Curable resin composition and electronic component device

Abstract

A curable resin composition comprising a curable resin and a compound represented by general formula (A). In general formula (A), R11 to R16 each independently represent a hydrogen atom, -CH2OH, or -CH2OR17, R17 representing an alkyl group having 1-3 carbon atoms, and at least one of R11 to R16 represents -CH2OR17.

Description

[Technical Field]

[0001] The present disclosure relates to a curable resin composition and an electronic component device. [Background technology]

[0002] In recent years, as electronic devices have become smaller, lighter, and more powerful, the density of packaging has increased. As a result, the mainstream of electronic component devices is shifting from conventional pin insertion type packages to surface mount type packages for ICs (Integrated Circuits), LSIs (Large Scale Integration), etc.

[0003] Surface-mount packages differ from conventional pin-insertion packages in their mounting method. Specifically, when attaching pins to a wiring board, conventional pin-insertion packages require soldering from the backside of the board after the pins are inserted into the board. This prevents the package from being directly exposed to high temperatures. However, with surface-mount packages, the entire electronic device is processed using a solder bath or reflow equipment, exposing the package directly to soldering (reflow) temperatures. As a result, if the package absorbs moisture, the moisture rapidly expands during soldering. The resulting vapor pressure acts as a peel stress, causing peeling between the insert (e.g., chip, lead frame) and the encapsulant, potentially resulting in package cracks and poor electrical characteristics. Therefore, there is a need for encapsulating materials that offer excellent adhesion to the insert and, ultimately, excellent solder heat resistance (reflow resistance).

[0004] To meet the above demands, the use of silane coupling agents as modifiers for inorganic fillers contained in sealing materials has been investigated. Specifically, the use of epoxy group-containing silane coupling agents or amino group-containing silane coupling agents (see, for example, Patent Document 1), the use of sulfur atom-containing silane coupling agents (see, for example, Patent Document 2), etc. has been investigated. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 11-147939 [Patent Document 2] Japanese Patent Application Laid-Open No. 2000-103940 Summary of the Invention [Problem to be solved by the invention]

[0006] However, methods using epoxy group-containing silane coupling agents or amino group-containing silane coupling agents may not sufficiently improve adhesion to the metal on the surface of the lead frame. Furthermore, when sulfur atom-containing silane coupling agents are used, there is a problem that they do not sufficiently improve adhesion to metals (noble metals such as gold and silver) or substrates with Ag plating on copper lead frames. Furthermore, additives containing sulfur atoms can corrode copper wiring, so a method for improving adhesion without using additives containing sulfur atoms has been sought.

[0007] The present disclosure has been made in consideration of the above-described conventional circumstances, and aims to provide a curable resin composition that has excellent adhesion to metal in a cured state, and an electronic component device that includes an element encapsulated with the curable resin composition. [Means for solving the problem]

[0008] Specific means for achieving the above object are as follows. <1> A curable resin composition comprising a curable resin and a compound represented by the following general formula (A):

[0009] [ka]

[0010] [In general formula (A), R 11 ~R 16 each independently represents a hydrogen atom, -CHOH, or -CHOR 17 represents R17 represents an alkyl group having 1 to 3 carbon atoms. 11 ~R 16 At least one of the following is -CH2OR 17 represents.] <2> The compound represented by the general formula (A) is 11 ~R 16 At least four of the 17 Contains compounds represented by <1> The curable resin composition according to claim 1. <3> The compound represented by the general formula (A) is 11 ~R 16 All of -CH2OR 17 Contains compounds represented by <1> The curable resin composition according to claim 1. <4> Further containing inorganic filler <1> ~ <3> The curable resin composition according to any one of the above. <5> The curable resin includes an epoxy resin. <1> ~ <4> The curable resin composition according to any one of the above. <6> The epoxy resin includes at least one selected from the group consisting of biphenyl-type epoxy resins, stilbene-type epoxy resins, diphenylmethane-type epoxy resins, sulfur-containing epoxy resins, novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenylmethane-type epoxy resins, copolymer-type epoxy resins, and aralkyl-type epoxy resins. <5> The curable resin composition according to claim 1. <7> Further containing a curing agent <1> ~ <6> The curable resin composition according to any one of the above. <8> The curing agent contains at least one selected from the group consisting of aralkyl-type phenolic resins, dicyclopentadiene-type phenolic resins, triphenylmethane-type phenolic resins, copolymerized phenolic resins of triphenylmethane-type phenolic resins and aralkyl-type phenolic resins, and novolac-type phenolic resins. <7> The curable resin composition according to claim 1. <9> Further containing a cure accelerator <1> ~ <8> The curable resin composition according to any one of the above. <10> The curing accelerator contains a phosphonium compound. <9> The curable resin composition according to claim 1. <11> The phosphonium compound includes a compound represented by the following general formula (I-1): <10> The curable resin composition according to claim 1.

[0011] [ka]

[0012] [In general formula (I-1), R 1 ~R 3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R 1 ~R 3 At least two of R may be bonded to each other to form a ring structure; 4 ~R 7 each independently represents a hydrogen atom, a hydroxyl group, or an organic group having 1 to 18 carbon atoms; R 4 ~R 7 At least two of the groups may be bonded to each other to form a ring structure. <12> The compound represented by the general formula (I-1) includes a compound represented by the following general formula (I-2): <11> The curable resin composition according to claim 1.

[0013] [ka]

[0014] [In general formula (I-2), R 1 ~R 3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R 1 ~R 3 At least two of R may be bonded to each other to form a ring structure; 4 ~R 6 each independently represents a hydrogen atom or an organic group having 1 to 18 carbon atoms; R 4 ~R 6 At least two of the groups may be bonded to each other to form a ring structure. <13> An element and a device for sealing the element <1> ~ <12> and an electronic component device comprising a cured product of the curable resin composition according to any one of claims 1 to 4. [Effects of the Invention]

[0015] According to the present disclosure, there are provided a curable resin composition that has excellent adhesion to metals in a cured state, and an electronic component device including an element encapsulated with the curable resin composition. DETAILED DESCRIPTION OF THE INVENTION

[0016] Hereinafter, embodiments for carrying out the present disclosure will be described in detail. However, the present disclosure is not limited to the following embodiments. In the following embodiments, components (including element steps, etc.) are not essential unless otherwise specified. The same applies to numerical values ​​and their ranges, and do not limit the present disclosure.

[0017] In the present disclosure, the term "process" includes not only a process that is independent of other processes, but also a process that cannot be clearly distinguished from other processes as long as the purpose of the process is achieved. In the present disclosure, numerical ranges indicated using "to" include the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in this disclosure, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in the numerical ranges described in this disclosure, the upper or lower limit value of that numerical range may be replaced with a value shown in the examples. In the present disclosure, each component may contain multiple substances corresponding to the component. When multiple substances corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple substances present in the composition, unless otherwise specified. In the present disclosure, the particles corresponding to each component may contain multiple types of particles. When multiple types of particles corresponding to each component are present in the composition, the particle size of each component means the value for a mixture of the multiple types of particles present in the composition, unless otherwise specified.

[0018] <Curable resin composition> The curable resin composition of the present disclosure contains a curable resin and a compound represented by the following general formula (A) (hereinafter, sometimes referred to as a specific alkylated melamine).

[0019] [ka]

[0020] In general formula (A), R 11 ~R 16 each independently represents a hydrogen atom, -CHOH, or -CHOR 17 represents R 17 represents an alkyl group having 1 to 3 carbon atoms. 11 ~R 16 At least one of the following is -CH2OR 17 Represents.

[0021] The inventors' investigations have revealed that curable resin compositions containing specific alkylated melamines, in a cured state, have excellent adhesion to metals (noble metals such as gold and silver), substrates such as copper lead frames plated with Ag, etc. The reason for this is not clear, but it is presumed that this is because the specific alkylated melamine in the cured product forms a coordinate bond with the metal.

[0022] The curable resin composition containing the specific alkylated melamine has excellent adhesion to metals in a cured state, and therefore when used as an encapsulant for a package including a lead frame whose surface is at least made of metal, peeling between the lead frame and the encapsulant is suppressed, resulting in excellent reflow resistance.

[0023] The curable resin composition of the present disclosure contains a curable resin and a specific alkylated melamine, and may contain other components such as an inorganic filler, a curing agent, and a curing accelerator, as necessary. Hereinafter, each component contained in the curable resin composition of the present disclosure will be described in detail.

[0024] (Specific alkylated melamine) The curable resin composition of the present disclosure contains a specific alkylated melamine. The specific alkylated melamine may be used alone or in combination of two or more types with different structures.

[0025] R in general formula (A) 17 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Among these, a methyl group or an ethyl group is preferred, and a methyl group is more preferred.

[0026] The specific alkylated melamine is represented by the general formula (A) 11 ~R 16 At least three of the -CH2OR 17 Preferably, the compound is represented by R 11 ~R 16 At least four of the 17 More preferably, the compound is represented by R 11 ~R 16 All of -CH2OR 17 More preferably, R 11 ~R 16 It is particularly preferable that all of the above are represented by —CH2OCH3.

[0027] Specific examples of the specific alkylated melamine include compounds represented by the following formula:

[0028] [ka]

[0029] The proportion of the compound represented by formula (A1) in the specific alkylated melamine is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 90% by mass or more.

[0030] The content of the specific alkylated melamine in the curable resin composition is not particularly limited. From the viewpoint of sufficiently obtaining the effect of improving adhesion to precious metals such as gold and silver, and to substrates such as copper lead frames plated with Ag, the content is preferably, for example, 0.1 parts by mass or more, more preferably 1.0 parts by mass or more, and even more preferably 2.5 parts by mass or more, per 100 parts by mass of the total of the curable resin and optional curing agent contained in the curable resin composition (hereinafter also referred to as the "resin component"). From the viewpoint of curability, the content is, for example, preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin component.

[0031] (curable resin) The curable resin is not particularly limited as long as it forms a three-dimensional crosslinked structure by reaction, and may be thermosetting or photocurable. From the viewpoint of mass production, thermosetting is preferable. The curable resin may be one that cures by self-polymerization or one that cures by reaction with a curing agent, crosslinking agent, etc.

[0032] The functional group contained in the curable resin that can cause a curing reaction is not particularly limited, and examples thereof include cyclic ether groups such as an epoxy group and an oxetanyl group, a hydroxyl group, a carboxy group, an amino group, an acryloyl group, a methacryloyl group, an isocyanate group, a maleimide group, an alkenyl group, etc. From the viewpoint of the balance of properties as an encapsulant, a curable resin containing a cyclic ether group is preferred, and a curable resin containing an epoxy group (epoxy resin) is more preferred.

[0033] When the curable resin is an epoxy resin, the type of epoxy resin is not particularly limited as long as it has two or more epoxy groups in one molecule. Specifically, novolac epoxy resins (phenol novolac epoxy resins, orthocresol novolac epoxy resins, etc.) are obtained by epoxidizing novolac resins obtained by condensing or co-condensing, under an acid catalyst, at least one phenolic compound selected from the group consisting of phenolic compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol A, bisphenol F, etc., and naphthol compounds such as α-naphthol, β-naphthol, dihydroxynaphthalene, etc., with an aliphatic aldehyde compound such as formaldehyde, acetaldehyde, propionaldehyde, etc.; triphenylmethane epoxy resins are obtained by epoxidizing triphenylmethane phenolic resins obtained by condensing or co-condensing, under an acid catalyst, the above phenolic compounds with aromatic aldehyde compounds such as benzaldehyde, salicylaldehyde, etc.; and novolac resins obtained by co-condensing, under an acid catalyst, the above phenolic compounds and naphthol compounds with an aldehyde compound, etc., are epoxidized. diphenylmethane-type epoxy resins, which are diglycidyl ethers of bisphenol A, bisphenol F, etc.; biphenyl-type epoxy resins, which are diglycidyl ethers of alkyl-substituted or unsubstituted biphenols; stilbene-type epoxy resins, which are diglycidyl ethers of stilbene-based phenolic compounds; sulfur-containing epoxy resins, which are diglycidyl ethers of bisphenol S, etc.; epoxy resins, which are glycidyl ethers of alcohols such as butanediol, polyethylene glycol, and polypropylene glycol; glycidyl ester-type epoxy resins, which are glycidyl esters of polycarboxylic acids such as phthalic acid, isophthalic acid, and tetrahydrophthalic acid; glycidylamine-type epoxy resins, in which the active hydrogen bonded to the nitrogen atom of aniline, diaminodiphenylmethane, isocyanuric acid, etc. is substituted with a glycidyl group; and dicyclopentadiene-type epoxy resins, which are epoxidized co-condensation resins of dicyclopentadiene and phenolic compounds.Alicyclic epoxy resins such as vinylcyclohexene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, and 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, which are produced by epoxidizing the olefin bonds in the molecule; paraxylylene-modified epoxy resins, which are glycidyl ethers of paraxylylene-modified phenolic resins; metaxylylene-modified epoxy resins, which are glycidyl ethers of metaxylylene-modified phenolic resins; terpene-modified epoxy resins, which are glycidyl ethers of terpene-modified phenolic resins; and dicyclopentadiene-modified phenolic resins, which are glycidyl ethers of dicyclopentadiene-modified phenolic resins. Examples of suitable epoxy resins include pentadiene-modified epoxy resins, cyclopentadiene-modified epoxy resins, which are glycidyl ethers of cyclopentadiene-modified phenolic resins; polycyclic aromatic ring-modified epoxy resins, which are glycidyl ethers of polycyclic aromatic ring-modified phenolic resins; naphthalene-type epoxy resins, which are glycidyl ethers of naphthalene ring-containing phenolic resins; halogenated phenol novolac-type epoxy resins; hydroquinone-type epoxy resins; trimethylolpropane-type epoxy resins; linear aliphatic epoxy resins obtained by oxidizing olefin bonds with peracids such as peracetic acid; and aralkyl-type epoxy resins obtained by epoxidizing aralkyl-type phenolic resins such as phenol aralkyl resins and naphthol aralkyl resins. Further examples of suitable epoxy resins include epoxidized silicone resins and epoxidized acrylic resins. These epoxy resins may be used alone or in combination of two or more.

[0034] Among the above epoxy resins, from the viewpoint of a balance between reflow resistance and fluidity, at least one epoxy resin selected from the group consisting of biphenyl-type epoxy resins, stilbene-type epoxy resins, diphenylmethane-type epoxy resins, sulfur-containing epoxy resins, novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenylmethane-type epoxy resins, copolymer-type epoxy resins, and aralkyl-type epoxy resins (these are referred to as "specific epoxy resins"). The specific epoxy resins may be used alone or in combination of two or more.

[0035] When the epoxy resin contains a specific epoxy resin, the content of the specific epoxy resin is preferably 30% by mass or more, and more preferably 50% by mass or more, of the total epoxy resin, from the viewpoint of exhibiting the performance of the specific epoxy resin.

[0036] Among the specific epoxy resins, biphenyl-type epoxy resins, stilbene-type epoxy resins, diphenylmethane-type epoxy resins, and sulfur-atom-containing epoxy resins are more preferred from the viewpoint of fluidity, and dicyclopentadiene-type epoxy resins, triphenylmethane-type epoxy resins, and aralkyl-type epoxy resins are preferred from the viewpoint of heat resistance. Specific examples of preferred epoxy resins are shown below.

[0037] The biphenyl type epoxy resin is not particularly limited as long as it is an epoxy resin having a biphenyl skeleton. For example, an epoxy resin represented by the following general formula (II) is preferred. Among the epoxy resins represented by the following general formula (II), R 8 When the oxygen atom is substituted at the 4 and 4' positions, the 3, 3', 5, and 5' positions are methyl groups, and the other R 8 YX-4000H (Mitsubishi Chemical Corporation, product name) where R is a hydrogen atom, 8 4,4'-bis(2,3-epoxypropoxy)biphenyl, where R is a hydrogen atom, 8 When is a hydrogen atom and R 8 When the oxygen atom is substituted at the 4 and 4' positions, the 3, 3', 5, and 5' positions are methyl groups, and the other R8 is a hydrogen atom, YL-6121H (trade name, Mitsubishi Chemical Corporation) and the like are commercially available.

[0038] [ka]

[0039] In formula (II), R 8 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aromatic group having 4 to 18 carbon atoms, and may all be the same or different. n is an average value and represents a number of 0 to 10.

[0040] The stilbene type epoxy resin is not particularly limited as long as it is an epoxy resin having a stilbene skeleton. For example, an epoxy resin represented by the following general formula (III) is preferred. Among the epoxy resins represented by the following general formula (III), R 9 When the oxygen atom is substituted at the 4 and 4' positions, the 3, 3', 5, and 5' positions are methyl groups, and the other R 9 is a hydrogen atom, and R 10 are all hydrogen atoms, and R 9 Three of the 3, 3', 5, and 5' positions are methyl groups, one is a t-butyl group, and the remaining R 9 is a hydrogen atom, and R 10 and mixtures of those in which all of the above are hydrogen atoms.

[0041] [ka]

[0042] In formula (III), R 9 and R 10 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different from each other. n is an average value and represents a number of 0 to 10.

[0043] The diphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin having a diphenylmethane skeleton. For example, an epoxy resin represented by the following general formula (IV) is preferred. Among the epoxy resins represented by the following general formula (IV), R 11 are all hydrogen atoms, and R 12 When the oxygen atom is substituted at the 4 and 4' positions, the 3, 3', 5, and 5' positions are methyl groups, and the other R 12 YSLV-80XY (Nippon Steel Chemical & Material Co., Ltd., product name) in which is a hydrogen atom is commercially available.

[0044] [ka]

[0045] In formula (IV), R 11 and R 12 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different from each other. n is an average value and represents a number of 0 to 10.

[0046] The sulfur atom-containing epoxy resin is not particularly limited as long as it is an epoxy resin containing a sulfur atom. For example, an epoxy resin represented by the following general formula (V) can be mentioned. Among the epoxy resins represented by the following general formula (V), R 13 When the oxygen atom is substituted at the 4 and 4' positions, the 3 and 3' positions are t-butyl groups, and the 6 and 6' positions are methyl groups. 13 YSLV-120TE (Nippon Steel Chemical & Material Co., Ltd., product name) in which is a hydrogen atom is commercially available.

[0047] [ka]

[0048] In formula (V), R 13represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different from each other. n is an average value and represents a number of 0 to 10.

[0049] The novolac epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a novolac phenolic resin. For example, epoxy resins obtained by epoxidizing a novolac phenolic resin such as a phenol novolac resin, a cresol novolac resin, or a naphthol novolac resin using a method such as glycidyl etherification are preferred, and epoxy resins represented by the following general formula (VI) are more preferred. Among the epoxy resins represented by the following general formula (VI), R 14 are all hydrogen atoms, and R 15 is a methyl group, and i=1, such as ESCN-190 and ESCN-195 (product names of Sumitomo Chemical Co., Ltd.), 14 are all hydrogen atoms and i=0, such as N-770 and N-775 (trade names of DIC Corporation), 14 are all hydrogen atoms, and the part where i=0 and the part where i=1 are R 15 YDAN-1000-10C (Nippon Steel Chemical & Material Co., Ltd., product name), a styrene-modified phenolic novolac epoxy resin having a moiety where R is -CH(CH3)-Ph; 14 are all hydrogen atoms, i=1, and R 15 is a methyl group and i=2, R 15 Benzyl group-modified cresol novolac epoxy resins, which have one methyl group and one benzyl group, are commercially available.

[0050] [ka]

[0051] In formula (VI), R 14 R represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. 15represents a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. Each i independently represents an integer of 0 to 3. n is an average value and represents a number of 0 to 10.

[0052] The dicyclopentadiene-type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a compound having a dicyclopentadiene skeleton as a raw material. For example, an epoxy resin represented by the following general formula (VII) is preferred. Among the epoxy resins represented by the following general formula (VII), HP-7200 (trade name, DIC Corporation), in which i = 0, is commercially available.

[0053] [ka]

[0054] In formula (VII), R 16 represents a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. Each i independently represents an integer of 0 to 3. n is an average value and represents a number of 0 to 10.

[0055] The triphenylmethane epoxy resin is not particularly limited as long as it is an epoxy resin made from a compound having a triphenylmethane skeleton. For example, an epoxy resin obtained by glycidyl etherifying a triphenylmethane phenolic resin obtained from an aromatic aldehyde compound and a phenolic compound is preferred, and an epoxy resin represented by the following general formula (VIII) is more preferred. Among the epoxy resins represented by the following general formula (VIII), 1032H60 (Mitsubishi Chemical Corporation, trade name) and EPPN-502H (Nippon Kayaku Co., Ltd., trade name), in which i is 0 and k is 0, are commercially available.

[0056] [ka]

[0057] In formula (VIII), R 17 and R 18represents a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i independently represents an integer of 0 to 3, and each k independently represents an integer of 0 to 4. n is an average value and represents a number of 0 to 10.

[0058] The copolymerized epoxy resin obtained by epoxidizing a novolac resin obtained from a naphthol compound, a phenol compound, and an aldehyde compound is not particularly limited as long as it is an epoxy resin made from a compound having a naphthol skeleton and a compound having a phenol skeleton as raw materials. For example, an epoxy resin obtained by glycidyl etherifying a novolac phenolic resin using a compound having a naphthol skeleton and a compound having a phenol skeleton is preferred, and an epoxy resin represented by the following general formula (IX) is more preferred. Among the epoxy resins represented by the following general formula (IX), R 21 is a methyl group, i is 1, j is 0, and k is 0, and NC-7300 (trade name, Nippon Kayaku Co., Ltd.) is available as a commercially available product.

[0059] [ka]

[0060] In formula (IX), R 19 ~R 21 represents a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i independently represents an integer of 0 to 3, each j independently represents an integer of 0 to 2, and each k independently represents an integer of 0 to 4. Each l and m is an average value and a number of 0 to 10, and (l+m) represents a number of 0 to 10. The terminal of the epoxy resin represented by formula (IX) is either formula (IX-1) or (IX-2) below. In formulas (IX-1) and (IX-2), R 19 ~R 21 , i, j and k are defined as R 19 ~R 21 The definitions of i, j, and k are the same as those of i, j, and k. n is 1 (when the bond is formed via a methylene group) or 0 (when the bond is not formed via a methylene group).

[0061] [ka]

[0062] Examples of the epoxy resin represented by the general formula (IX) include random copolymers containing l structural units and m structural units randomly, alternating copolymers containing them alternately, copolymers containing them regularly, block copolymers containing them in blocks, etc. Any one of these may be used alone, or two or more may be used in combination.

[0063] Another preferred copolymerized epoxy resin is Epiclon HP-5000 (trade name, DIC Corporation), a methoxynaphthalene-cresol-formaldehyde co-condensation epoxy resin containing the following two structural units in a random, alternating, or block order, and represented by the following general formula: In the following general formula, n and m each represent an average value and a number from 0 to 10, and (n+m) represents a number from 0 to 10, preferably n and m each represent an average value and a number from 1 to 9, and (n+m) represents a number from 2 to 10.

[0064] [ka]

[0065] The aralkyl epoxy resin is not particularly limited as long as it is an epoxy resin made from a phenolic resin synthesized from at least one selected from the group consisting of phenolic compounds such as phenol and cresol and naphthol compounds such as naphthol and dimethylnaphthol, and dimethoxyparaxylene, bis(methoxymethyl)biphenyl, or a derivative thereof. For example, epoxy resins obtained by glycidyl etherifying a phenolic resin synthesized from at least one selected from the group consisting of phenolic compounds such as phenol and cresol and naphthol compounds such as naphthol and dimethylnaphthol, and dimethoxyparaxylene, bis(methoxymethyl)biphenyl, or a derivative thereof are preferred, and epoxy resins represented by the following general formulas (X) and (XI) are more preferred.

[0066] Among the epoxy resins represented by the following general formula (X), those in which i is 0 and R 38 is a hydrogen atom, i is 0, and R 38 is a hydrogen atom and all R 8 CER-3000 (trade name, Nippon Kayaku Co., Ltd.), which is a mixture of an epoxy resin in which l is a hydrogen atom and an epoxy resin in which k is a hydrogen atom at a mass ratio of 80:20, is commercially available. Furthermore, among the epoxy resins represented by the following general formula (XI), ESN-175 (trade name, Nippon Steel Chemical & Material Co., Ltd.), in which l is 0, j is 0, and k is 0, is commercially available.

[0067] [ka]

[0068] In formulas (X) and (XI), R 38 R represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. 37 , R 39 ~R 41 represents a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i is independently an integer of 0 to 3, each j is independently an integer of 0 to 2, each k is independently an integer of 0 to 4, and each l is independently an integer of 0 to 4. Each n is an average value and is independently a number of 0 to 10.

[0069] R in the above general formulas (II) to (XI) 8 ~R 21 and R 37 ~R 41 In the formula (II), "all of them may be the same or different" means, for example, that 8 to 88 R 8 This means that all of the R may be the same or different. 9 ~R 21 and R 37 ~R 41In addition, the numbers of R may all be the same or different. 8 ~R 21 and R 37 ~R 41 may be the same or different. For example, R 9 and R 10 may all be the same or different. Furthermore, the monovalent organic group having 1 to 18 carbon atoms in the general formulae (III) to (XI) is preferably an alkyl group or an aryl group.

[0070] In the general formulas (II) to (XI), n is an average value, and each independently is preferably in the range of 0 to 10. When n is 10 or less, the melt viscosity of the resin component does not become too high, and the viscosity of the curable resin composition during melt molding tends to decrease, and the occurrence of filling defects, deformation of bonding wires (gold wires connecting elements to leads), etc. is more preferably set in the range of 0 to 4.

[0071] The functional group equivalent of the curable resin (epoxy equivalent in the case of an epoxy resin) is not particularly limited. From the viewpoint of the balance of various properties such as moldability, reflow resistance, and electrical reliability, the functional group equivalent of the curable resin is preferably 100 g / eq to 1000 g / eq, and more preferably 150 g / eq to 500 g / eq.

[0072] The softening point or melting point of the curable resin is not particularly limited, but is preferably 40°C to 180°C from the viewpoint of moldability and reflow resistance, and more preferably 50°C to 130°C from the viewpoint of handleability during preparation of the curable resin composition. In the present disclosure, the softening point refers to a value measured by the ring and ball method of JIS K 7234:1986. In the present disclosure, the melting point refers to a value measured in accordance with the visual method of JIS K 0064:1992.

[0073] The content of the curable resin in the curable resin composition is preferably 0.5 to 50% by mass, more preferably 2 to 30% by mass, from the viewpoints of strength, fluidity, heat resistance, moldability, etc.

[0074] (hardening agent) The curable resin composition may contain a curing agent. The type of curing agent is not particularly limited and can be selected depending on the type of curable resin, the desired properties of the curable resin composition, and the like. When the curable resin is an epoxy resin, examples of the curing agent include a phenol curing agent, an amine curing agent, an acid anhydride curing agent, a polymercaptan curing agent, a polyaminoamide curing agent, an isocyanate curing agent, a blocked isocyanate curing agent, etc. From the viewpoint of achieving both curability and pot life, at least one selected from the group consisting of a phenol curing agent, an amine curing agent, and an acid anhydride curing agent is preferred, and from the viewpoint of electrical reliability, a phenol curing agent is more preferred.

[0075] Examples of phenolic curing agents include phenolic resins and polyhydric phenolic compounds having two or more phenolic hydroxyl groups per molecule. Specific examples include polyhydric phenolic compounds such as resorcinol, catechol, bisphenol A, bisphenol F, and substituted or unsubstituted biphenols; novolac-type phenolic resins obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenolic compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol A, bisphenol F, phenylphenol, and aminophenol, and naphthol compounds such as α-naphthol, β-naphthol, and dihydroxynaphthalene, with an aldehyde compound such as formaldehyde, acetaldehyde, or propionaldehyde, under an acidic catalyst; and phenolic resins synthesized from the above-mentioned phenolic compounds and dimethoxyparaxylene, bis(methoxymethyl)biphenyl, or the like. Examples of suitable phenol curing agents include aralkyl-type phenolic resins such as aryl aralkyl resins and naphthol aralkyl resins; paraxylylene- and / or metaxylylene-modified phenolic resins; melamine-modified phenolic resins; terpene-modified phenolic resins; dicyclopentadiene-type phenolic resins and dicyclopentadiene-type naphthol resins synthesized by copolymerization of the above-mentioned phenolic compounds with dicyclopentadiene; cyclopentadiene-modified phenolic resins; polycyclic aromatic ring-modified phenolic resins; biphenyl-type phenolic resins; triphenylmethane-type phenolic resins obtained by condensing or co-condensing the above-mentioned phenolic compounds with aromatic aldehyde compounds such as benzaldehyde and salicylaldehyde under an acidic catalyst; and phenolic resins obtained by copolymerizing two or more of these. Furthermore, examples of phenolic curing agents include monohydric phenolic compounds having one phenolic hydroxyl group per molecule. These phenolic curing agents may be used alone or in combination.

[0076] Among phenolic curing agents, from the viewpoint of reflow resistance, at least one selected from the group consisting of aralkyl type phenolic resins, dicyclopentadiene type phenolic resins, triphenylmethane type phenolic resins, copolymer type phenolic resins of triphenylmethane type phenolic resins and aralkyl type phenolic resins, and novolac type phenolic resins (these are referred to as "specific phenolic curing agents"). The specific phenolic curing agents may be used alone or in combination of two or more.

[0077] When the curing agent contains a specific phenol curing agent, the content of the specific phenol curing agent is preferably 30% by mass or more, and more preferably 50% by mass or more, of the entire curing agent, from the viewpoint of fully exhibiting its performance.

[0078] Examples of aralkyl phenolic resins include phenol aralkyl resins and naphthol aralkyl resins synthesized from a phenolic compound and dimethoxyparaxylene, bis(methoxymethyl)biphenyl, etc. The aralkyl phenolic resin may be further copolymerized with other phenolic resins. Examples of copolymerized aralkyl phenolic resins include copolymerized phenolic resins of triphenylmethane phenolic resin and aralkyl phenolic resin, copolymerized phenolic resins of salicylaldehyde phenolic resin and aralkyl phenolic resin, and copolymerized phenolic resins of novolac phenolic resin and aralkyl phenolic resin.

[0079] The aralkyl phenolic resin is not particularly limited as long as it is a phenolic resin synthesized from at least one compound selected from the group consisting of phenol compounds and naphthol compounds, and dimethoxy-para-xylene, bis(methoxymethyl)biphenyl, or a derivative thereof. For example, phenolic resins represented by the following general formulas (XII) to (XIV) are preferred.

[0080] [ka]

[0081] In formulas (XII) to (XIV), R 23 R represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. 22 , R 24 , R 25 and R 28 R represents a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. 26 and R 27 represents a hydroxyl group or a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i is independently an integer of 0 to 3, each j is independently an integer of 0 to 2, each k is independently an integer of 0 to 4, and each p is independently an integer of 0 to 4. Each n is an average value and is independently a number of 0 to 10.

[0082] Among the phenolic resins represented by the general formula (XII), i is 0 and R 23 MEH-7851 (product name, Meiwa Kasei Co., Ltd.), in which all are hydrogen atoms, is commercially available.

[0083] Among the phenolic resins represented by the general formula (XIII) above, XL-225, XLC (Mitsui Chemicals, Inc., trade name), MEH-7800 (Meiwa Chemical Industry Co., Ltd., trade name), etc., in which i is 0 and k is 0, are commercially available.

[0084] Among the phenolic resins represented by the general formula (XIV), SN-170 (trade name, Nippon Steel Chemical & Material Co., Ltd.), in which j is 0, k is 0, and p is 0, and R 27 is a hydroxyl group and p is 0, and SN-395 (trade name, Nippon Steel Chemical & Material Co., Ltd.) is available as a commercially available product.

[0085] The dicyclopentadiene-type phenolic resin is not particularly limited as long as it is a phenolic resin obtained from a compound having a dicyclopentadiene skeleton as a raw material. For example, a phenolic resin represented by the following general formula (XV) is preferred. Among the phenolic resins represented by the following general formula (XV), phenolic resins in which i is 0 are commercially available.

[0086] [ka]

[0087] In formula (XV), R 29 represents a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. Each i independently represents an integer of 0 to 3. n is an average value and represents a number of 0 to 10.

[0088] The triphenylmethane type phenolic resin is not particularly limited as long as it is a phenolic resin obtained from an aromatic aldehyde compound and a phenolic compound as raw materials. For example, a phenolic resin represented by the following general formula (XVI) is preferred.

[0089] Among the phenolic resins represented by the following general formula (XVI), MEH-7500 (trade name, Meiwa Kasei Co., Ltd.), in which i and k are 0, is commercially available.

[0090] [ka]

[0091] In formula (XVI), R 30 and R 31 represents a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i is independently an integer of 0 to 3, and each k is independently an integer of 0 to 4. n is an average value and is a number of 0 to 10.

[0092] The copolymerized phenolic resin of a triphenylmethane type phenolic resin and an aralkyl type phenolic resin is not particularly limited as long as it is a copolymerized phenolic resin of a phenolic resin obtained from a compound having a benzaldehyde skeleton as a raw material and an aralkyl type phenolic resin. For example, a phenolic resin represented by the following general formula (XVII) is preferred.

[0093] [ka]

[0094] In formula (XVII), R 32 ~R 34 represents a monovalent organic group having 1 to 18 carbon atoms, and may all be the same or different. Each i is independently an integer of 0 to 3, each k is independently an integer of 0 to 4, and each q is independently an integer of 0 to 5. Each l and m is an average value and independently a number of 0 to 11, provided that the sum of l and m is a number of 1 to 11.

[0095] The novolac phenolic resin is not particularly limited as long as it is a phenolic resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol compounds and naphthol compounds with an aldehyde compound in the presence of an acid catalyst. For example, a phenolic resin represented by the following general formula (XVIII) is preferred.

[0096] Among the phenolic resins represented by the following general formula (XVIII), those in which i is 0 and R 35 are all hydrogen atoms, such as Tamanol 758 and 759 (trade names, Arakawa Chemical Industries, Ltd.) and H-4 (trade name, Meiwa Chemical Industry Co., Ltd.).

[0097] [ka]

[0098] In formula (XVIII), R 35R represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. 36 represents a monovalent organic group having 1 to 18 carbon atoms, and may be the same or different. Each i independently represents an integer of 0 to 3. n is an average value and represents a number of 0 to 10.

[0099] R in the above general formulas (XII) to (XVIII) 22 ~R 36 The expression "may be the same or different" means, for example, that i R 22 This means that all of the R may be the same or different from each other. 23 ~R 36 In addition, the numbers of R may be the same or different from each other. 22 ~R 36 may be the same or different. For example, R 22 and R 23 may be the same or different, and R 30 and R 31 may all be the same or different.

[0100] In the general formulas (XII) to (XVIII), n is preferably in the range of 0 to 10. If it is 10 or less, the melt viscosity of the resin component will not be too high, and the viscosity of the curable resin composition during melt molding will also be low, making it less likely that filling defects, deformation of bonding wires (gold wires connecting elements to leads), etc. will occur. The average n in one molecule is preferably set in the range of 0 to 4.

[0101] Examples of monohydric phenol compounds include "Tinuvin 405," "Tinuvin 900," "Tinuvin 99-2," "Tinuvin 326," "Tinuvin 384-2," and "Tinuvin 928" (all manufactured by BASF).

[0102] The functional group equivalent of the curing agent (hydroxyl group equivalent in the case of a phenolic curing agent) is not particularly limited, but from the viewpoint of the balance of various properties such as moldability, reflow resistance, and electrical reliability, it is preferably 70 g / eq to 1000 g / eq, and more preferably 80 g / eq to 600 g / eq.

[0103] The softening point or melting point of the curing agent is not particularly limited, but is preferably 40°C to 180°C from the viewpoint of moldability and reflow resistance, and more preferably 50°C to 130°C from the viewpoint of handleability during production of the curable resin composition.

[0104] The equivalent ratio between the curable resin and the curing agent, i.e., the ratio of the number of functional groups in the curing agent to the number of functional groups in the curable resin (number of functional groups in the curing agent / number of functional groups in the curable resin), is not particularly limited. In order to minimize the amount of unreacted components, it is preferably set in the range of 0.5 to 2.0, more preferably in the range of 0.6 to 1.3. In terms of moldability and reflow resistance, it is even more preferably set in the range of 0.8 to 1.2.

[0105] (curing accelerator) The curable resin composition may contain a curing accelerator. The type of curing accelerator is not particularly limited and can be selected depending on the type of curable resin, the desired properties of the curable resin composition, and the like.

[0106] From the viewpoint of curability and fluidity, the curing accelerator preferably contains a phosphonium compound. Specific examples of the phosphonium compound include triphenylphosphine, diphenyl(p-tolyl)phosphine, tris(alkylphenyl)phosphine, tris(alkoxyphenyl)phosphine, tris(alkylalkoxyphenyl)phosphine, tris(dialkylphenyl)phosphine, tris(trialkylphenyl)phosphine, tris(tetraalkylphenyl)phosphine, tris(dialkoxyphenyl)phosphine, tris(trialkoxyphenyl)phosphine, and tris(tetraalkoxyphenyl)phosphine. Tertiary phosphines such as sphines, trialkylphosphines, dialkylarylphosphines, and alkyldiarylphosphines are combined with quinone compounds such as maleic anhydride, 1,4-benzoquinone, 2,5-toluquinone, 1,4-naphthoquinone, 2,3-dimethylbenzoquinone, 2,6-dimethylbenzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, and phenyl-1,4-benzoquinone, and compounds with π bonds such as diazophenylmethane, which have intramolecular polarization. Compounds which react with tertiary phosphines include 4-bromophenol, 3-bromophenol, 2-bromophenol, 4-chlorophenol, 3-chlorophenol, 2-chlorophenol, 4-iodophenol, 3-iodophenol, 2-iodophenol, 4-bromo-2-methylphenol, 4-bromo-3-methylphenol, 4-bromo-2,6-dimethylphenol, 4-bromo-3,5-dimethylphenol, 4-bromo-2,6-di-tert-butylphenol, 4-chloro-1-naphthol, 1-bromo-2-naphthol, Examples of such compounds include compounds having intramolecular polarization obtained by reacting a halogenated phenol compound such as 2-naphthol, 6-bromo-2-naphthol, or 4-bromo-4'-hydroxybiphenyl, followed by a dehydrohalogenation step; salts of tetra-substituted phosphonium such as tetraphenylphosphonium and tetra-substituted borates such as tetra-p-tolylborate; salts of tetra-substituted phosphonium and anions obtained by removing a proton from a phenol compound, and salts of tetra-substituted phosphonium and anions obtained by removing a proton from a carboxylic acid compound.

[0107] The phosphonium compound preferably contains a compound represented by the following general formula (I-1) (hereinafter also referred to as a specific curing accelerator).

[0108] [ka]

[0109] In formula (I-1), R 1 ~R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and R 1 ~R 3 Two or more of R may be bonded to each other to form a cyclic structure; 4 ~R 7 are each independently a hydrogen atom, a hydroxyl group, or an organic group having 1 to 18 carbon atoms, and R 4 ~R 7 Two or more of these may be bonded to each other to form a cyclic structure.

[0110] R in general formula (I-1) 1 ~R 3 The "hydrocarbon group having 1 to 18 carbon atoms" described above includes an aliphatic hydrocarbon group having 1 to 18 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms.

[0111] From the viewpoint of flowability, the aliphatic hydrocarbon group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 4 to 6 carbon atoms.

[0112] The aliphatic hydrocarbon group having 1 to 18 carbon atoms may be a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms, or an alicyclic hydrocarbon group having 3 to 18 carbon atoms. From the viewpoint of ease of production, a linear or branched aliphatic hydrocarbon group is preferred.

[0113] Specific examples of linear or branched aliphatic hydrocarbon groups having 1 to 18 carbon atoms include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, octyl, decyl, and dodecyl, as well as allyl and vinyl groups. The linear or branched aliphatic hydrocarbon groups may or may not have a substituent. Examples of the substituent include alkoxy groups such as methoxy, ethoxy, n-butoxy, and t-butoxy, aryl groups such as phenyl and naphthyl, hydroxyl groups, amino groups, and halogen atoms. The linear or branched aliphatic hydrocarbon groups may have two or more substituents, and in such cases, the substituents may be the same or different. When the linear or branched aliphatic hydrocarbon group has a substituent, the total number of carbon atoms contained in the aliphatic hydrocarbon group and the substituent is preferably 1 to 18. From the viewpoint of curability, unsubstituted alkyl groups are preferred, unsubstituted alkyl groups having 1 to 8 carbon atoms are more preferred, and n-butyl, isobutyl, n-pentyl, n-hexyl and n-octyl groups are even more preferred.

[0114] Specific examples of alicyclic hydrocarbon groups having 3 to 18 carbon atoms include cycloalkyl groups such as cyclopentyl, cyclohexyl, and cycloheptyl, and cycloalkenyl groups such as cyclopentenyl and cyclohexenyl. The alicyclic hydrocarbon group may or may not have a substituent. Examples of the substituent include alkyl groups such as methyl, ethyl, n-butyl, and t-butyl; alkoxy groups such as methoxy, ethoxy, n-butoxy, and t-butoxy; aryl groups such as phenyl and naphthyl; hydroxyl groups; amino groups; and halogen atoms. The alicyclic hydrocarbon group may have two or more substituents, and in such cases, the substituents may be the same or different. When the alicyclic hydrocarbon group has a substituent, the total number of carbon atoms contained in the alicyclic hydrocarbon group and the substituent is preferably 3 to 18. When the alicyclic hydrocarbon group has a substituent, the position of the substituent is not particularly limited. From the viewpoint of curability, unsubstituted cycloalkyl groups are preferred, unsubstituted cycloalkyl groups having 4 to 10 carbon atoms are more preferred, and cyclohexyl, cyclopentyl and cycloheptyl groups are even more preferred.

[0115] The aromatic hydrocarbon group having 6 to 18 carbon atoms preferably has 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. The aromatic hydrocarbon group may or may not have a substituent. Examples of the substituent include alkyl groups such as methyl, ethyl, n-butyl, and t-butyl; alkoxy groups such as methoxy, ethoxy, n-butoxy, and t-butoxy; aryl groups such as phenyl and naphthyl; hydroxyl groups; amino groups; and halogen atoms. The aromatic hydrocarbon group may have two or more substituents, and in such cases, the substituents may be the same or different. When the aromatic hydrocarbon group has a substituent, the total number of carbon atoms contained in the aromatic hydrocarbon group and the substituent is preferably 6 to 18. When the aromatic hydrocarbon group has a substituent, the position of the substituent is not particularly limited.

[0116] Specific examples of aromatic hydrocarbon groups having 6 to 18 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, tolyl, dimethylphenyl, ethylphenyl, butylphenyl, t-butylphenyl, methoxyphenyl, ethoxyphenyl, n-butoxyphenyl, and t-butoxyphenyl. The position of the substituent in these aromatic hydrocarbon groups may be any of ortho, meta, and para positions. From the viewpoint of fluidity, unsubstituted aryl groups having 6 to 12 carbon atoms or 6 to 12 carbon atoms including substituents are preferred, unsubstituted aryl groups having 6 to 10 carbon atoms or 6 to 10 carbon atoms including substituents are more preferred, and phenyl, p-tolyl, and p-methoxyphenyl are even more preferred.

[0117] R in general formula (I-1) 1 ~R 3 The term "R" is written as 1 ~R 3 Two or more of R may be bonded to each other to form a cyclic structure. 1 ~R 3 In this case, two or three of the R 1 ~R 3 Examples of the substituent include alkylene groups such as ethylene, propylene, butylene, pentylene, and hexylene, alkenylene groups such as ethyleneylene, propylene, butylene, and butylene, aralkylene groups such as methylenephenylene, and arylene groups such as phenylene, naphthylene, and anthracenylene. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom, or the like.

[0118] R in the above general formula (I-1) 4 ~R 7The "organic group having 1 to 18 carbon atoms" described above is intended to include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aliphatic hydrocarbonoxy group, an aromatic hydrocarbonoxy group, an acyl group, a hydrocarbonoxycarbonyl group, and an acyloxy group, which have 1 to 18 carbon atoms and may be substituted or unsubstituted.

[0119] Examples of the aliphatic hydrocarbon group and aromatic hydrocarbon group include R 1 ~R 3 Examples of the aliphatic hydrocarbon group and aromatic hydrocarbon group represented by the formula (I) include those mentioned above.

[0120] Examples of the aliphatic hydrocarbon oxy group include oxy groups having a structure in which an oxygen atom is bonded to the above-mentioned aliphatic hydrocarbon group, such as a methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, 2-butoxy group, t-butoxy group, cyclopropyloxy group, cyclohexyloxy group, cyclopentyloxy group, allyloxy group, and vinyloxy group, as well as those aliphatic hydrocarbon oxy groups which are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom, or the like.

[0121] Examples of the aromatic hydrocarbon oxy group include oxy groups having a structure in which an oxygen atom is bonded to the above-mentioned aromatic hydrocarbon group, such as a phenoxy group, a methylphenoxy group, an ethylphenoxy group, a methoxyphenoxy group, a butoxyphenoxy group, or a phenoxyphenoxy group, and these aromatic hydrocarbon oxy groups are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom, or the like.

[0122] Examples of the acyl group include aliphatic hydrocarbon carbonyl groups such as formyl, acetyl, ethylcarbonyl, butyryl, cyclohexylcarbonyl, and allylcarbonyl; aromatic hydrocarbon carbonyl groups such as phenylcarbonyl and methylphenylcarbonyl; and these aliphatic hydrocarbon carbonyl groups or aromatic hydrocarbon carbonyl groups which are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom, or the like.

[0123] Examples of the hydrocarbon oxycarbonyl group include aliphatic hydrocarbon oxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, an allyloxycarbonyl group, and a cyclohexyloxycarbonyl group; aromatic hydrocarbon oxycarbonyl groups such as a phenoxycarbonyl group and a methylphenoxycarbonyl group; and these aliphatic hydrocarbon carbonyloxy groups or aromatic hydrocarbon carbonyloxy groups which are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom, or the like.

[0124] Examples of the acyloxy group include aliphatic hydrocarbon carbonyloxy groups such as a methylcarbonyloxy group, an ethylcarbonyloxy group, a butylcarbonyloxy group, an allylcarbonyloxy group, and a cyclohexylcarbonyloxy group; aromatic hydrocarbon carbonyloxy groups such as a phenylcarbonyloxy group and a methylphenylcarbonyloxy group; and these aliphatic hydrocarbon carbonyloxy groups or aromatic hydrocarbon carbonyloxy groups which are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom, or the like.

[0125] R in the above general formula (I-1) 4 ~R 7 The term "R" is written as 4 ~R 7 The phrase "two or more of R may be bonded to each other to form a cyclic structure" means that two to four R 4 ~R 7may be bonded to form a single divalent to tetravalent organic group as a whole. 4 ~R 7 Examples of the cyclic group include substituents capable of forming a cyclic structure, such as alkylene groups such as ethylene, propylene, butylene, pentylene, and hexylene, alkenylene groups such as ethyleneylene, propylene, and butylene, aralkylene groups such as methylenephenylene, and arylene groups such as phenylene, naphthylene, and anthracenylene, as well as oxy or dioxy groups thereof. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom, or the like.

[0126] R in the above general formula (I-1) 4 ~R 7 is not particularly limited. For example, it is preferable that each independently be selected from a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group. Among these, from the viewpoint of availability of raw materials, a hydrogen atom, a hydroxyl group, an aryl group unsubstituted or substituted with at least one selected from the group consisting of an alkyl group and an alkoxy group, or a linear or cyclic alkyl group is preferred. Examples of an unsubstituted aryl group or substituted with at least one selected from the group consisting of an alkyl group and an alkoxy group include a phenyl group, a p-tolyl group, a m-tolyl group, an o-tolyl group, and a p-methoxyphenyl group. Examples of linear or cyclic alkyl groups include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a 2-butyl group, a t-butyl group, an octyl group, and a cyclohexyl group. From the viewpoint of curability, R 4 ~R 7 are all hydrogen atoms, or R 4 ~R 7 It is preferred that at least one of the groups is a hydroxyl group and the rest are all hydrogen atoms.

[0127] In the general formula (I-1), R 1 ~R 3two or more of R are alkyl groups having 1 to 18 carbon atoms or cycloalkyl groups having 3 to 18 carbon atoms; 4 ~R 7 are all hydrogen atoms, or at least one is a hydroxyl group and the rest are all hydrogen atoms. 1 ~R 3 are all alkyl groups having 1 to 18 carbon atoms or cycloalkyl groups having 3 to 18 carbon atoms, and R 4 ~R 7 are all hydrogen atoms, or at least one is a hydroxyl group and the rest are all hydrogen atoms.

[0128] From the viewpoint of rapid curing properties, the specific curing accelerator preferably contains a compound represented by the following general formula (I-2).

[0129] [ka]

[0130] In formula (I-2), R 1 ~R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and R 1 ~R 3 Two or more of R may be bonded to each other to form a cyclic structure; 4 ~R 6 are each independently a hydrogen atom or an organic group having 1 to 18 carbon atoms, and R 4 ~R 6 Two or more of these may be bonded to each other to form a cyclic structure.

[0131] R in general formula (I-2) 1 ~R 6 Specific examples of R in general formula (I-1) 1 ~R 6 The specific examples and preferred ranges are the same as those of the above.

[0132] Specific examples of the specific curing accelerator include an addition reaction product of triphenylphosphine and 1,4-benzoquinone, an addition reaction product of tri-n-butylphosphine and 1,4-benzoquinone, an addition reaction product of tricyclohexylphosphine and 1,4-benzoquinone, an addition reaction product of dicyclohexylphenylphosphine and 1,4-benzoquinone, an addition reaction product of cyclohexyldiphenylphosphine and 1,4-benzoquinone, an addition reaction product of triisobutylphosphine and 1,4-benzoquinone, and an addition reaction product of tricyclopentylphosphine and 1,4-benzoquinone.

[0133] The specific curing accelerator can be obtained, for example, as an adduct of a tertiary phosphine compound and a quinone compound. Specific examples of the tertiary phosphine compound include triphenylphosphine, tributylphosphine, dibutylphenylphosphine, butyldiphenylphosphine, ethyldiphenylphosphine, triphenylphosphine, tris(4-methylphenyl)phosphine, tris(4-ethylphenyl)phosphine, tris(4-n-propylphenyl)phosphine, tris(4-n-butylphenyl)phosphine, tris(isopropylphenyl)phosphine, tris(t-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, etc. From the viewpoint of moldability, triphenylphosphine and tributylphosphine are preferred.

[0134] Specific examples of the quinone compound include o-benzoquinone, p-benzoquinone, diphenoquinone, 1,4-naphthoquinone, anthraquinone, etc. From the viewpoints of moisture resistance and storage stability, p-benzoquinone is preferred.

[0135] The curable resin composition may contain a curing accelerator other than the phosphonium compound. Specific examples of curing accelerators other than phosphonium compounds include diazabicycloalkenes such as 1,5-diazabicyclo[4.3.0]nonene-5 (DBN) and 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), cyclic amidine compounds such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-heptadecylimidazole; derivatives of the above cyclic amidine compounds; phenol novolac salts of the above cyclic amidine compounds or their derivatives; and combinations of these compounds with maleic anhydride, quinone compounds such as 1,4-benzoquinone, 2,5-toluquinone, 1,4-naphthoquinone, 2,3-dimethylbenzoquinone, 2,6-dimethylbenzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, and phenyl-1,4-benzoquinone. compounds having intramolecular polarization obtained by adding a compound having a π bond, such as a tetraphenylborate salt of DBU, a tetraphenylborate salt of DBN, a tetraphenylborate salt of 2-ethyl-4-methylimidazole, or a tetraphenylborate salt of N-methylmorpholine; tertiary amine compounds such as pyridine, triethylamine, triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, and tris(dimethylaminomethyl)phenol; derivatives of the above-mentioned tertiary amine compounds; and ammonium salt compounds such as tetra-n-butylammonium acetate, tetra-n-butylammonium phosphate, tetraethylammonium acetate, tetra-n-hexylammonium benzoate, and tetrapropylammonium hydroxide.

[0136] When the curable resin composition contains a specific curing accelerator as a curing accelerator, the content of the specific curing accelerator is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more of the total curing accelerator.

[0137] When the curable resin composition contains a curing accelerator, the amount thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 15 parts by mass, per 100 parts by mass of the resin components. When the amount of the curing accelerator is 0.1 part by mass or more per 100 parts by mass of the resin components, the composition tends to cure well in a short time. When the amount of the curing accelerator is 30 parts by mass or less per 100 parts by mass of the resin components, the curing speed is not too fast, and a good molded product tends to be obtained.

[0138] (Inorganic filler) The curable resin composition may contain an inorganic filler. In particular, when the curable resin composition is used as an encapsulant for a semiconductor package, it is preferable that the curable resin composition contains an inorganic filler.

[0139] The type of inorganic filler is not particularly limited. Specific examples include inorganic materials such as silica (e.g., spherical silica, crystalline silica), glass, alumina, calcium carbonate, zirconium silicate, calcium silicate, silicon nitride, aluminum nitride, boron nitride, beryllia, zirconia, zircon, fosterite, steatite, spinel, mullite, titania, talc, clay, and mica. Inorganic fillers with flame retardant properties may also be used. Examples of inorganic fillers with flame retardant properties include aluminum hydroxide, magnesium hydroxide, composite metal hydroxides (e.g., magnesium-zinc composite hydroxide), and zinc borate. Among these, spherical silica is preferred from the viewpoint of reducing the linear expansion coefficient, and alumina is preferred from the viewpoint of high thermal conductivity. One type of inorganic filler may be used alone, or two or more types may be used in combination. The inorganic filler may be in the form of powder, beads formed by spheroidizing powder, or fibers.

[0140] When the curable resin composition contains an inorganic filler, its content is not particularly limited. From the viewpoint of fluidity and strength, the content is preferably 30 to 90% by volume, more preferably 35 to 80% by volume, and even more preferably 40 to 70% by volume of the entire curable resin composition. When the content of the inorganic filler is 30% by volume or more of the entire curable resin composition, the properties of the cured product, such as the thermal expansion coefficient, thermal conductivity, and elastic modulus, tend to be further improved. When the content of the inorganic filler is 90% by volume or less of the entire curable resin composition, an increase in the viscosity of the curable resin composition is suppressed, and the fluidity is further improved, tending to result in better moldability.

[0141] The average particle size of the inorganic filler is not particularly limited, but for example, the volume average particle size is preferably 0.2 μm to 50 μm, and more preferably 0.5 μm to 30 μm. When the volume average particle diameter is 0.2 μm or more, an increase in viscosity of the curable resin composition tends to be further suppressed. When the volume average particle diameter is 50 μm or less, the filling ability into narrow gaps tends to be further improved. The volume average particle diameter of the inorganic filler can be measured as the volume average particle diameter (D50) using a laser diffraction scattering particle size distribution analyzer.

[0142] The volume-average particle size of the inorganic filler in the curable resin composition or its cured product can be measured by known methods. For example, the inorganic filler is extracted from the curable resin composition or cured product using an organic solvent, nitric acid, aqua regia, or the like, and then thoroughly dispersed using an ultrasonic disperser or the like to prepare a dispersion. Using this dispersion, the volume-average particle size of the inorganic filler can be measured from the volume-based particle size distribution measured using a laser diffraction / scattering particle size distribution analyzer. Alternatively, the cured product can be embedded in a transparent epoxy resin or the like, polished, and the resulting cross-section observed using a scanning electron microscope to obtain the volume-based particle size distribution. Furthermore, the volume-average particle size of the inorganic filler can also be measured by continuously observing two-dimensional cross-sections of the cured product using an FIB (focused ion beam SEM) device or the like and performing three-dimensional structural analysis.

[0143] From the viewpoint of the flowability of the curable resin composition, the particle shape of the inorganic filler is preferably spherical rather than angular, and the particle size distribution of the inorganic filler is preferably wide.

[0144] [Various additives] In addition to the components described above, the curable resin composition may contain various additives such as coupling agents, ion exchangers, release agents, flame retardants, colorants, and stress relaxation agents, as exemplified below. In addition to the additives exemplified below, the curable resin composition may also contain various additives known in the art, such as ultraviolet absorbers, as needed.

[0145] (coupling agent) When the curable resin composition contains an inorganic filler, it may contain a coupling agent to enhance adhesion between the resin component and the inorganic filler. Examples of the coupling agent include known coupling agents such as silane-based compounds such as epoxysilane, mercaptosilane, aminosilane, alkylsilane, ureidosilane, and vinylsilane, titanium-based compounds, aluminum chelate compounds, and aluminum / zirconium-based compounds.

[0146] When the curable resin composition contains a coupling agent, the amount of the coupling agent is preferably 0.05 to 5 parts by mass, more preferably 0.1 to 2.5 parts by mass, per 100 parts by mass of the inorganic filler. When the amount of the coupling agent is 0.05 parts by mass or more per 100 parts by mass of the inorganic filler, adhesion to the frame tends to be further improved. When the amount of the coupling agent is 5 parts by mass or less per 100 parts by mass of the inorganic filler, moldability of the package tends to be further improved.

[0147] (ion exchanger) The curable resin composition may contain an ion exchanger. In particular, when the curable resin composition is used as a molding material for encapsulation, it is preferable to contain an ion exchanger from the viewpoint of improving the moisture resistance and high-temperature storage characteristics of an electronic component device provided with an element to be encapsulated. The ion exchanger is not particularly limited, and conventionally known ones can be used. Specifically, examples include hydrotalcite compounds and hydrous oxides of at least one element selected from the group consisting of magnesium, aluminum, titanium, zirconium, and bismuth. The ion exchanger may be used alone or in combination of two or more. Among them, hydrotalcite represented by the following general formula (B) is preferable.

[0148] Mg (1-X) Al X (OH)2(CO3) X / 2 ·mH2O ……(B) (0<X≦0.5, m is a positive number)

[0149] When the curable resin composition contains an ion exchanger, its content is not particularly limited as long as it is sufficient to capture ions such as halogen ions. For example, it is preferably 0.1 to 30 parts by mass, more preferably 1 to 15 parts by mass, per 100 parts by mass of the resin component.

[0150] (Release agent) The curable resin composition may contain a release agent from the viewpoint of obtaining good mold release properties with the mold during molding. The release agent is not particularly limited, and conventionally known ones can be used. Specifically, examples include higher fatty acids such as carnauba wax, montanic acid, and stearic acid, metal salts of higher fatty acids, ester waxes such as montanic acid esters, and polyolefin waxes such as oxidized polyethylene and non-oxidized polyethylene. The release agent may be used alone or in combination of two or more.

[0151] When the curable resin composition contains a release agent, the amount thereof is preferably 0.01 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, per 100 parts by mass of the resin component. When the amount of the release agent is 0.01 part by mass or more per 100 parts by mass of the resin component, sufficient release properties tend to be obtained. When the amount is 15 parts by mass or less, better adhesion tends to be obtained.

[0152] (Flame retardant) The curable resin composition may contain a flame retardant. The flame retardant is not particularly limited, and conventionally known flame retardants can be used. Specific examples include organic or inorganic compounds containing halogen atoms, antimony atoms, nitrogen atoms, or phosphorus atoms, and metal hydroxides. The flame retardants may be used alone or in combination of two or more.

[0153] When the curable resin composition contains a flame retardant, the amount thereof is not particularly limited as long as it is an amount sufficient to obtain the desired flame retardant effect. For example, the amount is preferably 1 to 300 parts by mass, more preferably 2 to 150 parts by mass, per 100 parts by mass of the resin component.

[0154] (coloring agent) The curable resin composition may further contain a colorant. Examples of the colorant include known colorants such as carbon black, organic dyes, organic pigments, titanium oxide, red lead, and red iron oxide. The content of the colorant can be appropriately selected depending on the purpose, etc. One type of colorant may be used alone, or two or more types may be used in combination.

[0155] (stress reliever) The curable resin composition may contain a stress relief agent such as silicone oil or silicone rubber particles. The inclusion of a stress relief agent can further reduce package warpage and package cracking. Examples of stress relief agents include commonly used known stress relief agents (flexibilizers). Specific examples include thermoplastic elastomers such as silicone, styrene, olefin, urethane, polyester, polyether, polyamide, and polybutadiene elastomers; rubber particles such as NR (natural rubber), NBR (acrylonitrile-butadiene rubber), acrylic rubber, urethane rubber, and silicone powder; methyl methacrylate-styrene-butadiene copolymer (MBS), methyl methacrylate-silicone copolymer, methyl methacrylate-butyl acrylate copolymer; and copolymers of indenes (e.g., indene and alkylindene) with styrenes (e.g., alkylstyrene) and phenols, containing aromatic olefins such as coumarone as another constituent monomer. The stress relief agents may be used alone or in combination of two or more.

[0156] (Method for preparing curable resin composition) The method for preparing the curable resin composition is not particularly limited. A common method includes thoroughly mixing predetermined amounts of components using a mixer or the like, melt-kneading the mixture using a mixing roll, extruder, or the like, cooling, and pulverizing the mixture. More specifically, for example, a method includes uniformly stirring and mixing predetermined amounts of the components described above, kneading the mixture using a kneader, roll, extruder, or the like that has been preheated to 70°C to 140°C, cooling, and pulverizing the mixture.

[0157] The curable resin composition is preferably solid at room temperature and normal pressure (for example, 25°C, atmospheric pressure). When the curable resin composition is solid, its shape is not particularly limited, and examples thereof include powder, granules, tablets, pellets, and granules. When the curable resin composition is in tablet or pellet form, it is preferable that the dimensions and mass of the tablet or pellet form be such that they are suitable for the molding conditions of the package, from the viewpoint of ease of handling.

[0158] <Electronic component equipment> An electronic component device according to one embodiment of the present disclosure includes an element and a cured product of the above-described curable resin composition that encapsulates the element. Examples of electronic component devices include devices obtained by mounting elements (active elements such as semiconductor chips, transistors, diodes, and thyristors, and passive elements such as capacitors, resistors, and coils) on a support member such as a lead frame, a pre-wired tape carrier, a wiring board, glass, a silicon wafer, or an organic substrate, and then sealing the resulting element portion with a curable resin composition. More specifically, typical resin-sealed ICs such as DIP (Dual Inline Package), PLCC (Plastic Leaded Chip Carrier), QFP (Quad Flat Package), SOP (Small Outline Package), SOJ (Small Outline J-lead Package), TSOP (Thin Small Outline Package), and TQFP (Thin Quad Flat Package) have a structure in which an element is fixed on a lead frame, and terminal portions of the element such as bonding pads and lead portions are connected by wire bonding, bumps, or the like, and then sealed using a curable resin composition by transfer molding or the like; TCP (Tape Carrier Package) has a structure in which an element connected to a tape carrier by bumps is sealed with a curable resin composition; and COB (Chip On Board) has a structure in which an element connected to wiring formed on a support member by wire bonding, flip chip bonding, solder, or the like, is sealed with a curable resin composition. Examples of such devices include BGA (Ball Grid Array), CSP (Chip Size Package), and MCP (Multi Chip Package), which have a structure in which elements are mounted on the surface of a support member having terminals for connecting a wiring board formed on the back surface thereof, the elements are connected to wiring formed on the support member by bump or wire bonding, and then the elements are sealed with a curable resin composition. The curable resin composition can also be suitably used in printed wiring boards.

[0159] Methods for encapsulating electronic component devices using a curable resin composition include low-pressure transfer molding, injection molding, compression molding, etc. Among these, low-pressure transfer molding is the most common. [Example]

[0160] The present disclosure will be specifically described below using examples, but the scope of the present disclosure is not limited to these examples.

[0161] [Preparation of Curable Resin Composition] The curable resin compositions of Examples 1 and 2 and Comparative Examples 1 to 3 were prepared by mixing the following materials in the compositions (parts by mass) shown in Table 1 and performing roll kneading under conditions of a kneading temperature of 80°C and a kneading time of 15 minutes.

[0162] (epoxy resin) Epoxy resin 1: methoxynaphthalene-cresol-formaldehyde co-condensation epoxy resin with an epoxy equivalent of 250 g / eq and a softening point of 58°C (DIC Corporation, product name "HP-5000") Epoxy resin 2: Biphenyl-type epoxy resin with an epoxy equivalent of 196 g / eq and a softening point of 106°C (Mitsubishi Chemical Corporation, product name "YX-4000H") (hardening agent) Curing agent 1: Phenol aralkyl resin with a hydroxyl equivalent of 175 g / eq and a softening point of 70°C (Meiwa Kasei Co., Ltd., product name "MEH-7800SS") Hardener 2: Melamine-modified phenolic resin with a hydroxyl equivalent of 120 g / eq and a softening point of 90°C Curing agent 3: 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine (BASF, trade name "Tinuvin 405") Curing accelerator: Addition product of triphenylphosphine and 1,4-benzoquinone Coupling agent 1: 3-glycidoxypropyltrimethoxysilane Coupling agent 2: 3-phenylaminopropyltrimethoxysilane Release agent 1: Montan wax (Clariant, product name "Licowax E") Release agent 2: Polyethylene oxide (Dainichi Chemical Industry Co., Ltd., product name "PE-A") Colorant: Carbon black (Mitsubishi Chemical Corporation, product name "MA600") Ion exchanger: Hydrotalcite Stress reliever: Indene oligomer Flame retardant: Triphenylphosphine oxide Alkyl melamine: a compound represented by formula (A1) (Sanwa Chemical Co., Ltd., product name "MW-390") Methylated urea resin: a compound represented by the following formula (Sanwa Chemical Co., Ltd., product name "MX-270")

[0163] [ka]

[0164] Inorganic filler: Silica filler (volume average particle size 19 μm)

[0165] [Evaluation of Curable Resin Composition] The properties of the curable resin compositions prepared in Examples 1 and 2 and Comparative Examples 1 to 3 were evaluated by the following property tests. The evaluation results are shown in Table 1 below. The curable resin compositions were molded using a transfer molding machine at a mold temperature of 175°C, a molding pressure of 8.3 MPa, and a curing time of 120 seconds. Subsequently, post-curing was carried out at 175°C for 5 hours to obtain molded products.

[0166] (Evaluation of adhesive strength 1) The surface of a 9mm x 9mm substrate (PPF) with Ni-Pd-Au plating on a copper lead frame or a substrate (Ag) with Ag plating on a copper lead frame is bonded to the substrate using the above method so that the area of ​​the bonding surface is approximately 10mm. 2 A circular molded product was formed. Using a DAGE bond tester, a force was applied to the molded product in the shear direction at a position 50 μm above the substrate surface at a measurement speed of 50 μm / s at 25°C (room temperature), and the force at which the substrate and molded product broke or peeled was measured.

[0167] (Evaluation of adhesive strength 2) Adhesion strength 2 was evaluated in the same manner as in the evaluation of adhesion strength 1, except that the measurement was carried out with the substrate heated to 260°C.

[0168] [Table 1]

[0169] As is clear from the evaluation results in Table 1, the curable resin compositions of Examples 1 and 2, which contain the specific alkylated melamine, have superior adhesive strength at 260°C compared to the curable resin compositions of Comparative Example 1, which does not contain the specific alkylated melamine, and Comparative Examples 2 and 3, which contain a methylated urea resin instead of the specific alkylated melamine.

[0170] The disclosure of Japanese Patent Application No. 2020-170631, filed on October 8, 2020, is incorporated herein by reference in its entirety. All publications, patent applications, and technical standards mentioned in this specification are incorporated by reference into this specification to the same extent as if each individual publication, patent application, or technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. The composition includes a curable resin and a compound represented by the following general formula (A): the curable resin includes an epoxy resin, A curable resin composition that is solid at 25°C and atmospheric pressure. 【Chemical 1】 [In general formula (A), R １１ ~R １６ are each independently a hydrogen atom, —CH ２ OH or -CH ２ OR １７ represents R １７ represents an alkyl group having 1 to 3 carbon atoms. １１ ~R １６ At least one of the following is —CH ２ OR １７ represents.]

2. The compound represented by the general formula (A) is １１ ~R １６ At least four of the groups are -CH ２ OR １７ The curable resin composition according to claim 1, comprising a compound represented by the formula:

3. The compound represented by the general formula (A) is １１ ~R １６ All of -CH ２ OR １７ The curable resin composition according to claim 1, comprising a compound represented by the formula:

4. The curable resin composition according to any one of claims 1 to 3, further comprising an inorganic filler.

5. 5. The curable resin composition according to claim 1, wherein the epoxy resin comprises at least one selected from the group consisting of biphenyl-type epoxy resins, stilbene-type epoxy resins, diphenylmethane-type epoxy resins, sulfur-containing epoxy resins, novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenylmethane-type epoxy resins, copolymer-type epoxy resins, and aralkyl-type epoxy resins.

6. The curable resin composition according to any one of claims 1 to 5, further comprising a curing agent.

7. 7. The curable resin composition according to claim 6, wherein the curing agent comprises at least one selected from the group consisting of aralkyl phenolic resins, dicyclopentadiene phenolic resins, triphenylmethane phenolic resins, copolymerized phenolic resins of triphenylmethane phenolic resins and aralkyl phenolic resins, and novolac phenolic resins.

8. The curable resin composition according to any one of claims 1 to 7, further comprising a curing accelerator.

9. The curable resin composition according to claim 8 , wherein the curing accelerator comprises a phosphonium compound.

10. The curable resin composition according to claim 9, wherein the phosphonium compound comprises a compound represented by the following general formula (I-1): 【Chemistry 2】 [In general formula (I-1), R １ ~R ３ each independently represents a hydrocarbon group having 1 to 18 carbon atoms; R １ ~R ３ At least two of R may be bonded to each other to form a cyclic structure; ４ ~R ７ each independently represents a hydrogen atom, a hydroxyl group, or an organic group having 1 to 18 carbon atoms; R ４ ~R ７ At least two of these may be bonded to each other to form a cyclic structure.]

11. The curable resin composition according to claim 10, wherein the compound represented by the general formula (I-1) includes a compound represented by the following general formula (I-2): 【Chemistry 3】 [In general formula (I-2), R １ ~R ３ each independently represents a hydrocarbon group having 1 to 18 carbon atoms; R １ ~R ３ At least two of R may be bonded to each other to form a cyclic structure; ４ ~R ６ each independently represents a hydrogen atom or an organic group having 1 to 18 carbon atoms; R ４ ~R ６ At least two of these may be bonded to each other to form a cyclic structure.]

12. An electronic component device comprising: an element; and a cured product of the curable resin composition according to any one of claims 1 to 11 that encapsulates the element.

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