JP2006182912A - New compound, curing accelerator, resin composition and electronic component device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound exhibiting excellent fluidity and reconciling rapid curability and storage stability so as to realize electronic component devices having high reliability, to provide a curing accelerator and resin composition containing the compound, and to provide electronic component devices including an element sealed with the compound. <P>SOLUTION: The compound is represented by general formula (I). (Wherein, R<SP>1</SP>to R<SP>3</SP>and R<SP>7</SP>to R<SP>10</SP>are a (substituted) 1-18C hydrocarbon and may be the same or different; R<SP>4</SP>to R<SP>6</SP>are H or a (substituted) 1-18C hydrocarbon and may be the same or different; and R<SP>4</SP>and R<SP>5</SP>may combine to form a cyclic structure). <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a novel compound, a curing accelerator containing the compound, and a resin composition containing the compound, and in particular, a resin composition suitable as a molding material, a laminate, or an adhesive material, and the resin composition The present invention relates to an electronic component device including an element sealed with an object.

  Conventionally, curable resins such as epoxy resins have been widely used in fields such as molding materials, laminates, and adhesive materials. Since these curable resins are required to have fast curability from the viewpoint of improving productivity, a compound that accelerates the curing reaction, that is, a curing accelerator is generally used in the curable resin composition. In the field of sealing technology relating to elements of electronic components such as transistors and ICs, compositions based on epoxy resins are widely used among curable resins. The reason for this is that epoxy resins are balanced in various properties such as moldability, electrical properties, moisture resistance, heat resistance, mechanical properties, and adhesion to inserts. In particular, a combination of an ortho-cresol novolac type epoxy resin and a phenol novolac curing agent has an excellent balance in the above-mentioned characteristics, and therefore has become the mainstream as a base resin for molding materials for IC sealing. And also in such an epoxy resin composition, generally hardening accelerators, such as amine compounds, such as tertiary amine and imidazole, and phosphorus compounds, such as phosphines and phosphonium, are used.

  On the other hand, in recent years, electronic component element sealing technology has been progressing in high-density mounting of electronic components on printed wiring boards, and as a result, surface mount packages are becoming more popular than conventional pin insertion packages. is there. However, in the surface mount type package, the resistance against the package crack at the time of soldering, that is, the so-called reflow crack resistance tends to be reduced as compared with the pin insertion type package. That is, in surface-mounted ICs such as ICs and LSIs, the occupied volume of the element with respect to the package is gradually increased in order to increase the mounting density, and the thickness of the package is very thin. In addition, surface mount packages are subject to more severe conditions in the soldering process than pin insert packages. More specifically, in the pin insertion type package, since the soldering is performed from the back side of the wiring board after the pins are inserted into the wiring board, the package is not directly exposed to a high temperature. After temporarily fixing the plate surface, the package is directly exposed to a high soldering temperature because the solder bath or reflow apparatus is used for processing. As a result, when the IC package absorbs moisture, the moisture absorption moisture may rapidly expand at the time of soldering, resulting in a package crack, which is a big problem in package molding.

  Under such circumstances, an epoxy resin composition in which the content of the inorganic filler is increased has been reported in order to improve the reflow crack resistance in the surface mount package. However, as the content of the inorganic filler increases, the fluidity of the resin composition decreases, and defective molding during molding, such as defective filling, void formation, or poor conduction due to disconnection of the bonding wire of the IC chip. In many cases, the performance of the package is reduced. Therefore, there is a limit to the increase in the content of the inorganic filler, and as a result, it has been difficult to achieve a significant improvement in reflow crack resistance. In particular, such an epoxy resin composition is provided with a phosphorus curing accelerator such as triphenylphosphine and an amine curing accelerator such as 1,8-diazabicyclo [5.4.0] undecene-7 from the viewpoint of rapid curing. If added, the fluidity of the resin composition tends to decrease significantly, so that in addition to improving the resistance to reflow cracking of the package, it is currently desired to improve the fluidity of the resin composition. is there.

  In order to improve the fluidity of an epoxy resin composition containing a high proportion of inorganic filler, for example, a method using an addition reaction product of triphenylphosphine and 1,4-benzoquinone as a curing accelerator has been proposed. (See Patent Document 1). However, the epoxy resin composition containing such a curing accelerator tends to be affected by outside air humidity and tends to have poor storage stability. For this reason, variations in package characteristics are likely to occur, and strict management in the environment during manufacture, transportation, and use is required, and the handleability tends to be inferior. As another method, there is a method of using tetraphenylphosphonium tetraphenylborate as a curing accelerator (see Patent Document 2). However, while the epoxy resin composition by this method exhibits excellent storage stability, it takes time to cure and tends to reduce the productivity during the sealing operation.

JP-A-9-157497 Japanese Patent Publication No.51-24399

  As described above, it is difficult to realize an epoxy resin composition that exhibits excellent fluidity and is satisfactory in both storage stability and rapid curability, and there is a need for such a resin composition. Therefore, in the present invention, an appropriate curing accelerator for realizing a resin composition having such various characteristics, a resin composition containing the same, and a reliability provided with an element sealed with the resin composition It is an object to provide an electronic component device with high performance.

The inventors of the present invention have made extensive studies to solve the above problems, and have found a novel compound suitable as a curing accelerator, and have completed the invention shown below.
(1) A compound represented by the following general formula (I):

（式(I)中、Ｒ¹〜Ｒ^３及びＲ^７〜Ｒ^１０は、炭素数１〜１８の置換又は非置換の炭化水素基を示し、それぞれ全てが同一でも異なっていてもよく、Ｒ^４〜Ｒ^６は、水素原子又は炭素数１〜１８の置換又は非置換の炭化水素基を示し、それぞれ全てが同一でも異なっていてもよく、Ｒ^４とＲ^５が結合して環状構造となっていてもよい。）
（２）一般式（I）において、Ｒ^１〜Ｒ^３及びＲ^７〜Ｒ^１０がメチル基、エチル基、イソプロピル基、ｎ-ブチル基、sec-ブチル基、tert-ブチル基、オクチル基、シクロヘキシル基、ベンジル基、フェニル基、ｐ-トリル基、ｍ-トリル基、ｏ-トリル基、ｐ-メトキシフェニル基、ｍ-メトキシフェニル基、ｏ-メトキシフェニル基からなる群から選ばれる基であり、Ｒ^４〜Ｒ^６が水素原子であることを特徴とする上記（１）に記載の化合物。
（３）一般式（I）において、Ｒ^１〜Ｒ^３及びＲ^７〜Ｒ^１０がフェニル基であり、Ｒ^４〜Ｒ^６が水素原子であることを特徴とする上記（１）または（２）に記載の化合物。
（４）上記（１）から（３）のいずれかに記載の１種以上の化合物を含有することを特徴とする硬化促進剤。
（５）（Ａ）上記（４）に記載の１種以上の硬化促進剤と、（Ｂ）エポキシ樹脂とを含有することを特徴とする樹脂組成物。
（６）（Ｃ）硬化剤をさらに含有することを特徴とする上記（５）に記載の樹脂組成物。
（７）（Ｄ）無機充填剤をさらに含有することを特徴とする上記（５）又は（６）に記載の樹脂組成物。
（８）（Ｂ）エポキシ樹脂が、ビフェニル型エポキシ樹脂、スチルベン型エポキシ樹脂、ジフェニルメタン型エポキシ樹脂、硫黄原子含有型エポキシ樹脂、ノボラック型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、サリチルアルデヒド型エポキシ樹脂、ナフトール類とフェノール類との共重合型エポキシ樹脂、アラルキル型フェノール樹脂のエポキシ化物からなる群から選択される少なくとも１種のエポキシ樹脂を含有することを特徴とする上記（５）から（７）のいずれかに記載の樹脂組成物。
（９）（Ｃ）硬化剤が、アラルキル型フェノール樹脂、ジシクロペンタジエン型フェノール樹脂、サリチルアルデヒド型フェノール樹脂、ベンズアルデヒド型フェノール樹脂とアラルキル型フェノール樹脂の共重合型樹脂、ノボラック型フェノール樹脂からなる群から選択される少なくとも１種の硬化剤を含有することを特徴とする上記（６）から（８）のいずれかに記載の樹脂組成物。
（１０）上記（５）から（９）のいずれかに記載の樹脂組成物によって封止された素子を備えることを特徴とする電子部品装置。

(In the formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ represent a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, and each may be the same or different, and R ⁴ ˜R ⁶ represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, all of which may be the same or different, and R ⁴ and R ⁵ are bonded to form a cyclic structure. May be.)
(2) In the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are methyl group, ethyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, octyl group, cyclohexyl A group selected from the group consisting of a group, benzyl group, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, p-methoxyphenyl group, m-methoxyphenyl group, o-methoxyphenyl group, R < ⁴ > -R < ⁶ > is a hydrogen atom, The compound as described in said (1) characterized by the above-mentioned.
(3) In the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are phenyl groups, and R ^{4 to} R ⁶ are hydrogen atoms, (1) or (2) Compound described in 1.
(4) A curing accelerator comprising one or more compounds according to any one of (1) to (3) above.
(5) (A) One or more hardening accelerator as described in said (4), and (B) epoxy resin are contained, The resin composition characterized by the above-mentioned.
(6) The resin composition as described in (5) above, further comprising (C) a curing agent.
(7) The resin composition as described in (5) or (6) above, further comprising (D) an inorganic filler.
(8) (B) The epoxy resin is a biphenyl type epoxy resin, a stilbene type epoxy resin, a diphenylmethane type epoxy resin, a sulfur atom-containing type epoxy resin, a novolac type epoxy resin, a dicyclopentadiene type epoxy resin, a salicylaldehyde type epoxy resin, (5) to (7) above, characterized by containing at least one epoxy resin selected from the group consisting of epoxides of copolymerized naphthols and phenols and aralkyl-type phenolic resins The resin composition in any one.
(9) (C) The curing agent is made of an aralkyl type phenol resin, a dicyclopentadiene type phenol resin, a salicylaldehyde type phenol resin, a copolymer type resin of a benzaldehyde type phenol resin and an aralkyl type phenol resin, or a novolac type phenol resin. The resin composition as described in any one of (6) to (8) above, which contains at least one curing agent selected from the group consisting of:
(10) An electronic component device comprising an element sealed with the resin composition according to any one of (5) to (9).

  The curing accelerator containing the novel compound according to the present invention exhibits excellent fluidity, and can achieve both fast curability and excellent storage stability. Therefore, by using a resin composition composed of such a curing accelerator when sealing an element of an electronic component such as an IC or LSI, the productivity of sealing work is improved and reliability is improved. It is possible to provide a high electronic component, and its industrial value is high.

  Hereinafter, the present invention will be described in detail. The novel compound according to the present invention is a compound represented by the following general formula (I).

（式(I)中、Ｒ¹〜Ｒ^３及びＲ^７〜Ｒ^１０は、炭素数１〜１８の置換又は非置換の炭化水素基を示し、それぞれ全てが同一でも異なっていてもよく、Ｒ^４〜Ｒ^６は、水素原子又は炭素数１〜１８の置換又は非置換の炭化水素基を示し、それぞれ全てが同一でも異なっていてもよく、Ｒ^４とＲ^５が結合して環状構造となっていてもよい。）
なお、本明細書で使用する用語「炭素数１〜１８の置換又は非置換の炭化水素基」は、炭素数１〜１８を有し、それぞれ置換されても又は非置換であってもよい、脂肪族炭化水素基、脂環式炭化水素基、および芳香族炭化水素基を含む。

(In the formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ represent a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, and each may be the same or different, and R ⁴ ˜R ⁶ represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, all of which may be the same or different, and R ⁴ and R ⁵ are bonded to form a cyclic structure. May be.)
The term “substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms” used in the present specification has 1 to 18 carbon atoms and may be substituted or unsubstituted, respectively. Including an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.

  Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, decyl group, Examples thereof include alkyl groups such as dodecyl group, allyl groups, vinyl groups, and the like, and those substituted with alkyl groups, alkoxy groups, aryl groups, hydroxyl groups, amino groups, halogens, and the like. Although not particularly limited, a methyl group, ethyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, octyl group, or benzyl group is preferable.

  Examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, and the like, and an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a hydroxyl group, an amino group, and the like. And those substituted with a group, halogen and the like. Although not particularly limited, a cyclohexyl group is preferable.

  Examples of the aromatic hydrocarbon group include an aryl group such as a phenyl group and a tolyl group, an alkyl group-substituted aryl group such as a dimethylphenyl group, an ethylphenyl group, a butylphenyl group, and a tert-butylphenyl group, and a methoxyphenyl group. Alkoxy group-substituted aryl groups such as ethoxyphenyl group, butoxyphenyl group, tert-butoxyphenyl group, etc., and those substituted with alkyl groups, alkoxy groups, aryl groups, aryloxy groups, hydroxyl groups, amino groups, halogens, etc. Etc. Although not particularly limited, a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a p-methoxyphenyl group, an m-methoxyphenyl group, and an o-methoxyphenyl group are preferable.

In the general formula (I), when R ⁴ and R ⁵ are combined to form a cyclic structure, it is not particularly limited, but examples thereof include compounds represented by the following general formulas (II) to (IV). It is done.

特に限定されるものではないが、一般式(I)において、Ｒ¹〜Ｒ^３及びＲ^７〜Ｒ^１０がそれぞれ独立して、メチル基、エチル基、イソプロピル基、ｎ-ブチル基、sec-ブチル基、tert-ブチル基、オクチル基、シクロヘキシル基、ベンジル基、フェニル基、ｐ-トリル基、ｍ-トリル基、ｏ-トリル基、ｐ-メトキシフェニル基、ｍ-メトキシフェニル基、ｏ-メトキシフェニル基からなる群から選ばれる基であり、Ｒ^４〜Ｒ^６がそれぞれ独立して水素原子、メチル基、tert-ブチル基、フェニル基から選ばれる基であるか又はＲ^４とＲ^５が結合して上記一般式（II）で示される環状構造を有し、Ｒ^６が水素原子である化合物が好ましい。

Although not particularly limited, in the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are each independently methyl, ethyl, isopropyl, n-butyl, sec-butyl. Group, tert-butyl group, octyl group, cyclohexyl group, benzyl group, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, p-methoxyphenyl group, m-methoxyphenyl group, o-methoxyphenyl R ^{4 to} R ⁶ are each independently a group selected from a hydrogen atom, a methyl group, a tert-butyl group, and a phenyl group, or R ⁴ and R ⁵ are bonded to each other. A compound having a cyclic structure represented by the above general formula (II) and R ⁶ being a hydrogen atom is preferred.

In the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are each independently a methyl group, ethyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, octyl group. A group selected from the group consisting of cyclohexyl, benzyl, phenyl, p-tolyl, m-tolyl, o-tolyl, p-methoxyphenyl, m-methoxyphenyl, and o-methoxyphenyl And a compound in which R ^{4 to} R ⁶ are hydrogen atoms is more preferable. Specific examples of such compounds include compounds in which R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are each independently a phenyl group, and R ^{4 to} R ⁶ are each independently hydrogen.

  For example, as shown in the following scheme, the compound represented by the general formula (I) is formed by adding an acid to an addition reaction product of a tri-substituted phosphine and p-quinones to form an intermolecular salt, and then forming a metal tetra-substituted borate. Can be produced by a method in which the anion part of the intermolecular salt is exchange-reacted.

上記スキームにおいて、Ｒ¹〜Ｒ^３、Ｒ^４〜Ｒ^６、及びＲ^７〜Ｒ^１０は、先に説明した通りである。また、ＨＸは無機酸又は有機酸を示し、Ｘ^-はＨＸからプロトンが脱離した基を示し、Ｍは金属元素を示し、ｎはその価数であり正の整数を示す。

In the above scheme, R ^{1 to} R ³ , R ^{4 to} R ⁶ , and R ^{7 to} R ¹⁰ are as described above. HX represents an inorganic acid or an organic acid, X ⁻ represents a group in which a proton is eliminated from HX, M represents a metal element, n represents a valence thereof, and represents a positive integer.

  The inorganic acid and the organic acid are not particularly limited as long as they are Bronsted acids that form salts with adducts formed by reacting tri-substituted phosphines and p-quinones. Examples of the inorganic acid include, but are not limited to, hydrochloric acid, sulfuric acid, nitric acid, and the like. Examples of the organic acid include oxalic acid, acetic acid, benzoic acid, and the like, but are not limited thereto. .

M ^{n +} is not particularly limited as long as it is a metal ion capable of forming a salt with a tetra-substituted borate. For example, Li ⁻ , Na ⁻ , K ⁻ , Rb ⁻ , Cs ⁻ , Be ²⁻ , Mg ²⁻ , Ca ²⁻ , Ba ²⁻ , Be ²⁻ , Fe ³⁻ , Cu ²⁻ , Zn ²⁻ , Ni ^2- , Ag- ^{and the} like.

  In addition, when manufacturing the compound of this invention shown by general formula (I) according to the said scheme, a reaction solvent can also be used. Preferred examples of the reaction solvent for achieving the reaction of the addition reaction product of tri-substituted phosphine and p-quinones with the metal tetra-substituted borate include methanol, methanol / water mixed solvent and the like. However, the reaction solvent is not particularly limited as long as the above reaction can be achieved.

  The curing accelerator according to the present invention is characterized by containing one or more compounds represented by the above general formula (I). By using such a curing accelerator, it is possible to realize excellent fluidity, curability and storage stability in the resin composition. That is, the compound represented by the general formula (I) can be used as a suitable curing accelerator. The compounding amount of the above compound based on the total weight of the curing accelerator according to the present invention is preferably 30% by weight or more, and more preferably 50% by weight or more. When the compounding amount of the compound is less than 30% by weight, a sufficient effect cannot be obtained, and the resin composition tends to be inferior in curability and / or fluidity.

  The resin composition according to the present invention contains (A) a curing accelerator and (B) an epoxy resin, and (A) the curing accelerator contains one or more curing accelerators according to the present invention described above. It is characterized by. The resin composition according to the present invention may contain components such as (C) a curing agent and (D) an inorganic filler, and if necessary, an ion exchanger, a coupling agent, and a release agent. Various additives known in the art such as flame retardants and colorants may be added.

  In addition, the compounding quantity of (A) hardening accelerator in a resin composition will not be restrict | limited especially if the hardening promotion effect is acquired. However, from the viewpoints of curability and fluidity at the time of moisture absorption, it is preferable to blend 0.1 to 10 parts by weight of (A) a curing accelerator with respect to 100 parts by weight of the total of (B) epoxy resin. It is more preferable to set it to -7.0 weight part. When the blending amount is less than 0.1 parts by weight, it is difficult to cure the resin composition in a short time, and when the blending amount exceeds 10 parts by weight, the curing rate is too high to form a good molded product. Tend to be.

  Hereinafter, various components constituting the resin composition according to the present invention will be described in detail.

  The (A) curing accelerator contains one or more curing accelerators containing one or more compounds represented by the general formula (I) described above. In addition to such compounds, curing of the epoxy resin is possible. One or more known curing accelerators that promote the reaction may be used in combination.

  Examples of the curing accelerator that can be used in combination include diazabicycloalkenes such as 1,5-diazabicyclo [4.3.0] nonene-5, 1,8-diazabicyclo [5.4.0] undecene-7, and the like. Cycloamidine compounds, derivatives thereof, phenol novolac salts thereof and these compounds to maleic anhydride, 1,4-benzoquinone, 2,5-toluquinone, 1,4-naphthoquinone, 2,3-dimethylbenzoquinone, 2,6- Quinone compounds such as dimethylbenzoquinone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, phenyl-1,4-benzoquinone, and π bonds such as diazophenylmethane A compound having an intramolecular polarization formed by adding a compound having a triethylenediamine, benzyldimethylamine, Tertiary amines such as tanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol and their derivatives, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-heptadecylimidazole, etc. Imidazoles, tetrasubstituted phosphonium tetrasubstituted borates such as tetraphenylphosphonium tetraphenylborate, tetraphenylboron salts such as 2-ethyl-4-methylimidazole tetraphenylborate, N-methylmorpholine tetraphenylborate, tri Phenylphosphine, 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, tris (tetraalkoxyphenyl) phosphine, Organic phosphines such as trialkylphosphine, dialkylarylphosphine, alkyldiarylphosphine, etc., complexes of these organic phosphines with organic borons, organic phosphines with 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-benzene Zokinon, quinone compounds such as phenyl-1,4-benzoquinone, compounds having an addition to intramolecular polarization comprising a compound having a π bond, such as diazo methane may be mentioned.

  When the above-mentioned known curing accelerator is used in combination to constitute the (A) curing accelerator, the total content of one or more compounds represented by the general formula (I) with respect to the total curing accelerator is 30% by weight or more. More preferably, the total should be 50% by weight or more. (A) When the compounding quantity of the said compound in a hardening accelerator is less than 30 weight%, the sclerosis | hardenability and / or fluidity | liquidity at the time of moisture absorption will fall, and there exists a tendency for the effect which can be achieved by this invention to fall.

  (B) The epoxy resin may be a general epoxy resin having two or more epoxy groups in one molecule, and is not particularly limited. More specifically, for example, phenols such as phenol novolac type epoxy resin, orthocresol novolac type epoxy resin, cresol, xylenol, resorcin, catechol, bisphenol A, bisphenol F and the like, and / or α-naphthol, Epoxylated novolak resin obtained by condensation or cocondensation of naphthols such as β-naphthol and dihydroxynaphthalene with compounds having aldehyde groups such as formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, salicylaldehyde in the presence of an acidic catalyst. (Novolak-type epoxy resin); bisphenol A, bisphenol F, bisphenol S, alkyl-substituted or unsubstituted biphenol, stilbene phenols, etc. Glycidyl ether of alcohols such as sidyl ether (bisphenol type epoxy resin, biphenyl type epoxy resin, stilbene type epoxy resin), butanediol, polyethylene glycol, polypropylene glycol; glycidyl of carboxylic acids such as phthalic acid, isophthalic acid, tetrahydrophthalic acid, etc. Ester-type epoxy resin; Glycidyl-type or methylglycidyl-type epoxy resin such as aniline, isocyanuric acid, etc., in which active hydrogen bonded to nitrogen atom is substituted with glycidyl group; Vinylcyclohexene obtained by epoxidizing olefin bond in the molecule Diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 2- (3,4-epoxy) cyclohexyl-5,5-spiro (3,4 Poxy) cycloaliphatic epoxy resins such as cyclohexane-m-dioxane; glycidyl ether of paraxylylene and / or metaxylylene modified phenol resin; glycidyl ether of terpene modified phenol resin; glycidyl ether of dicyclopentadiene modified phenol resin; cyclopentadiene modified phenol resin Glycidyl ether of polycyclic aromatic ring modified phenolic resin; Glycidyl ether of phenol resin containing naphthalene ring; Halogenated phenol novolac type epoxy resin; Hydroquinone type epoxy resin; Trimethylolpropane type epoxy resin; Linear aliphatic epoxy resin obtained by oxidation with peracid of diphenylmethane type epoxy resin; phenol aralkyl resin, naphthol alcohol Epoxidized aralkyl phenolic resins such as alkyl resins; sulfur atom-containing epoxy resin, and the like. These epoxy resins may be used alone or in combination of two or more.

  Among the above-mentioned epoxy resins, from the viewpoint of reflow crack resistance and fluidity, biphenyl type epoxy resin, stilbene type epoxy resin, diphenylmethane type epoxy resin, sulfur atom-containing type epoxy resin, novolac type epoxy resin, dicyclopentadiene type epoxy An epoxidized product of an aralkyl type phenol resin such as a resin, a salicylaldehyde type epoxy resin, a copolymer type epoxy resin of naphthols and phenols, a phenol aralkyl resin, or a naphthol aralkyl resin is preferable. These epoxy resins may be used alone or in combination of two or more, but in order to exert their performance, the total amount is preferably 30% by weight or more based on the total epoxy resin. Preferably, the total amount is 50% by weight or more. Specific examples of preferable epoxy resins are shown below.

  The biphenyl type epoxy resin is not particularly limited as long as it is an epoxy resin having a biphenyl skeleton, but an epoxy resin represented by the following general formula (V) is preferable.

（一般式（V）中、Ｒ^８は水素原子又は炭素数１〜１２のアルキル基又は炭素数４〜１８のアリール基を示し、それぞれ全てが同一でも異なっていてもよく、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（V）で示されるエポキシ樹脂の中でも、Ｒ^８のうち酸素原子が置換している位置を４及び４´位とした時の３，３´，５，５´位がメチル基でそれ以外が水素原子であるＹＸ-４０００Ｈ(ジャパンエポキシレジン株式会社製商品名)、すべてのＲ^８が水素原子である４，４´−ビス（２，３−エポキシプロポキシ）ビフェニル、すべてのＲ^８が水素原子の場合及びＲ^８のうち酸素原子が置換している位置を４及び４´位とした時の３，３´，５，５´位がメチル基でそれ以外が水素原子である場合の混合品であるＹＬ-６１２１Ｈ(ジャパンエポキシレジン株式会社製商品名)等が市販品として入手可能である。

(In the general formula (V), R ⁸ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an aryl group having 4 to 18 carbon atoms, all of which may be the same or different, and n is an average value. Yes, and represents a positive integer from 0 to 10.)
Among the epoxy resins represented by the general formula (V), the methyl groups are located at the 3, 3 ′, 5, 5 ′ positions when the positions where oxygen atoms are substituted in the R ⁸ are the 4 and 4 ′ positions. Other than that, YX-4000H (trade name, manufactured by Japan Epoxy Resin Co., Ltd.), which is a hydrogen atom, 4,4′-bis (2,3-epoxypropoxy) biphenyl, in which all R ⁸ are hydrogen atoms, and all R ⁸ When hydrogen is a hydrogen atom and when the oxygen atom substitution positions in R ⁸ are the 4 and 4 'positions, the 3, 3', 5, 5 'positions are methyl groups, and the others are hydrogen atoms YL-6121H (trade name, manufactured by Japan Epoxy Resin Co., Ltd.), which is a mixture of these, is available as a commercial product.

  The stilbene type epoxy resin is not particularly limited as long as it is an epoxy resin having a stilbene skeleton, but an epoxy resin represented by the following general formula (VI) is preferable.

（一般式（VI）中、Ｒ^９及びＲ^１０は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（VI）で示されるエポキシ樹脂の中でも、Ｒ^９のうち酸素原子が置換している位置を４及び４´位とした時の３，３´，５，５´位がメチル基でそれ以外が水素原子でありＲ^１０の全てが水素原子の場合と、３，３´，５，５´位のうちの３つがメチル基、１つがtert−ブチル基でそれ以外が水素原子でありＲ^１０の全てが水素原子の場合との混合品である、ＥＳＬＶ-２１０(ジャパンエポキシレジン株式会社製商品名)等が市販品として入手可能である。

(In the general formula (VI), R ⁹ and R ^{10 each} represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, and n is an average value. Represents a positive integer of -10.)
Among the epoxy resins represented by the above general formula (VI), 3, ⁹ ′, 5 ′ and 5 ′ positions when the positions where oxygen atoms are substituted in R ⁹ are 4 and 4 ′ positions are methyl groups. The other is a hydrogen atom and all of R ¹⁰ are hydrogen atoms, and three of the 3, 3 ′, 5, 5 ′ positions are methyl groups, one is a tert-butyl group and the other are hydrogen atoms. ESLV-210 (trade name, manufactured by Japan Epoxy Resin Co., Ltd.), which is a mixed product with the case where all of R ¹⁰ are hydrogen atoms, is commercially available.

  The diphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin having a diphenylmethane skeleton, but an epoxy resin represented by the following general formula (VII) is preferable.

（一般式（VII）中、Ｒ^１１及びＲ^１２は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（VII）で示されるエポキシ樹脂の中でも、Ｒ^１１の全てが水素原子でありＲ^１２のうち酸素原子が置換している位置を４及び４´位とした時の３，３´，５，５´位がメチル基でそれ以外が水素原子であるＹＳＬＶ−８０ＸＹ(新日鐵化学株式会社製商品名)等が市販品として入手可能である。

(In the general formula (VII), R ¹¹ and R ^{12 each} represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different, and n is an average value, 0 Represents a positive integer of -10.)
Among the epoxy resins represented by the general formula (VII), all of R ¹¹ are hydrogen atoms, and the positions where oxygen atoms are substituted in R ¹² are 3, 3 ′, YSLV-80XY (trade name, manufactured by Nippon Steel Chemical Co., Ltd.), in which the 5,5′-position is a methyl group and the other is a hydrogen atom, is commercially available.

  Although it will not specifically limit if it is an epoxy resin containing a sulfur atom as a sulfur atom containing type epoxy resin, For example, the epoxy resin shown by the following general formula (VIII) is mentioned.

（一般式（VIII）中、Ｒ^１３は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（VIII）で示されるエポキシ樹脂の中でも、Ｒ^１３のうち酸素原子が置換している位置を４及び４´位とした時の３，３´位がtert−ブチル基で６，６´位がメチル基でそれ以外が水素原子であるＹＳＬＶ−１２０ＴＥ(新日鐵化学株式会社製商品名)等が市販品として入手可能である。

(In the general formula (VIII), R ¹³ represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, n is an average value, Indicates a positive integer.)
Among the epoxy resins represented by the above general formula (VIII), the tert-butyl group is 6, 6 when the position where the oxygen atom is substituted in R ¹³ is 4 and 4 ', YSLV-120TE (trade name, manufactured by Nippon Steel Chemical Co., Ltd.) in which the '-position is a methyl group and the other is a hydrogen atom is commercially available.

  The novolak type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a novolak type phenol resin, and a novolak type phenol resin such as phenol novolak, cresol novolak, naphthol novolak, etc. is glycidyl etherified, etc. Epoxy resins epoxidized using the above method are preferred. For example, an epoxy resin represented by the following general formula (IX) is more preferable.

（一般式（IX）中、Ｒ^１４及びＲ^１５は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（IX）で示されるエポキシ樹脂の中でも、Ｒ^１４の全てが水素原子でありＲ^１５がメチル基でｉ＝１であるＥＳＣＮ−１９０、ＥＳＣＮ−１９５(住友化学株式会社製商品名)等が市販品として入手可能である。

(In the general formula (IX), R ¹⁴ and R ¹⁵ represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, and i is an integer of 0 to 3, n is an average value and represents a positive integer of 0 to 10.)
Among the epoxy resins represented by the general formula (IX), ESCN-190 and ESCN-195 (trade names, manufactured by Sumitomo Chemical Co., Ltd.), in which all of R ¹⁴ are hydrogen atoms, R ¹⁵ is a methyl group and i = 1. Etc. are available as commercial products.

  The dicyclopentadiene type epoxy resin is not particularly limited as long as it is an epoxy resin epoxidized using a compound having a dicyclopentadiene skeleton as a raw material, but an epoxy resin represented by the following general formula (X) is preferable.

（一般式（X）中、Ｒ^１６は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（X）で示されるエポキシ樹脂の中でも、ｉ＝０であるＨＰ−７２００(大日本インキ化学株式会社製商品名)等が市販品として入手可能である。

(In the general formula (X), R ¹⁶ represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, i is an integer of 0 to 3, and n is an average. It is a value and represents a positive integer from 0 to 10.)
Among the epoxy resins represented by the general formula (X), HP-7200 (trade name, manufactured by Dainippon Ink & Chemicals, Inc.) where i = 0 is available as a commercial product.

  The salicylaldehyde type epoxy resin is not particularly limited as long as it is an epoxy resin made from a compound having a salicylaldehyde skeleton, but a salicyl such as a novolak type phenolic resin of a compound having a salicylaldehyde skeleton and a compound having a phenolic hydroxyl group. A salicylaldehyde type epoxy resin such as an epoxy resin obtained by converting an aldehyde type phenolic resin into a glycidyl ether is preferable, and an epoxy resin represented by the following general formula (XI) is more preferable.

（一般式（XI）中、Ｒ^１７及びＲ^１８は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｋは０〜４の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（XI）で示されるエポキシ樹脂の中でも、ｉ＝０、ｋ＝０であるＭＥＨ−７５００(明和化成株式会社製商品名)等が市販品として入手可能である。

(In the general formula (XI), R ¹⁷ and R ¹⁸ represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, and i is an integer of 0 to 3, k is an integer of 0 to 4, n is an average value, and represents a positive integer of 0 to 10.)
Among the epoxy resins represented by the general formula (XI), MEH-7500 (trade name, manufactured by Meiwa Kasei Co., Ltd.) where i = 0 and k = 0 is available as a commercial product.

  The copolymer type epoxy resin of naphthols and phenols 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, but a compound having a naphthol skeleton And a novolak-type phenol resin using a compound having a phenol skeleton, which is glycidyl etherified, and more preferably an epoxy resin represented by the following general formula (XII).

（一般式（XII）中、Ｒ^１９〜Ｒ^２１は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、
ｉは０〜３の整数、ｊは０〜２の整数、ｋは０〜４の整数を示し、ｐは平均値で０〜１の正の整数を示し、
ｌ、ｍはそれぞれ平均値で０〜１１の正の整数であり（ｌ＋ｍ）は１〜１１の正の整数を示す。）
上記一般式（XII）で示されるエポキシ樹脂の中でも、ｉ＝１、ｊ＝０、ｋ＝０であり、Ｒ^２１がメチル基であるＮＣ−７３００(日本化薬株式会社製商品名)等が市販品として入手可能である。

(In the general formula (XII), R ^{19 to} R ²¹ represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different,
i represents an integer of 0 to 3, j represents an integer of 0 to 2, k represents an integer of 0 to 4, p represents an average positive integer of 0 to 1,
Each of l and m is a positive integer of 0 to 11 on average, and (l + m) represents a positive integer of 1 to 11. )
Among the epoxy resins represented by the general formula (XII), NC-7300 (trade name, manufactured by Nippon Kayaku Co., Ltd.) where i = 1, j = 0, k = 0 and R ²¹ is a methyl group It is available as a commercial product.

  Epoxidized products of aralkyl-type phenol resins such as phenol aralkyl resins and naphthol aralkyl resins include phenols such as phenol and cresol and / or naphthols such as naphthol and dimethylnaphthol, dimethoxyparaxylene, bis (methoxymethyl) biphenyl, and the like. The epoxy resin is not particularly limited as long as it is made of a phenol resin synthesized from the above derivatives. Phenol resins such as phenol and cresol and / or naphthols such as naphthol and dimethylnaphthol, and phenol resins synthesized from dimethoxyparaxylene, bis (methoxymethyl) biphenyl, and derivatives thereof are preferably glycidyl etherified, Epoxy resins represented by the formulas (XIII) and (XIV) are more preferable.

（ここで、一般式（XIII）及び（XIV）中のＲ^３７〜Ｒ^４１は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよい。ｉは０〜３の整数、ｊは０〜２の整数、ｋは０〜４の整数を示す。）
上記一般式（XIII）で示されるエポキシ樹脂の中でも、ｉ＝０、Ｒ^３８が水素原子であるＮＣ−３０００Ｓ(日本化薬株式会社製商品名)、ｉ＝０、Ｒ^３８が水素原子であるエポキシ樹脂と一般式（V）のすべてのＲ^８が水素原子であるエポキシ樹脂を重量比８０：２０で混合したＣＥＲ-３０００(日本化薬株式会社製商品名)等が入手可能である。また上記一般式（XIV）で示されるエポキシ樹脂の中でも、ｉ＝０、ｊ＝０、ｋ＝０であるＥＳＮ−１７５(新日鐵化学株式会社商品名)等が市販品として入手可能である。

(Here, R ^{37 to} R ⁴¹ in the general formulas (XIII) and (XIV) each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and all may be the same or different. Is an integer from 0 to 3, j is an integer from 0 to 2, and k is an integer from 0 to 4.)
Among the epoxy resins represented by the general formula (XIII), i = 0, R- ³⁸ is a hydrogen atom, NC-3000S (trade name, manufactured by Nippon Kayaku Co., Ltd.), i = 0, R- ³⁸ is a hydrogen atom. CER-3000 (trade name, manufactured by Nippon Kayaku Co., Ltd.) in which an epoxy resin and an epoxy resin in which all R ^{8 in} the general formula (V) are hydrogen atoms are mixed at a weight ratio of 80:20 are available. Among the epoxy resins represented by the general formula (XIV), ESN-175 (trade name of Nippon Steel Chemical Co., Ltd.) where i = 0, j = 0, and k = 0 are available as commercial products. .

Regarding R ^{8 to} R ²¹ and R ^{37 to} R ^{41 in the} above general formulas (V) to (XII), (XIII) and (XIV), “all may be the same or different,” for example, It means that all of ^{8 to} 88 R ⁸ in (V) may be the same or different. It means that all of R ^{9 to} R ²¹ and R ^{37 to} R ⁴¹ may be the same or different with respect to the respective numbers contained in the formula. R ^{8 to} R ²¹ and R ^{37 to} R ⁴¹ may be the same as or different from each other. For example, all of R ⁹ and R ¹⁰ may be the same or different.

  As the epoxy resin represented by the general formula (XII), a random copolymer including 1 structural unit and m structural units randomly, an alternating copolymer including alternately, a copolymer including regularly, The block copolymer contained in a block shape is mentioned, Any one of these may be used independently or may be used in combination of 2 or more type.

  N in the above general formulas (V) to (XI), (XIII) and (XIV) needs to be in the range of 0 to 10, and when it exceeds 10, the melt viscosity of the component (B) becomes high. For this reason, the viscosity at the time of melt molding of the resin composition also increases, which tends to cause unfilling failure and deformation of the bonding wire (gold wire connecting the element and the lead). The average n per molecule is preferably set in the range of 0-4.

  The preferred (B) epoxy resin that can be used in the resin composition according to the present invention has been exemplified according to the general formulas (V) to (XIV). As a more specific preferred (B) epoxy resin, reflow cracking resistance 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl can be mentioned from the viewpoint of moldability, and 4,4′-bis from the viewpoint of moldability and heat resistance. (2,3-epoxypropoxy) -biphenyl.

  In the resin composition by this invention, (C) hardening | curing agent can be used as needed. The usable curing agent is not particularly limited as long as it is a compound that can cure the epoxy resin. For example, phenol compounds such as phenol resin, amine compounds such as diamine and polyamine, phthalic anhydride, trimellitic anhydride, organic anhydrides such as pyromellitic anhydride, carboxylic acid compounds such as dicarboxylic acid, polycarboxylic acid, etc. Of these, one type may be used alone, or two or more types may be used in combination. Among these, from the viewpoint that the effect of the (A) curing accelerator is sufficiently exhibited, a phenol resin is preferable.

  There is no restriction | limiting in particular as a phenol resin used as a (C) hardening | curing agent of an epoxy resin. For example, it may be a phenol resin having two or more phenolic hydroxyl groups in one molecule generally used as a curing agent, and in one molecule such as resorcin, catechol, bisphenol A, bisphenol F, substituted or unsubstituted biphenol. A compound having two phenolic hydroxyl groups; phenols such as phenol, cresol, xylenol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol and / or α-naphthol, β-naphthol, dihydroxynaphthalene, etc. A novolak-type phenolic resin obtained by condensation or cocondensation of naphthols with aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, salicylaldehyde in the presence of an acidic catalyst; Aralkyl-type phenol resins such as phenol aralkyl resins and naphthol aralkyl resins synthesized from enols and / or naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl; paraxylylene and / or metaxylylene-modified phenol resins; melamine-modified phenol resins; Terpene-modified phenolic resin; dicyclopentadiene-type phenol resin, dicyclopentadiene-type naphthol resin synthesized by copolymerization from phenols and / or naphthols and dicyclopentadiene; cyclopentadiene-modified phenol resin; polycyclic aromatic ring-modified phenol Resin; Biphenyl type phenol resin; Triphenylmethane type phenol resin; Phenol resin obtained by copolymerizing two or more of these may be used. It may be used in combination of two or more even.

  Among the above-mentioned phenol resins, from the viewpoint of reflow crack resistance, aralkyl-type phenol resins, dicyclopentadiene-type phenol resins, salicylaldehyde-type phenol resins, benzaldehyde-type and aralkyl-type copolymer phenol resins, novolak-type phenol resins Is preferred. These phenolic resins may be used alone or in combination of two or more as curing agents, but in order to exert their performance, a total of 30% by weight or more is used with respect to all phenolic resins. It is preferable to use 50% by weight or more in total. Hereinafter, specific examples of preferable phenol resins will be shown.

  The aralkyl type phenolic resin is not particularly limited as long as it is a phenolic resin synthesized from phenols and / or naphthols and dimethoxyparaxylene, bis (methoxymethyl) biphenyl or a derivative thereof. Phenol resins represented by (XV) to (XVII) are preferred.

（一般式（XV）〜（XVII）中、Ｒ^２２〜Ｒ^２８は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｋは０〜４の整数、ｊは０〜２の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（XV）で示されるフェノール樹脂の中でも、ｉ＝０、ｋ＝０であるＸＬ−２２５、ＸＬＣ(三井化学株式会社製商品名)、ＭＥＨ−７８００（明和化成株式会社商品名）等が市販品として入手可能である。上記一般式（XVI）で示されるフェノール樹脂の中でも、ｉ＝０、Ｒ^２５が全て水素原子であるＭＥＨ−７８５１（明和化成株式会社商品名）等が市販品として入手可能である。上記一般式（XVII）で示されるフェノール樹脂の中でも、ｊ＝０、Ｒ^２７のｋ＝０、Ｒ^２８のｋ＝０であるＳＮ−１７０（新日鐵化学株式会社商品名）等が市販品として入手可能である。

(In the general formulas (XV) to (XVII), R ^{22 to} R ^{28 each} represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different. 3 is an integer, k is an integer of 0 to 4, j is an integer of 0 to 2, n is an average value, and represents a positive integer of 0 to 10.)
Among the phenol resins represented by the general formula (XV), XL-225, XLC (trade name, manufactured by Mitsui Chemicals, Inc.), MEH-7800 (trade name, Meiwa Kasei Co., Ltd.), etc., where i = 0 and k = 0. Is commercially available. Among the phenol resins represented by the above general formula (XVI), ME = 07851 (trade name of Meiwa Kasei Co., Ltd.) in which i = 0 and R ²⁵ are all hydrogen atoms is commercially available. Among the phenolic resins represented by the general formula (XVII), SN-170 (trade name of Nippon Steel Chemical Co., Ltd.) where j = 0, R ²⁷ k = 0, and R ²⁸ k = 0 is a commercial product. Is available as

  The dicyclopentadiene type phenol resin is not particularly limited as long as it is a phenol resin using a compound having a dicyclopentadiene skeleton as a raw material, but a phenol resin represented by the following general formula (XVIII) is preferable.

（一般式（XVIII）中、Ｒ^２９は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（XVIII）で示されるフェノール樹脂の中でもｉ＝０であるＤＰＰ(日本石油化学株式会社製商品名)等が市販品として入手可能である。

(In the general formula (XVIII), R ²⁹ represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, i is an integer of 0 to 3, and n is an average. It is a value and represents a positive integer from 0 to 10.)
Among the phenol resins represented by the general formula (XVIII), DPP (trade name, manufactured by Nippon Petrochemical Co., Ltd.) where i = 0 is available as a commercial product.

  The salicylaldehyde type phenol resin is not particularly limited as long as it is a phenol resin using a compound having a salicylaldehyde skeleton as a raw material, but a phenol resin represented by the following general formula (XIX) is preferable.

（一般式（XIX）中、Ｒ^３０及びＲ^３１は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｋは０〜４の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（XIX）で示されるフェノール樹脂の中でも、ｉ＝０、ｋ＝０であるＭ
ＥＨ−７５００(明和化成株式会社製商品名)等が市販品として入手可能である。

(In the general formula (XIX), R ³⁰ and R ³¹ represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, all of which may be the same or different, and i is an integer of 0 to 3, k is an integer of 0 to 4, n is an average value, and represents a positive integer of 0 to 10.)
Among the phenol resins represented by the general formula (XIX), M in which i = 0 and k = 0
EH-7500 (trade name, manufactured by Meiwa Kasei Co., Ltd.) is available as a commercial product.

  The copolymer type phenol resin of benzaldehyde type and aralkyl type is not particularly limited as long as it is a copolymer type phenol resin of a phenol resin and an aralkyl type phenol resin using a compound having a benzaldehyde skeleton as a raw material, A phenol resin represented by the following general formula (XX) is preferred.

（一般式（XX）中、Ｒ^３２〜Ｒ^３４は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｋは０〜４の整数、ｑは０〜５の整数、ｌ、ｍはそれぞれ平均値で０〜１１の正の整数であり（ｌ＋ｍ）は１〜１１の正の整数を示す。）
上記一般式（XX）で示されるフェノール樹脂の中でもｉ＝０、ｋ＝０、ｑ＝０であるＨＥ−５１０(住金化工株式会社製商品名)等が市販品として入手可能である。

(In the general formula (XX), R ^{32 to} R ³⁴ represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and they may be all the same or different, and i is an integer of 0 to 3, k is an integer of 0 to 4, q is an integer of 0 to 5, l and m are positive integers of 0 to 11 on average, and (l + m) is a positive integer of 1 to 11.)
Among the phenolic resins represented by the general formula (XX), HE-510 (trade name, manufactured by Sumikin Kako Co., Ltd.) having i = 0, k = 0, and q = 0 is available as a commercial product.

  The novolac type phenol resin is not particularly limited as long as it is a phenol resin obtained by condensation or cocondensation of phenols and / or naphthols and aldehydes in the presence of an acidic catalyst, but the following general formula (XXI ) Is preferred.

（ここで、一般式（XXI）中のＲ^３５及びＲ^３６は水素原子又は炭素数１〜１８の１価の有機基を示し、それぞれ全てが同一でも異なっていてもよく、ｉは０〜３の整数、ｋは０〜４の整数、ｎは平均値であり、０〜１０の正の整数を示す。）
上記一般式（XXI）で示されるフェノール樹脂の中でも、ｉ＝０、Ｒ^３５が全て水素原子であるタマノル７５８、７５９(荒川化学工業株式会社製商品名)、ＨＰ−８５０Ｎ（日立化成工業株式会社商品名）等が市販品として入手可能である。

(Here, R ³⁵ and R ³⁶ in the general formula (XXI) each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different. , K is an integer of 0 to 4, n is an average value, and represents a positive integer of 0 to 10.)
Among the phenol resins represented by the general formula ^{(XXI), i = 0,} R 35 are all hydrogen atoms TAMANOL 758, 759 (Arakawa Chemical Industries, Ltd., trade name), HP-850N (Hitachi Chemical Co., Ltd. (Trade name) etc. are commercially available.

Incidentally, as described for R ²² to R ³⁶ in the general formula (XV) ~ (XXI) "all, each may be the same or different", for example, in the formula (XV), the i-number of R ²² This means that all may be the same or different from each other. The other R ^{23 to} R ³⁶ also mean that all of the numbers included in the formula may be the same or different from each other. R ^{22 to} R ³⁶ may be the same as or different from each other. For example, all of R ²² and R ²³ may be the same or different, and all of R ³⁰ and R ³¹ may be the same or different.

  N in the general formulas (XIII) to (XXI) should be in the range of 0 to 10. When n exceeds 10, (B) the melt viscosity of the epoxy resin component is increased, and accordingly, the viscosity at the time of melt molding of the resin composition is also increased, and unfilled defects or bonding wires (connecting the element and the lead) It becomes easy to cause problems during molding such as deformation of the gold wire. Therefore, the average n in one molecule is preferably set in the range of 0-4.

  In the resin composition according to the present invention, when a phenol resin is used as the (C) curing agent, the blending ratio of the (B) epoxy resin and the (C) curing agent is equal to the hydroxyl equivalent of all phenol resins relative to the epoxy equivalent of all epoxy resins. The ratio (number of hydroxyl groups in phenol resin / number of epoxy groups in epoxy resin) is in the range of 0.5 to 2.0, more preferably in the range of 0.7 to 1.5, and still more preferably in the range of 0.8 to 1.3. It is desirable to set it within the range. When the blending ratio is less than 0.5, the epoxy resin is not completely cured, and the heat resistance, moisture resistance, and electrical characteristics of the package obtained by the curing tend to decrease. On the other hand, when the blending ratio exceeds 2.0, not only the phenol resin component becomes excessive and the curing efficiency is lowered, but also a large amount of phenolic hydroxyl group remains in the cured resin, so that the electrical characteristics and moisture resistance of the package are lowered. Tend.

  If necessary, the resin composition according to the present invention can further contain (D) an inorganic filler. In particular, when the resin composition is used as a molding material for sealing, it is preferable to blend (D) an inorganic filler. The inorganic filler (D) that can be used in the resin composition according to the present invention may be generally used for a molding material for sealing, and is not particularly limited. For example, fused 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, Examples include talc, clay, mica and other fine powders, or beads obtained by spheroidizing these.

  Furthermore, examples of the inorganic filler having a flame retardant effect include aluminum hydroxide, magnesium hydroxide, composite metal hydroxides such as composite hydroxide of magnesium and zinc, and zinc borate. Among these, fused silica is preferable from the viewpoint of reducing the linear expansion coefficient, and alumina is preferable from the viewpoint of high thermal conductivity. These inorganic fillers may be used alone or in combination of two or more.

  (D) The amount of the inorganic filler may be in a range that does not adversely affect the effect of the present invention, and is not particularly limited, but is preferably in the range of 55 to 90% by volume with respect to the resin composition. . These inorganic fillers are blended for the purpose of improving the thermal expansion coefficient, thermal conductivity, elastic modulus, etc. of the cured product, and if the blending amount is less than 55% by volume, the improvement of these properties becomes insufficient. There is a tendency, and when it exceeds 90% by volume, the viscosity of the resin composition increases, the fluidity decreases, and the package tends to be difficult to mold.

  Moreover, 1-50 micrometers is preferable and, as for the average particle diameter of (D) inorganic filler, 10-30 micrometers is more preferable. If it is less than 1 μm, the viscosity of the resin composition tends to increase, and if it exceeds 50 μm, the resin component and the inorganic filler are likely to be separated, resulting in a non-uniform package due to curing, variations in characteristics, and narrow gaps. There is a tendency for the filling property to fall.

  From the viewpoint of fluidity, the particle shape of (D) inorganic filler is preferably spherical rather than rectangular, and (D) the particle size distribution of inorganic filler is preferably distributed over a wide range. For example, when blending 75% by volume or more of the inorganic filler, it is preferable that 70% by weight or more of them be spherical particles and the particle size is distributed over a wide range of 0.1 to 80 μm. Since such inorganic fillers are likely to have a close-packed structure, even if the blending amount is increased, there is little increase in the viscosity of the material, and a resin composition excellent in fluidity can be obtained.

  You may mix | blend the anion exchanger with the resin composition by this invention as needed. In particular, when the resin composition is used as a molding material for sealing, it is preferable to blend an anion exchanger from the viewpoint of improving the moisture resistance and high-temperature storage characteristics of an electronic component device including an element to be sealed. . There is no restriction | limiting in particular as an anion exchanger used in this invention, You may conventionally use what is generally used in this technical field. Examples thereof include hydrotalcites and hydrous oxides of elements selected from magnesium, aluminum, titanium, zirconium, and bismuth, and these can be used alone or in combination of two or more. Among these, hydrotalcite represented by the following general formula (XXII) is preferable.

(Chemical formula 19)
Mg _1-X Al _X (OH) ₂ (CO ₃ ) _{X / 2} · mH ₂ O (XXII)
(0 <X ≦ 0.5, m is a positive number)
The amount of the anion exchanger is not particularly limited as long as it is sufficient to capture anions such as halogen ions, but is preferably in the range of 0.1 to 30% by weight based on (B) the epoxy resin. 1 to 5 weight% is more preferable.

  In the resin composition of the present invention, a mold release agent may be blended in order to give good mold releasability from the mold during molding. There is no restriction | limiting in particular as a mold release agent which can be used in this invention, You may be a mold release agent well-known in this technical field. Examples include higher fatty acids such as carnauba wax, montanic acid and stearic acid, higher fatty acid metal salts, ester waxes such as montanic acid esters, polyolefin waxes such as polyethylene oxide and non-oxidized polyethylene, and the like. It may be used alone or in combination of two or more. Of these, oxidized or non-oxidized polyolefin waxes are preferable, and the blending amount thereof is preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, based on the epoxy resin (B). If the blending amount of the polyolefin wax is less than 0.01% by weight, the releasability tends to be insufficient, and if it exceeds 10% by weight, the adhesion may be inhibited. Examples of polyolefin waxes include low molecular weight polyethylene having a number average molecular weight of about 500 to 10,000, such as H4, PE, PED series manufactured by Hoechst. Moreover, when using another mold release agent together with a polyolefin-type wax, 0.1 to 10 weight% is preferable with respect to (B) epoxy resin, and 0.5 to 3 weight% is more preferable.

  In order to impart flame retardancy to the resin composition according to the present invention, a flame retardant may be blended as necessary. The flame retardant that can be used in the present invention is not particularly limited, and examples thereof include well-known organic or inorganic compounds containing a halogen atom, antimony atom, nitrogen atom or phosphorus atom, metal hydroxide, acenaphthylene, and the like. These may be used alone or in combination of two or more. Although there will be no restriction | limiting in particular if the flame-retardant effect is achieved, the compounding quantity of a flame retardant is 1-30 weight% with respect to (B) epoxy resin, and 2-15 weight% is more preferable.

  In the resin composition according to the present invention, a coupling agent may be used as necessary in order to improve the adhesion between the resin component and the inorganic filler. The coupling agent is not particularly limited. For example, various silane compounds such as epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, and vinyl silane, titanium compounds, aluminum chelates, and aluminum / zirconium compounds. A well-known coupling agent such as a compound can be added.

  The blending amount of the coupling agent is preferably 0.05 to 5% by weight, more preferably 0.1 to 2.5% by weight with respect to (D) the inorganic filler. If it is less than 0.05% by weight, the adhesion to the frame tends to be lowered, and if it exceeds 5% by weight, the moldability of the package tends to be lowered.

  Examples of the coupling agent include vinyltrichlorosilane, vinyltriethoxysilane, vinyltris (β-methoxyethoxy) silane, γ-methacryloxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane. Γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, vinyltriacetoxysilane, γ-mercaptopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-anilinopropyltrimethoxysilane , Γ-anilinopropylmethyldimethoxysilane, γ- [bis (β-hydroxyethyl)] aminopropyltriethoxysilane, N-β- (aminoethyl) -γ-aminopropyltrimethoxysilane, γ- (β-aminoethyl) ) Aminopropyldimethoxymethylsilane, N- (trimethoxysilylpropyl) ethylenediamine, N- (dimethoxymethylsilylisopropyl) ethylenediamine, methyltrimethoxysilane, dimethyldimethoxysilane, methyltriethoxysilane, N-β- (N-vinylbenzyl) Silane coupling agents such as (aminoethyl) -γ-aminopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, hexamethyldisilane, vinyltrimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, isopropyltriisostearoyl titanate, Isopropyltris (dioctylpyrophosphate) titanate, isopropyltri (N-aminoethyl-aminoethyl) titanate, tetraoctylbis (ditridecyl) Phosphite) titanate, tetra (2,2-diallyloxymethyl-1-butyl) bis (ditridecyl) phosphite titanate, bis (dioctylpyrophosphate) oxyacetate titanate, bis (dioctylpyrophosphate) ethylene titanate, isopropyltrioctanoyl Titanates such as titanate, isopropyl dimethacrylisostearoyl titanate, isopropyl tridodecylbenzenesulfonyl titanate, isopropyl isostearoyl diacryl titanate, isopropyl tri (dioctyl phosphate) titanate, isopropyl tricumyl phenyl titanate, tetraisopropyl bis (dioctyl phosphite) titanate Coupling agents and the like can be mentioned, and these can be used alone or in combination of two or more. It may be used in combination. Among these, a coupling agent having a secondary amino group is preferable from the viewpoints of fluidity and wire flow.

  If necessary, the resin composition according to the present invention can be blended with a stress relaxation agent such as silicone oil or silicone rubber powder. By adding a stress relaxation agent, the amount of warp deformation and package cracking of the package can be reduced. The usable stress relaxation agent is not particularly limited as long as it is a well-known flexible agent (stress relaxation agent) that is generally used in the art. Commonly used flexible agents include, for example, silicone-based, styrene-based, olefin-based, urethane-based, polyester-based, polyether-based, polyamide-based, polybutadiene-based thermoplastic elastomers, NR (natural rubber), NBR, and the like. (Acrylonitrile-butadiene rubber), rubber particles such as acrylic rubber, urethane rubber, silicone powder, methyl methacrylate-styrene-butadiene copolymer (MBS), methyl methacrylate-silicone copolymer, methyl methacrylate-butyl acrylate Examples thereof include rubber particles having a core-shell structure such as a copolymer, and these may be used alone or in combination of two or more. Among these, silicone-based flexible agents are preferable, and examples of the silicone-based flexible agents include those having an epoxy group, those having an amino group, and those obtained by modifying these with a polyether.

  The resin composition according to the present invention may contain a colorant such as carbon black, organic dye, organic pigment, titanium oxide, red lead, bengara and the like. In addition, if necessary, various additives may be added as long as the effects of the present invention are not lowered.

  Any method may be used for preparing the resin composition according to the present invention as long as various components can be uniformly dispersed and mixed. As a general method, there can be mentioned a method in which components of a predetermined blending amount are sufficiently mixed by a mixer or the like, then melt-kneaded by a mixing roll, an extruder or the like, and then cooled and pulverized. More specifically, the resin composition is, for example, uniformly stirred and mixed with a predetermined amount of the above-described components, kneaded with a kneader, a roll, an extruder, etc., heated to 70 to 140 ° C., cooled, It can be obtained by a method such as grinding. The resin composition is easy to handle when it is tableted with a size and weight suitable for the molding conditions of the package.

  An electronic component device according to the present invention includes an element sealed with the above-described resin composition. Electronic component devices include, for example, lead frames, wired tape carriers, wiring boards, glass, silicon wafers, and other supporting members, active elements such as semiconductor chips, transistors, diodes, thyristors, capacitors, resistors, coils, etc. These are mounted with an element such as a passive element, and the element part is sealed with the resin composition according to the present invention. More specifically, for example, after fixing a semiconductor element on a lead frame and connecting the terminal part of the element such as a bonding pad and the lead part by wire bonding or bump, transfer molding is performed using the resin composition of the present invention. 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), general resin encapsulated IC such as TQFP (Thin Quad Flat Package), TCP (Tape Carrier Package) in which a semiconductor chip connected to a tape carrier with bumps is encapsulated with the resin composition of the present invention, wiring Semiconductor chips, transistors, and damascenes connected by wire bonding, flip chip bonding, solder, etc. to wiring formed on a plate or glass COB (Chip On Board) module, hybrid IC, multichip module, and backside wiring in which active elements such as odes and thyristors and / or passive elements such as capacitors, resistors and coils are sealed with the resin composition of the present invention A BGA in which an element is mounted on the surface of an organic substrate on which terminals for connecting the plate are formed, the element is connected to the wiring formed on the organic substrate by bump or wire bonding, and the element is sealed with the resin composition of the present invention (Ball Grid Array), CSP (Chip Size Package), and the like. The resin composition of the present invention can also be used effectively for printed circuit boards.

  A method for sealing an electronic component device using the resin composition of the present invention is not particularly limited, and methods well known in the art can be applied. For example, the low pressure transfer molding method is the most common, but an injection molding method, a compression molding method, or the like may be used.

  EXAMPLES Hereinafter, although an Example demonstrates this invention, the scope of the present invention is not limited by the Example shown below.

Example 1
This example shows a synthesis example of a novel compound according to the present invention. The compound was synthesized according to the following procedure.

  First, 2000 ml of methanol was added to 185.2 g (0.5 mol) of an adduct of triphenylphosphine and 1,4-benzoquinone, and then 50.0 g of concentrated hydrochloric acid was added with stirring to obtain a uniform solution. Next, 171.0 g (0.5 mol) of sodium tetraphenylborate dissolved in 1000 ml of methanol / water (1: 1 mixed solvent) was added dropwise with stirring to the previously prepared uniform solution, and brown fine particles were added. Crystals precipitated. Stirring was continued at room temperature for 1 hour after completion of the dropwise addition, and the precipitated crystals were filtered, washed with water, and then dried to obtain 295.0 g of brown powdery crystals (yield 85.4%, chlorine The ion content was 10 ppm). The results of elemental analysis of the obtained crystals were calculated value C: 83.48%, H: 5.84%, measured value C: 83.39%, and H: 5.80%.

Furthermore, the crystals obtained by the above procedure were identified by ¹ H-NMR, ³¹ P-NMR and IR spectra, and confirmed to be a compound represented by the following formula (XXIII).

（式（XXIII）中、Ｐｈはフェニル基を示す。）
^１Ｈ−ＮＭＲ、^３１Ｐ−ＮＭＲ及びＩＲのスペクトルを図１〜３に示す。なお、各測定条件は以下のとおりである。
（１）^１Ｈ−ＮＭＲ
結晶１０ｍｇを約０.５ｍｌの重ジメチルスルホキシドに溶かし、φ５ｍｍの試料管に入れ、日本電子データム（株）社製ＪＮＭ-Ｌａｍｂｄａ３００で測定した。シフト値は、溶媒に微量含まれるＣＨＤ_２ＳＯＣＤ_３（２.５ｐｐｍ）を基準とした。
（２）^３１Ｐ−ＮＭＲ
結晶１０ｍｇを約０.５ｍｌの重ジメチルスルホキシドに溶かし、φ５ｍｍの試料管に入れ、日本電子データム（株）社製ＪＮＭ-Ｌａｍｂｄａ３００で測定した。シフト値は、リン酸を基準とした。
（３）ＩＲ
（株）島津製作所社製ＦＴＩＲ−８３００を用い、拡散反射法で測定した。

(In the formula (XXIII), Ph represents a phenyl group.)
The spectra of ¹ H-NMR, ³¹ P-NMR and IR are shown in FIGS. Each measurement condition is as follows.
(1) ¹ H-NMR
10 mg of crystals were dissolved in about 0.5 ml of heavy dimethyl sulfoxide, placed in a φ5 mm sample tube, and measured with JNM-Lambda300 manufactured by JEOL Datum Co., Ltd. The shift value was based on CHD ₂ SOCD ₃ (2.5 ppm) contained in a trace amount in the solvent.
(2) ³¹ P-NMR
10 mg of crystals were dissolved in about 0.5 ml of heavy dimethyl sulfoxide, placed in a φ5 mm sample tube, and measured with JNM-Lambda300 manufactured by JEOL Datum Co., Ltd. The shift value was based on phosphoric acid.
(3) IR
It measured by the diffuse reflection method using FTIR-8300 by Shimadzu Corporation Corp.

(Example 2)
Example 2 shows the preparation of resin compositions according to the present invention and the evaluation of their properties.

  Various components shown below were blended in parts by weight shown in Table 1, and roll kneading was carried out under conditions of a kneading temperature of 80 ° C. and a kneading time of 15 minutes to obtain a resin composition.

Epoxy resin 1: biphenyl type epoxy resin having an epoxy equivalent of 196 and a melting point of 106 ° C. (trade name YX-4000H manufactured by Japan Epoxy Resin Co., Ltd.)
Brominated epoxy resin: Epoxy equivalent 393, softening point 80 ° C., brominated bisphenol A type epoxy resin having a bromine content of 48% by weight Curing agent 1: Hydroxyl equivalent 176, phenol aralkyl resin having a softening point 70 ° C. (Mitsui Chemicals, Inc.) Product name Milex XL-225)
Curing accelerator 1: Compound prepared in Example 1 Inorganic filler: Spherical fused silica having an average particle size of 17.5 μm and a specific surface area of 3.8 m ² / g Coupling agent: Epoxysilane (γ-glycidoxypropyltrimethoxy Silane)
Colorant: Carbon black (trade name MA-100 manufactured by Mitsubishi Chemical Corporation)
Mold release agent: Carnauba wax (manufactured by Celerica NODA)
Flame retardant: antimony trioxide Next, characteristics of the obtained resin composition were evaluated by various tests. The results are shown in Table 2. The resin composition was molded using a transfer molding machine, and molding was performed under conditions of a mold temperature of 180 ° C., a molding pressure of 6.9 MPa, and a curing time of 90 seconds.

(Comparative Example 1)
This comparative example 1 shows the resin composition prepared using the conventional hardening accelerator and its characteristic evaluation. The resin composition according to Comparative Example 1 was prepared in the same manner as Example 2 except that an addition reaction product of triphenylphosphine and 1,4-benzoquinone (curing accelerator A) was used as a curing accelerator. That is, various components were blended in parts by weight shown in Table 1, and roll kneading was performed under conditions of a kneading temperature of 80 ° C. and a kneading time of 15 minutes to obtain a resin composition.

  Next, the characteristics of the obtained resin composition were evaluated by various tests. The results are shown in Table 2. The resin composition was molded using a transfer molding machine, and molding was performed under conditions of a mold temperature of 180 ° C., a molding pressure of 6.9 MPa, and a curing time of 90 seconds.

(Comparative Example 2)
This comparative example 2 shows the resin composition prepared using the conventional hardening accelerator and its characteristic evaluation. The resin composition according to Comparative Example 2 was prepared in the same manner as in Example 2 except that tetraphenylphosphonium tetraphenylborate (curing accelerator B) was used as the curing accelerator. That is, various components were blended in parts by weight shown in Table 1, and roll kneading was performed under conditions of a kneading temperature of 80 ° C. and a kneading time of 15 minutes to obtain a resin composition.

  Next, the characteristics of the obtained resin composition were evaluated by various tests. The results are shown in Table 2. The resin composition was molded using a transfer molding machine, and molding was performed under conditions of a mold temperature of 180 ° C., a molding pressure of 6.9 MPa, and a curing time of 90 seconds. However, since molding could not be performed at a curing time of 90 seconds, the evaluation was performed under the conditions of a curing time of 300 seconds.

Details of the various tests are as follows.
(1) Spiral flow (fluidity index)
A resin composition was molded under the conditions described in each Example using a spiral flow measurement mold according to EMMI-1-66, and the flow distance (cm) was measured.
(2) Spiral flow survival rate (index of storage stability)
The spiral flow of the resin composition left at 25 ° C. (sealed) for 48 hours was measured in the same manner as in the above (1), and the residual ratio (%) from the value (initial value) in the above (1) was determined.
(3) Heat hardness (index of fast curability)
The resin composition was molded into a disc having a diameter of 50 mm and a thickness of 3 mm under the conditions described in each example, and measured immediately using a Shore D type hardness meter after molding.

  As is clear from the results shown in Table 2, the resin composition (Example 1) of the present invention using the novel compound as a curing accelerator has good fluidity, storage stability, and fast curability. A balanced improvement has been achieved. On the other hand, the resin compositions prepared using conventional curing accelerators (Comparative Examples 1 and 2) cannot achieve a balanced improvement, Comparative Example 1 has low storage stability, and Comparative Example 2 has a high speed. The result was remarkably inferior in curability.

1 is a ¹ H-NMR spectrum of a compound according to the present invention obtained in Example 1. 2 is a ³¹ P-NMR spectrum of the compound according to the present invention obtained in Example 1. 2 is an IR spectrum of the compound according to the present invention obtained in Example 1.

Claims (10)

A compound represented by the following general formula (I):

(In formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ represent a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, and each may be the same or different,
R ^{4 to} R ^{6 each} represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms, all of which may be the same or different, and R ⁴ and R ⁵ are bonded to form a cyclic structure. It may be. ) In the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are methyl, ethyl, isopropyl, n-butyl, sec-butyl, tert-butyl, octyl, cyclohexyl, benzyl group, a phenyl group, p- tolyl group, a m- tolyl group, o- tolyl group, p- methoxyphenyl group, m- methoxyphenyl group, a group selected from the group consisting of o- methoxyphenyl group, R ⁴ ~ The compound according to claim 1, wherein R ⁶ is a hydrogen atom. The compound according to claim 1 or 2, wherein in the general formula (I), R ^{1 to} R ³ and R ^{7 to} R ¹⁰ are phenyl groups, and R ^{4 to} R ⁶ are hydrogen atoms. A curing accelerator comprising one or more compounds according to any one of claims 1 to 3. A resin composition comprising (A) one or more curing accelerators according to claim 4 and (B) an epoxy resin. The resin composition according to claim 5, further comprising (C) a curing agent. (D) The resin composition according to claim 5 or 6, further comprising an inorganic filler. (B) epoxy resin is biphenyl type epoxy resin, stilbene type epoxy resin, diphenylmethane type epoxy resin, sulfur atom containing type epoxy resin, novolac type epoxy resin, dicyclopentadiene type epoxy resin, salicylaldehyde type epoxy resin, naphthols The resin according to any one of claims 5 to 7, comprising at least one epoxy resin selected from the group consisting of a copolymerized epoxy resin with phenols and an epoxidized product of an aralkyl epoxy resin. Composition. (C) The curing agent is selected from the group consisting of aralkyl type phenol resins, dicyclopentadiene type phenol resins, salicylaldehyde type phenol resins, benzaldehyde type phenol resins and aralkyl type phenol resins, and novolak type phenol resins. The resin composition according to claim 6, further comprising at least one curing agent. An electronic component device comprising an element sealed with the resin composition according to claim 5.

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