JP4584028B2 - Adhesive film for semiconductor element and semiconductor device - Google Patents

Description

  The present invention relates to a pressure-sensitive adhesive film for a semiconductor element and a semiconductor device using the same, and more particularly, suitable for an adhesive material between an electronic component such as a semiconductor element and a support member such as a lead frame or an insulating support substrate, that is, for die bonding. The present invention relates to an adhesive film for adhering semiconductor elements and a semiconductor device manufactured using the adhesive film for adhering semiconductor elements.

As an adhesive material between an electronic component such as a semiconductor element and a support member such as a lead frame or an insulating support substrate, conventionally, an Au—Si eutectic alloy, solder, silver paste, an adhesive film, and the like are known. Among these, Au-Si eutectic alloy and solder have a large elastic modulus and are difficult to be applied to large chips corresponding to high integration of semiconductor elements. Is mainly used. Silver paste is mainly composed of thermosetting resin from the viewpoint of heat resistance reliability, and adhesive film is mainly composed of thermoplastic resin from the viewpoint of film formation. An adhesive film using a thermosetting resin has also been proposed. Especially in high-density mounting semiconductor devices with a small mounting area such as chip size package, stack package, and system-in package, film-like adhesives with excellent thickness accuracy and overhang controllability are widely applied compared to paste-like adhesives. It is becoming.
JP-A-5-331444 Japanese Patent No. 2996857 Japanese Patent Laid-Open No. 9-59589 JP-A-11-92744

  The silver paste containing thermosetting resin as a main component has a problem that the outgas generated from the silver paste contaminates the semiconductor element when the semiconductor package is assembled and heated, and the wire bondability (wire bond characteristic) in the wire bonding process is deteriorated. . Another problem is that the outgas contaminates the heating device.

  Adhesive films using thermoplastic resin generate less outgassing during heating, and can be used with a low melting point thermoplastic resin to reduce the bonding temperature and damage the chip, such as lead frame oxidation. Can be reduced. However, an adhesive film using a thermoplastic resin having a low melting point has a problem that it cannot withstand heat treatment after die bonding (for example, a wire bonding process, a sealing process, etc.) because of low adhesive force when heated.

  In addition, adhesive films using thermoplastic resins and thermosetting resins can be used to reduce the bonding temperature by selecting and using thermoplastic resins with a low melting point, and by using thermosetting resins, It can withstand the soldering heat treatment at around 260 ° C. at the time of mounting as well as the high adhesive strength at, but since it contains a thermosetting resin, there is a problem that outgas is likely to occur during heating.

  An object of the present invention is an adhesive film for adhering an electronic component such as a semiconductor element and a lead frame or an insulating support substrate, and withstands a heat treatment of soldering around 260 ° C. during mounting as well as a high adhesive force during heat. In addition, it is an object of the present invention to provide an adhesive film that generates less outgas and therefore solves problems such as contamination of semiconductor elements and heating devices and deterioration of wire bond characteristics.

  Analysis of the outgas component generated when the adhesive film for a semiconductor element containing a silver paste or thermosetting resin containing a thermosetting resin as a main component is heated. This is an unreacted resin of the thermosetting resin used mainly. It was found to be due to the solvent or reactive diluent. Therefore, various thermosetting resins have been studied and the present invention has been completed.

That is, the first invention is a pressure-sensitive adhesive film for bonding a semiconductor element containing a thermoplastic resin, an epoxy resin and an epoxy resin curing agent, wherein the epoxy resin curing agent has three or more aromatic rings in the molecule. It is related with the adhesive film which is an aralkyl phenol type compound represented by (1).



(In general formula (I), R1 to R11 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a phenyl group or a hydroxyl group, m represents a positive number of 1 to 10, and X represents a divalent group. Represents an organic group or a single bond.)
Here, the adhesive film may be one having an adhesive film attached to a substrate (that is, an adhesive film with a substrate).
It is a preferable aspect that the thermoplastic resin is a polyimide resin in terms of heat resistance.

  Moreover, it is a preferable aspect that a polyimide resin is a polyimide resin obtained by making the tetracarboxylic dianhydride represented by general formula (II) and diamine react.

(In General Formula (II), X is a divalent group selected from the group consisting of —O—, —O—Y—O—, —CO—O—Y—OCO—, and Y is a divalent group. Represents an organic group of
Furthermore, containing a filler is a preferred embodiment in terms of heat resistance.

  A second invention is a semiconductor device in which a semiconductor element is bonded to a support member using the above film, and the semiconductor element is sealed with a sealing material.

  The adhesive film for adhering semiconductor elements of the present invention has low-temperature adhesiveness, good thermal adhesiveness and high solder heat resistance as an adhesive material for electronic components such as semiconductor elements and support members such as lead frames and insulating support substrates. In addition, since the generation of outgas is small, problems such as contamination of the semiconductor element and the heating device and deterioration of wire bond characteristics are not caused. The semiconductor device of the present invention has high solder heat resistance that can withstand soldering heat treatment at around 260 ° C. during mounting, and has high reliability.

Hereinafter, the present invention will be described in detail.
The thermoplastic resin contained in the adhesive film for adhering a semiconductor element of the present invention is not limited. For example, polyimide resin, polyamide resin, polyamideimide resin, polyetherimide resin, polyester resin, siloxane polyimide resin, polyester There are imide resins, phenoxy resins, polysulfone resins, polyethersulfone resins, polyphenylene sulfide resins, polyester resins, polyether ketone resins, and the like, but preferred are polyimide resins. The polyimide resin will be described in detail later.

The epoxy resin contained in the pressure-sensitive adhesive film of the present invention is not limited as long as it contains at least two epoxy groups in the molecule, and examples thereof include compounds represented by the following formulas (1) to (3). .




(In formulas (1) to (3), R1 represents a divalent organic group, R2 represents a trivalent organic group, and R3 represents a tetravalent organic group.)
In the formula, examples of the divalent organic group include an alkyl group having 1 to 10 carbon atoms, examples of the trivalent organic group include an alkyl group having 1 to 10 carbon atoms, and examples of the tetravalent organic group include And an alkyl group having 1 to 10 carbon atoms.

  Examples of such epoxy resins include bisphenol A glycidyl ether, bisphenol F glycidyl ether, bisphenol AD glycidyl ether, bisphenol S glycidyl ether, 2,6-xylenol glycidyl ether, and water addition Bisphenol A type glycidyl ether, 1,4-cyclohexanedimethanol type glycidyl ether, diphenyl ether type glycidyl ether, ethylene oxide adduct bisphenol A type glycidyl ether, propylene oxide adduct bisphenol A type glycidyl ether, polyethylene glycol type Glycidyl ether, polypropylene glycol type glycidyl ether, neopentyl glycol type glycidyl ether, 1, -Hexanediol-type glycidyl ether, glycidyl ether of phenol novolac resin, glycidyl ether of cresol novolac resin, glycidyl ether of naphthalene resin, trifunctional glycidyl ether, tetrafunctional glycidyl ether, glycidyl ether of dicyclopentadiene phenol resin, dimer Examples include acid glycidyl ester, trifunctional glycidylamine, tetrafunctional glycidylamine, naphthalene resin glycidylamine, polysulfide-modified epoxy resin, polybutadiene-modified epoxy resin, and the like. These may contain a monofunctional epoxy.

The epoxy resin curing agent contained in the pressure-sensitive adhesive film of the present invention is an aralkylphenol compound having three or more aromatic rings in the molecule. What is preferable as such an epoxy resin curing agent is an aralkylphenol compound represented by the following general formula (4).


In the general formula (4), R1 to R11 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a phenyl group, or a hydroxyl group, and m represents a positive number of 1 to 10. X represents a single bond or a divalent organic group. Examples of X include the following groups.





Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, propyl, 2-methylethyl and the like.
Among such aralkylphenol compounds, a compound represented by the following general formula (5) is particularly preferable in terms of expressing strong adhesive force.

(In formula (5), m represents a positive number of 1 to 10.)
As fillers contained in the adhesive film of the present invention, metal fillers such as silver powder, gold powder and copper powder, silica, alumina, titania, glass, iron oxide, ceramic, boron nitride and other inorganic fillers, polymethyl methacrylate, butadiene-styrene And organic fillers such as silicone resins.

  The thermoplastic resin that can be used in the present invention is not particularly limited as described above, but is preferably a polyimide resin. The polyimide resin can be usually produced by reacting tetracarboxylic dianhydride and diamine.

  Examples of tetracarboxylic dianhydrides that can be used include pyromellitic dianhydride, 3,3 ′, 4,4′-diphenyltetracarboxylic dianhydride, and 2,2 ′, 3,3′-diphenyltetracarboxylic acid. Dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1-bis (2, 3-dicarboxyphenyl) ethane dianhydride, 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, bis (3,4 -Dicarboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, bis (3,4-dicarboxypheny ) Ether dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, 3,4,3 ', 4'-benzophenone tetracarboxylic dianhydride, 2,3,2', 3- Benzophenone tetracarboxylic dianhydride, 2,3,3 ', 4'-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 2,3,6,7- Naphthalenetetracarboxylic dianhydride, 1,2,4,5-naphthalene-tetracarboxylic dianhydride, 1,4,5,8-naphthalene-tetracarboxylic dianhydride, 2,6-dichloronaphthalene- 1,4,5,8-tetracarboxylic dianhydride, 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 2,3,6,7-tetrachloronaphthalene 1,4,5,8-tetra Rubonic dianhydride, phenanthrene-1,8,9,10-tetracarboxylic dianhydride, pyrazine-2,3,5,6-tetracarboxylic dianhydride, thiophene-2,3,4,5- Tetracarboxylic dianhydride, 2,3,3 ', 4'-biphenyltetracarboxylic dianhydride, 3,4,3', 4'-biphenyltetracarboxylic dianhydride, 2,3,2 ', 3'-biphenyltetracarboxylic dianhydride, bis (3,4-dicarboxyphenyl) dimethylsilane dianhydride, bis (3,4-dicarboxyphenyl) methylphenylsilane dianhydride, bis (3,4- Dicarboxyphenyl) diphenylsilane dianhydride, 1,4-bis (3,4-dicarboxyphenyldimethylsilyl) benzene dianhydride, 1,3-bis (3,4-dicarboxyphenyl) -1, 1,3,3-tetramethyldicyclohexane dianhydride, p-phenylenebis (trimellitate anhydride), ethylenetetracarboxylic dianhydride, 1,2,3,4-butanetetracarboxylic dianhydride, decahydro Naphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic acid Dianhydride, cyclopentane-1,2,3,4-tetracarboxylic dianhydride, pyrrolidine-2,3,4,5-tetracarboxylic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic Acid dianhydride, bis (exo-bicyclo [2,2,1] heptane-2,3-dicarboxylic dianhydride) sulfone, bicyclo- (2,2,2) -oct (7) -ene 2,3 , 5,6-tetra Rubonic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis [4- (3,4-dicarboxyphenoxy) phenyl] hexafluoropropane Anhydride, 4,4'-bis (3,4-dicarboxyphenoxy) diphenyl sulfide dianhydride, 1,4-bis (2-hydroxyhexafluoroisopropyl) benzenebis (trimellitic dianhydride), 1,3-bis (2-hydroxyhexafluoroisopropyl) benzenebis (trimellitic dianhydride), 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid Acid dianhydride, tetrahydrofuran-2,3,4,5-tetracarboxylic dianhydride, and the like, which are represented by the following general formula (II). The tetracarboxylic dianhydride is particularly preferred because of its strong adhesive strength and ease of handling.

(In General Formula (II), X is a divalent group selected from the group consisting of —O—, —O—Y—O—, —CO—O—Y—OCO—, and Y is a divalent group. Represents an organic group of
Examples of the divalent organic group for Y include an alkyl group having 1 to 10 carbon atoms.
A particularly preferred polyimide resin is a tetracarboxylic dianhydride in which the content of the tetracarboxylic dianhydride of the formula (II) is 30 mol% or more, more preferably 50 mol% or more of the total tetracarboxylic dianhydride. And a polyimide resin obtained by reacting diamine.

Specific examples of the tetracarboxylic dianhydride represented by the formula (II) include 4,4′-oxydiphthalic anhydride, 3,4′-oxydiphthalic anhydride, and 3,3′-oxydiphthalic anhydride. 4,4 ′-(4,4′-isopropylidenediphenoxy) bis (phthalic anhydride), 4,4′-hydroquinonebis (phthalic anhydride), 2,2′-bis (4-hydroxyphenyl) propane Dibenzoate-3,3 ′, 4,4′-tetracarboxylic dianhydride, 1,2 ethylenebis (trimellitic acid monoester anhydride), p-phenylenebis (trimellitic acid monoester anhydride), etc. Among them, 4,4′-oxydiphthalic anhydride is preferable.
By setting the amount of the tetracarboxylic dianhydride represented by the above formula (II) to be 30 mol% or more, more preferably 60% or more with respect to the total tetracarboxylic dianhydride, the low temperature of the adhesive film Stickiness can be maintained.

  Examples of the diamine that is one of the polyimide resin raw materials include 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1, Aliphatic diamines such as 7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, o-phenylenediamine, m -Phenylenediamine, p-phenylenediamine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4 , 4'-Diaminodiphenylmethane, 3,3'-diamy Diphenyldifluoromethane, 3,4'-diaminodiphenyldifluoromethane, 4,4'-diaminodiphenyldifluoromethane, 3,3'-diaminodiphenylsulfone, 3,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone 3,3'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl ketone, 3,4'-diaminodiphenyl Ketone, 4,4'-diaminodiphenyl ketone, 2,2-bis (3-aminophenyl) propane, 2,2 '-(3,4'-diaminodiphenyl) propane, 2,2-bis (4-aminophenyl) ) Propane, 2,2-bis (3-aminophenyl) hexafluoropropane, 2, -(3,4'-diaminodiphenyl) hexafluoropropane, 2,2-bis (4-aminophenyl) hexafluoropropane, 1,3-bis (3-aminophenoxy) benzene, 1,4-bis (3- Aminophenoxy) benzene, 1,4-bis (4-aminophenoxy) benzene, 3,3 '-(1,4-phenylenebis (1-methylethylidene)) bisaniline, 3,4'-(1,4-phenylene Bis (1-methylethylidene)) bisaniline, 4,4 ′-(1,4-phenylenebis (1-methylethylidene)) bisaniline, 2,2-bis (4- (3-aminophenoxy) phenyl) propane, 2 , 2-bis (4- (4-aminophenoxy) phenyl) propane, 2,2-bis (4- (3-aminophenoxy) phenyl) hexafluoropropane, , 2-bis (4- (4-aminophenoxy) phenyl) hexafluoropropane, bis (4- (3-aminophenoxy) phenyl) sulfide, bis (4- (4-aminophenoxy) phenyl) sulfide, bis (4- Aromatic diamines such as (3-aminophenoxy) phenyl) sulfone and bis (4- (4-aminophenoxy) phenyl) sulfone can be mentioned. Two or more of these may be mixed and used.

The condensation reaction of tetracarboxylic dianhydride and diamine is carried out in an organic solvent. In this case, tetracarboxylic dianhydride and diamine are preferably used in equimolar or almost equimolar amounts, and the order of addition of the components is arbitrary. Examples of the organic solvent to be used include dimethylacetamide, dimethylformamide, N-methyl-2-pyrrolidone, trimethylbenzene, dimethyl sulfoxide, hexamethylphosphorylamide, m-cresol, o-chlorophenol and the like.
The reaction temperature is 80 ° C. or lower, preferably 0 to 50 ° C. As the reaction proceeds, the viscosity of the reaction solution gradually increases. In this case, polyamic acid, which is a polyimide precursor, is generated.

Polyimide can be obtained by dehydrating and ring-closing the reactant (polyamic acid). Dehydration ring closure can be performed using a heat treatment method at 120 ° C. to 250 ° C. or a chemical method. In the present invention, the polyimide resin is a general term for polyimide and its precursor. The precursor of polyimide includes not only polyamic acid but also partially imidized polyamic acid.
The epoxy resin and the epoxy resin curing agent used in the production method of the present invention cause a crosslinking (crosslinking) reaction by heat. In order to accelerate this reaction, a curing accelerator (catalyst) can be appropriately used.

In the production of the pressure-sensitive adhesive film of the present invention, the epoxy resin is preferably used in an amount of 1 to 100 parts by weight, more preferably 2 to 50 parts by weight, based on 100 parts by weight of the thermoplastic resin. 02 to 120 parts by weight, more preferably 0.1 to 80 parts by weight are used.
When the amount of the epoxy resin used exceeds 100 parts by weight and the amount of the epoxy resin curing agent exceeds 120 parts by weight, the amount of weight loss and outgas generation during heating of the adhesive film increases, and the film formability is poor. Tend to be. Moreover, when the usage-amount of an epoxy resin is less than 1 weight part and the usage-amount of an epoxy resin hardening | curing agent is less than 0.02 weight part, it will become the tendency for the adhesive force at the time to fall.

  As the filler when the filler is contained together with the thermoplastic resin, the epoxy resin and the epoxy resin curing agent, the metal filler, the inorganic filler or the organic filler as described above is used. Among the fillers, the metal filler is added for the purpose of imparting conductivity or thixotropy to the adhesive film, the inorganic filler is added for the purpose of imparting low thermal expansion and low hygroscopicity to the adhesive film, and the organic filler is an adhesive film. It is added for the purpose of imparting toughness. Two or more of these metal fillers, inorganic fillers or organic fillers can be used. Mixing and kneading in the case of using a filler can be performed by appropriately combining dispersers such as a normal stirrer, a raking machine, a three-roller, and a ball mill.

Content of a filler is 0-100 weight part with respect to 100 weight part of thermoplastic resins, Preferably it is the range of 0-50 weight part. If it is more than 100 parts by weight, the tackiness may be lowered.
The filler-containing pressure-sensitive adhesive film is prepared by dissolving a thermoplastic resin, an epoxy resin, and the epoxy resin curing agent in an organic solvent, adding a filler, adding other components as necessary, and mixing and kneading. The obtained paste-like mixture is uniformly coated on a substrate, and heated and dried to produce.

  The organic solvent used in the production of the adhesive film is a solvent that can uniformly dissolve, knead, or disperse the material and can be easily removed by heating. Examples include dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, trimethylbenzene, dimethyl sulfoxide, diethylene glycol dimethyl ether, toluene, benzene, xylene, methyl ethyl ketone, tetrahydrofuran, ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve, dioxane and the like.

Heating and drying are performed by heating for 0.1 to 90 minutes under conditions where the solvent used is sufficiently volatilized, that is, at a temperature of approximately 60 to 200 ° C. Thereafter, the pressure-sensitive adhesive film is usually peeled off from the substrate at room temperature. Or it can also be used with a base material.
The base material used at the time of manufacture of an adhesive film will not be specifically limited if it can endure the heating and drying conditions at the time of said adhesive film manufacture. For example, there are a polyester film, a polypropylene film, a polyethylene terephthalate film, a polyimide film, a polyetherimide film, a polyether naphthalate film, a methylpentene film, and the like. These films may be treated with a silicone-based or silica-based release agent.

  The adhesive film can be used for bonding a semiconductor element such as an IC or LSI to a lead frame such as a 42 alloy lead frame or a copper lead frame, or a support member such as a resin substrate. That is, the pressure-sensitive adhesive film of the present invention is sandwiched between the semiconductor element and the support member as described above, and the two are bonded by thermocompression bonding at 100 to 300 ° C. for 0.1 to 300 seconds. Then, it is set as a semiconductor device (semiconductor package) through the wire bonding process and the sealing process with a sealing material.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.

(Polyimide synthesis example 1)
Polytetramethylene oxide-di-p-aminobenzoate (manufactured by Ihara Chemical Industry Co., Ltd.) was added to a 300 ml five-necked separable flask equipped with a stirrer, nitrogen inlet tube, thermometer, and Dean-Stark tube filled with mesitylene. Name: Elastomer 1000, average molecular weight 1268) 18.75 g, oxy-4,4′-diphthalic dianhydride (manac Co., Ltd., trade name: ODPA-M) 45.87 g, N-methyl-2-pyrrolidone 102 g Then, 44 g of mesitylene was weighed and dissolved in a nitrogen atmosphere, and 32.00 g of bisaminopropyltetramethyldisiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: PAM-E) was added little by little. Thereafter, a nitrogen introduction tube was inserted into the solution (bubbling state), the temperature in the system was heated to 170 ° C. to 180 ° C., and maintained for 12 hours while removing water azeotropically. After cooling, 146 g of mesitylene was added to dilute, 0.93 g of 4,4′-diamino-3,3′-dihydroxybiphenyl (manufactured by Wakayama Seika Kogyo Co., Ltd., trade name: HAB) was added, and polyimide (P— A solution of 1) was obtained. It was 0.81 dl / g as a result of measuring the logarithmic viscosity of this polyimide (P-1) at 35 degreeC using the Ubbelohde viscometer.

(Polyimide synthesis example 2)
Polytetramethylene oxide-di-p-aminobenzoate (product of Ihara Chemical Industry Co., Ltd. Name: Elastomer 1000, average molecular weight 1268) 18.16 g, oxy-4,4′-diphthalic dianhydride (manac Co., Ltd., trade name: ODPA-M) 44.43 g, N-methyl-2-pyrrolidone 100 g Then, 43 g of mesitylene was weighed and dissolved in a nitrogen atmosphere, and 31.00 g of bisaminopropyltetramethyldisiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: PAM-E) was added thereto little by little. Thereafter, a nitrogen introduction tube was inserted into the solution (bubbling state), the temperature in the system was heated to 170 ° C. to 180 ° C., and held for 12 hours while removing water azeotropically. After cooling, 143 g of mesitylene was added for dilution, 1.22 g of 1,3-bis (3-aminophenoxy) benzene (Mitsui Chemicals, trade name: APB) was added, and a solution of polyimide (P-2) Got. As a result of measuring the logarithmic viscosity of this polyimide (P-2) at 35 ° C. using an Ubbelohde viscometer, it was 0.88 dl / g.

(Examples 1-2, Comparative Examples 1-2)
Using the polyimide obtained in Polyimide Synthesis Example 1 and Polyimide Synthesis Example 2 as a thermoplastic resin, as shown in the recipe of Table 1, No. 1-4 varnishes were prepared. This varnish was applied on a base material (polyethylene terephthalate film) to a thickness of 25 μm, heated at 100 ° C. for 30 minutes, and then peeled off from the base material at room temperature to obtain an adhesive film. All of the obtained adhesive films were self-supporting films without tackiness at room temperature. In Table 1, each symbol means the following.
VG3101: Epoxy resin, manufactured by Mitsui Chemicals, Inc., trade name: TECHMORE
XLC-3L: Phenolic curing agent, manufactured by Mitsui Chemicals, Inc. (← In formula (I), R1 to R11 are hydrogen atoms, m is about 4, and x is methylene)
2MAOK: Imidazole-based curing agent, 1FX manufactured by Shikoku Kasei Kogyo Co., Ltd .: Silica-based filler, MS manufactured by Tatsumori Co., Ltd. MS: mesitylene (trimethylbenzene)
Table 2 shows the evaluation test results for the shear strength at 260 ° C. of the adhesive films of Examples 1-2 and Comparative Examples 1-3, and the weight loss when heated at 260 ° C. for 2 minutes. In addition, the comparative example 3 of Table 2 is a silver paste (The Hitachi Chemical Co., Ltd. make, brand name Epinal).

(Measurement method of shear adhesion)
A 5 × 5 mm silicon chip is adhered to a resin substrate with a 5 × 5 mm adhesive film at 130 ° C./0.1 MPa, and a heat history in the order of 180 ° C./10 min, 175 ° C./60 s / 10 MPa, 180 ° C./5 hr. Using the sample to which the pressure history was added, the shear adhesive strength after being held at 260 ° C. for 30 seconds was measured by a shear tester (SS-30WD manufactured by Nishijin Corporation).

(Measurement method of weight loss)
A metal plate on which an adhesive film cut to an appropriate size is placed is placed on a hot plate having a surface temperature of 260 ° C. and heated for 2 minutes. After cooling to room temperature, the weight of the pressure-sensitive adhesive film is measured, and the amount of change in the weight of the pressure-sensitive adhesive film (unit: μg / mm ³ (pressure-sensitive film)) is obtained by comparison with the weight of the pressure-sensitive adhesive film before the heat treatment. It was.

Table 1 Recipe

Table 2 Evaluation test results of adhesive film

  By using the adhesive resin composition of the present invention, it is possible to provide film-like adhesion that can withstand soldering heat treatment during mounting and generates less outgas, and is suitable as a material for die bonding in semiconductor package manufacturing. Can be used for

Claims (5)

An adhesive film containing a thermoplastic resin, an epoxy resin, and an epoxy resin curing agent,
The epoxy resin curing agent is an aralkylphenol compound represented by the following general formula (I):
The epoxy resin is a compound represented by any of formulas (1) to (3), the adhesive film for a semiconductor device.
(In the general formula (I), R _{1 to} R ₁₁ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a phenyl group or a hydroxyl group, m represents a positive number of 1 to 10, and X represents (Represents a divalent organic group or a single bond)
(R ₁ in the general formula (1) represents a divalent alkyl chain having 1 to 10 carbon atoms; R ₂ in the general formula (2) represents a trivalent alkyl chain having 1 to 10 carbon atoms; R ₃ in Formula (3) represents a tetravalent alkyl chain having 1 to 10 carbon atoms) The pressure-sensitive adhesive film for a semiconductor element according to claim 1, wherein the thermoplastic resin is a polyimide resin. The pressure-sensitive adhesive film for a semiconductor element according to claim 2, wherein the polyimide resin is a polyimide resin obtained by reacting a tetracarboxylic dianhydride represented by the general formula (II) with a diamine.

(In General Formula (II), X is a divalent group selected from the group consisting of —O—, —O—Y—O—, —CO—O—Y—OCO—, and Y is a divalent group. Represents an organic group of   Furthermore, the adhesive film for semiconductor elements of Claim 1 containing a filler.   The semiconductor device which adhere | attached the semiconductor element on the support member with the adhesive film in any one of Claims 1-4, and sealed the semiconductor element with the sealing material.