CN103222040B - The manufacture method of adhesive composite, semiconductor device and semiconductor device - Google Patents

The manufacture method of adhesive composite, semiconductor device and semiconductor device Download PDF

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Publication number
CN103222040B
CN103222040B CN201180047053.3A CN201180047053A CN103222040B CN 103222040 B CN103222040 B CN 103222040B CN 201180047053 A CN201180047053 A CN 201180047053A CN 103222040 B CN103222040 B CN 103222040B
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Prior art keywords
curing agent
system curing
adhesive composite
semiconductor device
carbon number
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CN201180047053.3A
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CN103222040A (en
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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
    • H—ELECTRICITY
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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 a kind of adhesive composite, the adhesive composite sealed by connecting portion in the semiconductor device that its respective connecting portion being the semiconductor device that is reciprocally electrically connected at the respective connecting portion of semiconductor chip and wired circuit board or multiple semiconductor chip is reciprocally electrically connected, described adhesive composite contains epoxy resin, curing agent and acrylic acid series surface treatment filler.

Description

The manufacture method of adhesive composite, semiconductor device and semiconductor device
Technical field
The present invention relates to adhesive composite, the manufacture method of semiconductor device and semiconductor device.
Background technology
In recent years, in order to be installed by semiconductor chip and be connected to substrate, the wire-bonded mode of the metal fines such as use spun gold (goldwire) has been widely used.On the other hand, in order to tackle for requirements such as the miniaturization of semiconductor device, slimming, high function, highly integrated, high speeds, between semiconductor chip with substrate, form the conductivity projection being called projection and flip-chip connected mode (FC connected mode) that semiconductor chip is connected with substrate in lasting expansion.
Such as, about the connection between semiconductor chip and substrate, the connected mode of active COB (ChipOnBoard) type be applied in BGA (BallGridArray), CSP (ChipSizePackage) etc. is also equivalent to FC connected mode.In addition, FC connected mode is also widely used in being formed on a semiconductor die connecting portion (projection, distribution) and by (such as with reference to patent documentation 1) in the connected mode of COC (ChipOnChip) type that connects between semiconductor chip.
But, in order to tackle further miniaturization, slimming, multifunction requirement, above-mentioned connected mode being carried out stacked, multistage chip stack stack-type packaging body (chipstacktypepackage), POP (PackageOnPackage), TSV (Through-SiliconVia) etc. and also starting extensively universal.Owing to dimensionally being configured by semiconductor chip etc. in stacked multistage technology like this, thus comparatively speaking packaging body can be reduced with the method configured two-dimensionally.Particularly, TSV technology improves for the performance of semiconductor, noise reducing, erection space are cut down, electric power savingization is also effective, and the semiconductor layout techniques as a new generation receives concern.
But, as the major metal for above-mentioned connecting portion (projection, distribution), there are scolding tin, tin, gold, silver, copper, nickel etc., also use the multiple electric conducting material comprised in them.About the metal for connecting portion, generate oxide-film because oxidation occurs on surface, at impurity such as surface attachment oxides, have the situation generating impurity at the joint face of connecting portion.During remaining such impurity, then have following possibility: the advantage of the connected mode connectivity between semiconductor chip and substrate, between 2 semiconductor chips, insulating reliability are reduced, making employing above-mentioned is impaired.
As suppressing the generation of these impurity and improving internuncial method, the method before proceeding surface of substrate, semiconductor chip being implemented to pre-treatment can be listed, can list be applied for OSP (OrganicSolderbilityPreservatives) and process pre-solder flux, anti-rust agent for treatment method.But, also there is the situation because thus remaining the and deterioration of solder flux pre-after pre-treatment, anti-rust agent for treatment causes connectivity to reduce.
On the other hand, according to by the method for semiconductor-encapsulating material (encapsulating semiconductor bonding agent) by the connecting portion sealing between semiconductor chip and substrate etc., while semiconductor chip and substrate, semiconductor chip connection each other, connecting portion can be sealed.Therefore, the oxidation of the metal for connecting portion, impurity can be suppressed the attachment of connecting portion, and protect connecting portion not by the infringement of external environment condition.Therefore, connectivity, insulating reliability, workability, productivity ratio can effectively be improved.
In addition, in the semiconductor device manufactured by flip-chip connected mode, in order to not make to be derived from the coefficient of thermal expansion differences of semiconductor chip and substrate, the thermal stress of semiconductor chip coefficient of thermal expansion differences each other concentrates on connecting portion and causes bad connection, thus needs the gap seals between semiconductor chip and substrate etc. with semiconductor-encapsulating material.Particularly, at semiconductor chip and the composition often using thermal coefficient of expansion different in substrate, require undertaken sealing by semiconductor-encapsulating material and improve resistance to sudden heating.
In the sealing means adopting above-mentioned semiconductor-encapsulating material, carry out larger differentiation and capillary flow flowing mode (Capillary-Flow) and pre-feed mode (Pre-applied) (such as with reference to patent documentation 2 ~ 6) can be listed.Capillary flow flowing mode refers to, the mode flow into aqueous semiconductor-encapsulating material between semiconductor chip and substrate space by capillarity after the connection of semiconductor chip and substrate in.Pre-feed mode refers to, before the connection of semiconductor chip and substrate, to semiconductor chip or substrate supply pasty state, membranaceous semiconductor-encapsulating material, then by mode that semiconductor chip is connected with substrate.About these sealing means, along with the progress of the miniaturization of semiconductor device in recent years, space between semiconductor chip and substrate etc. has narrowed, thus have in capillary flow flowing mode: inject the situation needing long-time and productivity ratio to reduce, situation about cannot inject, in addition, also there is non-filling part and the situation becoming the reason of pore even if can inject.Therefore, from the viewpoint of workability, productivity ratio, reliability, pre-feed mode as can realize high function, high integrated, high speed packaging body manufacture method and become main flow.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2008-294382 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2001-223227 publication
Patent documentation 3: Japanese Unexamined Patent Publication 2002-283098 publication
Patent documentation 4: Japanese Unexamined Patent Publication 2005-272547 publication
Patent documentation 5: Japanese Unexamined Patent Publication 2006-169407 publication
Patent documentation 6: Japanese Unexamined Patent Publication 2006-188573 publication
Summary of the invention
The problem that invention will solve
In above-mentioned pre-feed mode, due to by heating pressurization while being undertaken connecting, by semiconductor-encapsulating material by the gap seals between semiconductor chip and substrate, thus need to consider condition of contact and select semiconductor-encapsulating material containing composition.Generally speaking, in connecting portion connection each other, from the viewpoint of fully guaranteeing connectivity, insulating reliability employs metal bond.Because metal bond is the use of the connected mode of high temperature (such as more than 200 DEG C), therefore have following situation: result from volatile ingredient remaining in semiconductor-encapsulating material, because of the decomposition containing composition of semiconductor-encapsulating material newly-generated volatile ingredient, semiconductor-encapsulating material produces foaming.Thus, produce the bubble being referred to as pore, semiconductor-encapsulating material is from semiconductor chip, strippable substrate.In addition, when heat pressurization time, earth pressure release time, when producing resilience (springback) of above-mentioned pore, semiconductor chip etc., produce the bad connections such as the destruction of the connecting portion caused by the tearing of connection projection be connected to each other by connecting portion.Due to these reasons, in semiconductor-encapsulating material in the past, thus have the possibility of connectivity, insulating reliability reduction.
In addition, when semiconductor-encapsulating material does not have sufficient flux activity (oxide-film of metal surface, the removal effect of impurity), have oxide-film, the impurity that cannot remove metal surface, good metal-metal can not be formed and engage, the situation of conducting cannot be guaranteed.Further, when the insulating reliability of semiconductor-encapsulating material is low, is then difficult to the narrow spacing tackling connecting portion, defective insulation occurs.Also due to these reasons, in semiconductor-encapsulating material in the past, the possibility of connectivity, insulating reliability reduction is had.
About the semiconductor device using semiconductor-encapsulating material to manufacture, require to realize sufficient level in reliability, more specifically thermal endurance, moisture-proof and reflux-resisting welded property (フ of resistance to リ ロ ー).In order to ensure reflux-resisting welded property, thus require at the Reflow Soldering temperature of 260 DEG C of front and back, maintenance can suppress the stripping of patch layer (ダ イ ボ Application De Layer) (bond layer) or destroy such high adhesive strength.
The present invention develops in view of said circumstances, its object is to provide the adhesive composite of the semiconductor device that can make reflux-resisting welded property and connection reliability and insulating reliability excellence, the manufacture method employing the semiconductor device of this adhesive composite and semiconductor device.
For the scheme of dealing with problems
The invention provides a kind of adhesive composite, the adhesive composite sealed by connecting portion in the semiconductor device that its respective connecting portion being the semiconductor device that is reciprocally electrically connected at the respective connecting portion of semiconductor chip and wired circuit board or multiple semiconductor chip is reciprocally electrically connected, 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 following general formula (1).
[chemical formula 1]
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
The present invention provides a kind of adhesive composite in addition, the adhesive composite sealed by connecting portion in the semiconductor device that its respective connecting portion being the semiconductor device that is reciprocally electrically connected at the respective connecting portion of semiconductor chip and wired circuit board or multiple semiconductor chip is reciprocally electrically connected, it contains epoxy resin, curing agent and has the filler of the group shown in following general formula (1).
[chemical formula 2]
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
The adhesive composite of the invention described above is by the basis containing epoxy resin and curing agent, further containing acrylic acid series surface treatment filler or the filler with the group represented by above-mentioned general formula (1), even if thus when high temperature (such as more than 200 DEG C) carry out in the flip-chip connected mode of metal bond be suitable for make encapsulating semiconductor 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, need the bonding force after the moisture absorption under raising high temperature.But the filler always used can reduce hydroscopicity and thermal coefficient of expansion, in order to improve connectivity, insulating reliability is effective, but the cementability of filler self lacks usually.
Known herein, make silane coupler with do not carry out surface-treated filler together containing in resin time, then the surface of filler can be made to carry out silane coupled process, synthesized the filler of various surface state by the substituting group of silane coupler.But the volatility of silane coupler is high, in the manufacturing process of semiconductor device with the technique under the high temperature such as the metal bond that needs high temperature conjunction, become the reason producing pore.Similarly, under surface-treated situation is carried out to the filler always used, have the organic situation that volatility such as producing methyl alcohol is high, become pore Producing reason.
Generally speaking, be formed with the dielectric film being referred to as solder mask on a semiconductor substrate, solder mask includes acrylic material mostly.Therefore, the present inventor etc. have found, by containing aforesaid propylene acid being surface treatment filler or the filler with the group represented by above-mentioned general formula (1), thus improving the bonding force after adhesive composite modulus of elasticity at high temperature and moisture absorption, reflux-resisting welded property can be realized.The suppositions such as the present inventor, in adhesive composite of the present invention, use the filler having carried out surface-treated acrylic acid series surface treatment filler in advance or there is the group represented by above-mentioned general formula (1), thus the generation of the material that volatility is high can be suppressed, and thus can improve the connectivity with substrate due to acrylic compounds and the excellent in adhesion of solder mask.The present inventor waits supposition in addition, acrylic acid series surface treatment filler or the filler with the group represented by above-mentioned general formula (1) not easily reduce the insulating reliability of connecting portion, not easily reduce thermal coefficient of expansion and the modulus of elasticity of the solidfied material of adhesive composite, therefore can improve connection reliability.
Acrylic acid series surface treatment filler or there is the group represented by above-mentioned general formula (1) filler to the excellent dispersion in resinous principle, and can improve and use adhesive composite of the present invention and the intensity of packaging body (substrate-chip, chip-chip etc.) terminal part in the semiconductor device that makes.
Above-mentioned bonding force raising is not limited on solder mask, is apparent in (SiO, SiN etc.) between semiconductor chip yet.
The compound that the compound with the group represented by above-mentioned general formula (1) is preferably represented by following general formula (2).
[chemical formula 3]
In formula (2), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30, R 3represent the alkyl of carbon number 1 ~ 30.
Adhesive composite of the present invention has carried out surface-treated filler by containing by the compound shown in above-mentioned general formula (2), thus can further improve reflux-resisting welded property, connection reliability and insulating reliability.
In adhesive composite of the present invention, from the viewpoint of the thermal endurance and the film forming that improve adhesive composite, can contain weight average molecular weight is further the macromolecule component of more than 10000.
From the viewpoint of the attaching, the film forming that improve adhesive composite further, the weight average molecular weight of above-mentioned macromolecule component is preferably more than 30000, and vitrification point is preferably less than 100 DEG C.
Adhesive composite of the present invention, by further containing flux activity agent, can improve flux activity, removes oxide-film, the impurity of the metal surface of connecting portion, can form good metal-metal and engage.
Owing to can improve by pre-feed mode by workability when gap seals between the space of semiconductor chip and wired circuit board or multiple semiconductor chip, therefore 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 respective connecting portion of the semiconductor device that its respective connecting portion being semiconductor chip and wired circuit board is reciprocally electrically connected or multiple semiconductor chip is reciprocally electrically connected, described method possesses the operation using above-mentioned adhesive composite to be sealed by connecting portion.
According to the manufacture method of semiconductor device of the present invention, by using above-mentioned adhesive composite, thus the reflux-resisting welded property of semiconductor device, connection reliability and insulating reliability can be improved.
Above-mentioned connecting portion contains when being selected from least one metal in gold, silver, copper, nickel, tin and lead as main component, then can further improve the electrical conductivity of connecting portion, thermal conductivity, connection reliability.
The present invention provides the semiconductor device obtained by the manufacture method of above-mentioned semiconductor device in addition.
Semiconductor device of the present invention makes owing to using the manufacture method of above-mentioned semiconductor device, thus becomes the semiconductor device that reflux-resisting welded property, connection reliability and insulating reliability are fully excellent.
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, the manufacture method employing the semiconductor device of this adhesive composite and semiconductor device.Accompanying drawing explanation
Fig. 1 is the pattern cutaway view of the execution mode representing semiconductor device of the present invention.
Fig. 2 is the pattern cutaway view of another execution mode representing semiconductor device of the present invention.
Fig. 3 is the pattern cutaway view of another execution mode representing semiconductor device of the present invention.
Fig. 4 be pattern represent the operation cutaway view of an execution mode of the manufacture method of semiconductor device of the present invention.
Fig. 5 is the ideograph of the outward appearance of the sample representing insulating reliability test.
Embodiment
Below, optionally with reference to accompanying drawing while be described in detail to the preferred embodiment of the present invention.Be explained, in the accompanying drawings, same or equivalent part pays same-sign and the repetitive description thereof will be omitted.In addition, waiting position relationship as long as no illustrating in advance especially up and down, being just set to the position relationship based on position relationship shown in the drawings.Further, the dimensional ratios of accompanying drawing is not limited to illustrated ratio.
< adhesive composite >
The adhesive composite (encapsulating semiconductor bonding agent) of present embodiment be semiconductor chip and wired circuit board (following, optionally and referred to as " substrate ") the semiconductor device that is reciprocally electrically connected of respective connecting portion, or by adhesive composite that connecting portion seals in the semiconductor device that is reciprocally electrically connected of the respective connecting portion of multiple semiconductor chip, it is (following that it contains epoxy resin, optionally be called " (a) composition "), curing agent is (following, optionally be called " (b) composition "), and acrylic acid series surface treatment filler or to have the filler of the group represented by above-mentioned general formula (1) (following, optionally be called " (c) composition ").In addition, the macromolecule component of adhesive composite as required containing weight average molecular weight more than 10000 is (following, optionally be called " (d) composition ") or flux activity agent (following, be optionally called " (e) composition ".)。Below each composition of the adhesive composite forming present embodiment is described.
(a) composition: epoxy resin
As epoxy resin, if the epoxy resin in molecule with the epoxy radicals of more than 2 then can use with being not particularly limited.As (A) composition, bisphenol A-type, bisphenol-f type, naphthalene type, phenol novolak type, cresol novolak type, phenol aralkyl type, biphenyl type, triphenyl methane type, dicyclopentadiene type and various polyfunctional epoxy resin specifically can be used.They can be used alone or use in the mode of mixture of more than two kinds.
About (a) composition, this situation of volatile ingredient is produced from the viewpoint of decomposing during the connection suppressed at high temperature, temperature when connecting is 250 DEG C, thermogravimetric weight loss dose rate (a small amount of rate of Hot Chong Liang Minus) at preferred use 250 DEG C is the epoxy resin of less than 5%, when 300 DEG C, the thermogravimetric weight loss dose rate at preferably using 300 DEG C is the epoxy resin of less than 5%.
(b) composition: curing agent
As (b) composition, include, for example out phenolic resins system curing agent, acid anhydrides system curing agent, amine system curing agent, imidazoles system curing agent and phosphine system curing agent.If (b) composition comprises phenolic hydroxyl group, acid anhydrides, amine or imidazoles, so can manifest the flux activity suppressing to produce this situation of oxide-film at connecting portion, connection reliability, insulating reliability can be improved.Below each curing agent is described.
(i) phenolic resins system curing agent
As phenolic resins system curing agent, if the phenolic resins system curing agent in molecule with the phenolic hydroxyl group of more than 2 is then not particularly limited, such as, can use phenol novolacs, cresol novolak, phenol aralkyl resin, cresol naphthol formaldehyde condensation products, the multifunctional phenolic aldehyde of triphenyl methane type and various multifunctional phenolic resins.They can be used alone or use in the mode of mixture of more than two kinds.
Phenolic resins system curing agent is preferably 0.3 ~ 1.5 relative to the equivalent proportion (phenolic hydroxyl group/epoxy radicals, mol ratio) of above-mentioned (a) composition from the viewpoint of good curability, cementability and storage stability, be more preferably 0.4 ~ 1.0, more preferably 0.5 ~ 1.0.When equivalent proportion is more than 0.3, then there is curability and improve and the tendency of bonding force raising, when being less than 1.5, then there is unreacted phenolic hydroxyl group can not be excessively remaining, is suppressed by water absorption rate for low, the tendency that insulating reliability improves.
(ii) acid anhydrides system curing agent
As acid anhydrides system curing agent, such as, can use hexahydrotoluene tetracarboxylic dianhydride, trimellitic anhydride, pyromellitic acid dianhydride, benzophenone tetracarboxylic dianhydride and ethylene glycol bis dehydration trimellitate.They can be used alone or use in the mode of mixture of more than two kinds.
Acid anhydrides system curing agent is preferably 0.3 ~ 1.5 relative to the equivalent proportion (anhydride group/epoxy radicals, mol ratio) of above-mentioned (a) composition from the viewpoint of good curability, cementability and storage stability, be more preferably 0.4 ~ 1.0, more preferably 0.5 ~ 1.0.When equivalent proportion is more than 0.3, then there is curability and improve and the tendency of bonding force raising, when being less than 1.5, then there is unreacted acid anhydrides can not be excessively remaining, is suppressed by water absorption rate for low, the tendency that insulating reliability improves.
(iii) amine system curing agent
As amine system curing agent, such as dicyandiamide can be used.
Amine system curing agent is preferably 0.3 ~ 1.5 relative to the equivalent proportion (amine/epoxy radicals, mol ratio) of above-mentioned (a) composition from the viewpoint of good curability, cementability and storage stability, be more preferably 0.4 ~ 1.0, more preferably 0.5 ~ 1.0.When equivalent proportion is more than 0.3, then there is curability and improve and the tendency of bonding force raising, then there is unreacted amine when being less than 1.5 can not be excessively remaining, the tendency that insulating reliability improves.
(iv) imidazoles system curing agent
As imidazoles system curing agent, include, for example out 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), 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-bishydroxymethyl imidazoles, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and the addition product of epoxy resin and imidazoles.Among them, from the curability of 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, 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-bishydroxymethyl imidazoles and 2-phenyl-4-methyl-5-hydroxymethylimidazole.They can be used alone or and use with two or more.In addition, also can be made into and microencapsulation is carried out to them and the latent curing agent obtained.
The content of imidazoles system curing agent is preferably 0.1 ~ 20 mass parts relative to (a) composition 100 mass parts, is more preferably 0.1 ~ 10 mass parts.When the content of imidazoles system curing agent is more than 0.1 mass parts, then there is the tendency that curability improves, then having adhesive composite before formation metal bond when being below 20 mass parts can not solidify, and the tendency of bad connection not easily occurs.
(v) phosphine system curing agent
As phosphine system curing agent, include, for example out triphenylphosphine, tetraphenylphosphoniphenolate tetraphenylborate, tetraphenylphosphoniphenolate four (4-aminomethyl phenyl) borate and tetraphenylphosphoniphenolate (4-fluorophenyl) borate.
The content of phosphine system curing agent is preferably 0.1 ~ 10 mass parts relative to (a) composition 100 mass parts, is more preferably 0.1 ~ 5 mass parts.When the content of phosphine system curing agent is more than 0.1 mass parts, then there is the tendency that curability improves, then having adhesive composite before formation metal bond when being below 10 mass parts can not solidify, and the tendency of bad connection not easily occurs.
Phenolic resins system curing agent, acid anhydrides system curing agent and amine system curing agent, separately can use a kind or use in the mode of mixture of more than two kinds.Imidazoles system curing agent and phosphine system curing agent also can individually use, but also can use together with phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent.
When adhesive composite comprises phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent as (b) composition, the flux activity removing oxide-film can be manifested, more can improve connection reliability.
(c) composition: acrylic acid series surface treatment filler or there is the filler of the group represented by above-mentioned general formula (1)
As (c) composition, then be not particularly limited if carried out surface-treated filler by the compound with the group shown in above-mentioned general formula (1), such as, can use the filler that insulating properties inorganic filler, whisker (ウ ィ ス カ ー) and resin extender are carried out surface treatment and obtained.That is, as (C) composition, the filler with the group represented by above-mentioned general formula (1) can be used.
Herein, in formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, be preferably hydrogen atom, methyl or ethyl.Have following tendency: R 1carbon number more increase, volume more uprises, and then reactively when carbon number is more than 2 reduces.R 2represent the alkylidene of carbon number 1 ~ 30, be preferably the alkylidene of carbon number 1 ~ 15.R 2carbon number more than 30 time, then have and not easily surface-treated tendency carried out to filler.
Whether (c) composition has at filling surface the group represented by above-mentioned general formula (1), such as, confirm by following such method.
The adhesive composite of present embodiment is heated, uses gas chromatography (such as, SHIMADZU system, goods name " GC-17A ") to measure the methyl alcohol produced.Amount according to this methyl alcohol can confirm: have this situation of group represented by above-mentioned general formula (1) being present in filling surface.In the case, similarly measure the adhesive composite not comprising (C) composition quantity of methyl alcohol and as reference.
As insulating properties inorganic filler, include, for example out glass, silicon dioxide, aluminium oxide, titanium oxide, carbon black, mica and boron nitride, be preferably silicon dioxide, aluminium oxide, titanium oxide and boron nitride, be more preferably silicon dioxide, aluminium oxide and boron nitride.As whisker, include, for example out aluminium borate, aluminium titanates, zinc oxide, calcium silicates, magnesium sulfate and boron nitride.As resin extender, polyurethane, polyimides can be listed.These fillers and whisker can be used alone or use in the mode of mixture of more than two kinds.The shape of filler, particle diameter and use level are not particularly limited.Also fine nano silicon can be used.Among these fillers, due to surface-treated ease, compare well with the compatibility of resinous principle, therefore preferred silica filler.
As (c) composition, can use and carry out surface-treated filler by the compound shown in above-mentioned general formula (2).Specifically can use: by R in formula (2) 1acrylic compounds for hydrogen atom has carried out surface-treated silica filler, by R in formula (2) 1methacrylic acid based compound for methyl has carried out surface-treated silica filler and by R in formula (2) 1for the ethylacrylic acid based compound of ethyl has carried out surface-treated silica filler.Resinous principle contained from the viewpoint of Semiconductor bonding agent, to be formed with the reactivity of semiconductor substrate surface, key, in preferred above-mentioned formula (2), R 1for the group that volume is little, R 1for the alkyl of hydrogen atom or carbon number 1 or 2, hydrogen atom, methyl or ethyl.Have following tendency: R 1carbon number more increase, volume more uprises, and then reactively when carbon number is more than 2 reduces.That is, as (C) composition, can use and carry out surface-treated silica filler by acrylic compounds, methacrylic acid based compound or ethylacrylic acid based compound.
In above-mentioned general formula (1) or (2), R 2represent the alkylidene of carbon number 1 ~ 30, because thus volatile ingredient is preferably the alkylidene of carbon number 1 ~ 15 less.In formula (2), R 3represent the alkyl of carbon number 1 ~ 30, suitably can select according to the easy degree of surface-treated.R 3carbon number when being less than 30, then have and easily surface-treated tendency carried out to filler.
C shape, the particle diameter of () composition suitably set according to the purposes of adhesive composite, be not particularly limited.
About the average grain diameter of (c) composition, when filler shape is spherical, average grain diameter is preferably less than 2 μm, in the packaging body of narrow spacing, narrow gapization progress, in order to avoid reducing by catching the reliability that (ト ラ ッ ピ Application グ) cause, be more preferably less than 1.5 μm, be particularly preferably less than 1.0 μm.In addition, from the viewpoint of treatability, its lower limit is more preferably more than 0.005 μm, is particularly preferably less than 0.01 μm.
About the use level of (c) composition, all for benchmark with the solid constituent of adhesive composite, be preferably 5 ~ 80 quality %, be more preferably 10 ~ 70 quality %.When for more than 5 quality %, then have the tendency easily playing the raising of bonding force strongly, when being below 80 quality %, then exist and easily adjust viscosity, not easily there is the reduction of the mobility of adhesive composite, filler to the occlusion (catching) of connecting portion, the tendency that connection reliability improves.
In addition, for silane coupler, do not carry out surface treatment with filler in advance, as adhesive composite constituent and add, when carrying out surface treatment in system, then produce methyl alcohol etc., cause foaming when high-temperature technology.
By improving the bonding force after the moisture absorption of adhesive composite near 260 DEG C and the modulus of elasticity of raising near 260 DEG C, thus reflux-resisting welded property can be improved, the stripping after Reflow Soldering, bad connection can be prevented.
(d) composition: the macromolecule component of weight average molecular weight more than 10000
As (d) composition, include, for example out 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.From the viewpoint of thermal endurance and film forming excellence among them, be preferably phenoxy resin, polyimide resin, acrylic rubber, cyanate ester resin and poly-carbodiimide resin, be more preferably phenoxy resin, polyimide resin and acrylic rubber.These (d) composition can be used alone or uses in the mode of mixture of more than two kinds, copolymer.But, in (d) composition, do not comprise the epoxy resin as (A) composition.
The macromolecule components such as above-mentioned phenoxy resin, polyimide resin can use commercially available product, also can use composite.
Polyimide resin such as makes tetracarboxylic dianhydride and diamines carry out condensation reaction and obtain by known method.More specifically, in organic solvent, make tetracarboxylic dianhydride and diamines carry out waiting mole or roughly etc. mole mix (order of addition of each composition is any), reaction temperature being set as less than 80 DEG C, being preferably set to 0 ~ 60 DEG C and carry out addition reaction.Be explained, in order to suppress the reduction of all characteristics of adhesive composite, preferably above-mentioned tetracarboxylic dianhydride carries out recrystallization refinement treatment by acetic anhydride.
Along with the carrying out of above-mentioned addition reaction, the viscosity of reactant liquor raises lentamente, generates the polyamic acid of the precursor as polyimides.Polyimide resin can carry out dehydration closed-loop to above-mentioned polyamic acid and obtain.Dehydration closed-loop is by carrying out the hot closed loop method of heat treated, the chemical closed loop method of use dehydrating agent and carrying out.Above-mentioned polyamic acid is by the depolymerization 50 ~ 80 DEG C of heating, thus its molecular weight of adjustable.
As the tetracarboxylic dianhydride of the raw material as polyimide resin, be not particularly limited, include, for example out: pyromellitic acid dianhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 2,2 ', 3,3 '-biphenyl tetracarboxylic dianhydride, two (3, the 4-dicarboxyphenyi) propane dianhydride of 2,2-, two (2, the 3-dicarboxyphenyi) propane dianhydride of 2,2-, two (2,3-dicarboxyphenyi) the ethane dianhydride of 1,1-, two (3,4-dicarboxyphenyi) the ethane dianhydride of 1,1-, two (2,3-dicarboxyphenyi) methane dianhydride, two (3,4-dicarboxyphenyi) methane dianhydride, two (3,4-dicarboxyphenyi) sulfone dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, two (3,4-dicarboxyphenyi) ether dianhydride, benzene-1,2,3,4-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, Isosorbide-5-Nitrae, 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-Isosorbide-5-Nitrae, 5,8-tetracarboxylic dianhydride, 2,7-dichloronaphtalene-Isosorbide-5-Nitrae, 5,8-tetracarboxylic dianhydride, 2,3,6,7-Tetrachloronaphthalene-Isosorbide-5-Nitrae, 5,8-tetracarboxylic dianhydride, luxuriant and rich with fragrance-1,8,9,10-tetracarboxylic dianhydrides, pyrazine-2,3,5,6-tetracarboxylic dianhydride, thiophene-2,3,5,6-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-dicarboxyphenyi) dimethylsilane dianhydride, two (3,4-dicarboxyphenyi) aminomethyl phenyl silane dianhydride, two (3,4-dicarboxyphenyi) diphenyl silane dianhydride, Isosorbide-5-Nitrae-bis-(3,4-dicarboxyphenyi dimetylsilyl) benzene dianhydride, 1,3-two (3,4-dicarboxyphenyi)-1,1,3,3-tetramethyl bis cyclohexane dianhydride, TOPOT 2,2′ p phenylenebis (trimellitate acid anhydride), ethene tetracarboxylic dianhydride, 1,2,3,4-butane tetracarboxylic acid dianhydride, decahydronaphthalene-Isosorbide-5-Nitrae, 5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydro naphthalene-1,2,5,6-tetracarboxylic dianhydride, pentamethylene-1,2,3,4-tetracarboxylic dianhydride, pyrrolidines-2,3,4,5-tetracarboxylic dianhydride, 1,2,3,4-cyclobutane tetracarboxylic dianhydride, two (outer-dicyclo [2,2,1] heptane-2,3-dicarboxylic acid dianhydride, dicyclo-[2,2,2]-Xin-7-alkene-2,3,5,6-tetracarboxylic dianhydride, two (3, the 4-dicarboxyphenyi) propane dianhydride of 2,2-, two [4-(3, the 4-dicarboxyphenyi) phenyl] propane dianhydride of 2,2-, two (3, the 4-dicarboxyphenyi) hexafluoropropane dianhydride of 2,2-, two [4-(3, the 4-dicarboxyphenyi) phenyl] hexafluoropropane dianhydride of 2,2-, 4,4 '-bis-(3,4-di carboxyl phenyloxy) diphenyl sulfide dianhydride, Isosorbide-5-Nitrae-bis-(2-hydroxyl hexafluoro isopropyl) benzene two (trimellitic anhydride), two (the 2-hydroxyl hexafluoro isopropyl) benzene of 1,3-two (trimellitic anhydride), 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid dianhydride, oxolane-2,3,4,5-tetracarboxylic dianhydride, the tetracarboxylic dianhydride represented by following general formula (I) and the tetracarboxylic dianhydride represented by following formula (II).
[chemical formula 4]
In formula (I), a represents the integer of 2 ~ 20.
[chemical formula 5]
The tetracarboxylic dianhydride represented by above-mentioned general formula (I) can be synthesized by the glycol of trimellitic anhydride list acyl chlorides and correspondence, specifically can list: 1, 2-(ethylidene) two (trimellitate acid anhydride), 1, 3-(trimethylene) two (trimellitate acid anhydride), 1, 4-(tetramethylene) two (trimellitate acid anhydride), 1, 5-(pentamethylene) two (trimellitate acid anhydride), 1, 6-(hexa-methylene) two (trimellitate acid anhydride), 1, 7-(heptamethylene) two (trimellitate acid anhydride), 1, 8-(eight methylene) two (trimellitate acid anhydride), 1, 9-(nine methylene) two (trimellitate acid anhydride), 1, 10-(decamethylene) two (trimellitate acid anhydride), 1, 12-(ten dimethylenes) two (trimellitate acid anhydride), 1, 16-(ten hexa-methylenes) two (trimellitate acid anhydride) and 1, 18-(18 methylene) two (trimellitate acid anhydride).
As tetracarboxylic dianhydride, from the viewpoint of giving excellent moisture-proof reliability, the tetracarboxylic dianhydride preferably represented by above-mentioned formula (II).Above-mentioned tetracarboxylic dianhydride can be used alone or combines two or more to use.
The content of the tetracarboxylic dianhydride represented by above-mentioned formula (II) is preferably more than 40 % by mole relative to whole tetracarboxylic dianhydride, is more preferably more than 50 % by mole, more preferably more than 70 % by mole.When content is more than 40 % by mole, then have following tendency: easily guarantee the effect based on employing the tetracarboxylic dianhydride represented by above-mentioned formula (II) and the moisture-proof reliability obtained fully.
As the diamines of the raw material as above-mentioned polyimide resin, be not particularly limited, include, for example out: 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 (amino-3, the 5-3,5-dimethylphenyls of 4-) methane, two (amino-3, the 5-diisopropylbenzyls of 4-) 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, two (3-aminophenyl) propane of 2,2-, 2,2 '-(3,4 '-diamino-diphenyl) propane, two (4-aminophenyl) propane of 2,2-, two (3-aminophenyl) HFC-236fa of 2,2-, 2,2-(3,4 '-diamino-diphenyl) HFC-236fa, two (4-aminophenyl) HFC-236fa of 2,2-, two (3-amino-benzene oxygen) benzene of 1,3-, Isosorbide-5-Nitrae-bis-(3-amino-benzene oxygen) benzene, Isosorbide-5-Nitrae-bis-(4-amino-benzene oxygen) benzene, 3,3 '-(Isosorbide-5-Nitrae-phenylene two (1-methyl ethylidene)) dianil, 3,4 '-(Isosorbide-5-Nitrae-phenylene two (1-methyl ethylidene)) dianil, 4,4 '-(Isosorbide-5-Nitrae-phenylene two (1-methyl ethylidene)) dianil, 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 2,2-, 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, the aromatic diamines such as 5-diaminobenzoic acid, 1, two (amino methyl) cyclohexane of 3-, 2,2-two (4-aminophenoxy phenyl) propane, the fatty ether diamines represented by following general formula (III) or (IV), the aliphatic diamine represented by following general formula (V) and the siloxane diamine represented by following general formula (VI).
[chemical formula 6]
In formula (III), Q 1, Q 2and Q 3separately represent the alkylidene of carbon number 1 ~ 10, b represents the integer of 1 ~ 80.
[chemical formula 7]
In formula (IV), Q 4, Q 5, Q 6and Q 7separately represent the alkylidene of carbon number 1 ~ 10, c, d and e separately represent the integer of 1 ~ 50.
[chemical formula 8]
In formula (V), f represents the integer of 5 ~ 20.
[chemical formula 9]
In formula (VI), Q 8and Q 13separately represent that the alkylidene of carbon number 1 ~ 5 maybe can have or not have substituent phenylene, Q 9, Q 10, Q 11and Q 12separately represent the alkyl of carbon number 1 ~ 5, phenyl or phenoxy group, g represents the integer of 1 ~ 5.
Among them, from the viewpoint of giving low stress, low temperature plyability and low adhesion, the diamines preferably represented by above-mentioned general formula (III), (IV) or (V), from the viewpoint of low water absorbable and agent of low hygroscopicity can be given, the diamines preferably represented by above-mentioned general formula (VI).These diamines can be used alone or combine two or more to use.
The content of the fatty ether diamines represented by above-mentioned general formula (III) or (IV) is preferably 1 ~ 50 % by mole of whole diamines, the content of the aliphatic diamine represented by above-mentioned general formula (V) is preferably 20 ~ 80 % by mole of whole diamines, and the content of the siloxane diamine represented by above-mentioned general formula (VI) is preferably 20 ~ 80 % by mole of whole diamines.For in the scope of above-mentioned content time, then have the effect of giving low temperature plyability and low water absorbable and become large tendency.
In addition, as the fatty ether diamines represented by above-mentioned general formula (III), the fatty ether diamines of following formula (III-1) ~ (III-5) specifically can be listed.Be explained, in general formula (III-4) and (III-5), n represents the integer of more than 1.
[chemical formula 10]
The weight average molecular weight of the fatty ether diamines represented by above-mentioned general formula (III-4) is such as preferably 350,750,1100 or 2100.In addition, the weight average molecular weight of the fatty ether diamines represented by above-mentioned general formula (III-5) is such as preferably 230,400 or 2000.
Among above-mentioned fatty ether diamines, from the viewpoint of low temperature plyability and the good cementability to the substrate with organic resist can be guaranteed, be more preferably the fatty ether diamines represented by above-mentioned general formula (IV), following general formula (VII), (VIII) or (IX) respectively.
[chemical formula 11]
In formula (VII), h represents the integer of 2 ~ 80, is more preferably 2 ~ 70.
[chemical formula 12]
In formula (VIII), c, d and e represent the integer of 1 ~ 50, are more preferably 2 ~ 40.
[chemical formula 13]
In formula (IX), j and k separately represents the integer of 1 ~ 70.
As the fatty ether diamines represented by above-mentioned general formula (VII), specifically can list SUNTECHNOCHEMICAL(サ Application テ Network ノ ケ ミ カ Le) (strain) JEFFAMINED-230 of making, D-400, D-2000 and D-4000, the polyetheramine D-230 of BASF, D-400 and D-2000, as the fatty ether diamines represented by above-mentioned general formula (VIII), specifically can list SUNTECHNOCHEMICAL(strain) JEFFAMINEED-600 that makes, ED-900, ED-2001, as the fatty ether diamines represented by above-mentioned formula (IX), SUNTECHNOCHEMICAL(strain can be listed) JEFFAMINEEDR-148 that makes.
As the aliphatic diamine represented by above-mentioned general formula (V), include, for example out EDA, 1,3-diaminopropanes, 1,4-Diaminobutane, 1,5-1,5-DAP, 1,6-diamino hexane, 1,7-diaminoheptane, 1,8-diamino-octane, 1,9-diamino nonane, 1,10-diamino decane, 1,11-diamino undecane, 1,12-diamino dodecane and 1,2-DACH.Among them, preferably 1,9-diamino nonane, 1,10-diamino decane, 1,11-diamino undecane and 1,12-diamino dodecane.
As the siloxane diamine represented by above-mentioned general formula (VI), g in general formula (VI) is 1, can list: 1, 1, 3, 3-tetramethyl-1, two (4-aminophenyl) disiloxane of 3-, 1, 1, 3, 3-tetra-phenoxy group-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, two (3-aminobutyl) disiloxane and 1 of 3-, 3-dimethyl-1, 3-dimethoxy-1, two (4-aminobutyl) disiloxane of 3-.When g is 2, can list: 1, 1, 3, 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, two (4-aminobutyl) trisiloxanes of 5-, 1, 1, 5, 5-tetraphenyl-3, 3-dimethoxy-1, two (5-Aminopentyl) trisiloxanes of 5-, 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, two (4-aminobutyl) trisiloxanes of 5-, 1, 1, 5, 5-tetramethyl-3, 3-dimethoxy-1, two (5-Aminopentyl) trisiloxanes of 5-, 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 of 5-, 1, 3, 3, 5, 5-six propyl group-1, two (3-aminopropyl) trisiloxanes of 5-.
Above-mentioned polyimide resin can be used alone or uses in the mode of mixture of more than two kinds.
About the vitrification point (Tg) of (d) composition, from the viewpoint of the attaching excellence of adhesive composite to substrate, chip, be preferably less than 100 DEG C, be more preferably less than 85 DEG C.When Tg is below 100 DEG C, have easily that the projection of semiconductor chip, the electrode being formed at substrate, Wiring pattern etc. are concavo-convex to be imbedded by being formed at by adhesive composite, can not entrapped air pockets, not easily produce the tendency of pore.Be explained, above-mentioned Tg refers to, use DSC (Perkin-Elmer Inc. DSC-7 type), sample size 10mg, programming rate 10 DEG C/min, measure atmosphere be the condition of air under measure time Tg.
D the weight average molecular weight of () composition counts more than 10000 with polystyrene conversion, but in order to show good film forming individually, being preferably more than 30000, being more preferably more than 40000, more preferably more than 50000.When weight average molecular weight is more than 10000, then there is the tendency of film forming and thermal endurance raising.Be explained, in this manual, weight average molecular weight refers to, uses high performance liquid chromatography (such as, Shimadzu Seisakusho Ltd.'s system, goods name " C-R4A "), weight average molecular weight when measuring according to polystyrene conversion.
D the content of () composition is not particularly limited, but in order to keep membranaceous well, relative to (a) composition 100 mass parts, being preferably 1 ~ 500 mass parts, being more preferably 5 ~ 300 mass parts, more preferably 10 ~ 200 mass parts.When the content of () composition is more than 1 mass parts d, have the tendency of the raising effect easily obtaining film forming, when being below 500 mass parts, then there is the tendency that curability improves, bonding force improves of adhesive composite.
(e) composition: flux activity agent
(e) composition can be contained, that is, as the flux activity agent of the compound of display flux activity (removing the activity of oxide, impurity) in adhesive composite of the present invention.As flux activity agent, list nitrogen-containing compound, carboxylic acids, phenols and the alcohols as imidazoles, amine with unshared electron pair.
The state that among them, the flux activity of carboxylic acids reacts by force, with the epoxy resin as (a) composition, to dissociate in the solidfied material of adhesive composite exists, and therefore can prevent the reduction of insulating reliability.
As carboxylic acids, include, for example out: acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, sad, the fat formula saturated carboxylic acid such as n-nonanoic acid, capric acid, dodecylic acid, tetradecanoic acid, hexadecanoic acid, Heptadecanoic acide, octadecanoid acid; The fat formula unsaturated carboxylic acids such as oleic acid, linoleic acid, leukotrienes, arachidonic acid, DHA, eicosapentaenoic acid; The fat formula dicarboxylic acids such as maleic acid, fumaric acid, ethanedioic acid, malonic acid, butanedioic acid, glutaric acid, adipic acid; The aromatic carboxylic acid such as 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 (melliticacid).In addition, as the carboxylic acid with hydroxyl, include, for example out lactic acid, malic acid, citric acid and salicylic acid.
Further, also can be used in above-mentioned aromatic carboxylic acid and there is substituting group that is electron-withdrawing or electron donating property, the fragrant family carboxylic acid making according to substituting group the acidity of the carboxylic acid on aromatic series change.The acidity having carboxylic acid is higher, the tendency that flux activity more improves, but then has the situation of insulating reliability reduction when acidity is too high.As the electron-attracting substituent of the acidity of raising carboxylic acid, nitro, cyano group, trifluoromethyl, halogen group and phenyl can be listed.As the substituting group of electron donating property of acidity weakening carboxylic acid, methyl, ethyl, isopropyl, the tert-butyl group, dimethylamino and trimethylamino can be listed.Be explained, about above-mentioned substituent number, position, if do not reduce flux activity, insulating reliability, be not particularly limited.
(other composition)
In the adhesive composite of present embodiment, in order to control the physical property of viscosity, solidfied material, and in order to suppress the generation of pore when being connected to semiconductor chip and substrate, the rising of hydroscopicity, except (c) composition, also can coordinate filler further.
As filler, insulating properties inorganic filler, whisker or resin extender can be used.As insulating properties inorganic filler, whisker or resin extender, the material same with above-mentioned (c) composition can be used.These fillers, whisker and resin extender can use a kind or use in the mode of mixture of more than two 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 coordinate the additive such as antioxidant, silane coupler, titanium coupling agent, levelling agent, ion trap agent.They can be used alone a kind or also capable of being combinedly use two or more.About their use level, according to manifest each additive effect mode and suitably adjust.
The adhesive composite of present embodiment can be formed as membranaceous.Provide the manufacture method of the film-like adhesive of the adhesive composite employing present embodiment below.First, (a) composition, (b) composition and (c) composition and (d) composition added as required or (e) composition etc. are added in organic solvent, by being uniformly mixed, mixing etc. and dissolve or dispersion, thus prepare resin varnish.Thereafter, on the base material film implementing demoulding process, using blade coating machine, roll coater, spreader coating resin varnish, then by adding heat abstraction organic solvent, thus film-like adhesive can be obtained on base material film.
As the organic solvent for the preparation of resin varnish, preferably there is the organic solvent of the characteristic each uniform composition can dissolved or disperse, include, for example out dimethyl formamide, dimethylacetylamide, METHYLPYRROLIDONE, 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 be used alone or combine two or more to use.Being uniformly mixed when preparing resin varnish, mixingly such as can using mixer, mixing and kneading machine, three-roll grinder, ball mill, ball mill and homogenous disperse machine (ホ モ デ ィ ス パ ー) and carry out.
As base material film, if the base material film with the thermal endurance of heating condition when can tolerate volatile organic solvent is then not particularly limited, can exemplify: the polyolefin films such as polypropylene screen, polymethylpentene film, polyester film, polyimide film and the polyetherimde films such as PETG film, poly (ethylene naphthalate) film.Base material film is not limited to the base material film of the individual layer formed by these films, can for the multilayer film formed by material of more than two kinds yet.
Be preferably the condition of volatile organic solvent fully from drying condition when coating the resin varnish volatile organic solvent of base material film, specifically preferably carry out the heating of 50 ~ 200 DEG C, 0.1 ~ 90 minute.
In addition, about the adhesive composite of present embodiment, from the viewpoint of raising workability, also by being directly spun on wafer, carrying out drying as required, then wafer being carried out singualtion and using.
< semiconductor device >
The semiconductor device of Fig. 1 and 2 to present embodiment is below used to be described.Fig. 1 is the pattern cutaway view of the execution mode representing semiconductor device of the present invention.As shown in Fig. 1 (a), semiconductor device 100 has: the semiconductor chip 10 of mutual subtend and substrate (circuit layout substrate) 20, be configured at the distribution 15 in the face of the mutual subtend of semiconductor chip 10 and substrate 20 respectively, by the interconnective connection projection 30 of distribution 15 of semiconductor chip 10 and substrate 20, be filled in the adhesive composite 40 in the space between semiconductor chip 10 and substrate 20 very close to each otherly.Semiconductor chip 10 and substrate 20 are by distribution 15 and connect projection 30 and carry out flip-chip connection.Distribution 15 and connection projection 30 are sealed by adhesive composite 40 and block from external environment condition.
As shown in Fig. 1 (b), semiconductor device 200 has: the semiconductor chip 10 of mutual subtend and substrate 20, be configured at the projection 32 in the face of the mutual subtend of semiconductor chip 10 and substrate 20 respectively, the adhesive composite 40 in the space between ground very close to each other filling semiconductor chip 10 and substrate 20.Semiconductor chip 10 and substrate 20 are interconnected by the projection 32 of subtend and carry out flip-chip connection.Projection 32 is sealed by adhesive composite 40 and blocks from external environment condition.
Fig. 2 is the pattern cutaway view of another execution mode representing semiconductor device of the present invention.As shown in Fig. 2 (a), about semiconductor device 300, connect except this point except 2 semiconductor chips 10 carry out flip-chip by distribution 15 and connection projection 30, same with semiconductor device 100.As shown in Fig. 2 (b), about semiconductor device 400, connect except this point except 2 semiconductor chips 10 carry out flip-chip by projection 32, same with semiconductor device 200.
Be not particularly limited as semiconductor chip 10, the compound semiconductor such as elemental semiconductor, GaAs, indium phosphide be made up of the element of the identical type such as silicon, germanium can be used.
As substrate 20, if circuit substrate is then not particularly limited, can use: with glass epoxy resin (glass-epoxy), polyimides, polyester, pottery, epoxy resin, the surface for the insulated substrate of main composition such as Bismaleimide Triazine has the circuit substrate by the distribution (Wiring pattern) 15 formed not needing the position of metal film to carry out etching removal, defined the circuit substrate of distribution 15 by metal-plated etc. on the surface of above-mentioned insulated substrate, above-mentioned insulated substrate surface printing conductive material and define the circuit substrate of distribution 15.
For connecting portions such as distribution 15, projections 32, as main component, containing gold, silver, copper, scolding tin (main component is such as Xi-Yin, tin-lead, Sn-Bi, tin-copper, tin-silver-copper), nickel, tin, lead etc., also various metals can be contained.
Among above-mentioned metal, from the viewpoint of making the electrical conductivity of connecting portion, the packaging body of excellent thermal conductivity, being preferably gold, silver and copper, being more preferably silver and copper.From the viewpoint of making the packaging body making cost reduce, be preferably silver, copper and scolding tin, more preferably copper and scolding tin based on cheapness, further preferred scolding tin.The situation of productivity ratio reduction, the situation of cost increase is then had when metallic surface forms oxide-film in room temperature, therefore from the viewpoint of the formation suppressing 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, being also formed by such as plating with gold, silver, copper, scolding tin (main component is such as Xi-Yin, tin-lead, Sn-Bi, tin-copper), tin, nickel etc. is the metal level of main composition.This metal level also can only be assigned to form by single one-tenth, also can be made up of Multiple components.In addition, above-mentioned metal level also can be made into individual layer or stacked various metals layer and the structure obtained.
In addition, structure (packaging body) that also can be such shown in stacked multiple semiconductor device 100 ~ 400 in the semiconductor device of present embodiment.In the case, semiconductor device 100 ~ 400 also can by comprising gold, silver, copper, scolding tin (main component is such as Xi-Yin, tin-lead, Sn-Bi, tin-copper, tin-silver-copper), the projection of tin, nickel etc., distribution be reciprocally electrically connected.
As by technology stacked for multiple semiconductor device, as shown in Figure 3, include, for example out TSV (Through-SiliconVia) technology.Fig. 3 is the pattern cutaway view of another execution mode representing semiconductor device of the present invention, and is the use of the semiconductor device of TSV technology.In the semiconductor device 500 shown in Fig. 3, connect by being connected projection 30 with the distribution 15 of semiconductor chip 10 by making to be formed at the distribution 15 on intermediary layer (interposer) 50, thus semiconductor chip 10 carries out flip-chip with intermediary layer 50 is connected.Be filled with adhesive composite 40 in space between semiconductor chip 10 and intermediary layer 50 very close to each otherly.Is on the surface of opposition side with intermediary layer 50 side in above-mentioned semiconductor chip 10, repeatedly overlaps semiconductor chip 10 by distribution 15, connection projection 30 and adhesive composite 40.The distribution 15 of the surface of semiconductor chip 10 and the pattern plane at back side place is interconnected by the through electrode 34 be filled in the hole of the inside of through semiconductor chip 10.Be explained, as the material of through electrode 34, can copper, aluminium etc. be used.
By such TSV technology, also signal can be obtained from the back side of the semiconductor chip usually do not used.Further, owing to making through electrode 34 vertically through in semiconductor chip 10, the distance between the semiconductor chip 10 therefore shortening subtend, between semiconductor chip 10 and intermediary layer 50, can realize soft connection.The adhesive composite of present embodiment, in such TSV technology, the encapsulating semiconductor bonding agent between the applicable semiconductor chip 10 making subtend, between semiconductor chip 10 and intermediary layer 50.
In addition, in the bump forming method that the degrees of freedom such as face bumped chip technology (エ リ ャ バ Application プ チ ッ プ skill Intraoperative) are high, as former state semiconductor chip directly can not 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 semiconductor chip being directly installed on motherboard.Be explained, when by stacked for 2 wired circuit boards, at the adhesive composite by also applicable present embodiment during gap seals between substrate.
The manufacture method > of < semiconductor device
The manufacture method of Fig. 4 to the semiconductor device of present embodiment is below used to be described.Fig. 4 be pattern represent the operation cutaway view of an execution mode of the manufacture method of semiconductor device of the present invention.
First, as shown in Fig. 4 (a), on the substrate 20 with distribution 15, be formed in and form the solder mask 60 that the position connecting projection 30 has opening.This solder mask 60 is not necessarily arranged.But, by arranging solder mask on the base plate 20, the generation of the electric bridge (Block リ ッ ジ) between distribution 15 can be suppressed, connection reliability, insulating reliability can be improved.Solder mask 60 such as can use commercially available packaging body solder mask ink and be formed.As commercially available packaging body solder mask ink, SR series (Hitachi Chemical Co., Ltd.'s system, trade name) and PSR4000-AUS series (sun ink manufactures (strain) system, trade name) specifically can be listed.
Then, as shown in Fig. 4 (a), formed at the opening part of solder mask 60 and connect projection 30.Then, as shown in Fig. 4 (b), the substrate 20 being formed with connection projection 30 and solder mask 60 attaches membranaceous adhesive composite (following, to be optionally called " film-like adhesive ") 40.The attaching of film-like adhesive 40 is undertaken by hot pressing, roll laminating, vacuum lamination etc.The supply area of film-like adhesive 40, thickness can according to the size of semiconductor chip 10 and substrate 20, the height connecting projection 30 and suitably setting.
After as described above film-like adhesive 40 being attached at substrate 20, use the jockeys such as flip-chip bond machine by the distribution 15 of semiconductor chip 10 be connected projection 30 and carry out aligned in position.Then, while to heating temperatures more than the fusing point being connected projection 30 of semiconductor chip 10 and substrate 20 while crimp, as shown in Fig. 4 (c), semiconductor chip 10 is connected with substrate 20, and by film-like adhesive 40, sealing filling is carried out in the space between semiconductor chip 10 and substrate 20.By more than, semiconductor device 600 can be obtained.
In the manufacture method of the semiconductor device of present embodiment, also can carry out after having carried out aligned in position temporary fixed (state via Semiconductor bonding agent), in reflow soldering, carry out heat treated, thus semiconductor chip 10 is connected with substrate 20 by connection projection 30 melting.In the temporary fixed stage and nonessential formation metal bond, be thus compared to and above-mentioned heat the method crimped, based on the crimping of low load, short time, low temperature, can boost productivity, and the deterioration of connecting portion can be suppressed.
In addition, also semiconductor chip 10 can be connected with substrate 20, then carry out heat treated by baking oven etc., improve connection reliability, insulating reliability further.Heating-up temperature preferably carries out the temperature of the solidification of film-like adhesive, is 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 after film-like adhesive 40 is attached at semiconductor chip 10, substrate 20 can be connected.In addition, also after semiconductor chip 10 and substrate 20 being connected by distribution 15 and connection projection 30, the adhesive composite of pasty state can be filled in the space between semiconductor chip 10 and substrate 20.
Improve from the viewpoint of productivity ratio, also adhesive composite can be supplied in the semiconductor wafer that multiple semiconductor chip 10 is formed by connecting, then cut and carry out singualtion, thus obtain the structure supplying on semiconductor chip 10 and have adhesive composite.In addition, when adhesive composite is pasty state, be not particularly limited, but by coating processes such as spin coatings, the distribution on semiconductor chip 10, projection imbedded, thickness is carried out homogenizing.In this case, the quantity delivered due to resin becomes certain, and productivity ratio thus can be made to improve, and can suppress by the reduction of the generation and cutting imbedding the pore that deficiency causes.On the other hand, when adhesive composite is membranaceous, is not particularly limited, but supplies membranaceous resin combination by attaching modes such as hot pressing, roll laminating and vacuum laminations according to the mode of the distribution on embedded with semi-conductor chip 10, projection.In this case, the quantity delivered of resin becomes certain, and productivity ratio thus can be made to improve, and can suppress by the reduction of the generation and cutting imbedding the pore that deficiency causes.
Connect load consider connect projection 30 quantity, height deviation, based on pressurization connection projection 30 or accept connecting portion projection distribution deflection and set.About connection temperature, the temperature of preferred connecting portion is more than the fusing point of connection projection 30, as long as can form the temperature of the metal bond of each connecting portion (projection, distribution).When connection projection 30 is solder bump, be preferably more than about 240 DEG C.
Connect hours during connection is different because of the formation metal of connecting portion, but is more that the short time is then more preferred from the viewpoint of productivity ratio raising.When connection projection 30 is solder bump, the connect hours is preferably less than 20 seconds, is more preferably less than 10 seconds, more preferably less than 5 seconds.When the metal of copper-copper or copper-Jin connects, the connect hours is preferably less than 60 seconds.
Even if 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 limited to following embodiment.
(polyimides synthesis)
To in the 300mL flask having thermometer, mixer and calcium chloride tube, add 1,12-diamino 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 disiloxane of 3-(SHIN-ETSU HANTOTAI's chemistry system, trade name " LP-7100 ") 2.61g (0.035 mole) and METHYLPYRROLIDONE (Northeast chemistry system, hereinafter referred to as " NMP ") 150g and stirring.After above-mentioned two amine solvents, while flask is cooled in ice bath, marginally with the addition of on one side at every turn by acetic anhydride carry out recrystallization refine and obtain 4,4 '-(4,4 '-isopropylidene two phenoxy group) two (O-phthalic acid dianhydride) (ALDRICH system, trade name " BPADA ") 15.62g (0.10 mole).At room temperature react after 8 hours, add dimethylbenzene 100g, be blown into nitrogen 180 DEG C of heating, together xylenes removed with water, obtain polyimide resin.Remove solvent (NMP) from obtained polyimide resin, the material obtained being dissolved in methylethylketone (MEK) according to the mode becoming solid constituent 50 quality % is set to " polyimides A ".The Tg of polyimides A is 30 DEG C, and weight average molecular weight is 50000, SP value (solubility parameter) is 10.2.
The compound used in each embodiment and each comparative example is as described below.
(a) epoxy resin
(japan epoxy resin Co., Ltd. system, trade name " EP1032H60 ", hereinafter referred to as " EP1032 " for multifunctional solid epoxy resin containing triphenol methylmethane skeleton.)
(japan epoxy resin Co., Ltd. system, trade name " YL983U ", hereinafter referred to as " YL983 " for bisphenol-f type liquid epoxy resin.)
(japan epoxy resin Co., Ltd. system, trade name " YL7175 ", hereinafter referred to as " YL7175 " for flexibility epoxy resin.)
(b) curing agent
(four countries change into Co., Ltd.'s system to 2-phenyl-4,5-bishydroxymethyl imidazoles, and trade name " 2PHZ-PW ", hereinafter referred to as " 2PHZ ".)
(four countries change into Co., Ltd.'s system to 2,4-diaminourea-6-[2 '-methylimidazolyl-(1 ')]-ethyl-s-triazine isocyanuric acid addition product, and trade name " 2MAOK-PW ", hereinafter referred to as " 2MAOK ".)
(c) acrylic acid series surface treatment filler or there is the filler of the group represented by above-mentioned general formula (1)
(average grain diameter 0.5 μm, hereinafter referred to as " SM silicon dioxide " for Co., Ltd. Admatechs system, trade name " SE2050-SMJ " for methacrylic acid surface treated silica filler.)
(Co., Ltd. Admatechs system, trade name " YA050C-SM ", hereinafter referred to as " SM nano silicon " for methacrylic acid surface treating nano silica filler.)
(c ') other filler
(average grain diameter 0.5 μm, hereinafter referred to as " untreated silicon dioxide " for Co., Ltd. Admatechs system, trade name " SE2050 " for untreated silica filler.)
(average grain diameter 0.5 μm, hereinafter referred to as " SX silicon dioxide " for Co., Ltd. Admatechs system, trade name " SE2050-SXJ " for aminosilane-treated silica filler.)
(average grain diameter 0.5 μm, hereinafter referred to as " SE silicon dioxide " for Co., Ltd. Admatechs system, trade name " SE2050-SEJ " for epoxy silane process silica filler.)
(average grain diameter 0.5 μm, hereinafter referred to as " SP silicon dioxide " for Co., Ltd. Admatechs system, trade name " SE2050-SPJ " for phenyl silane process silica filler.)
(average grain diameter 50nm, hereinafter referred to as " SP nano silicon " for Co., Ltd. Admatechs system, trade name " YA050C-SP " for phenyl surface treating nano silica filler.)
(the beautiful sun system of Mitsubishi, trade name " W5500 ", hereinafter referred to as " W5500 " in organic filler (1).)
(hud typed organic fine particles, hereinafter referred to as " EXL2655 " for RohmandHaas Japan (strain) Inc., trade name " EXL-2655 " in organic filler (2).)
The macromolecule component of (d) molecular weight more than 10000
Phenoxy resin (Toto Kasei KK's system, trade name " ZX1356 ", Tg: about 71 DEG C, Mw: about 63000, hereinafter referred to as " ZX1356 ".)
The polyimides A synthesized 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 film-like adhesive
(embodiment 1)
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 are fed in raw material according to the mode that solid constituent is 60 quality %, the microballon of the microballon of diameter 0.8mm and diameter 2.0mm and solid constituent are added as such, ball mill (FritschJapan Co., Ltd., planet-shaped atomizer " P-7 ") is utilized to stir 30 minutes.Then, add polyimides A100 mass parts (converting by solid constituent), again utilize ball mill and after stirring 30 minutes, removing the microballon for stirring by filtering, obtaining resin varnish.
Utilize miniature precision apparatus for coating (Lian Jing essence mechanism) that obtained resin varnish is coated base material film (Di Ren Du Pont membrane Co., Ltd. system, trade name " PUREXA53 "), in cleaning oven (ESPEC Co., Ltd. system), 70 DEG C of dryings 10 minutes, thus produce film-like adhesive.
(embodiment 2 ~ 3 and comparative example 1 ~ 6)
Table 1 described as follows changes used 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, the evaluation method of the film-like adhesive obtained by embodiment and comparative example is provided.
The mensuration > of the modulus of elasticity at < 260 DEG C
Film-like adhesive is cut the size (length 37mm × width 4mm × thickness 0.13mm) of regulation, in cleaning oven (ESPEC Co., Ltd. system), solidify 180 DEG C of maintenances 3 hours.After solidification, use determination of viscoelasticity device (Rheometrics system, trade name " RASII "), determine the modulus of elasticity at 260 DEG C of the arrival temperature of reflow soldering when evaluating as reflux-resisting welded property.Measure and carry out with temperature range-30 ~ 270 DEG C, programming rate 5 DEG C/min, mensuration wavelength 10Hz.
The mensuration > of the bonding force at 260 DEG C after < moisture absorption
Film-like adhesive is cut the size (length 5mm × width 5mm × thickness 0.025mm) of regulation, silicon (length 5mm × width 5mm × thickness 0.725mm, oxide-film are coated with) is attached at 60 DEG C, use thermo-compressed testing machine (Hitachi changes into Techno-Plant Co., Ltd. system), be crimped on glass epoxy substrate (thickness 0.02mm) (the crimping condition: the arrival temperature 180 DEG C/10 seconds/0.5MPa of film-like adhesive being coated with solder mask (sun ink system, trade name " AUS308 ").Then, the arrival temperature 245 DEG C/10 seconds/0.5MPa of film-like adhesive).Then, in cleaning oven (ESPEC Co., Ltd. system), Post RDBMS (aftercure) (180 DEG C/3 hours) has been carried out.Thereafter, 85 DEG C, Constant Temperature and Humidity Chambers (ESPEC Co., Ltd. system of relative humidity 60%, trade name " PR-2KP ") in place 48 hours, after taking-up, the hot plate of 260 DEG C uses bonding force determinator (DAGE Inc., universal type bonding detector DAGE4000 type), measure under the condition from instrument (tool) the height 0.05mm of substrate, instrument speed 0.05mm/ second.
The initial internuncial evaluation > of <
Made film-like adhesive is cut the size (length 8mm × width 8mm × thickness 0.025mm) of regulation, be attached at glass epoxy substrate (glass epoxy resin base material: 420 μm thick, copper wiring: 9 μm thick, 80 μm of spacing) on, by flip-chip erecting device " FCB3 " (PANASONIC system, trade name) by semiconductor chip (chip size: the length 7mm × width 7mm × height 0.15mm with solder bump, projection: copper post and scolding tin, 80 μm of spacing) (mounting condition: the arrival temperature of film-like adhesive 180 DEG C is installed, 10 seconds, 0.5MPa.Then, the arrival temperature 245 DEG C of film-like adhesive, 10 seconds, 0.5MPa).Thus, obtain and make above-mentioned glass epoxy substrate and the semiconductor chip with solder bump carry out daisy chain (デ ィ ジ ー チ ェ ー Application) in the same manner as Fig. 4 to be connected and the semiconductor device obtained.
Use universal instrument (ADVANTEST system, trade name " R6871E ") to measure the contact resistance value of the semiconductor device obtained, thus evaluate initial turn-on could be carried out after installation.Be the average evaluation of 11 ~ 14 Ω by contact resistance value be connectivity good " A ", by the situation of contact resistance value in addition or bad connection (Open) occurs and does not show the average evaluation of resistance value for " B ".
The evaluation > of the reflux-resisting welded property of <
Use encapsulant (Hitachi Chemical Co., Ltd.'s system, trade name " CEL9700HF10K "), 180 DEG C, 6.75MPa, under the condition of 90 seconds, it is the shape of regulation by above-mentioned semiconductor device mold, in cleaning oven (ESPEC Co., Ltd. system), obtain packaging body 175 DEG C of solidifications 5 hours.Then, after this packaging body being carried out high temperature moisture absorption under JEDEClevel2 condition, packaging body is passed through in IR reflow soldering (FURUKAWAELECTRIC system, trade name " SALAMANDER ").By the connectivity of the packaging body after the method evaluation Reflow Soldering same with initial internuncial evaluation described later, as the evaluation of reflux-resisting welded property.Be set to not peeling off, connecting good situation " A ", by peeling off, bad connection and the situation not showing resistance value be set to " B ".
Evaluation (the resistance to TCT evaluates) > of < connection reliability
Use encapsulant (Hitachi Chemical Co., Ltd.'s system, trade name " CEL9700HF10K "), 180 DEG C, 6.75MPa, be the shape of regulation by above-mentioned semiconductor device mold under the condition of 90 seconds, in cleaning oven (ESPEC Co., Ltd. system), obtain packaging body 175 DEG C of solidifications 5 hours.Then, this packaging body is positioned over thermal cycling test machine (ETAC system, THERMALSHOCKCHAMBERNT1200) in, flow through the electric current of 1mA, 25 DEG C 2 minutes/-55 DEG C 15 minutes/25 DEG C 2 minutes/125 DEG C 15 minutes/25 DEG C are set to 1 for 2 minutes circulate and measure contact resistance, the change of the contact resistance after repeatedly carrying out 1000 circulations is evaluated.Compared with initial resistance value waveform, do not have the situation of large change to be set to " A " by after 1000 circulations yet, the situation of the difference creating 1 more than Ω is set to " B ".
Evaluation (the resistance to HAST evaluates) > of < insulating reliability
Made film-like adhesive is cut the size (length 10mm × width 5mm × thickness 25 μm) of regulation, be attached at the comb-type electrode substrate (wiring closet distance: 0.05mm) being formed with distribution copper wiring on polyimide substrate, as shown in Figure 5, stacked film-like adhesive 40 on the substrate 20 being formed with comb-type electrode 90 is produced and the sample obtained.Be explained, in Figure 5, conveniently eliminate the diagram of film-like adhesive.Then, sample is solidified 185 DEG C of maintenances 3 hours in cleaning oven (ESPEC Co., Ltd. system).After solidification, take out each sample, be arranged at accelerated life test device (HIRAYAMA Inc., trade name " PL-422R8 ", condition: 130 DEG C/relative humidity, 85%/200 hour/5V applies), determine insulation resistance.Through 200 hours, be 10 by insulation resistance 8the situation of more than Ω is established and is evaluated as " A ", by less than 10 8the average evaluation of Ω is " B ".
The raw-material composition (unit: mass parts) of the adhesive composite of each embodiment and each comparative example is shown in Table 1, the result of each test is shown in table 2.
Table 1
Table 2
Confirm: in the embodiment 1 ~ 3 employing acrylic acid series surface treatment filler, the bonding force at 260 DEG C after moisture absorption is high, and any one characteristic in reflux-resisting welded property, resistance to TCT and resistance to HAST is all excellent.
Symbol description
10 semiconductor chips, 15 distributions (connecting portion), 20 substrates (wired circuit board), 30 connect projections, 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 (34)

1. the application in the semiconductor device that the respective connecting portion that an adhesive composite is used for semiconductor device or the multiple semiconductor chip be reciprocally electrically connected at the respective connecting portion of semiconductor chip and wired circuit board is reciprocally electrically connected, described connecting portion sealed
Described adhesive composite contains epoxy resin, curing agent, carried out surface-treated acrylic acid series surface treatment filler by the compound with the group shown in following general formula (1) and weight average molecular weight is the macromolecule component of more than 10000,
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
2. application according to claim 1, wherein, described compound is the compound represented by following general formula (2),
In formula (2), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30, R 3represent the alkyl of carbon number 1 ~ 30.
3. the application in the semiconductor device that the respective connecting portion that an adhesive composite is used for semiconductor device or the multiple semiconductor chip be reciprocally electrically connected at the respective connecting portion of semiconductor chip and wired circuit board is reciprocally electrically connected, described connecting portion sealed
It is the macromolecule component of more than 10000 that described adhesive composite contains epoxy resin, curing agent, the filler with the group shown in following general formula (1) and weight average molecular weight,
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
4. the application according to any one of claims 1 to 3, wherein, described R 2for the alkylidene of carbon number 1 ~ 15.
5. the application according to any one of claims 1 to 3, wherein, described filler comprises silica filler.
6. the application according to any one of claims 1 to 3, wherein, when the shape of described filler is spherical, average grain diameter is less than 2 μm.
7. the application according to any one of claims 1 to 3, wherein, the use level of described filler with the solid constituent of described adhesive composite all for benchmark be 5 ~ 80 quality %.
8. the application according to any one of claims 1 to 3, wherein, the macromolecule component of described weight average molecular weight more than 10000 comprises at least one selected in the group be made up of phenoxy resin, polyimide resin, acrylic rubber, cyanate ester resin and poly-carbodiimide resin.
9. the application according to any one of claims 1 to 3, wherein, the content of the macromolecule component of described weight average molecular weight more than 10000 is 1 ~ 500 mass parts relative to described epoxy resin 100 mass parts.
10. the application according to any one of claims 1 to 3, wherein, the weight average molecular weight of described macromolecule component is more than 30000, and vitrification point is less than 100 DEG C.
11. application according to any one of claims 1 to 3, wherein, described adhesive composite is further containing flux activity agent.
12. application according to claim 11, wherein, described flux activity agent comprises carboxylic acids.
13. application according to any one of claims 1 to 3, wherein, described curing agent comprises at least one selected in the group be made up of phenolic resins system curing agent, acid anhydrides system curing agent, amine system curing agent, imidazoles system curing agent and phosphine system curing agent.
14. application according to claim 13, wherein, described imidazoles system curing agent is by 1-cyanoethyl-2-undecyl imidazole, 1-cyano group-2-phenylimidazole, 1-cyanoethyl-2-undecyl imidazole trimellitate, 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, the at least one selected in the group of 5-bishydroxymethyl imidazoles and 2-phenyl-4-methyl-5-hydroxymethylimidazole composition.
15. application according to claim 13, wherein, described curing agent is imidazoles system curing agent, and the content of described imidazoles system curing agent is 0.1 ~ 20 mass parts relative to described epoxy resin 100 mass parts.
16. application according to claim 13, wherein, described curing agent is phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent, and described phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent are 0.3 ~ 1.5 relative to the equivalent proportion of described epoxy resin.
17. application according to any one of claims 1 to 3, wherein, the shape of described adhesive composite is membranaceous.
18. 1 kinds of semiconductor devices, it is the semiconductor device that the respective connecting portion of the semiconductor device that is reciprocally electrically connected of the respective connecting portion of semiconductor chip and wired circuit board or multiple semiconductor chip is reciprocally electrically connected,
Described connecting portion is sealed by the solidfied material of adhesive composite,
Described adhesive composite contains epoxy resin, curing agent, carried out surface-treated acrylic acid series surface treatment filler by the compound with the group shown in following general formula (1) and weight average molecular weight is the macromolecule component of more than 10000,
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
19. semiconductor devices according to claim 18, wherein, described compound is the compound represented by following general formula (2),
In formula (2), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30, R 3represent the alkyl of carbon number 1 ~ 30.
20. 1 kinds of semiconductor devices, it is the semiconductor device that the respective connecting portion of the semiconductor device that is reciprocally electrically connected of the respective connecting portion of semiconductor chip and wired circuit board or multiple semiconductor chip is reciprocally electrically connected,
Described connecting portion is sealed by the solidfied material of adhesive composite,
It is the macromolecule component of more than 10000 that described adhesive composite contains epoxy resin, curing agent, the filler with the group shown in following general formula (1) and weight average molecular weight,
In formula (1), R 1represent the alkyl of hydrogen atom or carbon number 1 or 2, R 2represent the alkylidene of carbon number 1 ~ 30.
21. semiconductor devices according to any one of claim 18 ~ 20, wherein, described R 2for the alkylidene of carbon number 1 ~ 15.
22. semiconductor devices according to any one of claim 18 ~ 20, wherein, described filler comprises silica filler.
23. semiconductor devices according to any one of claim 18 ~ 20, wherein, when the shape of described filler is spherical, average grain diameter is less than 2 μm.
24. semiconductor devices according to any one of claim 18 ~ 20, wherein, the use level of described filler with the solid constituent of described adhesive composite all for benchmark be 5 ~ 80 quality %.
25. the semiconductor device according to any one of claim 18 ~ 20, wherein, the macromolecule component of described weight average molecular weight more than 10000 comprises at least one selected in the group be made up of phenoxy resin, polyimide resin, acrylic rubber, cyanate ester resin and poly-carbodiimide resin.
26. semiconductor devices according to any one of claim 18 ~ 20, wherein, the content of the macromolecule component of described weight average molecular weight more than 10000 is 1 ~ 500 mass parts relative to described epoxy resin 100 mass parts.
27. semiconductor devices according to any one of claim 18 ~ 20, wherein, the weight average molecular weight of described macromolecule component is more than 30000, and vitrification point is less than 100 DEG C.
28. semiconductor devices according to any one of claim 18 ~ 20, wherein, described adhesive composite is further containing flux activity agent.
29. semiconductor devices according to claim 28, wherein, described flux activity agent comprises carboxylic acids.
30. the semiconductor device according to any one of claim 18 ~ 20, wherein, described curing agent comprises at least one selected in the group be made up of phenolic resins system curing agent, acid anhydrides system curing agent, amine system curing agent, imidazoles system curing agent and phosphine system curing agent.
31. semiconductor devices according to claim 30, wherein, described imidazoles system curing agent is by 1-cyanoethyl-2-undecyl imidazole, 1-cyano group-2-phenylimidazole, 1-cyanoethyl-2-undecyl imidazole trimellitate, 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, the at least one selected in the group of 5-bishydroxymethyl imidazoles and 2-phenyl-4-methyl-5-hydroxymethylimidazole composition.
32. semiconductor devices according to claim 30, wherein, described curing agent is imidazoles system curing agent, and the content of described imidazoles system curing agent is 0.1 ~ 20 mass parts relative to described epoxy resin 100 mass parts.
33. semiconductor devices according to claim 30, wherein, described curing agent is phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent, and described phenolic resins system curing agent, acid anhydrides system curing agent or amine system curing agent are 0.3 ~ 1.5 relative to the equivalent proportion of described epoxy resin.
34. semiconductor devices according to any one of claim 18 ~ 20, wherein, the shape of described adhesive composite is membranaceous.
CN201180047053.3A 2010-09-30 2011-09-29 The manufacture method of adhesive composite, semiconductor device and semiconductor device Active CN103222040B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
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