WO2019150446A1 - Composition adhésive, film adhésif, feuille adhésive et procédé de production de dispositif à semi-conducteur - Google Patents

Composition adhésive, film adhésif, feuille adhésive et procédé de production de dispositif à semi-conducteur Download PDF

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Publication number
WO2019150446A1
WO2019150446A1 PCT/JP2018/003023 JP2018003023W WO2019150446A1 WO 2019150446 A1 WO2019150446 A1 WO 2019150446A1 JP 2018003023 W JP2018003023 W JP 2018003023W WO 2019150446 A1 WO2019150446 A1 WO 2019150446A1
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WIPO (PCT)
Prior art keywords
adhesive
film
component
adhesive composition
group
Prior art date
Application number
PCT/JP2018/003023
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English (en)
Japanese (ja)
Inventor
慎太郎 橋本
祐樹 中村
智陽 山崎
健太 菊地
大輔 舛野
Original Assignee
日立化成株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to PCT/JP2018/003023 priority Critical patent/WO2019150446A1/fr
Priority to KR1020207022893A priority patent/KR102444486B1/ko
Priority to KR1020227031592A priority patent/KR102553619B1/ko
Priority to CN201880087334.3A priority patent/CN111630126B/zh
Priority to JP2019568439A priority patent/JP7176536B2/ja
Priority to SG11202006826WA priority patent/SG11202006826WA/en
Priority to TW108103150A priority patent/TWI804569B/zh
Publication of WO2019150446A1 publication Critical patent/WO2019150446A1/fr
Priority to JP2022179719A priority patent/JP7472954B2/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • 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
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • C09J11/08—Macromolecular additives
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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    • 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
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    • H01L24/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
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    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
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    • H01L25/07—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L29/00
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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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
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    • H01L2224/484—Connecting portions
    • H01L2224/4847—Connecting portions the connecting portion on the bonding area of the semiconductor or solid-state body being a wedge bond
    • H01L2224/48472—Connecting portions the connecting portion on the bonding area of the semiconductor or solid-state body being a wedge bond the other connecting portion not on the bonding area also being a wedge bond, i.e. wedge-to-wedge
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    • H01L2224/92—Specific sequence of method steps
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Definitions

  • the present invention relates to an adhesive composition, a film adhesive, an adhesive sheet, and a method for manufacturing a semiconductor device.
  • silver paste is mainly used for joining a semiconductor chip and a support member for mounting the semiconductor chip.
  • the supporting members used are also required to be miniaturized and densified.
  • problems such as occurrence of defects during wire bonding due to protrusion of the paste or inclination of the semiconductor chip, difficulty in controlling the film thickness, and generation of voids may occur.
  • a film adhesive for joining a semiconductor chip and a support member has been used (see, for example, Patent Document 1).
  • an adhesive sheet comprising a dicing tape and a film adhesive laminated on the dicing tape
  • the film adhesive is attached to the back surface of the semiconductor wafer, and the semiconductor wafer is separated into pieces by dicing.
  • a semiconductor chip with an adhesive can be obtained.
  • the obtained semiconductor chip with a film adhesive can be attached to a support member via a film adhesive and bonded by thermocompression bonding.
  • the film-like adhesive is used as FOW (Film Over Wire) which is a wire-embedded film-like adhesive or FOD (Film Over Die) which is a semiconductor chip-embedded film-like adhesive
  • FOW Flexible Over Wire
  • FOD Fin Off Die
  • high fluidity is required at the time of thermocompression bonding. Therefore, the frequency and amount of bleed tend to increase further. In some cases, the bleed may occur even on the upper surface of the semiconductor chip, which may lead to electrical failure or wire bonding failure.
  • the present invention has been made in view of such circumstances, and has as its main object to provide an adhesive composition capable of suppressing bleeding while having good embedding properties during thermocompression bonding. To do.
  • thermosetting resin includes an epoxy resin having an alicyclic ring. According to such an adhesive composition, it is possible to suppress bleeding while having good embedding properties at the time of thermocompression bonding.
  • the curing agent may include a phenol resin.
  • the elastomer may contain an acrylic resin.
  • thermosetting resin may further contain an aromatic epoxy resin having no alicyclic ring.
  • Aromatic epoxy resins that do not have an alicyclic ring may be liquid at 25 ° C.
  • the adhesive composition may further contain an inorganic filler. Moreover, the adhesive composition may further contain a curing accelerator.
  • An adhesive composition is a semiconductor device in which a first semiconductor element is wire-bonded to a substrate via a first wire, and a second semiconductor element is pressure-bonded on the first semiconductor element.
  • the second semiconductor element may be used for pressure bonding and at least part of the first wire is embedded.
  • the present invention further includes a composition comprising a thermosetting resin, a curing agent, and an elastomer, wherein the thermosetting resin includes an epoxy resin having an alicyclic ring.
  • the thermosetting resin includes an epoxy resin having an alicyclic ring.
  • the present invention provides a film adhesive formed by forming the above-described adhesive composition into a film.
  • the present invention provides an adhesive sheet comprising a base material and the above-described film adhesive provided on the base material.
  • the substrate may be a dicing tape.
  • an adhesive sheet whose base material is a dicing tape may be referred to as a “dicing die bonding integrated adhesive sheet”.
  • the adhesive sheet may further include a protective film laminated on the surface opposite to the base of the film adhesive.
  • the present invention provides a wire bonding step of electrically connecting a first semiconductor element via a first wire on a substrate, and the above-described film shape on one side of the second semiconductor element.
  • a wire bonding step of electrically connecting a first semiconductor element via a first wire on a substrate, and the above-described film shape on one side of the second semiconductor element.
  • the first semiconductor chip is wire bonded to the semiconductor substrate via the first wire, and the second semiconductor chip is pressure-bonded to the first semiconductor chip via the adhesive film.
  • the first semiconductor chip may be a wire embedded type semiconductor device in which at least a part of the first wire is embedded in the adhesive film, and the first wire and the first semiconductor chip are embedded in the adhesive film. It may be a chip embedded semiconductor device.
  • an adhesive composition capable of suppressing bleeding while having good embedding properties at the time of thermocompression bonding. Therefore, the film-like adhesive formed by forming the adhesive composition into a film is FOD (Film Over Die) which is a semiconductor chip-embedded film-like adhesive or FOW (Film) which is a wire-embedded film-like adhesive. Over Wire) can be useful. Moreover, according to this invention, the manufacturing method of the adhesive sheet using such a film adhesive and a semiconductor device is provided.
  • FIG. 1 is a schematic cross-sectional view showing a semiconductor device according to an embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of the manufacturing method of the semiconductor device which concerns on one Embodiment. It is a schematic cross section which shows a series of processes of
  • (meth) acrylic acid means acrylic acid or methacrylic acid corresponding thereto.
  • the adhesive composition according to this embodiment contains (A) a thermosetting resin, (B) a curing agent, and (C) an elastomer.
  • the adhesive composition is thermosetting and can be in a completely cured product (C stage) state after the curing process through a semi-cured (B stage) state.
  • thermosetting resin may contain an epoxy resin from the viewpoint of adhesiveness.
  • the adhesive composition according to this embodiment includes (A-1) an epoxy resin having an alicyclic ring as a thermosetting resin.
  • the component (A-1) is a compound having an alicyclic ring and an epoxy group in the molecule.
  • the epoxy group may be bonded to a portion other than the alicyclic ring or the alicyclic ring of the compound via a single bond or a linking group (for example, an alkylene group, an oxyalkylene group, etc.).
  • the compound may be a compound having an epoxy group formed with two carbon atoms constituting the alicyclic ring (that is, an alicyclic epoxy compound).
  • the epoxy equivalent of the component (A-1) is not particularly limited, but may be 90 to 600 g / eq, 100 to 500 g / eq, or 120 to 450 g / eq. When the epoxy equivalent of the component (A-1) is in such a range, better reactivity and fluidity tend to be obtained.
  • the component (A-1) may be, for example, any of epoxy resins represented by the following general formulas (1) to (4).
  • E represents an alicyclic ring
  • G represents a single bond or an alkylene group
  • R 1 each independently represents a hydrogen atom or a monovalent hydrocarbon group.
  • n1 represents an integer of 1 to 10
  • m represents an integer of 1 to 3.
  • E may have from 4 to 12, 5 to 11, or 6 to 10 carbon atoms.
  • E may be monocyclic or polycyclic, but is preferably polycyclic and more preferably a dicyclopentadiene ring.
  • the alkylene group for G may be an alkylene group having 1 to 5 carbon atoms such as a methylene group, an ethylene group, a propylene group, a butylene group, or a pentylene group.
  • G is preferably a single bond.
  • the monovalent hydrocarbon group in R 1 is, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group, an aryl group such as a phenyl group or a naphthyl group, or a heteroaryl group such as a pyridyl group. It may be.
  • R 1 is preferably a hydrogen atom.
  • the epoxy resin represented by the general formula (1) may be an epoxy resin represented by the following general formula (1a).
  • n1 is as defined above.
  • Examples of commercially available epoxy resins represented by the general formula (1a) include HP-7200L, HP-7200H, HP-7200 (all manufactured by DIC Corporation), and XD-1000 (manufactured by Nippon Kayaku Co., Ltd.). Etc.
  • R 2 represents a divalent hydrocarbon group.
  • the divalent hydrocarbon group in R 2 is, for example, an alkylene group such as a methylene group, an ethylene group, a propylene group, a butylene group or a pentylene group, an arylene group such as a phenylene group or a naphthylene group, or a heteroarylene group such as a pyridylene group. It may be.
  • R 2 is preferably an alkylene group having 1 to 5 carbon atoms.
  • Examples of commercially available epoxy resins represented by the general formula (2) include Celoxide 2021P and Celoxide 2081 (both manufactured by Daicel Corporation).
  • R 3 , R 4 , and R 5 each independently represent a divalent hydrocarbon group.
  • Examples of the divalent hydrocarbon group for R 3 , R 4 , and R 5 include the same groups as those exemplified for the divalent hydrocarbon group for R 2 .
  • Examples of commercially available epoxy resins represented by the general formula (3) include Syna-Epoxy28 (manufactured by SYANASIA).
  • R 6 represents a hydrogen atom or a monovalent hydrocarbon group
  • n2 represents an integer of 1 to 10.
  • Examples of the monovalent hydrocarbon group for R 6 include the same groups as those exemplified for the monovalent hydrocarbon group for R 1 .
  • Examples of commercially available epoxy resins represented by the general formula (4) include EHPE3150 (manufactured by Daicel Corporation).
  • the component (A-1) is preferably an epoxy resin represented by the general formula (1), more preferably an epoxy resin represented by the general formula (1a), from the viewpoint of heat resistance.
  • the content of the component (A-1) may be 15 to 100% by mass based on the total amount of the component (A).
  • the content of the component (A-1) may be 40% by mass or more, 50% by mass or more, or 60% by mass or more.
  • the content of the component (A-1) may be 5% by mass or more, 10% by mass or more, or 20% by mass or more based on the total amount of the adhesive composition.
  • the content of the component (A-1) is 5% by mass or more based on the total amount of the adhesive composition, bleeding tends to be well suppressed while having better embedding property at the time of thermocompression bonding.
  • the component (A) may further contain (A-2) an aromatic epoxy resin having no alicyclic ring in addition to the component (A-1).
  • the aromatic epoxy resin having no alicyclic ring is a compound having an aromatic ring and an epoxy group in the molecule and not having an alicyclic ring.
  • the component (A-2) include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, bisphenol F.
  • Novolac type epoxy resin stilbene type epoxy resin, triazine skeleton containing epoxy resin, fluorene skeleton containing epoxy resin, triphenol phenol methane type epoxy resin, biphenyl type epoxy resin, xylylene type epoxy resin, phenyl aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin
  • Examples thereof include diglycidyl ether compounds of polycyclic aromatics such as resins, naphthalene type epoxy resins, polyfunctional phenols, and anthracene. You may use these individually by 1 type or in combination of 2 or more types.
  • the component (A-2) may be liquid at 25 ° C.
  • the epoxy equivalent of the component (A-2) is not particularly limited, but may be 90 to 600 g / eq, 100 to 500 g / eq, or 120 to 450 g / eq. When the epoxy equivalent of the component (A-2) is in such a range, better reactivity and fluidity tend to be obtained.
  • the content of component (A-2) may be 0 to 85% by mass based on the total amount of component (A).
  • the content of the component (A-2) may be 60% by mass or less, 50% by mass or less, or 40% by mass or less.
  • thermosetting resin contains an epoxy resin
  • examples of the component (B) include a phenol resin, an ester compound, an aromatic amine, an aliphatic amine, and an acid anhydride. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of reactivity and stability over time, the component (B) may contain a phenol resin.
  • the phenol resin can be used without particular limitation as long as it has a phenolic hydroxyl group in the molecule.
  • examples of the phenol resin include phenols such as phenol, cresol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol, and / or naphthols such as ⁇ -naphthol, ⁇ -naphthol, dihydroxynaphthalene, and formaldehyde.
  • a novolak-type phenol resin obtained by condensation or co-condensation with a compound having an aldehyde group in the presence of an acidic catalyst phenols such as allylated bisphenol A, allylated bisphenol F, allylated naphthalenediol, phenol novolak, phenol, and / or Or phenol aralkyl resins, naphthol aralkyl resins, biphenyl aralkyl type resins synthesized from naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl Examples thereof include an enol resin and a phenylaralkyl type phenol resin.
  • the phenol resin has a water absorption of 2% by mass or less in a constant temperature and humidity chamber of 85 ° C. and 85% RH for 48 hours, and a thermogravimetric analyzer (TGA). It is preferable that the heating mass decrease rate (heating rate: 5 ° C./min, atmosphere: nitrogen) at 350 ° C. measured in step 1 is less than 5% by mass.
  • phenol resins examples include Phenolite KA series, TD series (manufactured by DIC Corporation), Millex XLC series, XL series (manufactured by Mitsui Chemicals), and HE series (manufactured by Air Water Corporation). Can be mentioned.
  • the hydroxyl equivalent of the phenol resin is not particularly limited, but may be 80 to 400 g / eq, 90 to 350 g / eq, or 100 to 300 g / eq. When the hydroxyl equivalent of the phenol resin is in such a range, better reactivity and fluidity tend to be obtained.
  • the ratio of the epoxy equivalent of the epoxy resin to the hydroxyl equivalent of the phenol resin is: From the viewpoint of curability, 0.30 / 0.70 to 0.70 / 0.30, 0.35 / 0.65 to 0.65 / 0.35, 0.40 / 0.60 to 0.60 / It may be 0.40, or 0.45 / 0.55 to 0.55 / 0.45.
  • the equivalent ratio is 0.30 / 0.70 or more, more sufficient curability tends to be obtained.
  • the equivalent ratio is 0.70 / 0.30 or less, the viscosity can be prevented from becoming too high, and more sufficient fluidity can be obtained.
  • the total content of the component (A) and the component (B) may be 30 to 70% by mass based on the total amount of the adhesive composition.
  • the total content of the component (A) and the component (B) may be 33% by mass or more, 36% by mass or more, or 40% by mass or more, and is 65% by mass or less, 60% by mass or less, or 55% by mass. % Or less.
  • the adhesiveness tends to be improved.
  • the viscosity can be prevented from becoming too low, and bleeding can be further suppressed. There is a tendency to be able to.
  • the adhesive composition according to this embodiment contains (C) an elastomer.
  • the component (C) preferably has a glass transition temperature (Tg) of the polymer constituting the elastomer of 50 ° C. or lower.
  • component (C) examples include acrylic resins, polyester resins, polyamide resins, polyimide resins, silicone resins, butadiene resins, acrylonitrile resins, and modified products thereof.
  • the component (C) may contain an acrylic resin from the viewpoint of solubility in a solvent and fluidity.
  • the acrylic resin means a polymer containing a structural unit derived from a (meth) acrylic acid ester.
  • the acrylic resin is preferably a polymer containing a structural unit derived from a (meth) acrylic acid ester having a crosslinkable functional group such as an epoxy group, an alcoholic or phenolic hydroxyl group, or a carboxy group as a structural unit.
  • the acrylic resin may be an acrylic rubber such as a copolymer of (meth) acrylic acid ester and acrylonitrile.
  • the glass transition temperature (Tg) of the acrylic resin may be ⁇ 50 to 50 ° C. or ⁇ 30 to 30 ° C. If the Tg of the acrylic resin is ⁇ 50 ° C. or higher, the flexibility of the adhesive composition tends to be prevented from becoming too high. Thereby, it becomes easy to cut
  • the glass transition temperature (Tg) means a value measured using a DSC (thermal differential scanning calorimeter) (for example, “Thermo Plus 2” manufactured by Rigaku Corporation).
  • the weight average molecular weight (Mw) of the acrylic resin may be 100,000 to 3 million or 500,000 to 2 million.
  • Mw means a value measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.
  • acrylic resins examples include SG-70L, SG-708-6, WS-023 EK30, SG-280 EK23, HTR-860P-3CSP, HTR-860P-3CSP-3DB (all Nagase ChemteX Corporation) Company-made).
  • the content of the component (C) may be 20 to 200 parts by mass or 30 to 100 parts by mass with respect to 100 parts by mass of the total amount of the components (A) and (B).
  • the handleability for example, bendability
  • the film adhesive is better. It tends to be.
  • the adhesive composition is further prevented from becoming too flexible. There is a tendency to be able to. Thereby, it becomes easy to cut
  • the adhesive composition according to this embodiment may further contain (D) an inorganic filler.
  • the inorganic filler include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, aluminum borate whisker, boron nitride, crystal Examples thereof include crystalline silica and amorphous silica. These may be used individually by 1 type and may be used in combination of 2 or more type.
  • the inorganic filler may contain aluminum oxide, aluminum nitride, boron nitride, crystalline silica, or amorphous silica.
  • the inorganic filler is aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, Magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, crystalline silica or amorphous silica may be included.
  • the average particle diameter of the component (D) may be 0.005 to 0.5 ⁇ m or 0.05 to 0.3 ⁇ m from the viewpoint of further improving the adhesiveness.
  • an average particle diameter means the value calculated
  • the component (D) may be surface-treated with a surface treatment agent from the viewpoint of compatibility between the surface and the solvent, other components, and the like, and adhesive strength.
  • a surface treatment agent include a silane coupling agent.
  • the functional group of the silane coupling agent include a vinyl group, a (meth) acryloyl group, an epoxy group, a mercapto group, an amino group, a diamino group, an alkoxy group, and an ethoxy group.
  • the content of the component (D) may be 10 to 90 parts by mass or 10 to 50 parts by mass with respect to 100 parts by mass of the total amount of the components (A), (B), and (C).
  • the dicing property of the adhesive layer before curing is The adhesive strength of the adhesive layer after curing tends to be improved.
  • the content of the component (D) is 90 parts by mass or less with respect to 100 parts by mass of the total amount of the component (A), the component (B), and the component (C)
  • the adhesive composition according to this embodiment may contain (E) a curing accelerator.
  • a hardening accelerator is not specifically limited, What is generally used can be used.
  • Examples of the component (E) include imidazoles and derivatives thereof, organic phosphorus compounds, secondary amines, tertiary amines, quaternary ammonium salts, and the like. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of reactivity, the component (E) may be imidazoles and derivatives thereof.
  • imidazoles examples include 2-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, and the like. You may use these individually by 1 type or in combination of 2 or more types.
  • the content of the component (E) is 0.04 to 3 parts by mass or 0.04 to 0.2 parts by mass with respect to 100 parts by mass of the total amount of the components (A), (B) and (C). It may be.
  • content of (E) component exists in such a range, it exists in the tendency which can make sclerosis
  • the adhesive composition according to the present embodiment may further contain an antioxidant, a silane coupling agent, a rheology control agent and the like as other components.
  • the content of these components may be 0.02 to 3 parts by mass with respect to 100 parts by mass as the total of component (A), component (B), and component (C).
  • the adhesive composition according to this embodiment may be used as an adhesive varnish diluted with a solvent.
  • the solvent is not particularly limited as long as it can dissolve components other than the component (D).
  • the solvent include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene and p-cymene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; tetrahydrofuran, 1,4-dioxane and the like.
  • Cyclic ether such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone; ester such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, ⁇ -butyrolactone; Examples thereof include carbonic acid esters such as ethylene carbonate and propylene carbonate; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone. You may use these individually by 1 type or in combination of 2 or more types.
  • the solvent may be toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexane from the viewpoints of solubility and boiling point.
  • the solid component concentration in the adhesive varnish may be 10 to 80% by mass based on the total mass of the adhesive varnish.
  • Adhesive varnish is to mix and knead component (A), component (B), component (C), and solvent, and component (D), component (E), and other components as necessary.
  • Mixing and kneading can be performed by appropriately combining dispersers such as a normal stirrer, a raking machine, a triple roll, a ball mill, and a bead mill.
  • dispersers such as a normal stirrer, a raking machine, a triple roll, a ball mill, and a bead mill.
  • the mixing time can be shortened by blending the high molecular weight component.
  • bubbles in the varnish may be removed by vacuum degassing or the like.
  • FIG. 1 is a schematic cross-sectional view showing a film adhesive according to an embodiment.
  • the film adhesive 10 is formed by forming the above-described adhesive composition into a film.
  • the film adhesive 10 may be in a semi-cured (B stage) state.
  • Such a film adhesive 10 can be formed by applying an adhesive composition to a support film.
  • the film adhesive 10 can be formed by applying the adhesive varnish to a support film and removing the solvent by heating and drying.
  • the support film is not particularly limited, and examples thereof include films of polytetrafluoroethylene, polyethylene, polypropylene, polymethylpentene, polyethylene terephthalate, polyimide, and the like.
  • the thickness of the support film may be, for example, 60 to 200 ⁇ m or 70 to 170 ⁇ m.
  • a known method can be used, for example, knife coating method, roll coating method, spray coating method, gravure coating method, bar coating method, curtain coating method, etc. It is done.
  • the conditions for the heat drying are not particularly limited as long as the solvent used is sufficiently volatilized, but may be, for example, 50 to 200 ° C. for 0.1 to 90 minutes.
  • the thickness of the film adhesive can be appropriately adjusted according to the application.
  • the thickness of the film adhesive may be 20 to 200 ⁇ m, 30 to 200 ⁇ m, or 40 to 150 ⁇ m from the viewpoint of sufficiently embedding irregularities such as a semiconductor chip, a wire, and a wiring circuit of a substrate.
  • FIG. 2 is a schematic cross-sectional view showing an adhesive sheet according to an embodiment.
  • the adhesive sheet 100 includes a base material 20 and the above-described film adhesive 10 provided on the base material.
  • the substrate 20 is not particularly limited, but may be a substrate film.
  • the base film may be the same as the above support film.
  • the base material 20 may be a dicing tape.
  • Such an adhesive sheet can be used as a dicing die bonding integrated adhesive sheet. In this case, since the lamination process to the semiconductor wafer is performed once, the work efficiency can be improved.
  • the dicing tape examples include plastic films such as a polytetrafluoroethylene film, a polyethylene terephthalate film, a polyethylene film, a polypropylene film, a polymethylpentene film, and a polyimide film.
  • the dicing tape may be subjected to surface treatment such as primer coating, UV treatment, corona discharge treatment, polishing treatment, and etching treatment as necessary.
  • the dicing tape is preferably one having adhesiveness.
  • Such a dicing tape may be one obtained by imparting adhesiveness to the above-mentioned plastic film, or may be one obtained by providing an adhesive layer on one side of the above-mentioned plastic film.
  • the adhesive sheet 100 can be formed by applying an adhesive composition to a base film in the same manner as the above-described method for forming a film adhesive.
  • the method for applying the adhesive composition to the substrate 20 may be the same as the method for applying the adhesive composition to the support film.
  • the adhesive sheet 100 may be formed using a film adhesive prepared in advance.
  • the adhesive sheet 100 can be formed by laminating under a predetermined condition (for example, room temperature (20 ° C.) or a heated state) using a roll laminator, a vacuum laminator, or the like. Since the adhesive sheet 100 can be continuously manufactured and has high efficiency, it is preferably formed using a roll laminator in a heated state.
  • the thickness of the film adhesive 10 may be 20 to 200 ⁇ m, 30 to 200 ⁇ m, or 40 to 150 ⁇ m from the viewpoint of embedding properties such as unevenness of a semiconductor chip, a wire, a wiring circuit of a substrate, and the like.
  • the thickness of the film adhesive 10 is 20 ⁇ m or more, a sufficient adhesive force tends to be obtained, and when the thickness of the film adhesive 10 is 200 ⁇ m or less, it is economical and the semiconductor device It is possible to meet the demand for downsizing.
  • FIG. 3 is a schematic cross-sectional view showing an adhesive sheet according to another embodiment.
  • the adhesive sheet 110 further includes a protective film 30 laminated on the surface of the film adhesive 10 opposite to the base 20.
  • the protective film 30 may be the same as the above support film.
  • the thickness of the protective film may be, for example, 15 to 200 ⁇ m or 70 to 170 ⁇ m.
  • FIG. 4 is a schematic cross-sectional view showing a semiconductor device according to an embodiment.
  • the first semiconductor element Wa in the first stage is wire-bonded to the substrate 14 via the first wire 88, and the second semiconductor element Waa is formed on the first semiconductor element Wa.
  • the semiconductor device is a semiconductor device in which at least a part of the first wire 88 is embedded in the film adhesive 10 by being pressure-bonded via the film adhesive 10.
  • the semiconductor device is a semiconductor device in which the first wire 88 and the first semiconductor element Wa are embedded even if the semiconductor device is a wire embedded type semiconductor device in which at least a part of the first wire 88 is embedded. May be.
  • the substrate 14 and the second semiconductor element Waa are further electrically connected via the second wire 98, and the second semiconductor element Waa is sealed with the sealing material 42. ing.
  • the thickness of the first semiconductor element Wa may be 10 to 170 ⁇ m, and the thickness of the second semiconductor element Waa may be 20 to 400 ⁇ m.
  • the first semiconductor element Wa embedded in the film adhesive 10 is a controller chip for driving the semiconductor device 200.
  • the substrate 14 is composed of an organic substrate 90 having two circuit patterns 84 and 94 formed on the surface thereof.
  • the first semiconductor element Wa is pressure-bonded onto the circuit pattern 94 via an adhesive 41.
  • the second semiconductor element Waa is interposed via the film adhesive 10 so that the circuit pattern 94, the first semiconductor element Wa, and the circuit pattern 84 to which the first semiconductor element Wa is not bonded are covered. Crimped to the substrate 14.
  • a film adhesive 10 is embedded in the uneven steps due to the circuit patterns 84 and 94 on the substrate 14.
  • the second semiconductor element Waa, the circuit pattern 84, and the second wire 98 are sealed with a resin sealing material 42.
  • a die-bonding step embedded in the adhesive is
  • the semiconductor device 200 is a semiconductor device in which a first wire 88 and a first semiconductor element Wa are embedded, and is manufactured by the following procedure.
  • the first semiconductor element Wa having the adhesive 41 is crimped onto the circuit pattern 94 on the substrate 14, and the circuit pattern 84 on the substrate 14 and the first pattern are connected to each other via the first wire 88.
  • the first semiconductor element Wa is electrically bonded and connected (first wire bonding step).
  • the adhesive sheet 100 is laminated on one side of a semiconductor wafer (for example, thickness 100 ⁇ m, size: 8 inches), and the base material 20 is peeled off, whereby the film-like adhesive 10 (for example, thickness) is applied to one side of the semiconductor wafer. 110 ⁇ m). Then, after the dicing tape is bonded to the film adhesive 10, the dicing tape is diced to a predetermined size (for example, 7.5 mm square), whereby the second film adhesive 10 is applied as shown in FIG. The semiconductor element Waa is obtained (laminating step).
  • the temperature condition of the laminating process may be 50-100 ° C or 60-80 ° C.
  • the temperature in the laminating step is 50 ° C. or higher, good adhesion to the semiconductor wafer can be obtained.
  • the temperature of the laminating process is 100 ° C. or lower, the film-like adhesive 10 can be prevented from flowing excessively during the laminating process, so that it is possible to prevent a change in thickness and the like.
  • Examples of the dicing method include blade dicing using a rotary blade, and a method of cutting a film adhesive or both a wafer and a film adhesive with a laser.
  • the second semiconductor element Waa to which the film adhesive 10 is attached is pressure-bonded to the substrate 14 to which the first semiconductor element Wa is bonded via the first wire 88.
  • the first wire 88 and the first semiconductor element Wa are covered with the second semiconductor element Waa to which the film-like adhesive 10 is attached by the film-like adhesive 10.
  • the second semiconductor element Waa is fixed to the substrate 14 by pressing the second semiconductor element Waa to the substrate 14 (die bonding step).
  • the film adhesive 10 is preferably pressure-bonded for 0.5 to 3.0 seconds under conditions of 80 to 180 ° C. and 0.01 to 0.50 MPa.
  • the film adhesive 10 is pressed and heated for 5 minutes or more under the conditions of 60 to 175 ° C. and 0.3 to 0.7 MPa.
  • the circuit pattern 84, the second wire 98 and the second semiconductor element Waa are sealed with a sealing material 42.
  • the semiconductor device 200 can be manufactured through such steps.
  • the semiconductor device may be a wire embedded type semiconductor device in which at least a part of the first wire 88 is embedded.
  • Examples 1 to 8 and Comparative Examples 1 to 4 ⁇ Preparation of adhesive sheet>
  • a varnish of an adhesive composition having a solid content of 40% by mass was prepared using cyclohexanone as a solvent.
  • the obtained varnish was filtered through a 100-mesh filter and vacuum degassed.
  • the varnish after vacuum defoaming was applied as a base film onto a polyethylene terephthalate (PET) film that had been subjected to a release treatment with a thickness of 38 ⁇ m.
  • PET polyethylene terephthalate
  • the applied varnish was heat-dried in two stages of 90 ° C. for 5 minutes, followed by 140 ° C. for 5 minutes.
  • an adhesive sheet provided with a film adhesive having a thickness of 110 ⁇ m in a semi-cured (B stage) state was obtained on the base film.
  • Epoxy resin having alicyclic ring A-1-1 Epoxy resin represented by general formula (1a) (epoxy resin having dicyclopentadiene structure), DIC stock Product name: HP-7200L, epoxy equivalent: 250-280 g / eq A-1-2: Epoxy resin represented by the general formula (1a) (epoxy resin having a dicyclopentadiene structure), manufactured by Nippon Kayaku Co., Ltd., trade name: XD-1000, epoxy equivalent: 254 g / eq A-1-3: Epoxy resin represented by the general formula (2) (liquid at 25 ° C.), manufactured by Daicel Corporation, trade name: Celoxide 2021P, epoxy equivalent: 128 to 145 g / eq A-1-4: Epoxy resin represented by general formula (4), manufactured by Daicel Corporation, trade name: EHPE3150, epoxy equivalent: 170 to 190 g / eq (A-2) Aromatic epoxy resin having no alicyclic
  • an evaluation substrate having a total thickness of 260 ⁇ m coated with a solder resist (manufactured by Taiyo Nippon Sanso Co., Ltd., trade name: AUS308) is prepared, and the die bonding film of the semiconductor chip B with the die bonding film and the evaluation substrate solder Pressure-bonding was performed under the conditions of 120 ° C., 0.20 MPa, and 2 seconds so as to contact the resist.
  • the film adhesive of the semiconductor chip A and the semiconductor wafer of the semiconductor chip B were pressure-bonded under the conditions of 120 ° C., 0.20 MPa, and 1.5 seconds to obtain an evaluation sample.
  • alignment was performed so that the semiconductor chip B that was previously crimped was in the center of the semiconductor chip A.
  • the evaluation sample thus obtained was observed for the presence or absence of observation of voids with an ultrasonic digital diagnostic imaging apparatus (Insight Inc., probe: 75 MHz), and when voids were observed, The ratio of the void area was calculated, and these analysis results were evaluated as embeddability.
  • the evaluation criteria are as follows. The results are shown in Tables 1 and 2. A: No void was observed. B: Although voids were observed, the ratio was less than 5 area%. C: A void was observed, and the ratio was 5 area% or more.
  • Examples 1 to 3 including an epoxy resin having an alicyclic ring suppress bleed while maintaining good embedding properties as compared with Comparative Examples 1 to 3 not including the epoxy resin. I was able to. Further, from Examples 4 to 8 in Table 2, it was found that the same tendency was observed when an epoxy resin having another alicyclic ring was used. From these results, it was confirmed that the adhesive composition according to the present invention can suppress bleeding while having good embedding property at the time of thermocompression bonding.
  • a film adhesive formed by forming the adhesive composition into a film shape is It can be useful as FOD (Film Over Die), which is a chip-embedded film adhesive, or as FOW (Film Over Wire), which is a wire-embedded film adhesive.
  • SYMBOLS 10 Film adhesive, 14 ... Substrate, 20 ... Base material, 30 ... Protective film, 41 ... Adhesive, 42 ... Sealing material, 84, 94 ... Circuit pattern, 88 ... First wire, 90 ... Organic substrate 98, second wire, 100, 110, adhesive sheet, 200, semiconductor device, Wa, first semiconductor element, Waa, second semiconductor element.

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  • Adhesive Tapes (AREA)
  • Die Bonding (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Encapsulation Of And Coatings For Semiconductor Or Solid State Devices (AREA)
  • Dicing (AREA)

Abstract

L'invention concerne une composition adhésive qui comprend une ou plusieurs résines thermodurcissables, un durcisseur et un élastomère, les résines thermodurcissables comprenant une résine époxy ayant un noyau alicyclique. L'invention concerne également un film adhésif obtenu à partir de ladite composition adhésive. L'invention concerne également une feuille adhésive comprenant un tel film adhésif et un procédé de production d'un dispositif à semi-conducteur.
PCT/JP2018/003023 2018-01-30 2018-01-30 Composition adhésive, film adhésif, feuille adhésive et procédé de production de dispositif à semi-conducteur WO2019150446A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
PCT/JP2018/003023 WO2019150446A1 (fr) 2018-01-30 2018-01-30 Composition adhésive, film adhésif, feuille adhésive et procédé de production de dispositif à semi-conducteur
KR1020207022893A KR102444486B1 (ko) 2018-01-30 2018-01-30 접착제 조성물, 필름형 접착제, 접착 시트 및 반도체 장치의 제조 방법
KR1020227031592A KR102553619B1 (ko) 2018-01-30 2018-01-30 접착제 조성물, 필름형 접착제, 접착 시트 및 반도체 장치의 제조 방법
CN201880087334.3A CN111630126B (zh) 2018-01-30 2018-01-30 粘接剂组合物、膜状粘接剂、粘接片材及半导体装置的制造方法
JP2019568439A JP7176536B2 (ja) 2018-01-30 2018-01-30 接着剤組成物、フィルム状接着剤、接着シート、及び半導体装置の製造方法
SG11202006826WA SG11202006826WA (en) 2018-01-30 2018-01-30 Adhesive composition, filmy adhesive, adhesive sheet, and production method for semiconductor device
TW108103150A TWI804569B (zh) 2018-01-30 2019-01-28 接著劑組成物、膜狀接著劑、接著片及半導體裝置的製造方法
JP2022179719A JP7472954B2 (ja) 2018-01-30 2022-11-09 接着剤組成物、フィルム状接着剤、接着シート、及び半導体装置の製造方法

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SG11202006826WA (en) 2020-08-28
CN111630126A (zh) 2020-09-04
JP2023017948A (ja) 2023-02-07
KR20200113217A (ko) 2020-10-06
KR102444486B1 (ko) 2022-09-19
KR20220128678A (ko) 2022-09-21
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JP7472954B2 (ja) 2024-04-23
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