PCT) relative to the initial adhesive strength was calculated. In this invention, the adhesive strength retention rate is preferably 50% or higher, and more preferably 60% or higher. The results are shown in Table 1.

[0108] [Table 1]

[0109] Components (A), namely (A1) and (A2), are both (meth)acrylate compounds containing ester bonds. Component (B), namely (B1), is a polythiol compound containing ester bonds, while (B2) and (B3) are polythiol compounds that do not contain ester bonds. All of Examples 1-9 and Comparative Examples 1-4 contain (A1), (A2), and (B1), and were investigated under conditions where hydrolysis is likely to occur. It should be noted that the scope of the present invention is not necessarily limited to embodiments in which components (A) and (B) contain ester bonds. A comparison of Examples 1-4 and Comparative Example 1 shows that adding 5% by mass or more of (C) cyclic carbodiimide compound to the resin composition increased the adhesive strength retention rate after PCT and improved moisture resistance under both thermosetting and UV + thermosetting conditions. A comparison of Examples 5 and 6 and Comparative Example 2 shows that even when two or more types of component (B) are used in combination, adding (C) a cyclic carbodiimide compound to the resin composition similarly increases the adhesive strength retention rate after PCT and improves moisture resistance under both thermosetting and UV+ thermosetting conditions. A comparison of Examples 2 and 7 shows that, regardless of the type of curing catalyst (D), adding (C) a cyclic carbodiimide compound to the resin composition increased the adhesive strength retention rate after PCT and improved moisture resistance under both thermosetting and UV+thermosetting conditions. A comparison of Example 2 and Comparative Examples 1 and 3 shows that the (C) cyclic carbodiimide compound exhibits better moisture resistance under thermal curing conditions than the polycarbodiimide compound. Furthermore, under UV + thermal curing conditions, the (C) cyclic carbodiimide compound was able to improve moisture resistance, while the polycarbodiimide compound was not. A comparison of Examples 2, 8, and 9 and Comparative Example 4 shows that the presence of a coupling agent (E) is also necessary for improving moisture resistance. [Industrial applicability]

[0110] The present invention provides a photocurable and thermocurable resin composition that exhibits high moisture resistance not only after UV curing and heat curing, but also after heat curing alone. It is particularly useful as an adhesive for applications where UV curing is difficult.

[0111] The disclosures of Japanese Patent Application No. 2021-106245 (filed on June 28, 2021) and Japanese Patent Application No. 2021-133624 (filed on August 18, 2021) are incorporated herein by reference in their entirety. All documents, patent applications, and technical standards described herein are incorporated by reference to the same extent as if each individual document, patent application, and technical standard were specifically and individually noted to be incorporated by reference.

Claims

1. (A) (meth)acrylate compound, (B) Polythiol compounds, (C) A cyclic carbodiimide compound having multiple cyclic structures containing carbodiimide groups, (D) Curing catalyst, and (E) Coupling agent An adhesive comprising a resin composition containing, (A) The content of component is 10 to 70% by mass relative to the total mass of the resin composition. (C) The content of a cyclic carbodiimide compound having multiple cyclic structures containing carbodiimide groups is 5% by mass or more of the total mass of the resin composition. glue.

2. (C) A cyclic carbodiimide compound having multiple cyclic structures containing carbodiimide groups is given by the following general formula (5): 【Chemistry 1】 It is a cyclic carbodiimide compound represented by, In general formula (5), Ar １ ~Ar ４ Each of these is an aromatic group, X is a tetravalent group, The adhesive according to claim 1, wherein q is 1.

3. (E) The adhesive according to claim 1, wherein the coupling agent comprises an epoxy-based coupling agent containing an epoxy group.

4. Furthermore, the adhesive according to claim 1, comprising (F) a photoinitiator.

5. Furthermore, the adhesive according to claim 1, comprising at least one of (G) an inorganic filler and (H) a stabilizer.

6. Furthermore, the adhesive according to claim 4, comprising at least one of (G) an inorganic filler and (H) a stabilizer.

7. A cured product obtained by curing the adhesive according to any one of claims 1 to 6.

8. A semiconductor device comprising the cured product described in claim 7.

9. An electronic component including the semiconductor device described in claim 8.

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