WO2016009730A1 - Composition de résine pour scellement et dispositif à semi-conducteur - Google Patents

Composition de résine pour scellement et dispositif à semi-conducteur Download PDF

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Publication number
WO2016009730A1
WO2016009730A1 PCT/JP2015/065723 JP2015065723W WO2016009730A1 WO 2016009730 A1 WO2016009730 A1 WO 2016009730A1 JP 2015065723 W JP2015065723 W JP 2015065723W WO 2016009730 A1 WO2016009730 A1 WO 2016009730A1
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Prior art keywords
group
resin composition
sealing
compound
semiconductor element
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PCT/JP2015/065723
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English (en)
Japanese (ja)
Inventor
純一 田部井
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住友ベークライト株式会社
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Publication date
Application filed by 住友ベークライト株式会社 filed Critical 住友ベークライト株式会社
Priority to CN201580038820.2A priority Critical patent/CN106536591B/zh
Priority to KR1020177003859A priority patent/KR102166100B1/ko
Publication of WO2016009730A1 publication Critical patent/WO2016009730A1/fr

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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
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—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
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3218—Carbocyclic compounds
    • 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
    • C08G59/40—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 curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • 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
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Definitions

  • the present invention relates to a sealing resin composition and a semiconductor device.
  • the epoxy resin composition used for such a sealing material generally comprises a composition such as an epoxy resin, a phenol resin-based curing agent, an inorganic filler, and a coupling agent.
  • a composition such as an epoxy resin, a phenol resin-based curing agent, an inorganic filler, and a coupling agent.
  • Specific performance required for the sealing material includes, for example, adhesion, solder resistance, fluidity, heat resistance, and high-temperature storage characteristics.
  • Patent Document 1 a sealing resin composition containing a compound having a mercapto group such as a silane coupling agent having a mercapto group has been developed (see Patent Document 1 and Patent Document 2).
  • a compound having a mercapto group such as a silane coupling agent having a mercapto group
  • Patent Document 2 a sealing resin composition containing a compound having a mercapto group
  • the present invention has been made in view of such circumstances, and an object of the present invention is to provide a sealing resin composition having sufficient adhesion to a metal and having high-temperature storage characteristics of the obtained semiconductor device. .
  • the resin composition for sealing which molds a semiconductor element
  • the resin composition for sealing containing the following components is provided.
  • R is a monovalent organic group.
  • a semiconductor element A bonding wire connected to the semiconductor element; A sealing resin that is composed of a cured product of the above-described sealing resin composition and seals the semiconductor element and the bonding wire; A semiconductor device is provided.
  • the encapsulating resin composition of the present invention has sufficient adhesion to metal and can improve the high-temperature storage characteristics of the resulting semiconductor device.
  • the sealing resin composition according to this embodiment is a sealing resin composition for molding a semiconductor element, and includes the following components.
  • A Epoxy resin
  • B Curing agent
  • C Inorganic filler
  • D Diaminotriazine compound represented by the following general formula (1)
  • R is a monovalent organic group.
  • An epoxy resin refers to a compound (monomer, oligomer and polymer) having two or more epoxy groups in one molecule, and does not particularly limit the molecular weight and molecular structure.
  • the epoxy resin include crystalline epoxy resins such as biphenyl type epoxy resins, bisphenol type epoxy resins, and stilbene type epoxy resins; novolak type epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins; Polyfunctional epoxy resins such as phenol methane type epoxy resins and alkyl-modified triphenol methane type epoxy resins; phenol aralkyl type epoxy resins having a phenylene skeleton, phenol aralkyl type epoxy resins such as a phenol aralkyl type epoxy resin having a biphenylene skeleton; dihydroxynaphthalene -Type epoxy resin, naphthol-type epoxy resin such as epoxy resin obtained by glycidyl ether
  • epoxy resin a phenol aralkyl type epoxy resin represented by the following formula (3) and a biphenyl type epoxy resin represented by the following formula (4) are preferable.
  • Ar 1 is a phenylene group (a group consisting of a phenol structure, a structure obtained by removing a hydrogen atom of the number of bonds from phenol) or a naphthylene group (a group consisting of a naphthalene structure, and bonded from naphthalene) The structure excluding the number of hydrogen atoms in the hand).
  • the glycidyl ether group may be bonded to either the ⁇ -position or the ⁇ -position.
  • Ar 2 is any one of a phenylene group, a biphenylene group (a group having a biphenylene structure, and a structure in which a hydrogen atom having a number of bonds is removed from biphenyl), and a naphthylene group.
  • R 3 and R 4 are each independently a hydrocarbon group having 1 to 10 carbon atoms.
  • g is an integer of 0 to 5 (provided that when Ar 1 is a phenylene group, it is an integer of 0 to 3).
  • h is an integer of 0 to 8 (provided that when Ar 2 is a phenylene group, it is an integer of 0 to 4, and when Ar 2 is a biphenylene group, it is an integer of 0 to 6).
  • n 1 represents the degree of polymerization, and the average value is 1 to 3.
  • Ar 1 is preferably a phenylene group.
  • Ar 2 is preferably a phenylene group or a biphenylene group.
  • the hydrocarbon group having 1 to 10 carbon atoms includes an alkyl group such as a methyl group or an ethyl group, an alkenyl group such as a vinyl group, an aryl group such as a phenyl group, etc. Can be mentioned.
  • g and h are preferably 0.
  • a plurality of R 5 are each independently a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms.
  • n 2 represents the degree of polymerization, and the average value is 0-4.
  • the hydrocarbon group having 1 to 4 carbon atoms include alkyl groups such as a methyl group and an ethyl group, and alkenyl groups such as a vinyl group.
  • the content of the epoxy resin relative to the whole sealing resin composition is not particularly limited, but the lower limit is preferably 2% by mass or more, and more preferably 4% by mass or more.
  • Adhesiveness etc. can be exhibited by making content of an epoxy resin more than the said lower limit.
  • As an upper limit of content of an epoxy resin 20 mass% or less is preferable, and 10 mass% or less is more preferable.
  • the curing agent (B) is not particularly limited as long as it is a component capable of curing the epoxy resin (A), and examples thereof include a polyaddition type curing agent, a catalyst type curing agent, and a condensation type curing agent. .
  • polyaddition type curing agents include aliphatic polyamines such as diethylenetriamine (DETA), triethylenetetramine (TETA), and metaxylylene diamine (MXDA), diaminodiphenylmethane (DDM), and m-phenylenediamine (MPDA).
  • DETA diethylenetriamine
  • TETA triethylenetetramine
  • MXDA metaxylylene diamine
  • DDM diaminodiphenylmethane
  • MPDA m-phenylenediamine
  • Aromatic polyamines such as diaminodiphenylsulfone (DDS), polyamine compounds including dicyandiamide (DICY), organic acid dihydrazide, etc .; alicyclic rings such as hexahydrophthalic anhydride (HHPA), methyltetrahydrophthalic anhydride (MTHPA) Acid anhydrides, aromatic anhydrides such as trimellitic anhydride (TMA), pyromellitic anhydride (PMDA), benzophenone tetracarboxylic acid (BTDA); novolac-type phenolic resin, phenol polymer Polyphenol compounds, polymercaptan compounds such as polysulfide, thioester and thioether; isocyanate compounds such as isocyanate prepolymers and blocked isocyanates; organic acids such as carboxylic acid-containing polyester resins; phenol resin curing agents described in detail below; Can be mentioned.
  • DDS diaminodiphenylsulfone
  • DIY
  • catalyst-type curing agent examples include tertiary amine compounds such as benzyldimethylamine (BDMA) and 2,4,6-trisdimethylaminomethylphenol (DMP-30); Examples thereof include imidazole compounds such as 2-methylimidazole and 2-ethyl-4-methylimidazole (EMI24); Lewis acids such as BF 3 complex.
  • BDMA benzyldimethylamine
  • DMP-30 2,4,6-trisdimethylaminomethylphenol
  • imidazole compounds such as 2-methylimidazole and 2-ethyl-4-methylimidazole (EMI24)
  • Lewis acids such as BF 3 complex.
  • condensation type curing agent examples include a resol type phenol resin; a urea resin such as a methylol group-containing urea resin; and a resin such as a methylol group-containing melamine resin.
  • a phenol resin curing agent is preferable as the (B) curing agent.
  • a phenol resin-based curing agent By using a phenol resin-based curing agent, it is possible to exert a good balance of flame resistance, moisture resistance, electrical characteristics, curability, storage stability, and the like.
  • the phenol resin-based curing agent refers to a compound (monomer, oligomer and polymer) having two or more phenolic hydroxy groups in one molecule, and the molecular weight and molecular structure thereof are not particularly limited.
  • phenol resin-based curing agent examples include novolak resins such as phenol novolak resins and cresol novolak resins; polyfunctional phenol resins such as triphenolmethane phenol resins; terpene modified phenol resins, dicyclopentadiene modified phenol resins and the like. Modified phenolic resins; aralkyl type resins such as phenol aralkyl resins having a phenylene skeleton and / or biphenylene skeleton, naphthol aralkyl resins having a phenylene and / or biphenylene skeleton; bisphenol compounds such as bisphenol A and bisphenol F, etc. One type may be used alone or two or more types may be used in combination.
  • an aralkyl type resin represented by the following formula (5) is preferable.
  • Ar 3 is a phenylene group (a group consisting of a phenol structure, a structure in which a hydrogen atom having a number of bonds is removed from phenol) or a naphthylene group (a group consisting of a naphthalene structure, bonded from naphthalene) The structure excluding the number of hydrogen atoms in the hand).
  • the hydroxy group may be bonded to either the ⁇ -position or the ⁇ -position.
  • Ar 4 is any one of a phenylene group, a biphenylene group (a group consisting of a biphenylene structure, in which a hydrogen atom having a number of bonds is removed from biphenyl), and a naphthylene group.
  • R 6 and R 7 are each independently a hydrocarbon group having 1 to 10 carbon atoms.
  • i is an integer of 0 to 5 (provided that when Ar 3 is a phenylene group, it is an integer of 0 to 3).
  • j is an integer of 0 to 8 (provided that when Ar 4 is a phenylene group, it is an integer of 0 to 4, and when Ar 4 is a biphenylene group, it is an integer of 0 to 6).
  • n 3 represents the degree of polymerization, and the average value is 1 to 3.
  • Ar 3 is preferably a phenylene group.
  • Ar 4 is preferably a phenylene group or a biphenylene group.
  • the Ar 4 by a phenylene group or a biphenylene group (introducing a phenylene skeleton or biphenylene skeleton), it is possible to increase the flame retardancy and the like.
  • i and j are not 0 in R 6 and R 7 , examples of the hydrocarbon group having 1 to 10 carbon atoms include those exemplified for R 3 and R 4 in the formula (3). i and j are preferably 0.
  • (B) Although it does not specifically limit as content with respect to the whole resin composition for sealing of a hardening
  • (C) Inorganic filler The well-known thing used for the general resin composition for sealing can be used for an inorganic filler.
  • the inorganic filler (C) include silica such as fused spherical silica, fused crushed silica, and crystalline silica, talc, alumina, titanium white, and silicon nitride. Among these, silica is preferable, and spherical fused silica is more preferable.
  • These (C) inorganic fillers may be used alone or in combination of two or more.
  • the inorganic filler preferably has a spherical shape and a wide particle size distribution.
  • an increase in the melt viscosity of the sealing resin composition can be suppressed, and the content of (C) the inorganic filler can be increased.
  • the inorganic filler (C) having a wide particle size distribution there is a method of using a mixture of a plurality of types of inorganic fillers having different average particle diameters.
  • the inorganic filler may be surface-treated with a coupling agent.
  • an inorganic filler previously treated with an epoxy resin or the like may be used as necessary.
  • (C) Although it does not specifically limit as an average particle diameter of an inorganic filler, As a lower limit, 0.1 micrometer or more is preferable and 0.3 micrometer or more is more preferable. On the other hand, the upper limit is preferably 40 ⁇ m or less, and more preferably 35 ⁇ m or less. Moreover, as a lower limit of the specific surface area of (C) inorganic filler, 1 m ⁇ 2 > / g or more is preferable and 3 m ⁇ 2 > / g or more is more preferable. On the other hand, as an upper limit, 10 m ⁇ 2 > / g or less is preferable and 7 m ⁇ 2 > / g or less is more preferable. By using an inorganic filler having an average particle diameter or specific surface area in such a range, fluidity, low hygroscopicity, etc. can be improved.
  • two or more inorganic fillers in the above preferred range are used in combination, for example, an inorganic filler having an average particle diameter of 0.1 ⁇ m to 1 ⁇ m and an inorganic filler having an average particle diameter of 10 ⁇ m to 40 ⁇ m. It is also preferable.
  • (C) Although it does not specifically limit as content with respect to the whole resin composition for sealing of an inorganic filler, As a lower limit, 35 mass% or more is preferable, 70 mass% or more is more preferable, 75 mass% or more is especially preferable. preferable. (C) By making content of an inorganic filler more than the said lower limit, sufficient low hygroscopicity, low thermal expansibility, etc. can be exhibited. (C) As an upper limit of content of an inorganic filler, 95 mass% or less is preferable, and 92 mass% or less is more preferable. (C) Sufficient fluidity
  • the diaminotriazine compound is a compound represented by the following formula (1).
  • a diaminotriazine compound may be used individually by 1 type, or may use 2 or more types together. Since the sealing resin composition of the present embodiment contains a specific compound having two amino groups in the triazine ring structure, sufficient adhesion to metal and high-temperature storage characteristics of the resulting semiconductor device Coexistence can be achieved. The reason for this is not clear, but the organic group provided at the 6-position in the triazine skeleton improves the compatibility with the epoxy resin in the sealing resin composition. This is considered to be easy to flow. In addition, it is considered that the two amino groups provided at the 2-position and 4-position in the triazine skeleton and the nitrogen atom at the 3-position improve adhesion to a lead frame, an organic substrate, a chip and the like.
  • R is a monovalent organic group.
  • the substituent R in Formula (1) is a monovalent organic group, unless the objective of invention is impaired, it can set suitably.
  • the “monovalent organic group” means that at least one carbon atom is present in the substituent R existing at the 6-position of the triazine ring skeleton. That is, the linkage between the 6-position carbon of the triazine skeleton and the substituent R is not necessarily limited to a carbon-carbon bond, but is a bond between carbon and another heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom. It doesn't matter.
  • the number of carbon atoms contained in the substituent R is preferably 2 or more, and more preferably 3 or more.
  • Substituent R is carbon atom (C), hydrogen atom (H), nitrogen atom (N), oxygen atom (O), sulfur atom (S), silicon atom (Si), germanium atom (Ge), etc.
  • a halogen atom such as a fluorine atom (F), a chlorine atom (Cl), a bromine atom (Br), or an iodine atom (I) can also be employed.
  • the substituent R may have a bonding group such as an ether bond, an ester bond, an amide bond, a urethane bond, a sulfide bond, or a thioester bond in the substituent, and a phenyl group, a naphthyl group, or the like.
  • Aromatic substituents aromatic substituents containing heteroatoms such as pyrrole, pyridine, thiophene, furan, indole, cycloaliphatic substituents such as cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. Also good.
  • the (D) diaminotriazine compound represented by the general formula (1) has one or more groups having an active hydrogen atom selected from an alcoholic hydroxyl group, a phenolic hydroxyl group and a carboxyl group in the substituent R. preferable.
  • the substituent R contains such a group having an active hydrogen atom in the substituent, the compatibility between the (D) diaminotriazine compound and other components in the sealing resin composition can be further improved. it can.
  • the number of groups having an active hydrogen atom in one molecule of the diaminotriazine compound can be appropriately set.
  • the lower limit is 1 or more
  • the upper limit is, for example, 10 or less, preferably 5 It is as follows.
  • the molecular weight of the (D) diaminotriazine compound can be set as appropriate, but the lower limit thereof is, for example, 135 or more, preferably 150 or more, more preferably 180 or more. Moreover, as an upper limit of the molecular weight of this compound, it is 600 or less, for example, Preferably it is 500 or less, More preferably, it is 400 or less. By setting to such a range, a desired effect can be efficiently expressed.
  • Examples of the (D) diaminotriazine compound preferably used in the present embodiment include the following compound groups.
  • the content of the diaminotriazine compound with respect to the entire sealing resin composition is not particularly limited, but the lower limit is preferably 0.01% by mass or more, and more preferably 0.03% by mass or more.
  • the lower limit is preferably 0.01% by mass or more, and more preferably 0.03% by mass or more.
  • As an upper limit of content of a diamino triazine compound 1.0 mass% or less is preferable, 0.5 mass% or less is more preferable, 0.2 mass% or less is especially preferable.
  • liquidity etc. can be exhibited by making content of a diamino triazine compound below the said upper limit.
  • the resin composition for sealing may further contain (E) a coupling agent.
  • a coupling agent is a component which connects (A) epoxy resin etc. which are resin components, and (C) inorganic filler.
  • Examples of the coupling agent (E) include silane coupling agents such as epoxy silane, aminosilane, mercaptosilane (a silane coupling agent having a mercapto group) (E1). These (E) coupling agents may be used individually by 1 type, or may use 2 or more types together.
  • epoxy silane examples include ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (3,4 epoxycyclohexyl) ethyltrimethoxysilane, and the like.
  • aminosilanes include ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane (sometimes referred to as anilinosilane), and the like.
  • Examples of mercaptosilane (E1) include ⁇ -mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane.
  • the mercaptosilane includes compounds that exhibit similar functions by thermal decomposition, such as bis (3-triethoxysilylpropyl) tetrasulfide and bis (3-triethoxysilylpropyl) disulfide.
  • epoxysilane, anilinosilane, mercaptosilane (E1), or a combination thereof it is preferable to use epoxysilane, anilinosilane, mercaptosilane (E1), or a combination thereof.
  • Anilinosilane is effective in improving fluidity, and mercaptosilane (E1) can improve adhesion, but according to the sealing resin composition of this embodiment, it contains a specific triazine compound. Therefore, it is possible to achieve both high-temperature storage characteristics and high adhesion to metal, which are even better than when the above-described mercaptosilane is used.
  • the content of the coupling agent relative to the entire resin composition is not particularly limited, but the lower limit is preferably 0.01% by mass or more, and more preferably 0.05% by mass or more. As an upper limit, 1 mass% or less is preferable, and 0.5 mass% or less is more preferable. (E) By making content of a coupling agent into the said range, the function of (E) coupling agent can be expressed effectively.
  • the lower limit of the content of the mercaptosilane is preferably 0.01% by mass or more, and more preferably 0.02% by mass or more. .
  • the content of mercaptosilane (E1) is preferably 0.01% by mass or more, and more preferably 0.02% by mass or more.
  • the adhesion can be effectively increased.
  • As an upper limit of content of mercaptosilane (E1) 0.1 mass% or less is preferable, and 0.07 mass% or less is more preferable. By setting the content of mercaptosilane (E1) to the upper limit value or less, it is possible to achieve both excellent high-temperature storage characteristics and high adhesion to metal.
  • the sealing resin composition of the present embodiment may further contain (F) a curing accelerator.
  • a hardening accelerator is a component which has a function which accelerates
  • phosphorus atom-containing compounds such as organic phosphines, tetra-substituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, adducts of phosphonium compounds and silane compounds; -Amidines and tertiary amines such as diazabicyclo (5,4,0) undecene-7, benzyldimethylamine, 2-methylimidazole, and further nitrogen atom-containing compounds such as the quaternary salts of the amidines and amines. These can be used alone or in combination of two or more.
  • phosphorus atom-containing compounds are preferred from the viewpoints of curability and adhesion. Furthermore, from the viewpoint of solder resistance, fluidity, etc., an adduct of a phosphobetaine compound, a phosphine compound and a quinone compound is particularly preferable. From the point of slight contamination of the mold in continuous molding, tetra substitution Particularly preferred are phosphorus atom-containing compounds such as phosphonium compounds and adducts of phosphonium compounds and silane compounds.
  • organic phosphine examples include a first phosphine such as ethylphosphine and phenylphosphine; a second phosphine such as dimethylphosphine and diphenylphosphine; a third phosphine such as trimethylphosphine, triethylphosphine, tributylphosphine, and triphenylphosphine. it can.
  • Tetra-substituted phosphonium compound examples include a compound represented by the following formula (6).
  • P is a phosphorus atom.
  • R 8 , R 9 , R 10 and R 11 are an aromatic group or an alkyl group.
  • [A] — is an anion of an aromatic organic acid having at least one functional group selected from a hydroxy group, a carboxy group and a thiol group in the aromatic ring.
  • AH is an aromatic organic acid having at least one functional group selected from a hydroxy group, a carboxy group, and a thiol group in an aromatic ring.
  • x and y are numbers 1 to 3
  • z is a number 0 to 3
  • x y.
  • the compound represented by the formula (6) is obtained, for example, as follows, but is not limited thereto. First, a tetra-substituted phosphonium halide, an aromatic organic acid and a base are mixed in an organic solvent and mixed uniformly to generate an aromatic organic acid anion in the solution system. Subsequently, when water is added, the compound represented by Formula (6) can be precipitated.
  • R 8 , R 9 , R 10 and R 11 bonded to the phosphorus atom are phenyl groups
  • AH is a compound having a hydroxy group in an aromatic ring, that is, phenols.
  • [A] ⁇ is preferably an anion of the phenol.
  • Phenols include monocyclic phenols such as phenol, cresol, resorcin, and catechol, condensed polycyclic phenols such as naphthol, dihydroxynaphthalene, and anthraquinol, bisphenols such as bisphenol A, bisphenol F, and bisphenol S, and phenyl Examples thereof include polycyclic phenols such as phenol and biphenol.
  • P is a phosphorus atom.
  • R 12 is an alkyl group having 1 to 3 carbon atoms.
  • R 13 is a hydroxy group.
  • k is an integer of 0 to 5.
  • m is an integer of 0 to 3.
  • the compound represented by the formula (7) is obtained as follows, for example.
  • a triaromatic substituted phosphine that is a third phosphine and a diazonium salt are brought into contact with each other, and the triaromatic substituted phosphine and the diazonium group of the diazonium salt are substituted.
  • the present invention is not limited to this.
  • adduct of phosphine compound and quinone compound examples include a compound represented by the following formula (8).
  • P is a phosphorus atom.
  • R 14 , R 15 and R 16 are each independently an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • R 17 , R 18 and R 19 are each independently a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R 18 and R 19 may be bonded to form a cyclic structure.
  • Examples of the phosphine compound used as an adduct of a phosphine compound and a quinone compound include an aromatic ring such as triphenylphosphine, tris (alkylphenyl) phosphine, tris (alkoxyphenyl) phosphine, trinaphthylphosphine, and tris (benzyl) phosphine.
  • aromatic ring such as triphenylphosphine, tris (alkylphenyl) phosphine, tris (alkoxyphenyl) phosphine, trinaphthylphosphine, and tris (benzyl) phosphine.
  • Those having a substituent or a substituent such as an alkyl group or an alkoxyl group are preferred.
  • Examples of the substituent such as an alkyl group and an alkoxyl group include those having 1 to 6 carbon atoms. From the viewpoint of availability, tripheny
  • Examples of the quinone compound used in the adduct of the phosphine compound and the quinone compound include benzoquinone and anthraquinones. Among these, p-benzoquinone is preferable from the viewpoint of storage stability.
  • an adduct can be obtained by contacting and mixing them in a solvent in which both an organic tertiary phosphine and a benzoquinone can be dissolved. it can.
  • the solvent is preferably a ketone such as acetone or methyl ethyl ketone, which has low solubility in the adduct. However, it is not limited to this.
  • R 14 , R 15 and R 16 bonded to the phosphorus atom are phenyl groups, and R 17 , R 18 and R 19 are hydrogen atoms, that is, 1, 4 -A compound in which benzoquinone and triphenylphosphine are added is preferable in that it reduces the thermal elastic modulus of the cured product of the resin composition.
  • P is a phosphorus atom and Si is a silicon atom.
  • R 20 , R 21 , R 22 and R 23 are each independently an organic group having an aromatic ring or a heterocyclic ring, or an aliphatic group.
  • R 24 is an organic group bonded to the groups Y 2 and Y 3 .
  • R 25 is an organic group bonded to the groups Y 4 and Y 5 .
  • Y 2 and Y 3 are groups formed by releasing a proton from a proton donating group, and groups Y 2 and Y 3 in the same molecule are bonded to a silicon atom to form a chelate structure.
  • Y 4 and Y 5 represent a group formed by releasing a proton from a proton donating group, and groups Y 4 and Y 5 in the same molecule are bonded to a silicon atom to form a chelate structure.
  • R 24 and R 25 may be the same or different, and Y 2 , Y 3 , Y 4 and Y 5 may be the same or different from each other.
  • Z 1 is an organic group having an aromatic ring or a heterocyclic ring, or an aliphatic group.
  • R 20 , R 21 , R 22 and R 23 are, for example, phenyl group, methylphenyl group, methoxyphenyl group, hydroxyphenyl group, naphthyl group, hydroxynaphthyl group, benzyl group, methyl group, ethyl group, n-butyl. Group, n-octyl group, cyclohexyl group and the like.
  • alkyl groups such as phenyl group, methylphenyl group, methoxyphenyl group, hydroxyphenyl group and hydroxynaphthyl group, aromatic groups having substituents such as alkoxy groups and hydroxy groups, or unsubstituted aromatic groups are preferable. .
  • the groups represented by —Y 2 —R 24 —Y 3 — and Y 4 —R 25 —Y 5 — in the formula (9) are constituted by groups in which the proton donor releases two protons. It is what is done.
  • the proton donor is preferably an organic acid having at least two carboxy groups or hydroxy groups in the molecule. Furthermore, an aromatic compound having at least two carboxy groups or hydroxy groups respectively connected to adjacent carbons constituting one aromatic ring is preferred, and hydroxy groups respectively connected to adjacent carbons constituting one aromatic ring. An aromatic compound having at least two is more preferable.
  • proton donors examples include catechol, pyrogallol, 1,2-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,2′-biphenol, 1,1′-bi-2-naphthol, salicylic acid, 1 -Hydroxy-2-naphthoic acid, 3-hydroxy-2-naphthoic acid, chloranilic acid, tannic acid, 2-hydroxybenzyl alcohol, 1,2-cyclohexanediol, 1,2-propanediol, glycerin and the like.
  • catechol, 1,2-dihydroxynaphthalene, and 2,3-dihydroxynaphthalene are more preferable.
  • Examples of the organic group having an aromatic ring or heterocyclic ring represented by Z 1 in formula (9) or an aliphatic group include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, and an octyl group.
  • Examples thereof include reactive substituents such as alkyl groups and vinyl groups. Among these, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and a biphenyl group are preferable from the viewpoint of thermal stability.
  • Examples of a method for producing an adduct of a phosphonium compound and a silane compound include the following methods. First, a silane compound such as phenyltrimethoxysilane and a proton donor such as 2,3-dihydroxynaphthalene are added and dissolved in a flask containing methanol, and then a sodium methoxide-methanol solution is added dropwise with stirring at room temperature. Further, when a methanol solution of tetra-substituted phosphonium halide such as tetraphenylphosphonium bromide prepared in advance is added dropwise with stirring at room temperature, crystals are deposited. The precipitated crystals are filtered, washed with water, and vacuum dried to obtain an adduct of a phosphonium compound and a silane compound. However, it is not limited to this.
  • Examples of the (F) curing accelerator include compounds represented by the above formulas (6) to (9).
  • a tetra-substituted phosphonium compound for example, a formula The compound represented by (6)
  • an adduct of a phosphine compound and a quinone compound for example, a compound represented by formula (8)
  • an adduct of a phosphine compound and a quinone compound is more preferred.
  • the content of the curing accelerator in the entire sealing resin composition is not particularly limited, but the lower limit is preferably 0.1% by mass or more, and more preferably 0.2% by mass or more.
  • Sufficient curability etc. can be obtained by making content of a hardening accelerator more than the said lower limit.
  • As an upper limit of content of a hardening accelerator 1 mass% or less is preferable, and 0.5 mass% or less is more preferable.
  • liquidity etc. can be obtained by making content of a hardening accelerator into the said upper limit or less.
  • the sealing resin composition may further contain other components as necessary.
  • other components include a colorant, an ion scavenger, a release agent, a low stress component, and a flame retardant.
  • the colorant include carbon black and bengara.
  • the ion scavenger include hydrotalcite.
  • An ion scavenger may be used as a neutralizing agent.
  • the mold release agent include natural waxes such as carnauba wax, synthetic waxes, higher fatty acids such as zinc stearate, metal salts thereof, paraffin, and the like.
  • the low stress component include silicone oil and silicone rubber.
  • the flame retardant include aluminum hydroxide, magnesium hydroxide, zinc borate, zinc molybdate, and phosphazene.
  • the sealing resin composition of the present embodiment can be prepared, for example, by the following method. First, the above-described components are uniformly mixed at room temperature using a mixer or the like, and then melt-kneaded using a kneader such as a heating roll, a kneader, or an extruder as necessary. Subsequently, if necessary, the obtained kneaded product is cooled and pulverized, and adjusted to a desired degree of dispersion, fluidity, and the like to obtain a sealing resin composition.
  • the sealing resin composition of the present embodiment can be used as a powder composition, as well as a varnish using an organic solvent or a liquid composition using a liquid epoxy resin. When a solvent is included, the content of each component is converted to solid content.
  • FIG. 1 is a cross-sectional view showing a semiconductor device 100 according to the present embodiment.
  • the semiconductor device 100 of this embodiment includes a semiconductor element 20, a bonding wire 40 connected to the semiconductor element 20, and a sealing resin 50.
  • the sealing resin 50 is used for the above-described sealing. It is comprised by the hardened
  • the semiconductor element 20 to be sealed is, for example, a component (element) that outputs in response to power input.
  • the semiconductor element 20 is an integrated circuit, a large-scale integrated circuit, a transistor, a thyristor, a diode, or a solid development element. Other elements can be mentioned.
  • the bonding wire 40 can be set while taking into consideration the semiconductor element 20 and the like to be used. For example, a copper bonding wire can be used.
  • Examples of the semiconductor device 100 include a dual in-line package (DIP), a chip carrier with plastic lead (PLCC), a quad flat package (QFP), and a low profile quad flat package (LQFP). ), Small Outline Package (SOP), Small Outline J Lead Package (SOJ), Thin Small Outline Package (TSOP), Thin Quad Flat Package (TQFP), Tape Carrier Package (TCP) ), Ball grid array (BGA), chip size package (CSP), etc., but are not limited thereto.
  • DIP dual in-line package
  • PLCC chip carrier with plastic lead
  • QFP quad flat package
  • LQFP low profile quad flat package
  • SOP Small Outline Package
  • SOJ Small Outline J Lead Package
  • TSOP Thin Small Outline Package
  • TQFP Thin Quad Flat Package
  • TCP Tape Carrier Package
  • BGA Ball grid array
  • CSP chip size package
  • the semiconductor device 100 uses the die attach material 10 to fix the semiconductor element 20 on the die pad 32 (substrate 30), and connects the die pad 32 (base material 30), which is a lead frame, with the bonding wires 40.
  • This structure (sealed object) is manufactured by sealing with a sealing resin composition.
  • the sealing resin composition is molded and cured by a molding method such as a transfer mold, a compression mold, or an injection mold. Can be performed.
  • the resin composition for sealing is cured for about 10 minutes to 10 hours at a temperature of about 80 ° C. to 200 ° C. Installed in equipment.
  • the semiconductor device 100 uses the above-described sealing resin composition as the sealing resin 50, and the adhesiveness between the sealing resin 50 and the semiconductor element 20, the bonding wire 40, the electrode pad 22, and the like is sufficient. Excellent in high temperature storage characteristics. In particular, even when a copper wire is used as the bonding wire 40, sufficient high-temperature storage characteristics and the like can be exhibited.
  • Epoxy resin / epoxy resin 1 biphenyl type epoxy resin (trade name YX4000K manufactured by Mitsubishi Chemical Corporation)
  • Epoxy resin 2 biphenyl aralkyl type epoxy resin (trade name NC-3000, manufactured by Nippon Kayaku Co., Ltd.)
  • Epoxy resin 3 phenol aralkyl type epoxy resin (trade name NC-2000 manufactured by Nippon Kayaku Co., Ltd.)
  • (B) Curing Agent / Phenolic Resin Curing Agent 1 A phenol aralkyl resin having a biphenylene skeleton having a hydroxyl equivalent of 198 g / eq and a softening point of 64.5 ° C. (trade name “GPH-65” manufactured by Nippon Kayaku Co., Ltd.) ).
  • R 47 has a structure of 4,4′-dimethylenebiphenyl.
  • Phenol resin curing agent 2 A phenol resin having a trisphenol methane skeleton having a hydroxyl group equivalent of 97 g / eq and a softening point of 110 ° C. (product name “MEH-7500” manufactured by Meiwa Kasei Co., Ltd.).
  • R 47 has a structure of hydroxyphenylmethylene.
  • Phenolic resin curing agent 3 Phenol novolak resin (trade name PR-HF-3, manufactured by Sumitomo Bakelite Co., Ltd.)
  • Inorganic filler / inorganic filler 1 spherical fused silica with an average particle size of 30 ⁇ m and specific surface area of 1.7 m 2 / g 2: inorganic filler 2: average particle size of 0.5 ⁇ m, specific surface area of 5.9 m 2 / g Spherical fused silica
  • Diaminotriazine compound / Compound 1 Diaminotriazine compound represented by the following formula (1a) (2,4-diamino-6- (4,5-dihydroxypentyl) -1,3,5-triazine)
  • reaction solution was concentrated, dissolved in 200 ml of ethyl acetate, and washed with water.
  • the ethyl acetate solution of the reaction product was transferred to a flask, and 1 g of palladium carbon was added.
  • the reaction system was replaced with hydrogen, and the mixture was stirred for 12 hours while supplying hydrogen from the balloon filled with hydrogen into the flask.
  • the reaction solution was concentrated by filtration and recrystallized with a mixed solvent of hexane / ethyl acetate. The precipitated crystals were filtered and dried under reduced pressure to obtain Compound 1.
  • the reaction system was replaced with hydrogen, and the mixture was stirred for 12 hours while supplying hydrogen from the balloon filled with hydrogen into the flask.
  • the reaction solution was concentrated by filtration, recrystallized with a mixed solvent of hexane / ethyl acetate, and the precipitated crystals were filtered and dried under reduced pressure to obtain Compound 3.
  • Compound 4 a diaminotriazine compound represented by the following formula (1d) (product name VD-3 (manufactured by Shikoku Kasei Co., Ltd., where R is a linking group connecting the diol moiety and the triazine ring moiety))
  • Coupling agent / coupling agent 1 ⁇ -mercaptopropyltrimethoxysilane
  • Coupling agent 2 N-phenyl- ⁇ -aminopropyltrimethoxysilane
  • Curing accelerator 2 Tetra-substituted phosphonium compound represented by the following formula (13) synthesized by the following method
  • Curing accelerator 3 Tetra-substituted phosphonium compound represented by the following formula (14) synthesized by the following method (Synthesis of curing accelerator 3) A separable flask equipped with a condenser and a stirrer was charged with 12.81 g (0.080 mol) of 2,3-dihydroxynaphthalene, 16.77 g (0.040 mol) of tetraphenylphosphonium bromide and 100 ml of methanol, and dissolved uniformly. It was. When a sodium hydroxide solution prepared by previously dissolving 1.60 g (0.04 ml) of sodium hydroxide in 10 ml of methanol was gradually dropped into the flask, crystals were deposited. The precipitated crystals were filtered, washed with water, and vacuum-dried to obtain a curing accelerator 3.
  • Synthesis of curing accelerator 3 A separable flask equipped with a condenser and a stirrer was charged with 12.81 g (0.080
  • Curing accelerator 4 Tetra-substituted phosphonium compound represented by the following formula (15) synthesized by the following method (Synthesis of curing accelerator 4) In a separable flask equipped with a condenser and a stirrer, 12.81 g (0.080 mol) of 2,3-dihydroxynaphthalene, 7.92 g (0.04 mol) of trimethoxyphenylsilane, 16.77 g (0.040 mol) of tetraphenylphosphonium bromide ) And 100 ml of methanol were stirred and dissolved uniformly.
  • Coloring agent Carbon black / Ion scavenger: Hydrotalcite (DHT-4H manufactured by Kyowa Chemical Co., Ltd.)
  • Release agent Carnauba wax (Nikko Carnaba manufactured by Nikko Fine Products)
  • Epoxy resin 1 (5.80 parts by mass), phenol resin-based curing agent 1 (5.50 parts by mass), inorganic filler 1 (77.50 parts by mass), inorganic filler 2 (10.00 parts by mass), compound 1 (0.05 parts by mass), coupling agent 2 (0.20 parts by mass), curing accelerator 1 (0.25 parts by mass), colorant (0.40 parts by mass), ion scavenger (0.10) Parts by weight) and a release agent (0.20 parts by weight) were mixed at room temperature using a mixer, and then roll kneaded at 70 to 100 ° C. Subsequently, after cooling, it was pulverized to obtain a sealing resin composition of Example 1.
  • TEG Telement Group
  • 352 pin BGA substrate is 0.56 mm thick, bismaleimide / triazine resin / glass cloth substrate, package The size was mounted on 30 mm ⁇ 30 mm, thickness 1.17 mm). Subsequently, wire bonding was performed on the electrode pad with a wire pitch of 80 ⁇ m using a copper wire (copper purity 99.99 mass%, diameter 25 ⁇ m).
  • the obtained structure was subjected to each of the obtained conditions under conditions of a mold temperature of 175 ° C., an injection pressure of 6.9 MPa, and a curing time of 2 minutes. Sealing molding was performed using the sealing resin compositions of Examples and Comparative Examples to produce a 352-pin BGA package. Thereafter, the obtained BGA package was post-cured at 175 ° C. for 4 hours to obtain a semiconductor device (electronic component device).
  • Adhesion The adhesion to each metal (Ag, Cu, PPF (pre-plating frame), Ni) was evaluated by the following method. On the board
  • the obtained semiconductor device was subjected to HTSL (high temperature storage test) by the following method.
  • Each semiconductor device was stored under conditions of a temperature of 200 ° C. and 1000 hours.
  • the electrical resistance value between the wire and the electrode pad was measured.
  • a semiconductor device whose average value shows an electrical resistance value of less than 110% with respect to the average value of the initial resistance value is ⁇
  • a semiconductor device whose electrical resistance value is 110% or more and 120% or less is good, and is larger than 120%
  • Those showing electrical resistance values were marked with x.
  • each of the sealing resin compositions of Examples has sufficient adhesion, and the obtained electronic component device (semiconductor device) has excellent high-temperature storage characteristics.
  • Comparative Example 1-3 containing no diaminotriazine compound was difficult to achieve both adhesion and high-temperature storage characteristics.
  • Comparative Example 1 in which 3-amino-5-mercapto-1,2,4-triazole was used instead of the diaminotriazine compound resulted in poor high temperature storage.
  • Comparative Example 2-3 the high temperature storage property was relatively excellent, but the adhesion to metal was inferior.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Wire Bonding (AREA)

Abstract

L'invention concerne une composition de résine pour scellement qui peut être moulée autour d'un élément semi-conducteur, cette composition de résine pour scellement comprenant une résine époxy (A), un agent de traitement (B), une matière de charge inorganique (C) et un composé diaminotriazine (D) représenté par la formule générale (1) ci-dessous. Dans la formule, R est un groupe organique monovalent.
PCT/JP2015/065723 2014-07-16 2015-06-01 Composition de résine pour scellement et dispositif à semi-conducteur WO2016009730A1 (fr)

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JP2019006972A (ja) * 2017-06-23 2019-01-17 住友ベークライト株式会社 封止用樹脂組成物の製造方法及び電子装置の製造方法

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CN111032779A (zh) * 2017-08-14 2020-04-17 日立化成株式会社 密封用树脂组合物、半导体装置及半导体装置的制造方法
JP7329320B2 (ja) * 2018-11-01 2023-08-18 株式会社ダイセル 硬化性エポキシ樹脂組成物
JP7341828B2 (ja) * 2019-09-30 2023-09-11 太陽ホールディングス株式会社 硬化性樹脂組成物、ドライフィルム、樹脂付き銅箔、硬化物、及び電子部品
JPWO2021220726A1 (fr) * 2020-04-30 2021-11-04

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KR102166100B1 (ko) 2020-10-15
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