WO2009123285A1 - Activateur de flux, composition de résine adhésive, pâte adhésive, film adhésif, procédé de fabrication d'un dispositif semi-conducteur, et dispositif semi-conducteur - Google Patents

Activateur de flux, composition de résine adhésive, pâte adhésive, film adhésif, procédé de fabrication d'un dispositif semi-conducteur, et dispositif semi-conducteur Download PDF

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Publication number
WO2009123285A1
WO2009123285A1 PCT/JP2009/056889 JP2009056889W WO2009123285A1 WO 2009123285 A1 WO2009123285 A1 WO 2009123285A1 JP 2009056889 W JP2009056889 W JP 2009056889W WO 2009123285 A1 WO2009123285 A1 WO 2009123285A1
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Prior art keywords
adhesive
resin composition
adhesive resin
circuit board
semiconductor device
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PCT/JP2009/056889
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English (en)
Japanese (ja)
Inventor
榎本　哲也
一尊 本田
永井　朗
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日立化成工業株式会社
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Priority to CN2009801045384A priority Critical patent/CN101939379A/zh
Publication of WO2009123285A1 publication Critical patent/WO2009123285A1/fr

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    • 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
    • C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
    • C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
    • C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
    • C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances
    • 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
    • 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
    • H01L2224/81—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 bump connector
    • H01L2224/8119—Arrangement of the bump connectors prior to mounting
    • H01L2224/81191—Arrangement of the bump connectors prior to mounting wherein the bump connectors are disposed only on the semiconductor or solid-state body
    • 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
    • H01L2224/83192—Arrangement of the layer connectors prior to mounting wherein the layer connectors are disposed only on another item or body to be connected to the semiconductor or solid-state body
    • 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
    • H01L2224/838—Bonding techniques
    • H01L2224/8385—Bonding techniques using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester
    • H01L2224/83855—Hardening the adhesive by curing, i.e. thermosetting
    • H01L2224/83856—Pre-cured adhesive, i.e. B-stage adhesive
    • 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
    • H01L2224/90—Methods for connecting semiconductor or solid state bodies using means for bonding not being attached to, or not being formed on, the body surface to be connected, e.g. pressure contacts using springs or clips
    • 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
    • H01L24/10—Bump connectors ; Manufacturing methods related thereto
    • H01L24/15—Structure, shape, material or disposition of the bump connectors after the connecting process
    • H01L24/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
    • 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
    • H01L24/90—Methods for connecting semiconductor or solid state bodies using means for bonding not being attached to, or not being formed on, the body surface to be connected, e.g. pressure contacts using springs or clips
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01004—Beryllium [Be]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01012—Magnesium [Mg]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01046—Palladium [Pd]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01078—Platinum [Pt]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01079—Gold [Au]

Definitions

  • the present invention relates to a flux activator, an adhesive resin composition, an adhesive paste, an adhesive film, a semiconductor device manufacturing method, and a semiconductor device.
  • Known flip-chip connection methods include metal bonding using solder, tin, etc., metal bonding by applying ultrasonic vibration, and method of maintaining mechanical contact using the shrinkage force of the resin. ing.
  • a method of metal bonding using solder, tin, or the like is widely used.
  • a method using solder exhibits high connection reliability, and thus, such as MPU. Applied to the implementation.
  • a resin sealing and filling method a method in which a semiconductor chip and a substrate are connected using solder or the like and then a liquid sealing resin is injected into the gap using a capillary phenomenon.
  • a flux activator made of rosin, organic acid, or the like is used in order to reduce and remove an oxide film existing on the surface of solder or the like to facilitate metal bonding.
  • the flux activator residue may cause bubbles called voids when the liquid sealing resin is injected, or corrosion of the wiring may occur due to the acid component, resulting in reduced connection reliability. Therefore, a step of cleaning the flux activator residue is essential.
  • the connection pitch is narrowed, the gap between the semiconductor chip and the substrate is narrowed, and thus it may be difficult to clean the flux activator residue.
  • a sealing resin having a property (flux activity) for reducing and removing an oxide film present on the surface of a metal such as solder has been proposed. After supplying these sealing resins onto the substrate, the semiconductor chip and the substrate are connected simultaneously, and at the same time, the gap between the semiconductor chip and the substrate is sealed and filled with the resin, and cleaning of the flux activator residue is omitted. It is demanded.
  • a semiconductor sealing resin containing an epoxy resin and a curing agent containing an oxazine compound is known (see Patent Document 4).
  • the semiconductor sealing resin is for molding a semiconductor chip, a wire or the like on the circuit board, and does not electrically connect the semiconductor chip and the circuit board. That is, the flux activity is not required at all for the semiconductor sealing resin.
  • an oxazine compound is used as a curing agent for an epoxy resin, it is not known at all to be used as a flux activator.
  • the present invention has been made in view of the above circumstances, and shows a flux activator, an adhesive resin composition, an adhesive paste, an adhesive film, an electrical film, which exhibit good flux activity and easily ensure storage stability.
  • An object of the present invention is to provide a method for manufacturing a semiconductor device with high connection reliability and a semiconductor device.
  • the flux activator according to the first aspect of the present invention contains a compound having a condensed polycyclic oxazine skeleton.
  • the flux activator according to the second aspect of the present invention contains a compound obtained by ring-closing condensation of a compound having a phenolic hydroxyl group, formaldehyde, and a compound having a primary amino group.
  • the flux activator of the present invention exhibits good flux activity and easily secures storage stability. Although the detailed reason for showing good flux activity is not clear, it is reduced by a phenolic hydroxyl group formed by opening the oxazine ring by heating, and reduction by electron donating property derived from an unpaired electron of a tertiary nitrogen atom This is presumed to be due to the combined effects. In addition, it is presumed that the storage stability is easily secured because the oxazine ring is stable without opening at low temperatures.
  • the adhesive resin composition of the present invention contains an epoxy resin, a curing agent, and the flux activator.
  • the epoxy resin is cured by the action of the curing agent.
  • the adhesive resin composition of this invention contains the said flux activator, while ensuring favorable flux activity, ensuring of storage stability is easy.
  • the compound having the condensed polycyclic oxazine skeleton in the flux activator is preferably in a liquid state.
  • the adhesiveness of the adhesive resin composition is improved as compared with the case where the compound having a condensed polycyclic oxazine skeleton is a solid substance. Therefore, for example, a plurality of members can be favorably bonded.
  • the compound having a condensed polycyclic oxazine skeleton is preferably in a liquid state at any temperature within a temperature range of 40 to 50 ° C., for example.
  • the curing agent contains imidazoles. In this case, the storage stability of the adhesive resin composition and the heat resistance of the cured product of the adhesive resin composition are improved.
  • the adhesive resin composition further contains an inorganic filler.
  • the linear expansion coefficient (elastic modulus) of the cured product of the adhesive resin composition can be reduced.
  • the adhesive paste of the present invention contains the adhesive resin composition, and the epoxy resin and the curing agent in the adhesive resin composition are liquid. Since the adhesive paste of this invention contains the said adhesive resin composition, while ensuring favorable flux activity, ensuring of storage stability is easy.
  • the adhesive film of the present invention contains the above adhesive resin composition and a thermoplastic resin. Since the adhesive film of this invention contains the said adhesive resin composition, while ensuring favorable flux activity, ensuring of storage stability is easy.
  • the compounding amount of the compound having the condensed polycyclic oxazine skeleton in the adhesive resin composition is 0.5 to 20 parts by mass with 100 parts by mass as the total amount of the thermoplastic resin and the epoxy resin. Is preferred.
  • the compounding amount of the compound having a condensed polycyclic oxazine skeleton is less than 0.5 parts by mass, the flux activity tends not to be sufficiently exhibited.
  • the compounding amount exceeds 20 parts by mass, the film formability is reduced or the adhesive film is cured. The heat resistance of the steel tends to be reduced.
  • the method for manufacturing a semiconductor device of the present invention includes a step of interposing the adhesive resin composition between a circuit board having a first metal electrode and a semiconductor element having a second metal electrode, and the adhesive resin composition. Curing the substrate, bonding the circuit board and the semiconductor element, and electrically connecting the first metal electrode and the second metal electrode.
  • the adhesive resin composition since the adhesive resin composition is used, the electrical connection reliability between the circuit board and the semiconductor element can be improved.
  • a semiconductor device includes a circuit board having a first metal electrode, a semiconductor element having a second metal electrode electrically connected to the first metal electrode, and the circuit board and the semiconductor element. And an adhesive layer made of a cured product of the adhesive resin composition, and arranged to adhere the circuit board and the semiconductor element. Since the semiconductor device of the present invention includes an adhesive layer made of a cured product of the adhesive resin composition, the electrical connection reliability between the circuit board and the semiconductor element is increased.
  • a flux activator an adhesive resin composition, an adhesive paste, an adhesive film, and a semiconductor device with high electrical connection reliability that exhibit good flux activity and easily ensure storage stability.
  • a method and a semiconductor device are provided.
  • the flux activator according to this embodiment contains a compound having a condensed polycyclic oxazine skeleton.
  • a flux activator made of an organic acid such as carboxylic acid it is difficult to ensure storage stability, and problems such as corrosion of wiring due to an acid component occur.
  • the flux activator of the present embodiment exhibits good flux activity and easily secures storage stability.
  • the detailed reason for showing good flux activity is not clear, it is reduced by a phenolic hydroxyl group formed by opening the oxazine ring by heating, and reduction by electron donating property derived from an unpaired electron of a tertiary nitrogen atom This is presumed to be due to the combined effects.
  • the storage stability is easily secured because the oxazine ring is stable without opening at low temperatures.
  • the flux activator reduces and removes the oxide film on the metal surface so that the metal can be easily melted.
  • the flux activator does not inhibit the molten metal from spreading and can achieve a state in which a metal bond is formed.
  • the solder ball becomes larger than the initial diameter and spreads on the surface of the copper plate.
  • the solder ball after melting is subjected to a shear test, the solder ball is not broken at the interface between the solder ball and the copper plate, but is bulk broken of the solder ball.
  • solder wetting spread rate when the rate of change with respect to the initial diameter of the solder ball after melting is defined as a “solder wetting spread rate” described later, the solder wetting spread rate is preferably 20% or more in order to achieve good flux activity. 30% or more, more preferably 40% or more.
  • the compound having a condensed polycyclic oxazine skeleton is not particularly limited, but is a monofunctional compound represented by general formula (I) or a polyfunctional compound represented by general formula (II) or (III). Can be used. An example is benzoxazine.
  • [A] represents a monocyclic or condensed polycyclic aromatic hydrocarbon ring forming a condensed ring so as to share two adjacent carbon atoms with the oxazine ring
  • R 1 and R 2 each represents a functional group selected from a hydrogen atom, an alkyl group, an aryl group, a substituted aryl group, a vinyl group, and an allyl group, and may be all the same or different from each other
  • m is 0 to Represents an integer of 4.
  • [B] represents a monocyclic or condensed polycyclic aromatic hydrocarbon ring forming a condensed ring so as to share two adjacent carbon atoms with respect to the oxazine ring
  • R 3 represents a functional group selected from a hydrogen atom, an alkyl group, an aryl group, a substituted aryl group, a vinyl group, and an allyl group
  • R 4 represents any one of the structures of formulas (i) to (ix), where n is Represents an integer of 1 to 4.
  • [C] represents a monocyclic or condensed polycyclic aromatic hydrocarbon ring forming a condensed ring so as to share two adjacent carbon atoms with respect to the oxazine ring
  • R 5 and R 6 represent a functional group selected from a hydrogen atom, an alkyl group, an aryl group, a substituted aryl group, a vinyl group, and an allyl group
  • R 7 represents any one of the structures of formulas (i) to (ix)
  • N represents an integer of 1 to 4.
  • Preferred examples of the monofunctional compound represented by the general formula (I) include compounds represented by structural formulas (IV) to (XIII).
  • Preferred examples of the polyfunctional compound represented by general formulas (II) and (III) include compounds represented by structural formulas (XIV) to (XVIII).
  • examples of the polyfunctional compound include compounds represented by structural formulas (XIX) and (XX).
  • R 8 represents an aryl group or a substituted aryl group, and x and y represent an integer of 0 or more).
  • the above compounds having a condensed polycyclic oxazine skeleton may be used alone or in combination of two or more.
  • the flux activator according to this embodiment may contain a compound obtained by ring-closing condensation of a compound having a phenolic hydroxyl group, formaldehyde, and a compound having a primary amino group.
  • the flux activator according to the present embodiment can be synthesized by heat-mixing a compound having a phenolic hydroxyl group, formaldehyde, and a compound having a primary amino group, followed by ring-closing condensation.
  • the compound thus obtained is, for example, a compound having a condensed polycyclic oxazine skeleton.
  • phenol substituted phenols, naphthols, substituted naphthols, bisphenols, biphenols, triphenolmethanes, phenol novolacs, phenol aralkyls and the like
  • compound having a primary amino group for example, alkylamines, anilines, substituted anilines, diaminodiphenylmethanes and the like can be used.
  • the adhesive resin composition according to this embodiment contains an epoxy resin, a curing agent, and the flux activator of this embodiment.
  • the adhesive resin composition of the present embodiment exhibits good flux activity and is easy to ensure storage stability.
  • the adhesive resin composition according to the present embodiment is used to connect circuit members having metal electrodes such as bumps and wirings and to metal bond metal electrodes to each other.
  • the epoxy resin is not particularly limited as long as it is bifunctional or higher.
  • bisphenol A type epoxy resin bisphenol F type epoxy resin, naphthalene skeleton-containing polyfunctional epoxy resin, dicyclopentadiene skeleton-containing polyfunctional epoxy resin, tri It is desirable to use a polyfunctional epoxy resin containing a phenylmethane skeleton.
  • the properties of these epoxy resins may be liquid or solid at 25 ° C.
  • solid epoxy resin for example, when solder is connected by heating and melting, it is desirable to use a resin whose melting point or softening point of the epoxy resin is lower than the melting point of the solder.
  • imidazoles for example, imidazoles, acid anhydrides, amines, hydrazides, polymercaptans, Lewis acid-amine complexes and the like can be used.
  • imidazoles which are excellent in the storage stability of the adhesive resin composition and the heat resistance of the cured product of the adhesive resin composition are desirable.
  • the curing agent is an imidazole
  • those encapsulating these curing agents with a polyurethane-based or polyester-based polymer substance and making them into microcapsules are preferable because the pot life is extended. These may be used alone or in admixture of two or more.
  • the adhesiveness of the adhesive resin composition is improved as compared with the case where the compound having the condensed polycyclic oxazine skeleton is a solid. Therefore, for example, a plurality of members can be favorably bonded.
  • the compound having a condensed polycyclic oxazine skeleton is liquid at any temperature within a temperature range of 40 to 50 ° C., for example.
  • the adhesive resin composition according to this embodiment may contain an inorganic filler in order to reduce the average coefficient of linear expansion of the cured product of the adhesive resin composition.
  • the inorganic filler material is not particularly limited, and examples thereof include glass, silicon dioxide (silica), aluminum oxide (alumina), titanium oxide (titania), magnesium oxide (magnesia), carbon black, mica, and barium sulfate. It is done. You may use these individually or in mixture of 2 or more types.
  • the material of the inorganic filler is a composite oxide containing two or more types of metal oxides (two or more types of metal oxides are not simply mixed, but the metal oxides are chemically bonded and separated.
  • the average particle size of the inorganic filler is desirably 10 ⁇ m or less in order to prevent the inorganic filler from being trapped between the counter electrodes during the flip chip connection and hindering the electrical connection.
  • two or more inorganic fillers having different average particle diameters may be used in combination.
  • the adhesive resin composition according to this embodiment may contain additives such as a curing accelerator, a silane coupling agent, a titanium coupling agent, an antioxidant, a leveling agent, and an ion trapping agent. These may 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.
  • additives such as a curing accelerator, a silane coupling agent, a titanium coupling agent, an antioxidant, a leveling agent, and an ion trapping agent.
  • the flux activator when connecting the solder by heating and melting, it is preferable that the flux activator remains in the adhesive resin composition without being decomposed or volatilized during heating. That is, the minimum temperature at which the thermogravimetric change rate of the flux activator measured by the TGA (Thermal Gravimetry Analysis) method is 0% (the remaining weight is 0) is preferably higher than the melting temperature of the solder. Moreover, when using a solid thing at normal temperature as a flux activator, it is desirable that the melting temperature and softening point temperature of a flux activator are lower than the melting temperature of solder. That is, in order to uniformly remove the oxide film on the solder surface, it is desirable that the flux activator exists in a liquid state at the solder melting temperature.
  • the adhesive paste according to this embodiment contains the adhesive resin composition of this embodiment. Moreover, the epoxy resin and the curing agent in the adhesive resin composition are liquid.
  • the adhesive paste of the present embodiment exhibits good flux activity and easily ensures storage stability.
  • the adhesive film 6a (refer FIG. 2) which concerns on this embodiment contains the adhesive resin composition of this embodiment, and a thermoplastic resin.
  • the adhesive film 6a of the present embodiment exhibits a good flux activity, and it is easy to ensure storage stability.
  • Thermoplastic resins include phenoxy resin, polyimide resin, polyamide resin, polycarbodiimide resin, phenol resin, cyanate ester resin, acrylic resin, polyester resin, polyethylene resin, polyethersulfone resin, polyetherimide resin, polyvinyl acetal resin, urethane Examples thereof include resins and acrylic rubber. Among them, phenoxy resin, polyimide resin, cyanate ester resin, polycarbodiimide resin, and the like that are excellent in heat resistance and film formability are desirable, and phenoxy resin and polyimide resin are more preferable. Particularly preferred is a phenoxy resin having a fluorene skeleton in the molecule.
  • the weight average molecular weight of the thermoplastic resin is desirably greater than 5000, more desirably 10,000 or more, and even more desirably 20000 or more. When the weight average molecular weight is 5000 or less, the film forming ability tends to decrease.
  • the weight average molecular weight is a value measured in terms of polystyrene using GPC (Gel Permeation Chromatography).
  • these thermoplastic resins can be used alone or as a mixture or copolymer of two or more.
  • the blending amount of the thermoplastic resin is preferably 5 to 50 parts by mass, more preferably 5 to 40 parts by mass with respect to 100 parts by mass of the total amount of the thermoplastic resin and the epoxy resin. It is particularly preferable to use parts. If the blending amount is less than 5 parts by mass, film formation tends to be difficult, and if it exceeds 50 parts by mass, the viscosity tends to increase and the possibility of poor connection tends to increase.
  • the blending amount of the epoxy resin is preferably 10 to 90 parts by weight, more preferably 15 to 90 parts by weight, and more preferably 20 to 80 parts by weight with respect to 100 parts by weight of the total amount of the thermoplastic resin and the epoxy resin. It is particularly preferable that If this blending amount is less than 10 parts by mass, the heat resistance of the cured product tends to decrease, and if it exceeds 90 parts by mass, the film formability tends to decrease.
  • the blending amount of the curing agent varies depending on the type of the curing agent, but when the curing agent is an imidazole, it is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the epoxy resin, and 1 to 10 parts by mass. More preferably. If the blending amount is less than 0.1 parts by mass, curing is insufficient, and if it exceeds 20 parts by mass, the heat resistance of the cured product tends to be reduced.
  • the compounding amount of the compound having a condensed polycyclic oxazine skeleton is preferably 0.5 to 20 parts by mass, and preferably 0.5 to 15 parts by mass with respect to 100 parts by mass of the total amount of the thermoplastic resin and the epoxy resin. More preferred is 1 to 10 parts by mass. If the blending amount is less than 0.5 parts by mass, the flux activity tends not to be sufficiently exhibited, and if it exceeds 20 parts by mass, the film formability tends to decrease or the heat resistance of the cured product tends to decrease.
  • the type and the optimum blending amount of the compound having a condensed polycyclic oxazine skeleton are not only the presence or absence of flux activity, but also film formability, workability during film production (such as viscosity change of varnish), and film handling (tack) It is preferable to set in consideration of the property, workability such as punching and slit).
  • the compounding amount of the inorganic filler is preferably 200 parts by mass or less, and more preferably 150 parts by mass or less with respect to 100 parts by mass of the total amount of the thermoplastic resin and the epoxy resin. If this amount exceeds 200 parts by mass, the viscosity of the adhesive resin composition increases, the possibility of poor connection increases, and the flexibility of the adhesive film tends to decrease and become brittle.
  • the viscosity of the adhesive film 6a of the present embodiment in an uncured state is desirably 100 Pa ⁇ s or less at 150 ° C., more desirably 50 Pa ⁇ s or less, and further desirably 30 Pa ⁇ s or less.
  • the viscosity is higher than 100 Pa ⁇ s, the melted metal is prevented from spreading and the possibility of poor connection tends to increase.
  • a shear viscoelasticity measuring device for example, ARES manufactured by TA Instruments Co., Ltd.
  • the viscosity is set at a frequency of 1 to It can be measured under the condition of 10 Hz. Viscosity measurement is performed fully automatically.
  • the adhesive film 6a punched in a circular shape is sandwiched between glass plates, pressed at a predetermined temperature for a predetermined time at a predetermined temperature, and the viscosity is calculated from a change in the thickness of the adhesive film 6a (resin) before and after pressing.
  • the method can be used. That is, it is computable by following Formula (1) (Healey's formula regarding the uniaxial compression flow between parallel plates).
  • the gelation time of the adhesive film 6a of this embodiment at 260 ° C. is desirably 1 to 60 seconds, more desirably 3 to 40 seconds, and further desirably 5 to 30 seconds. If the gelation time is shorter than 1 second, the solder is hardened before melting, and there is a tendency that a connection failure is likely to occur. It tends to be insufficient and reliability is lowered.
  • the gelation time refers to the time until the adhesive film 6a is placed on a hot plate set at 260 ° C., stirred with a spatula or the like, and cannot be stirred.
  • the adhesive film 6a of the present embodiment can be manufactured, for example, as follows. First, a varnish is prepared by mixing a thermoplastic resin, an epoxy resin, a curing agent, an inorganic filler, the flux activator of this embodiment, and other additives in an organic solvent such as toluene, ethyl acetate, methyl ethyl ketone. Subsequently, the varnish is applied onto a film substrate made of a polyethylene terephthalate resin or the like that has been subjected to a release treatment using a knife coater or a roll coater, and then the organic solvent is removed by drying. Thereby, the adhesive film 6a of this embodiment can be formed on a film base material.
  • a varnish is prepared by mixing a thermoplastic resin, an epoxy resin, a curing agent, an inorganic filler, the flux activator of this embodiment, and other additives in an organic solvent such as toluene, ethyl acetate, methyl ethyl ket
  • FIG. 1 is a cross-sectional view schematically showing an example of a semiconductor device according to the embodiment.
  • a semiconductor device 10 shown in FIG. 1 includes a circuit board 21, a semiconductor element 22, and an adhesive layer 6 disposed between the circuit board 21 and the semiconductor element 22.
  • the adhesive layer 6 adheres the circuit board 21 and the semiconductor element 22 and is made of a cured product of the adhesive resin composition of the present embodiment.
  • the adhesive layer 6 may be made of a cured product of the adhesive film 6a or adhesive paste of the present embodiment.
  • the circuit board 21 includes a substrate 7 such as an interposer and a wiring 4 (first metal electrode) provided on one surface of the substrate 7. On the other surface of the substrate 7, an electrode pad 2 and a solder ball 1 are provided in this order.
  • the circuit board 21 may be a semiconductor chip.
  • the substrate 7 is made of an insulating material such as glass epoxy, polyimide, polyester, or ceramic.
  • the wiring 4 is made of a metal material such as copper, for example.
  • the wiring 4 may be patterned by forming a metal layer on the substrate 7 and removing unnecessary portions of the metal layer by etching.
  • the wiring 4 may be patterned on the substrate 7 by copper plating or the like, or may be patterned by printing a conductive substance on the substrate 7.
  • a metal layer made of low melting point solder, high melting point solder, tin, indium, gold, nickel, silver, copper, palladium, or the like may be formed on the surface of the wiring 4.
  • This metal layer may be composed of only a single component or may be composed of a plurality of components. Moreover, you may have the structure where the some metal layer was laminated
  • the semiconductor element 22 includes a semiconductor chip 5 and bumps 3 (second metal electrodes) electrically connected to the semiconductor chip 5.
  • the bump 3 is electrically connected to the wiring 4.
  • the constituent material of the semiconductor chip 5 is not particularly limited, and various semiconductors such as elemental semiconductors such as silicon and germanium, and compound semiconductors such as gallium arsenide and indium phosphide can be used.
  • the bump 3 is a conductive protrusion. Examples of the material of the bump 3 include low melting point solder, high melting point solder, tin, indium, gold, silver, and copper.
  • the bump 3 may be composed of only a single component or may be composed of a plurality of components.
  • the bump 3 may have a laminated structure including a metal layer made of these components.
  • the semiconductor element 22 may not include the bump 3, and the circuit board 21 may include the bump 3 on the wiring 4.
  • the wiring 4 of the circuit board 21 and the bump 3 of the semiconductor element 22 are metal-bonded. Since the semiconductor device 10 includes the adhesive layer 6 made of a cured product of the adhesive resin composition of the present embodiment, the electrical connection reliability between the wiring 4 of the circuit board 21 and the bump 3 of the semiconductor element 22 is improved. It can be improved. Further, the electrical insulation reliability between the adjacent wirings 4 and between the adjacent bumps 3 can be improved.
  • FIG. 2 is a process cross-sectional view schematically showing an example of a method for manufacturing a semiconductor device according to the embodiment.
  • a method for manufacturing the semiconductor device 10 shown in FIG. 1 will be described.
  • the circuit board 21 is prepared by forming the wiring 4 on the board 7.
  • the adhesive film 6 a of this embodiment is attached to the circuit board 21 so as to cover the wiring 4.
  • Affixing can be performed by a hot press, roll lamination, vacuum lamination, or the like.
  • the supply amount of the adhesive film 6a is preferably set according to the pasting area and the thickness of the adhesive film 6a.
  • the supply amount of the adhesive film 6a when the adhesive film 6a is attached to the circuit board 21 is defined by the size of the semiconductor chip 5, the height of the bump 3, etc., and can be easily controlled by the area and thickness of the adhesive film 6a. Can do.
  • the circuit board 21 with the adhesive film 6a attached is placed on the stage 20 of the connecting device such as a flip chip bonder. Further, the semiconductor element 22 is attached to the head 17 of the connection device.
  • the adhesive film 6 a is interposed between the wiring 4 of the circuit board 21 and the bump 3 of the semiconductor element 22. In addition, it may replace with the adhesive film 6a and may use the adhesive resin composition and adhesive paste of this embodiment.
  • the adhesive film 6a may be affixed to the semiconductor chip 5, and after adhering the adhesive film 6a to the semiconductor wafer, the semiconductor chip 5 to which the adhesive film 6a is affixed is diced into individual pieces. May be produced.
  • the adhesive film 6a is cured by heat and pressure using a connecting device such as a flip chip bonder.
  • a connecting device such as a flip chip bonder.
  • the circuit board 21 and the semiconductor element 22 are bonded together, and the wiring 4 of the circuit board 21 and the bumps 3 of the semiconductor element 22 are electrically connected.
  • the circuit board 21 and the semiconductor element 22 are aligned.
  • the circuit board 21 and the semiconductor element 22 are pressed while being heated at a temperature equal to or higher than the melting point of the bump 3 (for example, the melting point of solder).
  • the circuit board 21 and the semiconductor element 22 are connected, and the gap between the circuit board 21 and the semiconductor element 22 is sealed and filled with the molten adhesive film 6a.
  • the oxide film on the surface of the bump 3 is reduced and removed by the flux activity of the adhesive film 6a, the bump 3 is melted, and the wiring 4 and the bump 3 are metal-bonded.
  • the adhesive layer 6 is formed by curing the adhesive film 6a. In this way, the semiconductor device 10 is manufactured.
  • the wiring 4 and the bump 3 may be metal-bonded as follows. First, the circuit board 21 and the semiconductor element 22 are aligned. Subsequently, the circuit board 21 and the semiconductor element 22 are pressed while being heated at a temperature at which the bumps 3 do not melt. As a result, the adhesive film 6a is melted to remove the adhesive film 6a between the wiring 4 and the bump 3, and the gap between the circuit board 21 and the semiconductor element 22 is sealed and filled. As a result, the circuit board 21 and the semiconductor element 22 are temporarily fixed. Thereafter, the bump 3 is melted by heat treatment in a reflow furnace, and the circuit board 21 and the semiconductor element 22 are connected.
  • the semiconductor device 10 may be heat-treated in a heating oven or the like to further cure the adhesive film 6a.
  • the adhesive film 6a is used, the electrical connection reliability between the circuit board 21 and the semiconductor element 22 can be improved. Therefore, the productivity of the semiconductor device 10 is improved.
  • the adhesive film 6a cut out in pieces may be attached to the circuit board 21 or the bumps 3 of the semiconductor element 22 are formed. It may be pasted on the surface.
  • the adhesive film 6a is attached to the whole of the plurality of circuit boards 21 and the semiconductor elements 22 are connected. Also good.
  • the adhesive film 6a may be attached to a semiconductor wafer before being singulated into semiconductor elements 22 and diced into semiconductor elements 22 by dicing.
  • the transmittance of the adhesive film 6a is 10% or more with respect to light having a wavelength of 555 nm.
  • the transmittance of the adhesive film 6a is 10% or more with respect to light having a wavelength of 555 nm.
  • the above-described transmittance can be achieved by making the refractive index of the inorganic filler and the refractive index of the resin in the adhesive film 6a substantially the same.
  • the refractive index of the inorganic filler is 1.5 to 1.7 with respect to the refractive index of the epoxy resin of about 1.6.
  • the inorganic filler material exhibiting such a refractive index include barium sulfate, magnesium oxide, composite oxide composed of silicon dioxide and titanium oxide, composite oxide composed of silicon dioxide and aluminum oxide, and composite composed of boron oxide and aluminum oxide. Examples thereof include oxides, composite oxides composed of silicon dioxide, aluminum oxide, and magnesium oxide.
  • FIG. 3 is a cross-sectional view schematically showing an example of a semiconductor device according to another embodiment.
  • the semiconductor device 30 shown in FIG. 3 includes a circuit board 31, a semiconductor element 10a, and an adhesive layer 12 disposed between the circuit board 31 and the semiconductor element 10a.
  • the semiconductor element 10 a has a structure similar to that of the semiconductor device 10.
  • the adhesive layer 12 is made of a cured product of the adhesive resin composition of the present embodiment while adhering the circuit board 31 and the semiconductor element 10a.
  • the adhesive layer 12 may be made of a cured product of the adhesive film 6a or adhesive paste of the present embodiment.
  • the circuit board 31 is, for example, a motherboard.
  • the circuit board 31 includes a substrate 14 and an inner layer wiring 9 formed inside the substrate 14.
  • a wiring 11 (first metal electrode) is formed on the surface of the substrate 14.
  • the wiring 11 is electrically connected to the solder ball 1 (second metal electrode) of the semiconductor element 10a.
  • a via 15 is formed on the surface of the substrate 14, and a conductor layer 15 a is formed in the via 15.
  • a through hole 13 is formed in the substrate 14, and a conductor layer 13 a is formed in the through hole 13.
  • the semiconductor device 30 is, for example, a semiconductor package.
  • Examples of the semiconductor package in which the semiconductor chip is mounted on the interposer include CSP (chip size package) and BGA (ball grid array).
  • CSP chip size package
  • BGA ball grid array
  • a semiconductor package in which the semiconductor chip can be mounted on the circuit board 31 without using an interposer by rewiring the electrode portion of the semiconductor chip on the surface of the semiconductor chip for example, a so-called wafer level package is available. Can be mentioned.
  • the electrical connection reliability between the circuit board 31 and the semiconductor element 10a can be improved.
  • a semiconductor device may be manufactured using an adhesive paste or other adhesive resin composition.
  • thermoplastic resin 25 parts by mass of a phenoxy resin FX293 (manufactured by Toto Kasei Co., Ltd., product name), as an epoxy resin, 30 parts by mass of a solid polyfunctional epoxy resin EP1032H60 (manufactured by Japan Epoxy Resin, product name) and a liquid bisphenol A type epoxy Resin EP828 (manufactured by Japan Epoxy Resin, product name) 45 parts by mass, a compound having a condensed polycyclic oxazine skeleton (flux activator), 5 parts by mass of the compounds shown in Table 1, and SE6050 (AD Corporation) A varnish was prepared by dissolving and mixing 100 parts by mass of Matex, product name, average particle size 2 ⁇ m) in a toluene-ethyl acetate solvent so that the solid concentration was 60 to 70%.
  • the varnish was applied onto a separator film (PET film) using a knife coater and then dried in an oven at 70 ° C. for 10 minutes to produce adhesive films of Production Examples 1 to 5 having a thickness of 40 to 45 ⁇ m. did.
  • Two adhesive films were overlapped with a hot roll laminator to adjust the thickness to 80 to 90 ⁇ m.
  • the volatilization end temperature of the flux activator shown in Table 1 (the lowest temperature at which the thermogravimetric change rate becomes 0%) was measured. The measurement was performed using a TG / DTA6300 (product name) manufactured by Seiko Instruments Inc. at a temperature rising rate of 10 ° C./min, an air flow rate of 200 ml / min, a measurement temperature range of 30 to 300 ° C., and a sample weight of 5 to 10 mg. .
  • the measurement results of the volatilization end temperature are shown in Table 1.
  • a mode in which the fracture occurred at the interface between the solder ball and the copper foil was designated as an A mode
  • B mode a mode in which the solder ball was bulk fractured
  • the B mode was designated as acceptable.
  • the shear test was conducted using a bond tester series 4000 (product name) manufactured by Daisy Corporation at room temperature (25 ° C.) under conditions of a shear height of 50 ⁇ m and a shear rate of 100 ⁇ m / s.
  • the results of the flux activity evaluation (number of remaining solder balls, solder wetting spread rate, shear test result) are shown in Table 1.
  • thermoplastic resin 25 parts by mass of a phenoxy resin FX293 (manufactured by Toto Kasei Co., Ltd., product name), as an epoxy resin, 30 parts by mass of a solid polyfunctional epoxy resin EP1032H60 (manufactured by Japan Epoxy Resin, product name) and a liquid bisphenol A type epoxy Resin EP828 (made by Japan Epoxy Resin, product name) 45 parts by mass, as curing agent 2,4-dihydroxymethyl-5-phenylimidazole 2PHZ (product name, manufactured by Shikoku Kasei Kogyo Co., Ltd.), 3 parts by mass, condensed polycyclic oxazine As a compound having a skeleton (flux activator), 5 parts by mass of the compound shown in Table 2 and 100 parts by mass of SE6050 (product name, manufactured by Admatechs Co., Ltd.) as a spherical silica fill
  • Comparative Example 3 An adhesive film of Comparative Example 3 was produced in the same manner as Examples 1 to 3 and Comparative Examples 1 and 2 except that the amount of the spherical silica filler was 220 parts by mass.
  • the radius of the adhesive film after pressurization was measured with a microscope, and the viscosity (Pa ⁇ s) at 150 ° C. was calculated according to the above-described formula (1).
  • Z / Z 0 (r 0 / r) Formula 2 (3)
  • Z 0 Thickness of the adhesive film before pressurization
  • Z Thickness of the adhesive film after pressurization
  • r 0 Radius of the adhesive film before pressurization (Because it is punched at a diameter of 4 mm, it is 2 mm.)
  • r radius of the adhesive film after pressing
  • Adhesive film cut into a 10mm square in the chip mounting area of the printed circuit board JKIT TYPE III (product name, manufactured by Hitachi Ultra LSI Systems) with a receiving solder layer (Sn-3.0Ag-0.5Cu) formed on the copper wiring surface was affixed at 80 ° C. for 5 seconds with a load of 50 N. After that, the separator film is peeled off and chip Phase 2E175 (product name, size 10 mm square, thickness 550 ⁇ m, number of bumps 832, bump pitch 175 ⁇ m, manufactured by Hitachi ULSI Systems) on which high melting point solder bumps (95Pb-5Sn) are formed and printed.
  • Phase 2E175 product name, size 10 mm square, thickness 550 ⁇ m, number of bumps 832, bump pitch 175 ⁇ m, manufactured by Hitachi ULSI Systems
  • the substrate was connected using a flip chip bonder FCB3 (manufactured by Panasonic Factory Solutions, product name). Specifically, first, the position of the chip Phase2E175 and the printed circuit board is aligned, heated at 180 ° C. for 5 to 30 seconds while being pressurized with a load of 5N, and then heated at 230 to 280 ° C. for 5 seconds while being pressurized with a load of 5N. did. Subsequently, a heat treatment was performed in an oven at 165 ° C. for 2 hours to produce a connection sample.
  • FCB3 manufactured by Panasonic Factory Solutions, product name
  • connection sample was prepared. The thing which was able to take continuity was set as the pass. The cross section of the connection portion between the high melting point solder bump and the receiving solder layer was observed for the conductive material. Those in which the high melting point solder bumps and the receiving solder layer were uniformly wetted and joined were regarded as acceptable, and those in which they were not uniformly wetted and joined were regarded as unacceptable.
  • connection sample was left for 100 hours in a test tank set at a temperature of 130 ° C. and a relative humidity of 85%. Thereafter, a continuity test was performed. When the resistance change rate is within ⁇ 10% compared to the connection resistance before leaving, the test was accepted. In addition, about the thing which failed in the cross-sectional observation of solder joint evaluation, moisture resistance reliability evaluation was not performed.
  • An adhesive film was attached to a polyimide substrate having a comb pattern made of copper wiring formed with a wiring width of 20 ⁇ m and a distance between wirings of 40 ⁇ m at 80 ° C. for 5 seconds so as to cover the comb pattern with a load of 100 N. After the separator film was peeled off, heat treatment was performed in an oven at 165 ° C. for 2 hours to prepare a sample for evaluation.
  • the evaluation sample was left for 100 hours in a test tank set at a temperature of 130 ° C. and a relative humidity of 85%.
  • IMV migration tester MIG-8600 product name
  • the insulation resistance of the sample for evaluation in the test tank was continuously measured.
  • An evaluation sample having an insulation resistance of 10 6 ⁇ or more during measurement for 100 hours was regarded as acceptable.
  • the insulation reliability evaluation was not performed about the thing which failed in the cross-sectional observation of solder joint property evaluation.
  • ⁇ in Table 3 indicates “pass” and ⁇ indicates “fail”.
  • Examples 1 to 3 to which the flux activator was added did not lower the physical properties of the adhesive film compared to Comparative Example 1 to which no flux activator was added. .
  • Examples 1 to 3 showed good solderability, moisture resistance reliability, and insulation reliability.
  • the solderability was good, but a defect occurred in the insulation reliability evaluation.
  • Comparative Example 3 as a result of cross-sectional observation, the high melting point solder bump and the receiving solder layer were not wet uniformly. It is thought that since the adhesive film has a high viscosity, the molten solder has been inhibited from spreading.
  • the adhesive films of Examples 1 to 3 exhibit good flux activity.
  • the metal bonding is facilitated by using the adhesive films of Examples 1 to 3, the electrical connection reliability is improved.
  • 6a adhesive film, 6, 12 ... adhesive layer, 10, 30 ... semiconductor device, 21, 31 ... circuit board, 22, 10a ... semiconductor element.

Abstract

Cette invention concerne un activateur de flux comprenant un composé ayant un squelette oxazine polycyclique condensée.
PCT/JP2009/056889 2008-04-02 2009-04-02 Activateur de flux, composition de résine adhésive, pâte adhésive, film adhésif, procédé de fabrication d'un dispositif semi-conducteur, et dispositif semi-conducteur WO2009123285A1 (fr)

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JP2008210862A JP5581576B2 (ja) 2008-04-02 2008-08-19 フラックス活性剤、接着剤樹脂組成物、接着ペースト、接着フィルム、半導体装置の製造方法、及び半導体装置
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US11117872B2 (en) 2015-12-08 2021-09-14 Dic Corporation Oxazine compound, composition and cured product
WO2020116313A1 (fr) * 2018-12-03 2020-06-11 パナソニックＩｐマネジメント株式会社 Composition de résine de renforcement, composant électronique, procédé de fabrication de composant électronique, structure de montage et procédé de fabrication de structure de montage
CN111745324A (zh) * 2019-03-28 2020-10-09 松下知识产权经营株式会社 焊膏和安装结构体
JP2021084968A (ja) * 2019-11-28 2021-06-03 住友ベークライト株式会社 基材付き樹脂膜、プリント配線基板および電子装置

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