JPH0656964A - Epoxy resin composition for electronic component, epoxy resin, and production of epoxy resin - Google Patents

Abstract

PURPOSE:To obtain the epoxy resin composition excellent in reliability of humidity resistance by forming a composition essentially consisting of an epoxy resin, a curing agent and a cure accelerator, wherein the epoxy resin has a specified structure. CONSTITUTION:The resin composition essentially consists of an epoxy resin, a curing agent and a cure accelerator. The epoxy resin has desirably a structure composed of a glycidyloxyarylene bond, an ethylidene bond, an arylene bond and an ethylidene bond bonded to each other in the given order, glycidyloxynaphthylene, bis(glycidyloxy)-naphthylene or glycidyloxyphenylene, more desirably a structure of the formula [wherein G is glycidyl; A is a (lower- alkyl-substituted) benzene ring or naphthalene ring; m is 1 or 2; and n is 0-10].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin composition for electronic parts, which provides electronic parts having particularly excellent moisture resistance reliability.

[0002]

2. Description of the Related Art Semiconductors such as transistors, ICs and LSIs, and electric / electronic parts such as diodes and display elements are usually sealed in a ceramic package or a plastic package to form a device. The above packages are originally intended to improve the environmental resistance characteristics of electrical and electronic devices. Although plastic packages are inexpensive and have excellent mass productivity, they are ceramic packages with characteristics such as heat resistance, moisture permeation resistance, and moisture absorption resistance. It is inferior to the above, and its improvement has been strongly demanded.

Therefore, conventionally, an o-cresol novolac epoxy resin composition has been used in a plastic package.

[0004]

However, the above-mentioned o-cresol novolac epoxy resin has a drawback that sufficient moisture resistance cannot be obtained for a plastic package for sealing high-density electronic parts in recent years.

The problem to be solved by the present invention is to provide an epoxy resin having extremely excellent moisture resistance, and an epoxy resin composition for electronic parts using the same.

[0006]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that a glycidyloxyarylene bond, an ethylidene bond, an arylene bond,
When the ethylidene bond and the epoxy resin having an epoxy compound having a structure bonded in this order as an essential component are used for electronic part applications, the moisture resistance of the cured product is remarkably improved, and, for example, the crack occurrence rate of the package molded product. It was found that the thermal shock resistance represented by the decrease of the above was improved, and the present invention was completed.

That is, according to the present invention, in an epoxy resin composition for electronic parts, which comprises an epoxy resin, a curing agent and a curing accelerator as essential components, the epoxy resin comprises a glycidyloxyarylene bond, an ethylidene bond, an arylene bond and an ethylidene bond. And an epoxy resin composition for electronic parts, which has a structure bonded in this order, and an epoxy resin structural formula (1) represented by the following structural formula (1)

[0008]

[Chemical 2]

(In the formula, G represents a glycidyl group, A represents a benzene ring, a benzene ring substituted with a lower alkyl group or a naphthalene ring, m represents 1 or 2, and n represents an integer of 0 to 10.) And a method for producing an epoxy resin, which comprises reacting an aromatic hydrocarbon containing a phenolic hydroxyl group with an aromatic compound having at least two vinyl groups, and then reacting the obtained polyol compound with epihalohydrin Regarding the method.

The epoxy resin used in the epoxy resin composition for electronic parts of the present invention contains, as an essential component, an epoxy compound in which a glycidyloxyarylene bond, an ethylidene bond, an arylene bond and an ethylidene bond are bonded in this order.

The glycidyloxyarylene bond is not particularly limited, but glycidyloxyphenylene, glycidyloxynaphthylene, bis (glycidyloxy) naphthylene and the like are preferably mentioned.
Of these, glycidyloxynaphthylene and bis (glycidyloxy) naphthylene are preferable from the viewpoint of further improving the heat resistance and moisture resistance of the cured product.

Further, instead of the glycidyloxyarylene bond, glycidyloxyphenylene, glycidyloxynaphthylene, and bis (glycidyloxy) naphthylene are linked as a methylene group or a 2,2-propylene group to form a dimer. You may use the thing.

On the other hand, the arylene bond is not particularly limited, and examples thereof include phenylene and naphthylene. Among them, phenylene is preferable from the viewpoint of excellent moisture resistance of the cured product.

Specifically as such an epoxy resin,
For example, the epoxy resin of the present invention represented by the following structural formula (1) is preferable. Structural formula (1)

[0015]

[Chemical 3]

(In the formula, G represents a glycidyl group, A represents a benzene ring, a benzene ring substituted with a lower alkyl group or a naphthalene ring, m represents 1 or 2 and n represents an integer of 0 to 6, respectively.) Here, n represents the average number in the synthesized resin, and is usually an integer of 0 to 10, preferably 0 to 6.

The epoxy resin represented by the above structural formula is
The aralkyl group generated by the Friedel-Crafts reaction derived from a compound having a monofunctional ethylenically unsaturated double bond on the arylene skeleton to which a glycidyl group is bonded may be substituted.

The above-mentioned epoxy resin usually has a weight average molecular weight of 430 to 20,000 and an epoxy equivalent of 150.
However, the weight average molecular weight is preferably 430 to 10,000 from the viewpoint of excellent heat resistance.

Such an epoxy resin exhibits a particularly excellent balance in heat resistance and humidity resistance due to the characteristics of the molecular structure forming its skeleton. In other words, the epoxy resin has a structure in which hydrocarbon chain parts and naphthol (dihydroxynaphthalene) parts are alternately arranged, so that while maintaining the excellent heat resistance of the past, the effect of the hydrocarbon part significantly improves its moisture resistance. To do.

The production method of the above-mentioned epoxy resin is not particularly limited, but for example, the production method of the present invention described in detail below is preferable. That is, the method for producing an epoxy resin of the present invention comprises reacting an aromatic hydrocarbon containing a phenolic hydroxyl group with an aromatic compound having at least two vinyl groups, and then reacting the obtained polyol compound with epihalohydrin. Then, a glycidyl ether group is formed to obtain the desired epoxy resin.

The structure of the aromatic hydrocarbon containing a phenolic hydroxyl group is not particularly limited, but phenol, cresol, naphthol and dihydroxynaphthol are preferable because they are excellent in improving the moisture resistance of the cured product. Specific examples of these are phenol, o or p-cresol, p-tertiarybutylphenol, α-naphthol, β-naphthol, 1,
6-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-
Dihydroxynaphthalene may be mentioned. These may be used alone or in combination of two or more.

In addition to these, bisphenol A, bisphenol F, bis (hydroxynaphthyl) methane,
Bis (hydroxynaphthyl) propane, bis (dihydroxynaphthyl) methane, bis (dihydroxynaphthyl)
You may use propane etc.

Examples of the aromatic compound having at least two vinyl groups include divinylbenzene, divinylnaphthalene and divinylbiphenyl. These may be used alone or in combination of two or more.

Next, the method for producing the above-mentioned epoxy compound will be described in more detail. The method for producing an epoxy resin of the present invention relates to an aromatic hydrocarbon having a phenolic hydroxyl group and an aromatic compound having at least two vinyl groups. The first step of alternating polymerization of the two components by Friedel-Crafts type reaction in the presence of an acid catalyst to obtain a novolac resin (hereinafter referred to as a polyol compound), and epihalohydrin is added to this polyol compound as a basic compound such as NaOH or KOH. After the addition reaction is carried out in the presence of the compound, a desalting reaction is carried out to generate a glycidyl ether group, and the second step of obtaining the target epoxy resin is constituted.

In the first step, it is excellent in heat resistance that the aromatic compound having at least two vinyl groups is usually 0.3 to 1.0 mol per mol of the aromatic compound containing a phenolic hydroxyl group. It is preferable from the viewpoint that the molecular weight can be adjusted to an appropriate molecular weight, and it is particularly preferably 0.5 to 0.9 mol. The optimum value of this usage rate varies depending on the type of raw material or its purity.

The reaction catalyst used in the first step includes metal chlorides such as aluminum chloride and stannic chloride, mineral acids such as sulfuric acid, hydrochloric acid and phosphoric acid, and sulfonic acids such as benzenesulfonic acid and paratoluenesulfonic acid. Organic carboxylic acids such as acetic acid, acetic acid, oxalic acid and maleic acid are used. Preferably, a metal chloride that is a Friedel-Crafts catalyst, a mineral acid, or one that uses an organic sulfonic acid, whereby the reaction is completed in a short time,
It becomes easy to obtain a resin having a narrow molecular weight distribution. The amount of the catalyst used varies depending on the reaction system, but is generally preferably 0.1% by weight or more and 5.0% by weight or less with respect to the component (a).

The reaction temperature during the production of the polyol compound is not particularly limited, but is preferably 110 ° C. or higher, and a solvent inert to the reaction can be used if necessary. The polyol compound produced here may be isolated once and then led to the subsequent step of epoxidation, which is the second step.
It is also possible to deactivate the catalyst of the first step by neutralization, washing with water, etc. in the reactor and then carry out the epoxidation without isolation and acquisition.

The second step of producing an epoxy resin by reacting a polyol compound with epihalohydrin can be carried out by the same method as in the case of a known and conventional novolac type epoxy resin.

That is, an equivalent amount or more of epihalohydrin with respect to the phenolic hydroxyl group of the polyol compound is reacted in the presence of an equivalent amount or more of NaOH, KOH or the like, and then the inorganic salt or catalyst residue contained in the resin is washed with water or the like. The method of removing by a method is mentioned.

Examples of the epihalohydrin used in the present invention include epichlorohydrin, epibromohydrin,
β-methylepichlorohydrin and the like can be mentioned, with epichlorohydrin being preferred.

The epoxy resin of the present invention is characterized by excellent moisture resistance. For example, in the case of using the above-mentioned structural formula (1) with an equivalent amount of a phenol novolac resin as a curing agent, 85 ° C. and 85% R.V. H. After the lapse of 300 hours under the conditions of No. 1, the water absorption rate is about 48% as compared with the corresponding o-cresol novolac type epoxy resin having the same softening point.
Further, the storage elastic modulus in the cured product is only 20% in the region exceeding the glass transition point (220 ° C.).

This clearly indicates that the epoxy resin composition disclosed in the present invention is suitable for encapsulation of electronic parts, and more specifically, a cured molded article has a low water absorption rate and is subjected to thermal shock. In this case, it is expected that the generation of cracks is expected to be suppressed.

The epoxy resin composition for electronic parts of the present invention contains the above-mentioned epoxy resin, curing agent and curing accelerator as essential components, but the curing agent is not particularly limited. For example, any of those used as a curing agent for epoxy resins such as phenol novolac resins, amines, acid anhydrides and other latent curing agents can be used.

The mixing ratio of the epoxy resin and the curing agent is preferably such that the curing agent is 0.5 to 2.0 equivalents per equivalent of epoxy groups in the epoxy resin, more preferably 0.8 to 1.2 equivalents.

The curing accelerator used in the present invention is to assist the reaction between the epoxy resin and the curing agent,
For example, tertiary amines such as 2,4,6-tris (dimethylamino) phenol and benzyldimethylamine, 2
-Methyl-4-methylimidazoles may be mentioned.

As the epoxy resin used in the epoxy resin composition for electronic parts of the present invention, the above-mentioned epoxy resins may be used alone, but further other epoxy resins may be blended.

Other epoxy resins include general-purpose BPA.
Examples thereof include epoxy resins such as type epoxy resin, BPF type epoxy resin, phenol novolac type epoxy resin, and cresol novolac type epoxy resin.

In this case, the mixing ratio of the epoxy resin having the unit structure in which the glycidyloxynaphthylene bond, the ethylidene bond, the arylene bond, and the ethylidene bond are bonded in this order is determined by the characteristics depending on the mixing amount. In order to show, the mixing ratio may be selected within the range where the balance between the required water absorption rate and other characteristics is allowed.

In addition, an inorganic substance is generally used as a filler together with the above-mentioned essential components, and examples thereof include crystalline silica, fused silica, alumina, calcium carbonate, glass and the like. It is preferable to set such an inorganic substance filler in the range of 0 to 90% of the whole epoxy resin composition. Further, additives such as a surface treatment agent, a pigment, a flame retardant, and a lubricant may be used in combination for the purpose of assisting the moldability of the epoxy resin composition.

As a method for producing an epoxy resin composition for electronic parts, for example, a predetermined amount of an epoxy resin, a curing agent, and other additives and fillers if necessary, are mixed, and, for example, after sufficiently mixed by a mixer, The desired epoxy resin composition for electronic parts can be obtained by performing a mixing process such as melting or kneading, and if necessary, a molding process such as tableting.

The method for encapsulating electric / electronic parts using such an epoxy resin composition is not particularly limited, and a usual method such as transfer molding,
It can be carried out by a known method such as injection molding.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.

[0043]

【Example】

Production Example 1 [First Step] 940 parts of phenol and 5 parts of aluminum chloride were added in a reaction vessel equipped with a stirrer, a thermometer, and a cooling tube, and then reacted at 90 ° C. for 30 minutes. Then 80
% P-divinylbenzene (976 parts) was added dropwise over 2 hours, and then held at 140 ° C. for 3 hours, then the contents were taken out from the reactor in a molten state and a phenolic hydroxyl group equivalent (212 g / eq) of the polyol compound (A) was obtained. Obtained.

[Second Step] In a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, 100 parts of the polyol compound (A) was dissolved in 220 parts of epichlorohydrin, and then stirred at 80 ° C. for 20 minutes. A 1000% aqueous sodium hydroxide solution was added dropwise over 5 hours, the reaction was continued for 1 hour, and then the aqueous layer was discarded by liquid separation operation. Excess epichlorohydrin present in the organic layer was recovered by distillation to obtain a reaction crude product. 250 parts of methyl isobutyl ketone was added thereto to uniformly dissolve the contents, and then 8
The organic layer was washed with 0 part of water, the water was removed from the oil layer by azeotropic distillation, the insoluble matter precipitated was removed by filtration, and then methyl isobutyl ketone was distilled off to give a softening point of 78.4.
C., melt viscosity 3.0 (ps, 150.degree. C.), epoxy equivalent of 310 g / eq, weight average molecular weight of 3900, molecular weight distribution of 300 to 10,000 (polystyrene conversion) and the following structural formula. An epoxy resin (a) having an average n of 3 in (2) was obtained. Structural formula (2)

[0045]

[Chemical 4]

This substance was subjected to carbon 13 -NMR measurement using deuterium-substituted dimethyl sulfoxide as a solvent. This chart is shown in FIG. In FIG. 1, carbon 13-NM
The attribution of the signals in the R diagram is as follows. In addition, regarding the ppm value of the chemical shift, the value of carbon atoms in tetramethylsilane used as an internal standard is 0.

Multiple peaks of 21 to 24 ppm: Methyl group in crosslinked ethylidene group 38 ppm peak: Methine carbon in crosslinked ethylidene group 44 ppm peak: Methine carbon in crosslinked ethylidene group and methylene carbon in glycidyl group overlap 50 ppm Peak: methylene carbon in the three-membered ring in glycidyl group 69 ppm peak: methine carbon in glycidyl group 16 ppm and 30 ppm peaks are signals of terminal ethyl groups generated by addition of ethylvinylbenzene in divinylbenzene to phenol. .

All peaks from 115 to 160 ppm belong to aromatic hydrocarbons, of which 116 ppm and 1
21ppm, 128ppm, 153ppm is phenol part, 125-133ppm and 139-150pp
m is assigned to the benzene ring in the crosslinked divinylbenzene.

The infrared absorption spectrum of this substance was measured, and the results are shown in FIG. Example 2 [First step] The procedure of Example 1 was repeated except that 976 parts of p-divinylbenzene having a purity of 80% was replaced with 800 parts of p-divinylbenzene having a purity of 98%, and 1080 parts of cresol was replaced with 940 parts of phenol. The same reaction as in the first step was carried out to obtain a polyol compound (B). The polyol compound (B) obtained here had a melting point of 90 ° C. and a phenolic hydroxyl group equivalent of 231.

[Second Step] The softening point is the same as in Example 1 [second step] except that 80 parts of the polyol compound (B) obtained in the first step is used instead of the polyol compound (A). An epoxy resin (b) having a melt viscosity of 97 ° C., 3.2 (ps, 150 ° C.) and an epoxy equivalent of 320 g / eq was obtained.

Example 3 [First Step] In a reaction vessel equipped with a stirrer, a thermometer and a cooling tube, 117 parts of 80% p-divinylbenzene and 288 parts of β-naphthol were uniformly dissolved and then at 150 ° C. p-
8 parts of toluenesulfonic acid was added, and the reaction was carried out for 5 hours while maintaining the temperature. Thereafter, 1000 parts of methyl isobutyl ketone (MIBK) was added, the contents were dissolved and then 500 parts of water was added, and the organic layer was washed with water to remove the catalyst. Then, MIBK was distilled off to obtain 385 parts of a polyol compound (C) having a hydroxyl equivalent of 222 g / eq and having a structure in which a naphthol ring was knotted by an arylene alkylene bond as a unit structure.

[Second Step] In a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, 500 parts of the polyol compound (C) was dissolved in 1050 parts of epichlorohydrin, and then stirred at 80 ° C. for 20 minutes. % Aqueous sodium hydroxide solution (510 parts) was added dropwise over 5 hours, the reaction was further continued for 1 hour, and then the aqueous layer was discarded by liquid separation operation. Excess epichlorohydrin present in the organic layer was recovered by distillation to obtain a reaction crude product. To this, 300 parts of MIBK was added and the contents were uniformly dissolved.
The organic layer was washed and MIBK was distilled off from the oil layer to obtain a softening point of 85 ° C. and a melt viscosity of 2.3 (ps, 150
° C), the epoxy equivalent is 295 g / eq, the weight average molecular weight (converted to polystyrene) measured by gel permeation chromatography is 600, and n is represented by the following structural formula (3).
620 parts of an epoxy resin (C) having an average of 0.2 was obtained. Structural formula (3)

[0053]

[Chemical 5]

(In the formula, G represents a glycidyl group.) This substance was subjected to carbon 13-NMR measurement using deuterium-substituted dimethyl sulfoxide as a solvent. This chart is shown in FIG.

In FIG. 3, the attributions of signals in the carbon-13-NMR diagram are as follows. In addition, regarding the ppm value of the chemical shift, the value of carbon atoms in tetramethylsilane used as an internal standard is 0.

18 to 19 ppm peak: methyl group in crosslinked ethylidene group 35 ppm peak: methine carbon in crosslinked ethylidene group 45 ppm peak: three-membered ring methylene carbon in glycidyl group 50 ppm peak: methine in glycidyl group Carbon 70 ppm peak: Methylene carbon in glycidyl group The 15 ppm and 35 ppm peaks are signals of the terminal ethyl group produced by the addition of ethyl vinylbenzene in β-naphthol in divinylbenzene.

The peaks from 115 to 155 ppm are assigned to carbons in the naphthalene ring and the benzene ring. Moreover, the chart which measured the gel permeation chromatography of this epoxy resin (C) is shown in FIG.

Example 4 [First Step] β-Naphthol was replaced with 288 parts of 2,7
-In the same manner as in Example 1 [Step 1] except that 480 parts of dihydroxynaphthalene was used, 530 parts of a polyol compound (D) having 2,7-dihydroxynaphthalene in the skeleton and having a hydroxyl equivalent of 100 g / eq was obtained. .

[Second Step] 300 parts of the polyol compound (D) was dissolved in 1400 parts of epichlorohydrin in a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, and then stirred at 80 ° C. for 20 minutes. % Aqueous sodium hydroxide solution (675 parts) was added dropwise over 5 hours, the reaction was further continued for 1 hour, and then the aqueous layer was discarded by liquid separation operation. Excess epichlorohydrin present in the organic layer was recovered by distillation to obtain a reaction crude product. To this, 700 parts of MIBK was added to uniformly dissolve the contents, and then 320 parts of water were added.
The organic layer was washed three times, and MIBK was distilled off from the oil layer to give a softening point of 73 ° C. and a melt viscosity of 2.6 (ps, 150).
° C), the epoxy equivalent is 156 g / eq, the weight average molecular weight is 890 (measured by gel permeation chromatography) (in terms of polystyrene), and n is the following structural formula (4).
440 parts of epoxy resin (D) of epoxy resin having an average of 0.6 was obtained. Structural formula (4)

[0060]

[Chemical 6]

(In the formula, G represents a glycidyl group.) Also, a chart of measurement of gel permeation chromatography of this epoxy resin (D) is shown in FIG.

Examples 5 to 8 The epoxy resins (A) to (D) obtained in Examples 1 to 4
In addition, as a curing agent, phenol novolac resin ("Barcam TD-2131" manufactured by Dainippon Ink and Chemicals, Inc., melting point 8)
(0 ° C.) in an amount such that the epoxy groups and the hydroxyl groups of the phenol novolac resin are equivalent, and triphenylphosphine as a curing accelerator is added in 0.1 phr in Examples 1 and 2 and 0.2 phr in Examples 3 and 4, respectively. Then, an epoxy resin composition for electronic parts was obtained.

Then, one of these epoxy resin compositions was prepared.
Curing was carried out under the conditions of 50 ° C. for 2 hours and then 180 ° C. for 5 hours, and test pieces were prepared and measured for physical properties. The results are shown in Table 1.

Comparative Example 1 Ortho-cresol novolac type epoxy resin (“Epiclone N- manufactured by Dainippon Ink and Chemicals, Inc. as an epoxy resin
665 ", softening point 68 ° C, melt viscosity 2.9 (ps, 15
0 ° C.), an epoxy equivalent of 207 g / eq), and a phenol novolac resin (“Barcam TD-2131” manufactured by Dainippon Ink and Chemicals, Inc., melting point 80 ° C.) as a curing agent, with epoxy groups and hydroxyl groups of the phenol novolac resin equivalent Triphenylphosphine as a curing accelerator was further added in an amount of 0.1 phr to obtain an epoxy resin composition for electronic parts.

Next, this epoxy resin composition was added to 150
The test piece was prepared by curing the test piece at 2 ° C. for 2 hours and then at 180 ° C. for 5 hours, and the physical properties were measured. The results are shown in Table 1.

[0066]

[Table 1] (Method for measuring physical properties of cured epoxy resin) [Water absorption rate] 300 in a constant temperature and humidity tank at 85 ° C and 85% RH
It was calculated from the weight change when left for a time.

[Glass Transition Point] Dynamic Viscoelasticity Measuring Device (D
(MA) was used to measure the above-mentioned molded products. [Bending Strength / Tensile Strength] Bending strength / tensile strength was measured according to a general test method for thermosetting plastics (JIS K6911).

[0068]

EFFECT OF THE INVENTION According to the present invention, an epoxy resin composition for electronic parts having excellent performance in moisture resistance can be obtained.
By using this, excellent moisture resistance reliability can be imparted to electric / electronic parts.

[Brief description of drawings]

FIG. 1 is a carbon 13-NM of epoxy resin (A).
It is a measurement diagram of R.

FIG. 2 is a measurement diagram of an infrared absorption spectrum of epoxy resin (A).

FIG. 3 is a carbon 13-NM of epoxy resin (C).
It is a measurement diagram of R.

FIG. 4 is a measurement diagram of gel permeation chromatography of epoxy resin (C).

FIG. 5 is a measurement diagram of gel permeation chromatography of epoxy resin (D).

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shunji Ehara 1-929-1 Hondada-cho, Midori-ku, Chiba-shi, Chiba (72) Inventor Hiroshi Sakata 4-4 Tatsumidai-higashi, Ichihara-shi, Chiba

Claims (7)

[Claims] 1. An epoxy resin composition for electronic parts, which comprises an epoxy resin, a curing agent and a curing accelerator as essential components, wherein the epoxy resin has a glycidyloxyarylene bond, an ethylidene bond, an arylene bond and an ethylidene bond. An epoxy resin composition for electronic parts, which has a structure of bonding in this order. 2. The composition according to claim 1, wherein the glycidyloxyarylene bond in the epoxy resin is glycidyloxynaphthylene, bis (glycidyloxy) naphthylene or glycidyloxyphenylene. 3. An epoxy resin represented by the following structural formula (1). Structural formula (1) (In the formula, G represents a glycidyl group, A represents a benzene ring, a benzene ring substituted with a lower alkyl group or a naphthalene ring, m represents 1 or 2, and n represents an integer of 0 to 10.) 4. An epoxy resin characterized by reacting an aromatic hydrocarbon containing a phenolic hydroxyl group with an aromatic compound having at least two vinyl groups, and then reacting the obtained polyol compound with epihalohydrin. Manufacturing method. 5. The method according to claim 4, wherein the aromatic hydrocarbon containing a phenolic hydroxyl group is selected from the group consisting of phenol, cresol, naphthol and dihydroxynaphthalene. 6. The method according to claim 4, wherein the aromatic compound having at least two ethylenically unsaturated double bonds is p-divinylbenzene. 7. A vinyl group is used as an aromatic compound in an amount of 0.1 mol per mol of an aromatic hydrocarbon containing a phenolic hydroxyl group.
The method according to any one of claims 4 to 6, wherein 3 to 1.0 mol of the compound is reacted, and then the obtained polyol compound is reacted with epihalohydrin.