JP2010229295A - Epoxy resin composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an epoxy resin composition useful for forming an epoxy resin cured product having high thermal conductivity although the composition is soluble in a solvent, in the epoxy resin composition including a biphenyl epoxy resin. <P>SOLUTION: The epoxy resin composition includes a biphenyl type epoxy resin, wherein the composition contains, with a biphenyl type epoxy resin, a condensed polymer prepared by dehydration condensation of a hydrolyzed product, which is obtained by hydrolyzing an organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in the molecule, in the presence of the biphenyl type epoxy resin. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an epoxy resin composition, and more particularly to an epoxy resin composition containing a biphenyl type epoxy resin.

  Conventionally, an epoxy resin composition containing an epoxy resin is used for various applications because it is superior to other general resin compositions in terms of heat resistance and mechanical strength, For example, when forming a member that requires heat resistance, this epoxy resin composition is usually cured and used as a cured product (cured epoxy resin).

  This epoxy resin composition is widely used for electronic component applications such as semiconductor package sealing materials and circuit board insulation materials. In these applications, heat resistance and excellent thermal conductivity are required. For this reason, it is widely practiced to improve the thermal conductivity by highly filling the epoxy resin composition with inorganic particles as a filler.

  Regarding the thermal conductivity of this epoxy resin composition, not only measures by filling with an inorganic filler but also improving the thermal conductivity of the epoxy resin itself has been studied. For example, the following Non-Patent Document 1 discloses a mesogenic skeleton. An epoxy resin cured product having a thermal conductivity of about 5 times the thermal conductivity of 0.19 W / mK, which is the thermal conductivity of a general epoxy resin, is formed by using an epoxy resin having a high crystallinity. It is reported that it can be obtained.

In addition, since biphenyl type epoxy resins exhibit higher thermal conductivity than general epoxy resins, application of epoxy resin compositions containing biphenyl type epoxy has been widely attempted in recent years (Patent Document 1 below). reference).
However, since the biphenyl type epoxy resin has high crystallinity, it hardly dissolves in a general organic solvent. For example, it becomes difficult to use an epoxy resin composition containing a biphenyl type epoxy resin in a varnish state. Yes.

  Various attempts have been made to solubilize this biphenyl type epoxy resin, but it should be soluble in a solvent while suppressing a significant decrease in the effect of improving the thermal conductivity of the biphenyl type epoxy resin. Technology has not yet been established.

JP 2003-137971 A

Future materials vol. 7 No. No. 11 “Highly Thermally Conductive Liquid Crystal Epoxy Resin”

  The present invention provides an epoxy resin composition containing a biphenyl type epoxy resin, which is useful for forming a cured epoxy resin having a high thermal conductivity while being soluble in a solvent. It is an issue.

  The present invention according to an epoxy resin composition for solving the above problems is an epoxy resin composition containing a biphenyl type epoxy resin, and has a glycidyl group and a hydrolyzable alkoxysilane group in one molecule. A condensation polymer obtained by dehydrating and condensing a hydrolysis product obtained by hydrolyzing an organoalkoxysilane compound in the presence of a biphenyl type epoxy resin is contained together with the biphenyl type epoxy resin.

Since the epoxy resin composition according to the present invention contains a biphenyl type epoxy resin, it can form an epoxy resin cured product having excellent thermal conductivity.
Moreover, the epoxy resin composition according to the present invention is a hydrolyzed product obtained by hydrolyzing an organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in one molecule in the presence of a biphenyl type epoxy resin. Since the condensation polymer obtained by dehydration condensation is contained together with the biphenyl type epoxy resin, for example, it becomes soluble in a general organic solvent such as methyl ethyl ketone.
That is, according to the present invention, an epoxy resin composition useful for forming an epoxy resin cured product having high thermal conductivity while being soluble in a solvent can be provided.

The preferred embodiments of the present invention will be described below.
In the present embodiment, the epoxy resin composition dehydrates and condenses a hydrolysis product formed by hydrolyzing a biphenyl type epoxy resin and an organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in one molecule. In addition, the condensation polymer is a product obtained by the dehydration condensation in the presence of the biphenyl type epoxy resin.

Examples of the biphenyl type epoxy resin include 4,4′-bis (2,3-epoxypropoxy) biphenyl, 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5 ′. -Tetramethylbiphenyl, 4,4'-bis (2,3-epoxypropoxy) -3,3 ', 5,5'-tetraethylbiphenyl, 4,4'-bis (2,3-epoxypropoxy) -3, 3 ′, 5,5′-tetrabutylbiphenyl and the like can be mentioned.
Among these, 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl can be suitably used from the viewpoint of solubilization of the resin composition in an organic solvent.
On the other hand, 4,4′-bis (2,3-epoxypropoxy) biphenyl has strong crystal orientation, and 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5 ′. -Useful in combination with tetramethylbiphenyl to form a cured epoxy resin with high thermal conductivity.

That is, from the viewpoint of solubilization of the epoxy resin composition in an organic solvent, substantially other than 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl. The biphenyl type epoxy resin is preferably not contained, and from the viewpoint of improving the thermal conductivity of the cured epoxy resin, it is preferable to contain some 4,4′-bis (2,3-epoxypropoxy) biphenyl.
However, if the proportion of 4,4′-bis (2,3-epoxypropoxy) biphenyl in the entire biphenyl type epoxy resin becomes too large, even if the epoxy resin composition can be once dissolved in an organic solvent, There is a risk of causing a change and generating precipitates.
Therefore, the ratio of 4,4′-bis (2,3-epoxypropoxy) biphenyl to the entire biphenyl type epoxy resin is preferably about 50% in terms of moles.
That is, from the viewpoint of balancing solubilization in an organic solvent and the thermal conductivity of the cured product, 4,4′-bis (2,3-epoxypropoxy) biphenyl and 4,4′-bis (2,3 -Epoxypropoxy) -3,3 ', 5,5'-tetramethylbiphenyl is an epoxy resin so that the molar ratio is any ratio within the range of 1: 0.9 to 0.9: 1. It is preferable to make it contain in a composition.

  In the epoxy resin composition of the present embodiment, in addition to the biphenyl type epoxy resin, a general bisphenol type or novolac type epoxy resin can also be contained. When these epoxy resins are contained, the biphenyl type epoxy resin is contained. Since the effects of the resin may result in dilution with these epoxy resins, even if added, these epoxy resins are preferably less than 50% by weight of the total epoxy resin component, and 25% by weight or less. More preferably, it is most preferable not to contain at all.

An organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in one molecule, which is an important element constituting the epoxy resin composition in the present embodiment together with the biphenyl type epoxy resin (hereinafter, unless otherwise specified) The term “organoalkoxysilane compound” means “γ-glycidoxypropyltrimethoxy” as “an organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in one molecule”. Uses silane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltriisopropoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β- (3,4-epoxycyclohexyl) ethyldimethoxysilane, etc. can do.
Among these, γ-glycidoxypropyltrimethoxysilane is effective for improving the solubility of the epoxy resin composition in an organic solvent and for suppressing the decrease in physical properties of the cured epoxy resin at high temperatures.

The hydrolysis product obtained by hydrolyzing the organoalkoxysilane compound is usually obtained by bringing the organoalkoxysilane compound into contact with a hydrolysis catalyst such as dibutyltin diacetate, dibutyltin dilaurate, or dioctyltin dilaurate in the presence of water. Can be formed.
In order to obtain a condensation polymer obtained by dehydrating and condensing the hydrolysis product, the hydrolysis product is usually heated, for example, heated to a temperature of 100 ° C. or higher.
It is important that the dehydration condensation for obtaining this condensation polymer is carried out in the presence of the biphenyl type epoxy resin.

The epoxy resin composition of this embodiment may further contain a curing agent for thermally curing the biphenyl type epoxy resin.
Although it does not specifically limit as a hardening | curing agent contained in the epoxy resin composition of this embodiment, such as a phenol resin thing and an amine thing, In order to obtain the epoxy resin hardened | cured material which has a high glass transition temperature For this, a phenol resin is preferably used as a curing agent.
On the other hand, a diamine-based curing agent such as diaminodiphenylmethane is advantageous in that an epoxy resin cured product having excellent thermal conductivity can be easily obtained.

  The phenol resin used as the curing agent is not particularly limited, and examples thereof include phenol resins having two or more phenolic hydroxyl groups in one molecule that are generally used, and resorcin, catechol, Compounds having two phenolic hydroxyl groups in one molecule such as bisphenol A, bisphenol F, substituted or unsubstituted biphenol; phenol, cresol, xylenol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol, etc. Phenols or naphthols such as α-naphthol, β-naphthol and dihydroxynaphthalene and aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde and salicylaldehyde. And a novolak-type phenol resin obtained by condensation or co-condensation under a neutral catalyst.

In addition, phenols or aralkyl-type phenol resins such as phenol aralkyl resins and naphthol aralkyl resins synthesized from naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl; paraxylylene or metaxylylene-modified phenol resins; melamine-modified phenols Resin; Terpene-modified phenol resin; Dicyclopentadiene-type phenol resin and dicyclopentadiene-type naphthol resin synthesized by copolymerization from phenols or naphthols and dicyclopentadiene; Cyclopentadiene-modified phenol resin; Polycyclic aromatic ring modification Examples include phenol resin; biphenyl type phenol resin; triphenylmethane type phenol resin.
These may be used alone or in combination of two or more.

  The phenol resin is usually an epoxy composition in an amount of 40 to 100 parts by weight with respect to a total of 100 parts by weight of the condensation polymer starting from the organoalkoxysilane compound and the epoxy resin. Can be included.

  Further, in the epoxy resin composition of the present embodiment, as components other than those described above, for example, xylene resin, petroleum resin, coumarone-indene resin, terpene resin, rosin and other tackifiers, polybromodiphenyl oxide, tetrabromobisphenol Bromine compounds such as A, halogenated flame retardants such as chlorinated paraffin and perchlorocyclodecane, phosphorus flame retardants such as phosphate esters and halogen-containing phosphate esters, and hydrated metal compounds such as aluminum hydroxide and magnesium hydroxide Or general plastic compounding chemicals such as antimony trioxide, boron compounds and other flame retardants, phenolic, phosphorus, sulfur antioxidants, heat stabilizers, light stabilizers, UV absorbers, lubricants, pigments Silica, clay, calcium carbonate, aluminum oxide, magnesium oxide, boron nitride Silicon nitride, an inorganic filler can be mentioned such aluminum nitride, it may be contained in the epoxy resin composition in an amount in the range that the effect of the present invention is not significantly impaired.

Subsequently, the epoxy resin composition of this embodiment and the formation method of the epoxy resin hardened | cured material using this epoxy resin composition are demonstrated.
First, a mixture of an organoalkoxysilane compound, a hydrolysis catalyst, and water is prepared, and the organoalkoxysilane compound is hydrolyzed at room temperature or slightly under heating conditions.
A biphenyl type epoxy resin is mixed in a liquid containing the hydrolysis product of this organoalkoxysilane compound, and heated to a temperature equal to or higher than the melting point of the biphenyl type epoxy resin to prepare an epoxy resin mixed solution.
For example, when the biphenyl type epoxy resin is 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl, its melting point is a differential scanning calorimeter ( In the measurement by DSC), since it is usually about 105 ° C., in this case, for example, a heating condition of 120 ° C. or higher may be adopted to prepare an epoxy resin mixed solution.

And the dehydration condensation of a hydrolysis product can be implemented by maintaining this heating temperature.
When this dehydration condensation is carried out in the presence of a biphenyl type epoxy resin, the hydrolysis product or the condensation polymer obtained by the dehydration condensation reacts with the biphenyl type epoxy resin to relax the crystal orientation of the biphenyl type epoxy resin. The resulting epoxy resin composition can be made soluble in an organic solvent.
In particular, the mixture of the hydrolysis product and the epoxy resin is heated at any temperature of 80 ° C. or more and 160 ° C. or less for 1 minute or more and 50 minutes or less to perform dehydration condensation. An epoxy resin composition advantageous for improvement and solubility in an organic solvent can be obtained.
The maintenance of the heating temperature also has the function of volatilizing the residual water initially contained for the hydrolysis product, the alcohol generated by the hydrolysis, and the water generated in the dehydration condensation outside the system.
Accordingly, in the dehydration condensation, it is preferable to set the conditions such as the heating temperature and the heating time in consideration of the removal reaction as well as the condensation reaction.

In addition, the epoxy resin composition obtained by completing dehydration condensation (removal of water and alcohol) may be cooled to a temperature not higher than the boiling point of the organic solvent to be dispersed and then dispersed in the organic solvent to obtain an epoxy resin varnish. it can.
The addition of a curing agent such as a phenol resin to the epoxy resin varnish may be before or after the epoxy resin composition is dispersed in an organic solvent. When adding a curing agent before dispersion, It may be added to the epoxy resin composition side or the organic solvent side, and if necessary, a part may be added to the epoxy resin composition side and the rest may be added to the organic solvent side.
Similarly to this curing agent, for example, other components such as an inorganic filler can be added to the epoxy resin composition side or the organic solvent side to produce an epoxy resin varnish.
As the organic solvent used for producing the epoxy resin varnish, a general solvent such as methyl ethyl ketone (MEK) can be employed.

  Since the epoxy resin composition of the present embodiment can be used in a varnish state as described above, it can be used to produce a cured epoxy resin by performing steps such as coating and casting at room temperature. Since the conveyance by the liquid feeding to a point becomes easy, the epoxy resin hardened | cured material (molded object) excellent in heat conductivity can be produced simply.

For example, a metal foil such as copper foil is coated with an epoxy resin varnish, the organic solvent is removed and dried in a heating furnace or the like, and a prepreg sheet carrying a semi-cured epoxy resin composition is formed on the copper foil. The sheet can be hot pressed with an aluminum plate, a stainless plate or the like to form a metal base circuit board.
Thus, the metal base circuit board in which the insulating layer is formed of the cured epoxy resin obtained by thermally curing the epoxy resin composition according to the present embodiment is an aluminum plate or the like from the circuit layer side formed of the copper foil. Even when a heat generating element such as a power transistor with a relatively large amount of heat generated is mounted on a copper foil circuit, the generated heat is quickly transmitted to the metal through the insulating layer. It is transmitted to the plate layer side and can be radiated by a radiator attached to an aluminum plate or the like constituting the metal plate layer.

  In addition, when the epoxy resin composition according to the present embodiment is used as a sealing material for a semiconductor element, the junction temperature can be quickly transferred to the case side (outside) of heat generated in the internal semiconductor chip. Can be reduced.

In addition, the epoxy resin composition of this embodiment can be used not only for such an electronic component field but also for various applications, and in that case, various changes according to each application can be added.
Moreover, the technical matter well-known in the conventional epoxy resin composition which is not explained in full detail here can be employ | adopted also for the epoxy resin composition of this invention in the range by which the effect of this invention is not impaired remarkably.

  Next, the present invention will be described in more detail with specific examples, but the present invention is not limited thereto.

(Reference test 1)
First, in order to confirm the thermal conductivity of a general cured epoxy resin, the product names “JER828” and “JER1001”, which are bisphenol-type epoxy resins manufactured by JER, and phenol resins manufactured by Showa Polymer Co., Ltd. -Based curing agent (high molecular weight novolak: trade name “CRM-990”) and imidazole-based curing accelerator (1-cyanoethyl-2-ethyl-4-methylimidazole: trade name “2E4MZ-CN”) manufactured by Shikoku Kasei Co., Ltd. Is produced at a ratio of (JER828: JER1001: CRM-990: 2E4MZ-CN) = (50: 50: 40: 0.2) by weight (150 ° C. × 2 hours) + ( 180 ° C. × 2 hours).
The obtained cured epoxy resin was cooled and then processed into a disk-shaped test piece having a thickness of about 2 mm and a diameter of about 50 mm. 200 ") in accordance with ASTM E 1530.
As a result, it was found that the thermal conductivity of the cured epoxy resin was 0.195 (W / mK).

(Experimental example 1)
Next, the epoxy resin composition according to the present invention was examined.
The preparation shown in Table 1 below was used for the production of the epoxy resin composition.

(Preparation of liquid mixture A)
Γ-Glycidoxypropyltrimethoxysilane (trade name “KBM403”) manufactured by Shin-Etsu Chemical Co., Ltd., pure water and hydrolysis catalyst (dibutyltin dilaurate: DBTDL) are mixed in the mixing ratio shown in Table 1 and at room temperature for 1 day. The mixture was left to hydrolyze γ-glycidoxypropyltrimethoxysilane to prepare a mixed solution A containing the product produced by the hydrolysis.

(Preparation of epoxy resin mixture)
The epoxy resin was added to the previous mixed solution A, heated to 140 ° C. and stirred, and the added epoxy resin was dispersed in the mixed solution A to prepare an epoxy resin mixed solution.
More specifically, the mixture obtained by adding the epoxy resin to the mixed solution A is stirred while being heated from room temperature to 140 ° C. over 1 hour. After reaching the temperature of 140 ° C., the mixture is cooled with water within 5 minutes. The operation of returning to room temperature was performed again.
By heating at 140 ° C., the hydrolyzable organism of γ-glycidoxypropyltrimethoxysilane is subjected to dehydration condensation in the presence of an epoxy resin to form a condensation polymer, and water generated in the condensation polymerization, An epoxy resin composition was prepared by volatilizing and removing alcohol generated in the hydrolysis from the epoxy resin mixed solution.

(Production of epoxy resin varnish)
The obtained epoxy resin composition was dispersed in methyl ethyl ketone together with a curing agent and a curing accelerator so that the solid concentration was 60 parts by weight.
At this time, whether or not the entire solid content was soluble was observed with the naked eye, and what was soluble was determined as “soluble”. The results are also shown in Table 1.
Further, the stability of the solution was determined by observing whether precipitates were observed in the epoxy resin varnish during storage at room temperature. The case where a precipitate was not observed was judged as “◯”, and the case where a precipitate was observed was judged as “x”. The results are also shown in Table 1.

As shown in Table 1, the epoxy resin compositions “YX1-1” to “YX4-2” were soluble in MEK.
However, about "YX3-1" and "YX4-1", solution stability was low compared with other things, and the result was observed during storage at room temperature.

  In the above, dehydration condensation of hydrolyzable organisms of γ-glycidoxypropyltrimethoxysilane was carried out under heating conditions of 140 ° C. × (5 minutes or less). Similarly, after heating to 140 ° C., 4 hours The case where the temperature of 140 ° C. was maintained was also examined, but the result was almost the same as the above result, and it was found that the heat treatment exceeding 140 ° C. × (5 minutes or less) was not required. .

(Experimental example 2)
Next, the biphenyl type epoxy resin (4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl ”different from Experimental Example 1 and“ 4,4 About 1: 1 (molar ratio) mixture with “-bis (2,3-epoxypropoxy) biphenyl” was studied.
The preparation shown in Table 2 below was used for the production of the epoxy resin composition.

When the epoxy resin composition having the formulation shown in Table 2 was evaluated in the same manner as in Experimental Example 1, precipitates were observed during storage of the epoxy resin varnish at room temperature, and the solution stability was higher than that in Experimental Example 1. It was confirmed to be low.
In other words, 90% by weight or more of the epoxy resin is 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl for solution stability. It can be said that it can be in an excellent state.

(Experimental example 3)
“YX1-3”, “YX1-4”, “YX2-3” in which the curing systems of “YX1-1”, “YX1-2”, “YX2-1”, and “YX2-2” in Experimental Example 1 were changed , “YX2-4” and “YX2-5” were produced.
Specifically, an epoxy resin composition was prepared with the formulation shown in Table 3 below, and evaluated in the same manner as in the previous experimental example.

  When the epoxy resin composition having the composition shown in Table 3 was evaluated in the same manner as in Experimental Example 1, it was confirmed that the stability of the epoxy resin varnish at room temperature was good regardless of the curing system.

The epoxy resin varnish was collected in a polytetrafluoroethylene poly beaker, heated in a dryer at about 100 ° C., transferred to a vacuum chamber, and vacuum deaeration was performed with a vacuum pump.
Then, after repeatedly performing heating in the dryer and degassing under reduced pressure until generation of bubbles from the resin varnish is not observed in the degassing, heating is further performed at about 100 ° C. for 14 hours (150 ° C. × 2 hours) + (180 ° C. × 2 hours).
The obtained cured epoxy resin was cooled and then processed into a disk-shaped test piece having a thickness of about 2 mm and a diameter of about 50 mm. 200 ") in accordance with ASTM E 1530.
The results are shown in Table 3.

  As shown in Table 3, the cured epoxy resin using the epoxy resin composition according to the present invention is described in Non-Patent Document 1 as the thermal conductivity of a general cured epoxy resin. It can be seen that the value is higher than 19 W / m · K.

(Experimental example 4)
The examination was carried out by changing the curing systems of “YX3-1”, “YX3-2”, “YX4-1”, and “YX4-2” in Experimental Example 1 in the same manner as in Experimental Example 3. Specifically, as shown in Table 4 below, the same evaluation as before was performed for the blending of “YX3-3” and “YX4-3” using “CRM-990” manufactured by Showa Polymer Co., Ltd. .

  Here, as in Experimental Example 3, when the thermal conductivity (see Table 4) of the cured epoxy resin obtained by thermosetting each epoxy resin composition was measured, it was confirmed that it had excellent values. did it.

(Experimental example 5)
Similar to Experimental Example 3, 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl ”of Experimental Example 2 and“ 4,4′-bis ” It verified about the case where a hardening | curing agent was changed in the system using about 1: 1 (molar ratio) mixture with (2,3-epoxypropoxy) biphenyl.
Here, “YL1-3”, “YL1-4”, “YL2”, in which the curing systems of “YL1-1”, “YL1-2”, “YL2-1”, and “YL2-2” in Experimental Example 2 are changed, are changed. 3 ”and“ YL2-4 ”were prepared with the formulations shown in Table 5 below, and the same evaluation as before was performed on the obtained epoxy resin composition and the cured epoxy resin.
The results are also shown in Table 5.

In this experimental example, as in the previous experimental examples, solubility in MEK and solvent stability were evaluated, and a cured epoxy resin was prepared, and the thermal conductivity was evaluated in the same manner as in the previous experimental example. .
The solution stability was not improved.

(Experimental example 6)
Subsequently, the epoxy resin composition was prepared by changing the curing system of “YL3-1”, “YL3-2”, “YL4-1”, and “YL4-2” in Experimental Example 2 with the formulation shown in Table 6 below. did.

Even in Experimental Example 6, no improvement in the solution stability by the curing agent could be confirmed.
In addition, the value of the thermal conductivity of the cured epoxy resin obtained in the examination of the experimental examples 5 and 6 is generally higher than that obtained in the examination of the experimental examples 3 and 4, and the biphenyl epoxy resin is In a mixed system of 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl and 4,4′-bis (2,3-epoxypropoxy) biphenyl The use is advantageous in terms of the thermal conductivity of the cured product, although it is disadvantageous in terms of solution stability.
In particular, in the previous experimental example 5, in the system (YL2-4) cured with diaminodiphenylmethane, an epoxy resin cured product having an excellent thermal conductivity of 0.368 W / mK could be obtained.

(Experimental example 7)
Subsequently, addition of an epoxy resin (bisphenol A type epoxy resin) other than the biphenyl type epoxy resin was examined based on the same composition as “YL2-1”.
Specifically, an epoxy resin composition was prepared and examined with the system composition shown in Table 7 below.

Even in Experimental Example 7, no improvement in solution stability was observed.
In addition, the value of the thermal conductivity of the cured epoxy resin obtained in the examination of Experimental Example 7 is generally higher than that obtained in the examination of the experimental examples so far, and an excellent heat of 0.439 W / mK. An epoxy resin cured product having conductivity could be obtained.

  As described above, from the examination results of a series of experimental examples, according to the invention, it is possible to provide an epoxy resin composition useful for forming a cured epoxy resin having a high thermal conductivity while being soluble in a solvent. I understand that

Claims (4)

An epoxy resin composition containing a biphenyl type epoxy resin,
A condensation polymer obtained by dehydrating and condensing a hydrolysis product obtained by hydrolyzing an organoalkoxysilane compound having a glycidyl group and a hydrolyzable alkoxysilane group in one molecule in the presence of a biphenyl type epoxy resin is the biphenyl type epoxy. An epoxy resin composition, which is contained together with a resin.   The epoxy resin composition according to claim 1, wherein 4,4'-bis (2,3-epoxypropoxy) -3,3 ', 5,5'-tetramethylbiphenyl is used as the biphenyl type epoxy resin.   In addition to the 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl, 4,4′-bis (2,3-epoxypropoxy) biphenyl is The epoxy resin composition according to claim 2, which is used as a biphenyl type epoxy resin.   The epoxy resin composition according to any one of claims 1 to 3, wherein the organoalkoxysilane compound is γ-glycidoxypropyltrimethoxysilane.