TWI766025B - Active ester compound and curable composition - Google Patents

Abstract

An object of the present invention is to provide an active ester compound having a low elastic modulus of a cured product under high temperature conditions, a curable composition containing the same, a cured product thereof, a semiconductor sealing material, and a printed wiring board. Specifically, the present invention provides an active ester compound, a curable composition containing the same, a cured product thereof, a semiconductor sealing material, and a printed wiring board, the active ester compound being a dihydroxybenzene compound (a1) and an aromatic monocarboxylic acid or an ester product of an acid halide (a2) thereof, wherein the dihydroxybenzene compound (a1) is a 1,2-dihydroxybenzene compound or a 1,3-dihydroxybenzene compound.

Description

Active ester compound and curable composition

The present invention relates to an active ester compound with a low elastic modulus under high temperature conditions, a curable composition containing the same, a cured product thereof, a semiconductor sealing material, and a printed wiring board.

In the technical field of insulating materials used in semiconductors, multilayer printed circuit boards, etc., along with thinning and miniaturization of various electronic components, it is required to develop novel resin materials that match these market trends. As a performance required for a semiconductor sealing material, in order to improve reflow solderability, a low elastic modulus under high temperature conditions is required. In addition, the heat resistance or moisture absorption resistance of the cured product is of course important. As a countermeasure to increase the speed and frequency of signals, it is important that the dielectric constant and dielectric loss tangent of the cured product are low, which is important for reliability under high temperature conditions. In other words, it is important that the physical properties such as glass transition temperature (Tg) do not change, and it is also important that the curing shrinkage and the coefficient of linear expansion are low as measures against warpage and deformation accompanying thinning.

As a resin material excellent in the heat resistance and dielectric properties of the cured product, a technique using bis(1-naphthyl isophthalate) as a curing agent for epoxy resins is known (refer to the following Patent Document 1). The epoxy resin composition described in Patent Document 1 is different from conventional epoxy resin hardeners such as phenol novolac resins by using di(α-naphthyl isophthalate) as the epoxy resin hardener. Compared with the previous case, the value of the dielectric constant or the dielectric loss tangent of the cured product is indeed lower, but the elastic modulus of the cured product under high temperature conditions does not meet the level required in recent years. In addition, since the melt viscosity is high, there is a limitation in use in applications requiring low melt viscosity, such as a semiconductor sealing material.

[Prior Art Literature]

[Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open No. 2003-82063

Therefore, the subject to be solved by the present invention is to provide an active ester compound having a low elastic modulus under high temperature conditions, a curable composition containing the same, a cured product thereof, a semiconductor sealing material, and a printed wiring board.

The inventors of the present invention, as a result of diligent research in order to solve the above-mentioned problems, found that a 1,2-dihydroxybenzene compound or a 1,3-dihydroxybenzene compound and an aromatic monocarboxylic acid or its acid halide are the second The active ester compound of the esterified product not only has a low elastic modulus under high temperature conditions, but also has a low melt viscosity, thereby completing the present invention.

That is, the present invention relates to an active ester compound which is an ester product of a dihydroxybenzene compound (a1) and an aromatic monocarboxylic acid or its acid halide (a2), wherein the dihydroxybenzene compound (a1) is 1,2 - a dihydroxybenzene compound or a 1,3-dihydroxybenzene compound.

The present invention further relates to a curable composition containing the above-mentioned active ester compound and a curing agent.

The present invention further relates to a cured product which is a cured product of the above-mentioned curable composition.

The present invention further relates to a semiconductor sealing material using the above curable composition.

The present invention further relates to a printed wiring board using the above curable composition.

According to the present invention, an active ester compound having a low elastic modulus of a cured product under high temperature conditions, a curable composition containing the same, a cured product thereof, a semiconductor sealing material, and a printed wiring board can be provided.

FIG. 1 is a GPC diagram of the active ester compound (1) obtained in Example 1. FIG.

Hereinafter, the present invention will be described in detail.

The active ester compound of the present invention is characterized in that it is an ester product of a dihydroxybenzene compound (a1) and an aromatic monocarboxylic acid or its acid halide (a2), and the dihydroxybenzene compound (a1) is a 1,2- Dihydroxybenzene compound or 1,3-dihydroxybenzene compound.

As said dihydroxybenzene compound (a1), 1, 2- dihydroxy benzene, 1, 3- dihydroxy benzene, and the dihydroxy benzene compound which has one or more substituents in these aromatic rings are mentioned. As said substituent, an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, an aralkyl group, etc. are mentioned, for example. The above-mentioned aliphatic hydrocarbon group may be either a straight chain type or a branched chain type, and may have an unsaturated bond in the structure. Specifically, alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, and hexyl; cycloalkyl groups such as cyclohexyl; Base et al. As said alkoxy group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc. are mentioned. As said halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. are mentioned. Examples of the above-mentioned aryl group include a phenyl group, a naphthyl group, an anthracenyl group, and a structural site in which the above-mentioned aliphatic hydrocarbon group, an alkoxy group, a halogen atom, and the like are substituted on these aromatic nuclei. Examples of the above-mentioned aralkyl group include benzyl group, phenylethyl group, naphthylmethyl group, naphthylethyl group, and structural moieties in which the above-mentioned alkyl group, alkoxy group, halogen atom, etc. are substituted on the aromatic nucleus thereof. The said dihydroxybenzene compound (a1) may be used individually by 1 type, and may use 2 or more types together.

Examples of the above-mentioned aromatic monocarboxylic acid or its acid halide (a2) include benzenecarboxylic acid, naphthalenecarboxylic acid, one or more aliphatic hydrocarbon groups, alkoxy groups, halogen atoms, aromatic Compounds of substituents such as radicals, aralkyls, etc., and acid halides of these, etc. These may be used individually by 1 type, and may use 2 or more types together. Among them, benzenecarboxylic acid or a halide thereof is preferable in terms of becoming an active ester compound having a low modulus of elasticity under high temperature conditions and excellent curability of the cured product. Therefore, as a more preferable structure of the active ester compound of this invention, what is represented by following structural formula (1-1) or (1-2) is mentioned.

(in the formula, R ¹ are each independently any one of aliphatic hydrocarbon group, alkoxy group, halogen atom, aryl group, aralkyl group, and can be bonded to any carbon atom forming a benzene ring; R ² are each independently It is any one of aliphatic hydrocarbon group, alkoxy group, halogen atom, aryl group and aralkyl group, and can be bonded to any carbon atom forming a benzene ring; m is 0 or an integer from 1 to 4, and n is 0 or Integer from 1 to 5)

The reaction of the above-mentioned dihydroxybenzene compound (a1) with an aromatic monocarboxylic acid or its acid halide (a2) can be carried out, for example, by heating and stirring at a temperature of about 40 to 65°C in the presence of an alkali catalyst. method to proceed. The reaction can also be carried out in an organic solvent as required. Moreover, after completion|finish of reaction, you may refine|purify a reaction product by water washing, reprecipitation, etc. as needed.

Examples of the above-mentioned alkali catalyst include sodium hydroxide, potassium hydroxide, triethylamine, pyridine and the like. These may be used independently, respectively, and may use 2 or more types together. In addition, it can also be used in the form of an aqueous solution of about 3.0 to 30%. Among them, sodium hydroxide or potassium hydroxide with high catalytic ability is preferable.

Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ethyl acetate, butyl acetate, cellosolve acetate, and propylene glycol monomethyl ether. Acetate solvents such as acetate and carbitol acetate; carbitol solvents such as cellulose and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; dimethylformamide, dimethylformamide, etc. Ethylacetamide, N-methylpyrrolidone, etc. These may be used independently, respectively, and may be used as a mixed solvent of 2 or more types.

The reaction ratio of the above-mentioned dihydroxybenzene compound (a1) with the aromatic monocarboxylic acid or its acid halide (a2) is preferably a ratio relative to the above-mentioned dihydroxyl group in terms of obtaining the target active ester compound in high yield The above-mentioned aromatic monocarboxylic acid or its acid halide (a2) is in a ratio of 0.95 to 1.05 mol based on the total of 1 mol of the hydroxyl groups contained in the benzene compound (a1).

The melt viscosity of the above-mentioned active ester compound is preferably in the range of 0.01~50dPa·s, more preferably in the range of 0.01~5dPa·s, and particularly preferably in the range of 0.01~50dPa·s as measured by ICI viscometer at 150°C according to ASTM D4287. The range of 0.01~0.1dPa‧s.

The curable composition of the present invention may contain the above-mentioned active ester compound of the present invention together with other active ester compounds. Examples of the above-mentioned other active ester compounds include: esters of a compound having one phenolic hydroxyl group in the molecular structure and an aromatic polycarboxylic acid or its acid halide; polyhydroxynaphthalene and an aromatic monocarboxylic acid or its acid halide Esterates of compounds; esters of compounds having one phenolic hydroxyl group in the molecular structure, aromatic polycarboxylic acids or acid halides thereof, and compounds having two or more phenolic hydroxyl groups in the molecular structure; aromatic polycarboxylic acids Carboxylic acid or its acid halide, a compound having two or more phenolic hydroxyl groups in its molecular structure, an esterified product of an aromatic monocarboxylic acid or its acid halide, and the like.

In the case of using the above-mentioned other active ester compounds, the ratio of the active ester compound of the present invention to the total of the active ester compound of the present invention and the other active ester compounds in terms of fully exerting the effects of the present invention, Preferably it is 80 mass % or more, More preferably, it is 90 mass % or more. In addition, the melt viscosity of the formulation of the active ester compound of the present invention and other active ester compounds is preferably in the range of 0.01-50 dPa·s, more preferably in the range of 0.01-5 dPa·s, particularly preferably in the range of 0.01-0.1 dPa·s range. The melt viscosity of the formulation is measured at 150°C using an ICI viscometer in accordance with ASTM D4287.

The curable composition of the present invention contains the above-mentioned active ester compound and a curing agent. The above-mentioned curing agent is not particularly limited as long as it is a compound capable of reacting with the above-mentioned active ester compound, and various compounds can be applied. As an example of a hardening|curing agent, an epoxy resin is mentioned, for example.

Examples of the above epoxy resins include phenol novolak epoxy resins, cresol novolak epoxy resins, naphthol novolak epoxy resins, bisphenol novolak epoxy resins, and biphenol novolak epoxy resins. Resin, bisphenol type epoxy resin, biphenyl type epoxy resin, triphenolmethane type epoxy resin, tetraphenolethane type epoxy resin, dicyclopentadiene-phenol addition reaction type epoxy resin, phenol aromatic Alkyl type epoxy resin, naphthol aralkyl type epoxy resin, etc.

In the curable composition of the present invention, the mixing ratio of the above-mentioned active ester compound and the curing agent is not particularly limited, and may be appropriately adjusted depending on the desired properties of the cured product. As an example of preparation in the case of using an epoxy resin as a curing agent, it is preferable that the total of the functional groups in the active ester compound is 0.7 to 1.5 per mol of the total epoxy groups in the curable composition. Molar ratio.

樹脂；苯乙烯-順丁烯二酸酐樹脂；以二烯丙基雙酚或三聚異氰酸三烯丙酯(triallyl isocyanurate)為代表之含烯丙基之樹脂；多磷酸酯或磷酸酯-碳酸酯共聚物等。該等可分別單獨地使用，亦可併用2種以上。該等其他樹脂成分之調配比例並無特別限定，可視所需之硬化物性能等適當進行調整。 The curable composition of the present invention may further contain other resin components. As other resin components, for example, diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylene, isophoronediamine, imidazole, and BF3-amine zirconium can be mentioned. amine compounds such as compounds and guanidine derivatives; dicyandiamide, polyamide resins synthesized from dimers of hypolinoleic acid and ethylenediamine, and other amide compounds; phthalic anhydride, trimethylene Trimellitic anhydride, pyrometic dianhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic acid anhydride, hexahydrophthalic anhydride Anhydrides such as hydrogen phthalic anhydride and methylhexahydrophthalic anhydride; cyanate ester resin; bismaleimide resin; benzoic acid

resin; styrene-maleic anhydride resin; allyl-containing resin represented by diallyl bisphenol or triallyl isocyanurate; polyphosphate or phosphate- carbonate copolymers, etc. These may be used independently, respectively, and may use 2 or more types together. The blending ratio of these other resin components is not particularly limited, and may be appropriately adjusted depending on the desired properties of the cured product.

The curable composition of the present invention may also contain various additives such as a curing accelerator, a flame retardant, an inorganic filler, a silane coupling agent, a mold release agent, a pigment, and an emulsifier as necessary.

Examples of the above-mentioned curing accelerator include phosphorus-based compounds, tertiary amines, imidazole compounds, pyridine compounds, organic acid metal salts, Lewis acids, ammonium zirconium salts, and the like. Among them, among phosphorus-based compounds, triphenylphosphine is preferable, and among tertiary amines, 1,8-diazabicyclo is preferable in terms of being excellent in curability, heat resistance, electrical properties, and moisture resistance reliability. -[5.4.0]-undecene (DBU), among the imidazole compounds, 2-ethyl-4-methylimidazole is preferred, and among the pyridine compounds, 4-dimethylaminopyridine is preferred.

化合物、三聚氰酸(cyanuric acid)化合物、異三聚氰酸化合物、啡噻

等氮系阻燃劑；聚矽氧油、聚矽氧橡膠、聚矽氧樹脂等聚矽氧系阻燃劑；金屬氫氧化物、金屬氧化物、金屬碳酸鹽化合物、金屬粉、硼化合物、低熔點玻璃等無機阻燃劑等。於使用該等阻燃劑之情形時，較佳為硬化性組成物中0.1~20質量%之範圍。 Examples of the flame retardant include: red phosphorus, ammonium phosphates such as monoammonium phosphate, diammonium phosphate, triammonium phosphate, and ammonium polyphosphate; inorganic phosphorus compounds such as phosphamide; phosphate ester compounds, phosphonic acid compounds, phosphinic acid ( phosphinic acid) compound, phosphine oxide (phosphine oxide) compound, phosphine (phosphorane) compound, organic nitrogen-containing phosphorus compound, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,7-dihydroxynaphthyl)-10H-9-oxa - Cyclic organophosphorus compounds such as 10-phosphaphenanthrene-10-oxide, and organophosphorus compounds such as derivatives obtained by reacting them with compounds such as epoxy resins or phenol resins; III

Compounds, cyanuric acid compounds, isocyanuric acid compounds, phenothia

Nitrogen-based flame retardants; polysiloxane-based flame retardants such as polysiloxane oil, polysiloxane rubber, and polysiloxane resin; metal hydroxides, metal oxides, metal carbonate compounds, metal powders, boron compounds, Inorganic flame retardants such as low melting point glass, etc. When these flame retardants are used, the range of 0.1 to 20 mass % in the curable composition is preferable.

The above-mentioned inorganic filler is prepared, for example, when the curable composition of the present invention is used for a semiconductor sealing material. Examples of the above-mentioned inorganic filler include fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide, and the like. Among them, the above-mentioned fused silica is preferable in terms of being able to mix more inorganic fillers. The above-mentioned fused silica can be either crushed or spherical. In order to increase the amount of fused silica to be blended and suppress the increase in the melt viscosity of the curable composition, spherical ones are preferably used. In order to further increase the compounding amount of spherical silica, it is better to appropriately adjust the particle size distribution of spherical silica. The filling rate is preferably prepared in the range of 0.5 to 95 parts by mass in 100 parts by mass of the curable composition.

Furthermore, when the curable composition of the present invention is used for applications such as conductive pastes, conductive fillers such as silver powder or copper powder can be used.

As described above in detail, the active ester compound of the present invention and the curable composition containing the same are characterized in that the cured product has a low modulus of elasticity under high temperature conditions. In addition, other general requirements required for resin materials are also sufficiently high, such as solubility in general-purpose organic solvents, or heat resistance, water absorption resistance, low curing shrinkage, dielectric properties, etc. Excellent and low melt viscosity. Therefore, in addition to printed wiring boards, semiconductor sealing materials, resist materials, and other electronic material applications, it can be widely used in applications such as paints, adhesives, and molded articles.

When the curable composition of the present invention is used for a printed wiring board application or a build-up adhesive film application, it is generally preferable to prepare and dilute an organic solvent for use. The above-mentioned organic solvent includes methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, methoxypropanol, cyclohexanone, methyl cellulose, ethyl diethylene glycol Acetate, propylene glycol monomethyl ether acetate, etc. The type or compounding amount of the organic solvent can be appropriately adjusted depending on the use environment of the curable composition. For example, in the application of printed wiring boards, methyl ethyl ketone, acetone, dimethylformamide, etc., preferably have a boiling point below 160°C The polar solvent is preferably used in a proportion of 40 to 80% by mass of nonvolatile content. In the application of build-up adhesive film, it is preferable to use ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone; ethyl acetate, butyl acetate, cellulose acetate, propylene glycol monomethyl ether acetate, carbitol Acetate solvents such as alcohol acetate; carbitol solvents such as cellulose and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; dimethylformamide, dimethylacetamide, N - Methylpyrrolidone etc., it is preferable to use it in the ratio which becomes 30-60 mass % of nonvolatile content.

Moreover, the method of manufacturing a printed wiring board using the curable composition of the present invention includes, for example, a method of impregnating a reinforcing base material with the curable composition, curing it to obtain a prepreg, and stacking it with a copper foil, Perform heat crimping. Examples of the reinforcing base material include paper, glass cloth, glass nonwoven fabric, aramid paper, aramid cloth, glass mat, glass roving, and the like. The impregnation amount of the curable composition is not particularly limited, but it is usually preferably prepared so that the resin component in the prepreg is 20 to 60 mass %.

When the curable composition of the present invention is used for a semiconductor sealing material, it is generally preferable to prepare an inorganic filler. The semiconductor sealing material can be prepared by mixing the formulation using, for example, an extruder, a kneader, a roll, or the like. As a method of molding a semiconductor package using the obtained semiconductor sealing material, for example, the semiconductor sealing material is molded using a casting molding, a transfer molding machine, an injection molding machine, etc., and the semiconductor sealing material is further formed at a temperature of 50 to 200° C. A method of heating for 2 to 10 hours, and by this method, a semiconductor device as a molded product can be obtained.

[Example]

Next, the present invention will be specifically described with reference to Examples and Comparative Examples. The descriptions of "parts" and "%" in the examples are the quality standards unless otherwise specified.

◆Melt viscosity measurement method

In the examples of this case, the melt viscosity of the active ester compound is obtained by measuring the melt viscosity at 150°C with an ICI viscometer according to ASTM D4287.

Example 1 Production of active ester compound (1)

Add 110 g of resorcinol and 1000 g of methyl isobutyl ketone to a flask equipped with a thermometer, dropping funnel, condenser tube, fractionation tube, and stirrer, and dissolve the system while replacing it with nitrogen under reduced pressure. . Next, 218 g of benzyl chloride was added, and the inside of the system was substituted with nitrogen under reduced pressure and dissolved. 0.5 g of tetrabutylammonium bromide was added, and while blowing nitrogen, the system was controlled to be below 60°C, and 420 g of a 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the dropwise addition, the stirring was continued for 1 hour and the reaction was carried out. After the completion of the reaction, the reaction mixture was left to stand for liquid separation, and the aqueous layer was removed. Water was added to the remaining organic layer, and after stirring and mixing for about 15 minutes, the mixture was left to stand for liquid separation, and the aqueous layer was removed. After repeating this operation until the pH value of the water layer became 7, the water and toluene were removed by dehydration with a decanter to obtain an active ester compound (1). The melt viscosity of the active ester compound (1) was 0.02 dPa·s.

Example 2 Production of active ester compound (2)

Add 110 g of catechol and 1000 g of methyl isobutyl ketone to a flask equipped with a thermometer, dropping funnel, condenser tube, fractionation tube, and stirrer, and dissolve the system while replacing it with nitrogen under reduced pressure. . Next, 218 g of benzyl chloride was added, and the system was dissolved while purging the system with nitrogen under reduced pressure. 0.5 g of tetrabutylammonium bromide was added, and while blowing nitrogen, the system was controlled to be below 60°C, and 420 g of a 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the dropwise addition, the stirring was continued for 1 hour and the reaction was carried out. After the completion of the reaction, the reaction mixture was left to stand for liquid separation, and the aqueous layer was removed. Water was added to the remaining organic layer, and after stirring and mixing for about 15 minutes, the mixture was left to stand for liquid separation, and the aqueous layer was removed. After repeating this operation until the pH value of the water layer became 7, the water and toluene were removed by dehydration with a decanter, and an active ester compound (2) was obtained. The melt viscosity of the active ester compound (2) was 0.02 dPa·s.

Example 3 Production of active ester compound (3)

Add 166 g of tertiary butyl catechol and 1100 g of methyl isobutyl ketone to a flask equipped with a thermometer, dropping funnel, condenser tube, fractionation tube, and stirrer, and conduct nitrogen gas under reduced pressure in the system. Displace one side to dissolve. Next, 218 g of benzyl chloride was added, and the system was dissolved while purging the system with nitrogen under reduced pressure. 0.6 g of tetrabutylammonium bromide was added, and while blowing nitrogen gas, the system was controlled to be below 60°C, and 420 g of a 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the dropwise addition, the stirring was continued for 1 hour and the reaction was carried out. After the completion of the reaction, the reaction mixture was left to stand for liquid separation, and the aqueous layer was removed. Water was added to the remaining organic layer, and after stirring and mixing for about 15 minutes, the mixture was left to stand for liquid separation, and the aqueous layer was removed. After repeating this operation until the pH value of the water layer became 7, water and toluene were removed by dehydration with a decanter, and an active ester compound (3) was obtained. The melt viscosity of the active ester compound (3) was 0.02 dPa·s.

Comparative Production Example 1 Production of Active Ester Compound (1')

202 g of isophthalic chloride and 1250 g of toluene were added to a flask equipped with a thermometer, dropping funnel, condenser, fractionation tube, and agitator, and dissolved while displacing the system with nitrogen under reduced pressure. Next, 288 g of 1-naphthol was added, and it melt|dissolved while nitrogen-substituting the inside of the system under reduced pressure. 0.6 g of tetrabutylammonium bromide was added, and while blowing nitrogen, the system was controlled to be below 60° C., and 420 g of a 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the dropwise addition, the stirring was continued for 1 hour and the reaction was carried out. After the completion of the reaction, the reaction mixture was left to stand for liquid separation, and the aqueous layer was removed. Water was added to the remaining organic layer, and after stirring and mixing for about 15 minutes, the mixture was left to stand for liquid separation, and the aqueous layer was removed. After repeating this operation until the pH value of the water layer became 7, water and toluene were removed by dehydration with a decanter, and an active ester compound (1') was obtained. The melt viscosity of the active ester compound (1') was 0.65 dPa·s.

Examples 4 to 6 and Comparative Example 1

Each component was blended in the ratio shown in the following Table 1 to manufacture a curable composition. The curable composition was poured into a mold frame, and molding was performed at a temperature of 175° C. for 10 minutes using a press. The molded product was taken out from the mold frame and hardened at a temperature of 175° C. for 5 hours to obtain a hardened product. About the hardened|cured material, the evaluation test was performed by the following method. The results are shown in Table 1.

Determination of storage elastic modulus at high temperature

A test piece having a size of 5 mm×54 mm×2.4 mm was cut out from the above-mentioned cured product. For the test piece, a viscoelasticity measuring device (“solid viscoelasticity measuring device RSAII” manufactured by Rheometric Corporation) was used to measure the storage elastic modulus at 260°C under the conditions of a rectangular tension method, a frequency of 1 Hz, and a heating temperature of 3°C/min.

Determination of Flexural Modulus of Elasticity and Flexural Strain at High Temperature

A test piece having a size of 25 mm×70 mm×2.4 mm was cut out from the above-mentioned cured product. With respect to the test piece, the flexural modulus of elasticity and flexural strain were measured under the conditions of a test speed of 1.0 mm/min and a test temperature of 260° C. using a universal testing machine (“Model 5582” manufactured by Instron Corporation).

Epoxy resin (*1): cresol novolak type epoxy resin (“N-655-EXP-S” manufactured by DIC Co., Ltd., epoxy equivalent 202 g/equivalent)

Claims (4)

A curable composition comprising an active ester compound and a curing agent, the active ester compound being an ester compound of a dihydroxybenzene compound (a1) and an aromatic monocarboxylic acid or its acid halide (a2), the The dihydroxybenzene compound (a1) is a 1,2-dihydroxybenzene compound or a 1,3-dihydroxybenzene compound, and the active ester compound is represented by the following structural formula (1-1) or (1-2) Molecular Structure,

(in the formula, R ¹ are each independently any one of aliphatic hydrocarbon group, alkoxy group, halogen atom, aryl group, aralkyl group, and can be bonded to any carbon atom forming a benzene ring; R ² are each independently It is any one of aliphatic hydrocarbon group, alkoxy group, halogen atom, aryl group and aralkyl group, and can be bonded to any carbon atom forming a benzene ring; m is 0 or an integer from 1 to 4, and n is 0 or an integer from 1 to 5). A cured product of the curable composition of claim 1. A semiconductor sealing material using the curable composition of claim 1. A printed wiring board using the curable composition of claim 1.

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