JP2001098053A - Thermosetting resin composition and epoxy resin molding material and semiconductor device using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a thermosetting resin composition and an epoxy resin molding material exhibiting both a rapid curability and good storage stability, and a semiconductor device made by using the same. SOLUTION: A thermosetting resin composition comprises (A) a compound having at least two of an epoxy group in a molecule (B) another compound having at least two of a phenolic hydroxyl group in a molecule (C) a molecular compound as essential components. An epoxy resin molding material contains the composition; and a semiconductor device is sealed with a cured product of the material.

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 cured product thereof. The present invention relates to a semiconductor device sealed by the above.

[0002]

2. Description of the Related Art In recent years, electric and electronic materials, particularly IC encapsulating materials, have been required to have a rapid curing property for the purpose of improving production efficiency and a storage property for improving handling properties during distribution and storage. , Is being asked.

Heretofore, epoxy resins for the field of electronics have been used as curing catalysts such as amines, imidazole compounds, nitrogen-containing heterocyclic compounds such as diazabicycloundecene, quaternary ammonium, phosphonium or arsonium compounds. Various compounds have been used.

[0004] These commonly used curing catalysts often exhibit a curing promoting action even at a relatively low temperature such as room temperature. This causes a decrease in quality as a product, 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, a so-called latent curing accelerator which suppresses a change with time in viscosity and fluidity at a low temperature and causes a curing reaction only by heating during shaping and molding has been developed. Research is being actively pursued. As a means for protecting the active site of the curing accelerator with an ion pair, studies have been made to develop latentness.
In JP-A-41290, a latent curing accelerator having a salt structure of various organic acids and phosphonium ions is proposed. However, this phosphonium salt does not have a specific higher-order molecular structure, and the ion pair is relatively easily affected by the external environment. Therefore, the movement of molecules such as recent low-molecular epoxy resins and phenol aralkyl resins has occurred. A semiconductor sealing material using an easy curing agent has a problem that storage stability is reduced.

[0006]

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

[0007]

The present inventors use a molecular compound having a specific structure together with a compound having two or more epoxy groups in one molecule and a compound having two or more phenolic hydroxyl groups in one molecule. As a result, a resin composition having excellent curability and storage stability, and an epoxy resin molding material were obtained, and further, it was found that a semiconductor device having high moisture resistance reliability was obtained, and the present invention was completed. .

That is, the present invention provides 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) Molecular compound (C) represented by (2)
A thermosetting resin composition characterized by comprising an essential component,

[0009]

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[0010]

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(Where P is a phosphorus atom, R ¹ , R ² , R ³
And R ⁴ is a substituted or unsubstituted aromatic group or an alkyl group, A ¹ and A ³ are divalent aromatic groups, B is a single bond, or an ether group, a sulfone group, a sulfide group, a carbonyl group, or the like. A divalent substituent or a divalent organic group having 1 to 13 carbon atoms. )

The molecular compound (C) is represented by the general formula (3)
Or the thermosetting resin composition which is a molecular compound represented by (4),

[0013]

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[0014]

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(Where P is a phosphorus atom, R ¹ , R ² , R ³
And R ⁴ represent a substituted or unsubstituted aromatic group or an alkyl group, and R ⁵ , R ⁶ , R ⁷ and R ⁸ are a hydrogen atom or a halogen atom or a monovalent monovalent having 1 to 6 carbon atoms. Represents an organic group. X represents a single bond, a divalent substituent selected from an ether group, a sulfone group, a sulfide group, a carbonyl group and the like, or a divalent organic group having 1 to 13 carbon atoms. )

Further, a compound (A) having two or more epoxy groups in one molecule, a phenolic hydroxyl group in one molecule.
(B), a molecular compound (C) represented by the general formula (1) or (2), a molecular compound (C) represented by the general formula (3) or (4), and inorganic An epoxy resin molding material comprising a filler (D) as an essential component, and a semiconductor device sealed with a cured product thereof.

[0017]

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. Epoxy resins, epoxy compounds, etc. produced by reacting epichlorohydrin with hydroxyl groups such as biphenols, phenolic resins such as biphenol, phenolic resins, naphthols, etc., biphenyl type epoxy resin, novolak type epoxy resin, naphthalene type epoxy resin, etc. Can be Other examples include an epoxy resin such as an alicyclic epoxy resin obtained by oxidizing an olefin using a peracid and epoxidizing the same, or a resin obtained by epoxidizing dihydroxybenzenes such as hydroquinone with epichlorohydrin.

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

In the present invention, the molecular compound (C) which functions as a curing accelerator is a tetra-substituted phosphonium and a phenol compound represented by the general formula (1) or (2), and further represented by the general formula (3) or (4). Is a molecular association with
This molecular compound is composed of a unit of one tetra-substituted phosphonium cation, three phenolic hydroxyl groups and one phenoxide anion, and surrounds three positive phenolic hydroxyl groups with one phenolic hydroxyl group around the positive charge of the tetra-substituted phosphonium ion. It is considered that a single phenoxide anion surrounds and has a stabilized structure.

The phosphonium ion which can have such a structure is a tetra-substituted phosphonium ion having a substituted or unsubstituted aryl or alkyl group as a substituent.
Stable and preferable for hydrolysis, specifically, tetraphenylphosphonium, tetraaryl-substituted phosphonium such as tetratolylphosphonium, and phosphonium halide synthesized from triarylphosphine such as triphenylmethylphosphonium and alkyl halide. And tetraalkyl-substituted phosphoniums such as triarylmonoalkylphosphonium and tetrabutylphosphonium.

The 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), bisphenol S (2,2-bis (4-hydroxyphenyl) sulfone), bisphenol E (4,4-ethylidenebisphenol), bisphenolfluorene (4, Bisphenols such as 4- (9H-fluorene-9-ylidene) bisphenol), 4,4-methylidenebis (2,6-dimethylphenol), bis (4-hydroxyphenyl) methanone, 4,4-biphenol, 2,2 -Biphenols, biphenols such as 3,3,5,5-tetramethylbiphenol, hydroquinone, resorcinol, catechol,
Examples include 2,6-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,1-bi-2-naphthol, and 1,4-dihydroxyanthraquinone. In terms of the stability and curability of molecular compounds and physical properties of cured products, bisphenol A and bisphenol F (4,4-methylenebisphenol, 2,4-methylenebisphenol, 2,2-methylenebisphenol, and bisphenol F manufactured by Honshu Chemical Co., Ltd.) Preferred are bisphenol S, 4,4-biphenol, 2,2-biphenol, 2,6-dihydroxynaphthalene.

The molecular compound (C) is obtained by mixing the above-mentioned phenol compound with a base which finally helps dehydrohalogenation, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, pyridine or triethylamine. Is dissolved in a solvent such as alcohol, followed by adding and reacting the tetra-substituted phosphonium halide dissolved in an appropriate solvent, and finally taking out as a solid by an operation such as recrystallization or reprecipitation. It can be synthesized by a method or a method in which a tetra-substituted phosphonium tetra-substituted borate and a phenol compound are thermally reacted and then heated and reacted in a solvent such as alcohol.

The molecular compound (C) used in the present invention has a phosphonium-phenoxide type salt in its structure as described above, and this 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 is controlled only by the strength of the ionic bond. On the other hand, in the molecular compound (C), the ion pair at the reaction active site is surrounded by a higher-order structure at room temperature.
The active sites are protected, while in the actual shaping stage, the active sites are exposed due to the collapse of the higher-order structure, and so-called latency, which expresses reactivity, is imparted.

The compounding amount of the molecular compound (C), which functions as a curing accelerator and is used in the present invention, is a compound (A) having two or more epoxy groups in one molecule, and one molecule which functions as a curing agent. When the total weight of the compound (B) having two or more phenolic hydroxyl groups is 100 parts by weight,
About 0.5 to 20 parts by weight is suitable because the curability, storage stability and other properties are well balanced. 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 has two or more epoxy groups in one molecule. 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) per mole of the epoxy group of the compound (A). 0.5 to 2 mol, preferably 0.8
When used so as to have a molar ratio of about 1.2, the curability, heat resistance, electric characteristics, 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 silica powder, fused spherical silica powder, crystalline silica powder,
Sub-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 total amount of the compound (A) having two or more epoxy groups in one molecule and the compound (B) having two or more phenolic hydroxyl groups in one molecule. 200 to 2400 per part by weight
Parts by weight are preferred. If the amount is less than 200 parts by weight, the reinforcing effect of the inorganic filler may not be sufficiently exerted.
If the amount is more than 00 parts by weight, the fluidity of the resin composition is reduced, and there is a possibility that poor filling may occur during molding, which is not preferable. Particularly, the compounding amount of the inorganic filler is from 250 to 1400 per 100 parts by weight of the total amount of the components (A) and (B).
If it is part by weight, the moisture absorption of the cured product of the molding material will be low, it is possible to prevent the occurrence of solder cracks, and the viscosity of the molding material at the time of melting will be low. It is more preferable because it does not cause a risk.
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 when used in combination with other known catalysts such as undecene-7 and 2-methylimidazole.

The epoxy resin molding material of the present invention comprises (A)
-Component (D), other additives, etc. are mixed at room temperature using a mixer, kneaded with a kneader such as a roll or an extruder, cooled, and pulverized.

Using the epoxy resin molding material of the present invention,
In order to manufacture a semiconductor device by encapsulating an electronic component such as a semiconductor, curing and molding can be performed by a molding method such as transfer molding, compression molding, and injection molding.

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.

[0031]

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. The synthesized molecular compound (C) is reacted with a known excess amount of oxalic acid in a methanol / water-based solvent, and the remaining oxalic acid is quantified with an aqueous sodium hydroxide solution having a known normality. The normality per weight (N / g) was calculated. The reciprocal of this value is the phosphonium phenoxide equivalent.

(Synthesis Example 1) Bisphenol FD (mixture of bisphenol F isomers) manufactured by Honshu Chemical Industry Co., Ltd. was placed in a 1 liter separable flask equipped with a stirrer.
g (0.2 mol) and 100 ml of methanol were charged and dissolved by stirring at room temperature, and a solution of 4.0 g (0.1 mol) of sodium hydroxide previously dissolved in 50 ml of methanol was added with stirring. Next, a solution in which 41.9 g (0.1 mol) of tetraphenylphosphonium bromide was previously dissolved in 150 ml of methanol 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 is filtered and dried, and white crystals 7
1.9 g were obtained. This compound is designated as C1. C1 is NM
From the results of R, mass spectrum and elemental analysis, one molecule of tetraphenylphosphonium and bisphenol FD
It was confirmed that this was a target molecular compound represented by the general formula (3) complexed at a molar ratio of 1: 2. Also, from the value of the neutralization titration, the phosphonium phenoxide equivalent was close to the theoretical value of 738, indicating the above-mentioned structure. The yield of the synthesis was 97.4%.

(Synthesis Examples 2 to 6)
Under the conditions shown in (1), all the basic operations were performed in the same manner as in Synthesis Example 1 to prepare compounds C2 to C6, 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-3,5-
12.8 g (0.05 mol) of dimethylphenyl) methane and 50 ml of methanol were charged, and dissolved by stirring at room temperature.
(0.1 mol) was added in advance with a solution of 50 ml of methanol. Next, a solution in which 33.9 g (0.1 mol) of tetrabutylphosphonium bromide was previously dissolved in 150 ml of methanol 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 D1. As a result of performing the same analysis as in Synthesis Example 1,
A compound in which one molecule of tetrabutylphosphonium was ionically bonded to each phenoxide in which two protons of the two hydroxyl groups of bis (4-hydroxy-3,5-dimethylphenyl) methane were dissociated at a ratio of 1: 2. This D1 is a simple phosphonium salt and not a molecular compound used in the present invention.

(Comparative Synthesis Example 2) A 1-liter separable flask equipped with a stirrer was charged with p-phenylphenol 1
7.0 g (0.1 mol) and 50 ml of methanol were charged and dissolved by stirring at room temperature, and a solution in which 4.0 g (0.1 mol) of sodium hydroxide had been previously dissolved in 50 ml of methanol was added while stirring. Then, 41.9 g (0.1 mol) of tetraphenylphosphonium bromide was previously added to 1
A solution dissolved in 50 ml of methanol 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 with 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 added in advance with a solution of 50 ml of methanol. 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 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. Table 1 also summarizes the results of the comparative synthesis examples as in the other synthesis examples.

[0038]

[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 resin composition prepared by the above-described sample preparation method, a curast meter (JS, manufactured by Orientec, Inc.)
R Curastometer PS) at 175 ° C
The torque after 5 seconds was determined. Torque in a curast meter is a parameter of curability, and a larger value indicates higher curability. (2) Residual rate of curing heat generation (evaluation of storage stability) Using the resin 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. The measured calorific value after preservation (mJ / mg) relative to the initial curing calorific value (mJ / mg)
/ Mg) 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) For each of Examples 1 to 6 and Comparative Examples 1 to 4, a sample of the composition was prepared by the above-described method according to the formulation shown in Table 2. And evaluated. In Comparative Example 1, triphenylphosphine was used instead of the compound (C) in Examples, and Comparative Examples 2 to
4, compound D1 synthesized in Comparative Synthesis Examples 1 to 3 described above was used.
~ D3 was used. Table 2 shows the evaluation results of the obtained compositions.
As shown in FIG.

[0041]

[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
Those using a phosphonium salt which is not a molecular compound used in the present invention have good curability but poor storage stability.

[Evaluation of Epoxy Resin Molding Material] (Example 7) 52 parts by weight of YX-4000H (biphenyl type epoxy resin) made by Yuka Shell Epoxy 48 parts by weight of XL225 (phenol aralkyl resin) made by Mitsui Chemicals 3.0 parts by weight of molecular compound C1 Parts 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 kneaded at 95 ° C. for 8 minutes using a hot roll. After cooling, the mixture was pulverized to obtain an epoxy resin molding material. The obtained epoxy resin molding material was evaluated by the following method. Table 3 shows the results.

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 the larger the value, the better the fluidity. The unit is c
m. (2) The curing torque was measured at 175 ° C. for 45 seconds using a curastometer (manufactured by Orientec Co., Ltd., model JPS Curastometer IVPS). The larger the value, the better the curability. The unit is kgf ・ c
m. (3) The residual flow rate was obtained by measuring the spiral flow immediately after preparation and after storing at 30 ° C. for one week, and expressed as a percentage of the spiral flow immediately after preparation after storage. The larger the value, the better the preservability. Units%. (4) Moisture resistance reliability: mold temperature 175 ° C, pressure 70kg
/ Cm ² , and a curing time of 2 minutes to form a 16pDIP. The 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 6 pDIP, and the disconnection defect was examined. The time required until eight or more of the 15 packages failed was defined as a failure time. The unit is time. The measurement time is
The case where the number of defective packages was less than 8 at that time was 500 hours at the maximum, and 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 7) Example 8
~ 9 and Comparative Examples 5 to 7 according to the formulation in Table 3,
In the same manner as in Example 7, an epoxy resin molding material was prepared and evaluated. Table 3 shows the results.

[0046]

[Table 3]

The epoxy resin molding materials of the present invention of Examples 7 to 9 have extremely good storability and curability.
It can be seen that the semiconductor device sealed with the cured product of this epoxy resin molding material has good moisture resistance.

[0048]

The thermosetting resin composition and the epoxy resin molding material of the present invention have excellent curability and storage properties, and the semiconductor device sealed with the cured product of the epoxy resin molding material has a high moisture resistance. Excellent reliability and useful.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) H01L 23/31 (72) Inventor Akiko Okubo 2-5-8 Higashishinagawa, Shinagawa-ku, Tokyo Sumitomo Bakelite Co., Ltd. F term (reference) 4J002 CC042 CC052 CC072 CD021 CD041 CD051 CD061 DE137 DE147 DJ017 DJ037 DJ047 DL007 EJ026 EJ036 EV246 EW016 FA047 FD017 FD142 FD156 GQ05 4J036 AA01 AD07 AD08 AD13 AD15 AD07 DB07 FA06 JA07 4M109 EA03 EB03 EB04 EB06 EB07 EB08 EB09 EB12 EB19 EC01 EC03 EC14 EC20

Claims (5)

[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 Embedded image (Where P is a phosphorus atom, R ₁ , R ₂ , R ₃ and R ₄ are a substituted or unsubstituted aromatic or alkyl group, A ₁
And A ₂ is a divalent aromatic group, B ₁ is a single bond, or a divalent substituent selected from an ether group, a sulfone group, a sulfide group, and a carbonyl group, or a bivalent substituent group having 1 to 13 carbon atoms. Represents a valent organic group. 2. The thermosetting resin composition according to claim 1, wherein the molecular compound (C) is a molecular compound represented by the general formula (3) or (4). Embedded image Embedded image (However, 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 R ₅ , R ₆ , R ₇ and R ₈ represent a hydrogen atom or X represents a halogen atom or a monovalent organic group having 1 to 6 carbon atoms, and X represents a single bond, a divalent substituent selected from an ether group, a sulfone group, a sulfide group, and a carbonyl group, or a carbon atom number. Represents a divalent organic group composed of 1 to 13.) 3. 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 represented by the general formula (1) or (2). An epoxy resin molding material characterized by comprising a molecular compound (C) and an inorganic filler (D) as essential components. 4. The epoxy resin molding material according to claim 3, wherein the molecular compound (C) is a molecular compound represented by the general formula (3) or (4). 5. A semiconductor device sealed with a cured product of the epoxy resin molding material according to claim 3.