TWI452102B - The hardened composition, the linking structure and the (meth) acrylate compound containing a mercapto group - Google Patents

Description

Curable composition, bonded structure, and (meth) acrylate compound containing mercapto group

The present invention relates to a curable composition which can be used for connecting a connecting member such as an electronic component or a circuit board, and more particularly, the present invention relates to a thiol group containing a mercapto group and a (meth)acryl fluorenyl group. A curable composition of a acrylate compound and a bonded structure using the curable composition. Further, the present invention relates to a novel mercapto group-containing (meth) acrylate compound containing a fluorenyl group and a (meth) acryl fluorenyl group.

A curable composition is used to connect various connection target members such as an electronic component or a circuit board. The curable composition contains a photocurable resin or a thermosetting resin.

The above curable composition is used, for example, for connection of a semiconductor wafer provided with a metal bump electrode and a circuit substrate provided with an electrode.

Further, a curable composition containing conductive particles is known. The curable composition containing conductive particles is used, for example, for connection between an IC (Integrated Circuit) wafer and a flexible printed circuit board, or an IC wafer and an ITO (Indium-Tin Oxide) electrode. Connection of circuit boards, etc.

As an example of the curable composition, Patent Document 1 listed below discloses a thermosetting or photocurable composition containing conductive particles, a base resin, and a hindered phenol polymerization inhibitor. As the base resin, a polyacetal resin and a (meth)acrylic resin are described.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2003-20455

Development of materials that can be used for the curable composition as described in Patent Document 1 is underway. However, the cured product of such a curable composition sometimes requires low hygroscopicity. Further, when the member to be joined is joined by the cured product of the curable composition, the adhesion between the cured product and the member to be joined may be required to be high.

An object of the present invention is to provide a curable composition which can reduce the hygroscopicity of a cured product after curing and which can improve the adhesion between the cured product and the member to be joined, and a bonded structure using the curable composition.

Another object of the present invention is to provide a novel sulfhydryl group-containing (meth) acrylate compound which can be used as a material for a curable composition.

According to a broader aspect of the present invention, there is provided a curable composition comprising a mercapto group-containing (meth) acrylate compound and an active energy ray polymerization initiator.

In a specific aspect of the curable composition of the present invention, the mercapto group-containing (meth) acrylate compound is a thiol-containing (meth) acrylate compound having a structure represented by the following formula (31):

[Chemical 1]

In the above formula (31), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms; and in the above formula (31), X represents the following formula (11) to (13). a group represented by any one of the above formulas (31), wherein both Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group;

[Chemical 2]

[Chemical 3]

[Chemical 4]

In another specific aspect of the curable composition of the present invention, Z1 and Z2 in the above formula (31) are both fluorenyl groups.

In still another specific aspect of the curable composition of the present invention, the mercapto group-containing (meth) acrylate compound having the structure represented by the above formula (31) has a fluorenyl group having a structure represented by the following formula (1) (meth) acrylate compound:

[Chemical 5]

In the above formula (1), R1 and R2 each represent hydrogen or a methyl group, and X represents a group represented by any one of the above formulas (11) to (13).

The connection structure according to the present invention includes a first connection target member, a second connection target member, and a connection portion that connects the first and second connection target members, and the connection portion is formed by a hardening combination according to the present invention. The object is hardened to form.

Further, according to a broader aspect of the present invention, there is provided a (meth) acrylate compound having a thiol group having a structure represented by the following formula (31):

[Chemical 6]

In the above formula (31), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms; and in the above formula (31), X represents the following formula (11) to (13). a group represented by any one of the above formulas (31), wherein both Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group;

[Chemistry 7]

[化8]

[Chemistry 9]

In a specific aspect of the mercapto group-containing (meth) acrylate compound of the present invention, Z1 and Z2 in the above formula (31) are both fluorenyl groups.

In another specific aspect of the mercapto group-containing (meth) acrylate compound of the present invention, the mercapto group-containing (meth) acrylate compound having the structure represented by the above formula (31) has the following formula (1) a thiol-containing (meth) acrylate compound of the structure:

[化10]

In the above formula (1), R1 and R2 each represent hydrogen or a methyl group, and X represents a group represented by any one of the above formulas (11) to (13).

Since the curable composition of the present invention contains a mercapto group-containing (meth) acrylate compound and an active energy ray polymerization initiator, the hygroscopicity of the cured product after hardening can be lowered. Further, when the member to be joined is joined by the cured product of the curable composition of the present invention, the adhesion between the cured product and the member to be joined can be improved.

Since the mercapto group-containing (meth) acrylate compound of the present invention has a structure represented by the above formula (31), it can be used as a material of the curable composition. The curable composition can be used for the connection of various connecting object members.

Hereinafter, the present invention will be described in detail.

The curable composition of the present invention comprises a mercapto group-containing (meth) acrylate compound and an active energy ray polymerization initiator. The mercapto group-containing (meth) acrylate compound of the present invention is a fluorenyl group-containing (meth) acrylate compound having a structure represented by the formula (31). The fluorenyl group is based on SH. The curable composition of the present invention preferably contains a mercapto group-containing (meth) acrylate compound represented by the formula (31).

((meth)acrylate compound containing mercapto)

The mercapto group-containing (meth) acrylate compound contained in the curable composition of the present invention contains a mercapto group and a (meth) acrylonitrile group. By using the mercapto group-containing (meth) acrylate compound, the hygroscopicity of the cured product of the curable composition can be lowered. Further, the adhesion between the cured product and the member to be connected can be improved.

The mercapto group-containing (meth) acrylate compound of the present invention has a structure represented by the following formula (31).

The (meth) acrylate compound containing a mercapto group contained in the curable composition of the present invention is preferably a mercapto group-containing (meth) acrylate compound having a structure represented by the following formula (31). By using a mercapto group-containing (meth) acrylate compound having a structure represented by the following formula (31), the hygroscopicity of the cured product of the curable composition can be sufficiently reduced. Further, the adhesion between the cured product and the member to be connected can be sufficiently increased. However, the curable composition of the present invention may contain a mercapto group-containing (meth) acrylate compound other than the mercapto group-containing (meth) acrylate compound represented by the formula (31).

[11]

In the above formula (31), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. In the above formula (31), X represents a group represented by any one of the following formulas (11) to (13). In the above formula (31), both of Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group.

[化12]

[Chemistry 13]

[Chemistry 14]

In other words, the compound having the structure represented by the above formula (31) has a structure represented by any one of the following formulas (31A) to (31C).

[化15]

In the above formula (31A), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. In the above formula (31A), both of Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group.

[Chemistry 16]

In the above formula (31B), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. In the above formula (31B), both of Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group.

[化17]

In the above formula (31C), R1 and R2 each represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. In the above formula (31C), both of Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group.

The mercapto group-containing (meth) acrylate compound having the structure represented by the above formula (31) contains a fluorenyl group and a (meth) acrylonitrile group. The group having the above mercapto group and the above (meth)acrylinyl group is bonded to a specific aromatic ring bonded to a benzene ring or a naphthalene ring. Since such a structure is obtained, for example, an active energy ray polymerization initiator is added to a (meth) acrylate compound containing a mercapto group to obtain a curable composition, and then the curable composition is irradiated with an active energy ray. The hardenable composition is cured.

When the carbon number of the alkyl group of R3 and R4 in the above formula (31) exceeds 5, the curing rate of the curable composition is likely to be slowed down. R3 and R4 in the above formula (31) are preferably methylene groups, respectively. In this case, the hardening speed of the above curable composition becomes faster.

It is preferred that Z1 and Z2 in the above formula (31) are both fluorenyl groups. The compound of the above formula (31) wherein Z1 and Z2 are both a mercapto group can reduce the hygroscopicity of the cured product of the curable composition as compared with the compound of the above formula (31) wherein Z1 is a mercapto group and Z2 is a hydroxyl group. .

In the above formula (31), it is preferred that R3 and R4 are each a methylene group, and both Z1 and Z2 are a fluorenyl group. That is, it is preferred that the (meth) acrylate compound having a mercapto group having the structure represented by the above formula (31) has a structure represented by the following formula (1).

[化18]

In the above formula (1), R1 and R2 each represent hydrogen or a methyl group. In the above formula (1), X represents a group represented by any one of the above formulas (11) to (13).

In other words, the compound having the structure represented by the above formula (1) has a structure represented by any one of the following formulas (1A) to (1C).

[Chemistry 19]

In the above formula (1A), R1 and R2 each represent hydrogen or a methyl group.

[Chemistry 20]

In the above formula (1B), R1 and R2 each represent hydrogen or a methyl group.

[Chem. 21]

In the above formula (1C), R1 and R2 each represent hydrogen or a methyl group.

It is preferred that R1 and R2 in the above (31) and the above formula (1) are each hydrogen. In this case, the (meth) acrylate compound containing a mercapto group is more excellent in hardenability.

In the above formula (31), it is preferred that R1 and R2 are each hydrogen, R3 and R4 are each a methylene group, and Z1 and Z2 are each a fluorenyl group. In other words, it is preferred that the (meth) acrylate compound having a mercapto group having the structure represented by the above formula (31) has a structure represented by the following formula (21). The mercapto group-containing (meth) acrylate compound having a structure represented by the following formula (21) is more excellent in curability.

[化22]

In the above formula (21), X represents a group represented by any one of the above formulas (11) to (13).

In other words, the compound having the structure represented by the above formula (21) has a structure represented by any one of the following formulas (21A) to (21C).

[化23]

[Chem. 24]

[化25]

Further, the above "(meth) acrylate" means acrylate and methacrylate. The above "(meth)acrylic acid" means acrylic acid and methacrylic acid. The above "(meth)acryl fluorenyl group" means an acryl fluorenyl group and a methacryl fluorenyl group.

(Method for producing (meth) acrylate compound containing mercapto group)

A mercapto group-containing (meth) acrylate compound having a structure represented by the above formula (31), that is, a mercapto group-containing (meth) acrylate having a structure represented by any one of the above formulas (31A) to (31C) The method for producing the compound is not particularly limited and, for example, can be obtained as follows.

An epoxy compound (hereinafter also referred to as epoxy compound A) represented by any one of the following formulas (71A) to (71C) is prepared.

[Chem. 26]

In the above formula (71A), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化27]

In the above formula (71B), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化28]

In the above formula (71C), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

Then, all of the epoxy groups of the above epoxy compound A are converted into an episulfide group (thiol group) to obtain an episulfide compound represented by any one of the following formulas (81A) to (81C) (hereinafter also referred to as It is an episulfide compound B1). Alternatively, an epoxy group of one of the following formulas (82A) to (82C) is obtained by converting one of the epoxy groups A to an epoxy group (hereinafter also referred to as an episulfide compound B2). ). The above episulfide compound is a compound containing a thiopyranyl group. The episulfide compound represented by any one of the following formulas (82A) to (82C) is also an epoxy compound and is an epoxy group-containing episulfide compound.

[化29]

In the above formula (81A), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化30]

In the above formula (81B), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化31]

In the above formula (81C), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化32]

In the above formula (82A), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化33]

In the above formula (82B), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

[化34]

In the above formula (82C), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.

The epoxy compound A preferably has a structure represented by any one of the following formulas (51A) to (51C). An epoxy compound having a structure represented by the following formulas (51A) to (51C) is easily available.

[化35]

[化36]

[化37]

By using an epoxy compound having a structure represented by the above formulas (51A) to (51C), a structure having any one of the following formulae (61A) to (61C) and (62A) to (62C) can be obtained. Sulphur compound.

[化38]

[39]

[化40]

[化41]

[化42]

[化43]

The method for producing the above-described episulfide compounds B1 and B2 is preferably a production method in which a vulcanizing agent and the above epoxy compound A are mixed. By the production method, the epoxy group of the above epoxy compound A can be converted into an episulfide group.

Examples of the vulcanizing agent include thiocyanates, thioureas, phosphine sulfide, dimethylthiocarbamide, and N-benzothiazole-2-thione. Vulcanizing agents other than these may also be used. Among them, preferred are thiocyanates or thioureas, and more preferred are thiocyanates. Examples of the thiocyanate include sodium thiocyanate, potassium thiocyanate, and sodium thiocyanate. Examples of the thiourea include thiourea, N-methylthiourea, and 1,3-diethylthiourea.

The above-mentioned vulcanizing agent is preferably used in an amount of from 10 to 1,000 parts by weight based on 100 parts by weight of the above epoxy compound A. It is more preferred to use the above-mentioned vulcanizing agent in an amount of from 80 to 110 parts by weight based on 100 parts by weight of the above epoxy compound A. When the amount of the above-mentioned vulcanizing agent used is too small, the epoxy group may not be sufficiently converted into an episulfide group. If the amount of the above-mentioned vulcanizing agent is too large, the effect of converting an epoxy group into an episulfide group may be saturated.

When the above vulcanizing agent is mixed with the above epoxy compound A, a solvent can also be used. Further, the vulcanizing agent and the epoxy compound A may be added to a solvent to prepare a solution. Examples of the solvent include water and an organic solvent. Examples of the organic solvent include methanol and ethanol.

The solvent is preferably used in the range of 100 to 3000 parts by weight based on 100 parts by weight of the epoxy compound A. It is more preferred to use the above solvent in the range of 200 to 1,500 parts by weight based on 100 parts by weight of the above epoxy compound A. When the amount of the solvent used is too small, the epoxy compound A may be polymerized. If the amount of the solvent used is too large, the cost may increase.

After converting the epoxy group of the above epoxy compound A into an episulfide group, it is preferred to remove water, a solvent and an unreacted vulcanizing agent. The water, solvent and unreacted vulcanizing agent can be removed by previously known methods.

Further, when the reaction of the above epoxy compound A is carried out, a catalyst may also be used. By using the above catalyst, the conversion ratio to the sulfur group can be adjusted. Further, since the epoxy group can be converted into an episulfide group in a low temperature environment, the polymerization reaction of the above epoxy compound A can be suppressed.

Examples of the catalyst include a palladium catalyst, titanium dioxide, and cyanuric chloride. Examples of the palladium catalyst include palladium metal particles.

The above catalyst is preferably used in an amount of from 0.02 to 3 parts by weight based on 100 parts by weight of the above epoxy compound A. When the amount of the above-mentioned catalyst used is within the above range, the epoxy group can be more efficiently converted into an epoxide group in a low temperature environment.

Then, by reacting (meth)acrylic acid with the above-mentioned episulfide compounds B1 and B2, a mercapto group-containing (meth)acrylate compound having a structure represented by the above formula (31) can be obtained.

The above (meth)acrylic acid is preferably used in an amount of from 40 to 120 parts by weight based on 100 parts by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of the (meth)acrylic acid used is in the above range, the (meth)acrylonitrile group can be introduced more efficiently.

When the above-mentioned episulfide compounds B1 and B2 are mixed with the above (meth)acrylic acid, a solvent can also be used. Further, the above-mentioned episulfide compound B and the above (meth)acrylic acid may be added to a solvent to prepare a solution. Examples of the solvent include water and an organic solvent. Examples of the organic solvent include methanol, ethanol, toluene, and the like.

The solvent is preferably used in an amount of from 50 to 300 parts by weight based on 100 parts by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of the solvent used is in the above range, the (meth) acrylonitrile group can be introduced more efficiently.

When the above-mentioned episulfide compounds B1 and B2 are reacted with the above (meth)acrylic acid, a catalyst or a polymerization inhibitor or the like may be used.

Examples of the catalyst include triethylamine, dimethylbenzylamine, N,N'-trimethylpyridine, 2,4,6-tris(dimethylaminomethyl)phenol, and triethylenediamine. Trimethylbenzylammonium chloride, tetra-n-butylammonium bromide, lithium chloride, triphenylphosphine, and the like. Examples of the polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, benzoquinone, p-tert-butyl catechol, and 2,6-dibutyl-4-methylphenol. .

The above catalyst is preferably used in an amount of from 0.5 to 5 parts by weight based on 100 parts by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of use of the above catalyst is within the above range, the (meth)acrylonitrile group can be introduced more efficiently. The above polymerization inhibitor is preferably used in an amount of from 0.2 to 1.5 parts by weight based on 100 parts by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of the polymerization inhibitor used is in the above range, the (meth)acrylonitrile group can be introduced more efficiently.

(active energy ray polymerization initiator)

The curable composition of the present invention can be obtained by adding an active energy ray polymerization initiator to the above-mentioned fluorenyl group-containing (meth) acrylate compound. The curable composition can be cured by irradiating the curable composition with an active energy ray. As the above active energy ray polymerization initiator, a commercially available photopolymerization initiator can be usually used.

Specific examples of the photopolymerization initiator include an acetophenone photopolymerization initiator, a ketal photopolymerization initiator, a halogenated ketone, a mercaptophosphine oxide, and a mercaptophosphonate. Photopolymerization initiators other than these may also be used. The photopolymerization initiator may be used alone or in combination of two or more.

Specific examples of the acetophenone photopolymerization initiator include 4-(2-hydroxyethoxy)phenyl (2-hydroxy-2-propyl) ketone and 2-hydroxy-2-methyl- 1-phenylpropan-1-one, methoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, and 2-hydroxy-2-cyclohexylbenzene Ketones, etc. Specific examples of the ketal photopolymerization initiator include benzoin dimethyl ketal and the like.

The content of the active energy ray polymerization initiator is preferably in the range of 0.05 to 10 parts by weight based on 100 parts by weight of the above-mentioned fluorenyl group-containing (meth) acrylate compound. The content of the active energy ray polymerization initiator is preferably 0.1 part by weight or more, more preferably 7.5 parts by weight or less, more preferably 7.5 parts by weight or less based on 100 parts by weight of the above-mentioned fluorenyl group-containing (meth) acrylate compound. 5 parts by weight or less. When the content of the active energy ray polymerization initiator is at least the above lower limit, the effect of adding the above active energy ray polymerization initiator can be sufficiently obtained. When the content of the active energy ray polymerization initiator is not more than the above upper limit, the adhesion of the cured product of the curable composition is made higher.

(Adjustable to other ingredients in the hardenable composition)

The curable composition of the present invention preferably further contains a filler. By using a filler, the latent heat expansion of the cured product of the above curable composition can be suppressed. These fillers may be used alone or in combination of two or more.

Specific examples of the filler include cerium oxide, aluminum nitride, and aluminum oxide. It is preferred that the above filler is a filler particle. The average particle diameter of the above filler particles is preferably in the range of 0.1 to 1.0 μm. When the average particle diameter of the filler particles is within the above range, the latent heat expansion of the cured product of the curable composition can be further suppressed. In addition, the "average particle diameter" mentioned above shows the volume average diameter measured by the dynamic laser scattering method.

The content of the above filler is preferably in the range of 50 to 900 parts by weight based on 100 parts by weight of the above-mentioned mercapto group-containing (meth) acrylate compound. When the content of the filler is within the above range, the latent heat expansion of the cured product of the curable composition can be further suppressed.

The curable composition may further contain a solvent, an ion scavenger or a decane coupling agent as needed.

The solvent is not particularly limited. The solvent may, for example, be ethyl acetate, methyl ceramide, toluene, acetone, methyl ethyl ketone, cyclohexane, n-hexane, tetrahydrofuran or diethyl ether. These solvents may be used alone or in combination of two or more.

The above decane coupling agent is not particularly limited. The decane coupling agent may, for example, be N-(2-aminoethyl)-3-aminopropyltrimethoxydecane or N-(2-aminoethyl)-3-aminopropylmethyl. Dimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, N-(2-aminoethyl)-3-aminopropyltriethoxydecane , 3-aminopropyl dimethyl ethoxy decane, 3-aminopropyl methyl diethoxy decane, 3-aminopropyl trimethoxy decane, 3-aminopropyl triethoxy Decane, vinyl triethoxy decane, vinyl trimethoxy decane, vinyl triethoxy decane, vinyl trichloro decane, 3-glycidoxy propyl trimethoxy decane, 3-glycidyl oxygen Propylmethyldiethoxydecane, 3-glycidoxypropyltriethoxydecane, 3-mercaptopropyltrimethoxydecane, 3-mercaptopropylmethyldimethoxydecane, 3- Chloropropyltrimethoxydecane, 3-chloropropyltriethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-methylpropenyloxypropyltriethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, ethyltrimethoxydecane, propyl Trimethoxy decane, propyl triethoxy decane, dodecyl triethoxy decane, hexyl trimethoxy decane, isobutyl diethoxy decane, methyl phenyl diethoxy decane, methyl Phenyldimethoxydecane, imidazolium, and the like. Among them, preferred is imidazolium. The decane coupling agent may be used alone or in combination of two or more.

The ion trapping agent is not particularly limited. Specific examples of the ion scavenger include aluminosilicate, aqueous titanium oxide, aqueous cerium oxide, zirconium phosphate, titanium phosphate, hydrotalcite, ammonium phosphomolybdate, hexacyano zinc, and an ion exchange resin. The ion scavenger may be used alone or in combination of two or more.

The curable composition can be used as a one-liquid type adhesive for the subsequent bonding of a liquid crystal panel or a semiconductor wafer. The curable composition may be a paste-like adhesive or a film-like adhesive.

The method of processing the above curable composition into a film-like adhesive is not particularly limited. For example, a method in which the curable composition is applied onto a substrate such as release paper to form a film-form adhesive; or a solvent is added to the curable composition and applied to a base such as a release paper. After the material, the solvent is volatilized to form a film-like adhesive.

The active energy ray irradiated when the curable composition is cured includes ultraviolet rays, electron beams, α rays, β rays, γ rays, X rays, infrared rays, and visible rays. Among these active energy rays, an ultraviolet ray or an electron beam is preferred in order to achieve excellent hardenability and hardly deteriorate the cured product.

The light source used when the curable composition is irradiated with light such as ultraviolet rays is not particularly limited. As the light source, for example, a light source having a sufficient light emission distribution at a wavelength of 420 nm or less can be cited. Further, specific examples of the light source include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a chemical lamp, a black light lamp, a microwave excited mercury lamp, and a metal halide lamp. Among them, a chemical lamp is preferred. The chemical lamp not only efficiently emits light in the active wavelength region of the photopolymerization initiator, but also has a small amount of luminescence in the light absorption wavelength region of the composition component other than the photopolymerization initiator. Further, by using a chemical lamp, the light can efficiently reach the photopolymerization initiator present in the curable composition.

For example, in the case of a cleavage type photopolymerization initiator having an acetophenone group, the light irradiation intensity in the wavelength region of 365 nm to 420 nm is preferably in the range of 0.1 to 100 mW/cm ² .

The curable composition may also contain conductive particles. The curable composition containing conductive particles can be used as an anisotropic conductive material.

The conductive particles are electrically connected between the circuit board and the electrodes of the semiconductor wafer, for example. The conductive particles are not particularly limited as long as they are conductive particles. The surface of the conductive layer of the conductive particles may be covered by an insulating layer or insulating particles. In this case, when the connection of the connection member is performed, the insulating layer or the insulating particles between the conductive layer and the electrode are excluded. Examples of the conductive particles include conductive particles in which the surface of the organic particles, the inorganic particles, the organic-inorganic hybrid particles, and the metal particles are covered with a metal layer, and metal particles substantially composed only of a metal. The metal layer is not particularly limited. Examples of the metal layer include a gold layer, a silver layer, a copper layer, a nickel layer, a palladium layer, and a metal layer containing tin.

The content of the above conductive particles is not particularly limited. The content of the conductive particles is preferably 0.1 part by weight or more, more preferably 0.5 part by weight or more, and most preferably 10 parts by weight or less based on 100 parts by weight of the above-mentioned fluorenyl group-containing (meth) acrylate compound. More preferably, it is 5 parts by weight or less. When the content of the conductive particles is at least the above lower limit, each electrode or the like can be electrically connected more reliably. When the content of the conductive particles is at most the above upper limit, the conduction cannot be performed, and the short circuit between adjacent electrodes is more difficult to occur.

When the curable composition is in the form of a liquid or a paste, the viscosity (25 ° C) of the curable composition is preferably in the range of 20,000 to 100,000 mPa·s. When the viscosity of the above curable composition is within the above range, the curable composition can be easily applied. In addition, when the viscosity of the curable composition containing the conductive particles is too low, the conductive particles may precipitate, and if the viscosity is too high, the conductive particles may not be sufficiently dispersed.

(Use of curable composition)

The curable composition of the present invention can be used to follow various connecting object members.

The curable composition is suitable for obtaining a connection structure in which a first connection target member provided with a metal bump electrode and a second connection target member provided with an electrode are electrically connected.

Further, when the curable composition is an anisotropic conductive material containing conductive particles, the anisotropic conductive material can be used as an anisotropic conductive paste, an anisotropic conductive ink, or an anisotropic conductive adhesive. An anisotropic conductive film or an anisotropic conductive sheet is used. When the anisotropic conductive material is used as a film-like adhesive such as an anisotropic conductive film or an anisotropic conductive sheet, the film-like adhesive containing the conductive particles may be laminated without conductivity. A film-like adhesive of particles.

The anisotropic conductive material is suitable for obtaining a connection structure in which the first and second connection members are electrically connected.

Fig. 1 schematically shows 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 3, and a connection portion 4 that electrically connects the first and second connection object members 2, 3. The connecting portion 4 is formed by curing the curable composition. In the connection structure 1, an anisotropic conductive material containing the conductive particles 5 is used as the curable composition.

A plurality of electrodes 2b are provided on the upper surface 2a of the first connection object member 2. A plurality of electrodes 3b are provided on the lower surface 3a of the second connection member 3. The electrode 2b and the electrode 3b are electrically connected by the conductive particles 5.

Specifically, as the connection structure, an electronic component wafer such as a semiconductor wafer, a capacitor wafer, or a diode wafer is mounted on a circuit board, and an electrode of the electronic component wafer is electrically connected to an electrode on the circuit board. Connected to a structure, etc. Examples of the circuit board include various circuit boards such as a flexible printed circuit board, a glass substrate, and a substrate on which a metal foil is laminated.

The method for producing the above-described connection structure is not particularly limited. An example of the method of manufacturing the connection structure is to dispose the anisotropic conductive material between the first connection member such as an electronic component or a circuit board, and the second connection member such as an electronic component or a circuit board, and obtain a laminate. Thereafter, the laminate is heated and pressurized.

Since the curable composition contains the above-mentioned (meth) acrylate compound containing a mercapto group, the hygroscopicity of the cured product of the curable composition can be lowered. Further, the adhesion of the cured product of the curable composition to the metal can be improved. Therefore, the curable composition is more suitable for obtaining a connection structure in which a first connection target member provided with a metal bump electrode and a second connection target member provided with an electrode are electrically connected. Further, the curable composition is also suitable for forming the cured layer in a laminate comprising a metal plate and a cured layer laminated on at least one side of the metal plate.

Hereinafter, the present invention will be specifically described by way of examples and comparative examples. The invention is not limited to the following examples.

In the examples and comparative examples, the following active energy ray polymerization initiator, filler, and conductive particles were suitably used.

(active energy ray polymerization initiator)

Photopolymerization initiator A ("DAROCUR TPO" manufactured by Ciba)

Photopolymerization initiator B ("IRGUCURE 819" manufactured by Ciba)

Photopolymerization initiator C ("IRGUCURE 1122" manufactured by Ciba)

(filler)

Germanium dioxide (average particle size 0.25 μm)

Alumina (average particle size 0.5 μm)

(conductive particles)

Conductive particles (including a metal layer having a nickel plating layer formed on the surface of the divinylbenzene resin particles and a gold plating layer formed on the surface of the nickel plating layer)

(Example 1)

In Example 1, a mercapto group-containing (meth) acrylate compound represented by the following formula (21A) was synthesized.

[化44]

(1) Synthesis A of the episulfide compound represented by the above formula (61A)

100 parts by weight of resorcinol diglycidyl ether of the epoxy compound represented by the above formula (51A), 80 parts by weight of potassium thiocyanate, 20 parts by weight of acetonitrile, and a palladium catalyst ("Tanjin Precious Metals Co., Ltd." 0.005 parts by weight of chlorotetraamethylene bromide), 500 parts by weight of ethanol, and 50 parts by weight of water are mixed and stirred to convert an epoxy group into an epoxide group to obtain an episulfide compound represented by the above formula (61A).

The ¹ H-NMR measurement of the obtained episulfide compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the episulfide group in the region of 2.0 to 3.0 ppm appeared. Thereby, it was confirmed that the epoxy group of resorcinol diglycidyl ether has been converted into an episulfide group.

(2) Synthesis of a mercapto group-containing (meth) acrylate compound represented by the above formula (21A)

100 parts by weight of the obtained episulfide compound represented by the above formula (61A), 80 parts by weight of acrylic acid, 100 parts by weight of toluene, 5 parts by weight of hydroquinone, and 5 parts by weight of tetra-n-butylammonium bromide were mixed. Further, oxygen was introduced and heated to 100 ° C to obtain a mercapto group-containing (meth) acrylate compound represented by the above formula (21A).

The ¹ H-NMR measurement of the obtained mercapto group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating that the region of 2.0 to 3.0 ppm of the presence of the sulfhydryl group disappeared, indicating that the signal of the region of 2.5 to 3 ppm of the presence of the sulfhydryl group appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thus, it was confirmed that the mercapto group-containing (meth) acrylate compound represented by the above formula (21A) was obtained.

(3) Preparation of curable composition

0.5 parts by weight of a photopolymerization initiator A ("DAROCUR TPO" manufactured by Ciba Corporation) was added to 100 parts by weight of the obtained mercapto group-containing (meth) acrylate compound represented by the above formula (21A), and a planet was used. The mixer was stirred at 2000 rpm for 5 minutes, whereby a hardenable composition was obtained.

(Example 2)

In Example 2, a mercapto group-containing (meth) acrylate compound represented by the following formula (21B) was synthesized.

[化45]

(1) Synthesis of an episulfide compound represented by the above formula (61B)

The above formula is obtained in the same manner as in the synthesis of the (1) episulfide compound of the first embodiment, except that the compound represented by the above formula (51A) is changed to the epoxy compound represented by the above formula (51B). 61B) An episulfide compound as shown.

The ¹ H-NMR measurement of the obtained episulfide compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the episulfide group in the region of 2.0 to 3.0 ppm appeared. Thereby, it was confirmed that the epoxy group of the epoxy compound represented by the above formula (51B) has been converted into an episulfide group.

(2) Synthesis of a mercapto group-containing (meth) acrylate compound represented by the above formula (21B)

The (2) thiol-containing (meth)acrylic acid of (2) of Example 1 was changed except that the episulfide compound represented by the above formula (61A) was changed to the obtained episulfide compound represented by the above formula (61B). In the same manner as the synthesis of the ester compound, a mercapto group-containing (meth) acrylate compound represented by the above formula (21B) is obtained.

The ¹ H-NMR measurement of the obtained mercapto group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating that the region of 2.0 to 3.0 ppm of the presence of the sulfhydryl group disappeared, indicating that the signal of the region of 2.5 to 3 ppm of the presence of the sulfhydryl group appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thus, it was confirmed that the mercapto group-containing (meth) acrylate compound represented by the above formula (21B) was obtained.

(3) Preparation of curable composition

The sulfhydryl group-containing (meth) acrylate compound represented by the above formula (21A) is changed to the thiol group-containing (meth) acrylate compound represented by the above formula (21B), and is prepared and carried out. In the same manner as the preparation of the (3) curable composition of Example 1, a curable composition was obtained.

(Example 3)

In Example 3, a mercapto group-containing (meth) acrylate compound represented by the following formula (21C) was synthesized.

[Chem. 46]

(1) Synthesis of an episulfide compound represented by the above formula (61C)

The above formula is obtained in the same manner as in the synthesis of the (1) episulfide compound of the first embodiment, except that the compound represented by the above formula (51A) is changed to the epoxy compound represented by the above formula (51C). 61C) The episulfide compound shown.

The ¹ H-NMR measurement of the obtained episulfide compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the episulfide group in the region of 2.0 to 3.0 ppm appeared. Thereby, it was confirmed that the epoxy group of the epoxy compound represented by the above formula (51C) has been converted into an episulfide group.

(2) Synthesis of a mercapto group-containing (meth) acrylate compound represented by the above formula (21C)

The (2) thiol-containing (meth)acrylic acid of Example 2 is used, except that the episulfide compound represented by the above formula (61A) is changed to the obtained episulfide compound represented by the above formula (61C). In the same manner as the synthesis of the ester compound, a mercapto group-containing (meth) acrylate compound represented by the above formula (21C) can be obtained.

The ¹ H-NMR measurement of the obtained mercapto group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating that the region of 2.0 to 3.0 ppm of the presence of the sulfhydryl group disappeared, indicating that the signal of the region of 2.5 to 3 ppm of the presence of the sulfhydryl group appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thus, it was confirmed that the mercapto group-containing (meth) acrylate compound represented by the above formula (21C) was obtained.

(3) Preparation of curable composition

The sulfhydryl group-containing (meth) acrylate compound represented by the above formula (21A) is changed to the thiol group-containing (meth) acrylate compound represented by the above formula (21C), and is carried out and carried out. In the same manner as the preparation of the (3) curable composition of Example 1, a curable composition was obtained.

(Comparative Example 1)

In Comparative Example 1, a hydroxyl group-containing (meth) acrylate compound represented by the following formula (101A) was synthesized.

[化47]

(1) Synthesis of a hydroxyl group-containing (meth) acrylate compound represented by the above formula (101A)

100 parts by weight of resorcinol diglycidyl ether of the epoxy compound represented by the above formula (51A), 80 parts by weight of acrylic acid, 50 parts by weight of toluene, 5 parts by weight of hydroquinone, and tetra-n-butyl group 5 parts by weight of ammonium bromide was mixed and oxygen was added thereto, and the mixture was heated to 100 ° C to obtain a hydroxyl group-containing (meth) acrylate compound represented by the above formula (101A).

The ¹ H-NMR measurement of the obtained hydroxyl group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the hydroxyl group in the region of 2.5 to 3.5 ppm appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thereby, it was confirmed that the hydroxyl group-containing (meth) acrylate compound represented by the above formula (101A) was obtained.

(2) Preparation of curable composition

The hydroxy group-containing (meth) acrylate compound represented by the above formula (101A) obtained by changing the thiol group-containing (meth) acrylate compound represented by the above formula (21A) is used and carried out. In the same manner as the preparation of the (3) curable composition of Example 1, a curable composition was obtained.

(Comparative Example 2)

In Comparative Example 2, a hydroxyl group-containing (meth) acrylate compound represented by the following formula (101B) was synthesized.

[48]

(1) Synthesis of a hydroxyl group-containing (meth) acrylate compound represented by the above formula (101B)

In the same manner as in Comparative Example 1, except that the epoxy compound represented by the above formula (51A) was changed to the epoxy compound represented by the above formula (51B), the hydroxyl group represented by the above formula (101B) was obtained. (meth) acrylate compound.

The ¹ H-NMR measurement of the obtained hydroxyl group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the hydroxyl group in the region of 2.5 to 3.5 ppm appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thereby, it was confirmed that the hydroxyl group-containing (meth) acrylate compound represented by the above formula (101B) was obtained.

(2) Preparation of curable composition

The hydroxy group-containing (meth) acrylate compound represented by the above formula (101B) obtained by changing the thiol group-containing (meth) acrylate compound represented by the above formula (21A) is used and carried out. In the same manner as the preparation of the (3) curable composition of Example 1, a curable composition was obtained.

(Comparative Example 3)

In Comparative Example 3, a hydroxyl group-containing (meth) acrylate compound represented by the following formula (101C) was synthesized.

[化49]

(1) Synthesis of a hydroxyl group-containing (meth) acrylate compound represented by the above formula (101C)

The hydroxyl group represented by the above formula (101C) was obtained in the same manner as in Comparative Example 1, except that the epoxy compound represented by the above formula (51A) was changed to the epoxy compound represented by the above formula (51C). (meth) acrylate compound.

The ¹ H-NMR measurement of the obtained hydroxyl group-containing (meth) acrylate compound was carried out using chloroform as a solvent. As a result, the signal indicating the presence of the epoxy group in the region of 6.5 to 7.5 ppm disappeared, and the signal indicating the presence of the hydroxyl group in the region of 2.5 to 3.5 ppm appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thereby, it was confirmed that the hydroxyl group-containing (meth) acrylate compound represented by the above formula (101C) was obtained.

(2) Preparation of curable composition

The hydroxy group-containing (meth) acrylate compound represented by the above formula (101C) obtained by changing the thiol group-containing (meth) acrylate compound represented by the above formula (21A) is used and carried out. In the same manner as the preparation of the (3) curable composition of Example 1, a curable composition was obtained.

(Evaluation of Examples 1 to 3 and Comparative Examples 1 to 3)

(1) Hygroscopicity

Using the LED (Light Emitting Diode) Spot UV device manufactured by HOYA Corporation, the obtained curable composition was irradiated with light of 375 nm at a light irradiation intensity of 1500 mW/cm ^{2 for} 5 seconds to form a hardenable combination. The material was hardened to obtain a film-like cured product of the curable composition (6 mm in length × 6 mm in width × 1 mm in thickness). The obtained cured product was allowed to stand at 80 ° C and a relative humidity of 85% for 24 hours. The moisture absorption was evaluated by determining the weight change of the cured product before and after the placement according to the method of JIS K7209. The smaller the change in weight, the lower the hygroscopicity.

(2) Next force

A transparent glass substrate provided with an ITO electrode on its upper surface was prepared. Further, a semiconductor wafer having a gold bump electrode on its lower surface is prepared.

The curable composition obtained was applied to the above transparent glass substrate so as to have a thickness of 30 μm to form a curable composition layer. Then, the semiconductor wafer is laminated on the curable composition layer such that the electrodes face each other. Thereafter, the curable composition layer was irradiated with light of 375 nm for 5 seconds at a light irradiation intensity of 1500 mW/cm ² using an LED Spot UV device manufactured by HOYA Co., Ltd. to cure the curable composition layer, thereby obtaining a bonded structure.

The shear strength of the obtained joined structure was measured using a Universal Adhesion Tester Series 4000 manufactured by Days, Inc., and the adhesion was evaluated.

The results are shown in Table 1 below.

(Examples 4 to 12)

A mercapto group-containing (meth) acrylate compound containing a mercapto group-containing (meth) acrylate compound represented by the formula (31) shown in the following Table 2 was synthesized. A curable composition was obtained in the same manner as in the preparation of the (3) curable composition of Example 1 except that the obtained mercapto group-containing (meth) acrylate compound was used.

Further, in Examples 4 to 6, when (2) the thiol-containing (meth) acrylate compound of Examples 1 to 3 was synthesized, acrylic acid was changed to methacrylic acid. In the examples 7 to 12, when the episulfide compound represented by the formula (61A) of the first embodiment (1) is synthesized, the epoxy compound represented by the above formulas (71A) to (71C) is suitably used, that is, the formula ( In the 71A)~(71C), R3 and R4 are respectively an exo-butyl group (nC ₃ H ₆ ) or an exo-pentyl group (nC ₅ H ₁₀ ) epoxy compound instead of resorcinol diglycidyl ether.

(Examples 13 to 19)

A curable composition having the composition shown in Table 3 below was prepared. In Examples 13 to 19, the mercapto group-containing (meth) acrylate compound having the structure represented by the above formulas (21A) to (21C) obtained in Examples 1 to 3, and the above photopolymerization are suitably used. a starting agent, the above filler, and the above conductive particles.

(Embodiment 20)

(1) Synthesis of episulfide compounds

When the episulfide compound represented by the formula (61A) of the formula (1) is synthesized, the amount of potassium thiocyanate used is decreased, and the conversion ratio is adjusted to obtain an epoxy compound represented by the above formula (51A), and the above formula (62A) a mixture X1 of an epoxy group-containing episulfide compound and an episulfide compound represented by the above formula (61A). The conversion ratio of the epoxy group to the cyclic thio group in the whole of the obtained mixture X1 was 50%. That is, the ratio of the number of epoxy groups to the epoxy groups (epoxy group: episulfide group) in the obtained mixture X1 was 1:1.

(2) Synthesis of thiol-containing (meth) acrylate compounds

The modification of the episulfide compound represented by the above formula (61A) to the above-obtained mixture X1 is carried out in the same manner as in the synthesis of the (2) mercapto group-containing (meth)acrylate compound of Example 1. The (meth) acrylate compound containing a hydroxyl group represented by the above formula (101A), a (meth) acrylate compound having a hydroxyl group and a thiol group represented by the following formula (22A), and the formula (21A) A mixture Y1 containing a mercapto (meth) acrylate compound.

[化50]

(3) Preparation of curable composition

In the same manner as the preparation of the (3) curable composition of Example 1 except that the thiol group-containing (meth) acrylate compound represented by the above formula (21A) was changed to the obtained mixture Y1. , a curable composition is obtained.

(Example 21)

(1) Synthesis of episulfide compounds

When the episulfide compound represented by the formula (61B) of the formula (1) is synthesized, the amount of potassium thiocyanate used is reduced, and the conversion ratio is adjusted to obtain an epoxy compound represented by the above formula (51B), and the above formula (62B) a mixture X2 of an epoxy group-containing episulfide compound and an episulfide compound represented by the above formula (61B). The conversion ratio of the epoxy group to the cyclic thio group in the whole of the obtained mixture X2 was 50%. That is, the ratio of the number of epoxy groups to cyclothio groups (epoxy group: episulfide group) in the obtained mixture X2 was 1:1.

(2) Synthesis of thiol-containing (meth) acrylate compounds

The modification of the episulfide compound represented by the above formula (61B) to the above-obtained mixture X2 is carried out in the same manner as in the synthesis of the (2) mercapto group-containing (meth)acrylate compound of Example 2, The (meth) acrylate compound having a hydroxyl group represented by the above formula (101B), a (meth) acrylate compound having a hydroxyl group and a thiol group represented by the following formula (22B), and the formula (21B) A mixture Y2 containing a mercapto (meth) acrylate compound.

[化51]

(3) Preparation of curable composition

In the same manner as the preparation of the (3) curable composition of Example 1 except that the thiol group-containing (meth) acrylate compound represented by the above formula (21A) was changed to the obtained mixture Y2. , a curable composition is obtained.

(Example 22)

(1) Synthesis of episulfide compounds

When the episulfide compound represented by the formula (61C) of the formula (1) is synthesized, the amount of potassium thiocyanate used is reduced, and the conversion ratio is adjusted to obtain an epoxy compound represented by the above formula (51C), and the above formula (62C) a mixture X3 of an epoxy group-containing episulfide compound and an episulfide compound represented by the above formula (61C). The conversion ratio of the epoxy group to the cyclic thio group in the whole of the obtained mixture X3 was 50%. That is, the ratio of the number of epoxy groups to cyclothio groups (epoxy group: episulfide group) in the obtained mixture X3 was 1:1.

(2) Synthesis of thiol-containing (meth) acrylate compounds

In the same manner as the synthesis of the (meth)acrylate compound containing the mercapto group of (2) of Example 3, except that the episulfide compound represented by the above formula (61C) is changed to the above-mentioned mixture X3. The (meth) acrylate compound containing a hydroxyl group represented by the above formula (101C), a (meth) acrylate compound having a hydroxyl group and a thiol group represented by the following formula (22C), and the formula (21C) A mixture Y3 containing a mercapto (meth) acrylate compound.

[化52]

(3) Preparation of curable composition

In the same manner as the preparation of the (3) curable composition of Example 1 except that the thiol group-containing (meth) acrylate compound represented by the above formula (21A) was changed to the obtained mixture Y3. , a curable composition is obtained.

(Evaluation of Examples 4 to 22)

The evaluation items of Examples 4 to 22 and the same evaluation items as those of Examples 1 to 3 and Comparative Examples 1 to 3 were evaluated.

The results are shown in Tables 2 to 3 below. However, in the following Tables 2 to 3, the evaluation results of the hygroscopicity and the adhesion force indicate the results determined based on the following criteria.

[Determination of hygroscopicity]

○○: The weight change is less than 1.5%

○: The weight change is 1.5% or more and less than 2.5%.

△: The weight change was 2.5% or more and less than 3.5%.

×: The weight change is 3.5% or more

[Follow the benchmark of force]

○○: Shear strength is 800 N/cm ² or more

○: Shear strength is 675 N/cm ² or more and less than 800 N/cm ₂

△: Shear strength is 550 N/cm ² or more and less than 675 N/cm ₂

×: The shear strength is less than 550 N/cm ²

1. . . Connection structure

2. . . First connection object member

2a. . . Upper surface

2b, 3b. . . electrode

3. . . Second connection object member

3a. . . lower surface

4. . . Connection

5. . . Conductive particles

Fig. 1 is a front cross-sectional view schematically showing an example of a connection structure using a curable composition containing a mercapto group-containing (meth) acrylate compound according to an embodiment of the present invention.

1. . . Connection structure

2. . . First connection object member

2a. . . Upper surface

2b, 3b. . . electrode

3. . . Second connection object member

3a. . . lower surface

4. . . Connection

5. . . Conductive particles

Claims (7)

A curable composition comprising a mercapto group-containing (meth) acrylate compound and an active energy ray polymerization initiator; and the thiol group-containing (meth) acrylate compound has a structure represented by the following formula (31) a (meth) acrylate compound containing a mercapto group: In the above formula (31), R1 and R2 each represent hydrogen or a methyl group, R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms, and X represents any one of the following formulas (11) to (13). In the above formula (31), both Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group; [Chemical 4] The sclerosing composition of claim 1, wherein Z1 and Z2 in the above formula (31) are both fluorenyl groups. The curable composition of claim 1, wherein the mercapto group-containing (meth) acrylate compound having the structure represented by the above formula (31) is a thiol group having a structure represented by the following formula (1) )Acrylate compound: In the above formula (1), R1 and R2 each represent hydrogen or a methyl group, and X represents a group represented by any one of the above formulas (11) to (13). A connection structure including a first connection target member, a second connection target member, and a connection portion connecting the first and second connection target members; wherein the connection portion is caused by any one of claims 1 to 3 The curable composition of the article is formed by hardening. A mercapto group-containing (meth) acrylate compound having a structure represented by the following formula (31): [Chemical 6] In the above formula (31), R1 and R2 each represent hydrogen or a methyl group, R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms, and X represents any one of the following formulas (11) to (13). In the above formula (31), both Z1 and Z2 represent a fluorenyl group, or Z1 represents a fluorenyl group and Z2 represents a hydroxy group; The mercapto group-containing (meth) acrylate compound according to claim 5, wherein Z1 and Z2 in the above formula (31) are both fluorenyl groups. The mercapto group-containing (meth) acrylate compound according to claim 5, which is a thiol-containing (meth) acrylate compound having a structure represented by the following formula (1): In the above formula (1), R1 and R2 each represent hydrogen or a methyl group, and X represents a group represented by any one of the above formulas (11) to (13).