JP4935026B2 - Resin composition and semiconductor device produced using resin composition - Google Patents

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 based on the high filler content (see, for example, Patent Document 1).
Japanese Patent Laid-Open No. 11-43587

  This invention is providing the semiconductor device excellent in reliability by using the resin composition which has sufficient low-stress property, and this resin composition as a die attach paste for semiconductors, or a heat dissipation member adhesion | attachment material.

The present invention is achieved by the following [1] to [ 7 ].
[1] A resin composition used as a die attach paste or a material for adhering a heat dissipation member, comprising: (A) a compound having a structure represented by the general formula (1) and at least one polymerizable unsaturated bond ; B) a reaction product of a polycarbonate diol and (meth) acrylic acid or a derivative thereof obtained by the reaction of an aliphatic diol and a dialkyl carbonate, wherein the compound (A) contains a polymerization initiator and (C) a filler . resin composition, wherein the at.

R ¹ Is an aliphatic chain hydrocarbon group having 4 to 8 carbon atoms
n is 1-50

[ 2 ] The resin composition according to item [1 ], wherein the aliphatic diol contains at least one selected from butanediol, pentanediol, hexanediol, cyclohexanediol, and cyclohexanedimethanol.

[3] The resin according to any one of [1] or [2], further including a compound having a functional group represented by the general formula (2), wherein the compound is a polyether-based bismaleimide acetate. Composition.

R ² Is -C ₂ H ₂ -Or-C ₃ H ₄ -Either
R ³ Is a hydrocarbon group having 1 to 5 carbon atoms.

[ 4 ] The resin composition according to any one of [1] to [3] , further including a coupling agent.
[ 5 ] The resin composition according to item [ 4 ], wherein the coupling agent is a silane coupling agent having an S—S bond.
[ 6 ] The resin composition according to any one of [1] to [ 5 ], wherein the filler (C) is silver powder.
[ 7 ] A semiconductor device manufactured using the resin composition according to any one of items [1] to [ 6 ] as a die attach paste or a material for adhering a heat dissipation member.

  Since the resin composition of the present invention has a low elastic modulus and excellent stress relaxation properties, when used as a die attach paste or a heat radiation member bonding material, the obtained semiconductor device is excellent in solder crack resistance, and as a result. A highly reliable semiconductor device can be obtained.

The present invention is a resin composition comprising a compound having a structure represented by the general formula (1) and at least one polymerizable unsaturated bond, a polymerization initiator, and a filler, particularly having a low elastic modulus and a stress relaxation property. It provides the resin composition which is excellent in.
Hereinafter, the present invention will be described in detail.

In the present invention, the compound (A) having a structure represented by the general formula (1) and at least one polymerizable unsaturated bond is used. The structure represented by the general formula (1) is introduced in order to give flexibility to the cured product. However, since it is difficult to hydrolyze as compared with polyether and polyester introduced for the same purpose, the condition is particularly high temperature and high humidity. This is because it is preferable because it is less deteriorated even after being exposed to a long time. In the general formula (1), R ¹ is an organic group, but when R ¹ contains an aromatic ring, the cohesive force between the molecular chains increases and the elastic modulus of the cured product increases, so that it is aliphatic. preferable. A more preferable organic group is an aliphatic chain hydrocarbon group having 3 to 10 carbon atoms. A more preferable organic group is an aliphatic chain hydrocarbon group having 4 to 8 carbon atoms. If it is less than this, the hydrophilicity is high and the water absorption rate of the cured product becomes too high, and if it is more than this, the hydrophobicity is high and the adhesiveness is deteriorated. The number of repetitions n is 1 to 50, but if it is less than this, the intended flexibility cannot be sufficiently exhibited, and if it is more than this, the viscosity becomes too high. A more preferable repeating number is 5-20. At least one polymerizable unsaturated bond is required to react and give a cured product, and it is preferable that two polymerizable bonds are contained in one molecule from the viewpoint of curability. Any form of unsaturated bond can be used as long as it can be polymerized, but preferred examples include vinyl group, (meth) allyl group, (meth) acryloyl group, maleimide group, and the like. (Meth) acryloyl group. As such a compound, a compound obtained by reacting (meth) acrylic acid or a derivative thereof after obtaining a polycarbonate diol by transesterification of an aliphatic diol and a dialkyl carbonate is preferable, but not limited thereto. . Aliphatic diols having 3 to 10 carbon atoms are preferably used. For example, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 3-methyl- 1,5-pentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedim Methanol, 1,2-cyclohexanediethanol, 1,3-cyclohexanediethanol, 1,4-cyclo Although such hexane diethanol. Among them butanediol, pentanediol, hexanediol, cyclohexanediol, cyclohexanedimethanol are preferred, they may be used in combination of two or more kinds thereof may be used alone. As the dialkyl carbonate, dimethyl carbonate is preferable from the viewpoint of reactivity. In the reaction, a catalyst generally used as a transesterification catalyst is used. For example, organic tin compounds such as dibutyl tin oxide and dioctyl tin oxide, tetraalkyl titanates such as tetramethyl titanate, tetraisopropyl titanate, tetraalkyl titanates such as tetrabutyl titanate, alkali metal carbonates or alkaline earth metal 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. When multiple aliphatic diols are used, it is possible to obtain a random copolymer by simultaneously charging multiple aliphatic diols, or to obtain a block copolymer by reacting short-chain polycarbonate diols with each other. It is. Polycarbonate diol can be converted to polycarbonate di (meth) acrylate by esterification reaction with (meth) acrylic acid, or can be converted to polycarbonate di (meth) acrylate by transesterification with (meth) acrylic acid alkyl ester. Is possible.

In the present invention, a diluent can be used. Although it will not specifically limit if it is a compound which has a vinyl group generally used, For example, the following compounds can be used. 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, 2 -Hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, tartarb Lucyclohexyl (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, perfluoro Cutylethyl (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol 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, lauroxypolyalkylene Glycol mono (meth) acrylate, stearoxy polyalkylene glycol mono (meth) acrylate, allyloxy polyalkylene glycol mono (meth) acrylate, nonylphenoxy polyalkylene glycol mono (meth) acrylate, N, N′-methylenebis (meth) acrylamide N, N′-ethylenebis (meth) acrylamide, 1,2-di (meth) acrylamide ethylene glycol, di (meth) acryloyloxymethyltricyclodecane, 2- (meth) acryloyloxyethyl succinic acid, 2 -(Meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl, N- (meth) acryloyloxyethylmaleimide, N- (meth) acryloyloxyethyl hexahydrophthalimide, N- ( Data) acryloyloxyethyl phthalimide, n- vinyl-2-pyrrolidone, styrene derivatives, alpha-methylstyrene derivatives.

In the present invention, the polymerization initiator (B) is used for the purpose of reacting an unsaturated bond. The type of the polymerization initiator is not particularly limited, but since the resin composition of the present invention is usually used under illumination such as a fluorescent lamp, an increase in viscosity is observed due to a reaction during use when a photopolymerization initiator is contained. 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, etc., but these may 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, as filler (C), 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, Polymer powders such as polyethylene powder, polyacrylate 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, it is also possible to use a compound having at least one functional group represented by the general formula (2). The functional group represented by the general formula (2) can be copolymerized with the compound (A), and the adhesive force is improved due to the polarity of the functional group represented by the general formula (2). Such functional groups can be converted to maleimidated amino acids by reacting a compound having a primary amine and a carboxy group (amino acids such as glycine, alanine and caproic acid) with maleic anhydride to form maleamic acid, followed by dehydration cyclization. It can be obtained by esterification with a compound having a hydroxyl group. At least one functional group represented by the general formula (2) is necessary, but from the viewpoint of curability, it is preferably two or three in one molecule. If the amount is larger than this, it may cause a high viscosity, and two cases are particularly preferable in one molecule. In order to obtain such a compound, it can be obtained by esterifying the aforementioned maleimidated amino acid and diol.

  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 (C), 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.

Compound Preparation Compound A1: UH-100 (manufactured by Ube Industries, Ltd., polycarbonate diol synthesized from 1,6-hexanediol and dimethyl carbonate, molecular weight of about 1000) 200 g, methacrylic acid (reagent) 38 g and toluene 1200 ml separable flask The mixture was stirred for 30 minutes under reflux using a Dean-Stark trap to remove water. After cooling to room temperature, a solution prepared by dissolving 150 g of dicyclohexylcarbodiimide in 500 ml of ethyl acetate was added dropwise over 30 minutes with stirring, and then reacted at room temperature for 6 hours. Excess dicyclohexylcarbodiimide was precipitated by adding 50 ml of ion-exchanged water with stirring after the reaction, and then stirred for 30 minutes under reflux using a Dean-Stark trap to remove water. After cooling to room temperature, the reaction solution was filtered to remove solids, followed by separation and washing three times with ion exchange water at 70 ° C. and twice with ion exchange water at room temperature. The solvent was removed from the filtrate obtained by filtering the solvent layer again with an evaporator and a vacuum dryer to obtain a product. (Hereinafter, compound A1, yield of about 85%, waxy at room temperature, molecular weight in terms of styrene by GPC is about 1200. By proton NMR measurement using deuterated chloroform, a peak around 2.0 ppm based on the proton of the hydroxyl group of polycarbonate diol was observed. (The disappearance was confirmed. In formula (3), R ⁴ is — (CH ₂ ) ₆ — and n is about 5).

Compound A2: UM-90 (1/1) (manufactured by Ube Industries, Ltd., polycarbonate diol synthesized from 1,6-hexanediol / 1,4-dimethanolcyclohexane (= 1/1) and dimethyl carbonate and having a molecular weight of about 900 ) 180 g, 38 g of methacrylic acid (reagent) and 1200 ml of toluene were placed in a separable flask and stirred for 30 minutes under reflux using a Dean-Stark trap to remove water. After cooling to room temperature, a solution prepared by dissolving 150 g of dicyclohexylcarbodiimide in 500 ml of ethyl acetate was added dropwise over 30 minutes with stirring, and then reacted at room temperature for 6 hours. Excess dicyclohexylcarbodiimide was precipitated by adding 50 ml of ion-exchanged water with stirring after the reaction, and then stirred for 30 minutes under reflux using a Dean-Stark trap to remove water. After cooling to room temperature, the reaction solution was filtered to remove solids, followed by separation and washing three times with ion exchange water at 70 ° C. and twice with ion exchange water at room temperature. The solvent was removed from the filtrate obtained by filtering the solvent layer again with an evaporator and a vacuum dryer to obtain a product. (Compound A2, yield: about 86%, liquid at room temperature. Styrene-converted molecular weight by GPC is about 1100. Proton NMR measurement using deuterated chloroform shows disappearance of a peak around 2.0 ppm based on the hydroxyl group proton of polycarbonate diol. (In the formula (3), R ⁴ is a mixture of — (CH ₂ ) ₆ — and —CH ₂ —C ₆ H ₁₀ —CH ₂ —, and n is about 4.)

Compound X: Plaxel 210CP (manufactured by Daicel Chemical Industries, Ltd., poly ε-caprolactone diol with a molecular weight of about 1000) 200 g, methacrylic acid (reagent) 38 g and toluene 1200 ml are placed in a separable flask and refluxed using a Dean-Stark trap for 30 minutes. Water was removed by stirring. After cooling to room temperature, a solution prepared by dissolving 150 g of dicyclohexylcarbodiimide in 500 ml of ethyl acetate was added dropwise over 30 minutes with stirring, and then reacted at room temperature for 6 hours. Excess dicyclohexylcarbodiimide was precipitated by adding 50 ml of ion-exchanged water with stirring after the reaction, and then stirred for 30 minutes under reflux using a Dean-Stark trap to remove water. After cooling to room temperature, the reaction solution was filtered to remove solids, followed by separation and washing three times with ion exchange water at 70 ° C. and twice with ion exchange water at room temperature. The solvent was removed from the filtrate obtained by filtering the solvent layer again with an evaporator and a vacuum dryer to obtain a product. (Hereinafter, compound X, yield of about 84%, waxy at room temperature, styrene-equivalent molecular weight by GPC is about 1200. A peak around 2.0 ppm based on the proton of the hydroxyl group of polyester diol is measured by proton NMR using deuterated chloroform. . disappearance was confirmed ^{R 5} is an organic group of formula (4), ^{R 6} is _{-C 5 H 10 -, m1 +} m2 is about 8.)

[Example 1]
Compound (A) as the compound A1, polymerization initiator (B) as dicumyl peroxide (manufactured by NOF Corporation, Park Mill D, decomposition temperature in rapid heating test: 126 ° C., polymerization initiator hereinafter), filler As (C), flaky silver powder (hereinafter referred to as silver powder) having an average particle diameter of 8 μm and a maximum particle diameter of 30 μm, 2-hydroxypropyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., light ester HOP, hereinafter referred to as diluent 1), 1,6- Hexanediol dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., light ester 1, 6HX, hereinafter diluent 2), coupling agent having tetrasulfide bond (manufactured by Nihon Unicar Co., Ltd., A-1289, hereinafter coupling agent 1) Table 1 shows coupling agents having a glycidyl group (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-403E, hereinafter referred to as coupling agent 2). , Kneaded using three rolls, and defoamed to obtain a resin composition. 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, Comparative Examples 1 and 2]
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, compounds A1 and A2 are used, in Example 3, compound A2 is used, and in Example 4, polyether bismaleimide acetate (Dainippon Ink Industries, Ltd., LumiCure MIA-200, general formula (2) is used. In which R ² is —C ₂ H ₂ — and R ^{3 has} a carbon number of 1. Hereinafter, Compound Y) was used. In Comparative Example 2, Compound X was used.
The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.

Evaluation Method / Adhesive Strength: Using a 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.
-Modulus of elasticity: 4 × 20 × 0.1 mm film-like test pieces were prepared using the resin composition shown in Table 1 (curing conditions: 150 ° C. for 30 minutes), and using a dynamic viscoelasticity measuring machine (DMA) Measurements were made in 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 (7)

A resin composition used as a die attach paste or a material for adhering heat dissipation members, wherein (A) a compound having a structure represented by the general formula (1) and at least one polymerizable unsaturated bond , (B) polymerization Including an initiator and a filler (C) , the compound (A) is a reaction product of a polycarbonate diol obtained by the reaction of an aliphatic diol and a dialkyl carbonate and (meth) acrylic acid or a derivative thereof. A resin composition characterized by the above.

R ¹ is an aliphatic chain hydrocarbon group having 4 to 8 carbon atoms.
n is 1-50 The resin composition according to claim 1 , wherein the aliphatic diol contains at least one selected from butanediol, pentanediol, hexanediol, cyclohexanediol, and cyclohexanedimethanol. The resin composition according to claim 1, further comprising a compound having a functional group represented by the general formula (2), wherein the compound is a polyether-based bismaleimide acetate.

R ² Is -C ₂ H ₂ -Or-C ₃ H ₄ -Either
R ³ Is a hydrocarbon group having 1 to 5 carbon atoms. Furthermore, the resin composition of any one of Claims 1-3 containing a coupling agent. The resin composition according to claim 4 , wherein the coupling agent is a silane coupling agent having an S—S bond. The resin composition according to any one of claims 1 to 5 , wherein the filler (C) is silver powder. A semiconductor device manufactured using the resin composition according to any one of claims 1 to 6 as a die attach paste or a heat dissipation member bonding material.