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WO2019208513A1 - Composition de résine, feuille de résine, et corps multicouche - Google Patents

Composition de résine, feuille de résine, et corps multicouche Download PDF

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Publication number
WO2019208513A1
WO2019208513A1 PCT/JP2019/017071 JP2019017071W WO2019208513A1 WO 2019208513 A1 WO2019208513 A1 WO 2019208513A1 JP 2019017071 W JP2019017071 W JP 2019017071W WO 2019208513 A1 WO2019208513 A1 WO 2019208513A1
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Prior art keywords
resin composition
resin
thermosetting
component
composition according
Prior art date
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English (en)
Japanese (ja)
Inventor
泰紀 柄澤
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Lintec Corp
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Lintec Corp
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Priority to KR1020207029691A priority Critical patent/KR102744001B1/ko
Priority to CN201980028328.5A priority patent/CN112105677B/zh
Priority to JP2020516350A priority patent/JP7232247B2/ja
Publication of WO2019208513A1 publication Critical patent/WO2019208513A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/06—Interconnection of layers permitting easy separation
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/35—Heat-activated
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to a resin composition, a resin sheet, and a laminate.
  • Patent Document 1 includes a maleimide compound, a compound having at least one of an allyl group and an epoxy group, an amine compound, and a radical generator containing at least one of an acetophenone derivative and a tetraphenylethane derivative.
  • a resin composition is disclosed.
  • An object of the present invention is to provide a resin composition, a resin sheet, and a laminate that can achieve both low-temperature and short-time thermosetting conditions and peel strength after thermosetting.
  • the resin composition which concerns on 1 aspect of this invention is a resin composition containing (A) thermosetting component, Comprising: Said (A) thermosetting component is (A1) maleimide resin, and (A2) phosphorus A peel strength after thermal curing of a sheet-like material having a thickness of 25 ⁇ m formed of the resin composition and containing a system curing accelerator is 2.0 N / 10 mm or more.
  • the (A2) phosphorus curing accelerator is preferably a compound having a structure in which a phosphorus atom and an aryl group are bonded.
  • the (A2) phosphorus-based curing accelerator is preferably a phosphonium salt.
  • the content of the (A2) phosphorus curing accelerator is preferably 1% by mass or less based on the total solid content of the resin composition.
  • the content of the (A2) phosphorus curing accelerator is 2% by mass or less based on the total amount of the solid content of the (A) thermosetting component. preferable.
  • the resin composition according to one embodiment of the present invention it is preferable to further contain (A3) an allyl resin.
  • the resin composition according to one embodiment of the present invention it is preferable to further contain (B) a binder component.
  • the (B) binder component is preferably a phenoxy resin.
  • the resin composition according to one embodiment of the present invention preferably further contains (C) an inorganic filler.
  • the resin composition according to one embodiment of the present invention preferably further contains (D) a coupling agent.
  • the resin composition according to one embodiment of the present invention is preferably used for sealing a semiconductor element or interposing between the semiconductor element and another electronic component.
  • the resin composition according to one embodiment of the present invention is preferably used for sealing a power semiconductor element or interposing between the power semiconductor element and another electronic component.
  • the resin composition according to one embodiment of the present invention seals a semiconductor element using any one or more of silicon carbide and gallium nitride, or uses any one or more of the silicon carbide and gallium nitride. It is preferably used for interposing between the conventional semiconductor element and other electronic components.
  • the resin sheet which concerns on 1 aspect of this invention is a resin sheet formed from the resin composition containing (A) thermosetting component, Comprising: Said (A) thermosetting component is (A1) maleimide resin, And (A2) containing a phosphorus-based curing accelerator and having a peel strength after thermosetting of 2.0 N / 10 mm or more.
  • the laminate according to one embodiment of the present invention includes the above-described resin sheet according to one embodiment of the present invention and a release material, and the release material includes a release agent layer containing an alkyd resin release agent. It is characterized by that.
  • thermosetting it is possible to provide a resin composition, a resin sheet, and a laminate that can achieve both low-temperature and short-time thermosetting conditions and peel strength after thermosetting.
  • the resin composition according to the present embodiment contains (A) a thermosetting component.
  • the (A) thermosetting component according to this embodiment contains (A1) a maleimide resin and (A2) a phosphorus-based curing accelerator.
  • the peel strength after thermosetting of a sheet-like material having a thickness of 25 ⁇ m formed from the resin composition according to the present embodiment is 2.0 N / 10 mm or more.
  • thermosetting under low temperature and short time thermosetting conditions is possible, and process suitability can be improved.
  • the peel strength after thermosetting of a sheet material having a thickness of 25 ⁇ m formed from the resin composition according to the present embodiment is less than 2.0 N / 10 mm, when the resin composition is used as a sealing material or the like, the metal The peel strength with respect to the adherend such as the surface becomes insufficient.
  • the peel strength after thermosetting of the sheet-like material formed from the resin composition according to the present embodiment is adjusted, for example, by the type of component used for the resin composition (particularly, the type of phosphorus curing accelerator) and the blending amount. By doing so, it is possible to adjust to the above range.
  • the peel strength after thermosetting of a sheet-like material having a thickness of 25 ⁇ m formed from the resin composition according to the present embodiment is a sheet-like material in which the resin composition is formed into a sheet shape using a measurement method described later.
  • thermosetting component (hereinafter sometimes simply referred to as “component (A)”) has a property of forming a three-dimensional network when heated and firmly bonding the adherend.
  • component (A) a maleimide resin
  • component (A2) a phosphorus-based curing accelerator
  • A1 Maleimide resin in this embodiment will not be specifically limited if it is a maleimide resin which contains two or more maleimide groups in 1 molecule.
  • the (A1) maleimide resin in the present embodiment preferably includes, for example, a benzene ring, and more preferably includes a structure in which a maleimide group is linked to the benzene ring, from the viewpoint of heat resistance.
  • the maleimide compound preferably includes two or more structures in which a maleimide group is linked to a benzene ring.
  • the (A1) maleimide resin in the present embodiment is a maleimide resin containing two or more maleimide groups and one or more biphenyl skeletons in one molecule (hereinafter sometimes simply referred to as “biphenyl maleimide resin”). Is preferred.
  • the maleimide resin in this embodiment is preferably represented by the following general formula (1) from the viewpoint of heat resistance and adhesiveness.
  • k is an integer of 1 or more, and the average value of k is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, and 1 or more and 3 or less. More preferably it is.
  • m1 and m2 are each independently an integer of 1 or more and 6 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1.
  • n1 and n2 are each independently an integer of 0 or more and 4 or less, preferably an integer of 0 or more and 2 or less, and more preferably 0.
  • R 1 and R 2 are each independently an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group.
  • maleimide resin represented by the general formula (1) in the present embodiment include compounds represented by the following general formula (2) or the following general formula (3).
  • k is the same as k in the general formula (1).
  • n1, n2, R 1 and R 2 are the same as n1, n2, R 1 and R 2 in the general formula (1).
  • Examples of the maleimide resin product represented by the general formula (3) include “MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd.
  • the (A1) maleimide resin in this embodiment is preferably a maleimide resin containing two or more maleimide groups and two or more phenylene groups in one molecule. From the viewpoint of increasing solubility in a solvent and improving sheet formability, it is preferable to have a substituent on the phenylene group. Examples of the substituent include an alkyl group such as a methyl group and an ethyl group, and an alkylene group.
  • the maleimide resin (A1) in this embodiment is preferably a maleimide resin having an ether bond between a maleimide group and a phenylene group from the viewpoint of sheet formability.
  • the maleimide resin containing two or more maleimide groups and two or more phenylene groups in one molecule is represented, for example, by the following general formula (4).
  • R 3 to R 6 are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • L 1 is an alkylene group having 1 to 6 carbon atoms
  • L 2 And L 3 are each independently an alkylene group having 1 to 6 carbon atoms or an arylene group having 6 to 10 carbon atoms
  • p and q are each independently 0 or 1.
  • the maleimide resin represented by the general formula (4) in the present embodiment is specifically represented by, for example, the following general formula (5) or the following general formula (6).
  • L 1 is an alkylene group having 1 to 6 carbon atoms.
  • R 3 to R 6 are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Specific examples of the (A1) maleimide resin in the present embodiment include, for example, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane from the viewpoint of obtaining a cured product having high sheet formability and high heat resistance.
  • bis (3-ethyl-5-methyl-4-maleimidophenyl) methane is more preferable.
  • the content of the component (A1) in the component (A) is based on the total solid content of the component (A) (that is, the nonvolatile content of the component (A) excluding the solvent for dilution is 100% by mass). ) Is preferably 50% by mass or more, and more preferably 55% by mass or more.
  • the (A2) phosphorus curing accelerator in the present embodiment is not particularly limited as long as it is a compound that contains a phosphorus atom and accelerates the polymerization reaction of (A1) maleimide resin.
  • Examples of the (A2) phosphorus curing accelerator in the present embodiment include alkyl phosphine compounds, aryl phosphine compounds, alkyl aryl phosphine compounds, phosphine oxide compounds, and phosphonium salts.
  • alkylphosphine compound examples include trimethylphosphine, triethylphosphine, tri (n-propyl) phosphine, tri (n-butyl) phosphine, tri (n-hexyl) phosphine, tri (n-octyl) phosphine, and And tricyclohexylphosphine.
  • aryl phosphine compound examples include triphenylphosphine, tri (p-tolyl) phosphine, tri (m-tolyl) phosphine, tri (o-tolyl) phosphine, tris (2,3-dimethylphenyl) phosphine, Tris (2,4-dimethylphenyl) phosphine, tris (2,5-dimethylphenyl) phosphine, tris (2,6-dimethylphenyl) phosphine, tris (3,4-dimethylphenyl) phosphine, tris (3,5- Examples thereof include dimethylphenyl) phosphine, tribenzylphosphine, bis (diphenyl) phosphinoethane, and bis (diphenyl) phosphinobutane.
  • alkylarylphosphine compound examples include cyclohexyldiphenylphosphine, dicyclohexylphenylphosphine, butyldiphenylphosphine, dibutylphenylphosphine, n-octyldiphenylphosphine, and di (n-octyl) phenylphosphine.
  • phosphine oxide compound examples include triethylphosphine oxide, tri (n-propyl) phosphine oxide, tri (n-butyl) phosphine oxide, tri (n-hexyl) phosphine oxide, and tri (n-octyl) phosphine oxide. , Triphenylphosphine oxide, and tris (3-hydroxypropyl) phosphine oxide.
  • the phosphonium salt is a salt composed of a cation represented by PR 4 + and an anion represented by X ⁇ .
  • Examples of the cation represented by PR 4 + in the phosphonium salt include tetraethylphosphonium ion, triethylbenzylphosphonium ion, tetra (n-butyl) phosphonium ion, tri (n-butyl) methylphosphonium ion, and tri (n-butyl) octylphosphonium.
  • anion represented by X ⁇ in the phosphonium salt examples include bromide ion, chloride ion, iodide ion, o, o-diethyl phosphorodithioate ion, hydrogen hexahydrophthalate ion, sulfate ion, tetraphenylborate ion, and Examples thereof include tetrakis (4-methylphenyl) borate ion.
  • the phosphonium salt include tetraethylphosphonium bromide, triethylbenzylphosphonium chloride, tetra (n-butyl) phosphonium bromide, tetra (n-butyl) phosphonium chloride, tetra (n-butyl) phosphonium iodide, tri (n -Butyl) methylphosphonium iodide, tri (n-butyl) octylphosphonium bromide, tri (n-butyl) hexadecylphosphonium bromide, tri (n-butyl) allylphosphonium bromide, tri (n-butyl) benzylphosphonium chloride, tetra Phenylphosphonium bromide, tetra (n-butyl) phosphonium-o, o-diethyl phosphorodithioate, tetra (n-butyl
  • A2 phosphorus curing accelerators include tris (3-hydroxypropyl) phosphine, bisdiphenylphosphinoferrocene, and tri (n-butyl) phosphine sulfide.
  • the phosphorus-based curing accelerator includes a phosphorus atom and an aryl group directly from the viewpoint of increasing the peel strength of the cured product of the sheet-like product formed from the resin composition.
  • a compound having a bonded structure is preferred.
  • the aryl group directly bonded to the phosphorus atom of the compound in the phosphorus-based curing accelerator is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and among them, a phenyl group, a tolyl group and a xylyl group Is more preferable.
  • the compound having a structure in which a phosphorus atom and a phenyl group are directly bonded include triphenylphosphine, bisdiphenylphosphinoethane, bisdiphenylphosphinobutane, cyclohexyldiphenylphosphine, triphenylphosphine oxide, tetra Examples thereof include phenylphosphonium tetraphenylborate and tetraphenylphosphonium tetrakis (4-methylphenyl) borate.
  • Specific examples of the compound having a structure in which a phosphorus atom and a tolyl group are directly bonded include the aforementioned tri-p-tolylphosphine.
  • Specific examples of the compound having a structure in which a phosphorus atom and a xylyl group are directly bonded include the aforementioned tris (2,3-dimethylphenyl) phosphine.
  • the phosphorus-based curing accelerator (A2) in this embodiment is preferably a phosphonium salt from the viewpoint of the peel strength and reaction temperature of the cured product of the sheet-like material formed from the resin composition.
  • A2 When a phosphonium salt is used as the phosphorus-based curing accelerator, the peel strength is hardly lowered even if the amount of (A2) phosphorus-based curing accelerator is increased.
  • the content of the (A2) phosphorus curing accelerator in the resin composition is based on the total solid content of the resin composition (that is, when the total nonvolatile content excluding the dilution solvent is 100% by mass). ) Is preferably 1% by mass or less, and more preferably 0.75% by mass or less.
  • the content of the (A2) phosphorus curing accelerator in the resin composition is preferably 0.05% by mass or more and 0.1% by mass or more based on the total solid content of the resin composition. More preferred.
  • A2 When the content of the phosphorus curing accelerator is within the above range, the above peel strength can be obtained regardless of the type of (A2) phosphorus curing accelerator.
  • the content of the (A2) phosphorus curing accelerator is based on the total solid content of the component (A) (that is, when the nonvolatile content of the component (A) excluding the solvent for dilution is 100% by mass). ) Is preferably from 0.1% by mass to 2% by mass, and more preferably from 0.3% by mass to 1.5% by mass.
  • the (A2) phosphorus-based curing accelerator in the resin composition can be used singly or in combination of two or more.
  • thermosetting component contained in the resin composition in the present embodiment preferably further contains (A3) an allyl resin.
  • the (A3) allyl resin (hereinafter sometimes simply referred to as “(A3) component”) is preferably liquid at room temperature.
  • a thermosetting component contains an allyl resin, a network can be adjusted to an appropriate range after the resin composition is cured.
  • the mass ratio (A1 / A3) of (A1) maleimide resin to (A3) allyl resin is preferably 1.5 or more, and more preferably 4.5 or more. If mass ratio (A1 / A3) is the said range, there exists a tendency for the storage elastic modulus E 'in 250 degreeC of the hardened
  • the mass ratio (A1 / A3) is in the above range, the complex viscosity ⁇ of the resin composition is appropriately adjusted, and the fluidity of the resin composition at the time of application to an adherend is secured, while the resin composition Further improvement in heat resistance after curing of the product is realized. Furthermore, if mass ratio (A1 / A3) is the said range, the bleed out of the allyl resin from a resin composition will also be suppressed.
  • the upper limit value of the mass ratio (A1 / A3) is not particularly limited. For example, the mass ratio (A1 / A3) may be 50 or less.
  • the (A3) allyl resin in the present embodiment is not particularly limited as long as it is a resin having an allyl group.
  • the (A3) allyl resin in this embodiment is preferably an allyl resin containing two or more allyl groups in one molecule, for example.
  • the allyl resin in the present embodiment is more preferably represented by the following general formula (7).
  • R 7 and R 8 are each independently an alkyl group, preferably an alkyl group having 1 to 10 carbon atoms, and preferably an alkyl group having 1 to 4 carbon atoms. More preferred is an alkyl group selected from the group consisting of a methyl group and an ethyl group.
  • (A3) allyl resin in the present embodiment include diallyl bisphenol A (2,2-bis (3-allyl-4-hydroxyphenyl) propane).
  • thermosetting resin other than the component (A1) may be any thermosetting resin having high heat resistance, and examples thereof include an epoxy resin, a benzoxazine resin, a cyanate resin, and a melamine resin. These thermosetting resins can be used alone or in combination of two or more.
  • the curing accelerator other than the component (A2) include imidazole compounds (for example, 2-ethyl-4-methylimidazole) and the like.
  • curing accelerators can be used alone or in combination of two or more.
  • the cured resin other than the component (A3) include resins such as a phenol resin and a resin having a C ⁇ C double bond other than the component (A3), and amines, acid anhydrides, and formaldehyde. . These curable resins can be used alone or in combination of two or more.
  • the content of these components is the total solid content of the component (A). It is preferably 10% by mass or less, more preferably 5% by mass or less on the basis (that is, when the nonvolatile content of the component (A) excluding the diluent solvent is 100% by mass).
  • the content of the thermosetting component (A) in the resin composition is based on the total solid content of the resin composition (that is, when the total nonvolatile content excluding the dilution solvent is 100% by mass). It is preferably 2% by mass or more and 75% by mass or less, and more preferably 5% by mass or more and 70% by mass or less.
  • (A) Handling property of a resin composition, sheet formability, and the heat resistance of a resin sheet improve because content of a thermosetting component exists in the said range.
  • the resin composition preferably includes (B) a binder component (hereinafter, may be simply referred to as “(B) component”) in addition to the (A) component.
  • a binder component hereinafter, may be simply referred to as “(B) component”
  • film forming properties can be imparted and the resin composition can be easily formed into a sheet.
  • the binder component (B) of this embodiment is a resin component other than the component (A), and has a function of joining the component (A) or other components.
  • the binder component is preferably a thermoplastic resin or the like.
  • the component (B) may have a functional group as long as it has a function of bonding the component (A) or other components.
  • the (B) binder component when the (B) binder component has a functional group, the (B) binder component can be involved in the curing of the resin composition by heat. Differentiated from curable components.
  • the binder component can be selected from various resins, and may be an aliphatic compound or an aromatic compound.
  • the binder component is preferably at least one resin selected from the group consisting of, for example, a phenoxy resin, an acrylic resin, a methacrylic resin, a polyester resin, a urethane resin, and a polyamideimide resin. To phenoxy resin is more preferable.
  • the polyester resin is preferably a wholly aromatic polyester resin.
  • a binder component can be used individually by 1 type or in combination of 2 or more types.
  • phenoxy resin examples include a bisphenol A skeleton (hereinafter, bisphenol A may be referred to as “BisA”), a bisphenol F skeleton (hereinafter, bisphenol F may be referred to as “BisF”), a biphenyl skeleton, and a naphthalene skeleton.
  • BisA bisphenol A skeleton
  • BisF bisphenol F skeleton
  • a phenoxy resin having one or more skeletons selected from the group consisting of bisphenol A skeleton and bisphenol F skeleton is more preferable.
  • the weight average molecular weight (Mw) of the binder component is preferably from 100 to 1,000,000, preferably from 1,000 to 800,000 from the viewpoint of easily adjusting the complex viscosity of the resin composition to a desired range. More preferably, it is more preferably 10,000 or more and 100,000 or less.
  • the weight average molecular weight in the present specification is a standard polystyrene equivalent value measured by a gel permeation chromatography (GPC) method.
  • the content of the binder component (B) in the resin composition is based on the total solid content of the resin composition (that is, when the total nonvolatile content excluding the dilution solvent is 100% by mass), It is preferably 0.1% by mass or more and 50% by mass or less, and more preferably 1% by mass or more and 40% by mass or less.
  • the content of the component (A1) is based on the total amount of the solid contents of the component (A) and the component (B) (that is, when the total nonvolatile content excluding the dilution solvent is 100% by mass). 20 mass% or more and 80 mass% or less is preferable. If content of (A1) component is 20 mass% or more, the heat resistance of a resin composition can further be improved. On the other hand, if content of (A1) component is 80 mass% or less, a resin composition can be easily shape
  • the resin composition preferably includes (C) an inorganic filler (hereinafter, sometimes simply referred to as “(C) component”) in addition to the (A) component and the (B) component.
  • the component (C) can improve at least one of the thermal characteristics and mechanical characteristics of the resin composition.
  • an inorganic filler a silica filler, an alumina filler, a boron nitride filler, etc. are mentioned. Among these, silica filler is preferable. Examples of the silica filler include fused silica and spherical silica.
  • An inorganic filler can be used individually by 1 type or in combination of 2 or more types. Moreover, (C) the inorganic filler may be surface-treated.
  • the average particle size of the inorganic filler is not particularly limited.
  • the average particle diameter of the inorganic filler is preferably from 0.1 nm to 100 ⁇ m, more preferably from 10 nm to 10 ⁇ m, as determined from a general particle size distribution meter.
  • the average particle size of the inorganic filler (C) is a value measured by a dynamic light scattering method using a particle size distribution measuring device (manufactured by Nikkiso Co., Ltd., product name “Nanotrack Wave-UT151”). To do.
  • the content of the inorganic filler (C) in the resin composition is 10% by mass or more and 90% by mass based on the total solid content of the resin composition (that is, when the total nonvolatile content excluding the dilution solvent is 100% by mass). It is preferable that it is mass% or less, and it is more preferable that it is 20 mass% or more and 80 mass% or less.
  • the resin composition preferably further contains (D) a coupling agent in addition to the components (A) to (C).
  • the coupling agent preferably has a functional group that the above-described (A) thermosetting component has, or (B) a functional group that reacts with the functional group that the binder component has, and (A) the functional group that the thermosetting component has. It is more preferable to have a group that reacts with.
  • the coupling agent is preferably a silane (silane coupling agent) because of its versatility and cost merit.
  • a coupling agent can be used individually by 1 type or in combination of 2 or more types.
  • the coupling agent as described above is usually 0.1 parts by mass or more with respect to 100 parts by mass of the total amount of the solid content (nonvolatile content excluding the diluent solvent) of the component (A) and the component (B). It mix
  • the resin composition which concerns on this embodiment, the resin composition containing only (A) thermosetting component, (B) binder component, (C) inorganic filler, and (D) coupling agent is mentioned. .
  • thermosetting component thermosetting component
  • binder component binder component
  • inorganic filler inorganic filler
  • coupling agent coupling agent
  • the said Examples of the resin composition include components other than the components (A) to (D).
  • the resin composition may further contain other components.
  • other components include at least one selected from the group consisting of a crosslinking agent, pigment, dye, antifoaming agent, leveling agent, ultraviolet absorber, foaming agent, antioxidant, flame retardant, and ion scavenger.
  • the resin composition may further contain a crosslinking agent in order to adjust initial adhesiveness before curing and cohesion.
  • the crosslinking agent include organic polyvalent isocyanate compounds and organic polyvalent imine compounds.
  • a crosslinking agent can be used individually by 1 type or in combination of 2 or more types.
  • organic polyvalent isocyanate compounds include aromatic polyvalent isocyanate compounds, aliphatic polyvalent isocyanate compounds, alicyclic polyvalent isocyanate compounds, and trimers of these polyvalent isocyanate compounds, and Examples thereof include terminal isocyanate urethane prepolymers obtained by reacting these polyvalent isocyanate compounds and polyol compounds. More specific examples of the organic polyvalent isocyanate compound include, for example, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate, and 1,4-xylene diene.
  • An organic polyvalent isocyanate compound can be used individually by 1 type or in combination of 2 or more types.
  • organic polyvalent imine compound examples include, for example, N, N′-diphenylmethane-4,4′-bis (1-aziridinecarboxamide), trimethylolpropane-tri- ⁇ -aziridinylpropionate, tetra And methylolmethane-tri- ⁇ -aziridinylpropionate and N, N′-toluene-2,4-bis (1-aziridinecarboxamide) triethylenemelamine.
  • An organic polyvalent imine compound can be used individually by 1 type or in combination of 2 or more types.
  • the crosslinking agent as described above is usually blended at a ratio of 0.01 parts by weight or more and 12 parts by weight or less, preferably 0.1 parts by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the above-mentioned (B) binder component.
  • the resin composition according to this embodiment is preferably used for a semiconductor element. Specifically, the resin composition according to this embodiment is preferably used for sealing a semiconductor element. Moreover, it is preferable that the resin composition which concerns on this embodiment is used for interposing between a semiconductor element and another electronic component.
  • the semiconductor element is preferably a power semiconductor element. Since the resin composition according to this embodiment is excellent in heat resistance, it seals a power semiconductor element that is assumed to operate at a high temperature of 200 ° C. or higher, or is interposed between the power semiconductor element and another electronic component. Can be used. In addition, the use of the resin composition which concerns on this embodiment is not limited to these uses.
  • the resin composition which concerns on this embodiment is used for sealing the semiconductor element using any 1 or more types of silicon carbide and gallium nitride.
  • the resin composition according to the present embodiment is preferably used for interposing between a semiconductor element using any one or more of silicon carbide and gallium nitride and another electronic component. Examples of other electronic components include a printed wiring board and a lead frame. Since the upper limit of the operating temperature of the silicon semiconductor element is about 175 ° C., it is preferable to use a semiconductor element using at least one of silicon carbide and gallium nitride capable of high temperature operation as the power semiconductor element.
  • the resin composition according to the present embodiment is excellent in heat resistance, sealing a semiconductor element using any one or more of silicon carbide and gallium nitride assumed to operate at a high temperature of 200 ° C. or higher, or carbonizing. It can be used for interposing between a semiconductor element using any one or more of silicon and gallium nitride and another electronic component.
  • the resin composition before curing has an exothermic peak temperature of 170 ° C. or higher and 210 ° C. or lower as measured at a heating rate of 10 ° C./min by a differential scanning calorimetry (DSC) method.
  • the said exothermic peak temperature is the temperature which the exothermic peak with the largest intensity
  • the tact time in the semiconductor manufacturing process can be effectively shortened by the short time until the resin composition is cured.
  • a plurality of resin compositions existing between the semiconductor chips are added after laminating (temporarily placing) the semiconductor chips in order to improve process efficiency. It may be cured at once. Even in such a case, since the exothermic peak temperature is in the above-mentioned range, the resin composition attached to the semiconductor chip laminated at the initial stage of the process in an unintended stage such as before the completion of the lamination of the semiconductor chips. Can be cured.
  • thermosetting conditions In the thermosetting conditions in the resin composition according to this embodiment, the heating temperature is preferably 50 ° C. or higher and 200 ° C. or lower, and preferably 100 ° C. or higher and 190 ° C. or lower. In the thermosetting conditions in the resin composition according to this embodiment, the heating time is preferably 30 minutes or longer and 2 hours or shorter, and more preferably 45 minutes or longer and 1 hour 30 minutes or shorter. When the thermosetting conditions in the resin composition are in the above range, the resin composition can be thermoset at a low temperature and in a short time.
  • the peel strength after thermosetting of a sheet-like material having a thickness of 25 ⁇ m formed from the resin composition according to the present embodiment is 2.0 N / 10 mm or more. Further, the peel strength after thermosetting is preferably 3.0 N / 10 mm or more and 50 N / 10 mm or less, and more preferably 3.0 N / 10 mm or more and 40 N / 10 mm or less. When the peel strength after thermosetting of the resin composition is in the above range, it is possible to maintain high adhesion to the adherend.
  • the resin sheet according to the present embodiment is formed from a resin composition containing (A) a thermosetting component, and (A) the thermosetting component is (A1) a maleimide resin and (A2) a phosphorus-based curing accelerator. Containing.
  • the (A) thermosetting component, (A1) maleimide resin, and (A2) phosphorus-based curing accelerator are the same as those described above.
  • at least any component selected from the group which consists of (C) inorganic filler mentioned above, (D) coupling agent, and another component may be mix
  • thermosetting on the low temperature and short time thermosetting conditions is attained, and process suitability can be improved.
  • the peel strength after thermosetting of the resin sheet according to the present embodiment is 2.0 N / 10 mm or more.
  • the peel strength for the adherend such as a metal surface is insufficient when the resin composition is used as a sealing material.
  • the peel strength after thermosetting of the resin sheet according to the present embodiment is adjusted to the above range by adjusting, for example, the type of component used for the resin composition (particularly, the type of phosphorus-based curing accelerator) and the blending amount. can do.
  • the peeling strength after thermosetting of the resin sheet according to the present embodiment was determined by performing a peeling test with a peeling angle of 90 degrees between the resin sheet after thermosetting and the adherend using the measurement method described later. Sought by doing. Specifically, a test piece was prepared and a peel test was performed as follows.
  • the resin sheet according to the present embodiment obtained by forming the resin composition into a sheet is simple to apply to an adherend, and particularly easy to apply to a large-area adherend. Since the resin composition can be formed in advance into a shape suitable for the shape after the sealing step when the resin composition is processed into a sheet shape, the resin sheet can be applied to the adherend to achieve uniformity in thickness and component ratio. It functions as a maintained sealing material. Further, if the resin composition is in the form of a sheet, it is excellent in handleability because it has no fluidity.
  • the method for forming the resin composition into a sheet is not particularly limited, and a conventionally known method for forming a sheet can be employed.
  • the resin sheet according to the present embodiment may be a belt-shaped sheet or may be provided in a state of being wound in a roll shape.
  • the resin sheet according to the present embodiment wound up in a roll shape can be used by being unwound from a roll and cut into a desired size.
  • the thickness of the resin sheet according to this embodiment is preferably 10 ⁇ m or more, and more preferably 20 ⁇ m or more. Further, the thickness of the resin sheet according to the present embodiment is preferably 500 ⁇ m or less, more preferably 400 ⁇ m or less, and further preferably 300 ⁇ m or less.
  • the resin sheet according to the present embodiment is used for sealing a semiconductor element, or is interposed between the semiconductor element and another electronic component, like the resin composition according to another embodiment. It is preferable. Moreover, it is preferable that the resin sheet which concerns on this embodiment is applied collectively to a several semiconductor element. For example, if the resin composition is in the form of a sheet, the resin sheet is applied to the structure in which the semiconductor elements are arranged for each gap of the frame provided with a plurality of gaps, and the frame and the semiconductor elements are collectively It can be used for a so-called panel level package for sealing. In addition, the use of the resin sheet which concerns on this embodiment is not limited to these uses.
  • FIG. 1 shows a schematic cross-sectional view of a laminate 1 according to this embodiment.
  • the laminate 1 of the present embodiment includes a first release material 2, a second release material 4, and a resin sheet 3 provided between the first release material 2 and the second release material 4.
  • the resin sheet 3 is a resin sheet according to the present embodiment.
  • the first release material 2 and the second release material 4 have releasability, and there is a difference between the release force of the first release material 2 on the resin sheet 3 and the release force of the second release material 4 on the resin sheet 3. It is preferable.
  • the material of the first release material 2 and the second release material 4 is not particularly limited.
  • the ratio (P2 / P1) of the peeling force P2 of the second peeling material 4 to the peeling force P1 of the first peeling material 2 is preferably 0.02 ⁇ P2 / P1 ⁇ 1 or 1 ⁇ P2 / P1 ⁇ 50. .
  • the first release material 2 and the second release material 4 may be, for example, a member having a release property, a member subjected to a release treatment, or a member having a release agent layer laminated thereon. Good.
  • examples of the material of the first release material 2 and the second release material 4 include an olefin resin and a fluorine resin.
  • the first release material 2 and the second release material 4 can be a release material including a release substrate and a release agent layer formed by applying a release agent on the release substrate.
  • a release material comprising a release substrate and a release agent layer is easy to handle.
  • the 1st peeling material 2 and the 2nd peeling material 4 may be equipped with the releasing agent layer only on the single side
  • Examples of the peeling base material include a paper base material, a laminated paper obtained by laminating a thermoplastic resin such as polyethylene on the paper base material, and a plastic film.
  • Examples of the paper substrate include glassine paper, coated paper, and cast coated paper.
  • Examples of the plastic film include polyester films (for example, polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate), polyolefin films (for example, polypropylene, polyethylene, and the like), and the like. Among these, a polyester film is preferable.
  • the release agent examples include a silicone-based release agent composed of a silicone resin; a long-chain alkyl group-containing compound-based release agent composed of a compound containing a long-chain alkyl group such as polyvinyl carbamate and an alkylurea derivative; alkyd Alkyd resin-based release agents composed of resins (for example, non-convertible alkyd resins and convertible alkyd resins); olefin resins (for example, polyethylene (for example, high density polyethylene, low density polyethylene, and linear low density) Polyethylene, etc.), propylene homopolymers having an isotactic structure or syndiotactic structure, and crystalline polypropylene resins such as propylene- ⁇ -olefin copolymers, etc.); , And synthetic rubber (eg, butadiene rubber, isoprene) Rubber release agent composed of rubber such as styrene-butadiene rubber, methyl methacrylate-butadiene rubber, and
  • release agents can be used alone or in combination of two or more.
  • alkyd resin release agents are preferred.
  • a phenoxy resin is used as the (B) binder component of the resin composition included in the resin sheet 3
  • a general silicone release agent when used, the release material is not intended and the resin sheet 3 is not used. Therefore, it is preferable to use an alkyd resin release agent.
  • the thickness of the first release material 2 and the second release material 4 is not particularly limited.
  • the thicknesses of the first release material 2 and the second release material 4 are usually 1 ⁇ m or more and 500 ⁇ m or less, and preferably 3 ⁇ m or more and 100 ⁇ m or less.
  • the thickness of the release agent layer is not particularly limited.
  • the thickness of the release agent layer is preferably 0.01 ⁇ m or more and 3 ⁇ m or less, and more preferably 0.03 ⁇ m or more and 1 ⁇ m or less.
  • the manufacturing method of the laminated body 1 is not specifically limited.
  • the laminated body 1 is manufactured through the following processes. First, a resin composition is applied on the first release material 2 to form a coating film. Next, this coating film is dried to form the resin sheet 3. Next, the laminated body 1 is obtained by bonding the resin sheet 3 and the second release material 4 at room temperature.
  • the resin composition according to this embodiment can be suitably used for a power semiconductor element.
  • the semiconductor element is preferably a power semiconductor element.
  • the power semiconductor element is also assumed to operate at a high temperature of 200 ° C. or higher.
  • a material used for a semiconductor device having a power semiconductor element is required to have heat resistance. Since the resin composition and the resin sheet according to the present embodiment are excellent in heat resistance, they are used to cover the power semiconductor element in the semiconductor device or to be interposed between the power semiconductor element and other components. Is preferably used.
  • the resin composition according to the present embodiment can be suitably used for a semiconductor element using any one or more of silicon carbide and gallium nitride.
  • the semiconductor element is preferably a semiconductor element using at least one of silicon carbide and gallium nitride. Since a semiconductor element using at least one of silicon carbide and gallium nitride has characteristics different from those of a silicon semiconductor element, a power semiconductor element, a high-power device for a base station, a sensor, a detector, a Schottky barrier diode, etc.
  • the heat resistance of the semiconductor element using any one or more of silicon carbide and gallium nitride attention is also paid to the heat resistance of the semiconductor element using any one or more of silicon carbide and gallium nitride, and the resin composition and resin sheet of the present embodiment are excellent in heat resistance. It is preferably used in combination with a semiconductor element using at least one of silicon carbide and gallium nitride.
  • this invention is such It is not limited to the laminated body of a various aspect.
  • a laminate having a resin sheet and a release material provided only on one surface of the resin sheet may be used.
  • the semiconductor sealing application has been described.
  • the resin composition and the resin sheet of the present invention can be used in addition to insulating materials for circuit boards (for example, hard printed wiring board materials, flexible wirings). Substrate materials, build-up substrate interlayer insulating materials, etc.), build-up adhesive films, adhesives, and the like. Applications of the resin composition and the resin sheet of the present invention are not limited to these applications.
  • Resin compositions according to Examples 1 to 6 and Comparative Examples 1 to 7 were prepared at a blending ratio (mass% (solid content conversion ratio)) shown in Table 1.
  • the materials used for the preparation of the resin composition are as follows.
  • Maleimide resin Maleimide resin having a biphenyl group (maleimide resin represented by the general formula (3), “MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd.)
  • Curing accelerator-1 Tetraphenylphosphonium tetrakis (4-methylphenyl) borate (“TPP-MK” and “TPP-MK” manufactured by Hokuko Chemical Co., Ltd. are registered trademarks)
  • Curing accelerator-2 Triphenylphosphine ("Hokuko TPP” and "Hokuko TPP” manufactured by Hokuko Chemical Co., Ltd.
  • Curing accelerator-3 Tetrabutylphosphonium hydrogen hexahydrophthalate (“TBP-3S” manufactured by Hokuko Chemical Co., Ltd.)
  • Curing accelerator-4 2-ethyl-4-methylimidazole (“2E4MZ” manufactured by Shikoku Kasei Kogyo Co., Ltd.)
  • Allyl resin diallyl bisphenol A (“DABPA” manufactured by Daiwa Kasei Kogyo Co., Ltd.)
  • Binder component Binder resin: BisA / BisF mixed type phenoxy resin (“ZX-1356-2” manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., weight average molecular weight 65,000)
  • Silica filler fused silica (epoxysilane modification, average particle size 0.5 ⁇ m, maximum particle size 2.0 ⁇ m)
  • the dried resin composition and the second release material polyethylene terephthalate film provided with a release layer formed from a silicone-based release agent, thickness 38 ⁇ m
  • a first release material, a resin sheet made of a resin composition, and a second release material were laminated in this order.
  • a copper foil (size 50 mm ⁇ 10 mm, thickness 150 ⁇ m, JIS H 3100 specification) was bonded to the other surface of the resin sheet by pressure-bonding under the same conditions as the above ⁇ bonding conditions>.
  • the resin composition was cured under the thermosetting conditions shown in Table 1 to prepare a sample.

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Abstract

L'invention concerne une composition de résine qui contient (A) un composant thermodurcissable, et qui est caractérisée en ce que : le composant thermodurcissable (A) contient (A1) une résine maléimide et (A2) un accélérateur de durcissement à base de phosphore ; et la résistance au pelage après durcissement thermique d'un produit de type feuille, qui est formé à partir de cette composition de résine et a une épaisseur de 25 µm, est supérieure ou égale à 2,0 N/10 mm.
PCT/JP2019/017071 2018-04-26 2019-04-22 Composition de résine, feuille de résine, et corps multicouche Ceased WO2019208513A1 (fr)

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JP7232247B2 (ja) 2023-03-02
KR20210005579A (ko) 2021-01-14
CN112105677A (zh) 2020-12-18
TW201945452A (zh) 2019-12-01

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