JP2009062413A - Adhesive composition and die bond film - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an adhesive composition having excellent gap-filling properties and adhesiveness. <P>SOLUTION: The adhesive composition comprises (A) 100 pts.mass of a phenoxy resin, (B) 5-200 pts.mass of an epoxy resin, (C) 3-20 pts.mass of a phenol resin represented by formula (1) (wherein, m is an integer of 0-25; R<SP>1</SP>is a 1-5C organic group; R<SP>2</SP>and R<SP>3</SP>are each independently a hydrogen atom r a 1-5C organic group), (D) a catalytic amount of a curing catalyst of the epoxy resin, and (E) 5-900 pts.mass of an inorganic filler relative to 100 pts.mass of the total of the components (A), (B), (C) and (D). <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an adhesive composition, and in particular, includes a phenoxy resin and a phenol resin having a predetermined structure having a substituent at an ortho position with respect to a phenolic hydroxyl group, and is well aligned with the shape of the substrate surface. The present invention relates to an adhesive composition that can adhere to a substrate without voids and with high adhesive force.

  In semiconductor devices, a large-diameter silicon wafer on which an IC circuit is formed is cut into semiconductor chips in a dicing process, and the lead frame is thermocompression-bonded with a curable liquid adhesive (die-bonding agent), etc., and bonded (mounted) And after wire bonding between the electrodes, it is manufactured by sealing with resin or the like. As this sealing method, a transfer mold method using a resin is most commonly used because it is excellent in mass productivity and inexpensive.

  The substrate has a convex portion due to circuit elements such as wiring on the substrate. When thermobonding a semiconductor chip to such a substrate, if air remains without the die-bonding agent filling between the protrusions, it is heated in a reflow furnace and expands, destroying the adhesive layer. There is a case. In particular, in recent years, the temperature of reflow resistance corresponding to lead-free solder has also become high (265 ° C.), so that no voids are formed.

In addition, the liquid die bond agent has a problem in that it protrudes outward from the wafer bonded to the substrate and contaminates adjacent pads. In order to avoid this, a die bond film in which a layer of a die bond agent is provided on the film is known (for example, Patent Document 1). However, there was a tendency that it becomes more difficult to eliminate the above-mentioned void problem by using a film. Then, the adhesive film provided with the layer of the composition which consists of a low elasticity polyimide silicone resin and an epoxy resin is proposed (patent documents 2 and 3). However, these films also have insufficient filling properties (hereinafter referred to as “gap fill performance”) between the fine protrusions on the substrate surface. That is, a fine gap may be generated at the time of die attachment, and the adhesive film may be peeled off starting from the gap.
JP-A-6-302629 JP 7-224259 A JP-A-8-27427

The present inventors use an adhesive having an appropriate softness at a molding temperature when resin-sealing a semiconductor chip even after being heated in the wire bonding process, and between the adhesive and the substrate in the molding process. It was found that an adhesive layer without voids can be formed by removing the air remaining in the film (Japanese Patent Application No. 2007-91934).

（ここでｍは０から２５の整数であり、Ｒ^１は炭素数１〜５の有機基、Ｒ^２とＲ^３は、互いに独立に、水素原子または炭素数１〜５の有機基である） The present invention provides a new problem-solving method based on the same idea as the above-described invention, and provides an adhesive composition that is excellent in gap fill performance and maintains high adhesive force even after reflow. That is, the present invention is (A) 100 parts by mass of phenoxy resin (B) 5 to 200 parts by mass of epoxy resin (C) 3 to 20 parts by mass of phenol resin represented by the following formula (1) (D) Epoxy resin curing catalyst Catalyst Amount and (E) inorganic filler (A), (B), (C), and (D) It is an adhesive composition containing 5-900 mass parts with respect to 100 mass parts of total amounts.

(Where m is an integer from 0 to 25, R ¹ is an organic group having 1 to 5 carbon atoms, and R ² and R ³ are independently a hydrogen atom or an organic group having 1 to 5 carbon atoms)

  The adhesive composition of the present invention is excellent in gap fill property and cured by a combination of a phenoxy resin and a phenol resin having a substituent at the ortho position of the phenolic hydroxyl group represented by the above formula (1). A thing is excellent in the adhesive force with respect to a to-be-adhered body.

(A) Phenoxy resin Examples of the phenoxy resin include bisphenol type resins derived from epichlorohydrin and bisphenol A or F. As such phenoxy resins, trade names PKHC, PKHH, PKHJ (all manufactured by Sakai Chemical Co., Ltd.), bisphenol A, bisphenol F mixed type trade names Epicoat 4250, Epicoat 4275, Epicoat 1255HX30, Epicoat 5580BPX40 using brominated epoxy (All manufactured by Nippon Kayaku Co., Ltd.), bisphenol A type trade names YP-50, YP-50S, YP-55, YP-70 (all manufactured by Toto Kasei), JER E1256, E4250, E4275, YX6954BH30, YL7290BH30 (Both manufactured by Japan Epoxy Resin Co., Ltd.).

(B) Epoxy resin The epoxy resin (B) used in the present invention is preferably a resin having at least two epoxy groups in one molecule. As such an epoxy resin, for example, bis (4-hydroxyphenyl) methane, 2,2′-bis (4-hydroxyphenyl) propane or diglycidyl ether of this halide and a condensation polymer thereof (so-called bisphenol F) Type epoxy resin, bisphenol A type epoxy resin, etc.), butadiene diepoxide, vinylcyclohexene dioxide, diglycidyl ether of resorcin, 1,4-bis (2,3-epoxypropoxy) benzene, 4,4′-bis (2 , 3-epoxypropoxy) diphenyl ether, 1,4-bis (2,3-epoxypropoxy) cyclohexene, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 1,2-dioxybenzene or resorcinol, many Polyhydric phenol or polyhydric alcohol Epoxy novolac obtained by condensing novolak type phenolic resin (or halogenated novolak type phenolic resin) such as epoxy glycidyl ether or polyglycidyl ester, phenol novolak, cresol novolak and the like obtained by condensing cole and epichlorohydrin with epichlorohydrin ( In other words, novolac type epoxy resin), epoxidized polyolefin epoxidized by peroxidation method, epoxidized polybutadiene, naphthalene ring-containing epoxy resin, biphenyl type epoxy resin, phenol aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin, cyclopentadiene type epoxy Resin etc. are mentioned. Preferably, bisphenol A type epoxy resin and bisphenol F type epoxy resin are used.

  The monoepoxy compound may be added in an amount that does not impair the object of the present invention. Examples of the monoepoxy compound include styrene oxide, cyclohexene oxide, propylene oxide, methyl glycidyl ether, ethyl glycidyl ether, and phenyl glycidyl ether. , Allyl glycidyl ether, octylene oxide, dodecene oxide and the like. Moreover, the epoxy resin to be used is not necessarily limited to only one type, and two or more types can be used in combination.

  (B) It is preferable that the compounding quantity of an epoxy resin is 5-200 mass parts with respect to 100 mass parts of phenoxy resins, especially 10-100 mass parts. If the amount of the epoxy resin is too small, the adhesive strength may be inferior, and if too large, the flexibility of the adhesive layer may be insufficient.

式（１）において、Ｒ¹としては、炭素数１〜５の有機基である。炭素数が６以上の置換基では、フェノール性水酸基に対する立体障害が大きくなり過ぎるために、エポキシ基との反応阻害が発生して、エポキシとの未反応部が多くなることにより、硬化物が吸湿し、また接着力の低下等が発生する恐れがある。好ましくは、Ｒ¹は１〜４の有機基であり、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ−ブチル基などのアルキル基；ビニル基、アリル基、プロペニル基、ブテニル基等のアルケニル基；およびこれらの水素原子の一部又は全部を塩素、フッ素、臭素等のハロゲン原子で置換したフロロメチル基、ブロモエチル基、トリフルオロプロピル基等のハロゲン置換一価炭化水素基を挙げることができ、このうち、メチル基、エチル基、ビニル基、及びアリル基がより好ましい。 (C) Phenol resin The composition of the present invention is represented by the following formula (1): a phenol resin having a substituent in the ortho position with respect to the phenolic hydroxyl group (hereinafter referred to as "ortho-substituted phenol resin"). Included). The ortho-substituted phenolic resin acts as a curing agent for epoxy resins and phenoxy resins. By the ortho-position substituent, the reaction between the phenolic hydroxyl group and the epoxy group is moderately inhibited, the gelation rate of the composition is suppressed, and the composition has an appropriate flexibility and a high gap in the resin sealing process. It is considered that fill performance is achieved. In the case of a phenol resin having no substituent at the ortho position, the network formation between the epoxy resin and the phenol resin proceeds faster and the gelation speed increases, resulting in poor gap fill properties.

In Formula (1), R ¹ is an organic group having 1 to 5 carbon atoms. In the substituent having 6 or more carbon atoms, the steric hindrance to the phenolic hydroxyl group becomes too large, and reaction inhibition with the epoxy group occurs, and the unreacted portion with the epoxy increases, so that the cured product absorbs moisture. In addition, there is a risk of a decrease in adhesive strength. Preferably, R ¹ is an organic group of ¹ to 4, for example, an alkyl group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group; vinyl group, allyl group, Alkenyl groups such as propenyl group and butenyl group; and halogen-substituted monovalent carbonization such as fluoromethyl group, bromoethyl group and trifluoropropyl group in which some or all of these hydrogen atoms are substituted with halogen atoms such as chlorine, fluorine and bromine A hydrogen group can be mentioned, and among these, a methyl group, an ethyl group, a vinyl group, and an allyl group are more preferable.

R ² and R ³ are each independently a hydrogen atom or an organic group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a tert-butyl group. I can list them. Preferably they are a hydrogen atom and a methyl group.

m is an integer of 0 to 25, preferably 0 to 10, more preferably an integer of 0 to 5. In particular, it is preferable that the peak of the molecular weight distribution is 1 to 3. When m exceeds the upper limit, the viscosity is high and the handleability is poor.

これらの樹脂は市販されている（例えばＯＣＮ−３、旭有機材工業（株）製）。 Preferred phenolic resins are those of the following formula (2) and / or (3).

These resins are commercially available (for example, OCN-3, manufactured by Asahi Organic Materials Co., Ltd.).

3-20 mass parts is preferable with respect to 100 mass parts of phenoxy resins, and, as for the compounding quantity of this ortho substituted phenol resin, 4-12 mass parts is especially preferable. If the amount is less than the lower limit, the adhesiveness may be inferior, and if the amount is greater than the upper limit, the gap fill property tends to be inferior.

Moreover, in order to adjust curability, you may use together the phenol resin which does not have a substituent in an ortho position. In this case, preferably 50 mol% or more of the total phenolic hydroxyl groups are phenols of the formula (1), particularly 75% or more, that is, the phenol resin having no substituent in the ortho position is used in an amount of less than 25%. From the viewpoint of gap fill properties, it is more preferable. Here, when the phenol resin having no substituent at the ortho position is 50% or more, the gap fill property tends to be inferior. In addition, even if it is a case where the phenol resin without a substituent in ortho position is used together, the said (C) component is used 3 mass parts or more with respect to 100 mass parts of (A) component.

式中、Ｒ⁸〜Ｒ¹⁵は水素原子又はフッ素、臭素、よう素などのハロゲン原子、あるいは炭素原子数１〜８のアルキル基、アルケニル基、アルキニル基、又は炭素原子数１〜８のアルコキシ基、トリフルオロメチル基、フェニル基などの非置換もしくは置換一価炭化水素基であり、総ての置換基が同一でも、互いに異なっていても構わない。 (D) Epoxy resin curing catalyst Examples of the epoxy resin curing catalyst used in the present invention include phosphorus-based catalysts and amine-based catalysts. Examples of the phosphorus catalyst include triphenylphosphine, triphenylphosphonium triphenylborate, tetraphenylphosphonium tetraphenylborate, and compounds as shown below.

In the formula, R ^{8 to} R ¹⁵ are a hydrogen atom or a halogen atom such as fluorine, bromine or iodine, or an alkyl group, alkenyl group, alkynyl group, or alkoxy group having 1 to 8 carbon atoms. , An unsubstituted or substituted monovalent hydrocarbon group such as a trifluoromethyl group and a phenyl group, and all the substituents may be the same or different from each other.

  Examples of the amine catalyst include imidazole derivatives such as dicyandiamide, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and the like. It is done.

  The epoxy resin curing catalyst in the present invention can be used singly or in combination of two or more. Preferably dicyandiamide is used. The compounding amount of the epoxy resin curing catalyst can be a catalytic amount.

Inorganic filler (E)
As the inorganic filler (E) used in the present invention, a filler of conductive particles such as silica fine powder, alumina, titanium oxide, carbon black, silver particles can be used. As the compounding quantity, it is 5-900 mass parts with respect to 100 mass parts of total amounts of (A), (B), (C), (D) component, Preferably it is 50-500 weight part, More preferably 50 to 300 parts by weight. If the blending amount is less than the lower limit, it is difficult to sufficiently improve the physical properties of the cured adhesive product. On the other hand, if the blending amount exceeds the upper limit, the viscosity of the composition becomes high and the handleability becomes poor.

The average particle size of the inorganic filler is preferably from 0.1 to 10 μm, more preferably from 0.5 to 7 μm. When the average particle size of the inorganic filler is within this range, it is easy to keep the surface properties well when applied to the film. Further, the thickness of the adhesive layer is usually 15 to 50 μm, but if the average particle size of the inorganic filler is within the above range, even if secondary agglomerated particles are present, that portion is required for the film. It is difficult to exceed the thickness and it is easy to achieve the thickness.

  In addition to the above components, the resin composition of the present invention includes an epoxy resin curing agent, carbon black, silicone rubber spherical particles, inorganic or organic pigments, dyes and the like within a range not impairing the effects of the present invention. Additives such as coloring agents, wetting improvers, antioxidants and heat stabilizers can be added.

  Examples of the epoxy resin curing agent include acid anhydrides, amines, and imidazoles in addition to the above-described phenol resin having no substituent at the ortho position. Examples of acid anhydrides include aliphatic acid anhydrides such as dodecenyl succinic anhydride, polyadipic acid anhydride, polyazelinic acid anhydride, polysebacic acid anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, anhydrous Aliphatic acid anhydrides such as methyl hymic acid, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, methylcyclohexanedicarboxylic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride , Aromatic acid anhydrides such as benzophenone tetracarboxylic acid anhydride, ethylene glycol bis trimellitate, glycerol tris trimellitate, etc., and amines include ethylene dimine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, Aliphatic amines such as propylenediamine, diethylaminopropylamine, hexamethylenediamine, mensendiamine, isophoronediamine, bis (4-amino-3-methylzinc cyclohexyl) methane, diaminozine cyclohexylmethane, bis (aminomethyl) cyclohexane N-aminoethylpiperazine, alicyclic amines such as 3,9-bis (3-aminopropyl) 2,4,8,10-tetraoxaspiro (5,5) undecane, metaphenylenediamine, diaminodiphenylmethane, diamino And aromatic amines such as diphenylsulfone and diaminodiethyldiphenylmethane. Examples of imidazoles include 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, -Phenyl-4-methylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, etc., and a mixture of two or more of these. Also good.

Examples of the silicone rubber spherical fine particles include the following formula (6):
-(R ⁴ ₂ SiO) a- (6)
And particles having rubber elasticity, in which molecules having a linear organopolysiloxane block represented by the formula (1) are crosslinked. R ⁴ in the general formula (6) is an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, an aryl group such as a phenyl group or a tolyl group, an alkenyl group such as a vinyl group or an allyl group, β- Aralkyl groups such as phenylethyl group and β-phenylpropyl group, monovalent halogenated hydrocarbon groups such as chloromethyl group and 3,3,3-trifluoropropyl group, and part of hydrogen atoms of the above hydrocarbon groups Is a monovalent group having 1 to 20 carbon atoms selected from a group substituted with an organic group containing a reactive group such as an epoxy group, an amino group, a mercapto group, an acryloxy group, or a methacryloxy group It is. Preferably, 90 mol% or more thereof is a methyl group. a is an integer of 5 to 5,000, preferably 10 to 1,000. The spherical fine particles have an average particle size of 0.1 to 100 μm, preferably 1 to 50 μm.

The silicone rubber spherical fine particles have (a) a vinyl group-containing organopolysiloxane and (b) an organohydrogenpolysiloxane (c) a platinum-based polymer having a vinyl group at the end of the molecule having the linear organopolysiloxane block. It can be prepared by addition reaction in the presence of a catalyst.

Preparation and Use Method of Adhesive Composition The adhesive composition of the present invention comprises the above (A) phenoxy resin, (B) epoxy resin, (C) phenol resin, (D) epoxy resin curing catalyst, and (E) inorganic filling. It can be prepared by mixing an agent and other components such as a curing agent for an epoxy resin, if used, according to a conventional method.

Method of Using Adhesive Composition The adhesive composition of the present invention obtained as described above is, for example, an aprotic polarity such as toluene, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, or NMP. After being dissolved in a solvent at an appropriate concentration, coated on a substrate and dried, the adherend is pressure-bonded and then heated and cured before use. Alternatively, an adhesive composition dissolved in an appropriate concentration in a solvent is applied onto a supporting substrate and dried to prepare a film in which an adhesive layer is formed (hereinafter referred to as a die bond film). The die-bonding film is attached on the circuit board with the adhesive layer facing the circuit board, the support base material is peeled off, and an adherend such as a silicon chip is thermocompression bonded, followed by heat curing and bonding. Examples of the supporting substrate include polyethylene, polypropylene, polyester, polyamide, polyimide, polyamideimide, polyetherimide, polytetrafluoroethylene, etc., paper, metal foil, etc. The surface of which a pressure-sensitive adhesive layer is applied can be used.

  As drying conditions after apply | coating the adhesive composition on a support base material, it is preferable to set it as normal temperature -200 degreeC, especially 80-150 degreeC for 1 minute-1 hour, especially 3-10 minutes. The thickness of the adhesive layer can be selected according to the purpose, and is preferably 5 to 100 μm, particularly 10 to 40 μm. The pressure bonding of the adherend is performed at a pressure of 0.01 to 10 MPa, particularly 0.1 to 2 MPa, and the subsequent curing of the adhesive layer is performed at a temperature of 100 to 200 ° C., preferably 120 to 180 ° C. for 30 minutes to 5 hours. In particular, it is preferable to cure in 1 to 2 hours.

  The die bond film can also be used as an adhesive tape for dicing die bonding. In the dicing process, the substrate film is peeled off, and the wafer is fixed to the adhesive layer by thermocompression bonding. The thermocompression bonding conditions can be variously selected depending on the composition of the adhesive layer, but is usually 0.01 to 0.2 MPa at 40 to 120 ° C. Next, after dicing, the chip is taken out (pickup) with the adhesive layer attached, and the chip is bonded to the lead frame by thermocompression, followed by heat curing. The thermocompression bonding conditions can be the same as the thermocompression bonding conditions for the wafer and the adhesive layer, and the heat curing conditions are as described above. In addition to dicing and die bonding, the composition of the present invention can be used for various applications as an adhesive.

EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated further, this invention is not restrict | limited to the following Example.
[Examples 1-5, Comparative Examples 1-2, Reference Examples 1-3]
100 parts by mass of phenoxy resin (JER E1256 made by JER) is dissolved in 20 parts by mass of cyclohexanone, and ortho-substituted phenol resin, epoxy resin (RE310S, bisphenol A type epoxy resin, manufactured by Nippon Kayaku Co., Ltd.), curing catalyst dicyandiamide is dissolved in the solution. A 70 mass% cyclohexanone solution of (DICY-7, manufactured by JER Co., Ltd.) and silica (SE2050, manufactured by Admatex Co., Ltd.) is mixed in a blending amount (part by mass) shown in Table 1 below to prepare an adhesive composition. did. In Table 1, the numerical values are solid contents. The phenol resin 1 having a substituent at the ortho position, the phenol resin 2 having a substituent at the ortho position, and the phenol resin having no substituent at the ortho position are as follows.

（ｍ＝０〜５、ｍの平均は１）

（２）オルソ置換フェノール樹脂2、試薬

また、オルソ位に置換基の無いフェノール樹脂として、ビスフェノールＡ（本州化学製、ＤＡＬ−ＢＰＡ）を使用した。 As the ortho-substituted phenol resin, the following were used.
(1) Ortho-substituted phenolic resin 1 (OCN-3, manufactured by Asahi Organic Materials Co., Ltd.)

(M = 0-5, the average of m is 1)

(2) Ortho-substituted phenolic resin 2, reagent

In addition, bisphenol A (DAL-BPA manufactured by Honshu Chemical Co., Ltd.) was used as a phenol resin having no substituent at the ortho position.

Preparation of die bond film The adhesive composition obtained above was applied onto a 50 μm thick PET film coated with a fluorosilicone mold release agent and dried by heating at 120 ° C. for 10 minutes to form a 25 μm adhesive layer. Thus, a die bond film was produced.

  Using the die bond film, the characteristics of each composition were evaluated by the following methods. The results are shown in Table 1.

Adhesion Test A test piece was prepared by sandwiching a 3 mm × 3 mm × 25 μm adhesive layer between polished surfaces of a 10 mm × 10 mm silicon wafer and a 3 mm × 3 mm silicon wafer. That is, the die bond film obtained above is attached to a silicon wafer having a diameter of 8 inches, cut into 3 mm × 3 mm square chips, and picked up at 170 ° C. at the center of a 10 mm × 10 mm silicon wafer. And thermocompression bonding for 1 second under the condition of 0.1 MPa. The obtained laminate was heat-treated at 175 ° C. for 4 hours to cure the adhesive layer, thereby preparing an adhesive test piece. Thereafter, the shear adhesive force (MPa) was measured at a speed of 200 μm / second and a height of 50 μm using a shear tester (Dage 4000 manufactured by Dage).

Adhesion after wet heat After holding the above-mentioned test piece for adhesion under the condition of 85 ° C./60% RH for 168 hours, the IR reflow at 260 ° C. was passed three times, and the shear adhesive strength was measured in the same manner as described above. .

An adhesive layer (film thickness: 40 μm) of each resin composition was formed on one surface of a transparent glass chip of 25 μm gap fill performance 7 mm × 7 mm × 500 μm. The obtained transparent glass chip with an adhesive layer was placed on a PCB having a wiring pattern with a line / space = 10/10 μm and an average height of 25 μm at 170 ° C. and 0.degree. C. so that the adhesive layer was in contact with the PCB. Bonding was performed under conditions of 1 MPa and 1 second. After bonding, 170 ° C corresponding to the thermal history of wire bond and 1 hour of thermal history after bonding, a film bonder (manufactured by TOWA Co., Ltd.) was used under the conditions of 175 ° C, 7 MPa and 90 seconds corresponding to EMC sealing. Then, pressing was performed from above the glass chip, and the obtained pseudo device was observed with a microscope to confirm whether or not a gap of 25 μm was filled. The results are shown in Table 1.

20 layers of storage stable adhesive layers were laminated to form a laminate so as to have a thickness of about 500 μm. The shear viscosity of the obtained adhesive layered product was measured by MARS manufactured by HAAKE. The ratio of the viscosity of the test piece after standing for 168 hours at 75 ° C. (viscosity after thermal history / initial viscosity) with respect to the viscosity immediately after molding the laminate was determined. did. The results are shown in Table 1.

  As shown in Table 1, the cured product obtained from the compositions of Examples 1 to 4 containing a phenol resin having a substituent at the ortho position is significantly more in comparison with the cured product of the comparative example not containing the phenol resin. Excellent gap fill performance. In addition, Reference Examples 1 and 2 and Reference Example 3 in which the amount of the phenol resin having a substituent at the ortho position was blended in an amount greater than the appropriate amount were inferior in gap fill performance and storage stability.

  The composition of the present invention is useful as an adhesive for semiconductor packages having excellent gap fill properties. A film having an adhesive layer made of the composition is useful as a die bond film.

Claims (4)

(A) Phenoxy resin 100 parts by mass (B) Epoxy resin 5 to 200 parts by mass (C) Phenol resin represented by the following formula (1) 3 to 20 parts by mass (D) Epoxy resin curing catalyst Catalyst amount, and (E ) Inorganic filler An adhesive composition containing 5 to 900 parts by mass with respect to 100 parts by mass of the total amount of components (A), (B), (C) and (D).

(Where m is an integer from 0 to 25, R ¹ is an organic group having 1 to 5 carbon atoms, and R ² and R ³ are independently a hydrogen atom or an organic group having 1 to 5 carbon atoms) The adhesive composition of Claim 1 containing 4-12 mass parts component (C) with respect to 100 mass parts of components (A). The adhesive composition according to claim 1 or 2, wherein the component (C) is a phenol resin represented by the following formula (2) and / or (3).

A die bond film provided with the adhesive bond layer which consists of an adhesive composition of any one of Claims 1-3.