KR20210052058A - Epoxy resin composition for encapsulating semiconductor device and semiconductor device encapsulated using the same - Google Patents

Abstract

Provided are an epoxy resin composition for encapsulating a semiconductor device and the semiconductor device encapsulated by using the same, wherein the epoxy resin composition contains an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, the curing agent includes an acid anhydride-based curing agent, and the curing catalyst includes a compound of chemical formula 1.

Description

Epoxy resin composition for sealing semiconductor devices, and semiconductor devices sealed by using the same. {EPOXY RESIN COMPOSITION FOR ENCAPSULATING SEMICONDUCTOR DEVICE AND SEMICONDUCTOR DEVICE ENCAPSULATED USING THE SAME}

The present invention relates to an epoxy resin composition for sealing a semiconductor device and a semiconductor device sealed using the same. More specifically, the present invention relates to an epoxy resin composition for sealing semiconductor devices having low temperature curing properties and excellent storage stability, and a semiconductor device sealed using the same.

With the miniaturization of electronic devices, semiconductor products are also becoming thinner and smaller. In the state of a semiconductor wafer, a wafer-level-chip-size package technology in which a plurality of bare semiconductor chips are mounted and sealed is attracting attention. As the semiconductor sealing material is molded at high temperature and then cooled, the wafer-level-chip-size package formed of the sealing material inevitably causes warpage due to the difference in the coefficient of thermal expansion and elasticity between the bare semiconductor chip, the semiconductor sealing material, and the semiconductor wafer substrate. A problem arises. In order to solve this problem, there is an effort to lower the thermal expansion of the sealing material. In order to lower the thermal expansion of the sealing material, it is necessary to enable low-temperature curing and to ensure storage stability.

Meanwhile, in a general epoxy resin-acid anhydride-based curing agent system, an amine-based curing catalyst was applied as a curing catalyst to enable low-temperature curing. However, since this system has a curing temperature of 120 to 130° C., it is difficult to say that low-temperature curing properties are remarkably excellent, and storage stability is also poor.

It is an object of the present invention to provide an epoxy resin composition for sealing semiconductor devices with improved low-temperature curing properties and storage stability.

The epoxy resin composition for sealing a semiconductor device of the present invention includes an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, the curing agent includes an acid anhydride curing agent, and the curing catalyst includes a compound of Formula 1 below:

[Formula 1]

(In Chemical Formula 1,

R ¹ , R ² , R ³ , R ⁴ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group,

X is a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group,

Y is a hydroxyl group or a functional group represented by the following formula (2)

[Formula 2]

(In Formula 2, ~ is a linking site for X,

R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group)).

The semiconductor device of the present invention is sealed with the epoxy resin composition for sealing semiconductor devices of the present invention.

The present invention provides an epoxy resin composition for sealing semiconductor devices with improved low-temperature curing properties and storage stability.

When describing the numerical range in the present specification, "X to Y" means X or more and Y or less.

"Substituted" in "substituted or unsubstituted" in the present specification means that at least one hydrogen atom among the functional groups is a hydroxyl group, a halogen, an amine group, a nitro group, a cyano group, a C1 to C20 alkyl group, a C1 to C20 haloalkyl group, and a C6 to C30 aryl group, C3 to C30 heteroaryl group, C3 to C10 cycloalkyl group, C3 to C10 heterocycloalkyl group, C7 to C30 arylalkyl group or C1 to C30 heteroalkyl group substituted, "halo "Or "halogen" means fluorine, chlorine, iodine or bromine.

In the present specification, the "aliphatic hydrocarbon group" is a saturated or unsaturated hydrocarbon group consisting of carbon and hydrogen, and may be an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, or a cycloalkenyl group. The aliphatic hydrocarbon group of C1 to C30 has 1 to 30 carbon atoms and ranges between 1 and 30 carbon atoms, for example, 1, 2, 3, 4, 5, 6, 7, 8 It may mean an aliphatic hydrocarbon group having a number of, 9, 10, ..., 25, 26, 27, 28, 29, 30. The aliphatic hydrocarbon group can be straight or branched.

In the present specification, the "aromatic hydrocarbon group" is composed of carbon and hydrogen, and is an unsaturated cyclic hydrocarbon group, and may mean an aryl group or an arylalkyl group. The aromatic hydrocarbon group of C6 to C30 has 6 to 30 carbon atoms and ranges between 6 and 30 carbon atoms, for example 6, 7, 8, 9, 10, 11, 12, 13 , 14, 15, ..., it may mean an aromatic hydrocarbon group having 25, 26, 27, 28, 29, 30.

In the present specification, "aryl group" refers to a substituent in which all elements of a cyclic substituent have a p-orbital and a p-orbital forms a conjugate, and a mono or fused (ie, a ring in which carbon atoms divide adjacent pairs) functional group Including, "unsubstituted aryl group" refers to a C6 to C30 single or fused polycyclic aryl group, for example, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, etc. Can, but is not limited to this.

The epoxy resin composition for sealing a semiconductor device of the present invention includes an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst, the curing agent includes an acid anhydride curing agent, and the curing catalyst includes the curing catalyst of Formula 1. The composition had excellent low-temperature curing properties and high storage stability by including an acid anhydride-based curing agent and a curing catalyst of Formula 1 above.

Epoxy resin

Epoxy resin is one having two or more epoxy groups in the molecule, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolak type epoxy resin, tert-butyl catechol type epoxy resin, naphthalene type epoxy resin, glycidylamine type Epoxy resin, cresol novolak type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexanedimethanol type epoxy resin, trimethylol type epoxy resin, It may be a halogenated epoxy resin or the like. Epoxy resin may be included alone or in combination of two or more. The epoxy resin may include one or more of a solid epoxy resin and a liquid epoxy resin.

The epoxy resin may be contained in an amount of 2 to 17% by weight, for example 3 to 15% by weight, for example 3 to 12% by weight, based on the solid content of the epoxy resin composition. In the above range, the curability of the composition may not be deteriorated.

Hardener

The curing agent includes an acid anhydride type curing agent.

The acid anhydride-based curing agent may include a conventional acid anhydride-based curing agent known to those skilled in the art. For example, the acid anhydride-based curing agent is not particularly limited as long as it can cure the epoxy resin. For example, the acid anhydride-based curing agent may include at least one of phthalic anhydride, methyl hymic anhydride, and maleic anhydride. Specifically, the acid anhydride-based curing agent is 3,4-dimethyl-6-(2-methyl-1-propenyl)-1,2,3,6-tetrahydro phthalic anhydride, 1-isopropyl-4-methyl- Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, methyl hymic anhydride, pyromellitic dianhydride, Maleinized allo-ocimene, benzophenonetetracarboxylic dianhydride, 3,3',4,4'-biphenyltetrabisbenzophenonetetracarboxylic dianhydride, (3,4-dicarboxyphenyl) ether 2 anhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane may include at least one of dianhydride, but is not limited thereto. Does not. The acid anhydride-based curing agent may be included alone or in combination of two or more.

Specifically, the acid anhydride-based curing agent may include one or more of the following Formulas 5-1 to 5-4:

[Chemical Formula 5-1]

[Chemical Formula 5-2]

[Chemical Formula 5-3]

[Chemical Formula 5-4]

(In Formulas 5-1, 5-2, and 5-4, Me is a methyl group, and in Formula 5-2, i-Pr is an isopropyl group)

The curing agent may be included in an amount of 0.5 to 13% by weight, for example 1 to 10% by weight, for example 2 to 8% by weight, based on the solid content of the epoxy resin composition. In the above range, the curability of the composition may not be deteriorated.

Inorganic filler

The inorganic filler can improve mechanical properties and reduce stress of the epoxy resin composition. Examples of 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. have.

Preferably, the inorganic filler may include fused silica having a low coefficient of linear expansion in order to reduce stress. Fused silica refers to amorphous silica having a true specific gravity of 2.3 or less, and may also include amorphous silica made by melting crystalline silica or synthesized from various raw materials. The shape and particle diameter of the fused silica are not particularly limited, but fused silica containing 50 to 99% by weight of spherical fused silica having an average particle diameter of 5 to 30 μm, and 1 to 50% by weight of spherical fused silica having an average particle diameter of 0.001 to 1 μm. It is preferable to include the mixture so that it is 40 to 100% by weight of the total inorganic filler. In addition, the maximum particle diameter can be adjusted to one of 45 µm, 55 µm, and 75 µm according to the application.

The amount of inorganic filler used depends on the required physical properties such as moldability, low stress, and high temperature strength. In an embodiment, the inorganic filler may be included in an amount of 70 to 95% by weight, for example, 75 to 92% by weight of the epoxy resin composition. In the above range, it is possible to secure flame retardancy, fluidity and reliability of the epoxy resin composition.

Curing catalyst

The epoxy resin composition includes a curing catalyst of Formula 1 below as a curing catalyst:

[Formula 1]

(In Chemical Formula 1,

R ¹ , R ² , R ³ , R ⁴ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group,

X is a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group,

Y is a hydroxyl group or a functional group represented by the following formula (2)

[Formula 2]

(In Formula 2, ~ is a linking site for X,

R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group)).

The curing catalyst of Formula 1 acts as a latent catalyst to catalyze the curing reaction between the epoxy resin and the acid anhydride-based curing agent. The curing catalyst of Formula 1 includes a phosphonium-based cation and an anion derived from a polyol (eg, diol, triol, or tetraol). The curing catalyst of Formula 1 is a non-amine-based curing catalyst that does not have an amine group, and is included in the epoxy resin composition to which an acid anhydride-based curing agent is applied. Even if it is cured, it has excellent curing rate and increases storage stability when stored at room temperature.

In one embodiment, R ¹ , R ² , R ³ , R ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, specifically substituted or unsubstituted It may be a C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

In one embodiment, X may be a substituted or unsubstituted C1 to C30 alkylene group, specifically a substituted or unsubstituted C1 to C10 alkylene group, more specifically a substituted or unsubstituted C1 to C5 alkylene group. have. The "alkylene group" may be a straight-chain or branched-chain alkylene group. The C1 to C30 alkylene group may be substituted with a hydroxyl group.

In one embodiment, R ⁵ , R ⁶ , R ⁷ , R ⁸ are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, specifically substituted or unsubstituted It may be a C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

In one embodiment, the curing catalyst of Formula 1 may be represented by any one of the following Formula 3 and Formula 4:

[Formula 3]

(In Formula 3, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1,

X ¹ is an unsubstituted C1 to C30 alkylene group, or a C1 to C30 alkylene group substituted with a hydroxyl group)

[Formula 4]

(In Formula 4, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are as defined in Formula 1 and Formula 2, respectively,

X ¹ is an unsubstituted C1 to C30 alkylene group, or a C1 to C30 alkylene group substituted with a hydroxyl group)

In Chemical Formulas 3 and 4, the alkylene group may be linear or branched.

In one embodiment, the compound of Formula 1 may be represented by any one of the following Formulas 1-1 to 1-5, but is not limited thereto:

[Formula 1-1]

(In Formula 1-1, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)

[Formula 1-2]

(In Formula 1-2, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)

[Formula 1-3]

(In Formula 1-3, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are each of Formula 1 and Formula As defined in 2, and n is an integer of 2 to 5)

[Formula 1-4]

(In Formula 1-4, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)

[Formula 1-5]

(In Formula 1-5, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are as defined in Formula 1 and Formula 2, respectively).

The compound of Formula 1 may be prepared by a conventional method known to those skilled in the art. For example, the compound of Formula 1 may be prepared by reacting a salt containing an anion in Formula 1 with a salt having a cation in Formula 1, but is not limited thereto.

The compound of Formula 1 may be included alone or in combination of two or more, and may be included in an amount of 0.01 to 5% by weight, for example, 0.02 to 1.5% by weight, for example, 0.05 to 1.5% by weight of the epoxy resin composition. In the above range, the curing reaction time is not delayed, and the fluidity of the epoxy resin composition can be secured.

The epoxy resin composition may further include a curing catalyst other than the compound of Formula 1 above. These curing catalysts are For example, it may be a tertiary amine, an organometallic compound, an organophosphorus compound, an imidazole compound, or a boron compound. Tertiary amines include benzyldimethylamine, triethanolamine, triethylenediamine, diethylaminoethanol, tri(dimethylaminomethyl)phenol, 2-2-(dimethylaminomethyl)phenol, 2,4,6-tris(diaminomethyl) ) Phenol and tri-2-ethylhexyl acid salt. Organometallic compounds include chromium acetylacetonate, zinc acetylacetonate, and nickel acetylacetonate. The organophosphorus compound may be tris-4-methoxyphosphine, triphenylphosphine, triphenylphosphine triphenylborane, triphenylphosphine-1,4-benzoquinone adduct, or the like. Imidazole compounds are 2-methylimidazole, 2-phenylimidazole, 2-aminoimidazole, 2 - methyl-1-vinylimidazole, 2-ethyl-4-methylimidazole, 2-hepta Such as decylimidazole. Boron compounds include triphenylphosphine tetraphenylborate, tetraphenylboron salt, trifluoroborane-n-hexylamine, trifluoroborane monoethylamine, tetrafluoroboranetriethylamine, tetrafluoroboranamine, and the like. . In addition, 1,5-diazabicyclo[4.3.0]non-5-ene (1,5-diazabicyclo[4.3.0]non-5-ene: DBN), 1,8-diazabicyclo[5.4. 0]undec-7-ene (1,8-diazabicyclo[5.4.0]undec-7-ene: DBU), phenol novolac resin salt, and the like can be used.

As the curing catalyst, it is also possible to use an epoxy resin or an adduct made by pre-reacting with a curing agent.

Among the total curing catalysts, the compound of Formula 1 may be included in an amount of 10 to 100% by weight, for example, 60 to 100% by weight, and within the above range, the curing reaction time is not delayed and the fluidity of the composition may be secured.

The curing catalyst may be included in an amount of 0.01 to 5% by weight, for example, 0.02 to 1.5% by weight, for example, 0.05 to 1.5% by weight of the epoxy resin composition. In the above range, the curing reaction time is not delayed, and the fluidity of the composition can be secured.

The epoxy resin composition may further include conventional additives that may be included in the epoxy resin composition for sealing semiconductor devices. In embodiments, the additive may include one or more of a coupling agent, a release agent, a stress reliever, a crosslinking enhancer, a leveling agent, and a colorant.

The coupling agent may be one or more selected from the group consisting of epoxysilane, aminosilane, mercaptosilane, alkylsilane, and alkoxysilane, but is not limited thereto. The coupling agent may be included in an amount of 0.1 to 1% by weight of the epoxy resin composition.

The mold 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 included in an amount of 0.1 to 1% by weight of the epoxy resin composition.

The stress reliever may be one or more selected from the group consisting of modified silicone oil, silicone elastomer, silicone powder, and silicone resin, but is not limited thereto. The stress reliever may be contained in an amount of 0 to 6.5% by weight, for example 0 to 1% by weight, for example 0.1 to 1% by weight, in the epoxy resin composition.

The additive may be included in an amount of 0.1 to 10% by weight, for example, 0.1 to 3% by weight of the epoxy resin composition.

The method of preparing the epoxy resin composition is not particularly limited, but after uniformly mixing each component included in the composition using a Henschel mixer or a Lodige mixer, melt-kneading at 90 to 120°C with a roll mill or kneader , Can be prepared through cooling and grinding processes.

The semiconductor device of the present invention can be sealed using the epoxy resin composition for sealing semiconductor devices of the present invention. Transfer molding, injection molding, casting molding, compression molding, etc. may be used as a method of sealing a semiconductor device using the epoxy resin composition of the present invention, but is not limited thereto. In one embodiment, it may be sealed by a low pressure transfer molding method. In other embodiments, it may be sealed by compression molding.

Hereinafter, the configuration and operation of the present invention will be described in more detail through preferred embodiments of the present invention. However, this has been presented as a preferred example of the present invention and cannot be construed as limiting the present invention in any sense.

Preparation Example 1: Preparation of curing catalyst

In a base (sodium methoxide in methanol), through an ion exchange reaction (1:1 molar ratio) of diol (1,2-ethaneol) and tetraphenylphosphonium bromide, in Formula 1-1, R ¹ , R ² , A ^{curing catalyst in which R 3} and R ⁴ are each a phenyl group was prepared. In order to solidify, purification was carried out through a water washing process.

Preparation Example 2: Preparation of curing catalyst

In a base (sodium methoxide in methanol), through an ion exchange reaction (1:1 molar ratio) of diol (1,3-propanediol) and tetraphenylphosphonium bromide, R ¹ , R ² , A ^{curing catalyst in which R 3} and R ⁴ are each a phenyl group was prepared. In order to solidify, purification was carried out through a water washing process. In order to solidify, purification was carried out through a water washing process.

Preparation Example 3: Preparation of curing catalyst

In a base (sodium methoxide in methanol), through an ion exchange reaction (1:4 molar ratio) of diol (1,2-ethanol) and tetraphenylphosphonium bromide, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each a phenyl group and n is 2 to prepare a curing catalyst.

Preparation Example 4: Preparation of curing catalyst

^{In a base (sodium methoxide in methanol), R 1} in Formula 1-4 through an ion exchange reaction (1:1 molar ratio) of triol (1,2,3-propanetriol) and tetraphenylphosphonium bromide , R ² , R ³ , and R ⁴ are each a phenyl group to prepare a curing catalyst. In order to solidify, purification was carried out through a water washing process.

Preparation Example 5: Preparation of curing catalyst

^{In a base (sodium methoxide in methanol), R 1} in Formula 1-5 above through an ion exchange reaction (1:4 molar ratio) of triol (1,2,3-propanetriol) and tetraphenylphosphonium bromide, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R ⁸ were each a phenyl group to prepare a curing catalyst. In order to solidify, purification was carried out through a water washing process.

Specific specifications of the components used in the following Examples and Comparative Examples are as follows.

(A)(A1) Epoxy resin: Celloxide 2021P (Daicel)

(A2) Epoxy resin: KDS-8128 (Kukdo Chemical)

(B) Curing agent: Rikacid-MH (New Japan Chemical Co. Ltd, acid anhydride curing agent, the compound of Formula 5-4)

(C) Inorganic filler: a mixture of a spherical fused silica having an average particle diameter of 18 μm and a spherical fused silica having an average particle diameter of 0.5 μm in a ratio of 9:1 by weight

(D) Curing catalyst: (D1) the compound of Preparation Example 1, (D2) the compound of Preparation Example 2, (D3) the compound of Preparation Example 3, (D4) the compound of Preparation Example 4, (D5) the compound of Preparation Example 5 , (d1) Ajicure PN-23 (imidazole-based curing catalyst), (d2) 2P4MZ-PW (imidazole-based curing catalyst), (d3) propanediol

(E) Colorant: MA-600 (carbon black, Mitsubishi Chemical)

Examples 1 to 5 and Comparative Examples 1 to 3

After uniformly mixing for 30 minutes at 25 to 30° C. using a Henschel mixer (KEUM SUNG MACHINERY CO.LTD, KSM-22) according to the composition of Table 1 (unit: parts by weight) below, a continuous kneader (Kneader) After melt-kneading at a maximum of 110° C. for 30 minutes using, the mixture was cooled to 10 to 15° C. and pulverized to prepare an epoxy resin composition for sealing a semiconductor device.

Example Comparative example One 2 3 4 5 One 2 3 (A) (A1) 1.47 1.47 1.47 1.47 1.47 1.47 1.47 1.47 (A2) 6.23 6.23 6.23 6.23 6.23 6.23 6.23 6.23 (B) 5 5 5 5 5 5 5 5 (C) 86.5 86.5 86.5 86.5 86.5 86.5 86.5 86.5 (D) (D1) 0.5 0 0 0 0 0 0 0 (D2) 0 0.5 0 0 0 0 0 0 (D3) 0 0 0.5 0 0 0 0 0 (D4) 0 0 0 0.5 0 0 0 0 (D5) 0 0 0 0 0.5 0 0 0 (d1) 0 0 0 0 0 0.5 0 0 (d2) 0 0 0 0 0 0 0.5 0 (d3) 0 0 0 0 0 0 0 0.5 (E) 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 total 100 100 100 100 100 100 100 100

The following physical properties were evaluated for the prepared epoxy resin composition for sealing a semiconductor device, and the results are shown in Table 2 below.

(1) on set pont (unit: ℃): The intersection of two tangents was calculated as on set pont through DSC. DSC measurement was carried out while increasing the temperature from 30°C to 250°C with a sample amount of about 20 mg and a temperature increase rate of 10°C/min.

(2)peak point (unit: ℃): The inflection tangent through the largest slope point of the curve through DSC was taken as the peak point. DSC measurement was performed in the same manner as in (1).

(3) Curing rate (unit:%): ([Enthalpy before curing-Enthalpy after curing] / [Enthalpy before curing]) x 100. The enthalpy before curing was obtained by performing DSC immediately after preparing the compositions in Examples and Comparative Examples. After curing, the enthalpy was obtained by allowing the prepared composition to stand at 100° C. for 10 minutes and then performing DSC. DSC was carried out in the same manner as in (1).

(4) Thickening rate (unit:%): After leaving for 8 hours at room temperature (25℃) through a rheometer ([final viscosity-initial viscosity] / [Initial viscosity]) x 100.

Example Comparative example One 2 3 4 5 One 2 3 on set point 87 92 93 88 95 119 101 88 peak point 103 109 111 107 115 145 118 105 Curing rate 62 67 60 62 62 25 28 59 Thickening rate 9 11 8 6 12 21 19 75

As shown in Table 2, the epoxy resin composition for sealing a semiconductor device of the present invention has a high curing rate even at 100° C. and has low on set point and low peak point, so it has excellent low-temperature curing properties and low thickening rate and thus has excellent storage stability.

In the present invention, Comparative Examples 1 and 2 not including the phosphonium-based catalyst of Formula 1 had poor low temperature curing properties and storage stability. In addition, in the present invention, Comparative Example 3 provided with a diol catalyst without the phosphonium-based cation of Formula 1 had poor storage stability.

Simple modifications or changes of the present invention can be easily implemented by those of ordinary skill in the art, and all such modifications or changes can be considered to be included in the scope of the present invention.

Claims (7)

Including an epoxy resin, a curing agent, an inorganic filler and a curing catalyst, the curing agent includes an acid anhydride-based curing agent, and the curing catalyst comprises a compound of Formula 1
[Formula 1]

(In Chemical Formula 1,
R ¹ , R ² , R ³ , R ⁴ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group,
X is a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group,
Y is a hydroxyl group or a functional group represented by the following formula (2)
[Formula 2]

(In Formula 2, ~ is a linking site for X,
R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each independently a substituted or unsubstituted C1 to C30 aliphatic hydrocarbon group or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group)).
The epoxy resin composition for sealing a semiconductor device according to claim 1, wherein X is a linear or branched C1 to C10 alkylene group substituted or unsubstituted with a hydroxyl group.
The epoxy resin composition for sealing a semiconductor device according to claim 1, wherein the curing catalyst of Formula 1 is represented by any one of the following Formula 3 and Formula 4:
[Formula 3]

(In Formula 3, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1,
X ¹ is an unsubstituted C1 to C30 alkylene group, or a C1 to C30 alkylene group substituted with a hydroxyl group)
[Formula 4]

(In Formula 4, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are as defined in Formula 1 and Formula 2, respectively,
X ¹ is an unsubstituted C1 to C30 alkylene group, or a C1 to C30 alkylene group substituted with a hydroxyl group)
The epoxy resin composition of claim 1, wherein the compound of Formula 1 is represented by any one of the following Formulas 1-1 to 1-5:
[Formula 1-1]

(In Formula 1-1, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)
[Formula 1-2]

(In Formula 1-2, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)
[Formula 1-3]

(In Formula 1-3, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are each of Formula 1 and Formula As defined in 2, and n is an integer of 2 to 5)
[Formula 1-4]

(In Formula 1-4, R ¹ , R ² , R ³ , R ⁴ are each the same as defined in Formula 1)
[Formula 1-5]

(In Formula 1-5, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are as defined in Formula 1 and Formula 2, respectively).
The epoxy resin composition of claim 1, wherein the compound of Formula 1 is contained in an amount of 0.01 to 5% by weight of the epoxy resin composition.
The method according to claim 1, comprising 2 to 17% by weight of the epoxy resin, 0.5 to 13% by weight of the curing agent, 70 to 95% by weight of the inorganic filler, and 0.01 to 5% by weight of the curing catalyst. Epoxy resin composition.
A semiconductor device sealed using the epoxy resin composition for sealing a semiconductor device according to any one of claims 1 to 6.