KR101774629B1 - Epoxy compound, epoxy compound mixture, curable composition, and connecting structure - Google Patents

Abstract

The present invention provides an epoxy compound, a curable composition using the epoxy compound, and a connection structure using the curable composition, which can be rapidly cured and is excellent in adhesiveness and humidity resistance of a cured product. The epoxy compound according to the present invention has an epoxy group at both terminals and a vinyl group or an epoxy group in the side chain. The weight average molecular weight of the epoxy compound according to the present invention is 500 to 150,000. The curable composition according to the present invention comprises the above epoxy compound and a thermosetting agent. The connection structure 1 according to the present invention includes a first connection object member 2, a second connection object member 4 and a connection portion 3 connecting the first and second connection object members 2 and 4 . The connecting portion 3 is formed by the above-mentioned curable composition.

Description

[0001] EPOXY COMPOUND, EPOXY COMPOUND MIXTURE, CURABLE COMPOSITION, AND CONNECTING STRUCTURE [0002]

The present invention relates to, for example, an epoxy compound that can be rapidly cured and has excellent adhesion and moisture resistance of a cured product. The present invention also relates to a mixture of the epoxy compound containing the epoxy compound, a curable composition using the epoxy compound, and a connection structure using the curable composition.

The epoxy resin composition has high adhesive force of the cured product after curing, and is excellent in water resistance and heat resistance of the cured product. For this reason, epoxy resin compositions are widely used in various applications such as electric, electronic, construction, and automobile. In addition, in order to electrically connect various connection target members, conductive particles may be blended in the epoxy resin composition. The epoxy resin composition containing conductive particles is called an anisotropic conductive material.

The anisotropic conductive material is specifically used for connection between an IC chip and a flexible printed circuit board, and for connection between a IC chip and a circuit board having an ITO electrode. For example, after an anisotropic conductive material is disposed between the electrodes of the IC chip and the electrodes of the circuit board, the electrodes can be connected to each other by heating and pressing.

As an example of the anisotropic conductive material, Patent Document 1 below discloses an anisotropic conductive adhesive film comprising a thermosetting insulating adhesive, conductive particles, an imidazole-based latent curing agent, and an amine-based latent curing agent. The thermosetting insulating adhesive preferably includes a flexible epoxy resin. Patent Document 1 discloses that the connection reliability is excellent even when the anisotropic conductive adhesive film is cured at a relatively low temperature.

In addition, Patent Document 2 discloses a composition comprising a diglycidyl ether of a bisphenol A-alkylene oxide adduct, a bisphenol A diglycidyl ether, a diluent having no epoxy group, a carboxyl-terminated butadiene-acrylonitrile copolymer, Discloses an epoxy resin composition comprising chenic anhydridesuccinic acid and an inorganic filler.

Japanese Patent Application Laid-Open No. 9-115335 Japanese Patent Application Laid-Open No. 9-235350

In recent years, in order to efficiently connect the electrodes between electronic components, it is required to shorten the heating time required for curing the epoxy resin composition. In addition, by shortening the heating time, heat degradation of the obtained electronic component can be suppressed.

In the anisotropic conductive adhesive film described in Patent Document 1, if the heating time is shortened, the curing may not be sufficiently performed. For this reason, in order to connect the electrodes of the electronic component by using the anisotropic conductive adhesive film, it may be necessary to heat for a long time. Therefore, there is a case where the electrodes can not be efficiently connected. Further, even the epoxy resin composition described in Patent Document 2 requires long time heating in order to sufficiently cure.

In addition, the anisotropic conductive adhesive film described in Patent Document 1 and the epoxy resin composition disclosed in Patent Document 2 may have low adhesiveness and moisture resistance of a cured product.

On the other hand, development of a new curable compound capable of shortening the heating time is required. The development of new curable compounds diversifies the curable composition.

It is an object of the present invention to provide a novel epoxy compound which can be used in a curable composition.

Further, a limited object of the present invention is to provide an epoxy compound which can be rapidly cured and which is excellent in adhesiveness and moisture resistance of a cured product, a mixture of an epoxy compound containing the epoxy compound, a curable composition using the epoxy compound, To provide a connection structure using the composition.

According to a broad aspect of the present invention, there is provided an epoxy compound having an epoxy group at both terminals, a vinyl group or an epoxy group in the side chain, and a weight average molecular weight of 500 to 150,000.

In a specific aspect of the epoxy compound according to the present invention, the epoxy compound has two or more vinyl groups in total in the side chain or a total of two or more epoxy groups in the side chain.

In another specific aspect of the epoxy compound according to the present invention, the epoxy compound is added to the reaction product of bisphenol F or resorcinol with 1,6-hexanediol diglycidyl ether or resorcinol diglycidyl ether, Acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether.

In another particular aspect of the epoxy compound according to the present invention, the reactant is a first reactant of bisphenol F and 1,6-hexanediol diglycidyl ether, or a mixture of resorcinol and 1,6-hexanediol diglycidyl Ether, or a third reactant of resorcinol and resorcinol diglycidyl ether.

In another specific aspect of the epoxy compound according to the present invention, when there are two peaks in the molecular weight distribution of the epoxy compound when the reactant is the first reactant, and when the reactant is the second reactant, There are two peaks in the molecular weight distribution.

The reactant is preferably the first reactant, preferably the second reactant, and the third reactant. Also, the compound to be reacted with the reactant is preferably (meth) acrylic acid or 2- (meth) acryloyloxyethyl isocyanate, and is preferably 2- (meth) acryloyloxyethyl isocyanate.

The mixture of epoxy compounds according to the present invention contains at least two kinds of the above-mentioned epoxy compounds.

In a particular aspect of the mixture of epoxy compounds according to the present invention, a first reactant of bisphenol F and 1,6-hexanediol diglycidyl ether is admixed with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or (Meth) acrylic acid, 2- (meth) acrylic acid, or the like is added to a second reaction product of a first epoxy compound obtained by reacting 4-hydroxybutyl glycidyl ether and resorcinol and 1,6-hexanediol diglycidyl ether, Acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether. The second epoxy compound is obtained by reacting acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether.

In another specific aspect of the mixture of epoxy compounds according to the present invention, a second reaction product of resorcinol and 1,6-hexanediol diglycidyl ether is admixed with (meth) acrylic acid, 2- (meth) acryloyloxyethyl (Meth) acrylic acid, 2- (meth) acryloyloxyethyl acrylate or the like is added to a third reaction product of a second epoxy compound obtained by reacting isocyanate or 4-hydroxybutyl glycidyl ether with resorcinol and resorcinol diglycidyl ether, A tertiary epoxy compound obtained by reacting an epoxy group-containing epoxy compound, e.g.

In another specific aspect of the mixture of epoxy compounds according to the present invention, the viscosity at 23 캜 is not less than 50 Pa · s.

The curable composition according to the present invention comprises the above-mentioned epoxy compound and a thermosetting agent.

In a specific aspect of the curable composition according to the present invention, at least two epoxy compounds are included.

In another specific aspect of the curable composition according to the present invention, a photocurable compound and a photopolymerization initiator are further included.

In another specific aspect of the curable composition according to the present invention, conductive particles are further included.

In another specific aspect of the curable composition according to the present invention, an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with at least one of two epoxy groups at both terminals of the epoxy compound is further included in addition to the epoxy compound do.

The connecting structure according to the present invention includes a first connecting object member, a second connecting object member, and a connecting portion connecting the first and second connecting object members, and the connecting portion is formed by the above-mentioned curable composition have.

In a specific aspect of the connection structure according to the present invention, the curable composition includes conductive particles, and the first and second connection target members are electrically connected by the conductive particles.

The epoxy compound according to the present invention diversifies the curable composition. The epoxy compound according to the present invention has an epoxy group at both ends and a vinyl group or an epoxy group in the side chain and has a weight average molecular weight of 500 or more and 150,000 or less so that the epoxy compound can be rapidly cured and the adhesiveness and moisture resistance .

BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a partially cutaway cross-sectional view schematically showing an example of a connection structure using a curable composition according to an embodiment of the present invention. Fig.

Hereinafter, the present invention will be described in detail.

(Epoxy compound)

The epoxy compound according to the present invention has an epoxy group at both terminals and a vinyl group or an epoxy group in the side chain. The weight average molecular weight of the epoxy compound according to the present invention is 500 to 150,000.

The epoxy compound having the above-described structure can be rapidly cured. For example, the curable composition in which the epoxy compound and the thermosetting agent are blended can be rapidly cured. For example, it is possible to cure at a heating temperature of 150 ° C or higher within 5 seconds. In addition, adhesiveness and moisture resistance of the cured product using the epoxy compound can be enhanced. Therefore, the reliability of the connection structure in which the first and second connection target members are connected can be improved by using the curable composition including the epoxy compound.

The epoxy compound according to the present invention is more preferably a reaction product using a compound having a diol compound and two epoxy groups. The epoxy compound according to the present invention is preferably an epoxy compound obtained by reacting a compound having a vinyl group or a compound having an epoxy group with a reaction product of a diol compound and a compound having two epoxy groups.

The weight average molecular weight of the epoxy compound according to the present invention is 500 to 150,000. The weight average molecular weight of the epoxy compound according to the present invention is preferably 1,000 or more, preferably 50,000 or less, and more preferably 15,000 or less.

The epoxy compound according to the present invention has at least one vinyl group in the side chain or at least one epoxy group in the side chain. The epoxy compound according to the present invention may have at least one vinyl group in the side chain or at least one epoxy group in the side chain.

The epoxy compound according to the present invention preferably has two or more vinyl groups in total in the side chain or two or more epoxy groups in total in the side chain. As the number of vinyl groups or epoxy groups increases, the heating time can be further shortened, and the adhesiveness and moisture resistance of the cured product can be further increased. The epoxy compound according to the present invention may have two or more vinyl groups in total in the side chain, or may have two or more epoxy groups in total in the side chain.

The epoxy compound according to the present invention is preferably a reaction product of a compound having two or more phenolic hydroxyl groups and a compound having two or more epoxy groups.

Examples of the compound having two or more phenolic hydroxyl groups include bisphenol compounds, resorcinols, naphthalenols, and the like. Examples of the bisphenol compound include bisphenol F, bisphenol A, bisphenol S, bisphenol SA, and bisphenol E.

Examples of the compound having two or more epoxy groups include aliphatic epoxy compounds and aromatic epoxy compounds. The aliphatic epoxy compound includes a compound having a glycidyl ether group or an oxetanyl group at both terminals of an alkyl chain having 3 to 12 carbon atoms, and a polyether skeleton having 2 to 4 carbon atoms, wherein 2 to 10 of the polyether skeletons And a polyether type epoxy compound having a structural unit continuously bonded thereto.

The epoxy compound according to the present invention can be produced by reacting bisphenol F or a reaction product of resorcinol with 1,6-hexanediol diglycidyl ether or resorcinol diglycidyl ether (hereinafter also referred to as reactant (X)), ) Acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether. The epoxy compound synthesized by using such a compound can be rapidly cured, and the adhesion and humidity resistance of the cured product can be increased.

The reaction product (X) may be prepared by reacting bisphenol F represented by the following formula (1) or resorcinol represented by the following formula (2) with 1,6-hexanediol diglycidyl ether represented by the following formula (11) Is a reactant of resorcinol diglycidyl ether represented by the following formula (12).

The bonding site of one hydroxyl group to one benzene ring in the above formula (1) is not particularly limited. Examples of the bisphenol F include 4,4'-methylene bisphenol represented by the following formula (1-1), 2,4'-methylene bisphenol represented by the following formula (1-2) 2,2'-methylene bisphenol represented by the following formula (3). Generally, these are collectively referred to as bisphenol F. The bisphenol F may contain two or more compounds having different hydroxyl group bonding sites to one benzene ring. The bisphenol F is preferably 4,4'-methylene bisphenol, 2,4'-methylene bisphenol or 2,2'-methylene bisphenol.

As the reactant (X), a first reaction product of bisphenol F and 1,6-hexanediol diglycidyl ether, a second reaction product of resorcinol and 1,6-hexanediol diglycidyl ether, a second reaction product of resorcinol and resorcinol A third reactant of ricinodiglycidyl ether, and a fourth reactant of bisphenol F and resorcinol diglycidyl ether.

The first reactant has a structural unit in which a skeleton derived from bisphenol F and a skeleton derived from 1,6-hexanediol diglycidyl ether are bonded to each other in the main chain, and the structural unit derived from 1,6-hexanediol diglycidyl ether And an epoxy group at both ends. The second reactant has a structural unit derived from resorcinol and a structural unit derived from 1,6-hexanediol diglycidyl ether in the main chain, and an epoxy group derived from 1,6-hexanediol diglycidyl ether At both ends. The third reactant has a skeleton derived from resorcinol and a skeleton derived from resorcinol diglycidyl ether in its main chain, and has an epoxy group derived from resorcinol diglycidyl ether at both ends. The fourth reactant has a skeleton derived from bisphenol F and a skeleton derived from resorcinol diglycidyl ether in its main chain, and has an epoxy group derived from resorcinol diglycidyl ether at both ends thereof.

From the viewpoint of facilitating the synthesis and enabling the epoxy compound to be cured more rapidly and further enhancing the adhesiveness and moisture resistance of the cured product, it is preferable that among the first, second, third, and fourth reactants, 1 reactant, the second reactant or the third reactant is preferred. The reactant (X) is preferably the first reactant, preferably the second reactant, and the third reactant.

The first reactant preferably has a structure represented by the following formula (51).

In the above formula (51), n represents an integer. When n is an epoxy compound obtained by reacting an epoxy compound represented by the formula (51) with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

The second reactant preferably has a structure represented by the following formula (52).

In the above equation (52), n represents an integer. When n is an epoxy compound obtained by reacting an epoxy compound represented by the formula (52) with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

The third reactant preferably has a structure represented by the following formula (53).

In the above formula (53), n represents an integer. When n is an epoxy compound obtained by reacting an epoxy compound represented by the formula (53) with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

The fourth reactant preferably has a structure represented by the following formula (54).

In the above equation (54), n represents an integer. When n is an epoxy compound, the epoxy compound represented by the formula (54) is reacted with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

In the formula (51), formula (52), formula (53) and formula (54), n is preferably an integer such that the weight average molecular weight of the epoxy compound is 1,000 to 50,000, And more preferably an integer of from 1,000 to 15,000.

When there are two peaks in the molecular weight distribution of the epoxy compound, the peak on the high molecular weight side is larger than the peak on the low molecular weight side, preferably 10,000 or more, preferably 150,000 or less, more preferably 50,000 or less Is less than 15,000. When there are two peaks in the molecular weight distribution of the epoxy compound, the peak on the low molecular weight side is smaller than the peak on the high molecular weight side, preferably 1,000 or more, more preferably 2,000 or more, preferably 10,000 or less Is less than 6,000.

The bonding site of one oxygen atom to one benzene ring in the formulas (51) and (54) is not particularly limited. This bonding site is determined according to the kind of bisphenol F (for example, the above formulas (1-1) to (1-3)).

Specific reactions for reacting bisphenol F or resorcinol with 1,6-hexanediol diglycidyl ether or resorcinol diglycidyl ether include addition polymerization.

The bisphenol F represented by the above formula (1) is called a 2-core. Further, bisphenol F is commercially available. In addition to bisphenol F having two nucleus chains, this commercial product may contain a polynucleer having a bisphenol F skeleton and having three or more nuclei. The polynucleer is a triple nucleus or a polynuclear core having four or more nuclei. The nucleus is also the number of benzene rings. When reactant (X) is obtained, a polynuclear material having bisphenol F skeleton and having 3 or more nuclei together with bisphenol F may be used.

The polynucleer is, for example, represented by the following formula (X). In order to obtain the reactant (X), when a mixture of a bisphenol F having two nuclei and a polynucleer having a bisphenol F skeleton and having 3 or more nuclei is used, the content of the bisphenol F Is preferably not less than 70% by weight, more preferably not less than 85% by weight, preferably not more than 99.9% by weight, more preferably not more than 99% by weight. When the content of the bisphenol F 2 nucleus in 100 wt% of the mixture is lower than or equal to the lower limit and lower than or equal to the upper limit, the adhesiveness of the cured product using the epoxy compound is further increased, and the connection structure using the curable composition containing the epoxy compound Thereby further enhancing the reliability.

In the above formula (X), m represents an integer of 1 or more. m is preferably 10 or less, more preferably 5 or less, particularly preferably 3 or less. For example, in the formula (X), the polynucleer with m = 1 is a triple nucleus having a bisphenol F skeleton. In the formula (X), the bonding site of one hydroxyl group to one benzene ring is not particularly limited.

When a mixture of a bisphenol F having two nucleus chains and a polynucleer having a bisphenol F skeleton and having 3 or more nuclei is used, the first reactant of bisphenol F and 1,6-hexanediol diglycidyl ether has 2 nuclei In addition to the structural unit to which the skeleton derived from the chain bisphenol F and the skeleton derived from the 1,6-hexanediol diglycidyl ether are bonded, a skeleton derived from a multinuclear body having a bisphenol F skeleton and having 3 or more nuclei, And a skeleton-derived structural unit derived from 6-hexanediol diglycidyl ether may be included in the main chain. 2 nuclear chain bisphenol F and a multinuclear body having a bisphenol F skeleton and having 3 or more nuclei is used, the fourth reaction product contains a skeleton derived from a bisphenol F nucleus and a resorcinol diglycidyl ether The backbone may include a structural unit in which a skeleton derived from a polynuclear body having a bisphenol F skeleton and having 3 or more nuclei and a skeleton derived from resorcinol diglycidyl ether is combined.

That is, the first reactant may have a structure represented by the following formula (51X).

In the formula (51X), X represents a skeleton derived from bisphenol F having 2 nucleus or a skeleton derived from a polynucleer having a bisphenol F skeleton and having 3 or more nuclei, and n represents an integer. When n is an epoxy compound obtained by reacting an epoxy compound represented by the formula (51X) with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

The fourth reactant may have a structure represented by the following formula (54X).

In the formula (54X), X represents a skeleton derived from a bisphenol F having two nuclei, or a skeleton derived from a polynucleer having a bisphenol F skeleton and having three or more nuclei, and n represents an integer. When n is an epoxy compound obtained by reacting an epoxy compound represented by the above formula (54X) with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether , And the weight average molecular weight of the epoxy compound is 500 to 150,000.

In the formulas (51X) and (54X), X is a structural unit represented by the following formula (Xa).

In the formula (Xa), p represents an integer of 0 or more. p is preferably 10 or less, more preferably 5 or less, particularly preferably 3 or less. In the formula (Xa), when p is 0, it represents a skeleton derived from a bisphenol F nucleus, and when p is an integer of 1 or more in the formula (Xa), 3 or more nuclei having a bisphenol F skeleton And the like. In the formula (Xa), the bonding site of one hydroxyl group to one benzene ring is not particularly limited. The bonding site of one oxygen atom (-O- group) to one benzene ring in the formula (Xa) is not particularly limited.

(Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with the reactant (X) such as the first, second, third, A vinyl group or an epoxy group can be introduced into the side chain. (Meth) acrylic acid represented by the following formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the following formula (B), or a compound represented by the following formula ) Is preferably 4-hydroxybutyl glycidyl ether. The compound to be reacted with the reactant (X) may be (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether. The term "(meth) acryl" refers to acryl and methacryl. The "(meth) acryloyl" represents acryloyl and methacryloyl.

In the above formula (A), R represents a hydrogen atom or a methyl group.

In the above formula (B), R represents a hydrogen atom or a methyl group.

In order to introduce a vinyl group into the side chain of the epoxy compound according to the present invention, the compound to be reacted with the reactant (X) is preferably (meth) acrylic acid or 2- (meth) acryloyloxyethyl isocyanate. The compound to be reacted with the reactant (X) is preferably (meth) acrylic acid, and is preferably 2- (meth) acryloyloxyethyl isocyanate. When the epoxy compound according to the present invention has a vinyl group in the side chain, the epoxy compound according to the present invention can be photo-cured and thermally cured. Thus, for example, a curable composition containing an epoxy compound can be cured by irradiating it with B light (semi-cured) and then heating it. It is preferable that the epoxy compound according to the present invention has a urethane bond from the viewpoint of enabling the epoxy compound to be cured more rapidly and further enhancing the adhesiveness and humidity resistance of the cured product. Further, by using 2- (meth) acryloyloxyethyl isocyanate, the storage stability of the epoxy compound, the mixture of the epoxy compound and the curable composition can be further enhanced.

In order to introduce an epoxy group into the side chain of the epoxy compound according to the present invention, the compound to be reacted with the reactant (X) is preferably 4-hydroxybutyl glycidyl ether. By introducing an epoxy group into the side chain in this way, the cross-linking density of the cured product can be increased and the heat resistance of the cured product can be further improved.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B) or the above-mentioned formula (A) (61A), (61B) or (61C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the formula (61A), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (61A) is 500 or more and 150,000 or less.

In the formula (61B), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (61B) is 500 or more and 150,000 or less.

In the above formula (61C), n represents an integer. Herein, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (61C) is 500 or more and 150,000 or less.

The bonding site of one oxygen atom to one benzene ring in the formulas (61A), (61B) and (61C) is not particularly limited. This bonding site is determined according to the kind of bisphenol F (for example, the above formulas (1-1) to (1-3)).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (61XA), formula (61XB) or formula (61XC) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (61C)

X represents a skeleton derived from bisphenol F having two nucleus chains or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having three or more nuclei, R represents a hydrogen atom or a methyl group, and n represents a Represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (61XA) is 500 or more and 150,000 or less.

X represents a skeleton derived from bisphenol F having two nuclei or a skeleton derived from a polynuclear nucleus having a bisphenol F skeleton and having three or more nuclei, R represents a hydrogen atom or a methyl group, and n represents Represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (61XB) is 500 or more and 150,000 or less.

In the formula (61XC), X represents a skeleton derived from bisphenol F having two nuclei, or a skeleton derived from a polynucleer having a bisphenol F skeleton and having three or more nuclei, and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (61XC) is 500 or more and 150,000 or less.

In the formulas (61XA), (61XB) and (61XC), X is a structural unit represented by the formula (Xa).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (62A), (62B) or (62C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the formula (62A), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (62A) is 500 or more and 150,000 or less.

In the above formula (62B), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (62B) is 500 or more and 150,000 or less.

In the above formula (62C), n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (62C) is 500 or more and 150,000 or less.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (63A), (63B) or (63C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the formula (63A), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (63A) is 500 or more and 150,000 or less.

In the formula (63B), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (63B) is 500 or more and 150,000 or less.

In the above equation (63C), n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (63C) is 500 or more and 150,000 or less.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B) or the above-mentioned formula (A) (64A), (64B) or (64C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the above formula (64A), R represents a hydrogen atom or a methyl group, and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (64A) is 500 or more and 150,000 or less.

In the above formula (64B), R represents a hydrogen atom or a methyl group, and n represents an integer. N is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (64B) is 500 or more and 150,000 or less.

In the above formula (64C), n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (64C) is 500 or more and 150,000 or less.

The bonding site of one oxygen atom to one benzene ring in the formulas (64A), (64B) and (64C) is not particularly limited. This bonding site is determined according to the kind of bisphenol F (for example, the above formulas (1-1) to (1-3)).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (64XA), formula (64XB) or formula (64XC) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (64)

X represents a skeleton derived from a bisphenol F having two nucleus chains or a skeleton derived from a polynuclear nucleus having a bisphenol F skeleton and having three or more nuclei, R represents a hydrogen atom or a methyl group, n is Represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (64XA) is 500 or more and 150,000 or less.

X represents a skeleton derived from bisphenol F having 2 nucleus chains or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having 3 or more nuclei, R represents a hydrogen atom or a methyl group, and n represents Represents an integer. N is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (64XB) is 500 or more and 150,000 or less.

In the formula (64XC), X represents a skeleton derived from bisphenol F having two nuclei, or a skeleton derived from a polynucleer having a bisphenol F skeleton and having three or more nuclei, and n represents an integer. Here, n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (64XC) is 500 or more and 150,000 or less.

In the formulas (64XA), (64XB) and (64XC), X is a structural unit represented by the formula (Xa).

(61A), (61B), (61C), (61XA), (61XB), (61XC), (62A), (62B), (62C) (61A), (61A), and (61B) among the formulas (63B), (63C), (64A), (64B), (64C) 61A, 61B, 61C, 61XA, 61XC, 62A, 62B, 62C, 63A, 63B, 63C) is preferable, and it is preferable that the above equations (61XA), 61XB, 61XC, 62A, 62B, 62C, 63A, 63B, ) Is more preferable. (61A), (61B), (61C), (61XA), (61XB), (61XC), (62A), (62B), (62C) (64B), (64B), and (64XC), n is the number of epoxy groups represented by the formulas (63B), 63C, 64A, 64B, 64C, The compound is preferably an integer in which the weight average molecular weight of the compound is 1,000 or more and 50,000 or less, more preferably 1,000 or more and 15,000 or less. Further, n may be 1 or more, or may be 2 or more. (61A), (61B), (61C), (61XA), (61XB), (61XC), (62A), (62B), (62C) , The weight average molecular weight of the epoxy compound in the formula (63B), the formula (63C), the formula (64A), the formula (64B), the formula (64C), the formula (64XA) More preferably not less than the value of the weight average molecular weight in the case of n = 1, more preferably not less than 500 and not less than the value of the weight average molecular weight in the case of n = 2.

(61A), (61B), (61C), (61XA), (61XB), (61XC), (62A), (62B), (62C) Representatively all of the hydroxyl groups (100) are represented in the formulas (63B), (63C), (64A), (64B), (64C), (64XA), (64XB) %) Is reacted, but the unreacted hydroxyl group may remain. The ratio of the number of the hydroxyl groups (the formula (a), the formula (b), and the formula (c) described below) to the number of the hydroxyl groups which are reacted in the total number of hydroxyl groups before the reaction may be 0.1% Or more, more preferably 3% or more, 5% or more, 100% or less, preferably 80% or less, more preferably 60% or less, still more preferably 40% % Or less. The ratio of the number of hydroxyl groups can be measured by NMR.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or a combination thereof with a part of the hydroxyl group of the first reactant represented by the above- Or a 4-hydroxybutyl glycidyl ether represented by the above formula (C) is reacted to obtain a first epoxy compound represented by the following formula (71A), (71B) or (71C).

In the formula (71A), Z represents a hydroxyl group or a group represented by the following formula (a), a plurality of Zs include a group represented by the following formula (a), and n represents an integer. Herein, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (71A) is 500 or more and 150,000 or less.

In the above formula (a), R represents a hydrogen atom or a methyl group.

In the formula (71B), Z represents a hydroxyl group or a group represented by the following formula (b), a plurality of Zs include a group represented by the following formula (b), and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (71B) is 500 or more and 150,000 or less.

In the above formula (b), R represents a hydrogen atom or a methyl group.

In the formula (71C), Z represents a hydroxyl group or a group represented by the following formula (c), a plurality of Zs include a group represented by the following formula (c), and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (71C) is 500 or more and 150,000 or less.

In the formulas (71A), (71B) and (71C), the bonding site of one oxygen atom to one benzene ring is not particularly limited. This bonding site is determined according to the kind of bisphenol F (for example, the above formulas (1-1) to (1-3)).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (71XA), formula (71XB) or formula (71XC) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (71)

In the formula (71XA), X represents a skeleton derived from a bisphenol F having 2 nucleus chains or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having 3 or more nuclei, and Z is a hydroxyl group or a group derived from the formula , A plurality of Zs contain a group represented by the above formula (a), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (71XA) is 500 or more and 150,000 or less.

In the formula (71XB), X represents a skeleton derived from bisphenol F having two nucleus chains, or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having three or more nuclei, and Z is a hydroxyl group or a group derived from the formula , A plurality of Z's include a group represented by the above formula (b), and n represents an integer. Herein, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (71XB) is 500 or more and 150,000 or less.

In the formula (71XC), X represents a skeleton derived from a bisphenol F having two nuclei or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having three or more nuclei, and Z represents a hydroxyl group or a group derived from the formula (c) , Z represents a group represented by the above formula (c), and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (71XC) is 500 or more and 150,000 or less.

In the formulas (71XA), (71XB) and (71XC), X is a structural unit represented by the formula (Xa).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (72A), (72B) or (72C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the formula (72A), Z represents a hydroxyl group or a group represented by the formula (a), a plurality of Zs include a group represented by the formula (a), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (72A) is 500 or more and 150,000 or less.

In the formula (72B), Z represents a hydroxyl group or a group represented by the formula (b), a plurality of Zs include a group represented by the formula (b), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (72B) is 500 or more and 150,000 or less.

In the formula (72C), Z represents a hydroxyl group or a group represented by the formula (c), a plurality of Zs contain a group represented by the formula (c), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (72C) is 500 or more and 150,000 or less.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (73A), (73B) or (73C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (C)

In the formula (73A), Z represents a hydroxyl group or a group represented by the formula (a), a plurality of Zs contain a group represented by the formula (a), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (73A) is 500 or more and 150,000 or less.

In the formula (73B), Z represents a hydroxyl group or a group represented by the formula (b), a plurality of Zs contain a group represented by the formula (b), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (73B) is 500 or more and 150,000 or less.

In the formula (73C), Z represents a hydroxyl group or a group represented by the formula (c), a plurality of Zs include a group represented by the formula (c), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (73C) is 500 or more and 150,000 or less.

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B) or the above-mentioned formula (A) (74A), (74B) or (74C) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the following formula (74C)

In the formula (74A), Z represents a hydroxyl group or a group represented by the formula (a), a plurality of Zs include a group represented by the formula (a), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (74A) is 500 or more and 150,000 or less.

In the above formula (74B), Z represents a hydroxyl group or a group represented by the above formula (b), a plurality of Zs contain a group represented by the above formula (b), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (74B) is 500 or more and 150,000 or less.

In the formula (74C), Z represents a hydroxyl group or a group represented by the formula (c), a plurality of Zs include a group represented by the formula (c), and n represents an integer. Provided that n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (74C) is 500 or more and 150,000 or less.

The bonding site of one oxygen atom to one benzene ring in the formulas (74A), (74B) and (74C) is not particularly limited. This bonding site is determined according to the kind of bisphenol F (for example, the above formulas (1-1) to (1-3)).

(Meth) acrylic acid represented by the above formula (A), 2- (meth) acryloyloxyethyl isocyanate represented by the above formula (B), or the above-mentioned formula (74XA), formula (74XB) or formula (74XC) is obtained by reacting 4-hydroxybutyl glycidyl ether represented by the formula (C)

In the formula (74XA), X represents a skeleton derived from bisphenol F having two nucleus chains or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having three or more nuclei, and Z is a hydroxyl group or a group derived from the formula , A plurality of Zs contain a group represented by the above formula (a), and n represents an integer. Herein, n is an integer such that the weight average molecular weight of the epoxy compound represented by the formula (74XA) is 500 or more and 150,000 or less.

In the above formula (74XB), X represents a skeleton derived from a bisphenol F having 2 nucleus chains or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having 3 or more nuclei, and Z is a hydroxyl group or a group represented by the formula (b) , A plurality of Z's include a group represented by the above formula (b), and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (74XB) is 500 or more and 150,000 or less.

In the formula (74XC), X represents a skeleton derived from a bisphenol F having two nuclei or a skeleton derived from a polynuclear body having a bisphenol F skeleton and having three or more nuclei, and Z is a hydroxyl group or a group derived from the formula (c) , Z represents a group represented by the above formula (c), and n represents an integer. Here, n is an integer in which the weight average molecular weight of the epoxy compound represented by the formula (74XC) is 500 or more and 150,000 or less.

In the formulas (74XA), (74XB) and (74XC), X is a structural unit represented by the formula (Xa).

(71A), (71B), (71C), (71XA), (71XB), (71XC), (72A), (72B), (72C) (71A), the equation (71A), and the equation (71A) in the equation (73B), the equation (73C), the equation (74A), the equation (74B), the equation (74C), the equation 71B, 71C, 71XA, 71XC, 72A, 72B, 72C, 73A, 73B, 73C) are preferable, and it is preferable to use the above equations (71XA), (71XB), (71XC), 72A, 72B, 72C, 73A, ) Is more preferable. (71A), (71B), (71C), (71XA), (71XB), (71XC), (72A), (72B), (72C) N is expressed by these formulas in the formulas (73B), (73C), (74A), (74B), (74C), (74XA), (74XB) The epoxy compound preferably has an average molecular weight of 1,000 or more and 50,000 or less, more preferably 1,000 or more and 15,000 or less. Further, n may be 1 or more, or may be 2 or more. (71A), (71B), (71C), (71XA), (71XB), (71XC), (72A), (72B), (72C) , The weight average molecular weight of the epoxy compound in the formula (73B), the formula (73C), the formula (74A), the formula (74B), the formula (74C), the formula (74XB) And is preferably at least the value of the weight average molecular weight in the case of n = 1, more preferably at least 500 or more and at least the value of the weight average molecular weight in the case of n = 2.

(Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with the first reactant in order to further improve the adhesiveness of the cured product It is preferable that there are two peaks in the molecular weight distribution of the epoxy compound. (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with the second reactant in order to further improve the adhesiveness of the cured product, It is preferable that there are two peaks in the molecular weight distribution of the epoxy compound.

A specific reaction for reacting the reactant (X) with (meth) acrylic acid is a condensation reaction.

Specific reactions for reacting the reactant (X) with 2- (meth) acryloyloxyethyl isocyanate include addition reaction.

Specific reaction for reacting the reactant (X) with 4-hydroxybutyl glycidyl ether includes a condensation reaction.

In order to obtain an epoxy compound according to the present invention, in the case of using a reaction product using a mixture of bisphenol F and bisphenol F skeleton having two nucleus chains and a polynuclear body having three or more nuclei, bisphenol F , The proportion of the structural unit derived from bisphenol F having two nucleus out of the total of 100% by weight of the derived structural unit and the structural unit derived from the multinuclear body having the bisphenol F skeleton and having 3 or more nuclei is preferably 70% by weight or more , More preferably not less than 85 wt%, preferably not more than 99.9 wt%, and more preferably not more than 99 wt%. If the proportion of the structural units derived from bisphenol F having two nuclei in the total of 100% by weight of the structural units is not less than the lower limit and not more than the upper limit, the adhesiveness of the cured product using the epoxy compound is further increased, The reliability of the connection structure using the above-mentioned curable composition is further enhanced.

(Mixture of epoxy compounds)

The mixture of epoxy compounds according to the present invention contains at least two kinds of the above-mentioned epoxy compounds. As described above, the above-mentioned epoxy compounds may be used in combination of two or more. By using two or more of the above-mentioned epoxy compounds in combination, the viscosity of the mixture of epoxy compounds can be easily adjusted.

From the viewpoint of enabling the epoxy compound to be cured even more rapidly and further increasing the adhesiveness and moisture resistance of the cured product and suppressing the generation of voids in the connection structure, the mixture of epoxy compounds according to the present invention is bisphenol F (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with a first reactant of 1,6-hexanediol diglycidyl ether and 1,6- (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl (meth) acrylate is added to a second reaction product of an epoxy compound and resorcinol and 1,6-hexanediol diglycidyl ether And a second epoxy compound obtained by reacting an ether.

From the viewpoint of enabling the epoxy compound to be cured more rapidly and further enhancing the adhesiveness and moisture resistance of the cured product and suppressing the generation of voids in the connection structure, the mixture of the epoxy compound according to the present invention is a resorcin (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with a second reactant of 1,6-hexanediol diglycidyl ether (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with a third reaction product of a 2-epoxy compound, resorcinol and resorcinol diglycidyl ether And a third epoxy compound obtained by subjecting the first epoxy compound to a polymerization reaction.

The mixture of epoxy compounds according to the present invention preferably comprises the first epoxy compound and the second epoxy compound or comprises the second epoxy compound and the third epoxy compound.

From the viewpoint of enhancing the coatability and making it difficult to generate pores in the connection structure, the mixture of epoxy compounds preferably has a viscosity at 23 ° C of preferably 50 Pa · s or more, more preferably 100 Pa · s or more, It is 1,200 Pa · s or less, more preferably 600 Pa · s or less, and further preferably 400 Pa · s or less.

(Curable composition)

The curable composition according to the present invention comprises the above-mentioned epoxy compound and a thermosetting agent. That is, the curable composition according to the present invention comprises an epoxy compound having an epoxy group at both terminals, a vinyl group or an epoxy group in the side chain, and a weight average molecular weight of 500 to 150,000, and a thermosetting agent. The curable composition according to the present invention can be rapidly cured, and the adhesive property and moisture resistance of the cured product can be increased.

The curable composition according to the present invention preferably contains at least two kinds of epoxy compounds. The viscosity of the curable composition can be easily adjusted by using two or more of the above-mentioned epoxy compounds in combination.

From the viewpoint of enhancing the coatability and making it difficult to generate pores in the connection structure, the viscosity of the curable composition at 23 캜 is preferably 50 Pa · s or more, more preferably 100 Pa · s or more, preferably 1,200 Pa S or less, more preferably 600 Pa s or less, and even more preferably 400 Pa s or less.

The curable composition according to the present invention is characterized in that (1) the epoxy compound is added to the first reaction product of bisphenol F and 1,6-hexanediol diglycidyl ether with (meth) acrylic acid, 2- (meth) acryloyloxyethyl Isocyanate or 4-hydroxybutyl glycidyl ether, and comprises bisphenol F diglycidyl ether or 1,6-hexanediol diglycidyl ether, or (2) the above-mentioned first epoxy compound obtained by reacting The epoxy compound is reacted with a second reaction product of resorcinol and 1,6-hexanediol diglycidyl ether with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl Ether, and comprises a resorcinol diglycidyl ether or 1,6-hexanediol diglycidyl ether, or (3) the epoxy compound contains a resorcinol and a resorcinol Nodiglycidyl ether (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether to a third reactant of the resorcinol diglycidyl ether, and a third epoxy compound obtained by reacting (Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is added to the fourth reaction product of bisphenol F and resorcinol diglycidyl ether. And a fourth epoxy compound obtained by reacting a cidyl ether, and more preferably a bisphenol F diglycidyl ether or a resorcinol diglycidyl ether. In this case, the crosslinking density of the cured product of the curable composition is increased, the adhesiveness of the cured product using the epoxy compound is further increased, and the reliability of the connecting structure using the curable composition containing the epoxy compound is further increased.

The curable composition according to the present invention comprises (1) the epoxy compound includes the first epoxy compound, and includes bisphenol F diglycidyl ether or 1,6-hexanediol diglycidyl ether, (2) Wherein the epoxy compound comprises the second epoxy compound and contains resorcinol diglycidyl ether or 1,6-hexanediol diglycidyl ether, or (3) the epoxy compound contains the third epoxy compound And more preferably contains resorcinol diglycidyl ether. In this case, the crosslinking density of the cured product of the curable composition is increased, the adhesiveness of the cured product using the epoxy compound is further increased, and the reliability of the connecting structure using the curable composition containing the epoxy compound is further increased.

When the curable composition according to the present invention contains the first, second, third and fourth epoxy compounds and bisphenol F diglycidyl ether, resorcinol diglycidyl ether or 1,6-hexanediol diglycidyl ether It is preferable that bisphenol F diglycidyl ether, resorcinol diglycidyl ether and 1,6-hexanediol diglycidyl ether are added to 100 parts by weight in total of the first, second, third and fourth epoxy compounds, The content of the total amount of the cidyl ether is preferably at least 0.1 part by weight, more preferably at least 1 part by weight, preferably at most 100 parts by weight, more preferably at most 20 parts by weight. If the content of the sum of bisphenol F diglycidyl ether, resorcinol diglycidyl ether and 1,6-hexanediol diglycidyl ether is lower than or equal to the lower limit and below the upper limit, the crosslinking density of the cured product of the curable composition is further increased The adhesiveness of the cured product using the epoxy compound is further increased, and the reliability of the connection structure using the curable composition containing the epoxy compound is further increased.

The curable composition according to the present invention is characterized in that in addition to the above-mentioned epoxy compound (epoxy compound according to the present invention), epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with at least one of two epoxy groups at both ends of the epoxy compound It is preferable to further include a rate. In this case, the crosslinking density of the cured product of the curable composition is increased, the adhesiveness of the cured product using the epoxy compound is further increased, and the reliability of the connecting structure using the curable composition containing the epoxy compound is further increased.

The epoxy (meth) acrylate obtained by reacting the above-mentioned epoxy compound with (meth) acrylic acid in at least one of the two epoxy groups at both terminals of the epoxy compound has both terminal portions (epoxy group or (meth) acryloyl group) It is preferable to have the same structure. The epoxy compound and the epoxy (meth) acrylate together preferably have a skeleton derived from bisphenol F, and are preferably derived from resorcinol. The epoxy compound and the epoxy (meth) acrylate together preferably have a skeleton derived from 1,6-hexanediol diglycidyl ether and preferably have a skeleton derived from resorcinol diglycidyl ether Do. By using the epoxy compound and the epoxy (meth) acrylate as described above, the crosslinking density of the cured product of the curable composition is further increased, the adhesiveness of the cured product using the epoxy compound is further increased, and the curability The reliability of the connection structure using the composition is further enhanced.

When the curable composition according to the present invention contains the epoxy compound and the epoxy (meth) acrylate, the content of the epoxy (meth) acrylate is preferably 0.1 parts by weight or more based on 100 parts by weight of the epoxy compound, More preferably 1 part by weight or more, preferably 100 parts by weight or less, and more preferably 20 parts by weight or less. If the content of the epoxy (meth) acrylate is lower than or equal to the lower limit and lower than or equal to the upper limit, the crosslinking density of the cured product of the curable composition becomes even higher, the adhesiveness of the cured product using the epoxy compound becomes further higher, The reliability of the connection structure using the above-mentioned curable composition is further enhanced.

The heat curing agent contained in the curable composition according to the present invention is not particularly limited. The thermosetting agent cures the epoxy compound according to the invention, or a mixture of the epoxy compounds according to the invention. As the thermosetting agent, conventionally known thermosetting agents may be used. The thermosetting agent includes a thermal radical initiator. The thermosetting agent may be used alone or in combination of two or more.

Examples of the heat curing agent include a cation curing agent, an imidazole curing agent, an amine curing agent, a phenol curing agent, a polythiol curing agent, an acid anhydride, and a thermal radical initiator. Among them, a cationic curing agent, an imidazole curing agent, a polythiol curing agent or an amine curing agent is preferable because the curable composition can be cured much more quickly. Further, since the storage stability of the curable composition can be enhanced, a latent curing agent is preferable. The latent curing agent is preferably a latent imidazole curing agent, a latent polythiol curing agent or a latent amine curing agent. Further, the thermosetting agent may be coated with a high molecular substance such as a polyurethane resin or a polyester resin.

Examples of the imidazole curing agent include, but are not limited to, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl- Imidazolium trimellitate, 2,4-diamino-6- [2'-methylimidazolyl- (1 ')] - ethyl -s- triazine and 2,4- -Methylimidazolyl- (1 ')] - ethyl-s-triazine isocyanuric acid adduct.

Examples of the polythiol curing agent include, but are not limited to, trimethylolpropane tris-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate and dipentaerythritol hexa-3-mercaptopropionate Nate and so on.

Examples of the amine curing agent include, but are not limited to, hexamethylenediamine, octamethylenediamine, decamethylenediamine, 3,9-bis (3-aminopropyl) -2,4,8,10-tetaspiro [5.5] undecane, Bis (4-aminocyclohexyl) methane, metaphenylenediamine and diaminodiphenylsulfone.

Among these thermosetting agents, polythiol compounds or acid anhydrides are preferred. Since the curing speed of the curable composition can be further increased, a polythiol compound is preferable.

Among the polythiol compounds, pentaerythritol tetrakis-3-mercaptopropionate is more preferable. By using the polythiol compound, the curing speed of the curable composition can be further increased.

The thermal radical initiator is not particularly limited, and examples thereof include azo compounds and peroxides. Examples of the peroxide include a diacyl peroxide compound, a peroxy ester compound, a hydroperoxide compound, a peroxydicarbonate compound, a peroxyketal compound, a dialkyl peroxide compound, and a ketone peroxide compound.

Examples of the azo compound include 2,2'-azobisisobutyronitrile, 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis (2,4-dimethyl Azobis-1-cyclohexanecarbonitrile, dimethyl-2,2'-azobisisobutyrate, dimethyl-2,2'-azobis (2-methylpropionate) Azo compounds such as dimethyl-1,1'-azobis (1-cyclohexanecarboxylate), 4,4'-azobis (4-cyanovaleric acid), 2,2'-azobis Azo compounds such as 2,2'-azobis (2-methylpropionamide) dihydrate, and 2,2'-azobis (2,4,4-trimethylpentane) And the like.

Examples of the diacyl peroxide compound include benzoyl peroxide, diisobutyryl peroxide, di (3,5,5-trimethylhexanoyl) peroxide, dilauryl peroxide, and dicosyl peroxide. Examples of the peroxy ester compounds include cumyl peroxyneodecanoate, 1,1,3,3-tetramethyl butyl peroxyneodecanoate, tert-hexyl peroxyneodecanoate, tert-butyl peroxyneodecane Tert-butyl peroxyneoheptanoate, tert-hexyl peroxy pivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl- Tert-butylperoxy-2-ethylhexanoate, tert-butylperoxy-2-ethylhexanoate, tert-butylperoxy- Butyl peroxy isobutyrate, tert-butyl peroxylaurate, tert-butyl peroxyisophthalate, tert-butyl peroxyacetate, tert-butyl peroxy octoate and tert-butyl peroxybenzoate. Examples of the hydroperoxide compound include cumene hydroperoxide, p-menthol hydroperoxide, and the like. Examples of the peroxydicarbonate compound include di-sec-butyl peroxydicarbonate, di (4-t-butylcyclohexyl) peroxydicarbonate, di- -Ethylhexyl) peroxycarbonate, and the like. Other examples of the peroxide include methyl ethyl ketone peroxide, potassium persulfate, and 1,1-bis (tert-butylperoxy) -3,3,5-trimethylcyclohexane.

The decomposition temperature for obtaining the 10-hour half-life of the thermal radical initiator is preferably 30 占 폚 or higher, more preferably 40 占 폚 or higher, preferably 90 占 폚 or lower, more preferably 80 占 폚 or lower, still more preferably 70 占 폚 Or less. When the decomposition temperature for obtaining the 10-hour half-life of the thermal radical initiator is less than 30 ° C, the storage stability of the curable composition tends to be lowered, and if it exceeds 90 ° C, the curable composition tends to be insufficiently thermally cured.

The content of the thermosetting agent is not particularly limited. In the curable composition according to the present invention, the content of the thermosetting agent is preferably 0.01 parts by weight or more, more preferably 1 part by weight or more, preferably 200 parts by weight or less, more preferably 100 parts by weight or less, Is not more than 100 parts by weight, more preferably not more than 75 parts by weight. When the content of the thermosetting agent is lower than the lower limit described above, it is easy to sufficiently cure the curable composition. If the content of the thermosetting agent is less than the upper limit, an excess of the thermosetting agent that is not involved in curing after curing is hardly left, and the heat resistance of the cured product is further increased.

When the heat curing agent is an imidazole curing agent or a phenolic curing agent, the content of the imidazole curing agent or the phenolic curing agent is preferably 1 part by weight or more, and preferably 15 parts by weight or less based on 100 parts by weight of the total amount of the epoxy compound . When the heat curing agent is an amine curing agent, a polythiol curing agent or an acid anhydride, the content of the amine curing agent, the polythiol curing agent or the acid anhydride is preferably 15 parts by weight or more based on 100 parts by weight of the total amount of the epoxy compound, Is not more than 40 parts by weight.

When the heat curing agent is a thermal radical initiator, the content of the heat radical initiator is not particularly limited. The content of the thermal radical initiator is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, preferably 10 parts by weight or less, more preferably 5 parts by weight or less, based on 100 parts by weight of the total amount of the epoxy compound to be. If the content of the thermal radical curing agent is lower than or equal to the lower limit and lower than or equal to the upper limit, the thermosetting composition can be sufficiently thermally cured.

[Other components]

The curable composition according to the present invention preferably further comprises a curing accelerator. By using the curing accelerator, the curing speed of the curable composition can be further increased. The curing accelerator may be used alone or in combination of two or more.

Specific examples of the curing accelerator include imidazole curing accelerators and amine curing accelerators. Among them, an imidazole curing accelerator is preferable. The imidazole curing accelerator or amine curing accelerator can also be used as an imidazole curing agent or an amine curing agent.

Examples of the imidazole curing accelerator include 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl- Methyl-imidazolyl- (1 ')] - ethyl-s-triazine and 2,4-diamino-6- [2'-methyl (1 ')] - ethyl-s-triazine isocyanuric acid adduct.

The content of the curing accelerator is preferably at least 0.5 part by weight, more preferably at least 1 part by weight, preferably at most 6 parts by weight, more preferably at most 4 parts by weight, based on 100 parts by weight of the total amount of the epoxy compound to be. If the content of the curing accelerator is the above lower limit, it is easy to sufficiently cure the curable composition. If the content of the curing accelerator is less than the upper limit, excess curing accelerator which is not involved in curing after curing is hard to remain.

The curable composition according to the present invention may further comprise a photocurable compound and a photopolymerization initiator so as to be cured by light irradiation. By using the photocurable compound and the photopolymerization initiator, the curable composition can be cured by light irradiation. In addition, the curable composition can be semi-cured and the flowability of the curable composition can be lowered.

The photocurable compound is not particularly limited. As the photocurable compound, a (meth) acrylic resin or a cyclic ether group-containing resin is preferably used, and a (meth) acrylic resin is more preferably used. The (meth) acrylic resin is a methacrylic resin and an acrylic resin. The (meth) acrylic resin has a (meth) acryloyl group. The (meth) acryloyl group represents a methacryloyl group and an acryloyl group.

An ester compound obtained by reacting (meth) acrylic acid with a compound having a hydroxyl group, an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with an epoxy compound, or an epoxy (meth) acrylate having a hydroxyl group in the isocyanate (Meth) acrylate obtained by reacting an acrylic acid derivative with an acrylate or the like is preferably used.

The ester compound obtained by reacting the above (meth) acrylic acid with a compound having a hydroxyl group is not particularly limited. As the ester compound, a monofunctional ester compound, a bifunctional ester compound and an ester compound having three or more functional groups can be used.

The photocurable compound preferably contains a photocurable compound having an epoxy group or a thiadiene group and a (meth) acryloyl group.

The photo-curing compound having an epoxy group or a thiiranyl group and a (meth) acryloyl group may be a compound having two or more epoxy groups or a part of the epoxy group of a compound having two or more epoxy groups, Is preferably a photo-curable compound obtained by conversion. Such photocurable compounds are partial (meth) acrylated epoxy compounds or partial (meth) acrylated episulfide compounds.

The photocurable compound is preferably a reaction product of (meth) acrylic acid with a compound having two or more epoxy groups or two or more epoxy groups. This reaction product is obtained by reacting a compound having two or more epoxy groups or two or more epoxy groups with (meth) acrylic acid in the presence of a catalyst such as a basic catalyst according to a conventional method. It is preferable that at least 20% of the epoxy group or the (meth) acryloyl group is converted into (meth) acryloyl group (conversion ratio). The conversion rate is more preferably 30% or more, preferably 80% or less, more preferably 70% or less. It is most preferable that not less than 40% and not more than 60% of the epoxy group or the (meth) acryloyl group is converted into a (meth) acryloyl group.

Examples of the photocurable compound having an epoxy group or a thiiranyl group and a (meth) acryloyl group include bisphenol epoxy (meth) acrylate, cresol novolak epoxy (meth) acrylate, carboxylic anhydride modified epoxy , And phenol novolak type epoxy (meth) acrylate.

As the photocurable compound, a modified phenoxy resin obtained by converting part of an epoxy group or a part of thienyl groups of a phenoxy resin having two or more epoxy groups or two or more epoxy groups into a (meth) acryloyl group may be used. That is, a modified phenoxy resin having an epoxy group or a (meth) acryloyl group can be used.

When the photocurable compound other than the above-mentioned photocurable compound is contained, the photocurable compound may be a crosslinkable compound or a non-crosslinkable compound.

Specific examples of the crosslinkable compound include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (Meth) acrylate, (poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, neopentyl glycol di (Meth) acrylate, urethane (meth) acrylate, urethane (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane trimethacrylate, And the like.

Specific examples of the non-crosslinkable compound include ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, isobutyl (meth) acrylate, isobutyl (meth) acrylate, isobutyl (Meth) acrylate, decyl (meth) acrylate, decyl (meth) acrylate, decyl (meth) acrylate, ) Acrylate, and the like.

From the viewpoint of efficiently curing the curable composition, the content of the photocurable compound is preferably 0.1 parts by weight or more, more preferably 1 part by weight or more, and even more preferably 1 part by weight or more, based on 100 parts by weight of the total amount of the epoxy compound 10 parts by weight or more, particularly preferably 50 parts by weight or more, preferably 10,000 parts by weight or less, more preferably 1,000 parts by weight or less, further preferably 500 parts by weight or less.

The photopolymerization initiator is not particularly limited. The photopolymerization initiator includes a photo radical initiator. The above-mentioned photopolymerization initiator may be used alone, or two or more thereof may be used in combination.

Specific examples of the photopolymerization initiator include an acetophenone photopolymerization initiator (acetophenone photoradical initiator), a benzophenone photopolymerization initiator (benzophenone photoradical initiator), a thioxanthone, a ketal photopolymerization initiator (a ketal photoradical initiator), a halogenated Ketones, acylphosphine oxides and acylphosphonates. Other photopolymerization initiators may be used.

Specific examples of the acetophenone photopolymerization initiator include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone, 2-hydroxy- , Methoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, and 2-hydroxy-2-cyclohexylacetophenone. Specific examples of the ketal photopolymerization initiator include benzyl dimethyl ketal and the like.

The content of the photopolymerization initiator is not particularly limited. The content of the photopolymerization initiator is preferably 0.1 parts by weight or more, more preferably 0.2 parts by weight or more, still more preferably 2 parts by weight or more, and preferably 10 parts by weight or less, based on 100 parts by weight of the photocurable composition Preferably 5 parts by weight or less. If the content of the photopolymerization initiator is lower than the above lower limit, it is easy to sufficiently obtain the effect of adding the photopolymerization initiator. If the content of the photopolymerization initiator is not more than the upper limit, the adhesive force of the cured product of the curable composition becomes sufficiently high.

The curable composition according to the present invention preferably further comprises a phenolic compound. The phenolic compound has a phenolic hydroxyl group bonded to a benzene ring with a hydroxyl group. Examples of the phenolic compound include polyphenols, triols, hydroquinone, and tocopherol (vitamin E). The phenolic compound may be used alone, or two or more thereof may be used in combination.

The curable composition according to the present invention preferably further comprises a filler. By the use of the filler, latent heat expansion of the cured product of the curable composition can be suppressed. Specific examples of the filler include silica, aluminum nitride, and alumina. Only one type of filler may be used, or two or more types may be used in combination.

The content of the filler is not particularly limited. The content of the filler is preferably 5 parts by weight or more, more preferably 15 parts by weight or more, preferably 200 parts by weight or less, and even more preferably 100 parts by weight or less, based on 100 parts by weight of the total amount of the curable compound. When the content of the filler is not less than the lower limit and not more than the upper limit, the latent heat expansion of the cured product can be sufficiently suppressed, and the filler can be sufficiently dispersed in the curable composition. The curable compound includes the epoxy compound and the photo-curable compound.

The curable composition according to the present invention may contain a solvent. By using the above-mentioned solvent, the viscosity of the curable composition can be easily adjusted.

Examples of the solvent include ethyl acetate, methyl cellosolve, toluene, acetone, methyl ethyl ketone, cyclohexane, n-hexane, tetrahydrofuran and diethyl ether.

The curable composition according to the present invention may further contain, if necessary, a storage stabilizer, an ion scavenger or a silane coupling agent.

(Curable composition containing conductive particles)

When the curable composition according to the present invention further comprises conductive particles, the curable composition may be used as a conductive material. The conductive material is preferably an anisotropic conductive material. The mixture of the epoxy compound and the epoxy compound is preferably used as the conductive material together with the conductive particles and more preferably used as the anisotropic conductive material together with the conductive particles.

The conductive particles electrically connect the electrodes of the first and second connection target members. Specifically, the conductive particles electrically connect, for example, the circuit board and the electrodes of the semiconductor chip. The conductive particles are not particularly limited as long as they are conductive particles. The conductive particles may have a conductive portion on the conductive surface. The surface of the conductive part of the conductive particles may be covered with the insulating layer. In this case, at the time of connection of the member to be connected, the insulating layer between the conductive portion and the electrode is excluded. Examples of the conductive particles include conductive particles obtained by coating the surface of an organic particle, an inorganic particle other than a metal, an organic-inorganic hybrid particle or metal particle with a conductive layer (metal layer), or a metal particle . The conductive portion is not particularly limited. Examples of the metal constituting the conductive portion include gold, silver, copper, nickel, palladium and tin. Examples of the conductive layer include a gold layer, a silver layer, a copper layer, a nickel layer, a palladium layer, or a conductive layer containing tin.

From the viewpoint of increasing the contact area between the electrode and the conductive particles and further enhancing the conduction reliability between the electrodes, the conductive particles have the resin particles and the conductive layer (first conductive layer) disposed on the surface of the resin particles . From the viewpoint of further enhancing the conduction reliability between the electrodes, it is preferable that the above-mentioned conductive particles are conductive particles whose at least conductive outer surface is a low-melting-point metal layer. It is more preferable that the conductive particle has resin particles and a conductive layer disposed on the surface of the resin particle, and at least the outer surface of the conductive layer is a low melting point metal layer.

The low melting point metal layer is a layer containing a low melting point metal. The low melting point metal means a metal having a melting point of 450 캜 or lower. The melting point of the low melting point metal is preferably 300 DEG C or lower, more preferably 160 DEG C or lower. Further, the low-melting-point metal layer preferably contains tin. The content of tin is preferably 30% by weight or more, more preferably 40% by weight or more, still more preferably 70% by weight or more, particularly preferably 90% by weight or more, in 100% by weight of the metal contained in the low melting point metal layer to be. When the content of the low melting point metal layer is lower than the lower limit, the connection reliability between the low melting point metal layer and the electrode is further increased. The content of the tin was measured using a high frequency inductively coupled plasma emission spectrochemical analyzer ("ICP-AES" manufactured by Horiba Seisakusho Co., Ltd.) or a fluorescent X-ray analyzer ("EDX-800" manufactured by Shimadzu Seisakusho Co., HS "). ≪ / RTI >

When the outer surface of the conductive portion is a low-melting-point metal layer, the low-melting-point metal layer is melted and bonded to the electrode, and the low-melting-point metal layer conducts between the electrodes. For example, since the low-melting-point metal layer and the electrode are likely to contact each other if they are not in point contact, the connection resistance is lowered. Further, the use of the conductive particles having at least the conductive outer surface as the low-melting-point metal layer increases the bonding strength between the low-melting-point metal layer and the electrode. As a result, peeling of the electrode from the low- melting- point metal layer becomes more difficult and the reliability of conduction is effectively increased.

The low melting point metal constituting the low melting point metal layer is not particularly limited. The low melting point metal is preferably an alloy containing tin or tin. Examples of the alloy include tin-silver alloy, tin-copper alloy, tin-silver-copper alloy, tin-bismuth alloy, tin-zinc alloy and tin-indium alloy. Among them, the low melting point metal is preferably tin, a tin-silver alloy, a tin-silver-copper alloy, a tin-bismuth alloy or a tin-indium alloy from the viewpoint of excellent wettability to electrodes. Tin-bismuth alloy, and tin-indium alloy.

It is preferable that the low melting point metal layer is a solder layer. The material constituting the solder layer is not particularly limited, but it is preferably a filler metal having a liquidus line of 450 DEG C or less based on JIS Z3001: welding terminology. The composition of the solder includes, for example, a metal composition including zinc, gold, lead, copper, tin, bismuth, indium and the like. Among them, a lead-free tin-indium based (117 占 폚 eutectic) or tin-bismuth (139 占 폚) process is preferable at a low melting point. That is, the solder layer preferably does not contain lead, and is preferably a solder layer containing tin and indium or a solder layer containing tin and bismuth.

In order to further increase the bonding strength between the low-melting-point metal layer and the electrode, the low-melting-point metal layer may include at least one of nickel, copper, antimony, aluminum, zinc, iron, gold, titanium, phosphorus, germanium, tellurium, cobalt, bismuth, , Molybdenum, palladium, and the like. From the viewpoint of further increasing the bonding strength between the low melting point metal and the electrode, it is preferable that the low melting point metal includes nickel, copper, antimony, aluminum or zinc. From the viewpoint of further increasing the bonding strength between the low melting point metal layer and the electrode, the content of these metals for increasing the bonding strength is preferably 0.0001 wt% or more, and preferably 1 wt% or less, based on 100 wt% of the low melting point metal layer.

Wherein the conductive particle has resin particles and a conductive layer disposed on a surface of the resin particle, wherein an outer surface of the conductive layer is a low melting point metal layer, and between the resin particle and the low melting point metal layer (solder layer or the like) And a second conductive layer may be provided separately from the low melting point metal layer. In this case, the low melting point metal layer is a part of the entire conductive layer, and the second conductive layer is a part of the whole conductive layer.

The second conductive layer, which is separate from the low melting point metal layer, may include a metal. The metal constituting the second conductive layer is not particularly limited. Examples of the metal include gold, silver, copper, platinum, palladium, zinc, lead, aluminum, cobalt, indium, nickel, chromium, titanium, antimony, bismuth, germanium and cadmium, have. Also, tin-doped indium oxide (ITO) may be used as the metal. These metals may be used singly or two or more of them may be used in combination.

The second conductive layer is preferably a nickel layer, a palladium layer, a copper layer or a gold layer, more preferably a nickel layer or a gold layer, and more preferably a copper layer. The conductive particles preferably have a nickel layer, a palladium layer, a copper layer or a gold layer, more preferably a nickel layer or a gold layer, and more preferably a copper layer. By using the conductive particles having these preferable conductive layers for connection between the electrodes, the inter-electrode connection resistance is further lowered. Further, a low melting point metal layer can be formed more easily on the surface of these preferable conductive layers. The second conductive layer may be a low melting point metal layer such as a solder layer. The conductive particles may have a plurality of low melting point metal layers.

The thickness of the low melting point metal layer is preferably 0.1 μm or more, more preferably 0.5 μm or more, still more preferably 1 μm or more, preferably 50 μm or less, more preferably 10 μm or less, still more preferably 5 Mu m or less, particularly preferably 3 mu m or less. When the thickness of the low melting point metal layer is not lower than the lower limit, the conductivity is sufficiently high. When the thickness of the low melting point metal layer is less than the upper limit, the difference in thermal expansion coefficient between the resin particles and the low melting point metal layer becomes small, and the low melting point metal layer becomes difficult to peel off.

When the conductive layer is a conductive layer other than the low melting point metal layer, or when the conductive layer has a multilayer structure, the total thickness of the conductive layer is preferably 0.1 占 퐉 or more, more preferably 0.5 占 퐉 or more, Mu] m or more, preferably 50 m or less, more preferably 10 m or less, further preferably 5 m or less, particularly preferably 3 m or less.

The average particle diameter of the conductive particles is preferably 100 占 퐉 or less, more preferably 20 占 퐉 or less, still more preferably 20 占 퐉 or less, further preferably 15 占 퐉 or less, particularly preferably 10 占 퐉 or less. The average particle diameter of the conductive particles is preferably 0.5 占 퐉 or more, and more preferably 1 占 퐉 or more. From the viewpoint of further enhancing the connection reliability of the connection structure in the case of receiving a thermal history, the average particle diameter of the conductive particles is particularly preferably 1 m or more and 10 m or less, and most preferably 1 m or more and 4 m or less.

It is particularly preferable that the average particle diameter of the conductive particles is in the range of 1 to 100 mu m since the size of the conductive particles in the anisotropic conductive material is appropriate and the interval between the electrodes can be further reduced.

The resin particles can be used in accordance with the electrode size or the land diameter of the substrate to be mounted.

The ratio (C / C) of the average particle diameter (C) of the conductive particles to the average particle diameter (A) of the resin particles is more preferably from the viewpoint of more reliable connection between the upper and lower electrodes and further suppressing short- A) is more than 1.0, preferably not more than 3.0. When the second conductive layer is present between the resin particles and the solder layer, the ratio (B / A) of the average particle diameter (B) of the conductive particle portion excluding the solder layer to the average particle diameter (A) ) Is more than 1.0, preferably not more than 2.0. When the second conductive layer is present between the resin particle and the solder layer, the average particle diameter (B) of the conductive particle portion excluding the solder layer of the average particle diameter (C) of the conductive particles including the solder layer The ratio (C / B) is more than 1.0, preferably not more than 2.0. When the ratio (B / A) is within the above range or the ratio (C / B) is within the above range, the upper and lower electrodes are connected more reliably and the short circuit between the electrodes adjacent in the horizontal direction is further suppressed can do.

Conductive material for FOB and FOF applications (anisotropic conductive material):

The conductive material is preferably used for connection (FOB (Film on Board)) between a flexible printed substrate and a glass epoxy substrate, or connection (FOF (Film on Film) between a flexible printed substrate and a flexible printed substrate.

In the FOB and FOF applications, L & S, which is a dimension of a portion (line) where an electrode exists and a portion (space) where no electrode exists, is generally 100 to 500 mu m. The average particle diameter of the resin particles used for FOB and FOF applications is preferably 10 to 100 mu m. When the average particle diameter of the resin particles is 10 m or more, the thickness of the conductive material and the connecting portion disposed between the electrodes becomes sufficiently thick, and the adhesive force is further increased. When the average particle diameter of the resin particles is 100 m or less, it is further difficult to cause short-circuiting between adjacent electrodes.

Conductive material for flip chip application (anisotropic conductive material):

The conductive material is preferably used for flip chip applications.

In flip chip applications, the land diameter is generally 15 to 80 占 퐉. The average particle diameter of the resin particles used for the flip chip application is preferably 1 to 15 mu m. When the average particle diameter of the resin particles is 1 占 퐉 or more, the thickness of the solder layer disposed on the surface of the resin particle can be made sufficiently thick, and the electrodes can be electrically connected more reliably. When the average particle diameter of the resin particles is 10 m or less, occurrence of short-circuiting between adjacent electrodes becomes even more difficult.

Conductive material for COF (anisotropic conductive material):

The conductive material is preferably used for connection (COF (Chip on Film)) between a semiconductor chip and a flexible printed board.

In the COF application, L & S, which is a dimension of a portion (line) where the electrode is present and a portion (space) where no electrode exists, is generally 10 to 50 mu m. The average particle diameter of the resin particles used for the COF application is preferably 1 to 10 mu m. When the average particle diameter of the resin particles is 1 占 퐉 or more, the thickness of the solder layer disposed on the surface of the resin particle can be made sufficiently thick, and the electrodes can be electrically connected more reliably. When the average particle diameter of the resin particles is 10 m or less, occurrence of short-circuiting between adjacent electrodes becomes even more difficult.

The " average particle diameter " of the conductive particles indicates the number average particle diameter. The average particle diameter of the conductive particles is obtained by observing 50 arbitrary conductive particles with an electron microscope or an optical microscope and calculating an average value.

The surface of the conductive particles may be insulated by an insulating material such as insulating particles, a flux, or the like. The insulating material, flux and the like are preferably removed from the connecting portion by softening and flowing by heat at the time of connection. Accordingly, it is possible to suppress the occurrence of a short circuit between the electrodes.

The content of the conductive particles is not particularly limited. The content of the conductive particles in 100 wt% of the curable composition is preferably 0.1 wt% or more, more preferably 0.5 wt% or more, preferably 40 wt% or less, more preferably 20 wt% or less, Is not more than 15% by weight. When the content of the conductive particles is not less than the lower limit and not more than the upper limit, conductive particles can be easily disposed between the upper and lower electrodes to be connected. Further, it is difficult for the adjacent electrodes, which should not be connected, to be electrically connected through the plurality of conductive particles. That is, it is possible to prevent a short circuit between adjacent electrodes.

(Uses of Curable Composition)

The curable composition according to the present invention can be used for bonding various members to be connected.

When the curable composition according to the present invention is a conductive material containing conductive particles, the conductive material may be used as a conductive paste or a conductive film. When the conductive material is used as the conductive film, a film not containing the conductive particles may be laminated on the conductive film containing the conductive particles. The film also includes a sheet. The curable composition according to the present invention is preferably a paste-like conductive paste. The conductive paste is preferably an anisotropic conductive paste. The conductive film is preferably an anisotropic conductive film.

The conductive material is preferably used to obtain a connection structure in which the first and second connection target members are electrically connected.

1 is a cross-sectional view schematically showing an example of a connection structure using a curable composition according to an embodiment of the present invention.

The connection structure 1 shown in Fig. 1 includes a first connection target member 2, a second connection target member 4 and a connection portion 3 connecting the first and second connection target members 2 and 4 . The connection portion 3 is formed by curing the curable composition containing the conductive particles 5, that is, the conductive material.

The first connection target member 2 has a plurality of electrodes 2b on the upper surface 2a (surface). The second connection target member 4 has a plurality of electrodes 4b on the lower surface 4a (surface). The electrode 2b and the electrode 4b are electrically connected by one or a plurality of conductive particles 5. Therefore, the first and second connection target members 2 and 4 are electrically connected by the conductive particles 5. [

Preferably, the curable composition according to the present invention is a paste-like conductive paste, and is a conductive paste to be applied on the first connection target member in a paste state.

The first and second connection target members are not particularly limited. Specific examples of the first and second connection target members include electronic parts such as semiconductor chips, capacitors and diodes, and electronic parts such as printed boards, flexible printed boards and circuit boards such as glass boards. The first and second connection target members are preferably electronic parts. The curable composition according to the present invention is preferably a curable composition for connecting electronic components.

The manufacturing method of the connection structure is not particularly limited. As an example of a manufacturing method of the connection structure, there is a method of arranging the curable composition between the first connection object member and the second connection object member to obtain a laminate, and then heating and pressing the laminate.

In addition, the curable composition may not contain conductive particles. In this case, the curable composition is used so that the first and second connection target members are bonded and connected without electrically connecting the first and second connection target members.

In the case where the curable composition according to the present invention is a conductive material, the conductive material may be, for example, a flexible printed board and a glass substrate (FOG), a semiconductor chip and a flexible printed board on Film), connection between a semiconductor chip and a glass substrate (COG (Chip on Glass)), or connection between a flexible printed substrate and a glass epoxy substrate (FOB (Film on Board)). Among these, the conductive material is preferable for FOG application or COG application, and more preferable for COG application. The curable composition according to the present invention is preferably a conductive material used for connection between a flexible printed board and a glass substrate or for connection between a semiconductor chip and a flexible printed board and is preferably a conductive material used for connection between a semiconductor chip and a flexible printed board More preferable.

As the connection structure according to the present invention, it is preferable that a flexible printed substrate and a glass substrate are used as the second connection target member and the first connection target member, or a semiconductor chip and a glass substrate are used, It is more preferable to use a substrate.

In the FOG application, since the L / S is relatively wide, the particle diameter of the conductive particles is large and the concentration is low, so that the pressure at the time of connection is low, sufficient indentation and resin filling property can not be obtained, Voids (voids) are often a problem. On the other hand, by using the curable composition according to the present invention, it is possible to effectively increase the conduction reliability between the electrodes in the FOG application, and to effectively suppress the occurrence of voids (voids) in the cured layer.

In COG applications, since the L / S is a relatively narrow pitch, the conductive material is not sufficiently filled between the electrode lines when the conductive material is heated to a low degree of fluidity. Therefore, Pore generation is often a problem. On the other hand, by using the curable composition according to the present invention, it is possible to effectively increase conduction reliability between electrodes in the use of COG, and to effectively suppress the generation of voids in the cured layer.

Hereinafter, the present invention will be described in detail with reference to examples and comparative examples. The present invention is not limited to the following examples.

The weight average molecular weight of the epoxy compound obtained in the following synthesis example is the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

In addition, the viscosity of the mixture of the epoxy compound and the curable composition obtained in the following Examples show the viscosity measured at 23 캜 and 2.5 rpm using a viscosity measuring apparatus (manufactured by Toki Sangyo K.K.).

(Synthesis Example 1)

(1) Synthesis of first reaction product of bisphenol F and 1,6-hexanediol diglycidyl ether:

72 parts by weight of bisphenol F (including 4,4'-methylene bisphenol, 2,4'-methylene bisphenol and 2,2'-methylene bisphenol in a weight ratio of 31:52:17), 1,6-hexane diol di 100 parts by weight of glycidyl ether and 1 part by weight of triphenylphosphine were placed in a three-necked flask and dissolved at 150 占 폚. Thereafter, an addition polymerization reaction was carried out at 180 DEG C for 6 hours to obtain a first reaction product.

It was confirmed that the addition polymerization reaction had proceeded so that the first reactant had a structural unit in which a skeleton derived from bisphenol F and a skeleton derived from 1,6-hexanediol diglycidylether were bonded, It was confirmed that epoxy groups derived from hexanediol diglycidyl ether were present at both terminals.

(2) Synthesis of an epoxy compound obtained by reacting the first reactant with acrylic acid:

100 parts by weight of the obtained first reaction product and 4 parts by weight of acrylic acid were mixed and the temperature was raised to 80 캜. After elevating the temperature, 1 part by weight of dimethyisilylammonium pentafluorobenzenesulfonate as a catalyst was added and condensation reaction was carried out for 4 hours to have an epoxy group at both ends, and a vinyl group in the side chain was added to the total number of hydroxyl groups before the reaction of 20% To obtain an epoxy compound.

The weight average molecular weight of the obtained epoxy compound was 8,000. The obtained epoxy compound had only one peak in the molecular weight distribution, and no acrylic acid-derived low molecular weight was observed. Further, it was confirmed by NMR that acrylic acid reacted with the hydroxyl group and 20% of the vinyl group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 2)

Synthesis of an epoxy compound obtained by reacting the first reactant obtained in Synthesis Example 1 with 2-methacryloyloxyethyl isocyanate:

100 parts by weight of the first reaction product obtained in Synthesis Example 1, 4 parts by weight of 2-methacryloyloxyethyl isocyanate and 0.3 parts by weight of dibutyl tin laurate were combined and then subjected to an addition reaction at 80 DEG C for 4 hours, And an epoxy compound having a vinyl group in the side chain of 20% with respect to 100% of the total number of hydroxyl groups before the reaction was obtained.

The weight average molecular weight of the obtained epoxy compound was 12,000. The peak in the molecular weight distribution of the obtained epoxy compound was only one, and no peak for the low molecular weight derived from the methacrylic acid compound was observed. Further, it was confirmed by NMR that 2-methacryloyloxyethyl isocyanate reacted with the hydroxyl group and 20% of the vinyl groups were introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 3)

Synthesis of an epoxy compound obtained by reacting the first reactant obtained in Synthesis Example 1 with 4-hydroxybutyl glycidyl ether:

100 parts by weight of the first reaction product obtained in Synthesis Example 1, 4 parts by weight of 4-hydroxybutyl glycidyl ether and 0.2 parts by weight of dimethyisilylammonium pentafluorobenzenesulfonate were blended, An epoxy compound having an epoxy group at both terminals and having an epoxy group in the side chain of 20% with respect to 100% of the total number of hydroxyl groups before the reaction was obtained.

The weight average molecular weight of the obtained epoxy compound was 12,000. There was only one peak in the molecular weight distribution of the obtained epoxy compound, and no peak for the low molecular weight derived from the 4-hydroxybutyl glycidyl ether compound was observed. Further, it was confirmed that the condensation reaction proceeded, and it was confirmed that 4-hydroxybutyl glycidyl ether reacted with the hydroxyl group and 20% of the epoxy group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 4)

(1) Synthesis of second reactant of resorcinol and 1,6-hexanediol diglycidyl ether:

48 parts by weight of resorcinol, 100 parts by weight of 1,6-hexanediol diglycidyl ether and 1 part by weight of triphenylphosphine were placed in a three-necked flask and dissolved at 150 占 폚. Thereafter, an addition polymerization reaction was carried out at 180 DEG C for 6 hours to obtain a second reaction product.

It was confirmed that the addition polymerization reaction proceeded, and the second reactant had a structural unit in which a skeleton derived from resorcinol and a skeleton derived from 1,6-hexanediol diglycidylether were bonded to each other in the main chain, and 1,6 -Hexanediol diglycidyl ether at both ends of the copolymer.

(2) Synthesis of an epoxy compound obtained by reacting the second reactant with acrylic acid:

A condensation reaction was carried out in the same manner as in Synthesis Example 1 using the obtained second reactant instead of the first reactant to obtain an epoxy resin having an epoxy group at both terminals and a vinyl group in the side chain in an amount of 20% To obtain an epoxy compound.

The weight average molecular weight of the obtained epoxy compound was 15,000, and one peak was present in the molecular weight distribution of the epoxy compound. It was also confirmed by NMR that acrylic acid was reacted with the hydroxyl group to introduce the vinyl group into the side chain at 20% with respect to the total number of hydroxyl groups before the reaction of 100%.

(Synthesis Example 5)

Synthesis of an epoxy compound obtained by reacting the second reactant obtained in Synthesis Example 4 with 4-hydroxybutyl glycidyl ether:

Using the second reactant obtained in Synthesis Example 4 instead of the first reactant, a condensation reaction was carried out in the same manner as in Synthesis Example 3 to obtain a compound having an epoxy group at both terminals, an epoxy group in the side chain, and a total number of hydroxyl groups To obtain an epoxy compound having 20% based on 100%.

The weight average molecular weight of the obtained epoxy compound was 15,000. There was one peak in the molecular weight distribution of the obtained epoxy compound. Further, it was confirmed by NMR that 4-hydroxybutyl glycidyl ether undergoes a condensation reaction to introduce an epoxy group into the side chain in an amount of 20% based on 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 6)

Synthesis of an epoxy compound obtained by reacting the second reactant obtained in Synthesis Example 4 with 2-methacryloyloxyethyl isocyanate:

The second reaction product obtained in Synthesis Example 4 was used in place of the first reaction product to carry out an addition reaction in the same manner as in Synthesis Example 2 to obtain a compound having an epoxy group at both terminals and a vinyl group in the side chain and a total number of hydroxyl groups To obtain an epoxy compound having 20% based on 100%.

The weight average molecular weight of the obtained epoxy compound was 15,000. There was one peak in the molecular weight distribution of the obtained epoxy compound. Further, it was confirmed by the addition reaction that 2-methacryloyloxyethyl isocyanate reacted, and the vinyl group was introduced into the side chain in an amount of 20% based on 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 7)

(1) Synthesis of a third reactant of resorcinol and resorcinol diglycidyl ether:

33 parts by weight of resorcinol, 100 parts by weight of resorcinol diglycidyl ether and 1 part by weight of triphenylphosphine were placed in a three-necked flask and dissolved at 150 占 폚. Thereafter, an addition polymerization reaction was carried out at 180 DEG C for 6 hours to obtain a third reaction product.

It was confirmed that the addition polymerization reaction had proceeded so that the third reactant had a structural unit in which a skeleton derived from resorcinol and a skeleton derived from resorcinol diglycidylether were bonded to each other in the main chain and resorcinol diglycidyl ether Having epoxy groups at both terminals.

(2) Synthesis of an epoxy compound reacting the third reactant with acrylic acid:

Using the obtained third reactant instead of the first reactant, a condensation reaction was carried out in the same manner as in Synthesis Example 1 to obtain a compound having an epoxy group at both terminals and a vinyl group in the side chain in a proportion of 100% To obtain an epoxy compound having 20%.

The weight average molecular weight of the obtained epoxy compound was 11,000. There was one peak in the molecular weight distribution of the obtained epoxy compound. Further, it was confirmed that acrylic acid reacted with the hydroxyl group by the condensation reaction, and the vinyl group was introduced into the side chain by 20% with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 8)

Synthesis of the vinyl compound obtained by reacting the third reactant obtained in Synthesis Example 7 with 2-methacryloyloxyethyl isocyanate:

The third reaction product obtained in Synthesis Example 7 was used in place of the first reaction product to carry out an addition reaction in the same manner as in Synthesis Example 2 to obtain a compound having an epoxy group at both ends and a vinyl group in the side chain and a total number of hydroxyl groups To obtain an epoxy compound having 20% based on 100%.

The weight average molecular weight of the obtained epoxy compound was 11,000. There was one peak in the molecular weight distribution of the obtained epoxy compound. Further, it was confirmed by NMR that 2-methacryloyloxyethyl isocyanate reacted with the hydroxyl group and 20% of the vinyl groups were introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 9)

Synthesis of an epoxy compound obtained by reacting the third reactant obtained in Synthesis Example 7 with 4-hydroxybutyl glycidyl ether:

Using the third reactant obtained in Synthesis Example 7 instead of the first reactant, a condensation reaction was carried out in the same manner as in Synthesis Example 3 to obtain a compound having an epoxy group at both terminals, an epoxy group in the side chain, and a total number of hydroxyl groups To obtain an epoxy compound having 20% based on 100%.

The weight average molecular weight of the obtained epoxy compound was 11,000. There was one peak in the molecular weight distribution of the obtained epoxy compound. Further, by NMR, it was confirmed that 4-hydroxybutyl glycidyl ether reacted with the hydroxyl group and 20% of the epoxy group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Example 1)

The epoxy compound obtained in Synthesis Example 1 and the epoxy compound obtained in Synthesis Example 2 were mixed at a weight ratio of 5: 3 to obtain a mixture (1) of an epoxy compound. The viscosity of the obtained mixture (1) of the epoxy compound was 320 Pa · s.

Next, to 33 parts by weight of the obtained mixture (1) of the epoxy compound (1), 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a heat curing agent and 20 parts by weight of a curing accelerator 2-ethyl- , 5 parts by weight of a photo-curing compound epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Industries, Inc.), and 5 parts by weight of an acylphosphine oxide-based compound (DAROCUR manufactured by Shiba, Japan K.K. TPO "), 20 parts by weight of silica having an average particle diameter of 0.25 mu m as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 mu m and 2 parts by weight of conductive particles having an average particle diameter of 3 mu m were added, The mixture was stirred at rpm for 5 minutes to obtain an anisotropic conductive paste (1). The conductive particles used are conductive particles having a nickel plating layer formed on the surface of the divinylbenzene resin particle and a metal layer having a gold plating layer formed on the surface of the nickel plating layer. The viscosity of the obtained curable composition (1) was 350 Pa · s.

(Example 2)

The epoxy compound obtained in Synthesis Example 2 and the epoxy compound obtained in Synthesis Example 3 were mixed at a weight ratio of 5: 3 to obtain a mixture (2) of an epoxy compound. The obtained mixture (2) of the epoxy compound had a viscosity of 300 Pa · s.

The curable composition (2) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (2) of the obtained epoxy compound. The viscosity of the obtained curable composition (2) was 340 Pa · s.

(Example 3)

The epoxy compound obtained in Synthesis Example 3 and the epoxy compound obtained in Synthesis Example 4 were mixed at a weight ratio of 5: 3 to obtain a mixture (3) of an epoxy compound. The obtained mixture (3) of the epoxy compound had a viscosity of 280 Pa · s.

The curable composition (3) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (3) of the obtained epoxy compound. The viscosity of the obtained curable composition (3) was 310 Pa s.

(Example 4)

The epoxy compound obtained in Synthesis Example 4 and the epoxy compound obtained in Synthesis Example 5 were mixed at a weight ratio of 5: 3 to obtain a mixture (4) of an epoxy compound. The obtained mixture (4) of the epoxy compound had a viscosity of 330 Pa · s.

A curable composition (4) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (4) of the obtained epoxy compound. The viscosity of the obtained curable composition (4) was 360 Pa · s.

(Example 5)

The epoxy compound obtained in Synthesis Example 5 and the epoxy compound obtained in Synthesis Example 6 were mixed at a weight ratio of 5: 3 to obtain a mixture (5) of an epoxy compound. The obtained mixture (5) of the epoxy compound had a viscosity of 260 Pa · s.

The curable composition (5) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (5) of the obtained epoxy compound. The viscosity of the obtained curable composition (5) was 290 Pa 占 퐏.

(Example 6)

20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate and 1 part by weight of 2-ethyl-4-methylimidazole were dissolved in a mixture of 0.6 weight of cationic curing agent (Sun Aid Si-60 (manufactured by Sanzuka Chemical Co., Ltd.) , The curable composition (6) was obtained in the same manner as in Example 1. The viscosity of the obtained curable composition (6) was 180 Pa · s.

(Example 7)

Curable composition (7) was obtained in the same manner as in Example 1 except that 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate was changed to 20 parts by weight of ethylenediamine as an amine curing agent. The viscosity of the obtained curable composition (7) was 150 Pa · s.

(Example 8)

, 5 parts by weight of an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Co., Ltd.) as a photo-curing compound, and 5 parts by weight of a photo-curing compound urethane acrylate (EBECRYL8804 manufactured by Daicel- , A curable composition (8) was obtained in the same manner as in Example 1. The viscosity of the obtained curable composition (8) was 280 Pa · s.

(Example 9)

Except that an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Industries, Inc.) and an acylphosphine oxide-based compound (DAROCUR TPO, manufactured by Shiba Japan K.K.) were not blended A curable composition (9) was obtained in the same manner as in Example 1. The viscosity of the obtained curable composition (9) was 260 Pa · s.

(Example 10)

Except that an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Industries, Inc.) and an acylphosphine oxide-based compound (DAROCUR TPO, manufactured by Shiba Japan K.K.) were not blended In the same manner as in Example 2, a curable composition (10) was obtained. The viscosity of the obtained curable composition (10) was 310 Pa · s.

(Comparative Example 1)

33 parts by weight of a bisphenol A type epoxy resin, 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a heat curing agent, 1 part by weight of 2-ethyl-4-methylimidazole as a curing accelerator, , 5 parts by weight of a curing compound epoxy acrylate ("EBECRYL3702" manufactured by Daicel-Cytech Corporation) and 0.1 part by weight of an acylphosphine oxide-based compound (DAROCUR TPO, manufactured by Shiba Japan K.K.) 20 parts by weight of silica having an average particle diameter of 0.25 mu m as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 mu m and 2 parts by weight of conductive particles having an average particle diameter of 3 mu m were added and stirred at 2,000 rpm for 5 minutes using a planetary stirrer To obtain a curable composition which is an anisotropic conductive paste.

(Comparative Example 2)

Except that an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Industries, Inc.) and an acylphosphine oxide-based compound (DAROCUR TPO, manufactured by Shiba Japan K.K.) were not blended In the same manner as in Comparative Example 1, a curable composition was obtained.

(Evaluation of Examples 1 to 10 and Comparative Examples 1 and 2)

(1) Curing time 1

A transparent glass substrate having an ITO electrode pattern having an L / S of 10 mu m / 10 mu m on its upper surface was prepared. In addition, a semiconductor chip having a gold electrode pattern having a L / S of 10 占 퐉 / 10 占 퐉 was prepared.

The (meth) acrylic resin was cured on the transparent glass substrate by coating the obtained curable composition to a thickness of 30 占 퐉 and further irradiating with UV light to form a curable composition layer. Next, the semiconductor chip was laminated on the curable composition layer so that the electrodes were connected to each other so as to be opposed to each other. Thereafter, the heating head was placed on the upper surface of the semiconductor chip while the temperature of the heating head was adjusted so that the temperature of the curable composition layer became 150 ° C, and the curable composition layer was cured at 150 ° C to obtain a connection structure A. The time required for curing of the curable composition layer by heating when the connection structure was obtained was measured.

(2) Curing time 2

A transparent glass substrate having an ITO electrode pattern having an L / S of 10 mu m / 10 mu m on its upper surface was prepared. In addition, a semiconductor chip having a gold electrode pattern having a L / S of 10 占 퐉 / 10 占 퐉 was prepared.

The obtained curable composition was coated on the transparent glass substrate to a thickness of 30 占 퐉 to form a curable composition layer. Next, the semiconductor chip was laminated on the curable composition layer so that the electrodes were connected to each other so as to be opposed to each other. Thereafter, the heating head was placed on the upper surface of the semiconductor chip while adjusting the temperature of the heating head so that the temperature of the curable composition layer was 150 ° C, and the curable composition layer was cured at 150 ° C to obtain a connection structure B. The time required for curing of the curable composition layer by heating when the connection structure was obtained was measured.

(3) Adhesiveness

The adhesiveness was evaluated by measuring the peel strength using the connection structures A and B obtained by the evaluation of (1) the curing time 1 and (2) the curing time 2 described above. Adhesiveness was determined based on the following criteria.

[Evaluation criteria for adhesiveness]

○: 8 N / cm or more

X: less than 8 N / cm

(4) Moisture resistance

The connection structures A and B (15 pieces each) obtained by the evaluation of the above-mentioned (1) curing time 1 and (2) the curing time 2 were allowed to stand at 85 ° C and 85% RH for 1,000 hours, . The resistance values at 20 points in the connection structures A and B were evaluated by a four-terminal method. The conduction reliability was judged to be the criterion below.

[Criteria for moisture resistance evaluation]

○: Resistance value is less than 3Ω at all points

X: At least one portion not conducting at all

(5) presence or absence of voids

Whether or not voids were formed in the cured layer formed by the curable composition layer in the connection structures A and B obtained by the evaluation of (1) the curing time 1 and (2) the curing time 2 was evaluated on the lower surface side of the transparent glass substrate And observed with naked eyes.

The results are shown in Table 1 below.

(Synthesis Example 10)

(1) Synthesis of first reaction product of bisphenol F and 1,6-hexanediol diglycidyl ether:

72 parts by weight of bisphenol F (including 4,4'-methylene bisphenol, 2,4'-methylene bisphenol and 2,2'-methylene bisphenol in a weight ratio of 31:52:17), bisphenol F (4,4 ' 64 parts by weight of methylene bisphenol, 2,4'-methylene bisphenol and 2,2'-methylene bisphenol in a weight ratio of 31:52:17) and a multinuclear body (3) having a bisphenol F skeleton and having 3 or more nuclei Except that the mixture was changed to 72 parts by weight of a mixture of 8 parts by weight of a core and 9 parts by weight of a multi-nucleating material having four or more nuclei.

(2) Synthesis of an epoxy compound obtained by reacting the first reactant with acrylic acid:

A condensation reaction was carried out in the same manner as in Synthesis Example 1, except that the obtained first reaction product was used, to obtain an epoxy compound having an epoxy group at both terminals and a vinyl group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 7,000. It was also confirmed by NMR that acrylic acid reacted with the hydroxyl group and a vinyl group was introduced into the side chain.

(Synthesis Example 11)

Synthesis of an epoxy compound obtained by reacting the first reactant obtained in Synthesis Example 10 with 2-methacryloyloxyethyl isocyanate:

100 parts by weight of the first reaction product obtained in Synthesis Example 10, 4 parts by weight of 2-methacryloyloxyethyl isocyanate and 0.3 parts by weight of dibutyl tin laurate were mixed and then subjected to an addition reaction at 80 DEG C for 4 hours, An epoxy compound having an epoxy group at the terminal and a vinyl group in the side chain was obtained.

The weight average molecular weight of the obtained epoxy compound was 10,000. Further, it was confirmed by NMR that 2-methacryloyloxyethyl isocyanate reacted with the hydroxyl group to introduce a vinyl group into the side chain.

(Synthesis Example 12)

Synthesis of an epoxy compound obtained by reacting the first reactant obtained in Synthesis Example 10 with 4-hydroxybutyl glycidyl ether:

100 parts by weight of the first reaction product obtained in Synthesis Example 10, 4 parts by weight of 4-hydroxybutyl glycidyl ether, and 0.2 parts by weight of dimethyisilylammonium pentafluorobenzenesulfonate were blended, The condensation reaction was carried out to obtain an epoxy compound having an epoxy group at both terminals and an epoxy group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 10,000. Further, confirming that the condensation reaction proceeded, it was confirmed that the hydroxyl group was reacted with 4-hydroxybutyl glycidyl ether to introduce an epoxy group into the side chain.

(Synthesis Example 13)

(1) 54 parts by weight of bisphenol F (including 4,4'-methylene bisphenol, 2,4'-methylene bisphenol and 2,2'-methylene bisphenol in a weight ratio of 31:52:17), 1,6- 75 parts by weight of hexanediol diglycidyl ether and 0.75 part by weight of triphenylphosphine were placed in a three-necked flask and dissolved at 150 占 폚. Thereafter, an addition polymerization reaction was carried out at 180 DEG C for 4 hours, and 25 parts by weight of bisphenol F, 9.5 parts by weight of 1,6-hexanediol diglycidyl ether and 0.25 part by weight of triphenylphosphine were added, An addition polymerization reaction was carried out to obtain a first reaction product.

It was confirmed that the addition polymerization reaction had proceeded so that the first reactant had a structural unit in which a skeleton derived from bisphenol F and a skeleton derived from 1,6-hexanediol diglycidylether were bonded, It was confirmed that epoxy groups derived from hexanediol diglycidyl ether were present at both terminals.

(2) Synthesis of an epoxy compound obtained by reacting the first reactant with acrylic acid:

100 parts by weight of the obtained first reaction product and 4 parts by weight of acrylic acid were combined and heated to 80 캜. After elevating the temperature, 1 part by weight of dimethyisilylammonium pentafluorobenzenesulfonate as a catalyst was added and condensation reaction was carried out for 4 hours to obtain an epoxy compound having an epoxy group at both terminals and a vinyl group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 6,000. There were two peaks in the molecular weight distribution of the obtained epoxy compound. It was also confirmed by NMR that acrylic acid reacted with the hydroxyl group and a vinyl group was introduced into the side chain.

(Synthesis Example 14)

100 parts by weight of the first reaction product obtained in Synthesis Example 13, 4 parts by weight of 2-methacryloyloxyethyl isocyanate, and 0.3 part by weight of dibutyl tin laurate were combined and then subjected to an addition reaction at 80 DEG C for 4 hours, An epoxy compound having an epoxy group at the terminal and a vinyl group in the side chain was obtained.

The weight average molecular weight of the obtained epoxy compound was 7,500. There were two peaks in the molecular weight distribution of the obtained epoxy compound. Further, it was confirmed by NMR that 2-methacryloyloxyethyl isocyanate reacted with the hydroxyl group to introduce a vinyl group into the side chain.

(Example 11)

The epoxy compound obtained in Synthesis Example 10 and the epoxy compound obtained in Synthesis Example 11 were mixed at a weight ratio of 5: 3 to obtain a mixture (11) of an epoxy compound.

The curable composition (11) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (11) of the obtained epoxy compound. The viscosity of the obtained curable composition (11) was 390 Pa 占 퐏.

(Example 12)

The epoxy compound obtained in Synthesis Example 11 and the epoxy compound obtained in Synthesis Example 12 were mixed at a weight ratio of 5: 3 to obtain a mixture (12) of an epoxy compound.

The curable composition (12) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (12) of the obtained epoxy compound. The viscosity of the obtained curable composition (12) was 380 Pa · s.

(Example 13)

A mixture (1) of the epoxy compound obtained in Example 1 was prepared. The mixture (1) of the epoxy compound contains the epoxy compound obtained in Synthesis Example 1 and the epoxy compound obtained in Synthesis Example 2 at a weight ratio of 5: 3.

To 33 parts by weight of the mixture (1) of the epoxy compound, 3 parts by weight of bisphenol F diglycidyl ether, 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a heat curing agent, , Ethyl-4-methylimidazole (1 part by weight), and 5 parts by weight of a photo-curable compound epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec KK), and an acylphosphine oxide-based compound Ltd., "DAROCUR TPO" manufactured by Japan KK), 20 parts by weight of silica having an average particle diameter of 0.25 μm as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 μm, and 2 parts by weight of the conductive particles used in Example 1 , And the mixture was stirred for 5 minutes at 2,000 rpm using a planetary stirrer to obtain a curable composition (13) as an anisotropic conductive paste. The viscosity of the obtained curable composition (13) was 330 Pa · s.

(Example 14)

A mixture (1) of the epoxy compound obtained in Example 1 was prepared. The mixture (1) of the epoxy compound contains the epoxy compound obtained in Synthesis Example 1 and the epoxy compound obtained in Synthesis Example 2 at a weight ratio of 5: 3.

To 33 parts by weight of the mixture (1) of the epoxy compound, 3 parts by weight of resorcinol diglycidyl ether, 20 parts by weight of pentaerythritoltetrakis-3-mercaptopropionate as a thermosetting agent, 2 parts by weight of curing accelerator 2 , Ethyl-4-methylimidazole (1 part by weight), and 5 parts by weight of a photo-curable compound epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec KK), and an acylphosphine oxide-based compound Ltd., "DAROCUR TPO" manufactured by Japan KK), 20 parts by weight of silica having an average particle diameter of 0.25 μm as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 μm, and 2 parts by weight of the conductive particles used in Example 1 And the mixture was stirred for 5 minutes at 2,000 rpm using a planetary stirrer to obtain a curable composition 14 as an anisotropic conductive paste. The viscosity of the obtained curable composition (14) was 320 Pa · s.

(Example 15)

A mixture (1) of the epoxy compound obtained in Example 1 was prepared. The mixture (1) of the epoxy compound contains the epoxy compound obtained in Synthesis Example 1 and the epoxy compound obtained in Synthesis Example 2 at a weight ratio of 5: 3.

To 33 parts by weight of the mixture (1) of the epoxy compound, 3 parts by weight of bisphenol F glycidyl ether epoxy acrylate, 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a heat curing agent, 1 part by weight of 2-ethyl-4-methylimidazole, which is a photopolymerization initiator, 5 parts by weight of an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec KK) as a photopolymerizable compound, , 20 parts by weight of silica having an average particle size of 0.25 mu m as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 mu m, 2 parts by weight of the conductive particles 2 used in Example 1 (weight And the mixture was stirred for 5 minutes at 2,000 rpm using a planetary stirrer to obtain a curable composition (15) as an anisotropic conductive paste. The viscosity of the obtained curable composition (15) was 320 Pa · s.

(Example 16)

A mixture (1) of the epoxy compound obtained in Example 1 was prepared. The mixture (1) of the epoxy compound contains the epoxy compound obtained in Synthesis Example 1 and the epoxy compound obtained in Synthesis Example 2 at a weight ratio of 5: 3.

To 33 parts by weight of the mixture (1) of the epoxy compound, 3 parts by weight of resorcinol glycidyl ether epoxy acrylate, 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a thermosetting agent, 1 part by weight of 2-ethyl-4-methylimidazole as a promoter, 5 parts by weight of an epoxy acrylate (EBECRYL3702, manufactured by Daicel-Cytec Co., Ltd.) as a photopolymerizable compound, 5 parts by weight of an acylphosphine oxide- , 20 parts by weight of silica having an average particle diameter of 0.25 占 퐉 as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 占 퐉, and 0.1 part by weight of a conductive particle 2 used in Example 1 (trade name: DAROCUR TPO, manufactured by Shiba, Japan) And the mixture was stirred for 5 minutes at 2,000 rpm using a planetary stirrer to obtain a curable composition (16) as an anisotropic conductive paste. The viscosity of the obtained curable composition (16) was 320 Pa · s.

(Example 17)

The epoxy compound obtained in Synthesis Example 13 and the epoxy compound obtained in Synthesis Example 14 were mixed at a weight ratio of 5: 3 to obtain a mixture (17) of an epoxy compound.

The curable composition (17) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (17) of the obtained epoxy compound. The viscosity of the obtained curable composition (17) was 280 Pa · s.

(Example 18)

The epoxy compound obtained in Synthesis Example 4 and the epoxy compound obtained in Synthesis Example 7 were mixed at a weight ratio of 5: 3 to obtain a mixture (18) of an epoxy compound.

The curable composition (18) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (18) of the obtained epoxy compound. The viscosity of the obtained curable composition (18) was 310 Pa · s.

(Example 19)

The epoxy compound obtained in Synthesis Example 4 and the epoxy compound obtained in Synthesis Example 8 were mixed at a weight ratio of 5: 3 to obtain a mixture (19) of an epoxy compound.

A curable composition (19) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (19) of the obtained epoxy compound. The viscosity of the obtained curable composition (19) was 320 Pa · s.

(Example 20)

The epoxy compound obtained in Synthesis Example 4 and the epoxy compound obtained in Synthesis Example 9 were mixed at a weight ratio of 5: 3 to obtain a mixture (20) of an epoxy compound.

The curable composition (20) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (20) of the obtained epoxy compound. The viscosity of the obtained curable composition (20) was 320 Pa · s.

(Evaluation of Examples 11 to 20)

Evaluation items such as Examples 1 to 10 and Comparative Examples 1 and 2 were evaluated.

The results are shown in Table 2 below.

In addition, the evaluation results of the adhesiveness of Examples 1 to 20 were all "O". The measured value of the peel strength was higher in Example 11 than in Example 1, higher in Example 12 than Example 2, higher in Example 13 than in Example 1, higher in Example 14 than Example 1, Example 15 was higher than Example 1, and Example 16 was higher than Example 1.

(Synthesis Example 15)

(1) Synthesis of the fourth reaction product of bisphenol F and resorcinol diglycidyl ether:

72 parts by weight of bisphenol F (including 4,4'-methylene bisphenol, 2,4'-methylene bisphenol and 2,2'-methylene bisphenol in a weight ratio of 31:52:17), 2,2'- And 1 part by weight of triphenylphosphine were placed in a three-necked flask and dissolved at 150 占 폚. Thereafter, an addition polymerization reaction was carried out at 180 DEG C for 6 hours to obtain a fourth reaction product.

It was confirmed that the addition polymerization reaction proceeded so that the fourth reaction product had a structural unit in which the skeleton derived from bisphenol F and the skeleton derived from resorcinol diglycidyl ether were bonded to each other in the main chain and the resorcinol diglycidyl ether It was confirmed that the resulting epoxy group was present at both terminals.

(2) Synthesis of an epoxy compound reacting the above-mentioned fourth reactant and acrylic acid:

Using the obtained third reactant instead of the first reactant, a condensation reaction was carried out in the same manner as in Synthesis Example 1 to obtain an epoxy compound having an epoxy group at both terminals and a vinyl group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 132,000. There was only one peak in the molecular weight distribution of the obtained epoxy compound, and no peak for an acrylic acid-derived low molecule was observed. It was also confirmed by NMR that acrylic acid reacted with the hydroxyl group and 100% of the vinyl group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 16)

Synthesis of an epoxy compound obtained by reacting the above-mentioned fourth reactant obtained in Synthesis Example 15 with 2-methacryloyloxyethyl isocyanate:

The fourth reaction product obtained in Synthesis Example 15 was used instead of the first reaction product to carry out an addition reaction in the same manner as in Synthesis Example 2 to obtain an epoxy compound having an epoxy group at both terminals and a vinyl group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 132,000. The peak in the molecular weight distribution of the obtained epoxy compound was only one, and no peak for the low molecular weight derived from the methacrylic acid compound was observed. Further, it was confirmed by NMR that 2-methacryloyloxyethyl isocyanate reacted with the hydroxyl group and 100% of the vinyl group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Synthesis Example 17)

Synthesis of an epoxy compound obtained by reacting the above-mentioned fourth reactant obtained in Synthesis Example 15 with 4-hydroxybutyl glycidyl ether:

Using the fourth reactant obtained in Synthesis Example 15 instead of the first reactant, a condensation reaction was carried out in the same manner as in Synthesis Example 3 to obtain an epoxy compound having an epoxy group at both terminals and an epoxy group in the side chain.

The weight average molecular weight of the obtained epoxy compound was 132,000. There was only one peak in the molecular weight distribution of the obtained epoxy compound, and no peak for the low molecular weight derived from the 4-hydroxybutyl glycidyl ether compound was observed. Further, confirming that the condensation reaction proceeded, it was confirmed that 4-hydroxybutyl glycidyl ether reacted with the hydroxyl group and 100% of the epoxy group was introduced into the side chain with respect to 100% of the total number of hydroxyl groups before the reaction.

(Example 21)

The epoxy compound obtained in Synthesis Example 15 and the epoxy compound obtained in Synthesis Example 16 were mixed at a weight ratio of 5: 3 to obtain a mixture (21) of an epoxy compound. The resulting mixture (21) of epoxy compound had a viscosity of 1,000 Pa · s.

The curable composition (21) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (21) of the obtained epoxy compound. The viscosity of the obtained curable composition (21) was 1070 Pa · s.

(Example 22)

The epoxy compound obtained in Synthesis Example 16 and the epoxy compound obtained in Synthesis Example 17 were mixed at a weight ratio of 5: 3 to obtain a mixture (22) of an epoxy compound. The viscosity of the resulting mixture (22) of the epoxy compound was 1130 Pa · s.

The curable composition (22) was obtained in the same manner as in Example 1 except that the mixture (1) of the epoxy compound was changed to the mixture (22) of the obtained epoxy compound. The viscosity of the obtained curable composition (22) was 1200 Pa · s.

(Evaluation of Examples 21 and 22)

Evaluation items similar to those of Examples 1 to 10 were evaluated.

The results are shown in Table 3 below.

Further, in each of the synthesis examples, it is preferable that the hydroxyl groups of the first, second, third, and fourth reactants are (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate, or 4-hydroxybutyl glycidyl ether (The above-mentioned formula (a), (b), (c))] among the total number of hydroxyl groups before the reaction is from 3% to 100 % (All). As a result, it was confirmed that when the number ratio was in the range of 3% to 100%, the curing rate was fast, the adhesion and the moisture resistance were excellent, and the generation of pores became difficult, as in the above-mentioned examples.

One… Connection structure
2… The first connection object member
2a ... Top surface
2b ... electrode
3 ... Connection
4… The second connection object member
4a ... if
4b ... electrode
5 ... Conductive particle

Claims (21)

An epoxy group at both terminals, a vinyl group or an epoxy group in the side chain,
A weight average molecular weight of 500 or more and 150,000 or less,
(Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxycyclohexyl glycidyl ether is added to the reaction product of bisphenol F or resorcinol and 1,6-hexanediol diglycidyl ether or resorcinol diglycidyl ether. Hydroxybutyl glycidyl ether. ≪ / RTI > The epoxy compound according to claim 1, which has two or more vinyl groups in total in the side chain, or two or more epoxy groups in total in the side chain. The process of claim 1, wherein the reactant is a first reactant of bisphenol F and 1,6-hexanediol diglycidyl ether, a second reactant of resorcinol and 1,6-hexanediol diglycidyl ether, Or a third reactant of resorcinol and resorcinol diglycidyl ether. 4. The method according to claim 3, wherein when the reactant is the first reactant, there are two peaks in the molecular weight distribution of the epoxy compound,
Wherein two peaks are present in the molecular weight distribution of the epoxy compound when the reactant is the second reactant. The epoxy compound according to claim 3 or 4, wherein the reactant is the first reactant. The epoxy compound according to claim 3 or 4, wherein the reactant is the second reactant. The epoxy compound according to claim 3, wherein the reactant is the third reactant. 5. The epoxy compound according to any one of claims 1 to 4, wherein the compound to be reacted with the reactant is (meth) acrylic acid or 2- (meth) acryloyloxyethyl isocyanate. The epoxy compound according to claim 8, wherein the compound to be reacted with the reactant is 2- (meth) acryloyloxyethyl isocyanate. A mixture of an epoxy compound comprising at least two epoxy compounds according to any one of claims 1 to 4. 11. The process according to claim 10, wherein a first reaction product of bisphenol F and 1,6-hexanediol diglycidyl ether is reacted with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl A first epoxy compound obtained by reacting a diester with a first epoxy compound,
(Meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether is reacted with a second reactant of resorcinol and 1,6-hexanediol diglycidyl ether And a second epoxy compound to be obtained. 11. The method of claim 10, wherein a second reaction product of resorcinol and 1,6-hexanediol diglycidyl ether is reacted with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycol A second epoxy compound obtained by reacting a cidyl ether,
A third epoxy obtained by reacting a third reactant of resorcinol and resorcinol diglycidyl ether with (meth) acrylic acid, 2- (meth) acryloyloxyethyl isocyanate or 4-hydroxybutyl glycidyl ether, A compound of an epoxy compound, comprising a compound. The mixture of epoxy compounds according to claim 10, wherein the viscosity at 23 캜 is 50 Pa s or more. A curable composition comprising the epoxy compound according to any one of claims 1 to 4 and a heat curing agent. 15. The curable composition according to claim 14, which comprises at least two epoxy compounds. 15. The curable composition according to claim 14, further comprising a photocurable compound and a photopolymerization initiator. 15. The curable composition of claim 14, further comprising conductive particles. The curable composition according to claim 14, further comprising an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with at least one of two epoxy groups at both ends of the epoxy compound in addition to the epoxy compound. A first connecting object member, a second connecting object member, and a connecting portion connecting the first and second connecting object members,
Wherein the connecting portion is formed from the curable composition according to Claim 14. 20. The method of claim 19, wherein the curable composition comprises conductive particles,
And the first and second connection target members are electrically connected by the conductive particles. delete

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