KR20110079612A

KR20110079612A - Episulfide compound, episulfide compound-containing mixture, method for producing episulfide compound-containing mixture, curable composition and connection structure

Info

Publication number: KR20110079612A
Application number: KR1020117004390A
Authority: KR
Inventors: 다까시 구보따
Original assignee: 세키스이가가쿠 고교가부시키가이샤
Priority date: 2008-09-25
Filing date: 2009-09-24
Publication date: 2011-07-07
Also published as: TWI491601B; CN102164907A; CN105175727A; KR101619558B1; JP2011105942A; JP5530392B2; TW201020243A; JP4730695B2; WO2010035459A1; JPWO2010035459A1; JP4729128B2; JP2011173901A

Abstract

The present invention provides an episulfide compound that can be cured quickly at low temperatures, can be efficiently connected to the connection object member when used for connection of the connection object member, and can suppress the generation of voids after connection. The episulfide compound of the present invention has a structure represented by the following formula (1-1), (2-1) or (3).
<Formula 1-1>

(In Formulas 1-1, 2-1, or 3, R1 and R2, R51 and R52, and R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms, and 2 to 4 of 4 groups of R3 to R6). Group represents hydrogen, another group represents a group containing episulfide, 4-6 groups out of 6 groups of R53 to R58 represent hydrogen, another group represents group comprising an episulfide group, and 8 groups of R103 to R110 6-8 groups in the group represent hydrogen and other groups represent groups comprising episulfide groups)

Description

EPISULFIDE COMPOUND, EPISULFIDE COMPOUND-CONTAINING MIXTURE, METHOD FOR PRODUCING EPISULFIDE COMPOUND-CONTAINING MIXTURE, CURABLE COMPOSITION AND CONNECTION STRUCTURE}

The present invention can be quickly cured at a low temperature, the episulfide compound capable of effectively connecting the connection object member when used for the connection of the connection object member, and suppressing the generation of voids after the connection, and the epi The present invention relates to an episulfide compound-containing mixture containing a sulfide compound, a method for producing the episulfide compound-containing mixture, a curable composition, and a bonded structure.

Anisotropic conductive materials, such as an anisotropic conductive paste, an anisotropic conductive ink, an anisotropic conductive adhesive agent, an anisotropic conductive film, or an anisotropic conductive sheet, are widely known.

The anisotropic conductive material is used for connecting an IC chip and a flexible printed circuit board, or for connecting a circuit board having an IC chip and an ITO electrode. For example, after arrange | positioning an anisotropic conductive material between the electrode of an IC chip and the electrode of a circuit board, these electrodes can be connected by heating and pressurizing.

As an example of the anisotropic conductive material, Patent Document 1 discloses an anisotropic conductive adhesive film containing a thermosetting insulating adhesive, conductive particles, an imidazole series latent curing agent, and an amine latent curing agent. Patent Document 1 describes that the connection reliability is excellent even when the anisotropic conductive adhesive film is cured at a relatively low temperature.

Japanese Patent Publication No. 9-115335

In recent years, in order to connect between the electrodes of an electronic component efficiently, the heating temperature required for connection is reduced and the pressurization time is shortened. In addition, since electronic components are likely to deteriorate by heating, it is strongly required to lower the heating temperature.

In the anisotropic conductive adhesive film of patent document 1, the heating temperature required for initiating hardening is comparatively low. However, in this anisotropic conductive adhesive film, hardening reaction may not fully advance at low temperature. Therefore, in order to connect between the circuit board and the electrode of an electronic component using an anisotropic conductive adhesive film, you may need to raise heating temperature or heat for a long time. Therefore, there may be a case where the electrodes cannot be connected efficiently.

Further, in recent years, miniaturization of electrodes formed on circuit boards and the like is progressing. That is, L / S which shows the dimension L of the width direction of the line in which the electrode is formed, and the dimension S of the width direction of the space in which the electrode is not formed is becoming smaller. When the circuit board on which such a fine electrode is formed is connected by said anisotropic conductive adhesive film, since the hardening rate of an anisotropic conductive adhesive film is slow, a space | gap may arise in the space between electrodes.

An object of the present invention is an episulfide compound which can be cured rapidly at a low temperature, can be efficiently connected to the connection object member when used for connection of a connection object member, and can suppress the generation of voids after the connection, and It is providing the episulfide compound containing mixture containing the said episulfide compound, the manufacturing method of the said episulfide compound containing mixture, a curable composition, and a bonded structure.

According to a broad aspect of the present invention, an episulfide compound having a structure represented by the following Chemical Formula 1-1, 2-1 or 3 is provided.

(In Formula 1-1, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen, and R3, R4, R5 and A group other than hydrogen in R6 represents a group represented by the following Chemical Formula 4)

(In Formula 2-1, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 each represent hydrogen, and R53, A group other than hydrogen among R54, R55, R56, R57, and R58 represents a group represented by Formula 5 below)

(In Formula 3, R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms, and 6 to 8 groups of 8 groups of R103, R104, R105, R106, R107, R108, R109 and R110 represent hydrogen, A group other than hydrogen among R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 represents a group represented by the following formula (6):

(In Formula 4, R7 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 5, R59 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 6, R 111 represents an alkylene group having 1 to 5 carbon atoms.)

In certain specific aspects of the episulfide compound according to the present invention, the episulfide compound has a structure represented by the following formula (1) or (2).

(In Formula 1, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen, and among R3, R4, R5 and R6 A group other than hydrogen represents a group represented by the following formula (4)

(In Formula 2, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms, 4 to 6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 each represent hydrogen, and R53, R54, R55, R56, R57 and R58 of the non-hydrogen group represents a group represented by the formula (5)

(In Formula 4, R7 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 5, R59 represents an alkylene group having 1 to 5 carbon atoms.)

In another specific aspect of the episulfide compound according to the present invention, the structure represented by Formula 1 or 2 is a structure represented by Formula 1A or 2A.

(In Formula 1A, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms.)

(In Formula 2A, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms.)

The episulfide compound-containing mixture according to the present invention contains the episulfide compound of the present invention and an epoxy compound represented by the following general formulas (11-1), (12-1) or (13).

(In Formula 11-1, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R13, R14, R15, and R16 represent hydrogen, and R13, R14, R15 and A group other than hydrogen in R16 represents a group represented by the following Formula 14)

(In Formula 12-1, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 represent hydrogen, and R63, A group other than hydrogen among R64, R65, R66, R67, and R68 represents a group represented by the following Formula 15)

(In Formula 13, R121 and R122 each represent an alkylene group having 1 to 5 carbon atoms, and 6 to 8 groups of 8 groups of R123, R124, R125, R126, R127, R128, R129, and R130 each represent hydrogen, A group other than hydrogen among R123, R124, R125, R126, R127, R128, R129, and R130 represents a group represented by the following Chemical Formula 16)

(In Formula 14, R17 represents an alkylene group having 1 to 5 carbon atoms.)

&Lt; Formula 15 >

(In Formula 15, R69 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 16, R131 represents an alkylene group having 1 to 5 carbon atoms.)

In certain specific aspects of the episulfide compound-containing mixture according to the present invention, the epoxy compound is an epoxy compound represented by the following formula (11) or (12).

(In Formula 11, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms, and 2 to 4 groups of 4 groups of R13, R14, R15, and R16 represent hydrogen, and among R13, R14, R15, and R16. A group other than hydrogen represents a group represented by the following formula (14))

(In Formula 12, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 each represent hydrogen, and R63, R64, A group other than hydrogen among R65, R66, R67, and R68 represents a group represented by the following Formula 15)

(In Formula 14, R17 represents an alkylene group having 1 to 5 carbon atoms.)

&Lt; Formula 15 >

(In Formula 15, R69 represents an alkylene group having 1 to 5 carbon atoms.)

In another specific aspect of the episulfide compound-containing mixture according to the present invention, the structure represented by Formula 11 or 12 is a structure represented by Formula 11A or 12A.

(In Formula 11A, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms.)

(In Formula 12A, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms.)

In the method for producing an episulfide compound-containing mixture according to the present invention, an epoxy compound represented by Formula 11-1, 12-1 or 13 or a solution containing the epoxy compound is added to a first solution containing thiocyanate. After addition continuously or intermittently, some epoxy groups of the epoxy compound are converted to episulfide groups by further or continuously adding a second solution comprising thiocyanate.

In a specific aspect of the method for producing an episulfide compound-containing mixture according to the present invention, a solution containing the epoxy compound or the epoxy compound, and the solution containing the epoxy compound represented by the formula (11) or (12) or the epoxy compound This is used.

The curable composition which concerns on this invention contains the episulfide compound of this invention, and a hardening | curing agent.

Or the curable composition which concerns on this invention contains the episulfide compound containing mixture of this invention, and a hardening | curing agent. This curable composition also contains the said episulfide compound in the said episulfide compound containing mixture.

In certain specific aspects of the curable composition according to the present invention, the photocurable compound and the photopolymerization initiator are further contained.

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

The connection structure which concerns on this invention is equipped with the 1st connection object member, the 2nd connection object member, and the connection part which connects the said 1st, 2nd connection object member, The said connection part is made of the curable composition of this invention. Formed.

In the specific aspect of the bonded structure which concerns on this invention, the said curable composition contains electroconductive particle, and the said 1st, 2nd connection object member is electrically connected by the said electroconductive particle.

Since the episulfide compound according to the present invention has a structure represented by the formula (1-1), (2-1) or (3), it can be quickly cured at low temperature.

When the episulfide compound according to the present invention has a structure represented by the formula (1) or (2), it can be cured more quickly at low temperature.

The episulfide compound-containing mixture according to the present invention can be cured rapidly at low temperature because it contains the episulfide compound having the structure represented by the above formula (1-1) or (2-1).

When the episulfide compound-containing mixture according to the present invention has a structure represented by the formula (1) or (2), it can be cured more quickly at low temperature.

Moreover, the said connection object member can be efficiently connected by using the episulfide compound which concerns on this invention or the episulfide compound containing mixture which concerns on this invention for connection of a connection object member. Moreover, it can suppress that a space | gap arises after connection. Even if the connection object member which has an unevenness | corrugation on the surface is connected, it can suppress that a space | gap generate | occur | produces.

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

Hereinafter, the present invention will be described in detail.

(Episulfide Compound)

The episulfide compound according to the present invention has a structure represented by the following formula (1-1), (2-1) or (3). The bonding site of the six groups bonded to the benzene ring in the following formula (1-1) is not particularly limited. The binding site of the eight groups which are bonded to the naphthalene ring in the following formula (2-1) is not particularly limited.

In said Formula (1-1), R1 and R2 represent a C1-C5 alkylene group, respectively. Two to four groups out of four groups of R 3, R 4, R 5 and R 6 represent hydrogen. A group other than hydrogen among R 3, R 4, R 5 and R 6 represents a group represented by the following formula (4). All four groups of R 3, R 4, R 5 and R 6 may be hydrogen. One or two of four groups of R3, R4, R5 and R6 is a group represented by the following formula (4), and among the four groups of R3, R4, R5 and R6, a group other than the group represented by the following formula (4) may be hydrogen have.

In said Formula (2-1), R51 and R52 represent a C1-C5 alkylene group, respectively. Four to six of the six groups of R53, R54, R55, R56, R57 and R58 represent hydrogen. A group other than hydrogen among R53, R54, R55, R56, R57, and R58 represents a group represented by the following formula (5). The six groups of R53, R54, R55, R56, R57 and R58 may all be hydrogen. One or two of six groups of R53, R54, R55, R56, R57, and R58 are groups represented by the following Chemical Formula 5, and R53, R54, R55, R56, R57, and R58 are not groups represented by the following Chemical Formula 5 The group may be hydrogen.

In said Formula (3), R101 and R102 represent a C1-C5 alkylene group, respectively. Six to eight of the eight groups of R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 represent hydrogen. A group other than hydrogen among R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 represents a group represented by the following formula (6). Eight groups of R103, R104, R105, R106, R107, R108, R109 and R110 may all be hydrogen. One or two of eight groups of R103, R104, R105, R106, R107, R108, R109, and R110 are represented by the following formula (6), and among R103, R104, R105, R106, R107, R108, R109, and R110 A group other than the group represented by the following formula (6) may be hydrogen.

(In Formula 4, R7 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 5, R59 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 6, R 111 represents an alkylene group having 1 to 5 carbon atoms.)

From the viewpoint of curing more rapidly at low temperature, the episulfide compound according to the present invention preferably has a structure represented by the following formula (1), (2) or (3). From the viewpoint of curing at a lower temperature even more rapidly, the episulfide compound according to the present invention preferably has a structure represented by the following formula (1) or (2).

(In Formula 1, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen, and among R3, R4, R5 and R6 A group other than hydrogen represents a group represented by Formula 4)

(In Formula 2, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms, 4 to 6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 each represent hydrogen, and R53, R54, R55, R56, R57 and R58 of the non-hydrogen group represents a group represented by the formula (5))

The episulfide compounds having the structures represented by the above formulas (1-1), (2-1) or (3) and the above formulas (1) or (2) all have at least two episulfide groups. Moreover, the group which has an episulfide group is couple | bonded with a benzene ring, a naphthalene ring, or an anthracene ring. Since it has such a structure, a mixture can be hardened rapidly at low temperature by heating the mixture which added the hardening | curing agent, for example to an episulfide compound.

An episulfide compound having a structure represented by Formula 1-1, 2-1 or 3 is more reactive than a compound in which the episulfide group in Formula 1-1, 2-1 or 3 is an epoxy group. The episulfide compound having the structure represented by the above formula (1) or (2) is more reactive than the compound in which the episulfide group in the above formula (1) or (2) is an epoxy group. This is because the episulfide group is more easily ring-opened than the epoxy group and has a higher reactivity. The episulfide compound having the structure represented by Formula 1-1, 2-1 or 3, and the episulfide compound having the structure represented by Formula 1 or 2 may be cured rapidly at low temperature because of its high reactivity. .

R1 and R2 in Formulas 1-1 and 1, R51 and R52 in Formulas 2-1 and 2, R101 and R102 in Formula 3, R7 in Formula 4, R59 in Formula 5, and R111 in Formula 6 Are all alkylene groups having 1 to 5 carbon atoms. When carbon number of the said alkylene group exceeds 5, the hardening rate of the said episulfide compound will fall easily.

R1 and R2 in Formulas 1-1 and 1, R51 and R52 in Formulas 2-1 and 2, R101 and R102 in Formula 3, R7 in Formula 4, R59 in Formula 5, and R111 in Formula 6 It is preferable that it is a C1-C3 alkylene group, respectively, and it is more preferable that it is a methylene group. The alkylene group may be an alkylene group having a straight chain structure, or may be an alkylene group having a branched structure.

It is preferable that the structure represented by the said Formula (1) is a structure represented by following formula (1A). The episulfide compound having a structure represented by the following formula (1A) is excellent in curability.

As for the structure represented by the said Formula (1), it is more preferable that it is a structure represented by following formula (1B). The episulfide compound having a structure represented by the following formula (1B) is more excellent in curability.

It is preferable that the structure represented by the said Formula (2) is a structure represented by following formula (2A). The episulfide compound having a structure represented by the following formula (2A) is excellent in curability.

As for the structure represented by the said Formula (2), it is more preferable that it is a structure represented by following formula (2B). The episulfide compound having a structure represented by the following formula (2B) is more excellent in curability.

It is preferable that the structure represented by the said Formula (3) is a structure represented by following formula (3A). The episulfide compound having a structure represented by the following formula (3A) is excellent in curability.

(In Formula 3A, R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms.)

As for the structure represented by the said General formula (3), it is more preferable that it is a structure represented by following General formula (3B). The episulfide compound having a structure represented by the following formula (3B) is more excellent in curability.

(Episulfide compound-containing mixture)

The episulfide compound-containing mixture according to the present invention contains an episulfide compound represented by Formula 1-1, 2-1 or 3 and an epoxy compound represented by Formula 11-1, 12-1 or 13 below. . The bonding site of the six groups which are bonded to the benzene ring in the formula (11-1) is not particularly limited. The binding site of the eight groups which are bonded to the naphthalene ring in the following formula (12-1) is not particularly limited.

In said Formula (11-1), R11 and R12 represent a C1-C5 alkylene group, respectively. Two to four of the four groups of R 13, R 14, R 15 and R 16 represent hydrogen. A group other than hydrogen among R13, R14, R15, and R16 represents a group represented by the following formula (14). All four groups of R13, R14, R15 and R16 may be hydrogen. One or two of four groups of R13, R14, R15, and R16 is a group represented by the following formula (14), and among the four groups of R13, R14, R15, and R16, a group other than the group represented by the following formula (14) may be hydrogen have.

In said Formula (12-1), R61 and R62 represent a C1-C5 alkylene group, respectively. Four to six groups out of six groups of R63, R64, R65, R66, R67 and R68 represent hydrogen. A group other than hydrogen among R63, R64, R65, R66, R67, and R68 represents a group represented by the following formula (15). The six groups of R63, R64, R65, R66, R67 and R68 may all be hydrogen. One or two of six groups of R63, R64, R65, R66, R67, and R68 is a group represented by the following formula (15), and among the six groups of R63, R64, R65, R66, R67, and R68, A group other than the group represented may be hydrogen.

In said Formula (13), R121 and R122 represent a C1-C5 alkylene group, respectively. Six to eight of the eight groups of R 123, R 124, R 125, R 126, R 127, R 128, R 129 and R 130 represent hydrogen. A group other than hydrogen in R123, R124, R125, R126, R127, R128, R129, and R130 represents a group represented by the following formula (16). Eight groups of R123, R124, R125, R126, R127, R128, R129 and R130 may all be hydrogen. One or two of eight groups of R123, R124, R125, R126, R127, R128, R129, and R130 are represented by the following formula (16), and among eight groups of R123, R124, R125, R126, R127, and R128 A group other than the group represented by the following formula (16) may be hydrogen.

(In Formula 14, R17 represents an alkylene group having 1 to 5 carbon atoms.)

&Lt; Formula 15 >

(In Formula 15, R69 represents an alkylene group having 1 to 5 carbon atoms.)

(In Formula 16, R131 represents an alkylene group having 1 to 5 carbon atoms.)

In view of the faster curing at low temperature, the episulfide compound-containing mixture according to the present invention is represented by the compound represented by the formula (1), (2) or (3), (11), (12) or (13) It is preferable to contain the epoxy compound which becomes. From the viewpoint of curing at a lower temperature even more rapidly, the episulfide compound-containing mixture according to the present invention preferably contains a compound represented by the above formula (1) or (2) and an epoxy compound represented by the following formula (11) or (12).

(In Formula 11, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms, and 2 to 4 groups of 4 groups of R13, R14, R15, and R16 represent hydrogen, and among R13, R14, R15, and R16. A group other than hydrogen represents a group represented by Formula 14)

(In Formula 12, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 each represent hydrogen, and R63, R64, A group other than hydrogen among R65, R66, R67, and R68 represents a group represented by Formula 15)

R11 and R12 in Formulas 11-1 and 11, R61 and R62 in Formulas 12-1 and 12, R121 and R122 in Formula 13, R17 in Formula 14, R69 in Formula 15, and R131 in Formula 16 Are all alkylene groups having 1 to 5 carbon atoms. When carbon number of the said alkylene group exceeds 5, the hardening rate of the said episulfide compound containing mixture will fall easily.

R11 and R12 in Formulas 11-1 and 11, R61 and R62 in Formulas 12-1 and 12, R121 and R122 in Formula 13, R17 in Formula 14, R69 in Formula 15, and R131 in Formula 16 It is preferable that it is a C1-C3 alkylene group, respectively, and it is more preferable that it is a methylene group. The alkylene group may be an alkylene group having a straight chain structure, or may be an alkylene group having a branched structure.

It is preferable that the structure represented by said 11 is a structure represented by following formula (11A). Epoxy compounds having a structure represented by the following formula (11A) are commercially available and can be easily obtained.

As for the structure represented by the said Formula (11), it is more preferable that it is a structure represented by following formula (11B). The epoxy compound which has a structure represented by following formula (11B) is resorcinol diglycidyl ether. Resorcinol diglycidyl ether is commercially available and can be obtained easily.

It is preferable that the structure represented by the said Formula (12) is a structure represented by following formula (12A). The epoxy compound which has a structure represented by following formula (12A) can be obtained easily.

As for the structure represented by the said Formula (12), it is more preferable that it is a structure represented by following formula (12B). The epoxy compound which has a structure represented by following formula (12B) can be obtained easily.

It is preferable that the structure represented by the said Formula (13) is a structure represented by following formula (13A). Epoxy compounds having a structure represented by the following formula (13A) can be easily obtained.

(In Formula 13A, R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms.)

As for the structure represented by the said Formula (13), it is more preferable that it is a structure represented by following formula (13B). Epoxy compounds having a structure represented by the following formula (13B) can be easily obtained.

The episulfide compound-containing mixture according to the present invention contains 10 to 99.9% by weight of the episulfide compound having a structure represented by the above formulas (1-1), (2-1) or (3), It is preferable to contain 90 to 0.01 weight% of the epoxy compound represented by 1 or 13. The episulfide compound-containing mixture according to the present invention contains 80 to 99.9% by weight of the episulfide compound having a structure represented by the above formulas (1-1), (2-1) or (3), It is more preferable to contain 0.1 to 20 weight% of the epoxy compound represented by 1 or 13.

The episulfide compound-containing mixture according to the present invention contains 10 to 99.9% by weight of the episulfide compound having the structure represented by the above formula (1) or (2), and 90 to 0.1 of the epoxy compound represented by the above formula (11) or (12). It is preferable to contain by weight%. The episulfide compound-containing mixture according to the present invention contains 80 to 99.9% by weight of the episulfide compound having the structure represented by the above formula (1) or (2), and contains 0.1 to 20 epoxy compounds represented by the above formula (11) or (12). It is more preferable to contain weight%.

If the content of the episulfide compound having the structure represented by the formula (1-1), 2-1 or 3 and the episulfide compound having the structure represented by the formula (1) or (2) is too small, the episulfide compound is contained. In some cases, the curing rate of the mixture may not be sufficiently high. If the content of the episulfide compound having the structure represented by the above formula (11-1), 12-1 or 13 and the episulfide compound having the structure represented by the above formula (1) or (2) is too large, the episulfide compound-containing mixture The viscosity of the compound may be too high or the episulfide compound-containing mixture may become a solid.

(Method for producing episulfide compound and method for producing episulfide compound-containing mixture)

The manufacturing method of the said episulfide compound and the manufacturing method of the said episulfide compound containing mixture are not specifically limited. As this manufacturing method, the epoxy compound represented by the said General formula (11-1, 12-1 or 13) or the said Formula (11 or 12) is prepared, for example, and all or some epoxy groups of the said epoxy compound are converted into an episulfide group. A manufacturing method is mentioned.

The method for producing the episulfide compound and the method for producing the episulfide compound-containing mixture include an epoxy compound or the epoxy represented by Formula 11-1, 12-1 or 13 in a first solution containing thiocyanate Preference is given to a method in which the solution comprising the compound is added continuously or intermittently, followed by further addition of the second solution comprising thiocyanate continuously or intermittently. By the said method, all or some epoxy groups of the said epoxy compound can be converted into an episulfide group. It is preferable that the solution containing the said epoxy compound or the said epoxy compound is a solution containing the epoxy compound represented by the said Formula (1) or (2), or the said epoxy compound.

As a result of converting all the epoxy groups to episulfide groups, an episulfide compound having a structure represented by Formula 1-1, 2-1 or 3 can be obtained. Moreover, the episulfide compound which has a structure represented by the said Formula (1) or (2) can also be obtained. As a result of conversion of some epoxy groups to episulfide groups, episulfide compounds having a structure represented by Formula 1-1, 2-1 or 3 and an epoxy compound represented by Formula 11-1, 12-1 or 13 The episulfide compound containing mixture containing can be obtained. In addition, an episulfide compound-containing mixture containing an episulfide compound having a structure represented by Formula 1 or 2 and an epoxy compound represented by Formula 11 or 12 may be obtained.

The said episulfide compound and the said episulfide compound containing mixture can be manufactured as follows specifically ,.

A solvent, water and thiocyanate are added to a vessel equipped with a stirrer, a cooler and a thermometer, and the thiocyanate is dissolved to prepare a first solution in the vessel. Methanol or ethanol etc. are mentioned as a solvent. Examples of thiocyanate include ammonium thiocyanate, potassium thiocyanate or sodium thiocyanate.

The concentration of thiocyanate in the first solution is preferably in the range of 0.001 to 0.2 g / mL, more preferably in the range of 0.005 to 0.1 g / mL. When the concentration of thiocyanate is too high, an epoxy compound may superpose | polymerize. When the thiocyanate concentration is too low, an epoxy group may not be converted into an episulfide group.

In addition, apart from the first solution, an epoxy compound having a structure represented by Formula 11-1, 12-1, 13, 11, or 12 or a solution containing the epoxy compound is prepared.

Subsequently, an epoxy compound having a structure represented by Formula 11-1, 12-1, 13, 11 or 12 or a solution containing the epoxy compound is added continuously or intermittently in the first solution. It is preferable that the temperature of the 1st solution at this time exists in the range of 15-30 degreeC. After addition of the epoxy compound, it is preferable to stir for 0.5 to 12 hours. You may add the said epoxy compound or the solution containing the said epoxy compound in several steps. For example, after adding some of the epoxy compound or the solution containing the epoxy compound, stirring for at least 0.5 hours, and then further adding the remaining epoxy compound or the solution containing the epoxy compound to 0.5 to 12 It can also be stirred for hours. When using the solution containing the said epoxy compound, the density | concentration of the epoxy compound of the said solution is not specifically limited.

The addition rate of the epoxy compound or the solution containing the epoxy compound in the first solution is preferably in the range of 1 to 10 mL / min, more preferably in the range of 2 to 8 mL / min. When the addition rate of the said epoxy compound or the solution containing the said epoxy compound is too fast, an epoxy compound may superpose | polymerize. When the addition rate of the said epoxy compound or the solution containing the said epoxy compound is too slow, the production efficiency of an episulfide compound may fall.

In the mixed solution in which the epoxy compound or the solution containing the epoxy compound is added to the first solution, the concentration of the epoxy compound is preferably in the range of 0.05 to 0.8 g / mL, and is in the range of 0.1 to 0.5 g / mL. It is more preferable to stay inside. If the concentration of the epoxy compound is too high, the epoxy compound may be polymerized.

Subsequently, a second solution containing a solvent, water and thiocyanate is further continuously or intermittently added to the mixed solution in which the epoxy compound or the solution containing the epoxy compound is added to the first solution. After addition of the second solution, it is preferred to stir for 0.5 to 12 hours. Moreover, after addition of the said 2nd solution, it is preferable to stir in the range of 15-60 degreeC. The second solution may be added in a plurality of steps. For example, after the addition of some of the second solution, the mixture may be stirred for at least 0.5 hours, and then the remaining second solution may be further added, followed by stirring for 0.5 to 12 hours.

The concentration of thiocyanate in the second solution is preferably in the range of 0.001 to 0.7 g / mL, more preferably in the range of 0.005 to 0.5 g / mL. When the concentration of thiocyanate is too high, an epoxy compound may superpose | polymerize. When the thiocyanate concentration is too low, an epoxy group may not be converted into an episulfide group.

The addition rate of the second solution into the mixed solution is preferably in the range of 1 to 10 mL / min, more preferably in the range of 2 to 8 mL / min. When the addition rate of the said 2nd solution is too fast, an epoxy compound may superpose | polymerize. When the addition rate of the said 2nd solution is too slow, the production | generation efficiency of an episulfide compound may fall.

After the second solution is added to the mixed solution to which the epoxy compound is added in the first solution, it is preferable to remove water, a solvent or an unreacted thiocyanate. As a method of removing water, a solvent, or an unreacted thiocyanate, a conventionally known method is used.

The first solution or the second solution may contain a catalyst such as palladium metal particles or titanium oxide. The conversion rate of the episulfide group can be adjusted according to the use of the solution containing the catalyst. Moreover, since an epoxy group can be converted into an episulfide group in low temperature environment, the polymerization reaction of an epoxy compound can be suppressed. It is preferable that the density | concentration of the catalyst of the said 1st solution or the density | concentration of the catalyst of a said 2nd solution exists in the range of 0.05-1.0 g / mL.

As mentioned above, all or some epoxy groups of the said epoxy compound can be converted into an episulfide group. As a result, an episulfide compound or an episulfide compound-containing mixture can be obtained. Specifically, for example, an episulfide compound containing 100% by weight of an episulfide compound having a structure represented by Formula 1-1, 2-1, 3, 1 or 2 can be obtained. Further, for example, 10 to 99.9% by weight or 10 to 50% by weight of an episulfide compound having a structure represented by Formula 1-1, 2-1, 3, 1 or 2 is contained, and Formula 11-1 , An episulfide compound-containing mixture containing 90 to 0.1% by weight or 90 to 50% by weight of the epoxy compound represented by 12-1, 13, 11 or 12 can be obtained.

(Curable composition)

The curable composition which concerns on this invention contains the episulfide compound of this invention, and a hardening | curing agent. Or the curable composition which concerns on this invention contains the episulfide compound containing mixture of this invention, and a hardening | curing agent. That is, the curable composition which concerns on this invention contains the episulfide compound or the episulfide compound containing mixture of this invention, and a hardening | curing agent. Only 1 type may be used for hardening | curing agents, and 2 or more types may be used together.

The curable composition which concerns on this invention contains at least 1 sort (s) of the said episulfide compound. Alternatively, the curable composition according to the present invention contains at least one episulfide compound-containing mixture. Alternatively, the curable composition according to the present invention contains at least one episulfide compound and at least one episulfide compound-containing mixture. Therefore, 2 or more types of the said episulfide compound may be used together as curable resin, 2 or more types of the said episulfide compound containing mixture may be used together, and the said episulfide compound and the said episulfide compound containing mixture This may be used in combination.

The said hardening | curing agent is not specifically limited. Examples of the curing agent include an imidazole curing agent, an amine curing agent, a phenol curing agent, a polythiol curing agent or an acid anhydride. Especially, an imidazole hardening | curing agent, a polythiol hardening | curing agent, or an amine hardening | curing agent is preferable because a curable composition can be hardened more quickly at low temperature. Moreover, since storage stability can be improved when the said episulfide compound, the said episulfide compound containing mixture, and the said hardening | curing agent are mixed, latent hardening | curing agent is preferable. The latent curing agent is preferably a latent imidazole curing agent, a latent polythiol curing agent or a latent amine curing agent. Only 1 type may be used for these hardening | curing agents and 2 or more types may be used together. In addition, the said hardening | curing agent may be coat | covered with high molecular materials, such as a polyurethane resin or a polyester resin.

Although it does not specifically limit as said imidazole hardening | curing agent, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-phenyl Imidazolium trimellitate, 2,4-diamino-6- [2'-methylimidazolyl- (1 ')]-ethyl-s-triazine or 2,4-diamino-6- [2' -Methyl imidazolyl- (1 ')]-ethyl-s-triazine isocyanuric acid addition product etc. are mentioned.

Although it does not specifically limit as said polythiol hardening | curing agent, Trimethylol propane tris-3- mercapto propionate, pentaerythritol tetrakis-3 mercapto propionate, or dipentaerythritol hexa-3- mercapto propionate Etc. can be mentioned.

Although it does not specifically limit as said amine hardening | curing agent, Hexamethylenediamine, octamethylenediamine, decamethylenediamine, 3,9-bis (3-aminopropyl) 2,4,8,10- tetraspiro [5.5] undecane, bis ( 4-aminocyclohexyl) methane, metaphenylenediamine, diaminodiphenyl sulfone, etc. are mentioned.

Among the above curing agents, polythiol compounds or acid anhydrides are preferably used. More preferably, a polythiol compound is used because the curing speed of the curable composition can be made faster.

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

Content of the said hardening | curing agent is not specifically limited. 100 parts by weight of the episulfide compound or the episulfide compound-containing mixture (when the epoxy compound is not included, 100 parts by weight of the episulfide compound, and when the epoxy compound is included, contains the episulfide compound. 100 parts by weight of the mixture), the curing agent is preferably contained within the range of 1 to 40 parts by weight. If content of the said hardening | curing agent is less than 1 weight part, a curable composition may not fully harden. When content of the said hardening agent exceeds 40 weight part, the heat resistance of the hardened | cured material of a curable composition may fall. The minimum with more preferable content of the said hardening | curing agent with respect to 100 weight part of said episulfide compound or the said episulfide compound containing mixture is 30 weight part, A more preferable minimum is 45 weight part, The especially preferable upper limit is 100 weight part, The most preferable upper limit Is 75 parts by weight. When there is too little content of a hardening | curing agent, it becomes difficult to fully harden a curable composition. When there is too much content of a hardening | curing agent, the excess hardening | curing agent which does not participate in hardening may remain after hardening.

Moreover, when the said hardening | curing agent is an imidazole hardening | curing agent or a phenol hardening | curing agent, it is contained in the range of 1-15 weight part with respect to 100 weight part of said episulfide compound or the said episulfide compound containing mixture. desirable. Further, when the curing agent is an amine curing agent, a polythiol curing agent or an acid anhydride, the amine curing agent, polythiol curing agent or acid anhydride is 15 to 40 parts by weight based on 100 parts by weight of the episulfide compound or the episulfide compound-containing mixture. It is preferable to contain in a negative range.

It is preferable that the curable composition which concerns on this invention further contains a storage stabilizer. It is preferable that the curable composition which concerns on this invention further contains at least 1 sort (s) chosen from the group which consists of a phosphate ester, a phosphite ester, and a boric acid ester as said storage stabilizer, and it is more preferable to contain a phosphite ester. By using phosphite ester, the storage stability of the said episulfide compound or the mixture containing an episulfide compound can be improved further. Only 1 type may be used for the said storage stabilizer, and 2 or more types may be used together.

Examples of the phosphate esters include diethylbenzyl phosphate, trimethyl phosphate, triethyl phosphate, tri n-butyl phosphate, tris (butoxyethyl) phosphate, tris (2-ethylhexyl) phosphate, and (RO) ₃ P = O [R = L. Uryl group, cetyl group, stearyl group or oleyl group], tris (2-chloroethyl) phosphate, tris (2-dichloropropyl) phosphate, triphenyl phosphate, butyl pyrophosphate, tricresyl phosphate, trixylenyl phosphate , Octyl diphenyl phosphate, cresyl diphenyl phosphate, xylenyl diphosphate, monobutyl phosphate, dibutyl phosphate, di-2-ethylhexyl phosphate, monoisodecyl phosphate, ammonium ethyl phosphate and 2-ethylhexyl phosphate salt Can be mentioned. Among these, diethyl benzyl phosphate is used preferably.

Examples of the phosphite ester include trimethyl phosphite, triethyl phosphite, tri n-butyl phosphite, tris (2-ethylhexyl) phosphite, triisooctyl phosphite, tridecyl phosphite, triisodecyl phosphite, and tris (tri Decyl) phosphite, trioleyl phosphite, tristearyl phosphite, triphenyl phosphite, tris (nonylphenyl) phosphite, tris (2,4-di-t-butylphenyl) phosphite, phenyl diisooctyl Phosphite, phenyl diisodecyl phosphite, diphenyl mono (2-ethylhexyl) phosphite, diphenylisooctyl phosphite, diphenyl monodecyl phosphite, diphenyl monoisodecyl phosphite, diphenyl mono (tridecyl ) Phosphite, bis (nonylphenyl) dinonylphenyl phosphite, tetraphenyl dipropylene glycol diphosphite, poly (dipropylene glycol) phenyl phosphite, diisodecyl pentaerythritol diphospha , Bis (tridecyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, bis (nonylphenyl) pentaerythritol diphosphite, tetraphenyl tetra (tridecyl) pentaerythritol tetraphosphite, tetra (tri Decyl) -4,4'-isopropylidenediphenylphosphite, trilauryl trithiophosphite, dimethylhydrogenphosphite, dibutylhydrogenphosphite, di (2-ethylhexyl) hydrogenphosphite, dira Uryl hydrogen phosphite, dioleyl hydrogen phosphite, diphenyl hydrogen phosphite, diphenyl mono (2-ethylhexyl) phosphite, diphenyl monodecyl phosphite and diphenyl mono (tridecyl) phosphite Can be mentioned. Among these, diphenyl mono (2-ethylhexyl) phosphite, diphenyl monodecyl phosphite, or diphenyl mono (tridecyl) phosphite is preferable, and diphenyl monodecyl phosphite or diphenyl mono (tridecyl) phosphite is preferable. It is more preferable, and diphenyl mono (tridecyl) phosphite is further more preferable.

Examples of the boric acid esters include trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate and tricyclohexyl borate , Trioctyl borate, trinonyl borate, tridecyl borate, tridodecyl borate, trihexadecyl borate, trioctadecyl borate, tribenzyl borate, triphenyl borate, tri-o-tolyl borate, tri-m-tolyl borate, Triethanolamine borate, tris (2-ethylhexyloxy) borane, bis (1,4,7,10-tetraoxoundecyl) (1,4,7,10,13-pentaoxatetradecyl) (1,4 , 7-trioxoundecyl) borane, 2- (β-dimethylaminoisopropoxy) -4,5-dimethyl-1,3,2-dioxaborolane, 2- (β-diethylaminoethoxy) -4,4,6-trimethyl-1,3,2-dioxaborinane, 2- (β-dimethylaminoethoxy) -4,4,6-trimeth -1,3,2-dioxaborinane, 2- (β-diisopropylaminoethoxy) -1,3,2-dioxaborinane, 2- (β-diisopropylaminoethoxy) -4 -Methyl-1,3,2-dioxaborinane, 2- (γ-dimethylaminopropoxy) -1,3,6,9-tetraoxa-2-boracycloundecane and 2- (β-dimethylamino Ethoxy) -4,4- (4-hydroxybutyl) -1,3,2-dioxaborinane, 2,2-oxybis (5,5-dimethyl-1,3,2-dioxaborinane ) And an epoxy-phenol-boric acid ester compound.

It is preferable that content of the said storage stabilizer exists in the range of 0.001-0.1 weight part with respect to 100 weight part of said episulfide compound or the said episulfide compound containing mixture. The minimum with more preferable content of the said storage stabilizer is 0.005 weight part with respect to 100 weight part of said episulfide compound or the said episulfide compound containing mixture, and a more preferable upper limit is 0.05 weight part. When content of a storage stabilizer, especially a phosphite ester is in the said range, the storage stability of the said episulfide compound or the said episulfide compound containing mixture can be improved further.

It is preferable that the curable composition which concerns on this invention further contains a hardening accelerator. The use of a curing accelerator can further speed up the curing of the curable composition. Only 1 type of hardening accelerator may be used, and 2 or more types may be used together.

As an example of the said hardening accelerator, an imidazole hardening accelerator, an amine hardening accelerator, etc. are mentioned. Among these, imidazole hardening accelerator is preferable. In addition, an imidazole hardening accelerator or an amine hardening accelerator can be used also as an imidazole hardening agent or an amine hardening agent.

As said imidazole hardening accelerator, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-phenyl imidazolium Trimellitate, 2,4-diamino-6- [2'-methylimidazolyl- (1 ')]-ethyl-s-triazine or 2,4-diamino-6- [2'-methyl Midazolyl- (1 ')]-ethyl-s-triazine isocyanuric acid addition product etc. are mentioned.

The lower limit of the content of the curing accelerator is preferably 0.5 parts by weight, more preferably 1 part by weight, more preferably 6 parts by weight, and more preferably an upper limit of 100 parts by weight of the episulfide compound or the episulfide compound-containing mixture. Is 4 parts by weight. When there is too little content of a hardening accelerator, a curable composition will become hard to fully harden. When there is too much content of a hardening accelerator, the excess hardening accelerator which does not participate in hardening after hardening may remain.

It is preferable that the curable composition which concerns on this invention further contains a filler. By use of a filler, latent heat expansion of the hardened | cured material of a curable composition can be suppressed. Only 1 type may be used for a filler and 2 or more types may be used together.

Specific examples of the filler include silica, aluminum nitride, alumina, and the like. It is preferable that the said filler is filler particle. It is preferable that the average particle diameter of a filler particle exists in the range of 0.1-1.0 micrometer. If the average particle diameter of a filler particle is in the said range, latent heat expansion of the hardened | cured material of a curable composition can be further suppressed. "Average particle diameter" shows the volume average diameter measured by the dynamic laser scattering method.

It is preferable that content of the said filler exists in the range of 50-900 weight part with respect to 100 weight part of said episulfide compound or the said episulfide compound containing mixture. If content of a filler is in the said range, latent heat expansion of the hardened | cured material of a curable composition can be further suppressed.

The curable composition which concerns on this invention may further contain a solvent, an ion trapping agent, or a silane coupling agent as needed.

The solvent is not particularly limited. As said solvent, ethyl acetate, methyl cellosolve, toluene, acetone, methyl ethyl ketone, cyclohexane, n-hexane, tetrahydrofuran, diethyl ether, etc. are mentioned, for example. Only 1 type of solvents may be used, and 2 or more types may be used together.

The said silane coupling agent is not specifically limited. As said silane coupling agent, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2- Aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyldimethylethoxysilane, 3-aminopropylmethyldiethoxysilane, 3 -Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, vinyltriacetoxysilane, vinyltrichlorosilane, 3-glycidoxypropyltrimethoxysilane , 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-chloropropyltrimethoxy Silane, 3-chloropropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methac Oxypropyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ethyltrimethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, dodecyltriethoxysilane, hexyl Trimethoxysilane, isobutyl diethoxysilane, methylphenyl diethoxysilane, methylphenyl dimethoxysilane, or imidazole silane etc. are mentioned. Among these, imidazolesilane is preferable. Only 1 type may be used for a silane coupling agent, and 2 or more types may be used together.

The said ion trapping agent is not specifically limited. Specific examples of the ion trapping agent include aluminosilicate, hydrous titanium oxide, hydrous bismuth oxide, zirconium phosphate, titanium phosphate, hydrotalcite, ammonium molybdate phosphate, hexacyano zinc or ion exchange resin. Only 1 type of ion trapping agents may be used, and 2 or more types may be used together.

The curable composition which concerns on this invention may further contain the photocurable compound and a photoinitiator so that it may also harden by light irradiation. According to the use of the said photocurable compound and the said photoinitiator, a curable composition can be hardened by irradiation of light. Moreover, curable composition can be semi-hardened and the fluidity | liquidity of a curable composition can be reduced.

The said photocurable compound is not specifically limited. As said photocurable compound, (meth) acrylic resin, cyclic ether group containing resin, etc. are used preferably. The said (meth) acrylic resin represents a methacryl resin and an acrylic resin.

As said (meth) acrylic resin, the ester compound obtained by making the compound which has (meth) acrylic acid and a hydroxyl group react, the epoxy (meth) acrylate obtained by making (meth) acrylic acid and an epoxy compound react, or (meth) which has a hydroxyl group in isocyanate Urethane (meth) acrylate obtained by making an acrylic acid derivative react is used preferably.

The ester compound obtained by making the said (meth) acrylic acid and the compound which has a hydroxyl group react is not specifically limited. As said ester compound, a monofunctional ester compound, a bifunctional ester compound, and a trifunctional or more than trifunctional ester compound can all be used.

It is preferable that the said photocurable compound contains at least 1 sort (s) of group of epoxy groups, and the photo- and thermosetting compound (henceforth partial (meth) acrylated epoxy resin) which has a (meth) acryl group.

The said partial (meth) acrylated epoxy resin is obtained by reacting an epoxy resin and (meth) acrylic acid in presence of a basic catalyst according to a conventional method, for example. It is preferable that 20% or more of an epoxy group is converted into the (meth) acryloyl group (conversion ratio), and is partially (meth) acrylated. It is more preferable that 50% of an epoxy group is converted into the (meth) acryloyl group. The said (meth) acryloyl represents acryloyl and methacryloyl.

From the viewpoint of improving the curability of the curable composition, the lower limit of the content of the partially (meth) acrylated epoxy resin is preferably 0.1% by weight, more preferably 0.5% by weight, and preferably 2% by weight in 100% by weight of the curable compound. , And a more preferable upper limit is 1.5 weight%.

As said epoxy (meth) acrylate, bisphenol-type epoxy (meth) acrylate, cresol novolak-type epoxy (meth) acrylate, carboxylic anhydride modified epoxy (meth) acrylate, and phenol novolak-type epoxy (meth) acryl The rate etc. are mentioned.

As an epoxy compound used for obtaining the said epoxy (meth) acrylate, and a commercial item of the said epoxy compound, For example, bisphenol-A epoxy resins, such as Epicoat 828EL and Epicoat 1004 (all are the Japan epoxy resin company make), Epi Bisphenol F type epoxy resins, such as coat 806 and Epicoat 4004 (all are manufactured by Japan Epoxy Resin Co., Ltd.), bisphenol S type epoxy resins, such as Epiclone EXA1514 (made by DIC Corporation), and RE-810NM (made by Nippon Kayaku Co., Ltd.) Hydrogenated bisphenol-type epoxy resins, such as a 2'- diallyl bisphenol A epoxy resin and Epiclone EXA7015 (made by DIC Corporation), and propylene oxide addition bisphenol A-type epoxy resins, such as EP-4000S (made by Adeka Corporation), EX- Resorcinol type epoxy resins, such as 201 (made by Nagase Chemtex Co., Ltd.), biphenyl type epoxy resins, such as Epicoat YX-4000H (made by Japan epoxy resin company), YSLV-50TE (made by Toto Kasei Co., Ltd.), etc. Sulfide type epoxy resins, ether type epoxy resins such as YSLV-80DE (manufactured by Tohto Kasei Co., Ltd.), dicyclopentadiene type epoxy resins such as EP-4088S (manufactured by Adeka Co., Ltd.), epiclon HP4032 and epiclon EXA-4700 Orthocresol, such as naphthalene type epoxy resins, such as (all made by DIC Corporation), phenol novolak-type epoxy resins, such as epiclon N-770 (made by DIC Corporation), and epiclon N-670-EXP-S (made by DIC Corporation) Dicyclopentadiene novolak-type epoxy resins, such as a novolak-type epoxy resin, Epiclone HP7200 (made by DIC Corporation), biphenyl novolak-type epoxy resins, such as NC-3000P (made by Nippon Kayaku Co., Ltd.), ESN-165S (Doto Naphthalene phenol novolak-type epoxy resins, such as Kasei Co., Ltd., Epicoat 630 (made by Japan epoxy resin), Epiclone 430 (made by DIC Corporation), and TETRAD-X (made by Mitsubishi Gas Chemical Corporation), etc. Glycidylamine type epoxy resin, ZX-1542 (manufactured by Tohto Kasei Co., Ltd.), Epi Alkylpolyol type epoxy resins such as Ron 726 (manufactured by DIC Corporation), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) and Denacol EX-611 (manufactured by Nagase Chemtex Corporation), YR-450 and YR-207 (all Glycidyl ester compounds such as rubber modified epoxy resins such as Doto Kasei Co., Ltd.) and Eporide PB (manufactured by Daicel Chemical Co., Ltd.), Denacol EX-147 (manufactured by Nagase Chemtex Co., Ltd.), and epicoat YL-7000 Bisphenol A episulfide resins such as (manufactured by Japan Epoxy Resin Co., Ltd.), YDC-1312, YSLV-80XY, and YSLV-90CR (both manufactured by Toto Kasei Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Co., Ltd.), Epicoat 1031, and Epi And other epoxy resins such as coat 1032 (all manufactured by Japan Epoxy Resin Co., Ltd.), EXA-7120 (manufactured by DIC Corporation), and Tepic (TEPIC) (manufactured by Nissan Chemical Industries, Ltd.).

As a commercial item of the said epoxy (meth) acrylate, for example, ebecryl 3700, ebecryl 3600, ebecryl 3701, ebecryl 3703, ebecryl 3200, ebecryl 3201, ebecryl 3600, ebecryl 3702, ebecryl 3412, Evercryl 860, Evercryl RDX63182, Evercryl 6040 and Evercryl 3800 (all manufactured by Daicel BC Corporation), EA-1020, EA-1010, EA-5520, EA-5323, EA-CHD and EMA-1020 (all new) Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy ester 200PA, epoxy ester 80MFA, epoxy ester 3002M, epoxy ester 3002A, epoxy ester 1600A, epoxy ester 3000M, epoxy ester 3000A, Epoxy ester 200EA and epoxy ester 400EA (both manufactured by Kyowa Co., Ltd.), Denacol acrylate DA-141, Denacol acrylate DA-314 and Denacol acrylate DA-911 (both Naga Sechemtex Co., Ltd.) etc. are mentioned.

When photocurable compounds other than the photocurable compound mentioned above are contained, the said photocurable compound may be a crosslinkable compound or a non-crosslinkable compound may be sufficient as it.

As a specific example of the said crosslinkable compound, 1, 4- butanediol di (meth) acrylate, 1, 6- hexanediol di (meth) acrylate, 1, 9- nonane diol di (meth) acrylate, ( Poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, glycerin methacrylate acrylate, Pentaerythritol tri (meth) acrylate, trimethylolpropanetrimethacrylate, allyl (meth) acrylate, vinyl (meth) acrylate, divinylbenzene, polyester (meth) acrylate, urethane (meth) acrylate, etc. Can be mentioned.

As a specific example of the said noncrosslinkable compound, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t -Butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (Meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate and tetradecyl (meth) acryl The rate etc. are mentioned.

From the viewpoint of photocuring the curable composition efficiently, the lower limit of the content of the photocurable compound is preferably 1 part by weight, and more preferably 10 parts by weight based on 100 parts by weight of the episulfide compound or the episulfide compound-containing mixture. The lower limit is 50 parts by weight, the upper limit is preferably 10000 parts by weight, the upper limit is more preferably 1000 parts by weight, and the upper limit is 500 parts by weight.

The photoinitiator is not particularly limited. Only 1 type may be used for the said photoinitiator, and 2 or more types may be used together.

As a specific example of the said photoinitiator, an acetophenone photoinitiator, a benzophenone photoinitiator, thioxanthone, a ketal photoinitiator, a halogenated ketone, an acylphosphine oxide, an acyl phosphonate, etc. are mentioned.

As a specific example of the said acetophenone photoinitiator, 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2- propyl) ketone and 2-hydroxy-2- methyl-1- phenyl propane- 1-one And methoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one or 2-hydroxy-2-cyclohexylacetophenone. As a specific example of the said ketal photoinitiator, benzyl dimethyl ketal etc. are mentioned.

Content of the said photoinitiator is not specifically limited. The minimum with preferable content of the said photoinitiator is 0.1 weight part with respect to 100 weight part of said photocurable compositions, A more preferable minimum is 0.2 weight part, A more preferable minimum is 2 weight part, A preferable upper limit is 10 weight part, A more preferable upper limit is 5 parts by weight. When there is too little content of a photoinitiator, the effect which added the photoinitiator may not be fully acquired. When there is too much content of a photoinitiator, the adhesive force of the hardened | cured material of a curable composition may fall.

Curable resin composition may further contain other epoxy compounds other than the epoxy compound represented by the said General formula (11-1), 12-1, 13, 11, or 12. As said epoxy compound, the epoxy compound used in order to obtain the above-mentioned epoxy (meth) acrylate can be used.

The preferable minimum of content of an episulfide compound in 100 weight% of a total of an episulfide compound, the epoxy compound represented by the said Formula (11-1, 12-1, 13, 11, or 12), and the said other epoxy compound is 10 weight %, More preferable minimum is 25 weight%, a preferable upper limit is 100 weight%, and a more preferable upper limit is 50 weight%.

The curable composition which concerns on this invention can be used for adhesion | attachment of a liquid crystal panel, a semiconductor chip, etc. as a one-component adhesive. The curable composition may be a paste adhesive or a film adhesive.

The method of processing the curable composition which concerns on this invention with a film adhesive is not specifically limited. For example, after coating a curable composition on base materials, such as a release paper, and processing it into a film adhesive, or adding a solvent to a curable composition, and coating on a base material, such as a release paper, a solvent at a temperature lower than the active temperature of the said hardening | curing agent The method of volatilizing and processing into a film adhesive is mentioned.

As a method of curing the curable composition according to the present invention, a method of heating the curable composition, a method of heating the curable composition to which the light is irradiated after irradiating light to the curable composition, or simultaneously irradiating light to the curable composition and simultaneously curable composition The method of heating this etc. are mentioned.

It is preferable to exist in the range of 160-250 degreeC, and, as for the heating temperature at the time of hardening curable composition which concerns on this invention, it is more preferable to exist in the range of 160-200 degreeC. Since the curable composition can be cured quickly at low temperatures, the amount of energy required for heating can be reduced.

When the said heating temperature is 200 degrees C or less, hardening time becomes long, and the hardening time exceeds 10 second, for example, when heating temperature is 200 degreeC. On the other hand, in the curable composition which concerns on this invention, even if the said heating temperature is 200 degrees C or less, it can harden in a short time.

When the curable composition which concerns on this invention is photocured, the light source used when irradiating light to a curable composition is not specifically limited. As said light source, the light source etc. which have sufficient emission distribution in wavelength 420 nm or less are mentioned, for example. As a specific example of the said light source, 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 light lamp, a microwave excited mercury lamp, a metal halide lamp, etc. are mentioned, for example. Among these, chemical lamps are preferable. The chemical lamp efficiently emits light in the active wavelength region of the photopolymerization initiator and has a small amount of light emission in the light absorption wavelength region of the composition components other than the photopolymerization initiator. Moreover, when a chemical lamp is used, light can be efficiently reached even to the photocuring component which exists in the inside of a composition.

For example, when the cleavage type photoinitiator which has an acetophenone group is contained, it is preferable that the light irradiation intensity | strength in the wavelength range of 365 nm-420 nm exists in the range of 0.1-100 mW / cm <2>.

When the curable composition according to the present invention further contains conductive particles, the curable composition can be used as the anisotropic conductive material.

The said electroconductive particle electrically connects between a circuit board and an electrode of a semiconductor chip, for example. The said electroconductive particle will not be specifically limited if it is a particle | grain which has electroconductivity at least. As said electroconductive particle, the electroconductive particle which coat | covered the surface of organic particle | grains, an inorganic particle, organic inorganic hybrid particle | grains, or a metal particle with a metal layer, the metal particle comprised substantially only with metal, etc. are mentioned, for example. 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, or a metal layer containing tin.

Content of the said electroconductive particle is not specifically limited. To 100 parts by weight of the episulfide compound or the episulfide compound-containing mixture, the lower limit of the content of the conductive particles is preferably 0.1 parts by weight, more preferably 0.5 parts by weight, more preferably 10 parts by weight, and more preferably an upper limit. Is 5 parts by weight. When content of the said electroconductive particle is too small, it may not be able to make electrically conductive etc. reliably. When there is too much content of the said electroconductive particle, the short circuit between adjacent electrodes which should not be conducted may generate | occur | produce.

When the curable composition is in a liquid or paste form, the viscosity (25 ° C) of the curable composition is preferably in the range of 20000 to 100000 mPa · s. When the said viscosity is too low, electroconductive particle may precipitate. When the said viscosity is too high, electroconductive particle may not fully disperse.

(Use of Curable Composition)

The curable composition which concerns on this invention can be used for bonding various connection object members.

When the curable composition according to the present invention is an anisotropic conductive material containing conductive particles, the anisotropic conductive material can be used as an anisotropic conductive paste, an anisotropic conductive ink, an anisotropic conductive adhesive, an anisotropic conductive film or an anisotropic conductive sheet. When an anisotropic conductive material is used as film adhesives, such as an anisotropic conductive film and an anisotropic conductive sheet, the film adhesive which does not contain electroconductive particle may be laminated | stacked on the film adhesive containing the said electroconductive particle.

The said anisotropic electrically-conductive material is used suitably for obtaining the connection structure which electrically connects the 1st, 2nd connection object member.

An example of the bonded structure using the curable composition which concerns on one Embodiment of this invention in FIG. 1 is typically shown with sectional drawing.

The connection structure shown in FIG. 1 is the connection part 3 which connects the 1st connection object member 2, the 2nd connection object member 4, and the 1st, 2nd connection object member 2, (4). It is provided. The connection part 3 is formed by hardening | curing the curable composition containing the electroconductive particle 5, ie, an anisotropic conductive material.

A plurality of electrodes 2b are provided on the upper surface 2a of the first connection object member 2. The lower surface 4a of the second connection object member 4 is provided with a plurality of electrodes 4b. The electrode 2b and the electrode 4b are electrically connected by the one or some electroconductive particle 5. Therefore, the 1st, 2nd connection object members 2 and 4 are electrically connected by the electroconductive particle 5. As shown in FIG.

Specifically as the connection structure, an electronic component chip such as a semiconductor chip, a condenser chip, or a diode chip is mounted on a circuit board, and a connection structure in which an electrode of the electronic component chip is electrically connected to an electrode on the circuit board is used. Can be mentioned. As a circuit board, various circuit boards, such as various printed circuit boards, such as a flexible printed circuit board, a glass substrate, or the board | substrate with which metal foil was laminated | stacked, are mentioned. It is preferable that a 1st, 2nd connection object member is an electronic component or a circuit board.

The manufacturing method of the said bonded structure is not specifically limited. As an example of the manufacturing method of a bonded structure, after arrange | positioning the said anisotropic conductive material between 1st connection object members, such as an electronic component or a circuit board, and 2nd connection object members, such as an electronic component or a circuit board, and obtaining a laminated body, And a method of heating and pressurizing the laminate.

In addition, the said curable composition may not contain electroconductive particle. In this case, the said curable composition is used in order to adhere | attach and connect a 1st, 2nd connection object member, without electrically connecting a 1st, 2nd connection object member.

Hereinafter, an Example and a comparative example are shown and this invention is demonstrated concretely. This invention is not limited only to a following example.

(Example 1)

(1) Preparation of Episulphide Compound-Containing Mixture

In a 2 L vessel equipped with a stirrer, a cooler and a thermometer, 250 mL of ethanol, 250 mL of pure water and 20 g of potassium thiocyanate were added, and potassium thiocyanate was dissolved to prepare a first solution in the vessel. Thereafter, the temperature in the vessel was maintained in the range of 20 to 25 ° C.

Subsequently, 160 g of resorcinol diglycidyl ether was added dropwise to the first solution at a rate of 5 mL / min while stirring the first solution maintained at 20 to 25 ° C. After dripping, it stirred further for 30 minutes and obtained the solution containing an epoxy compound.

Next, a second solution in which 20 g of potassium thiocyanate was dissolved in a solution containing 100 mL of pure water and 100 mL of ethanol was prepared. The second solution prepared in the obtained epoxy compound-containing solution was added at a rate of 5 mL / min, and then stirred for 30 minutes. After stirring, a second solution in which 20 g of potassium thiocyanate was dissolved in a solution containing 100 mL of pure water and 100 mL of ethanol was further prepared, and the second solution was further added at a rate of 5 mL / min. Stirred for a minute. Thereafter, the temperature in the vessel was cooled to 10 ° C, and stirred for 2 hours to react.

Subsequently, 100 mL of saturated brine was added to the vessel, followed by stirring for 10 minutes. After stirring, 300 mL of toluene was added to the vessel and stirred for 10 minutes. Thereafter, the solution in the container was transferred to a separatory funnel and allowed to stand for 2 hours, and the solution was separated. The lower solution in the separating funnel was discharged and the supernatant was taken out. 100 mL of toluene was added to the extracted supernatant, followed by stirring for 2 hours. Furthermore, 100 mL of toluene was further added and stirred, and it left still for 2 hours.

Subsequently, 50 g of magnesium sulfate was added to the supernatant to which toluene was added, and it stirred for 5 minutes. After stirring, the magnesium sulfate was removed by filter paper to separate the solution. The remaining solvent was removed by drying the solution separated using a vacuum dryer at 80 ° C. under reduced pressure. In this way, an episulfide compound-containing mixture was obtained.

¹ H-NMR of the mixture containing episulfide compound obtained by using chloroform as a solvent was measured. As a result, a signal in the 6.5 to 7.5 ppm region indicating the presence of an epoxy group was decreased, and a signal appeared in the 2.0 to 3.0 ppm region indicating the presence of an episulfide group. This confirmed that some epoxy groups of resorcinol diglycidyl ether were converted into episulfide groups. From the integrated value of the ¹ H-NMR measurement result, the episulfide compound-containing mixture contains 70% by weight of resorcinol diglycidyl ether and 30% by weight of episulfide compound represented by the above formula (1B). Confirmed.

(2) Preparation of Curable Composition

33 parts by weight of the obtained episulfide compound-containing mixture, 20 parts by weight of pentaerythritol tetrakis-3-mercaptopropionate as a curing agent, 0.01 part by weight of diphenylmono (tridecyl) phosphite as a phosphite ester, a curing accelerator 1 part by weight of 2-ethyl-4-methylimidazole, 20 parts by weight of silica having an average particle diameter of 0.25 μm as a filler, 20 parts by weight of alumina having an average particle diameter of 0.5 μm, and 2 parts by weight of conductive particles having an average particle diameter of 3 μm Then, by stirring at 2000 rpm for 5 minutes using an planetary stirrer, a curable composition as an anisotropic conductive paste was obtained. In addition, the used electroconductive particle is electroconductive particle which has a metal plating in which the nickel plating layer is formed in the surface of the divinylbenzene resin particle, and the gold plating layer is formed in the surface of the said nickel plating layer.

(Example 2)

A curable composition as an anisotropic conductive paste was prepared in the same manner as in Example 1 except that no pentaerythritol tetrakis-3-mercaptopropionate and diphenylmono (tridecyl) phosphite were added during the preparation of the curable composition. Got it.

(Comparative Example 1)

The mixture was obtained by adding 100 weight part of bisphenol-A epoxy resins, and 5 weight part of 1, 2- dimethyl imidazole as a hardening | curing agent, and stirring at 2000 rpm for 5 minutes using an oil type stirrer.

To the obtained mixture, 7 parts by weight of silica particles having an average particle diameter of 0.02 µm and 2 parts by weight of conductive particles having an average particle diameter of 3 µm were added, and a blend was obtained by stirring at 2000 rpm for 8 minutes using a planetary stirrer. In addition, the used electroconductive particle is electroconductive particle which has a metal plating in which the nickel plating layer is formed in the surface of the divinylbenzene resin particle, and the gold plating layer is formed in the surface of the said nickel plating layer.

The cured composition as an anisotropic electrically conductive paste was obtained by filtering the obtained compound with nylon filter paper (pore diameter of 10 micrometers).

(Evaluation of Examples 1 and 2 and Comparative Example 1)

(1) curing time

The transparent glass substrate in which the ITO electrode pattern whose L / S is 10 micrometers / 10 micrometers was formed in the upper surface was prepared. In addition, a semiconductor chip with a copper electrode pattern having a L / S of 10 µm / 10 µm was prepared.

On the said transparent glass substrate, the obtained curable composition was coated so that it might be set to 30 micrometers in thickness, and the curable composition layer was formed. Subsequently, the said semiconductor chip was laminated | stacked on the curable composition layer so that electrodes might mutually face each other. Thereafter, the heating head was placed on the upper surface of the semiconductor chip while adjusting the temperature of the heating head so that the temperature of the curable composition layer was 185 ° C, and the curable composition layer was cured at 185 ° C to obtain a bonded structure. When obtaining this bonded structure, the time until the curable composition layer hardens by heating was measured.

(2) presence or absence of voids

In the bonded structure obtained by evaluation of the said hardening time, whether or not the space | gap generate | occur | produced in the hardened | cured material layer formed by the curable composition layer was observed visually from the lower surface side of a transparent glass substrate.

The results are shown in Table 1 below.

(Example 3)

5 parts by weight of an epoxy acrylate ("EBECRYL 3702" manufactured by Daicel Cytec Co., Ltd.) and an acylphosphine oxide compound (manufactured by Ciba Japan Co., Ltd. A curable composition as an anisotropic conductive paste was obtained in the same manner as in Example 1 except that 0.1 part by weight of DAROCUR) TPO ″) was further added.

(Example 4)

5 parts by weight of a urethane acrylate (manufactured by Daicel Cytec Co., Ltd., "Ebecryl 8904") and an acylphosphine oxide-based compound (Ciba Japan Co., Ltd. "Darocure TPO") 0.1 Except having added the weight part further, it carried out similarly to Example 1, and obtained the curable composition as an anisotropic electrically conductive paste.

(Evaluation of Examples 3 and 4)

(1) curing time

Transparent glass substrates and semiconductor chips used in the evaluations of Examples 1 and 2 and Comparative Example 1 were prepared.

On the upper surface of the said transparent glass substrate, the obtained curable composition was coated so that it might be set to 30 micrometers in thickness, and the curable composition layer was formed. Moreover, while apply | coating an anisotropic electrically conductive paste, 420 nm ultraviolet-ray was irradiated to the curable composition layer using an ultraviolet irradiation lamp so that light irradiation intensity might be 50 mW / cm <2>, and the curable composition layer was B staged by photopolymerization. After coating, ie, the time T from when the coated curable composition layer was in contact with the transparent glass substrate to when light was irradiated to the curable composition layer was 0.5 second.

Subsequently, the semiconductor chip was laminated on the upper surface of the B-stage curable composition layer so as to connect the electrodes to face each other. Thereafter, the pressure heating head is placed on the upper surface of the semiconductor chip while adjusting the temperature of the head so that the temperature of the curable composition layer is 185 ° C, and a pressure of 10 kg / cm 2 is applied to the B staged curable composition layer at 185 ° C. The bonded structure was obtained by complete hardening. When obtaining this bonded structure, the time until the curable composition layer hardens by heating was measured.

(2) presence or absence of voids

In the bonded structure obtained by evaluation of the said hardening time, the presence or absence of the space | gap was evaluated like Example 1, 2 and Comparative Example 1.

The results are shown in Table 2 below.

(Examples 5 to 24)

(1) Preparation of Episulfide Compound or Mixture containing Episulfide Compound

Example 1 An episulfide compound or an episulfide compound-containing mixture containing the episulfide compound represented by Formula 1, 2 or 3 and the epoxy compound represented by Formula 11, 12 or 13 in the following content Prepared by the same procedure as The episulfide compound or the episulfide compound-containing mixture of each example was obtained by appropriately adjusting the amount of potassium thiocyanate used and adjusting the conversion ratio.

(2) Preparation of Curable Composition

At the time of preparation of a curable composition, 33 parts by weight of the episulfide compound-containing mixture used in Example 1 was the same as in Example 1 except for changing to the episulfide compound or the episulfide compound-containing mixture shown in Tables 3 to 5 below. The curable composition as an anisotropic conductive paste was obtained.

(Example 25)

33 parts by weight of the episulfide compound-containing mixture used in Example 1 at the time of preparing the curable composition, 10 parts by weight of the episulfide compound-containing mixture used in Example 1 and 20 parts by weight of the episulfide compound-containing mixture used in Example 9 Except having changed, it carried out similarly to Example 1, and obtained the curable composition.

(Example 26)

Except for changing 33 parts by weight of the episulfide compound-containing mixture used in Example 1 at the time of preparing the curable composition into 20 parts by weight of the episulfide compound-containing mixture used in Example 1 and 10 parts by weight of resorcinol glycidyl ether In the same manner as in Example 1, a curable composition was obtained.

(Example 27)

Except for changing 33 parts by weight of the episulfide compound-containing mixture used in Example 1 at the time of preparing the curable composition, 20 parts by weight of the episulfide compound-containing mixture used in Example 1 and 10 parts by weight of bisphenol A glycidyl ether In the same manner as in Example 1, a curable composition was obtained.

(Evaluation of Examples 5 to 27)

Curing time and the presence or absence of voids were evaluated in the same manner as in the evaluations of Examples 1 and 2 and Comparative Example 1.

The results are shown in Tables 3 to 6 below.

One… Connection structure
2… First connection object member
2a... Top
2b... electrode
3 ... Connection
4… Second connection object member
4a... if
4b... electrode
5... Conductive particles

Claims

An episulfide compound having a structure represented by the following Formula 1-1, 2-1 or 3.
<Formula 1-1>

(In Formula 1-1, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen, and R3, R4, R5 and A group other than hydrogen in R6 represents a group represented by the following Chemical Formula 4)
<Formula 2-1>

(In Formula 2-1, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 each represent hydrogen, and R53, A group other than hydrogen among R54, R55, R56, R57, and R58 represents a group represented by Formula 5 below)
<Formula 3>

(In Formula 3, R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms, and 6 to 8 groups of 8 groups of R103, R104, R105, R106, R107, R108, R109 and R110 represent hydrogen, A group other than hydrogen among R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 represents a group represented by the following formula (6):
<Formula 4>

(In Formula 4, R7 represents an alkylene group having 1 to 5 carbon atoms.)
<Formula 5>

(In Formula 5, R59 represents an alkylene group having 1 to 5 carbon atoms.)
<Formula 6>

(In Formula 6, R 111 represents an alkylene group having 1 to 5 carbon atoms.)

The episulfide compound according to claim 1, which has a structure represented by the following general formula (1) or (2).
<Formula 1>

(In Formula 1, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen, and among R3, R4, R5 and R6 A group other than hydrogen represents a group represented by the following formula (4)
<Formula 2>

(In Formula 2, R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms, 4 to 6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 each represent hydrogen, and R53, R54, R55, R56, R57 and R58 of the non-hydrogen group represents a group represented by the formula (5)
<Formula 4>

(In Formula 5, R59 represents an alkylene group having 1 to 5 carbon atoms.)

The episulfide compound according to claim 2, wherein the structure represented by Formula 1 or 2 is a structure represented by Formula 1A or 2A.
<Formula 1A>

(In Formula 1A, R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms.)
<Formula 2A>

The episulfide compound containing mixture containing the episulfide compound in any one of Claims 1-3, and the epoxy compound represented by following formula (11-1), 12-1, or 13.
<Formula 11-1>

(In Formula 11-1, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms, 2 to 4 groups out of 4 groups of R13, R14, R15, and R16 represent hydrogen, and R13, R14, R15 and A group other than hydrogen in R16 represents a group represented by the following Formula 14)
<Formula 12-1>

(In Formula 12-1, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 represent hydrogen, and R63, A group other than hydrogen among R64, R65, R66, R67, and R68 represents a group represented by the following Formula 15)
<Formula 13>

(In Formula 13, R121 and R122 each represent an alkylene group having 1 to 5 carbon atoms, and 6 to 8 groups of 8 groups of R123, R124, R125, R126, R127, R128, R129, and R130 each represent hydrogen, A group other than hydrogen among R123, R124, R125, R126, R127, R128, R129, and R130 represents a group represented by the following Chemical Formula 16)
<Formula 14>

(In Formula 14, R17 represents an alkylene group having 1 to 5 carbon atoms.)
<Formula 15>

(In Formula 15, R69 represents an alkylene group having 1 to 5 carbon atoms.)
<Formula 16>

(In Formula 16, R131 represents an alkylene group having 1 to 5 carbon atoms.)

The episulfide compound-containing mixture according to claim 4, wherein the epoxy compound is an epoxy compound represented by the following Chemical Formula 11 or 12.
<Formula 11>

(In Formula 11, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms, and 2 to 4 groups of 4 groups of R13, R14, R15, and R16 represent hydrogen, and among R13, R14, R15, and R16. A group other than hydrogen represents a group represented by the following formula (14))
<Formula 12>

(In Formula 12, R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, 4-6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 each represent hydrogen, and R63, R64, A group other than hydrogen among R65, R66, R67, and R68 represents a group represented by the following Formula 15)
<Formula 14>

(In Formula 15, R69 represents an alkylene group having 1 to 5 carbon atoms.)

The episulfide compound-containing mixture according to claim 5, wherein the structure represented by Formula 11 or 12 is a structure represented by Formula 11A or 12A.
<Formula 11A>

(In Formula 11A, R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms.)
<Formula 12A>

It is a manufacturing method of the episulfide compound containing mixture of any one of Claims 4-6,
After adding the epoxy compound represented by the formula (11-1, 12-1 or 13) or the solution containing the epoxy compound continuously or intermittently to the first solution containing the thiocyanate, the agent comprising a thiocyanate 2 A method for producing an episulfide compound-containing mixture, in which some epoxy groups of the epoxy compound are converted into episulfide groups by further continuously or intermittently adding the solution.

The method for producing an episulfide compound-containing mixture according to claim 7, wherein the epoxy compound or the solution containing the epoxy compound is used as the epoxy compound represented by the formula (11) or (12) or the solution containing the epoxy compound. .

The curable composition containing the episulfide compound in any one of Claims 1-3, and a hardening | curing agent.

The curable composition containing the episulfide compound containing mixture of any one of Claims 4-6, and a hardening | curing agent.

The curable composition of Claim 9 or 10 which further contains a photocurable compound and a photoinitiator.

The curable composition according to any one of claims 9 to 11, further comprising conductive particles.

It is provided with the 1st connection object member, the 2nd connection object member, and the connection part which connects the said 1st, 2nd connection object member,
The bonded structure in which the said connection part is formed of the curable composition in any one of Claims 9-11.

The method according to claim 13, wherein the curable composition contains conductive particles,
The said 1st, 2nd connection object member is connected structure electrically by the said electroconductive particle.