Epoxy compound, composition, material for semiconductor packaging, molded product, electric and electronic device, and semiconductor packaging

Abstract

An epoxy compound, a composition, a material for semiconductor packaging, a molded product, an electric and electronic device, and a semiconductor package. The epoxy compound is represented by the following chemical formula 1 and has at least one mesogenic naphthalene unit. In chemical formula 1, M as a mesogenic unit 1 、M 2 or M 3 At least one of M is a naphthalene unit. 1 、M 2 、M 3 , L 1 , L 2 and E 1 and E 2 As defined in the detailed description. Formula 1E 1 ‑M 1 ‑L 1 ‑M 2 ‑L 2 ‑M 3 ‑E 2 .

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the priority of Korean Patent Application No. 10-2019-0145923 filed in the Korean Intellectual Property Office on November 14, 2019, and all rights and interests arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a high thermal conductivity epoxy compound, a composition each comprising the high thermal conductivity epoxy compound, a material for semiconductor packaging, a molded (molded) product, an electric and electronic device, and a semiconductor package (package). The high thermal conductivity epoxy compound can be applied to various electrical and electronic fields requiring heat dissipation performance and semiconductors, and a composition each comprising the high thermal conductivity epoxy compound, a material for semiconductor packaging, a molded product, an electric and electronic device, and a semiconductor package. Background Art

[0004] With the development of electronic devices, semiconductors have become lighter, thinner and smaller in size, and therefore semiconductor circuits have become more complex at higher circuit densities. In line with this trend, the electrical, thermal and mechanical stability of molding materials have become increasingly important factors. In particular, the heating problem generated in the application processor (AP) of mobile products can have a great impact on the performance and reliability of mobile products. Molding is an encapsulation (encapsulation, encapsulating) process of semiconductors using molding compounds, which produces semiconductor packages for protecting semiconductor chips from external environmental influences, and may include achieving electrical insulation effects, and effectively dissipating heat during the operation of the chip. In practice, the purpose of molding is to protect semiconductors that may include wire bonding or flip chip bonding from electrical degradation. Electrical degradation can be caused by a variety of factors, including corrosion caused by exposure to air (oxygen) or other oxidative external contaminants, and molding provides the necessary mechanical stability and effectively releases the heat generated by the semiconductor during operation.

[0005] Typically, epoxy molding compound (EMC), which is a thermosetting resin, is used as a molding material for semiconductor packaging. However, epoxy molding compound has limitations in terms of coefficient of thermal expansion (CTE), warpage and thermal conductivity. In order to solve some or most of the limitations, a method of adding a relatively large amount of high thermal conductivity inorganic filler to EMC is often used. However, even if the thermal conductivity of the conductive inorganic filler material is increased to about 100 watts / meter-Kelvin (W / m·K) or more, the improvement of the thermal conductivity of the composite material is still limited. In particular, in the case of EMC, even if there is 90% or more filler content in the EMC composition, the thermal conductivity of the final product cannot exceed about 5W / mK. In addition, as the filler loading content increases, an aggravated degradation of mechanical properties may be exhibited. Therefore, the following molding composition is of interest: the molding composition is capable of achieving high thermal conductivity and also limiting or minimizing the amount of inorganic filler in the EMC composition.

[0006] Therefore, it is highly desirable and necessary to develop or improve high thermal conductivity materials that can be applied in the field of semiconductors and electronic devices with heat dissipation performance. Summary of the invention

[0007] One aspect of the present disclosure provides a high thermal conductivity epoxy compound, that is, an epoxy compound having high heat dissipation performance.

[0008] Another aspect of the present disclosure provides a composition including the high thermal conductivity epoxy compound.

[0009] Yet another aspect of the present disclosure provides a material for a semiconductor package, the package including the high thermal conductivity epoxy compound.

[0010] Yet another aspect of the present disclosure provides a molded product obtained using the high thermal conductivity epoxy compound.

[0011] Still another aspect of the present disclosure provides electrical and electronic devices including the high thermal conductivity epoxy compound.

[0012] Yet another aspect of the present disclosure provides a semiconductor package including the high thermal conductivity epoxy compound.

[0013] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the embodiments presented in the disclosure.

[0014] According to one aspect of the present disclosure, an epoxy compound having a naphthalene unit represented by the following Chemical Formula 1 is provided.

[0015] Chemical formula 1

[0016] E 1 -M 1-L 1 -M 2 -L 2 -M 3 -E 2

[0017] In chemical formula 1

[0018] M 1 、M 2 and M 3 Each is independently a mesogen unit (unit) represented by the following Chemical Formula 2, wherein M 1 、M 2 or M 3 At least one of them is a naphthalene unit represented by formula (2-1),

[0019] L 1 and L 2 are each independently a single bond, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH 2 ) 2 -C(=O)-, -C(=O)-(CH 2 ) 2 -, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -NHC(=O)-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH 2 (C 6 H 4 )C(=O)-, or -C(=O)(C 6 H 4 )CH 2 -,and

[0020] E 1 and E 2 are the same or different epoxy-containing groups.

[0021] Chemical formula 2

[0022]

[0023]

[0024] In chemical formula 2

[0025] R 1 To R 12each independently represents a hydrogen atom, a halogen atom, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, a C1-C30 heteroalkyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C2-C30 heteroaryl group, a C3-C30 heteroaralkyl group, a C2-C30 heteroaryloxy group, a C3-C30 heteroaryloxyalkyl group, a C3-C30 heteroaralkyloxy group, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonyl group, a sulfamoyl group, a sulfonic acid group or a salt thereof, or a phosphate group or a salt thereof,

[0026] L in the chemical formula (2-3) 3 is -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH 2 ) 2 -C(=O)-, -C(=O)-(CH 2 ) 2 -, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -NHC(=O)-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH 2 (C 6 H 4 )C(=O)-, or -C(=O)(C 6 H 4 )CH 2 -,

[0027] X is N, P or As, Y is O, S or Se, and n is an integer from 1 to 10.

[0028] According to another aspect of the present disclosure, a composition including the epoxy compound is provided.

[0029] According to still another aspect of the present disclosure, a material for semiconductor packaging is provided, which includes the epoxy compound.

[0030] According to still another aspect of the present disclosure, provided is a molded product including the epoxy compound or a cured product thereof.

[0031] According to still another aspect of the present disclosure, provided are electric and electronic devices including the epoxy compound or a cured product thereof.

[0032] According to yet another aspect of the present disclosure, there is provided a semiconductor package, comprising:

[0033] Base,

[0034] at least one chip mounted on the substrate,

[0035] a connecting portion for electrically connecting the at least one chip and the substrate, and

[0036] a molding part encapsulating the at least one chip on the substrate,

[0037] wherein the molded part is formed using the composition. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] The above and other aspects, features and advantages of some embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:

[0039] Figure 1 Schematic diagram for explaining the molecular design principle of the epoxy compound according to the embodiment.

[0040] Figure 2 is a graph showing changes in thermal conductivity of a composite material according to thermal conductivity of a filler.

[0041] Figure 3 is a graph showing changes in thermal conductivity of a composite material according to thermal conductivity of a polymer.

[0042] Figure 4 is a cross-sectional view showing a schematic configuration of a semiconductor package according to an embodiment.

[0043] Figure 5 is a cross-sectional view showing main elements of an integrated circuit device according to an embodiment.

[0044] Figure 6 is a plan view showing main elements of an integrated circuit device according to an embodiment.

[0045] Figure 7 is a diagram showing main elements of an integrated circuit device according to an embodiment.

[0046] Figure 8 is a diagram schematically showing a mobile radio telephone according to an embodiment. DETAILED DESCRIPTION

[0047] Embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals represent the same elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects.

[0048] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. When a statement such as "at least one of..." precedes or follows a list of elements, it modifies the entire list of elements and does not modify the individual elements of the list. It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element, or there can be intervening elements therebetween. Conversely, when an element is referred to as being "directly on" another element, there are no intervening elements.

[0049] The inventive concept described below can be modified in various forms and has many embodiments, and specific embodiments are shown in the drawings and described in detail in the detailed description. However, the inventive concept should not be interpreted as being limited to specific embodiments, but should be understood to cover all modifications, equivalents or replacements included in the technical scope of the inventive concept.

[0050] The terms herein are only used to describe specific embodiments and are not intended to limit the inventive concept. Unless the context clearly indicates otherwise, the singular form also includes the plural form. It will be further understood that when used herein, the term "include" or "comprises" indicates the existence of the stated features, numbers, steps, operations, elements, parts, ingredients, materials or combinations thereof, but does not exclude the existence or addition of one or more other features, numbers, steps, operations, elements, parts, ingredients, materials or combinations thereof disclosed in the specification, and does not intend to exclude the possibility that one or more other features, numbers, steps, actions, ingredients, parts, components, materials or combinations thereof may exist or may be added.

[0051] In the drawings, the thickness of layers and regions are exaggerated or reduced for clarity of illustration. The same reference numerals are used throughout for similar (identical) elements.

[0052] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, 10%, or 5% relative to the stated value.

[0053] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as those commonly understood by those of ordinary skill in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and the present disclosure, and unless so defined herein, will not be interpreted in an idealized or excessive form of meaning. Hereinafter, materials for semiconductor packaging, molding compositions for semiconductor packaging, and semiconductor packaging using the same according to example embodiments will be described in detail.

[0054] In the related art, there are operational limitations in improving the thermal conductivity of fillers, and although the thermal conductivity of fillers may be as high as about 100 W / mK, it may be very difficult or almost impossible to achieve a thermal conductivity of a final composite material of about 5 W / mK or more.

[0055] Figure 2 is a graph showing changes in thermal conductivity of a composite material according to thermal conductivity of a filler. Figure 2 The plot of thermal conductivity of is calculated based on the Maxwell Model when the content of filler increases from 0 volume % to 90 volume % in a commonly used polymer resin having a thermal conductivity of about 0.2 W / mK. As shown in the plot, it can be confirmed that if the filler content is about 90%, if a filler having a thermal conductivity of about 50 W / mK or more is used, there is little difference (if any) in the thermal conductivity of the final composite material.

[0056] Polymer materials may be thermal insulators and are known to have bulk thermal conductivity of about 0.2 W / mK or less, such as in the range of about 0.1 W / mK to about 0.2 W / mK, in the case of thermosetting polymers that may be used as materials for semiconductor packaging.

[0057] In the case of insulating (thermal adiabatic) polymers, since heat transfer is governed by the vibrational transfer of phonons, polymers that maximize phonon pathways and minimize phonon scattering can improve the heat transfer properties of the polymer and thus reduce the insulating effect of the polymer.

[0058] Figure 3 is a graph showing the variation of thermal conductivity of a composite material (polymer plus filler) according to the thermal conductivity of the polymer. The data plot based on the Maxwell model depicts that for a given filler (Al 2 O 3 ), the change in the thermal conductivity of the composite material when the thermal conductivity of the polymer resin increases from about 0.2 W / mK to about 1.0 W / mK. Figure 2 )Different Figure 3, we can confirm that if the thermal conductivity of the resin is increased from about 0.2 W / mK to about 1.0 W / m, the thermal conductivity of the composite material can be increased to 18 W / mK with a filler content of 90%.

[0059] We therefore recognize that the thermal conductivity of composites can be improved by selectively engineering the pathways of phonons through π-π stacking, for example by introducing π conjugation into the backbone structure of thermosetting epoxies using mesogenic units, which enhances chain rigidity.

[0060] The epoxy compound according to the embodiment is represented by the following Chemical Formula 1 and has a naphthalene unit:

[0061] Chemical formula 1

[0062] E 1 -M 1 -L 1 -M 2 -L 2 -M 3 -E 2

[0063] Wherein in Chemical Formula 1,

[0064] M 1 、M 2 and M 3 Each is independently a mesogen unit represented by the following Chemical Formula 2, wherein M 1 、M 2 or M 3 At least one of them is a naphthalene unit represented by formula (2-1),

[0065] L 1 and L 2 are each independently a single bond, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH 2 ) 2 -C(=O)-, -C(=O)-(CH 2 ) 2 -, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -NHC(=O)-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH 2 (C 6 H 4 )C(=O)-, and

[0066] E 1 and E2 are the same or different epoxy-containing groups:

[0067] Chemical formula 2

[0068]

[0069] Among them, in chemical formula 2

[0070] R 1 To R 12 each independently represents a hydrogen atom, a halogen atom, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, a C1-C30 heteroalkyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C2-C30 heteroaryl group, a C3-C30 heteroaralkyl group, a C2-C30 heteroaryloxy group, a C3-C30 heteroaryloxyalkyl group, a C3-C30 heteroaralkyloxy group, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonyl group, a sulfamoyl group, a sulfonic acid group or a salt thereof, or a phosphate group or a salt thereof,

[0071] L in the chemical formula (2-3) 3 is -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH 2 ) 2 -C(=O)-, -C(=O)-(CH 2 ) 2 -, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH 2 (C 6 H 4 )C(=O)-, or -C(=O)(C 6 H 4 )CH 2 -,

[0072] X is N, P or As, Y is O, S or Se, and n is an integer from 1 to 10.

[0073] The term "naphthalene unit" refers to a divalent naphthyl group which is unsubstituted or in which 1 to 6 hydrogen atoms are replaced by substituents as defined herein. 1 or L 2 Or one of the divalent attachment points of an epoxy-containing group (end group).

[0074] Figure 1Schematic diagram showing the molecular design principle of an epoxy compound according to an embodiment. Figure 1 , the epoxy compound introduces a mesogen unit into the main chain structure, and π-π stacking through π conjugation is possible between the epoxy compounds. Therefore, the epoxy compound can form a resin cured product having an arrangement structure with relatively strong interactions between the mesogen units. The molecular arrangement structure can promote the transmission of phonon vibrations between the mesogen units and in the same direction, and lead to enhanced or improved active (active) heat transfer, and a corresponding increase in the thermal conductivity of the epoxy compound.

[0075] The mesogen unit means a functional group that can exhibit liquid crystallinity in the epoxy compound as described herein. The epoxy compound includes three identical or different mesogen units and is independently represented by Chemical Formula 2. In Chemical Formula 2, refers to another linking group such as L 1 or L 2 Or the point of attachment of an epoxy-containing group.

[0076] In the epoxy compound, the three mesogen units M 1 、M 2 or M 3 At least one or more of includes a naphthalene unit represented by formula (2-1) of Chemical Formula 2.

[0077]

[0078] The epoxy compound includes one or more naphthalene units and can increase the π-π stacking effect between adjacent epoxy compounds, enhance the interaction between mesogen units between epoxy compounds in a stacked state, and further improve intermolecular stacking and alignment. Therefore, the epoxy compound can further enhance heat transfer between intermolecular mesogen units to improve thermal conductivity.

[0079] In chemical formula 2, R 1 To R 12 Each of them can be independently a hydrogen atom, a halogen atom, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, a C1-C30 heteroalkyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C2-C30 heteroaryl group, a C3-C30 heteroaralkyl group, a C2-C30 heteroaryloxy group, a C3-C30 heteroaryloxyalkyl group, a C3-C30 heteroaralkyloxy group, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonyl group, a sulfamoyl group, a sulfonic acid group or a salt thereof, or a phosphate group or a salt thereof. For example, R 1 To R 12may each independently be a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group or a C1-C30 heteroalkyl group, and specifically, for example, a hydrogen atom or a C1-C10 alkyl group.

[0080] According to an embodiment, R 1 To R 12 At least six of R 1 To R 12 At least eight of R are hydrogen atoms, i.e., unsubstituted. In yet another embodiment, R 1 To R 12 Each is hydrogen. 1 To R 12 The smaller the size or number of substituents, the greater the chance of arranged stacking of the epoxides (eg, π-π stacking of adjacent epoxides).

[0081] According to an embodiment, the mesogen unit may be at least one of the following Chemical Formula 2a:

[0082] Chemical formula 2a

[0083]

[0084]

[0085] In Chemical Formula 2a, n is an integer of 1 to 10.

[0086] According to an embodiment, in the epoxy compound of Chemical Formula 1, M 1 and M 3 The mesogen units may be the same.

[0087] For example, in the epoxy compound of Chemical Formula 1, M 1 or M 3 or M 1 and M 3 Both may be naphthalene units, and M 2 The mesogen unit may be the mesogen unit of Chemical Formula 2, but does not include the naphthalene unit.

[0088] In the epoxy compound, if M 1 and M 3 With identical mesogenic units, particularly naphthalene units, the resulting structure can result in increased symmetry. In addition, the symmetrical structure can provide an increase in the overall π-π stacking of adjacent epoxides, i.e., stronger stacking interactions, and thus more regular or consistent molecular alignment, and thus an even greater increase in thermal conductivity.

[0089] In Chemical Formula 1, the epoxy-containing groups are located at both ends of the mesogen unit in the main chain of the epoxy compound in the length direction. By having the epoxy-containing groups located not on the side chain in the length direction but on both ends of the mesogen unit, a favorable structure for π-π stacking is formed.

[0090] Epoxy-containing group E 1 and E 2 An epoxy group is included, which means -O- bonded to two carbon atoms bonded to one carbon chain, and according to an embodiment, the epoxy-containing group in the epoxy compound of Chemical Formula 1 is independently represented by a group of Chemical Formula 3:

[0091] Chemical formula 3

[0092]

[0093] Wherein in chemical formula 3,

[0094] R 1 and R 2 Each is independently a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group or a C1-C30 heteroalkyl group, and n is an integer of 1 to 10.

[0095] For example, the epoxy group E 1 and E 2 Each is independently represented by a group of Chemical Formula 3a, but is not limited thereto:

[0096] Chemical formula 3a

[0097]

[0098] In an embodiment, E 1 and E 2 According to an embodiment, the epoxy compound may include at least one compound of Chemical Formula 4, but is only illustrative and not limited thereto:

[0099] Chemical formula 4

[0100]

[0101]

[0102] According to an embodiment, the melting temperature of the epoxy compound may be about 190° C. or less, for example, about 160° C. to about 190° C. Within the above range, the epoxy compound may have excellent processability.

[0103] According to an embodiment, the thermal conductivity of the epoxy compound may be about 0.4 W / mK or higher, for example, 0.4 W / mK to about 50 W / mK, or 0.4 W / mK to about 30 W / mK, or 2 W / mK to about 20 W / mK. The epoxy compound has a high thermal conductivity within the above range, and thus can exhibit high heat dissipation and form a composite material with high thermal conductivity. In addition, even with a relatively small amount of filler, improvement in heat transfer can be achieved.

[0104] According to another embodiment, the epoxy compound is a component of a composition.

[0105] The composition includes the high thermal conductivity epoxy compound and can be applied to various electrical and electronic fields requiring heat dissipation performance as well as semiconductors.

[0106] The composition may further comprise a filler. The filler may comprise an inorganic material, an organic material or a combination thereof.

[0107] If the filler includes an inorganic material, the inorganic material may include, without limitation, at least one of silicon oxide, calcium carbonate, magnesium carbonate, aluminum oxide, magnesium oxide, clay, titanium dioxide, talc, calcium silicate, antimony oxide, glass fiber, or eucryptite ceramic. 2 O、Al 2 O 3 and SiO 2 Composition of crystal glass.

[0108] If the filler includes an organic material, the organic material may include, without limitation, at least one of the following: polyethyleneimine, ethylene glycol, or polyethylene glycol.

[0109] According to an embodiment, the composition may be formed using an inorganic material to improve heat dissipation performance, mechanical properties, and / or reduce stress of the epoxy resin composition. The filler may include, without limitation, an inorganic filler used as an encapsulation material for a semiconductor, and is not particularly limited.

[0110] According to an embodiment, the filler in the composition may be in the range of about 40 parts by weight to about 99 parts by weight, based on about 100 parts by weight of the epoxy compound. For example, the filler may be in the range of about 50 parts by weight to about 99 parts by weight, about 60 parts by weight to about 99 parts by weight, about 70 parts by weight to about 95 parts by weight, or about 75 parts to about 92 parts by weight, based on about 100 parts by weight of the epoxy compound. Within the above range, desired physical properties such as mechanical strength, moldability and low stress at high temperatures can be achieved, maintained or controlled.

[0111] The composition may further include at least one additive, such as a curing agent, a curing accelerator, a reaction control agent, a release agent, a coupling agent, a stress relief agent, or an auxiliary flame retardant.

[0112] In the case of a curing agent, for example, phenol alkyl type phenol resins, phenol novolac type phenol resins, naphthol type phenol resins, multifunctional phenol resins, dicyclopentadiene-based phenol resins, amine-based curing agents, anhydride-based curing agents, polyamine curing agents, polysulfide curing agents, bisphenol A type curing agents, novolac type phenol resins, aromatic amines including diaminodiphenylmethane, diaminodiphenyl sulfone, etc. can be used, or one or more selected from the above curing agent list can be used.

[0113] The curing agent may be, for example, a multifunctional phenol-based curing agent, and the multifunctional phenol-based curing agent is a compound having three or more phenolic hydroxyl groups and may have the following structure.

[0114]

[0115] Wherein n is an integer from 1 to 10,000.

[0116] The multifunctional phenol-based curing agent may have a number average molecular weight of, for example, about 40 to about 30,000 g / mol, specifically, for example, about 60 to about 10,000 g / mol, and more specifically, for example, about 80 to about 10,000 g / mol.

[0117] The amount of the curing agent present in the composition is not particularly limited, but may be about 0.1 parts by weight to about 10 parts by weight based on about 100 parts by weight of the composition. By increasing the curing rate within the above range and by minimizing the amount of unreacted curing agent, deterioration of the insulating properties of the molding material may be prevented or at least minimized.

[0118] The composition may further include an epoxy resin in the field of electronic packaging. By further adding the epoxy resin to the composition, the thermal expansion coefficient, warpage and processing properties may be further improved, and the peel strength may also be improved.

[0119] The epoxy resin may include, for example, biphenyl epoxy resin, novolac epoxy resin, dicyclopentadienyl epoxy resin, bisphenol epoxy resin, terpene epoxy resin, aralkyl epoxy resin, multifunctional epoxy resin, naphthalene epoxy resin or halogenated epoxy resin, etc. The above epoxy resins may be used alone or by mixing two or more of the listed epoxy resins.

[0120] Based on about 100 parts by weight of the composition, the epoxy resin may be included in an amount of, for example, about 1 part by weight to about 15 parts by weight, without particular limitation. Within the above range, the improved effects may include: an increase in the bonding strength between the molding material and the substrate of the semiconductor package, an increase in the coefficient of thermal expansion, and / or an improvement in the heat dissipation performance of the molding composition.

[0121] In an embodiment, the method for preparing the composition is not particularly limited, but the composition can be prepared by uniformly mixing all ingredients of the composition using a Henschel mixer or a Redige mixer, a melting and kneading process at about 90° C. to about 120° C. by means of a roll mill or a kneader, a cooling process, and a pulverizing process.

[0122] The above-described composition may be used to form a semiconductor package.

[0123] A molded part can be used to encapsulate a printed circuit board on which a semiconductor chip is mounted to form a semiconductor package, and the molded part is used to protect the semiconductor chip from the external environment, provide insulation properties, and achieve effective heat dissipation during the operation of the chip. In this case, the molded part can be formed by applying the molding composition according to the embodiment to the semiconductor chip.

[0124] In addition, by electrically connecting semiconductor packages formed using the molding composition through solder bumps, semiconductor packages may be connected above and below to form a semiconductor package having a package-on-package type.

[0125] Figure 4 is a cross-sectional view showing a schematic configuration of a semiconductor package 100 according to an embodiment.

[0126] Reference Figure 4 The semiconductor package 100 includes a substrate 5, an adhesive film (chip attaching film) 4 located on the substrate 5, a chip 3 located above the substrate 5 and attached to the substrate 5 through the adhesive film 4, a connecting portion 6 such as a bonding wire (welding wire) for electrically interconnecting the chip 3 and the substrate 5, and a molding portion 110 that encapsulates the chip 3 and the connecting portion 6 and protects the mounted structure, wherein the mounted structure includes the substrate 5, the chip 3 mounted above the substrate 5, and the connecting portion 6.

[0127] The molding portion 110 may be applied to completely cover the chip 3 and the connection portion 6 on the substrate 5 .

[0128] The molded part 110 may be obtained from the molded composition for semiconductor encapsulation according to the embodiment described herein. The molded part 110 includes a molded resin 1 and one or more fillers 2 dispersed in the molded resin 1. The molded part 110 may have a dispersed shape of the filler in a matrix formed by curing a liquid crystal epoxy compound.

[0129] On the opposite surface 5B to the mounting surface 5A of the substrate 5 on which the chip 3 is mounted, there are a plurality of solder balls 7 for electrically connecting the chip 3 to an external circuit (not shown).

[0130] In order to manufacture a semiconductor package using the composition, for example, Figure 4 In the semiconductor package 100 shown in FIG. 1 , a low-pressure transfer molding process may be used to form a molding portion 110 encapsulating a chip 3 mounted on a substrate 5. However, the present inventive concept is not limited thereto, and, for example, an injection molding process or a casting (pouring) process may be used instead of the low-pressure transfer molding process.

[0131] The composition according to the embodiment can protect the chip area in the semiconductor package from moisture, and thus can improve the reliability of the semiconductor package under relatively humid conditions.

[0132] Figure 5 is a cross-sectional view showing main elements of an integrated circuit device 300 according to an embodiment.

[0133] Reference Figure 5 The integrated circuit device 300 includes a plurality of semiconductor chips 320 stacked on a package substrate 310 and separated by connecting conductor spacers 350. 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 encapsulated on the substrate 310 by a molding part 340. The molding part 340 may have the same Figure 4 The molding part 340 may be formed using a molding composition for semiconductor packaging according to an embodiment. The molding part 340 includes a molding resin 341 and one or more fillers 342 dispersed in the molding resin 341. The chemical properties of the molding resin 341 and the one or more fillers 342 are as follows. Figure 4 The molding resin 1 and the one or more fillers 2 are the same.

[0134] exist Figure 5 , a stacking structure of six semiconductor chips 320 in a vertical direction is described, but the number and stacking direction of the semiconductor chips 320 are not limited thereto. The number of semiconductor chips 320 may be determined to be more or less than six as required. A plurality of semiconductor chips 320 may be arranged in a horizontal direction on the package substrate 310, or in a connection structure obtained by a combination of mounting in a vertical direction and mounting in a horizontal direction. In some embodiments, the control chip 330 may be omitted.

[0135] The package substrate 310 may be formed using a flexible printed circuit board, a rigid printed circuit board, or a combination thereof. The package substrate 310 is provided with a substrate internal wiring 312 and a connection terminal 314. The connection terminal 314 may be formed on one side of the package substrate 310. On the other side of the package substrate 310, a solder ball 316 is formed. The connection terminal 314 is electrically connected to the solder ball 316 via the substrate internal wiring 312.

[0136] In some embodiments, solder balls 316 may be replaced with conductive bumps or a land grid array (LGA).

[0137] The plurality of semiconductor chips 320 and the control chip 330 include connection structures 322 and 332, respectively. In some embodiments, the connection structures 322 and 332 may be formed as through silicon via (TSV) contact structures.

[0138] The respective connection structures 322 and 332 of the plurality of semiconductor chips 320 and the control chip 330 may be electrically connected to the connection terminals 314 of the package substrate 310 through the connection portions 350 such as bumps.

[0139] Each of the plurality of semiconductor chips 320 may include a system LSI, a flash memory, a DRAM, an SRAM, an EEPROM, a PRAM, an MRAM, or an RRAM. The control chip 330 may include a logic circuit such as a serial-parallel conversion / serial-to-parallel conversion (SER / DES) circuit.

[0140] Figure 6 is a plan view showing main elements of an integrated circuit device 400 according to an embodiment.

[0141] The integrated circuit device 400 includes a module substrate 410, a control chip 420 mounted on the module substrate 410, and a plurality of semiconductor chips 430. On the module substrate 410, a plurality of input and output terminals 450 are formed.

[0142] The plurality of semiconductor chips 430 include reference Figure 4 The semiconductor package 100 described herein or with reference to Figure 5 At least one of the integrated circuit devices 300 is described.

[0143] Figure 7 is a diagram showing main elements of an integrated circuit device 500 according to an embodiment.

[0144] The integrated circuit device 500 includes a controller 510, an input / output device 520, a memory 530, and an interface 540. The integrated circuit device 500 may be a mobile system or a system for transmitting or receiving information. In some embodiments, the mobile system may be at least one of the following: a personal digital assistant (PDA), a portable computer, a web tablet, a wireless phone, a mobile phone, a digital music player, or a memory card.

[0145] In some embodiments, the controller 510 may be a microprocessor, a digital signal processor, or a microcontroller.

[0146] The input / output device 520 is used to input and output data of the integrated circuit device 500. The integrated circuit device 500 can be connected to an external device such as a personal computer or a network, and can exchange data with the external device using the input / output device 520. In some embodiments, the input / output device 520 can be a keypad, a keyboard, or a display.

[0147] In some embodiments, the memory 530 stores code and / or data for running the controller 510. In some other embodiments, the memory 530 stores data processed in the controller 510. At least one of the controller 510 and the memory 530 includes a reference Figure 4 The semiconductor package 100 and the reference Figure 5 At least one of the integrated circuit devices 300 is described.

[0148] The interface 540 functions as a data transmission channel between the integrated circuit device 500 and other external devices. The controller 510 , the input / output device 520 , the memory 530 , and the interface 540 may communicate with each other via a bus 550 .

[0149] The integrated circuit device 500 may be included in a mobile phone, an MP3 player, a navigation system, a portable multimedia player (PMP), a solid state drive (SSD), or a home appliance.

[0150] Figure 8 Schematically shows a mobile wireless phone 600 according to an embodiment. The mobile wireless phone 600 includes at least one of the following: Figure 4 The semiconductor package 100 described above, referring to Figure 5 The integrated circuit device 300 described herein, referring to Figure 6 The integrated circuit device 400 and the reference Figure 7 An integrated circuit device 500 is illustrated.

[0151] Meanwhile, the definitions of substituents used in the chemical formulas described in the specification will be examined as follows.

[0152] The term "alkyl" as used in chemical formulae refers to a fully saturated (no carbon-carbon multiple bonds), branched or unbranched (straight chain or linear), substituted or unsubstituted hydrocarbon group.

[0153] Non-limiting examples of “alkyl” may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, and the like.

[0154] One or more hydrogen atoms in the "alkyl" group may be replaced by a halogen atom, a C1-C20 alkyl group substituted with a halogen atom (e.g., CF 3 , CHF 2 , CH 2 F、CCl 3 The invention also includes but is not limited to aryl, aryl, arylalkyl, C5-C20 heteroaryl, C7-C20 heteroarylalkyl, C6-C20 heteroaryloxy, C6-C20 heteroaryloxyalkyl or C6-C20 heteroarylalkyl.

[0155] The term "substituted", for example, with respect to R 1 To R 12 , refers to one or more hydrogen atoms replaced by: halogen atoms, halogen-substituted C1-C8 alkyl (e.g. CF 3 , CHF 2 , CH 2 F、CCl 3 The invention also includes but is not limited to alkyl, aryl, aryl, arylalkyl, C5-C10 heteroaryl, C7-C8 heteroarylalkyl, C6-C10 heteroaryloxy, C6-C10 heteroaryloxyalkyl or C6-C10 heteroarylalkyl.

[0156] The term "halogen atom" includes fluorine, bromine, chlorine, iodine and the like.

[0157] The term "halogen atom-substituted C1-C20 alkyl group" refers to a C1-C20 alkyl group in which one or more halogen groups are substituted, and non-limiting examples thereof may include a monohalogenated alkyl group, a dihalogenated alkyl group or a polyhalogenated alkyl group, including a perhalogenated alkyl group.

[0158] Monohaloalkyl refers to the case where there is one iodine, bromine, chlorine or fluorine atom in the alkyl group, and dihaloalkyl and polyhaloalkyl refer to alkyl groups having two or more halogen atoms which are the same or different.

[0159] The term "alkoxy" used in the chemical formula represents alkyl-O-, and the alkyl is the same as described above. Non-limiting examples of alkoxy include methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclohexyloxy, etc. One or more hydrogen atoms in the alkoxy may be replaced by the same substituents as in the above-mentioned alkyl.

[0160] The term "alkoxyalkyl" used in the chemical formula refers to the case where the alkyl group is substituted by the above-mentioned alkoxy group. One or more hydrogen atoms in the alkoxyalkyl group may be replaced by the same substituents as in the above-mentioned alkyl group. As mentioned above, the term "alkoxyalkyl" includes substituted alkoxyalkyl moieties.

[0161] The term "alkenyl" used in the chemical formula refers to a branched or unbranched, substituted or unsubstituted hydrocarbon group having at least one carbon-carbon double bond. Non-limiting examples of alkenyl groups may include vinyl, allyl, butenyl, isopropenyl, isobutenyl, etc., and one or more hydrogen atoms in the alkenyl group may be replaced by the same substituents as in the above-mentioned alkyl group.

[0162] The term "alkynyl" used in the chemical formula refers to a branched or unbranched, substituted or unsubstituted hydrocarbon group having at least one carbon-carbon triple bond. Non-limiting examples of "alkynyl" may include ethynyl, butynyl, isobutynyl, isopropynyl, etc.

[0163] One or more hydrogen atoms in the "alkynyl group" may be replaced by the same substituents as described above for the alkyl group.

[0164] The term "aryl" group used in the chemical formula is used alone or in combination and refers to a substituted or unsubstituted aromatic hydrocarbon group including one or more rings.

[0165] The term "aryl" also includes groups where an aromatic ring is fused to one or more cycloalkyl rings.

[0166] Non-limiting examples of "aryl" include phenyl, naphthyl, tetrahydronaphthyl, and the like.

[0167] In addition, one or more hydrogen atoms in the "aryl group" may be replaced by the same substituents as those in the above-mentioned alkyl group.

[0168] The term "aralkyl" refers to an alkyl group substituted with an aryl group. Examples of aralkyl groups may include benzyl- or phenyl-CH 2 CH 2 -.

[0169] The term "aryloxy" used in the chemical formula refers to -O-aryl, and examples of the aryloxy group include phenoxy, etc. One or more hydrogen atoms in the "aryloxy" group may also be replaced by the same substituents as in the above-mentioned alkyl group.

[0170] The term "heteroaryl" used in the chemical formula refers to a monocyclic or bicyclic aromatic organic group including one or more heteroatoms (which may be N, O, P or S) and the remaining ring-forming carbon atoms. The heteroaryl group may include, for example, 1 to 5 heteroatoms and 5 to 10 ring members. S or N may be oxidized to have a variety of oxidation states.

[0171] Monocyclic heteroaryl groups may include thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, 1,2,3- Oxazolyl, 1,2,4- Oxazolyl, 1,2,5- Oxazolyl, 1,3,4- oxadiazole, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, Oxazol-2-yl, Oxazol-4-yl, oxazol-5-yl, isoxazol-5-yl Oxazol-3-yl, iso Oxazol-4-yl, iso oxazol-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, tetrazolyl, pyridin-2-yl, pyridin-3-yl, pyrazin-2-yl, pyrazin-4-yl, pyrazin-5-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl.

[0172] The term heteroaryl includes those in which a heteroaromatic ring is fused to one or more aryl, alicyclic or heterocyclic rings.

[0173] Examples of bicyclic heteroaryl groups may include indolyl, isoindolyl, indazolyl, indolizinyl, purinyl, quinolinazinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, naphthyridinyl, quinazolinyl, quinoxalinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenanthridinyl, phenanthrolinyl, phenanthroline ... oxazine, benzoisoquinolyl, thieno[2,3-b]furanyl, furano[3,2-b]-pyranyl, 5H-pyrido[2,3-d]-o- Oxazine, 1H-pyrazolo[4,3-d]- oxazolyl, 4H-imidazo[4,5-d]thiazolyl, pyrazino[2,3-d]pyridazinyl, imidazo[2,1-b]thiazolyl, imidazo[1,2-b][1,2,4]triazinyl, 7-benzo[b]thienyl, benzo[ Azolyl, benzimidazolyl, benzothiazolyl, benzoxazepine Benzo Oxazine, 1H-pyrrolo[1,2-b][2]benzazepine yl, benzofuranyl, benzothiophenyl, benzotriazolyl, pyrrolo[2,3-b]pyridinyl, pyrrolo[3,2-c]pyridinyl, pyrrolo[3,2-b]pyridinyl, imidazo[4,5-b]pyridinyl, imidazo[4,5-c]pyridinyl, pyrazolo[4,3-d]pyridinyl, pyrazolo[4,3-c]pyridinyl, pyrazolo[3,4-c]pyridinyl, pyrazolo[3,4-d]pyridinyl, pyrazolo[3,4-b]pyridinyl, imidazo[1,2-a]pyridinyl pyrimidinyl, pyrazolo[1,5-a]pyridinyl, pyrrolo[1,2-b]pyridazinyl, imidazo[1,2-c]pyrimidinyl, pyrido[3,2-d]pyrimidinyl, pyrido[4,3-d]pyrimidinyl, pyrido[3,4-d]pyrimidinyl, pyrido[2,3-d]pyrimidinyl, pyrido[2,3-b]pyrazinyl, pyrido[3,4-b]pyrazinyl, pyrimido[5,4-d]pyrimidinyl, pyrazino[2,3-b]pyrazinyl or pyrimido[4,5-d]pyrimidinyl.

[0174] One or more hydrogen atoms in the "heteroaryl" may be replaced by the same substituents as those in the above-mentioned alkyl group.

[0175] The term "heteroaralkyl" refers to an alkyl group substituted with a heteroaryl group.

[0176] The term "heteroaryloxy" refers to an -O-heteroaryl moiety. One or more hydrogen atoms in the heteroaryloxy group may also be replaced by the same substituents as those in the above-mentioned alkyl group.

[0177] The term "heteroaryloxyalkyl" refers to an alkyl group substituted with a heteroaryloxy group. One or more hydrogen atoms in the heteroaryloxyalkyl group may be replaced by the same substituents as those in the above-mentioned alkyl group.

[0178] The "carbocycle" used in the chemical formula includes a saturated or partially unsaturated non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon group.

[0179] Examples of monocyclic hydrocarbon groups include cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, and the like.

[0180] Examples of bicyclic hydrocarbon groups include bornyl, decalinyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]heptenyl or bicyclo[2.2.2]octyl.

[0181] Examples of the tricyclic hydrocarbon group include adamantyl and the like.

[0182] One or more hydrogen atoms in the "carbocycle" may be replaced by the same substituents as those in the above-mentioned alkyl group.

[0183] The "heterocyclic" group used in the chemical formula refers to a ring group composed of 5 to 10 atoms and containing heteroatoms such as nitrogen, sulfur, phosphorus and oxygen, and includes pyridyl as a specific example, and one or more hydrogen atoms in the heterocyclic group may also be replaced as in the above-mentioned alkyl group.

[0184] The term "heterocyclyloxy" refers to an -O-heterocyclic ring, and one or more hydrogen atoms in the heterocyclyloxy group may be replaced as in the above-mentioned alkyl group.

[0185] The term "sulfonyl" refers to R"-SO 2 -, and R" is hydrogen, alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, alkoxy, aryloxy, cycloalkyl or heterocyclic group.

[0186] The term "sulfamoyl" includes H 2 NS(O 2 )-, alkyl-NHS(O 2 )-,(alkyl) 2 NS(O 2 )-, aryl-NHS(O 2 )-, alkyl-(aryl)-NS(O 2 )-、(aryl) 2 NS(O) 2 , heteroaryl-NHS(O 2 )-、(Arylalkyl)-NHS(O 2 )- or (heteroaralkyl)-NHS(O 2 )-.

[0187] One or more hydrogen atoms in the sulfamoyl group may be replaced as in the above-mentioned alkyl group.

[0188] The term "amino" refers to a situation where a nitrogen atom forms a covalent bond with at least one carbon or heteroatom. Amino groups include, for example, -NH 2 In addition, "alkylamino" groups in which the nitrogen atom is bonded to at least one additional alkyl group, and "arylamino" and "diarylamino" groups in which at least the nitrogen atom is independently bonded to one or two selected aryl groups are included.

[0189] The alkylene group, arylene group and heteroarylene group refer to a divalent group derived from an alkyl group, an aryl group and a heteroaryl group, respectively.

[0190] Hereinafter, example embodiments will be described in more detail with reference to examples and comparative examples. However, these examples are only for illustrating the technical spirit, and the scope of the present disclosure is not limited thereto.

[0191] Example 1

[0192] (1) Preparation of Epoxides

[0193] The epoxy compound of formula (4-1) is prepared by the following preparation method.

[0194]

[0195] To a 500 ml glass reactor were added ethyl 4-hydroxybenzoate (0.2 mol, 33.2 g), 3-propene bromide (0.25 mol, 30.3 g), K 2 CO 3 (0.3mol, 42.0g) and acetone (300ml). After fully exchanging the interior of the reactor with nitrogen, the reactant was refluxed under nitrogen flow for 24 hours. After adding diethyl ether (150ml) and water (100ml), the diethyl ether layer was washed 3 times with NaOH10% solution (100ml). Diethyl ether was evaporated, and 2N HCl solution was added until pH reached 2. The reaction product was washed with cold water and recrystallized with ethanol to prepare a compound represented by the following chemical formula 4-1-1.

[0196]

[0197] The compound of chemical formula 4-1-1 (0.033 mol, 6.6 g) and SOCl 2 (0.13 mol, 9.7 ml) was refluxed for 2 hours. Excess SOCl was removed under vacuum 2 Then, pyridine (30 ml) was added. 2,6-naphthalene diol (0.017 mol, 2.7 g) was added, and the reaction mixture was cooled in an ice bath for 2 hours and then at room temperature for 24 hours. 2N HCl solution (500 ml) was added, and then the resulting solution was washed with Na 2 CO 3 The resulting product was washed with an aqueous solution (300 ml) and water (300 ml), and recrystallized with ethyl acetate to prepare a compound represented by the following Chemical Formula 4-1-2.

[0198]

[0199] The compound of Chemical Formula 4-1-2 (0.010 mol, 5.4 g), 75% 3-chloroperoxybenzoic acid (0.027 mol, 6.2 g) and dichloromethane (200 ml) were refluxed for 4 days. The reaction product was filtered and washed with 5% Na 2 SO 3 Aqueous solution (200 ml), 5% Na 2 CO 3 The resulting product was washed with aqueous solution (200 ml) and aqueous NaCl solution (200 ml), dichloromethane was evaporated, and the resulting product was recrystallized with ethyl acetate to prepare a compound represented by Formula 4-1.

[0200] (2) Formation of composite materials

[0201] The epoxy resin thus prepared and 0.45 mol of diaminodiphenyl sulfone (DDS) as a curing agent based on the epoxy resin were added to a dichloromethane / acetone mixed solvent, followed by stirring at about 300 rpm and dissolving at room temperature (25° C.) to prepare a mixture. The mixture was placed in a container having a thickness of 10 mm and a diameter of 40 mm, and the solvent was evaporated in a vacuum oven at room temperature.

[0202] Then, the first curing was performed at 200° C. for 6 hours, and the second curing was performed at 240° C. for 4 hours to prepare a completely cured composite material, ie, an epoxy-cured compound sample having a thickness of 3 mm and a diameter of 20 mm.

[0203] Example 2

[0204] (1) Preparation of Epoxides

[0205] The epoxy compound of formula (4-2) is prepared by the following preparation method.

[0206]

[0207] 2,6-naphthalene dicarboxylic acid (0.2mol, 37.6g), 2,6-dihydroxynaphthalene (0.1mol, 16.0g), cyclopentane (50ml) and p-TSA (p-toluenesulfonic acid) (5mmol, 0.9g) were added to a 150ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to 180°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-2-1.

[0208]

[0209] Add the compound (10.5mmol, 5.1g) represented by chemical formula 4-2-1, epichlorohydrin (0.42mol, 39.2g) and isopropyl alcohol (0.32mol, 19.1g) to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants are refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and NaOH solution (30% by weight, 8.5ml) is added dropwise to the reactor within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-2.

[0210] (2) Formation of composite materials

[0211] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-2) was used.

[0212] Example 3

[0213] (1) Preparation of Epoxides

[0214] The epoxy compound of formula (4-3) is prepared by the following preparation method.

[0215]

[0216] 6-Hydroxy-2-naphthoic acid (0.2 mol, 37.6 g), 4,4'-bisphenol (0.1 mol, 18.6 g), sulfolane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180° C. under a nitrogen flow, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-3-1.

[0217]

[0218] Add the compound (10.5mmol, 5.1g) represented by chemical formula 4-3-1, epichlorohydrin (0.42mol, 39.2g) and isopropyl alcohol (0.32mol, 19.1g) to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants are refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and NaOH solution (30% by weight, 8.5ml) is added dropwise to the reactor within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-3.

[0219] (2) Formation of composite materials

[0220] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-3) was used.

[0221] Example 4

[0222] (1) Preparation of Epoxides

[0223] The epoxy compound of formula (4-4) is prepared by the following preparation method.

[0224]

[0225] 4-Hydroxybenzoic acid (0.1 mol, 13.8 g) and hydroquinone (0.9 mol, 99.0 g) were added to a 500 ml glass reactor, the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to 260° C. under a nitrogen stream, and the reaction was performed for 2.5 hours. Water (1000 ml) was added, filtered to obtain a reaction product, and recrystallized using ethanol and water to prepare a compound represented by the following chemical formula 4-4-1.

[0226]

[0227] A 150 ml glass reactor was added with a compound represented by chemical formula 4-4-1 (0.1 mol, 23 g), 6-hydroxy-2-naphthoic acid (0.2 mol, 37.6 g), p-xylene (120 ml) and p-TSA (5 mmol, 0.9 g). After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 150 ° C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 48 hours. The reaction product was filtered and washed with water to prepare a compound represented by the following chemical formula 4-4-2.

[0228]

[0229] Add the compound (10.5mmol), epichlorohydrin (0.42mol) and isopropyl alcohol (0.32mol) represented by chemical formula 4-4-2 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-4.

[0230] (2) Formation of composite materials

[0231] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-4) was used.

[0232] Example 5

[0233] (1) Preparation of Epoxides

[0234] The epoxy compound of formula (4-5) is prepared by the following preparation method.

[0235]

[0236] 6-hydroxy-2-naphthoic acid (0.2 mol, 37.6 g), 2,7-dihydroxyfluorene (0.1 mol, 19.8 g), cyclopentane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180° C. under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-5-1.

[0237]

[0238] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-5-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-5.

[0239] (2) Formation of composite materials

[0240] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-5) was used.

[0241] Example 6

[0242] (1) Preparation of Epoxides

[0243] The epoxy compound of formula (4-6) is prepared by the following preparation method.

[0244]

[0245] 6-hydroxy-2-naphthoic acid (0.1 mol, 18.8 g), 4-hydroxybenzoic acid (0.1 mol, 13.8 g), 4,4'-bisphenol (0.1 mol, 18.6 g), sulfolane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180° C. under a nitrogen flow, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-6-1.

[0246]

[0247] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-6-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare the compound represented by Chemical Formula 4-6.

[0248] (2) Formation of composite materials

[0249] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-6) was used.

[0250] Example 7

[0251] (1) Preparation of Epoxides

[0252] The epoxy compound of formula (4-7) is prepared by the following preparation method.

[0253]

[0254] 6-Hydroxy-2-naphthaldehyde (0.12 mol, 34.4 g), 4,4'-diaminodiphenyl sulfone (0.1 mol, 24.8 g), ethanol (100 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the reactants were refluxed for 24 hours. The reaction product was washed with ethanol to prepare a compound represented by the following chemical formula 4-7-1.

[0255]

[0256] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-7-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-7.

[0257] (2) Formation of composite materials

[0258] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-7) was used.

[0259] Example 8

[0260] (1) Preparation of Epoxides

[0261] The epoxy compound of formula (4-8) is prepared by the following preparation method.

[0262]

[0263] 6-hydroxy-2-naphthoic acid (0.2 mol, 37.6 g), 4,4'-sulfonyl diphenol (0.1 mol, 25.3 g), cyclopentane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180° C. under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-8-1.

[0264]

[0265] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-8-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare the compound represented by Chemical Formula 4-8.

[0266] (2) Formation of composite materials

[0267] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-8) was used.

[0268] Example 9

[0269] (1) Preparation of Epoxides

[0270] The epoxy compound of formula (4-9) is prepared by the following preparation method.

[0271]

[0272] 6-hydroxy-2-naphthoic acid (0.1 mol, 18.8 g), 4-hydroxybenzoic acid (0.1 mol, 13.8 g), a compound represented by 4-4-1 (0.1 mol, 23 g), cyclopentane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180° C. under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-9-1.

[0273]

[0274] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-9-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-9.

[0275] (2) Formation of composite materials

[0276] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-9) was used.

[0277] Example 10

[0278] (1) Preparation of Epoxides

[0279] The epoxy compound of formula (4-10) is prepared by the following preparation method.

[0280]

[0281] 6-hydroxy-2-naphthoic acid (0.1 mol, 18.8 g), 4-hydroxybenzoic acid (0.1 mol, 13.8 g), 2,7-dihydroxyfluorene (0.1 mol, 19.8 g), cyclopentane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 180 ° C under a nitrogen flow, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following chemical formula 4-10-1.

[0282]

[0283] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-10-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-10.

[0284] (2) Formation of composite materials

[0285] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-10) was used.

[0286] Embodiment 11

[0287] (1) Preparation of Epoxides

[0288] The epoxy compound of formula (4-11) is prepared by the following preparation method.

[0289]

[0290] 6-Hydroxy-2-naphthoic acid (0.1 mol, 18.8 g), 1,1:4,1-triphenyl-4,4"-diphenol (0.1 mol, 26.2 g), cyclopentane (50 ml) and p-TSA (5 mmol, 0.9 g) were added to a 150 ml glass reactor. After the inside of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to 180° C. under a nitrogen flow, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 4 hours. The reaction product was washed with cold water and ethanol to prepare a compound represented by the following Chemical Formula 4-11-1.

[0291]

[0292] Add the compound (10.5mmol) and epichlorohydrin (0.42mol) represented by chemical formula 4-11-1 to a 150ml glass reactor. After fully exchanging the inside of the reactor with nitrogen, the temperature in the reactor is raised to a temperature of 50°C under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactant is refluxed for 5 hours. The temperature in the reactor is lowered to room temperature, and a NaOH solution (30% by weight, 8.5ml) is added dropwise thereto within 1 hour. The temperature of the reactor is raised to 60°C, and stirred for 4 hours. The temperature of the reactor is lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare a compound represented by Chemical Formula 4-11.

[0293] (2) Formation of composite materials

[0294] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound of formula (4-11) was used.

[0295] Comparative Example 1

[0296] (1) Preparation of Epoxides

[0297] As the epoxy compound, NC-3000, a product of Nippon Kayaku Co., was used. The epoxy compound had the following structure.

[0298]

[0299] (2) Formation of composite materials

[0300] 10 g of the epoxy compound, 3.5 g of curing agent MEH7500 (Myungsung Chemical Co., multifunctional phenol) and 0.01 g of triphenylphosphine (TPP) were injected into a hot press molding container and cured under conditions of 170° C., 2 hours and 5 MPa to form a disk-shaped composite material having a thickness of 3 mm and a diameter of 20 mm.

[0301] Comparative Example 2

[0302] (1) Preparation of Epoxides

[0303] The epoxy compound having the following formula was prepared by the following preparation method.

[0304]

[0305] A compound (5.66 g) represented by chemical formula 4-4-1, epichlorohydrin (50 ml), N-butyl-N,N-dipropylbutane-1-ammonium bromide (TBAB, 0.12 g) and methanol (30 ml) were added to a 150 ml glass reactor. After the interior of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 50° C. under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 5 hours. The temperature in the reactor was lowered to room temperature, and a NaOH solution (30% by weight, 8.5 ml) was added dropwise thereto within 1 hour. The temperature of the reactor was raised to 60° C., and stirred for 4 hours. The temperature of the reactor was lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare the compound of the above formula.

[0306] (2) Formation of composite materials

[0307] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound prepared above was used.

[0308] Comparative Example 3

[0309] (1) Preparation of Epoxides

[0310] The epoxy compound having the following formula was prepared by the following preparation method.

[0311]

[0312] 3,3',5,5'-tetramethyl[1,1'-biphenyl]-4,4'-diphenol (5.7 g), epichlorohydrin (50 ml), N-butyl-N,N-dipropylbutane-1-ammonium bromide (TBAB, 0.12 g) and methanol (30 ml) were added to a 150 ml glass reactor. After the inside of the reactor was fully exchanged with nitrogen, the temperature in the reactor was raised to a temperature of 50° C. under a nitrogen stream, and while maintaining the internal temperature of the reactor, the reactants were refluxed for 5 hours. The temperature in the reactor was lowered to room temperature, and a NaOH solution (30 wt %, 8.5 ml) was added dropwise thereto within 1 hour. The temperature of the reactor was raised to 60° C., and stirring was performed for 4 hours. The temperature of the reactor was lowered to room temperature, and CH 2 Cl 2 / CH 3 OH was recrystallized to prepare the compound.

[0313] (2) Formation of composite materials

[0314] A composite material was prepared by carrying out the same procedure as in Example 1, except that the epoxy compound prepared above was used.

[0315] Evaluation Example 1: Evaluation of physical properties

[0316] Thermal conductivity was evaluated for the epoxy compounds prepared in Examples 1 to 11 and Comparative Examples 1 to 3 using a thermal conductivity measuring device (model name TCi) of Scinco Co., and the results are shown in Table 1 below.

[0317] Table 1

[0318]

[0319]

[0320] As shown in Table 1 above, the thermal conductivity of conventional commercial epoxy compounds (Comparative Examples 1, 2, and 3) in which a naphthalene structure is not included in the mesogenic unit is about 0.21 Watts / meter.Kelvin (W / mK) to 0.33 W / mK. In contrast, the epoxy compounds prepared according to Examples 1-11 in which 1-3 naphthalene units are included in the mesogenic unit exhibit a thermal conductivity value of about 0.4 W / mK or more. In particular, in the case in which a biphenyl group is located at the center of the mesogenic unit and a naphthalene unit is located at both ends of the mesogenic unit, a high thermal conductivity value of about 0.64 W / mK can be obtained.

[0321] In addition, it can be found that the epoxy compounds prepared in Examples 1 to 11 exhibit excellent thermal conductivity and excellent processability, and have a melting temperature of 190° C. or less.

[0322] In contrast, the composite materials of Comparative Examples 1 to 3 had a melting temperature of 190° C. or higher, and although the melting temperature was generally acceptable, each of the comparative examples was not suitable as a material for semiconductor packaging because the thermal conductivity was too low.

[0323] The epoxy compound according to the embodiment is highly thermally conductive and exhibits high heat dissipation performance. In addition, the composition including the epoxy compound according to the embodiment exhibits high thermal conductivity. The composition including the epoxy compound may further include a relatively small amount of filler content. The high thermal conductivity epoxy compound can be applied to various semiconductor packaging and electronic fields that require heat dissipation performance.

[0324] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should typically be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. An epoxy compound comprising a naphthalene unit and represented by Chemical Formula 1: Chemical formula 1 E1-M1-L1-M2-L2-M3-E2 In Chemical Formula 1, M1, M2 and M3 are each independently a mesogen unit represented by Chemical Formula 2, wherein at least one of M1 or M3 is a naphthalene unit represented by Formula (2-1), L1 and L2 are each independently -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH2)2-C(=O)-, -C(=O)-(CH2)2-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -NHC(=O)-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH2(C6H4)C(=O)-, or -C(=O)(C6H4)CH2-, and E1 and E2 are the same or different epoxy-containing groups: Chemical formula 2 in, In chemical formula 2 R1 to R 12 each independently represents a hydrogen atom, a halogen atom, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, a C1-C30 heteroalkyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C2-C30 heteroaryl group, a C3-C30 heteroaralkyl group, a C2-C30 heteroaryloxy group, a C3-C30 heteroaryloxyalkyl group, a C3-C30 heteroaralkyloxy group, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonyl group, a sulfamoyl group, a sulfonic acid group or a salt thereof, or a phosphate group or a salt thereof, L3 in the chemical formula (2-3) is -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -(CH2)2-C(=O)-, -C(=O)-(CH2)2-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -S(=O)-, -CH=N-, -N=CH-, -NHC(=O)O-, -OC(=O)NH-, -C(=O)NH-, -NHC(=O)-, -OC(=O)NHS(=O)O-, -OS(=O)NHC(=O)O-, -CH2(C6H4)C(=O)-, or -C(=O)(C6H4)CH2-, X is N, P or As, Y is O, S or Se, and n is an integer from 1 to 10.

2. The epoxy compound according to claim 1, wherein In Chemical Formula 2, R1 to R 12 Each is independently a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, or a C1-C30 heteroalkyl group.

3. The epoxy compound of claim 1, wherein M1, M2 and M3 are each independently a mesogen unit represented by Chemical Formula 2a: Chemical formula 2a In Chemical Formula 2a, n is an integer of 1 to 10.

4. The epoxy compound according to claim 1, wherein In Chemical Formula 1, M1 and M3 are the same mesogenic unit.

5. The epoxy compound according to claim 1, wherein In Chemical Formula 1, at least one of M1 or M3 is a naphthalene unit, and M2 is the mesogen unit of Chemical Formula 2 but does not include a naphthalene unit.

6. The epoxy compound of claim 1, wherein the epoxy-containing groups E1 and E2 are each independently represented by a group of Chemical Formula 3: Chemical formula 3 In chemical formula 3, R1 and R2 are each independently a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C1-C30 alkoxy group, a C2-C30 alkoxyalkyl group, or a C1-C30 heteroalkyl group, and n is an integer from 1 to 10.

7. The epoxy compound of claim 1, wherein the epoxy-containing groups E1 and E2 are each independently represented by a group of Chemical Formula 3a: Chemical formula 3a 8. The epoxy compound of claim 1, wherein the mesogen unit is selected from L1 and L2 are selected from -C(=O)O-, -OC(=O)-, -CH=N-, and -N=CH-, and E1 and E2 are 9. The epoxy compound according to claim 1, having a melting temperature of 190°C or less.

10. The epoxy compound of claim 1, having a thermal conductivity of 0.4 Watts / meter-Kelvin or more.

11. An epoxy compound, which is a compound of any one of formulas (4-2) to (4-11):

12. A composition comprising the epoxy compound according to any one of claims 1 to 11.

13. The composition of claim 12, further comprising a filler, wherein the filler comprises an inorganic material, an organic material or a combination thereof.

14. The composition of claim 13, wherein the inorganic material comprises at least one of silicon oxide, calcium carbonate, magnesium carbonate, aluminum oxide, magnesium oxide, clay, titanium dioxide, talc, calcium silicate, antimony oxide, glass fiber or eucryptite ceramic, and The organic material includes at least one of the following: polyethyleneimine or polyethylene glycol.

15. The composition of claim 13, wherein the filler is 40 to 99 parts by weight based on 100 parts by weight of the epoxy compound.

16. The composition of claim 12, further comprising at least one of the following: a curing agent, a curing accelerator, a reaction control agent, a release agent, a coupling agent, a stress relief agent, or an auxiliary flame retardant.

17. The composition of claim 12, wherein the composition is used for molding a semiconductor package.

18. A material for semiconductor packaging, the material comprising the epoxy compound according to any one of claims 1 to 11.

19. A molded product comprising the epoxy compound according to any one of claims 1 to 11 or a cured product thereof.

20. Electrical and electronic equipment comprising the epoxy compound according to any one of claims 1 to 11 or a cured product thereof.

21. Semiconductor packaging, including: a substrate, wherein at least one chip is mounted on the substrate, a connecting portion for electrically connecting the at least one chip and the substrate, and a molding part encapsulating the at least one chip on the substrate, wherein the molded part is formed using the composition according to any one of claims 12-17.

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