JP5499516B2 - Adhesive composition, circuit member connecting adhesive sheet, and method for manufacturing semiconductor device - Google Patents

Description

  The present invention relates to an adhesive composition, an adhesive sheet for connecting a circuit member using the same, and a method for manufacturing a semiconductor device. More specifically, the semiconductor device is obtained by soldering a semiconductor element to a circuit board by a face-down bonding method. The present invention relates to an adhesive composition used in a method for manufacturing a sheet, and an adhesive sheet for connecting a circuit member using the same.

  As a semiconductor chip mounting technique, a face-down bonding method is known in which solder bumps are formed on electrode portions of a semiconductor chip and the semiconductor chip is directly connected to a circuit board by solder bonding. This method is advantageous for small and thin packaging. In mounting a semiconductor chip, a liquid adhesive or a film adhesive is usually used between the circuit board and the semiconductor chip for the purpose of alleviating thermal stress due to the difference in thermal expansion coefficient between the semiconductor chip and the circuit board. Filled.

  When using a liquid adhesive, a method of performing solder bonding after first applying a liquid adhesive to a circuit board and mounting a semiconductor chip; and soldering the semiconductor chip to the circuit board; There is a method of filling the liquid adhesive from between. However, in any of the methods, it is difficult to accurately control the amount of liquid adhesive applied by a dispenser. If the amount of application is too large, the resin exuded during bonding scoops up the side of the chip and contaminates the bonding tool. This is a factor, which necessitates cleaning of the tool and complicates the mass production process. In particular, in recent thinned chips, contamination with a liquid adhesive tends to occur.

  In the case of using a film adhesive, the above-mentioned contamination hardly occurs. Furthermore, in recent years, a method using a chip with a film adhesive has attracted attention from the viewpoint of workability and high-density mounting. For example, in Patent Document 1 below, a process for forming a film-like adhesive layer containing liquid epoxy resin, a solid resin having a functional group, and a thermally activated microcapsule type curing agent as essential components on the protruding electrode surface of a semiconductor wafer is disclosed. , Cutting the wafer provided with the film adhesive layer together with the adhesive layer into a chip, and aligning the protruding electrode of the obtained chip with the opposite circuit on the wiring board through the adhesive layer There has been proposed a circuit connection method including a step of placing, a step of bringing a protruding electrode into contact with an opposing circuit by heating and pressing a chip and a wiring board, and then substantially curing an adhesive.

Japanese Patent No. 2833111

  The method of Patent Document 1 has an advantage that it is difficult to be displaced because solder bonding and curing of the adhesive are simultaneously performed by the heating and pressing. However, when solder bonding is performed by heating for a short time, the conventional adhesive may not provide the flux activity for removing the oxide film on the surface of the solder, resulting in insufficient solder wetting. In addition, the film-like adhesive used for connecting circuit members has a embeddability in which voids are unlikely to occur during crimping and has a high adhesive force after curing in order to ensure connection reliability. Etc. are needed. Therefore, it is not desirable that these properties be impaired by the application of flux activity.

  The present invention has been made in view of the above circumstances, and is excellent in embeddability when formed into a film and adhesive strength after curing, and can exhibit sufficient flux activity even in short-time solder bonding. An object of the present invention is to provide an adhesive composition, an adhesive sheet for connecting a circuit member using the same, and a method for manufacturing a semiconductor device.

［式（１）中、Ｘは、炭素数１〜１０のアルキル基を示し、炭素数が２以上でありメチレン基を有する場合、メチレン基の少なくとも一つが−Ｏ−、−ＮＨ−、−Ｓ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−で置換されていてもよく、炭素数が３以上でありメチン基（−ＣＨ＜）を有する場合、メチン基の少なくとも一つが窒素原子で置換されていてもよい。］

The adhesive composition of the present invention that solves the above problems includes ( A) a high molecular weight component having a weight average molecular weight of 100,000 or more, (B) an epoxy resin, (C) a phenolic epoxy resin curing agent, a methylol compound having one phenolic hydroxyl groups in D) 1 molecule, viewed contains a (E) a curing accelerator, methylol compounds, characterized in that it is a methylol compound represented by the following general formula (1) .

[In the formula (1), X represents an alkyl group having 1 to 10 carbon atoms, and when the carbon number is 2 or more and has a methylene group, at least one of the methylene groups is -O-, -NH-, -S. -, -CO-, -OCO- or -COO- may be substituted, and when it has 3 or more carbon atoms and has a methine group (-CH <), at least one of the methine groups is substituted with a nitrogen atom. It may be. ]

  According to the adhesive composition of the present invention, by blending the components (A), (B), (C) and (E) and the methylol compound having the specific structure, embedding and It is possible to form a film-like adhesive that is excellent in adhesive strength after curing and that can exhibit sufficient flux activity even in soldering in a short time. The inventors of the present invention obtain the reason why such an effect is obtained because the component (D) having the flux activity is not easily increased in molecular weight even by heat at the time of forming the film, so that the flux activity is sufficiently maintained even after the film is formed. In addition, since the component (D) reacts with the epoxy resin and the phenolic epoxy resin curing agent at the time of high-temperature pressure bonding, it is taken into the film system, so the above (A), (B), (C) and ( E) It is considered that the good embedding property and adhesiveness obtained by the combination of the components are not deteriorated.

［式（１）中、Ｘは、炭素数１〜１０のアルキル基を示し、炭素数が２以上でありメチレン基を有する場合、メチレン基の少なくとも一つが−Ｏ−、−ＮＨ−、−Ｓ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−で置換されていてもよく、炭素数が３以上でありメチン基（−ＣＨ＜）を有する場合、メチン基の少なくとも一つが窒素原子で置換されていてもよい。］ In the adhesive composition of the present invention, the methylol compound is preferably a methylol compound represented by the following general formula (1).

[In the formula (1), X represents an alkyl group having 1 to 10 carbon atoms, and when the carbon number is 2 or more and has a methylene group, at least one of the methylene groups is -O-, -NH-, -S. -, -CO-, -OCO- or -COO- may be substituted, and when it has 3 or more carbon atoms and has a methine group (-CH <), at least one of the methine groups is substituted with a nitrogen atom. It may be. ]

  Moreover, the adhesive composition of this invention contains 5-500 mass parts of (B) component with respect to 100 mass parts of (A) component, and the phenolic hydroxyl group of (C) component with respect to the epoxy group of (B) component. The equivalent ratio is 0.5 to 1.5, the ratio of the hydroxyl group of component (D) to the total of hydroxyl groups of component (C) and component (D) is 25% or more, component (B), (C) It is preferable that 0.1-20 mass parts of (E) components are included with respect to a total of 100 mass parts of a component and (D) component.

  Moreover, it is preferable that the said (A) component is a glycidyl group containing (meth) acrylic copolymer which contains 0.5-6 mass% of repeating units which have a glycidyl group.

  The adhesive composition of the present invention preferably further comprises (F) a radiation polymerizable compound and (G) a photoinitiator.

  The adhesive composition of the present invention can be used for adhering circuit members by interposing them between circuit members having circuit electrodes that are opposed to each other and soldered. In this case, the circuit members can be bonded together with a sufficient adhesive force while suppressing the generation of voids by thermocompression bonding, and the circuit electrodes can be soldered well. Thereby, the connection body excellent in connection reliability can be obtained.

  The adhesive sheet for circuit member connection of this invention is equipped with a support base material and the adhesive bond layer which is provided on this support base material and consists of the adhesive composition of the said invention, It is characterized by the above-mentioned.

  Moreover, the adhesive sheet for circuit member connection of this invention can be used between the circuit members which have the circuit electrode mutually opposed and solder-joined, and to adhere circuit members. In this case, the circuit members can be bonded together with a sufficient adhesive force while suppressing the generation of voids by thermocompression bonding, and the circuit electrodes can be soldered well. Thereby, the connection body excellent in connection reliability can be obtained.

  The present invention also provides a semiconductor wafer having a plurality of circuit electrodes on one of its main surfaces, and an adhesive layer made of the adhesive composition of the present invention is provided on the side of the semiconductor wafer on which the circuit electrodes are provided. A step of thinning the semiconductor wafer by grinding the side of the semiconductor wafer opposite to the side where the circuit electrodes are provided, and a semiconductor with a film adhesive by dicing the thinned semiconductor wafer and the adhesive layer Provided is a method for manufacturing a semiconductor device, comprising a step of dividing into elements and a step of solder-bonding circuit electrodes of a semiconductor element with a film adhesive to a circuit electrode of a support member for mounting a semiconductor element.

  According to the present invention, it is possible to provide an adhesive composition that is excellent in embedding property when formed into a film and adhesive strength after curing, and that can exhibit sufficient flux activity even in solder bonding in a short time. it can. In addition, according to the adhesive sheet for connecting circuit members of the present invention, the oxide film on the solder surface can be removed at the time of pressure bonding, enabling solder bonding in a short time, generating less voids at the time of pressure bonding, and after curing. Since the adhesive force is also high, it is possible to obtain a circuit member assembly excellent in reflow crack resistance and connection reliability. Further, according to the method for manufacturing a semiconductor device of the present invention, a semiconductor device having excellent connection reliability can be obtained.

1 is a schematic cross-sectional view showing a preferred embodiment of an adhesive sheet for connecting circuit members according to the present invention. It is a schematic cross section for explaining one embodiment of a manufacturing method of a semiconductor device concerning the present invention. It is a schematic cross section for explaining one embodiment of a manufacturing method of a semiconductor device concerning the present invention. It is a schematic cross section for explaining one embodiment of a manufacturing method of a semiconductor device concerning the present invention. It is a schematic cross section for explaining one embodiment of a manufacturing method of a semiconductor device concerning the present invention. It is a schematic cross section for explaining one embodiment of a manufacturing method of a semiconductor device concerning the present invention. It is a schematic cross section for demonstrating other embodiment of the manufacturing method of the semiconductor device which concerns on this invention. It is a schematic cross section for demonstrating other embodiment of the manufacturing method of the semiconductor device which concerns on this invention. It is a schematic cross section for demonstrating other embodiment of the manufacturing method of the semiconductor device which concerns on this invention.

  FIG. 1 is a schematic cross-sectional view showing a preferred embodiment of an adhesive sheet for connecting circuit members according to the present invention. An adhesive sheet 10 for connecting circuit members shown in FIG. 1 includes a support base 3, an adhesive layer 2 provided on the support base 3 and made of the adhesive composition of the present invention, and an adhesive layer 2. And a protective film 1 to be coated.

  First, the adhesive composition of the present invention constituting the adhesive layer 2 will be described.

  The adhesive composition of the present invention comprises (A) a high molecular weight component having a weight average molecular weight of 100,000 or more, (B) an epoxy resin, (C) a phenolic epoxy resin curing agent, and (D) one intramolecular. A methylol compound having one phenolic hydroxyl group and (E) a curing accelerator.

  (A) As a high molecular weight component having a weight average molecular weight of 100,000 or more, those having a functional group such as a glycidyl group, an acryloyl group, a methacryloyl group, a carboxyl group, a hydroxyl group, and an episulfide group are preferable from the viewpoint of improving adhesiveness. . Examples of such a high molecular weight component include (meth) acrylic ester copolymers and acrylic rubber. In particular, acrylic rubber is more preferable. The acrylic rubber is a rubber mainly composed of an acrylate ester and mainly composed of a copolymer with butyl acrylate and acrylonitrile or a copolymer with ethyl acrylate and acrylonitrile. Examples of the copolymer monomer include butyl acrylate, ethyl acrylate methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, acrylonitrile and the like.

  The component (A) is preferably a high molecular weight component having a glycidyl group from the viewpoint of crosslinkability. Specific examples include a glycidyl group-containing (meth) acrylic copolymer having a weight average molecular weight of 100,000 or more obtained by polymerizing a raw material monomer containing glycidyl acrylate or glycidyl methacrylate. In addition, in this specification, a glycidyl group containing (meth) acryl copolymer is a phrase which shows both a glycidyl group containing acrylic copolymer and a glycidyl group containing methacryl copolymer.

  As the glycidyl group-containing (meth) acrylic copolymer having a weight average molecular weight of 100,000 or more, a glycidyl group-containing (meth) acrylic copolymer prepared by appropriately selecting a monomer from the copolymerization monomer and glycidyl acrylate or glycidyl methacrylate can be used. Commercial products (for example, “HTR-860P-3” manufactured by Nagase ChemteX Corporation) can also be used.

  (A) The high molecular weight component having a weight average molecular weight of 100,000 or more can adjust the crosslinking density by appropriately changing the content of the functional group. When the high molecular weight component is a copolymer of a plurality of monomers, the functional group-containing monomer used as a raw material is preferably contained in an amount of about 0.5 to 6.0% by mass of the copolymer.

  In the case of a glycidyl group-containing (meth) acrylic copolymer, the repeating unit having a glycidyl group such as glycidyl acrylate or glycidyl methacrylate is preferably 0.5 to 6.0 mass%, more preferably 0.5 to 5.0 mass. %, Even more preferably 0.8 to 5.0% by mass of a glycidyl group-containing (meth) acrylic copolymer is used. When the amount of the repeating unit having a glycidyl group is in the above range, the glycidyl group is slowly crosslinked, and thus it is easy to prevent gelation while securing the adhesive force. Moreover, since it becomes incompatible with (B) epoxy resin, it will be excellent in stress relaxation property.

  In addition to the glycidyl acrylate or glycidyl methacrylate, other functional groups may be incorporated in the glycidyl group-containing (meth) acrylic copolymer. In this case, the mixing ratio is preferably determined in consideration of the glass transition temperature of the glycidyl group-containing (meth) acrylic copolymer. Specifically, it is preferable to set the mixing ratio so that the glass transition temperature of the polymer is -10 ° C or higher. It is preferable for the glass transition temperature of the polymer to be −10 ° C. or higher, since the tackiness of the adhesive layer in the B-stage state is appropriate and no problem is caused in handleability.

  When the glycidyl group-containing acrylic copolymer obtained by polymerizing the glycidyl group-containing monomer is used as the component (A), the polymerization method is not particularly limited, and examples thereof include methods such as pearl polymerization and solution polymerization. Can be used.

  In the present invention, the weight average molecular weight of the component (A) is 100,000 or more, preferably 300,000 to 3,000,000, more preferably 400,000 to 2,500,000, and particularly preferably 500,000 to 2,000,000. preferable. When the weight average molecular weight is within this range, it becomes easy to satisfactorily balance the strength, flexibility and tackiness of the adhesive layer made into a sheet or film, and the flowability of the adhesive layer becomes good. Therefore, the circuit filling property (embedding property) of the wiring can be sufficiently secured. In the present specification, the weight average molecular weight is a value measured by gel permeation chromatography and converted using a standard polystyrene calibration curve.

  Moreover, it is preferable that (A) component is incompatible with (B) epoxy resin at the point of reflow resistance. However, since compatibility is not determined only by the characteristics of the component (A), a combination in which both the components (A) and (B) are not compatible is selected.

  (B) The epoxy resin is not particularly limited as long as it is cured and has an adhesive action. For example, epoxy resins described in an epoxy resin handbook (Shinho Masaki, edited by Nikkan Kogyo Shimbun) are widely used. be able to. Specifically, for example, a bifunctional epoxy resin such as a bisphenol A type epoxy, a novolac type epoxy resin such as a phenol novolac type epoxy resin or a cresol novolac type epoxy resin, a trisphenolmethane type epoxy resin, or the like can be used. Moreover, what is generally known, such as a polyfunctional epoxy resin, a glycidyl amine type epoxy resin, a heterocyclic ring-containing epoxy resin, or an alicyclic epoxy resin, can be applied.

  As the bisphenol A type epoxy resin, Epicoat 807, 815, 825, 827, 828, 834, 1001, 1004, 1007, 1009 manufactured by Japan Epoxy Resin Co., Ltd., DER-330, 301, 361 manufactured by Dow Chemical Co., Ltd. Examples thereof include YD8125, YDF8170, and the like. Examples of the phenol novolac type epoxy resin include Epicoat 152,154 manufactured by Japan Epoxy Resin Co., Ltd., EPPN-201 manufactured by Nippon Kayaku Co., Ltd., DEN-438 manufactured by Dow Chemical Co., Ltd., and o-cresol novolac type epoxy resin. Examples include EOCN-102S, 103S, 104S, 1012, 1025, 1027 manufactured by Nippon Kayaku Co., Ltd., YDCN701, 702, 703, 704 manufactured by Toto Kasei Co., Ltd., and the like. As the polyfunctional epoxy resin, E1032-H60 manufactured by Japan Epoxy Resins Co., Ltd., Araldite 0163 manufactured by Ciba Specialty Chemicals Co., Ltd., Denacor EX-611, 614, 614B, 622, 512, 521, 421 manufactured by Nagase Kasei Co., Ltd. 411, 321 and the like. As amine type epoxy resins, Japan Epoxy Resin Co., Ltd. Epicoat 604, Tohto Kasei Co., Ltd. YH-434, Mitsubishi Gas Chemical Co., Ltd. TETRAD-X, TETRAD-C, Sumitomo Chemical Co., Ltd. ELM- 120 etc. are mentioned. Examples of the heterocyclic ring-containing epoxy resin include ERL4234, 4299, 4221, 4206 and the like manufactured by UCC, such as Araldite PT810 manufactured by Ciba Specialty Chemicals. These epoxy resins can be used alone or in combination of two or more.

  In this invention, it is preferable to use a polyfunctional epoxy resin from a viewpoint of providing high adhesive force.

  The content of the component (B) in the adhesive composition according to the present invention is preferably 5 to 500 parts by weight, and preferably 10 to 400 parts by weight with respect to 100 parts by weight of the component (A). It is more preferable to set it as 40-300 mass parts. When content of (B) component exists in said range, the elasticity modulus of the adhesive bond layer formed in the film form and the flow property suppression at the time of shaping | molding can fully be ensured, and the handleability in high temperature can be made favorable.

  (C) When combined with an epoxy resin, the phenol-based epoxy resin curing agent has excellent impact resistance under high temperature and high pressure, and can maintain sufficient adhesive properties even under severe thermal moisture absorption.

  Examples of the component (C) include phenol resins such as phenol novolak resin, bisphenol A novolak resin, and cresol novolak resin. More specifically, for example, manufactured by Dainippon Ink & Chemicals, Inc., trade names: Phenolite LF4871, Phenolite LF2822, Phenolite TD-2090, Phenolite TD-2149, Phenolite VH-4150, Phenolite VH4170 , Manufactured by Shin Nippon Oil Co., Ltd., trade name: DPP-M, and the like can be used, and these can be used alone or in combination of two or more.

  The content of the component (C) in the adhesive composition according to the present invention is such that the equivalent ratio of the phenolic hydroxyl group of the component (C) to the epoxy group of the component (B) is 0 from the viewpoint of imparting electric corrosion resistance during moisture absorption. 0.5 to 1.5 is preferable, and 0.8 to 1.2 is more preferable. By containing the component (C) at such an equivalent ratio, the curing (crosslinking) of the epoxy resin can proceed to a sufficient level, and the glass transition temperature of the cured product can be sufficiently increased. Thereby, the moisture resistance of the cured adhesive layer and the connection reliability at a high temperature can be sufficiently ensured, and as a result, the electric corrosion resistance at the time of moisture absorption is more reliably improved.

  (D) As a methylol compound having one phenol hydroxyl group in one molecule, those capable of aggregating solder balls into almost one in the following flux activity test are preferable. In the test, 10 solder balls of 3 mmφ are placed on a copper plate, about 200 mg of a methylol compound is placed thereon, heated on a hot plate heated to 260 ° C., and the state of the solder balls after 30 seconds is observed.

  In addition, the component (D) has a methylol group on both sides of the phenolic hydroxyl group from the viewpoint of design that the reaction is suppressed and the activity is maintained at the time of film formation and the activity is exhibited after high temperature pressure bonding and then reacted and taken into the system. Is preferably a methylol compound.

式（１）中、Ｘは、炭素数１〜１０のアルキル基を示し、炭素数が２以上でありメチレン基を有する場合、メチレン基の少なくとも一つが−Ｏ−、−ＮＨ−、−Ｓ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−で置換されていてもよく、炭素数が３以上でありメチン基（−ＣＨ＜）を有する場合、メチン基の少なくとも一つが窒素原子で置換されていてもよい。 Furthermore, the component (D) is preferably a methylol compound represented by the following general formula (1).

In formula (1), X represents an alkyl group having 1 to 10 carbon atoms, and when the carbon number is 2 or more and has a methylene group, at least one of the methylene groups is —O—, —NH—, —S—. , -CO-, -OCO- or -COO-, and when it has 3 or more carbon atoms and has a methine group (-CH <), at least one of the methine groups is substituted with a nitrogen atom May be.

  From the viewpoint of flux activity and solubility in a coating solvent, it is preferable to use a methylol compound in which X in the general formula (1) is a linear or branched alkyl group having 1 to 10 carbon atoms. . Furthermore, from the viewpoint of solubility in a coating solvent, it is preferable to use a methylol compound in which X is a methyl group or the like. Specific examples include trade names: DML-POP and DML-PC manufactured by Honshu Chemical Co., Ltd.

  In the adhesive composition according to the present invention, from the viewpoint of obtaining good flux activity, the ratio of the hydroxyl group of the (D) component to the total of the hydroxyl groups of the (C) component and the (D) component is preferably 15% or more. 25% or more is more preferable. Further, from the viewpoint of achieving both adhesive strength and flux activity at a high level, the ratio of the hydroxyl group of the component (D) is more preferably 20 to 80%, and most preferably 25 to 75%.

  (E) Examples of the curing accelerator include imidazoles, dicyandiamide derivatives, dicarboxylic acid dihydrazide, triphenylphosphine, tetraphenylphosphonium tetraphenylborate, 2-ethyl-4-methylimidazoletetraphenylborate, 1,8-diazabicyclo ( 5,4,0) undecene-7-tetraphenylborate and the like. These can be used individually by 1 type or in combination of 2 or more types.

  The content of the component (E) in the adhesive composition according to the present invention is 100 parts by mass in total from the component (B), the component (C) and the component (D) from the viewpoint of achieving both curability and storage stability. Is preferably 0.1 to 20 parts by weight, more preferably 0.1 to 5 parts by weight, and even more preferably 0.2 to 3 parts by weight.

  In addition to the above components (A) to (E), the adhesive composition according to the present invention includes (F) a radiation polymerizable compound and (G) photoinitiation for the purpose of controlling fluidity and tackiness by photocuring. An agent can be included. Due to the above action by these components, the flexibility and reflow crack resistance can be further improved.

  (F) As a radiation polymerizable compound, the compound which can be bridge | crosslinked by irradiation of a radiation is mentioned. Specifically, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, trimethylolpropane triacrylate, isocyanuric acid EO-modified triacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol tetraacrylate, dicyclopentenyloxy Examples include acrylates such as ethyl acrylate and 2.2-bis [4- (methacryloxy-diethoxy) phenyl] propane acrylate. These compounds can be used alone or in combination of two or more. Commercial products such as Shin-Nakamura Chemical Co., Ltd .: A-DPH, Hitachi Chemical Co., Ltd .: FA-512AS, FA-513AS can be used.

  Examples of the (G) photoinitiator include 1-hydroxy-cyclohexyl phenyl ketone, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, and the like. Commercial products such as Irg-184 and Irg-819 manufactured by Ciba Specialty Chemicals can be used.

  As for the compounding quantity of (F) component in the adhesive composition which concerns on this invention, 10-200 mass parts is preferable with respect to 100 mass parts of (A) component. When the blending amount is 10 parts by mass or more, the polymerization reaction of the radiation-polymerizable compound by irradiation with radiation such as ultraviolet rays can be sufficiently advanced, and the fluidity at the time of high-temperature pressure bonding can be suppressed. On the other hand, if the blending amount exceeds 200 parts by mass, cross-linking occurs excessively, and it becomes difficult to obtain the fluidity necessary for pressure bonding. The blending amount is more preferably 15 to 150 parts by mass, and particularly preferably 20 to 100 parts by mass.

  It is preferable that the compounding quantity of (G) component in the adhesive composition which concerns on this invention is 0.1-30 mass parts with respect to 100 mass parts of (A) component. If the blending amount is less than 0.1 parts by mass, the unreacted component (F) tends to remain. In this case, voids increase at the time of high-temperature pressure bonding, and the embedding property tends to be adversely affected. On the other hand, when the blending amount exceeds 30 parts by mass, it is difficult to sufficiently increase the molecular weight by the polymerization reaction, and there is a tendency that many low molecular weight components exist. In this case, the low molecular weight component may affect the fluidity during heating. The blending amount is more preferably 0.5 to 20 parts by mass, and particularly preferably 1 to 10 parts by mass.

  In order to improve flexibility and reflow crack resistance, the adhesive composition according to the present invention is compatible with (H) an epoxy resin and may contain a high molecular weight resin other than the component (A). it can. As such a component (H), those that are incompatible with the component (A) are preferable from the viewpoint of improving reliability, and examples thereof include phenoxy resins, high molecular weight epoxy resins, and ultrahigh molecular weight epoxy resins. These can be used alone or in combination of two or more.

  When using the (A) component and the (B) epoxy resin that are compatible with each other, the above (H) component is blended to make the (B) epoxy resin more compatible with the (H) component. (B) It may be possible to make the epoxy resin and the component (A) incompatible with each other. By such an action, flexibility and reflow crack resistance can be further improved.

  The blending amount of the component (H) is 40 parts by mass or less with respect to a total of 100 parts by mass of the (B) epoxy resin and the (C) phenolic epoxy resin curing agent, from the viewpoint of securing Tg of the adhesive layer. Is preferred.

  An inorganic filler can be added to the adhesive composition according to the present invention for the purpose of improving the handleability of the formed adhesive layer, improving thermal conductivity, adjusting the melt viscosity, and imparting thixotropic properties. The inorganic filler is not particularly limited. For example, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, boron nitride, Examples thereof include crystalline silica and amorphous silica. These fillers can be used alone or in combination of two or more. Further, the shape of the filler is not particularly limited.

  Among the above fillers, aluminum oxide, aluminum nitride, boron nitride, crystalline silica, amorphous silica and the like are preferable for improving thermal conductivity. For the purpose of adjusting melt viscosity and imparting thixotropic properties, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, crystallinity Silica, amorphous silica and the like are preferable. Moreover, it is more preferable to use a nanofiller in order to improve the hot fluidity of the film.

  As for the compounding quantity of an inorganic filler, 1-100 mass parts is preferable with respect to 100 mass parts of adhesive composition whole quantity. If the blending amount is less than 1 part by mass, the effect of addition tends not to be obtained sufficiently. There is a tendency that problems such as deterioration of characteristics tend to occur.

  In addition, various coupling agents can be added to the adhesive composition according to the present invention in order to improve interfacial bonding between different materials. Examples of the coupling agent include silane, titanium, and aluminum.

  Examples of the silane coupling agent include γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, and 3-aminopropylmethyl. Examples include diethoxysilane, 3-ureidopropyltriethoxysilane, and 3-ureidopropyltrimethoxysilane. These can be used alone or in combination of two or more. Moreover, commercial items, such as Nippon Unicar A-189 and A-1160, can also be used.

  It is preferable that the compounding quantity of the said coupling agent shall be 0.01-10 mass parts with respect to 100 mass parts of (A) component from the surface of an addition effect, heat resistance, and cost.

  Furthermore, an ion scavenger can be further added to the adhesive composition according to the present invention for the purpose of adsorbing ionic impurities and improving insulation reliability during moisture absorption. Examples of such ion-trapping agents include triazine thiol compounds and bisphenol-based reducing agents, such as compounds known as copper damage inhibitors to prevent copper ionization and dissolution, zirconium-based, and antimony bismuth-based magnesium. Examples include inorganic ion adsorbents such as aluminum compounds.

  The blending amount of the ion scavenger is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the component (A) from the viewpoints of addition effect, heat resistance and cost.

  The adhesive layer 2 is formed by dissolving or dispersing the above-described adhesive composition according to the present invention in a solvent to form a varnish, applying the varnish on the support substrate 3, and removing the solvent by heating. Can do. Or it can form by apply | coating the said varnish on the protective film 1, and removing a solvent by heating.

  The solvent to be used is not particularly limited, but is preferably determined in consideration of the volatility at the time of forming the adhesive layer from the boiling point. Specifically, for example, a solvent having a relatively low boiling point such as methanol, ethanol, 2-methoxyethanol, 2-ethoxyethanol, 2-butoxyethanol, methyl ethyl ketone, acetone, methyl isobutyl ketone, toluene, and xylene forms an adhesive layer. It is preferable in that the curing of the adhesive layer is difficult to proceed. In addition, for the purpose of improving the coating property, it is preferable to use a comparative high boiling point solvent such as dimethylacetamide, dimethylformamide, N-methylpyrrolidone or cyclohexanone. These solvents can be used alone or in combination of two or more.

  Examples of the support substrate 3 include a plastic film such as a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polymethylpentene film, and polyethylene terephthalate. Examples of commercially available products include polyethylene terephthalate films such as “A-31” manufactured by Teijin DuPont Films. Further, the support base 3 may be a mixture of two or more selected from the above materials, or a multilayer of the above film.

  Although the thickness of the support base material 3 does not have a restriction | limiting in particular, 5-250 micrometers is preferable. If the thickness is less than 5 μm, the support substrate may be cut during grinding (back grinding) of the semiconductor wafer, and if it is more than 250 μm, it is not economical, which is not preferable.

  The support base material 3 preferably has high light transmittance. Specifically, the minimum light transmittance in a wavelength region of 500 to 800 nm is preferably 10% or more.

  Examples of a method for applying the varnish on the supporting substrate include generally known methods such as knife coating, roll coating, spray coating, gravure coating, bar coating, and curtain coating.

  Although there is no restriction | limiting in particular in the thickness of the adhesive bond layer 2, 3-200 micrometers is preferable. If the thickness is smaller than 3 μm, the stress relaxation effect tends to be poor. If the thickness is larger than 200 μm, it is not economical and it becomes difficult to meet the demand for downsizing of the semiconductor device.

  As the protective film 3, for example, a polymer film having heat resistance and solvent resistance such as polyethylene terephthalate can be used. Examples of commercially available products include polyethylene terephthalate films such as “A-31” manufactured by Teijin Limited. The thickness of the protective film is preferably 10 to 100 μm, more preferably 30 to 75 μm, and particularly preferably 35 to 50 μm. If the thickness is less than 10 μm, the protective film tends to be broken during coating, and if it exceeds 100 μm, the cost tends to be inferior.

  The above-described adhesive sheet 10 for connecting a circuit member is interposed between a circuit member and a semiconductor element having circuit electrodes which are opposed to each other and solder-bonded, or between semiconductor elements, and the circuit member and the semiconductor elements or the semiconductor elements are interleaved. Can be used for bonding. In this case, the circuit member and the semiconductor element or the semiconductor elements can be bonded together with sufficient adhesive force while suppressing generation of voids, and the circuit electrodes can be soldered well. Thereby, the connection body excellent in connection reliability can be obtained.

  Next, a method for manufacturing a semiconductor device using the adhesive sheet 10 for connecting circuit members will be described.

2 to 6 are schematic cross-sectional views for explaining a preferred embodiment of a semiconductor device manufacturing method according to the present invention. The manufacturing method of the semiconductor device of this embodiment is as follows:
(A) preparing a semiconductor wafer having a plurality of circuit electrodes on one of the main surfaces, and providing an adhesive layer made of the adhesive composition of the present invention on the side of the semiconductor wafer on which the circuit electrodes are provided; ,
(B) a step of grinding the opposite side of the semiconductor wafer to the side where the circuit electrodes are provided to thin the semiconductor wafer;
(C) irradiating the adhesive layer with radiation;
(D) a step of dicing the thinned semiconductor wafer and the adhesive layer irradiated with radiation into individual semiconductor elements with a film adhesive;
(E) soldering the circuit electrode of the semiconductor element with a film adhesive to the circuit electrode of the semiconductor element mounting support member;
Is provided.

  In the step (a) in this embodiment, the adhesive layer is provided by sticking the adhesive layer 2 of the adhesive sheet 10 to the side of the semiconductor wafer where the circuit electrodes are provided. In the step (e) in the present embodiment, the solder bonding is performed by heating, and the film adhesive interposed between the semiconductor element and the semiconductor element mounting support member is also cured. Hereinafter, each process will be described with reference to the drawings.

(A) Process First, the adhesive sheet 10 is arrange | positioned to a predetermined apparatus, and the protective film 1 is peeled off. Subsequently, a semiconductor wafer A having a plurality of circuit electrodes 20 on one of the main surfaces is prepared, the adhesive layer 2 is pasted on the side of the semiconductor wafer A on which the circuit electrodes are provided, and the support substrate 3 / adhesive layer 2 / A laminated body in which the semiconductor wafers A are laminated is obtained (see FIG. 2). The circuit electrode 20 is provided with solder bumps for solder bonding. It is also possible to provide solder bumps on the circuit electrodes of the semiconductor element mounting support member without providing the circuit electrodes 20 with solder bumps.

(B) Process Next, as shown in FIG. 3A, the side of the semiconductor wafer A opposite to the side where the circuit electrodes 20 are provided is ground by the grinder 4 to thin the semiconductor wafer. The thickness of the semiconductor wafer can be, for example, 10 μm to 300 μm. From the viewpoint of miniaturization and thinning of the semiconductor device, the thickness of the semiconductor wafer is preferably 20 μm to 100 μm.

(C) Process When the adhesive layer 2 contains the (F) component and (G) component mentioned above, it is preferable to implement this (c) process. As shown in FIG. 3B, the adhesive layer 2 is cured by irradiating the adhesive layer 2 with radiation from the support base 3 side, and adhesion between the adhesive layer 2 and the support base 3 is performed. The power can be reduced. Here, examples of the radiation used include ultraviolet rays, electron beams, and infrared rays. In the present embodiment, it is preferable to use radiation having a wavelength of 300 to 800 nm, and the irradiation condition is such that the irradiation intensity is such that the (F) component such as the acrylic monomer is polymerized at an illuminance of 15 to 100 mW / cm ^2. It is preferable to irradiate with.

(D) Process Next, as FIG.4 (a) shows, the dicing tape 5 is affixed on the semiconductor A of a laminated body, this is arrange | positioned to a predetermined apparatus, and the support base material 1 is peeled off. At this time, since the adhesive layer 2 includes the component (F) and the component (G) described above and the step (c) is performed, the support substrate 1 can be easily peeled off. After the support substrate 1 is peeled off, the semiconductor wafer A and the adhesive layer 2 are diced by a dicing saw 6 as shown in FIG. Thus, the semiconductor wafer A is divided into a plurality of semiconductor elements A ′, and the adhesive layer 2 is divided into a plurality of film adhesives 20a.

  Next, by expanding (expanding) the dicing tape 5, the semiconductor elements A ′ obtained by the above-mentioned dicing are separated from each other, and the semiconductor element A ′ pushed up with a needle from the dicing tape 5 side and a film-like adhesive The film-like adhesive-attached semiconductor element 12 made of the agent 20a is sucked by the suction collet 7 and picked up.

(E) Process Next, as shown in FIG. 6, the circuit electrode 20 of the semiconductor element A ′ to which the film adhesive 2 a is attached and the circuit electrode 22 of the semiconductor element mounting support member 8 are aligned, The semiconductor element with film adhesive 12 and the semiconductor element mounting support member 8 are thermocompression bonded. By this thermocompression bonding, the circuit electrode 20 and the circuit electrode 22 are electrically and mechanically connected by solder bonding, and the film adhesive 2a is interposed between the semiconductor element A ′ and the semiconductor element mounting support member 8. A cured product is formed.

  The temperature during thermocompression bonding is preferably 200 ° C. or higher, more preferably 220 ° C. to 260 ° C., from the viewpoint of solder bonding. The thermocompression bonding time can be 1 to 20 seconds. The pressure for thermocompression bonding can be 0.1 to 5 MPa.

  The semiconductor device 30 is obtained through the above steps. The film adhesive comprising the adhesive composition according to the present invention is excellent in embedding property and adhesive strength after curing, and can exhibit sufficient flux activity even in solder bonding in a short time. Therefore, the semiconductor device 30 is sufficiently resistant to reflow cracks in which generation of voids is sufficiently suppressed, the circuit electrodes are well soldered, and the semiconductor element A ′ and the semiconductor element mounting support member are bonded with sufficient adhesive force. And excellent connection reliability.

7 to 9 are schematic cross-sectional views for explaining another embodiment of the method for manufacturing a semiconductor device according to the present invention. The manufacturing method of the semiconductor device of this embodiment is as follows:
(F) providing a film adhesive comprising the adhesive composition of the present invention covering the circuit electrode on the surface of the semiconductor mounting support member on which the circuit electrode is provided;
(G) preparing a semiconductor element provided with a circuit electrode and soldering the circuit electrode of the semiconductor element to the circuit electrode of the semiconductor element mounting support member;
Is provided.

  In the step (f) in this embodiment, the adhesive film for connecting circuit members of the present invention is cut onto the surface on which the circuit electrodes of the support member for semiconductor mounting are crimped, whereby the film adhesive is obtained. Provided. In the step (g) in this embodiment, solder bonding is performed by heating, and the film adhesive interposed between the semiconductor element and the semiconductor element mounting support member is also cured. Hereinafter, each process will be described with reference to the drawings.

(F) Process As shown in FIGS. 7A and 7B, a circuit member connecting adhesive sheet 10 is prepared and cut into a predetermined size using a cutting blade 24 or the like. In this way, a laminate of the film adhesive 2b formed by dividing the adhesive layer 2 and the divided support substrate 3b formed by dividing the support substrate 3 is obtained. The protective film 1 may be peeled off at any time before and after cutting, but is preferably peeled off after cutting.

  Next, as shown in FIG. 8, the film-like adhesive 2b of the above laminate is coated on the surface of the semiconductor mounting support member 8 on which the circuit electrode 22 is provided. Crimp. After the pressure bonding, the divided support base material 3b is peeled off from the film adhesive 2b. The pressure bonding conditions can be appropriately set according to the tack force of the film, for example, pressure bonding at a temperature of 25 to 100 ° C.

(G) Step Next, as shown in FIG. 9, the circuit electrode 20 of the semiconductor element A ″ provided with the circuit electrode 20 and the circuit electrode 22 of the semiconductor element mounting support member 8 are aligned, The semiconductor element A ″ and the semiconductor element mounting support member 8 are thermocompression bonded via the film adhesive 2b. By this thermocompression bonding, the circuit electrode 20 and the circuit electrode 22 are electrically and mechanically connected by solder bonding, and the film adhesive 2b is provided between the semiconductor element A ″ and the semiconductor element mounting support member 8. The cured product is formed. The circuit electrode 20 is provided with solder bumps for solder bonding. It is also possible to provide solder bumps on the circuit electrodes 22 of the semiconductor element mounting support member 8 without providing the circuit electrodes 20 with solder bumps.

  The conditions for thermocompression bonding can be the same as those in the step (e).

  The semiconductor device 40 is obtained through the above steps. Also by the manufacturing method of the semiconductor device of this embodiment, by using the adhesive sheet for connecting circuit members of the present invention, generation of voids is sufficiently suppressed, and the circuit electrodes are well soldered to each other. A semiconductor device excellent in connection reliability in which the mounting support member is bonded with a sufficient adhesive force can be obtained.

  Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples. However, the present invention is not limited to these examples.

Example 1
First, to cyclohexanone, 100 parts by mass of “HTR-860P-3” (trade name, manufactured by Nagase ChemteX Corp., glycidyl group-containing acrylic rubber, weight average molecular weight of 800,000, Tg: −7 ° C.), “E1032-H60” (Japan Epoxy Resin Co., Ltd. trade name, high purity special polyfunctional epoxy resin) 80 parts by mass, “DPP-M” (Shin Nippon Petrochemical Co., Ltd. trade name, dicyclopentadiene type phenol resin, OH equivalent: 169 g / eq) 60 parts by mass, “DML-POP” (trade name, manufactured by Honshu Chemical Co., Ltd., methylol compound having one phenol hydroxyl group in the molecule represented by the following formula (A), softening point 70 ° C., OH Equivalent: 89 g / eq) 10 parts by mass, “FA-513AS” (trade name, acrylic monomer, manufactured by Hitachi Chemical Co., Ltd.), 30 parts by mass, “2P as a curing accelerator” -CN "(trade name, manufactured by Shikoku Kasei Co., Ltd., imidazole compound) 1.5 parts by mass, and" Irg-184 "(trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.) 1.5 parts by mass as a photoinitiator The mixture was stirred and mixed, and vacuum degassed to obtain an adhesive varnish.

  Next, the adhesive varnish obtained above was applied to a surface release-treated polyethylene terephthalate (manufactured by Teijin DuPont Films, Teijin Tetron Film: A-31, thickness 50 μm) to a thickness of 30 μm after drying. Heat drying at 30 ° C. for 30 minutes. Thus, an adhesive sheet for connecting circuit members in which an adhesive layer was formed on the support base material was obtained.

(Example 2)
Except having changed the compounding quantity of "E1032-H60", "DPP-M", and "DML-POP" in preparation of adhesive varnish into 85 mass parts, 42 mass parts, and 22 mass parts, respectively, it carried out similarly to Example 1. Thus, an adhesive sheet for connecting circuit members was obtained.

(Example 3)
Except that the blending amounts of “E1032-H60”, “DPP-M” and “DML-POP” in the preparation of the adhesive varnish were changed to 90 parts by mass, 23 parts by mass and 35 parts by mass, respectively, in the same manner as in Example 1. Thus, an adhesive sheet for connecting circuit members was obtained.

(Example 4)
An adhesive sheet for connecting circuit members was obtained in the same manner as in Example 1 except that “FA-513AS” and “Irg-184” were not blended.

(Example 5)
In the preparation of the adhesive varnish, the blending amounts of “E1032-H60” and “DPP-M” were changed to 75 parts by mass and 75 parts by mass, respectively, and “DML-POP” (Honshu Chemical ( Example 1 except that 10 parts by mass of a trade name, a methylol compound containing one phenolic hydroxyl group in the molecule represented by the following formula (B), a softening point of 130 ° C., and an OH equivalent: 56 g / eq) In the same manner as above, an adhesive sheet for connecting circuit members was obtained.

(Comparative Example 1)
The same as Example 1 except that the blending amounts of “E1032-H60” and “DML-POP” in the preparation of the adhesive varnish were changed to 100 parts by weight and 50 parts by weight, respectively, and “DPP-M” was not blended. Thus, an adhesive sheet for connecting circuit members was obtained.

(Comparative Example 2)
30 mass of “TMOM-BP” (trade name, manufactured by Honshu Chemical Co., Ltd., biphenyl type methylol compound represented by the following formula (C), softening point 100 ° C., OH equivalent 181 g / eq) instead of “DML-POP” An adhesive sheet for connecting circuit members was obtained in the same manner as in Example 1 except that the components were mixed.

(Comparative Example 3)
In place of “DML-POP”, “TMOM-BPA” (trade name, manufactured by Honshu Chemical Co., Ltd., BPA type methylol compound represented by the following formula (D), softening point 65 ° C., OH equivalent: 58 g / eq () In the same manner as in Example 1, except that 10 parts by mass and 30 parts by mass of “FA-512AS” (trade name, manufactured by Hitachi Chemical Co., Ltd., acrylic monomer) instead of “FA-513AS” were added. An adhesive sheet for member connection was obtained.

(Comparative Example 4)
Implemented except that “DML-POP” was not blended and “A-DPH” (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd., dipentaerythritol hexaacrylate) was blended in place of “FA-513AS”. In the same manner as in Example 1, an adhesive sheet for connecting circuit members was obtained.

[Evaluation of adhesive sheet for connecting circuit members]
About the adhesive sheet for circuit member connection obtained above, embedding property, flux activity, and adhesive force were evaluated according to the following test procedure. In addition, about the flux activity, the flux activity of the mix | blended methylol compound was evaluated. The results are shown in Table 1. The comparative example 4 which does not contain a methylol compound made flux activity "x".

<Embedment>
A chip (10 mm square, thickness 280 μm) with gold wire bumps (leveled, bump height 30 μm, 184 bumps) was placed on the stage of the temporary pressure bonding apparatus with the bump surface facing up. Next, the circuit board connecting adhesive sheet is cut into 11 mm squares together with the supporting substrate, and this is placed on the chip so that the adhesive layer side faces the bump surface, and further, a silicone heat conductive cover film is placed thereon, Heating and pressing were performed at 80 ° C. and 1 MPa.

After heating and pressing, the supporting base material was peeled off from the adhesive layer, and the adhesive layer was exposed to 500 mJ at an illuminance of 15 mW / cm ² using ultraviolet rays to obtain a chip with an adhesive. Next, the obtained chip with adhesive was aligned with a Ni / Au plated Cu circuit printed circuit board, and then heated and pressurized at 250 ° C., 5 MPa, and 10 seconds. About the semiconductor device obtained in this way, the void situation was observed with the ultrasonic microscope, and embedding property was evaluated based on the following reference | standard.
○: There are almost no voids, and the voids are less than 10% of the embedded area.
X: Many voids exist and the voids are 10% or more of the embedded area.

<Flux activity test>
Ten solder balls of 3 mmφ were placed on a copper plate, and about 200 mg of a methylol compound was placed thereon and heated on a hot plate heated to 260 ° C. The state of the solder ball after 30 seconds was observed, and the flux activity was evaluated according to the following criteria.
○: Solder balls are aggregated into almost one piece.
Δ: Solder balls are aggregated into several pieces.
X: Solder balls are not agglomerated at all and there are 10 solder balls after the test.

<Adhesive strength>
First, the adhesive sheet for connecting circuit members was exposed to 500 mJ at an illuminance of 15 mW / cm ² using ultraviolet rays. Next, the exposed sheet was cut into 6.5 mm × 6.5 mm. Circuit member connection by laminating the obtained film-like adhesive on the surface on which the SiO ₂ film of a 280 μm-thick chip diced to 6.5 mm × 6.5 mm exists at 25 to 80 ° C. A semiconductor chip with an adhesive was obtained.

  The semiconductor chip with adhesive obtained above is die-bonded on an organic substrate (PSR-4000, SR-AUS308 (outside), 0.2 mm thickness) under the conditions of 250 ° C., 0.5 MPa, 10 seconds, Further, post-curing was performed by heating at 175 ° C. for 2 hours. Thus, an evaluation sample was obtained.

The obtained sample for evaluation was held on a hot plate at 265 ° C. for 30 seconds, and then the shear adhesive strength between the chip and the organic substrate was measured, and the adhesive strength was evaluated based on the following criteria.
○: The shear bond strength is 1 MPa or more.
X: The shear bond strength is less than 1 MPa.

DESCRIPTION OF SYMBOLS 1 ... Protective film, 2 ... Adhesive layer, 3 ... Support base material, 4 ... Grinder, 5 ... Dicing tape, 6 ... Dicing saw, 7 ... Suction collet, 8 ... Support member for mounting semiconductor elements, 10 ... Connection of circuit members Adhesive sheet, 12 ... semiconductor element with film adhesive, 20, 22 ... circuit electrode, 30, 40 ... semiconductor device, A ... semiconductor wafer, B ... radiation.

Claims (8)

( A) a high molecular weight component having a weight average molecular weight of 100,000 or more;
(B) an epoxy resin;
(C) a phenolic epoxy resin curing agent;
(D) a methylol compound having one phenolic hydroxyl group in one molecule;
(E) only contains a curing accelerator, the,
The adhesive composition whose said methylol compound is a methylol compound shown by following General formula (1) .

[In the formula (1), X represents an alkyl group having 1 to 10 carbon atoms, and when the carbon number is 2 or more and has a methylene group, at least one of the methylene groups is -O-, -NH-, -S. -, -CO-, -OCO- or -COO- may be substituted, and when it has 3 or more carbon atoms and has a methine group (-CH <), at least one of the methine groups is substituted with a nitrogen atom. It may be. ] 5 to 500 parts by mass of the component (B) with respect to 100 parts by mass of the component (A),
The equivalent ratio of the phenolic hydroxyl group of the component (C) to the epoxy group of the component (B) is 0.5 to 1.5,
The ratio of the hydroxyl group of the component (D) to the total of hydroxyl groups of the component (C) and the component (D) is 25% or more,
The adhesive composition of Claim 1 which contains 0.1-20 mass parts of said (E) components with respect to a total of 100 mass parts of said (B) component, (C) component, and (D) component. The adhesive composition according to claim 1 or 2, wherein the component (A) is a glycidyl group-containing (meth) acrylic copolymer containing 0.5 to 6% by mass of a repeating unit having a glycidyl group. (F) radiation-polymerizable compounds and further containing (G) a photoinitiator, the adhesive composition according to any one of claims 1-3. The adhesive composition according to any one of claims 1 to 4, which is used for adhering the circuit members by interposing them between circuit members having circuit electrodes which are opposed to each other and soldered. An adhesive sheet for connecting a circuit member, comprising: a support base material; and an adhesive layer provided on the support base material and made of the adhesive composition according to any one of claims 1 to 4 . The adhesive sheet for connecting circuit members according to claim 6, which is used for interposing between circuit members having circuit electrodes that are opposed to each other and solder-bonded to bond the circuit members together. A semiconductor wafer having a plurality of circuit electrodes on one of the main surfaces is prepared, and the adhesive composition according to any one of claims 1 to 4 is provided on the side of the semiconductor wafer on which the circuit electrodes are provided. Providing an adhesive layer comprising:
Grinding the opposite side of the semiconductor wafer from the side where the circuit electrodes are provided to thin the semiconductor wafer;
Dicing the thinned semiconductor wafer and the adhesive layer into individual semiconductor elements with a film adhesive; and
Soldering the circuit electrode of the semiconductor element with the film adhesive to the circuit electrode of the semiconductor element mounting support member.

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