WO2010128611A1 - Agent adhésif de type film destiné à sceller un semi-conducteur, dispositif semi-conducteur, et procédé de fabrication du dispositif semi-conducteur - Google Patents

Agent adhésif de type film destiné à sceller un semi-conducteur, dispositif semi-conducteur, et procédé de fabrication du dispositif semi-conducteur Download PDF

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Publication number
WO2010128611A1
WO2010128611A1 PCT/JP2010/056004 JP2010056004W WO2010128611A1 WO 2010128611 A1 WO2010128611 A1 WO 2010128611A1 JP 2010056004 W JP2010056004 W JP 2010056004W WO 2010128611 A1 WO2010128611 A1 WO 2010128611A1
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film
semiconductor
adhesive
curing agent
bis
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PCT/JP2010/056004
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English (en)
Japanese (ja)
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一尊 本田
榎本　哲也
祐樹 中村
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日立化成工業株式会社
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Priority to JP2011512322A priority Critical patent/JP5578174B2/ja
Publication of WO2010128611A1 publication Critical patent/WO2010128611A1/fr

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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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • 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
    • 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
    • C09J2463/00—Presence of epoxy resin
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/10—Bump connectors; Manufacturing methods related thereto
    • H01L2224/15—Structure, shape, material or disposition of the bump connectors after the connecting process
    • H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
    • H01L2224/161—Disposition
    • H01L2224/16151—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/16221—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/16225—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/10—Bump connectors; Manufacturing methods related thereto
    • H01L2224/15—Structure, shape, material or disposition of the bump connectors after the connecting process
    • H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
    • H01L2224/161—Disposition
    • H01L2224/16151—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/16221—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/16225—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • H01L2224/16227—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation the bump connector connecting to a bond pad of the item
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/80—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
    • H01L2224/83—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 using a layer connector
    • H01L2224/8319—Arrangement of the layer connectors prior to mounting
    • H01L2224/83191—Arrangement of the layer connectors prior to mounting wherein the layer connectors are disposed only on the semiconductor or solid-state body
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L24/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L24/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
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    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/00014—Technical content checked by a classifier the subject-matter covered by the group, the symbol of which is combined with the symbol of this group, being disclosed without further technical details
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    • H01L2924/01005—Boron [B]
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    • H01L2924/01006—Carbon [C]
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    • H01L2924/01029—Copper [Cu]
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    • H01L2924/0105—Tin [Sn]
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    • H01L2924/01322—Eutectic Alloys, i.e. obtained by a liquid transforming into two solid phases
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    • H01L2924/06—Polymers
    • H01L2924/0665—Epoxy resin

Definitions

  • the present invention relates to a film sealing adhesive for semiconductor sealing, a semiconductor device, and a manufacturing method thereof.
  • connection methods As a method of connecting the bump and the electrode by the flip chip connection method, metal bonding using solder, tin, gold or copper, metal bonding by applying ultrasonic vibration, mechanical contact by the shrinkage force of the resin There are known methods for holding the above. Among these connection methods, since the reliability of the connection portion is excellent, a method of metal bonding using solder, tin, gold, or copper has become the mainstream.
  • COF Chip On Film
  • the gap between the semiconductor chip and the substrate is filled with a sealing resin to protect the connection portion from the external environment and prevent external stress from concentrating on the connection portion, and narrow pitch.
  • the insulation reliability between wiring is ensured (for example, refer patent document 1).
  • a method of injecting a liquid resin by capillary action and curing the resin after connecting the semiconductor chip and the substrate is generally used.
  • the above-described method has a problem that it takes a long time to inject the liquid resin and the productivity is lowered. It has become. Therefore, there is a need for a method for forming a sealing resin that is sufficiently excellent in productivity even when the gap between the chip and the substrate is small.
  • Voids due to springback in flip chip connection are due to deformation of the substrate and metal (wiring, bump) due to high temperature connection, and are likely to occur mainly at the connection portion between wiring and bump.
  • flip chips must be connected in a short time from the viewpoint of improving productivity. Therefore, in order to reduce voids in a short connection time, it is required to cure the adhesive in a shorter time.
  • the present invention has been made in view of the above circumstances, is sufficiently excellent in connectivity in a short time, can sufficiently suppress the generation of voids accompanying high-temperature heating, and sufficiently excellent in connection reliability. It is an object of the present invention to provide a film sealing adhesive for semiconductor sealing capable of manufacturing a semiconductor device and a method for manufacturing the semiconductor device. Another object of the present invention is to provide a semiconductor device in which the amount of voids in the sealing resin is sufficiently reduced and the connection reliability is sufficiently excellent.
  • the present invention comprises (a) an epoxy resin and (b) a catalyst-type curing agent, which becomes an active species by the catalyst-type curing agent or a curing agent that reacts with the catalyst-type curing agent.
  • a catalyst-type curing agent which becomes an active species by the catalyst-type curing agent or a curing agent that reacts with the catalyst-type curing agent.
  • Conventional film-like adhesives for semiconductor encapsulation contain an epoxy resin, a curing agent such as phenols, acid anhydrides or amines, and a catalytic curing agent.
  • the curing reaction of the epoxy resin by the curing agent is facilitated by the catalytic curing agent acting as a curing accelerator. This is presumably because the catalyst-type curing agent acts as a base, and the curing agent acts as an active species to cause a ring-opening reaction of the epoxy group and promote the reaction between the epoxy resin and the curing agent.
  • curing agent is a hardening
  • the curing reaction of the epoxy resin with the catalyst type curing agent is such that the electron pair of the catalyst type curing agent directly attacks the epoxy group and generates an oxygen anion, and this oxygen anion further reacts with the epoxy group. It is thought to proceed by anionic polymerization, and curing proceeds in a very short time.
  • the film-like adhesive for semiconductor encapsulation contains an epoxy resin, a curing agent, and a catalyst-type curing agent
  • the catalyst-type curing is caused by a reaction between the epoxy resin and the curing agent and a reduction in reaction points of the epoxy resin.
  • the homoanionic polymerization of the epoxy resin by the agent becomes difficult to proceed. For this reason, when a conventional film-like adhesive for semiconductor encapsulation is used, there is a limit to shortening the curing time.
  • the present inventors have a structure that does not contain a curing agent that is generally used as a film-like adhesive for semiconductor encapsulation, whereby the reaction of the epoxy resin by the catalytic curing agent proceeds more effectively,
  • the inventors have found that it can be cured in a short time while sufficiently suppressing generation of voids, and have completed the present invention.
  • the film-like adhesive for semiconductor encapsulation may further contain (c) a polymer component having a weight average molecular weight of 10,000 or more. preferable.
  • the polymer component having a weight average molecular weight of 10,000 or more preferably further includes (d) a polyimide resin.
  • the (d) polyimide resin preferably has a weight average molecular weight of 30000 or more and a glass transition temperature of 100 ° C. or less.
  • the (b) catalytic curing agent contains imidazoles.
  • the reaction between the epoxy resin and the imidazole is very fast because the electron pair of nitrogen directly attacks the epoxy group, generates an oxygen anion, and this oxygen anion further proceeds with a single anionic polymerization that reacts with the epoxy group. Indicates a curing reaction. Further, in high-temperature connection that requires metal-to-metal connection such as flip-chip connection, it is desired that there are few volatile components at high temperature (no resin foaming at 300 ° C. or higher). The reaction using is more preferable.
  • the present invention also provides a method of manufacturing a semiconductor device comprising a semiconductor chip having bumps and a substrate having metal wiring, wherein the semiconductor chip and the substrate are bumped via the above-mentioned film-like adhesive for semiconductor sealing. Arranged so that the metal wiring faces each other, pressurizes the semiconductor chip and the substrate in the facing direction and heats to cure the film-like adhesive for semiconductor sealing, and electrically connects the bump and the metal wiring.
  • a method for manufacturing a semiconductor device having a connecting step is provided.
  • the semiconductor chip and the substrate are pressurized in the opposing direction and heated to 300 ° C. or higher, and between the bump containing gold and the metal wiring having the tin plating layer It is preferable to form a gold-tin eutectic on the bump and electrically connect the bump and the metal wiring. As a result, it is possible to manufacture a semiconductor device having further excellent connection reliability.
  • the present invention it is sufficiently excellent in connectivity in a short time, and even when heated to a high temperature of 300 ° C. or higher, generation of voids can be sufficiently suppressed and connection reliability is sufficiently excellent. It is possible to provide a film-like adhesive for sealing a semiconductor capable of manufacturing a semiconductor device and a method for manufacturing the semiconductor device. In addition, the amount of voids in the sealing resin is sufficiently reduced, and a semiconductor device that is sufficiently excellent in connection reliability can be provided.
  • the film-like adhesive for semiconductor encapsulation of the present invention contains (a) an epoxy resin and (b) a catalytic curing agent, and reacts with a curing agent or a catalytic curing agent that becomes an active species by the catalytic curing agent. None of the curing agent is contained.
  • a curing agent that becomes an active species by the catalyst-type curing agent or a curing agent that reacts with the catalyst-type curing agent for example, a phenol-based curing agent or an acid anhydride-based curing agent A curing agent can be mentioned.
  • the phenolic curing agent has two or more phenolic hydroxyl groups in the molecule, and specifically, phenol novolak resin, cresol novolac resin, phenol aralkyl resin, cresol naphthol formaldehyde polycondensate, triphenylmethane type A polyfunctional phenol and various polyfunctional phenol resins are mentioned.
  • acid anhydride-based curing agent examples include methylcyclohexanetetracarboxylic dianhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic dianhydride, and ethylene glycol bisanhydro trimellitate.
  • the film-like adhesive for semiconductor encapsulation of the present invention can be cured in a shorter time than before by being provided with a structure not containing the above-mentioned other curing agents, and is suitable for flip chip connection.
  • the detail of each component contained in the film adhesive of this embodiment is demonstrated.
  • Epoxy resin is not particularly limited as long as it has two or more epoxy groups in the molecule.
  • the epoxy resin for example, bisphenol A type, bisphenol F type, naphthalene type, phenol novolac type, cresol novolak type, phenol aralkyl type, biphenyl type, triphenylmethane type, dicyclopentadiene type and various polyfunctional epoxy resins are used. be able to. These epoxy resins can be used individually by 1 type or in combination of 2 or more types.
  • the liquid epoxy resin of bisphenol A type or bisphenol F type has a 1% thermogravimetric reduction temperature of 250 ° C. or less, and therefore may decompose during high temperature heating to generate volatile components. For this reason, it is preferable to use a solid epoxy resin at room temperature (1 atm, 25 ° C.).
  • the catalytic curing agent is a component that is different from the other curing agents in the reaction mechanism with respect to the epoxy resin.
  • Examples of the catalyst-type curing agent include imidazoles and phosphines. Among these, imidazoles are preferable from the viewpoint of enabling connection in a shorter time.
  • imidazoles examples include 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyano.
  • phosphines include triphenylphosphine, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra (4-methylphenyl) borate, and tetraphenylphosphonium (4-fluorophenyl) borate.
  • phosphines include triphenylphosphine, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra (4-methylphenyl) borate, and tetraphenylphosphonium (4-fluorophenyl) borate.
  • those in which the potential is increased by microencapsulating them can also be used. You may use these individually by 1 type or in combination of 2 or more types. Among these, tetraphenylphosphonium tetraphenylborate having a phenyl group is more preferable.
  • the blending amount of the (b) catalyst-type curing agent is preferably 0.1 to 50 parts by mass, more preferably 0.1 to 35 parts by mass with respect to 100 parts by mass of the (a) epoxy resin. preferable. If the blending amount of the catalyst-type curing agent is less than 0.1 parts by mass, the curability tends to be impaired, and if it exceeds 50 parts by mass, the film-like adhesion is formed before the connection part by the gold-tin eutectic is formed. There is a tendency that the agent is hardened and it is difficult to sufficiently suppress the occurrence of poor connection.
  • the film adhesive preferably includes (c) a polymer component having a weight average molecular weight of 10,000 or more (hereinafter referred to as “(c) polymer component” for convenience).
  • the polymer component is a resin different from (a) the epoxy resin.
  • As a polymer component for example, (a) epoxy resin different from epoxy resin, phenoxy resin, polyimide resin, polyamide resin, polycarbodiimide resin, cyanate ester resin, acrylic resin, polyester resin, polyethylene resin, polyethersulfone Examples thereof include resins, polyetherimide resins, polyvinyl acetal resins, urethane resins, and acrylic rubbers.
  • These polymer components can be used singly or in combination of two or more or as a copolymer of two or more.
  • the weight average molecular weight of the polymer component is preferably 10,000 to 1,000,000, more preferably 20,000 to 900,000, and still more preferably 30,000 to 800,000.
  • the (c) polymer component preferably contains (d) a polyimide resin.
  • the polyimide resin can be obtained, for example, by subjecting tetracarboxylic dianhydride and diamine to a condensation reaction by a known method. More specifically, tetracarboxylic dianhydride and diamine are blended in an equimolar ratio or almost equimolar ratio in an organic solvent (the order of addition of each component is arbitrary), and is 80 ° C. or less, preferably The addition reaction is carried out at 0 to 60 ° C.
  • the tetracarboxylic dianhydride is preferably subjected to a recrystallization purification treatment with acetic anhydride in order to suppress deterioration of various properties of the film adhesive.
  • the molecular weight of the produced polyamic acid can be adjusted by heating at a temperature of 50 to 80 ° C. for depolymerization.
  • the polyimide resin can be obtained by dehydrating and ring-closing the reaction product (polyamic acid).
  • the dehydration ring closure can be performed by a thermal ring closure method in which heat treatment is performed and a chemical ring closure method using a dehydrating agent.
  • the tetracarboxylic dianhydride used as a raw material for the polyimide resin is not particularly limited, and examples thereof include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,2 ′.
  • 3,3′-biphenyltetracarboxylic dianhydride 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, bis (2,3-dicarboxyphenyl) Methane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, 3,4,9,10-perylenetetracarboxylic Dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, 3,4,3 ′, 4′-benzophenone
  • tetracarboxylic dianhydrides represented by the following general formulas (I) and (II) can be used.
  • r represents an integer of 2 to 20.
  • the tetracarboxylic dianhydride represented by the above general formula (I) can be synthesized from, for example, trimellitic anhydride monochloride and the corresponding diol.
  • the tetracarboxylic dianhydride represented by the above general formula (II) is preferable from the viewpoint of imparting excellent moisture resistance reliability to the film adhesive.
  • These tetracarboxylic dianhydrides can be used alone or in combination of two or more.
  • the amount of the tetracarboxylic dianhydride represented by the above formula (II) is preferably 40 mol% or more, more preferably 50 mol% or more with respect to the total tetracarboxylic dianhydride. 70 mol% or more is more preferable. When the blending amount is less than 40 mol%, it tends to be difficult to sufficiently obtain the effect of moisture resistance reliability due to the use of the tetracarboxylic dianhydride represented by the above formula (II).
  • the diamine used as a raw material for the polyimide resin is not particularly limited.
  • an aliphatic ether diamine represented by the following general formula (III), an aliphatic diamine represented by the following general formula (IV), or a siloxane diamine represented by the following general formula (V) may also be used. Can do.
  • Q 1 , Q 2 and Q 3 each independently represents an alkylene group having 1 to 10 carbon atoms, and s represents an integer of 2 to 80.
  • k represents an integer of 5 to 20.
  • Q 4 and Q 9 each independently represent an alkylene group having 1 to 5 carbon atoms or a phenylene group which may have a substituent
  • Q 5 , Q 6 , Q 7 , and Q 8 independently represents an alkyl group having 1 to 5 carbon atoms, a phenyl group or a phenoxy group
  • p represents an integer of 1 to 5.
  • diamines represented by the above general formula (III) or (IV) are preferable from the viewpoint of obtaining a film adhesive having excellent low stress properties, laminating properties, and low-temperature adhesiveness.
  • diamine represented by the said general formula (V) is preferable from a viewpoint of obtaining the film adhesive which has favorable low water absorption and low hygroscopicity.
  • the aliphatic ether diamine represented by the general formula (III) is 1 to 50 mol% of the total diamine
  • the aliphatic diamine represented by the general formula (IV) is 20 to 80 mol% of the total diamine
  • the siloxane diamine represented by the general formula (V) is preferably 20 to 80 mol% of the total diamine.
  • aliphatic ether diamine represented by the general formula (III) include aliphatic ether diamines of the formulas (III-1) to (III-5).
  • n represents an integer of 1 or more.
  • the weight average molecular weight of the aliphatic ether diamine represented by the general formula (III-4) is preferably 350, 750, 1100 or 2100, for example.
  • the weight average molecular weight of the aliphatic ether diamine represented by the general formula (III-5) is preferably 230, 400 or 2000, for example.
  • aliphatic ether diamines represented by the following general formula (VI) are more preferable in that low-temperature laminating properties and good adhesion to a substrate with an organic resist can be ensured.
  • m represents an integer of 2 to 80.
  • aliphatic ether diamine represented by the general formula (VI) include Jeffamine, D-230, D-400, D-2000, D-4000, ED-600, manufactured by Sun Techno Chemical Co., Ltd. , ED-900, ED-2001 and EDR-148 (above, trade names), and polyoxyalkylene diamines such as BASF polyether amines D-230, D-400 and D-2000 (above, trade names), etc. Aliphatic diamines may be mentioned.
  • Examples of the aliphatic diamine represented by the general formula (IV) include 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1, 6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 1,2- Diaminocyclohexane is mentioned. Among these, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane and 1,12-diaminododecane are preferable.
  • siloxane diamine represented by the general formula (V) for example, in the general formula (V), ⁇ when p is 1>, 1,1,3,3-tetramethyl-1,3-bis (4 -Aminophenyl) disiloxane, 1,1,3,3-tetraphenoxy-1,3-bis (4-aminoethyl) disiloxane, 1,1,3,3-tetraphenyl-1,3-bis (2 -Aminoethyl) disiloxane, 1,1,3,3-tetraphenyl-1,3-bis (3-aminopropyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (2 -Aminoethyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane, 1,1,3,3-te
  • the above polyimide resins may be used alone or in combination of two or more as required.
  • the glass transition temperature (Tg) of the polyimide resin is preferably 100 ° C. or less, and preferably 75 ° C. or less, from the viewpoint of obtaining a film-like adhesive that is more excellent in adhesion to a substrate or a semiconductor chip. More preferred.
  • the lower limit of Tg of a polyimide resin is about 20 degreeC from a viewpoint of handleability.
  • the glass transition temperature was determined by using DSC (Differential Scanning Thermal Analysis, manufactured by Perkin Elmer, trade name: DSC-7), sample amount: 10 mg, heating rate: 5 ° C./min, measurement atmosphere: air conditions It is a value measured by.
  • DSC Different Scanning Thermal Analysis, manufactured by Perkin Elmer, trade name: DSC-7
  • sample amount 10 mg
  • heating rate 5 ° C./min
  • measurement atmosphere air conditions It is a value measured by.
  • the weight average molecular weight of the polyimide resin is preferably 30000 or more, more preferably 40000 or more, and more preferably 50000 or more in terms of polystyrene in order to have good film-forming properties. Further preferred. When the weight average molecular weight is less than 30000, good film formability tends to be impaired when the film adhesive is formed. Moreover, the upper limit of the weight average molecular weight of a polyimide resin is about 100,000 from a viewpoint of handleability.
  • the above-mentioned weight average molecular weight is a value measured in terms of polystyrene using high performance liquid chromatography (manufactured by Shimadzu Corporation, trade name: C-R4A).
  • the content of the polyimide resin is not particularly limited. However, from the viewpoint of improving the retention of the film shape, it is preferable to blend such that the mass ratio of (a) the epoxy resin to (d) the polyimide resin is 0.01 to 5, preferably 0.05 to 3. More preferred is 0.1-2. When the mass ratio is less than 0.01, the curability of the film-like adhesive tends to be reduced, and the excellent adhesive force tends to be impaired. When the mass ratio exceeds 5, the film-forming property at the time of forming the film-like adhesive Tends to decrease.
  • the film adhesive of the present embodiment may contain a filler in order to control the viscosity and the physical properties of the cured product.
  • a filler an insulating inorganic filler, whisker, or resin filler can be used.
  • the insulating inorganic filler include glass, silica, alumina, titanium oxide, carbon black, mica, and boron nitride. Among these, silica, alumina, titanium oxide, and boron nitride are preferable, and silica, alumina, and boron nitride are more preferable.
  • whiskers examples include aluminum borate, aluminum titanate, zinc oxide, calcium silicate, magnesium sulfate, and boron nitride.
  • resin filler polyurethane, polyimide, or the like can be used. These fillers and whiskers can be used alone or in combination of two or more.
  • the shape, particle size, and blending amount of the filler are not particularly limited.
  • the film adhesive of the present embodiment may further contain a silane coupling agent, a titanium coupling agent, a leveling agent, an antioxidant, and an ion trap agent. These can be used alone or in combination of two or more. What is necessary is just to adjust about a compounding quantity so that the effect of each additive may express.
  • an epoxy resin and a catalyst-type curing agent and, if necessary, a polymer component having a weight average molecular weight of 10,000 or more, a polyimide resin and / or an additive (such as a filler) are added to an organic solvent, and agitation and mixing are performed.
  • a polymer component having a weight average molecular weight of 10,000 or more, a polyimide resin and / or an additive (such as a filler) are added to an organic solvent, and agitation and mixing are performed.
  • agitation and mixing are performed.
  • dissolve or disperse the resin varnish After applying the prepared resin varnish using a knife coater, roll coater or applicator on the base film subjected to the mold release treatment, the organic solvent is removed by heating, and a film adhesive is applied on the base film.
  • organic solvent used for preparing the resin varnish those having characteristics capable of uniformly dissolving or dispersing each component are preferable.
  • organic solvents include dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, diethylene glycol dimethyl ether, toluene, benzene, xylene, methyl ethyl ketone, tetrahydrofuran, ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve, dioxane. , Cyclohexanone, and ethyl acetate.
  • These organic solvents can be used individually by 1 type or in combination of 2 or more types. Mixing, kneading, and the like in preparing the resin varnish can be performed using a stirrer, a raking machine, a three roll, a ball mill, a homodisper, or the like.
  • a film having heat resistance capable of withstanding the heating conditions when the organic solvent is volatilized can be used.
  • a base film examples include a polyester film, a polypropylene film, a polyethylene terephthalate film, a polyimide film, a polyetherimide film, a polyether naphthalate film, and a methylpentene film.
  • the base film is not limited to a single-layer film made of only one of these film materials, and may be a multilayer film in which two or more film materials are laminated.
  • the conditions for volatilizing the organic solvent from the resin varnish applied to the base film are preferably such that the organic solvent is sufficiently volatilized.
  • the condition is 0.1 to at a temperature of 50 to 200 ° C. It is preferable to perform heating for 90 minutes.
  • the heating temperature at this time is preferably a temperature at which the curing reaction does not proceed so much.
  • the above-described film-like adhesive for semiconductor sealing is interposed between the semiconductor chip and the substrate, and the bump on the semiconductor chip and the metal wiring on the substrate are opposed to each other.
  • a second step of electrically connecting the metal wiring Details of each step will be described below.
  • FIG. 1 is a process cross-sectional view schematically showing a first process of a semiconductor device manufacturing method according to a preferred embodiment of the present invention.
  • a semiconductor sealing film adhesive 12 is interposed between the semiconductor chip 14 and the substrate 16.
  • Bumps 15 are formed on one surface of the semiconductor chip 14.
  • the material of the bump 15 formed on the semiconductor chip 14 is not particularly limited, and examples thereof include gold, low melting point solder, high melting point solder, nickel, tin and the like. Among these, in the case of COF, it is preferable to contain gold.
  • a metal wiring 18 is formed on one surface of the substrate 16.
  • the material of the substrate 16 is not particularly limited, and an inorganic substrate such as ceramic or an organic substrate such as epoxy resin, bismaleimide triazine resin, or polyimide resin can be used. Among these, in the case of COF, a polyimide resin is preferable.
  • the material of the metal wiring 18 includes copper, aluminum, silver, gold, nickel and the like.
  • the wiring is formed by etching or pattern plating.
  • the metal wiring 18 may have a plating layer on the surface by plating with gold, nickel, tin or the like.
  • a copper wiring having a tin plating layer on the surface by tin plating is preferably used.
  • the film-like adhesive 12 for semiconductor sealing may be cut out to a predetermined size and then attached to the substrate 16, or may be attached to the bump 15 forming surface of the semiconductor chip 14 and then diced into individual pieces.
  • the semiconductor chip 14 to which the film-like adhesive 12 for semiconductor sealing is attached may be produced.
  • the area and thickness of the film sealing adhesive 12 for semiconductor sealing are appropriately set depending on the size of the semiconductor chip 14 and the height of the bumps 15.
  • the metal wiring 18 of the substrate 16 and the bump 15 of the semiconductor chip 14 are aligned, and the semiconductor chip 14 and the substrate are arranged in the direction in which the metal wiring 18 and the bump 15 oppose (arrows A and B directions).
  • 16 is pressurized using a pressure head 30 and a stage 32.
  • the bump 15 is press-fitted into the film-like adhesive 12 for semiconductor sealing.
  • FIG. 2 is a process cross-sectional view schematically showing a second process of the semiconductor device manufacturing method according to the preferred embodiment of the present invention.
  • the pressure head 30 and the stage 32 are used to press the bump 15 and the metal wiring 18 in the opposite direction (arrows A and B directions), and 0.5 to 5 at a connection temperature of 300 to 450 ° C. Heat for seconds.
  • the bump 15 and the metal wiring 18 are in direct contact and are electrically connected, and the film sealing adhesive 12 for semiconductor encapsulation is cured to become a cured resin 22.
  • the pressurizing pressure can be adjusted as appropriate in consideration of the number of bumps, bump height and variation, bump deformation amount, and the like.
  • the semiconductor chip 14 and the metal wiring 18 are each heated to 300 to 450 ° C., when the semiconductor chip 14 contains gold and the surface of the metal wiring 18 has a tin plating layer, the gold And tin react to form a gold-tin eutectic at the contact portion between the bump 15 and the metal wiring 18. As a result, the bonding between the bump 15 and the metal wiring 18 becomes stronger, and the connection reliability can be further improved.
  • the film-like adhesive 12 for semiconductor encapsulation is made of a material that does not easily generate a void even when heated at a high temperature of 300 to 450 ° C., the insulation reliability can be sufficiently maintained.
  • the void generation rate of the semiconductor device obtained by the manufacturing method of the above embodiment is preferably 5% or less, more preferably 3% or less, and further preferably 1% or less. If the void generation rate is greater than 5%, voids remain between narrow pitch wirings, and the insulation reliability tends to decrease.
  • a heat treatment step of heating the entire semiconductor device in an oven or the like may be further performed.
  • Example 1 Synthetic polyimide 100 parts by mass (converted to solid content), epoxy resin (trade name: EP1032) 30 parts by weight, catalytic curing agent (trade name: 2MAOK-PW) 5 parts by weight and N-methyl- 2-pyrrolidone (manufactured by Kanto Chemical Co., Inc.) was charged so that the total solid content was 40% (about 200 parts by mass), and stirred with an agitation / defoaming device “AR-250” (trade name, manufactured by Shinky Corp.) Defoaming was performed to obtain a resin varnish.
  • epoxy resin trade name: EP1032
  • catalytic curing agent trade name: 2MAOK-PW
  • N-methyl- 2-pyrrolidone manufactured by Kanto Chemical Co., Inc.
  • the obtained resin varnish is coated on a base film (trade name: Purex A53, manufactured by Teijin DuPont Films, Ltd.) with a coating machine “PI1210FILMCOATER” (trade name, manufactured by Tester Sangyo Co., Ltd.), and a clean oven (Espec (Sold at 80 ° C. for 30 minutes and 120 ° C. for 20 to 30 minutes) to produce a film-like adhesive for semiconductor encapsulation.
  • PI1210FILMCOATER trade name, manufactured by Tester Sangyo Co., Ltd.
  • Examples 2 to 3 and Comparative Examples 1 to 4 Except that the composition of the raw materials used was changed as shown in Table 1 below, a film-like adhesive for semiconductor encapsulation was prepared in the same manner as the above-described method for producing a film-like adhesive for semiconductor encapsulation. Produced.
  • the evaluation test of the obtained film adhesive was performed as follows.
  • the produced film adhesive was cut into a predetermined size (10 mm ⁇ 10 mm ⁇ thickness 0.03 mm) and pasted on a cover glass (size: 18 mm ⁇ 18 mm) having a thickness of 0.12 to 0.17 mm, and then 300 ° C.
  • the film adhesive was examined for the presence or absence of resin foaming by visually observing the appearance of the film adhesive.
  • FIG. 3 is an explanatory diagram for explaining a method for producing the sample A for measuring the void generation rate.
  • the produced film adhesive 12 was cut into a predetermined size (diameter 6 mm, thickness about 0.1 mm) and pasted on a 0.7 mm thick glass chip 11 (size: 15 mm ⁇ 15 mm). Thereafter, as shown in FIG. 3, the glass chip 11, the film adhesive 12 and the cover glass 13 were sequentially laminated by covering the cover glass 13 (size: 18 mm ⁇ 18 mm) having a thickness of 0.12 to 0.17 mm. Sample A was prepared.
  • sample A was subjected to a flip chip bonder (trade name: FCB3, manufactured by Matsushita Electric Industrial Co., Ltd.) under the conditions of a heating temperature of 350 ° C., a pressing pressure of 1 MPa, and a heating and pressing time of 0.5 seconds or 1 second.
  • FCB3 manufactured by Matsushita Electric Industrial Co., Ltd.
  • FIG. 4A is a photograph taken from above (semiconductor chip side) of the semiconductor device used for connection resistance evaluation
  • FIG. 4B is a photograph taken of a cross section of the semiconductor device used for connection resistance evaluation. It is.
  • a semiconductor device for connection resistance evaluation was manufactured as follows.
  • the produced film adhesive was cut into a predetermined size (2.5 mm ⁇ 15.5 mm ⁇ thickness 0.03 mm), and polyimide substrate 16 (manufactured by Hitachi Ultra LSI Systems, Inc., trade name: JKIT COF TEG_30-B, polyimide)
  • the thickness of the substrate was 38 ⁇ m, the thickness of the copper wiring: 8 ⁇ m, the thickness of the wiring tin plating: 0.2 ⁇ m).
  • a chip 14 having a gold bump 15 formed on the surface opposite to the polyimide substrate of the film adhesive attached on the polyimide substrate (manufactured by Hitachi Ultra LSI Systems, Product name: JTEG PHASE6_30, chip size: 1.6 mm ⁇ 15.1 mm ⁇ thickness 0.4 mm, bump size: 20 ⁇ m ⁇ 100 ⁇ m ⁇ height 15 ⁇ m, bump number 726) were mounted by pressure bonding.
  • the pressure bonding conditions were a head temperature: 350 ° C., a stage temperature: 100 ° C., a pressure bonding time: 1 second, and a pressure bonding pressure: 50 to 100 N.
  • a semiconductor device in which the polyimide substrate 16 and the chip 14 with the gold bumps were daisy chain connected as shown in FIGS. 4A and 4B was obtained.
  • connection resistance value in the daisy chain connection of the obtained semiconductor device was measured using a multimeter. Since the connection resistance value in a daisy chain connection of a semiconductor device manufactured without using a film adhesive was around 160 ⁇ , the case where the connection resistance value is 120 to 190 ⁇ is “A”, less than 120 ⁇ or more than 190 ⁇ Was evaluated as “B”.
  • Table 1 summarizes the blending amount (parts by mass) of raw materials for the film-like adhesive for semiconductor encapsulation and the evaluation results.
  • reaction time The calorific value when measured under conditions and the time taken from the reaction start peak to the peak top (hereinafter referred to as “reaction time”) were measured. The results are shown in Table 2.
  • Example 2 From Table 2, the film-like adhesive of Example 1 containing only the catalyst-type curing agent is more cured than the film-like adhesive of Comparative Example 1 containing the catalyst-type curing agent and other curing agents. It was confirmed that it was fast enough.
  • SYMBOLS 11 Glass chip, 12 ... Film adhesive for semiconductor sealing (film adhesive), 13 ... Cover glass, 14 ... Chip (semiconductor chip), 15 ... Gold bump (bump), 16 ... Substrate (polyimide substrate) , 18 ... metal wiring (copper wiring), 22 ... cured resin, 30 ... pressure head, 32 ... stage.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Wire Bonding (AREA)

Abstract

La présente invention concerne un agent adhésif de type film destiné à sceller un semi-conducteur, qui comprend (a) une résine époxy et (b) un agent de durcissement de type catalyseur et qui ne contient aucun agent de durcissement qui pourrait être converti en une espèce active par le biais de l'action de l'agent de durcissement de type catalyseur ou qui pourrait réagir avec l'agent de durcissement de type catalyseur.
PCT/JP2010/056004 2009-05-08 2010-04-01 Agent adhésif de type film destiné à sceller un semi-conducteur, dispositif semi-conducteur, et procédé de fabrication du dispositif semi-conducteur WO2010128611A1 (fr)

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WO2016139985A1 (fr) * 2015-03-05 2016-09-09 住友ベークライト株式会社 Composition de résine d'étanchéité, procédé de fabrication de bloc de commande électronique à bord d'un véhicule et bloc de commande électronique à bord d'un véhicule
JP2019208054A (ja) * 2013-10-14 2019-12-05 コーニング インコーポレイテッド 半導体及びインターポーザ加工のためのキャリア結合方法及び物品
US11097509B2 (en) 2016-08-30 2021-08-24 Corning Incorporated Siloxane plasma polymers for sheet bonding
US11123954B2 (en) 2014-01-27 2021-09-21 Corning Incorporated Articles and methods for controlled bonding of thin sheets with carriers
US11167532B2 (en) 2015-05-19 2021-11-09 Corning Incorporated Articles and methods for bonding sheets with carriers
US11192340B2 (en) 2014-04-09 2021-12-07 Corning Incorporated Device modified substrate article and methods for making
US11331692B2 (en) 2017-12-15 2022-05-17 Corning Incorporated Methods for treating a substrate and method for making articles comprising bonded sheets
US11535553B2 (en) 2016-08-31 2022-12-27 Corning Incorporated Articles of controllably bonded sheets and methods for making same
US11905201B2 (en) 2015-06-26 2024-02-20 Corning Incorporated Methods and articles including a sheet and a carrier
US11999135B2 (en) 2017-08-18 2024-06-04 Corning Incorporated Temporary bonding using polycationic polymers

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011026374A (ja) * 2009-07-21 2011-02-10 Hitachi Chem Co Ltd 接着剤組成物及びそれを用いた半導体装置の製造方法、半導体装置
JP2019208054A (ja) * 2013-10-14 2019-12-05 コーニング インコーポレイテッド 半導体及びインターポーザ加工のためのキャリア結合方法及び物品
US11123954B2 (en) 2014-01-27 2021-09-21 Corning Incorporated Articles and methods for controlled bonding of thin sheets with carriers
US11192340B2 (en) 2014-04-09 2021-12-07 Corning Incorporated Device modified substrate article and methods for making
CN107251665A (zh) * 2015-03-05 2017-10-13 住友电木株式会社 密封用树脂组合物、车载用电子控制单元的制造方法和车载用电子控制单元
JP5994961B1 (ja) * 2015-03-05 2016-09-21 住友ベークライト株式会社 封止用樹脂組成物、車載用電子制御ユニットの製造方法、および車載用電子制御ユニット
WO2016139985A1 (fr) * 2015-03-05 2016-09-09 住友ベークライト株式会社 Composition de résine d'étanchéité, procédé de fabrication de bloc de commande électronique à bord d'un véhicule et bloc de commande électronique à bord d'un véhicule
US11167532B2 (en) 2015-05-19 2021-11-09 Corning Incorporated Articles and methods for bonding sheets with carriers
US11660841B2 (en) 2015-05-19 2023-05-30 Corning Incorporated Articles and methods for bonding sheets with carriers
US11905201B2 (en) 2015-06-26 2024-02-20 Corning Incorporated Methods and articles including a sheet and a carrier
US11097509B2 (en) 2016-08-30 2021-08-24 Corning Incorporated Siloxane plasma polymers for sheet bonding
US11535553B2 (en) 2016-08-31 2022-12-27 Corning Incorporated Articles of controllably bonded sheets and methods for making same
US11999135B2 (en) 2017-08-18 2024-06-04 Corning Incorporated Temporary bonding using polycationic polymers
US11331692B2 (en) 2017-12-15 2022-05-17 Corning Incorporated Methods for treating a substrate and method for making articles comprising bonded sheets

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