CN103222040A - Adhesive composition, method for manufacturing semiconductor device, and semiconductor device - Google Patents

Adhesive composition, method for manufacturing semiconductor device, and semiconductor device Download PDF

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Publication number
CN103222040A
CN103222040A CN2011800470533A CN201180047053A CN103222040A CN 103222040 A CN103222040 A CN 103222040A CN 2011800470533 A CN2011800470533 A CN 2011800470533A CN 201180047053 A CN201180047053 A CN 201180047053A CN 103222040 A CN103222040 A CN 103222040A
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Prior art keywords
semiconductor device
adhesive composite
connecting portion
semiconductor
expression
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Granted
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CN2011800470533A
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Chinese (zh)
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CN103222040B (en
Inventor
本田一尊
永井朗
榎本哲也
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Lishennoco Co ltd
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Hitachi Chemical Co Ltd
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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
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    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
    • H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract

The present invention relates to an adhesive composition for encapsulating connection parts in a semiconductor device in which respective connection parts of a semiconductor chip and a wiring circuit board are electrically connected with each other or alternatively in a semiconductor device in which respective connection parts of a plurality of semiconductor chips are electrically connected with each other. The adhesive composition contains an epoxy resin, a curing agent and an acrylic surface-treated filler.

Description

The manufacture method of adhesive composite, semiconductor device and semiconductor device
Technical field
The present invention relates to the manufacture method and the semiconductor device of adhesive composite, semiconductor device.
Background technology
In recent years, for semiconductor chip being installed and being connected in substrate, be extensive use of the wire-bonded mode of use spun gold metal fines such as (gold wire).On the other hand, in order to tackle requirements such as miniaturization for semiconductor device, slimming, high function, highly integrated, high speed, between semiconductor chip and substrate, form the conductivity projection that is called projection and the flip-chip connected mode (FC connected mode) that semiconductor chip is connected with substrate is expanded lasting.
For example, about being connected between semiconductor chip and the substrate, the active connected mode that is applied to COB (the Chip On Board) type among BGA (Ball Grid Array), the CSP (Chip Size Package) etc. also is equivalent to the FC connected mode.In addition, the FC connected mode also is widely used in forming connecting portion (projection, distribution) on semiconductor chip and with in the connected mode of COC (the Chip On Chip) type that connects between the semiconductor chip (for example with reference to patent documentation 1).
But, in order to tackle further miniaturization, slimming, multifunction requirement, with above-mentioned connected mode carry out stacked, the chip-stacked type packaging body (chip stack type package) of multistageization, POP (Package On Package), TSV (Through-Silicon Via) etc. also begin extensively to popularize.Because semiconductor chip etc. is disposed three-dimensionally, thereby comparatively speaking can reduce packaging body in the stacked multistage technology like this with the method for configuration two-dimensionally.Particularly, the TSV technology for semi-conductive performance improve, noise lowers, erection space is cut down, it is also effective to economize electrification, has received concern as the semiconductor distribution technology of a new generation.
Yet the major metal as being used for above-mentioned connecting portion (projection, distribution) has scolding tin, tin, gold, silver, copper, nickel etc., also uses the multiple electric conducting material that comprises in them.About being used for the metal of connecting portion, generate oxide-film owing to oxidation takes place on the surface, at impurity such as surface attachment oxides, have the situation that generates impurity at the joint face of connecting portion.During remaining such impurity, then have following may: make between semiconductor chip and the substrate, connectivity, insulating reliability between 2 semiconductor chips reduce, make and adopt the advantage of above-mentioned connected mode impaired.
As the generation that suppresses these impurity and improve internuncial method, the method of before connecting, the surface of substrate, semiconductor chip being implemented pre-treatment can be listed, the pre-solder flux that is used for OSP (Organic Solderbility Preservatives) and handles, the method for anti-rust agent for treatment of applying can be listed.Yet, also exist since pre-treatment after pre-solder flux, anti-rust agent for treatment is remaining and deterioration thereby cause the situation of connectivity reduction.
On the other hand, according to the method that the connecting portion between semiconductor chip and the substrate etc. is sealed with semiconductor-encapsulating material (encapsulating semiconductor bonding agent), can semiconductor chip and substrate, semiconductor chip being connected each other, connecting portion be sealed.Therefore, oxidation, the impurity that can suppress to be used for the metal of connecting portion adhere to connecting portion, and the protection connecting portion is not subjected to the infringement of external environment condition.Therefore, can effectively improve connectivity, insulating reliability, operation, productivity ratio.
In addition, in the semiconductor device of making by the flip-chip connected mode,, the thermal stress that does not make the coefficient of thermal expansion differences that is derived from semiconductor chip and substrate, semiconductor chip coefficient of thermal expansion differences each other causes bad connection for concentrating on connecting portion, thereby need be with semiconductor-encapsulating material with the space sealing between semiconductor chip and the substrate etc.Particularly, in semiconductor chip and substrate, often use the different composition of thermal coefficient of expansion, require to seal and improve resistance to sudden heating by semiconductor-encapsulating material.
In adopting the sealing means of above-mentioned semiconductor-encapsulating material, carry out bigger differentiation and can list capillary flow flowing mode (Capillary-Flow) and supply mode (Pre-applied) (for example with reference to patent documentation 2～6) in advance.The capillary flow flowing mode is meant, by capillarity aqueous semiconductor-encapsulating material flow into the mode in the space between semiconductor chip and the substrate after being connected of semiconductor chip and substrate.Pre-supply mode is meant, before being connected of semiconductor chip and substrate, to semiconductor chip or substrate supply pasty state, membranaceous semiconductor-encapsulating material, then with semiconductor chip and substrate ways of connecting.About these sealing means, be accompanied by the progress of the miniaturization of semiconductor device in recent years, space between semiconductor chip and the substrate etc. has narrowed down, thereby in the capillary flow flowing mode, have: the situation that injection needs for a long time and productivity ratio reduces, situation about can't inject, in addition, even can inject the situation that also has filling part not and become the reason of pore.Therefore, consider that pre-supply mode becomes main flow as the manufacture method of the packaging body that can realize high function, high integrated, high speed from the viewpoint of operation, productivity ratio, reliability.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2008-294382 communique
Patent documentation 2: TOHKEMY 2001-223227 communique
Patent documentation 3: TOHKEMY 2002-283098 communique
Patent documentation 4: TOHKEMY 2005-272547 communique
Patent documentation 5: TOHKEMY 2006-169407 communique
Patent documentation 6: TOHKEMY 2006-188573 communique
Summary of the invention
The problem that invention will solve
In above-mentioned pre-supply mode, because when connecting, with the sealing of the space between semiconductor chip and the substrate, thereby need to consider condition of contact and the composition that contains of selecting semiconductor-encapsulating material by semiconductor-encapsulating material by heating and pressurizing.Generally speaking in connecting portion connection each other, consider to have used metal bond from the viewpoint of fully guaranteeing connectivity, insulating reliability.Because metal bond has been to use the connected mode of high temperature (for example more than 200 ℃), therefore have following situation: result from remaining volatile ingredient in the semiconductor-encapsulating material, because of the newly-generated volatile ingredient of the decomposition that contains composition of semiconductor-encapsulating material, semiconductor-encapsulating material produces foaming.Thus, produce the bubble that is known as pore, semiconductor-encapsulating material is from semiconductor chip, strippable substrate.In addition, when in heating and pressurizing, when pressure discharges, when producing the resilience (spring back) of above-mentioned pore, semiconductor chip etc., produce bad connections such as destruction by the connecting portion that tearing of connecting portion connection projection connected to one another caused.Owing to these reasons, thereby in semiconductor-encapsulating material in the past, have the possible of connectivity, insulating reliability reduction.
In addition, do not have at semiconductor-encapsulating material under the situation of sufficient flux activity (oxide-film of metal surface, the removal effect of impurity), have oxide-film, the impurity that to remove the metal surface, can not form good metal-metal bond, can't guarantee the situation of conducting.Further, when the insulating reliability of semiconductor-encapsulating material hangs down, then be difficult to tackle the narrow spacingization of connecting portion, defective insulation takes place.Also, in semiconductor-encapsulating material in the past, have the possibility of connectivity, insulating reliability reduction owing to these reasons.
About the semiconductor device that uses semiconductor-encapsulating material to make, require in reliability, more specifically realize sufficient level aspect thermal endurance, moisture-proof and the reflux-resisting welded property (フ of anti-リ ロ ー).In order to ensure reflux-resisting welded property, thereby require under the Reflow Soldering temperature of 260 ℃ of front and back, keep can suppress patch layer (ダ イ ボ Application De Layer) (bond layer) peel off or destroy such high adhesive strength.
The present invention develops in view of said circumstances, its purpose be to provide the semiconductor device that can make reflux-resisting welded property and connection reliability and insulating reliability excellence adhesive composite, used the manufacture method and the semiconductor device of the semiconductor device of this adhesive composite.
The scheme that is used to deal with problems
The invention provides a kind of adhesive composite, with the adhesive composite of connecting portion sealing, it contains epoxy resin, curing agent and has carried out surface-treated acrylic acid series surface treatment filler by the compound with the group shown in the following general formula (1) in its semiconductor device that reciprocally is electrically connected for the connecting portion separately of the semiconductor device that reciprocally is electrically connected at the connecting portion separately of semiconductor chip and wired circuit board or a plurality of semiconductor chips.
[Chemical formula 1]
Figure BDA00002982623900041
In the formula (1), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30.
The present invention provides a kind of adhesive composite in addition, in its semiconductor device that reciprocally is electrically connected for the connecting portion separately of the semiconductor device that reciprocally is electrically connected at the connecting portion separately of semiconductor chip and wired circuit board or a plurality of semiconductor chips with the adhesive composite of connecting portion sealing, the filler that it contains epoxy resin, curing agent and has the group shown in the following general formula (1).
[Chemical formula 2]
In the formula (1), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30.
The adhesive composite of the invention described above is by on the basis of containing epoxy resin and curing agent, further contain acrylic acid series surface treatment filler or have filler by the group of above-mentioned general formula (1) expression, even if thereby carrying out being suitable in the flip-chip connected mode of metal bond at high temperature (for example more than 200 ℃) makes encapsulating semiconductor with under the situation of bonding agent, also can realize high reflux-resisting welded property, connection reliability and insulating reliability.
In order to improve the reflux-resisting welded property of adhesive composite, the bonding force after the moisture absorption under the needs raising high temperature.But always the filler of Shi Yonging can reduce hydroscopicity and thermal coefficient of expansion, be effectively in order to improve connectivity, insulating reliability, but the cementability of filler self lacks usually.
Known herein, make silane coupler and do not carry out the surface-treated filler when together containing in resin, then can make the surface of filler carry out silane coupled processing, synthesize the filler of various surface state by the substituting group of silane coupler.Yet the volatility height of silane coupler becomes the reason that produces pore in the manufacturing process of the semiconductor device of the technology under having the high temperature such as metal bond that need the high temperature connection.Similarly, the filler that always uses is carried out under the surface-treated situation, have the high organic situations of volatility such as producing methyl alcohol, become the reason that pore produces.
Generally speaking, be formed with the dielectric film that is known as solder mask on semiconductor substrate, solder mask includes the acrylic acid series material mostly.Therefore, the inventor etc. have found, by to contain aforesaid propylene acid is the surface treatment filler or have filler by the group of above-mentioned general formula (1) expression, thus improve adhesive composite at high temperature modulus of elasticity and the bonding force after the moisture absorption, can realize reflux-resisting welded property.Suppositions such as the inventor, in adhesive composite of the present invention, use the filler that has carried out surface-treated acrylic acid series surface treatment filler in advance or had the group of representing by above-mentioned general formula (1), thereby can suppress the generation of the high material of volatility, and because acrylic acid series compound and solder mask excellent in adhesion thereby can improve connectivity with substrate.The inventor waits supposition in addition, acrylic acid series surface treatment filler or have the insulating reliability that is difficult for reducing connecting portion by the filler of the group of above-mentioned general formula (1) expression, be difficult for the thermal coefficient of expansion and the modulus of elasticity of the solidfied material of reduction adhesive composite, therefore can improve connection reliability.
Acrylic acid series surface treatment filler or have the excellent dispersion of filler in resinous principle by the group of above-mentioned general formula (1) expression, and can improve the intensity of packaging body (substrate-chip, the chip-chip etc.) terminal part in the semiconductor device that uses adhesive composite of the present invention and make.
Above-mentioned bonding force raising is not subject on the solder mask, is apparent in (SiO, SiN etc.) between the semiconductor chip yet.
Compound with group of being represented by above-mentioned general formula (1) is preferably the compound of being represented by following general formula (2).
[chemical formula 3]
Figure BDA00002982623900051
In the formula (2), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30, R 3The alkyl of expression carbon number 1～30.
Adhesive composite of the present invention has carried out the surface-treated filler by containing by the compound shown in the above-mentioned general formula (2), thereby can further improve reflux-resisting welded property, connection reliability and insulating reliability.
In adhesive composite of the present invention, consider from the thermal endurance that improves adhesive composite and the viewpoint of film forming, can further contain weight average molecular weight and be the macromolecule component more than 10000.
Consider that from the attaching of further raising adhesive composite, the viewpoint of film forming the weight average molecular weight of above-mentioned macromolecule component is preferably more than 30000, vitrification point is preferably below 100 ℃.
Adhesive composite of the present invention can improve flux activity by further containing the flux activity agent, removes oxide-film, the impurity of the metal surface of connecting portion, can form good metal-metal bond.
Owing to can improve by pre-supply mode the operation under the situation of the space of semiconductor chip and wired circuit board or the sealing of the space between a plurality of semiconductor chip, so the shape of adhesive composite of the present invention is preferably membranaceous.
The present invention provides a kind of manufacture method of semiconductor device in addition, the manufacture method of the semiconductor device that the semiconductor device that it reciprocally is electrically connected for the connecting portion separately of semiconductor chip and wired circuit board or the connecting portion separately of a plurality of semiconductor chips reciprocally are electrically connected, described method possesses uses the operation of above-mentioned adhesive composite with the connecting portion sealing.
According to the manufacture method of semiconductor device of the present invention, by using above-mentioned adhesive composite, thereby can improve reflux-resisting welded property, connection reliability and the insulating reliability of semiconductor device.
When above-mentioned connecting portion contains at least a metal that is selected from gold, silver, copper, nickel, tin and the lead as main component, then can further improve electrical conductivity, thermal conductivity, the connection reliability of connecting portion.
The present invention provides the semiconductor device by the manufacture method acquisition of above-mentioned semiconductor device in addition.
Semiconductor device of the present invention is owing to the manufacture method of using above-mentioned semiconductor device is made, thereby becomes the fully excellent semiconductor device of reflux-resisting welded property, connection reliability and insulating reliability.
The effect of invention
Can provide according to the present invention: the adhesive composite of reflux-resisting welded property, connection reliability and insulating reliability excellence, used the manufacture method and the semiconductor device of the semiconductor device of this adhesive composite.Description of drawings
Fig. 1 is the pattern cutaway view of an execution mode of expression semiconductor device of the present invention.
Fig. 2 is the pattern cutaway view of another execution mode of expression semiconductor device of the present invention.
Fig. 3 is the pattern cutaway view of another execution mode of expression semiconductor device of the present invention.
Fig. 4 is the operation cutaway view of an execution mode of the manufacture method of pattern ground expression semiconductor device of the present invention.
Fig. 5 is the ideograph of the outward appearance of the sample of expression insulating reliability test usefulness.
Embodiment
Below, on one side preferred implementation of the present invention is elaborated with reference to accompanying drawing on one side according to circumstances.Illustrated that in the accompanying drawings, identical or considerable part pays same-sign and the repetitive description thereof will be omitted.In addition, wait the short of explanation in advance especially of position relation up and down, just be made as position relation based on position shown in the drawings relation.Further, the dimensional ratios of accompanying drawing is not limited to illustrated ratio.
＜adhesive composite＞
The adhesive composite of present embodiment (encapsulating semiconductor bonding agent) be semiconductor chip and wired circuit board (below, abbreviate " substrate " according to circumstances as) the semiconductor device that reciprocally is electrically connected of connecting portion separately, or in the semiconductor device that reciprocally is electrically connected of the connecting portion separately of a plurality of semiconductor chips with the adhesive composite of connecting portion sealing, its contain epoxy resin (below, be called " (a) composition " according to circumstances), curing agent (below, be called " (b) composition " according to circumstances), and acrylic acid series surface treatment filler or have by the filler of the group of above-mentioned general formula (1) expression (below, be called " (c) composition " according to circumstances).In addition, adhesive composite contain as required the macromolecule component of weight average molecular weight more than 10000 (below, be called " (d) composition " according to circumstances) or flux activity agent (below, be called " (e) composition " according to circumstances.)。Below each composition of the adhesive composite that constitutes present embodiment is described.
(a) composition: epoxy resin
As epoxy resin, then can use if in molecule, have the epoxy resin of the epoxy radicals more than 2 with being not particularly limited.As (A) composition, specifically can use bisphenol A-type, Bisphenol F type, naphthalene type, phenol phenolic varnish type, cresols phenolic varnish type, phenol aralkyl-type, biphenyl type, triphenyl methane type, dicyclopentadiene type and various polyfunctional epoxy resin.They can use separately or use in the mode of the mixture more than 2 kinds.
About (a) composition, the viewpoint of decomposing when suppressing connection at high temperature and producing this situation of volatile ingredient is considered, temperature when connecting is under 250 ℃ the situation, thermogravimetric loss dose rate (Hot heavily measures a small amount of rate of Minus) under preferably using 250 ℃ is the epoxy resin below 5%, under 300 ℃ situation, preferably using thermogravimetric loss dose rate under 300 ℃ is epoxy resin below 5%.
(b) composition: curing agent
As (b) composition, for example can list phenolic resins is that curing agent, acid anhydrides are that curing agent, amine are that curing agent, imidazoles are that curing agent and phosphine are curing agent.If (b) composition comprises phenol hydroxyl, acid anhydrides, amine or imidazoles, can manifest being suppressed at the flux activity that connecting portion produces this situation of oxide-film so, can improve connection reliability, insulating reliability.Below each curing agent is described.
(i) phenolic resins is curing agent
As phenolic resins is curing agent, if have the phenolic resins of the phenol hydroxyl more than 2 in molecule is that curing agent then is not particularly limited, and for example can use phenol novolaks, cresols novolaks, phenol aralkyl resin, cresol naphthol formaldehyde condensation products, the multifunctional phenolic aldehyde of triphenyl methane type and various multifunctional phenolic resins.They can use separately or use in the mode of the mixture more than 2 kinds.
Phenolic resins is that curing agent is considered to be preferably 0.3～1.5 from the viewpoint of good curable, cementability and storage stability with respect to the equivalent proportion (phenol hydroxyl/epoxy radicals, mol ratio) of above-mentioned (a) composition, more preferably 0.4～1.0, more preferably 0.5～1.0.Equivalent proportion is 0.3 when above, then has the tendency that curable improves and bonding force improves, and is 1.5 when following, then exists the unreacted phenol hydroxyl can be excessively not remaining, water absorption rate is suppressed for low the tendency of insulating reliability raising.
(ii) acid anhydrides is a curing agent
As acid anhydrides is curing agent, for example can use hexahydrotoluene tetracarboxylic dianhydride, trimellitic anhydride, pyromellitic acid dianhydride, benzophenone tetracarboxylic dianhydride and ethylene glycol bis dehydration trimellitate.They can use separately or use in the mode of the mixture more than 2 kinds.
Acid anhydrides is that curing agent is considered to be preferably 0.3～1.5 from the viewpoint of good curable, cementability and storage stability with respect to the equivalent proportion (anhydride group/epoxy radicals, mol ratio) of above-mentioned (a) composition, more preferably 0.4～1.0, more preferably 0.5～1.0.Equivalent proportion is 0.3 when above, then has the tendency that curable improves and bonding force improves, and is 1.5 when following, then exists the unreacted acid anhydrides can be excessively not remaining, water absorption rate is suppressed for low the tendency of insulating reliability raising.
(iii) amine is curing agent
As amine is curing agent, can use for example dicyandiamide.
To be curing agent consider to be preferably 0.3～1.5 from the viewpoint of good curable, cementability and storage stability with respect to the equivalent proportion (amine/epoxy radicals, mol ratio) of above-mentioned (a) composition amine, and more preferably 0.4～1.0, more preferably 0.5～1.0.Equivalent proportion is 0.3 when above, then has the tendency that curable improves and bonding force improves, and is 1.5 then to exist when following the unreacted amine can be excessively not remaining the tendency of insulating reliability raising.
(iv) imidazoles is a curing agent
As imidazoles is curing agent, for example can list the 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1 benzyl 2 methyl imidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-undecyl imidazole, 1-cyano group-2-phenylimidazole, 1-cyanoethyl-2-undecyl imidazole trimellitate (ト リ メ リ テ イ ト), the 1-cyanoethyl-2-phenylimidazole trimellitate, 2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-ethyl-s-triazine, 2,4-diaminourea-6-[2 '-undecyl imidazole base-(1 ')]-ethyl-s-triazine, 2,4-diaminourea-6-[2 '-ethyl-4 '-methylimidazolyl-(1 ')]-ethyl-s-triazine, 2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-ethyl-s-triazine isocyanuric acid addition product, 2-phenylimidazole isocyanuric acid addition product, 2-phenyl-4,5-dihydroxy methylimidazole, 2-phenyl-4-methyl-5-hydroxymethyl imidazoles, and the addition product of epoxy resin and imidazoles.Among them, curable from excellence, the viewpoint of storage stability and connection reliability is considered, preferred 1-cyanoethyl-2-undecyl imidazole, 1-cyano group-2-phenylimidazole, 1-cyanoethyl-2-undecyl imidazole trimellitate, the 1-cyanoethyl-2-phenylimidazole trimellitate, 2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-ethyl-s-triazine, 2,4-diaminourea-6-[2 '-ethyl-4 '-methylimidazolyl-(1 ')]-ethyl-s-triazine, 2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-ethyl-s-triazine isocyanuric acid addition product, 2-phenylimidazole isocyanuric acid addition product, 2-phenyl-4,5-dihydroxy methylimidazole and 2-phenyl-4-methyl-5-hydroxymethyl imidazoles.They can use separately or and with 2 kinds with on use.In addition, also can be made into they are carried out microencapsulation and the latent curing agent that obtains.
Imidazoles is that the content of curing agent is preferably 0.1～20 mass parts with respect to (a) composition 100 mass parts, more preferably 0.1～10 mass parts.Imidazoles is that the content of curing agent is 0.1 mass parts when above, and the tendency that then exists curable to improve is that 20 mass parts then have that adhesive composite can not solidify before forming metal bond when following, is difficult for the tendency of generation bad connection.
(v) phosphine is a curing agent
As phosphine is curing agent, for example can list triphenylphosphine, tetraphenylphosphoniphenolate tetraphenyl borate, tetraphenylphosphoniphenolate four (4-aminomethyl phenyl) borate and tetraphenylphosphoniphenolate (4-fluorophenyl) borate.
Phosphine is that the content of curing agent is preferably 0.1～10 mass parts with respect to (a) composition 100 mass parts, more preferably 0.1～5 mass parts.Phosphine is that the content of curing agent is 0.1 mass parts when above, and the tendency that then exists curable to improve is that 10 mass parts then have that adhesive composite can not solidify before forming metal bond when following, is difficult for the tendency of generation bad connection.
Phenolic resins is that curing agent, acid anhydrides are that curing agent and amine are curing agent, can distinguish and use a kind or use in the mode of the mixture more than 2 kinds individually.Imidazoles is that curing agent and phosphine are that curing agent also can be distinguished use separately, but can be that curing agent, acid anhydrides are that curing agent or amine are that curing agent uses with phenolic resins also.
It is that curing agent, acid anhydrides are that curing agent or amine are under the curing agent conduct situation of (b) composition that adhesive composite comprises phenolic resins, can manifest the flux activity of removing oxide-film, can more improve connection reliability.
(c) composition: acrylic acid series surface treatment filler or have filler by the group of above-mentioned general formula (1) expression
As (c) composition, then be not particularly limited if carried out the surface-treated filler, for example can use insulating properties inorganic filler, whisker (ウ ィ ス カ ー) and resin extender are carried out surface treatment and the filler that obtains by compound with the group shown in the above-mentioned general formula (1).That is,, can use the filler that has by the group of above-mentioned general formula (1) expression as (C) composition.
Herein, in the formula (1), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2 is preferably hydrogen atom, methyl or ethyl.Have following tendency: R 1Carbon number increase more then that volume uprises more, carbon number surpasses at 2 o'clock then reactive the reduction.R 2The alkylidene of expression carbon number 1～30 is preferably the alkylidene of carbon number 1～15.R 2Carbon number surpass at 30 o'clock, then have and be difficult for filler is carried out the surface-treated tendency.
(c) whether composition has the group of being represented by above-mentioned general formula (1) at filling surface, for example can confirm by following such method.
With the adhesive composite heating of present embodiment, use gas chromatography (for example, SHIMADZU system, goods name " GC-17A ") to measure the methyl alcohol that is produced.Amount according to this methyl alcohol can be confirmed: have this situation of group by above-mentioned general formula (1) expression that is present in filling surface.In the case, similarly measure the adhesive composite do not comprise (C) composition quantity of methyl alcohol and as reference.
As the insulating properties inorganic filler, for example can list glass, silicon dioxide, aluminium oxide, titanium oxide, carbon black, mica and boron nitride, be preferably silicon dioxide, aluminium oxide, titanium oxide and boron nitride, more preferably silicon dioxide, aluminium oxide and boron nitride.As whisker, for example can list aluminium borate, aluminium titanates, zinc oxide, calcium silicates, magnesium sulfate and boron nitride.As resin extender, can list polyurethane, polyimides.These fillers and whisker can use separately or use in the mode of the mixture more than 2 kinds.The shape of filler, particle diameter and use level are not particularly limited.Also can use fine nano silicon.Among these fillers, since the simple and easy degree of surface-treated, better with the compatibility of resinous principle, therefore preferred silica filler.
As (c) composition, can use by the compound shown in the above-mentioned general formula (2) and carry out the surface-treated filler.Specifically can use: by R in the formula (2) 1For the acrylic acid series compound of hydrogen atom carried out the surface-treated silica filler, by R in the formula (2) 1For the methacrylic acid based compound of methyl has carried out the surface-treated silica filler and by R in the formula (2) 1For the ethylacrylic acid based compound of ethyl has carried out the surface-treated silica filler.From the semiconductor bonding agent contained resinous principle, consider with the reactivity of semiconductor substrate surface, the viewpoint that key forms, in the preferred above-mentioned formula (2), R 1Be the little group of volume, R 1Alkyl, hydrogen atom, methyl or ethyl for hydrogen atom or carbon number 1 or 2.Have following tendency: R 1Carbon number increase more then that volume uprises more, carbon number surpasses at 2 o'clock then reactive the reduction.That is,, can use by acrylic acid series compound, methacrylic acid based compound or ethylacrylic acid based compound and carry out the surface-treated silica filler as (C) composition.
In above-mentioned general formula (1) or (2), R 2The alkylidene of expression carbon number 1～30 is because volatile ingredient is few thereby be preferably the alkylidene of carbon number 1～15.In the formula (2), R 3The alkyl of expression carbon number 1～30 can suitably be selected according to the easy degree of surface-treated.R 3Carbon number be 30 when following, then have easily filler carried out the surface-treated tendency.
(c) shape of composition, particle diameter are suitably set according to the purposes of adhesive composite and are got final product, and are not particularly limited.
Average grain diameter about (c) composition, be shaped as under the spherical situation at filler, average grain diameter is preferably below the 2 μ m, in the packaging body of narrow spacingization, narrow gap progress, for fear of reducing by catching the reliability that (ト ラ ッ ピ Application グ) cause, more preferably below the 1.5 μ m, be preferably especially below the 1.0 μ m.In addition, consider that from the viewpoint of the property handled its lower limit more preferably more than the 0.005 μ m, is preferably below the 0.01 μ m especially.
About the use level of (c) composition, be benchmark all with the solid constituent of adhesive composite, be preferably 5～80 quality %, more preferably 10～70 quality %.When being that 5 quality % are when above, then having the tendency of bringing into play easily the raising of bonding force strongly, is 80 quality % when following, then has adjustment viscosity easily, the reduction, filler of the flowability of the adhesive composite interlock (catching) to connecting portion be difficult for to take place, the tendency that connection reliability improves.
In addition,, do not carry out surface treatment with filler in advance, as the constituent of adhesive composite and add, when in system, carrying out surface treatment, then produce methyl alcohol etc., cause when high-temperature technology, foaming for silane coupler.
By improving adhesive composite at the bonding force after near the moisture absorption 260 ℃ and improve near 260 ℃ modulus of elasticity, thereby reflux-resisting welded property can be improved, peeling off after the Reflow Soldering, bad connection can be prevented.
(d) composition: the macromolecule component of weight average molecular weight more than 10000
As (d) composition, for example can list phenoxy resin, polyimide resin, polyamide, poly-carbodiimide resin, cyanate ester resin, acrylic resin, mylar, polyvinyl resin, polyethersulfone resin, polyetherimide resin, polyvinyl acetal resin, carbamate resins and acrylic rubber.Viewpoint from thermal endurance and film forming excellence among them is considered, be preferably phenoxy resin, polyimide resin, acrylic rubber, cyanate ester resin and poly-carbodiimide resin, more preferably phenoxy resin, polyimide resin and acrylic rubber.These (d) compositions can use separately or use in the mode of the mixture more than 2 kinds, copolymer.But, in (d) composition, do not comprise epoxy resin as (A) composition.
Macromolecule compositions such as above-mentioned phenoxy resin, polyimide resin can use commercially available product, also can use composite.
Polyimide resin for example can make tetracarboxylic dianhydride and diamines carry out condensation reaction by known method and obtain.More specifically, in organic solvent, make tetracarboxylic dianhydride and diamines wait mole or roughly waits mole to mix (interpolation of each composition in proper order be any), reaction temperature is set at below 80 ℃, is preferably set to 0～60 ℃ and carry out addition reaction and get final product.Illustrated that for the reduction of all characteristics of suppressing adhesive composite, preferred above-mentioned tetracarboxylic dianhydride carries out crystal refining by acetic anhydride again and handles.
Along with the carrying out of above-mentioned addition reaction, the viscosity of reactant liquor raises lentamente, generates the polyamic acid as the precursor of polyimides.Polyimide resin can carry out dehydration closed-loop and obtains above-mentioned polyamic acid.Dehydration closed-loop can be undertaken by the hot closed loop method of carrying out heat treated, the chemical closed loop method of use dehydrating agent.Above-mentioned polyamic acid passes through to heat and depolymerization at 50～80 ℃, thereby can adjust its molecular weight.
Tetracarboxylic dianhydride as the raw material that is used as polyimide resin, be not particularly limited, for example can list: pyromellitic acid dianhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 2,2 ', 3,3 '-biphenyl tetracarboxylic dianhydride, 2,2-two (3,4-dicarboxyl phenyl) propane dianhydride, 2, two (2,3-dicarboxyl phenyl) the propane dianhydrides of 2-, 1,1-two (2,3-dicarboxyl phenyl) ethane dianhydride, 1, two (3,4-dicarboxyl phenyl) the ethane dianhydrides of 1-, two (2,3-dicarboxyl phenyl) methane dianhydride, two (3,4-dicarboxyl phenyl) methane dianhydride, two (3,4-dicarboxyl phenyl) sulfone dianhydride, 3,4,9, the 10-perylenetetracarboxylic dianhydride, two (3,4-dicarboxyl phenyl) ether dianhydride, benzene-1,2,3, the 4-tetracarboxylic dianhydride, 3,4,3 ', 4 '-benzophenone tetracarboxylic dianhydride, 2,3,2 ', 3 '-benzophenone tetracarboxylic dianhydride, 3,3,3 ', 4 '-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic acid dianhydride, 1,4,5,8-naphthalene tetracarboxylic acid dianhydride, 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, 1,2,4,5-naphthalene tetracarboxylic acid dianhydride, 2,6-dichloronaphtalene-1,4,5, the 8-tetracarboxylic dianhydride, 2,7-dichloronaphtalene-1,4,5, the 8-tetracarboxylic dianhydride, 2,3,6,7-Tetrachloronaphthalene-1,4,5, the 8-tetracarboxylic dianhydride, luxuriant and rich with fragrance-1,8,9, the 10-tetracarboxylic dianhydride, pyrazine-2,3,5, the 6-tetracarboxylic dianhydride, thiophene-2,3,5, the 6-tetracarboxylic dianhydride, 2,3,3 ', 4 '-biphenyl tetracarboxylic dianhydride, 3,4,3 ', 4 '-biphenyl tetracarboxylic dianhydride, 2,3,2 ', 3 '-biphenyl tetracarboxylic dianhydride, two (3,4-dicarboxyl phenyl) dimethylsilane dianhydride, two (3,4-dicarboxyl phenyl) aminomethyl phenyl silane dianhydride, two (3,4-dicarboxyl phenyl) diphenyl silane dianhydride, 1, two (3, the 4-dicarboxyl phenyl dimetylsilyl) benzene dianhydrides of 4-, 1,3-two (3,4-dicarboxyl phenyl)-1,1,3,3-tetramethyl bis cyclohexane dianhydride, TOPOT 2,2 (trimellitate acid anhydride), the ethene tetracarboxylic dianhydride, 1,2,3,4-butane tetracarboxylic acid dianhydride, decahydronaphthalene-1,4,5, the 8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydro naphthalene-1,2,5, the 6-tetracarboxylic dianhydride, pentamethylene-1,2,3, the 4-tetracarboxylic dianhydride, pyrrolidines-2,3,4, the 5-tetracarboxylic dianhydride, 1,2,3,4-cyclobutane tetracarboxylic dianhydride, two (outer-dicyclo [2,2,1] heptane-2, the 3-dicarboxylic acid dianhydride, dicyclo-[2,2,2]-and Xin-7-alkene-2,3,5, the 6-tetracarboxylic dianhydride, 2, two (3,4-dicarboxyl phenyl) the propane dianhydrides of 2-, 2,2-is two, and [4-(3,4-dicarboxyl phenyl) phenyl] the propane dianhydride, 2, two (3, the 4-dicarboxyl phenyl) hexafluoropropane dianhydrides of 2-, 2,2-is two, and [4-(3,4-dicarboxyl phenyl) phenyl] hexafluoropropane dianhydride, 4,4 '-two (3, the 4-di carboxyl phenyloxy) diphenyl sulfide dianhydride, 1, two (2-hydroxyl hexafluoro isopropyl) benzene of 4-two (trimellitic anhydride), 1, two (2-hydroxyl hexafluoro isopropyl) benzene of 3-two (trimellitic anhydride), 5-(2, the 5-dioxotetrahydrofuryl)-and 3-methyl-3-cyclohexene-1, the 2-dicarboxylic acid dianhydride, oxolane-2,3,4, the 5-tetracarboxylic dianhydride, by the tetracarboxylic dianhydride of following general formula (I) expression and the tetracarboxylic dianhydride who represents by following formula (II).
[chemical formula 4]
Figure BDA00002982623900131
In the formula (I), a represents 2～20 integer.
[chemical formula 5]
Figure BDA00002982623900141
Tetracarboxylic dianhydride by above-mentioned general formula (I) expression can be synthesized by trimellitic anhydride list acyl chlorides and corresponding glycol, specifically can list: 1,2-(ethylidene) two (trimellitate acid anhydrides), 1,3-(trimethylene) two (trimellitate acid anhydrides), 1,4-(tetramethylene) two (trimellitate acid anhydrides), 1,5-(pentamethylene) two (trimellitate acid anhydrides), 1,6-(hexa-methylene) two (trimellitate acid anhydrides), 1,7-(heptamethylene) two (trimellitate acid anhydrides), 1,8-(eight methylene) two (trimellitate acid anhydrides), 1,9-(nine methylene) two (trimellitate acid anhydrides), 1,10-(decamethylene) two (trimellitate acid anhydrides), 1,12-(ten dimethylenes) two (trimellitate acid anhydrides), 1,16-(ten hexa-methylenes) two (trimellitate acid anhydrides) and 1,18-(18 methylene) two (trimellitate acid anhydrides).
As the tetracarboxylic dianhydride, consider from the viewpoint that can give excellent moisture-proof reliability, preferably the tetracarboxylic dianhydride who represents by above-mentioned formula (II).Above-mentioned tetracarboxylic dianhydride can use separately or make up 2 kinds with on use.
Content by the tetracarboxylic dianhydride of above-mentioned formula (II) expression is preferably 40 moles more than the % with respect to whole tetracarboxylic dianhydrides, and more preferably 50 moles more than the %, more preferably 70 moles more than the %.Content is 40 moles of % when above, then has following tendency: guarantee fully easily based on the effect of having used the moisture-proof reliability that is obtained by the tetracarboxylic dianhydride of above-mentioned formula (II) expression.
Diamines as the raw material that is used as above-mentioned polyimide resin, be not particularly limited, for example can list: o-phenylenediamine, m-phenylene diamine (MPD), p-phenylenediamine (PPD), 3,3 '-diamino-diphenyl ether, 3,4 '-diamino-diphenyl ether, 4,4 '-diamino-diphenyl ether, 3,3 '-diaminodiphenyl-methane, 3,4 '-diaminodiphenyl-methane, 4,4 '-diamino-diphenyl ether methane, two (4-amino-3, the 5-3,5-dimethylphenyl) methane, two (4-amino-3, the 5-diisopropylbenzyl) methane, 3,3 '-diamino-diphenyl difluoromethane, 3,4 '-diamino-diphenyl difluoromethane, 4,4 '-diamino-diphenyl difluoromethane, 3,3 '-diamino diphenyl sulfone, 3,4 '-diamino diphenyl sulfone, 4,4 '-diamino diphenyl sulfone, 3,3 '-diaminodiphenyl sulfide, 3,4 '-diaminodiphenyl sulfide, 4,4 '-diaminodiphenyl sulfide, 3,3 '-diamino-diphenyl ketone, 3,4 '-diamino-diphenyl ketone, 4,4 '-diamino-diphenyl ketone, 2, two (3-aminophenyl) propane of 2-, 2,2 '-(3,4 '-diamino-diphenyl) propane, 2, two (4-aminophenyl) propane of 2-, 2, two (3-aminophenyl) HFC-236fa of 2-, 2,2-(3,4 '-diamino-diphenyl) HFC-236fa, 2, two (4-aminophenyl) HFC-236fa of 2-, 1, two (3-amino-benzene oxygen) benzene of 3-, 1, two (3-amino-benzene oxygen) benzene of 4-, 1, two (4-amino-benzene oxygen) benzene of 4-, 3,3 '-(1,4-phenylene two (1-methyl ethylidene)) dianil, 3,4 '-(1,4-phenylene two (1-methyl ethylidene)) dianil, 4,4 '-(1,4-phenylene two (1-methyl ethylidene)) dianil, 2, two (4-(3-amino-benzene oxygen) phenyl) propane of 2-, 2, two (4-(3-amino-benzene oxygen) phenyl) HFC-236fa of 2-, 2, two (4-(4-amino-benzene oxygen) phenyl) HFC-236fa of 2-, two (4-(3-amino-benzene oxygen) phenyl) thioether, two (4-(4-amino-benzene oxygen) phenyl) thioether, two (4-(3-amino-benzene oxygen) phenyl) sulfone, two (4-(4-amino-benzene oxygen) phenyl) sulfone, 3, aromatic diamines such as 5-diaminobenzoic acid, 1, two (amino methyl) cyclohexanes of 3-, 2, two (the 4-amino-benzene oxygen phenyl) propane of 2-, by the following general formula (III) or (IV) the fatty ether diamines of expression, by the aliphatic diamine of following general formula (V) expression and by the siloxane diamine of following general formula (VI) expression.
[chemical formula 6]
Figure BDA00002982623900151
In the formula (III), Q 1, Q 2And Q 3Represent the alkylidene of carbon number 1～10 respectively independently, b represents 1～80 integer.
[chemical formula 7]
In the formula (IV), Q 4, Q 5, Q 6And Q 7The alkylidene of representing carbon number 1～10 respectively independently, c, d and e are represented 1～50 integer respectively independently.
[chemical formula 8]
Figure BDA00002982623900153
In the formula (V), f represents 5～20 integer.
[chemical formula 9]
Figure BDA00002982623900154
In the formula (VI), Q 8And Q 13The alkylidene of representing carbon number 1～5 respectively independently maybe can have or not have substituent phenylene, Q 9, Q 10, Q 11And Q 12Represent alkyl, phenyl or the phenoxy group of carbon number 1～5 respectively independently, g represents 1～5 integer.
Among them, consider from the viewpoint that can give low stress, low temperature plyability and low-temperature adhesion, be preferably by above-mentioned general formula (III), (IV) or (V) diamines of expression, consider, preferably by the diamines of above-mentioned general formula (VI) expression from the viewpoint that can give low water absorbable and agent of low hygroscopicity.These diamines can use separately or make up 2 kinds with on use.
By above-mentioned general formula (III) or (IV) content of fatty ether diamines of expression be preferably 1～50 mole of % of whole diamines, be preferably 20～80 moles of % of whole diamines by the content of the aliphatic diamine of above-mentioned general formula (V) expression, be preferably 20～80 moles of % of whole diamines by the content of the siloxane diamine of above-mentioned general formula (VI) expression.For in the scope of above-mentioned content the time, then have the effect of giving low temperature plyability and low water absorbable and become big tendency.
In addition, as fatty ether diamines, specifically can list the fatty ether diamines of following formula (III-1)～(III-5) by above-mentioned general formula (III) expression.Illustrated that at general formula (III-4) with (III-5), n represents the integer more than 1.
[Chemical formula 1 0]
Figure BDA00002982623900161
Weight average molecular weight by the fatty ether diamines of above-mentioned general formula (III-4) expression for example is preferably 350,750,1100 or 2100.In addition, the weight average molecular weight by the fatty ether diamines of above-mentioned general formula (III-5) expression for example is preferably 230,400 or 2000.
Among the above-mentioned fatty ether diamines, from can guaranteeing the low temperature plyability and the viewpoint of the good cementability of the substrate that has organic resist considered, more preferably respectively by above-mentioned general formula (IV), following general formula (VII), (VIII) or (IX) the fatty ether diamines of expression.
[Chemical formula 1 1]
Figure BDA00002982623900171
In the formula (VII), h represents 2～80 integer, more preferably 2～70.
[Chemical formula 1 2]
Figure BDA00002982623900172
In the formula (VIII), c, d and e represent 1～50 integer, more preferably 2～40.
[Chemical formula 1 3]
In the formula (IX), j and k represent 1～70 integer respectively independently.
As fatty ether diamines by above-mentioned general formula (VII) expression, specifically can list SUN TECHNO CHEMICAL(サ Application テ Network ノ ケ ミ カ Le) (strain) system JEFFAMINE D-230, D-400, D-2000 and D-4000, the polyetheramine D-230 of BASF system, D-400 and D-2000, as fatty ether diamines by above-mentioned general formula (VIII) expression, specifically can list SUN TECHNO CHEMICAL(strain) system JEFFAMINE ED-600, ED-900, ED-2001, fatty ether diamines as by above-mentioned formula (IX) expression can list SUN TECHNO CHEMICAL(strain) the JEFFAMINE EDR-148 of system.
Aliphatic diamine as by above-mentioned general formula (V) expression for example can list 1,2-diaminoethanes, 1,3-diaminopropanes, 1,4-diaminobutane, 1,5-diaminourea pentane, 1,6-diamino hexane, 1,7-diaminourea heptane, 1,8-diaminourea octane, 1,9-diaminourea nonane, 1,10-diamino decane, 1,11-diaminourea hendecane, 1,12-diaminourea dodecane and 1,2-DACH.Among them, preferred 1,9-diaminourea nonane, 1,10-diamino decane, 1,11-diaminourea hendecane and 1,12-diaminourea dodecane.
As the siloxane diamine by above-mentioned general formula (VI) expression, the g in general formula (VI) under 1 the situation, can list: 1,1,3,3-tetramethyl-1, two (4-aminophenyl) disiloxane of 3-, 1,1,3,3-four phenoxy groups-1, two (4-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetraphenyl-1, two (2-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetraphenyl-1, two (3-aminopropyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1, two (2-amino-ethyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1, two (3-aminopropyl) disiloxane of 3-, 1,1,3,3-tetramethyl-1,3-two (the amino butyl of 3-) disiloxane and 1,3-dimethyl-1,3-dimethoxy-1,3-two (the amino butyl of 4-) disiloxane.Be under 2 the situation, can list: 1,1,3 at g, 3,5,5-vegolysen, two (4-aminophenyl) trisiloxanes of 5-, 1,1,5,5-tetraphenyl-3,3-dimethyl-1, two (3-aminopropyl) trisiloxanes of 5-, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-two (the amino butyl of 4-) trisiloxanes, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-two (the amino amyl group of 5-) trisiloxanes, 1,1,5,5-tetramethyl-3,3-dimethoxy-1, two (2-amino-ethyl) trisiloxanes of 5-, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-two (the amino butyl of 4-) trisiloxanes, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-two (the amino amyl group of 5-) trisiloxanes, 1,1,3,3,5,5-vegolysen, two (3-aminopropyl) trisiloxanes of 5-, 1,1,3,3,5,5-Hexaethyl-1, two (3-aminopropyl) trisiloxanes and 1,1 of 5-, 3,3,5,5-six propyl group-1, two (3-aminopropyl) trisiloxanes of 5-.
Above-mentioned polyimide resin can use separately or use in the mode of the mixture more than 2 kinds.
About the vitrification point (Tg) of (d) composition, from adhesive composite the viewpoint of the attaching excellence of substrate, chip is considered, be preferably below 100 ℃, more preferably below 85 ℃.Under Tg is situation below 100 ℃, have easily and will be formed at concavo-convex imbedding such as the projection of semiconductor chip, the electrode that is formed at substrate, Wiring pattern by adhesive composite, can entrapped air pockets, be difficult for producing the tendency of pore.Illustrated that above-mentioned Tg is meant, used DSC (Perkin-Elmer corporate system DSC-7 type), at sample size 10mg, 10 ℃/minute of programming rates, to measure atmosphere be Tg when measuring under the conditions of air.
(d) weight average molecular weight of composition is counted more than 10000 with polystyrene conversion, but in order to show good film forming individually, is preferably more than 30000, more preferably more than 40000, more preferably more than 50000.Weight average molecular weight is 10000 when above, the tendency that then exists film forming and thermal endurance to improve.Illustrated that in this manual, weight average molecular weight is meant, uses high performance liquid chromatography (for example, Shimadzu Seisakusho Ltd.'s system, goods name " C-R4A "), the weight average molecular weight when measuring according to polystyrene conversion.
(d) content of composition is not particularly limited, but in order to keep membranaceous well, with respect to (a) composition 100 mass parts, is preferably 1～500 mass parts, more preferably 5～300 mass parts, more preferably 10～200 mass parts.(d) content of composition is 1 mass parts when above, has the tendency of the raising effect of easy acquisition film forming, is 500 mass parts when following, then has the tendency that curable improves, bonding force improves of adhesive composite.
(e) composition: flux activity agent
In adhesive composite of the present invention, can contain (e) composition, that is, and as the flux activity agent of the compound that shows flux activity (removing the activity of oxide, impurity).As the flux activity agent, list the nitrogen-containing compound, carboxylic acids, phenols and the alcohols that as imidazoles, amine, have unshared electron pair.
Among them, the flux activity of carboxylic acids is strong, with exist as the epoxy resin reaction of (a) composition, the state that in the solidfied material of adhesive composite, to dissociate, therefore can prevent the reduction of insulating reliability.
As carboxylic acids, for example can list: fat formula saturated carboxylic acid such as acetate, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, sad, n-nonanoic acid, capric acid, dodecylic acid, tetradecanoic acid, hexadecanoic acid, Heptadecanoic acide, octadecanoid acid; Fat formula unsaturated carboxylic acids such as oleic acid, linoleic acid, leukotrienes, arachidonic acid, DHA, eicosapentaenoic acid; Fat formula dicarboxylic acids such as maleic acid, fumaric acid, ethanedioic acid, malonic acid, butanedioic acid, glutaric acid, adipic acid; Benzoic acid, phthalic acid, M-phthalic acid, terephthalic acid (TPA), trimellitic acid, trimesic acid, 1,2,3-benzenetricarboxylic acid, PMA, pentane carboxylic acid, mellic acid aromatic carboxylic acids such as (mellitic acid).In addition, as carboxylic acid, for example can list lactic acid, malic acid, citric acid and salicylic acid with hydroxyl.
Further, also can use the substituting group that in above-mentioned aromatic carboxylic acid, has the electrophilic or the sub-property of powering, the fragrant family carboxylic acid that the acidity of the carboxylic acid on the aromatic series is changed according to substituting group.Have the tendency that the high more then flux activity of acidity of carboxylic acid improves more, but then have the situation that insulating reliability reduces when acidity is too high.Electron-attracting substituent as the acidity that improves carboxylic acid can list nitro, cyano group, trifluoromethyl, halogen group and phenyl.As the substituting group of the sub-property of the power supply of the acidity that weakens carboxylic acid, can list methyl, ethyl, isopropyl, the tert-butyl group, dimethylamino and trimethyl amino.Illustrated, about above-mentioned substituent number, position, if do not reduce flux activity, insulating reliability then be not particularly limited.
(other composition)
In the adhesive composite of present embodiment, in order to control the rerum natura of viscosity, solidfied material, and the air holes in order to suppress to have connected semiconductor chip and substrate, the rising of hydroscopicity, except (c) composition, also can further cooperate filler.
As filler, can use insulating properties inorganic filler, whisker or resin extender.As insulating properties inorganic filler, whisker or resin extender, can use and the same material of above-mentioned (c) composition.These fillers, whisker and resin extender can use a kind or use in the mode of the mixture more than 2 kinds individually.The shape of filler, average grain diameter and content are not particularly limited.
Further, in the adhesive composite of present embodiment, also can cooperate additives such as antioxidant, silane coupler, titanium coupling agent, levelling agent, ion trap agent.They can use a kind or use also capable of being combined more than 2 kinds separately.About their use level, suitably adjustment gets final product according to the mode of the effect that manifests each additive.
The adhesive composite of present embodiment can form membranaceous.Provide the manufacture method of the film-like adhesive of the adhesive composite that has used present embodiment below.At first, with (a) composition, (b) composition and (c) composition and (d) composition that adds as required or (e) become to grade and add in the organic solvent, dissolve or disperse by mix, mixing etc., thereby prepare resin varnish., implementing base material film that the demoulding handle on use blade coating machine, roll coater, spreader coating resin varnish,, thereby can on base material film, obtain film-like adhesive then by adding the heat abstraction organic solvent thereafter.
As the organic solvent that is used to prepare resin varnish, be preferably and have and the organic solvent of the characteristic of each composition uniform dissolution or dispersion for example can be able to be listed dimethyl formamide, dimethylacetylamide, N-N-methyl-2-2-pyrrolidone N-, dimethyl sulfoxide (DMSO), diethylene glycol dimethyl ether, toluene, benzene, dimethylbenzene, methylethylketone, oxolane, ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve, diox, cyclohexanone and ethyl acetate.These organic solvents can use separately or make up 2 kinds with on use.Preparation mixing during resin varnish, mixingly for example can use mixer, mixing and kneading machine, three-roll grinder, ball mill, ball mill and homogeneous dispersion machine (ホ モ デ ィ ス パ ー) and carry out.
As base material film, then be not particularly limited if having the stable on heating base material film of the heating condition in the time of can tolerating the volatilization organic solvent, can example illustrate: polyolefin films such as polypropylene screen, polymethylpentene film, polyester film, polyimide film and polyetherimde films such as PETG film, poly (ethylene naphthalate) film.Base material film is not subject to the base material film by these film formed individual layers, can be the multilayer film that is formed by the material more than 2 kinds yet.
Drying condition when coating the resin varnish volatilization organic solvent of base material film is preferably the condition of the organic solvent that volatilizees fully, specifically preferably carries out 50～200 ℃, 0.1～90 minute heating.
In addition,, consider, also can carry out drying as required, then wafer is carried out singualtion and use by directly being spun on the wafer from the viewpoint that improves operation about the adhesive composite of present embodiment.
＜semiconductor device＞
Below use Fig. 1 and 2 that the semiconductor device of present embodiment is described.Fig. 1 is the pattern cutaway view of an execution mode of expression semiconductor device of the present invention.Shown in Fig. 1 (a), semiconductor device 100 has: the semiconductor chip 10 and the substrate (circuit layout substrate) 20 of mutual subtend, be disposed at the distribution 15 of face of the mutual subtend of semiconductor chip 10 and substrate 20 respectively, with the distribution 15 interconnective connection projections 30 of semiconductor chip 10 and substrate 20, be filled in the adhesive composite 40 in the space of 20 of semiconductor chip 10 and substrates very close to each otherly.Semiconductor chip 10 and substrate 20 carry out flip-chip by distribution 15 and connection projection 30 and connect.Distribution 15 and connection projection 30 seal and block from external environment condition by adhesive composite 40.
Shown in Fig. 1 (b), semiconductor device 200 has: the semiconductor chip 10 and the substrate 20 of mutual subtend, be disposed at the projection 32 of face of the mutual subtend of semiconductor chip 10 and substrate 20 respectively, the adhesive composite 40 in the space that ground very close to each other filling semiconductor chip 10 and substrate are 20.Semiconductor chip 10 and substrate 20 projection 32 by subtend interconnects and carries out flip-chip and connect.Projection 32 seals and blocks from external environment condition by adhesive composite 40.
Fig. 2 is the pattern cutaway view of another execution mode of expression semiconductor device of the present invention.Shown in Fig. 2 (a), about semiconductor device 300, except 2 semiconductor chips 10 by distribution 15 and connect projection 30 and carry out flip-chip and connect this point, same with semiconductor device 100.Shown in Fig. 2 (b), about semiconductor device 400,, 2 semiconductor chips 10 connect this point except carrying out flip-chip by projection 32, and same with semiconductor device 200.
Be not particularly limited as semiconductor chip 10, can use compound semiconductors such as elemental semiconductor that the element by identical type such as silicon, germanium constitutes, GaAs, indium phosphide.
As substrate 20, if circuit substrate then is not particularly limited, can use: with glass epoxy resin (glass-epoxy), polyimides, polyester, pottery, epoxy resin, have on the surface for the insulated substrate of major ingredients such as Bismaleimide Triazine by the position that does not need metal film being carried out etching and remove the circuit substrate of the distribution (Wiring pattern) 15 that forms, formed the circuit substrate of distribution 15 by metal-plated etc. on the surface of above-mentioned insulated substrate, at the surface printing conductive material of above-mentioned insulated substrate and formed the circuit substrate of distribution 15.
For connecting portions such as distribution 15, projections 32, as main component, contain gold, silver, copper, scolding tin (main component for example is Xi-Yin, tin-lead, Sn-Bi, tin-copper, tin-silver-copper), nickel, tin, lead etc., also can contain multiple metal.
Among the above-mentioned metal, consider, be preferably gold, silver and copper, more preferably silver and copper from the viewpoint of the packaging body of the electrical conductivity of making connecting portion, excellent thermal conductivity.From making the viewpoint of the packaging body that cost lowered is considered, based on cheap and be preferably silver, copper and scolding tin, more preferably copper and scolding tin, further preferred scolding tin.When forming oxide-film, metallic surface then has the situation of productivity ratio reduction, the situation that cost increases in room temperature, therefore consider from the viewpoint of the formation that suppresses oxide-film, be preferably gold, silver, copper and scolding tin, more preferably gold, silver, scolding tin, further preferred gold, silver.
On the surface of above-mentioned distribution 15 and projection 32, also can be formed with gold, silver, copper, scolding tin (main component for example is Xi-Yin, tin-lead, Sn-Bi, tin-copper), tin, nickel etc. by for example plating be the metal level of major ingredients.This metal level also can only be assigned to constitute by single one-tenth, also can be made of multiple composition.In addition, above-mentioned metal level also can be made into individual layer or stacked multiple metal level and the structure that obtains.
In addition, such structure (packaging body) shown in also can stacked a plurality of semiconductor devices 100～400 in the semiconductor device of present embodiment.In the case, semiconductor device 100～400 also can reciprocally be electrically connected by the projection, the distribution that comprise gold, silver, copper, scolding tin (main component is for example Xi-Yin, tin-lead, Sn-Bi, tin-copper, tin-silver-copper), tin, nickel etc.
As the technology that a plurality of semiconductor devices are stacked, as shown in Figure 3, for example can list TSV (Through-Silicon Via) technology.Fig. 3 is the pattern cutaway view of another execution mode of expression semiconductor device of the present invention, and has been to use the semiconductor device of TSV technology.In semiconductor device shown in Figure 3 500, connect by being connected projection 30 with the distribution 15 of semiconductor chip 10 by making the distribution 15 that is formed on the intermediary layer (interposer) 50, thereby carrying out flip-chip with intermediary layer 50, semiconductor chip 10 is connected.Filling adhesive composite 40 in the space between semiconductor chip 10 and intermediary layer 50 very close to each otherly.In above-mentioned semiconductor chip 10 with intermediary layer 50 sides be on the surface of opposition side, by distribution 15, connect projection 30 and adhesive composite 40 and overlapping repeatedly semiconductor chip 10.The distribution 15 of the pattern plane at the surface of semiconductor chip 10 and place, the back side interconnects by the through electrode 34 in the hole that is filled in the inside that connects semiconductor chip 10.Illustrated,, can be used copper, aluminium etc. as the material of through electrode 34.
By such TSV technology, also can obtain signal from common obsolete semiconductor chip backside.Further, owing to make through electrode 34, therefore shorten between the semiconductor chip 10 of subtend, the distance between semiconductor chip 10 and the intermediary layer 50, can realize the connection of softness vertically by in the semiconductor chip 10.The adhesive composite of present embodiment, in such TSV technology, the encapsulating semiconductor bonding agent between the applicable semiconductor chip 10 of making subtend, between semiconductor chip 10 and the intermediary layer 50.
In addition, in the high projection formation method of the face projection chip technology degrees of freedom such as (エ リ ャ バ Application プ チ ッ プ skill Intraoperative), can former state semiconductor chip directly be installed on motherboard (マ ザ ー ボ ー De) by intermediary layer.The adhesive composite of present embodiment is also applicable to such situation that semiconductor chip directly is installed on motherboard.Illustrated, under the situation that 2 wired circuit boards is stacked, the also adhesive composite of applicable present embodiment when the space between substrate is sealed.
The manufacture method of＜semiconductor device＞
Below use Fig. 4 that the manufacture method of the semiconductor device of present embodiment is described.Fig. 4 is the operation cutaway view of an execution mode of the manufacture method of pattern ground expression semiconductor device of the present invention.
At first, shown in Fig. 4 (a), on substrate 20, be formed on and form the solder mask 60 that the position that connects projection 30 has opening with distribution 15.This solder mask 60 may not need to be provided with.But, by on substrate 20, solder mask being set, can suppress the generation of the electric bridge (Block リ ッ ジ) of 15 of distributions, can improve connection reliability, insulating reliability.Solder mask 60 for example can use commercially available packaging body to form with printing ink with solder mask.With solder mask printing ink, specifically can list SR series (Hitachi Chemical Co., Ltd.'s system, trade name) and PSR4000-AUS series (sun printing ink is made (strain) system, trade name) as commercially available packaging body.
Then, shown in Fig. 4 (a), at the opening part formation connection projection 30 of solder mask 60.Then shown in Fig. 4 (b), attach membranaceous adhesive composite (below, be called " film-like adhesive " according to circumstances) 40 on the substrate 20 that connects projection 30 and solder mask 60 being formed with.The attaching of film-like adhesive 40 can be undertaken by hot pressing, roll laminating, vacuum lamination etc.The supply area of film-like adhesive 40, thickness can be according to the sizes of semiconductor chip 10 and substrate 20, connect the height of projection 30 and suitably set.
After as described above film-like adhesive 40 being attached at substrate 20, use jockey such as flip-chip bond machine with the distribution 15 of semiconductor chip 10 be connected projection 30 and carry out aligned in position.Then, on one side to semiconductor chip 10 and the temperature heating on one side crimping of substrate 20 more than the fusing point that is connected projection 30, shown in Fig. 4 (c), semiconductor chip 10 is connected with substrate 20, and the space of 20 of semiconductor chip 10 and substrates is sealed filling by film-like adhesive 40.By more than, can obtain semiconductor device 600.
In the manufacture method of the semiconductor device of present embodiment, also can after having carried out aligned in position, carry out temporary fixed (Jie) by the state of semiconductor bonding agent, in reflow soldering, carry out heat treated, thereby will connect projection 30 fusions and semiconductor chip 10 is connected with substrate 20.In the temporary fixed stage and nonessential formation metal bond, while thereby be compared to the above-mentioned method that heat crimping, get final product based on the crimping of hanging down load, short time, low temperature, can boost productivity, and can suppress the deterioration of connecting portion.
In addition, also semiconductor chip 10 can be connected with substrate 20, carry out heat treated by baking oven etc. then, further improve connection reliability, insulating reliability.Heating-up temperature is preferably the temperature of the curing of carrying out film-like adhesive, more preferably the temperature of fully solidifying.Can suitably set heating-up temperature, heating time.
In the manufacture method of the semiconductor device of present embodiment, also can after film-like adhesive 40 is attached at semiconductor chip 10, substrate 20 be connected.In addition, also can be by distribution 15 and after connecting projection 30 semiconductor chip 10 and substrate 20 being connected, in the space of 20 of semiconductor chip 10 and substrates, fill the adhesive composite of pasty state.
Consider from the viewpoint that productivity ratio improves, also adhesive composite can be supplied in the semiconductor wafer that a plurality of semiconductor chips 10 are formed by connecting, cut then and carry out singualtion, thereby obtain on semiconductor chip 10, to supply with the structure that adhesive composite is arranged.In addition, be under the situation of pasty state at adhesive composite, be not particularly limited, but, the distribution on the semiconductor chip 10, projection imbedded by coating processes such as spin coatings, thickness is carried out homogenizing get final product.In this case, because the quantity delivered of resin becomes necessarily, thereby can make the productivity ratio raising, and can suppress by imbedding the air holes that deficiency causes and the reduction of cutting.On the other hand, under adhesive composite is membranaceous situation, be not particularly limited, get final product but supply with membranaceous resin combination according to the mode of imbedding distribution on the semiconductor chip 10, projection by attaching modes such as hot pressing, roll laminating and vacuum laminations.In this case, the quantity delivered of resin becomes necessarily, thereby productivity ratio is improved, and can suppress by imbedding the air holes that deficiency causes and the reduction of cutting.
Connect load consider to connect the deviation of the quantity of projection 30, height, based on the connection projection 30 of pressurization or accept connecting portion projection distribution deflection and set.About connecting temperature, the temperature of preferred connecting portion gets final product so long as can form the temperature of the metal bond of each connecting portion (projection, distribution) for more than the fusing point that connects projection 30.Connecting projection 30 is under the situation of solder bump, is preferably about more than 240 ℃.
Connect hours during connection is different because of the formation metal of connecting portion, but considers to be that the short time is then preferred more more from the viewpoint that productivity ratio improves.Connecting projection 30 is under the situation of solder bump, and the connect hours was preferably below 20 seconds, more preferably below 10 seconds, more preferably below 5 seconds.Under the situation that the metal of copper-copper or copper-Jin connects, the connect hours was preferably below 60 seconds.
Even at the flip-chip connecting portion of above-mentioned various package body structures, adhesive composite of the present invention also shows excellent reflux-resisting welded property, connection reliability and insulating reliability.
Embodiment
Below use embodiment, comparative example and the present invention is described, but the present invention is not subject to following embodiment.
(polyimides is synthetic)
To possessing thermometer is arranged, in the 300mL flask of mixer and calcium chloride tube, add 1,12-diaminourea dodecane 2.10g (0.035 mole), polyether diamine (BASF system, trade name " ED2000 ", molecular weight: 1923) 17.31g (0.03 mole), 1, two (3-aminopropyl) tetramethyl disiloxanes of 3-(SHIN-ETSU HANTOTAI's chemistry system, trade name " LP-7100 ") 2.61g (0.035 mole) and N-N-methyl-2-2-pyrrolidone N-(Northeast chemistry system, hereinafter referred to as " NMP ") 150g and stirring.Behind above-mentioned two amine solvents, on one side flask is cooled off in ice bath, added slightly on one side at every turn by acetic anhydride carry out again crystal refining and obtain 4,4 '-(4,4 '-isopropylidene, two phenoxy groups) two (O-phthalic acid dianhydrides) (ALDRICH system, trade name " BPADA ") 15.62g (0.10 mole).After at room temperature reacting 8 hours, add dimethylbenzene 100g,, together the dimethylbenzene azeotropic is removed, obtained polyimide resin with water while be blown into nitrogen 180 ℃ of heating.Remove solvent (NMP) from the polyimide resin that obtained, will be dissolved in methylethylketone (MEK) and the material that obtains is made as " polyimides A " according to the mode that becomes solid constituent 50 quality %.The Tg of polyimides A is 30 ℃, and weight average molecular weight is 50000, and SP value (solubility parameter) is 10.2.
The compound that uses in each embodiment and each comparative example is as described below.
(a) epoxy resin
(japan epoxy resin Co., Ltd. system, trade name " EP1032H60 " is hereinafter referred to as " EP1032 " to contain the multifunctional solid epoxy resin of triphenol methylmethane skeleton.)
(japan epoxy resin Co., Ltd. system, trade name " YL983U " is hereinafter referred to as " YL983 " for Bisphenol F type liquid epoxy resin.)
(japan epoxy resin Co., Ltd. system, trade name " YL7175 " is hereinafter referred to as " YL7175 " for flexibility epoxy resin.)
(b) curing agent
2-phenyl-4, (four countries change into Co., Ltd.'s system to 5-dihydroxy methylimidazole, and trade name " 2PHZ-PW " is hereinafter referred to as " 2PHZ ".)
2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-(four countries change into Co., Ltd.'s system to ethyl-s-triazine isocyanuric acid addition product, and trade name " 2MAOK-PW " is hereinafter referred to as " 2MAOK ".)
(c) acrylic acid series surface treatment filler or have filler by the group of above-mentioned general formula (1) expression
(average grain diameter 0.5 μ m is hereinafter referred to as " SM silicon dioxide " for the Admatechs of Co., Ltd. system, trade name " SE2050-SMJ " for methacrylic acid surface treatment silica filler.)
(Admatechs of Co., Ltd. system, trade name " YA050C-SM " is hereinafter referred to as " SM nano silicon " for methacrylic acid surface treating nano silica filler.)
(c ') other filler
The untreated silica filler (Admatechs of Co., Ltd. system, trade name " SE2050 ", average grain diameter 0.5 μ m, below, be called " silicon dioxide is untreated ".)
(average grain diameter 0.5 μ m is hereinafter referred to as " SX silicon dioxide " for the Admatechs of Co., Ltd. system, trade name " SE2050-SXJ " for the aminosilane-treated silica filler.)
Epoxy silane is handled silica filler, and (average grain diameter 0.5 μ m is hereinafter referred to as " SE silicon dioxide " for the Admatechs of Co., Ltd. system, trade name " SE2050-SEJ ".)
Phenyl silane is handled silica filler, and (average grain diameter 0.5 μ m is hereinafter referred to as " SP silicon dioxide " for the Admatechs of Co., Ltd. system, trade name " SE2050-SPJ ".)
(average grain diameter 50nm is hereinafter referred to as " SP nano silicon " for the Admatechs of Co., Ltd. system, trade name " YA050C-SP " for phenyl surface treating nano silica filler.)
(the beautiful sun system of Mitsubishi, trade name " W5500 " is hereinafter referred to as " W5500 " in organic filler (1).)
(hud typed organic fine particles is hereinafter referred to as " EXL2655 " for Rohm and Haas Japan (strain) corporate system, trade name " EXL-2655 " in organic filler (2).)
(d) macromolecule component of molecular weight more than 10000
Phenoxy resin (Toto Kasei KK's system, trade name " ZX1356 ", Tg: about 71 ℃, Mw: about 63000, hereinafter referred to as " ZX1356 ".)
The polyimides A that synthesizes as described above
(e) flux activity agent (solder flux, Off ラ ッ Network ス drug)
Diphenoliac acid (Tokyo changes into Co., Ltd.'s system)
Adipic acid (Wako Pure Chemical Industries, Ltd.'s system)
The making of＜encapsulating semiconductor usefulness film-like adhesive＞
(embodiment 1)
Is that the mode of 60 quality % is reinforced with epoxy resin (EP1032) 100 mass parts, curing agent (2PHZ) 7.5 mass parts, filler (SM silicon dioxide) 175 mass parts, flux activity agent (diphenoliac acid) 25 mass parts and MEK solvent according to solid constituent, the microballon of diameter 0.8mm and microballon and the solid constituent of diameter 2.0mm are added as such, utilize ball mill (Fritsch Japan Co., Ltd., planet-shaped atomizer " P-7 ") to stir 30 minutes.Then, add polyimides A100 mass parts (press the solid constituent conversion), utilize ball mill once more and after stirring 30 minutes, remove the microballon that is used to stir, obtained resin varnish by filtration.
Utilize miniature precision apparatus for coating (the smart mechanism of Lian Jing) that the resin varnish that is obtained is coated base material film (film Co., Ltd. of Supreme Being people Du Pont system, trade name " PUREX A53 "), in cleaning oven (ESPEC Co., Ltd. system),, thereby produce film-like adhesive 70 ℃ of dryings 10 minutes.
(embodiment 2～3 and comparative example 1～6)
Table 1 described as follows has changed employed raw-material composition like that, in addition, produces the film-like adhesive of embodiment 2～3 and comparative example 1～6 similarly to Example 1.
Below, provide evaluation method by the film-like adhesive of embodiment and comparative example acquisition.
Determination of Modulus under＜260 ℃＞
Film-like adhesive is cut the size (length 37mm * width 4mm * thickness 0.13mm) of regulation, in cleaning oven (ESPEC Co., Ltd. system), kept 3 hours and solidify at 180 ℃.After the curing, use determination of viscoelasticity device (Rheometrics system, trade name " RASII "), the modulus of elasticity under 260 ℃ of the arrival temperature of the reflow soldering when determining as reflux-resisting welded property evaluation.Mensuration with temperature range-30～270 ℃, 5 ℃/minute of programming rates, measure wavelength 10Hz and carry out.
The mensuration of the bonding force under 260 ℃ after the＜moisture absorption＞
Film-like adhesive is cut the size (length 5mm * width 5mm * thickness 0.025mm) of regulation, be attached at silicon (length 5mm * width 5mm * thickness 0.725mm, oxide-film coating) at 60 ℃, use thermo-compressed testing machine (Hitachi changes into Techno-Plant Co., Ltd. system), be crimped on glass epoxy resin substrate (thickness 0.02mm) (the crimping condition: 180 ℃/10 seconds/0.5MPa of the arrival temperature of film-like adhesive that is coated with solder mask (sun printing ink system, trade name " AUS308 ").Then, the arrival temperature of film-like adhesive 245 ℃/10 seconds/0.5MPa).Then, in cleaning oven (ESPEC Co., Ltd. system), carried out back curing (aftercure) (180 ℃/3 hours).Thereafter, 85 ℃, Constant Temperature and Humidity Chambers (ESPEC Co., Ltd. system of relative humidity 60%, trade name " PR-2KP ") placed 48 hours in, after the taking-up, on 260 ℃ hot plate, use bonding force determinator (DAGE corporate system, the bonding detector DAGE4000 of universal type type), under the instrument (tool) of substrate height 0.05mm, the instrument speed 0.05mm/ condition of second, measuring.
＜initial internuncial evaluation＞
The film-like adhesive of made is cut the size (length 8mm * width 8mm * thickness 0.025mm) of regulation, (the glass epoxy resin base material: 420 μ m are thick to be attached at the glass epoxy resin substrate, copper wiring: 9 μ m are thick, 80 μ m spacings) on, with flip-chip erecting device " FCB3 " (PANASONIC system, trade name) will have semiconductor chip (chip size: length 7mm * width 7mm * height 0.15mm, the projection: copper post and scolding tin of solder bump, 80 μ m spacings) (mounting condition: 180 ℃ of the arrival temperature of film-like adhesive is installed, 10 seconds, 0.5MPa.Then, the arrival temperature of film-like adhesive 245 ℃, 10 seconds, 0.5MPa).Thus, obtained similarly to make above-mentioned glass epoxy resin substrate and the semiconductor chip that has solder bump carry out that daisy chain (デ ィ ジ ー チ ェ ー Application) is connected and the semiconductor device that obtains with Fig. 4.
Use universal instrument (ADVANTEST system, trade name " R6871E ") to measure the connection resistance value of the semiconductor device that is obtained, thereby estimate carrying out initial conducting after installing.With connecting resistance value is that the average evaluation of 11～14 Ω is connectivity good " A ", with the situation of in addition connection resistance value or bad connection (Open) takes place and do not show that the average evaluation of resistance value is " B ".
The evaluation of＜reflux-resisting welded property＞
Use encapsulant (Hitachi Chemical Co., Ltd.'s system, trade name " CEL9700HF10K "), under 180 ℃, 6.75MPa, 90 seconds condition, with the shape of above-mentioned semiconductor device mold for regulation, in cleaning oven (ESPEC Co., Ltd. system), obtained packaging body 175 ℃ of curing 5 hours.Then, after under the JEDEC level2 condition this packaging body being carried out the high temperature moisture absorption, packaging body is passed through in IR reflow soldering (FURUKAWA ELECTRIC system, trade name " SALAMANDER ").By estimating the connectivity of the packaging body after the Reflow Soldering, as the evaluation of reflux-resisting welded property with the same method of initial internuncial evaluation described later.To not peel off, connect good situation and be made as " A ", with peel off, bad connection and do not show that the situation of resistance value is made as " B ".
The evaluation of＜connection reliability (anti-TCT estimates)＞
Use encapsulant (Hitachi Chemical Co., Ltd.'s system, trade name " CEL9700HF10K "), under 180 ℃, 6.75MPa, 90 seconds condition with the shape of above-mentioned semiconductor device mold for regulation, in cleaning oven (ESPEC Co., Ltd. system), obtained packaging body 175 ℃ of curing 5 hours.Then, this packaging body is positioned over thermal cycling test machine (ETAC system, THERMAL SHOCK CHAMBER NT1200) in, flow through the electric current of 1mA, 25 ℃ 2 minutes/-55 ℃ 15 minutes/25 ℃ 2 minutes/125 ℃ 15 minutes/25 ℃ were made as 1 circulation in 2 minutes and measure and connect resistance, the connection changes in resistance of carrying out repeatedly after 1000 circulations is estimated.Compare with initial resistance value waveform, will after 1000 circulations, also not have the situation of big variation to be made as " A ", the situation that has produced the difference more than 1 Ω is made as " B ".
The evaluation of＜insulating reliability (anti-HAST estimates)＞
The film-like adhesive of made is cut the size (length 10mm * width 5mm * thickness 25 μ m) of regulation, be attached at comb-type electrode substrate (the wiring closet distance: 0.05mm) that on polyimide substrate, is formed with the distribution copper wiring, as shown in Figure 5, produce stacked film-like adhesive 40 on the substrate 20 that is formed with comb-type electrode 90 and the sample that obtains.Illustrated, in Fig. 5, omitted the diagram of film-like adhesive for convenience.Then, sample is solidified 185 ℃ of maintenances 3 hours in cleaning oven (ESPEC Co., Ltd. system).After the curing, take out each sample, be arranged at accelerated life test device (condition: 85%/200 hour/5V of 130 ℃/relative humidity applies for HIRAYAMA corporate system, trade name " PL-422R8 "), measured insulation resistance.Through 200 hours, be 10 with insulation resistance 8The above situation of Ω is established and is evaluated as " A ", with less than 10 8The average evaluation of Ω is " B ".
Raw-material composition (unit: mass parts) be shown in Table 1, with the adhesive composite of each embodiment and each comparative example with the table 2 that the results are shown in of each test.
Table 1
Figure BDA00002982623900301
Table 2
Figure BDA00002982623900302
Confirmed: in the embodiment 1～3 that has used acrylic acid series surface treatment filler, the bonding force height under 260 ℃ after the moisture absorption, any characteristic among reflux-resisting welded property, anti-TCT and the anti-HAST is all excellent.
Symbol description
10 semiconductor chips, 15 distributions (connecting portion), 20 substrates (wired circuit board), 30 connect projection, 32 projections (connecting portion), 34 through electrodes, 40 adhesive composites (film-like adhesive), 50 intermediary layers, 60 solder masks, 90 comb-type electrodes, 100,200,300,400,500,600 semiconductor devices.

Claims (10)

1. adhesive composite, in its semiconductor device that reciprocally is electrically connected for the connecting portion separately of the semiconductor device that reciprocally is electrically connected at the connecting portion separately of semiconductor chip and wired circuit board or a plurality of semiconductor chips with the adhesive composite of described connecting portion sealing
It contains epoxy resin, curing agent and has carried out surface-treated acrylic acid series surface treatment filler by the compound with the group shown in the following general formula (1),
Figure FDA00002982623800011
In the formula (1), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30.
2. adhesive composite according to claim 1, wherein, described compound is the compound by following general formula (2) expression,
Figure FDA00002982623800012
In the formula (2), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30, R 3The alkyl of expression carbon number 1～30.
3. adhesive composite, in its semiconductor device that reciprocally is electrically connected for the connecting portion separately of the semiconductor device that reciprocally is electrically connected at the connecting portion separately of semiconductor chip and wired circuit board or a plurality of semiconductor chips with the adhesive composite of described connecting portion sealing
The filler that it contains epoxy resin, curing agent and has the group shown in the following general formula (1),
Figure FDA00002982623800013
In the formula (1), R 1The alkyl of expression hydrogen atom or carbon number 1 or 2, R 2The alkylidene of expression carbon number 1～30.
4. according to each described adhesive composite in the claim 1～3, it further contains weight average molecular weight is macromolecule component more than 10000.
5. adhesive composite according to claim 4, wherein, the weight average molecular weight of described macromolecule component is more than 30000, vitrification point is below 100 ℃.
6. according to each described adhesive composite in the claim 1～5, it further contains the flux activity agent.
7. according to each described adhesive composite in the claim 1～6, it is shaped as membranaceous.
8. the manufacture method of a semiconductor device, the manufacture method of the semiconductor device that the semiconductor device that it reciprocally is electrically connected for the connecting portion separately of semiconductor chip and wired circuit board or the connecting portion separately of a plurality of semiconductor chips reciprocally are electrically connected
It possesses the operation that each described adhesive composite seals described connecting portion in the use claim 1～7.
9. manufacture method according to claim 8, wherein, described connecting portion contains at least a metal that is selected from gold, silver, copper, nickel, tin and the lead as main component.
10. semiconductor device, it obtains by claim 8 or 9 described manufacture methods.
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