Epoxy compounds, compositions obtained therefrom, semiconductor devices, electronic devices, articles, and methods for manufacturing articles.

Abstract

To provide an epoxy compound having improved heat radiation properties, a composition prepared from the epoxy compound, a semiconductor device prepared from the epoxy compound, an electronic device prepared from the epoxy compound, an article prepared from the epoxy compound, and a method of preparing the article.SOLUTION: The present invention discloses an epoxy compound including a 5-membered aromatic heterocyclic ring represented by, for example, chemical formula 11a.SELECTED DRAWING: Figure 2

Description

Technical Field

[0001] The present invention relates to an epoxy compound, a composition obtained therefrom, a semiconductor device, an electronic device, an article, and a method for manufacturing an article.

Background Art

[0002] Due to the trend of complication and high density of semiconductor circuits, the thermal stability of molding materials is important for releasing heat generated in semiconductor circuits. As a molding material for semiconductor packages, an epoxy molding compound (EMC) containing a thermosetting resin is used. In order to increase the thermal conductivity of the epoxy molding compound, a high thermal conductivity inorganic filler is added. However, despite the addition of the high thermal conductivity inorganic filler, the increase in the thermal conductivity of the epoxy molding compound is negligible.

Summary of the Invention

Problems to be Solved by the Invention

[0003] The problem to be solved by the present invention is to provide an epoxy compound having an improved heat dissipation characteristic by having a new structure. The problem to be solved by the present invention is also to provide an epoxy resin composition containing the epoxy compound. The problem to be solved by the present invention is also to provide a semiconductor device including a cured product obtained from the composition. The problem to be solved by the present invention is also to provide an electronic device including a cured product obtained from the composition. The problem to be solved by the present invention is also to provide an article including a cured product obtained from the composition. The problem to be solved by the present invention is also to provide a method for manufacturing the article. [Means for Solving the Problem]

[0004] On one side, An epoxy compound having a 5-membered aromatic heterocyclic ring represented by the following Chemical Formula 1 or the following Chemical Formula 2 is provided: [Chemical Formula 1] E1-(M1) , , 12 , a4 , b3 , , , 12 , 12 , b4 , a3 , -(L1) b1 -M3-(L2) b2 -(M2) a2 -E2 [Chemical Formula 2] E1-(M1) a1 -(L1) b1 -M3-(L2) <​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​Alkynylene group, or substituted or unsubstituted C4-C 12 It is an alkadierine group. E1 and E2 are independently epoxy-containing groups. a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2. [ka] In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 and R 12 These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C 10 It is an alkyl group.

[0005] From another perspective, Epoxy compounds and, An epoxy resin composition containing a curing agent is provided.

[0006] Furthermore, from another perspective, Substrate, semiconductor, The epoxy resin composition comprises a cured product of an epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or A semiconductor device is provided, comprising an adhesive portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent.

[0007] Furthermore, from another perspective, Substrate, electronic components, The epoxy resin composition comprises a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or An electronic device is provided, comprising an adhesive part made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent.

[0008] Furthermore, from another perspective, Substrate and The epoxy resin composition comprises a cured product of an epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or An article is provided comprising an adhesive portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent.

[0009] Furthermore, from another perspective, The steps include providing the epoxy resin composition described above on a substrate, A method for manufacturing an article is provided, comprising the step of curing the epoxy resin composition. [Effects of the Invention]

[0010] According to the present invention, the thermal conductivity of a cured epoxy resin composition containing an epoxy compound having a five-membered aromatic heterocycle is improved, and the thermal stability of semiconductor devices, electronic devices, and articles containing such cured products is improved. [Brief explanation of the drawing]

[0011] [Figure 1] This graph shows the change in the thermal conductivity of the compound due to the thermal conductivity of the filler. [Figure 2] This graph shows the change in the thermal conductivity of a compound based on the thermal conductivity of the resin. [Figure 3] This is a schematic cross-sectional view of a semiconductor device based on one example. [Figure 4] This is a schematic cross-sectional view of an electronic device based on one example. [Figure 5] This is a schematic plan view of an electronic device based on a real-world example. [Modes for carrying out the invention]

[0012] Various embodiments are illustrated in the accompanying drawings. However, the concept of the present invention can be embodied in many different forms and should not be construed as being limited to the embodiments described herein. Rather, these embodiments are provided to ensure that this disclosure is thorough and complete, and will fully convey the scope of the concept of the present invention to those skilled in the art. Identical reference numerals in the drawings refer to identical components.

[0013] When one component is described as being "on top of" another, it can be understood that it may also be directly on top of the other, or that the other component may be interposed between them. In contrast, when one component is described as being "directly on top of" another, it means that no component is interposed between them.

[0014] Terms such as “First,” “Second,” and “Third” may be used herein to describe a variety of components, elements, regions, layers, and / or areas, but such components, elements, regions, layers, and / or areas are not limited by these terms. These terms are used solely to distinguish one component, element, region, layer, or area from other elements, elements, regions, layers, or areas. Accordingly, the first component, element, region, layer, or area described below will also be referred to as the second component, element, region, layer, or area without exception in connection with the teachings herein.

[0015] The terms used herein are for illustrative purposes only and do not limit the concepts of the invention. The singular forms used herein include plural forms, including “at least one,” unless explicitly indicated otherwise. “At least one” is not to be construed as being limited to the singular. As used herein, the terms “and / or” include all any combination of one or more items in the list. The terms “including” and / or “including” as used in the detailed description identify the presence of expressed features, regions, integers, stages, operations, components, and / or ingredients, but do not exclude the presence or addition of one or more other features, regions, integers, stages, operations, components, ingredients, and / or groups thereof.

[0016] Spatially relative terms such as “down,” “underside,” “bottom,” “up,” “top,” and “upper” may be used herein to facilitate the description of the relationship of one component or feature to other components or features. When spatially relative terms are used or acted upon in addition to the directions illustrated in the drawings, they will be understood to be intended to include different orientations of the apparatus. For example, if the apparatus in the drawing is inverted, a component described as “below” or “underside” of another component or feature will be oriented “above” of the other component or feature. Thus, the exemplary term “underside” can encompass both the up and down directions. The apparatus may also be positioned in other directions (rotated 90° or in other directions), and the spatially relative terms used herein will be interpreted in such ways as well.

[0017] Unless otherwise specifically defined, all terms used herein (including technical and scientific terms) have the same meaning as those generally understood by those skilled in the art to which this disclosure pertains. Furthermore, commonly used, dictionary-defined terms should be interpreted to have a meaning consistent with their meaning in the context of the relevant art and the content of this disclosure, and should not be interpreted in an idealized or overly formal sense.

[0018] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic diagrams of idealized embodiments. Thus, deformations from the illustrated shapes should be expected, for example, as a result of manufacturing techniques and / or tolerances. Accordingly, the embodiments described herein should not be construed as being limited to specific shapes of regions as illustrated herein, but include, for example, deviations of shape resulting from manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Furthermore, a corner illustrated as acute may be rounded. Accordingly, the regions illustrated in the drawings are essentially schematic, and their shapes are not intended to illustrate the exact shape of the region and do not limit the scope of the claims.

[0019] While specific examples are described, alternatives, modifications, variations, improvements, and substantial equivalents may arise that are not currently anticipated or foreseeable to the applicant or those skilled in the art. Accordingly, the scope of the claims, which may be filed and modified, is intended to include all such alternatives, modifications, variations, improvements, and substantial equivalents.

[0020] The following provides further details on epoxy compounds, compositions obtained therefrom, semiconductor devices, electronic devices, articles, and methods for manufacturing articles, based on one or more exemplary examples.

[0021] [Composition (I)] One example of an epoxy compound is an epoxy compound having a 5-membered aromatic heterocyclic ring represented by the following chemical formula 1 or chemical formula 2: [Chemical formula 1] E1-(M1) a1 -(L1) b1 -M3-(L2) b2 -(M2) a2 -E2 [Chemical formula 2] E1-(M1) a1 -(L1) b1-M3-(L2) b2 -(M2) a2 -(L5) b5 -A-(L6) b6 -(M4) a3 -(L3) b3 -M6-(L4) b4 -(M5) a4 -E2 In the aforementioned chemical formulas 1 and 2, M1, M2, M4, and M5 are arylene groups selected independently from among the arylene groups represented by the following chemical formulas 3a to 3e. M3 and M6 are heteroarylene groups independently selected from among the heteroarylene groups represented by the following chemical formulas 4a to 4r. L1, L2, L3, L4, L5, and L6 are, independently of each other, -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, -OC(=O)O-, -(CH2)2-C(=O)-, -CH=CH-C(=O)-, -CH=N-, -NH-C(=O)O-, -C(=O)-NH- or -OC(=O)-NH-S(=O)O-, A is a substituted or non-substituted C4-C 12 Alkylene group, substituted or unsubstituted C4-C 12 Alkenylene group, substituted or unsubstituted C4-C 12 Alkynylene group, or substituted or unsubstituted C4-C 12 It is an alkadierine group. E1 and E2 are epoxy-containing groups, independently of each other. a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2. [ka] In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R11 and R 12 These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C 10 It is an alkyl group.

[0022] In the aforementioned chemical formula 2, A is, for example, a halogen-substituted or unsubstituted C4-C 12 Alkylene group, halogen-substituted or unsubstituted C4-C 12 Alkenylene group, halogen-substituted or unsubstituted C4-C 12 Alkynylene group, or C4-C substituted or unsubstituted with halogen 12 This is an alkadienylene group.

[0023] Resins are generally thermal insulators, and the thermal conductivity of conventional resins is approximately 0.1 to 0.2 W / mK. In resins, which are thermal insulators, heat is transferred by the vibrational transmission of phonons, but in conventional resins, the thermal conductivity is low due to phonon scattering. The thermal conductivity of resins used as semiconductor packaging materials is, for example, approximately 0.1 to 0.2 W / mK. Even if a filler with high thermal conductivity is added to such a resin, the increase in the thermal conductivity of the resulting compound is not significant. For example, Figure 1 is a graph showing the change in the thermal conductivity of a compound due to the thermal conductivity of the filler. Figure 1 shows the results of calculating the thermal conductivity of a compound containing a filler and resin, based on the Maxwell model, while increasing the filler content from 0 vol% to 90 vol% in a resin with a thermal conductivity of 0.2 W / mK. As can be seen from Figure 1, when the filler content is 90 vol%, even if the thermal conductivity of the filler rises to 50 W / mK or higher, the thermal conductivity of the compound converges to 5 W / mK. In other words, in a compound containing filler and resin, even if the thermal conductivity of the filler is increased to 100 W / mK, the thermal conductivity of the compound converges to 5 W / mK and does not rise any further.

[0024] In contrast, epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 have a mesogen unit in the main chain containing multiple aromatic rings. The multiple aromatic rings contained in the mesogen unit form π·π stacking, and intermolecular hydrogen bonding increases the chain stiffness of the epoxy compound main chain and increases the molecular ordering. As a result, a phonon transfer pathway is provided within the epoxy compound and / or its cured resin. Therefore, the thermal conductivity of the epoxy compound and / or its cured resin is increased. In particular, the mesogen unit contained in the epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 contains a heteroaromatic ring. The heteroatoms of the heteroaromatic ring provide further phonon transfer pathways by forming further bonds, such as hydrogen bonding, with adjacent epoxy compounds. Therefore, the thermal conductivity of the epoxy compound and / or its cured resin is further increased. Furthermore, epoxy compounds having aromatic heterocycles represented by chemical formula 2 further contain flexible spacers between mesogenic units. The addition of spacers to the epoxy compound can form a liquid crystal-like structure, such as a smectic phase. The inclusion of highly ordered domains, such as this liquid crystal-like structure, increases the regularity of the molecular arrangement of the epoxy compound and / or the resin obtained therefrom. As a result, phonon scattering is suppressed within the epoxy compound and / or its cured resin. Consequently, the thermal conductivity of the epoxy compound and / or its cured resin is further increased. Therefore, the high thermal conductivity of the cured resin obtained from the epoxy compounds represented by chemical formulas 1 and / or 2 significantly increases the thermal conductivity of the compound containing it. For example, Figure 2 is a graph showing the change in thermal conductivity of a compound due to the thermal conductivity of the resin.Figure 2 shows the results of calculating the change in thermal conductivity due to filler content based on the Maxwell model, while fixing the thermal conductivity of the Al2O3 filler, which has a thermal conductivity of 50 W / mK, and increasing the thermal conductivity of the resin from 0.2 W / mK to 1.0 W / mK. As can be seen from Figure 2, when the thermal conductivity of the resin was increased from 0.2 to 1.0 W / mK, the thermal conductivity of the compound increased to 18 W / mK at a filler content of 90 vol%.

[0025] An epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 is also, for example, an epoxy compound having a five-membered aromatic heterocycle represented by the following chemical formulas 5a to 5f: [Chemical formula 5a] E1-M1-L7-M3-L8-M2-E2 [Chemical formula 5b] E1-M1-L7-M3-E2 [Chemical formula 5c] E1-M3-L8-M2-E2 [Chemical formula 5d] E1-M1-M3-M2-E2 [Chemical formula 5e] E1-M1-M3-E2 [Chemical formula 5f] E1-M3-M2-E2 In the aforementioned chemical formulas 5a to 5f, M1 and M2 are independently one or more arylene groups selected from the arylene groups represented by the aforementioned chemical formulas 3a to 3e, M3 is a heteroarylene group selected from the heteroarylene groups represented by the aforementioned chemical formulas 4a to 4r, L7 and L8 are independently -O-, -C(=O)-, -C(=O)O-, or -OC(=O)O-, and E1 and E2 are independently epoxy-containing groups.

[0026] Epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 are also, for example, epoxy compounds having a five-membered aromatic heterocycle represented by the following chemical formulas 6a to 6f: [Chemical formula 6a] E1-M1-L9-M3-L10-M2-L13-A1-L14-M4-L11-M6-L12-M5-E2 [Chemical formula 6b] E1-M1-L9-M3-L13-A1-L14-M4-L11-M6-E2 [Chemical formula 6c] E1-M3-L10-M2-L13-A1-L14-M6-L12-M5-E2 [Chemical formula 6d] E1-M1-M3-M2-L13-A1-L14-M4-M6-M5-E2 [Chemical formula 6e] E1-M1-M3-L13-A1-L14-M4-M6-E2 [Chemical formula 6f] E1-M3-M2-L13-A1-L14-M6-M5-E2

[0027] In the aforementioned chemical formulas 6a to 6f, M1 and M2 are independently one or more arylene groups selected from the arylene groups represented by the aforementioned chemical formulas 3a to 3e, M3 is a five-membered ring heteroarylene group selected from the heteroarylene groups represented by the aforementioned chemical formulas 4a to 4r, L9, L10, L11 and L12 are independently -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O- or -OC(=O)O-, L13 and L14 are independently -O- or -S-, and A1 is a C4-C that is partially or completely substituted with a halogen. 12 Alkylene group, unsubstituted C4-C 12 Alkylene group, C4-C partially or completely substituted with halogen 12 Alkadieniene group, or unsubstituted C4-C 12 These are alkadieniene groups, and E1 and E2 are independently epoxy-containing groups.

[0028] In epoxy compounds having a five-membered aromatic heterocycle represented by chemical formulas 6a to 6f, for example, A1 is a butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecylene group, dodecylene group, butadienylene group, pentadienylene group, hexadienylene group, heptadienylene group, octadienylene group, nonadienylene group, decadienylene group, undecadienylene group, or dodecadienylene group. For example, A1 is a butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecienylene group, or dodecien group. For example, A1 is a butylene group, hexylene group, octylene group, or decylene group.

[0029] In an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 or 2, for example, E1 and E2 are also epoxy-containing groups independently selected from among the epoxy-containing groups represented by the following chemical formulas 7a to 7d: [ka] In the aforementioned chemical formulas 7a to 7d, R a and R b These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C 10 It is an alkyl group, and n is between 1 and 10.

[0030] In an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 or 2, for example, M1, M2, M4, and M5 are independently one or more arylene groups selected from the active groups represented by the following chemical formulas 8a to 8e, and E1 and E are independently epoxy-containing groups selected from the epoxy-containing groups represented by the following chemical formulas 9a to 9d: [ka] In the aforementioned chemical formulas 8a to 8e and 9a to 9d, n is 1 to 10.

[0031] Epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 are, for example, epoxy compounds having a five-membered aromatic heterocycle represented by the following chemical formulas 10a to 10o and 11a to 11r: [ka] TIFF0007831899000006.tif244170TIFF0007831899000007.tif233170TIFF0007831899000008.tif135170

[0032] Epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 are, for example, epoxy compounds having a five-membered aromatic heterocycle represented by the following chemical formulas 12a to 12r and 13a to 13r: [ka] TIFF0007831899000010.tif232170TIFF0007831899000011.tif231170TIFF0007831899000012.tif185170

[0033] The melting points of epoxy compounds represented by chemical formula 1 or chemical formula 2 are, for example, 200°C or less, 195°C or less, 190°C or less, or 185°C or less. The melting points of epoxy compounds represented by chemical formula 1 or chemical formula 2 are also, for example, 30°C to 200°C, 50°C to 200°C, 80°C to 195°C, 100°C to 190°C, or 120°C to 185°C. When an epoxy compound represented by chemical formula 1 or chemical formula 2 has a melting point in such a range, the curing temperature of the epoxy resin composition can be lowered. However, if the curing temperature of the epoxy resin composition is excessively high, damage such as thermal deformation of electronic components may occur due to the high temperature.

[0034] The epoxy compound of chemical formula 2 has an even lower melting point than the epoxy compound of chemical formula 1 due to the inclusion of spacer (A). For example, the melting point of the epoxy compound of chemical formula 2 is 95% or less, 90% or less, or 80% or less of the melting point of the epoxy compound of chemical formula 1. For example, if the melting point of the epoxy compound of chemical formula 1 is 180°C, the melting point of the epoxy compound of chemical formula 2 is 171°C or less.

[0035] [Epoxy resin composition] Another embodiment of the epoxy resin composition comprises epoxy compounds represented by the aforementioned chemical formulas 1, 2, 5a to 5f, 6a to 6f, 10a to 10o, 11a to 11r, 12a to 12r, and 13a to 13r, and a curing agent. The inclusion of such epoxy compounds in the epoxy resin composition allows the cured product of the epoxy resin composition to provide improved thermal conductivity. The epoxy resin composition can also be molded into a variety of forms.

[0036] The curing agent included in the epoxy resin composition may be selected from, for example, amine-based curing agents, acid anhydride-based curing agents, polyamine curing agents, polysulfide curing agents, phenol novolac-type curing agents, bisphenol A-type curing agents, and dicyandiamide curing agents, but is not necessarily limited to these. The curing agent may also be, for example, a polyfunctional phenol-based curing agent. The polyfunctional phenol-based curing agent may be, for example, a compound having three or more phenolic hydroxyl groups and may have the following structure. [ka] In the aforementioned chemical formula, n is an integer between 1 and 10,000.

[0037] The number-average molecular weight of the polyfunctional phenolic curing agent can be, for example, 300 daltons to 30,000 daltons, 400 daltons to 30,000 daltons, 600 daltons to 10,000 daltons, or 800 daltons to 10,000 daltons.

[0038] The content of the curing agent is not particularly limited, but it may be 0.1 to 10 parts by weight, 0.1 to 5 parts by weight, or 0.1 to 1 part by weight per 100 parts by weight of the epoxy resin composition. By including a curing agent in such a range, it is possible to accelerate the curing rate of the epoxy resin composition while minimizing the amount of unreacted curing agent and preventing a decrease in the insulating properties of the compound.

[0039] The epoxy resin composition further comprises, for example, a filler, which may be an inorganic filler, an organic filler, or a combination thereof.

[0040] The inorganic filler may include, but is not limited to, at least one selected from, for example, silicon oxide, calcium carbonate, magnesium carbonate, magnesia, clay, alumina (Al2O3), titania (TiO2), talc, calcium silicate, antimony oxide, glass fiber, and eucryptite ceramic. The eucryptite ceramic is a crystallized glass composed of Li2O, Al2O3, and SiO2. The organic filler may include, but is not limited to, at least one selected from, for example, polyethyleneimine, ethylene glycol, and polyethylene glycol. The filler is preferable to be an inorganic filler in that it has high thermal conductivity, can strengthen the rigidity of the compound, and can reduce the coefficient of linear expansion.

[0041] The filler content may be, for example, 20 to 99% by weight, 30 to 99% by weight, 40 to 99% by weight, 50 to 99% by weight, 60 to 99% by weight, 70 to 99% by weight, 80 to 99% by weight, 90 to 99% by weight, or 95 to 99% by weight of the total weight of the epoxy resin composition. By having such a range of filler content, the epoxy resin composition can effectively control physical properties such as moldability, low stress, high-temperature strength, and thermal expansion coefficient.

[0042] The epoxy resin composition may further contain one or more additives selected from curing accelerators, reaction modifiers, mold release agents, coupling agents, stress relievers, and auxiliary flame retardants. These additives may be included independently of each other in amounts of, for example, 0.1 to 10 parts by weight, 0.1 to 5 parts by weight, 0.1 to 3 parts by weight, or 0.1 to 1 part by weight per 100 parts by weight of the epoxy resin composition.

[0043] The epoxy resin composition may further contain other conventional epoxy resins in addition to the epoxy compound of the present invention. Further inclusion of conventional epoxy resins can further improve the thermal expansion coefficient, warp characteristics, and processing characteristics of the compound, and can also improve the peel strength. Examples of other conventional epoxy resins include biphenyl epoxy resin, novolac epoxy resin, dicyclopentadienyl epoxy resin, bisphenol epoxy resin, terpene epoxy resin, aralkyl epoxy resin, multi-functional epoxy resin, naphthalene epoxy resin, and halogenated epoxy resin. Such epoxy resins can be used individually or in mixtures of two or more. The content of other conventional epoxy resins is not particularly limited, but for example, it may be included in amounts of 1 to 15 parts by weight, 1 to 10 parts by weight, or 1 to 5 parts by weight per 100 parts by weight of the epoxy resin composition. By further including other conventional epoxy resins in such a range in the epoxy resin composition, the adhesion between the epoxy resin composition and the substrate, the coefficient of thermal expansion, and the processing characteristics may be further improved, for example, on semiconductor packages.

[0044] The epoxy resin composition can be used in a variety of applications. For example, the epoxy resin composition can be used as a encapsulating resin composition or a fixing resin composition. The encapsulating resin composition (a encapsulating resin composition for encapsulating electronic components) is, for example, a semiconductor encapsulating resin composition that can encapsulate electronic components such as semiconductor chips and is used in semiconductor packages; a resin composition for encapsulating vehicle electronic control units that encapsulate substrates on which electronic components are mounted; or a resin composition for encapsulating sensors, sensor modules, cameras, camera modules, modules with displays, modules with dry cell batteries or coin batteries, etc. The fixing resin composition is, for example, a resin composition for fixing motor components. The fixing resin composition for motor components is, for example, a resin composition for fixing rotor core magnets, a resin composition for fixing stators, etc. The epoxy resin composition can also be used in applications other than those described above.

[0045] The method for producing the epoxy resin composition is not particularly limited. The method for producing the epoxy resin composition includes the steps of selecting components such as epoxy compounds and curing agents, and mixing the components. For example, an epoxy compound suitable for the epoxy resin composition is selected from epoxy compounds represented by chemical formulas 1 and / or 2. Next, the epoxy resin composition is produced by mixing the selected epoxy compound with other components such as curing agents and additives.

[0046] In the stage of mixing the components, the mixture is obtained by mixing by known means. Alternatively, a kneaded product can be obtained by melt-kneading the mixture at a temperature lower than the curing temperature, for example. As a kneading method, an extruder such as a single-screw kneading extruder or a twin-screw kneading extruder, or a roll-type kneader such as a mixing roll can be used, but a twin-screw kneading extruder can be used. After cooling the molten kneaded product, the product can be molded into powder, granules, tablets, or sheets. As a method for obtaining a powder-like resin composition, for example, the product can be crushed using a crushing device. Alternatively, the product can be molded into a sheet and then crushed. As a crushing device, for example, a hammer mill, a die-type grinder, or a roll crusher can be used. As a method for obtaining a granular or powdered resin composition, for example, an assembly method such as the hot-cut method, in which a small-diameter die is provided at the outlet of a kneading device, and the molten kneaded material discharged from the die is cut to a predetermined length with a cutter or the like, can be used. After obtaining a granular or powdered resin composition by an assembly method such as the hot-cut method, degassing can be performed before the temperature of the resin composition becomes excessively low.

[0047] [Semiconductor device] Another embodiment of a semiconductor device comprises: a substrate; a semiconductor; a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or a sealing part comprising: a sealing part comprising a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and a five-membered aromatic heterocycle represented by chemical formula 2 The semiconductor device comprises: a base portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among the epoxy compounds and a curing agent; a reinforcing portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent; or an adhesive portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent. By including one or more selected from the aforementioned cured product, sealing portion, base portion, reinforcing portion and adhesive portion, the heat dissipation characteristics of the semiconductor device are improved, and as a result, the thermal stability of the semiconductor device is improved.

[0048] The thermal conductivity of the cured epoxy resin composition contained in the semiconductor device is, for example, 0.4 W / mK or higher, 0.45 W / mK or higher, 0.5 W / mK or higher, 0.55 W / mK or higher, or 0.6 W / mK or higher. The thermal conductivity of the cured epoxy resin composition contained in the semiconductor device is, for example, 0.4 to 50 W / mK, 0.45 to 45 W / mK, 0.5 to 40 W / mK, 0.55 to 30 W / mK, 0.55 to 20 W / mK, 0.55 to 10 W / mK, or 0.6 to 10 W / mK. The thermal stability of the semiconductor device is further improved by having one or more selected from the cured material, sealing part, substrate part, reinforcing part, and adhesive part contained in the semiconductor device have a thermal conductivity within such a range.

[0049] The cured product of an epoxy resin composition containing the epoxy compound of chemical formula 2 has a higher thermal conductivity than the cured product of an epoxy resin composition containing the epoxy compound of chemical formula 1, due to the inclusion of the epoxy compound of chemical formula 2 with the addition of spacer (A). For example, the thermal conductivity of the cured product of an epoxy resin composition containing the epoxy compound of chemical formula 2 is 110% to 200%, 120% to 200%, 130% to 200%, 150% to 200%, or 160% to 200% of the thermal conductivity of the cured product of an epoxy resin composition containing the epoxy compound of chemical formula 1. For example, if the thermal conductivity of the cured product of an epoxy resin composition containing the epoxy compound of chemical formula 1 is 0.50 W / mK, the thermal conductivity of the cured product of an epoxy resin composition containing the epoxy compound of chemical formula 2 may be 0.55 W / mK or higher.

[0050] The semiconductor device is, for example, a semiconductor package. Referring to Figure 3, the semiconductor package 100 includes a substrate 5, a die attach film 4 located on the substrate 5, a semiconductor chip 3 located on the substrate 5 and attached to the substrate 5 via the die attach film 4, a connection portion 6 such as a bonding wire for electrically connecting the semiconductor chip 3 and the substrate 5, and a molding portion 110 for encapsulating the semiconductor chip 3 and the connection portion 6 and protecting the mounting structure including the substrate 5, the chip 3 mounted on the substrate 5, and the connection portion 6. The molding portion 110 is formed on the substrate 5 so as to completely cover the semiconductor chip 3 and the connection portion 6. The molding portion 110 is formed from the epoxy resin composition described above. The molding portion 110 includes an epoxy resin 1 and a filler 2 dispersed within the epoxy resin 1. The molding portion 110 has a form in which the filler is dispersed within a resin matrix formed by curing the epoxy compound. On the substrate 5, a plurality of solder balls 7 are formed on the surface 5B opposite to the mounting surface 5A on which the semiconductor chip 3 is mounted, for electrically connecting the semiconductor chip 3 to an external circuit (not shown). Using the epoxy resin composition, a process can be carried out to form a molding portion 110 that seals the semiconductor chip 3 mounted on the substrate 5 using a low-pressure transfer molding process in order to manufacture a semiconductor package, for example, a semiconductor package 100 as illustrated in Figure 3. In one embodiment, for example, instead of the low-pressure transfer molding process, an injection molding process or a casting process can be used. The molding portion 100 formed from the epoxy resin composition protects the semiconductor chip 3 area from moisture and other elements within the semiconductor package and provides excellent heat dissipation characteristics. Therefore, the reliability of the semiconductor package is improved even in humid environments.

[0051] [Electronic equipment] Another embodiment of an electronic device comprises: a substrate; electronic components; a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or a sealing part comprising a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and a five-membered aromatic heterocycle represented by chemical formula 2 The electronic device comprises: a base portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among the epoxy compounds and a curing agent; a reinforcing portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent; or an adhesive portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent. By including one or more selected from the aforementioned cured product, sealing portion, base portion, reinforcing portion, and adhesive portion, the heat dissipation characteristics of the electronic device are improved, and as a result, the thermal stability of the electronic device is improved.

[0052] The thermal conductivity of the cured epoxy resin composition contained in the electronic device is, for example, 0.4 W / mK or higher, 0.45 W / mK or higher, 0.5 W / mK or higher, 0.55 W / mK or higher, or 0.6 W / mK or higher. The thermal conductivity of the cured epoxy resin composition contained in the electronic device is, for example, 0.4 to 50 W / mK, 0.45 to 45 W / mK, 0.5 to 40 W / mK, 0.55 to 30 W / mK, 0.55 to 20 W / mK, 0.55 to 10 W / mK, or 0.6 to 10 W / mK. The thermal stability of the electronic device is further improved by having one or more selected from the cured product, sealing part, base material part, reinforcing part, and adhesive part contained in the electronic device have a thermal conductivity within such a range.

[0053] The electronic device includes, for example, an electronic control unit, a sensor, a sensor module, a camera, a camera module, a module with a display, a module with a dry cell battery or coin cell battery, a motor, etc. The electronic device also includes, for example, an integrated circuit element with electronic components, a printed circuit board with electronic components. Referring to Figure 4, the integrated circuit element 300 includes a plurality of semiconductor chips 320 stacked sequentially on a package substrate 310. A control chip 330 is connected to the plurality of semiconductor chips 320. The stacked structure of the plurality of semiconductor chips 320 and the control chip 330 is sealed on the package substrate 310 by a molding portion 340. The molding portion 340 can have the same configuration as the molding portion 110 in Figure 3. The molding portion 340 is formed using the epoxy resin composition described above. The molding portion 340 includes epoxy resin 341 and a plurality of fillers 342 dispersed in the epoxy resin 341. The details relating to epoxy resin 341 and filler 342 are the same as those for epoxy resin 1 and filler 2 in Figure 3. Figure 4 illustrates a structure in which multiple semiconductor chips 320 are stacked vertically. The multiple semiconductor chips 320 are also arranged horizontally on the package substrate 310, and are arranged in a linked structure that combines vertical and horizontal mounting. The control chip 330 is optional. The package substrate 310 is made of a flexible printed circuit board, a rigid printed circuit board, or a combination thereof. The package substrate 310 is equipped with internal wiring 312 and connection terminals 314. The connection terminals 314 are formed on one side of the package substrate 310. Solder balls 316 are formed on the other side of the package substrate 310. The connection terminals 314 are electrically connected to the solder balls 316 via the internal wiring 312. Solder balls 316 can also be replaced by conductive bumps or LGA (lead grid array). Multiple semiconductor chips 320 and control chips 330 each include connecting structures 322, 332, respectively. Connecting structures 322, 332 are examples. For example, it consists of a TSV (through silicon via) contact structure. The connecting structures 322, 332 of the multiple semiconductor chips 320 and the control chip 330, respectively, are electrically connected to the connection terminals 314 of the package substrate 310 via bump-like connection parts 350. The multiple semiconductor chips 320 each include a system LSI (large-scale integration), flash memory, DRAM (dynamic random access memory), SRAM (static random access memory), EEPROM (electrically erasable programmable read-only memory), PRAM (phase change random access memory), MRAM (magnetic random access memory), or RRAM (resistive random access memory). The control chip 330 includes logic circuits such as SER / DES (serializer / deserializer) circuits. Referring to Figure 5, the integrated circuit element 400 includes a module substrate 410, a control chip 420 mounted on the module substrate 410, and multiple semiconductor packages 430. Multiple input / output terminals 450 are formed on the module substrate 410. Multiple semiconductor packages 430 include one or more of the semiconductor package 100 shown in Figure 3 and the integrated circuit element 300 shown in Figure 4.

[0054] [Goods] An article according to another embodiment comprises: a base material; a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or a sealing part comprising a cured product of an epoxy resin composition comprising one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; or an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2. The article comprises a base portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds and a curing agent; or a reinforcing portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent; or an adhesive portion consisting of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from among epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2 and a curing agent. By including one or more of the aforementioned cured product, sealing portion, base portion, reinforcing portion, and adhesive portion, the heat dissipation characteristics of the article are improved, and as a result, the thermal stability of the article is improved.

[0055] The thermal conductivity of the cured epoxy resin composition contained in the article is, for example, 0.4 W / mK or higher, 0.45 W / mK or higher, 0.5 W / mK or higher, 0.55 W / mK or higher, or 0.6 W / mK or higher. The thermal conductivity of the cured epoxy resin composition contained in the article is, for example, 0.4 to 50 W / mK, 0.45 to 45 W / mK, 0.5 to 40 W / mK, 0.55 to 30 W / mK, 0.55 to 20 W / mK, 0.55 to 10 W / mK, or 0.6 to 10 W / mK. The thermal stability of the article is further improved if one or more selected from the cured product, sealing part, base material part, reinforcing part, and adhesive part contained in the article have a thermal conductivity within such a range.

[0056] These items include, but are not limited to, mobile phones, MP3 players, navigation systems, portable multimedia players (PMPs), solid-state disks (SSDs), or household appliances.

[0057] Another embodiment of the method for manufacturing an article includes the steps of providing the aforementioned epoxy resin composition on a substrate and curing the epoxy resin composition.

[0058] The epoxy resin composition can be provided on a substrate in various states, such as liquid, solid, or semi-cured. Epoxy resin compositions provided in liquid form may be provided in a molten state or dissolved in a solvent. Epoxy resin compositions provided in solid form may be provided on a substrate in various forms, such as powder, granules, or sheets. The epoxy resin composition may be provided on a substrate in an uncured state, or in a partially cured or semi-cured state. After being provided on a substrate, the epoxy resin composition may be molded into a specific form, or molded into a specific form and then provided on a substrate.

[0059] After an epoxy resin composition is provided on a substrate, the epoxy resin composition is cured to manufacture an article. The cured epoxy resin composition constitutes, but is not limited to, the sealing part, substrate part, reinforcing part, adhesive part, etc., of the article.

[0060] The method for curing the epoxy resin composition includes, but is not limited to, thermocuring and ultraviolet curing. The epoxy resin composition can also be cured by heat, for example. The curing temperature of the epoxy resin composition can be 100°C or higher, 110°C or higher, or 120°C or higher. The curing of the epoxy resin composition can also be carried out at temperatures of, for example, 200°C or lower, 195°C or lower, 190°C or lower, 185°C or lower, or 180°C or lower. The curing step of the epoxy resin composition can also be in a temperature range of, for example, 100°C to 200°C, 110°C to 200°C, 120°C to 200°C, 130°C to 200°C, 150°C to 195°C, 160°C to 190°C, 150°C to 185°C, or 150°C to 180°C. By curing the epoxy resin composition in such a temperature range, damage due to thermal deformation of semiconductors, electronic components, etc., can be prevented.

[0061] The definitions of substituents used in the chemical formulas of this specification are described below. The substituents of substituted alkyl groups, substituted alkylene groups, substituted alkenylene groups, substituted alkynylene groups, and substituted alkadieniene groups used herein are halogens, hydroxyl groups, C1-C5 alkyl groups, C1-C5 alkoxy groups, or combinations thereof. In chemical formulas, the term "alkyl" refers to a fully saturated, branched or unbranched (or straight-chain or linear) hydrocarbon. Non-restrictive examples of the aforementioned "alkyl" include methyl, ethyl, i-propyl, isopropyl, i-butyl, isobutyl, sec-butyl, i-pentyl, isopentyl, neopentyl, i-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, and i-heptyl. One or more hydrogen atoms in the aforementioned "alkyl" are halogen atoms, hydroxyl groups, alkoxy groups, nitro groups, cyano groups, amino groups, azide groups, amidino groups, hydrazino groups, hydrazono groups, carbonyl groups, carbamyl groups, thiol groups, ester groups, carboxylic acids and their salts, sulfonic acid groups and their salts, phosphate groups and their salts, C1-C 20 Alkyl alkyl group, C2-C 20 Alkenyl group, C2-C 20 Alkynyl group, C6-C 30 Aryl group, C7-C 30 Arylalkyl groups, C1-C 30 Alkoxy group, C1-C 20 Heteroalkyl groups, C3-C 20 Heteroarylalkyl groups, C3-C 30 Cycloalkyl groups, C3-C 15 Cycloalkenyl group, C6-C 15 Cycloalkynyl group, C3-C 30 It can also be substituted with heterocycloalkyl groups and selected substituents from combinations thereof.

[0062] The term "alkenyl" refers to an alkyl group containing one carbon-carbon double bond. The term "alkynyl" refers to an alkyl group containing one carbon-carbon triple bond. The term "alkadinyl" refers to an alkyl group containing two carbon-carbon double bonds. The term "halogen atom" includes elements such as fluorine, bromine, chlorine, and iodine.

[0063] The term "alkoxy" used in chemical formulas refers to alkyl-O-, where the alkyl group is as described above. Non-restrictive examples of the alkoxy include methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, cyclopropoxy, and cyclohexyloxy. One or more hydrogen atoms in the alkoxy group can be substituted with the same substituents as in the alkyl group described above.

[0064] The term "aryl" used in chemical formulas refers to an aromatic hydrocarbon containing one or more rings, used alone or in combination. Furthermore, unless otherwise defined herein, "hetero" means a material containing one to four heteroatoms selected from I, O, S, Se, Te, Si, and P. The term "aryl" includes groups in which an aromatic ring is fused to one or more cycloalkyl rings. Non-restrictive examples of "aryl" include phenyl, naphthyl, and tetrahydronaphthyl. Furthermore, one or more hydrogen atoms in the "aryl" group can be substituted with the same substituents as in the alkyl group described above.

[0065] In chemical formulas, the term "heteroaryl group" refers to an aryl group in which one or more carbon atoms, CH, or CH2 are substituted with a heteroatom or a chemical group containing at least one heteroatom. The term "alkylene" used in chemical formulas refers to a divalent aliphatic hydrocarbon, which corresponds to the "alkyl" group. The term "alkenylene" used in chemical formulas refers to a divalent aliphatic hydrocarbon, corresponding to the "alkenyl" group. The term "alkynylene" used in chemical formulas refers to a divalent aliphatic hydrocarbon, corresponding to the "alkynyl" group.

[0066] The term "alkadienylene" used in chemical formulas refers to a divalent aliphatic hydrocarbon, corresponding to the "alkadienyl" group. The term "arylene" used in chemical formulas refers to a divalent aromatic hydrocarbon corresponding to the "aryl" group. In chemical formulas, the term "heteroarylene" refers to a divalent aryl group in which one or more carbon atoms, CH, or CH2 are substituted with a heteroatom or a chemical group containing at least one heteroatom. [Examples]

[0067] The concept of the present invention will be described in more detail through the following examples and comparative examples. However, these examples are for illustrative purposes only and do not limit the scope of the concept of the present invention.

[0068] (Manufacturing of epoxy compounds and cured products) Example 1 (Manufacturing of epoxy compounds) In a 500 ml glass reactor, 16 g of 2,5-franzicarboxylic acid (FDA), 100 ml of THF, and 0.05 ml of DMF were added, and 20 g of oxalyl chloride was added. The mixture was reacted at room temperature for 2 hours to obtain furan-2,5-dicarbonyl dichloride (FDCDCl). 9 g of hydroquinone was dissolved in 100 ml of pyridine, and then 8 g of FDCDCl was added. The mixture was reacted at room temperature for 4 hours. Water was added to the resulting solution, and the precipitate was obtained by filtration. After washing the precipitate several times with water, it was recrystallized with pyridine and dried in a vacuum oven at 60°C for 12 hours to produce intermediate 1-1. 5g of intermediate 1-1, 50g of epichlorohydrin, and 20g of isopropyl alcohol were added to a 250ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow, and reflux was maintained at that temperature for 5 hours. The reactor temperature was lowered to room temperature, and 1.2g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula 11a. [ka] 1 1H NMR (500MHz, CDCl3): δ7.5(s,2H),7.2(d,4H),6.9-6.8(d,4H),4.2-3.9(m,4H),3.0(m,2H),2.9(s,2H),2.8-2.4(m,4H) (Manufacturing of hardened products) The manufactured epoxy compound and the phenolic curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals Co., Ltd.) were mixed in an equivalent ratio of 1:1 to prepare an epoxy resin composition. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0069] Example 2 (Manufacturing of epoxy compounds) In a 500 ml glass reactor, 10 g of 1H-pyrrole-2,5-diol, 20 g of hydroquinone, 3 g of p-toluenesulfonic acid, and 200 ml of 1,2-dichlorobenzene were added and reacted at 160°C for 4 hours under a nitrogen gas flow. Water was added to the resulting solution, and the precipitate formed was obtained by filtration. The precipitate was washed several times with water and dried in a vacuum oven at 60°C for 12 hours to produce intermediate 2-1. 2-15 g of the intermediate, 50 g of epichlorohydrin, and 20 g of isopropyl alcohol were added to a 250 ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow, and reflux was maintained at that temperature for 5 hours. The reactor temperature was lowered to room temperature, and 1.2 g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula 10c. [ka] 1 1H NMR (500MHz, CDCl3): δ11.9(s,1H), 7.9(d,4H), 7.1(d,4H), 4.2-3.9(m,4H), 3.0(m,2H), 2.6-2.4(m,4H) (Manufacturing of hardened products) The manufactured epoxy compound and the phenolic curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals Co., Ltd.) were mixed in an equivalent ratio of 1:1 to prepare an epoxy resin composition. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0070] Example 3 (Manufacturing of epoxy compounds) In a 1L glass reactor, 200ml of 95% ethanol, 170g of intermediate 1-1 prepared in Example 1, 0.09g of sodium hydrosulfite, and 21g of 1,4-dibromobutane were added and mixed. While stirring and refluxing, 8.4g of potassium hydroxide dissolved in 100ml of 95% ethanol was gradually added to the reactor over 1 hour, and the mixture was refluxed for 8 hours. After cooling to room temperature, the solution was neutralized with 30wt% sulfuric acid, and 500ml of 95% ethanol was added. A precipitate was obtained by filtration. This precipitate was washed several times with ethanol and then vacuum dried to prepare intermediate 1-2. 30 g of intermediate 1-2, 148 g of epichlorohydrin, and 80 g of isopropyl alcohol were added to a 500 ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow and refluxed for 5 hours while maintaining the reactor temperature. The reactor temperature was lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula 13a. [ka] 1 1H NMR (500MHz, CDCl3): δ7.8(s,4H), 7.1(d,8H), 6.9(d,8H), 4.2-4.1(m,6H), 3.04(m,2H), 2.6-2.4(m,4H), 1.9(m,4H) (Manufacturing of hardened products) The manufactured epoxy compound and the phenolic curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals Co., Ltd.) were mixed in an equivalent ratio of 1:1 to prepare an epoxy resin composition. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0071] Example 4 (Manufacturing of epoxy compounds) In a 1L glass reactor, 200ml of 95% ethanol, 170g of intermediate 2-1 prepared in Example 2, 0.09g of sodium hydrosulfite, and 21g of 1,4-dibromobutane were added and mixed. While stirring and refluxing, 8.4g of potassium hydroxide dissolved in 100ml of 95% ethanol was gradually added to the reactor over 1 hour, and refluxed for 8 hours. After cooling to room temperature, the solution was neutralized with 30wt% sulfuric acid, and 500ml of 95% ethanol was added. A precipitate was obtained by filtration. This precipitate was washed several times with ethanol and then vacuum dried to prepare intermediate 2-2. 30 g of intermediate 2-2, 148 g of epichlorohydrin, and 80 g of isopropyl alcohol were added to a 500 ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow and refluxed for 5 hours while maintaining the reactor temperature. The reactor temperature was lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula 12c. [ka] 1 1H NMR (500MHz, CDCl3): δ12.0(s,2H), 7.9(d,8H), 7.1(d,8H), 6.5(s,4H), 4.2-4.1(m,6H), 3.9(m,2H), 3.0(m,2H), 2.6(m,2H), 2.3(m,2H), 1.9(m,4H) (Manufacturing of hardened products) The manufactured epoxy compound and the phenolic curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals Co., Ltd.) were mixed in an equivalent ratio of 1:1 to prepare an epoxy resin composition. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0072] Example 5 (Manufacturing of epoxy compounds) In a 500 ml glass reactor, 20.0 g of 3-(2-trimethylsilylethynyl)phenol (3-TMSEphenol) and 150 ml of DMF were added and mixed at room temperature under nitrogen gas flow. Then, 85 g of 2-azidophenol (3-azidophenol), 0.1 g of CuBr (copper bromide), and 0.2 g of 2,2-bipyridyl were added and mixed, and the mixture was reacted at 80°C for 24 hours. After the resulting solution was cooled to room temperature, the organic mixture was washed with 1 L of ethyl acetate and water, and the mixture was dried over MgSO4. After removing the solvent from the dried solution by vacuum distillation, the resulting precipitate was recrystallized with acetic acid / water to produce intermediate 3-1. In a 1L glass reactor, 200ml of 95% ethanol, 180g of intermediate 3-1, 0.09g of sodium hydrosulfite, and 21g of 1,4-dibromobutane were added and mixed. While stirring and refluxing, 8.4g of potassium hydroxide was dissolved in 100ml of 95% ethanol and gradually added to the reactor over 1 hour, followed by refluxing for 8 hours. After cooling to room temperature, the solution was neutralized with 30wt% sulfuric acid, and 500ml of 95% ethanol was added. A precipitate was obtained by filtration. This precipitate was washed several times with ethanol and then vacuum-dried to produce intermediate 3-2. 3-230 g of the intermediate, 148 g of epichlorohydrin, and 80 g of isopropyl alcohol were added to a 500 ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow and refluxed for 5 hours while maintaining the reactor temperature. The reactor temperature was lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula 12L. [ka] 1 1H NMR (500MHz, CDCl3): δ8.1(s,2H), 7.6(d,4H), 7.5(d,4H), 7.1(d,4H), 4.2(m,2H), 4.1(m,4H), 3.9(m,2H), 3.0(m,2H), 2.6(m,2H), 2.4(m,2H), 1.9(m,4H) (Manufacturing of hardened products) The manufactured epoxy compound and the phenolic curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals Co., Ltd.) were mixed in an equivalent ratio of 1:1 to prepare an epoxy resin composition. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0073] Comparative Example 1 (Manufacturing of epoxy compounds) We obtained NC3000 (Nippon Kayaku Co., Ltd.), a phenol aralkyl type epoxy resin represented by the following chemical formula A, and used it as is. [ka] (Manufacturing of hardened products) An epoxy resin composition was prepared by mixing the aforementioned epoxy compound with the phenol-based curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals, Inc.) in an equivalent ratio of 1:1. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0074] Comparative Example 2 (Manufacturing of epoxy compounds) We obtained SH400E (DIC Japan), an epoxy compound represented by the chemical formula B below, and used it as is. [ka] (Manufacturing of hardened products) An epoxy resin composition was prepared by mixing the aforementioned epoxy compound with the phenol-based curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals, Inc.) in an equivalent ratio of 1:1. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0075] Comparative Example 3 (Manufacturing of epoxy compounds) We obtained and used TMBO(H) (Hitachi Chemical), an epoxy compound represented by the chemical formula C shown below. [ka] (Manufacturing of hardened products) An epoxy resin composition was prepared by mixing the aforementioned epoxy compound with the phenol-based curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals, Inc.) in an equivalent ratio of 1:1. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0076] Comparative Example 4 (Manufacturing of epoxy compounds) The epoxy compound represented by the chemical formula D below was synthesized and used by the following method. In a 500 ml glass reactor, 75 g of hydroquinone, 35 g of 4-hydrobenzoic acid, 0.5 g of p-toluenesulfonic acid, and 300 ml of 1,2-dichlorobenzene were added and mixed under a nitrogen gas flow, then reacted at 160°C for 4 hours. Water was added to the resulting solution, and the precipitate that formed was obtained by filtration. After washing the precipitate several times with water, it was recrystallized with methanol / water and dried in a vacuum oven at 60°C for 12 hours to produce intermediate 4-1. 5g of intermediate 4-1, 50g of epichlorohydrin, and 20g of isopropyl alcohol were added to a 250ml reactor. After thoroughly purging the reactor with nitrogen gas, the reactor temperature was raised to 50°C under nitrogen gas flow and refluxed for 5 hours while maintaining the reactor temperature. The reactor temperature was lowered to room temperature, and 1.2g of NaOH (25% aqueous solution) was added dropwise for 1 hour. The reactor temperature was raised to 60°C and stirred for 4 hours. The reactor temperature was lowered to room temperature, and recrystallization was performed with CH2Cl2 / CH3OH to produce the compound represented by chemical formula D. [ka] (Manufacturing of hardened products) An epoxy resin composition was prepared by mixing the aforementioned epoxy compound with the phenol-based curing agent MEH7500 (polyfunctional phenol, Meiwa Chemicals, Inc.) in an equivalent ratio of 1:1. 5 g of the prepared epoxy resin composition was placed in an aluminum mold and then cured by raising the temperature to 190°C to produce a sample, which is a cured epoxy resin composition.

[0077] Evaluation Example 1: Thermal Conductivity Measurement The thermal conductivity of samples that were cured epoxy resin compositions containing the epoxy compounds produced in Examples 1 to 5 and Comparative Examples 1 to 4, along with a curing agent, was measured. The measurement results are shown in Table 1 below. Thermal conductivity was evaluated using the MTPS (modified transient plane source) method with a C-THERM TCITM thermal conductivity meter.

[0078] [Table 1]

[0079] As can be seen from Table 1, the cured products obtained from the epoxy compounds of Examples 1 to 5 showed a thermal conductivity improvement of 50% or more compared to the cured products obtained from the epoxy compounds of Comparative Examples 1 to 4. Furthermore, the cured products obtained from the epoxy compounds of Examples 3 to 5 showed a thermal conductivity improvement of 10% or more compared to the cured products obtained from the epoxy compounds of Examples 1 to 2. [Explanation of symbols]

[0080] 1,341 Molding resin 2,342 fillers 3,320 semiconductor chips 4. Die Touch Film 5 Base material 6,350 connection part 7,316 Soldaball 100,430 semiconductor packages 110,340 Molding section 300,400 integrated circuit elements 310 circuit board 312 Internal wiring of circuit board 314 Connection terminals 322,332 Connection structure 330,420 control chips 410 Module Board 450 input / output terminal

Claims

1. An epoxy compound having a five-membered aromatic heterocycle represented by the following chemical formula 1 or chemical formula 2: [Chemical formula 1] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ -E2 [Chemical formula 2] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ --(L5) ｂ５ -A-(L6) ｂ６ -(M4) ａ３ --(L3) ｂ３ -M6-(L4) ｂ４ -(M5) ａ４ -E2 In the aforementioned chemical formulas 1 and 2, M1, M2, M4, and M5 are arylene groups selected independently from among the arylene groups represented by the following chemical formulas 3a to 3e. M3 and M6 are heteroarylene groups independently selected from among the heteroarylene groups represented by the following chemical formulas 4a to 4r. L1, L2, L3, L4, L5 and L6 are independent of each other: -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, -O-C(=O)O-, -(CH ２ ) ２ -C(=O)-, -CH=CH-C(=O)-, or -CH=N-, A is either substituted or non-substituted C ４ -C １２ Alkylene group, substituted or unsubstituted C ４ -C １２ Alkenylene group, substituted or unsubstituted C ４ -C １２ Alkynylene group, or substituted or unsubstituted C ４ -C １２ It is an alkadierine group. E1 and E2 are independently epoxy-containing groups. E1 and E2 are independently epoxy-containing groups selected from among the epoxy-containing groups represented by the following chemical formulas 7a to 7d: 【Chemistry 1】 In the aforementioned chemical formulas 7a to 7d, Ra and Rb are independently hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C10 alkyl group, and n is 1 to 10; a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2; 【Chemistry 2】 In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C １ -C １０ It is an alkyl group.

2. The epoxy compound having a five-membered aromatic heterocycle represented by the aforementioned chemical formula 1 is one of the following chemical formulas 5a to 5f: [Chemical formula 5a] E1-M1-L7-M3-L8-M2-E2 [Chemical formula 5b] E1-M1-L7-M3-E2 [Chemical formula 5c] E1-M3-L8-M2-E2 [Chemical formula 5d] E1-M1-M3-M2-E2 [Chemical formula 5e] E1-M1-M3-E2 [Chemical formula 5f] E1-M3-M2-E2 (In the above chemical formulas 5a to 5f, M1 and M2 are independently one or more arylene groups selected from the arylene groups represented by the chemical formulas 3a to 3e. M3 is a heteroarylene group selected from among the heteroarylene groups represented by the chemical formulas 4a to 4r, L7 and L8 are independently -O-, -C(=O)-, -C(=O)O-, or -O-C(=O)O-, E1 and E2 are epoxy-containing groups, independently of each other. An epoxy compound having a five-membered aromatic heterocycle represented by one of the following: The epoxy compound having a five-membered aromatic heterocycle represented by the chemical formula 2 is one of the following chemical formulas 6a to 6f: [Chemical formula 6a] E1-M1-L9-M3-L10-M2-L13-A1-L14-M4-L11-M6-L12-M5-E2 [Chemical formula 6b] E1-M1-L9-M3-L13-A1-L14-M4-L11-M6-E2 [Chemical formula 6c] E1-M3-L10-M2-L13-A1-L14-M6-L12-M5-E2 [Chemical formula 6d] E1-M1-M3-M2-L13-A1-L14-M4-M6-M5-E2 [Chemical formula 6e] E1-M1-M3-L13-A1-L14-M4-M6-E2 [Chemical formula 6f] E1-M3-M2-L13-A1-L14-M6-M5-E2 (In the above chemical formulas 6a to 6f, M1 and M2 are one or more arylene groups selected independently from the arylene groups represented by the chemical formulas 3a to 3e. M3 is a five-membered ring heteroarylene group selected from the heteroarylene groups represented by the chemical formulas 4a to 4r, L9, L10, L11, and L12 are independently -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, or -O-C(=O)O-. L13 and L14 are independently -O- or -S-. A1 is C, which is partially or completely replaced with a halogen. ４ -C １２ Alkylene group, unsubstituted C ４ -C １２ Alkylene group, C partially or completely substituted with halogen ４ -C １２ Alkadieniene group, or unsubstituted C ４ -C １２ It is an alkadierine group. E1 and E2 are epoxy-containing groups, independently of each other. The epoxy compound according to claim 1, which is an epoxy compound having a five-membered aromatic heterocycle represented by any one of the following.

3. The epoxy compound according to claim 2, wherein A1 is a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, an undecylene group, a dodecylene group, a butadienylene group, a pentadienylene group, a hexadienylene group, a heptadienylene group, an octadienylene group, a nonadienylene group, a decadienylene group, an undecadienylene group, or a dodecadienylene group.

4. The M1, M2, M4, and M5 are independently one or more arylene groups selected from the active groups represented by the following chemical formulas 8a to 8e. The epoxy compound according to any one of claims 1 to 3, wherein E1 and E2 are independently selected epoxy-containing groups from among epoxy-containing groups represented by the following chemical formulas 9a to 9d: 【Transformation 3】 In the above formula, n is between 1 and 10.

5. The epoxy compound having a five-membered aromatic heterocycle represented by the chemical formula 1 is one of the following chemical formulas 10a to 10o and 11a to 11r: [Chemistry 4A] 【Chemistry 4B】 【Chemistry 4C】 [Transformation 4D] An epoxy compound having a five-membered aromatic heterocycle represented by one of the following: The epoxy compound having a five-membered aromatic heterocycle represented by the aforementioned chemical formula 2 is one of the following chemical formulas 12a to 12r and 13a to 13r: [Chemical 5A] 【Chem.5B】 【5C】 [5D Transformation] The epoxy compound according to any one of claims 1 to 4, which is an epoxy compound having a five-membered aromatic heterocycle represented by any one of the following.

6. The epoxy compound according to any one of claims 1 to 5, wherein the melting point of the epoxy compound represented by chemical formula 1 or chemical formula 2 is 200°C or less.

7. The epoxy compound according to any one of claims 1 to 6, An epoxy resin composition containing a curing agent.

8. The epoxy resin composition according to claim 7, further comprising a filler, wherein the filler is an inorganic filler, an organic filler, or a combination thereof.

9. The epoxy resin composition according to claim 8, wherein the content of the filler is 20 to 99% by weight of the total weight of the epoxy resin composition.

10. Substrate and Semiconductors and, The epoxy resin composition comprises a cured product of one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or A semiconductor device comprising: an adhesive portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent; and a curing agent: [Chemical formula 1] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ -E2 [Chemical formula 2] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ --(L5) ｂ５ -A-(L6) ｂ６ -(M4) ａ３ --(L3) ｂ３ -M6-(L4) ｂ４ -(M5) ａ４ -E2 In the aforementioned chemical formulas 1 and 2, M1, M2, M4, and M5 are arylene groups selected independently from among the arylene groups represented by the following chemical formulas 3a to 3e. M3 and M6 are heteroarylene groups independently selected from among the heteroarylene groups represented by the following chemical formulas 4a to 4r. L1, L2, L3, L4, L5 and L6 are independent of each other: -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, -O-C(=O)O-, -(CH ２ ) ２ -C(=O)-, -CH=CH-C(=O)-, or -CH=N-, A is either substituted or non-substituted C ４ -C １２ Alkylene group, substituted or unsubstituted C ４ -C １２ Alkenylene group, substituted or unsubstituted C ４ -C １２ Alkynylene group, or substituted or unsubstituted C ４ -C １２ It is an alkadierine group. E1 and E2 are independently epoxy-containing groups. E1 and E2 are independently epoxy-containing groups selected from among the epoxy-containing groups represented by the following chemical formulas 7a to 7d: 【Transformation 6】 In the aforementioned chemical formulas 7a to 7d, Ra and Rb are independently hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C10 alkyl group, and n is 1 to 10; a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2. 【Transformation 7】 In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C １ -C １０ It is an alkyl group.

11. The semiconductor device according to claim 10, wherein the thermal conductivity of the cured product of the epoxy resin composition is 0.4 W / mK or higher.

12. Substrate and Electronic components and, The epoxy resin composition comprises a cured product of one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or An electronic device comprising: an adhesive part made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent: [Chemical formula 1] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ -E2 [Chemical formula 2] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ --(L5) ｂ５ -A-(L6) ｂ６ -(M4) ａ３ --(L3) ｂ３ -M6-(L4) ｂ４ -(M5) ａ４ -E2 In the aforementioned chemical formulas 1 and 2, M1, M2, M4, and M5 are arylene groups selected independently from among the arylene groups represented by the following chemical formulas 3a to 3e. M3 and M6 are heteroarylene groups independently selected from among the heteroarylene groups represented by the following chemical formulas 4a to 4r. L1, L2, L3, L4, L5 and L6 are independent of each other: -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, -O-C(=O)O-, -(CH ２ ) ２ -C(=O)-, -CH=CH-C(=O)-, or -CH=N-, A is either substituted or non-substituted C ４ -C １２ Alkylene group, substituted or unsubstituted C ４ -C １２ Alkenylene group, substituted or unsubstituted C ４ -C １２ Alkynylene group, or substituted or unsubstituted C ４ -C １２ It is an alkadierine group. E1 and E2 are independently epoxy-containing groups. E1 and E2 are independently epoxy-containing groups selected from among the epoxy-containing groups represented by the following chemical formulas 7a to 7d: 【Transformation 8】 In the aforementioned chemical formulas 7a to 7d, Ra and Rb are independently hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C10 alkyl group, and n is 1 to 10; a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2. 【Chemistry 9】 In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C １ -C １０ It is an alkyl group.

13. The electronic device according to claim 12, wherein the thermal conductivity of the cured product of the epoxy resin composition is 0.4 W / mK or higher.

14. Substrate and The epoxy resin composition comprises a cured product of one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a sealing portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The invention comprises a base portion made of a cured product of an epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, The device comprises a reinforcing part made of a cured epoxy resin composition containing one or more epoxy compounds selected from epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 1 and epoxy compounds having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent, or An article comprising: an adhesive portion made of a cured epoxy resin composition containing one or more epoxy compounds selected from an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 1 and an epoxy compound having a five-membered aromatic heterocycle represented by chemical formula 2, and a curing agent: [Chemical formula 1] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ -E2 [Chemical formula 2] E1-(M1) ａ１ --(L1) ｂ１ -M3-(L2) ｂ２ -(M2) ａ２ --(L5) ｂ５ -A-(L6) ｂ６ -(M4) ａ３ --(L3) ｂ３ -M6-(L4) ｂ４ -(M5) ａ４ -E2 In the aforementioned chemical formulas 1 and 2, M1, M2, M4, and M5 are arylene groups selected independently from among the arylene groups represented by the following chemical formulas 3a to 3e. M3 and M6 are heteroarylene groups independently selected from among the heteroarylene groups represented by the following chemical formulas 4a to 4r. L1, L2, L3, L4, L5 and L6 are independent of each other: -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, -O-C(=O)O-, -(CH ２ ) ２ -C(=O)-, -CH=CH-C(=O)-, or -CH=N-, A is either substituted or non-substituted C ４ -C １２ Alkylene group, substituted or unsubstituted C ４ -C １２ Alkenylene group, substituted or unsubstituted C ４ -C １２ Alkynylene group, or substituted or unsubstituted C ４ -C １２ It is an alkadierine group. E1 and E2 are independently epoxy-containing groups. E1 and E2 are independently epoxy-containing groups selected from among the epoxy-containing groups represented by the following chemical formulas 7a to 7d: 【Chemistry 10】 In the aforementioned chemical formulas 7a to 7d, Ra and Rb are independently hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C1-C10 alkyl group, and n is 1 to 10; a1, a2, a3, and a4 are mutually independent and are between 0 and 2, provided that the sum of a1 and a2 is between 1 and 4, and the sum of a3 and a4 is between 1 and 4. b1, b2, b3, and b4 are independently 0 or 1, and b5 and b6 are independently 1 or 2. 【Chemistry 11】 In the aforementioned chemical formulas 3a to 3e and 4a to 4r, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are, independently of each other, hydrogen, halogen, hydroxyl group, or substituted or unsubstituted C １ -C １０ It is an alkyl group.

15. The article according to claim 14, wherein the thermal conductivity of the cured product of the epoxy resin composition is 0.4 W / mK or higher.

16. The steps include providing the epoxy resin composition according to any one of claims 7 to 9 on a substrate, A method for manufacturing an article, comprising the step of curing the epoxy resin composition.

17. The method for manufacturing an article according to claim 16, wherein the step of curing the epoxy resin composition is carried out at a temperature of 200°C or lower.

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