JP2002284848A - Thermosetting resin composition, epoxy resin molding material and semiconductor device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an epoxy resin molding material which reconciles quick curability and storage stability. SOLUTION: The epoxy resin molding material comprises (A) a compound having two or more epoxy groups in the molecule, (B) a compound having two or more phenolic hydroxyl groups in the molecule, (C) a compound to be represented by formula (1) (wherein P is a phosphorus atom; R1 , R2 , R3 and R4 are each substituted or nonsubstituted aromatic group or an alkyl group; A1 is a divalent aromatic group; B1 is a single bond or a divalent substituent to be selected from an ether group, a sulfone group, a sulfide group, and a carbonyl group or a divalent organic group composed of 1-13 carbon atoms; and m is a number of 0<=m<1) or formula (2) (wherein P is a phosphorus atom; R1 , R2 , R3 and R4 are each substituted or nonsubstituted aromatic group or an alkyl group; A2 is a divalent aromatic group; and m is a number of 0<=m<1), and (D) an inorganic filler as the essential components.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a thermosetting resin composition having good curability and preservability and useful in the field of electric and electronic materials, an epoxy resin molding material using the same, and a semiconductor device. .

[0002]

2. Description of the Related Art In recent years, electrical and electronic materials, particularly semiconductor encapsulating materials, have been required to have rapid curability for the purpose of improving production efficiency and to improve storability for improving handling during distribution and storage. It is becoming possible. Conventionally, epoxy resins for electric and electronic materials have used amines,
Various compounds such as imidazole compounds, nitrogen-containing heterocyclic compounds such as diazabicycloundecene, quaternary ammonium, phosphonium and arsonium compounds have been used. Although amines, especially imidazoles, show excellent curability, they cause corrosion of internal wiring under high temperature and high humidity conditions as a semiconductor encapsulant, that is, they tend to have low moisture resistance reliability. There is a problem with the use of phosphorus, and the use of phosphorus compounds such as phosphonium compounds has become common. These generally used curing catalysts often exhibit a curing promoting action even at a relatively low temperature such as room temperature. This means
This is a cause of lowering the quality of the resin composition such as an increase in viscosity during production and storage of the resin composition, a decrease in fluidity, and a variation in curability.

In order to solve this problem, in recent years, studies on so-called latent curing accelerators, which suppress changes over time in viscosity and fluidity at low temperatures and develop a curing reaction only by molding and heating during molding, have been actively conducted. Has been made. As a means for protecting the active site of the curing accelerator with an ion pair, studies have been made to develop latentness.
No. 90 discloses a latent curing accelerator having a salt structure of various organic acids and phosphonium ions.
However, since this phosphonium salt does not have a specific higher molecular structure and the ion pair is relatively easily affected by the external environment, molecules such as low molecular weight epoxy resin and phenol aralkyl resin in recent years are easy to move. In the case of a semiconductor sealing material using a phenol resin curing agent, there is a problem that storage stability is reduced.

[0004]

SUMMARY OF THE INVENTION The present invention relates to a thermosetting resin composition having good curability and preservability, and useful in the field of electric and electronic materials, an epoxy resin molding material using the same, and moisture resistance reliability. It is an object to provide an excellent semiconductor device.

[0005]

According to the present invention, there is provided [1] a compound having two or more epoxy groups in one molecule (A), and a compound (B) having two or more phenolic hydroxyl groups in one molecule.
And a thermosetting resin composition comprising a molecular compound (C) represented by the general formula (1) or (2) as an essential component;

Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, A ₁ is a divalent aromatic group, B ₁ is a single bond or an ether group, Represents a divalent substituent selected from a sulfone group, a sulfide group, and a carbonyl group, or a divalent organic group having 1 to 13 carbon atoms, and m is a number satisfying 0 ≦ m <1.)

[0006]

Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, and A ₂ is a divalent aromatic group. M is 0 ≦ m <1. Indicates the number.)

[2] A compound (A) having two or more epoxy groups in one molecule, and a phenolic hydroxyl group in one molecule.
An epoxy resin molding material comprising, as essential components, a compound (B) having at least one compound (B), a molecular compound (C) represented by the general formula (1) or (2), and an inorganic filler (D).

Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, A ₁ is a divalent aromatic group, B ₁ is a single bond or an ether group, Represents a divalent substituent selected from a sulfone group, a sulfide group, and a carbonyl group, or a divalent organic group having 1 to 13 carbon atoms, and m is a number satisfying 0 ≦ m <1.)

[0008]

Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, and A ₂ is a divalent aromatic group. M is 0 ≦ m <1. Indicates the number.)

[3] General formula (1) or general formula (2)
In the molecular compound (C) represented by the formula (2), the value of m is represented by m = 0 or 0.5, the epoxy resin molding material according to the item [2], [4] wherein the phenol component of the general formula (1) is bis ( 4-hydroxyphenyl) sulfone, 2,2-bis (4-hydroxyphenyl) 1,1,1-3,3,3-
The epoxy resin molding material according to item [3], which is hexafluoropropane or bis (4-hydroxyphenyl) ether; [5] the item [3], wherein the phenol component of the general formula (2) is 2,3-dihydroxynaphthalene. [6] A semiconductor element is sealed with the epoxy resin molding material according to any one of [6], [2], [3], [4] or [5]. Semiconductor device characterized by the above-mentioned. By using these, it is possible to obtain an epoxy resin molding material having extremely excellent curability and storage stability.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The compound (A) having two or more epoxy groups in one molecule used in the present invention is not limited as long as it has two or more epoxy groups in one molecule. Examples thereof include phenols such as biphenol, phenol resins such as biphenol type epoxy resin, novolak type epoxy resin, and naphthalene type epoxy resin, and epoxy resins and epoxy compounds obtained by reacting epichlorohydrin with hydroxyl groups such as naphthols. Other examples include an epoxy resin such as an alicyclic epoxy resin obtained by oxidizing an olefin using a peracid and epoxidizing it, and a resin obtained by epoxidizing dihydroxybenzenes such as hydroquinone with epichlorohydrin.

The compound (B) having two or more phenolic hydroxyl groups in one molecule has two epoxy groups in one molecule.
It acts as a curing agent for the compound (A) having at least one compound. Specifically, phenol novolak resins, cresol novolak resins, alkyl-modified novolak resins (including resins obtained by reacting and co-condensing double bonds of cycloalkene with phenols by a Friedel-Crafts type reaction), phenol aralkyl resins, naphthols Examples thereof include resins obtained by co-condensing phenols and phenols with a carbonyl group-containing compound. A compound in which two or more hydrogen atoms bonded to an aromatic ring in one molecule are substituted with a hydroxyl group may be used.

In the present invention, the molecular compound (C) acting as a curing accelerator is represented by the general formula (1) or (2):
And a molecular association of a tetra-substituted phosphonium and a phenol compound. Consisting of one tetra-substituted phosphonium cation, one or more and less than three phenolic hydroxyl groups and one phenoxide anion unit, and one or more and less than three phenolic groups around the positive charge of the tetra-substituted phosphonium ion It is considered that the structure is stabilized by surrounding the hydroxyl group and one phenoxide anion.

A phosphonium ion having such a structure is a tetra-substituted phosphonium ion having a substituted or unsubstituted aryl or alkyl group as a substituent.
It is stable against heat and hydrolysis and is preferable. Specifically, triarylmonophosphorium such as tetraphenylphosphonium and tetratolylphosphonium, and triarylmono synthesized from triarylphosphine such as triphenylmethylphosphonium and alkyl halide Examples thereof include tetraalkyl-substituted phosphonium such as alkylphosphonium and tetrabutylphosphonium.

Phenol compounds which are the other components forming the molecular compound (C) include bisphenol A (2,2-bis (4-hydroxyphenyl) propane) and bisphenol F (4,4'-methylene). Bisphenol, 2,4'-methylenebisphenol, 2,2
-Methylenebisphenol), bis (4-hydroxyphenyl) sulfone (bisphenol S), bisphenol E (4,4'-ethylidenebisphenol), bisphenolfluorene (4,4 '-(9H-fluorene-
Bisphenols such as 9-ylidene) bisphenol), 4,4′-methylidenebis (2,6-dimethylphenol) and bis (4-hydroxyphenyl) methanone;
4,4′-biphenol, 2,2′-biphenol,
3,3 ′, 5,5′-tetramethylbiphenol, 2,
2-bis (4-hydroxyphenyl) 1,1,1-3,
Biphenols such as 3,3-hexafluoropropane, hydroquinone, resorcinol, catechol, bis (4-hydroxyphenyl) ether, 2,6-dihydroxynaphthalene, 1,4-dihydroxynaphthalene,
2,3-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,1′-bi-2-naphthol, 1,4
-Dihydroxyanthraquinone, etc., but in view of the stability, curability and physical properties of the cured product of the molecular compound, bisphenol A, bisphenol F (4,4′-methylenebisphenol, 2,4′-methylenebisphenol,
2,2'-methylenebisphenol and a mixture of these isomers such as bisphenol FD manufactured by Honshu Chemical Industry Co., Ltd.), bisphenol S, 4,4'-biphenol, 2,2-bis (4- Hydroxyphenyl) 1,
1,1-3,3,3-hexafluoropropane and bis (4-hydroxyphenyl) ether 2,3-dihydroxynaphthalene are preferred.

The molecular compound (C) comprises a phenol compound as described above and a base which ultimately assists dehydrohalogenation,
For example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an organic base such as pyridine or triethylamine is dissolved in a solvent such as an alcohol, and then the tetra-substituted phosphonium halide dissolved in an appropriate solvent is added. It is synthesized by a method of reacting and finally taking out as a solid content by an operation such as recrystallization or reprecipitation, or a method of thermally reacting a tetra-substituted phosphonium tetra-substituted borate and a phenol compound and then heating and reacting in a solvent such as alcohol. It is possible.

The molecular compound (C) used in the present invention has a phosphonium-phenoxide-type salt in its structure as described above, which is different from the conventional phosphonium-organic acid anion salt-type compound in that the molecular compound (C) In C), a tertiary structure due to a hydrogen bond involving a proton of a phenolic hydroxyl group surrounds this ionic bond.
In the conventional salt, the reactivity was controlled only by the strength of the ionic bond. On the other hand, in the molecular compound (C), the ion pair of the reaction active site was surrounded by the higher-order structure at room temperature, and the active site was controlled. On the other hand, at the stage of actual molding, the active sites are exposed due to the collapse of this higher-order structure, and so-called latency, which expresses reactivity, is imparted.

The compounding amount of the molecular compound (C) acting as a curing accelerator used in the present invention is such that the compound (A) having two or more epoxy groups in one molecule and the compound (A) acting as a curing agent are used.
When the total weight of the compound (B) having two or more phenolic hydroxyl groups in the molecule is 100 parts by weight, 0.5 to
About 20 parts by weight is suitable because of good balance of curability, storage stability and other properties. The compounding ratio of the compound (A) having two or more epoxy groups in one molecule to the compound (B) having two or more phenolic hydroxyl groups in one molecule is such that the compound having two or more epoxy groups in one molecule is used. The sum of the phenolic hydroxyl group of the compound (B) having two or more phenolic hydroxyl groups in one molecule and the phenolic hydroxyl group contained in the molecular compound (C) is 0. When used in a molar ratio of about 5 to 2 mol, preferably about 0.8 to 1.2, the curability, heat resistance, electric properties, and the like are further improved.

The type of the inorganic filler (D) used in the present invention is not particularly limited, and those generally used for a sealing material can be used. For example, fused crushed silica powder, fused spherical silica powder, crystalline silica powder, secondary agglomerated silica powder, alumina, titanium white, aluminum hydroxide, talc, clay, glass fiber, etc., are preferred, and fused spherical silica powder is particularly preferred. The shape is preferably infinitely spherical, and the filling amount can be increased by mixing particles having different particle sizes.

The compounding amount of the inorganic filler is a compound (A) having two or more epoxy groups in one molecule and a compound (B) having two or more phenolic hydroxyl groups in one molecule.
Is preferably 200 to 2400 parts by weight per 100 parts by weight of the total amount of If the amount is less than 200 parts by weight, the reinforcing effect of the inorganic filler may not be sufficiently exhibited. If the amount exceeds 2400 parts by weight, the fluidity of the molding material may be reduced, and poor filling may occur at the time of molding. In particular, if the compounding amount of the inorganic filler is 250 to 1400 parts by weight per 100 parts by weight of the total of the components (A) and (B), the moisture absorption of the cured product of the molding material is low, and the solder cracks Since generation can be prevented and the viscosity of the molding material at the time of melting is reduced, there is no possibility of causing gold wire deformation inside the semiconductor device, which is more preferable. It is preferable that the inorganic filler is sufficiently mixed in advance.

The epoxy resin molding material of the present invention comprises (A)
In addition to the components (D), if necessary, a coupling agent such as γ-glycidoxypropyltrimethoxysilane, a coloring agent such as carbon black, a brominated epoxy resin, an antimony oxide, a flame retardant such as a phosphorus compound, Various additives such as low-stress components such as silicone oil and silicone rubber, natural wax, synthetic wax, higher fatty acids or metal salts thereof, release agents such as paraffin, antioxidants and the like can be blended. And triphenylphosphine, 1,8-diazabicyclo (5,4,4) in a range that does not impair the properties of the molecular compound (C) that functions as a curing accelerator in
0) There is no problem even when used in combination with a catalyst such as undecene-7, 2-methylimidazole.

The epoxy resin molding material of the present invention comprises (A)
To (D) are mixed at room temperature using a mixer, kneaded with a kneader such as a roll or an extruder, cooled, and pulverized. In order to manufacture a semiconductor device by encapsulating an electronic component such as a semiconductor using the epoxy resin molding material of the present invention, the molding can be performed by a molding method such as a transfer mold, a compression mold, and an injection mold. The semiconductor device sealed with the cured product of the epoxy resin molding material of the present invention is included in the technical scope of the present invention and exhibits excellent moisture resistance.

[0022]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited by these examples. [Synthesis of Curing Accelerator] The structure of the synthesized molecular compound (C) was confirmed by NMR, elemental analysis and neutralization titration (measurement of phosphonium phenoxide equivalent) by the following method. Reacting the synthesized molecular compound (C) with a known excess amount of oxalic acid in a methanol / water solvent,
The remaining oxalic acid was quantified with an aqueous sodium hydroxide solution having a known normality, and the normality (N) per weight of the molecular compound (C) was determined.
/ G) was calculated. The reciprocal of this value is the phosphonium phenoxide equivalent.

(Synthesis Example 1) A 1-liter separable flask equipped with a stirrer was charged with BPS- manufactured by Nikka Chemical Co., Ltd.
N (mainly composed of 4,4'-bisphenol S) 3
7.5 g (0.15 mol) and 100 ml of methanol were charged, and dissolved by stirring at room temperature. A solution in which 4.0 g (0.1 mol) of sodium hydroxide was previously dissolved in 50 ml of methanol was added while stirring. . Next, a solution in which 41.9 g (0.1 mol) of tetraphenylphosphonium bromide was dissolved in 150 ml of methanol in advance was added. Stirring was continued for a while, and after adding 300 ml of methanol, the solution in the flask was dropped into a large amount of water while stirring to obtain a white precipitate. The precipitate was filtered and dried to obtain 66.0 g of white crystals. This compound is designated as C1. C1
Is a target molecular compound in which one molecule of tetraphenylphosphonium and 4,4′-bisphenol S are complexed at a molar ratio of 1: 1.5 from the results of NMR, mass spectrum, and elemental analysis. Was. Also, from the value of the neutralization titration, the phosphonium phenoxide equivalent was close to the theoretical value of 713,
The structure described above is shown. The yield of the synthesis was 92.6%. (Synthesis Examples 2 to 6) In Synthesis Examples 2 to 6, the basic operations were all performed in the same manner as in Synthesis Example 1 under the conditions shown in Table 1.
Compounds C2 to C6 were prepared respectively. Table 1 shows the results.

(Comparative Synthesis Example 1) A 1-liter separable flask equipped with a stirrer was charged with bis (4-hydroxy-
12.8 g of 3,5-dimethylphenyl) methane (0.
05 mol) and 50 ml of methanol, stirred and dissolved at room temperature, and 4.0 g of sodium hydroxide with further stirring.
(0.1 mol) was previously dissolved in 50 ml of methanol. Then, 33.9 g (0.1 mol) of tetrabutylphosphonium bromide was previously added to 150 ml.
Was dissolved in methanol. Stirring was continued for a while, and 100 ml of pure water was dropped into the flask while stirring, and 100 ml of 2-propanol was further added to obtain a white precipitate. The precipitate was filtered and dried to obtain white crystals. This compound is designated as D1. As a result of performing the same analysis as in Synthesis Example 1, one molecule of tetrabutylphosphonium was added to each phenoxide in which the protons of two hydroxyl groups of bis (4-hydroxy-3,5-dimethylphenyl) methane were dissociated. The compound was ionically bonded at 1: 2. This D1
Is a simple phosphonium salt, not a molecular compound used in the present invention.

(Comparative Synthesis Example 2) p-Phenylphenol 1 was placed in a 1-liter separable flask equipped with a stirrer.
A solution in which 4.0 g (0.1 mol) of sodium hydroxide was previously dissolved in 50 ml of methanol was added while stirring and dissolving 7.0 g (0.1 mol) of methanol and 50 ml of methanol at room temperature. Next, a solution in which 41.9 g (0.1 mol) of tetraphenylphosphonium bromide was dissolved in 150 ml of methanol in advance was added. Stirring was continued for a while, and 100 ml of pure water was dropped into the flask while stirring, and 100 ml of 2-propanol was further added to obtain a white precipitate. The precipitate was filtered and dried to obtain white crystals. This compound is designated as D2. As a result of performing the same analysis as in Synthesis Example 1, it was a compound in which one molecule of tetraphenylphosphonium was ion-bonded 1: 1 to phenoxide from which the proton of the hydroxyl group of p-phenylphenol was eliminated. D2 is a simple phosphonium salt and not a molecular compound used in the present invention.

(Comparative Synthesis Example 3) In a 1-liter separable flask equipped with a stirrer, 12.2 g (0.1
Mol) and methanol (50 ml), stirred and dissolved at room temperature, and further stirred to obtain 4.0 g of sodium hydroxide.
(0.1 mol) was previously dissolved in 50 ml of methanol. Next, 41.9 g (0.1 mol) of tetraphenylphosphonium bromide was added to 150 ml in advance.
Was dissolved in methanol. Stirring was continued for a while, and the solution in the flask was added dropwise to 100 ml of water while stirring, and 100 ml of 2-propanol was further added to obtain a white precipitate. The precipitate was filtered and dried to obtain white crystals. This compound is designated as D3. As a result of performing the same analysis as in Synthesis Example 1, it was a compound in which one molecule of tetraphenylphosphonium was ion-bonded 1: 1 to the carboxylate from which the proton of the carboxyl group of benzoic acid was eliminated. This D3 is a simple phosphonium salt and not a molecular compound used in the present invention. The result of the comparative synthesis example is also
Table 1 summarizes the results as in the other synthesis examples.

[0027]

[Table 1]

[Evaluation of Thermosetting Resin Composition] First, the synthesized molecular compound (C) was compounded with a compound (A) having two or more epoxy groups in one molecule and a phenolic hydroxyl group in one molecule. In addition to the above compound (B), the mixture was pulverized and mixed, further melt-kneaded at 100 ° C. for 5 minutes on a hot plate, and then cooled and pulverized to prepare a sample of the composition for evaluation. The evaluation method is as follows. (1) Curing torque Using a composition prepared by the above-described sample preparation method, a curast meter (manufactured by Orientec Co., Ltd., JS
R Curastometer PS) at 175 ° C
The torque after 5 seconds was determined. The torque in the curast meter is a parameter of curability, and the larger the value, the better the curability. The unit is kgf · cm. (2) Residual rate of curing heat generation (evaluation of storage stability) Using the composition prepared by the above-described sample preparation method, the initial curing heat generation immediately after preparation and the curing heat generation after storage at 40 ° C for 3 days were measured. , Initial curing heat value (mJ
/ Mg) of curing heat after storage (mJ / m
The percentage of g) was calculated. In addition, the measurement of the calorific value of the curing was performed by differential thermal analysis under the condition of a heating rate of 10 ° C./min.
A larger value indicates better storage stability.

(Examples 1 to 6 and Comparative Examples 1 to 4) With respect to Examples 1 to 6 and Comparative Examples 1 to 4, samples of the compositions were prepared by the above-described method according to the formulations shown in Table 2, and evaluated. did. In Comparative Example 1, triphenylphosphine was used instead of the compound (C) in Examples, and in Comparative Examples 2 to 4,
Compounds D1 to D3 synthesized in Comparative Synthesis Examples 1 to 3 were used. The evaluation results of the obtained compositions were as shown in Table 2.

[0030]

[Table 2]

As shown in the Examples, the thermosetting resin composition of the present invention has good curability and storage stability, whereas the resin composition using triphenylphosphine of Comparative Example 1 as a curing accelerator. The products were also poor in curability and storage stability, and Comparative Examples 2 to 4
The phosphonium salt which is not a molecular compound used in the present invention has good curability but poor storage stability.

[Evaluation of Epoxy Resin Molding Material] (Example 7) YX-4000H manufactured by Yuka Shell Epoxy Co., Ltd. (52 parts by weight of biphenyl type epoxy resin) XL-225 (phenol aralkyl resin) manufactured by Mitsui Chemicals, Inc. 48 2.9 parts by weight Molecular compound C1 2.9 parts by weight Fused spherical silica (average particle size 15 μm) 500 parts by weight Carbon black 2 parts by weight Brominated bisphenol A type epoxy resin 2 parts by weight Carnauba wax 2 parts by weight and mixed using a hot roll Then, the mixture was kneaded for 8 minutes at 95 ° C., cooled and pulverized to obtain an epoxy resin molding material, and the obtained epoxy resin molding material was evaluated by the following method.

Evaluation method (1) Spiral flow was measured using a mold for measuring spiral flow according to EMMI-I-66.
The measurement was performed at 5 ° C., an injection pressure of 70 kg / cm ² , and a curing time of 2 minutes. Spiral flow is a parameter of fluidity, and a larger value indicates better fluidity. The unit is cm. (2) Curing torque is measured by a curameter (Orientec Co., Ltd., JSR curameter IVPS type)
Was used to measure the torque after 175 ° C. and 45 seconds. The larger the value, the better the curability. The unit is kgf ・ c
m (3) The residual flow rate was measured as a spiral flow immediately after preparation and after storage for one week at 30 ° C., and expressed as a percentage of the spiral flow immediately after preparation after storage. Units%. (4) Moisture resistance reliability: mold temperature 175 ° C, pressure 70kg
/ Cm ² , and a curing time of 2 minutes to form a 16pDIP. This molded product is post-cured at 175 ° C. for 8 hours,
In water vapor at 100 ° C. and 100% relative humidity, a voltage of 20 V
The voltage was applied to 6pDIP, and the disconnection defect was examined. The time until a defect appeared in eight or more of the 15 packages was defined as a defect time. The unit is time. The measurement time is up to 50
When the number of defective packages was 7 or less at that time, the defective time was indicated as 500 hours or more. The longer the failure time, the better the moisture resistance reliability.

(Examples 8 to 9, Comparative Examples 5 to 8) Example 8
~ 9 and Comparative Examples 5 to 8 according to the formulation in Table 3,
An epoxy resin molding material was prepared and evaluated in the same manner as in Example 7. Table 3 shows the results.

[0035]

[Table 3]

The epoxy resin molding materials of the present invention of Examples 7 to 9 have extremely good preservability and curability, and the semiconductor device sealed with the cured product of the epoxy resin molding material has moisture resistance. It turns out that it is favorable. On the other hand, the epoxy resin molding materials of Comparative Examples 5 to 8 are inferior to those of Examples 7 to 9 in any of fluidity, storage stability, and moisture resistance reliability.

[0037]

As described above, the thermosetting resin composition and the epoxy resin molding material of the present invention have excellent curability and preservability. It has excellent properties and is industrially useful.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) H01L 23/31 F-term (Reference) 4J002 CC04X CC05X CC07X CD04W CD05W CD06W CE00X DE137 DE147 DJ017 DJ047 DL007 EW176 FA047 FD017 FD130 FD156 FD160 FD200 GQ05 4J036 AA01 AD01 AF01 AF06 DB05 DD07 FA01 FA05 FB07 4M109 AA01 EA03 EB03 EB04 EB08 EB09 EB12

Claims (6)

[Claims] 1. A compound (A) having two or more epoxy groups in one molecule, a compound (B) having two or more phenolic hydroxyl groups in one molecule, and a compound represented by the general formula (1) or (2). A thermosetting resin composition comprising the represented molecular compound (C) as an essential component. Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, A ₁ is a divalent aromatic group, B ₁ is a single bond or an ether group, Represents a divalent substituent selected from a sulfone group, a sulfide group, and a carbonyl group, or a divalent organic group having 1 to 13 carbon atoms, and m represents a number of 0 ≦ m <1.) 2] (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, and A ₂ is a divalent aromatic group. M is 0 ≦ m <1. Indicates the number.) 2. A compound having two or more epoxy groups in one molecule (A), a compound having two or more phenolic hydroxyl groups in one molecule (B), a compound represented by the general formula (1) or the general formula (2). An epoxy resin molding material, comprising the molecular compound (C) and the inorganic filler (D) represented as essential components. Embedded image (P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic group or an alkyl group, A ₁ is a divalent aromatic group, B ₁ is a single bond or an ether group, Represents a divalent substituent selected from a sulfone group, a sulfide group, and a carbonyl group, or a divalent organic group having 1 to 13 carbon atoms, and m represents a number of 0 ≦ m <1.) 4] (P represents a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ represent a substituted or unsubstituted aromatic group or an alkyl group, and A ₂ represents a divalent aromatic group. Is shown.) 3. The epoxy resin molding material according to claim 2, wherein in the molecular compound (C) represented by the general formula (1) or (2), the value of m is represented by m = 0 or 0.5. 4. The phenol component of the general formula (1) is bis (4-hydroxyphenyl) sulfone, 2,2-bis (4-hydroxyphenyl) 1,1,1-3,3,3-
The epoxy resin molding material according to claim 3, which is hexafluoropropane or bis (4-hydroxyphenyl) ether. 5. The phenol component of the general formula (2) contains a few
The epoxy resin molding material according to claim 3, which is -dihydroxynaphthalene. 6. A semiconductor device comprising a semiconductor element encapsulated with the epoxy resin molding material according to claim 2.