WO2015107990A1 - 接着組成物ならびにそれを有する接着フィルム、接着組成物付き基板、半導体装置およびその製造方法 - Google Patents
接着組成物ならびにそれを有する接着フィルム、接着組成物付き基板、半導体装置およびその製造方法 Download PDFInfo
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- WO2015107990A1 WO2015107990A1 PCT/JP2015/050483 JP2015050483W WO2015107990A1 WO 2015107990 A1 WO2015107990 A1 WO 2015107990A1 JP 2015050483 W JP2015050483 W JP 2015050483W WO 2015107990 A1 WO2015107990 A1 WO 2015107990A1
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- adhesive composition
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- film
- polyimide
- manufactured
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Classifications
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- H05K3/00—Apparatus or processes for manufacturing printed circuits
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Definitions
- the present invention relates to an electronic component used for a personal computer and a portable terminal, a heat sink and a printed circuit board, an adhesive composition that can be used for bonding a flexible substrate and bonding substrates, and an adhesive composition that can be used for wafer protection. More specifically, the present invention relates to the bonding of semiconductor chips such as IC and LSI to circuit boards such as flexible substrates, glass epoxy substrates, glass substrates, ceramic substrates, silicon interposers, and bonding between semiconductor chips. In particular, the present invention relates to an adhesive composition used for stacking semiconductor chips such as three-dimensional mounting. Moreover, it is related with the adhesive film which has the adhesive composition of this invention, a board
- an underfill material is filled between the chip and the substrate.
- a method of filling the underfill material a method of filling between the chip and the substrate using a capillary phenomenon is common, but there is a problem that unfilling is likely to occur and the manufacturing cost is increased.
- a technique for solving these problems a technique has been devised in which an underfill material is formed on a wafer and individual chips are bonded.
- a method of forming on a wafer there are a method of forming a resin composition applied in the form of a film on a wafer by vacuum heat laminating or the like, a method of directly applying a resin coating agent and forming on a wafer, and the like.
- the coating agent for forming the resin layer on the wafer is required to have storage stability at room temperature and curing characteristics in a short time, and the cured product is required to have high strength.
- the epoxy composition has a feature of excellent adhesiveness, but has a problem of low strength. Therefore, a resin composition containing polyimide has been reported as a method for improving this. (For example, Patent Document 1 and Patent Document 2).
- an object of the present invention is to provide an adhesive composition excellent in strength in a state where cracks are formed.
- the present invention contains (A) a polyimide, (B) a polyfunctional epoxy compound, (C) an epoxy curing agent, and (D) inorganic particles, and the ratio of the (A) polyimide in the nonvolatile organic component is 3. 0 wt% or more and 30 wt% or less, the proportion of the (C) epoxy curing agent in the nonvolatile organic component is 0.5 wt% or more and 10 wt% or less, and the total number of grams of the nonvolatile organic component is T,
- An adhesive composition wherein the number of moles of epoxy groups in the nonvolatile organic component is M, and T / M is 400 or more and 8000 or less.
- an adhesive composition having excellent strength in a state where cracks are formed can be obtained.
- the adhesive composition of the present invention contains (A) a polyimide, (B) a polyfunctional epoxy compound, (C) an epoxy curing agent, and (D) inorganic particles, and the ratio of the (A) polyimide in the nonvolatile organic component Is 3.0 wt% or more and 30 wt% or less, the proportion of the (C) epoxy curing agent in the non-volatile organic component is 0.5 wt% or more and 10 wt% or less, and the total number of grams of the non-volatile organic component Where T is M and the number of moles of epoxy groups in the nonvolatile organic component is M, T / M is 400 to 8000.
- the non-volatile organic component mentioned here refers to an organic chemical substance that does not lose weight by 5% or more when thermogravimetric measurement is performed at 200 ° C. for 1 hour.
- the adhesive composition of the present invention contains (A) polyimide.
- (B) ring opening of a polyfunctional epoxy compound and (A) addition reaction to polyimide are accelerated during heat treatment.
- the functional group capable of reacting with the epoxy group include a phenolic hydroxyl group, a sulfonic acid group, and a thiol group.
- the method for synthesizing such a polyimide (A) is not limited to the following examples.
- an acid dianhydride having a group capable of reacting with an epoxy group is reacted with a diamine to obtain a polyimide precursor.
- terminal modification of this polyimide precursor is performed using primary monoamine as a terminal blocking agent, followed by heat treatment at 150 ° C. or higher to perform polyimide ring closure.
- a diamine is added to synthesize a terminal precursor-modified polyimide precursor, and polyimide ring closure is performed at a high temperature of 150 ° C. or higher.
- the method of performing is mentioned.
- a preferred example of the polyimide (A) used in the present invention has a structure represented by the general formula (2) or the general formula (3), and a structure represented by the general formula (1) is represented by the general formula (2).
- R 4 in the general formula (3) is 5 to 15% by weight based on the total amount of the polymer.
- the total amount of the polymer (polyimide) obtained by the synthesis of the polyimide here means the weight obtained by the polymerization of the components composed of the diamine, the acid dianhydride, and the end-capping agent, and is excessive during the synthesis.
- the diamine, acid dianhydride and terminal blocker charged in the above are not included in the weight of the polyimide.
- R 1 is a divalent hydrocarbon group.
- R 1 is preferably an alkylene group having 1 to 5 carbon atoms or a phenylene group.
- R 2 is a monovalent hydrocarbon group.
- R 2 is preferably an alkyl group having 1 to 5 carbon atoms or a phenyl group. May contain R 1 and R 2 in different structures in one molecule of the polyimide may contain R 1 and R 2 in different structures between different polyimide molecules.
- N represents an integer of 1 to 10, preferably 1 to 2.
- R 3 is a 4 to 14 valent organic group
- R 4 is a 2 to 12 valent organic group
- at least one of R 3 and R 4 is 1,1,1,3,3, It contains at least one group selected from the group consisting of 3-hexafluoropropyl group, isopropyl group, ether group, thioether group and SO 2 group (hereinafter referred to as “specific group”).
- R 3 and R 4 preferably contain an aromatic group.
- R 5 and R 6 represent an organic group having at least one group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group, and a thiol group.
- One molecule of polyimide may contain R 3 to R 6 having different structures, and different polyimide molecules may contain R 3 to R 6 having different structures.
- X represents a monovalent organic group.
- m is 8 to 200.
- the (A) polyimide used for this invention is an organic solvent soluble polyimide which melt
- the solubility of an organic solvent-soluble polyimide that dissolves in an organic solvent means that it is dissolved in at least one solvent selected from the following by 20% by weight or more at 23 ° C.
- Ketone solvents acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, ether solvents 1,4-dioxane, tetrahydrofuran, diglyme, glycol ether solvents methyl cellosolve, ethyl cellosolve, propylene glycol monomethyl ether, propylene glycol Monoethyl ether, propylene glycol monobutyl ether, diethylene glycol methyl ethyl ether, other benzyl alcohol, N-methylpyrrolidone, ⁇ -butyrolactone, ethyl acetate, N, N-dimethylformamide.
- R 3 represents a structural component of acid dianhydride, and among them, a C 4 to C 14 valent organic group is preferable.
- R 4 represents a structural component of diamine, and among them, a divalent to 12-valent organic group having 5 to 40 carbon atoms is preferable. Moreover, it is preferable that both R 3 and R 4 contain at least one specific group.
- R 5 is an acid dianhydride substituent, and is preferably a group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group, and a thiol group.
- R 6 is a substituent of diamine, and is preferably a group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group, and a thiol group.
- the acid dianhydride used will be described.
- Specific examples of the acid dianhydride having at least one specific group include 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride and 2,2-bis (2,3-dicarboxy).
- R 9 represents C (CF 3 ) 2 , C (CH 3 ) 2 , SO 2 , S or O.
- R 10 and R 11 represent a hydrogen atom, a hydroxyl group, a thiol group or a sulfonic acid group. However, R 10 and R 11 are not simultaneously hydrogen atoms.
- the acid dianhydride having no specific group and having at least one group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group and a thiol group is specifically an aromatic acid diacid having the structure shown below. Mention may be made of anhydrides.
- R 7 and R 8 represent a hydrogen atom, a hydroxyl group, a thiol group or a sulfonic acid group. However, R 7 and R 8 are not simultaneously hydrogen atoms.
- acid dianhydride having no specific group and having no phenolic hydroxyl group, sulfonic acid group, and thiol group include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetra Carboxylic dianhydride, 2,3,3 ′, 4′-biphenyltetracarboxylic dianhydride, 2,2 ′, 3,3′-biphenyltetracarboxylic dianhydride, 3,3 ′, 4,4 '-Benzophenone tetracarboxylic dianhydride, 2,2', 3,3'-benzophenone tetracarboxylic dianhydride, 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, 1,1 -Bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, bis (2
- these acid dianhydrides are used alone or in combination of two or more.
- diamine used will be described.
- Specific examples of the diamine having at least one specific group include 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl ether, and 4,4'-diamino.
- Diphenyl ether 3,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, bis (4-aminophenoxyphenyl) sulfone, bis (3-aminophenoxyphenyl) sulfone, bis (4-aminophenoxy) biphenyl, bis [4- (4-aminophenoxy) phenyl] ether, 1,4-bis (4-aminophenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 2,2-bis [4- (4- Aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (4-a Nofenokishi) phenyl] propane, or compounds substituted with alkyl group or halogen atom in the aromatic ring.
- diamine having at least one specific group and at least one group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group, and a thiol group include 2,2-bis (3- Amino-4-hydroxyphenyl) hexafluoropropane, 2,2-bis (3-hydroxy-4-aminophenyl) hexafluoropropane, 2,2-bis (3-amino-4-hydroxyphenyl) propane, 2,2 -Bis (3-hydroxy-4-aminophenyl) propane, 3,3'-diamino-4,4'-dihydroxydiphenyl ether, 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone, 3,3'- Diamino-4,4'-dihydroxydiphenylsulfide or an aromatic ring thereof can be substituted with an alkyl group or a halogen atom.
- R 16 represents C (CF 3 ) 2 , C (CH 3 ) 2 , SO 2 , S or O.
- R 17 to R 18 represent a hydrogen atom, a hydroxyl group, a thiol group, or a sulfonic acid group. However, R 17 and R 18 are not simultaneously hydrogen atoms.
- diamine having no specific group and having at least one group selected from the group consisting of a phenolic hydroxyl group, a sulfonic acid group, and a thiol group include 3,3′-diamino-4,4′-dihydroxy.
- Biphenyl 2,4-diamino-phenol, 2,5-diaminophenol, 1,4-diamino-2,5-dihydroxybenzene, diaminodihydroxypyrimidine, diaminodihydroxypyridine, hydroxydiaminopyrimidine, 9,9-bis (3- Amino-4-hydroxyphenyl) fluorene, a compound in which these aromatic rings are substituted with an alkyl group or a halogen atom, or a diamine having the structure shown below.
- R 12 to R 15 represent a hydrogen atom, a hydroxyl group, a thiol group, or a sulfonic acid group. However, R 12 and R 13 are not simultaneously hydrogen atoms.
- diamines that do not have a specific group and do not have a phenolic hydroxyl group, sulfonic acid group, or thiol group include 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, benzidine, and m-phenylenediamine.
- P-phenylenediamine 1,5-naphthalenediamine, 2,6-naphthalenediamine, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, 3,3′-dimethyl-4,4′-diaminobiphenyl, 3,3′-diethyl-4,4′-diaminobiphenyl, 2,2 ′, 3,3′-tetramethyl-4,4′-diaminobiphenyl 3,3 ′, 4,4′-tetramethyl-4,4′-diaminobiphenyl, 2,2′-di (trifluoromethyl) -4,4′-di Minobiphenyl or a compound in which these aromatic rings are substituted with an alkyl group or a halogen atom, terephthalic acid hydrazide, isophthalic acid hydrazide, phthaloic acid hydrazide, 2,
- the structure represented by the general formula (1) is general formula (2), because it contains as R 4 in (3), a constituent of a diamine.
- Examples of the diamine having the structure represented by the general formula (1) include bis (3-aminopropyl) tetramethyldisiloxane and bis (p-amino-phenyl) octamethylpentasiloxane.
- R 5 and R 6 in the general formulas (2) and (3), the reaction rate between the polyimide and the epoxy compound during the heat treatment can be adjusted, and the crosslinking density of the adhesive composition can be adjusted. This makes it possible to impart the required heat resistance and chemical resistance to the adhesive composition.
- ⁇ and ⁇ each represents an integer of 0 to 10
- ⁇ + ⁇ represents an integer of 0 to 10.
- 20 to 90% of the total of R 5 and R 6 is preferably a phenolic hydroxyl group, a sulfonic acid group or a thiol group.
- X which is a structural component of the general formulas (2) and (3) is a component derived from a primary monoamine which is a terminal blocking agent. These may be used alone or in combination of two or more with other end-capping groups.
- Specific examples of the primary monoamine include 5-aminoquinoline, 4-aminoquinoline, 3-aminonaphthalene, 2-aminonaphthalene, 1-aminonaphthalene, aniline and the like. Of these, aniline is preferably used.
- a primary monoamine that does not have any other substituent that can react with the epoxy compound.
- This makes it possible to obtain a polyimide that does not have a substituent that reacts with the epoxy compound at the terminal portion of the polyimide having high molecular mobility. By using this, the reaction between the polyimide and the epoxy compound does not easily proceed at room temperature, and the storage stability of the adhesive composition can be further improved.
- the introduction ratio of the X component in the general formulas (2) and (3) is 0.1 to 60 mol% with respect to the total diamine component, when converted in terms of the primary monoamine component of the terminal blocker that is the original component.
- the range is preferable, and particularly preferably 5 to 50 mol%.
- m represents the number of polymer repetitions, and ranges from 8 to 200. The preferred range is 10 to 150.
- weight average molecular weight it is preferably 4000 to 80,000, particularly preferably 8000 to 60,000 in terms of polystyrene by gel filtration chromatography.
- m By setting m to 8 or more, the viscosity can be increased to enable thick film coating, and by setting m to 200 or less, solubility in a solvent can be improved.
- the weight average molecular weight of (A) polyimide can be determined by the following method.
- a weight average molecular weight in terms of polystyrene is calculated by a GPC apparatus Waters 2690 (manufactured by Waters Co., Ltd.).
- GPC measurement conditions are such that the moving bed is NMP in which LiCl and phosphoric acid are dissolved at a concentration of 0.05 mol / L, and the development rate is 0.4 ml / min.
- Detector Waters 996 System controller: Waters 2690 Column oven: Waters HTR-B Thermo Controller: Waters TCM Column: TOSOH (TSK-GEL Guard Column) Column: TOSOH TSK-GEL ⁇ -4000 Column: TOSOH TSK-GEL ⁇ -2500 and the like.
- the polyimide (A) used in the present invention may be only one having a structure represented by the general formulas (2) and (3), or a structure represented by the general formulas (2) and (3). It may be a copolymer having another structure as a copolymerization component, or a mixture thereof. Furthermore, the polyimide represented by another structure may be mixed with any of these. In that case, it is preferable to contain 50 mol% or more of the structures represented by the general formulas (2) and (3).
- the type and amount of the structure used for copolymerization or mixing are preferably selected within a range that does not impair the heat resistance of the heat resistant resin film obtained by heat treatment.
- the structure of the general formula (1) introduced into the polymer and the end capping agent used in the present invention can be easily detected and quantified by the following method.
- a polymer in which the structure of the general formula (1) and the end-capping agent are introduced is dissolved in an acidic solution or a basic solution, and decomposed into a diamine component and an acid anhydride component which are constituent units of the polymer.
- the structure of the general formula (1) and the end-capping agent used can be easily detected and quantified by gas chromatography (GC) or NMR measurement.
- the structure of the general formula (1) is also used by directly measuring the pyrolysis gas chromatograph (PGC), infrared spectrum and 13C NMR spectrum of the polyimide into which the end-capping agent is introduced.
- PPC pyrolysis gas chromatograph
- the end capping agent can be easily detected and quantified.
- the content of the polyimide is 30% by weight or less in the non-volatile organic component from the viewpoint of the coating property to the substrate with bumps and the filling property between the bumps.
- the resin coating agent as used herein refers to a coating liquid whose viscosity is adjusted with an organic solvent in order to form a film on a wafer, a substrate, a support film or the like by a coating method such as a spin coater.
- the proportion of (A) polyimide in the nonvolatile organic component is 3.0% by weight or more.
- the proportion of the (A) polyimide in the nonvolatile organic component is more preferably 5.0% by weight or more and 30% by weight or less.
- the adhesive composition of the present invention further contains (B) a polyfunctional epoxy compound.
- the polyfunctional epoxy compound mentioned here refers to a compound containing two or more glycidyl groups or epoxycyclohexyl groups in one molecule.
- the polyfunctional epoxy compound (A) has a phenolic hydroxyl group, a sulfonic acid group or a thiol group in the side chain, it reacts with these to form a cured product having a network structure with higher density.
- the resulting cured adhesive composition exhibits strong resistance to various chemicals.
- an epoxy compound is generally cured by a ring-opening reaction that is not accompanied by shrinkage, it is possible to reduce shrinkage during curing of the adhesive composition.
- As a polyfunctional epoxy compound that whose epoxy equivalent is 100 or more is preferable. By setting the epoxy equivalent to 100 or more, the strength of the cured adhesive composition can be increased.
- the polyfunctional epoxy compound is not particularly limited as long as it is bifunctional or higher.
- bisphenol A type epoxy resin bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy Resin, Biphenyl type epoxy resin, Hydroquinone type epoxy resin, Diphenyl sulfide skeleton containing epoxy resin, Phenol aralkyl type polyfunctional epoxy resin, Naphthalene skeleton containing polyfunctional epoxy resin, Dicyclopentadiene skeleton containing polyfunctional epoxy resin, Triphenylmethane skeleton containing A polyfunctional epoxy resin, an aminophenol type epoxy resin, a diaminodiphenylmethane type epoxy resin, and other various polyfunctional epoxy resins can be used.
- the bisphenol A type epoxy resin obtained by the reaction of bisphenol A and epichlorohydrin includes jER828 and YL980 having one bisphenol A skeleton, jER1010 and jER1256 having a plurality of bisphenol A skeletons, etc. Co., Ltd.).
- the epoxy equivalent (g / eq, which may be omitted hereinafter) is preferably 1000 or more, and more preferably 2000 or more.
- the epoxy equivalent is preferably 7000 or less, more preferably 5000 or less, and even more preferably 4000 or less.
- Examples of such bisphenol A type epoxy resins having an epoxy equivalent of 1000 or more and 7000 or less include jER1007, jER1009, jER1010 (above, trade name, manufactured by Mitsubishi Chemical Corporation).
- the proportion of the epoxy resin having an epoxy equivalent of 1000 or more and 7000 or less in the non-volatile organic component is preferably 20% by weight or more and 70% by weight or less, and 20% by weight or more and 60% by weight or less from the viewpoint of film forming property. More preferred.
- liquid epoxy compound from the viewpoint of the fluidity of the adhesive composition and the filling property between protrusions such as copper pillar bumps and solder bumps.
- the liquid epoxy compound is an epoxy compound having a viscosity of 150 Pa ⁇ s or less at 25 ° C. and 1 atm.
- Epototo PG-207GS manufactured by Nippon Steel Chemical Co., Ltd.
- YL980, jER828, jER806, jER807, YL983U (trade name, manufactured by Mitsubishi Chemical Corporation) and the like can be mentioned.
- the proportion of the liquid epoxy compound in the non-volatile organic component is 5% by weight or more and 60% by weight or less from the viewpoint of fluidity of the adhesive composition and filling property between protrusions such as copper pillar bumps and solder bumps. Is more preferable, and more preferably 10 wt% or more and 50 wt% or less.
- the adhesive composition of the present invention contains (C) an epoxy curing agent.
- the epoxy curing agent it is preferable that the viscosity does not increase greatly in the state of a resin coating agent containing an organic solvent, and an imidazole curing agent is preferable from the viewpoint of reactivity and storage stability.
- imidazole curing agents examples include imidazole, 2-methylimidazole, 2-undecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2E4MZ, 2PZ, C11Z, 2P4MZ (above trade names, manufactured by Shikoku Kasei Kogyo Co., Ltd.) and the like.
- the curing rate time of the imidazole curing agent is preferably 20 days or less, more preferably 5 days or less, and even more preferably 2 days or less. Further, from the viewpoint of storage stability, the curing rate time of the imidazole curing agent is preferably 0.2 days or more, more preferably 0.5 days or more. Specific examples of the imidazole curing agent having a curing speed of 0.5 days or more and 2 days or less include 2PZ, 2PZ-OK (trade names, manufactured by Shikoku Kasei Kogyo Co., Ltd.) and the like.
- Curing speed time means that when 100 mL of a sample to which 5 parts by weight of an imidazole-based curing agent is added with respect to 100 parts by weight of bisphenol A type liquid epoxy resin is stored in a sealed state at 25 ° C. It refers to the number of days until the viscosity of the sample becomes twice the initial viscosity.
- the proportion of the (C) epoxy curing agent in the nonvolatile organic component is 0.5% by weight or more and 10% by weight or less.
- the proportion of the epoxy curing agent (C) in the non-volatile organic component exceeds 10% by weight, the adhesive composition is cured, but the usable time at room temperature is shortened.
- the proportion of the (C) epoxy curing agent in the nonvolatile organic component is preferably 5% by weight or less, more preferably 3% by weight or less.
- the proportion of the (C) epoxy curing agent in the nonvolatile organic component is 0.5% by weight or more, and preferably 1.0% by weight or more. By setting the content to 0.5% by weight or more, a semiconductor device with more excellent connection reliability can be manufactured.
- the adhesive composition of the present invention contains (D) inorganic particles.
- the inorganic particles can adjust the melt viscosity of the adhesive composition to such an extent that it does not foam when the adhesive composition is heat-cured.
- the material of the inorganic particles includes silica, alumina, titania, silicon nitride, boron nitride, aluminum nitride, iron oxide, glass and other metal oxides, metal nitrides, metal carbonates, barium sulfate and other metal sulfates Etc. can be used alone or in admixture of two or more. Among these, silica can be preferably used in terms of low thermal expansion, heat dissipation, low moisture absorption, and dispersion stability in the adhesive composition.
- the shape of the inorganic particles may be any of spherical, crushed, flaky and other non-spherical shapes, but the spherical inorganic particles can be preferably used because they are easily dispersed uniformly in the adhesive composition.
- the average particle size of the spherical inorganic particles is preferably 3 ⁇ m or less, more preferably 1.0 ⁇ m or less, and even more preferably 700 nm or less, from the viewpoint of filling between projections such as copper pillar bumps and solder bumps. It is.
- the average particle diameter is preferably 10 nm or more, and when it is 10 nm or more, the dispersibility is excellent, and the adhesive composition can be filled with inorganic particles at a high concentration. Further, from the viewpoint of the coatability of the prepared resin coating agent, the average particle size is preferably 100 nm or more, more preferably 300 nm or more.
- the particle size of the inorganic particles is preferably 100 nm or less, and more preferably 60 nm or less.
- the particle size of the inorganic particles is preferably 100 nm or less, and more preferably 60 nm or less.
- (D) inorganic particles When preparing the resin coating agent, (D) inorganic particles may be added in a slurry state dispersed in an organic solvent, or powder without solvent may be added. Moreover, you may add both the inorganic particle of a slurry state, and the inorganic particle of a powder. From the viewpoint of dispersibility of inorganic particles, it is preferable to use inorganic particles in a slurry state.
- the average particle size of the inorganic particles indicates the particle size when the inorganic particles are present alone, and indicates the most frequent particle size.
- the shape is spherical, the diameter is represented, and when the shape is elliptical or flat, the maximum length of the shape is represented. Furthermore, in the case of rod shape or fiber shape, it represents the maximum length in the longitudinal direction.
- SEM scanning electron microscope
- the inorganic particles are preferably surface-treated.
- a general silane coupling agent can be used, but from the viewpoint of dispersibility and adhesiveness, a silane coupling agent containing an epoxy group or a silane coupling containing an amino group. Agents are preferred.
- the content of the inorganic particles is preferably 50% by weight or more and 80% by weight or less, more preferably 60% by weight or more and 75% by weight or less, and more preferably 60% by weight with respect to the total amount of the nonvolatile components. More preferably, it is 70 weight% or less.
- the content of the inorganic particles is 50% by weight or more, when this adhesive composition is used, a semiconductor device that is superior in connection reliability can be manufactured. Moreover, the dispersibility of an inorganic particle becomes it more favorable that content of (D) inorganic particle is 80 weight% or less.
- nonvolatile component refers to a component that combines a nonvolatile organic component and a nonvolatile inorganic component.
- the adhesive composition of the present invention may contain a thermoplastic resin for the purpose of reducing the stress of the cured film within a range that does not impair the effects of the present invention.
- a thermoplastic resin include phenoxy resin, polyester, polyurethane, polyamide, polypropylene, acrylonitrile-butadiene copolymer (NBR), styrene-butadiene copolymer, (SBR), acrylonitrile-butadiene-methacrylic acid copolymer, Examples include, but are not limited to, acrylonitrile-butadiene-acrylic acid copolymers.
- the adhesive composition of the present invention and the resin coating agent comprising the adhesive composition may contain a surfactant for the purpose of improving the affinity with the substrate as long as the effects of the present invention are not impaired.
- a surfactant is not particularly limited, and examples thereof include a fluorine-based surfactant, a silicone-based surfactant, and a nonionic surfactant. Among these, a fluorine-based surfactant having a high effect of improving affinity with the substrate is preferable.
- fluorosurfactant hereinafter referred to as “trade name”
- Megafac F171, F173, and R-30 DIC Corporation (formerly Dainippon Ink and Chemicals)
- Florard FC430 and FC431 Sumitomo 3M Co., Ltd.
- Asahi Guard AG710 Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by Asahi Glass Co., Ltd.) and the like.
- silicone surfactants are BYK-378, BYK-337, BYK-306, BYK-333, BYK-375, BYK-370, BYK-377, BYK-323. , BYK-325 (manufactured by Big Chemie Japan Co., Ltd.) and the like, but are not limited thereto.
- surfactant can also be used in combination of multiple types.
- the adhesive composition of the present invention and the resin coating agent comprising the adhesive composition may contain an adhesion promoter for the purpose of improving the adhesion to the substrate within a range not impairing the effects of the present invention. At that time, a plurality of types of adhesion promoters may be used in combination.
- adhesion promoter examples include chlorosilanes such as trimethylchlorosilane, vinyltrichlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane; ⁇ -chloropropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (N-piperidinyl) propyltrimethoxysilane, trimethylmethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethylvinylethoxysilane, Alkoxysilanes such as diphenyldimethoxysilane and phenyltriethoxysilane; Silaza such as hexamethyldisilazane and methyl
- the adhesive composition of the present invention and the resin coating agent comprising the adhesive composition may contain a flux agent.
- a flux agent an organic acid compound having a carboxylic acid group or the like can be used.
- a resin coating agent from the adhesive composition of the present invention (A) polyimide, (B) polyfunctional epoxy compound, (C) epoxy curing agent, and (D) inorganic particles are mixed and stirred (A It can be prepared by dissolving polyimide), (B) polyfunctional epoxy compound, (C) epoxy curing agent in an organic solvent, and dispersing (D) inorganic particles.
- the organic solvent used here may be any solvent that dissolves (A) polyimide, (B) polyfunctional epoxy compound, and (C) epoxy curing agent.
- organic solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol monoethyl ether.
- Ethers such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate, lactic acid Acetates such as butyl, acetone, methyl ethyl ketone, Ketones such as tylacetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, cyclopentanone, 2-heptanone, butyl alcohol, isobutyl alcohol, pentaanol, 4-methyl-2-pentanol, 3-methyl-2 -Alcohols such as butanol, 3-methyl-3-methoxybutanol and diacetone alcohol, aromatic hydrocarbons such as toluene and xylene,
- the boiling point in the present invention is a boiling point under a pressure of 1 atm, that is, 1.013 ⁇ 10 5 N / m 2 .
- the boiling point can be measured using a known technique and is not particularly limited. For example, the boiling point can be measured using a boiling point meter of Switzerland.
- particularly preferred organic solvents having such boiling point include cyclopentanone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate, Examples include acetone alcohol and 3-methyl-3-methoxybutanol.
- the resin coating agent obtained by mixing, dissolving and dispersing as described above may be filtered using a filter paper or a filter.
- the filtration method is not particularly limited, a method of filtering by pressure filtration using a filter having a retained particle diameter of 10 ⁇ m or more is preferable in order to pass the dispersed (D) inorganic particles.
- the non-volatile organic component of the present invention refers to an organic chemical that does not decrease in weight by 5% or more when thermogravimetrically measured at 200 ° C. for 1 hour among the components contained in the adhesive composition or resin coating agent.
- the adhesive composition of the present invention has a T / M of T (M in units), where T is the total number of grams of non-volatile organic components (unit is g), and M is the number of moles of epoxy groups in the non-volatile organic components. It is 400 or more and 8000 or less.
- T / M When T / M is 400 or more, it becomes a material that is not easily broken even in a cracked state. When T / M is less than 400, strength in a state where cracks are generated is weakened. From the viewpoint of strength, T / M is preferably 450 or more, and more preferably 500 or more. Moreover, T / M is 8000 or less from an adhesive viewpoint. Further, from the viewpoint of reliability, T / M is preferably 4000 or less, more preferably 2000 or less, and still more preferably 1000 or less.
- the adhesive film of the present invention is characterized by having a layer comprising the adhesive composition of the present invention and a support film.
- the adhesive film of the present invention can be obtained by applying the above-mentioned resin coating agent on a support film and then drying it if necessary.
- the adhesive film of the present invention has a layer composed of the adhesive composition of the present invention and a support film.
- a support film used in that case is not particularly limited, various commercially available films such as a polyethylene terephthalate (PET) film, a polyphenylene sulfide film, and a polyimide film can be used.
- PET polyethylene terephthalate
- HP2 polyethylene HP terephthalate film HP2 (U) (manufactured by Toray Film Processing Co., Ltd.) and the like can be mentioned.
- the joint surface between the layer made of the adhesive composition of the present invention and the support film may be subjected to a surface treatment such as silicone, silane coupling agent or aluminum chelating agent in order to improve adhesion and peelability.
- a surface treatment such as silicone, silane coupling agent or aluminum chelating agent in order to improve adhesion and peelability.
- the thickness of the support film is not particularly limited, but is preferably in the range of 10 to 75 ⁇ m from the viewpoint of workability.
- the adhesive film of the present invention may have a protective film on the film in order to protect the layer made of the adhesive composition of the adhesive film. Thereby, the surface of the layer made of the adhesive composition of the adhesive film can be protected from contaminants such as dust and dust in the atmosphere.
- the protective film examples include a polyethylene film, a polypropylene (PP) film, and a polyester film.
- PP polypropylene
- SR3 which is a polyethylene terephthalate film (manufactured by Otsuchi Industry Co., Ltd.) and the like can be mentioned.
- the protective film is preferably one having a small adhesive force with the layer made of the adhesive composition of the adhesive film.
- the resin coating agent comprising the adhesive composition of the present invention to the support film
- the method include a coater, a gravure coater, a screen coater, and a slit die coater.
- the film thickness after drying is usually 0.5 ⁇ m or more and 100 ⁇ m or less.
- Oven, hot plate, infrared, etc. can be used for drying.
- the drying temperature and the drying time may be in a range in which the organic solvent can be volatilized, and it is preferable to appropriately set a range in which the layer made of the adhesive composition of the adhesive film is in an uncured or semi-cured state. . Specifically, it is preferable to carry out from 1 minute to several tens of minutes in the range of 40 ° C to 120 ° C. Moreover, you may heat up in steps combining these temperatures, for example, you may heat-process at 50 degreeC, 60 degreeC, and 70 degreeC for 1 minute each.
- the elastic modulus at ⁇ 40 ° C. of the adhesive composition after curing is preferably 10 GPa or more and 15 GPa or less, more preferably 11 GPa or more and 14 GPa or less, and further preferably 11 GPa or more and 13 GPa or less.
- the elastic modulus at minus 40 ° C. here refers to a test piece having a size of 5 mm ⁇ 50 mm ⁇ 0.5 mm and dynamic viscoelasticity measurement at a frequency of 1 Hz, a heating rate of 5 ° C./min, and a measurement strain of 0.02%. It refers to the elastic modulus at minus 40 ° C. when performed.
- the maximum strength of the cured product of the adhesive composition of the present invention is preferably 28N or more.
- the maximum strength referred to here is parallel to the both sides of the 2 mm width at the position of 10 mm in the length direction from the both sides of the width 2 mm, that is, the center position on the 2 mm ⁇ 20 mm surface of the rectangular parallelepiped of 4 mm ⁇ 20 mm ⁇ 2 mm size.
- test piece in which a groove having a depth of 1.84 mm and a width of 300 ⁇ m was formed in the direction, and a crack was produced in the groove part, under conditions of a test speed of 166.6 ⁇ m / sec and a fulcrum height of 200 ⁇ m at 23 ° C.
- the substrate with the adhesive composition of the present invention is characterized by having a layer and a substrate made of the adhesive composition of the present invention.
- a resin coating agent is spin-coated using a spinner, screen printing, blade coater, die coater, calendar coater, meniscus coater, bar coater, roll coater, comma roll. It may be applied by a method such as coater, gravure coater, screen coater, slit die coater, etc., or the adhesive film prepared by coating on the support film is subjected to heat press treatment, heat lamination treatment, heat vacuum lamination treatment, etc. You may form by thermocompression bonding.
- the semiconductor device of the present invention has a layer made of the adhesive composition of the present invention.
- the adhesive composition, resin coating agent, and adhesive film of the present invention are used as a semiconductor adhesive or semiconductor coating agent for bonding, fixing or sealing a semiconductor element, circuit board, or metal wiring material, or reinforcing a wafer. It can be preferably used.
- the semiconductor device as used in the present invention refers to all devices that can function by utilizing the characteristics of semiconductor elements, and electro-optical devices, semiconductor circuits, and electronic devices are all included in the semiconductor devices.
- the method for manufacturing a semiconductor device using the adhesive composition of the present invention includes interposing the adhesive composition of the present invention between a first circuit member and a second circuit member, and heating and pressing the first circuit member and the second circuit member.
- the first circuit member having the first electrode and the second circuit member having the second electrode are arranged so that the first electrode and the second electrode face each other.
- the adhesive composition of the present invention is interposed between the first circuit member and the second circuit member that are arranged to face each other.
- the adhesive composition may be directly applied to the surface of the circuit member and then the volatile component may be removed, or the adhesive film of the present invention is bonded to the surface of the circuit member.
- the support film may be removed from.
- the adhesive composition may be formed on the electrode-side surface of only one of the circuit members, or may be formed on both electrode-side surfaces of the first and second circuit members.
- the first circuit member and the second circuit member are heated and pressed to bond the first circuit member and the second circuit member, and at the same time, the first electrode and the second electrode arranged to face each other are electrically connected.
- the electrical connection between the electrodes may be made by mechanical pressing, or may be made by metal bonding using solder or the like.
- the through electrode may be formed on the first circuit member and / or the second circuit member, and the electrode may be formed on one side and / or both sides of the circuit member.
- the gap between the semiconductor chip and the circuit board on which the wiring pattern is formed can be sealed with a cured product of the adhesive composition.
- the adhesive film is cut out to a predetermined size and bonded to the wiring pattern surface of the circuit board on which the wiring pattern is formed, and the support film is removed. Or, after cutting the semiconductor chip, the adhesive film is bonded to the bump forming surface of the semiconductor wafer and the support film is removed, and then the semiconductor wafer is diced into individual pieces, thereby removing the support film. A semiconductor chip to which is attached may be manufactured.
- the bonding of the adhesive film can be performed using a bonding apparatus such as a roll laminator or a vacuum laminator.
- the semiconductor chip After bonding the adhesive film to the circuit board or the semiconductor chip and removing the support film, the semiconductor chip is mounted on the circuit board with a bonding apparatus.
- the bonding conditions are not particularly limited as long as the electrical connection is satisfactorily obtained.
- the temperature is 100 ° C. or higher
- the pressure is 1 mN / bump or higher
- the time is 0. It is preferable to carry out under heating and pressurizing conditions for 1 second or more. More preferably, the temperature is 120 ° C. or more and 300 ° C. or less, more preferably 150 ° C. or more and 250 ° C.
- the bump on the semiconductor chip and the pad electrode on the circuit board are brought into contact with each other by heating and pressurizing at a temperature of 50 ° C. or higher, a pressure of 1 mN / bump or higher, and a time of 0.1 second or longer as temporary pressure bonding. It is also preferable to perform bonding under the above conditions. If necessary, after bonding, the circuit board with a semiconductor chip may be heated at a temperature of 50 ° C. to 200 ° C. for 10 seconds to 24 hours.
- the adhesive composition of the present invention can be suitably used as an adhesive composition for bonding, fixing or sealing circuit members constituting a semiconductor device. Moreover, it can be used for an insulating layer, a permanent resist, a solder resist, a sealant, etc., which constitute a circuit board such as a build-up multilayer board, and an etching resist used for manufacturing a semiconductor device.
- the circuit member means a member such as a semiconductor chip, a chip component, a circuit board, or a metal wiring material constituting the semiconductor device.
- circuit members include semiconductor chips on which bumps such as plating bumps and stud bumps are formed, chip components such as resistor chips and capacitor chips, semiconductor chips having TSV (through silicon via) electrodes, silicon interposers, and the like. Is mentioned.
- a semiconductor device in the present invention refers to all devices that can function by utilizing characteristics of a semiconductor element, and all semiconductor circuits and electronic devices are included in the semiconductor device.
- the adhesive composition of the present invention includes a die attach film, a dicing die attach film, a lead frame fixing tape, a heat sink, a reinforcing plate, an adhesive for a shield material, a solder resist, and the like. Can be used as a thing.
- Synthesis Example 1 Synthesis of Polyimide 4.82 g (0.0165 mol) of 1,3-bis (3-aminophenoxy) benzene, 3,3′-diamino-4,4′-dihydroxydiphenylsulfone in a dry nitrogen stream 08 g (0.011 mol), 4.97 g (0.02 mol) of bisaminopropyltetramethyldisiloxane, and 0.47 g (0.005 mol) of aniline as an end-capping agent were dissolved in 130 g of NMP.
- each example and comparative example are as follows.
- Epoxy curing agent 2PZ manufactured by Shikoku Chemicals Co., Ltd., imidazole curing agent
- Novacure HX-3941HP Aligni Kasei E-Materials Co., Ltd., aromatic polyamine curing agent
- E Organic solvent propylene glycol monomethyl ether acetate (hereinafter sometimes referred to as “PGMEA”) (manufactured by Tokyo Chemical Industry Co., Ltd.).
- T total grams of non-volatile organic components
- 5.83 + 9.32 + 17.48 + 0.67 M number of moles of epoxy group in nonvolatile organic component
- T / M (5.83 + 9.32 + 17.48 + 0.67)
- / (9.32 / 314 + 17.48 / 3770) 970
- Example 2 51.45 g of polyimide obtained in Synthesis Example 1, 65.17 g of YL980 (manufactured by Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq), and 51.61 g of jER1009 (manufactured by Mitsubishi Chemical Corporation, epoxy equivalent 2719 g / eq).
- Example 4 18.15 g of polyimide obtained in Synthesis Example 1, 8.82 g of YL980 (Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq), and 18.82 g of jER1010 (Mitsubishi Chemical Corporation, epoxy equivalent 3770 g / eq).
- Example 5 The resin coating agent 1 prepared in Example 1 was applied to a support film therapy HP2 (U) (made by Toray Film Processing Co., Ltd.) having a thickness of 75 ⁇ m using a bar coater and heated in an oven heated to 100 ° C. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was attached as a protective film to the coating surface to produce a laminate of the protective film and the adhesive film 1.
- the thickness of the layer obtained from the resin coating agent 1 in the adhesive film 1 was 30 ⁇ m.
- Example 6 Multipurpose under the condition that the resin coating agent 2 prepared in Example 2 is dried for 10 minutes in an oven heated to 100 ° C. on a support film therapy HP2 (U) having a thickness of 75 ⁇ m (manufactured by Toray Film Processing Co., Ltd.). Coating is performed using a coater (Inoue Metal Industry Co., Ltd.), and a protective film and adhesive film 2 laminate are manufactured by pasting SR3 (made by Ohtsuki Kogyo Co., Ltd.) with a thickness of 25 ⁇ m as a protective film on the coating surface. did. The thickness of the layer obtained from the resin coating agent 2 in the adhesive film 2 was 30 ⁇ m.
- Example 7 Multipurpose under the condition that the resin coating agent 3 prepared in Example 3 is dried for 10 minutes in an oven heated to 100 ° C. on a support film therapy HP2 (U) having a thickness of 75 ⁇ m (manufactured by Toray Film Processing Co., Ltd.). Coating is performed using a coater (Inoue Metal Industry Co., Ltd.), and a protective film and adhesive film 3 laminate are manufactured by pasting 25 ⁇ m thick SR3 (manufactured by Oiso Kogyo Co., Ltd.) as a protective film on the coating surface. did. The thickness of the layer obtained from the resin coating agent 3 in the adhesive film 3 was 30 ⁇ m.
- Example 8 The resin coating agent 4 prepared in Example 4 was applied to a support film therapy HP2 (U) (made by Toray Film Processing Co., Ltd.) having a thickness of 75 ⁇ m using a bar coater and heated in an oven heated to 100 ° C. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was pasted as a protective film on the coating surface to produce a laminate of the protective film and the adhesive film 4.
- the thickness of the layer obtained from the resin coating agent 4 in the adhesive film 4 was 30 ⁇ m.
- Example 9 A laminate of the protective film and the adhesive film 1 produced in Example 5 was cut into an 8 cm square size, and two were obtained by removing the protective film therefrom. Next, the layers obtained from the resin coating agent 1 were laminated so as to overlap each other, and a laminate of support film-layers obtained from the resin coating agent 1 (for two) -support film was obtained. Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.). The temperature of the upper and lower heating plates is 90 ° C., the vacuum time is 20 seconds, and the applied pressure is 0.3 MPa. The pressure time was 30 seconds.
- MVLP-500 / 600 manufactured by Meiki Seisakusho Co., Ltd.
- the support film on both sides of the laminate was peeled off, and a “Teflon (registered trademark)” film was attached on both sides instead.
- the obtained “Teflon (registered trademark)” film—the layer (thickness 2 mm) obtained from the resin coating agent 1—the “Teflon (registered trademark)” film laminate was first heated to 200 ° C. over 1 hour. Then, the layer (thickness 2 mm) obtained from the resin coating agent 1 was cured by leaving it at 200 ° C. for 2 hours.
- the produced cured product 1 was cut using a dicing apparatus DAD3350 (manufactured by DISCO Corporation) to produce a rectangular parallelepiped having a width of 2 mm, a length of 20 mm, and a height of 4 mm.
- a dicing device DAD3350 manufactured by Disco Corporation
- a groove having a thickness of 1.84 mm and a width of 300 ⁇ m was formed.
- the produced cured product 1A was cut using a dicing apparatus DAD3350 (manufactured by Disco Corporation) to produce a plate-shaped test piece 1A having a width of 5 mm, a length of 50 mm, and a height of 0.5 mm. It was 13 GPa when the elastic modulus in minus 40 degreeC was measured by said method about the obtained plate-shaped test piece 1A.
- Example 10 Except for changing the adhesive film 1 to the adhesive film 2, the cured product 2 is produced in the same manner as in Example 9, and the same method as in Example 9 except that the cured product 1 is changed to the cured product 2. The test piece 2 was produced. Next, when the maximum strength of the obtained test piece 2 was measured by the above method, the maximum strength was 30.0N.
- the cured product 2A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 2A, as in Example 9.
- the plate-shaped test piece 2A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured by the above method for the obtained plate-shaped test piece 2A, it was 11 GPa.
- Example 11 Except for changing the adhesive film 1 to the adhesive film 3, the cured product 3 is produced in the same manner as in Example 9, and the same method as in Example 9 except that the cured product 1 is changed to the cured product 3. The test piece 3 was produced. Next, when the maximum strength of the obtained test piece 3 was measured by the above method, the maximum strength was 33.0N.
- the cured product 3A is produced in the same manner as in the example 9, and the cured product 1A is changed to the cured product 3A.
- the plate-shaped test piece 3A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured for the obtained plate-shaped test piece 3A by the above method, it was 13 GPa.
- Example 12 Except for changing the adhesive film 1 to the adhesive film 4, a cured product 4 is prepared in the same manner as in Example 9, and the same method as in Example 9 is used except that the cured product 1 is changed to the cured product 4. Thus, a test piece 4 was prepared. Next, when the maximum strength of the obtained test piece 4 was measured by the above method, the maximum strength was 38.9N.
- the cured product 4A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 4A, as in Example 9.
- the plate-shaped test piece 4A was produced by the method. Next, when the elastic modulus at minus 40 ° C. was measured by the above method for the obtained plate-shaped test piece 4A, it was 13 GPa.
- T / M 275 g / mol.
- the viscosity at 1 rpm was measured with a viscometer RE105L (manufactured by Toki Sangyo Co., Ltd.), it was 280 cP.
- the viscosity at 1 rpm was measured and found to be 280 cP, indicating no change in viscosity.
- Comparative Example 4 jER1009 (Mitsubishi Chemical Corporation, epoxy equivalent 2719 g / eq) 10.96 g, N865 (DIC Corporation, epoxy equivalent 205 g / eq) 12.63 g, SE2050-KNK (manufactured by Admatechs) was added to a 250 mL plastic container, and the mixture was stirred at room temperature on a ball mill stand for 72 hours. Further, 12.81 g of a microcapsule type curing accelerator Novacure HX-3941HP (manufactured by Asahi Kasei E-Materials Co., Ltd.) was added, and the mixture was stirred at room temperature on a ball mill stand for 2 hours.
- a microcapsule type curing accelerator Novacure HX-3941HP manufactured by Asahi Kasei E-Materials Co., Ltd.
- the viscosity at 0.1 rpm was measured with a viscometer RE105L (manufactured by Toki Sangyo Co., Ltd.), it was 3200 cP. Further, after storing for 24 hours in a constant temperature and humidity chamber at a temperature of 25 ° C. and a humidity of 50%, the viscosity at 0.1 rpm was measured and found to be 4030 cP, indicating a significant increase in viscosity. Furthermore, after storing for 48 hours in a constant temperature and humidity chamber at a temperature of 25 ° C. and a humidity of 50%, the viscosity at 0.1 rpm was measured and found to be 5700 cP. Confirmed that there was a problem.
- Comparative Example 5 9.82 g of polyimide obtained in Synthesis Example 1, YL980 (Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq) 11.49 g, N865 (DIC Corporation, epoxy equivalent 205 g / eq) 11.32 g 2PZ (manufactured by Shikoku Kasei Kogyo Co., Ltd.) 0.67 g, SE2050-KNK (manufactured by Admatechs Co., Ltd.) 111.0 g and PGMEA 5.70 g were added to a 250 mL plastic container, and a ball mill frame was added at room temperature. Stir for 96 hours above.
- the obtained mixed solution is subjected to pressure filtration using a filter having a reserved particle diameter of 10 ⁇ m.
- About 100 parts by weight of the epoxy compound is about 43 parts by weight of polyimide, and about 2.
- the resin coating agent 9 (T / M 284 g / mol) which is 7 weight part was obtained.
- Comparative Example 6 4.66 g of the polyimide obtained in Synthesis Example 1, 6.66 g of YL980 (Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq), and 4.66 g of jER1009 (Mitsubishi Chemical Corporation, epoxy equivalent 2719 g / eq).
- Comparative Example 7 6.88 g of polyimide obtained in Synthesis Example 1, 5.88 g of YL980 (Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq), jER1010 (Mitsubishi Chemical Corporation, epoxy equivalent 3770 g / eq) 7.
- Comparative Example 8 The resin coating agent 5 prepared in Comparative Example 1 was coated on a support film therapy HP2 (U) (manufactured by Toray Film Processing Co., Ltd.) having a thickness of 75 ⁇ m using a bar coater and heated to 100 ° C. in an oven. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsuchi Kogyo Co., Ltd.) was pasted as a protective film on the coating surface to produce a laminate of the protective film and the adhesive film 5.
- the thickness of the layer obtained from the resin coating agent 5 in the adhesive film 5 was 30 ⁇ m.
- Comparative Example 9 The resin coating agent 6 prepared in Comparative Example 2 was applied to a support film therapy HP2 (U) having a thickness of 75 ⁇ m (manufactured by Toray Film Processing Co., Ltd.) using a bar coater and heated to 100 ° C. in an oven. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was attached as a protective film to the coating surface to produce a laminate of the protective film and the adhesive film 6.
- the thickness of the layer obtained from the resin coating agent 6 in the adhesive film 6 was 30 ⁇ m.
- Comparative Example 10 The resin coating agent 7 prepared in Comparative Example 3 was applied to a support film therapy HP2 (U) having a thickness of 75 ⁇ m using a bar coater and heated in an oven heated to 100 ° C. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was pasted as a protective film on the coating surface to produce a laminate of the protective film and the adhesive film 7.
- the thickness of the layer obtained from the resin coating agent 7 in the adhesive film 7 was 30 ⁇ m.
- Comparative Example 11 The resin coating agent 9 prepared in Comparative Example 5 was applied to a support film therapy HP2 (U) having a thickness of 75 ⁇ m (made by Toray Film Processing Co., Ltd.) using a bar coater, and heated in an oven heated to 100 ° C. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was attached as a protective film to the coating surface to produce a laminate of the protective film and the adhesive film 9.
- the thickness of the layer obtained from the resin coating agent 9 in the adhesive film 9 was 30 ⁇ m.
- Comparative Example 12 The resin coating agent 10 prepared in Comparative Example 6 was applied to a support film therapy HP2 (U) (made by Toray Film Processing Co., Ltd.) having a thickness of 75 ⁇ m using a bar coater and heated in an oven heated to 100 ° C. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Otsugi Kogyo Co., Ltd.) was attached as a protective film to the coating surface to produce a laminate of the protective film and the adhesive film 10.
- the thickness of the layer obtained from the resin coating agent 10 in the adhesive film 10 was 30 ⁇ m.
- Comparative Example 13 The resin coating agent 11 prepared in Comparative Example 7 was applied to a support film therapy HP2 (U) having a thickness of 75 ⁇ m using a bar coater and heated to 100 ° C. in an oven. Dry for 10 minutes.
- SR3 having a thickness of 25 ⁇ m (manufactured by Daegyo Kogyo Co., Ltd.) was attached as a protective film to the coating surface to produce a laminate of the protective film and the adhesive film 11.
- the thickness of the layer obtained from the resin coating agent 11 in the adhesive film 11 was 30 ⁇ m.
- Comparative Example 14 Except for changing the adhesive film 1 to the adhesive film 5, the cured product 5 is produced in the same manner as in Example 9 and the cured product 1 is changed to the cured product 5 in the same manner as in Example 9 A test piece 5 was prepared. Next, when the maximum strength of the obtained test piece 5 was measured by the above method, the maximum strength was 15.1N.
- the cured product 5A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 5A, as in Example 9.
- the plate-shaped test piece 5A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured for the obtained plate-like test piece 5A by the above method, it was 13 GPa.
- Comparative Example 15 Except for changing the adhesive film 1 to the adhesive film 6, the cured product 6 is produced in the same manner as in Example 9, and the cured product 1 is changed to the cured product 6 in the same manner as in Example 9. Thus, a test piece 6 was produced. Next, when the maximum strength of the obtained test piece 6 was measured by the above method, the maximum strength was 14.4N.
- the cured product 6A is produced in the same manner as in the example 9, and the cured product 1A is changed to the cured product 6A.
- the plate-shaped test piece 6A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured by the above method for the obtained plate-shaped test piece 6A, it was 13 GPa.
- Comparative Example 16 Except for changing the adhesive film 1 to the adhesive film 7, the cured product 7 is produced in the same manner as in Example 9 and the cured product 1 is changed to the cured product 7 in the same manner as in Example 9. A test piece 7 was prepared. Next, when the maximum strength of the obtained test piece 7 was measured by the above method, the maximum strength was 13.9N.
- the cured product 7A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 7A, as in Example 9.
- the plate-shaped test piece 7A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured for the obtained plate-shaped test piece 7A by the above method, it was 13 GPa.
- Comparative Example 17 Except for changing the adhesive film 1 to the adhesive film 9, the cured product 9 is produced in the same manner as in Example 9, and the same method as in Example 9 except that the cured product 1 is changed to the cured product 9. Thus, a test piece 9 was produced. Next, when the maximum strength of the obtained test piece 9 was measured by the above method, the maximum strength was 15.4N.
- the cured product 9A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 9A, as in Example 9.
- the plate-shaped test piece 9A was produced by the method described above. Next, when the elastic modulus at minus 40 ° C. was measured for the obtained plate-shaped test piece 9A by the above method, it was 13 GPa.
- Comparative Example 18 Except for changing the adhesive film 1 to the adhesive film 10, the cured product 10 is prepared in the same manner as in Example 9, and the cured product 1 is changed to the cured product 10 in the same manner as in Example 9. The test piece 10 was produced. Next, when the maximum strength of the obtained test piece 10 was measured by the above method, the maximum strength was 19.6N.
- the cured product 10A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 10A, as in Example 9.
- the plate-shaped test piece 10A was produced by the method. Next, when the elastic modulus at minus 40 ° C. was measured by the above method for the obtained plate-shaped test piece 10A, it was 13 GPa.
- Comparative Example 19 Except for changing the adhesive film 1 to the adhesive film 11, a cured product 11 is prepared in the same manner as in Example 9, and the cured product 1 is changed to the cured product 11 in the same manner as in Example 9. Thus, a test piece 11 was produced. Next, when the maximum strength of the obtained test piece 11 was measured by the above method, the maximum strength was 18.0 N.
- the cured product 11A is produced in the same manner as in Example 9, and the cured product 1A is changed to the cured product 11A, as in Example 9.
- the plate-shaped test piece 11A was produced by the method. Next, when the elastic modulus at minus 40 ° C. was measured for the obtained plate-shaped test piece 11A by the above method, it was 13 GPa.
- Example 13 15.78 g of the polyimide obtained in Synthesis Example 1, 15.12 g of YL980 (Mitsubishi Chemical Corporation, epoxy equivalent 185 g / eq), 15 NC of NC3000H (Nippon Kayaku Co., Ltd., epoxy equivalent 287 g / eq) 15 .12 g, jER1009 (Mitsubishi Chemical Corporation, epoxy equivalent 2719 g / eq) 28.73 g, jER1010 (Mitsubishi Chemical Corporation, epoxy equivalent 3770 g / eq) 11.34 g, 2PZ (Shikoku Chemicals Co., Ltd.) )), 1.520 g of SE2050-ENA (manufactured by Admatechs) and 22.40 g of carbitol were added to a 500 mL plastic container, and the mixture was stirred at room temperature on a ball mill stand for 96 hours. Then, pressure filtration of the obtained liquid mixture was performed using the filter with a reservation particle diameter of 10 micro
- Example 15 Multipurpose under the condition that the resin coating agent 1B prepared in Example 13 is dried for 10 minutes in an oven heated to 100 ° C. on a support film therapy HP2 (U) having a thickness of 75 ⁇ m (manufactured by Toray Film Processing Co., Ltd.). Coating is performed using a coater (Inoue Metal Industry Co., Ltd.), and a protective film and an adhesive film 1B are manufactured by pasting SR3 (manufactured by Oiso Kogyo Co., Ltd.) with a thickness of 25 ⁇ m as a protective film on the coating surface. did. The thickness of the layer obtained from the resin coating agent 1B in the adhesive film 1B was 30 ⁇ m.
- Example 16 Multipurpose under the condition that the resin coating agent 2B prepared in Example 14 is dried for 10 minutes in an oven heated to 100 ° C. on a support film therapy HP2 (U) having a thickness of 75 ⁇ m (manufactured by Toray Film Processing Co., Ltd.). Coating is performed using a coater (Inoue Metal Industry Co., Ltd.), and a protective film and adhesive film 2B laminate are manufactured by attaching SR3 (made by Otsuchi Industry Co., Ltd.) with a thickness of 25 ⁇ m as a protective film to the coating surface. did. The thickness of the layer obtained from the resin coating agent 2B in the adhesive film 2B was 30 ⁇ m.
- Example 17 Except for changing the adhesive film 1 to the adhesive film 1B, a cured product 1B is produced in the same manner as in Example 9, and the cured product 1 is changed to the cured product 1B in the same manner as in Example 9. Thus, a test piece 1B was produced. Next, when the maximum strength of the obtained test piece 1B was measured by the above method, the maximum strength was 34.3N.
- the cured product 1B is produced in the same manner as in the example 9, and the cured product 1A is changed to the cured product 1B.
- the plate-shaped test piece 1B was produced by the method. Next, it was 13 GPa when the elasticity modulus in minus 40 degreeC was measured with said method about the obtained plate-shaped test piece 1B.
- Example 18 Except for changing the adhesive film 1 to the adhesive film 2B, a cured product 2B is produced in the same manner as in Example 9, and the same method as in Example 9 except that the cured product 1 is changed to the cured product 2B. Thus, a test piece 2B was produced. Next, when the maximum strength of the obtained test piece 2B was measured by the above method, the maximum strength was 29.0N.
- the cured product 2B is produced in the same manner as in the example 9, and the cured product 1A is changed to the cured product 2B.
- the plate-shaped test piece 2B was produced by the method of. Next, when the elastic modulus at minus 40 ° C. was measured by the above method for the obtained plate-shaped test piece 2B, it was 13 GPa.
- Example 19 The resin coating agent 2 prepared in Example 2 was applied to a 12-inch wafer using a slit coater, and the substrate was dried on a hot plate at 80 ° C. for 10 minutes.
- the film thickness at a point of 5 cm, 10 cm, 15 cm, 20 cm, and 25 cm from the coating start edge on a straight line in the same direction as the coating direction and passing through the center of the 300 mm wafer was 36 ⁇ 1 ⁇ m. It was confirmed that a coating film excellent in in-plane uniformity could be formed.
- the obtained substrate was baked in an oven set at 200 ° C. for 15 minutes to form a cured film on the wafer. It was visually confirmed that there was no peeling between the wafer and the cured film.
- Example 20 The resin coating agent 4 prepared in Example 4 was applied to a 12-inch wafer using a slit coater, and the substrate was dried on a hot plate at 80 ° C. for 10 minutes. On the straight line in the same direction as the coating direction and on the straight line passing through the center of the 300 mm wafer, the film thickness at a point of 5 cm, 10 cm, 15 cm, 20 cm, and 25 cm from the coating start edge was measured, and the thickness was 25 ⁇ 1 ⁇ m. It was confirmed that a coating film excellent in in-plane uniformity could be formed. The obtained substrate was baked in an oven set at 200 ° C. for 15 minutes to form a cured film on the wafer. It was visually confirmed that there was no peeling between the wafer and the cured film.
- Example 21 The resin coating agent 2 prepared in Example 2 was applied to a 12-inch wafer having a diameter of 70 ⁇ m and copper pillars (height 20 ⁇ m) arranged at a pitch of 100 ⁇ m using a slit coater, and the substrate was hot-plated. And dried at 80 ° C. for 10 minutes. It was confirmed that the film thickness of the part without the copper pillar was 41 ⁇ m, and the step between the part with the copper pillar and the part without the copper pillar was less than 1 ⁇ m. The obtained substrate was baked in an oven set at 200 ° C. for 15 minutes to form a cured film on the wafer. It was visually confirmed that there was no peeling between the wafer and the cured film.
- Example 22 What prepared by peeling off the protective film from the laminated body of the protective film manufactured in Example 6 and the adhesive film 2 was prepared, and the layer obtained from the resin coating agent 2 prepared in Example 2 and a 1 cm ⁇ 1 cm size Chips (chips having a silicon wafer thickness of 625 ⁇ m, a diameter of 25 ⁇ m and a copper pillar (height of 25 ⁇ m) arranged at a pitch of 50 ⁇ m) were laminated so that the copper pillar formation surfaces overlapped to produce a substrate laminate 1. Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.).
- the temperature of the upper and lower heating plates is 90 ° C., the vacuum time is 20 seconds, and the applied pressure is 0.3 MPa. The pressure time was 30 seconds.
- the thing which peeled off the protective film from the laminated body of the protective film manufactured in Example 6, and the adhesive film 2, and the layer obtained from the resin coating agent 2 prepared in Example 2, and 15 mm x 15 mm Laminated glass epoxy substrates (thickness 10 mm) were laminated so that a substrate laminate 2 was produced. Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.).
- the temperature of the upper and lower heating plates is 90 ° C., the vacuum time is 20 seconds, and the applied pressure is 0.3 MPa.
- the pressure time was 30 seconds.
- the substrate laminate 3 was produced.
- Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.).
- the temperature of the upper and lower heating plates is 90 ° C.
- the vacuum time is 20 seconds
- the applied pressure is 0.3 MPa.
- the pressure time was 30 seconds.
- substrate laminated body 3 was heated at 180 degreeC for 1 hour, and the board
- the obtained substrate laminate 4 was left in a constant temperature and humidity chamber (Enomoto Kasei Co., Ltd., FX214P) having a temperature of 85 ° C. and a humidity of 85% for 168 hours to obtain a substrate laminate 5.
- the process of allowing the obtained substrate laminate 5 to stand at a temperature of ⁇ 55 ° C. for 30 minutes and at a temperature of 125 ° C. for 30 minutes in a thermal shock apparatus (manufactured by ESPEC Corp., TSE-11-A) is repeated 1000 times.
- a substrate laminate 6 was obtained.
- the cross section of the substrate laminate 6 is observed with a scanning electron microscope (JSM-6510A, manufactured by JEOL Ltd.), and there is no gap between the layer obtained from the resin coating agent 2 and the silicon wafer portion of the chip. It was confirmed. Moreover, it confirmed that there was no clearance gap between the layer obtained from the resin coating agent 2, and a copper pillar part.
- Example 23 What prepared by peeling off the protective film from the laminated body of the protective film manufactured in Example 6 and the adhesive film 2 was prepared, and the layer obtained from the resin coating agent 2 prepared in Example 2 was 1 cm ⁇ 1 cm in size. It laminated
- Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.).
- the temperature of the upper and lower heating plates is 90 ° C.
- the vacuum time is 20 seconds
- the applied pressure is 0.3 MPa.
- the pressure time was 30 seconds.
- the substrate laminate 9 was produced.
- Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.).
- the temperature of the upper and lower heating plates is 90 ° C.
- the vacuum time is 20 seconds
- the applied pressure is 0.3 MPa.
- the pressure time was 30 seconds.
- the obtained substrate laminate 9 was heated at 180 ° C. for 1 hour to produce a substrate laminate 10.
- the process of allowing the obtained substrate laminate 10 to stand at a temperature of ⁇ 55 ° C. for 30 minutes and at a temperature of 125 ° C. for 30 minutes with a thermal shock apparatus (manufactured by Espec Corp., TSE-11-A) is repeated 1000 times. It was visually confirmed that the copper plate was adhered.
- Example 24 Prepared by removing the protective film from the laminate of the protective film and adhesive film 2 produced by the same method as in Example 6 (the thickness of the layer obtained from the resin coating agent 2 is 50 ⁇ m), and obtained from the resin coating agent 2
- the laminated layer was laminated so that the copper pillar bump forming surface of the TEG chip with a copper pillar bump (WALTS-TEG CC80-0101JY (SiN) _ModelI, manufactured by Waltz Co., Ltd.) was overlapped to produce a substrate laminate 11.
- Lamination is performed using a vacuum laminator MVLP-500 / 600 (manufactured by Meiki Seisakusho Co., Ltd.). The pressure time was 30 seconds.
- a support film was peeled and the evaluation chip
- the substrate to be attached manufactured by Waltz Co., Ltd., WALTS-KIT CC80-0103JY [MAP] _ModelI (Cu + OSP specification)
- Flip chip bonding was performed to obtain a semiconductor device.
- Flip chip bonding conditions are as follows: a substrate is placed on a bonding stage heated to 140 ° C., pre-bonded under conditions of a temperature of 140 ° C., a pressure of 150 N / chip, and a time of 1 second, and then a temperature of 250 ° C.
- composition of the resin coating agent is shown in Table 1, and the maximum strength and the elastic modulus at minus 40 ° C. are summarized in Table 2.
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Abstract
Description
検出器:Waters996
システムコントローラー:Waters2690
カラムオーブン:Waters HTR-B
サーモコントローラー:Waters TCM
カラム:TOSOH (TSK-GEL Guard Column)
カラム:TOSOH TSK-GEL α-4000
カラム:TOSOH TSK-GEL α-2500などが挙げられる。
中心距離が16mmになるように治具SHR-250-CAP-05-3(デイジ(株)製)を固定し、ダイシェア試験機DAGE-SERIES-4000PXY(デイジ(株)製)を用いて、各実施例・比較例で得られた試験片の溝の反対部分から三点曲げ試験を行った。ダイシェア試験は、DS100制御版を用い、23℃下、試験速度166.6μm/秒、支点高さ200μmにて行った。
5mm×50mm×0.5mmサイズの試験片を、動的粘弾性装置DVA-200(アイティー計測制御(株)製)を用いて、周波数1Hz、昇温速度5℃/分、測定ひずみ0.02%にて動的粘弾性測定を行い、マイナス40℃における弾性率(GPa)を測定した。
乾燥窒素気流下、1,3-ビス(3-アミノフェノキシ)ベンゼン4.82g(0.0165モル)、3,3’-ジアミノ-4,4’-ジヒドロキシジフェニルスルホン3.08g(0.011モル)、ビスアミノプロピルテトラメチルジシロキサン4.97g(0.02モル)、末端封止剤としてアニリン0.47g(0.005モル)をNMP130gに溶解した。ここに2,2-ビス{4-(3,4-ジカルボキシフェノキシ)フェニル}プロパン二無水物26.02g(0.05モル)をNMP20gとともに加えて、25℃で1時間反応させ、次いで50℃で4時間撹拌した。その後、180℃で5時間撹拌した。撹拌終了後、溶液を水3Lに投入し、ろ過して沈殿を回収し、水で3回洗浄した後、真空乾燥機を用いて80℃20時間乾燥した。得られたポリマー固体の赤外吸収スペクトルを測定したところ、1780cm-1付近、1377cm-1付近にポリイミドに起因するイミド構造の吸収ピークが検出された。このようにしてエポキシ基と反応可能な官能基を有し、一般式(1)で表される構造が11.6重量%含まれるポリイミドを得た。4gのポリイミドにテトラヒドロフラン6gを加え、23℃で撹拌したところ溶解した。
(B)多官能エポキシ化合物
エポトートPG-207GS(新日鐵化学(株)製)、エポキシ当量314g/eq、液状エポキシ化合物
jER1010(三菱化学(株)製)、エポキシ当量3770g/eq
YL980(三菱化学(株)製)、エポキシ当量185g/eq、液状エポキシ化合物
jER1009(三菱化学(株)製)、エポキシ当量2719g/eq
N865(DIC(株)製)、エポキシ当量205g/eq
NC3000H(日本化薬(株)製)、エポキシ当量287g/eq。
(C)エポキシ硬化剤
2PZ(四国化成工業(株)製、イミダゾール系硬化剤)
ノバキュアHX-3941HP(旭化成イーマテリアルズ(株)製、芳香族ポリアミン系硬化剤)。
(D)無機粒子
SE2050-KNK((株)アドマテックス製)、フェニルアミノ基含有シランカップリング剤にて処理したシリカ、メチルイソブチルケトン溶媒分散品、固形分濃度70.0重量%、シリカの平均粒子径0.57μm)
SE2050-ENA((株)アドマテックス製)、フェニルアミノ基含有シランカップリング剤にて処理したシリカ、カルビトール溶媒分散品、固形分濃度70.0重量%、シリカの平均粒子径0.6μm)。
(E)有機溶剤
プロピレングリコールモノメチルエーテルアセテート(以下、「PGMEA」という場合がある)(東京化成工業(株)製)。
合成例1で得られたポリイミド5.83g、エポトートPG-207GS(新日鐵化学(株)製、エポキシ当量314g/eq)を9.32g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を17.48g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.0g、プロピレングリコールモノメチルエーテルアセテートを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤1(T/M=970g/mol)を得た。
T(不揮発性有機成分の総グラム数)=5.83+9.32+17.48+0.67
M(不揮発性有機成分中のエポキシ基のモル数)=9.32/314+17.48/3770
T/M=(5.83+9.32+17.48+0.67)/(9.32/314+17.48/3770)=970
実施例2
合成例1で得られたポリイミド51.45g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を65.17g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を51.45g、2PZ(四国化成工業(株)製)を3.43g、SE2050-KNK((株)アドマテックス製)を455.0g、PGMEAを73.50gを2Lポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤2(T/M=462g/mol)を得た。粘度計RE105L(東機産業(株)製)にて0.1rpmでの粘度を測定したところ、2600cPであった。また、温度25℃、湿度50%の恒温恒湿器にて24時間保管した後に、0.1rpmでの粘度を測定したところ、2800cPであり、室温での保存安定性に優れることを確認した。
合成例1で得られたポリイミド44.10g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を55.86g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を44.10g、2PZ(四国化成工業(株)製)を2.94g、SE2050-KNK((株)アドマテックス製)を490.0g、PGMEAを63.00gを2Lポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤3(T/M=462g/mol)を得た。
合成例1で得られたポリイミド3.15g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を8.82g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を18.90g、2PZ(四国化成工業(株)製)を0.63g、SE2050-KNK((株)アドマテックス製)を105.0g、PGMEAを13.50gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤4(T/M=598g/mol)を得た。
実施例1で調製した樹脂コーティング剤1を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム1の積層体を製造した。接着フィルム1における樹脂コーティング剤1より得られた層の厚みは30μmであった。
実施例2で調製した樹脂コーティング剤2を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)に、100℃に加熱したオーブンにて10分間乾燥させる条件にて多目的コーター(井上金属工業(株))を用いて塗工し、塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム2の積層体を製造した。接着フィルム2における樹脂コーティング剤2より得られた層の厚みは30μmであった。
実施例3で調製した樹脂コーティング剤3を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)に、100℃に加熱したオーブンにて10分間乾燥させる条件にて多目的コーター(井上金属工業(株))を用いて塗工し、塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム3の積層体を製造した。接着フィルム3における樹脂コーティング剤3より得られた層の厚みは30μmであった。
実施例4で調製した樹脂コーティング剤4を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム4の積層体を製造した。接着フィルム4における樹脂コーティング剤4より得られた層の厚みは30μmであった。
実施例5にて製造した保護フィルムと接着フィルム1の積層体を8cm角サイズに切断し、これから保護フィルムを剥がしたものを2つ作製した。次に樹脂コーティング剤1より得られた層同士が重なるように積層し、支持フィルム-樹脂コーティング剤1より得られた層(2つ分)-支持フィルムの積層体を得た。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。
接着フィルム1を接着フィルム2に変更する以外は、実施例9と同様の方法にて、硬化物2を作製し、硬化物1を硬化物2に変更する以外は、実施例9と同様の方法にて、試験片2を作製した。次に、得られた試験片2について上記の方法で最大強度を測定したところ、最大強度は30.0Nであった。
接着フィルム1を接着フィルム3に変更する以外は、実施例9と同様の方法にて、硬化物3を作製し、硬化物1を硬化物3に変更する以外は、実施例9と同様の方法にて、試験片3を作製した。次に、得られた試験片3について上記の方法で最大強度を測定したところ、最大強度は33.0Nであった。
接着フィルム1を接着フィルム4に変更する以外は、実施例9と同様の方法にて、硬化物4を作製し、硬化物1を硬化物4に変更する以外は、実施例9と同様の方法にて、試験片4を作製した。次に、得られた試験片4について上記の方法で最大強度を測定したところ、最大強度は38.9Nであった。
YL980(三菱化学(株)製、エポキシ当量185g/eq)を11.49g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を9.82g、N865(DIC(株)製、エポキシ当量205g/eq)を11.32g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.0g、PGMEAを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤5(T/M=275g/mol)を得た。粘度計RE105L(東機産業(株)製)にて1rpmでの粘度を測定したところ、280cPであった。また、温度25℃、湿度50%の恒温恒湿器にて24時間保管した後に、1rpmでの粘度を測定したところ、280cPであり、粘度の変化は見られなかった。さらに温度25℃、湿度50%の恒温恒湿器にて120時間保管した後に、1rpmでの粘度を測定したところ、280cPであり、粘度の変化はほとんど見られず、室温での保存安定性に優れることを確認した。
合成例1で得られたポリイミドを0.98g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を11.49g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を8.84g、N865(DIC(株)製、エポキシ当量205g/eq)を11.32g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.00g、PGMEAを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤6(T/M=276g/mol)を得た。
YL980(三菱化学(株)製、エポキシ当量185g/eq)を11.49g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を9.82g、N865(DIC(株)製、エポキシ当量205g/eq)を11.32g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.00g、PGMEAを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤7(T/M=278g/mol)を得た。
jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を10.96g、N865(DIC(株)製、エポキシ当量205g/eq)を12.63g、SE2050-KNK((株)アドマテックス製)を78.00g、PGMEAを15.60gを250mLポリ容器に添加し、室温下、ボールミル架台上で72時間攪拌した。さらにマイクロカプセル型硬化促進剤ノバキュアHX-3941HP(旭化成イーマテリアルズ(株)製)を12.81g加え、室温下、ボールミル架台上で2時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤8を得た。粘度計RE105L(東機産業(株)製)にて0.1rpmでの粘度を測定したところ、3200cPであった。また、温度25℃、湿度50%の恒温恒湿器にて24時間保管した後に、0.1rpmでの粘度を測定したところ、4030cPであり、粘度の大幅な上昇が見られた。さらに温度25℃、湿度50%の恒温恒湿器にて48時間保管した後に、0.1rpmでの粘度を測定したところ、5700cPであり、粘度が上昇しているために室温での保存安定性に問題があることを確認した。
合成例1で得られたポリイミド9.82g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を11.49g、N865(DIC(株)製、エポキシ当量205g/eq)を11.32g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.0g、PGMEAを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、エポキシ化合物100重量部に対して、ポリイミドが約43重量部であり、かつエポキシ硬化剤が約2.7重量部である樹脂コーティング剤9(T/M=284g/mol)を得た。
合成例1で得られたポリイミド4.91g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を6.66g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を4.91g、NC3000H(日本化薬(株)製、エポキシ当量287g/eq)を16.15g、2PZ(四国化成工業(株)製)を0.67g、SE2050-KNK((株)アドマテックス製)を111.0g、PGMEAを5.70gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤10(T/M=354g/mol)を得た。
合成例1で得られたポリイミド0.88g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を5.88g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を7.79g、NC3000H(日本化薬(株)製、エポキシ当量287g/eq)を14.26g、2PZ(四国化成工業(株)製)を0.59g、SE2050-KNK((株)アドマテックス製)を98.00g、PGMEAを12.60gを250mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤11(T/M=352g/mol)を得た。
比較例1で調製した樹脂コーティング剤5を、厚み75μmの支持フィルムのセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム5の積層体を製造した。接着フィルム5における樹脂コーティング剤5より得られた層の厚みは30μmであった。
比較例2で調製した樹脂コーティング剤6を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム6の積層体を製造した。接着フィルム6における樹脂コーティング剤6より得られた層の厚みは30μmであった。
比較例3で調製した樹脂コーティング剤7を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム7の積層体を製造した。接着フィルム7における樹脂コーティング剤7より得られた層の厚みは30μmであった。
比較例5で調製した樹脂コーティング剤9を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム9の積層体を製造した。接着フィルム9における樹脂コーティング剤9より得られた層の厚みは30μmであった。
比較例6で調製した樹脂コーティング剤10を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム10の積層体を製造した。接着フィルム10における樹脂コーティング剤10より得られた層の厚みは30μmであった。
比較例7で調製した樹脂コーティング剤11を、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)にバーコーターを用いて塗工し、100℃に加熱したオーブンにて10分間乾燥させた。塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム11の積層体を製造した。接着フィルム11における樹脂コーティング剤11より得られた層の厚みは30μmであった。
接着フィルム1を接着フィルム5に変更する以外は、実施例9と同様の方法にて、硬化物5を作製し、硬化物1を硬化物5に変更する以外は、実施例9と同様の方法にて、試験片5を作製した。次に、得られた試験片5について上記の方法で最大強度を測定したところ、最大強度は15.1Nであった。
接着フィルム1を接着フィルム6に変更する以外は、実施例9と同様の方法にて、硬化物6を作製し、硬化物1を硬化物6に変更する以外は、実施例9と同様の方法にて、試験片6を作製した。次に、得られた試験片6について上記の方法で最大強度を測定したところ、最大強度は14.4Nであった。
接着フィルム1を接着フィルム7に変更する以外は、実施例9と同様の方法にて、硬化物7を作製し、硬化物1を硬化物7に変更する以外は、実施例9と同様の方法にて、試験片7を作製した。次に、得られた試験片7について上記の方法で最大強度を測定したところ、最大強度は13.9Nであった。
接着フィルム1を接着フィルム9に変更する以外は、実施例9と同様の方法にて、硬化物9を作製し、硬化物1を硬化物9に変更する以外は、実施例9と同様の方法にて、試験片9を作製した。次に、得られた試験片9について上記の方法で最大強度を測定したところ、最大強度は15.4Nであった。
接着フィルム1を接着フィルム10に変更する以外は、実施例9と同様の方法にて、硬化物10を作製し、硬化物1を硬化物10に変更する以外は、実施例9と同様の方法にて、試験片10を作製した。次に、得られた試験片10について上記の方法で最大強度を測定したところ、最大強度は19.6Nであった。
接着フィルム1を接着フィルム11に変更する以外は、実施例9と同様の方法にて、硬化物11を作製し、硬化物1を硬化物11に変更する以外は、実施例9と同様の方法にて、試験片11を作製した。次に、得られた試験片11について上記の方法で最大強度を測定したところ、最大強度は18.0Nであった。
合成例1で得られたポリイミド3.78g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を15.12g、NC3000H(日本化薬(株)製、エポキシ当量287g/eq)を15.12g、jER1009(三菱化学(株)製、エポキシ当量2719g/eq)を28.73g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を11.34g、2PZ(四国化成工業(株)製)を1.51g、SE2050-ENA((株)アドマテックス製)を252.0g、カルビトールを22.40gを500mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤1B(T/M=511g/mol)を得た。
合成例1で得られたポリイミド8.64g、YL980(三菱化学(株)製、エポキシ当量185g/eq)を16.85g、jER1010(三菱化学(株)製、エポキシ当量3770g/eq)を17.28g、2PZ(四国化成工業(株)製)を0.43g、SE2050-ENA((株)アドマテックス製)を144.0g、カルビトールを12.80gを500mLポリ容器に添加し、室温下、ボールミル架台上で96時間攪拌した。その後、保留粒子径10μmのフィルターを用いて、得られた混合液の加圧ろ過を行い、樹脂コーティング剤2B(T/M=452g/mol)を得た。
実施例13で調製した樹脂コーティング剤1Bを、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)に、100℃に加熱したオーブンにて10分間乾燥させる条件にて多目的コーター(井上金属工業(株))を用いて塗工し、塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム1Bの積層体を製造した。接着フィルム1Bにおける樹脂コーティング剤1Bより得られた層の厚みは30μmであった。
実施例14で調製した樹脂コーティング剤2Bを、厚み75μmの支持フィルムセラピールHP2(U)(東レフィルム加工(株)製)に、100℃に加熱したオーブンにて10分間乾燥させる条件にて多目的コーター(井上金属工業(株))を用いて塗工し、塗膜面に保護フィルムとして厚み25μmのSR3(大槻工業(株)製)を貼り付け、保護フィルムと接着フィルム2Bの積層体を製造した。接着フィルム2Bにおける樹脂コーティング剤2Bより得られた層の厚みは30μmであった。
接着フィルム1を接着フィルム1Bに変更する以外は、実施例9と同様の方法にて、硬化物1Bを作製し、硬化物1を硬化物1Bに変更する以外は、実施例9と同様の方法にて、試験片1Bを作製した。次に、得られた試験片1Bについて上記の方法で最大強度を測定したところ、最大強度は34.3Nであった。
接着フィルム1を接着フィルム2Bに変更する以外は、実施例9と同様の方法にて、硬化物2Bを作製し、硬化物1を硬化物2Bに変更する以外は、実施例9と同様の方法にて、試験片2Bを作製した。次に、得られた試験片2Bについて上記の方法で最大強度を測定したところ、最大強度は29.0Nであった。
実施例2にて調製した樹脂コーティング剤2を、スリットコーターを用いて12インチウェハに塗工し、基板をホットプレートにて80℃で10分乾燥させた。塗工方向と同方向の直線上かつ300mmウェハの中心を通る直線上で、塗工始端から5cm、10cm、15cm、20cm、25cmの地点の膜厚を測定したところ、厚さ36±1μmであり、面内均一性に優れた塗膜を形成できたことを確認した。得られた基板を200℃に設定したオーブンにて15分間焼成し、ウェハ上に硬化膜を形成した。ウェハと硬化膜の間に剥がれがないことを目視にて確認した。
実施例4にて調製した樹脂コーティング剤4を、スリットコーターを用いて12インチウェハに塗工し、基板をホットプレートにて80℃で10分乾燥させた。塗工方向と同方向の直線上かつ300mmウェハの中心を通る直線上で、塗工始端から5cm、10cm、15cm、20cm、25cmの地点の膜厚を測定したところ、厚さ25±1μmであり、面内均一性に優れた塗膜を形成できたことを確認した。得られた基板を200℃に設定したオーブンにて15分間焼成し、ウェハ上に硬化膜を形成した。ウェハと硬化膜の間に剥がれがないことを目視にて確認した。
実施例2にて調製した樹脂コーティング剤2を、直径70μmで100μmピッチにて銅ピラー(高さ20μm)が配置されている12インチウェハに、スリットコーターを用いて塗工し、基板をホットプレートにて80℃で10分乾燥させた。銅ピラーのない部分の膜厚が41μmで、銅ピラーのある部分と銅ピラーのない部分の段差が1μm未満であることを確認した。得られた基板を200℃に設定したオーブンにて15分間焼成し、ウェハ上に硬化膜を形成した。ウェハと硬化膜の間に剥がれがないことを目視にて確認した。
実施例6にて製造した保護フィルムと接着フィルム2の積層体から保護フィルムを剥がしたものを準備し、実施例2にて調製した樹脂コーティング剤2より得られた層と、1cm×1cmサイズのチップ(シリコンウェハの厚みが625μmで、直径25μmで50μmピッチにて銅ピラー(高さ25μm)が配置されたチップ)の銅ピラー形成面が重なるように積層し、基板積層体1を作製した。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。次に、実施例6にて製造した保護フィルムと接着フィルム2の積層体から保護フィルムを剥がしたものを準備し、実施例2にて調製した樹脂コーティング剤2より得られた層と15mm×15mmサイズのガラスエポキシ基板(厚さ10mm)が重なるように積層し、基板積層体2を作製した。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。
実施例23
実施例6にて製造した保護フィルムと接着フィルム2の積層体から保護フィルムを剥がしたものを準備し、実施例2にて調製した樹脂コーティング剤2より得られた層を、1cm×1cmサイズの銅板(厚さ15mm)に積層し、基板積層体7を作製した。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。次に、実施例6にて製造した保護フィルムと接着フィルム2の積層体から保護フィルムを剥がしたものを準備し、実施例2にて調製した樹脂コーティング剤2より得られた層と15mm×15mmサイズのガラスエポキシ基板(厚さ10mm)が重なるように積層し、基板積層体8を作製した。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。
実施例6と同様の方法により製造した保護フィルムと接着フィルム2の積層体(樹脂コーティング剤2より得られた層の厚み50μm)から保護フィルムを剥がしたものを準備し、樹脂コーティング剤2から得られた層と、銅ピラーバンプ付きTEGチップ((株)ウォルツ製、WALTS-TEG CC80-0101JY(SiN)_ModelI)の銅ピラーバンプ形成面が重なるように積層し、基板積層体11を作製した。積層は真空ラミネート装置MVLP-500/600((株)名機製作所製)を用いて、上熱盤と下熱盤の温度を90℃、真空時間を20秒、加圧力を0.3MPa、加圧時間を30秒として行った。そして、支持フィルムを剥離し、接着組成物付きの評価チップを作製した。その後、フリップチップボンディング装置(東レエンジニアリング(株)製、FC-3000WS)にて、被着体となる基板((株)ウォルツ製、WALTS-KIT CC80-0103JY[MAP]_ModelI(Cu+OSP仕様))にフリップチップボンディングを行い、半導体装置を得た。フリップチップボンディングの条件は、140℃に加熱されたボンディングステージ上に基板を置き、温度140℃、圧力150N/チップ、時間1秒の条件で仮圧着した後、温度250℃、圧力150℃の条件で時間を5秒にして本圧着を行った。得られた半導体装置を、冷熱衝撃装置(エスペック(株)製、TSE-11-A)にて、温度-55℃で30分間放置して温度125℃で30分間放置する工程を500回繰り返し、導通することを確認した。
Claims (11)
- (A)ポリイミド、(B)多官能エポキシ化合物、(C)エポキシ硬化剤および(D)無機粒子を含有し、不揮発性有機成分中における前記(A)ポリイミドの割合が3.0重量%以上30重量%以下、不揮発性有機成分中における前記(C)エポキシ硬化剤の割合が0.5重量%以上10重量%以下であり、かつ不揮発性有機成分の総グラム数をT、不揮発性有機成分中のエポキシ基のモル数をMとして、T/Mが400以上8000以下であることを特徴とする接着組成物。
- 前記(A)ポリイミドが一般式(2)または一般式(3)で表される構造を有し、かつエポキシ基と反応可能な官能基を側鎖に少なくとも一つ有し、かつ一般式(1)で表される構造を一般式(2)または一般式(3)中のR4としてポリマー全量に対し5~15重量%有していることを特徴とする請求項1に記載の接着組成物。
- (B)多官能エポキシ化合物として、少なくともエポキシ当量が1000以上7000以下のエポキシ化合物を用いることを特徴とする請求項1または2に記載の接着組成物。
- (B)多官能エポキシ化合物として、さらに液状エポキシ化合物を用いることを特徴とする請求項3に記載の接着組成物。
- 不揮発性成分に占める(D)無機粒子の含有量が50重量%以上80重量%以下であることを特徴とする請求項1~4のいずれかに記載の接着組成物。
- 硬化後の接着組成物のマイナス40℃における弾性率が10GPa以上15GPa以下であることを特徴とする請求項1~5のいずれかに記載の接着組成物。
- 硬化後の接着組成物の23℃における最大強度が28N以上であることを特徴とする請求項1~6のいずれかに記載の接着組成物。
- 請求項1~7のいずれかに記載の接着組成物からなる層および支持フィルムを有することを特徴とする接着フィルム。
- 請求項1~7のいずれかに記載の接着組成物からなる層および基板を有することを特徴とする接着組成物付き基板。
- 請求項1~7のいずれかに記載の接着組成物からなる層を有する半導体装置。
- 第一の回路部材と第二の回路部材の間に、請求項1~7のいずれかに記載の接着組成物を介在させ、加熱加圧することにより前記第一の回路部材と前記第二の回路部材を電気的に接続させる半導体装置の製造方法。
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- 2015-01-09 JP JP2015502415A patent/JP6504050B2/ja active Active
- 2015-01-09 SG SG11201605819SA patent/SG11201605819SA/en unknown
- 2015-01-09 US US15/111,265 patent/US9617451B2/en active Active
- 2015-01-09 KR KR1020167021047A patent/KR102186795B1/ko active IP Right Grant
- 2015-01-09 CN CN201580004584.2A patent/CN105916956B/zh active Active
- 2015-01-14 TW TW104101197A patent/TWI639668B/zh not_active IP Right Cessation
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2016
- 2016-07-14 PH PH12016501392A patent/PH12016501392A1/en unknown
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WO2019142866A1 (ja) * | 2018-01-17 | 2019-07-25 | 旭化成株式会社 | ポリイミド前駆体樹脂組成物 |
JP2021093412A (ja) * | 2019-12-09 | 2021-06-17 | 東レ株式会社 | アンダーフィル用のシート状樹脂組成物、及びそれを用いた半導体装置 |
JP7276105B2 (ja) | 2019-12-09 | 2023-05-18 | 東レ株式会社 | アンダーフィル用のシート状樹脂組成物、及びそれを用いた半導体装置 |
Also Published As
Publication number | Publication date |
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KR20160108399A (ko) | 2016-09-19 |
JP6504050B2 (ja) | 2019-04-24 |
US20160340558A1 (en) | 2016-11-24 |
PH12016501392B1 (en) | 2017-02-06 |
CN105916956A (zh) | 2016-08-31 |
US9617451B2 (en) | 2017-04-11 |
PH12016501392A1 (en) | 2017-02-06 |
TWI639668B (zh) | 2018-11-01 |
JPWO2015107990A1 (ja) | 2017-03-23 |
CN105916956B (zh) | 2019-04-12 |
TW201533198A (zh) | 2015-09-01 |
SG11201605819SA (en) | 2016-08-30 |
KR102186795B1 (ko) | 2020-12-04 |
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