Epoxy resin composition for encapsulating semiconductor device and semiconductor device encapsulated using the same

Abstract

To provide an epoxy resin composition for encapsulating a semiconductor device that has high thermal conductivity with significantly improved heat dissipation effect, and improved fluidity, and a semiconductor device encapsulated using the same.SOLUTION: An epoxy resin composition for encapsulating semiconductor devices comprises an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, wherein the epoxy resin includes an epoxy resin represented by Formula 1. The epoxy resin composition for encapsulating semiconductor devices may comprise 2 wt.% to 17 wt.% of the epoxy resin, 0.5 wt.% to 13 wt.% of the curing agent, 50 wt.% to 95 wt.% of an inorganic filler, and 0.01 wt.% to 5 wt.% of the curing catalyst. (Detailed description of Formula 1 is provided in the specification.)SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an epoxy resin composition for sealing semiconductor elements and a semiconductor element sealed using the same.

Background Art

[0002] In recent years, the integration degree of semiconductor elements has been improving. In semiconductor devices in which laminated and highly integrated semiconductor elements are sealed in small and thin packages, the frequency of occurrence of failures such as malfunction of the package and generation of package cracks may become very high due to the heat generated during operation of the semiconductor.

[0003] As a solution to heat dissipation, a heat dissipation material such as a metal material is used during the molding of the epoxy resin for sealing, and heat is dissipated by a heat sink. However, the heat sink can only be used in some packages such as FBGA (fine pitch ball grid array) and QFP (quad flat package), and there are problems such as a decrease in productivity due to an additional process during assembly and an increase in cost due to the high cost of the heat sink. Therefore, there is a strong demand for a molding material for an epoxy resin for sealing with high heat dissipation due to high thermal conductivity. In some semiconductor packages, spherical aluminum oxide (alumina) is used.

[0004] Alumina has a thermal conductivity of about 25 W / m·K to 30 W / m·K. However, since the epoxy resin contained in the epoxy resin composition for sealing has a very low thermal conductivity of 0.2 W / m·K, there is a limit to improving the thermal conductivity of the sealing layer formed of the composition to 6 W / m·K or more. In addition, copper, aluminum, or silver particles having high thermal conductivity do not have good insulation performance, and aluminum nitride, boron nitride, and silicon carbide fillers having relatively good insulation performance cannot increase the filling rate because the fluidity of the fillers is not good. In recent years, there have been many cases of increasing the thermal conductivity of epoxy resins, but the widespread use of insulating and thermosetting compression resin-sealed semiconductor materials has not yet been achieved.

[0005] Therefore, by applying an epoxy resin having higher thermal conductivity and fluidity than conventional epoxy resins to increase the thermal conductivity and improve the heat dissipation effect, it is necessary to develop an epoxy resin composition for sealing semiconductor elements that suppresses malfunction and defects of semiconductor packages due to heat.

Summary of the Invention

Problems to be Solved by the Invention

[0006] To provide an epoxy resin composition for sealing semiconductor elements having high thermal conductivity, significantly improved heat dissipation effect, and improved fluidity.

[0007] According to one embodiment, an epoxy resin composition for sealing semiconductor elements is provided.

Means for Solving the Problems

[0008] The epoxy resin composition for sealing semiconductor elements contains an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, and the epoxy resin contains an epoxy resin represented by the following Chemical Formula 1.

[0009] [Chemical Formula 1]

Chemical

Chemical

[0010] According to one embodiment, a semiconductor device is provided.

[0011] The semiconductor device is sealed with the epoxy resin composition for sealing the semiconductor device.

Advantages of the Invention

[0012] Provided is an epoxy resin composition for sealing a semiconductor device, which has high thermal conductivity, so that the heat dissipation effect is significantly improved, and the fluidity is improved.

Embodiments for Carrying Out the Invention

[0013] Hereinafter, a detailed description will be given so that those having ordinary knowledge in the technical field can easily implement specific embodiments. However, the present invention can be embodied in various different forms and is not limited to the embodiments described herein.

[0014] The terms used herein are for the purpose of describing exemplary embodiments only and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise.

[0015] When describing a numerical range in this specification, "X~Y" means X or more and Y or less.

[0016] In the present specification, in "substituted or unsubstituted", "substituted" means that one or more hydrogen atoms in the corresponding functional group are a hydroxyl group, an amino group, a nitro group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 3 to 10 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heteroalkyl group having 1 to 30 carbon atoms.

[0017] When imparting high thermal conductivity to an epoxy resin composition for sealing semiconductor elements, it is necessary to use a relatively large amount of inorganic filler. However, when a large amount of inorganic filler is used, the viscosity of the composition increases and the fluidity deteriorates, which may cause problems in the moldability of semiconductor packages. Among inorganic fillers, a method of using alumina, which is an inorganic filler having a relatively high thermal conductivity, can be considered. However, since the thermal conductivity of the epoxy resin essentially contained in the composition is about 0.2 W / m·K, which is very low, there is a limit to increasing the thermal conductivity of the composition even when alumina is used.

[0018] According to one embodiment, the epoxy resin composition for sealing semiconductor elements contains an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, and the epoxy resin contains the epoxy resin of Chemical Formula 1 described below. Since the epoxy resin of Chemical Formula 1 has high thermal conductivity, it improves the heat dissipation characteristics of the composition, and since it has low viscosity, it improves the fluidity of the composition. This can suppress malfunction and defects of the semiconductor package due to heat, and enhance reliability by keeping the surface temperature of the semiconductor low. Further, the epoxy resin of Chemical Formula 1 can provide the effect of reducing the water absorption of the composition and enhancing the solder stress resistance.

[0019] (Epoxy resin) The epoxy resin contains the epoxy resin of Chemical Formula 1 below. Since the epoxy resin of Chemical Formula 1 has high thermal conductivity, it significantly improves the heat dissipation characteristics of the composition, and since it has low viscosity, it also enhances the fluidity of the composition and improves the processability of the composition.

[0020] [Chemical Formula 1] [Chemical Structure] (In Chemical Formula 1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10is, independently of each other, hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a hydroxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms, or the following Chemical Formula 2, [Chemical Formula 2]

Chemical Structure

[0021] Preferably, among R 1 , R 2 , R 3 , R 4 , R 5 of which, R 3 is the above Chemical Formula 2, and R 1 , R 2 , R 4 , R 5 are, independently of each other, hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, for example, hydrogen, an unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms may be used.

[0022] Preferably, R 6 , R 7 , R 8 , R 9 , R 10 Among them, R 8 is the aforementioned Chemical Formula 2, and R 6 , R 7 , R 9 , R 10 are each independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, for example, hydrogen, an unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms may be used.

[0023] In one embodiment, the epoxy resin of Chemical Formula 1 can include one or more of Chemical Formulas 1-1, 1-2, 1-3, 1-4, and 1-5.

[0024] [Chemical Formula 1-1](1,4-Bis(4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diyne)

Chem.

[0025] [Chemical Formula 1-2](2-((3-methyl-4-(4-(2-methyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)phenoxy)methyl)oxirane)

Chem.

[0026] [Chemical Formula 1-3](2-((4-(4-(2,6-dimethyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)-3,5-dimethylphenoxy)methyl)oxirane)

Chem.

[0027] [Chemical Formula 1-4] (2-((3-methoxy-4-(4-(2-methoxy-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)phenoxy)methyl)oxirane)

Chem.

[0028] [Chemical Formula 1-5] (2-((4-(4-(2,6-diethyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)-3,5-diethylphenoxy)methyl)oxirane)

Chem.

[0029] The epoxy resin of Chemical Formula 1 may be included as one or more types in the epoxy resin composition, and may be included in the epoxy resin composition at 0.1% by weight to 17% by weight, preferably 2% by weight to 17% by weight, more preferably 2% by weight to 10% by weight. Within the above range, the heat dissipation characteristics of the composition can be improved, and the curability of the composition may not decrease.

[0030] The epoxy resin of Chemical Formula 1 can be manufactured by the methods for manufacturing ordinary epoxy resins known to those skilled in the art with reference to Chemical Formula 1, or products commercially sold can be purchased and used.

[0031] In the epoxy resin composition for encapsulating semiconductor elements, the epoxy resin may consist only of the epoxy resin of Chemical Formula 1. That is, among the epoxy resins contained in the epoxy resin composition for encapsulating semiconductor elements, the epoxy resin of Chemical Formula 1 may be contained at 100% by weight.

[0032] However, within a range that does not affect the effects of the present invention, an epoxy resin other than the epoxy resin of Chemical Formula 1 can be further included. For convenience, the epoxy resin of Chemical Formula 1 is referred to as the first epoxy resin, and the epoxy resin other than the epoxy resin of Chemical Formula 1 is referred to as the second epoxy resin.

[0033] The second epoxy resin has two or more epoxy groups in the molecule, and may be a bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, tert-butylcatechol type epoxy resin, naphthalene type epoxy resin, glycidylamine type epoxy resin, cresol novolac type epoxy resin, biphenyl type epoxy resin, phenol aralkyl type epoxy resin, linear aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexanedimethanol type epoxy resin, trimethylol type epoxy resin, halogenated epoxy resin, etc. The second epoxy resin can be included alone or as a mixture of two or more.

[0034] The epoxy resin may be contained in the epoxy resin composition in an amount of 2% to 17% by weight, preferably 2% to 10% by weight. Within the above range, the curability of the composition may not decrease.

[0035] (Curing agent) Examples of the curing agent include polyfunctional phenol resins, phenol aralkyl type phenol resins, phenol novolac type phenol resins, xylock type phenol resins, cresol novolac type phenol resins, naphthol type phenol resins, terpene type phenol resins, dicyclopentadiene-based phenol resins, novolac type phenol resins synthesized from bisphenol A and resole; polyhydric phenol compounds containing tris(hydroxyphenyl)methane and dihydroxybiphenyl; acid anhydrides containing maleic anhydride and phthalic anhydride; aromatic amines such as metaphenylenediamine, diaminodiphenylmethane, and diaminodiphenylsulfone. Preferably, the curing agent may be a xylock type phenol resin or a phenol aralkyl type phenol resin.

[0036] The curing agent may be contained in the epoxy resin composition at 0.5% to 13% by weight. Within the above range, the curability of the composition may not decrease.

[0037] (Inorganic filler) The inorganic filler can enhance the mechanical properties and reduce the stress of the epoxy resin composition. Furthermore, in the present invention, the inorganic filler can increase the thermal conductivity to enhance the heat dissipation effect, improve the fluidity, and reduce the thermal expansion and water absorption.

[0038] The inorganic filler can include one or more of fused silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, titanium oxide, antimony oxide, and glass fiber.

[0039] Preferably, the inorganic filler can include alumina. Alumina has a thermal conductivity of 25 W / m·K to 30 W / m·K and can easily increase the thermal conductivity of the composition.

[0040] The shape of alumina is not limited and may be spherical or non-spherical. Spherical can improve the fluidity of the composition. The average particle size (D50) of alumina may be 0.5 μm to 50 μm, preferably 0.5 μm to 30 μm. Within the above range, the fluidity and the thermal conductivity can be improved. In one embodiment, alumina can include a mixture of two types with different average particle sizes (D50). For example, alumina is mixed with a weight ratio of the first alumina: the second alumina of 1:1 to 10:1, and the average particle size (D50) of the first alumina may be larger than that of the second alumina. Alumina may be contained in the composition after being pre-coated with an epoxy resin or a curing agent as needed.

[0041] The amount of the inorganic filler used varies depending on required physical properties such as thermal conductivity, moldability, low stress property, and high-temperature strength. In an embodiment, the inorganic filler may be contained in the epoxy resin composition at 50 wt% to 95 wt%, specifically 70 wt% to 95 wt%, more specifically 85 wt% to 95 wt%. Within the above range, the flame retardancy, fluidity, and reliability of the epoxy resin composition can be ensured.

[0042] (Curing catalyst) Examples of the curing catalyst may include tertiary amine compounds, organometallic compounds, organic phosphorus compounds, imidazole-based compounds, or boron compounds. Examples of the tertiary amine compounds include benzyldimethylamine, triethanolamine, triethylenediamine, diethylaminoethanol, tri(dimethylaminomethyl)phenol, 2-2-(dimethylaminomethyl)phenol, 2,4,6-tris(diaminomethyl)phenol, and tri-2-ethylhexanoate. Examples of the organometallic compounds include chromium acetylacetonate, zinc acetylacetonate, nickel acetylacetonate, etc. Examples of the organic phosphorus compounds may include triphenylphosphine, tris-4-methoxyphosphine, triphenylphosphine triphenylborane, triphenylphosphine-1,4-benzoquinone adduct, etc. Examples of the imidazole-based compounds include 2-methylimidazole, 2-phenylimidazole, 2-aminoimidazole, 2-methyl-1-vinylimidazole, 2-ethyl-4-methylimidazole, 2-heptadecylimidazole, etc. Examples of the boron compounds include triphenylphosphine tetraphenylborate, tetraphenylboron salts, trifluoroborane-n-hexylamine, trifluoroborane monoethylamine, tetrafluoroborane triethylamine, tetrafluoroborane amine, etc. In addition, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and phenol novolak resin salts can also be used.

[0043] The curing catalyst can also use an adduct formed by reacting with an epoxy resin or a curing agent in advance.

[0044] The curing catalyst may be contained in the epoxy resin composition at 0.01% by weight to 5% by weight. Within the above range, the curing reaction time is not delayed, and the fluidity of the composition can be ensured.

[0045] The epoxy resin composition can further contain ordinary additives in the epoxy resin composition for semiconductor element encapsulation. In an embodiment, the additives can include one or more of a coupling agent, a release agent, a coloring agent, a stress reliever, a crosslinking promoter, and a leveling agent.

[0046] The coupling agent is for reacting between the epoxy resin and the inorganic filler to improve the interfacial strength. For example, it may be a silane coupling agent. The silane coupling agent only needs to react between the epoxy resin and the inorganic filler to improve the interfacial strength between the epoxy resin and the inorganic filler, and the type is not particularly limited. Specific examples of the silane coupling agent can include epoxy silane, amino silane, ureido silane, mercapto silane, and alkyl silane, etc. The coupling agent can be used alone or in combination. The coupling agent may be contained in the epoxy resin composition for semiconductor element encapsulation at 0.01% by weight to 5% by weight, preferably 0.05% by weight to 3% by weight. Within the above range, the strength of the cured product of the epoxy resin composition can be improved.

[0047] As the release agent, one or more selected from the group consisting of paraffin wax, ester wax, higher fatty acid, higher fatty acid metal salt, natural fatty acid, and natural fatty acid metal salt can be used. The release agent may be contained in the epoxy resin composition at 0.1% by weight to 1% by weight.

[0048] As the coloring agent, carbon black can be used. The coloring agent may be contained in the epoxy resin composition at 0.1% by weight to 1% by weight.

[0049] The stress relaxant can be one or more selected from the group consisting of modified silicone oil, silicone elastomer, silicone powder, and silicone resin, but is not limited thereto. The stress relaxant may be contained in the epoxy resin composition in an amount of 0 wt% to 2 wt%, for example, 0 wt% to 1 wt%, for example, 0.1 wt% to 1 wt%.

[0050] The additive may be contained in the epoxy resin composition in an amount of 0.1 wt% to 5 wt%, for example, 0.1 wt% to 3 wt%.

[0051] The method for producing the epoxy resin composition is not particularly limited. After uniformly mixing each constituent component contained in the composition using a Henschel mixer or a Lodige mixer, it can be melt-kneaded at 90°C to 120°C using a roll mill or a kneader, and then produced through a cooling and pulverization process.

[0052] The semiconductor element is sealed using the epoxy resin composition for sealing semiconductor elements of the present invention. The method for sealing a semiconductor element or the like using the epoxy resin composition can use transfer molding, injection molding, casting molding, compression molding, etc., and is not necessarily limited thereto. In one embodiment, it can be sealed by a low-pressure transfer molding method. In other embodiments, it can be sealed by compression molding.

[0053] Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to preferred examples of the present invention. However, this is presented as a preferred exemplification of the present invention and should not be construed as limiting the present invention in any way.

[0054] (Production Example: Production and Analysis of Epoxy Resin) The epoxy resins of Chemical Formulas 1-1, 1-2, 1-3, 1-4, and 1-5 were produced by the following method.

[0055] [Chemical Formula 1-1] (1,4-Bis(4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diyne)

Chem.

[0056] Into a 1,000 mL reactor, 500 mL of DMF solvent, 4-Iodophenol (30 g, 136.2 mmol), Propiolic acid (18.5 mL, 300 mmol), Et3N (70 mL), and as catalysts PdCl2(PPh3)2 (5 g, 7.1 mmol), CuI (1.7 g, 9.0 mmol), and Ag2CO3 (83 g, 300 mmol) were added. After reacting at 130 °C for 24 hours, the solvent was dried and purified by passing through a silica column. The solvent used during column passage was Ethyl acetate / Hexane (1:6). After passing through the silica column, the solvent was reduced in pressure to obtain 17 g of a bright yellow compound powder, benzyltrimethylammonium bromide (5.0 g, 21.7 mmol), and an excess of epichlorohydrin (300 mL) were placed into a 500 mL reactor. After reacting at 110 °C for 1 hour, NaOH (6 g, 145.0 mmol) was added and the reaction was carried out for another 2 hours. After the reaction was completed, the solvent was reduced in pressure and purified with DI water to obtain 21 g of a bright yellow powder of compound [Chemical Formula 1-1] with a yield of 42%.

[0057] It was confirmed to be the compound of [Chemical Formula 1-1] by NMR, LC-MS and elemental analysis. 1 H NMR (400 MHz, CDCl3) 7.53 (m, 2H), 7.01 (m, 4H), 4.40 (m, 2H), 3.88, (m, 2H), 3.33 (m, 2H), 2.85 (m, 2H), 2.71 (m, 2H)) ppm; 13 C NMR (100 MHz, CDCl3) 159.1, 133.9, 114.9, 112.6, 81.3, 72.6, 69.9, 49.9, 43.3 ppm; LC-MS m / z = 346 (M +); Anal. Calcd for C 22 H 18 O4: C, 76.29; H, 5.24; Found: C, 76.54; H, 5.39

[0058] [Chemical formula 1-2] (2-((3-methyl-4-(4-(2-methyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)phenoxy)methyl)oxirane)

Chem.

[0059] Into a 1,000 mL reactor, 500 mL of DMF solvent, 4-iodo-3-methylphenol (32 g, 136.2 mmol), propiolic acid (18.5 mL, 300 mmol), Et3N (70 mL), and PdCl2(PPh3)2 (5 g, 7.1 mmol) as a catalyst, CuI (1.7 g, 9.0 mmol) and Ag2CO3 (83 g, 300 mmol) were added. After reacting at 130 °C for 24 hours, the solvent was dried and purified by passing through a silica column. The solvent used during column passing was Ethyl acetate / Hexane (1:6). After passing through the silica column, the solvent was depressurized to obtain 18 g of a bright yellow compound powder, benzyltrimethylammonium bromide (5.0 g, 21.7 mmol), and an excess of epichlorohydrin (300 mL) were placed into a 500 mL reactor. After reacting at 110 °C for 1 hour, NaOH (6 g, 145.0 mmol) was added and the reaction was carried out for another 2 hours. After the reaction was completed, the solvent was depressurized and purified with DI water to obtain 20 g of a bright yellow powder of compound [Chemical formula 1-2] with a yield of 40%.

[0060] It was confirmed to be the compound of [Chemical formula 1-2] by NMR, LC-MS and elemental analysis. 11H NMR (400 MHz, CDCl3) δ 7.19 (m, 2H), 6.57 - 6.54 (m, 4H), 4.20 (m, 2H), 3.95 (m, 2H), 3.05 (m, 2H), 2.63 (m, 2H), 2.35 (m, 2H), 2.33 (s, 6H) ppm; 13 13C NMR (100 MHz, CDCl3) δ 157.1, 142.8, 132.8, 115.2, 112.8, 111.0, 77.0, 74.7, 69.5, 50.0, 44.2, 17.2 ppm; LC-MS m / z = 374 (M + +); Anal. Calcd for C 24 19 22 H

[0061] [Chemical Formula 1-3] (2-((4-(4-(2,6-dimethyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)-3,5-dimethylphenoxy)methyl)oxirane) [Chem.]

[0062] Into a 1,000 mL reactor, 500 mL of DMF solvent, 4-iodo-3,5-dimethylphenol (34 g, 136.2 mmol), propiolic acid (18.5 mL, 300 mmol), Et3N (70 mL), and as catalysts PdCl2(PPh3)2 (5 g, 7.1 mmol), CuI (1.7 g, 9.0 mmol) and Ag2CO3 (83 g, 300 mmol) were added. After reacting at 130 °C for 24 hours, the solvent was dried and purified by passing through a silica column. The solvent used during column passage was Ethyl acetate / Hexane (1:6). After passing through the silica column, the solvent was reduced in pressure to obtain 18 g of a bright yellow compound powder, benzyltrimethylammonium bromide (5.0 g, 21.7 mmol), and an excess of epichlorohydrin (300 mL) were placed into a 500 mL reactor. After reacting at 110 °C for 1 hour, NaOH (6 g, 145.0 mmol) was added and the reaction was carried out for another 2 hours. After the reaction was completed, the solvent was reduced in pressure and purified with DI water to obtain 20 g of a bright yellow powder of compound [Chemical formula 1-3] with a yield of 39%.

[0063] It was confirmed by NMR, LC-MS and elemental analysis that it was the compound of [Chemical formula 1-3]. 1 H NMR (400 MHz, CDCl3) 6.35 (m, 4H), 4.20 (m, 2H), 3.95, (m, 2H), 3.05 (m, 2H), 2.63 (m, 2H), 2.38 (m, 2H), 2.35 (s, 12H) ppm; 13 C NMR (100 MHz, CDCl3) 157.1, 142.5, 113.2, 110.1, 109.9, 77.0, 74.7, 69.5, 50.0, 44.2, 17.4 ppm; LC-MS m / z = 402 (M + ); Anal. Calcd for C 26 H 26 O4: C, 77.59; H, 6.51; Found: C, 77.81; H, 6.58

[0064] [Chemical Formula 1-4](2-((3-methoxy-4-(4-(2-methoxy-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)phenoxy)methyl)oxirane)

Chem.

[0065] Into a 1,000 mL reactor, 500 mL of DMF solvent, 4-iodo-3-methoxyphenol (34 g, 136.2 mmol), Propiolic acid (18.5 mL, 300 mmol), Et3N (70 mL), and as a catalyst PdCl2(PPh3)2 (5 g, 7.1 mmol), CuI (1.7 g, 9.0 mmol) and Ag2CO3 (83 g, 300 mmol) were added and reacted at 130 °C for 24 hours. Then the solvent was dried and purified by passing through a silica column. The solvent used during column passage was Ethyl acetate / Hexane (1:6). After passing through the silica column, the solvent was reduced in pressure to obtain 18 g of a bright yellow compound powder, benzyltrimethylammonium bromide (5.0 g, 21.7 mmol), and an excess of epichlorohydrin (300 mL) were placed into a 500 mL reactor and reacted at 110 °C for 1 hour. Then NaOH (6 g, 145.0 mmol) was added and the reaction was carried out for another 2 hours. After the reaction was completed, the solvent was reduced in pressure and purified with DI water to obtain 20 g of a bright yellow powder of compound [Chemical Formula 1-4] with a yield of 38%.

[0066] It was confirmed to be the compound of [Chemical Formula 1-4] through NMR, LC-MS and elemental analysis. 1 H NMR (400 MHz, CDCl3) 7.20 (s, 2H), 6.32 - 6.25 (m, 4H), 4.20 (m, 2H), 3.95, (m, 2H), 3.73 (s, 6H), 3.05 (m, 2H), 2.63 (m, 2H), 2.35 (m, 2H) ppm; 1313C NMR (100 MHz, CDCl3) δ 164.01, 158.1, 142.8, 133.9, 133.8, 106.3, 106.2, 103.5, 100.1, 100.0, 77.0, 74.7, 69.5, 55.3, 50.0, 44.2 ppm; LC-MS m / z = 408 (M + ); Anal. Calcd for C 24 H 22 O6: C, 70.92; H, 5.46; Found: C, 70.91; H, 5.71.

[0067] [Chemical Formula 1-5] (2-((4-(4-(2,6-diethyl-4-(oxiran-2-ylmethoxy)phenyl)buta-1,3-diynyl)-3,5-diethylphenoxy)methyl)oxirane)

Chem.

[0068] Into a 1,000 mL reactor, 500 mL of DMF solvent, 3,5-diethyl-4-iodophenol (38 g, 136.2 mmol), propiolic acid (18.5 mL, 300 mmol), Et3N (70 mL), and PdCl2(PPh3)2 (5 g, 7.1 mmol) as a catalyst, CuI (1.7 g, 9.0 mmol), and Ag2CO3 (83 g, 300 mmol) were added. After reacting at 130 °C for 24 hours, the solvent was dried and purified by passing through a silica column. The solvent used during column passing was Ethyl acetate / Hexane (1:6). After passing through the silica column, the solvent was reduced in pressure to obtain 18 g of a bright yellow compound powder. Then, benzyltrimethylammonium bromide (5.0 g, 21.7 mmol) and an excess of epichlorohydrin (300 mL) were added to a 500 mL reactor and reacted at 110 °C for 1 hour. Then, NaOH (6 g, 145.0 mmol) was added and the reaction was carried out for another 2 hours. After the reaction was completed, the solvent was reduced in pressure and purified with DI water to obtain 19 g of a bright yellow powder of compound [Chemical Formula 1-5] with a yield of 35%.

[0069] It was confirmed to be a compound of [Chemical Formula 1-5] by NMR, LC-MS and elemental analysis. 1 H NMR (400 MHz, CDCl3) δ 6.42 (s, 4H), 4.20 (m, 2H), 3.95 (m, 2H), 3.05 (m, 2H), 2.63 - 2.52 (m, 10H), 2.38 (m, 2H), 1.24 (m, 12H) ppm; 13 C NMR (100 MHz, CDCl3) δ 157.1, 148.6, 148.5, 111.1, 111.0, 109.0, 108.9, 77.0, 74.7, 69.5, 50.0, 44.2, 25.6, 25.4, 14.0 ppm; LC-MS m / z = 458 (M + ); Anal. Calcd for C 30 H 34 O4: C, 78.57; H, 7.47; Found: C, 78.19; H, 7.58.

[0070] The specific specifications of the components used in the following examples and comparative examples are as follows.

[0071] (A) Epoxy resin (A1) Epoxy resins of Production Examples (A1-1 (Chemical Formula 1-1), A1-2 (Chemical Formula 1-2), A1-3 (Chemical Formula 1-3), A1-4 (Chemical Formula 1-4), A1-5 (Chemical Formula 1-5)) (A2) Phenol aralkyl type epoxy resin (NC-3000, Nippon Kayaku Co., Ltd.) (A3) Epoxy resin of the following chemical formula

Chemical formula

[0072] (B) Hardening agent (B1) KPH-F3065 (Xyloque type phenol resin, Kolon Chemical Co., Ltd.) (B2) MEH-7851 (Phenol aralkyl type phenol resin, Meiwa Co., Ltd.)

[0073] (C) Curing Catalyst: Triphenylphosphine (Hokko Chemical)

[0074] (D) Inorganic Filler: A mixture of spherical fused alumina with an average particle size (D50) of 20 μm and spherical fused alumina with an average particle size (D50) of 0.5 μm at a weight ratio of 9:1

[0075] (E) Coupling Agent (E1) Methyltrimethoxysilane (SZ - 6070, Dow Corning) (E2) KBM - 573 (N - Phenyl - 3 - aminopropyltrimethoxysilane, Shinetsu)

[0076] (F) Carbon Black (MA - 600B, Mitsubishi Chemical)

[0077] (Examples 1 - 6 and Comparative Examples 1 - 4) According to the composition in Table 1 below (unit: parts by weight), using a Henschel mixer (KEUM SUNG MACHINERY CO.LTD, KSM - 22), it was uniformly mixed at 25°C to 30°C for 30 minutes, then melt - kneaded at a maximum of 110°C for 30 minutes using a continuous kneader, cooled at 10°C to 15°C, and pulverized to produce an epoxy resin composition for semiconductor element encapsulation. In Table 1 below, "-" means that the corresponding component is not included.

[0078] The following physical properties were evaluated for the produced epoxy resin composition for semiconductor element encapsulation, and the results are shown in Table 1 below. (1) Fluidity (unit: inch, spiral flow): Using a low - pressure transfer molding machine, according to EMMI - 1 - 66, the epoxy resin composition for semiconductor element encapsulation was injected into a mold for fluidity measurement at a mold temperature of 175°C, 70 kgf / cm 2 , an injection pressure of 9 MPa, and a curing time of 90 seconds, and the flow length was measured. The higher the measured value, the better the fluidity. (2) Thermal Conductivity (unit: W / m·K): Evaluation specimens were produced from the epoxy resin composition according to ASTM D5470 and measured at 25°C.

[0079]

Table 1

[0080] As shown in Table 1 above, the epoxy resin composition for sealing semiconductor elements in the examples was excellent in fluidity and had high thermal conductivity, so it had excellent heat dissipation characteristics and the effect of maintaining a low semiconductor surface temperature during semiconductor operation.

[0081] On the other hand, the composition of the comparative example that does not contain the epoxy resin of Chemical Formula 1 had problems that the heat dissipation characteristics were not good because the thermal conductivity was low and / or it was difficult to mold because the fluidity was also low.

[0082] Simple modifications or changes of the present invention can be easily implemented by those having ordinary knowledge in this field, and all such modifications and changes can be regarded as being included in the scope of the present invention.

Claims

1. An epoxy resin composition for sealing a semiconductor element, comprising an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, wherein the epoxy resin includes an epoxy resin represented by the following Chemical Formula 1. [Chemical Formula 1] 【Chemical 1】 (In the above Chemical Formula 1, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ is, independently of one another, hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a hydroxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 30 carbon atoms or the following Chemical Formula 2, [Chemical Formula 2] 【Chemical Formula 2】 (In the above Chemical Formula 2, * represents the bonding site of the element) R １ , R ２ , R ３ , R ４ , R ５ At least one of them is the chemical formula 2, R ６ , R ７ , R ８ , R ９ , R １０ At least one of them is the said Chemical Formula 2.)

2. In the formula (1), R １ , R ２ , R ３ , R ４ , R ５ Among them, R ３ is the formula (2), and R １ , R ２ , R ４ , R ５ are each independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. Among R ６ , R ７ , R ８ , R ９ , R １０ , R ８ is the formula (2), and R ６ , R ７ , R ９ , R １０ are each independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. The epoxy resin composition for sealing a semiconductor element according to claim 1.

3. The epoxy resin composition for sealing a semiconductor element according to Claim 1, wherein the epoxy resin represented by Chemical Formula 1 includes one or more of the following Chemical Formulas 1-1, 1-2, 1-3, 1-4, and 1-5. [Chemical Formula 1-1] [Chemical Formula 3] [Chemical Formula 1-2] 【Chemical Formula 4】 [Chemical Formula 1-3] 【Chemical Formula 5】 [Chemical Formula 1-4] 【Chemical Formula 6】 [Chemical Formula 1-5] 【Chemical Formula 7】

4. The epoxy resin composition for sealing a semiconductor element according to Claim 1, wherein the epoxy resin represented by Chemical Formula 1 is contained in the epoxy resin composition in an amount of 0.1% by weight to 17% by weight.

5. The epoxy resin composition for sealing a semiconductor element according to Claim 1, wherein the inorganic filler includes alumina.

6. The epoxy resin composition for sealing a semiconductor element according to Claim 1, comprising 2% by weight to 17% by weight of the epoxy resin, 0.5% by weight to 13% by weight of the curing agent, 50% by weight to 95% by weight of the inorganic filler, and 0.01% by weight to 5% by weight of the curing catalyst.

7. A semiconductor element sealed using the epoxy resin composition for sealing a semiconductor element according to any one of Claims 1 to 6.

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