JP5115096B2 - Adhesive film - Google Patents

Description

  The present invention relates to an adhesive film and a semiconductor device using the adhesive film.

  In recent years, the demand for higher density and higher integration of semiconductor devices has become stronger in response to higher functionality of electronic devices and the like, and semiconductor packages have been increasing in capacity and density.

  In order to meet such a demand, for example, a method for realizing a reduction in size, thickness and capacity of a semiconductor package by stacking semiconductor elements in multiple stages on the semiconductor element has been studied. In such a package, an organic substrate such as a bismaleimide-triazine substrate or a polyimide substrate may be used (Patent Document 1).

  Usually, in such a semiconductor package, as a method of electrically connecting a semiconductor element and a substrate, a wire bonding method of connecting using a bonding wire is widely used.

  When the wire bonding method is used to connect the semiconductor element and the substrate, when the semiconductor elements are stacked, the wire bonded portion of the semiconductor element already mounted on the substrate is electrically connected without being deformed or cut. It is necessary to maintain a secure connection.

  Therefore, when stacking semiconductor elements, a structure in which semiconductor elements smaller in size than those already mounted are stacked, or when the size of both semiconductor elements is approximately the same, between the stacked semiconductor elements. It is necessary to introduce a spacer to prevent the overlapping of the wire-bonded portion with the stacked semiconductor elements. (Patent Document 2)

  However, in a configuration in which semiconductor elements having a size smaller than that of already mounted semiconductor elements are stacked, semiconductor elements having the same size cannot be stacked, and the structure on the semiconductor device is restricted.

  In the method of introducing a spacer between stacked semiconductor elements, a new man-hour for introducing the spacer is required, and further, a bonding wire connected to the semiconductor element mounted on the substrate, and stacked on the bonding wire. Since it is necessary to use a spacer having a sufficient thickness in order to prevent contact with a semiconductor element, there is a problem that it is not suitable for thinning a semiconductor device.

  In order to solve such a problem, a plurality of semiconductor elements of the same size are stacked on a substrate, and an adhesive layer for enclosing the bonding wire portion is interposed between the semiconductor elements. A semiconductor device is disclosed. (Patent Document 3)

  Here, the adhesive used is required to have a function of bonding between semiconductor elements, a function of embedding the vicinity of the terminal of the bonding wire, and the like. However, in this case, since the adhesive adhesive layer is used for the adhesive layer, it is difficult to control the adhesive layer, and the adhesive layer protrudes during lamination, resulting in bonding on the substrate side. There was a problem blocking the terminal.

JP 2006-73982 A JP 2002-222913 A JP 2001-308262 A

  An object of the present invention is to provide a bonding apparatus in which a portion of the bonding wire in the vicinity of the terminal passes through the adhesive layer, and is softened by thermocompression bonding as the adhesive and does not protrude from the semiconductor chip. An object of the present invention is to provide an adhesive film having improved embedding properties near the terminals.

Such an object is achieved by the present invention described in the following (1) to (8).
(1) At least a first semiconductor element, an adhesive layer, and a second semiconductor element are laminated in this order on one surface side of the substrate, and a terminal formed on the functional surface of the first semiconductor element is bonded to the substrate. It is an adhesive film that is electrically connected by a wire, and a part near the terminal of the bonding wire is used as the adhesive layer of the semiconductor device that passes through the adhesive layer, and the adhesive film is An adhesive film comprising a resin composition comprising (A) a (meth) acrylic resin, (B) an epoxy resin, (C) a curing agent, and (D) a curing accelerator. .
(2) The adhesive film according to (1), wherein the (B) epoxy resin includes an epoxy resin having an aralkyl structure.
(3) The adhesive film according to (1) or (2), wherein the epoxy resin having the aralkyl structure is an epoxy resin represented by the general formula (1)
(In the formula, R1 is an alkyl group having 1 to 4 carbon atoms, a is an integer of 0 to 3, R2 is an alkyl group of 1 to 4 carbon atoms, b is an integer of 0 to 4, and they are the same as each other. (N is an average value and a positive number of 1 to 10.)
(4) The adhesive film according to any one of (1) to (3), wherein the epoxy resin having the aralkyl structure contains 30 to 80% by weight with respect to the entire epoxy resin (B).
(5) The adhesive film according to any one of (1) to (4), wherein the (C) curing agent includes a liquid phenol compound.
(6) The adhesive film according to any one of (1) to (5), wherein the liquid phenol compound is contained in an amount of 30 to 80% by weight with respect to the entire curing agent (C).
(7) The adhesive film according to any one of (1) to (6), wherein the (D) curing accelerator includes a phosphorus compound.
(8) The adhesive film according to any one of (1) to (7), wherein the phosphorus compound is a molecular compound of a tetra-substituted phosphonium and a polyfunctional phenol compound.

According to the present invention, it is possible to provide an adhesive film in which the adhesive film is softened by heating in the joining step and does not protrude from the semiconductor chip, and the embedding property of the bonding wire in the vicinity of the terminal is improved.

Hereinafter, the adhesive film of the present invention will be described.
The adhesive film of the present invention is
(A) acrylic resin,
(B) epoxy resin,
It is comprised with the resin composition containing (C) hardening | curing agent and (D) hardening accelerator.

  First, each component of the resin composition constituting the adhesive film will be described. Each component may be a single compound or a combination of a plurality of compounds.

  The (A) (meth) acrylic resin according to the present invention is a copolymer of (meth) acrylic acid ester and other monomers, and (meth) acrylic acid and its derivatives are the main monomers. A (meth) acrylic resin is preferred.

  Examples of (meth) acrylic acid esters include acrylic acid esters such as methyl acrylate and ethyl acrylate, and methacrylic acid esters such as methyl methacrylate and ethyl methacrylate. Moreover, acrylic acid, methacrylic acid, acrylonitrile, acrylamide etc. are mentioned as another monomer.

  Since the (A) (meth) acrylic resin has a low glass transition temperature, the initial adhesion can be improved by blending it in the resin composition. Here, the initial adhesion refers to adhesion when the adhesive film is bonded to the semiconductor element, and particularly refers to adhesion to the back surface of the wafer when the semiconductor element is in a wafer state.

  The (A) (meth) acrylic resin is preferably a (meth) acrylic acid ester copolymer having an epoxy group, a hydroxyl group, a carboxyl group, a nitrile group or the like. Thereby, the adhesiveness to adherends, such as the back surface of a semiconductor element, and the coating material on a semiconductor element, can be improved more. Specific examples of the compound having such a functional group include glycidyl (meth) acrylate having a glycidyl ether group, hydroxy (meth) acrylate having a hydroxyl group, carboxy (meth) acrylate having a carboxyl group, and (meth) having a nitrile group. Examples include acrylonitrile.

  Among these, it is particularly preferable to use a (meth) acrylic acid ester copolymer containing a monomer unit having a carboxyl group. Thereby, since hardening of an adhesive film is further accelerated | stimulated, it can be made to adhere | attach to a to-be-adhered body more quickly and firmly.

  The content of the (meth) acrylic acid ester copolymer containing a monomer unit having a carboxyl group is, for example, (A) from the viewpoint of firmly adhering to the adherend in a shorter time, 0.5% by weight or more, preferably 1% by weight or more. In addition, the content of the compound having a carboxyl group is, for example, 10% by weight or less, preferably 5% by weight or less, based on the whole (A) (meth) acrylic resin, from the viewpoint of further improving the storage stability of the adhesive film. .

The weight average molecular weight of the (A) (meth) acrylic resin is, for example, from 100,000 to 1.3 million, preferably from 150,000 to 1,000,000. By setting it as the said range, the film formability of an adhesive film can be improved further, and it becomes possible to ensure the fluidity | liquidity at the time of adhesion | attachment. In addition, even when the (A) (meth) acrylic resin contains a thermosetting functional group such as an epoxy group, a hydroxyl group, or a carboxyl group, it is further ensured that the resin exhibits a curing behavior by heat treatment. Can be suppressed.

  The weight average molecular weight of the (A) (meth) acrylic resin can be measured, for example, by gel permeation chromatography (GPC). As an example of measurement conditions, a high-speed GPC SC-8020 apparatus manufactured by Tosoh Corporation. In the column, TSK-GEL GMHXL-L, temperature 40 ° C., solvent tetrahydrofuran and the like can be mentioned.

  The glass transition temperature of the (A) (meth) acrylic resin is, for example, 0 ° C. or higher, preferably 5 ° C. or higher, from the viewpoint of further improving workability by suppressing the adhesion of the adhesive film from becoming too strong. . In addition, the glass transition temperature of the (A) acrylic resin is, for example, 30 ° C. or less, preferably 20 ° C. or less, from the viewpoint of further improving the adhesion at low temperatures.

  The glass transition temperature of the (A) (meth) acrylic resin is, for example, from −65 ° C. at a constant load (10 mN) using a thermomechanical property analyzer (manufactured by Seiko Instruments Inc., TMA / SS6100). It can be measured from the inflection point when pulled while raising the temperature at a heating rate of 5 ° C./min.

  Although content of the said (A) (meth) acrylic-type resin is not specifically limited, It is preferable that it is less than the sum total of the compounding quantity of (B) epoxy resin and (C) hardening | curing agent. By doing so, it is possible to effectively suppress the outgassing when the adhesive film is heat-treated, so that it is possible to prevent contamination by the outgas of the adherend and to improve the adhesion between the adhesive film and the adhesive surface. Can do.

The (B) epoxy resin according to the present invention refers to any of monomers, oligomers and polymers having an epoxy group.
Specific examples of the (B) epoxy resin include novolac epoxy resins such as phenol novolac epoxy resins and cresol novolac epoxy resins;
Bisphenol type epoxy resins such as bisphenol A type epoxy resins and bisphenol F type epoxy resins;
Hydroquinone type epoxy resin;
Biphenyl type epoxy resin;
Stilbene type epoxy resin;
Triphenolmethane epoxy resin;
Triazine nucleus-containing epoxy resin;
Dicyclopentadiene modified phenolic epoxy resin;
Examples include naphthol type epoxy resins, aralkyl type epoxy resins such as phenol aralkyl type epoxy resins having a phenylene and / or biphenylene skeleton, and naphthol aralkyl type epoxy resins having a phenylene and / or biphenylene skeleton.

Among these, novolac type epoxy resins, aralkyl type epoxy resins, and the like are preferably used. By using an aralkyl epoxy resin, the change in complex viscosity | * | of the adhesive film can be kept constant at around 100 ° C. to 150 ° C., which is the temperature at which the semiconductor element is thermocompression bonded. The fluctuation | variation of the flow amount of an adhesive film can be suppressed in the temperature range of 100 to 150 degreeC which is a crimping | compression-bonding temperature. Moreover, the glass transition temperature after hardening of an adhesive film can be raised by using a novolak-type epoxy resin, and the adhesiveness of an adhesive film and an adhesive surface can be improved.

Among the aralkyl type epoxy resins, the aralkyl type epoxy resin represented by the general formula (1) that can further suppress the fluctuation of the flow amount of the adhesive film in a temperature range of 100 ° C. to 150 ° C. is particularly preferable.
(In the formula, R1 is an alkyl group having 1 to 4 carbon atoms, a is an integer of 0 to 3, R2 is an alkyl group of 1 to 4 carbon atoms, b is an integer of 0 to 4, and they are the same as each other. (N is an average value and a positive number of 1 to 10.)

  The content of the (B) epoxy resin is not particularly limited, but is preferably 100 parts by weight or more and 1000 parts by weight or less with respect to 100 parts by weight of the (A) (meth) acrylic acid ester copolymer, 200 parts by weight or more and 500 parts by weight or less are particularly preferable. By setting it as the said range, the low linear expansion coefficient after adhesive film hardening and toughness can be made compatible.

Although content of the said aralkyl type epoxy resin is not specifically limited, 30 to 80 weight% is preferable with respect to the said whole (B) epoxy resin, and 40 to 70 weight% is especially preferable. By setting the above range, the change in the complex viscosity | * | of the adhesive film can be kept constant at around 100 ° C. to 150 ° C., which is a temperature at which a general semiconductor element is thermocompression bonded. It becomes possible to suppress the fluctuation | variation of the flow amount, Furthermore, it becomes possible to raise the glass transition temperature of the adhesive film after hardening.

  The softening point of the (B) epoxy resin is not particularly limited as long as it has compatibility with the (A) (meth) acrylic resin, but is preferably 40 ° C. or higher and 100 ° C. or lower, 50 ° C. or more and 90 ° C. or less is particularly preferable. By setting it as the said range, since the tack property of an adhesive film can be reduced, the workability | operativity in a semiconductor device assembly process can be improved. Furthermore, since the wettability fall at the time of the thermocompression bonding accompanying the melt viscosity raise of an adhesive film can be suppressed, the adhesiveness of an adhesive film and an adhesive surface can be improved.

  Moreover, you may use combining the several epoxy resin from which a softening point differs as said (B) epoxy resin. Thereby, there exists an advantage of making it easier to make compatible the effect which reduces the tackability of an adhesive film, and the effect which suppresses the wettability fall at the time of thermocompression bonding. For example, a combination of a plurality of epoxy resins having different softening points includes a combination of an epoxy resin having a softening point of 40 ° C. or higher and lower than 70 ° C. and an epoxy resin having a softening point of 70 ° C. or higher and 100 ° C. or lower.

The (C) curing agent according to the present invention can be appropriately selected and used as long as it acts as a curing agent for the epoxy resin. Specifically, polyamines including aliphatic polyamines such as diethylenetriamine, triethylenetetramine, and metaxylylenediamine, aromatic polyamines such as diaminodiphenylmethane, m-phenylenediamine, and diaminodiphenylsulfone, dicyandiamide, and organic acid dihydrazide Acid anhydrides such as amine-based curing agents such as compounds, aliphatic acid anhydrides such as hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, tritometic anhydride, benzophenone tetracarboxylic anhydride, etc. Physical curing agent, phenol novolak resin, cresol novolak resin, phenol aralkyl (including phenylene and biphenylene skeleton) resin, naphthol aralkyl resin, triphenol methane resin, dicyclopen Diene type phenol resin, bis (mono or di t-butylphenol) propane, methylene bis (2-propenyl) phenol, propylene bis (2-propenyl) phenol, bis [(2-propenyloxy) phenyl] methane, bis [(2- Propenyloxy) phenyl] propane, 4,4'-
(1-Methylethylidene) bis [2- (2-propenyl) phenol], 4,4 ′-(1-methylethylidene) bis [2- (1-phenylethyl) phenol], 4,4 ′-(1 -Methylethylidene) bis [2-methyl-6-hydroxymethylphenol], 4,4 '-(1-methylethylidene) bis [2-methyl-6- (2-propenyl) phenol], 4,4'-(1 -Phenolic curing agents such as -methyltetradecylidene) bisphenol.

  The content of the (C) curing agent used in the present invention can be determined by calculating the equivalent ratio of (B) epoxy resin and (C) curing agent. When (C) the curing agent is a phenol resin, the equivalent ratio of the epoxy equivalent of (B) epoxy resin and the functional group of (C) curing agent is preferably 0.5 or more and 1.5 or less, particularly 0.7 or more and 1 .3 or less is preferable. By setting it as the above range, both heat resistance and storage stability of the adhesive fill can be achieved.

  The (C) curing agent is preferably a liquid curing agent having a viscosity of 30 Pa · s (30,000 cps) or less at 25 ° C. Further, a liquid curing agent having a viscosity of 10 Pa · s (10,000 cps) or less at 25 ° C. is preferable. By setting the viscosity of the curing agent (C) at 25 ° C. to the specified value or less, the initial adhesiveness of the adhesive film and the reliability of the semiconductor device are improved.

The content of the liquid curing agent having a viscosity of 30 Pa · s (30,000 cps) or less at 25 ° C. is not particularly limited, but is preferably 30 to 80% by weight with respect to the entire (C) curing agent, particularly 40 ~ 70 wt% is preferred. By setting the above range, it is possible to suppress a decrease in wettability at the time of thermocompression bonding of the adhesive film, so that the adhesion between the adhesive film and the adhesive surface can be improved, and the tackiness of the adhesive film is further reduced. Therefore, workability can be improved.

Examples of the liquid curing agent having a viscosity of 30 Pa · s (30,000 cps) or less at 25 ° C. include liquid phenol compounds. Specifically, bis (mono or di-t-butylphenol) propane, methylene bis (2-propenyl) phenol, propylene bis (2-propenyl) phenol, bis [(2-propenyloxy) phenyl] methane, bis [(2- Propenyloxy) phenyl] propane, 4,4 '-(1-methylethylidene) bis [2- (2-propenyl) phenol], 4,4'-(1-methylethylidene) bis [2-
(1-Phenylethyl) phenol], 4,4 ′-(1-methylethylidene) bis [2-methyl-6-hydroxymethylphenol], 4,4 ′-(1-methylethylidene) bis [2-methyl-6 -(2-propenyl) phenol], 4,4 '-(1-methyltetradecylidene)
Bisphenol is mentioned. The viscosity of these liquid phenol compounds can be controlled by the number of nuclei n and the type of benzene ring substituent.

As the liquid phenol compound, those obtained by polymerizing allylphenol and formaldehyde are preferable, and a polycondensate of 2- (2-propenyl) phenol and formaldehyde represented by the formula (2) is particularly preferable.
(In the formula, p, q and r represent an integer of ^{1 to 3.} R ¹ , R ² and R ³ represent an allyl group.)

  As said (C) hardening | curing agent, it is also possible to add together with a solid phenol resin other than the said liquid phenol compound. Solid means a solid state at 25 ° C. and normal pressure. By using the solid phenolic resin in combination, tackiness of the adhesive film for semiconductor at room temperature can be reduced and workability can be improved. Moreover, this solid phenol resin refers to monomers, oligomers, and polymers in general having at least two phenolic hydroxyl groups capable of forming a crosslinked structure by curing reaction with the (B) epoxy resin, for example, Phenol novolac resins, cresol novolac resins, phenol aralkyl (including phenylene and biphenylene skeleton) resins, naphthol aralkyl resins, triphenol methane resins, dicyclopentadiene type phenol resins, and the like can be used. It may be used.

  The content of the solid phenol resin is not particularly limited, but the ratio of the epoxy equivalent of the (B) epoxy resin and the functional group equivalent of the liquid phenol compound and the solid phenol resin is 0.5 to 1.5. Particularly preferred is 0.7 or more and 1.3 or less. By setting it as the said range, heat resistance and preservability of an adhesive film can be made compatible.

  The (D) curing accelerator according to the present invention can be appropriately selected and used as long as it accelerates the curing reaction between the (B) epoxy resin and the (C) curing agent. Specific examples include imidazoles, amine-based catalysts such as 1,8-diazabicyclo (5,4,0) undecene, and phosphorus compounds such as molecular compounds of triphenylphosphine and tetra-substituted phosphonium and polyfunctional phenol compounds. . Among these, a phosphorus compound that achieves both fast curing of the adhesive film and corrosivity of the aluminum pad on the semiconductor element is preferable.

  The content of the (D) curing accelerator is preferably 0.01 to 10 parts by weight, and 0.1 to 5 parts by weight with respect to a total of 100 parts by weight of the (B) epoxy resin and the (C) curing agent. Particularly preferred. By setting it as the said range, it becomes possible to maintain the balance of the quick-hardening property and preservability of an adhesive film, and the physical property after hardening.

  Among the phosphorus compounds, a molecular compound of a tetra-substituted phosphonium and a polyfunctional phenol compound, which is excellent in quick curing of an adhesive film, corrosiveness to an aluminum pad of a semiconductor element, and storage stability of the adhesive film is particularly preferable.

  The molecular compound of the tetra-substituted phosphonium and the polyfunctional phenol compound is not a simple mixture but a compound having a structure such as a salt structure or a supramolecular structure.

  The tetra-substituted phosphonium, which is a molecular compound of the tetra-substituted phosphonium and the polyfunctional phenol compound, is a compound in which four alkyl groups and aromatic compounds are coordinated to the phosphorus atom from the balance between curability and storage stability of the adhesive film. preferable.

The substituent of the tetra-substituted phosphonium is not particularly limited, and the substituents may be the same or different from each other, and a tetra-substituted phosphonium having a substituted or unsubstituted aryl group or alkyl group as a substituent. Ions are preferred because they are stable to heat and hydrolysis. Specific examples of the tetra-substituted phosphonium include tetraphenylphosphonium, tetratolylphosphonium, tetraethylphenylphosphonium, tetramethoxyphenylphosphonium, tetranaphthylphosphonium, tetrabenzylphosphonium, ethyltriphenylphosphonium, n-butyltriphenylphosphonium, 2-hydroxyethyl. Examples include triphenylphosphonium, trimethylphenylphosphonium, methyldiethylphenylphosphonium, methyldiallylphenylphosphonium, and tetra-n-butylphosphonium. Among these, tetraphenylphosphonium is preferred from the balance between fast curability and storage stability of the adhesive film.

The polyfunctional phenol compound, which is a molecular compound of the tetra-substituted phosphonium and the polyfunctional phenol compound, has a phenolic hydroxyl group and is a phenoxide-type compound in which at least one of the hydroxyl groups is removed from hydrogen. ,In particular,
Examples thereof include a hydroxybenzene compound, a biphenol compound, a bisphenol compound, a hydroxy naphthalene compound, a phenol novolac resin, and a phenol aralkyl resin.

  Examples of the polyfunctional phenol compound include bis (4-hydroxy-3,5-dimethylphenyl) methane (common name: tetramethylbisphenol F), 4,4′-sulfonyldiphenol, and 4,4′-isopropylidene diene. Phenol (commonly called bisphenol A), bis (4-hydroxyphenyl) methane, bis (2-hydroxyphenyl) methane, (2-hydroxyphenyl) (4-hydroxyphenyl) methane and bis (4-hydroxyphenyl) methane Bisphenols such as bis (2-hydroxyphenyl) methane and a mixture of three kinds of (2-hydroxyphenyl) (4-hydroxyphenyl) methane (for example, bisphenol FD manufactured by Honshu Chemical Industry Co., Ltd.), 1,2-benzenediol, 1,3-benzenediol, 1 Dihydroxybenzenes such as 4-benzenediol, trihydroxybenzenes such as 1,2,4-benzenetriol, various isomers of dihydroxynaphthalene such as 1,6-dihydroxynaphthalene, 2,2′-biphenol, 4, Examples of the compound include various isomers of biphenols such as 4′-biphenol, and 1,2-dihydroxynaphthalene and 4,4′-sulfonyldiphenol, which are excellent in the balance between fast curability and storage stability, are preferable.

  In addition, the resin composition which comprises the adhesive film of this invention may contain components other than the said (A)-(D) component.

  The resin composition constituting the adhesive film of the present invention may contain (E) a coupling agent. Thereby, the adhesiveness of the resin component in an adhesive film and a to-be-adhered member, and the adhesiveness of the interface of the resin component in an adhesive film and a filler can be improved further.

  Examples of the (E) coupling agent include silane-based, titanium-based, and aluminum-based. Among these, a silane-based coupling agent that is excellent in the storage stability of the adhesive film and the adhesion between the adhesive film and the adhesive surface. Is preferred.

Examples of the silane coupling agent include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycol. Sidoxypropylmethyldimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-methacryloxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldimethoxysilane, N
-Β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-γ -Aminopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane and the like.

  The blending amount of the (E) coupling agent is preferably 0.01 parts by weight or more and 10 parts by weight or less, and 0.1 parts by weight or more and 5 parts by weight or less with respect to 100 parts by weight of the (A) acrylate ester copolymer. The following are particularly preferred: By setting it as the said range, the adhesiveness of an adhesive film and an adhesive surface and the suppression effect of outgas and a void are compatible.

  Moreover, the resin composition which comprises an adhesive film may contain the (F) inorganic filler. Thereby, the workability improvement of an adhesive film and the function to reduce the linear expansion coefficient after hardening can be provided.

  Examples of the inorganic filler (F) include silver, titanium oxide, silica, mica and the like. Among these, silica is preferable. By using the silica filler, the workability during the production of the adhesive film can be further improved. Moreover, although there exist crushing silica and fused silica as a shape of a silica filler, fused silica is preferable.

  (F) Although the average particle diameter of an inorganic filler is not specifically limited, 0.01 micrometer or more and 20 micrometers or less are preferable, and 0.1 micrometer or more and 5 micrometers or less are especially preferable. By setting it as the said range, aggregation of a filler can be suppressed in an adhesive film, an external appearance can be improved, and also it can suppress destroying a chip | tip at the time of thermocompression bonding.

(F) The content of the inorganic filler is not particularly limited, but is preferably 1 part by weight or more and 200 parts by weight or less, and preferably 5 parts by weight or more and 100 parts by weight or less with respect to 100 parts by weight of the resin component excluding the inorganic filler (F). Part by weight or less is particularly preferred. By setting the above range, the difference in linear expansion coefficient between the cured adhesive film and the adherend can be reduced, and the stress generated during thermal shock can be reduced. Furthermore, it can suppress reliably. Furthermore, since it can suppress that the elastic modulus of the adhesive film after curing becomes too high,
It becomes possible to further improve the adhesion between the adhesive film and the adherend interface.

  Moreover, the thickness of the adhesive film of the present invention is not particularly limited, but is, for example, 30 μm or more and 100 μm or less, preferably 40 μm or more and 80 μm or less. By setting the above range, it becomes possible to control the thickness accuracy more easily, and it is possible to perform electrical operation without deforming or cutting the wire-bonded portion of the semiconductor element already mounted on the substrate. Secure connections.

Next, the manufacturing method of the adhesive film of this invention is demonstrated.
The adhesive film of the present invention is prepared by, for example, dissolving the resin composition in a solvent such as methyl ethyl ketone, acetone, toluene, dimethylformaldehyde or the like to form a varnish, and then using a comma coater, a die coater, a gravure coater or the like as a release sheet. It is obtained by removing the release sheet after the solvent is volatilized by coating and drying.

  Next, an example of a semiconductor device using the adhesive film of the present invention will be described with reference to the drawings. In all the drawings, common constituent elements are denoted by the same reference numerals, and description thereof is omitted as appropriate.

FIG. 1 is a cross-sectional view showing the configuration of the semiconductor device of this embodiment.
The semiconductor device shown in FIG. 1 shows the case where the area of the first semiconductor element 11 in plan view and the area of the second semiconductor element 21 are substantially the same. As shown in FIG. In FIG. 1, an adhesive layer 2, a first semiconductor element 11, an adhesive film 1a, and a second semiconductor element 21 are laminated in this order on one surface side of the substrate 1 (upper side in FIG. 1). The terminal 101 formed on the functional surface of the first semiconductor element 11 and the substrate 1 are electrically connected by the first bonding wire 31. At that time, the terminal 101 near the terminal 101 of the first bonding wire 31 is connected. In the part 201, the first bonding wire 31 passes through the adhesive film 1a. The adhesive film 1a is composed of a resin composition containing (A) (meth) acrylic resin, (B) epoxy resin, (C) curing agent, and (D) curing accelerator as described above. .

Since the adhesive film 1a is composed of the resin composition as described above, it has excellent heat flow properties. As shown in FIG. 1, the portion 201 near the terminal 101 of the first bonding wire 31 is the first Even if the bonding wire 31 passes through the adhesive film 1a, the first bonding wire 31 can be electrically connected without being deformed or cut.
Moreover, since the adhesive film 1a has a small linear expansion coefficient, it can be thermally cured without damaging the first bonding wire 31 at the time of heat curing.

  In FIG. 1, the area in which the area of the first semiconductor element 11 in a plan view and the area of the second semiconductor element 21 in a plan view are substantially the same has been described. However, the present invention is not limited to this. The area of the second semiconductor element 21 may be smaller than the area of the second semiconductor element 21 in plan view, and vice versa.

Moreover, the adhesive layer 2 between the board | substrate 1 and the 1st semiconductor element 11 can also use the adhesive film 1a mentioned above, and the adhesive layer 2 may use adhesive agents, such as a paste form.
In addition, as shown in FIG. 2, the first semiconductor element 11 and the second semiconductor element 21 are preferably sealed with a sealing material 401.

  As mentioned above, although embodiment of this invention was described with reference to drawings, these are the illustrations of this invention, Various structures other than the above are also employable.

EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example and a comparative example, this invention is not limited to this.
Example 1
(Preparation of adhesive film resin varnish)
(A) As a (meth) acrylic resin, an acrylic ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 ° C., weight average molecular weight: 800,000) 100 parts by weight;
(B) 105 parts by weight of EOCN-1020-80 (orthocresol novolac type epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., manufactured by Nippon Kayaku Co., Ltd.) and NC3000P (aralkyl type epoxy resin, epoxy equivalent 272 g) / Eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 157 parts by weight;
(C) 82 parts by weight of a liquid phenol compound MEH-8000H (hydroxyl equivalent: 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent and solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, Sumitomo Bakelite Co., Ltd.) 55 parts by weight;
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula (3) and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. (Manufactured by Admatechs) was dissolved in methyl ethyl ketone (MEK) to obtain a resin varnish having a resin solid content of 41%.

(Manufacture of adhesive film with base film I)
After applying the resin varnish obtained by the above-described method to a polyethylene terephthalate film (Mitsubishi Chemical Polyester Film Co., Ltd., product number MRX50, thickness 50 μm) which is a base film (I) using a comma coater, The film was further dried for 5 minutes at 150 ° C. for 2 minutes to obtain an adhesive film having a thickness of 60 μm.

(Manufacture of adhesive layer with base film (II))
As the base film (II), Cleartech CT-H717 (manufactured by Kuraray Co., Ltd.) consisting of 60 parts by weight of Hibler and 40 parts by weight of polypropylene was used to form a film having a thickness of 100 μm with an extruder, and the surface was subjected to corona treatment. Next, a copolymer having a weight average molecular weight of 500,000 obtained by copolymerizing 50 parts by weight of 2-ethylhexyl acrylate, 10 parts by weight of butyl acrylate, 37 parts by weight of vinyl acetate, and 3 parts by weight of 2-hydroxyethyl methacrylate. It applied to the 38-micrometer-thick polyester film which peeled the unification | combination so that the thickness after drying might be set to 10 micrometers, and it dried for 5 minutes at 80 degreeC, and obtained the adhesive layer. Thereafter, the pressure-sensitive adhesive layer was laminated on the corona-treated surface of the base film (II) to obtain a pressure-sensitive adhesive layer with the base film (II).

(Manufacture of adhesive film with dicing sheet function)
A protective film is pasted on the adhesive film with the base film (I) described above, the adhesive film with the base film (I) is half-cut, and the adhesive film of the adhesive layer with the base film (II) is pasted on the adhesive material surface. The base film (II), the pressure-sensitive adhesive layer, the base film (I), and the adhesive film were laminated in this order to obtain an adhesive film with a dicing sheet function by attaching and peeling off the protective film.

(Manufacture of semiconductor device (FIG. 2))
The semiconductor device shown in FIG. 2 was manufactured according to the following procedure. The basic configuration of the semiconductor device shown in FIG. 2 is the same as that of the semiconductor device described above with reference to FIG. However, FIG. 2 does not have the second bonding wire 41 in FIG. 1 and the terminal 301 formed on the functional surface of the second semiconductor element.

  An organic substrate (circuit level difference of 5 to 10 μm) containing bismaleimide / triazine coated with a solder resist (manufactured by Taiyo Ink Co., Ltd., AUS308) as a substrate of a semiconductor device was prepared. In addition, copper foil, nickel plating, and gold plating are patterned in order on the part where the solder resist on one side of the simulated board is not applied to form terminals for wire bonding, with solder ball mounting areas and via holes provided on the opposite side of the simulated board. Conducted.

A semiconductor element of 10.5 mm × 10.5 mm (thickness 200 μm) is mounted on the substrate using a die bonder (manufactured by ASM, AD898) with silver paste (Sumitomo Bakelite Co., Ltd., Sumire Resin Excel CRM1525). The silver paste was cured by performing a heat treatment at 60 ° C. for 60 minutes, and the first semiconductor element was mounted. Next, wire bonding was performed between the die pad portion of the first semiconductor element and the wire bonding terminal of the substrate using a wire bonding apparatus (Eagle 60 manufactured by ASM). At this time, the height of the wire from the surface of the first semiconductor element was about 50 μm.

  Furthermore, the adhesive film with a dicing sheet function was affixed at 40 degreeC on the 8-inch 200-um wafer in which the 2nd semiconductor element was formed, and the wafer with an adhesive film with a dicing sheet function was obtained.

  Thereafter, the wafer was diced (cut) into a size of each semiconductor element of 10.5 mm × 10.5 mm square at a spindle rotation speed of 30,000 rpm and a cutting speed of 50 mm / sec using a dicing saw. Next, it pushed up from the back surface of the die attach film with a dicing function, peeled between the base film and the adhesive layer, and obtained the semiconductor element with an adhesive film.

The second semiconductor element with the adhesive film is bonded onto the wire-bonded first semiconductor element using a die bonder (manufactured by ASM Co., AD898) under conditions of 130 ° C., 10 N, 2 seconds, and then 130 ° C., The adhesive film is semi-cured by performing a heat treatment for 60 minutes, further sealed with a sealing resin EME-G790 (manufactured by Sumitomo Bakelite Co., Ltd.), and subjected to a heat treatment at 175 ° C. for 2 hours. Curing was performed to obtain a total of 10 semiconductor devices.

(Example 2)
(A) Acrylate ester copolymer (butyl acrylate-acrylonitrile-ethyl acrylate-glycidyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-80H, Tg: 10 ° C., weight average as (meth) acrylic resin Molecular weight: 350,000) 100 parts by weight;
(B) 105 parts by weight of EOCN-1020-80 (orthocresol novolac type epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., manufactured by Nippon Kayaku Co., Ltd.) and NC3000P (aralkyl type epoxy resin, epoxy equivalent 272 g) / Eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 157 parts by weight;
(C) 82 parts by weight of a liquid phenol compound MEH-8000H (hydroxyl equivalent: 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent, solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, Sumitomo Bakelite Co., Ltd.) 55 parts by weight;
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula 3 and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Example 3)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) EOCN-1020-80 (orthocresol novolac type epoxy resin) as an epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., manufactured by Nippon Kayaku Co., Ltd.) 246 parts by weight;
(C) Liquid phenol compound MEH-8000H as a curing agent (hydroxyl equivalent: 141 g / O
H group, manufactured by Meiwa Kasei Co., Ltd.) 92 parts by weight, solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, manufactured by Sumitomo Bakelite Co., Ltd.) 61 parts by weight;
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula 3 and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

Example 4
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) NC3000P as an epoxy resin (aralkyl type epoxy resin, epoxy equivalent 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 274 parts by weight;
(C) Liquid phenol compound (MEH-8000H, hydroxyl group equivalent 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) 75 parts by weight as a curing agent, solid phenol resin PR-HF-3 (hydroxyl group equivalent 104 g / OH group, Sumitomo Bakelite) 50 parts by weight)
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula 3 and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Example 5)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) EOCN-1020-80 (orthocresol novolac type epoxy resin) as an epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., Nippon Kayaku Co., Ltd.) 111 parts by weight and NC3000P (aralkyl type epoxy resin, epoxy equivalent) 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 166 parts by weight;
(C) 122 parts by weight of a solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, manufactured by Sumitomo Bakelite Co., Ltd.) as a curing agent;
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula 3 and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Example 6)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) EOCN-1020-80 (orthocresol novolac type epoxy resin) as an epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., manufactured by Nippon Kayaku Co., Ltd.) and NC3000P (aralkyl type epoxy resin, epoxy equivalent) 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 150 parts by weight;
(C) 148 parts by weight of a liquid phenol compound MEH-8000H (hydroxyl equivalent: 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent;
(D) 0.8 part by weight of a molecular compound of a tetra-substituted phosphonium represented by formula 3 and a polyfunctional phenol compound as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Example 7)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) 105 parts by weight of epoxy resin (EOCN-1020-80 (orthocresol novolac type epoxy resin), epoxy equivalent 200 g / eq, softening point 80 ° C., Nippon Kayaku Co., Ltd.) and NC3000P (aralkyl type epoxy resin, epoxy equivalent) 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 157 parts by weight;
(C) 82 parts by weight of a liquid phenol compound MEH-8000H (hydroxyl equivalent: 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent, solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, Sumitomo Bakelite Co., Ltd.) 55 parts by weight;
(D) 0.8 part by weight of an imidazole compound (2PHZ-PW, manufactured by Shikoku Kasei Kogyo Co., Ltd.) as a curing accelerator;
Γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and spherical silica (SE2050, average particle size 0.5 μm, manufactured by Admatechs) as an inorganic filler 56 parts by weight were used.
The experiment was conducted according to the method of Example 1.

(Comparative Example 1)
Polyimide resin as a thermoplastic resin (1,3-bis (3-aminophenoxy) benzene (made by Mitsui Chemicals, Inc.) APB as a diamine component) 43.85 g (0.15 mol) and α, ω-bis (3- Aminopropyl) polydimethylsiloxane (average molecular weight 837) (G9 manufactured by Fuso Chemical Co., Ltd.) 125.55 g (0.15 mol) and 4,4′-oxydiphthalic dianhydride (manac manufactured by Manac Co., Ltd.) as the acid component (ODPA-M) polyimide resin obtained by synthesizing 93.07 g (0.30 mol), Tg: 70 ° C., weight average molecular weight 30,000) 100 parts by weight,
(B) EOCN-1020-80 (orthocresol novolak type epoxy resin) as an epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., Nippon Kayaku Co., Ltd.) 105 parts by weight and NC3000P (aralkyl type epoxy resin, epoxy equivalent) 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 157 parts by weight;
(C) 82 parts by weight of a liquid phenol compound (MEH-8000H, hydroxyl group equivalent 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent, solid phenol resin PR-HF-3 (hydroxyl group equivalent 104 g / OH group, Sumitomo Bakelite) 55 parts by weight)
(D) 0.8 part by weight of an imidazole compound (2PHZ-PW, manufactured by Shikoku Kasei Kogyo Co., Ltd.) as a curing accelerator;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Comparative Example 2)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

(Comparative Example 3)
(A) Acrylate ester copolymer (ethyl acrylate-butyl acrylate-acrylonitrile-acrylic acid-hydroxyethyl methacrylate copolymer, manufactured by Nagase ChemteX Corporation, SG-708-6, Tg: 6 as (meth) acrylic resin ° C, weight average molecular weight: 800,000) 100 parts by weight;
(B) EOCN-1020-80 (orthocresol novolak type epoxy resin) as an epoxy resin, epoxy equivalent 200 g / eq, softening point 80 ° C., Nippon Kayaku Co., Ltd.) 105 parts by weight and NC3000P (aralkyl type epoxy resin, epoxy equivalent) 272 g / eq, softening point 58 ° C., manufactured by Nippon Kayaku Co., Ltd.) 157 parts by weight;
(C) 82 parts by weight of a liquid phenol compound MEH-8000H (hydroxyl equivalent: 141 g / OH group, manufactured by Meiwa Kasei Co., Ltd.) as a curing agent, solid phenol resin PR-HF-3 (hydroxyl equivalent: 104 g / OH group, Sumitomo Bakelite Co., Ltd.) 55 parts by weight;
(E) γ-glycidoxypropyltrimethoxysilane (KBM403E, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.5% by weight as a coupling agent; and (F) spherical silica (SE2050, average particle size 0.5 μm) as an inorganic filler. 56 parts by weight (manufactured by Admatechs).
The experiment was conducted according to the method of Example 1.

  The following evaluation was performed about the adhesive film obtained by each Example and the comparative example. The evaluation items are shown together with the contents. The obtained results are shown in Table 1.

1. Low temperature sticking property The adhesive films obtained in each Example and Comparative Example were attached to the back surface of a wafer having a thickness of 550 μm at a temperature of 40 ° C., a pressure of 0.3 MPa, and a laminating speed of 10 mm / sec, and 180 ° peel strength was evaluated.
The 180 ° peel strength was measured by using Tensilon (RTC-1250A manufactured by ORIENTEC Co., Ltd.) and peeling in a 180 ° direction at a peeling speed of 50 mm / min and a peeling width of 25 mm.
A: The peel strength was 200 N / m or more.
○: The peel strength was 100 N / m or more and less than 200 N / m.
Δ: The peel strength was 50 N / m or more and less than 100 N / m.
X: The peel strength was less than 50 N / m.

2. Preservability The preservability of the obtained adhesive film is determined by measuring the heat value of curing after treating the adhesive film at 50 ° C. for 1 day as an accelerated test, and the heat value of curing after storage treatment relative to the initial heat value (mJ / mg). Evaluation was made as a percentage of the amount (mJ / mg). Units%. The closer this value is to 100%, the higher the storage stability.
The curing calorific value was measured using a differential scanning calorimeter (DSC) (DSC6200, manufactured by Seiko Instruments Inc.) at a measurement range of 30 to 300 ° C. and a heating rate of 10 ° C./min.
(Double-circle): The percentage of the ratio of the calorific value was 90% or more.
◯: The percentage of the ratio of the heat generation amount during curing was 70% or more and less than 90%.
(Triangle | delta): Percentage of ratio of the calorific value was 50% or more and less than 70%.
X: The percentage of the ratio of the calorific value was less than 50%.

3. Wire penetrability In the semiconductor device manufactured by the Example and the comparative example, it was observed by SEM whether the wire penetrated the adhesive film from the side surface of the semiconductor device after mounting the second semiconductor element. Each code is as follows.
(Double-circle): The wire has penetrated into the adhesive film.
X: The adhesive film is deforming the wire.
Or the wire does not penetrate the adhesive film.

4). Protrusion of Adhesive Film In the semiconductor devices manufactured in Examples and Comparative Examples, it was observed by SEM whether the adhesive film protruded from the side surface of the semiconductor device after mounting the second semiconductor element. Each code is as follows.
(Double-circle): The protrusion length from the side surface was less than 20um.
A: The protruding length from the side surface was 20 μm or more and less than 50 μm.
(Triangle | delta): The protrusion length from the side surface was 50 to 100 micrometer.
X: The protrusion length from the side surface was 100 μm or more.

5. Adhesiveness after moisture absorption treatment The semiconductor device before resin sealing obtained in each example and comparative example was subjected to moisture absorption treatment at 85 ° C./60% RH / 168 hours, and then 260 of the first semiconductor element and the second semiconductor element. The shear strength at 0 ° C. was evaluated.
The shear strength at 260 ° C. is obtained by holding a sample obtained by moisture absorption treatment of the semiconductor device before resin sealing at 85 ° C./60% RH / 168 hours on a hot plate at 260 ° C. for 20 seconds, and then on the second semiconductor element side. Further, the shear strength was measured when a shear stress was applied at a rate of 0.5 mm / min.
◎: Shear strength is 2.0 MPa or more ○: Shear strength is 1.0 or more and less than 2.0 MPa △: Shear strength is 0.5 or more and less than 0.1 MPa ×: Shear strength is less than 0.5 MPa

6). Crack resistance Crack resistance is determined by scanning ultrasonic flaw detection by subjecting the semiconductor devices obtained in the examples and comparative examples to moisture absorption treatment at 85 ° C./60% RH / 168 hours, followed by IR reflow at 260 ° C. three times. Machine (SAT). Each code is as follows.
A: Generated cracks 0 out of 10 O: Generated cracks 1 to 3 out of 10 Δ: Generated cracks 4 to 9 out of 10 ×: Generated cracks 10 out of 10

As is clear from Table 1, the adhesive films obtained in Examples 1 to 7 were excellent in wire penetration.
Moreover, the adhesive films obtained in Examples 1 to 6 were excellent in storage stability.
Moreover, the adhesive films obtained in Examples 1 to 5 and 7 were also excellent in film protrusion.
In addition, the adhesive films obtained in Examples 1, 2, 4, 6, and 7 were excellent in film protrusion.
Further, the semiconductor devices obtained in Examples 1 to 7 were excellent in crack resistance.

FIG. 1 is a schematic diagram schematically illustrating an example of a semiconductor device. FIG. 2 is a schematic diagram schematically showing the semiconductor device in the example. DESCRIPTION OF SYMBOLS 1a Adhesive film 1 Substrate 2 Adhesive layer 11 1st semiconductor element 21 2nd semiconductor element 31 1st bonding wire 41 2nd bonding wire 101 Terminal 201 formed in the functional surface of the 1st semiconductor element Part 301 Terminal 401 formed on functional surface of second semiconductor element Sealing resin

Claims (6)

On one surface side of the substrate, at least a first semiconductor element, an adhesive layer, and a second semiconductor element are laminated in this order,
The terminal formed on the functional surface of the first semiconductor element and the substrate are electrically connected by a bonding wire,
A part of the bonding wire near the terminal is an adhesive film used as the adhesive layer of the semiconductor device that passes through the adhesive layer,
The adhesive film is
(A) a (meth) acrylic resin;
(B) an epoxy resin;
(C) a curing agent;
(D) a curing accelerator;
An adhesive film comprising an epoxy resin having an aralkyl structure represented by the general formula (1), wherein the epoxy resin (B) includes an aralkyl structure represented by the general formula (1) .

(In the formula, R1 is an alkyl group having 1 to 4 carbon atoms, a is an integer of 0 to 3, R2 is an alkyl group of 1 to 4 carbon atoms, b is an integer of 0 to 4, and they are the same as each other. (N is an average value and a positive number of 1 to 10.) The adhesive film of Claim 1 which contains 30-80 weight% of epoxy resins which have the aralkyl structure represented by the said General formula (1) with respect to the said whole (B) epoxy resin. The curing agent (C) are those containing liquid phenolic compound, the adhesive film according to claim 1 or 2. The adhesive film according to any one of claims 1 to 3 , wherein the liquid phenol compound is contained in an amount of 30 to 80% by weight based on the whole (C) curing agent. The curing accelerator (D) are those containing a phosphorus compound, the adhesive film according to any one of claims 1 to 4. The adhesive film according to any one of claims 1 to 5 , wherein the phosphorus compound is a molecular compound of a tetra-substituted phosphonium and a polyfunctional phenol compound.