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 provides high toughness for enhanced crack resistance.SOLUTION: An epoxy resin composition for semiconductor element sealing comprises an epoxy resin, a curing agent, an inorganic filler, a curing catalyst, and an additive, the additive comprising a compound represented by the following formula (where A represents a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; R1 and R2 each independently represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms; R3 and R4 each independently represent a single bond or a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms; T1 and T2 each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; and n1 and n2 each independently represent an integer of 1 or more).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] As electronic devices are becoming smaller, lighter, and more powerful, the integration density of semiconductors is also accelerating every year. As the demand for surface mounting of semiconductor devices increases, problems that cannot be solved with conventional epoxy resin compositions arise. Low shrinkage and low elasticity are required to solve problems such as package warpage caused by thermal expansion and contraction between the substrate and the epoxy resin composition, and chip breakage and defects caused by highly elastic cured products.

[0003] The reliability of epoxy molding compounding (EMC) ensures the excellence of semiconductors in their operating environment. Unreliable EMC can cause external cracks in semiconductors, making them unusable. To improve EMC reliability, it is necessary to improve the toughness of the epoxy resin composition and achieve high elasticity to increase crack resistance. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Publication No. 10-2023-0044982 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide an epoxy resin composition for sealing semiconductor elements that provides high toughness and thereby has a crack-reducing effect. [Means for solving the problem]

[0006] According to one embodiment, there is provided an epoxy resin composition for encapsulating a semiconductor device.

[0007] The epoxy resin composition for encapsulating a semiconductor device includes an epoxy resin, a curing agent, an inorganic filler, a curing catalyst, and an additive, and the additive includes a compound represented by the following Chemical Formula 1: [Chemical formula 1] [ka] (In the above Chemical Formula 1, A is a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R1 and R2 each independently represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms; R3 and R4 each independently represent a single bond or an unsubstituted or unsubstituted alkylene group having 1 to 5 carbon atoms; T1 and T2 each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; n1 and n2 are each independently an integer of 1 or greater.

[0008] According to one embodiment, a semiconductor device is provided.

[0009] The semiconductor element is sealed with the epoxy resin composition for sealing a semiconductor element. [Effects of the Invention]

[0010] The present invention can provide an epoxy resin composition for encapsulating semiconductor elements that has high toughness and thus has a crack-reducing effect. DETAILED DESCRIPTION OF THE INVENTION

[0011] Although the present invention may be embodied in many different forms, it is not intended to be limited to the embodiments set forth herein.

[0012] 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.

[0013] In this specification, when describing a range of values, "X to Y" means X or more and Y or less.

[0014] 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.

[0015] As used herein, the term "cycloalkylene group" refers to a chemical group obtained by removing one or more hydrogen atoms from a monocyclic or polycyclic compound having 3 to 20 carbon atoms and containing one or more cycloalkyl groups, or a derivative thereof. For example, the cycloalkylene group may be a cyclohexylene group or a cyclopentylene group.

[0016] As used herein, the term "arylene group" refers to a chemical group obtained by removing two or more hydrogen atoms from a monocyclic or polycyclic compound having 6 to 20 carbon atoms and containing one or more benzene rings, or a derivative thereof. For example, the monocyclic or polycyclic compound containing a benzene ring may include a benzene ring, toluene or xylylene having an alkyl side chain attached to the benzene ring, biphenyl having two or more benzene rings bonded by a single bond, fluorene, xanthene or anthraquinone having a benzene ring fused with a cycloalkyl group or heterocycloalkyl group, naphthalene or anthracene having two or more benzene rings fused, etc.

[0017] The epoxy resin composition contains a compound represented by the following Chemical Formula 1: [Chemical formula 1] [ka] (In the above Chemical Formula 1, A is a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R1 and R2 each independently represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms; R3 and R4 each independently represent a single bond or a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms; T1 and T2 each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; n1 and n2 are each independently an integer of 1 or more.

[0018] Epoxy resin compositions with a high inorganic filler content have low cure shrinkage and thermal expansion coefficients, but may have low toughness after curing. Low toughness can cause damage and cracks in semiconductors when subjected to external impact or during reliability testing. When applied to epoxy resin compositions with a high inorganic filler content, the compound represented by Chemical Formula 1 can significantly increase toughness, thereby improving crack resistance and rigidity. In addition, the compound represented by Chemical Formula 1 can maintain low cure shrinkage, low expansion coefficient, and high elastic modulus due to the high inorganic filler content.

[0019] The compound represented by Chemical Formula 1 is an amide-based compound having two or more terminal carboxylic acid groups, and can provide the effect of increasing the toughness of the epoxy resin composition after curing.

[0020] In one embodiment, A in Chemical Formula 1 may be a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. For example, A may be a substituted or unsubstituted cyclopentylene group, a substituted or unsubstituted cyclohexylene group, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenylene group.

[0021] In one embodiment, T1 and T2 in Chemical Formula 1 may each independently be a substituted or unsubstituted alkylene group having 3 to 8 carbon atoms or an alkylene group having 4 to 8 carbon atoms.

[0022] In one embodiment, R3 and R4 in Chemical Formula 1 may be the same or different and may be a single bond or a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms. Here, the "single bond" refers to a chemical bond in which A and nitrogen (N) in Chemical Formula 1 are directly bonded.

[0023] In one embodiment, R1 and R2 in Chemical Formula 1 may be the same or different and may be hydrogen or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, preferably hydrogen.

[0024] In one embodiment, n1 and n2 in Chemical Formula 1 may be the same or different and may be an integer of 1 to 5, or an integer of 1 to 3.

[0025] The compound of Chemical Formula 1 may include one or more compounds of Chemical Formula 2 and Chemical Formula 3 below. [Chemical formula 2] [ka] (In Chemical Formula 2, R1, R2, R3, R4, T1, and T2 are each the same as defined in Chemical Formula 1; Ra and Rb each independently represent 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; n3 and n4 each independently represent an integer of 1 or more, m1 and m2 are each independently an integer of 0 or greater.

[0026] In one embodiment, Ra and Rb may each be a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0027] In one embodiment, n3 and n4 may each independently be an integer of 1 to 11, or 1 to 6.

[0028] In one embodiment, m1 and m2 may each independently be an integer of 0 to 10, or an integer of 0 to 6.

[0029] [Chemical formula 3] [ka] (In Chemical Formula 3, R1, R2, R3, R4, T1, and T2 are the same as defined in Chemical Formula 1, Ra and Rb each independently represent 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; n5 and n6 are each independently an integer of 1 or greater, and m3 and m4 are each independently an integer of 0 or greater.

[0030] In one embodiment, Ra and Rb may each be a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0031] In one embodiment, n5 and n6 may each independently be an integer of 1 to 5, or an integer of 1 to 3.

[0032] In one embodiment, m3 and m4 may each independently be an integer of 0 to 4, or an integer of 0 to 2.

[0033] For example, the compound represented by Chemical Formula 1 may include one or more compounds selected from the following Chemical Formulas 4 to 7. [Chemical formula 4] [ka] [Chemical formula 5] [ka] [Chemical formula 6] [ka] [Chemical formula 7] [ka]

[0034] The epoxy resin composition may contain one or more compounds represented by Chemical Formula 1.

[0035] The compound represented by Chemical Formula 1 may be contained in the epoxy resin composition in an amount of 0.5 to 5% by weight. This range can provide the effect of increasing toughness. Preferably, the compound represented by Chemical Formula 1 may be contained in the epoxy resin composition in an amount of 0.8 to 3% by weight.

[0036] The epoxy resin composition further comprises an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst.

[0037] Epoxy resin The epoxy resin has two or more epoxy groups in the molecule and may be a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a phenol novolac type epoxy resin, a tert-butylcatechol type epoxy resin, a naphthalene type epoxy resin, a glycidylamine type epoxy resin, a cresol novolac type epoxy resin, a biphenyl type epoxy resin, a phenol aralkyl type epoxy resin, a linear aliphatic epoxy resin, an alicyclic epoxy resin, a heterocyclic epoxy resin, a spiro ring-containing epoxy resin, a cyclohexanedimethanol type epoxy resin, a trimethylol type epoxy resin, or a halogenated epoxy resin. Preferably, the epoxy resin may be a biphenyl type epoxy resin or a phenol aralkyl type epoxy resin. The epoxy resin may be used alone or in a mixture of two or more types.

[0038] 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, in which case the curability of the composition will not decrease.

[0039] hardener Examples of curing agents include polyfunctional phenolic resins, phenol aralkyl phenolic resins, phenol novolac phenolic resins, Xylok phenolic resins, cresol novolac phenolic resins, naphthol phenolic resins, terpene phenolic resins, dicyclopentadiene-based phenolic resins, novolac phenolic resins 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 Xylok phenolic resin or a phenol aralkyl phenolic resin.

[0040] The curing agent may be contained in the epoxy resin composition in an amount of 0.5% by weight to 13% by weight, in which case the curability of the composition will not decrease.

[0041] inorganic fillers The inorganic filler can improve the mechanical properties of the epoxy resin composition and can further reduce stress.

[0042] 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.

[0043] Preferably, the inorganic filler can contain fused silica, which has a low linear expansion coefficient to reduce stress. Fused silica refers to amorphous silica with a true specific gravity of 2.3 or less, and can be produced by melting crystalline silica or synthesized from a variety of raw materials. The shape and particle size of the fused silica are not particularly limited, but a fused silica mixture containing 50% to 99% by weight of spherical fused silica with an average particle size of 5 μm to 30 μm and 1% to 50% by weight of spherical fused silica with an average particle size of 0.001 μm to 1 μm is preferably included in the inorganic filler at 40% to 100% by weight. Furthermore, the maximum particle size of the fused silica can be adjusted to any one of 45 μm, 55 μm, and 75 μm depending on the application.

[0044] The amount of inorganic filler used varies depending on the required physical properties, such as fluidity, low stress, and high-temperature strength. In an embodiment, 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. Within this range, the flame retardancy, fluidity, and reliability of the epoxy resin composition can be ensured.

[0045] 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.

[0046] As the curing catalyst, an adduct formed by a prior reaction with an epoxy resin or a curing agent can also be used.

[0047] The curing catalyst may be contained in the epoxy resin composition in an amount of 0.01 to 5% by weight, which ensures that the curing reaction time is not delayed and the fluidity of the composition is maintained.

[0048] The epoxy resin composition may further include additives included in the epoxy resin composition for encapsulating a semiconductor device, such as one or more of a coupling agent, a release agent, a colorant, a stress relief agent, a crosslinking promoter, and a leveling agent.

[0049] The coupling agent is used to improve the interfacial strength by reacting with the epoxy resin and the inorganic filler, and may be, for example, a silane coupling agent. The type of silane coupling agent is not particularly limited as long as it reacts with the epoxy resin and the inorganic filler to improve the interfacial strength between the epoxy resin and the inorganic filler. Specific examples of silane coupling agents include epoxysilane, aminosilane, ureidosilane, mercaptosilane, and alkylsilane. The coupling agents can be used alone or 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. Within this range, the strength of the cured product of the epoxy resin composition can be improved.

[0050] 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. The release agent may be contained in the epoxy resin composition in an amount of 0.1 to 1% by weight.

[0051] 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% by weight to 1% by weight.

[0052] 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.

[0053] The additive may be contained in the epoxy resin composition in an amount of 0.1% by weight to 5% by weight, for example, 0.1% by weight to 3% by weight.

[0054] The method for producing the epoxy resin composition is not particularly limited, but the composition may be produced by uniformly mixing the components contained in the composition using a Henschel mixer or a Loedige mixer, melt-kneading the components at 90°C to 120°C using a roll mill or a kneader, and then cooling and pulverizing the components.

[0055] 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]

[0056] The structure and operation of the present invention will be described in more detail below through preferred examples of the present invention, which are presented as preferred examples of the present invention and should not be construed as limiting the present invention in any way.

[0057] Preparation Example 1: Preparation of Compound of Formula 4 The compound of the above formula 4 was prepared according to the following reaction scheme 1.

[0058] [Reaction Scheme 1] [ka]

[0059] Sebacic acid (40.4 g, 2 equivalents), isophoronediamine (15.6 g, 1 equivalent), and 200 ml of ethanol were placed in a round-bottom flask and stirred at 60° C. for 6 hours. The resulting reaction mixture was cooled to room temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove excess ethanol, yielding 50.1 g of the compound of formula 4 in a 94% yield. NMR confirmed the production of the compound of formula 4. 1 H NMR (400MHz, CDCl3) 4.43(t,1H), 3.41(br.s,2H), 2.77(br.s,4H), 2.55(t,4H), 1.68-1. 98(m,10H), 1.30-1.56(m,19H), 1.23-1.30(m,4H), 1.20(br.s,3H), 1.08(br.s,3H)ppm; 13 C NMR (100MHz, CDCl3)177.3, 172.4, 172.2, 49.1, 48.1, 45.1, 43.0, 36.8, 36.5, 36.1 , 29.4, 29.2, 29.1, 29.0, 28.7, 28.6, 27.9, 27.8, 25.7, 24.8, 24.6, 22.8, 22.4, 18.3 ppm;LC-MS m / z=539(M + );Anal.Calcd for C 30 H 54 N2O6:C, 66.88;H, 10.10;N, 5.20;Found:C, 66.49;H, 10.17;N, 5.33

[0060] Preparation Example 2: Preparation of Compound of Formula 5 [Chemical formula 5] [ka]

[0061] Sebacic acid (300 mmol, 2 equivalents), 3-amino-5-methylbenzenemethanamine (13.6 g, 1 equivalent), and 200 ml of ethanol were placed in a round-bottom flask and stirred at 60°C for 6 hours. The resulting reaction mixture was cooled to room temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40°C) to remove excess ethanol, yielding 47.8 g of the compound of Formula 5 in a 95% yield. NMR confirmed the production of the compound of Formula 5. 1 H NMR (400MHz, CDCl3) 11.1 (br.s, 2H), 7.81 (br s,2H), 7.25(s,1H), 7.20(s,1H), 6.60(s,1H), 4.46(s,2H), 2.35(s,3H), 2.23-2.18(m,8H), 1.67-1.56(m,8H), 1.30-128(m,16)ppm; 13 C NMR (100MHz, CDCl3)177.3, 172.4, 172.2, 141.8, 138.4, 138.2, 124.4, 119.3, 116.2 , 44.4, 36.5, 36.3, 36.1, 29.4, 29.2, 29.1, 28.7, 27.9, 25.7, 25.6, 24.9, 24.8, 24.6 ppm;LC-MS m / z=504.1(M + );Anal.Calcd for C 28 H 44 N2O6:C, 66.64;H, 8.79;N, 5.51;Found:C, 66.58;H, 9.01;N, 5.84

[0062] Preparation Example 3: Preparation of Compound of Formula 6 [Chemical formula 6] [ka]

[0063] Adipic acid (30.0 g, 2 equivalents), isophoronediamine (15.6 g, 1 equivalent), and 200 ml of ethanol were placed in a round-bottom flask and stirred at 60° C. for 6 hours. The resulting reaction mixture was cooled to room temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove excess ethanol, yielding 35.4 g of the compound of formula 6 in an 83% yield. NMR confirmed that the compound of formula 6 had been produced. 1 H NMR (400MHz, CDCl3) 11.1(br.s,2H), 7.81(brs,2H), 7.25(s,1H), 3.54(m,1H), 3.24(m,1H), 2.99(m,1H), 2. 23-2.18(m,8H), 1.71-1.15(m,14H), 1.71-1.20(m,14H), 1.19(br.s,3H), 1.19(s,3H), 1.08(br.s,3H)ppm; 13 LC-MS m / z=426.2(M + );Anal.Calcd for C 22 H 38 N2O6:C, 61.95;H, 8.98;N, 6.57;Found:C, 61.59;H, 9.14;N, 6.35

[0064] Preparation Example 4: Preparation of Compound of Formula 7 [Chemical formula 7] [ka]

[0065] Sebacic acid (60.6 g, 3 equivalents), 1,3,5-cyclohexanetriamine (13.0 g, 1 equivalent), and 200 ml of ethanol were placed in a round-bottom flask and stirred at 60°C for 8 hours. The resulting reaction mixture was cooled to room temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40°C) to remove excess ethanol, yielding 50.1 g of the compound of formula 7 in a 94% yield. NMR confirmed the production of the compound of formula 7. 1 H NMR (400MHz, CDCl3) 11.1 (br s 3H), 7.9 (br s 3H), 3.54(m,3H), 2.20-2.17(m,12H), 2.01-1.75(m,6H), 1.58-1.55(m,12H), 1.30-1.25(m,24H)ppm; 13 C NMR (100MHz, CDCl3)177.3, 172.4, 41.9, 36.8, 36.1, 29.4, 29.1, 29.0, 28.7, 25.7, 24.8 ppm; LC-MS m / z=681(M + );Anal.Calcd for C 36 H 63 N3O9:C, 63.41;H, 9.31;N, 6.16;Found:C, 63.38;H, 9.46;N, 6.30

[0066] The specific specifications of the components used in the following examples and comparative examples are as follows: (A) Epoxy resin: phenol aralkyl epoxy resin (NC-3000, Nippon Kayaku Co., Ltd.) (B) Curing agent: MEH-7851 (phenol aralkyl type phenolic resin, Meiwa Co., Ltd.) (C) Curing catalyst: triphenylphosphine (Hokko Chemical Co.) (D) Inorganic filler: a 9:1 weight ratio mixture of spherical fused silica with an average particle size (D50) of 20 μm and spherical fused silica with an average particle size (D50) of 0.5 μm. (E) Additives: (E1) Compound of Chemical Formula 4, (E2) Compound of Chemical Formula 5, (E3) Compound of Chemical Formula 6, (E4) Compound of Chemical Formula 7 (F) Coupling agent (F1) Methyltrimethoxysilane (SZ-6070, Dow Corning) (F2) KBM-573 (N-phenyl-3-aminopropyltrimethoxysilane, Shinetsu) (G) Carbon black (MA-600B, Mitsubishi Chemical Co., Ltd.)

[0067] Examples 1 to 6 and Comparative Example 1

[0068] The epoxy resin compositions for semiconductor element encapsulation were prepared by uniformly mixing the components (unit: parts by weight) in Table 1 below using a Henschel mixer (KEUM SUNG MACHINERY CO. LTD, KSM-22) at 25-30°C for 30 minutes, then melt-kneading them using a continuous kneader at a maximum of 110°C for 30 minutes, cooling them to 10-15°C, and pulverizing them. In Table 1 below, "-" means that the corresponding component is not included.

[0069] The prepared epoxy resin compositions for sealing semiconductor elements were evaluated for the following physical properties, and the results are shown in Table 1 below.

[0070] (1) Fluidity (spiral flow): Using a low-pressure transfer molding machine, the fluidity measurement mold was measured at a mold temperature of 175°C and 70 kgf / cm in accordance with EMMI-1-66. 2 The epoxy resin composition for sealing semiconductor elements was injected 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 measured value, the better the flowability.

[0071] (2) Elastic modulus: The epoxy resin composition was cured using a transfer molding machine under conditions of a mold temperature of 90°C ± 5°C, an injection pressure of 1,000 psi ± 200 psi, and a cure time of 120 seconds to form test specimens (length × width × thickness, 20 mm × 13 mm × 1.6 mm). The test specimens were post-cured in a hot air oven at 90°C ± 5°C for 2 hours, and then the elastic modulus was measured using a dynamic mechanical analyzer (DMA) Q8000 (TA Corporation). The temperature was increased from -10°C to 300°C at a rate of 5°C / min, and the values ​​at 25°C and 260°C were used as storage modulus values.

[0072] (3) Toughness: Standard test pieces (125 mm wide x 12.6 mm thick x 6.4 mm long) were prepared using the epoxy resin composition for semiconductor element encapsulation in accordance with ASTM D-790, and then cured at 175°C for 4 hours. The toughness was measured by performing a three-point bending test on the test pieces at 25°C using a Universal Testing Machine (UTM).

[0073] (4) Reliability: After drying a semiconductor package for evaluation made using the epoxy resin composition for sealing semiconductor elements at 125°C for 24 hours, it underwent a thermal shock test of 5 cycles (one cycle is the package being left at -65°C for 10 minutes, 25°C for 10 minutes, and 150°C for 10 minutes).The package was then left at 85°C and 60% relative humidity for 168 hours, and subjected to IR reflow at 260°C for 30 seconds once, which was repeated three times.After this preconditioning, the appearance of the package was observed with an optical microscope for the presence or absence of cracks.

[0074] [Table 1]

[0075] As shown in Table 1, the epoxy resin compositions for sealing semiconductor elements of the examples provided high toughness and were therefore excellent in crack prevention effects.

[0076] On the other hand, in the case of the composition of Comparative Example 1 which did not contain the compound represented by Chemical Formula 1, cracks occurred, and a semiconductor device with low reliability was provided.

[0077] 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 epoxy resin, hardener, inorganic filler, curing catalyst and additives, The epoxy resin composition for encapsulating semiconductor devices includes a compound represented by the following Chemical Formula 1: [Chemical formula 1] 【Chemical 1】 (In the above Chemical Formula 1, A is a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; R １ , R ２ are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, R ３ , R ４ are each independently a single bond or a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms, T １ , T ２ are each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, n1 and n2 are each independently an integer of 1 or more.

2. 2. The epoxy resin composition for encapsulating semiconductor devices according to claim 1, wherein the compound represented by Chemical Formula 1 is contained in the epoxy resin composition in an amount of 0.5 to 5% by weight.

3. 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein the compound represented by Formula 1 comprises at least one compound selected from the group consisting of Formulas 2 and 3: [Chemical formula 2] 【Chemistry 2】 (In the above Chemical Formula 2, R １ , R ２ , R ３ , R ４ , T １ , T ２ are the same as defined in Chemical Formula 1, Ra and Rb each independently represent 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; n3 and n4 each independently represent an integer of 1 or more, m1 and m2 are each independently an integer of 0 or greater. [Chemical formula 3] 【Chemistry 3】 (In the above Chemical Formula 3, R １ , R ２ , R ３ , R ４ , T １ , T ２ are the same as defined in Chemical Formula 1, Ra and Rb each independently represent 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; n5 and n6 each independently represent an integer of 1 or more; m3 and m4 are each independently an integer of 0 or more.

4. 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein the compound represented by Formula 1 comprises one or more compounds selected from the following Formulas 4 to 7: [Chemical formula 4] 【Chemistry 4】 [Chemical formula 5] 【Chemistry 5】 [Chemical formula 6] 【Chemistry 6】 [Chemical formula 7] 【Chemistry 7】

5. 2. The epoxy resin composition for encapsulating a semiconductor device according to claim 1, wherein the epoxy resin is included in an amount of 2 wt % to 17 wt %, the curing agent is included in an amount of 0.5 wt % to 13 wt %, the inorganic filler is included in an amount of 50 wt % to 95 wt %, the compound represented by Chemical Formula 1 is included in an amount of 0.5 wt % to 5 wt %, and the curing catalyst is included in an amount of 0.01 wt % to 5 wt %.

6. A semiconductor element sealed with the epoxy resin composition for sealing a semiconductor element according to any one of claims 1 to 5.

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