JP2007262244A - Resin composition and semiconductor device manufactured using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a die attach paste for semiconductors or a material for the adhesion of heat dissipating members that has particularly a low elastic modulus, exhibits excellent stress relaxation properties and is low viscous, and a semiconductor device excellent particularly in reliabilities such as reflow resistance. <P>SOLUTION: The resin composition comprises a polycarbonate di(meth)acrylate compound (A) which is prepared by causing a polycarbonate diol (A1) obtained by reacting 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate to react with (meth)acrylic acid or a derivative thereof (A2), and a filler (B). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a resin composition and a semiconductor device manufactured using the resin composition.

  The problem of heat generated during the operation of semiconductor products has become more prominent with the increase in capacity, high-speed processing, and fine wiring of semiconductor products. So-called thermal management, which releases heat from semiconductor products, is an increasingly important issue. It has become to. For this reason, a method of attaching a heat radiating member such as a heat spreader or a heat sink to a semiconductor product is generally adopted, but a material having a higher thermal conductivity has been desired. On the other hand, depending on the form of the semiconductor product, the semiconductor element itself is bonded to a metal heat spreader, or the heat spreader is bonded to the die pad part of the lead frame to which the semiconductor element is bonded, or the die pad part is exposed on the package surface to dissipate heat. In some cases, the plate may be attached, and further, it may be adhered to an organic substrate having a heat dissipation mechanism such as a thermal via. In this case as well, a high thermal conductivity is required for the material to which the semiconductor element is bonded. In this way, high thermal conductivity is required for die attach paste or heat dissipation member bonding material, but at the same time, it is necessary to withstand reflow processing when mounting a semiconductor product on a substrate, and even when large area bonding is required In order to suppress the occurrence of warpage or the like due to the difference in thermal expansion coefficient between the constituent members, it is necessary to have low stress properties.

Here, metal fillers such as silver powder and copper powder and ceramic fillers such as aluminum nitride and boron nitride are usually added to organic binders at a high content, but the amount that can be contained is limited. When high thermal conductivity cannot be obtained, a large amount of solvent is contained and the cured product itself has good thermal conductivity, but in semiconductor products, after the solvent remains or volatilizes in the cured product, it becomes voids and the thermal conductivity is low. When it is not stable, there is no satisfactory case such as a case where the low stress property is insufficient and the viscosity is low based on the high filler content (see, for example, Patent Document 1).
Japanese Patent Laid-Open No. 11-43587

  The present invention provides a resin composition having a sufficiently low stress property and a low viscosity, and a semiconductor device having excellent reliability by using the resin composition as a die attach material for a semiconductor or a material for adhering a heat dissipation member. It is to be.

Such an object is achieved by the present invention described in the following [1] to [6].
[1] Reacting polycarbonate diol (A1) obtained by reacting 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate with (meth) acrylic acid or its derivative (A2). The resin composition characterized by including the polycarbonate di (meth) acrylate compound (A) obtained by this, and a filler (B).
[2] The polycarbonate diol (A1) according to [1], wherein 1,4-cyclohexanedimethanol and 1,6-hexanediol are reacted with dimethyl carbonate in a weight ratio of 20/80 to 80/20. Resin composition.
[3] The resin composition according to [1] or [2], wherein the polycarbonate diol (A1) has a molecular weight of 400 to 2000.
[4] The resin composition according to any one of [1] to [3], wherein the filler (B) is silver powder.
[5] The resin composition according to any one of items [1] to [4], further including a polymerization initiator.
[6] A semiconductor device produced by using the resin composition according to any one of items [1] to [5] as a die attach material or a heat dissipation member connection material.

  Since the resin composition of the present invention has a low elastic modulus, excellent stress relaxation properties and low viscosity, it has good workability (dispensability, printability) when used as a die attach material or a heat radiation member adhesive material. A semiconductor device manufactured using these materials is excellent in reflow resistance, and as a result, a highly reliable semiconductor device can be obtained.

The present invention relates to a polycarbonate diol obtained by reacting a polycarbonate diol obtained by reacting 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate with (meth) acrylic acid or a derivative thereof. A resin composition comprising a meth) acrylate compound and a filler, and particularly provides a resin composition having a low elastic modulus and excellent stress relaxation properties and a low viscosity.
Hereinafter, the present invention will be described in detail.

  In the present invention, the polycarbonate diol (A1) obtained by reacting 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate is reacted with (meth) acrylic acid or its derivative (A2). The polycarbonate di (meth) acrylate compound (A) obtained by Compound (A) has a carbonate bond, which is introduced to give flexibility to the cured product, and is not easily hydrolyzed as compared to polyether and polyester introduced for the same purpose. Even after being exposed to a long period of time, it is suitable for its deterioration. In general, those using bisphenol A as a raw material are known as polycarbonates. However, when a bisphenol-based polycarbonate is included in the skeleton, the cohesive force between molecular chains is increased due to the presence of an aromatic ring, and the cured product has a high elastic modulus. There is a problem of becoming too much. On the other hand, even in the case of an aliphatic polycarbonate, for example, polycarbonate di (meth) acrylate using only 1,4-cyclohexanedimethanol or polycarbonate di (meth) acrylate using only 1,6-hexanediol. In this case, the regularity of the molecular chain becomes high, and when the resin composition is formed from a waxy state, the viscosity is high and the workability is poor. Therefore, in the present invention, 1,4-cyclohexanedimethanol and 1,6 are used in order to obtain a polycarbonate di (meth) acrylate compound having a low viscosity, that is, good workability (dispensability, printability) when a resin composition is obtained. -React with polycarbonate diol (A1) which transesterified with dimethyl carbonate in the state which mixed hexanediol beforehand, and (meth) acrylic acid or its derivative (A2). The mixing ratio of 1,4-cyclohexanedimethanol and 1,6-hexanediol is preferably 20/80 to 80/20 by weight. This is because the viscosity of the polycarbonate di (meth) acrylate obtained with more or less 1,6-hexanediol becomes too high. The reaction of 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate uses a catalyst generally used as a transesterification catalyst. For example, organic tin compounds such as dibutyltin oxide and dioctyltin oxide, tetraalkyl titanates such as tetramethyl titanate, tetraisopropyl titanate, tetraalkyl titanates such as tetrabutyl titanate, alkali carbonates or alkaline earth carbonates such as potassium carbonate and calcium carbonate, Alkali metal alkyl alkoxides such as potassium methoxide, sodium methoxide, potassium ethoxide, potassium t-butoxide, dimethylaniline, tertiary amines such as 1,4-diazabicyclo (2,2,2) octane, acetylacetone hafnium, etc. An organometallic complex of hafnium.

The molecular weight of the polycarbonate diol (A1) is preferably 400 to 2000. A more preferred molecular weight is 500 to 1500, and an even more preferred value is 800 to 1200. If it is lower than this, the elastic modulus of the cured product becomes too high when the resin composition is made after (meth) acrylate conversion, and if it is higher than this, the viscosity in the (meth) acrylate conversion state becomes too high.
Polycarbonate diol (A1) can be converted to polycarbonate di (meth) acrylate by esterification reaction with (meth) acrylic acid (A2), or by transesterification with (meth) acrylic acid alkyl ester (A2). Polycarbonate di (meth) acrylate can also be used.

  In the present invention, the filler (B) is used. Filler (B) includes metal powder such as silver powder, gold powder, copper powder, aluminum powder, nickel powder and palladium powder, ceramic powder such as alumina powder, titania powder, aluminum nitride powder and boron nitride powder, polyethylene powder, polyacrylic Polymer powders such as acid ester powder, polytetrafluoroethylene powder, polyamide powder, polyurethane powder, and polysiloxane powder can be used. When the resin composition is used, it may be discharged using a nozzle. Therefore, in order to prevent nozzle clogging, the average particle size is preferably 30 μm or less, and it is preferable that there are few ionic impurities such as sodium and chlorine. In particular, silver powder is preferably used when electrical conductivity and thermal conductivity are required.

  If it is the silver powder currently marketed for electronic materials normally, reduced powder, atomized powder, etc. can be obtained, and as an average particle diameter, an average particle diameter is 1 micrometer or more and 30 micrometers or less. This is because the viscosity of the resin composition becomes too high below the lower limit, and can cause nozzle clogging during dispensing as described above above the upper limit, and silver powder other than for electronic materials may have a large amount of ionic impurities. Because there is, attention is necessary. The shape is not particularly limited, such as flaky shape or spherical shape, but preferably flaky shape is used, and it is usually contained in the resin composition in an amount of 70% by weight to 95% by weight. This is because when the proportion of silver powder is less than the lower limit, the conductivity deteriorates, and when it is higher than the upper limit, the viscosity of the resin composition becomes too high.

  In the present invention, a diluent can be used. Of these, the following compounds are preferably used for obtaining good adhesion. 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl ( (Meth) acrylate, 1,2-cyclohexanediol mono (meth) acrylate, 1,3-cyclohexanediol mono (meth) acrylate, 1,4-cyclohexanediol mono (meth) acrylate, 1,2-cyclohexanedimethanol mono (meta) ) Acrylate, 1,3-cyclohexanedimethanol mono (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, 1,2-cyclohexanediethanol mono (meth) acrylate, 1 3-cyclohexanediethanol mono (meth) acrylate, 1,4-cyclohexanediethanol mono (meth) acrylate, glycerin mono (meth) acrylate, glycerin di (meth) acrylate, trimethylolpropane mono (meth) acrylate, trimethylolpropane di ( (Meth) acrylate, pentaerythritol mono (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, neopentylglycol mono (meth) acrylate-containing (meth) acrylate compounds, and these hydroxyl groups A (meth) acrylate compound having a carboxy group obtained by reacting a (meth) acrylate compound with a dicarboxylic acid. Examples of the dicarboxylic acid usable here include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid, and tetrahydrophthalic acid. Hexahydrophthalic acid and derivatives thereof. Among them, an acid anhydride obtained by dehydrating these dicarboxylic acids is preferably used because it can easily react with a hydroxyl group to obtain a half-esterified product. Either a (meth) acrylate compound having a hydroxyl group or a (meth) acrylate compound having a carboxy group may be used in combination, or a plurality of types may be used.

  In addition to the above, it is also possible to use a (meth) acrylate compound having no hydroxyl group or carboxy group and a compound having a vinyl group. For example, the following compounds are mentioned. Methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tertiary butyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) Acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isoamyl (meth) acrylate, isostearyl (meth) acrylate, behenyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, other alkyl (meth) acrylates, cyclohexyl (Meth) acrylate, tertiary butyl cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (Meth) acrylate, isobornyl (meth) acrylate, glycidyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, zinc mono (meth) acrylate, zinc di (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) Acrylate, neopentyl glycol (meth) acrylate, trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2,2,3,3,4,4-hexafluorobutyl ( (Meth) acrylate, perfluorooctyl (meth) acrylate, perfluorooctylethyl (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4- Tandiol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,10-decanediol di ( (Meth) acrylate, tetramethylene glycol di (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxypolyalkylene glycol mono (meth) acrylate, octoxypolyalkylene glycol mono (Meth) acrylate, Lauroxy polyalkylene glycol mono (meth) acrylate, Stearoxy polyalkylene glycol mono (meth) acrylate, Allyloxy polyalkylene glycol Rumono (meth) acrylate, nonylphenoxypolyalkylene glycol mono (meth) acrylate, N, N'-methylenebis (meth) acrylamide, N, N'-ethylenebis (meth) acrylamide, 1,2-di (meth) acrylamide ethylene Glycol, di (meth) acryloyloxymethyltricyclodecane, N- (meth) acryloyloxyethyl maleimide, N- (meth) acryloyloxyethyl hexahydrophthalimide, N- (meth) acryloyloxyethyl phthalimide, n -Vinyl-2-pyrrolidone, styrene derivatives, α-methylstyrene derivatives.

  In the present invention, a polymerization initiator is preferably used for the purpose of reacting an unsaturated bond. The type of the polymerization initiator is not particularly limited, but the resin composition of the present invention is usually used under illumination such as a fluorescent lamp. Therefore, when a photopolymerization initiator is contained, an increase in viscosity is observed due to a reaction during use. Therefore, it is not preferable to substantially contain a photopolymerization initiator. “Substantially” means that a small amount of the photopolymerization initiator may be present to such an extent that no increase in viscosity is observed, and it is preferably not contained.

  For this reason, a thermal radical polymerization initiator is preferably used. Although it is not particularly limited as long as it is normally used as a thermal radical polymerization initiator, it is desirable that a rapid heating test (decomposition start temperature when a sample is placed on an electric heating plate and heated at 4 ° C./min. In which the decomposition temperature is 40 to 140 ° C. If the decomposition temperature is less than 40 ° C., the preservability of the resin composition at normal temperature deteriorates, and if it exceeds 140 ° C., the curing time becomes extremely long, which is not preferable. Specific examples of the thermal radical polymerization initiator satisfying this include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, acetylacetone peroxide, 1,1-bis (t-butylperoxy) 3, 3, 5 -Trimethylcyclohexane, 1,1-bis (t-hexylperoxy) cyclohexane, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) ) Cyclohexane, 2,2-bis (4,4-di-t-butylperoxycyclohexyl) propane, 1,1-bis (t-butylperoxy) cyclododecane, n-butyl 4,4-bis (t- Butyl peroxy) valerate, 2,2-bis (t-butylperoxy) Tan, 1,1-bis (t-butylperoxy) -2-methylcyclohexane, t-butyl hydroperoxide, P-menthane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t -Hexyl hydroperoxide, dicumyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane, α, α'-bis (t-butylperoxy) diisopropylbenzene, t-butyl Cumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide , Octanoyl peroxide, lauroyl peroxide, cinnamic acid peroxide m-toluoyl peroxide, benzoyl peroxide, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxide Carbonate, di-sec-butylperoxydicarbonate, di (3-methyl-3-methoxybutyl) peroxydicarbonate, di (4-t-butylcyclohexyl) peroxydicarbonate, α, α′-bis (neo) Decanoylperoxy) diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecano Eate, t-hexyl par Xineodecanoate, t-butylperoxyneodecanoate, t-hexylperoxypivalate, t-butylperoxypivalate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylper) Oxy) hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2- Ethyl hexanoate, t-butyl peroxy-2-ethyl hexanoate, t-butyl peroxyisobutyrate, t-butyl peroxymaleic acid, t-butyl peroxylaurate, t-butyl peroxy- 3,5,5-trimethylhexanoate, t-butylperoxyisopropyl monocarbonate, -Butylperoxy-2-ethylhexyl monocarbonate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyacetate, t-hexylperoxybenzoate, t-butylperoxy-m -Toluoyl benzoate, t-butyl peroxybenzoate, bis (t-butylperoxy) isophthalate, t-butylperoxyallyl monocarbonate, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl ) Benzophenone and the like can be mentioned, but these can be used alone or in combination of two or more in order to control curability. Although not particularly limited, it is preferably contained in the resin composition in an amount of 0.001% by weight to 2% by weight.

  In the present invention, a coupling agent can be used. Generally used silane coupling agents and titanium-based coupling agents can be used. In particular, when a silane coupling agent having an S—S bond is used as a filler (B), silver powder is used. Since the bonding with the surface also occurs, not only the adhesion strength to the adherend surface but also the cohesive strength of the cured product is improved, so that it can be suitably used. Specifically, bis (trimethoxysilylpropyl) tetrasulfide, bis (triethoxysilylpropyl) tetrasulfide, bis (tributoxysilylpropyl) tetrasulfide, bis (dimethoxymethylsilylpropyl) tetrasulfide, bis (diethoxymethyl) Silylpropyl) tetrasulfide, bis (dibutoxymethylsilylpropyl) tetrasulfide, bis (trimethoxysilylpropyl) disulfide, bis (triethoxysilylpropyl) disulfide, bis (tributoxysilylpropyl) disulfide, bis (dimethoxymethylsilylpropyl) ) Disulfide, bis (diethoxymethylsilylpropyl) disulfide, bis (dibutoxymethylsilylpropyl) disulfide and the like. A combination with other than the silane coupling agent having an S—S bond is also preferred.

In the resin composition of the present invention, additives such as an antifoaming agent, a surfactant, various polymerization inhibitors, and antioxidants can be used as necessary.
The resin composition of the present invention can be produced, for example, by premixing the components, kneading using three rolls, and degassing under vacuum.

As a method of manufacturing a semiconductor device using the resin composition of the present invention, a known method can be used. For example, using a commercially available die bonder, the resin composition is dispensed on a predetermined portion of the lead frame, and then the chip is mounted and heat-cured. Then, a semiconductor device is manufactured by wire bonding and transfer molding using an epoxy resin. Alternatively, it is possible to use a method in which a resin composition is dispensed on the back side of a chip such as a flip chip BGA sealed with an underfill material after flip chip bonding, and a heat dissipating component such as a heat spreader or lid is mounted and cured.
EXAMPLES The present invention will be specifically described below using examples, but is not limited thereto. The blending ratio is expressed in parts by weight.

[Example 1]
Reaction of methyl methacrylate with a polycarbonate diol having a molecular weight of about 900 synthesized from 1,4-dimethanolcyclohexane / 1,6-hexanediol (= 3/1 (weight ratio)) and dimethyl carbonate as compound (A). As a filler (B), a flaky silver powder having an average particle size of 8 μm and a maximum particle size of 30 μm is obtained as a polycarbonate dimethacrylate compound (Ube Industries, Ltd., UM-90 (3/1) DM, hereinafter referred to as Compound A1). (Hereinafter referred to as silver powder), dicumyl peroxide (manufactured by NOF Corporation, Park Mill D, decomposition temperature in rapid heating test: 126 ° C., hereinafter referred to as polymerization initiator), 1,4-cyclohexanedimethanol monoacrylate (hereinafter referred to as “polymerization initiator”) Nippon Kasei Co., Ltd., CHDMMA, hydroxyl-containing acrylate compound, hereinafter referred to as compound Y1), 2 -Methacryloyloxyethyl succinic acid (manufactured by Kyoeisha Chemical Co., Ltd., light ester HO-MS, methacrylate compound having a carboxy group, hereinafter compound Y2), 1,6-hexanediol dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., light ester) 1, 6HX, methacrylate compound having no hydroxyl group or carboxy group, hereinafter referred to as compound Y3), coupling agent having a tetrasulfide bond (manufactured by Nippon Unicar Co., Ltd., A-1289, hereinafter referred to as coupling agent 1), having a glycidyl group A coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-403E, hereinafter coupling agent 2) is blended as shown in Table 1, kneaded using three rolls, and defoamed to obtain a resin composition. It was. The blending ratio is parts by weight. The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.

[Examples 2 to 4 and Comparative Examples 1 to 4]
The resin composition was obtained in the same manner as in Example 1 by blending at the ratio shown in Table 1.
In Example 2, methyl methacrylate is reacted with polycarbonate diol having a molecular weight of about 900 synthesized from 1,4-dimethanolcyclohexane / 1,6-hexanediol (= 1/3 (weight ratio)) and dimethyl carbonate. In Example 3, a polycarbonate dimethacrylate compound (UME-90 (1/3) DM, hereinafter referred to as Compound A2) manufactured by Ube Industries Co., Ltd. was obtained in Example 3, and 1,4-dimethanolcyclohexane / 1,6-hexanediol. (= 1/1 (weight ratio)) and a polycarbonate dimethacrylate compound obtained by reacting methyl methacrylate with a polycarbonate diol having a molecular weight of about 900 synthesized from dimethyl carbonate (manufactured by Ube Industries, Ltd., UM-90 (1 / 1) DM, hereinafter referred to as compound A3) in Example 4, 1,4-dimethanol Polycarbonate dimethacrylate compound (Ube Industries, Ltd.) obtained by reacting methyl methacrylate with polycarbonate diol having a molecular weight of about 900 synthesized from hexane / 1,6-hexanediol (= 1/3 (weight ratio)) and dimethyl carbonate UM-90 (1/3) DM, hereinafter referred to as Compound A2), 1,4-dimethanolcyclohexane / 1,6-hexanediol (= 1/1 (weight ratio)) and dimethyl carbonate The polycarbonate dimethacrylate compound (Ube Industries, Ltd. make, UM-90 (1/1) DM, the following compound A3) obtained by making methyl methacrylate react with 900 polycarbonate diol was used.

In Comparative Example 1, a polycarbonate dimethacrylate compound obtained by reacting methyl methacrylate with 1,000-hexanediol and dimethyl carbonate and having a molecular weight of about 1000 polycarbonate diol (UH-100DM, UH-100DM, the following compound) X1), and in Comparative Example 2, a polycarbonate dimethacrylate compound obtained by reacting methyl methacrylate with a polycarbonate diol having a molecular weight of about 1000 synthesized from 1,4-dimethanolcyclohexane and dimethyl carbonate (manufactured by Ube Industries, Ltd.) , UC-100DM, hereinafter referred to as Compound X2), in Comparative Example 3, polytetramethylene glycol dimethacrylate (manufactured by NOF Corporation, Blemmer PDT-800, hereinafter referred to as Compound X3), and in Comparative Example 4, Compound X1 and Compound X2 It was used.
The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.

Evaluation method and viscosity: Measured at 25 ° C. and 2.5 rpm using an E-type viscometer (3 ° cone). The thing with the viscosity in the range of 15-25 Pa.s was set as the pass. The unit of viscosity is Pa · s.
Adhesive strength: Using the resin composition shown in Table 1, a 6 × 6 mm silicon chip was mounted on a Ni—Pd / Au plated copper frame and cured in an oven at 150 ° C. for 30 minutes. After curing and after moisture absorption treatment (85 ° C., 85%, 72 hours), the hot die shear strength at 260 ° C. was measured using an automatic adhesive force measuring apparatus. The case where the die shear strength when heated at 260 ° C. was 30 N / chip or more was regarded as acceptable. The unit of adhesive strength is N / chip.
-Elastic modulus: Using the resin composition shown in Table 1, a 4 × 20 × 0.1 mm film-like test piece was prepared (curing conditions: 150 ° C. for 30 minutes), and the dynamic viscoelasticity measuring machine (DMA) was used. The measurement was performed in the pull mode. The measurement conditions are as follows.
Measurement temperature: -100 to 300 ° C
Temperature increase rate: 5 ° C / min Frequency: 10Hz
Load: 100mN
The storage elastic modulus at 25 ° C. was regarded as the elastic modulus, and the case of 3000 MPa or less was regarded as acceptable. The unit of elastic modulus is MPa.
Reflow resistance: Using the resin composition shown in Table 1, the following lead frame and silicon chip were cured and bonded at 150 ° C. for 30 minutes. Sealing material (Sumicon EME-7026, manufactured by Sumitomo Bakelite Co., Ltd.) was used for sealing to produce a package. This package was subjected to a moisture absorption treatment at 30 ° C. and a relative humidity of 60% for 168 hours, followed by an IR reflow treatment (260 ° C., 10 seconds, 3 times reflow). The degree of peeling of the treated package was measured with an ultrasonic flaw detector (transmission type). The case where the peeling area of the die attach part was less than 10% was regarded as acceptable. The unit of the peeled area is%.
Package: QFP (14 x 20 x 2.0 mm)
Lead frame: Ni-Pd / Au plated copper frame Chip size: 6 x 6 mm
Curing conditions for resin composition: 150 ° C. in oven for 30 minutes

Since the resin composition of the present invention has a particularly low elastic modulus and excellent stress relaxation properties, it can be suitably used as a die attach paste for semiconductors or a material for adhering heat dissipation members.

Claims (6)

Obtained by reacting polycarbonate diol (A1) obtained by reacting 1,4-cyclohexanedimethanol, 1,6-hexanediol and dimethyl carbonate with (meth) acrylic acid or its derivative (A2). A resin composition comprising a polycarbonate di (meth) acrylate compound (A) and a filler (B). The resin composition according to claim 1, wherein the polycarbonate diol (A1) is obtained by reacting 1,4-cyclohexanedimethanol and 1,6-hexanediol with dimethyl carbonate in a weight ratio of 20/80 to 80/20. The resin composition according to claim 1 or 2, wherein the polycarbonate diol (A1) has a molecular weight of 400 to 2,000. The resin composition according to any one of claims 1 to 3, wherein the filler (B) is silver powder. Furthermore, the resin composition of any one of Claims 1-4 containing a polymerization initiator. The semiconductor device produced using the resin composition of any one of Claims 1-5 as a die-attach material or a heat radiating member connection material.