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

Abstract

Epoxy resin composition for encapsulating semiconductor device, epoxy resin composition comprising epoxy resin, curing agent, inorganic filler, curing catalyst, and additive comprising at least one compound represented by Formula 1 [Formula 1] # imgabs0 #, and semiconductor device encapsulated using epoxy resin composition, epoxy resin composition comprising epoxy resin, curing agent, inorganic filler, curing catalyst, and additive comprising at least one compound represented by Formula 1 [Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0035274 filed in the Korean Intellectual Property Office on March 13, 2024, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] Various embodiments relate to an epoxy resin composition for encapsulating a semiconductor device and a semiconductor device encapsulated using the epoxy resin composition. Background Art

[0004] As electronic devices continue to become smaller, lighter, and offer higher performance, semiconductor integration is accelerating annually. The increasing demand for surface-mounted semiconductor devices presents challenges that conventional epoxy resin compositions cannot address. Low shrinkage and low elasticity are required to prevent issues such as package warping due to differential thermal expansion and contraction between the substrate and the epoxy resin composition, and semiconductor chip breakage or failure due to the high elasticity of the composition's cured product. Summary of the Invention

[0005] Each embodiment relates to an epoxy resin composition for encapsulating a semiconductor device, the epoxy resin composition comprising an epoxy resin, a curing agent, an inorganic filler, a curing catalyst, and an additive, wherein the additive comprises at least one compound represented by Formula 1:

[0006] [Formula 1]

[0007]

[0008] wherein A is a substituted or unsubstituted C3 to C 20 Cycloalkylene or substituted or unsubstituted C6 to C 20 Arylene, R1 and R2 are each independently hydrogen or a substituted or unsubstituted C1 to C5 alkyl group, R3 and R4 are each independently a single bond or a substituted or unsubstituted C1 to C5 alkylene group, T1 and T2 are each independently a substituted or unsubstituted C1 to C 10 alkylene, and n1 and n2 are each independently an integer greater than or equal to 1.

[0009] The at least one compound represented by Formula 1 may be included in the epoxy resin composition in an amount of 0.5 wt % to 5 wt % based on the total amount of the epoxy resin composition.

[0010] The additive comprising at least one compound represented by Formula 1 may comprise at least one compound represented by Formula 2 or Formula 3,

[0011] [Formula 2]

[0012]

[0013] wherein each of R1, R2, R3, R4, T1 and T2 may be defined as the same as in Formula 1, R a and R b may be independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 aryl, n3 and n4 may each independently be an integer greater than or equal to 1, and m1 and m2 may each independently be an integer greater than or equal to 0,

[0014] [Formula 3]

[0015]

[0016] wherein each of R1, R2, R3, R4, T1 and T2 may be defined as the same as in Formula 1, R a and R b may be independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 aryl group, n5 and n6 may each independently be an integer greater than or equal to 1, and m3 and m4 may each independently be an integer greater than or equal to 0.

[0017] The additive comprising at least one compound represented by Formula 1 may comprise at least one compound represented by Formula 4 to Formula 7,

[0018] [Formula 4]

[0019]

[0020] [Formula 5]

[0021]

[0022] [Formula 6]

[0023]

[0024] [Formula 7]

[0025]

[0026] The epoxy resin composition may include 2 wt % to 17 wt % of an epoxy resin, 0.5 wt % to 13 wt % of a curing agent, 50 wt % to 95 wt % of an inorganic filler, 0.5 wt % to 5 wt % of the at least one compound represented by Formula 1, and 0.01 wt % to 5 wt % of a curing catalyst, based on the total weight of the epoxy resin composition.

[0027] The embodiments may be achieved by providing a semiconductor device encapsulated using the epoxy resin composition according to some embodiments. DETAILED DESCRIPTION

[0028] Various exemplary embodiments will now be described more fully below; however, the exemplary embodiments may be embodied in different forms and should not be construed as limited to only the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey exemplary implementations to those skilled in the art.

[0029] It should also be understood that when a layer or element is referred to as being "on" another layer or substrate, the layer or element may be directly on the other layer or substrate, or intervening layers may also be present. Furthermore, it should be understood that when a layer is referred to as being "under" another layer, the layer may be directly under the other layer, and one or more intervening layers may also be present. Furthermore, it should be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intervening layers may also be present. Throughout, the same reference numbers refer to the same elements. As used herein, the term "or" is not exclusive; for example, "A or B" will include A, B, or A and B.

[0030] As used herein, "X to Y" to express a particular numerical range means "greater than or equal to X and less than or equal to Y."

[0031] The term "substituted" in the expression "substituted or unsubstituted" used herein means that at least one hydrogen atom of the corresponding functional group is replaced by a hydroxyl group, an amino group, a nitro group, a cyano group, a C1 to C 20 Alkyl, C1 to C 20 Halogenated alkyl, C6 to C 30 Aryl, C3 to C 30 Heteroaryl, C3 to C 10 Cycloalkyl, C3 to C 10 Heterocycloalkyl, C7 to C 30 Aralkyl, or C1 to C 30 Heteroalkyl substitution.

[0032] In this context, "cycloalkylene" refers to a monocyclic or polycyclic C3 to C4 group containing one or more cycloalkyl groups. 20A chemical group obtained by removing one or more hydrogen atoms from a compound or its derivative. For example, a cycloalkylene group may include cyclohexylene or cyclopentylene.

[0033] In this context, "arylene" refers to a monocyclic or polycyclic C6 to C6 containing one or more benzene rings. 20 A chemical group obtained by removing two or more hydrogen atoms from a compound or its derivative. For example, a monocyclic or polycyclic compound containing a benzene ring may include a toluene or xylene compound in which an alkyl side chain is attached to the benzene ring, a biphenyl compound in which two or more benzene rings are linked by a single bond, a fluorene, xanthene, or anthraquinone compound in which a benzene ring is fused with a cycloalkyl or heterocycloalkyl group, a naphthalene or anthracene compound in which two or more benzene rings are fused with each other, and the like.

[0034] According to one aspect of the present disclosure, the epoxy resin composition may include an additive including at least one compound represented by Formula 1.

[0035] [Formula 1]

[0036]

[0037] In Formula 1, A may be or include, for example, substituted or unsubstituted C3 to C 20 Cycloalkylene, or substituted or unsubstituted C6 to C 20 Arylene.

[0038] R1 and R2 may each independently be or include, for example, hydrogen or a substituted or unsubstituted C1 to C5 alkyl group.

[0039] R3 and R4 may each independently be or include, for example, a single bond or a substituted or unsubstituted C1 to C5 alkylene group.

[0040] T1 and T2 may each independently be or include, for example, substituted or unsubstituted C1 to C 10 Alkylene.

[0041] n1 and n2 may each independently be or include, for example, an integer greater than or equal to 1.

[0042] Although the epoxy resin composition with a high content of inorganic filler has a low cure shrinkage and a low thermal expansion coefficient, it may have low toughness after curing. If the semiconductor is subjected to external impact or reliability testing, the low toughness of the composition may cause damage and cracking of the semiconductor. If an additive comprising at least one compound represented by Formula 1 is used in an epoxy resin composition with a high content of inorganic filler, the additive can help improve the crack resistance and rigidity of the composition by significantly increasing the toughness of the composition. In one embodiment, an additive comprising at least one compound represented by Formula 1 may help provide the above-mentioned effects without sacrificing the low cure shrinkage, low thermal expansion coefficient and high modulus of the composition due to a high content of inorganic filler.

[0043] The at least one compound represented by Formula 1 may be, for example, an amide compound including two or more terminal carboxylic acid groups, and may contribute to improving the toughness of the epoxy resin composition after curing.

[0044] In one embodiment, in Formula 1, A may be, for example, a substituted or unsubstituted C3 to C 10 Cycloalkylene, or substituted or unsubstituted C6 to C 10 Arylene. In one embodiment, in Formula 1, A may be, for example, a substituted or unsubstituted cyclopentylene group, a substituted or unsubstituted cyclohexylene group, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthyl group.

[0045] In one embodiment, in Formula 1, T1 and T2 may each independently be, for example, a substituted or unsubstituted C3 to C8 alkylene group, or a substituted or unsubstituted C4 to C8 alkylene group.

[0046] In one embodiment, in Formula 1, R3 and R4 may be the same as or different from each other and may each independently be, for example, a single bond or a substituted or unsubstituted C1 to C3 alkylene group. Here, "single bond" may refer to a direct chemical bond between A and nitrogen (N) in Formula 1.

[0047] In one embodiment, in Formula 1, R1 and R2 may be the same as or different from each other, and may each independently be, for example, hydrogen or a substituted or unsubstituted C1 to C3 alkyl group, such as hydrogen.

[0048] In one embodiment, in Formula 1, n1 and n2 may be equal to or different from each other, and each may independently be an integer of, for example, 1 to 5 or an integer of 1 to 3.

[0049] The additive including at least one compound represented by Formula 1 may include at least one compound represented by Formula 2 or Formula 3.

[0050] [Formula 2]

[0051]

[0052] In Formula 2, each of R1, R2, R3, R4, T1, and T2 may be defined the same as in Formula 1,

[0053] R a and R b Each independently can be, for example, substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl.

[0054] n3 and n4 may each independently be, for example, an integer greater than or equal to 1.

[0055] m1 and m2 may each independently be, for example, an integer greater than or equal to 0.

[0056] In one embodiment, R a and R b Each of may be, for example, a substituted or unsubstituted C1 to C5 alkyl group.

[0057] In one embodiment, n3 and n4 may each independently be an integer from 1 to 11 or an integer from 1 to 6, for example.

[0058] In one embodiment, m1 and m2 may each independently be an integer from 0 to 10 or an integer from 0 to 6, for example.

[0059] [Formula 3]

[0060]

[0061] In Formula 3, each of R1, R2, R3, R4, T1, and T2 may be defined the same as in Formula 1.

[0062] R a and R b Each independently can be, for example, substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl.

[0063] n5 and n6 may each independently be, for example, an integer greater than or equal to 1.

[0064] m3 and m4 may each independently be, for example, an integer greater than or equal to 0.

[0065] In one embodiment, R a and R b Each of can independently be, for example, a C1 to C5 alkyl group.

[0066] In one embodiment, n5 and n6 may each independently be an integer of, for example, 1 to 5 or an integer of 1 to 3.

[0067] In one embodiment, m3 and m4 may each independently be, for example, an integer from 0 to 4 or an integer from 0 to 2.

[0068] In one embodiment, the additive including at least one compound represented by Formula 1 may include at least one compound represented by Formulas 4 to 7.

[0069] [Formula 4]

[0070]

[0071] [Formula 5]

[0072]

[0073] [Formula 6]

[0074]

[0075] [Formula 7]

[0076]

[0077] The epoxy resin composition may include one or more types of compounds represented by Formula 1.

[0078] The at least one compound represented by Formula 1 may be included in the epoxy resin composition in an amount of 0.5 wt % to 5 wt % based on the total weight of the epoxy resin composition. Maintaining the at least one compound represented by Formula 1 within this range may help ensure that the at least one compound represented by Formula 1 may help increase the toughness of the composition. In one embodiment, the at least one compound represented by Formula 1 may be included in the epoxy resin composition in an amount of 0.8 wt % to 3 wt % based on the total weight of the epoxy resin composition.

[0079] The epoxy resin composition may further include, for example, an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst.

[0080] epoxy resin

[0081] The epoxy resin may be, for example, an epoxy resin containing at least two epoxy groups in its molecular structure, and may include, for example, bisphenol A epoxy resin, bisphenol F epoxy resin, phenol novolac epoxy resin, tert-butyl catechol epoxy resin, naphthalene epoxy resin, glycidylamine epoxy resin, cresol novolac epoxy resin, biphenyl epoxy resin, phenol aralkyl epoxy resin, linear aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, spirocyclic epoxy resin, cyclohexanedimethanol epoxy resin, trimethylol epoxy resin, halogenated epoxy resin, etc. In one embodiment, the epoxy resin may include, for example, biphenyl epoxy resin or phenol aralkyl epoxy resin. These epoxy resins may be used alone or in the form of a mixture thereof.

[0082] The epoxy resin can be included in the epoxy resin composition in an amount of 2 wt % to 17 wt %, for example 2 wt % to 10 wt %, based on the total weight of the epoxy resin composition. Maintaining the amount of epoxy resin within these ranges can help ensure that the composition can avoid a decrease in curability.

[0083] curing agent

[0084] The curing agent may include, for example, multifunctional phenol resins, including aralkyl-type phenol resins, novolac-type phenol resins, xylok-type phenol resins, cresol-type phenol resins, naphthol-type phenol resins, terpene-type phenol resins, dicyclopentadiene phenol resins, and novolac-type phenol resins synthesized from bisphenol A or resol resins; polyphenol compounds, including, for example, tris(hydroxyphenyl)methane and dihydroxybiphenyl; acid anhydrides, including, for example, maleic anhydride and phthalic anhydride; and aromatic amines, including, for example, m-phenylenediamine, diaminodiphenylmethane, and diaminodiphenyl sulfone. In one embodiment, the curing agent may include, for example, a xylok-type phenol resin or an aralkyl-type phenol resin.

[0085] The curing agent may be included in the epoxy resin composition in an amount of 0.5 wt % to 13 wt % based on the total weight of the epoxy resin composition. Maintaining the amount of curing agent within this range can help ensure that the composition avoids a decrease in curability.

[0086] Inorganic fillers

[0087] Inorganic fillers can be used to help improve the mechanical properties of the epoxy resin composition while helping to reduce the internal stress of the epoxy resin composition.

[0088] The inorganic filler may include, for example, fused silica, crystalline silica, calcium carbonate, magnesium carbonate, aluminum oxide, magnesium oxide, clay, talc, calcium silicate, titanium oxide, antimony oxide, or glass fiber.

[0089] In one embodiment, the inorganic filler may include, for example, fused silica with a low linear expansion coefficient to reduce the internal stress of the epoxy resin composition. Here, fused silica may refer to, for example, amorphous silica having a true specific gravity of 2.3 or less than 2.3, and may include amorphous silica prepared by melting crystalline silica, or may be synthesized from various raw materials. In one embodiment, a fused silica mixture comprising 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 based on the total weight of the inorganic filler may be included in the inorganic filler in an amount of 40% to 100% by weight. In one embodiment, the maximum particle size of the fused silica may be, for example, adjusted to any one of 45 μm, 55 μm, or 75 μm according to its intended application.

[0090] In the composition, the content of inorganic filler can be changed according to the required property of composition (for example, thermal conductivity, moldability, low stress or high temperature intensity).In certain embodiments, with the gross weight of composition epoxy resin, inorganic filler can be included in composition epoxy resin with the amount of 50 wt % to 95 wt %, for example 70 wt % to 95 wt % or 85 wt % to 95 wt %.Maintaining the amount of inorganic filler in these scopes can help to ensure that composition epoxy resin can have good property in terms of flame retardancy, mobility and reliability.

[0091] Curing catalyst

[0092] The curing catalyst may include, for example, a tertiary amine compound, an organometallic compound, an organophosphorus compound, an imidazole compound or a boron compound. The tertiary amine compound may include, for example, benzyldimethylamine, triethanolamine, triethylenediamine, diethylaminoethanol, tris (dimethylaminomethyl) phenol, 2,2- (dimethylaminomethyl) phenol, 2,4,6-tris (diaminomethyl) phenol, tri-2-ethylhexanoate, etc. The organometallic compound may include, for example, chromium acetylacetonate, zinc acetylacetonate, nickel acetylacetonate, etc. The organophosphorus compound may include, for example, triphenylphosphine, tri-4-methoxyphosphine, triphenylphosphine-triphenylborane, triphenylphosphine-1,4-benzoquinone adduct, etc. The imidazole compound may include, for example, 2-methylimidazole, 2-phenylimidazole, 2-aminoimidazole, 2-methyl-1-vinylimidazole, 2-ethyl-4-methylimidazole, 2-heptadecylimidazole, etc. Boron compounds may include, for example, triphenylphosphine tetraphenylborate, tetraphenylboron salt, trifluoroborane-n-hexylamine, trifluoroborane monoethylamine, tetrafluoroborane triethylamine, tetrafluoroborane amine, etc. In one embodiment, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or phenol novolac resin salt may be used as a curing catalyst.

[0093] The curing catalyst may be included, for example, in the form of an adduct prepared by pre-reacting the curing catalyst with the epoxy resin or the curing agent.

[0094] The curing catalyst can be included in the epoxy resin composition in an amount of, for example, 0.01 wt % to 5 wt % based on the total weight of the epoxy resin composition. Maintaining the amount of the curing catalyst within this range can help ensure that the curing catalyst can help promote the curing of the composition without sacrificing the fluidity of the composition.

[0095] The epoxy resin composition may further include suitable additives for epoxy resin compositions for encapsulating semiconductor devices. In some embodiments, the additives may include, for example, coupling agents, release agents, colorants, stress relievers, crosslinking enhancers, or leveling agents.

[0096] The coupling agent can be used to increase the interfacial strength between the epoxy resin and the inorganic filler by reacting with the epoxy resin and the inorganic filler, and can include, for example, a silane coupling agent. The silane coupling agent can include any silane coupling agent that can increase the interfacial strength between the epoxy resin and the inorganic filler by reacting with the epoxy resin and the inorganic filler. The silane coupling agent can include, for example, epoxy silane, aminosilane, urea silane, mercapto silane, alkyl silane, etc. These coupling agents can be used alone or in combination. Based on the gross weight of the epoxy resin composition, the coupling agent can be included in the epoxy resin composition in an amount of 0.01 wt % to 5 wt %, for example, 0.05 wt % to 3 wt %. Maintaining the amount of the coupling agent within these ranges can help ensure that the cured product of the epoxy resin composition has enhanced strength.

[0097] The stripping agent may include, for example, paraffin wax, ester wax, higher fatty acid, metal salt of higher fatty acid, natural fatty acid and metal salt of natural fatty acid. The stripping agent may be included in the epoxy resin composition in an amount of 0.1 wt % to 1 wt % based on the total weight of the epoxy resin composition.

[0098] The colorant may include, for example, carbon black. The colorant may be included in the epoxy resin composition in an amount of 0.1 wt % to 1 wt % based on the total weight of the epoxy resin composition.

[0099] The stress reliever may include, for example, modified silicone oil, silicone elastomer, silicone powder, and silicone resin. The stress reliever may be included in the epoxy resin composition in an amount of 2 wt % or less, such as 1 wt % or less, or 0.1 wt % to 1 wt %, based on the total weight of the epoxy resin composition.

[0100] The additive may be included in the epoxy resin composition in an amount of 0.1 wt % to 5 wt %, for example, 0.1 wt % to 3 wt %, based on the total weight of the epoxy resin composition.

[0101] The mixture can be prepared, for example, by mixing in a Henschel mixer or a Roediger mixer. The epoxy resin composition is prepared by uniformly mixing the aforementioned components in a mixer, melt-kneading the mixture in a roll mill or a kneader at, for example, 90° C. to 120° C., and cooling and pulverizing the resultant product.

[0102] According to another aspect of the present disclosure, the semiconductor device can be encapsulated using the epoxy resin composition for encapsulating the semiconductor device according to the embodiment. The semiconductor device can be encapsulated using the epoxy resin composition by any suitable method (e.g., transfer molding, injection molding, casting, or compression molding). In one embodiment, the semiconductor device can be encapsulated using the epoxy resin composition by low pressure transfer molding. In another embodiment, the semiconductor device can be encapsulated using the epoxy resin composition by compression molding.

[0103] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it should be understood that the examples and comparative examples should not be interpreted as limiting the scope of the embodiments, nor should the comparative examples be interpreted as being outside the scope of the embodiments. It should also be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0104] Preparation Example 1: Preparation of the compound represented by Formula 4

[0105] The compound represented by Formula 4 was prepared according to Reaction Formula 1:

[0106]

[0107] Sebacic acid (40.4 g, 2 equivalents), isophorone diamine (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 obtained reaction mixture was cooled to ambient temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove the remaining ethanol, thereby obtaining 50.1 g of the compound represented by Formula 4 with a yield of 94%. Nuclear magnetic resonance (NMR) confirmed that the obtained product was the compound represented by Formula 4.

[0108] 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 45.1,43.0,36.8,36.5,36.1,29.4,29.2,29.1,29.0,28.7,28.6,27.9,27.8,25.7,24.8,24.6,22.8,22.4,18.3ppm; LC-MS m / z=539 (M + );C 30 H 54 Theoretical calculated values ​​of N2O6: C, 66.88; H, 10.10; N, 5.20; measured values: C, 66.49; H, 10.17; N, 5.33.

[0109] Preparation Example 2: Preparation of the compound represented by Formula 5

[0110]

[0111] Sebacic acid (300 mmol, 2 equivalents), 3-amino-5-methylbenzylamine (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 obtained reaction mixture was cooled to ambient temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove the remaining ethanol, thereby obtaining 47.8 g of the compound represented by Formula 5 with a yield of 95%. NMR confirmed that the obtained product was the compound represented by 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 CNMR (100MHz, CDCl3)177.3,172.4,172.2,141.8,138.4,138.2,124.4,119.3,116.2,44. 4,36.5,36.3,36.1,29.4,29.2,29.1,28.7,27.9,25.7,25.6,24.9,24.8,24.6ppm; LC-MS m / z=504.1(M + );C 28 H 44 Theoretical calculation values ​​of N2O6: C, 66.64; H, 8.79; N, 5.51; Found values: C, 66.58; H, 9.01; N, 5.84

[0112] Preparation Example 3: Preparation of the compound represented by Formula 6

[0113]

[0114] Adipic acid (30.0 g, 2 equivalents), isophorone diamine (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 obtained reaction mixture was cooled to ambient temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove the remaining ethanol, thereby obtaining 35.4 g of the compound represented by Formula 6 with a yield of 83%. NMR confirmed that the obtained product was the compound represented by Formula 6. 1H NMR(400MHz, CDCl3)11.1(br.s,2H),7.81(br s,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 C NMR (100MHz, CDCl3)177.3,172.4,49.1,48.1,45.0,43.0,37.4,36.5,36.2,35.4,27.9,27.8,25.1,25.0,23.8,23.7,22.8,22.4,18.3ppm; LC-MS m / z=426.2(M + );C 22 H 38 Theoretical calculation values ​​of N2O6: C, 61.95; H, 8.98; N, 6.57; Found values: C, 61.59; H, 9.14; N, 6.35

[0115] Preparation Example 4: Preparation of the compound represented by Formula 7

[0116]

[0117] 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 obtained reaction mixture was cooled to ambient temperature and then distilled under vacuum (pressure: 15 mbar, temperature: 40° C.) to remove the remaining ethanol, thereby obtaining 50.1 g of the compound represented by Formula 7 with a yield of 94%. NMR confirmed that the obtained product was the compound represented by 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, 24.8ppm; LC-MS m / z=681 (M + );C 36 H 63Theoretical calculated values ​​of N3O9: C, 63.41; H, 9.31; N, 6.16; measured values: C, 63.38; H, 9.46; N, 6.30.

[0118] The details of the components used in the Examples and Comparative Examples are as follows:

[0119] (A) Epoxy resin: phenol aralkyl epoxy resin (NC-3000, Nippon Kayaku Co., Ltd.)

[0120] (B) Curing agent: MEH-7851 (aralkyl type phenol resin, Meiwa Corporation)

[0121] (C) Curing catalyst: triphenylphosphine (Hokko Chemical Co., Ltd.)

[0122] (D) Inorganic filler: average particle size (D 50 ) is 20 μm and the average particle size (D 50 ) is a mixture of 0.5 μm spherical fused alumina (weight ratio: 9:1)

[0123] (E) Additives: (E1) a compound represented by Formula 4, (E2) a compound represented by Formula 5, (E3) a compound represented by Formula 6, (E4) a compound represented by Formula 7

[0124] (F) Coupling agent

[0125] (F1) Methyltrimethoxysilane (SZ-6070, Dow Corning Corporation)

[0126] (F2) KBM-573 (N-phenyl-3-aminopropyltrimethoxysilane, Shin-Etsu Chemical Co., Ltd.)

[0127] (G) Carbon black (MA-600B, Mitsubishi Chemical Co., Ltd.)

[0128] Examples 1 to 6 and Comparative Example 1

[0129] The above components were uniformly mixed in the amounts (parts by weight) shown in Table 1 in a Henschel mixer (KSM-22, KEUM SUNG MACHINERY Co., Ltd.) at 25°C to 30°C for 30 minutes. Thereafter, the mixture was melt-kneaded in a continuous kneader at a temperature of up to 110°C for 30 minutes, cooled to a temperature of 10°C to 15°C, and pulverized to prepare an epoxy resin composition for encapsulating semiconductor devices. In Table 1, "-" means that the corresponding component was not used.

[0130] The following properties were evaluated for each of the epoxy resin compositions prepared in Examples 1 to 6 and Comparative Example 1. The results are shown in Table 1.

[0131] (1) Flowability (spiral flow length): According to EMMI-1-66, using a low-pressure transfer molding machine, at a mold temperature of 175°C and a load of 70 kgf / cm 2 Under the conditions of 9 MPa injection pressure and 90 seconds curing time, each of the prepared epoxy resin compositions was injected into a mold to measure fluidity, and then the flow length was measured. A larger flow length indicates better fluidity.

[0132] (2) Modulus: Using a transfer molding machine, each of the prepared epoxy resin compositions was cured under the conditions of a mold temperature of 90°C ± 5°C, an injection pressure of 1,000 psi ± 200 psi, and a curing time of 120 seconds to prepare a sample (size: 20 mm × 13 mm × 1.6 mm (length × width × thickness)). The sample was post-cured in a hot air dryer at 90°C ± 5°C for 2 hours, and then the modulus of the sample was measured using a dynamic mechanical analyzer (DMA) (Q8000, TA Instruments Inc.). When measuring the modulus, the sample was heated from -10°C to 300°C at a heating rate of 5°C / min, thereby obtaining the storage modulus of the sample at 25°C and 260°C.

[0133] (3) Toughness: According to the American Society for Testing Material (ASTM) D-790, a standard specimen (size: 125 mm × 12.6 mm × 6.4 mm (length × width × thickness)) was prepared from each prepared epoxy resin composition and cured at 175°C for 4 hours. The toughness of the specimen at 25°C was then measured by a 3-point bending test using a Universal Testing Machine (UTM).

[0134] (4) Reliability: Semiconductor packages manufactured using each of the prepared epoxy resin compositions were dried at 125° C. for 24 hours and then subjected to a 5-cycle thermal shock test (1 cycle is defined as the package being left at rest at −65° C. for 10 minutes, at rest at 25° C. for 10 minutes, and at rest at 150° C. for 10 minutes). Thereafter, after a pretreatment treatment in which the package was left at rest at 85° C. and 60% RH for 168 hours and then IR reflowed at 260° C. for 30 seconds was repeated three times, the presence of external cracks was observed under an optical microscope.

[0135] Table 1

[0136]

[0137] As can be seen from Table 1, the epoxy resin compositions of Examples 1 to 6 have good crack resistance due to their high toughness.

[0138] In contrast, the composition of Comparative Example 1, which did not contain the at least one compound represented by Formula 1, generated cracks and thus could not provide a reliable semiconductor device.

[0139] In summary, high-reliability epoxy molding compounds (EMCs) can help ensure better performance in semiconductors during use. Low-reliability EMCs can lead to external cracks in semiconductors, rendering them unusable. To improve EMC reliability, it may be necessary to enhance the toughness of epoxy resin compositions to achieve high elasticity and crack resistance.

[0140] One aspect of the present disclosure may be to provide an epoxy resin composition for encapsulating a semiconductor device, which may have high toughness and improved crack resistance.

[0141] Embodiments of the present disclosure may provide an epoxy resin composition for encapsulating a semiconductor device that may have high toughness and thus improved crack resistance.

[0142] Example embodiments have been disclosed herein, and although specific terms are employed, these terms should be used and interpreted in a generic and illustrative sense only and not for purposes of limitation. In some cases, as would be apparent to one of ordinary skill in the art prior to the filing of this application, features, characteristics, and / or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically indicated. Accordingly, it should be understood by those skilled in the art that various changes in form and details may be made thereto without departing from the spirit and scope of the invention as set forth in the following claims.

Claims

1. An epoxy resin composition for encapsulating a semiconductor device, the epoxy resin composition comprising: Epoxy resin; Curing agent; Inorganic fillers; a curing catalyst; and An additive comprising at least one compound represented by Formula 1: Formula 1 wherein A is a substituted or unsubstituted C3 to C 20 Cycloalkylene or substituted or unsubstituted C6 to C 20 arylene groups, R1 and R2 are each independently hydrogen or a substituted or unsubstituted C1 to C5 alkyl group, R3 and R4 are each independently a single bond or a substituted or unsubstituted C1 to C5 alkylene group, T1 and T2 are each independently substituted or unsubstituted C1 to C 10 alkylene, and n1 and n2 are each independently an integer greater than or equal to 1. 2 . The epoxy resin composition according to claim 1 , wherein the at least one compound represented by Formula 1 is contained in the epoxy resin composition in an amount of 0.5 wt % to 5 wt % based on the total amount of the epoxy resin composition.

3. The epoxy resin composition according to claim 1, wherein the additive comprising at least one compound represented by Formula 1 comprises at least one compound represented by Formula 2 or Formula 3, Formula 2 wherein each of R1, R2, R3, R4, T1 and T2 is defined as the same as in Formula 1, R a and R b are each independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl, n3 and n4 are each independently an integer greater than or equal to 1, and m1 and m2 are each independently an integer greater than or equal to 0, Formula 3 wherein each of R1, R2, R3, R4, T1 and T2 is defined as the same as in Formula 1, R a and R b are each independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl, n5 and n6 are each independently an integer greater than or equal to 1, and m3 and m4 are each independently an integer greater than or equal to 0.

4. The epoxy resin composition according to claim 1, wherein the additive comprising at least one compound represented by Formula 1 comprises at least one compound represented by Formula 4 to Formula 7, Formula 4 Formula 5 Formula 6 Formula 7 5. The epoxy resin composition according to claim 1, wherein the epoxy resin composition comprises, based on the total weight of the epoxy resin composition: 2 wt% to 17 wt% of said epoxy resin; 0.5 wt % to 13 wt % of the curing agent; 50 wt % to 95 wt % of the inorganic filler; 0.5 wt % to 5 wt % of the at least one compound represented by Formula 1; as well as 0.01 wt% to 5 wt% of the curing catalyst. 6 . A semiconductor device encapsulated using the epoxy resin composition for encapsulating a semiconductor device according to claim 1 . 7 . The semiconductor device according to claim 6 , wherein the at least one compound represented by Formula 1 is contained in the epoxy resin composition in an amount of 0.5 wt % to 5 wt % based on the total amount of the epoxy resin composition.

8. The semiconductor device according to claim 6, wherein the additive containing at least one compound represented by Formula 1 contains at least one compound represented by Formula 2 or Formula 3, Formula 2 wherein each of R1, R2, R3, R4, T1 and T2 is defined as the same as in Formula 1, R a and R b are each independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl, n3 and n4 are each independently an integer greater than or equal to 1, and m1 and m2 are each independently an integer greater than or equal to 0, Formula 3 wherein each of R1, R2, R3, R4, T1 and T2 is defined as the same as in Formula 1, R a and R b are each independently substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 10 Aryl, n5 and n6 are each independently an integer greater than or equal to 1, and m3 and m4 are each independently an integer greater than or equal to 0.

9. The semiconductor device according to claim 6, wherein the additive comprising at least one compound represented by Formula 1 comprises at least one compound represented by Formula 4 to Formula 7, Formula 4 Formula 5 Formula 6 Formula 7 10. The semiconductor device according to claim 6, wherein the epoxy resin composition comprises, based on the total weight of the epoxy resin composition: 2 wt% to 17 wt% of said epoxy resin; 0.5 wt % to 13 wt % of the curing agent; 50 wt % to 95 wt % of the inorganic filler; 0.5 wt % to 5 wt % of the at least one compound represented by Formula 1; as well as 0.01 wt% to 5 wt% of the curing catalyst.

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