Epoxy compounds, compositions, semiconductor devices, electronic devices and articles made from them, and methods of making articles

Abstract

Disclosed are epoxy compounds, compositions, semiconductor devices, electronic devices and articles prepared therefrom, and methods of preparing articles. The epoxy compounds include a 5-membered aromatic heterocyclic ring and are represented by Formula 1 or Formula 2, wherein in Formula 1 and 2, M1, M2, M3, M4, M5, M6, L1, L2, L3, L4, L5, L6, E1, E2, a1, a2, a3, a4, b1, b2, b3, b4, b5, and b6 are the same as those defined in the detailed description. Formula 1 E1-(M1) a1 -(L1) b1 -M3-(L2) b2 -(M2) a2 -E2 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.

Description

[0001] Cross-reference to related applications

[0002] This application is based on and claims priority to Korean Patent Application No. 10-2020-0103436 filed with the Korean Intellectual Property Office on August 18, 2020, and all the contents thereof are incorporated herein by reference. Technical Field

[0003] This disclosure relates to epoxy compounds, compositions prepared using said epoxy compounds, semiconductor devices prepared using said epoxy compounds, electronic devices prepared using said epoxy compounds, articles prepared using said epoxy compounds, and methods for preparing said articles. Background Technology

[0004] Due to the trend towards manufacturing semiconductor circuits with high complexity and high density, the thermal stability of molding materials used to dissipate heat generated from semiconductor circuits has become important.

[0005] Epoxy molding compounds (EMCs), including thermosetting resins, are used as molding materials for semiconductor packaging.

[0006] Inorganic fillers with high thermal conductivity are added to increase the thermal conductivity of EMC.

[0007] However, despite the addition of inorganic fillers with high thermal conductivity, the increase in the thermal conductivity of EMC is slight. Summary of the Invention

[0008] Epoxides are provided that offer improved heat release properties through novel structures.

[0009] An epoxy resin composition comprising the epoxy compound is provided.

[0010] A semiconductor device comprising a cured product prepared using the composition is provided.

[0011] Provide an electronic device that includes a cured product prepared using the composition.

[0012] Articles comprising a cured product prepared using the composition are provided.

[0013] A method for preparing the article is provided.

[0014] Other aspects will be set forth in part in the description which follows, and will also be apparent in part from the description, or may be learned by practice of the embodiments presented in this disclosure.

[0015] According to an aspect of the implementation, the epoxide compound comprising a 5-membered aromatic heterocyclic ring is represented by Formula 1 or Formula 2:

[0016] Formula 1

[0017] E1-(M1) a1 -(L1) b1 -M3-(L2) b2 -(M2) a2 -E2

[0018] Formula 2

[0019] 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

[0020] In equations 1 and 2,

[0021] M1, M2, M4, and M5 are each independently a aryl group represented by one of equations 3a to 3e.

[0022]

[0023] Among them, in equations 3a to 3e,

[0024] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and R 12 Each is independently hydrogen, halogen, hydroxyl, or a substituted or unsubstituted C1-C10 alkyl group, and M3 and M6 are independently heteroaryl groups represented by one of formulas 4a to 4r.

[0025]

[0026]

[0027] L1, L2, L3, L4, L5, and L6 are each independently -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-.

[0028] A is a substituted or unsubstituted C4-C12 alkylene group, a substituted or unsubstituted C4-C12 alkenyl group, a substituted or unsubstituted C4-C12 alkyne group, or a substituted or unsubstituted C4-C12 diene group (sub-chain diene group);

[0029] E1 and E2 are each independently groups containing epoxy (epoxy groups).

[0030] a1, a2, a3, and a4 are each independent integers from 0 to 2, where the sum of a1 and a2 is 1 to 4, and the sum of a3 and a4 is 1 to 4.

[0031] b1, b2, b3, and b4 are each independently 0 or 1, and b5 and b6 are each independently 1 or 2.

[0032] According to an aspect of the embodiment, the epoxy resin composition includes:

[0033] The above-mentioned epoxy compounds; and

[0034] Curing agent.

[0035] According to an aspect of the implementation, the semiconductor device includes:

[0036] Substrate (substrate);

[0037] Semiconductors; and

[0038] Cured products of epoxy resin compositions, said epoxy resin compositions comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or combinations thereof.

[0039] Including the sealed portion of the cured product of the epoxy resin composition,

[0040] The substrate portion includes the cured product of the epoxy resin composition.

[0041] Including the reinforcing portion of the cured product of the epoxy resin composition, or

[0042] This includes the attachment portion of the cured product of the epoxy resin composition.

[0043] According to one aspect of the implementation, the electronic device includes:

[0044] substrate;

[0045] Electronic components (parts); and

[0046] Cured products of epoxy resin compositions, said epoxy resin compositions comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or combinations thereof.

[0047] Including the sealed portion of the cured product of the epoxy resin composition,

[0048] The substrate portion includes the cured product of the epoxy resin composition.

[0049] Including the reinforcing portion of the cured product of the epoxy resin composition, or

[0050] Includes the attachment portion of the cured product of the epoxy resin composition.

[0051] According to an aspect of the implementation, the article of manufacture includes:

[0052] substrate; and

[0053] Cured products of epoxy resin compositions, said epoxy resin compositions comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or combinations thereof.

[0054] Including the sealed portion of the cured product of the epoxy resin composition,

[0055] The substrate portion includes the cured product of the epoxy resin composition.

[0056] Including the reinforcing portion of the cured product of the epoxy resin composition, or

[0057] Includes the attachment portion of the cured product of the epoxy resin composition.

[0058] According to an aspect of the implementation method, the method for preparing the article includes:

[0059] The above-described epoxy resin composition is provided on a substrate; and

[0060] The epoxy resin composition is then cured. Attached Figure Description

[0061] The above and other aspects, features, and advantages of some embodiments of this disclosure will become clearer from the following description taken in conjunction with the accompanying drawings, wherein:

[0062] Figure 1 It is a graph illustrating the change in thermal conductivity of a compound (also called a complex) based on the thermal conductivity of the filler.

[0063] Figure 2 It is a graph illustrating the change in thermal conductivity of the compound based on the thermal conductivity of the resin;

[0064] Figure 3 This is a schematic cross-sectional view of a semiconductor device according to an embodiment;

[0065] Figure 4 This is a schematic cross-sectional view of an electronic device according to one embodiment; and

[0066] Figure 5 This is a schematic cross-sectional view of an electronic device according to one embodiment. Detailed Implementation

[0067] The embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements and not individual elements of the list when preceding or following it; for example, “at least one of a, b, or c” means only a, only b, only c, both a and b, both a and c, both b and c, all a, b, and c, or variations thereof.

[0068] Various exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the inventive concept can be embodied in many different forms and should not be construed as limited to the exemplary embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be exhaustive and complete, and will fully convey the scope of the inventive concept to those skilled in the art. The same reference numerals in the drawings denote the same elements.

[0069] It will be understood that when a component is referred to as being "on" another component, the component may be directly on the other component or there may be an intermediate component in between. Conversely, when a component is referred to as being "directly on" another component, there is no intermediate component in between.

[0070] Although terms such as “first,” “second,” and “third” can be used to describe various elements, components, regions, layers, and / or portions, such elements, components, regions, layers, and / or portions should not be limited to these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this specification, the first element, component, region, layer, or portion described below may be referred to as the second element, component, region, layer, or portion.

[0071] The terminology used in this specification is for the purpose of describing particular embodiments only and is not intended to limit the inventive concept. The singular usage covers the plural usage, including "at least one," unless it has a distinctly different meaning in the context. The term "at least one" should not be construed as limited to the singular. As used herein, the term "or" means "and / or," and the term "and / or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprising," "having," and / or "including," when used in this specification, indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.

[0072] For ease of description, spatially related terms such as “below,” “under,” “lower,” “above,” and “upper” are used herein to describe the relationship of one element or feature to another element or feature as shown in the figures. It will be understood that, in addition to the orientation shown in the figures, spatially related terms are also intended to include different orientations of the device in use or operation. For example, if the device in the figure is flipped, the element described as “below” or “under” other elements or features will be oriented “above” those other elements or features. Therefore, the term “below” can include both orientations of above and below. Devices may be oriented in other ways (rotated 90 degrees or in other orientations), and the spatially related descriptive terms used herein may be interpreted accordingly.

[0073] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having meanings consistent with their meanings in the context of the relevant field and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0074] The exemplary embodiments are described herein with reference to cross-sectional views that serve as idealized examples. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the exemplary embodiments should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the actual shapes of the regions or to limit the scope of this description.

[0075] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±20%, 10%, or 5%.

[0076] Although specific embodiments have been described, alternatives, modifications, alterations, improvements, and substantial equivalents that are currently difficult to foresee or anticipate, or that are currently difficult to foresee or anticipate, may be conceived by the applicant or those skilled in the art. Therefore, the appended claims, as filed and as may be modified, are intended to cover all such alternatives, modifications, alterations, improvements, and substantial equivalents.

[0077] Hereinafter, according to embodiments, epoxy compounds, compositions prepared from said epoxy compounds, semiconductor devices prepared from said epoxy compounds, electronic devices prepared from said epoxy compounds, articles prepared from said epoxy compounds, and methods for preparing said articles will be described in detail.

[0078] Epoxy compounds

[0079] According to embodiments, epoxides comprising a 5-membered aromatic heterocyclic ring are represented by formula 1 or formula 2:

[0080] Formula 1

[0081] E1-(M1) a1 -(L1) b1 -M3-(L2) b2 -(M2) a2 -E2

[0082] Formula 2

[0083] 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

[0084] In equations 1 and 2,

[0085] M1, M2, M4, and M5 are each independently a aryl group represented by one of equations 3a to 3e.

[0086] M3 and M6 are each independently represented by one of formulas 4a to 4r, a heteroaryl group.

[0087] L1, L2, L3, L4, L5, and L6 are each independently -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-.

[0088] A is a substituted or unsubstituted C4-C12 alkylene group, a substituted or unsubstituted C4-C12 alkenyl group, a substituted or unsubstituted C4-C12 alkyne group, or a substituted or unsubstituted C4-C12 diene group;

[0089] E1 and E2 are each independently groups containing epoxy groups, and E1 and E2 are independently the same or different;

[0090] a1, a2, a3, and a4 are each independent integers from 0 to 2, where the sum of a1 and a2 is 1 to 4, and the sum of a3 and a4 is 1 to 4.

[0091] b1, b2, b3, and b4 are each independently 0 or 1, and b5 and b6 are each independently 1 or 2.

[0092]

[0093]

[0094] In equations 3a to 3e, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and R 12 Each is independently hydrogen, halogen, hydroxyl, or a substituted or unsubstituted C1-C10 alkyl group.

[0095] In Formula 2, A can be, for example, an unsubstituted or halogenated C4-C12 alkylene group, an unsubstituted or halogenated C4-C12 alkenylene group, an unsubstituted or halogenated C4-C12 alkyne group, or an unsubstituted or halogenated C4-C12 diene group.

[0096] Epoxides represented by Formula 1 or 2 that include a 5-membered aromatic heterocyclic ring do not contain the following structures: -OO-, -OS-, or -SS-.

[0097] Resins are typically thermal insulators, and their thermal conductivity ranges from about 0.1 watts per meter (W / mK) to about 0.2 W / mK. Heat is transferred within the resin, which acts as an insulator, through the vibration of phonons; however, the thermal conductivity can be low due to phonon scattering. Resins used as semiconductor encapsulation materials may have thermal conductivity, for example, in the range of about 0.1 W / mK to about 0.2 W / mK. Even when fillers with high thermal conductivity are added to the resin, the increase in the thermal conductivity of the compound is not significant. For example, Figure 1 It is a graph illustrating the change in thermal conductivity of the compound based on the thermal conductivity of the filler. Figure 1 The diagram shows the change in thermal conductivity of the compound, including both filler and resin, as the amount of filler in a resin with a thermal conductivity of approximately 0.2 W / mK increases from approximately 1 vol% to approximately 90 vol%, with the results calculated based on the Maxwell model. Figure 1 As shown, with a filler content of approximately 90% by volume, even when the thermal conductivity of the filler increases to approximately 50 W / mK or higher, the thermal conductivity of the compound converges to approximately 5 W / mK. In other words, in a compound comprising both filler and resin, even when the thermal conductivity of the filler increases to approximately 100 W / mK, the thermal conductivity of the compound converges to approximately 5 W / mK and does not increase further.

[0098] In an embodiment, the epoxy compound represented by Formula 1, comprising a 5-membered aromatic heterocyclic ring, has a mesogenic unit in its main chain containing multiple aromatic rings. While not wishing to be bound by theory, it is understood that when the multiple aromatic rings in the mesogenic unit form π-π stacks and intermolecular hydrogen bonds, the chain stiffness of the epoxy compound's main chain can increase, and the molecular ordering of the epoxy compound can increase. As a result, phonon transport pathways can be provided in the resin as the epoxy compound and / or its cured product. Therefore, the thermal conductivity of the epoxy compound and / or its cured product can increase. In an embodiment, the mesogenic unit in the epoxy compound represented by Formula 1, comprising a 5-membered aromatic heterocyclic ring, may include a heteroaromatic ring. The heteroatoms of the heteroaromatic ring can form additional bonds, such as hydrogen bonds, with adjacent epoxy compounds, and thus provide additional phonon transport pathways in the resin. In an embodiment, the thermal conductivity of the resin as the epoxy compound and / or its cured product can be further increased. In embodiments, the epoxy compound represented by Formula 2, comprising aromatic heterocyclic rings, may further include flexible spacer groups between mesocrystalline units. When the spacer groups are further introduced into the epoxy compound, for example, a liquid crystal-like structure, such as a smectic phase, may be formed. The molecular ordering of the epoxy compound and / or the resin prepared therefrom can be increased by including highly ordered domains, such as a liquid crystal-like structure. As a result, phonon scattering in the resin as the epoxy compound and / or its cured product can be suppressed. Therefore, the thermal conductivity of the resin as the epoxy compound and / or its cured product can be further increased. In embodiments, when the resin as a cured product prepared from the epoxy compound represented by Formula 1 and / or 2 has high thermal conductivity, the thermal conductivity of the compound comprising the resin can be significantly increased. For example, Figure 2 It is a graph illustrating the change in thermal conductivity of the compound based on the thermal conductivity of the resin. Figure 2 This shows the change in thermal conductivity of the compound, including both filler and resin, based on the amount of filler, when the thermal conductivity of the Al2O3 filler is fixed at approximately 50 W / mK and the thermal conductivity of the resin increases from approximately 0.2 W / mK to approximately 1.0 W / mK. The results are calculated based on the Maxwell model. Figure 2 As shown, with a filler content of about 90% by volume, the thermal conductivity of the compound increases up to about 18 W / mK as the thermal conductivity of the resin increases from about 0.2 W / mK to about 1.0 W / mK.

[0099] The epoxy compound represented by Formula 1 can be, for example, an epoxy compound represented by one of Formulas 5a to 5f:

[0100]

[0101] In formulas 5a to 5f, M1 and M2 may each be independently represented by one of formulas 3a to 3e, M3 may be represented by one of formulas 4a to 4r, L7 and L8 may each be independently represented by -O-, -C(=O)-, -C(=O)O-, or -OC(=O)O-, and E1 and E2 may each be independently represented by a group containing an epoxy group, and E1 and E2 may each be independently the same or different.

[0102] The epoxy compound represented by Formula 2 can be, for example, an epoxy compound represented by one of Formulas 6a to 6f:

[0103] Formula 6a

[0104] E1-M1-L9-M3-L10-M2-L13-A1-L14-M4-L11-M6-L12-M5-E2

[0105] Formula 6b

[0106] E1-M1-L9-M3-L13-A1-L14-M4-L11-M6-E2

[0107] Formula 6c

[0108] E1-M3-L10-M2-L13-A1-L14-M6-L12-M5-E2

[0109] Formula 6d

[0110] E1-M1-M3-M2-L13-A1-L14-M4-M6-M5-E2

[0111] Formula 6e

[0112] E1-M1-M3-L13-A1-L14-M4-M6-E2

[0113] Formula 6f

[0114] E1-M3-M2-L13-A1-L14-M6-M5-E2

[0115] In formulas 6a to 6f, M1, M2, M4, and M5 can each independently be an aryl group represented by one of formulas 3a to 3e; M3 and M6 can each independently be a heteroaryl group represented by one of formulas 4a to 4r; L9, L10, L11, and L12 can each independently be -O-, -S-, -C(=O)-, -S(=O)-, -C(=O)O-, or -OC(=O)O-; L 13 and L14 can each be independently -O- or -S-, A1 can be a C4-C12 alkylene group that is partially or completely substituted with a halogen, an unsubstituted C4-C12 alkylene group, a C4-C12 diene group that is partially or completely substituted with a halogen, or an unsubstituted C4-C12 diene group, and E1 and E2 can each be independently groups containing an epoxy group, and E1 and E2 can each be independently the same or different.

[0116] In an epoxide compound comprising a 5-membered aromatic heterocyclic ring represented by any one of formulas 6a to 6f, A1 may be, for example, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, butyladienyl, pentylene, hexadienyl, heptylene, octylene, nonylene, decylene, undecadienyl, or dodecadienyl. For example, A1 may be butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, or dodecylene. For example, A1 may be butylene, hexylene, octylene, or decylene.

[0117] In epoxides comprising a 5-membered aromatic heterocyclic ring represented by Formula 1 or Formula 2, E1 and E2 may be independently the same or different. For example, E1 and E2 may each be independently an epoxide-containing group represented by one of Formulas 7a to 7d.

[0118]

[0119]

[0120] In equations 7a to 7d, R a and R b Each can be independently hydrogen, halogen, hydroxyl, or substituted or unsubstituted C1-C10 alkyl, and n is an integer from 1 to 10.

[0121] In an epoxide compound comprising a 5-membered aromatic heterocyclic ring represented by Formula 1 or Formula 2, M1, M2, M4, and M5 may be independently the same or different. For example, M1, M2, M4, and M5 may each be independently an arylene group represented by one of Formulas 8a to 8e, and E1 and E2 may each be independently the same or different. For example, E1 and E2 may each be independently an epoxide-containing group represented by one of Formulas 9a to 9d.

[0122]

[0123] In equations 9a to 9d, n is an integer from 1 to 10.

[0124] Epoxides comprising a 5-membered aromatic heterocyclic ring, as represented by Formula 1, can be epoxides represented by one of Formulas 10a to 10o and 11a to 11r:

[0125] Formula 10a

[0126]

[0127] Formula 10b

[0128]

[0129] Formula 10c

[0130]

[0131] Formula 10d

[0132]

[0133] Formula 10e

[0134]

[0135] Formula 10f

[0136]

[0137] Formula 10g

[0138]

[0139] Formula 10h

[0140]

[0141] Formula 10i

[0142]

[0143] Formula 10j

[0144]

[0145] Formula 10k

[0146]

[0147] Formula 10l

[0148]

[0149] 10m

[0150]

[0151] Equation 10n

[0152]

[0153] Formula 10o

[0154]

[0155] Formula 11a

[0156]

[0157] Formula 11b

[0158]

[0159] Formula 11c

[0160]

[0161] Formula 11d

[0162]

[0163] Formula 11e

[0164]

[0165] Formula 11f

[0166]

[0167] Formula 11g

[0168]

[0169] Formula 11h

[0170]

[0171] Formula 11i

[0172]

[0173] Formula 11j

[0174]

[0175] Formula 11k

[0176]

[0177] Formula 11l

[0178]

[0179] Formula 11m

[0180]

[0181] Equation 11n

[0182]

[0183] Formula 11o

[0184]

[0185] Formula 11p

[0186]

[0187] Formula 11q

[0188]

[0189] Formula 11r

[0190]

[0191] Epoxides comprising a 5-membered aromatic heterocyclic ring, as represented by Formula 2, can be epoxides represented by one of Formulas 12a to 12r and 13a to 13r:

[0192] Formula 12a

[0193]

[0194] Formula 12b

[0195]

[0196] Formula 12c

[0197]

[0198] Formula 12d

[0199]

[0200] Formula 12e

[0201]

[0202] Formula 12f

[0203]

[0204] Formula 12g

[0205]

[0206] Formula 12h

[0207]

[0208] Formula 12i

[0209]

[0210] Equation 12j

[0211]

[0212] Formula 12k

[0213]

[0214] Formula 12l

[0215]

[0216] Formula 12m

[0217]

[0218] Equation 12n

[0219]

[0220] Formula 12o

[0221]

[0222] Formula 12p

[0223]

[0224] Equation 12q

[0225]

[0226] Formula 12r

[0227]

[0228] Formula 13a

[0229]

[0230] Formula 13b

[0231]

[0232] Formula 13c

[0233]

[0234] Formula 13d

[0235]

[0236] Formula 13e

[0237]

[0238] Formula 13f

[0239]

[0240] Formula 13g

[0241]

[0242] Formula 13h

[0243]

[0244] Formula 13i

[0245]

[0246] Formula 13j

[0247]

[0248] Formula 13k

[0249]

[0250] Formula 13l

[0251]

[0252] Formula 13m

[0253]

[0254] Equation 13n

[0255]

[0256] Formula 13o

[0257]

[0258] Formula 13p

[0259]

[0260] Equation 13q

[0261]

[0262] Formula 13r

[0263]

[0264] The melting point of the epoxy compound represented by Formula 1 or Formula 2 may be, for example, about 200°C or lower, about 195°C or lower, about 190°C or lower, or about 185°C or lower. The melting point of the epoxy compound represented by Formula 1 or Formula 2 may be, for example, about 30°C to about 200°C, about 50°C to about 200°C, about 80°C to about 195°C, about 100°C to about 190°C, or about 120°C to about 185°C. While not wishing to be bound by theory, it is understood that when the epoxy compound represented by Formula 1 and Formula 2 has a melting point within these ranges, the curing temperature of the epoxy resin composition can be reduced, and therefore damage to electronic components, such as thermal deformation, due to excessively high curing temperatures can be prevented during the curing of the epoxy resin composition.

[0265] Because the epoxy compound of Formula 2 further includes a spacer group (A), the melting point of the epoxy compound of Formula 2 may be lower than that of the epoxy compound of Formula 1. For example, the melting point of the epoxy compound of Formula 2 may be about 95% or less, about 90% or less, or about 80% or less of the melting point of the epoxy compound of Formula 1. For example, the melting point of the epoxy compound of Formula 2 may be about 95% to about 1%, about 80% to about 1%, about 60% to about 5%, about 50% to about 5%, about 40% to about 10%, or about 30% to about 10% lower than that of the epoxy compound of Formula 1. For example, when the melting point of the epoxy compound of Formula 1 is about 180°C, the melting point of the epoxy compound of Formula 2 may be about 171°C or lower.

[0266] Epoxy Resin Composition

[0267] According to an embodiment, the epoxy resin composition comprises: an epoxy compound represented by any one of the formulas 1, 2, 5a to 5f, 6a to 6f, 10a to 10o, 11a to 11r, 12a to 12r, and 13a to 13r as described above; and a curing agent. When the epoxy resin composition includes the epoxy compound, the cured product of the epoxy resin composition can provide improved thermal conductivity. The epoxy resin composition can be molded into various forms.

[0268] The curing agent in the epoxy resin composition may be, for example, an amine-based curing agent, an anhydride-based curing agent, a polyamine curing agent, a polysulfide curing agent, a linear phenolic resin type curing agent, a bisphenol A type curing agent, and a dicyandiamide curing agent, but the embodiments are not limited thereto. The curing agent may be, for example, a polyfunctional phenol-based curing agent. The polyfunctional phenol-based curing agent may be, for example, a compound having at least three phenolic hydroxyl groups, and the compound may have the following structure.

[0269]

[0270] Where n is an integer from 1 to 10000.

[0271] The number-average molecular weight of the polyfunctional phenol-based curing agent may, for example, be in the range of about 300 Daltons to about 30,000 Daltons, about 400 Daltons to about 30,000 Daltons, about 600 Daltons to about 10,000 Daltons, or about 800 Daltons to about 10,000 Daltons.

[0272] The amount of the curing agent can range from about 0.1 parts by weight to about 10 parts by weight, about 0.1 parts by weight to about 5 parts by weight, or about 0.1 parts by weight to about 1 part by weight based on 100 parts by weight of the epoxy resin composition, but the embodiments are not limited thereto. When the amount of the curing agent is within these ranges, the deterioration of the insulating properties of the compound (component) can be prevented by minimizing the amount of unreacted curing agent while increasing the curing rate of the epoxy resin composition.

[0273] The epoxy resin composition may further include, for example, fillers, and the fillers may be inorganic fillers, organic fillers, or combinations thereof.

[0274] The inorganic filler may be at least one of, for example, silicon dioxide, calcium carbonate, magnesium carbonate, magnesium oxide, clay, alumina (Al2O3), titanium dioxide (TiO2), talc, calcium silicate, antimony oxide, glass fiber, or nepheline ceramic, but the embodiments are not limited thereto. The nepheline ceramic may be a crystalline glass composed of Li2O, Al2O3, and SiO2 components. The organic filler may include at least one of, for example, polyethyleneimine or polyethylene glycol, but the embodiments are not limited thereto. The filler may be inorganic in terms of high thermal conductivity, enhanced rigidity of the compound, and reduced coefficient of linear expansion.

[0275] The amount of filler may, for example, range from about 20 wt% to about 99 wt%, about 30 wt% to about 99 wt%, about 40 wt% to about 99 wt%, about 50 wt% to about 99 wt%, about 60 wt% to about 99 wt%, about 70 wt% to about 99 wt%, about 80 wt% to about 99 wt%, about 90 wt% to about 99 wt%, or about 95 wt% to about 99 wt%, based on the total weight of the epoxy resin composition. When the amount of filler in the epoxy resin composition is within these ranges, properties such as moldability, low-stress properties, high-temperature strength, and coefficient of thermal expansion can be effectively controlled.

[0276] The epoxy resin composition may further comprise at least one additive derived from: a curing accelerator, a reaction regulator, a release agent, a coupling agent, a stress-reducing agent, or an auxiliary flame retardant. Each additive may be included independently in the epoxy resin composition in an amount ranging from about 0.1 parts by weight to about 10 parts by weight, about 0.1 parts by weight to about 5 parts by weight, about 0.1 parts by weight to about 3 parts by weight, or about 0.1 parts by weight to about 1 part by weight, based on 100 parts by weight of the epoxy resin composition.

[0277] In addition to the epoxy compound according to the embodiments, the epoxy resin composition may further comprise any conventional or suitable epoxy resin. When the epoxy resin composition comprises any conventional or suitable epoxy resin, the coefficient of thermal expansion, warpage, and processing characteristics of the compound can be further improved, and the peel strength of the epoxy resin composition can also be improved. Examples of conventional or suitable epoxy resins may include biphenyl epoxy resins, phenolic varnish epoxy resins, dicyclopentadienyl epoxy resins, bisphenol epoxy resins, terpene epoxy resins, aralkyl epoxy resins, polyfunctional epoxy resins, naphthalene epoxy resins, and halogenated epoxy resins. These epoxy resins may be used alone or in mixtures of two or more. The amount of the conventional or suitable epoxy resin may, for example, range from about 1 part by weight to about 15 parts by weight, about 1 part by weight to about 10 parts by weight, or about 1 part by weight to about 5 parts by weight based on 100 parts by weight of the epoxy resin composition, but the embodiments are not limited thereto. When the epoxy resin composition further includes conventional epoxy resin in amounts within these ranges, for example, the adhesion between the substrate and the epoxy resin composition on a semiconductor package, as well as the coefficient of thermal expansion and processability of the compound, can be further improved.

[0278] The epoxy resin composition can be used for a variety of purposes. For example, the epoxy resin composition can be used as an encapsulating resin composition or a fixing resin composition. The encapsulating resin composition (a resin composition for encapsulating electronic compartments (cabins, grids, compartments)) can be, for example: a resin composition for encapsulating semiconductors, capable of encapsulating electronic compartments such as semiconductor chips and used in semiconductor packages; a resin composition for encapsulating electronic control units for vehicles, wherein a substrate having electronic compartments mounted thereon is encapsulated; or a resin composition for encapsulating sensors, sensor modules, cameras, camera modules, modules with indicators, modules with batteries, or modules with coin cells. The fixing resin composition can be, for example, a fixing resin composition for engine compartments. The fixing resin composition for engine compartments can be, for example, a resin composition for fixing rotor core magnets or for fixing stators. The epoxy resin composition can be used for purposes other than those described above.

[0279] There are no particular limitations on the method for preparing the epoxy resin composition. The method may include selecting components such as an epoxy compound and a curing agent; and mixing the components. For example, an epoxy compound suitable for use in an epoxy resin composition may be represented by Formula 1 and / or Formula 2. Subsequently, the epoxy compound may be mixed with other components such as a curing agent or additives to prepare a mixture as an epoxy resin composition.

[0280] In mixing the components, any suitable method can be used to obtain the mixture. Alternatively, the mixture can be melt-kneaded, for example, at a temperature below the curing temperature of the epoxy resin composition, to obtain a kneaded product. As a kneading method, a kneading extruder, such as a single-shaft or bi-shaft kneading extruder, or a roller kneader, such as a mixing roller, can be used, but a bi-shaft kneading extruder is preferred. After cooling the molten kneaded product, it can be molded into powder, granules, small pieces (flakes), or sheet shapes. As a method for preparing a powdered resin composition, for example, a method of pulverizing the kneaded product using a pulverizing device can be used. The kneaded product can be molded into sheets and then pulverized. The equipment used in pulverization can be, for example, a hammer mill, a mortar and pestle mill, or a roller crusher. Methods for preparing resin compositions in granular or powder form may include processing methods, such as thermal cutting techniques, in which small pieces (dice) of a small diameter are mounted on the discharge port of a kneading device, and the molten kneaded product discharged from the small pieces is cut to a predetermined length by a cutter. After preparing the resin composition in granular or powder form using the processing method such as thermal cutting techniques, the resin composition may be degassed without significantly reducing its temperature.

[0281] semiconductor devices

[0282] According to an embodiment, a semiconductor device includes: a substrate; a semiconductor; and a cured product of an epoxy resin composition, said epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof; a sealing portion formed by the cured product of the epoxy resin composition, said epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof; and a substrate portion formed by the cured product of the epoxy resin composition, said epoxy resin composition comprising a curing agent and The semiconductor device comprises an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound having a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof; a reinforcing portion formed by a cured product of an epoxy resin composition, the epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof; or an attachment portion formed by a cured product of an epoxy resin composition, the epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof. When the semiconductor device includes at least one of the cured product, a sealing portion, a substrate portion, a reinforcing portion, or an attachment portion, the heat release characteristics of the semiconductor device can be improved, and as a result, the thermal stability of the semiconductor device can be improved.

[0283] The thermal conductivity of the cured product of the epoxy resin composition in the semiconductor device may be, for example, about 0.4 W / mK or higher, about 0.45 W / mK or higher, about 0.5 W / mK or higher, about 0.55 W / mK or higher, or about 0.6 W / mK or higher. The thermal conductivity of the cured product of the epoxy resin composition in the semiconductor device may, for example, be in the range of about 0.4 W / mK to about 50 W / mK, about 0.45 W / mK to about 45 W / mK, about 0.5 W / mK to about 40 W / mK, about 0.55 W / mK to about 30 W / mK, about 0.55 W / mK to about 20 W / mK, about 0.55 W / mK to about 10 W / mK, or about 0.6 W / mK to about 10 W / mK. When the thermal conductivity of at least one of the cured product, sealing portion, substrate portion, reinforcement portion, or attachment portion in the semiconductor device is within these ranges, the thermal stability of the semiconductor device can be further improved.

[0284] Because the epoxy compound of Formula 2 further includes a spacer group (A), the thermal conductivity of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 2 can be higher than that of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 1. For example, the thermal conductivity of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 2 can be, for example, about 110% to about 200%, about 120% to about 200%, about 130% to about 200%, about 150% to about 200%, or about 160% to about 200% of the thermal conductivity of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 1. For example, when the thermal conductivity of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 1 is about 0.50 W / mK, the thermal conductivity of the cured product of the epoxy resin composition comprising the epoxy compound of Formula 2 can be about 0.55 W / mK or higher.

[0285] The semiconductor device may be, for example, a semiconductor package. (See reference) Figure 3 Semiconductor package 100 includes: a substrate 5; a die attachment film 4 disposed on the substrate 5; a semiconductor chip 3 disposed on the substrate 5 and attached to the substrate 5 via the die attachment film 4; coupling portions 6, such as bonding wires, electrically connecting the semiconductor chip 3 and the substrate 5; and a molding portion 110 encapsulating the semiconductor chip 3 and the coupling portions 6 and serving to protect the substrate 5 and a receiving structure including the semiconductor chip 3 and the coupling portions 6 mounted on the substrate 5. The molding portion 110 is formed to completely encapsulate the semiconductor chip 3 and the coupling portions 6 on the substrate 5. The molding portion 110 may be prepared from an epoxy resin composition described herein. The molding portion 110 may include an epoxy resin 1 and a filler 2 dispersed in the epoxy resin 1. The molding portion 110 may have a form in which the filler is dispersed in a resin matrix formed by curing the epoxy compound. A plurality of solder balls 7 electrically connecting the semiconductor chip 3 to an external circuit (not shown) are formed on a surface 5B of the substrate 5 opposite to the receiving surface 5A on which the semiconductor chip 3 is mounted. To prepare semiconductor packages using epoxy resin compositions, for example... Figure 3 The semiconductor package 100 shown can be formed using a low-pressure transfer molding process to create a molded portion 110 that encapsulates the semiconductor chip 3 mounted on the substrate 5. In embodiments, injection molding or casting processes can be used instead of the low-pressure transfer molding process, for example. The molded portion 110 formed using the epoxy resin composition protects areas of the semiconductor chip 3 from moisture within the semiconductor package 100 and provides improved heat release characteristics. Therefore, the reliability of the semiconductor package 100 is improved even in humid environments.

[0286] electronic devices

[0287] According to an embodiment, an electronic device includes: a substrate; electronic components; and a cured product of an epoxy resin composition, said epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof, comprising a sealing portion of the cured product of said epoxy resin composition, a substrate portion comprising the cured product of said epoxy resin composition, a reinforcing portion comprising the cured product of said epoxy resin composition, or an attachment portion comprising the cured product of said epoxy resin composition. When the electronic device includes at least one of said cured product, sealing portion, substrate portion, reinforcing portion, or attachment portion, the heat release characteristics of the electronic device can be improved, and as a result, the thermal stability of the electronic device can be improved.

[0288] The thermal conductivity of the cured product of the epoxy resin composition in the electronic device may be, for example, about 0.4 W / mK or higher, about 0.45 W / mK or higher, about 0.5 W / mK or higher, about 0.55 W / mK or higher, or about 0.6 W / mK or higher. The thermal conductivity of the cured product of the epoxy resin composition in the electronic device may, for example, be in the range of about 0.4 W / mK to about 50 W / mK, about 0.45 W / mK to about 45 W / mK, about 0.5 W / mK to about 40 W / mK, about 0.55 W / mK to about 30 W / mK, about 0.55 W / mK to about 20 W / mK, about 0.55 W / mK to about 10 W / mK, or about 0.6 W / mK to about 10 W / mK. When the thermal conductivity of at least one of the cured product, sealing portion, substrate portion, reinforcing portion, or attachment portion in the electronic device is within these ranges, the thermal stability of the electronic device can be further improved.

[0289] The electronic device may be, for example, an electronic control unit, sensor, sensor module, camera, camera module, module with indicator, module with battery, or module with coin cell battery, wherein a substrate having an electronic compartment mounted thereon is encapsulated. The electronic device may be, for example, an integrated circuit device or a printed circuit board having electronic components mounted thereon. (Reference) Figure 4 The integrated circuit device 300 includes a plurality of semiconductor chips 320 sequentially stacked on a packaging substrate 310. A control chip 330 is connected to the plurality of semiconductor chips 320. The stack of the plurality of semiconductor chips 320 and the control chip 330 is sealed on the packaging substrate 310 by a molding portion 340. The molding portion 340 may have a... Figure 3The molding portion 340 has similar characteristics to the molded portion 110 described herein. The molding portion 340 can be prepared using the epoxy resin composition described herein. The molding portion 340 includes an epoxy resin 341 and a plurality of fillers 342 dispersed in the epoxy resin 341. Details regarding the epoxy resin 341 and the fillers 342 can be found in [the following text is missing from the original extract]. Figure 3 The details of epoxy resin 1 and filler 2 are the same. Figure 4 This diagram illustrates an example structure in which multiple semiconductor chips 320 are vertically stacked. The multiple semiconductor chips 320 can be arranged horizontally on a packaging substrate 310, or in a combination of vertical and horizontal mounting arrangements. The control chip 330 may be omitted. The packaging substrate 310 can be a flexible printed circuit board, a rigid printed circuit board, or a combination thereof. The packaging substrate 310 includes internal distribution lines 312 and connection terminals 314. The connection terminals 314 can be formed on one surface of the packaging substrate 310. Solder balls 316 are formed on another surface of the packaging substrate 310. The connection terminals 314 are electrically connected to the solder balls 316 via the internal distribution lines 312. The solder balls 316 can be replaced by conductive bumps or lead gate arrays (LGAs). The multiple semiconductor chips 320 and the control chip 330 may each include connection structures 322 and 332, respectively. The connection structures 322 and 332 can each be formed using, for example, through-silicon via (TSV) contact structures. Interconnection structures 322 and 332 in the plurality of semiconductor chips 320 and the control chip 330 are electrically connected to the connection terminals 314 of the package substrate 310 via connection portions 350, such as bumps. The plurality of semiconductor chips 320 may each include a system LSI, flash memory, DRAM, SRAM, EEPROM, PRAM, MRAM, or RRAM. The control chip 330 may include logic circuitry such as a serializer / deserializer (SER / DES) circuit. Reference Figure 5 The integrated circuit device 400 includes a module substrate 410; and a control chip 420 and multiple semiconductor packages 430 mounted on the module substrate 410. Multiple input / output terminals 450 are formed on the module substrate 410. The multiple semiconductor packages 430 include... Figure 3 Semiconductor package 100 or Figure 4 At least one of the integrated circuit devices 300.

[0290] Products

[0291] According to an embodiment, the article comprises: a substrate; and a cured product of an epoxy resin composition, said epoxy resin composition comprising a curing agent and an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 1, an epoxy compound containing a 5-membered aromatic heterocyclic ring and represented by Formula 2, or a combination thereof, including a sealing portion of the cured product of the epoxy resin composition, a substrate portion of the cured product of the epoxy resin composition, a reinforcing portion of the cured product of the epoxy resin composition, or an attachment portion of the cured product of the epoxy resin composition. When the article comprises at least one of the cured product, the sealing portion, the substrate portion, the reinforcing portion, or the attachment portion, the heat release characteristics of the article are improved, and as a result, the thermal stability of the article is improved.

[0292] The thermal conductivity of the cured product of the epoxy resin composition in the article can be, for example, about 0.4 W / mK or higher, about 0.45 W / mK or higher, about 0.5 W / mK or higher, about 0.55 W / mK or higher, or about 0.6 W / mK or higher. The thermal conductivity of the cured product of the epoxy resin composition in the article can be, for example, in the range of about 0.4 W / mK to about 50 W / mK, about 0.45 W / mK to about 45 W / mK, about 0.5 W / mK to about 40 W / mK, about 0.55 W / mK to about 30 W / mK, about 0.55 W / mK to about 20 W / mK, about 0.55 W / mK to about 10 W / mK, or about 0.6 W / mK to about 10 W / mK. When the thermal conductivity of at least one of the cured product, sealing portion, substrate portion, reinforcing portion, and attachment portion in the article is within these ranges, the thermal stability of the article can be further improved.

[0293] The product may be, for example, an MP3 player, a navigation system, a portable multimedia player (PMP), a solid-state drive (SSD), or a home appliance, but the implementation is not limited thereto.

[0294] According to an embodiment, a method for preparing an article includes: providing an epoxy resin composition described herein on a substrate; and curing the epoxy resin composition.

[0295] The epoxy resin composition can be provided on the substrate in various states, such as liquid, solid, and semi-cured. The epoxy resin composition provided in a liquid state can be provided in a molten state or dissolved in a solvent. The epoxy resin composition provided in a solid state can be provided on the substrate in various shapes, such as powder, granules, or flakes. The epoxy resin composition can be provided on the substrate in an uncured, partially cured, or semi-cured state. The epoxy resin composition can be molded into a predetermined shape after being provided on the substrate, or it can be provided on the substrate after being molded into a predetermined shape.

[0296] Once the epoxy resin composition is provided on the substrate, it can be cured to prepare an article. The cured epoxy resin composition may form a sealing portion, substrate portion, reinforcing portion, or attachment portion of the article, but the embodiments are not limited thereto.

[0297] Methods for curing the epoxy resin composition may include heat curing or ultraviolet curing, but are not limited thereto. The epoxy resin composition can be cured by heat. The curing temperature of the epoxy resin composition may be about 100°C or higher, about 110°C or higher, or about 120°C or higher. The curing temperature of the epoxy resin composition may, for example, be about 200°C or lower, about 195°C or lower, about 190°C or lower, about 185°C or lower, or about 180°C or lower. The curing temperature of the epoxy resin composition may, for example, be in the range of about 100°C to about 200°C, about 110°C to about 200°C, about 120°C to about 200°C, about 130°C to about 200°C, about 150°C to about 195°C, about 160°C to about 190°C, about 150°C to about 185°C, or about 150°C to about 180°C. When the epoxy resin composition is cured at a curing temperature within these ranges, it can prevent damage caused by thermal deformation of semiconductors or electronic components.

[0298] In the following text, the definitions of substituents used in the formulas of this specification are the same as those in the following description.

[0299] As used herein, the substituents of substituted alkyl, substituted alkylene, substituted alkenyl, substituted alkyne, and substituted diene may each independently be a halogen atom, a hydroxyl group, a C1-C5 alkyl, a C1-C5 alkoxy, a C1-C5 alkylthio, a C6-C30 aryloxy, a C6-C30 arylthio, or a combination thereof.

[0300] As used herein, the term "alkyl" refers to a fully saturated branched or unbranched (straight-chain or linear) hydrocarbon group.

[0301] Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, and isoheptyl.

[0302] At least one hydrogen atom of an alkyl group may be replaced by the following substituents: halogen atom, hydroxyl group, alkoxy group, nitro group, cyano group, amino group, amido group, hydrazine group, hydrazone group, carboxyl group, carbamoyl group, thiol group, ester group, carboxyl group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C20 alkyl group, C2-C20 alkenyl group, C2-C20 alkynyl group, C6-C30 aryl group, C7-C30 aralkyl group, C1-C30 alkoxy group, C1-C30 alkylthio group, C6-C30 aryloxy group, C6-C30 arylthio group, C1-C20 heteroalkyl group, C3-C20 heterocyclic alkyl group, or combinations thereof.

[0303] As used herein, the term "alkenyl" refers to an alkyl group that includes at least one carbon-carbon double bond.

[0304] As used herein, the term "alkynyl" refers to an alkyl group that includes at least one carbon-carbon triple bond.

[0305] As used herein, the term “dienyl” refers to an alkyl group comprising two carbon-carbon double bonds.

[0306] Examples of "halogen atoms" include fluorine, bromine, chlorine, and iodine.

[0307] As used herein, the term "alkoxy" means "alkyl-O-", where the alkyl group is the same as defined above. Examples of alkoxy groups may include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, hexoxy, cyclopropoxy, and cyclohexoxy. At least one hydrogen atom in an alkoxy group may be replaced by the same substituents described above with respect to alkyl groups.

[0308] As used herein, the term "alkathioyl" means "alkyl-S-", where the alkyl group is the same as defined above. Examples of alkathioyl groups may include methylthioyl, ethylthioyl, propylthioyl, isopropylthioyl, butylthioyl, tert-butylthioyl, pentylthioyl, hexylthioyl, cyclopropylthioyl, and cyclohexylthioyl. At least one hydrogen atom in the alkathioyl group may be replaced by the same substituents described above with respect to alkyl groups.

[0309] As used herein, the term "aryl" is used alone or in combination and refers to an aromatic hydrocarbon group having one or more rings. The term "aryl" includes groups in which an aromatic ring is fused to one or more cycloalkyl rings. Examples of aryl groups may include phenyl, naphthyl, or tetrahydronaphthyl. At least one hydrogen atom of an aryl group may be replaced by the same substituents described above with respect to alkyl groups.

[0310] As used herein, the term "aryloxy" refers to aryl-O-, where the aryl group is the same as defined above. Non-limiting examples of aryloxy groups may include phenoxy, naphthoxy, or tetrahydronaphthoxy. At least one hydrogen atom of an "aryloxy" group may be replaced by the same substituents described above with respect to alkyl groups.

[0311] As used herein, “arylthio” refers to aryl-S-, where the aryl group is the same as defined above. Non-limiting examples of arylthio may include phenylthio, naphthio, or tetrahydronaphthio. At least one hydrogen atom of “arylthio” may be replaced by the same substituents described above with respect to alkyl groups.

[0312] In addition, as used herein, unless otherwise defined, “heterogeneous” can refer to one to four heteroatoms selected from the following: I, O, S, Se, Te, Si, or P.

[0313] As used herein, when the linking group Ln (e.g., n can be an integer from 1 to 12) is defined as -C(=O)O-, it means that Ln can be -C(=O)O- or -OC(=O)-. The same logic applies to -(CH2)2-C(=O)-, -CH=CH-C(=O)-, -CH=N-, -NH-C(=O)O-, -C(=O)-NH-, and -OC(=O)-NH-S(=O)O-. Taking -(CH2)2-C(=O)- as an example, when Ln is defined as -(CH2)2-C(=O)-, it means that Ln can be -(CH2)2-C(=O)- or -C(=O)-(CH2)2-.

[0314] As used herein, the term "heteroaryl" refers to an aryl group in which at least one carbon atom or CH is replaced by a heteroatom or a chemical group containing at least one heteroatom.

[0315] As used herein, the term "alkylene" refers to a divalent aliphatic hydrocarbon group corresponding to "alkyl".

[0316] As used herein, the term "alkenyl" refers to a divalent aliphatic hydrocarbon group corresponding to "alkenyl".

[0317] As used herein, the term "hydrinyl" refers to the divalent aliphatic hydrocarbon group corresponding to "ynyl".

[0318] As used herein, the term “dienyl” refers to a divalent aliphatic hydrocarbon group corresponding to “dienyl”.

[0319] As used herein, the term "aryl" refers to a divalent aromatic hydrocarbon group corresponding to "aryl".

[0320] As used herein, the term "hybrid aryl" refers to a divalent aryl group in which at least one carbon atom or CH is replaced by a heteroatom or a chemical group containing at least one heteroatom.

[0321] As used herein, an open "—" indicates a single bond or a methyl group. For example, in the following structures, an open "—" without any R substituents indicates a single bond or a methyl group.

[0322]

[0323] The term "room temperature" as used in this article refers to a temperature of approximately 25°C.

[0324] One or more embodiments will now be described in more detail with reference to the following examples. However, these embodiments are not intended to limit the scope of the one or more embodiments. The phrase “using 'B' instead of 'A'” used in describing synthetic embodiments means that the amount of 'A' used is the same as the amount of 'B' used in molar equivalent.

[0325] Example

[0326] Preparation of epoxy compounds and cured products

[0327] Example 1

[0328] Preparation of epoxides

[0329] 16 g of 2,5-furandicarboxylic acid (FDA), 100 mL of tetrahydrofuran (THF), and 0.05 mL of dimethylformamide (DMF) were added to a 500 mL glass reactor, followed by the addition of 20 g of oxaloyl chloride. The mixture was allowed to react at room temperature for 2 hours to obtain furan-2,5-dicarboxylic chloride (FDCDCl). After dissolving 9 g of hydroquinone in 100 mL of pyridine, 8 g of FDCDCl was added and the mixture was allowed to react at room temperature for 4 hours. Water was added to the resulting solution, and a precipitate was obtained by filtration. The precipitate was washed several times with water, recrystallized in pyridine, and dried in a vacuum oven at 60 °C for 12 hours to prepare intermediate 1-1.

[0330] Intermediate 1-1

[0331]

[0332] 5 g of intermediate 1-1, 50 g of epichlorohydrin, and 20 g of isopropanol were added to a 250 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 1.2 g of sodium hydroxide (NaOH) (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH, thereby preparing the compound represented by Formula 11a.

[0333] Formula 11a

[0334]

[0335] 1 H 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).

[0336] Preparation of cured products

[0337] An epoxy resin composition was prepared by mixing the epoxy compound represented by Formula 11a and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0338] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0339] Example 2

[0340] Preparation of epoxides

[0341] 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 to a 500 ml glass reactor and reacted at 160 °C for 4 hours under a nitrogen atmosphere. Water was added to the resulting solution, and a precipitate 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 prepare intermediate 2-1.

[0342] Intermediate 2-1

[0343]

[0344] 5 g of intermediate 2-1, 50 g of epichlorohydrin, and 20 g of isopropanol were added to a 250 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 1.2 g of NaOH (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was then raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH, thereby preparing the compound represented by formula 10c.

[0345] Formula 10c

[0346]

[0347] 1 H 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)

[0348] Preparation of cured products

[0349] An epoxy resin composition was prepared by mixing the epoxy compound represented by formula 10c and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0350] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0351] Example 3

[0352] Preparation of epoxides

[0353] 200 ml of 95% ethanol, 170 g of intermediate 1-1 prepared in Example 1, 0.09 g of sodium dithionite, and 21 g of 1,4-dibromobutane were added to a 1-liter (L) glass reactor, and the contents were mixed. Then, while stirring and refluxing the mixture for 1 hour, 8.4 g of potassium hydroxide (KOH) dissolved in 100 ml of 95% ethanol was slowly added to the reactor, and the contents were refluxed for 8 hours. The solution was cooled to room temperature and neutralized with 30% by weight sulfuric acid, and 500 ml of 95% ethanol was added. A precipitate was obtained by filtration. The precipitate was washed several times with ethanol and then vacuum dried to prepare intermediate 1-2.

[0354] Intermediate 1-2

[0355]

[0356] 30 g of intermediates 1-2, 148 g of epichlorohydrin, and 80 g of isopropanol were added to a 500 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was then raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH, thereby preparing the compound represented by Formula 13a.

[0357] Formula 13a

[0358]

[0359] 1 H 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)

[0360] Preparation of cured products

[0361] An epoxy resin composition was prepared by mixing the epoxy compound represented by Formula 13a and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0362] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0363] Example 4

[0364] Preparation of epoxides

[0365] 200 ml of 95% ethanol, 170 g of intermediate 2-1 prepared in Example 2, 0.09 g of sodium dithionite, and 21 g of 1,4-dibromobutane were added to a 1 L glass reactor, and the contents were mixed. Then, while stirring and refluxing the mixture for 1 hour, 8.4 g of potassium hydroxide dissolved in 100 ml of 95% ethanol was slowly added to the reactor, and the contents were refluxed for 8 hours. The solution was cooled to room temperature and neutralized with 30% sulfuric acid, and then 500 ml of 95% ethanol was added. A precipitate was obtained by filtration. The precipitate was washed several times with ethanol and then vacuum dried to prepare intermediate 2-2.

[0366] Intermediate 2-2

[0367]

[0368] 30 g of intermediate 2-2, 148 g of epichlorohydrin, and 80 g of isopropanol were added to a 500 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was then raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH, thereby preparing the compound represented by formula 12c.

[0369] Formula 12c

[0370]

[0371] 1 H 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)

[0372] Preparation of cured products

[0373] An epoxy resin composition was prepared by mixing the epoxy compound represented by Formula 12c and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0374] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0375] Example 5

[0376] Preparation of epoxides

[0377] 20.0 g of 3-(2-trimethylsilylethynyl)phenol and 150 ml of DMF were added to a 500 ml glass reactor and mixed at room temperature under a nitrogen atmosphere. Then, 85 g of 3-azidophenol, 0.1 g of cuprous bromide (I) (CuBr), and 0.2 g of 2,2-bipyridine were added, and the mixture was reacted at 80 °C for 24 hours. The resulting solution was cooled to room temperature, and water and 1 L of ethyl acetate were added to wash the organic mixture layer. The layer was then dried using anhydrous MgSO4. The solvent was removed from the dried solution by vacuum distillation, and the resulting precipitate was recrystallized from it using acetic acid / water to prepare intermediate 3-1.

[0378] Intermediate 3-1

[0379]

[0380] 200 ml of 95% ethanol, 180 g of intermediate 3-1, 0.09 g of sodium dithionite, and 21 g of 1,4-dibromobutane were added to a 1 L glass reactor, and the contents were mixed. Then, while stirring and refluxing the mixture for 1 hour, 8.4 g of potassium hydroxide dissolved in 100 ml of 95% ethanol was slowly added to the reactor, and the contents were refluxed for 8 hours. The solution was cooled to room temperature and neutralized with 30% sulfuric acid, and then 500 ml of 95% ethanol was added. The precipitate was obtained by filtration. The precipitate was washed several times with ethanol and dried under vacuum to prepare intermediate 3-2.

[0381] Intermediate 3-2

[0382]

[0383] 30 g of intermediate 3-2, 148 g of epichlorohydrin, and 80 g of isopropanol were added to a 500 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 3.2 g of NaOH (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was then raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH to prepare the compound represented by Formula 12l.

[0384] Formula 12l

[0385]

[0386] 1 H 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)

[0387] Preparation of cured products

[0388] An epoxy resin composition was prepared by mixing the epoxy compound represented by Formula 12l and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0389] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0390] Comparative Example 1

[0391] Preparation of epoxides

[0392] Purchase and use, as received, NC3000, a phenolic aryl epoxy resin represented by Formula A (available from Nippon Kayaku Co., Ltd.).

[0393] Formula A

[0394]

[0395] Preparation of cured products

[0396] An epoxy resin composition was prepared by mixing the prepared epoxy compound represented by formula A and the phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0397] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0398] Comparative Example 2

[0399] Preparation of epoxides

[0400] Purchase and use, as received, the epoxy compound SH400E represented by Formula B (available from DIC Inc., Japan).

[0401] Formula B

[0402]

[0403] Preparation of cured products

[0404] An epoxy resin composition was prepared by mixing the prepared epoxy compound represented by Formula B and the phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0405] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0406] Comparative Example 3

[0407] Preparation of epoxides

[0408] Purchase and use, as received, the epoxy compound TMBO(H) represented by formula C (available from Hitachi Chemical).

[0409] Formula C

[0410]

[0411] Preparation of cured products

[0412] An epoxy resin composition was prepared by mixing the prepared epoxy compound represented by formula C and the phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0413] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0414] Comparative Example 4

[0415] Preparation of epoxides

[0416] Synthesize and use the epoxy compound represented by formula D as described below.

[0417] 75 g of hydroquinone, 35 g of 4-hydroxybenzoic acid, 0.5 g of p-toluenesulfonic acid, and 300 ml of 1,2-dichlorobenzene were added to a 500 ml glass reactor and mixed under a nitrogen stream. The contents were then reacted at 160 °C for 4 hours. Water was added to the resulting solution, and a precipitate was obtained by filtration. The precipitate was washed several times with water, recrystallized using methanol / water, and dried in a vacuum oven at 60 °C for 12 hours to prepare intermediate 4-1.

[0418] Intermediate 4-1

[0419]

[0420] 5 g of intermediate 4-1, 50 g of epichlorohydrin, and 20 g of isopropanol were added to a 250 ml reactor. Once the reactor interior was fully purged with nitrogen, the temperature was raised to 50 °C under a nitrogen flow, and the reactor contents were refluxed for 5 hours while maintaining the temperature at 50 °C. The reactor temperature was then lowered to room temperature, and 1.2 g of NaOH (25% aqueous solution) was added dropwise to the reactor over a 1-hour period. The reactor temperature was then raised to 60 °C, and the reactor contents were stirred for 4 hours. The reactor temperature was then lowered to room temperature, and the reactor contents were recrystallized using CH2Cl2 / CH3OH to prepare the compound represented by formula D.

[0421] Formula D

[0422]

[0423] Preparation of cured products

[0424] An epoxy resin composition was prepared by mixing the epoxy compound represented by formula D and a phenol-based curing agent MEH7500 (a polyfunctional phenol available from Meiwa Plastic Industries, Ltd.) in a 1:1 equivalent ratio.

[0425] 5g of the prepared epoxy resin composition was added to an aluminum mold and cured by raising the temperature of the composition to 190°C, thereby preparing a cured product of the epoxy resin composition as a sample.

[0426] Evaluation Example 1: Measurement of Thermal Conductivity

[0427] The thermal conductivity of each sample was measured. The samples were cured products of epoxy resin compositions comprising a curing agent and an epoxy compound prepared in Examples 1-5 and Comparative Examples 1-4, respectively. The results are shown in Table 1.

[0428] Thermal conductivity was evaluated using the modified transient planar heat source (MTPS) method with a C-THERM TCI™ thermal conductivity analyzer.

[0429] Table 1: Thermal conductivity of the samples

[0430]

[0431] As shown in Table 1, the thermal conductivity of the cured products obtained from the epoxy compounds of Examples 1-4 is increased by about 50% or more compared to that of the cured products obtained from the epoxy compounds of Comparative Examples 1-4.

[0432] Furthermore, the thermal conductivity of the cured products obtained from the epoxy compounds of Examples 3-5 is increased by about 10% or more compared to that of the cured products obtained from the epoxy compounds of Examples 1 and 2.

[0433] As described above, according to one or more aspects of the embodiments, the cured product of an epoxy resin composition comprising an epoxy compound having a 5-membered aromatic heterocyclic ring may have improved thermal conductivity, and semiconductor devices comprising the cured product, electronic devices comprising the cured product, and articles comprising the cured product may have improved thermal stability.

[0434] It should be understood that the embodiments described herein are to be considered in the descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope of this detailed description as defined by the appended claims.

Claims

1. An epoxide compound having a 5-membered aromatic heterocyclic ring, represented by formula 2: 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 wherein In Equation 2, M1, M2, M4, and M5 are each independently an aryl group represented by one of equations 3a to 3c. ， Among them, in equations 3a to 3c, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , and R 12 are each independently hydrogen, halogen, or substituted or unsubstituted C1-C10 alkyl, M3 and M6 are each independently a heteroaryl group represented by one of formulas 4a to 4c and 4l. ， L1, L2, L3, and L4 are each independently -C(=O)-, -S(=O)-, -C(=O)O-, or -OC(=O)O-. L5 and L6 are each independently -O- or -S-. A is a substituted or unsubstituted C4-C12 alkylene group. a1, a2, a3, and a4 are each independent integers greater than 0 and less than 2. b1, b2, b3, and b4 are each independently 0 or 1, and b5 and b6 are each independently 1. E1 and E2 are each independently an epoxy-containing group represented by one of formulas 7a to 7c: Among them, in equations 7a to 7c, R a and R b each independently is hydrogen, halogen, or substituted or unsubstituted C1-C10 alkyl, and R1to R 12 and R a and R b each of the substituents of the substituted C1-C10 alkyl group in the definition of R and the substituents of the substituted C4-C12 alkylene group in the definition of A is independently a halogen atom, a C1-C5 alkyl group, or a combination thereof.

2. The epoxy compound of claim 1, wherein the epoxy compound represented by formula 2 is represented by one of formulas 6a and 6d: Formula 6a E1-M1-L9-M3-L10-M2-L13-A1-L14-M4-L11-M6-L12-M5-E2 Formula 6d E1-M1-M3-M2-L13-A1-L14-M4-M6-M5-E2 wherein In equations 6a and 6d, M1, M2, M4, and M5 are each independently an aryl group represented by one of equations 3a to 3c. M3 and M6 are each independently a heteroaryl group represented by one of formulas 4a to 4c and 4l. L9, L10, L11, and L12 are each independently -C(=O)-, -S(=O)-, -C(=O)O-, or -OC(=O)O-. L13 and L14 are each independently -O- or -S-. A1 is a C4-C12 alkylene group that is partially or completely substituted with a halogen, or an unsubstituted C4-C12 alkylene group, and E1 and E2 are each independently defined as in claim 1.

3. The epoxy compound of claim 2, wherein A1 is butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, or dodecylene.

4. The epoxy compound of claim 1, wherein M1, M2, M4, and M5 are each independently an arylene group represented by one of formulas 8a to 8c. ， E1 and E2 are each independently an epoxy-containing group represented by one of formulas 9a to 9c. 。 5. The epoxy compound of claim 1, wherein the epoxy compound represented by formula 2 is represented by one of formulas 12a to 12c, 12l, 13a to 13c, and 13l: Formula 12a Formula 12b Formula 12c Formula 12l Formula 13a Formula 13b Formula 13c Formula 13l 。 6. The epoxy compound of claim 1, wherein the epoxy compound represented by formula 2 has a melting point of 30°C to 200°C.

7. An epoxy resin composition comprising: The epoxy compound as described in any one of claims 1-6; and Curing agent.

8. The epoxy resin composition of 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 of claim 8, wherein the amount of the filler is in a range of 20 to 99 weight percent, based on the total weight of the epoxy resin composition.

10. A semiconductor device, comprising: a substrate; a semiconductor; and a cured product of an epoxy resin composition, the epoxy resin composition comprising a curing agent and the epoxy compound having a 5-membered aromatic heterocyclic ring represented by Formula 2 according to any one of claims 1-6.

11. The semiconductor device of claim 10, wherein the semiconductor device comprises: a sealing portion comprising the cured product of the epoxy resin composition, a substrate portion comprising the cured product of the epoxy resin composition, a reinforcing portion comprising the cured product of the epoxy resin composition, or an attaching portion comprising the cured product of the epoxy resin composition.

12. The semiconductor device of claim 10, wherein the cured product of the epoxy resin composition has a thermal conductivity of 0.4 to 50 watt / meter-Kelvin.

13. An electronic device, comprising: a substrate; an electronic component; and a cured product of an epoxy resin composition, the epoxy resin composition comprising a curing agent and the epoxy compound having a 5-membered aromatic heterocyclic ring represented by Formula 2 according to any one of claims 1-6.

14. The electronic device of claim 13, wherein the electronic device comprises: a sealing portion comprising the cured product of the epoxy resin composition, a substrate portion comprising the cured product of the epoxy resin composition, a reinforcing portion comprising the cured product of the epoxy resin composition, or an attaching portion comprising the cured product of the epoxy resin composition.

15. The electronic device of claim 13, wherein the cured product of the epoxy resin composition has a thermal conductivity of 0.4 to 50 watt / meter-Kelvin.

16. An article, comprising: a substrate; and a cured product of an epoxy resin composition, the epoxy resin composition comprising a curing agent and the epoxy compound having a 5-membered aromatic heterocyclic ring represented by Formula 2 according to any one of claims 1-6.

17. The article of claim 16, wherein the article comprises: a sealing portion comprising the cured product of the epoxy resin composition, a substrate portion comprising the cured product of the epoxy resin composition, a reinforcing portion comprising the cured product of the epoxy resin composition, or an attaching portion comprising the cured product of the epoxy resin composition.

18. The article of claim 16, wherein the cured product of the epoxy resin composition has a thermal conductivity of 0.4 to 50 watt / meter-Kelvin.

19. A method of making an article, the method comprising: providing the epoxy resin composition of any one of claims 7-9 on a substrate; and curing the epoxy resin composition. ​ 20. The method of claim 19, wherein the curing of the epoxy resin composition is performed at a temperature of 100 °C to 200 °C.

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