Thermally conductive epoxy-based thermoplastic resin, molded article derived from resin, and electronic device including molded article

Abstract

To provide a thermally conductive epoxy-based thermoplastic resin which enables re-molding and exhibits high thermal conductivity.SOLUTION: A thermally conductive epoxy-based thermoplastic resin is formed by curing a curable composition, wherein the curable composition comprises a bifunctional epoxy monomer having a mesogenic group and a bifunctional amine monomer represented by the following formula (2).SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a thermally conductive epoxy thermoplastic resin, a molded article made from the resin, and an electronic device including the molded article. [Background technology]

[0002] Lightweight and insulating (low electrical resistivity) resins are often used for electronic device housings, but their low thermal conductivity can cause problems with heat dissipation. Polymers with relatively high inherent thermal conductivity (for example, about 0.4 W / mK) include homopolymers such as polyethylene (PE) and polytetrafluoroethylene (PTFE), but they do not have sufficient heat dissipation properties.

[0003] In order to obtain a higher thermal conductivity (for example, about 1 W / mK), it has been proposed to add inorganic fillers such as silica, alumina, and silver to the resin. Patent Document 1 also discloses a technique for increasing the thermal conductivity of a plastic (resin) by adding an organic thermally conductive additive to the plastic. Patent Document 1 discloses, as the organic thermally conductive additive, a liquid crystalline thermoplastic resin (ester resin) in which a mesogen group and a flexible group are linked by an ester bond. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent No. 6193340 Summary of the Invention [Problem to be solved by the invention]

[0005] However, if the amount of inorganic filler or organic thermally conductive additive is increased in order to obtain high thermal conductivity, the physical properties of the base polymer may be affected. Furthermore, the organic thermally conductive additive of Patent Document 1 is an ester resin, so it requires a high synthesis temperature (up to 280°C) and has the problem of low water resistance. From this perspective, there is a demand to increase the thermal conductivity of the base polymer itself and not add fillers or additives, or to reduce the amount of fillers or additives added.

[0006] On the other hand, epoxy resins, which have high electrical insulation and water resistance, are widely used in electronic components such as printed circuit boards for electrical appliances and electronic devices, as well as memories and CPUs. However, epoxy resins are generally thermosetting resins, and therefore cannot be remolded once they have hardened (polymerized). This has led to the problem that their applications are limited. Under these circumstances, there has been a demand for epoxy resins that can be remolded and that have high thermal conductivity themselves.

[0007] The present invention is intended to solve the above problems by providing a thermally conductive epoxy thermoplastic resin that is remoldable and has high thermal conductivity. [Means for solving the problem]

[0008] As a result of extensive investigations aimed at achieving the above object, the present inventors have found that the above object can be achieved by the following configuration.

[0009] [1] A thermally conductive epoxy thermoplastic resin obtained by curing a curable composition, The curable composition is a bifunctional epoxy monomer containing a mesogenic group; A thermally conductive epoxy thermoplastic resin comprising a bifunctional amine monomer represented by formula (2) described below. [2] The thermally conductive epoxy thermoplastic resin according to [1], wherein the bifunctional epoxy monomer is represented by the following formula (1). [3] The thermally conductive epoxy thermoplastic resin according to [1] or [2], wherein the mesogen group is represented by formula (1A) described below. [4] The thermally conductive epoxy thermoplastic resin according to any one of [1] to [3], wherein the mesogen group is represented by formula (1B) described below. [5] In the formula (2) representing the bifunctional amine monomer, R 2 , R 3 and R 4 and each of the R, R and R groups is a substituted or unsubstituted aliphatic group which may contain a heteroatom. [6] The thermally conductive epoxy thermoplastic resin according to any one of [1] to [5], wherein the bifunctional amine monomer has one primary aliphatic amino group or two secondary aliphatic amino groups. [7] The thermally conductive epoxy thermoplastic resin according to any one of [1] to [6], wherein the curable composition further contains a bifunctional monomer represented by the formula (3) described later. [8] The thermally conductive epoxy thermoplastic resin according to [7], wherein in formula (3), c is a substituted or unsubstituted aliphatic group which may contain a heteroatom. [9] The thermally conductive epoxy thermoplastic resin according to [7], wherein in formula (3), c includes at least one structure selected from the group consisting of a polyalkylene oxide structure, a polysiloxane structure, and a fluorinated alkylene structure.

[10] The thermally conductive epoxy thermoplastic resin according to any one of [7] to [9], wherein the bifunctional monomer represented by formula (3) has a melting point of 80° C. or lower.

[11] The thermally conductive epoxy thermoplastic resin according to any one of [1] to

[10] , wherein a molded article consisting of only the thermally conductive epoxy thermoplastic resin has a thermal conductivity of 1 W / mK or more.

[12] The thermally conductive epoxy thermoplastic resin according to any one of [1] to

[11] , which is a crystalline resin.

[13] The thermally conductive epoxy thermoplastic resin according to any one of [1] to

[12] , which has a melting point.

[14] The thermally conductive epoxy thermoplastic resin according to

[13] , wherein the melting point is 200°C to 300°C.

[15] The thermally conductive epoxy thermoplastic resin according to any one of [1] to

[14] , wherein a molded article consisting of only the thermally conductive epoxy thermoplastic resin has a breaking strain of 10% or more.

[16] A resin composition comprising the thermally conductive epoxy thermoplastic resin according to any one of [1] to

[15] .

[17] The resin composition according to

[16] , further comprising a thermally conductive filler.

[18] A molded article obtained by molding the resin composition according to

[16] or

[17] .

[19] An electronic device comprising the molded article according to

[18] . Effect of the Invention

[0010] The thermally conductive epoxy thermoplastic resin of the present invention is remoldable and has high thermal conductivity. [Brief description of the drawings]

[0011] [Figure 1] FIG. 2 is a schematic diagram showing how mesogen groups are oriented in a thermally conductive epoxy thermoplastic resin (specific epoxy resin) according to an embodiment. [Diagram 2] FIG. 2 is a diagram showing the chemical structural formula of a specific example of a bifunctional amine monomer (second monomer) of the embodiment. [Diagram 3] FIG. 2 is a diagram showing the chemical structural formula of a specific example of a bifunctional monomer (third monomer) of the embodiment. [Figure 4] FIG. 2 is a diagram showing the chemical structural formulas of monomers used in the examples. [Diagram 5] 1 is a cross-sectional SEM image of a molded body molded in an example. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will be described in detail below. The following description of the components may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[0013] In the description of groups (atomic groups) in this specification, the description that does not indicate whether substituted or unsubstituted includes both unsubstituted and substituted groups, as long as it does not impair the effects of the present invention. For example, "alkyl group" includes not only alkyl groups that do not have a substituent (unsubstituted alkyl groups), but also alkyl groups that have a substituent (substituted alkyl groups). This also applies to each compound.

[0014] [Thermal conductive epoxy thermoplastic resin] The thermally conductive epoxy thermoplastic resin of this embodiment (hereinafter, may be referred to as the "specific epoxy resin") is a cured product (polymer, polymerization product) of a curable composition (monomer mixture) containing a bifunctional epoxy monomer (hereinafter, may be referred to as the "first monomer") containing a mesogen group and a bifunctional amine monomer represented by formula (2) described below (hereinafter, may be referred to as the "second monomer"). In this specification, a "bifunctional" monomer means a monomer that is bifunctional with respect to the chain growth reaction of the cured product (polymer, specific epoxy resin). For example, the "bifunctional" monomer includes a monomer having only two reactive functional groups (reactive groups) that are monofunctional with respect to the chain growth reaction (for example, a monomer containing only two epoxy groups), a monomer having only one reactive group that is bifunctional with respect to the chain growth reaction (for example, a primary amino group (-NH 2 ) is a monomer having only one aryl group.

[0015] The specific epoxy resin of the present embodiment contains a unit MA composed of a unit M derived from a bifunctional epoxy monomer (first monomer) containing a mesogen group and a unit A derived from a bifunctional amine monomer (second monomer) represented by formula (1), as shown in the following formula (I).

[0016] [ka]

[0017] The specific epoxy resin does not have a three-dimensional crosslinked structure, but has a linear structure, and therefore exhibits thermoplasticity. For this reason, the specific epoxy resin can be remolded many times by adding heat or a solvent even after curing (polymerization) while retaining the high electrical insulation and high water resistance that are characteristics of epoxy resins (high moldability), and is expected to be used in a variety of applications. In addition, the specific epoxy resin has the advantage that it can be synthesized under milder conditions (molding temperature, for example, 60°C to 160°C) compared to polyester resins (molding temperature, for example, up to 280°C).

[0018] In formula (I), unit M is a rigid unit having a mesogen, while unit A is a flexible unit having no mesogen. By arranging flexible unit A between rigid units M, orientation such as stacking due to π-π interaction is easily generated between rigid units M. In addition, in the specific epoxy resin that can be molded (remolded after polymerization), the orientation of unit M is further promoted during molding. As a result, as shown in FIG. 1, the obtained molded body has high crystallinity and high thermal conductivity due to the oriented mesogen. The characteristic of the specific epoxy resin that the thermal conductivity is improved by molding is a major difference from conventional thermosetting epoxy resins. For example, when a thermosetting epoxy resin has a mesogen group, a region (domain) where the mesogen group is partially oriented is generated in the obtained molded body. However, the movement of the resin molecular chain is restricted by the three-dimensional crosslinking structure, so that the mesogen group cannot be oriented throughout the entire molded body. In contrast, in the molded body using the specific epoxy resin, the mesogen group is easily oriented throughout the entire molded body. For this reason, the molded article of the specific epoxy resin has higher thermal conductivity than the molded article of the conventional thermosetting epoxy resin. Note that the mechanism explained above is merely speculation and does not affect the scope of the present invention.

[0019] [Curable composition] <Difunctional epoxy monomer containing a mesogenic group (first monomer)> The first monomer contained in the curable composition is a bifunctional monomer having a mesogen group and two epoxy groups as reactive groups. The mesogen group refers to an atomic group that facilitates the development of crystallinity or liquid crystallinity through intermolecular interactions.

[0020] The first monomer is represented, for example, by the following formula (1).

[0021] [ka] In formula (1), M 1 is the mesogenic group, Two a's each represent a single bond or a divalent linking group and may be the same or different.

[0022] A mesogenic group (e.g., M 1 ) may be, for example, a divalent group represented by the following formula (1A):

[0023] [ka] In formula (1A), M 2 and M 3 are each a group selected from the group consisting of an aromatic group, a fused aromatic group, an alicyclic group, and an alicyclic heterocyclic group, and may be the same or different; b is a single bond or -CH 2 -, -O-, -S-, -CH 2 -CH 2 a divalent group selected from the group consisting of -, -CH=CH-, -C≡C-, -CO-, -CO-O-, -CO-NH-, -CH=N-, -CH=NN=CH-, -N=N-, and -N(O)=N-; * indicates the linking position.

[0024] M in formula (1A) 2 and M 3 may be selected from, for example, a hydrocarbon group having a benzene ring and having 6 to 12 carbon atoms, a hydrocarbon group having a naphthalene ring and having 10 to 20 carbon atoms, a hydrocarbon group having a biphenyl structure and having 12 to 24 carbon atoms, a hydrocarbon group having three or more benzene rings and having 12 to 36 carbon atoms, a hydrocarbon group having a condensed aromatic group and having 12 to 36 carbon atoms, and an alicyclic heterocyclic group having 4 to 36 carbon atoms.

[0025] M in formula (1A) 2 and M 3 Specific examples of the alkyl group include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, a cyclohexyl group, a pyridyl group, a pyrimidyl group, and a thiophenylene group, and these may be unsubstituted or may be derivatives having a substituent.

[0026] The substituent is not particularly limited, and examples thereof include an aliphatic hydrocarbon group (which may be linear, branched, or cyclic, and preferably has 20 or less carbon atoms), a halogen atom, and the like. However, the first monomer is a bifunctional monomer. Therefore, it is preferable that the substituent does not contain a reactive group that participates in the chain growth reaction of the cured product (polymer) under the synthesis conditions of this embodiment. This is to suppress the formation of a crosslinked structure in the obtained specific epoxy resin.

[0027] In formula (1A), M 2 and M 3 There are no particular limitations on b linking the above divalent groups, but from the viewpoint of further promoting crystallization of the mesogenic group and / or from the viewpoint of antioxidant and chemical resistance, a single bond or a conjugated bond (-CH=CH-, -C≡C-, -CO-, -CO-NH-, -CH=N-, -CH=NN=CH-, -N=N-, and -N(O)=N-) is preferred, and a single bond is more preferred.

[0028] In addition, a mesogenic group (e.g., M 1 Specific examples of the divalent group include biphenyl, terphenyl, quaterphenyl, stilbene, diphenyl ether, 1,2-diphenylethylene, diphenylacetylene, benzophenone, phenylbenzoate, phenylbenzamide, azobenzene, 2-naphthoate, and phenyl-2-naphthoate, and are preferably groups obtained by removing two hydrogen atoms from biphenyl, terphenyl, and quaterphenyl, and more preferably groups obtained by removing two hydrogen atoms from a biphenyl group (for example, a biphenylene group represented by the following formula (1B)). In formula (1B), * represents a linking position. These groups may be unsubstituted or may be derivatives having a substituent. Examples of the substituent include those similar to those described above, and the same applies to preferred embodiments.

[0029] [ka]

[0030] In formula (1), the mesogenic group M 1 The two a's that bond the epoxy group to the aryl group are each independently a single bond or a divalent linking group. The divalent linking group is not particularly limited, and examples thereof include substituted or unsubstituted linear, branched, or cyclic hydrocarbon groups (e.g., having 1 to 10 carbon atoms) that may have a heteroatom. Examples of the heteroatom include an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom. Examples of the substituent include those similar to those described above, and the preferred embodiments are also the same. In formula (1), a is, for example, * 1 -O-CH 2 -* 2 (* 1 is mesogen M 1 Indicates the connection position with * 2 represents the linking position with the epoxy group).

[0031] The curable composition of the present embodiment may contain one type of first monomer, or may contain two or more types of first monomers.

[0032] <Difunctional amine monomer (second monomer)> The second monomer contained in the curable composition contains at least one amino group and is represented by the following formula (2).

[0033] [ka] In formula (2), Y is a sulfur atom (S), an oxygen atom (O), or -N(R 4 )-, R 2 , R 3 and R 4 are groups not containing the mesogenic group, and R 2 and R 4 may be the same or different, R 2 and R 3 may be linked to form a ring, R 2 and R 4 may be linked to form a ring, R 3 and R 4 may be linked to form a ring, m is an integer of 0 or 1.

[0034] In formula (2), R 2 , R 3 and R 4 Since R does not contain a mesogenic group, the second monomer constitutes a flexible unit A in the formula (I) of the specific epoxy resin, and promotes the orientation of the rigid unit M. 2 , R 3 and R 4 Examples of the mesogen group not contained in the second monomer include the same mesogen group as the first monomer, and the preferred embodiments are also the same. In addition, by adjusting the properties (chemical structure) of the second monomer, it is also possible to adjust the thermal properties (e.g., thermal conductivity, melting point, etc.) and mechanical properties (tensile strength, tensile modulus, breaking strain, toughness, etc.) of the specific epoxy resin obtained.

[0035] In formula (2), R 2 , R 3 and R 4 is not particularly limited except that it does not contain a mesogenic group, and may be, for example, a substituted or unsubstituted aliphatic group that may contain a heteroatom. The aliphatic group may be linear, branched, or cyclic. Examples of the heteroatom include an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom.

[0036] R 2 , R 3 and R 4 The main chain of may be an aliphatic group that may contain heteroatoms. For example, R 2 , and R 4 may be a monovalent aliphatic group having 1 to 38 carbon atoms in the main chain, R 3 R may be a divalent aliphatic group having 1 to 38 carbon atoms in the main chain. 2 and R 3When R 2 and R 4 When R 3 and R 4 When they are linked to form a ring, the main chain may have 2 to 38 carbon atoms, for example.

[0037] R 2 , R 3 and R 4 The substituent that may be carried by R is not particularly limited, and examples thereof include an aliphatic hydrocarbon group (which may be linear, branched, or cyclic, and preferably has 20 or less carbon atoms), a halogen atom, etc. 2 , R 3 and R 4 may contain an aromatic group (preferably having 20 or less carbon atoms). However, the second monomer is a bifunctional monomer. Therefore, it is preferable that the substituent does not contain a reactive group that participates in the chain growth reaction of the cured product (polymer) under the synthesis conditions of this embodiment. This is to suppress the formation of a crosslinked structure in the obtained specific epoxy resin. Examples of substituents that should not be contained include a carboxy group (-COOH) and the like.

[0038] The second monomer has one primary aliphatic amino group (-NH 2 ) (when m=0 in formula (2)). In this case, each of the two hydrogen atoms contained in the primary aliphatic amino group is capable of reacting with an epoxy group. The second monomer may also have two secondary aliphatic amino groups (-NH-) capable of reacting with one epoxy group (when m=1 and Y is -N(R 4 Here, the term "aliphatic amino group" refers to an amino group in which an aliphatic group is directly bonded to the nitrogen atom. Therefore, for example, amino groups contained in aniline, pyridine, etc. are not included in the term "aliphatic amino group" in the present specification.

[0039] The second monomer may also have one secondary aliphatic amino group (-NH-) capable of reacting with one epoxy group, and one thiol group (-SH) or one hydroxyl group (-OH) capable of reacting with one epoxy group (when m=1 and Y is a sulfur atom (S) or an oxygen atom (O) in formula (2)).

[0040] The total number of atoms in the second monomer may be, for example, 4 to 200 or 6 to 40.

[0041] Examples of the second monomer include compounds represented by formulas (2A) to (2E) shown in FIG. The compound of formula (2A) is a piperazine, and in formula (2), m=1 and Y is -N(R 4 )- and R 2 and R 4 is linked to -CH 2 CH 2 - Form R 3 Ha-CH 2 CH 2 -It is. The compound of formula (2B) is a compound of formula (2) in which m=1 and Y is -N(R 4 )- and R 2 and R 4 Ha-CH 3 and R 3 -C 6 H 12 -It is. The compound of formula (2C) is a compound of formula (2), wherein m=1, Y is -S-, and R 2 Ha-CH 2 CH 3 and R 3 Ha-CH 2 CH 2 -It is. The compound of formula (2D) is a compound of formula (2) in which m=0 and the moiety other than the primary amino group is R 2 It is. The compound of formula (2E) is a compound of formula (2) in which m=0 and the moiety other than the primary amino group is R 2 Five R 5are each a hydrogen atom, an aliphatic group (preferably having 1 to 6 carbon atoms), or a halogen atom.

[0042] Stoichiometrically, the first monomer and the second monomer react in equivalent amounts (molar ratio 1:1), and in the specific epoxy resin obtained, the molar ratio (unit M / unit A) is 1:1. Therefore, in the curable composition, it is preferable that the number of moles of the first monomer and the number of moles of the second monomer are approximately equal. For example, in the curable composition, the molar ratio (first monomer / second monomer) may be 0.9 to 1.1.

[0043] The curable composition of the present embodiment may contain one type of second monomer, or may contain two or more types of second monomers.

[0044] <Difunctional monomer (third monomer)> The curable composition of the present embodiment may further contain, as an optional component, a bifunctional monomer represented by the following formula (3) (hereinafter, sometimes referred to as a "third monomer").

[0045] [ka] In formula (3), Z 1 and Z 2 are each a reactive group selected from the group consisting of an epoxy group, an isocyanate group, and a vinyl group, c is a divalent group that does not contain the mesogenic group.

[0046] Z in formula (3), which is the reactive group of the third monomer 1 and Z 2 (more specifically, an epoxy group, an isocyanate group, or a vinyl group) is reacted with a reactive group (specifically, -NH 2, -NH-, -OH, or -SH). Since the third monomer is a bifunctional polymer, even in a system to which the third monomer is added, the resulting specific epoxy resin does not form a three-dimensional crosslinked structure, but has a linear structure and exhibits thermoplasticity.

[0047] The specific epoxy compound obtained by curing (polymerizing) the curable composition containing the third monomer contains, in addition to the unit MA represented by formula (I), a unit XA composed of a unit X derived from the third monomer and a unit A derived from the second monomer represented by formula (II).

[0048] [ka]

[0049] The unit XA is a flexible unit that does not have a mesogen. Examples of mesogen groups that the third monomer does not contain include the same as the mesogen groups of the first monomer, and the same applies to the preferred embodiments. By containing the flexible unit XA, the orientation of the rigid unit M is further promoted, and the obtained molded body is more likely to have higher thermal conductivity. In addition, by adjusting the characteristics (chemical structure), ratio, etc. of the third monomer, it is also possible to adjust the thermal characteristics (e.g., thermal conductivity, melting point, etc.) and mechanical characteristics (tensile strength, tensile modulus, breaking strain, toughness, etc.) of the obtained specific epoxy resin.

[0050] In formula (3), Z 1 and Z 2 is highly reactive and does not require a catalyst, 1 and Z 2 It is preferable that either of Z is an epoxy group. 1 and Z 2 It is preferred that both of the above groups are epoxy groups.

[0051] In formula (3), c is not particularly limited except that it does not contain a mesogenic group, but may be, for example, a substituted or unsubstituted aliphatic group that may contain a heteroatom. The aliphatic group may be linear, branched, or cyclic (e.g., having 2 to 90 carbon atoms). Examples of the heteroatom include an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom.

[0052] The substituent that c in formula (3) may have is not particularly limited, and examples thereof include an aliphatic hydrocarbon group (which may be linear, branched, or cyclic, and preferably has 20 or less carbon atoms), a halogen atom, and the like. In addition, c may contain an aromatic group (preferably has 20 or less carbon atoms) as long as it is a substituent, not a main chain. However, the third monomer is a bifunctional monomer. Therefore, it is preferable that the substituent does not contain a reactive group that participates in the chain growth reaction of the cured product (polymer) under the synthesis conditions of this embodiment. This is to suppress the formation of a crosslinked structure in the obtained specific epoxy resin. Examples of substituents that should not be contained include a carboxy group (-COOH) and the like.

[0053] In addition, in formula (3), c may include at least one structure selected from the group consisting of a polyalkylene oxide structure (e.g., a polyethylene oxide structure having a repeating number of 1 to 25), a polysiloxane structure (e.g., a polydimethylsiloxane structure having a repeating number of 1 to 25), and a fluorinated alkylene structure (e.g., a polyalkylene structure having a repeating number of 1 to 25).

[0054] The total number of atoms in the third monomer may be, for example, 4 to 200 or 6 to 40.

[0055] The third monomer may, for example, be the compounds represented by formulae (3A) and (3B) shown in FIG. The compound of formula (3A) is a compound of formula (3), 1 and Z 2 is an epoxy group, and c is a polyalkylene oxide structure (polyethylene oxide structure). The compound of formula (3B) is a compound of formula (3),1 and Z 2 is an epoxy group, and c is a polysiloxane structure (polydimethylsiloxane structure).

[0056] The melting point of the third monomer is preferably 80° C. or lower. If the melting point is 80° C. or lower, the unit X derived from the third monomer is likely to have sufficient flexibility. The lower limit of the melting point of the third monomer is not particularly limited, but is, for example, −50° C. or higher.

[0057] In addition, in the obtained specific epoxy resin, the ratio of the number of moles of the unit MA to the total number of moles of the unit MA and the unit XA (molar ratio r in the following formula (III)) is not particularly limited, but may be, for example, a molar ratio r = 0.6 to 1.0, or 0.8 to 1.0. By setting the molar ratio r within the above range, it becomes easier to increase the thermal conductivity of the specific epoxy resin. In addition, formula (III) is simply a formula showing the molar ratio of the unit MA and the unit XA in the specific epoxy resin, and does not limit the structure of the specific epoxy resin to a structure in which the unit MA and the unit XA are alternately bonded. The structure of the specific epoxy resin of this embodiment is not particularly limited, and may be, for example, a structure in which the unit MA and the unit XA are randomly bonded, or a structure in which they are alternately bonded. In addition, it may be a block polymer formed of a block consisting of the unit MA and a block consisting of the unit XA.

[0058] [ka]

[0059] In order to obtain a specific epoxy resin in which the molar ratio r in formula (III) falls within the above range, in the curable composition, the ratio of the number of moles of the first monomer to the total number of moles of the first monomer and the third monomer may be set to 0.6 to 1.0, or 0.8 to 1.0, similarly to the molar ratio r.

[0060] In addition, stoichiometrically, the first monomer and the second monomer react in equivalent amounts (molar ratio 1:1), and the third monomer and the second monomer also react in equivalent amounts (molar ratio 1:1). Therefore, in the curable composition, it is preferable that the total number of moles of the first monomer and the third monomer and the number of moles of the second monomer are approximately equal. For example, in the curable composition, the ratio (total number of moles of the first monomer and the third monomer / number of moles of the second monomer) may be 0.9 to 1.1.

[0061] The curable composition of the present embodiment may contain one type of third monomer, or may contain two or more types of third monomers.

[0062] As described above, the curable composition from which the specific epoxy resin of the present embodiment can be obtained contains the first monomer and the second monomer, and may further contain a third monomer as an optional component. The curable composition may further contain other monomers different from the first to third monomers, or may not contain other monomers, within the range in which the effects of the present invention are achieved. From the viewpoint of obtaining better effects of the present invention, it is preferable that the curable composition does not contain other monomers. For example, when the curable composition does not contain a third monomer, the total content of the first monomer and the second monomer in the total amount of the curable composition may be 90 mol% or more, 95 mol% or more, or 100 mol%. When the curable composition contains a third monomer, the total content of the first monomer, the second monomer, and the third monomer in the total amount of the curable composition may be 90 mol% or more, 95 mol% or more, or 100 mol%.

[0063] [Method of synthesis of specific epoxy resin] The synthesis method of the specific epoxy resin is not particularly limited, and the specific epoxy resin can be synthesized by a general-purpose method. Compared with polyester resins, the specific epoxy resin can be synthesized under milder conditions (low reaction temperature). For example, a solvent, a polymerization initiator, etc. are added to the curable composition (monomer mixture) of the present embodiment as necessary, and the mixture is reacted at a temperature of 20°C to 150°C for 2 hours to 24 hours to obtain a desired specific epoxy compound.

[0064] [Physical properties of specific epoxy resins] The specific epoxy resin of this embodiment preferably has a thermal conductivity of 1 W / mK or more for a molded body made of only the specific epoxy resin. In this way, the thermal conductivity of the specific epoxy resin itself is sufficiently high, so that, for example, additives such as thermally conductive fillers are not required, or the content of additives can be reduced. The molding method of the molded body and the method of measuring the thermal conductivity may be, for example, a method (press molding) described in the examples below to mold the molded body and obtain the thermal conductivity. In addition, the upper limit of the thermal conductivity of the molded body made of only the specific epoxy resin is not particularly limited, but may be, for example, 20 W / mK or less, or 10 W / mK or less.

[0065] The specific epoxy resin is preferably a crystalline resin and preferably has a melting point. The crystallinity and melting point are expressed by orienting the unit M containing a mesogen group of the specific epoxy resin (see FIG. 1). The melting point of the specific epoxy resin is preferably 200° C. to 300° C., for example. If the melting point is 200° C. or higher, the resin can have high heat resistance despite being a thermoplastic resin, and at the same time, if the melting point is 300° C. or lower, sufficient moldability can be maintained. The crystallinity and melting point of the specific epoxy resin can be measured by thermal analysis using a differential scanning calorimeter (DSC) or X-ray diffraction (XRD), for example, as described in the examples below.

[0066] In addition, the specific epoxy resin is preferably such that the breaking strain of a molded product made only of the specific epoxy resin is 10% or more. The specific epoxy resin of this embodiment has a flexible unit A (and, if necessary, a unit X) in addition to the rigid unit M. A molded product using such a specific epoxy resin can have high toughness. The upper limit of the breaking strain of a molded product made only of the specific epoxy resin is not particularly limited, but may be, for example, 60% or less, or 50% or less. The molding method of the molded product and the breaking strain measurement method may be, for example, a method (press molding) described in the examples below to mold the molded product and measure the breaking strain.

[0067] [Resin composition] The resin composition containing the specific epoxy resin will now be described. As described above, since the specific epoxy resin is a thermoplastic resin, the resin composition containing the specific epoxy resin can be molded by various molding methods.

[0068] The resin composition may contain one type of specific epoxy resin, or may contain two or more types of specific epoxy resin. The resin composition may be composed of only the specific epoxy resin, or may contain other components. The content of the specific epoxy resin in the resin composition is not particularly limited, but may be, for example, 10% by mass to 100% by mass, 20% by mass to 100% by mass, or 50% by mass to 100% by mass, from the viewpoint of obtaining better effects of the present invention.

[0069] Since the specific epoxy resin itself has high thermal conductivity, a molded body having high thermal conductivity can be obtained without containing a thermally conductive filler. However, in order to obtain a molded body having higher thermal conductivity, the resin composition may contain a thermally conductive filler in addition to the specific epoxy resin. The type of the thermally conductive filler is not particularly limited, but for example, it is preferable that the thermal conductivity of the thermally conductive filler itself is 5 W / mK or more, 10 W / mK or more, or 100 W / mK or more. The thermally conductive filler may be particles (spheres, platelets, whiskers), fibers (short fibers or continuous fibers), etc. Examples of the thermally conductive filler include ceramics, such as boron nitride (e.g., hexagonal boron nitride, h-BN), silicon nitride (β-Si 3 N 4 ), inorganic nitrides such as aluminum nitride (AlN); diamond; aluminum oxide (Al 2 O 3 ), silicon oxide (SiO 2), inorganic oxides such as magnesium oxide (MgO); β-silicon carbide (β-SiC); etc. Among them, boron nitride is preferable. Boron nitride has advantages such as (i) improving the physical properties of the composition as well as the thermal conductivity, (ii) low reactivity and high stability, and (iii) being less expensive than metal-based fillers. In addition, as the thermally conductive filler, metals such as aluminum (Al), copper (Cu), silver (Ag), etc.; and carbon materials such as carbon nanotubes (CNT), graphene, graphite, etc. may be used. The resin composition may contain one type of thermally conductive filler, or may contain two or more types of thermally conductive fillers.

[0070] The content of the thermally conductive filler in the resin composition is not particularly limited, but may be, for example, 1% by mass to 90% by mass, 10% by mass to 80% by mass, or 10% by mass to 50% by mass. If the content of the thermally conductive filler is within the above range, a molded product having the desired high thermal conductivity and sufficient mechanical properties is easily obtained.

[0071] The resin composition may further contain general-purpose additives other than the thermally conductive filler, as necessary, within the scope of the effects of the present invention. Examples of general-purpose additives include fillers, antioxidants, light stabilizers, flame retardants, heat stabilizers, antistatic agents, plasticizers, lubricants, crystallization accelerators, colorants, and foaming agents.

[0072] The resin composition may contain only the specific epoxy resin as the thermoplastic resin, or may further contain other thermoplastic resins different from the specific epoxy resin within the range in which the effects of the present invention are achieved. From the viewpoint of obtaining better effects of the present invention, it is preferable that the resin composition does not contain other thermoplastic resins. The content of the specific epoxy resin in all thermoplastic resins contained in the resin composition is, for example, 90 mass% or more, 95 mass% or more, or 100 mass%.

[0073] The resin composition can be prepared by mixing the specific epoxy resin and, if necessary, other components such as a thermally conductive filler, by a general-purpose method.

[0074] [Molded body] The molded article obtained by molding the resin composition containing the specific epoxy resin described above will now be described. The molded article has substantially the same composition as the resin composition used for molding.

[0075] The molding method for the molded body is not particularly limited, and any known molding method for thermoplastic resins can be used, such as press molding, injection molding, blow molding, vacuum molding, extrusion molding, and calendar molding.

[0076] The orientation of the unit M of the specific epoxy resin is further promoted during molding (see FIG. 1), and as a result, the crystallinity and thermal conductivity of the obtained molded body are further improved due to the oriented mesogen group. The thermal conductivity of the molded body made only of the specific epoxy resin is preferably 1 W / mK or more. The upper limit of the thermal conductivity of the molded body made only of the specific epoxy resin is not particularly limited, but may be, for example, 20 W / mK or less, or 10 W / mK or less. The molded body can further improve its thermal conductivity by containing a thermally conductive filler. The thermal conductivity may be measured, for example, by the method described in the examples below.

[0077] Since the specific epoxy resin contained in the molded body has a high melting point, the molded body also has a high melting point (for example, 200°C to 300°C) and has high heat resistance. In addition, since the molded body contains the specific epoxy resin, it has high toughness. For example, the breaking strain of the molded body made only of the specific epoxy resin is preferably 10% or more. The upper limit of the breaking strain of the molded body made only of the specific epoxy resin is not particularly limited, but may be, for example, 60% or less, or 50% or less. In general, when the molded body contains other components (for example, conductive filler) other than the resin component, the breaking strain tends to decrease. However, since the specific epoxy resin has high toughness, the molded body of this embodiment can maintain a sufficiently high breaking strain value even if it contains an appropriate amount of other components (for example, conductive filler). The breaking strain may be measured by, for example, the method described in the examples described later.

[0078] As described above, the molded article of the present embodiment is excellent in thermal conductivity, heat resistance, and mechanical properties. In addition, it also has high electrical insulation and high water resistance, which are characteristics of epoxy resins. The molded article of the present embodiment can be used in various applications such as electronic devices. For example, it can be used in cases of personal computers, battery cases, circuit / semiconductor substrates, heat dissipation sheets, automobile headlight cases, and cases of medical devices (cameras, lasers, etc.), which require insulation and thermal conductivity. EXAMPLES

[0079] The present invention will be described below with reference to examples, but the present invention is not limited to these.

[0080] In Examples 1 to 7 and Comparative Examples 1 to 3, epoxy thermoplastic resins were synthesized from curable compositions (monomer mixtures) and resin compositions containing the resins were prepared. The molar ratios of the monomers contained in the curable compositions of Examples 1 to 7 and Comparative Examples 1 to 3 and the composition ratios (mass%) of the resin compositions are shown in Table 1.

[0081] [Example 1] An epoxy thermoplastic resin was synthesized from a curable composition containing two types of monomers, 4,4'-diglycidyloxybiphenyl (BP) and piperazine (PZ) (see Figure 4), to obtain a resin composition consisting only of this epoxy thermoplastic resin. BP is a bifunctional epoxy monomer (first monomer) containing a mesogen group, and PZ is a bifunctional amine monomer (second monomer) represented by formula (2).

[0082] First, a mixture of BP and PZ (molar ratio BP:PZ=1:1) was added to a reaction vessel containing a solvent (N,N'-dimethylformamide (DMF)) so that the solid content was about 20-30% by weight, to obtain a reaction mixture. Without using a catalyst or an inert atmosphere, the reaction mixture was kept at 80°C for 6 hours, then at 160°C for 2 hours, and then cooled to room temperature and precipitated in a poor solvent (e.g., water). The precipitate (product) was dried to obtain the desired epoxy thermoplastic resin (yield: 93-97% by weight).

[0083] [Example 2] An epoxy thermoplastic resin was synthesized from a curable composition containing three types of monomers (see FIG. 4): BP, PZ, and poly(ethylene glycol) diglycidyl ether (number average molecular weight Mn=500, melting point: 35-40°C) (DGE-PEG500), and a resin composition consisting only of this epoxy thermoplastic resin was obtained. DGE-PEG500 is a bifunctional monomer (third monomer) represented by formula (3).

[0084] In this example, the target epoxy thermoplastic resin was obtained (yield: 91-95% by weight) in the same manner as in Example 1, except that a mixture of BP, PZ, and DGE-PEG500 (molar ratio BP:PZ:DGE-PEG500=0.9:1:0.1) was used instead of the mixture of BP and PZ.

[0085] [Example 3] An epoxy thermoplastic resin was synthesized from a curable composition containing three types of monomers (see FIG. 4): BP, PZ, and poly(ethylene glycol) diglycidyl ether (number average molecular weight Mn=1000, melting point: 40-45°C) (DGE-PEG1000), and a resin composition consisting only of this epoxy thermoplastic resin was obtained. DGE-PEG1000 is a bifunctional monomer (third monomer) represented by formula (3).

[0086] In this example, the target epoxy thermoplastic resin was obtained (yield: 90 to 93% by weight) in the same manner as in Example 2, except that DGE-PEG1000 was used instead of DGE-PEG500.

[0087] [Example 4] A resin composition was prepared by mixing the epoxy thermoplastic resin of Example 1 with a thermally conductive filler, boron nitride (h-BN) (platelet, average particle size: 10 μm) (mass ratio 90:10, see Table 1).

[0088] First, the epoxy thermoplastic resin of Example 1 was dissolved in a solvent (DMF) at a mass ratio (resin:solvent) of 1:2, and stirred at 70°C for 30 minutes to prepare a resin solution. Separately, a thermally conductive filler (h-BN powder) was dispersed in a solvent (DMF) at a mass ratio (filler:solvent) of 1:3, and ultrasonically treated for 10 minutes to prepare a thermally conductive filler dispersion. The resin solution and the thermally conductive filler dispersion were mixed so that the mass ratio (epoxy thermoplastic resin:thermally conductive filler) was 90:10, and the mixture was passed through a three-roll mill for five cycles, after which the mixture was precipitated in a poor solvent and dried to obtain the desired resin composition.

[0089] [Examples 5 to 7] In Examples 5 to 7, resin compositions were prepared by mixing the epoxy thermoplastic resin of Example 1 with a thermally conductive filler (h-BN) in the same manner as in Example 4. Specifically, the target resin compositions were obtained by the same method as in Example 4, except that the mixing ratio of the resin solution to the thermally conductive filler dispersion was changed so that the mass ratio of the epoxy thermoplastic resin to the thermally conductive filler was the value shown in Table 1 (epoxy thermoplastic resin:thermal conductive filler=75-20:25-80).

[0090] [Comparative Example 1] The target epoxy-based thermoplastic resin was synthesized (yield: 91-95% by weight) in the same manner as in Example 1, except that bisphenol A diglycidyl ether (DGEBA, see FIG. 4) was used instead of BP, and a resin composition composed only of this epoxy-based thermoplastic resin was obtained.

[0091] [Comparative Examples 2 and 3] In Comparative Examples 2 and 3, resin compositions were prepared by mixing the epoxy thermoplastic resin of Comparative Example 1 with a thermally conductive filler (h-BN). Specifically, the epoxy thermoplastic resin of Comparative Example 1 was used instead of the epoxy thermoplastic resin of Example 1, and the mixing ratio of the resin solution to the thermally conductive filler dispersion was changed so that the mass ratio of the epoxy thermoplastic resin to the thermally conductive filler was the value shown in Table 1 (epoxy thermoplastic resin:thermal conductive filler=75-50:25-50), and the target resin compositions were obtained by the same method as in Example 4.

[0092] [Table 1]

[0093] [evaluation] <Crystalline> The epoxy thermoplastic resins used in Examples 1 to 7 and Comparative Examples 1 to 3 were analyzed by X-ray diffraction (XRD). As a result, it was confirmed that the epoxy thermoplastic resins used in Examples 1 to 7 were crystalline resins having a crystalline phase. In the epoxy thermoplastic resins of Examples 1 to 7, the biphenylene group (-C 6 H 4 -C 6 H 4 It is presumed that the - groups were oriented as mesogenic groups to form a crystalline phase.

[0094] On the other hand, the epoxy thermoplastic resins used in Comparative Examples 1 to 3 were amorphous resins that did not have a crystalline phase. In the epoxy thermoplastic resins of Comparative Examples 1 to 3, the group (-C 6 H 4 -C(CH 3 ) 2 -C 6 H 4 Although the benzene ring is contained, it is presumed that the degree of rotational freedom of the ring is too high to function as a mesogenic group and thus the orientation could not be achieved.

[0095] <Moldability> The resin compositions of Examples 1 to 7 and Comparative Examples 1 to 3 were hot pressed under the molding conditions shown in Table 1 (temperatures about 5 to 15°C higher than Tm), and then immediately transferred to a cooling press (at room temperature) and cooled at the same pressure for 1 minute or more to remove the molded bodies. As a result, sheet-shaped molded bodies (thickness 0.25 mm to 0.35 mm) were obtained from all the resin compositions of Examples 1 to 7 and Comparative Examples 1 to 3. From these results, it was confirmed that the resin compositions of Examples 1 to 7 and Comparative Examples 1 to 3 have high moldability despite being epoxy resins.

[0096] <Glass transition temperature (Tg), melting point (Tm)> The glass transition temperature (Tg) and melting point (Tm) of the resin compositions of Examples 1 to 7 and Comparative Examples 1 to 3 were measured by a differential scanning calorimeter (DSC) (measurement temperature range: 20 to 280°C, heating rate: 10°C / min, sapphire standard substance). The results are shown in Table 1. All of the resins of Examples 1 to 7 were crystalline resins with high melting points (Tm) of 200°C or higher. This confirmed that the epoxy thermoplastic resins of Examples 1 to 7 had moldability and could give molded articles with high heat resistance.

[0097] On the other hand, the melting point (Tm) could not be confirmed for the resin compositions of Comparative Examples 1 to 3. When the softening points of the resin compositions of Comparative Examples 1 to 3 were measured by dynamic viscoelasticity measurement (DMA), they were low values ​​of 90 to 100° C. This shows that the molded articles of Comparative Examples 1 to 3 have lower heat resistance than the molded articles of Examples 1 to 7.

[0098] <Thermal conductivity (λ)> The thermal conductivity (λ) in the in-plane direction of the molded bodies of Examples 1 to 7 and Comparative Examples 1 to 3 was calculated using the following formula. The results are shown in Table 1.

[0099] λ=α ρ C p λ: thermal conductivity, α: thermal diffusivity, ρ: density, C p : Specific heat capacity

[0100] The thermal diffusivity (α) in the in-plane direction was measured by the Angstrom method at room temperature and a frequency of 0.2 Hz using an optical AC thermal diffusivity measuring device (LaserPIT, manufactured by Advance Riko Co., Ltd.). The density (ρ) was measured by the immersion method. The results (density) are shown in Table 1. The specific heat capacity (C p ) was measured using DSC under the same conditions as those for Tg and Tm described above.

[0101] The molded bodies of Examples 1 to 3 and Comparative Example 1 did not contain a thermally conductive filler (h-BN) and were composed only of an epoxy-based thermoplastic resin. As shown in Table 1, the molded bodies of Examples 1 to 3 had higher thermal conductivity than the molded body of Comparative Example 1. This is presumably because the mesogen groups of the thermoplastic resins of Examples 1 to 3 were oriented to form a crystalline phase, and it was confirmed that the thermoplastic resins themselves had sufficiently high thermal conductivity even without containing a thermally conductive filler.

[0102] In addition, when Examples 1 to 3 are compared, the molded articles of Examples 2 and 3 using three types of monomers had higher thermal conductivity than the molded article of Example 1 using two types of monomers. This is presumably because Examples 2 and 3 contained monomers (DGE-PEG500, DGE-PEG1000) that constitute flexible units, which made it easier for the mesogen groups to move (become oriented).

[0103] To evaluate the effect of the thermally conductive filler (h-BN) in the resin composition, Examples 1 and 4 to 7 (using crystalline resin) in which the content of the thermally conductive filler was changed were compared. Similarly, Comparative Examples 1 to 3 (using amorphous resin) in which the content of the thermally conductive filler was changed were compared. In both Examples 1 and 4 to 7 (crystalline resin) and Comparative Examples 1 to 3 (amorphous resin), the thermal conductivity improved as the content of the thermally conductive filler increased. However, comparing Example 5 with Comparative Example 2 (both with a thermally conductive filler content of 25% by mass), the thermal conductivity of Example 5 was higher. Similarly, comparing Example 6 with Comparative Example 3 (both with a thermally conductive filler content of 50% by mass), the thermal conductivity of Example 6 was higher. This is because the thermal conductivity of the crystalline resin used in Examples 5 and 6 was higher than that of the amorphous resin used in Comparative Examples 2 and 3. This confirmed that the amount of thermally conductive filler contained could be reduced by using a crystalline resin with high thermal conductivity.

[0104] <Tensile Strength, Tensile Modulus, and Strain at Break> The tensile strength, tensile modulus, and breaking strain of the molded bodies of Examples 1 to 7 and Comparative Examples 1 to 3 were measured using an electromechanical testing machine (EZ-LX) at a displacement rate of 1 mm / min according to ASTM D638. The elongation was measured using a video extensometer. The results are shown in Table 1.

[0105] The molded bodies of Examples 1 to 6 had practically acceptable values ​​(practical acceptable mechanical properties) for the tensile strength, tensile modulus, and breaking strain. In addition, since the values ​​of Examples 1 to 3, which have different monomer compositions, were different, it was confirmed that the mechanical properties could be adjusted by adjusting the monomer composition of the curable composition.

[0106] The fracture strains of Examples 1 to 3 are compared with that of Comparative Example 1. None of the molded bodies of Examples 1 to 3 and Comparative Example 1 contain a thermally conductive filler (h-BN) and are composed of only an epoxy-based thermoplastic resin. Compared with the molded body of Comparative Example 1, the molded bodies of Examples 1 to 3 have a high fracture strain (10% or more) and high toughness.

[0107] Examples 1 and 4 to 7 are compared. As the content of the thermally conductive filler (h-BN) increases, the thermal conductivity improves while the mechanical properties (for example, breaking strain) decrease. In Example 7, the mechanical properties could not be evaluated. From this result, it is presumed that, from the viewpoint of obtaining a molded product having high mechanical properties, the content of the thermoplastic resin (epoxy thermoplastic resin) in the molded product (resin composition) is preferably more than 20 mass%, and more preferably 50 mass% or more. That is, from the same viewpoint, the content of the thermally conductive filler is preferably less than 80 mass% or 50 mass% or less. For the evaluation of mechanical properties, a thin sheet-like molded body (test piece) was used that can also be used for evaluating thermal conductivity. It is presumed that if a thicker molded body is used, sufficient mechanical properties that are not problematic in practical use can be obtained even when the resin composition of Example 7 is used.

[0108] <Cross-section observation of molded body> The cross sections of the molded bodies of Examples 1 and 4 to 6 (fracture surfaces of the samples after measuring the fracture strain) were observed using a scanning electron microscope (SEM). FIG. 5 shows the pressing direction (z direction) of the molded body (plate-like body) 10, and the x and y directions perpendicular to the pressing direction. The x and y directions are orthogonal to each other. In the molded body 10, a cross section approximately parallel to the xz plane was observed from the y direction. As shown in the SEM image in FIG. 5, it was confirmed that the crystalline phase of the resin was oriented along the x direction (the flow direction of the resin during press molding). In Examples 4 to 6, it was confirmed that the thermally conductive filler (h-BN) was also oriented in the same direction as the crystalline phase of the resin. [Industrial Applicability]

[0109] The thermally conductive epoxy thermoplastic resin of the present invention is remoldable and has high thermal conductivity, making it suitable for a variety of applications, such as housings for electronic devices.

Claims

1. A heat-conductive epoxy thermoplastic resin obtained by curing a curable composition, The curable composition is A difunctional epoxy monomer containing a mesogenic group, A thermally conductive epoxy thermoplastic resin comprising a difunctional amine monomer represented by the following formula (2). 【Chemistry 1】 In equation (2), Y consists of a sulfur atom (S), an oxygen atom (O), and -N (R). ４ ) - is one selected from the group consisting of R ２ , R ３ and R ４ Each of these is a group that does not contain the aforementioned mesogenic group, R ２ and R ４ They may be the same or different. R ２ and R ３ They may be connected to form a ring. R ２ and R ４ may be linked to form a ring, R ３ and R ４ They may be connected to form a ring. m is an integer, either 0 or 1.

2. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the bifunctional epoxy monomer is represented by the following formula (1). 【Chemistry 2】 In equation (1), M １ This is the aforementioned mesogenic group, The two 'a's are either single bonds or divalent linking groups, and may be the same or different.

3. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the mesogenic group is represented by the following formula (1A). 【Transformation 3】 In equation (1A), M ２ and M ３ These are groups selected from the group consisting of aromatic groups, fused aromatic groups, alicyclic groups, and alicyclic heterocyclic groups, and may be the same or different. b is a single bond or -CH ２ -, -O-, -S-, -CH ２ -CH ２ A divalent group selected from the group consisting of -, -CH=CH-, -C≡C-, -CO-, -CO-O-, -CO-NH-, -CH=N-, -CH=N-N=CH-, -N=N-, and -N(O)=N-, * indicates the connection position.

4. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the mesogenic group is represented by the following formula (1B). 【Chemistry 4】 In equation (1B), * represents the connection position.

5. In formula (2) representing the aforementioned difunctional amine monomer, R ２ , R ３ and R ４ The thermally conductive epoxy thermoplastic resin according to claim 1, wherein each of the groups is a substituted or unsubstituted aliphatic group that may contain a heteroatom.

6. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the difunctional amine monomer has one primary aliphatic amino group or two secondary aliphatic amino groups.

7. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the curable composition further comprises a bifunctional monomer represented by the following formula (3). 【Transformation 5】 In equation (3), Z １ and Z ２ These are reactive groups selected from the group consisting of epoxy groups, isocyanate groups, and vinyl groups, respectively. c is a divalent group that does not contain the aforementioned mesogenic group.

8. The thermally conductive epoxy thermoplastic resin according to claim 7, wherein in formula (3), c is a substituted or unsubstituted aliphatic group which may contain a heteroatom.

9. The thermally conductive epoxy thermoplastic resin according to claim 7, wherein in formula (3), c comprises at least one structure selected from the group consisting of a polyalkylene oxide structure, a polysiloxane structure, and a fluorinated alkylene structure.

10. The thermally conductive epoxy thermoplastic resin according to claim 7, wherein the melting point of the bifunctional monomer represented by formula (3) is 80°C or lower.

11. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the thermal conductivity of a molded article consisting solely of the thermally conductive epoxy thermoplastic resin is 1 W / mK or higher.

12. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the resin is a crystalline resin.

13. A thermally conductive epoxy thermoplastic resin according to claim 1, having a melting point.

14. The thermally conductive epoxy thermoplastic resin according to claim 13, wherein the melting point is 200°C to 300°C.

15. The thermally conductive epoxy thermoplastic resin according to claim 1, wherein the fracture strain of a molded article consisting solely of the thermally conductive epoxy thermoplastic resin is 10% or more.

16. A resin composition comprising a thermally conductive epoxy thermoplastic resin according to any one of claims 1 to 15.

17. Furthermore, the resin composition according to claim 16, further comprising a thermally conductive filler.

18. A molded article obtained by molding the resin composition according to claim 16.

19. An electronic device comprising the molded body described in claim 18.

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