WO2016085115A1 - Composé à base de phosphonium, composition de résine époxy le contenant et dispositif à semi-conducteur fabriqué à l'aide de celui-ci - Google Patents

Composé à base de phosphonium, composition de résine époxy le contenant et dispositif à semi-conducteur fabriqué à l'aide de celui-ci Download PDF

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WO2016085115A1
WO2016085115A1 PCT/KR2015/010729 KR2015010729W WO2016085115A1 WO 2016085115 A1 WO2016085115 A1 WO 2016085115A1 KR 2015010729 W KR2015010729 W KR 2015010729W WO 2016085115 A1 WO2016085115 A1 WO 2016085115A1
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epoxy resin
resin composition
formula
phenol
curing
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Korean (ko)
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천진민
권기혁
김민겸
이동환
정주영
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삼성에스디아이 주식회사
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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
    • 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
    • C08G59/688—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 containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
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    • 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
    • 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
    • C08G59/20—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 epoxy compounds used
    • 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
    • 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
    • C08G59/70—Chelates
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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    • 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
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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
    • H01L2224/26—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
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29199—Material of the matrix
    • H01L2224/2929—Material of the matrix with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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    • 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
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • 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
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73201—Location after the connecting process on the same surface
    • H01L2224/73203—Bump and layer connectors
    • H01L2224/73204—Bump and layer connectors the bump connector being embedded into the layer connector
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    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/91—Methods for connecting semiconductor or solid state bodies including different methods provided for in two or more of groups H01L2224/80 - H01L2224/90
    • H01L2224/92—Specific sequence of method steps
    • H01L2224/921—Connecting a surface with connectors of different types
    • H01L2224/9212—Sequential connecting processes
    • H01L2224/92122—Sequential connecting processes the first connecting process involving a bump connector
    • H01L2224/92125—Sequential connecting processes the first connecting process involving a bump connector the second connecting process involving a layer connector
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    • 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
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    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/73—Means for bonding being of different types provided for in two or more of groups H01L24/10, H01L24/18, H01L24/26, H01L24/34, H01L24/42, H01L24/50, H01L24/63, H01L24/71
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    • H01L24/91—Methods for connecting semiconductor or solid state bodies including different methods provided for in two or more of groups H01L24/80 - H01L24/90
    • H01L24/92—Specific sequence of method steps
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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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
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
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    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation

Definitions

  • the present invention relates to a phosphonium compound, an epoxy resin composition comprising the same, and a semiconductor device manufactured using the same.
  • the epoxy resin composition includes an epoxy resin, a curing agent, a curing catalyst, and the like, and as the curing catalyst, an imidazole catalyst, an amine catalyst, and a phosphine catalyst have been generally used.
  • the progress of such a curing reaction may cause an increase in viscosity and a decrease in fluidity when the epoxy resin composition is a liquid, and may exhibit viscosity when the epoxy resin composition is a solid.
  • such a change of state does not appear uniformly in an epoxy resin composition. Therefore, when the epoxy resin composition is actually cured at a high temperature, moldability may be decreased due to fluidity decrease, and mechanical, electrical and chemical properties of the product may be reduced after molding.
  • An object of the present invention is to provide a curing catalyst compound that can promote curing of an epoxy resin, has excellent fluidity during molding, exhibits high curing strength, and can be cured in a short curing time.
  • Another object of the present invention is to provide a compound for a curing catalyst that can promote curing of an epoxy resin even at low temperatures.
  • Still another object of the present invention is to provide an epoxy resin composition comprising the compound for the curing catalyst and a semiconductor device manufactured using the same.
  • the present invention provides a phosphonium-based compound represented by the following [Formula 1].
  • R 1 , R 2 , R 3 , R 4 , X 1 , X 2 , Y 1 , Y 2 , Y 3 , and Y 4 are as defined in the following detailed description).
  • the phosphonium-based compound may be one of the compounds represented by the following Chemical Formulas 1a to 1e.
  • the present invention provides an epoxy resin composition
  • an epoxy resin composition comprising an epoxy resin, a curing agent, an inorganic filler and a curing catalyst, wherein the curing catalyst includes the phosphonium-based compound that acts as a curing accelerator.
  • the said epoxy resin is a bisphenol-A epoxy resin, a bisphenol F-type epoxy resin, a phenol novolak-type epoxy resin, a tert- butyl catechol-type epoxy resin, a naphthalene type epoxy resin, a glycidylamine type epoxy resin, a cresol novolak-type epoxy Resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring containing epoxy resin, cyclohexanedimethanol type epoxy resin, trimethylol type epoxy resin, phenol aralkyl type epoxy resin, and halogenated It may include one or more of the epoxy resins.
  • curing agent is a phenol aralkyl type phenol resin, a phenol novolak-type phenol resin, a xylox phenol resin, a cresol novolak-type phenol resin, a naphthol type phenol resin, a terpene type phenol resin, a polyfunctional phenol resin, a dicyclopentadiene type phenol Novolak-type phenolic resin synthesized from resin, bisphenol A and resol, polyhydric phenol compound including tris (hydroxyphenyl) methane, dihydroxybiphenyl, acid anhydride including maleic anhydride and phthalic anhydride, metaphenylenediamine , Diaminodiphenylmethane and diaminodiphenylsulfone.
  • the curing catalyst may be included in 0.01 to 5% by weight of the epoxy resin composition.
  • the phosphonium-based compound may be included in 10 to 100% by weight of the curing catalyst.
  • the epoxy resin composition may include 2 to 17 wt% of the epoxy resin, 0.5 to 13 wt% of the curing agent, 70 to 95 wt% of the inorganic filler, and 0.01 to 5 wt% of the curing catalyst.
  • the epoxy resin composition may have a storage stability of 80% or more after 72 hours.
  • the epoxy resin composition may have a curing shrinkage ratio of less than 0.4% represented by the following [Formula 1]:
  • Cure Shrinkage Rate
  • C is the length of the specimen obtained by the transfer molding press epoxy resin composition at 175, 70kgf / cm 2 , D is obtained after the post-cure (PMC: post molding cure) at 175, and cooled) Length of the specimen).
  • the present invention provides a semiconductor device sealed with the epoxy resin composition.
  • the present invention provides a compound for a curing catalyst that can promote the curing of the epoxy resin, can promote the curing of the epoxy resin even at low temperatures, and in a mixture containing an epoxy resin, a curing agent and the like even in a predetermined range of time and temperature conditions
  • a compound for storage catalyst with high storage stability was provided.
  • FIG. 1 is a cross-sectional view of a semiconductor device in accordance with an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of a semiconductor device of another embodiment of the present invention.
  • substituted in “substituted or unsubstituted” means that at least one hydrogen atom of the functional group is a hydroxyl group, a halogen, an amino group, a nitro group, a cyano group, an oxo group, a C1-C20 alkyl group, a C1-C20 haloalkyl group , C6-C30 aryl group, C3-C30 heteroaryl group, C3-C10 cycloalkyl group, C3-C10 heterocycloalkyl group, C7-C30 arylalkyl group, C1-C30 heteroalkyl group
  • the 'halo' means fluorine, chlorine, iodine or bromine.
  • aryl group refers to a substituent in which all elements of a cyclic substituent have p-orbital and p-orbital forms a conjugate, and a single ring structure or multiple at least two rings are fused. It may include, but is not limited to, a phenyl group, biphenyl group, naphthyl group, naphthol group, anthracenyl group, and the like.
  • 'hetero' in the 'heterocycloalkyl group', 'heteroaryl group', 'heterocycloalkylene group', and 'heteroarylene group' means a nitrogen, oxygen, sulfur or phosphorus atom.
  • the phosphonium-based compound of the present invention includes a phosphonium-based cation and an anion having a cyclic structure in which the central metal is zinc (Zn), and may be represented by the following Chemical Formula 1.
  • R 1 , R 2 , R 3 and R 4 are each independently substituted or unsubstituted C1-C30 aliphatic hydrocarbon group, substituted or unsubstituted C6-C30 aromatic hydrocarbon group, or Substituted or unsubstituted C1-C30 hydrocarbon group containing a hetero atom,
  • X 1 and X 2 are each independently a substituted or unsubstituted C 1 to C 30 aliphatic hydrocarbon group, a substituted or unsubstituted C 6 to C 30 aromatic hydrocarbon group, or a substituted or unsubstituted C 1 to C 30 containing a hetero atom
  • a hydrocarbon group Y 1 , Y 2 , Y 3 , and Y 4 are each independently an oxygen atom (O), a sulfur atom (S) or a substituted nitrogen atom (N)).
  • the phosphonium compound of the present invention may be one of the compounds represented by the following Chemical Formulas 1a to 1e.
  • the phosphonium-based compound as described above may be a water-insoluble compound.
  • the phosphonium-based compound of the present invention may be prepared by reacting a phosphonium-based cation-containing compound with an anion-containing compound having a cyclic structure having zinc as a central metal in a molar ratio of 2: 1.
  • the phosphonium-based cation-containing compound may be prepared by combining a phosphine-based compound with an alkyl halide, an aryl halide or an aralkyl halide in a solvent, or a phosphonium-based cation-containing salt (eg, tetraphenylphosphonium halide).
  • a phosphine-based compound with an alkyl halide, an aryl halide or an aralkyl halide in a solvent, or a phosphonium-based cation-containing salt (eg, tetraphenylphosphonium halide).
  • the phosphine-based compound may be triphenylphosphine, methyldiphenylphosphine, dimethylphenylphosphine, ethyldiphenylphosphine, diphenylpropylphosphine, isopropyldiphenylphosphine, diethylphenylphosphine, and the like.
  • the present invention is not limited thereto.
  • the anion-containing compound of the cyclic structure having zinc as the central metal may be an anion-containing salt.
  • the anion-containing compound may be prepared by combining an alkali salt and a zinc compound (eg, biscatechol zincate, bisthiocatechol zincate, bisthiosalicylic zincate) in a solvent.
  • a zinc compound eg, biscatechol zincate, bisthiocatechol zincate, bisthiosalicylic zincate
  • the present invention is not limited thereto.
  • the phosphonium-based compound of the present invention as described above can be used as a latent curing catalyst by being added to the epoxy resin composition to be described later.
  • the phosphonium-based compound reacts with the epoxide group in the epoxy resin to perform a ring-opening reaction, and the ring-opening reaction of the epoxide group by the reaction with a hydroxyl group in the epoxy resin after the ring-opening reaction, the chain terminal and the epoxide of the activated epoxy resin
  • the hardening reaction is accelerated by the reaction of .
  • the phosphonium-based compound catalyzes curing only when the desired curing temperature or more, and there is no curing catalyst activity when the phosphonium compound is not the desired curing temperature. This is believed to be because the ionic bond between the phosphonium cation and the zinc center metal anion is dissociated at a specific temperature and becomes active.
  • the progress of the curing reaction may cause an increase in viscosity and a decrease in fluidity when the epoxy resin composition is a liquid, and may exhibit viscosity when the epoxy resin composition is a solid.
  • the phosphonium-based compound of the present invention has a catalytic activity only at the curing temperature as described above, when added to the epoxy resin composition, it is possible to minimize the viscosity change of the epoxy resin, thereby realizing excellent storage stability for a long time Can be.
  • the epoxy resin composition of the present invention may include at least one of an epoxy resin, a curing agent, an inorganic filler, and a curing catalyst.
  • the epoxy resin may have at least one epoxy group in a molecule, for example, may have at least two or more epoxy groups in a molecule, or may have two or more epoxy groups and one or more hydroxyl groups in a molecule.
  • the epoxy resin may include at least one of a solid epoxy resin and a liquid epoxy resin, and preferably a solid epoxy resin may be used.
  • epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol novolak type epoxy resins, tert-butyl catechol type epoxy resins, naphthalene type epoxy resins, glycidylamine type epoxy resins, and cresolno. Volac type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring containing epoxy resin, cyclohexane dimethanol type epoxy resin, trimethylol type epoxy resin, phenol aralkyl type epoxy resin And halogenated epoxy resins. These may be included alone or in combination of two or more thereof.
  • the epoxy resin may be a biphenyl type epoxy resin represented by the following [Formula 2] and / or a phenol aralkyl type epoxy resin represented by the following [Formula 3].
  • R is an alkyl group having 1 to 4 carbon atoms, the average value of n is 0 to 7
  • the epoxy resin may be included 2 to 17% by weight, for example 3 to 15% by weight, for example 3 to 12% by weight based on the solids content of the composition. In the above range, the curability of the composition may not be lowered.
  • the curing agent is a phenol aralkyl type phenol resin, a phenol novolak type phenol resin, a xylock type phenol resin, a cresol novolak type phenol resin, a naphthol type phenol resin, a terpene type phenol resin, a polyfunctional phenol resin, a dicyclopentadiene type phenol resin, Novolac-type phenolic resins synthesized from bisphenol A and resol, polyhydric phenol compounds including tris (hydroxyphenyl) methane, dihydroxybiphenyl, acid anhydrides including maleic anhydride and phthalic anhydride, metaphenylenediamine, dia Aromatic amines, such as a minodiphenylmethane and a diamino diphenyl sulfone, etc. are mentioned.
  • the curing agent may be a phenol resin having one or more hydroxyl groups.
  • the curing agent may be a xylox phenol resin of Formula 4 and / or a phenol aralkyl type phenol resin of Formula 5 below.
  • the curing agent may be included in the epoxy resin composition 0.5 to 13% by weight, for example 1 to 10% by weight, for example 2 to 8% by weight based on the solids content. In the above range, the curability of the composition may not be lowered.
  • the epoxy resin composition of the present invention may include an inorganic filler.
  • Inorganic fillers can increase the mechanical properties and low stress of the composition.
  • examples of the inorganic fillers include molten silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, titanium oxide, antimony oxide, and glass fibers.
  • molten silica having a low coefficient of linear expansion is preferable in terms of low stress.
  • Molten silica refers to amorphous silica having a true specific gravity of 2.3 or less, and also includes amorphous silica made by melting crystalline silica or synthesized from various raw materials.
  • the shape and particle size of the molten silica are not particularly limited, but the molten silica includes 50 to 99% by weight of spherical molten silica having an average particle diameter of 5 to 30 ⁇ m and 1 to 50% by weight of spherical molten silica having an average particle diameter of 0.001 to 1 ⁇ m.
  • the mixture it is preferable to include the mixture to be 40 to 100% by weight based on the total inorganic filler. Moreover, according to a use, the maximum particle diameter can be adjusted and used in any one of 45 micrometers, 55 micrometers, and 75 micrometers.
  • conductive carbon may be included as a foreign matter on the silica surface, but it is preferable to select a material having a small amount of polar foreign matter mixed therein.
  • the amount of the inorganic filler used depends on the required physical properties such as formability, low stress, and high temperature strength.
  • the inorganic filler may be included in 70 to 95% by weight, for example 75 to 92% by weight of the epoxy resin composition. Within this range, flame retardancy, fluidity and reliability of the epoxy resin composition can be ensured.
  • the epoxy resin composition of the present invention may include a curing catalyst containing a phosphonium-based compound represented by the above [Formula 1].
  • the phosphonium-based compound represented by [Formula 1] may be included in 0.01 to 5% by weight, for example 0.02 to 1.5% by weight, for example 0.05 to 1.5% by weight in the epoxy resin composition.
  • the curing reaction time is not delayed, and the fluidity of the composition can be ensured.
  • the epoxy resin composition of the present invention may further include a non-phosphonium-based curing catalyst containing no phosphonium.
  • a non-phosphonium-based curing catalyst containing no phosphonium As the non-phosphonium-based curing catalysts, tertiary amine curing catalysts, organometallic compound curing catalysts, organophosphorus compound curing catalysts, imidazole curing catalysts and boron compound curing catalysts can be used.
  • Tertiary amine curing catalysts include benzyldimethylamine, triethanolamine, triethylenediamine, diethylaminoethanol, tri (dimethylaminomethyl) phenol, 2-2- (dimethylaminomethyl) phenol, 2,4,6-tris (dia) Minomethyl) phenol and tri-2-ethylhexyl acid salt.
  • Organometallic compound curing catalysts include chromium acetylacetonate, zinc acetylacetonate, nickel acetylacetonate, and the like.
  • organophosphorus curing catalysts include tris-4-methoxyphosphine, triphenylphosphine, triphenylphosphine triphenylborane, triphenylphosphine-1,4-benzoquinone adduct and the like.
  • the imidazole curing catalysts include 2-methylimidazole, 2-phenylimidazole, 2-aminoimidazole, 2 - methyl-1-vinylimidazole, 2-ethyl-4-methylimidazole, 2- Heptadecylimidazole and the like.
  • Examples of the boron compound curing catalyst include triphenylphosphine tetraphenylborate, tetraphenylboron salt, trifluoroborane-n-hexylamine, trifluoroborane monoethylamine, tetrafluoroboranetriethylamine, tetrafluoroboraneamine, and the like. There is this. In addition, 1,5- diazabicyclo [4.3.0] non-5-ene (1, 5- diazabicyclo [4.3.0] non-5-ene: DBN), 1, 8- diazabicyclo [5.4.
  • undec-7-ene (1,8-diazabicyclo [5.4.0] undec-7-ene: DBU) and phenol novolak resin salts
  • a non-phosphonium-based curing catalyst an organophosphorus curing catalyst, a boron compound curing catalyst, an amine curing catalyst, or an imidazole curing catalyst may be used alone or in combination. It is also possible to use an adduct made by pre-reaction with an epoxy resin or a curing agent as the non-phosphonium-based curing catalyst.
  • the phosphonium-based compound of the present invention may be included in 10 to 100% by weight, for example 60 to 100% by weight of the total curing catalyst, the curing reaction time is not delayed in the above range, there is an effect of ensuring the fluidity of the composition Can be.
  • the curing catalyst may be included in 0.01 to 5% by weight, for example 0.02 to 1.5% by weight, for example 0.05 to 1.5% by weight of the epoxy resin composition. In the above range, the curing reaction time is not delayed, and the fluidity of the composition can be ensured.
  • the epoxy resin composition of the present invention may further include conventional additives included in the epoxy resin composition in addition to the above components.
  • the additive may include one or more of a coupling agent, a release agent, a stress relaxer, a crosslinking enhancer, a leveling agent, and a coloring agent.
  • the coupling agent may be one or more selected from the group consisting of epoxysilane, aminosilane, mercaptosilane, alkylsilane and alkoxysilane, but is not limited thereto.
  • the coupling agent may be included in 0.1 to 1% by weight of the epoxy resin composition.
  • the release agent may be used at least one selected from the group consisting of paraffin wax, ester wax, higher fatty acid, higher fatty acid metal salt, natural fatty acid and natural fatty acid metal salt.
  • the release agent may be included in 0.1 to 1% by weight of the epoxy resin composition.
  • the stress relaxing agent may be used one or more selected from the group consisting of modified silicone oil, silicone elastomer, silicone powder and silicone resin, but is not limited thereto.
  • the stress relaxation agent is preferably contained in 0 to 6.5% by weight, for example 0 to 1% by weight, for example 0.1 to 1% by weight in the epoxy resin composition.
  • the modified silicone oil a silicone polymer having excellent heat resistance is good, and silicone oil having an epoxy functional group, silicone oil having an amine functional group, silicone oil having a carboxyl functional group, and the like may be used alone or in combination of two or more kinds.
  • the silicone oil is preferably included in an amount of about 0.05 to 1.5% by weight based on the total epoxy resin composition.
  • the content of silicone oil exceeds 1.5% by weight, surface contamination is likely to occur and the resin bleed may be long, and when used below 0.05% by weight, sufficient low modulus of elasticity may not be obtained. have.
  • the silicone powder having a central particle diameter of 15 ⁇ m or less from the viewpoint of preventing moldability deterioration.
  • the silicon powder may be contained in 0 to 5% by weight, for example 0.1 to 5% by weight based on the total resin composition.
  • the additive may be included in 0.1 to 10% by weight, for example 0.1 to 3% by weight of the epoxy resin composition.
  • the epoxy resin composition of the present invention preferably has a flow length of about 59-75 inches (about 1.4986 m to 1.905 m) at 175 ° C. and 70 kgf / cm 2 in EMMI-1-66.
  • the flow length satisfies the above range, it may be usefully used as a sealing material of a semiconductor device.
  • the epoxy resin composition of the present invention preferably has a curing shrinkage rate of less than about 0.4%, for example, about 0.01 to about 0.39% measured by the following [formula 1].
  • the curing shrinkage satisfies the numerical range, it may be usefully used as a sealing material for semiconductor devices.
  • Cure Shrinkage Rate
  • C is the length of the specimen obtained by transfer molding press the epoxy resin composition at 175 °C, 70kgf / cm 2
  • D is post-cure (PMC: post molding cure), and cooled the specimen at 175 °C Is the length of the specimen obtained).
  • the epoxy resin in the epoxy resin composition may be used alone, the additives such as the epoxy resin and the curing agent, curing catalyst, release agent, coupling agent, and stress release agent by a linear reaction such as melt master batch (melt master batch) It may be included in the form of additional compounds made.
  • the method for producing the epoxy resin composition is not particularly limited, and for example, each component contained in the composition may be uniformly mixed using a Henschel mixer or a Rodige mixer, and then 90 to 120 ° C with a roll mill or kneader. It can be prepared by melt kneading in the cooling, cooling and grinding process.
  • the epoxy resin composition preferably has a glass transition temperature of 100 °C to 130 °C, for example, about 123 °C to 125 °C.
  • a glass transition temperature of 100 °C to 130 °C, for example, about 123 °C to 125 °C.
  • the resin composition of the present invention is required for use in epoxy resin compositions such as semiconductor device sealing applications, adhesive films, insulating resin sheets such as prepregs, circuit boards, solder resists, underfill agents, die bonding materials, and component supplement resin applications. It can be applied to a wide range of applications and is not particularly limited.
  • the semiconductor element of this invention is sealed using the epoxy resin composition of this invention mentioned above.
  • a semiconductor device 100 may include a wiring board 10, a bump 30 formed on the wiring board 10, and a semiconductor chip 20 formed on the bump 30. ), And the gap between the wiring board 10 and the semiconductor chip 20 may be sealed by the epoxy resin composition 40, wherein the epoxy resin composition may be the epoxy resin composition of the present invention described above. have.
  • a semiconductor device 200 may include a wiring board 10, a bump 30 formed on the wiring board 10, and a semiconductor chip 20 formed on the bump 30. It includes, the gap between the wiring board 10 and the semiconductor chip 20 and the entire upper surface of the semiconductor chip 30 may be sealed with an epoxy resin composition 40, wherein the epoxy resin composition is It may be an epoxy resin composition of the present invention.
  • the sizes of the wiring boards, bumps, and semiconductor chips, and the number of bumps are arbitrary and may be changed.
  • the low pressure transfer molding method can be used most commonly.
  • the present invention is not limited thereto, and may be molded by an injection molding method or a casting method.
  • a semiconductor device of a copper lead frame, an iron lead frame, or a lead frame pre-plated with at least one material selected from the group consisting of palladium with nickel and copper on the lead frame, or an organic laminate frame can be manufactured. Can be.
  • NC-3000 (Nippon Kayaku), a biphenyl type epoxy resin, was used.
  • Inorganic filler A 9: 1 (weight ratio) mixture of spherical molten silica having an average particle diameter of 18 ⁇ m and spherical molten silica having an average particle diameter of 0.5 ⁇ m was used.
  • KBM-803 (Shinetsu), which is (e1) mercaptopropyltrimethoxysilane, and SZ-6070 (Dow Corning chemical), which is (e2) methyltrimethoxysilane, were mixed and used.
  • Carnauba wax was used as the release agent (f1) and carbon black MA-600 (Matsusita Chemical) was used as the colorant (f2).
  • the components were weighed according to the composition (unit: parts by weight) of Table 1 below, and then uniformly mixed using a Henschel mixer to prepare a primary composition in powder form. After the melt kneading at 95 °C using a continuous kneader and then cooled and pulverized to prepare an epoxy resin composition for sealing a semiconductor device.
  • Cure Shrinkage Rate
  • C is the length of the specimen obtained by the transfer molding press of the epoxy resin composition at 175 °C, 70kgf / cm 2
  • D is the specimen obtained after curing and cooling the specimen at 175 °C 4 hours
  • TMA thermomechanical analyzer
  • Hygroscopicity (%): molding the epoxy resin composition to be evaluated under the conditions of mold temperature 170 ⁇ 180 °C, clamp pressure 70kgf / cm 2 , transfer pressure 1000psi, transfer rate 0.5 ⁇ 1cm / s, curing time 120 seconds
  • the obtained specimens were placed in an oven at 170 to 180 ° C., and after 4 hours of post-curing (PMC: post molding cure), they were left at 85 ° C. and 85 RH% relative humidity for 168 hours, and then the weight change due to moisture absorption was measured. The moisture absorption was calculated by 3.
  • Hygroscopicity (weight of test piece after moisture absorption-weight of test piece before moisture absorption) ⁇ (weight of test piece before moisture absorption) ⁇ 100
  • Adhesion force (kgf): A copper metal element is prepared in a size suitable for a mold for measuring adhesion, and the epoxy resin composition to be evaluated on the prepared copper metal element is at a mold temperature of 170 to 180 ° C., a clamp pressure of 70 kgf / cm 2 , and transferred. Curing specimens were obtained by molding under conditions of a pressure of 1000 psi, a feed rate of 0.5 to 1 cm / s, and a curing time of 120 seconds. The obtained specimens were put in an oven at 170 to 180 ° C. and post-cured (PMC: post molding cure) for 4 hours. At this time, the area of the epoxy resin composition in contact with the copper metal element is 40 ⁇ 1mm2, the adhesion was measured by the average value after measuring by using a universal testing machine (UTM) for 12 specimens per measurement process.
  • UPM universal testing machine
  • Shore-D Using a multi-plunger system (MPS) molding machine equipped with a mold for an eTQFP (exposed thin quad flat package) package having a width of 24 mm, a length of 24 mm, and a thickness of 1 mm containing a copper metal element. After curing the epoxy resin composition to be evaluated at 175 ° C. for 50, 60, 70, 80 and 90 seconds, the hardness of the cured product according to the curing time was measured with a Shore-D hardness tester directly on the package on the mold. The higher the value, the better the degree of curing.
  • MPS multi-plunger system
  • Examples 1 to 5 show high fluidity, and in the case of storage stability, it can be seen that there is almost no difference in fluidity even after 72 hours. When the external crack does not occur, the crack resistance is good and no peeling occurs. It can be seen that the moisture resistance is also excellent.
  • Examples 4 and 5 show high fluidity and have low cure shrinkage when compared with Comparative Examples 1 and 2.
  • the degree of cure by curing time it can be seen that the degree of higher curing is shown even in a short curing time.
  • compositions of Comparative Examples 1 and 2 which do not contain the phosphonium-based compound of the present invention, have low storage stability, high curing shrinkage rate, low fluidity, low adhesion, and reliability problems. It can be seen that the effects of the invention can not be implemented.

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Abstract

La présente invention concerne un composé à base de phosphonium représenté par la formule chimique 1, une résine époxy le contenant et un dispositif à semi-conducteur scellé à l'aide de celui-ci.
PCT/KR2015/010729 2014-11-28 2015-10-12 Composé à base de phosphonium, composition de résine époxy le contenant et dispositif à semi-conducteur fabriqué à l'aide de celui-ci WO2016085115A1 (fr)

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US11482224B2 (en) 2020-05-20 2022-10-25 Sonos, Inc. Command keywords with input detection windowing

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JP2004002574A (ja) * 2002-06-03 2004-01-08 Sumitomo Bakelite Co Ltd エポキシ樹脂組成物及び半導体装置
JP2005048110A (ja) * 2003-07-30 2005-02-24 Sumitomo Bakelite Co Ltd 硬化促進剤、エポキシ樹脂組成物および半導体装置
JP2006307131A (ja) * 2005-03-28 2006-11-09 Sumitomo Bakelite Co Ltd 潜伏性触媒の製造方法およびエポキシ樹脂組成物
KR20070103419A (ko) * 2005-01-20 2007-10-23 스미토모 베이클리트 컴퍼니 리미티드 에폭시 수지 조성물, 그 잠복화 방법 및 반도체 장치
JP2013107917A (ja) * 2010-03-17 2013-06-06 Sumitomo Seika Chem Co Ltd 置換ベンゼンジチオール金属錯体の微粒子を含有する光吸収分散液、ならびにこれを用いた光吸収部材用組成物および光吸収部材

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JP2004300256A (ja) 2003-03-31 2004-10-28 Sumitomo Bakelite Co Ltd 硬化促進剤、エポキシ樹脂組成物および半導体装置

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Publication number Priority date Publication date Assignee Title
JP2004002574A (ja) * 2002-06-03 2004-01-08 Sumitomo Bakelite Co Ltd エポキシ樹脂組成物及び半導体装置
JP2005048110A (ja) * 2003-07-30 2005-02-24 Sumitomo Bakelite Co Ltd 硬化促進剤、エポキシ樹脂組成物および半導体装置
KR20070103419A (ko) * 2005-01-20 2007-10-23 스미토모 베이클리트 컴퍼니 리미티드 에폭시 수지 조성물, 그 잠복화 방법 및 반도체 장치
JP2006307131A (ja) * 2005-03-28 2006-11-09 Sumitomo Bakelite Co Ltd 潜伏性触媒の製造方法およびエポキシ樹脂組成物
JP2013107917A (ja) * 2010-03-17 2013-06-06 Sumitomo Seika Chem Co Ltd 置換ベンゼンジチオール金属錯体の微粒子を含有する光吸収分散液、ならびにこれを用いた光吸収部材用組成物および光吸収部材

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11482224B2 (en) 2020-05-20 2022-10-25 Sonos, Inc. Command keywords with input detection windowing

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