TW201113344A - Curable composition, connected structures, and mercapto-containing (meth)acrylate compound - Google Patents

Abstract

Provided is a curable composition which can yield a cured product that exhibits a reduced moisture absorption and an enhanced bond strength to a member to be connected. Also provided is a novel (meth)acrylate compound containing a thiol group, which is usable as a material for the curable composition. The curable composition contains both a mercapto-containing (meth)acrylate compound and an initiator for actinic energy ray polymerization. The novel mercapto-containing (meth)acrylate compound has a structure represented by general formula (31) [wherein R1 and R2 are each hydrogen or a methyl group; R3 and R4 are each a C1-5 alkylene group; X is a specific aromatic group; and Z1 and Z2 are each a mercapto group, or alternatively Z1 is a mercapto group with Z2 being a hydroxyl group].

Description

[Technical Field] 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 method comprising a sparing agent A curable composition of a (meth) acrylate compound containing a sulfhydryl group of a (fluorenyl) acrylonitrile group, and a bonded structure using the curable composition. Further, the present invention relates to a novel mercapto group-containing (meth) acrylate compound containing a thiol group and a (fluorenyl) propylene group. [Prior Art] A curable composition is used in order 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 the 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 a 1C wafer and an ITO (Indium-Tin Oxide) electrode. Connection of circuit boards, etc. As an example of the above-mentioned curable composition, Patent Document 1 listed below discloses a thermosetting or photocurable composition containing conductive particles, a base resin, and a polymerization inhibitor. As the base resin, a polyacetal resin and a (fluorenyl) acrylic resin are described. [Prior Art Document] 150186.doc 201113344 [Patent Document 1] [Patent Document 1] Japanese Patent Laid-Open Publication No. 2003-20455 [Draft of the Invention] [Problems to be Solved by the Invention] It is being used as described in Patent Document 1. Development of materials for the curable composition. 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 connecting member is sometimes 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 hardening 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. [Technical means for solving the problem] According to a broader aspect of the present invention, there is provided a curable composition comprising a mercapto group-containing (fluorenyl) 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 (meth) acrylate compound having a structure represented by the following formula (3). : 150186.doc 201113344 [Chemical 1]

In the above formula (1), R1 and R2 respectively represent hydrogen or a sulfhydryl group, and R3 and sigma are respectively represented by a ruthenium of 1 to 5, and a methyl group of the above formula (3 U,乂 denotes the base of _ ^ ^ ^ _ _ in any of the following (11) to (13); in the above formula (31), both Z1 and Z2 are not Wei-based, or Z1 represents a base and Z2 Express the base; [Chemical 2]

Formula (12) Formula (13) όα· In the other specific g-form of the curable composition of the present invention, Z1 and Z2 in the above formula (3D are both fluorenyl groups. The curable composition of the present invention Further, in another specific aspect, the (meth)acrylic acid-containing compound having a structure represented by the above formula (9) is a thiol-containing (methyl group) having a structure represented by the following formula (1): 150186.doc 201113344 )Acrylate compound: [Chemical 5]

(11) The base shown in any of (13)t. The connection structure of this month includes 帛! The connection target member, the second connection object member, and the connection portion connecting the second and second connection target members are formed by curing the curable composition configured according to the present invention. Further, according to a broader aspect of the present invention, there is provided a (meth)acrylic acid vinegar compound which has a structure having a structure represented by the following formula (1)): [Chemical 6]

In the above formula (31), ... and each represent hydrogen or a mercapto group, and each of them represents a stretching group having a carbon number of 1 to 5; in the above formula (31), X represents a formula () (13) Any one of the above formulas; in the above formula (1)), the system and the 22 sentences represent a radical " or 21 represents a radical and Z2 represents a radical; _·· (31) 150I86.doc 201113344 [Chem. 7]

Equation (11) [Chemical 8] ... (12) "a.

[Chemistry 9]

(13) In a specific aspect of the mercapto group-containing (meth) acrylate compound of the present invention, 21 and 22 in the above formula (31) are fluorenyl groups. In another specific aspect of the (meth)acrylic compound containing a thiol group of the invention, the (meth) propylene I vine compound having the thiol group having the above formula (3 ^ ^ ) is not The following A > formula (the structure of the thiol-containing (meth) acrylate compound: [Chemical 10] R2

(1) In the above formula (1), the old and the respective 矣(11) to (13, φ knives (1) represent hydrogen or sulfhydryl groups, and X represents a group represented by any of the above. 150186.doc 201113344 [Effects of the Invention] Since the curable composition of the present invention contains a mercapto group-containing (fluorenyl) acrylate compound and an active energy ray polymerization initiator, the hygroscopicity of the cured product after hardening can be reduced. When the cured object of the curable composition of the present invention is connected to the member to be joined, the adhesion between the cured product and the member to be joined can be improved. Since the mercapto group-containing (fluorenyl) acrylate compound of the present invention has the above formula (3) 1) The structure shown in Fig. 1 can be used as a material for a curable composition. The curable composition can be used for connection of various members to be joined. [Embodiment] Hereinafter, the present invention will be described in detail. The curable composition of the present invention The present invention comprises a mercapto-containing (fluorenyl)-acrylic acid vinegar compound and an active energy ray polymerization initiator. The mercapto group-containing (fluorenyl) acrylate compound of the present invention has a structure represented by formula (3丨). The (meth) acrylate compound containing a whale group is a fluorenyl group-based SH group. The curable composition of the present invention preferably contains a mercapto group-containing (fluorenyl) acrylate vinegar compound represented by the formula (31). The sulfhydryl group-containing (meth) acrylate compound contained in the curable composition of the present invention contains a sulfhydryl group and a (fluorenyl) acrylonitrile group. The (meth) acrylate compound can reduce the hygroscopicity of the cured product of the curable composition. Further, the adhesion between the cured product and the member to be joined can be improved. The sulfhydryl group-containing acrylic acid of the present invention The ester compound has a structure represented by the following formula 150186.doc 201113344 (31). The thiol group-containing (meth) acrylate compound contained in the curable composition of the present invention preferably has the following formula (3 1) The fluorenyl-containing (fluorenyl) acrylate compound having a structure shown in the above formula can be sufficiently reduced by using a (meth)acrylic acid vinegar compound having a sulfhydryl group having a structure of the following formula (31) The hygroscopicity of the cured product of the curable composition can further increase the adhesion between the cured product and the member to be joined. However, the curable composition of the present invention may further comprise a sulfhydryl group represented by the formula (31). A mercapto group-containing (fluorenyl) acrylate compound other than the acrylate group.

Ζ 2 R2 [^0, /%4 people ^.丫4^ (8) In the above formula (31), the ruthenium and the hydrazine respectively represent hydrogen or a methyl group, and R3 and R4 each represent an alkylene group having a number of from 1 to 5. In the above formula (31), X represents a group represented by any one of the following formulas (11) and (13). In the above formula (31), both of Ζ1 and Ζ2 represent a fluorenyl group, or Z1 represents a sulfhydryl group and Ζ2 represents a hydroxy group. [化 12]

[11] (11)

...(12) 150186.doc 201113344 [Chem. 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), ri&R2 represents hydrogen or a methyl group, respectively, and R3 and 4 represent an alkylene group having a carbon number of 1 to 5, respectively. In the above formula (31A), both of the groups 21 and 22 represent a fluorenyl group, or Z1. Represents a thiol group and Z2 represents a hydroxy group. [Chemistry 16]

In the above formula (31B), 'R1' and R2 each represent hydrogen or a fluorenyl group, and R3' and R4 each represent an alkylene group having 1 to 5 carbon atoms. In the above formula (31B), both of the groups Z1 and Z2 represent a thiol group or Z1 represents a thiol group and Z2 represents a hydroxy group. 150186.doc -10· 201113344 [Chem. 17]

In the above formula (31(:), 111 and 1^2 respectively represent hydrogen or a mercapto group, and the scales 3 and 4 represent an alkylene group having a carbon number of 1 to 5, respectively. In the above formula (31C), both the zi and the z2 are And a sulfhydryl group-containing (meth) acrylate compound having a structure represented by the above formula (31), which contains a fluorenyl group and a (meth) acrylonitrile group, and has a sulfhydryl group and The group of the above (meth)acrylinyl group is bonded to a specific aromatic ring and bonded to a benzene ring or a naphthalene ring. Since it has such a structure, it can be, for example, a (mercapto) acrylate having a sulfhydryl group. After the active energy ray polymerization initiator is added to the compound to obtain a curable composition, the curable composition is cured by irradiating the curable composition with an active energy ray. If R3 and R4 in the above formula (31) are stretched. When the carbon number of the alkyl group exceeds $, the curing rate of the curable composition is likely to be slowed down. R3 and R4 in the above formula (31) are each preferably a methylene group. In this case, the above-mentioned hardenable combination The hardening speed of the object becomes faster. It is preferred that Z1 and Z2 in the above formula (31) are both sulfhydryl groups. Z1 and Z2 in the formula (31) are all a compound of a Wei group, and the hygroscopicity of the cured product of the curable composition can be lowered as compared with the compound of the above formula (31) which is a sulfhydryl group and the Z2 is a hydroxyl group. 150186.doc 201113344 In the above formula (31), it is preferred that R3 and R4 are an anthracenylene group, and both Z1 and Z2 are a sulfhydryl group. That is, it is preferred to have a hydrazine represented by the above formula (3i). The (meth) propylene oxime ester compound has a lower structure.

In the above formula (1), R1 and each represent hydrogen or a methyl group. ·.* in (1),? C represents a group represented by any one of the above formulas (11) to (13). That is, the compound having the structure represented by the above formula (1) has a structure represented by any one of the following (1A) to (1C). [Chem. 19]

R1 SH

• Formula (U) In the above formula (1A), 'R1 and R2 respectively represent hydrogen or a fluorenyl group. [化20] ^

Ο

Formula (1B) In the above formula (1B), R1 and R2 respectively represent hydrogen or methyl group 150186.doc •12· 201113344 [Chem. 21]

〇 Formula (1C) SH R2 In the above formula (I C), R1 and R2 each represent hydrogen or a methyl group. Preferably, the above-mentioned (31) and the above-mentioned formulae are each hydrogen. In this case, the (meth) acrylate compound containing a mercapto group is more excellent in curability. In the above formula (31), it is preferred that R1 & R2 are each hydrogen, and each of them is a methylene group, and both of 21 and 22 are a sulfhydryl group. In other words, it is preferred that the (meth)acrylic acid s-containing compound having the structure represented by the above formula (31) has a structure represented by the following formula (21). The (meth)acrylic acid s-containing compound having a structure represented by the following formula (21) is more resistant to curability.

SH

Ο

SH

In the formula (9), where x represents the above formula (1)) to (13), that is, the compound having the structure represented by the above formula (21) (2 i A)% i The structure shown in any of C). -There is a return type 150186.doc 201113344 [Chem. 23] Γ SH I [Chem. 24] SH 〇 , QU [Chem. 25J 〇Π ... (21A) ... (21B)

Further, the above "(meth) acrylate" means acrylate and mercapto acrylate. The above "(indenyl) acrylic acid" means acrylic acid and methacrylic acid. The above "(meth)acrylylene group" means an acryloyl group and a methyl propyl group. (Manufacturing Method of (Indenyl) Acrylate Compound Containing Mercapto Group) The mercapto group-containing (fluorenyl) acrylic acid vinegar compound having the structure represented by the above formula (31) has the above formula (3 1 A) to (3 1C) The method for producing a mercapto group-containing (fluorenyl) acrylate compound having a structure shown by any of them is not specifically defined by, for example, 150186.doc • 14·201113344, and can be obtained, for example, in the following manner. The epoxy compound shown in the following formula (71A) to (7 1C) is prepared (hereinafter also referred to as epoxy compound A). [Chem. 26]

Formula (71A) In the above formula (71A), R3 and R4 each represent an alkylene group of a carbon number of 5.

In the above formula (71B), [Chem. 28] 〇 ′ R3 and R4 represent a C.

丄 Μ 中 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Then, Jiang 1 μ , Ben, m (4) South base Λ; 4; all epoxy groups of the oxidized compound are converted into a ring hard compound heart: a ring represented by any of Γ(81Α)~(81C) " A 丌% is the episulfide compound B1). Alternatively, the partial epoxy group of the above epoxidized A is converted into an episulfide group, and an episulfide compound represented by any one of the following formulas 150186.doc -15-201113344 (82A) to (82C) is obtained (hereinafter also It is called an episulfide compound B2). The above episulfide compound is a compound containing a pyranyl group. The episulfide compound represented by any one of the following formulae (82A) to (82C) is also an epoxy compound and is an epoxy group-containing episulfide compound. [Chem. 29] S, • R3

R4 Ο.

S Formula (81A) In the above formula (81A), R3 and R4 each represent a C 1 to 5 alkyl group [Chemical 30] S, R4

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

S

, 0 R3

R4 type (81C)

In the above formula (81C), R3 and R4 represent an alkylene group having a carbon number of 1 to 5, respectively. [Chem. 32] 150186.doc •16-201113344

(Expression (82A) In the above formula (82A), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. [化33]

Formula (82B) In the above formula (82B), R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms. [34]

(Expression (82C) 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 formulae (5 1A) to (51C). An epoxy compound having a structure represented by the following formulas (51 A) to (5 1C) is easily available. [化35]

...(51Α) [化36] 150186.doc 17· 201113344

Formula (51B) Formula (51C) By using an epoxy compound having a structure represented by the above formula (51A) to (5 1C), it is possible to obtain the following formulas (61A) to (61C), (62A). An episulfide compound of the structure shown in any of ~(62C). [化38]

[化39]

Formula (61A) Formula (61B) Formula (61C) 150186.doc -18- 201113344

[化42]

[化43]

砸 砸 · · · 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 62 . The epoxy group of the above epoxy compound A can be converted into an episulfide group by the production method. Examples of the vulcanizing agent's include thiocyanates, thioureas, phosphine sulfides: monomethyl thiazide and benzothiazole-2-thione. It is also possible to use a sulfonate or a thiocyanate, and more preferably a thiocyanate. Examples of the thiocyanate include sulfuric acid, potassium brothate, sodium thiocyanate, and the like. Examples of the thiourea include L ^ & methylthiourea and 1,3-diethylthiourea. Compared with the 1% by weight of j*, +, „%% Oxygen Compound A, the above vulcanizing agent is used in the range of 10 to 1000 lbs. .doc 19 201113344 100 parts by weight of oxygen compound A, more preferably in the range of 8 〇 to 11 〇 parts by weight. If the amount of the above-mentioned vulcanizing agent is too small, the ring reduction may not be fully converted. A ring-forming thio group. If the amount of the domain wei agent is too large, the effect of converting the epoxy group to the epoxide group may be saturated. When the above-mentioned vulcanizing agent is mixed with the above epoxy compound A, it may also be used. Further, the vulcanizing agent and the epoxy compound A may be added to a solvent to prepare a solution. The solvent may, for example, be water and an organic solvent 4. Examples of the organic solvent include methanol and Ethyl alcohol, etc. It is preferred to use the above solvent in a range of 100 to 3000 parts by weight based on 1 part by weight of the above epoxy compound A. It is more preferably 1 part by weight based on the above epoxidation. It is in 2〇〇~15〇〇 When the amount of the solvent used is too small, the epoxy compound may be polymerized. If the amount of the solvent used is too large, the cost may be increased. After the epoxy group of A is converted into an episulfide group, it is preferred to remove water, a solvent and an unreacted vulcanizing agent. The water, the solvent and the unreacted vulcanizing agent can be removed by a conventionally known method. In the reaction of the epoxy compound A, a catalyst can 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 in the lower blood % si brother Further, the polymerization reaction of the above-mentioned epoxy compound A can be suppressed. Examples of the catalyst include palladium catalyst, titanium oxide, and melamine chloride, and the above-mentioned catalysts include, for example, metal particles. -20- 201113344 It is preferred to use the above catalyst in a range of 0.02 to 3 parts by weight based on 100 parts by weight of the above epoxy compound. When the amount of the above-mentioned catalyst is within the above range, At low temperatures More preferably, the epoxy group is converted into an alkylthio group. Then, by reacting the (indenyl)acrylic acid with the above-mentioned episulfide compounds B1 and B2, a mercapto group having the structure represented by the above formula (31) can be obtained ( The above-mentioned (mercapto)acrylic acid is preferably used in the range of 40 to 120 parts by weight based on 1 part by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of the fluorenyl group-acrylic acid 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 (mercapto)acrylic acid, 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. The organic solvent may, for example, be methanol, ethanol or toluene. It is preferred to use the above solvent in a range of 50 to 300 parts by weight based on 1 part by weight of the above-mentioned episulfide compounds Bi and B2. When the use of the above solvent is within the above range, the (meth) acrylonitrile group can be introduced more efficiently. A catalyst or a polymerization inhibitor may be used in the reaction of the above-mentioned episulfide compounds B1 and B2 with the above (meth)acrylic acid. Examples of the catalyst include triethylamine, dibenzylamine, N,N,-trimethyl sulfonium 2,4,6-di(monomethylaminoindenyl)benzene, triethylenediamine, and trimethyl. 150186.doc 21 201113344 basal-based ammonium hydride, tetra-n-butylammonium bromide, lithium gasification and tri-phenylphosphine. Examples of the polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, benzoquinone, p-tert-butyl catechol, and 2,6-dibutyl-4-indolylphenol. . The above catalyst is preferably used in an amount of from 0.5 to 5 parts by weight based on 1 part by weight of the above-mentioned episulfide compound B 1 and B 2 . When the use of the above catalyst 1 is within the above range, the (meth) propyl 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 1 part by weight of the above-mentioned episulfide compounds B1 and B2. When the amount of the polymerization inhibitor to be used is within 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 amount linear polymerization initiator to the above mercapto group-containing (fluorenyl) 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 self-chemical ketone, a mercaptophosphine oxide, and a decylphosphonate. 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-hydrazine. _Phenylpropan-1-one, decyloxyacetophenone, 2,2-dimethoxy 4,2-diphenylethane a·150l86.doc -22- 201113344 ketone, and 2-hydroxy-2- Cyclohexyl acetophenone and the like. Specific examples of the ketal photopolymerization initiator include benzoin dimethyl ketal and the like. It is preferred that the content of the above active energy ray polymerization initiator is in the range of 0.05 to 10 parts by weight based on the weight loss of the above-mentioned (meth) acrylate compound containing fluorenyl group. The amount of the above active energy ray polymerization initiator is preferably 0.1 part by weight or more, more preferably 75 parts by weight or less, based on 100 parts by weight of the above-mentioned mercapto group-containing (meth) acrylate compound. It is preferably 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 becomes higher. (Other components which can be formulated in the curable composition) The curable composition of the present invention preferably further contains a filler. By using a filler, the latent thermal 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 oxygen cutting, nitriding, and aluminum oxide. It is preferred that the above filler is a filler particle. The average particle size of the above filler particles is preferably in the range of 〇 Η 〇 μιη. 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 above-mentioned "average particle diameter" means a volume average diameter measured by a dynamic laser scattering method. _ The content of the above filler is preferably in the range of 50 parts by weight based on the weight of the above-mentioned (meth) acrylate compound containing fluorenyl group of 150186.doc -23 to 201113344 parts. When the content of the above 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 trapping agent or a decane coupling agent as needed. The solvent is not particularly limited. The solvent may, for example, be ethyl acetate, methyl sarbuta, toluene or acetone. Base ethyl hydrazine, cyclohexanone, hexanol, tetrahydrofuran and bis. 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, Ν(2-aminoethylmethyl)-3-aminopropyl fluorenyl Alkoxy money, hydrazine (2 aminoethyl 3-aminopropyl trimethoxy decane, hydrazine (2_. ylethyl) 3 -aminopropyl triethoxy decane, 3-aminopropyl Dimethyl ethoxy decane, 3-aminopropyl methyl diethoxy decane, 3-aminopropyl trimethoxy decane, 3-aminopropyl triethoxy decane, vinyl triethoxy Base decane, vinyl trimethoxy decane, vinyl triethoxy decane, vinyl trichloro decane, 3 - glycidoxypropyl trimethoxy decane, 3-glycidoxy propyl methyl Ethoxy decane, 3-glycidoxypropyl triethoxy decane, 3 sulfopropyl dimethoxy zeoxime, 3- benzyl propyl methoxide, 3 propyl propyl Dioxalate, tris-propyltriethoxy zeoxime, 3-mercaptopropenyloxypropyltrimethoxysulfonate, 3-methylpropenyloxypropyltriethoxydecane , 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, Trimethyltrioxane, propyltrimethoxysulfide, propyltriethoxylate, decene 150186.doc -24- 201113344 dialkyltriethoxydecane, hexyltrimethoxydecane, isobutyl Diethoxy decane, methylphenyl diethoxy decane, methyl phenyl dimethoxy oxane, and sodium salin. Among them, 'immediately, imidazolium. The above decane coupling agent can be used only. The above-mentioned ion scavenger is not particularly limited. Specific examples of the ion scavenger include succinate, aqueous titanium oxide, aqueous cerium oxide, phosphoric acid, titanium phosphate, and hydrotalcite. And the above-mentioned ion scavenger may be used alone or in combination of two or more. The curable composition may be used as a one-liquid type adhesive for liquid crystal. The curable composition may be a paste-like adhesive or a film-like adhesive. The method of processing the curable composition into a film-like adhesive is not particularly limited. Can be cited - a method in which the curable composition is applied to 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 release paper # substrate, and then a method in which a solvent is volatilized to form a film-like adhesive agent, etc. The active energy ray irradiated when the curable composition is cured includes ultraviolet rays, electron beams, α rays, β rays, read lines, xenon rays, infrared rays, and visible light. Among these active energy rays, an ultraviolet light or an electron beam is preferably used for the purpose of achieving excellent hardenability and hardening of the cured product. The curable composition is irradiated with a light source such as a violet external line and the like. In particular, as the light source, for example, a light source having a sufficient light emission distribution at a wavelength of 420 nm or less is used. I50I86.doc -25·201113344 Examples include, for example, a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a chemical lamp, a black lamp, a microwave-excited mercury lamp, and a metal-chemical 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 the amount of luminescence in the light absorption wavelength region of the composition component other than the photopolymerization initiator is small. Further, by using a chemical lamp, light can be efficiently obtained by the photopolymerization initiator present in the curable composition. For example, the light irradiation intensity in the wavelength region of 365 nm to 420 nm when the cleavage type photopolymerization initiator having an acetophenone group is contained is preferably in the range of 0.1 to 100 mW/cm2. 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 to, for example, a circuit board and an electrode of a semiconductor wafer. 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, the insulating layer or the insulating particles between the conductive layer and the electrode are excluded when the connection of the connection member is performed. Examples of the conductive particles include conductive particles in which a surface of an organic particle, an inorganic particle, an organic-inorganic hybrid particle, and a metal particle is covered with a metal layer, and a metal particle 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 '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 150186.doc -26 - 201113344 is preferably 重量·1 parts by weight or more, more preferably 〇5, based on 1 part by weight of the thiol group-containing (meth) acrylate compound. The parts by weight or more are preferably 10 parts by weight or less, more preferably 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 more reliably turned on. When the content of the conductive particles is less than or equal to the above upper limit, the conduction cannot be performed, and the short circuit between the 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 200 Å to 1 〇〇〇〇〇 in the range of 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 be swelled, and if the viscosity is too high, the conductive particles may not be dispersed. (Use of Curable Composition) The curable composition of the present invention can be used in combination with various bonding pairs, and the above-mentioned curable composition is suitable for obtaining a second connection object member to which a metal bump electrode is provided and an electrode provided. The connection structure. When the connecting member is electrically connected and is in the case of the above-described hardenable composite helium conductive material, the === anisotropic conductive paste of the conductive particles and the anisotropic conductive material can be used as anisotropic anisotropy Conductive film, or two-direction conductive adhesive, each .. _ _ raw ¥ electric sheet, etc. In the case of the winter life 'conductive material as a direction (four) guide f thin electric ^ _ adhesive use In the case of containing the conductive (tetra) adhesive, the film layer of the film can be expanded to have a film shape containing no conductive particles, and then 150186.doc -27- 201113344

(2) Curing property of the second connection object configuration form The anisotropic conductive material is suitable for obtaining a connection structure in which the first member is electrically connected. Fig. 1 schematically shows an example of a connection structure using the actual composition of the present invention. The connection structure 图 shown in Fig. 1 includes the first connection object member Μ~π1 丹/丁么, the brother 2 nd object 3, and the second and second connection object members 2, 3 are electrically connected. The connecting portion 4. The connection portion 4 is stored by curing the curable composition. Connect the structure! In the above curable composition, an anisotropic conductive material having conductive particles 5 on its shoulder is used. A plurality of electrode electrodes are provided on the upper surface of the first connection object member 2. On the lower surface of the second connection object member 3, a plurality of electric powers (four) are called. The electrode electrode 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 and an electrode on the circuit board are electrically connected: The connection structure P is a circuit board, and various circuit boards such as a printed circuit board such as a printed circuit board, a glass substrate, or a metal foil-clad substrate are used. The method for manufacturing the connection structure is not particularly limited. In the example of the method of manufacturing the connection structure, the anisotropic conductive material is placed between the first connection target 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 the laminate is obtained. After the body, the laminate is heated and pressurized. 150186.doc •28· 201113344 The curable composition contains the above-mentioned (meth) acrylate compound containing a mercapto group, so that 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 embodiments. 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 ("DAROCURTPO" manufactured by Ciba) Photopolymerization initiator B ("IRGUCURE 819" manufactured by Ciba) Photopolymerization initiator C (Ciba "IRGUCURE 1122" (manufactured by the company) (filler) dioxide dioxide (average particle size 0.25 μηι) alumina (average particle size 0.5 μπι) (conductive particles) conductive particles (including metal layer, the metal layer in diethylene A nickel plating layer is formed on the surface of the benzene resin particles, and a gold plating layer is formed on the surface of the nickel plating layer) (Example 1) 150186.doc • 29· 201113344 In the examples! In the above, a (meth) acetoacetate compound containing a thiol group represented by the following formula (21A) is synthesized. [化44]

SH

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

Formula (21A) 100 parts by weight of isophthalic diglycidyl ether of the epoxy compound represented by the above formula (51A), 8 parts by weight of potassium thiocyanate, 2 parts by weight of acetonitrile, and a catalyst ( "Dichlorotetramium" manufactured by Tanaka Precious Metals Co., Ltd. 0 005 Heavy-duty ethanol 500 parts by weight, 50 parts by weight of water, mixed and stirred, thereby converting the epoxy group into an epoxide group to obtain the above formula ( 61A) The episulfide compound shown. The measurement of 1 h nmr of the obtained episulfide compound was carried out using chloroform as a solvent. As a result, the signal indicating that the region of 6 5 to 7 5 ppm of the epoxy group disappeared, and the signal indicating the presence of the ring thio group in the region of 2. 〇 3 〇 ppm appeared. Thereby, it was confirmed that the epoxy group of resorcinol diglycidyl ether has been converted into a bad thio group. (2) One part by weight of the episulfide compound represented by the above formula (61A) and 80 parts by weight of acrylic acid obtained by synthesizing the mercapto group-containing (fluorenyl) acrylate compound represented by the above formula (21A) 100 parts by weight of toluene, 5 parts by weight of hydroquinone, and 5 parts by weight of tetra-n-butyl bromide, and the mixture is heated to 100 ° C to obtain a thiol group represented by the above formula (21A).曱基)丙150186.doc •30· 201113344 enoate compound. The h-NMR measurement of the obtained mercapto group-containing (fluorenyl) acrylate compound was carried out using a gas imitation as a solvent. As a result, the signal indicating the presence of the ring thio group in the region of 2_0 to 3.0 ppm disappeared, indicating that the signal of the region of 2.5 to 3 ppm in the presence of the sulfhydryl group appeared. Further, a signal indicating a region of 4 to 6 ppm in the presence of the 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 A photopolymerization initiator A (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). DAROCUR TPO") 会5 will be my part, 占田> θ』 also 1 J 〇 里 伤 injury, using a comet mixer at 2000 rpm for 5 minutes, thereby obtaining a hardening composition. (Example 2) In Example 2, a (meth)acrylic acid sulfonic acid compound containing a thiol group represented by the following formula (21B) was synthesized. [化45]

SH

SH (1) Formula (21B) (1) Synthesis of the episulfide compound represented by the above formula (61B): The compound represented by the above formula (51A) is changed to the epoxy compound represented by the above formula (51B), and In the same manner as in the synthesis of the (1) episulfide compound of the Example ', the ring-vulcanization 150186.doc • 31·201113344 represented by the above formula (61B) was obtained. The 1H-NMR measurement of the obtained episulfide compound was carried out using a solvent as a solvent. The result 'is a region of 6.5 to 7.5 ppm in the presence of an epoxy group, and the signal disappears, and a signal indicating a region of 2. G to 3.0 ppm in which the sulfenyl group is present appears. Thus, it was confirmed that the epoxy group of the epoxy compound represented by the above formula (51B) was converted into an episulfide group. (2) Synthesis of a mercapto group-containing (meth) acrylate compound represented by the above formula (21B): The episulfide compound represented by the above formula (61A) is changed to the obtained episulfide compound represented by the above formula (61B) The mercapto group-containing (fluorenyl) acrylate compound represented by the above formula (21B) is obtained in the same manner as the synthesis of the (meth) oxime group-containing (meth) acrylate compound of the example (2). . The obtained 1H-NMR measurement of the obtained mercapto-containing (fluorenyl) acrylic acid vinegar compound was carried out using a gas imitation as a solvent. As a result, the signal indicating the presence of the episulfide group in the region of 2.0 to 3.0 ppm 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 the acrylonitrile group appears. Thus, it was confirmed that the (meth) acrylate compound containing a thiol group represented by the above formula (21B) was obtained. (3) Preparation of curable composition The mercapto group-containing (mercapto) acrylate compound represented by the above formula (21A) is changed to the obtained mercapto group-containing (meth) acrylate represented by the above formula (21B). A curable composition was obtained in the same manner as in the preparation of the (3) curable composition of the Example except the compound. 150186.doc • 32·201113344 (Example 3) The sulfhydryl group-containing (meth) acrylate compound represented by the following formula (21c) was synthesized in Example 3. [Chem. 46]

0 'η

(21C) SH (1) Synthesis of the episulfide compound represented by the above formula (61C): The compound represented by the above formula (51A) is changed to the epoxy compound represented by the above formula (5ic), and The episulfide compound represented by the above formula (61C) was obtained in the same manner as in the synthesis of the episulfide compound of the Example. The obtained episulfide compound 21h_nmr was measured by using a gas imitation as a solvent. As a result, the signal indicating the region of 6·5 to 7 5 ppm in the presence of the epoxy group disappeared, and the signal indicating the region of 2·0 to 3 G ppm in the presence of the episulfide group appeared. Thus, it was confirmed that the epoxy group of the epoxy compound represented by the above formula (51C) has been converted into an episulfide group. <Base acrylate compound (2) The thiol group represented by the above formula (21C) (the synthesis of the oxime is carried out by changing the epoxidized compound represented by the above formula (61A) to the obtained formula (61C) The above formula (150186.doc -33 - 201113344) was obtained in the same manner as in the example 丨2 (2) in which the sulfhydryl group-containing (meth) acrylate compound was formed in the same manner as the epoxidized compound shown in the example (2). 21C) The present invention #3 has a thiol-based acrylate compound. The chloroform is used as a solvent to carry out the measurement of iH-Wei containing the (meth)acrylic acid vinegar compound of the county. As a result, the signal indicating that the region of 2.0 to 3.0 ppm of the presence of the sulfenyl group disappeared, indicating that the signal of the region of 2.5 to 3 ppm of the presence of the sulfhydryl group appeared. Further, it indicates that the presence of the acrylonitrile group was 4 to 6 ppm. The signal of the region appears. This confirms that the (meth) acrylate compound containing the thiol group represented by the above formula (21C) is obtained. (3) Preparation of the curable composition The thiol group represented by the above formula (21A) is contained. The (meth) acrylate compound k is more obtained by the above formula A curable composition was obtained in the same manner as in the preparation of the curable composition of the Example (2) except that the thiol-containing (meth) acrylate compound (2 ic) was used. (Comparative Example 1) In Comparative Example 1, a hydroxyl group-containing (meth) acrylate compound represented by the following formula (101A) was synthesized. [化47]

OH

OH

Formula (I01A) (1) Resorcinol-glycidol which is an epoxy compound represented by the above formula (5 1A) on the side of the synthesis of the hydroxyl group-containing (meth) acrylate compound represented by the above formula (101A) Shouting 100 parts by weight, 80 parts by weight of bupropion acid, 5,156 parts by weight of toluene, 150,186.doc -34 to 201113344 parts, 5 parts by weight of hydroquinone, and 5 parts by weight of tetra-n-butylammonium bromide, and putting in oxygen, The one-step (f-based) acrylate compound represented by the above formula (i〇ia) is obtained by heating to 1 〇〇〇c. The measurement of 丨H_NMR of the obtained hydroxyl group-containing (meth) acrylate compound was carried out using a gas imitation 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 that the region of 4 to 6 Ppm of the presence of the acrylonitrile group appears appears. Thus, it was confirmed that a hydroxyl group-containing (meth) acrylate compound represented by the above formula (101Α) was obtained. (2) Preparation of curable composition The thiol group-containing (meth) acrylate compound represented by the above formula (2 1 Α) is changed to the obtained formula (101 Α), t contains a trans group (meth) A curable composition was obtained in the same manner as in the preparation of the (3) curable composition of the Example acetonitrile compound except the above. (Comparative Example 2) In Comparative Example 2, a fluorenyl group-containing acrylate compound represented by the following formula (101B) was obtained. [化48]

OH

OH U) Synthesis of a hydroxyl group-containing (meth) acrylate compound of the above formula (101B) 150l86.doc 35· 201113344 The epoxy compound represented by the above formula (5 1A) is changed to the above formula (1) (7). In the same manner as in the comparative example, except that the epoxy compound was obtained, the (meth)acrylic acid sulfonic acid compound containing the radical represented by the above formula (101) was obtained. The gas chromatography of the obtained (meth)acrylic acid-acid vinegar compound obtained was carried out using a gas-like method as a solvent. As a result, the signal indicating that the epoxy group is present in the region of 6_5 to 7.5 ppm disappears, and the signal indicating the presence of the hydroxyl group in the region of 2.5 to 3.5 ppm appears. Further, s indicates that a signal of a region of 4 to 6 ppm in the presence of an acrylonitrile group appears. Thus, 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 thiol group-containing (meth) acrylate compound represented by the above formula (21A) is changed to the hydroxy group-containing (meth) group represented by the above formula (1〇1Β) obtained. A curable composition was obtained in the same manner as in the preparation of the composition of the composition of the acrylate according to the acrylate compound. (Comparative Example 3) In Comparative Example 3, a compound containing a trans group-containing (meth)acrylic acid represented by the following formula (1 〇 1C) was synthesized. [化49]

150186.doc -36·201113344 () Synthesis of a hydroxyl group-containing (meth) acrylate compound not represented by the above formula (101C) The epoxy compound represented by the above formula (5 1A) is changed to the above formula (5 1 c In addition to the above, the hydroxyl group-containing (meth) acrylate compound represented by the above formula (101C) was obtained in the same manner as in the comparative example. The 1H-NMR measurement of the obtained hydroxyl group-containing (meth) acrylate compound was carried out using a gas-like solvent as a solvent. As a result, the signal indicating that the epoxy group exists in the region of 6.5 to 7.5 ppm disappears, and the signal indicating the presence of the hydroxyl group in the region of 2.5 to 3.5 ppm appears. Further, a signal indicating a region of 4 to 6 ppm in the presence of the acrylonitrile group appears. Thus, 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 thiol-containing (meth) acrylate compound represented by the above formula (21A) is changed to the obtained thiol-containing acrylic acid represented by the above formula (101C). A curable composition was obtained in the same manner as in the preparation of the curable composition of (3) of Example 1 except for the ester compound. (Evaluation of Examples 1 to 3 and Comparative Examples 1 to 3) (1) Hygroscopicity Using an LED (Light Emitting Diode) Spot UV apparatus manufactured by HOYA Corporation, the obtained curable composition was used. The light irradiation intensity of 1500 mW/cm2 was irradiated with light of 375 nm for 5 seconds to harden the curable composition, and a film-like cured product of the curable composition (vertical 6 mm x width 6 mm x thickness 1 mm) was obtained. The obtained cured product was allowed to stand under the conditions of 8 (TC and relative humidity 85% 150186.doc -37-201113344 for 24 hours. The weight change of the cured product before and after the placement was determined by the method according to JIS K7209, thereby evaluating Hygroscopicity: The smaller the change in weight, the lower the hygroscopicity. (2) The transparent glass substrate on which the ITO electrode is provided on the upper surface is prepared, and the semiconductor wafer on which the gold bump electrode is provided on the lower surface is prepared. The obtained curable composition is applied to the 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 so 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 Azbil Corporation, and the curable composition layer was cured to obtain a bonded structure. The universal adhesion tester series 4000 manufactured by the company measures the shear strength of the obtained joined structure and evaluates the adhesion. The results are shown in Table 1 below. [Table 1] Hygroscopicity Weight change (%) Next force shear strength (N/cm2) Example 1 1.4 865 Example 2 1.3 840 Example 3 1.4 833 Comparative Example 1 3.8 521 Comparative Example 2 3.6 531 Comparative Example 3 3.9 522 (Example 4~ 12) Synthesis of a mercapto group-containing (meth) acrylate containing a (meth) acrylate compound having a hydrazine 150186.doc -38 - 201113344 group represented by the formula (31) of the following Table 2 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 (fluorenyl) acrylate compound was used. In 4 to 6, in the case of synthesizing the (meth) acrylate compound containing the thiol group (2), the acrylic acid was changed to methacrylic acid. In Examples 7 to 12, the synthesis example 1 was synthesized ( 1) In the case of the episulfide compound represented by the formula (61A), the epoxy compounds represented by the above formulas (71A) to (71C) are suitably used, that is, R3 and R4 in the formulae (71A) to (71C) are respectively positively stretched. An epoxy compound of propyl (n_C3H6) or n-type thiol (nC^Hio) instead of isophthalic acid Diglycidyl ether. (Examples 13 to 19) A curable composition having the composition shown in the following Table 3 was prepared. In Examples 13 to 19, the above formula (obtained in Example u) was suitably used. 21A) to (21C), a mercapto group-containing (meth) acrylate compound, the photopolymerization initiator, the filler, and the conductive particles described above (Example 20) (1) an episulfide compound When the episulfide compound represented by the formula (61A) of the formula (1) is synthesized and synthesized, the amount of potassium thiocyanate used is reduced to adjust the conversion ratio, and the epoxy compound represented by the above formula (51A) is obtained. (The mixture of the epoxy group-containing episulfide compound and the episulfide compound represented by the above formula (6) is shown. The conversion ratio of the epoxy group to the cyclic thio group in the static mixture (4) was 5 %. That is, the ratio of the number of epoxy groups to cyclothio groups in the obtained mixture X1 is 150186.doc -39- 201113344 (epoxy oxime: episulfide group) is 1:1. (2) Synthesis of a (meth) acrylate compound containing a mercapto group The above-mentioned mixture XI obtained by the above formula (61A) is changed to the above-mentioned mixture XI, and (2) The hydroxy group-containing (meth) acrylate compound represented by the above formula (101A) and the hydroxy group and thiol group represented by the following formula (22A) are obtained in the same manner as in the synthesis of the fluorenyl group-containing (meth) acrylate compound. A mixture (Y) of a (meth) acrylate compound and a thiol-containing (meth) acrylate compound represented by the above formula (21A). [化 50]

(3) Preparation of Curable Composition The thiol-containing (meth) acrylate compound represented by the above formula (21A) was changed to the above-mentioned mixture γ 获得 obtained, and the same as Example 1 (3) The hardening composition is obtained in the same manner as the hardening composition. (Example 21) (1) Synthesis of episulfide compound When the episulfide compound represented by the formula (61B) of the formula (1) of Example 2 was synthesized, the amount of potassium thiocyanate used was decreased, and the conversion ratio was adjusted to obtain the above formula ( The epoxy compound shown in 51B), the epoxy group-containing episulfide compound represented by the above formula (62B), and the mixture of the episulfide compound represented by the above formula (61B) are χ2. The conversion of the epoxy group to the cyclic thio group in the whole mixture of X2 obtained from 150186.doc -40·201113344 was 5%. 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 a mercapto group-containing (fluorenyl) acrylate compound The above-mentioned mixture X2 obtained by the above formula (61B) is changed to the above-obtained mixture X2, and (2) is taken in addition to the second embodiment. In the same manner as the synthesis of the mercapto-containing (fluorenyl) acrylate compound, the (meth)acrylic acid sulfonic acid compound represented by the above formula (101B) is obtained, which is represented by the following formula (22B). A mixture Y2 containing a hydroxyl group and a thiol group-containing (meth) acrylate compound and a thiol group-containing (meth) acrylate compound represented by the above formula (21B). [化 51]

SH

Preparation of OH (3) Curable Composition The thiol-containing (fluorenyl) acrylate compound represented by the above formula (21A) was changed to the above-obtained mixture Y2, and the same as in Example 1 (3). The hardening composition is obtained in the same manner as the hardening composition. (Example 22) (1) Synthesis of episulfide compound When the episulfide compound represented by the formula (61C) of the formula (1) of Example 3 was synthesized, the amount of potassium cyanate used in the reduction of 琉150186.doc -41 · 201113344 was adjusted and adjusted. The conversion ratio is obtained by obtaining an epoxy compound represented by the above formula (51C), an epoxy group-containing episulfide compound represented by the above formula (62C), and a mixture of the episulfide compound represented by the above formula (61C). The conversion ratio of the epoxy group to the episulfide group in the obtained mixture X3 as a whole was 5 〇 0 / 〇. That is, the ratio of the number of epoxy groups to the epoxy groups (epoxy group: episulfide group) in the obtained mixture X3 was 1:1. (2) Synthesis of a mercapto group-containing (fluorenyl) acrylate compound The above-mentioned mixture X3 represented by the above formula (61C) is changed to the obtained mixture X3, and (2) is taken in addition to the third embodiment. The hydroxy group-containing (meth) acrylate compound represented by the above formula (101C) and the hydroxy group represented by the following formula (22C) are obtained in the same manner as in the synthesis of the mercapto group-containing (meth) acrylate compound. And a mixture of a mercapto (meth) acrylate compound and a thiol-containing (meth) acrylate compound represented by the above formula (21C). [化52]

丨) ... (22C)

Preparation of the OH (3) curable composition The above-mentioned mixture γ3 obtained by changing the sulfhydryl group containing the sulfhydryl group shown in the above formula (21A) was used. (3) Preparation of the curable composition In the same manner, a hardenable combination of 150l86.doc - 42·201113344 was obtained. (Evaluation of Examples 4 to 22) With respect to the curable compositions of Examples 4 to 22, evaluations were carried out in the same manner as in Examples 1 to 3 and Comparative Examples 1 to 3. The results are shown in Tables 2 to 3 below. However, in Tables 2 to 3 below, the results of evaluation of hygroscopicity and adhesion indicate the results determined based on the following criteria. [Criteria for determining hygroscopicity] 〇〇: The weight change is less than 1.5% 〇: The weight change is 1.5°/◦ or more and less than 2.5% △: The weight change is 2·5〇/〇 or more and less than 3.5%. χ : The change in weight is 3.5% or more [Base of judgment of force] 〇〇: Shear strength is 800 N/cm2 or more 〇: Shear strength is 675 N/cm2 or more, less than 800 N/cm2 △: Shear strength 550 N/cm2 or more, less than 675 N/cm2 x: Shear strength is less than 550 N/cm2 150186.doc -43- 201113344 Example 12 XX X1-C5H10 II-C5H10 X zn XC/3 〇〇〇 〇Example 11 X I1-C5HIO II-C5H10 ffi Xfl ffi 00 〇〇〇〇1 Example 10 Κ I1-C5HIO n-CjHio /—N ____^ K 00 ffi C/J 〇〇〇〇Example 9 X n -C3H6 n-C3H6 ffi m ffi 00 〇〇〇〇 施 Example 8 XX n-C3H6 II-C3H6 Nw/ XC/) K m 〇〇〇〇 Example 7 ffi n-C3H6 II-C3H6 /—SWC/3 Ffi Xfl ! 00 〇〇Example 6 u ffi U (NK υ ch2 s—✓ ffi C/DKC/D 〇〇Example 5 K um ffi Ο ch2 ch2 S' s*·/ ffi CO ffi CO 〇〇Example 4 u ffi ο <NX u (N ffi u /—V rH Sp^ X ΚΠ ffi 〇ss & 2 x(式) N CN N Hygroscopic weight change ^ V ^ ^ ^ mw 7 ^ ^ <Λ, Q ^ 喊乐!:命150186.doc • 44· 201113344 cn Example 22 Mixture Y3 (101C)(2 2C)(21C) 〇κη 〇〇〇 Example 21 Mixture Y2(101B)(2 2B)(21B) 1 〇ir> ο 〇〇 Example 20 Mixture Y1(101A)(2 2A)( 21A) 〇in Ο 〇〇 Example 19 (21C) 〇ο CN 〇〇〇〇Example 18 (2 IB) 〇ο CNI 〇〇〇〇Example 17 (2 ΙΑ) 〇1—Η ο <N 〇 〇〇〇Example 16 (21A) 1 _ 〇in ο 〇〇 Example 15 (2 ΙΑ) _1 〇Ο 〇〇 Example 14 (2 ΙΑ) _1 〇ΓΊ 〇〇 Example 13 (21Α) _ί 〇〇〇 1 S Φ1 *4〇φ! φ| Umbrella 伞 Umbrella hygroscopicity change ♦ V? Photopolymerization initiator A photopolymerization initiator Β Photopolymerization initiator c cerium oxide alumina conductive particles collapse ( Tong BW Umbrella) 150186.doc -45- 201113344 [Simplified Schematic Description] FIG. 1 is a schematic representation of an embodiment of the present invention. Connection structure comprising a curable composition containing it has a front sectional view of a body of the mercapto group of (meth) acrylate compound made. [Description of main component symbols] 1 Connection structure 2 First connection target member 2a Upper surface 2b > 3b Electrode 3 Second connection target member 3a Lower surface 4 Connection part 5 Conductive particle 150186.doc -46-

Claims (1)

201113344 VII. Scope of application: 1. A curable composition containing (+)', 匕3 § a sulfhydryl (meth) acrylate compound, and an active energy ray polymerization initiator. 2. The curable composition according to item 1, wherein the (meth)acrylic acid s-containing compound having a thiol group has a mercapto-containing (fluorenyl)acrylic acid S having a structure represented by the following formula (31). Compound: [Chemical 1] 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 a compound of the following formulas (11) to (13). Any of the groups shown in the above formula (31), wherein both of the groups 21 and 22 represent a thiol group or Z1 represents a thiol group and Z2 represents a hydroxy group; [Chemical 3] Formula (12) 150186.doc 201113344 [Chemical 4] Formula (13) 3. 4. The curable composition of claim 2, wherein the 21 and 22 of the above formula (31) are both fluorenyl groups. The sclerosing composition of claim 2, which is a thiol-containing compound having a structure represented by the above formula (31) and having a structure represented by the above formula (31). A thiol-containing thiol I, fluorenyl acrylate compound having the structure represented by the following formula (1): [Chemical 5] In the above formula (1), RMR2 represents hydrogen or a methyl group, respectively, and χ represents a group represented by any one of the above formulae (Π) to (13). A connection structure including an i-th connection object member, a second connection object member, and a connection portion that connects the first and second connection object members; wherein the connection portion is made by requesting items 1-4 to 4 Any of the curable compositions is formed by hardening. A fluorenyl-containing (fluorenyl) acrylate compound having a structure represented by the following formula (31): 150186.doc • 2-201113344 [Chem. 6] In the above formula (31), R1 and R2 each bear hydrogen or a methyl group, and each of them represents an alkylene group having a carbon number of 1 to 5, and X represents the following formula (11) to (13). Any of the groups shown in any one of the above formulas (31), wherein both Z1 and Z2 represent a fluorenyl group, or Z1 represents a sulfhydryl group and Z2 represents a thiol group; Equation (11) [Chem. 8] Equation (12) [Chemistry 9] The fluorenyl-containing (fluorenyl) acrylate compound of the above formula (31), wherein Z1 and Z2 in the above formula (31) are both fluorenyl groups. A thiol-containing (meth) acrylate compound having a structure of <F, 〆 & formula (1), which has a mercapto group-containing (fluorenyl) acrylate compound 150186.doc 201113344 Object: [Chemical] R1 SH SH R2 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). 150186.doc 4-