Epoxy resin composition for sealing semiconductor element and semiconductor element sealed using the same

Abstract

To provide an epoxy resin composition for semiconductor element sealing that exhibits excellent fluidity, has high thermal conductivity, provides significantly improved heat dissipation, and yields a cured product having enhanced crack resistance.SOLUTION: An epoxy resin composition for semiconductor element sealing comprises an epoxy compound, a curing agent, an inorganic filler, and a curing catalyst, the epoxy compound comprising an epoxy compound represented by the following formula 1. In formula 1, A is an ethylene group or a propylene group; n is an integer of 1 to 10; T1 and T2 each independently represent a single bond, -O-, or -S-; and T3 and T4 are epoxy groups.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an epoxy resin composition for sealing semiconductor devices and a semiconductor device sealed with the same. [Background technology]

[0002] In recent years, the integration density of semiconductor devices has been increasing. In semiconductor devices in which stacked and highly dense semiconductor devices are sealed in small, thin packages, the frequency of package malfunctions and package cracks due to heat generated during semiconductor operation can become very high.

[0003] One solution to heat dissipation is to use a heat sink made of a heat-dissipating material such as a metal material when molding the epoxy resin for sealing. However, heat sinks can only be used with certain packages, such as FBGA (fine pitch ball grid array) and QFP (quad flat package), and they have problems such as reduced productivity due to the additional assembly process and increased costs due to the high cost of the heat sink. Therefore, there is a growing need for epoxy resin molding materials for sealing with high thermal conductivity and high heat dissipation. Some semiconductor packages use spherical aluminum oxide (alumina).

[0004] A relatively well-known method for imparting high thermal conductivity to a resulting resin composition or epoxy molding compound is to use aluminum oxide (alumina), which has a higher thermal conductivity (25 W / m·K to 30 W / m·K) than silicon oxide. However, the resins used in resin compositions have a very low thermal conductivity of approximately 0.2 W / m·K, making it difficult to obtain a semiconductor sealing composition with a thermal conductivity of 6 W / m·K or higher.

[0005] On the other hand, using a large amount of inorganic filler increases the viscosity, which can lead to wire sweeping, and decreases fluidity, which can lead to poor package moldability and void formation. Increasing the inorganic filler fill rate to improve thermal conductivity can result in chip damage and package cracks due to package stress during external impact and moisture absorption reliability tests, so there is a limit to how much the inorganic filler can be increased. Furthermore, since heat must pass through the resin for heat transfer, even if the filler has high thermal conductivity, heat is not transferred effectively if the resin has low thermal conductivity. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide an epoxy resin composition for encapsulating semiconductor devices that exhibits excellent fluidity, or that gives a cured product with high thermal conductivity, significantly improved heat dissipation, and excellent crack prevention effects. [Means for solving the problem]

[0007] According to one embodiment, there is provided an epoxy resin composition for encapsulating a semiconductor device.

[0008] The epoxy resin composition for encapsulating a semiconductor device includes an epoxy compound, a curing agent, an inorganic filler, and a curing catalyst, and the epoxy compound includes an epoxy compound represented by the following Chemical Formula 1:

[0009] [ka]

[0010] In Chemical Formula 1, A is an ethylene or propylene group; n is an integer from 1 to 10, T1 and T2 each independently represent a single bond, —O—, or —S—; T3 and T4 are each independently represented by the following chemical formula 2.

[0011] [ka] In Chemical Formula 2, * is the linking site of the element, B is a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms.

[0012] In Chemical Formula 1, Ra, Rb, Rc, and Rd each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 10 carbon atoms; m1 and m2 each independently represent an integer from 0 to 4; m3 and m4 each independently represent an integer of 0 to 4.

[0013] According to one embodiment, a semiconductor device is provided.

[0014] The semiconductor element is sealed with the epoxy resin composition for sealing a semiconductor element. [Effects of the Invention]

[0015] The present invention can provide an epoxy resin composition for encapsulating semiconductor devices that has excellent fluidity and high thermal conductivity, thereby significantly improving heat dissipation and providing a cured product with excellent crack prevention effects. DETAILED DESCRIPTION OF THE INVENTION

[0016] Although the present invention may be embodied in various different forms, it is not intended to be limited to the embodiments set forth herein.

[0017] The terms used herein are merely used to describe exemplary embodiments and are not intended to limit the present invention. The singular expressions include the plural expressions unless the context clearly indicates otherwise.

[0018] In this specification, when describing a range of values, "X to Y" means X or more and Y or less.

[0019] In this specification, the term "substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms of the functional group are substituted with a hydroxyl group, an amino group, a nitro group, a cyano group, an alkyl 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.

[0020] To impart high thermal conductivity to the cured epoxy resin composition for semiconductor device encapsulation, a relatively large amount of inorganic filler is required. However, using a large amount of inorganic filler increases the viscosity of the composition, reducing its flowability, which can lead to problems with the moldability of the semiconductor package. One possible solution is to use alumina, an inorganic filler with relatively high thermal conductivity. However, the thermal conductivity of the epoxy resin, which is an essential component of the cured composition, is very low, at approximately 0.2 W / m·K, so even using alumina limits the effectiveness of increasing the composition's thermal conductivity.

[0021] According to one embodiment, an epoxy resin composition for encapsulating semiconductor devices (hereinafter simply referred to as the epoxy resin composition) includes an epoxy compound, a curing agent, an inorganic filler, and a curing catalyst, and the epoxy compound includes an epoxy compound represented by Chemical Formula 1, as described below. A cured product of the epoxy resin composition (hereinafter simply referred to as the cured product) exhibits high thermal conductivity and thus improved heat dissipation properties. The epoxy compound represented by Chemical Formula 1 has low viscosity, thereby improving the fluidity of the composition. The epoxy compound represented by Chemical Formula 1 increases the toughness of the cured product, thereby reducing cracking and improving reliability. The cured product can suppress thermal-induced malfunctions and defects in semiconductor packages and maintain a low semiconductor surface temperature, thereby improving the reliability of the semiconductor package. In addition, the cured product has low moisture absorption and can provide improved solder stress resistance.

[0022] Epoxy compounds The epoxy compound is represented by the following chemical formula 1.

[0023] [ka]

[0024] In Chemical Formula 1, A is an ethylene or propylene group; n is an integer from 1 to 10, T1 and T2 each independently represent a single bond, —O—, or —S—; T3 and T4 are each independently represented by the following chemical formula 2:

[0025] [ka]

[0026] In Chemical Formula 2, * is the linking site of the element, B is a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms.

[0027] In Chemical Formula 1, Ra, Rb, Rc, and Rd each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 10 carbon atoms; m1 and m2 each independently represent an integer from 0 to 4; m3 and m4 each independently represent an integer of 0 to 4.

[0028] The epoxy compound of Chemical Formula 1 is a liquid crystal epoxy compound having a repeating unit of an ethylene oxide or propylene oxide group and a biphenyl group, biphenyl ether, or biphenyl thioether group. Therefore, the cured product obtained by curing the epoxy compound of Chemical Formula 1 has high thermal conductivity and significantly improved heat dissipation properties. Furthermore, the epoxy compound of Chemical Formula 1 provides high toughness to the cured product, suppressing damage and cracking of semiconductor devices when they are subjected to external impact or during reliability evaluation. Furthermore, the epoxy compound of Chemical Formula 1 has low viscosity, which increases the fluidity of the composition and improves the processability of the composition.

[0029] In Chemical Formula 1, a "single bond" means that each aromatic group is directly connected.

[0030] In one specific example, T1 and T2 in Chemical Formula 1 may be a single bond or -O-, preferably a single bond.

[0031] In one embodiment, n in Chemical Formula 1 may be an integer of 3 to 8, preferably an integer of 3 to 5.

[0032] In one embodiment, A in Formula 1 can be ethylene, n-propylene, or iso-propylene.

[0033] In one specific example, Ra, Rb, Rc, and Rd in Chemical Formula 1 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0034] In one embodiment, m1, m2, m3, and m4 in Chemical Formula 1 may each independently be 0, 1, 2, 3, or 4, and preferably 0 or 1.

[0035] In the epoxy resin composition, one or more epoxy compounds of Formula 1 may be included.

[0036] The epoxy compound of Chemical Formula 1 may include one or more of the following Chemical Formulas 3 and 4. [ka]

[0037] In Chemical Formula 3 and Chemical Formula 4, Ra', Rb', Rc', and Rd' each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and A, n, m1, m2, m3, and m4 are the same as defined in Chemical Formula 1.

[0038] The epoxy compound of Chemical Formula 1 may include one or more of the following Chemical Formulas 5 to 8. [ka]

[0039] The epoxy resin composition may contain one or more epoxy compounds of Chemical Formula 1, and may contain 0.1 to 17% by weight, preferably 2 to 17% by weight, and more preferably 2 to 10% by weight in the epoxy resin composition. By adopting the above range, the heat dissipation properties of the cured product can be improved and a decrease in the curability of the composition can be suppressed.

[0040] The epoxy compound of Chemical Formula 1 can be prepared by a method for preparing a general epoxy compound known to those skilled in the art, with reference to Chemical Formula 1.

[0041] The epoxy compound of the epoxy resin composition for encapsulating a semiconductor device may consist solely of the epoxy compound of Chemical Formula 1. That is, the epoxy compound of Chemical Formula 1 may be contained in an amount of 100% by weight in the epoxy compound contained in the epoxy resin composition for encapsulating a semiconductor device.

[0042] However, within the scope that does not affect the effects of the present invention, an epoxy compound other than the epoxy compound of Chemical Formula 1 may be further included. For convenience, the epoxy compound of Chemical Formula 1 is referred to as the first epoxy compound, and an epoxy compound other than the epoxy compound of Chemical Formula 1 is referred to as the second epoxy compound.

[0043] The second epoxy compound has two or more epoxy groups in the molecule, and may be a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a phenol novolac type epoxy compound, a tert-butylcatechol type epoxy compound, a naphthalene type epoxy compound, a glycidylamine type epoxy compound, a cresol novolac type epoxy compound, a biphenyl type epoxy compound, a phenol aralkyl type epoxy compound, a linear aliphatic epoxy compound, an alicyclic epoxy compound, a heterocyclic epoxy compound, a spiro ring-containing epoxy compound, a cyclohexanedimethanol type epoxy compound, a trimethylol type epoxy compound, a halogenated epoxy compound, etc. The second epoxy compound may be contained alone or in a mixture of two or more types.

[0044] The epoxy compound may be contained in the epoxy resin composition in an amount of 2 to 17% by weight, preferably 2 to 10% by weight. By adopting this range, it is possible to prevent a decrease in the curability of the composition.

[0045] hardener Examples of curing agents include polyfunctional phenolic compounds, phenol aralkyl phenolic compounds, phenol novolac phenolic compounds, zylok phenolic compounds, cresol novolac phenolic compounds, naphthol phenolic compounds, terpene phenolic compounds, dicyclopentadiene phenolic compounds, novolac phenolic compounds synthesized from bisphenol A and resol, polyhydric phenolic compounds including tris(hydroxyphenyl)methane and dihydroxybiphenyl, acid anhydrides including maleic anhydride and phthalic anhydride, and aromatic amines such as metaphenylenediamine, diaminodiphenylmethane, and diaminodiphenyl sulfone. Preferably, the curing agent may be a zylok phenolic compound or a phenol aralkyl phenolic compound.

[0046] The curing agent may be contained in the epoxy resin composition in an amount of 0.5 to 13% by weight, which can prevent a decrease in the curability of the composition.

[0047] inorganic fillers The inorganic filler can improve the mechanical properties of the epoxy resin composition and reduce stress. Furthermore, in the present invention, the inorganic filler can increase the thermal conductivity of the cured product, enhance the heat dissipation effect, improve the fluidity of the epoxy resin composition, and reduce the thermal expansion and moisture absorption of the cured product.

[0048] The inorganic filler may 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.

[0049] Preferably, the inorganic filler can include alumina, which has a thermal conductivity of 25 W / m·K to 30 W / m·K and can easily improve the thermal conductivity of the composition.

[0050] The shape of the alumina is not limited, and may be spherical or non-spherical. A spherical shape can improve the fluidity of the composition. The average particle size (D50) of the alumina may be 0.5 μm to 50 μm, preferably 0.5 μm to 30 μm. By adopting the above range, the fluidity and thermal conductivity can be improved. In one specific example, the alumina may include a mixture of two types of alumina having different average particle sizes (D50). For example, the alumina may be mixed in a weight ratio of 1:1 to 10:1 between the first alumina and the second alumina, and the average particle size (D50) of the first alumina may be larger than the average particle size (D50) of the second alumina. If necessary, the alumina may be pre-coated with an epoxy compound or a curing agent before being included in the composition.

[0051] The amount of inorganic filler used varies depending on the required physical properties, such as thermal conductivity, moldability, stress reduction, and high-temperature strength. In one specific example, the inorganic filler may be contained in the epoxy resin composition in an amount of 50 to 95% by weight, specifically 70 to 95% by weight, and more specifically 85 to 95% by weight. By adopting this range, the flame retardancy and flowability of the epoxy resin composition and the reliability of the cured product can be ensured.

[0052] curing catalyst The curing catalyst may be a tertiary amine compound, an organometallic compound, an organophosphorus compound, an imidazole compound, or a boron compound. Examples of tertiary amine compounds include benzyldimethylamine, triethanolamine, triethylenediamine, diethylaminoethanol, tri(dimethylaminomethyl)phenol, 2-2-(dimethylaminomethyl)phenol, 2,4,6-tris(diaminomethyl)phenol, and tri-2-ethylhexyl salt. Examples of organometallic compounds include chromium acetylacetonate, zinc acetylacetonate, and nickel acetylacetonate. Examples of organophosphorus compounds include triphenylphosphine, tris-4-methoxyphosphine, triphenylphosphine triphenylborane, and triphenylphosphine-1,4-benzoquinone adduct. Examples of imidazole compounds include 2-methylimidazole, 2-phenylimidazole, 2-aminoimidazole, 2-methyl-1-vinylimidazole, 2-ethyl-4-methylimidazole, and 2-heptadecylimidazole. Examples of boron compounds include triphenylphosphine tetraphenylborate, tetraphenylboron salts, trifluoroborane-n-hexylamine, trifluoroborane monoethylamine, tetrafluoroborane triethylamine, and tetrafluoroborane amine. Other compounds that can be used include 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and phenol novolac resin salts.

[0053] As the curing catalyst, an adduct obtained by first reacting with an epoxy compound or a curing agent can also be used.

[0054] The curing catalyst may be contained in the epoxy resin composition in an amount of 0.01 to 5% by weight, which ensures the fluidity of the composition without increasing the curing reaction time.

[0055] The epoxy resin composition may further include typical additives that may be included in epoxy resin compositions for encapsulating semiconductor devices. In one embodiment, the additives may include one or more of a coupling agent, a release agent, a colorant, a stress relief agent, a crosslinking enhancer, and a leveling agent.

[0056] The coupling agent is used to improve the interfacial strength by reacting between the epoxy compound and the inorganic filler, and may be, for example, a silane coupling agent. The silane coupling agent may be any agent that reacts between the epoxy compound and the inorganic filler to improve the interfacial strength between the epoxy compound and the inorganic filler, and the type is not particularly limited. Specific examples of silane coupling agents include epoxysilane, aminosilane, ureidosilane, mercaptosilane, and alkylsilane. The coupling agent may be used alone, or multiple types of coupling agents may be used in combination. The coupling agent may be contained in the epoxy resin composition for encapsulating semiconductor elements in an amount of 0.01% by weight to 5% by weight, preferably 0.05% by weight to 3% by weight. By adopting the above range, the strength of the cured product can be improved.

[0057] The release agent may be 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, and may be contained in an amount of 0.1 to 1% by weight in the epoxy resin composition.

[0058] Carbon black can be used as the colorant, and the colorant may be contained in the epoxy resin composition in an amount of 0.1 to 1% by weight.

[0059] The stress relaxation agent may be at least one selected from the group consisting of modified silicone oil, silicone elastomer, silicone powder, and silicone resin, but is not limited thereto. The stress relaxation agent may be contained in the epoxy resin composition in an amount of 0 to 2% by weight, for example, 0 to 1% by weight, particularly 0.1 to 1% by weight.

[0060] The additive may be included in the epoxy resin composition at 0.1 wt % to 5 wt %, for example, 0.1 wt % to 3 wt %.

[0061] The method for producing the epoxy resin composition is not particularly limited. The epoxy resin composition may be produced by uniformly mixing the components contained in the composition using a Henschel mixer or a Loedige mixer, melt-kneading the mixture at 90°C to 120°C using a roll mill or a kneader, and then cooling and pulverizing the mixture.

[0062] Semiconductor devices are encapsulated using the epoxy resin composition for encapsulating semiconductor devices of the present invention. Methods for encapsulating semiconductor devices using the epoxy resin composition include, but are not limited to, transfer molding, injection molding, casting molding, and compression molding. In one embodiment, the semiconductor device of the present invention may be encapsulated by low-pressure transfer molding, and in another embodiment, by compression molding. [Example]

[0063] The present invention will be described in more detail with reference to preferred embodiments thereof below, however, these are merely preferred examples of the present invention and should not be construed as limiting the present invention in any way.

[0064] Preparation Example 1: Preparation of epoxy compound A1 [ka]

[0065] A 500 mL microwave reactor (CEM Co., Discover) was charged with 100 mL of DMF (dimethylformamide), 37.2 g of 4,4'-dihydroxybiphenyl, and 15 g of triethylene glycol, followed by 20 mL of triethylamine. The reaction was carried out at 150 W and 150°C for 1 hour. The solvent was then removed under reduced pressure, and the residue was purified by silica gel column chromatography using 1:6 ethyl acetate / hexane as the eluent to obtain 38 g of a solid powder (78% yield). This solid powder, benzyltrimethylammonium bromide (5.0 g), and excess epichlorohydrin (300 mL) were placed in a 500 mL reactor and reacted at 110°C for 1 hour. NaOH (6 g) was then added and the reaction continued for another 2 hours. After the reaction was complete, the solvent was removed under reduced pressure, and the residue was purified with deionized water to yield 37 g of a semi-solid compound in a 62% yield. NMR, LC-MS, and elemental analysis confirmed that this compound was epoxy compound A1.

[0066] 1 H NMR(400MHz,DMSO-d6):7.52-7.46(m,4H), 7.43-7.37(m,4H), 7.03-6.93(m,4H), 6.89-6.78(m,4H), 4.20(m,2H)4. 14-4.01(m,4H), 3.90(m,2H)3.81-3.73(m,4H), 3.48-3.44(m,4H), 3.33(m,2H), 2.75(m,2H), 2.61(m,2H)ppm;LC-MS m / z=598(M + );Anal.Calcd for C 36 H 38 O8:C, 72.22;H, 6.40;Found:C, 72.38;H, 6.46

[0067] Preparation Example 2: Preparation of epoxy compound A2 [ka]

[0068] A 500 mL microwave reactor (CEM Co., Discover) was charged with 100 mL of DMF (dimethylformamide), 40.4 g of 4,4'-dihydroxydiphenyl ether, and 15 g of triethylene glycol. Then, 20 mL of triethylamine was added and the mixture was reacted at 150 W and 150 °C for 1 hour. The solvent was then removed under reduced pressure, and the residue was purified by silica gel column chromatography using ethyl acetate / hexane (1:6) as the eluent to obtain 42 g of solid powder (82% yield). This solid powder, 5.0 g of benzyltrimethylammonium bromide, and an excess of epichlorohydrin (300 mL) were added to the 500 mL reactor and reacted at 110 °C for 1 hour. Then, 6 g of NaOH was added, and the mixture was reacted for another 2 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the residue was purified with deionized water to obtain 44 g of a semi-solid compound in 70% yield. NMR, LC-MS, and elemental analysis confirmed that this compound was epoxy compound A2.

[0069] 1 H NMR(400MHz,DMSO-d6):6.94-6.68(m,16H), 4.21(m,2H)4.15-4.01(m,4H), 3.92(m,2H) 3.80-3.72(m,4H), 3.48-3.44(m,4H), 3.30(m,2H), 2.75(m,2H), 2.59(m,2H)ppm;LC-MS m / z=630(M + );Anal.Calcd for C 36 H 38 O 10 :C, 68.56;H, 6.07;Found:C, 68.78;H, 6.28

[0070] Preparation Example 3: Preparation of epoxy compound A3 [ka]

[0071] A 500 mL microwave reactor (CEM Co., Discover) was charged with 100 mL of DMF (dimethylformamide), 37.2 g of 4,4'-dihydroxybiphenyl, and 19 g of tripropylene glycol, followed by 20 mL of triethylamine. The mixture was reacted at 150 W and 150 °C for 1 hour, after which the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate / hexane (1:6) as the eluent to obtain 30 g of a solid powder (57% yield). This solid powder, 5.0 g of benzyltrimethylammonium bromide, and an excess of epichlorohydrin (300 mL) were added to a 500 mL reactor and reacted at 110 °C for 1 hour. NaOH (6 g) was then added, and the mixture was reacted again for 2 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the residue was purified with deionized water to obtain 31 g of semi-solid compound in a 48% yield. NMR, LC-MS, and elemental analysis confirmed that this compound was epoxy compound A3.

[0072] 1 H NMR(400MHz,DMSO-d6):7.50-7.45(m,4H), 7.43-7.37(m,4H), 7.02-6.92(m,4H), 6.88-6.76(m,4H), 4.20(m,2H), 3.95( LC-MS m / z=640(M + );Anal.Calcd for C 39 H 44 O8:C, 73.10;H, 6.92;Found:C, 73.54;H, 6.62

[0073] Preparation Example 4: Preparation of epoxy compound A4 [ka]

[0074] A 500 mL microwave reactor (CEM Co., Discover) was charged with 100 mL of DMF (dimethylformamide), 4,4'-dihydroxybiphenyl ether (40.4 g), and tripropylene glycol (19 g), followed by 20 mL of triethylamine. The mixture was reacted at 150 W and 150 °C for 1 hour, after which the solvent was distilled off. The residue was purified by silica gel column chromatography using ethyl acetate / hexane (1:6) as the eluent to obtain 31 g of a solid powder (54% yield). This solid powder, benzyltrimethylammonium bromide (5.0 g), and an excess of epichlorohydrin (300 mL) were added to a 500 mL reactor and reacted at 110 °C for 1 hour. NaOH (6 g) was then added, and the mixture was reacted again for 2 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was purified with deionized water to obtain 31 g of a semi-solid compound in 45% yield. Through NMR, LC-MS and elemental analysis, this compound was confirmed to be epoxy compound A4.

[0075] 1 H NMR(400MHz,DMSO-d6):6.94-6.68(m,16H), 4.20(m,2H), 3.95(m,2H), 3.94-3.90(m,4H), 3. 58-3.40(m,8H), 3.23(m,2H), 2.75(m,2H), 2.41(m,2H), 1.89(m,4H), 1.68(m,2H)ppm;LC-MS m / z=672(M + );Anal.Calcd for C 39 H 44 O 10 :C, 69.63;H, 6.59;Found:C, 69.58;H, 6.37

[0076] The components used in the following examples and comparative examples are as follows.

[0077] (A) Epoxy compound (A1) Epoxy compound of Preparation Example 1 (A2) Epoxy compound of Preparation Example 2 (A3) Epoxy compound of Preparation Example 3 (A4) Epoxy compound of Preparation Example 4 (A5) Epoxy compounds of the following chemical formula [ka] (A6) Biphenyl-type epoxy compound (NC-3000, Nippon Kayaku Co., Ltd.)

[0078] (B) Hardener (B1) KPH-F3065 (Zylok type phenolic resin, Kolon Chemical Co.) (B2) MEH-7851 (phenol aralkyl type phenolic resin, Meiwa Co., Ltd.)

[0079] (C) Curing catalyst Triphenylphosphine (Hokko Chemical)

[0080] (D) Inorganic filler A 9:1 weight ratio 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.

[0081] (E) Coupling Agent (E1) Methyltrimethoxysilane (SZ-6070, Dow Corning) (E2) KBM-573 (N-phenyl-3-aminopropyltrimethoxysilane, Shinetsu)

[0082] (F) Carbon black (MA-600B, Mitsubishi Chemical Co., Ltd.)

[0083] Examples 1 to 5 and Comparative Examples 1 to 4 The above-mentioned components were uniformly mixed at 25-30°C for 30 minutes using a Henschel mixer (KEUM SUNG MACHINERY CO., LTD, KSM-22) according to the composition (unit: parts by weight) in Table 1 below, and then melt-kneaded at a maximum of 110°C for 30 minutes using a continuous kneader, cooled to 10-15°C, and pulverized to prepare an epoxy resin composition for encapsulating a semiconductor device. In Table 1 below, "-" means that the corresponding component was not included.

[0084] The prepared epoxy resin compositions for sealing semiconductor elements and the cured products were evaluated for the following physical properties, and the results are shown in Table 1.

[0085] (1) Fluidity (unit: inch, spiral flow): Using a low-pressure transfer molding machine, conforming to EMMI-1-66, mold temperature 175°C, 70 kgf / cm 2 The epoxy resin composition for sealing semiconductor elements was injected into a mold for measuring fluidity under conditions of an injection pressure of 9 MPa and a curing time of 90 seconds, and the flow length was measured. The higher the measurement value, the better the fluidity.

[0086] (2) Toughness (unit: kgf / mm 2 ): The toughness was measured at 25°C using a UTM (Universal Testing Machine) on a standard test piece (125 mm wide x 12.6 mm long x 6.4 mm thick) prepared from an epoxy resin composition for sealing semiconductor elements in accordance with ASTM D-790 and cured at 175°C for 4 hours.

[0087] (3) Thermal conductivity (unit: W / m K): Thermal conductivity was measured at 25°C by preparing test specimens from the epoxy resin composition in accordance with ASTM D5470. Specifically, the epoxy resin composition was injected into a transfer molding machine under the following conditions: mold temperature 175°C, injection pressure 9 MPa, and curing time 120 seconds to prepare thermal conductivity test specimens. Thermal conductivity was measured at 25°C using a flash laser type thermal conductivity meter (LFA467, manufactured by Netzsh).

[0088] (4) Reliability (unit: piece): Semiconductor packages for evaluation, fabricated using the epoxy resin composition for semiconductor element encapsulation, were dried at 125°C for 24 hours and then subjected to five cycles of thermal shock testing (each cycle consisting of 10 minutes at -65°C, 10 minutes at 25°C, and 10 minutes at 150°C). The packages were then left at 85°C and 60% relative humidity for 168 hours, and then subjected to preconditioning conditions, including one 30-second IR reflow at 260°C, repeated three times. The packages were then examined for external cracking using an optical microscope. The presence of delamination between the cured epoxy resin composition and the lead frame was then evaluated using scanning acoustic microscopy (C-SAM), a nondestructive testing method. The presence of external cracking or delamination between the cured epoxy resin composition and the package indicates that the package is not reliable.

[0089] [Table 1]

[0090] As shown in Table 1, it was found that the epoxy resin compositions for encapsulating semiconductor elements of the Examples have excellent heat dissipation effects due to high thermal conductivity of the cured product, and excellent crack prevention effects due to excellent fluidity.

[0091] On the other hand, the cured product obtained from the comparative example composition containing an epoxy compound with a structure different from that of the epoxy compound of Chemical Formula 1 had lower thermal conductivity than the examples and was also less reliable due to the occurrence of cracks.

[0092] Simple variations and modifications of the present invention can be easily implemented by those skilled in the art, and all such variations and modifications can be considered to be included within the scope of the present invention.

Claims

1. Contains an epoxy compound, a curing agent, an inorganic filler and a curing catalyst, The epoxy compound includes an epoxy compound represented by the following Chemical Formula 1: 【Chemical 1】 In the above Chemical Formula 1, A is an ethylene or propylene group; n is an integer from 1 to 10; T １ , T ２ each independently represents a single bond, —O—, or —S—; T ３ , T ４ are each independently represented by the following chemical formula 2: 【Chemistry 2】 In the above Chemical Formula 2, * is the linking site of the element, B is a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms; In the above Chemical Formula 1, Ra, Rb, Rc, and Rd each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 10 carbon atoms; m1 and m2 each independently represent an integer of 0 to 4; m3 and m4 each independently represent an integer of 0 to 4.

2. The epoxy compound of Formula 1 includes at least one of the following Formulas 3 and 4: 【Chemistry 3】 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein in Formula 3 and Formula 4, Ra', Rb', Rc', and Rd' each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and A, m1, m2, m3, m4, and n are the same as defined in Formula 1.

3. 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein the epoxy compound of Formula 1 comprises at least one of the epoxy compounds of Formulas 5 to 8: 【Chemistry 4】

4. 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein the epoxy compound of Formula 1 is contained in the epoxy resin composition in an amount of 0.1 to 17 wt %.

5. 2. The epoxy resin composition for sealing semiconductor elements according to claim 1, wherein the inorganic filler comprises alumina.

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

7. A semiconductor element sealed with the epoxy resin composition for sealing semiconductor elements according to any one of claims 1 to 6.

Images