WO2019111707A1 - Composition de résine époxy et dispositif à composants électroniques - Google Patents

Composition de résine époxy et dispositif à composants électroniques Download PDF

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Publication number
WO2019111707A1
WO2019111707A1 PCT/JP2018/042951 JP2018042951W WO2019111707A1 WO 2019111707 A1 WO2019111707 A1 WO 2019111707A1 JP 2018042951 W JP2018042951 W JP 2018042951W WO 2019111707 A1 WO2019111707 A1 WO 2019111707A1
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epoxy resin
resin composition
chlorine
atm
containing particles
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PCT/JP2018/042951
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English (en)
Japanese (ja)
Inventor
和田　雅浩
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住友ベークライト株式会社
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Priority to KR1020207018977A priority Critical patent/KR102244206B1/ko
Priority to CN201880079022.8A priority patent/CN111433284B/zh
Priority to JP2019558122A priority patent/JP6677360B2/ja
Publication of WO2019111707A1 publication Critical patent/WO2019111707A1/fr

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    • 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
    • C08K5/02—Halogenated hydrocarbons
    • 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
    • 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
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/095—Carboxylic acids containing halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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
    • C08K5/54—Silicon-containing compounds
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers

Definitions

  • the present invention relates to an epoxy resin composition and an electronic device.
  • Patent Document 1 describes that an epoxy compound produced by a method not using epichlorohydrin (epichlorohydrin) as a raw material is used to reduce the content of hydrolyzable chlorine derived from the raw material ( Paragraph 0012 of Patent Document 1).
  • the inventors further studied and found that the properties of the epoxy resin composition can be modified by appropriately controlling the state of the chlorine contained in the epoxy resin composition.
  • metal adhesion in an epoxy resin composition can be improved by incorporating chlorine-containing particles containing an organic substance in the epoxy resin composition, and the present invention is completed. It came to Although the detailed mechanism is not clear, the chlorine-containing particles have an oxidizing action on a metal such as Cu, and the oxidation action modifies the surface of the metal to improve the affinity to the epoxy resin composition, It is believed that metal adhesion is improved.
  • An epoxy resin composition comprising an epoxy resin, a curing agent and an inorganic filler, An epoxy resin composition is provided which comprises organic containing chlorine containing particles.
  • an electronic device comprising a cured product of the above epoxy resin composition.
  • FIG. 2 is a cross-sectional view showing an example of a semiconductor device.
  • FIG. 2 is a cross-sectional view showing an example of a semiconductor device. It is a sectional view showing an example of a structure.
  • Epoxy resin composition The epoxy resin composition of the present embodiment can include an epoxy resin, a curing agent and an inorganic filler. This epoxy resin composition contains chlorine-containing particles containing an organic substance.
  • chlorine-containing particles containing organic matter hereinafter sometimes simply referred to as “chlorine-containing particles”. It has been found that the chlorine of the chlorine-containing particles is different from the hydrolyzable chlorine and the chlorine derived from free chlorine in the form of presence, and is present locally to the epoxy resin composition, in the particles. It becomes high concentration.
  • chlorine-containing particles can be confirmed significantly by, for example, element mapping of energy dispersive X-ray spectroscopy (EDX).
  • EDX energy dispersive X-ray spectroscopy
  • the surface of the metal is modified to have an affinity with the epoxy resin composition. It is thought that it can improve and the metal adhesiveness in an epoxy resin composition can be improved. Therefore, the metal adhesiveness in an epoxy resin composition can be improved by containing chlorine containing particle
  • the chlorine-containing particles are obtained by mixing the epoxy resin composition in acetone to obtain a solution, and filtering the obtained solution through a filter with an opening size of 75 ⁇ m, and contained in the residue on the filter It can be
  • chlorine-containing particles can be detected by the following inspection method (hereinafter sometimes referred to as inspection method of chlorine-containing particles).
  • a raw material component for example, an epoxy resin, a curing agent, an inorganic filler, etc.
  • an epoxy resin composition one obtained by mixing and kneading each raw material component and cooling the obtained kneaded product (epoxy resin composition in a B-stage state) is used.
  • the epoxy resin composition one obtained by mixing and kneading each raw material component and cooling the obtained kneaded product (epoxy resin composition in a B-stage state) is used.
  • the acetone to be used uses what was filtered by the filter of 12 micrometers of mesh sizes.
  • the filter used is a nylon filter with an opening size of 75 ⁇ m, which has been subjected to ultrasonic cleaning.
  • (4) The container shaken in (2) was allowed to stand, and then the solution in the container was poured from the top of the funnel of (3) and suction filtered through a filter. If the particle size of the filler such as the inorganic filler contained in the sample is larger than the pore size of the filter, the supernatant in the solution may be filtered by a filter.
  • the inspection method of the above-mentioned chlorine content particles is a method of detecting stably chlorine content particles contained in an epoxy resin composition or its raw material component, and chlorine contained in the particles concerned, and the present invention It is a method newly established by the inspection method of the above-mentioned chlorine content particles.
  • the organic substance in the above-mentioned chlorine-containing particles contained in the epoxy resin can include one or more selected from the group consisting of carbonates, amide compounds, and silicates. These organic substances may be a mixture with an epoxy resin.
  • the organic substance in the above-mentioned chlorine-containing particles contained in the epoxy resin composition can contain one or more selected from the group consisting of cellulose, polyethylene terephthalate, polypropylene, silk, a silicone compound, and an amide compound. These may be used alone or in combination of two or more. Or it may be a mixture of these.
  • the above-mentioned chlorine-containing particles may contain organic substances other than these. Organic substances can be identified from the spectrum results of chlorine-containing particles using FT-IR (Fourier transform infrared spectroscopy).
  • the lower limit value of the chlorine concentration in the chlorine-containing particles is, for example, 0.01 Atm% or more, and may be 0.5 Atm% or more, or 0.1 Atm% or more. Thereby, metal adhesiveness can be improved.
  • the upper limit of the chlorine concentration in the chlorine-containing particles is, for example, 20 Atm% or less, preferably 10 Atm% or less, and more preferably 7 Atm% or less. This can improve the reliability.
  • the lower limit value of the carbon concentration in the chlorine-containing particles is, for example, 40 Atm% or more, preferably 50 Atm% or more, and more preferably 60 Atm% or more. This makes it possible to stably fix chlorine in the chlorine-containing particles.
  • the upper limit value of the carbon concentration in the above-mentioned chlorine-containing particles may be appropriately changed depending on other constituent components and is not particularly limited, but may be 99 Atm% or less, 90 Atm% or less, or 85 Atm% or less It may be 70 Atm% or less.
  • the chlorine-containing particles may contain an oxygen component.
  • the oxygen concentration in the chlorine-containing particles may be, for example, 1 Atm% to 50 Atm%, 2 Atm% to 35 Atm%, 3 Atm% to 30 Atm%, or 3 Atm% to 28 Atm%. “ ⁇ ” indicates including upper limit value and lower limit value unless otherwise specified.
  • the chlorine-containing particles contain one or more selected from the group consisting of Al element, Mg element, Si element, Fe element, Zn element, Ti element, Ca element, Na element, K element, S element, carbonate compound be able to. These may be used alone or in combination of two or more.
  • the Al concentration in the chlorine-containing particles may be 0.1 Atm% to 4 Atm%, or 0.1 Atm% to 1.0 Atm%.
  • the Mg concentration in the chlorine-containing particles may be 0.1 Atm% to 0.5 Atm%, or 0.1 Atm% to 0.4 Atm%.
  • the Si concentration in the chlorine-containing particles may be 0.1 Atm% to 5 Atm%, 0.1 Atm% to 2.0 Atm%, or 0.1 Atm% to 1 Atm%.
  • the Fe concentration in the chlorine-containing particles may be 0.1 Atm% to 4 Atm%, or may be 0.1 Atm% to 2.0 Atm%.
  • the Zn concentration in the chlorine-containing particles may be 0.1 Atm% to 5 Atm%, or may be 0.1 Atm% to 1.0 Atm%.
  • the Ti concentration in the chlorine-containing particles may be 0.01 Atm% to 1.0 Atm%, or may be 0.04 Atm% to 0.8 Atm%.
  • the Ca concentration in the chlorine-containing particles may be 0.01 Atm% to 17 Atm%, may be 0.02 Atm% to 6 Atm%, and may be 0.1 Atm% to 3 Atm%.
  • the concentration of Na in the chlorine-containing particles may be 0.01 Atm% to 2 Atm%, or 0.1 Atm% to 1.5 Atm%.
  • the K concentration in the chlorine-containing particles may be 0.01 Atm% to 5 Atm%, or 0.1 Atm% to 1.0 Atm%.
  • the S concentration in the chlorine-containing particles may be 0.01 Atm% to 2 Atm%, or may be 0.02 Atm% to 1.0 Atm%.
  • 1 type or more may be sufficient, 2 types or more may be sufficient, or 5 or more types of other elements may be contained.
  • the elemental composition and the elemental concentration in the chlorine-containing particles can be measured based on energy dispersive X-ray spectroscopy (EDX).
  • EDX energy dispersive X-ray spectroscopy
  • the number of chlorine-containing particles in the epoxy resin composition or the number of chlorine-containing particles in the epoxy resin can be measured by using the above-mentioned ⁇ Method for inspecting chlorine-containing particles>.
  • the number of chlorine-containing particles in the 50 g of the epoxy resin composition can be one or more.
  • the number of chlorine-containing particles in the epoxy resin composition may be, for example, 10 or less, 5 or less, 3 or less, or 2 or less. Thereby, when an epoxy resin composition is used as a sealing material which seals electronic parts, reliability can be improved. Regarding each component used for the above epoxy resin composition, for example, in 50 g of epoxy resin, the number of chlorine-containing particles may be 1 to 5 or less, 1 to 3 or less, or 1 to 2 or less. , May be one.
  • thermosetting resin composition for example, types, blending amounts, preparation methods of each component contained in the thermosetting resin composition (production method or purification method after production), preparation method of the thermosetting resin composition, etc. are appropriately made.
  • each component such as an epoxy resin and a curing agent
  • filtering a liquid substance such as a solution dissolved in an organic solvent with a filter, and in that case using the filter with a small opening size
  • the liquid is centrifuged to remove the lower layer containing foreign matter, and only the upper layer is used, or the HCL generated during the reaction is thoroughly removed to eradicate the chlorine source.
  • Inorganic filler, reducing the size of the guarantee screen, selecting appropriate ones from a plurality of lots, and the like can be mentioned as factors for setting the amount of the above-mentioned chlorine-containing particles in the desired numerical range.
  • the epoxy resin composition contains an epoxy resin.
  • the epoxy resin is generally a monomer, an oligomer or a polymer having two or more epoxy groups in one molecule, and the molecular weight and molecular structure thereof are not particularly limited.
  • the epoxy resin include bifunctional or crystalline epoxy resins such as biphenyl type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, stilbene type epoxy resin, hydroquinone type epoxy resin; cresol novolac type epoxy resin Novolak type epoxy resin such as phenol novolac type epoxy resin and naphthol novolac type epoxy resin; Phenol aralkyl type such as phenylene skeleton containing phenol aralkyl type epoxy resin, biphenylene skeleton containing phenol aralkyl type epoxy resin, phenylene skeleton containing naphthol aralkyl type epoxy resin Epoxy resin; Trifunctional epoxy resin such as triphenolmethane epoxy resin and alkyl-modified triphenolmethane epoxy resin
  • the lower limit of the content of the epoxy resin in the epoxy resin composition is, for example, preferably 8% by mass or more, and more preferably 10% by mass or more based on the total solid content of the epoxy resin composition. And 12% by mass or more is particularly preferable.
  • the upper limit value of the content of the epoxy resin is, for example, preferably 30% by mass or less, and more preferably 20% by mass or less, based on the total solid content of the epoxy resin composition.
  • the total solid content of the epoxy resin composition refers to the non-volatile content in the epoxy resin composition, and refers to the remainder excluding volatile components such as water and solvent.
  • the content with respect to the entire epoxy resin composition refers to the content with respect to the entire solid content excluding the solvent in the resin composition when the solvent is included.
  • the epoxy resin composition can include a curing agent.
  • the curing agent is not particularly limited as long as it is generally used in epoxy resin compositions, but, for example, a phenol resin curing agent, an amine curing agent, an acid anhydride curing agent, a mercaptan curing agent, etc. , Is mentioned. Among these, from the viewpoint of balance such as flame resistance, moisture resistance, electric properties, curability, storage stability, etc., a phenol resin-based curing agent is preferable.
  • the phenolic resin-based curing agent is not particularly limited as long as it is generally used in epoxy resin compositions, and examples thereof include phenol novolac resin, phenol including cresol novolac resin, cresol, resorcinol, catechol, Novolak resin obtained by condensation or cocondensation of phenols such as bisphenol A, bisphenol F, phenylphenol, aminophenol, ⁇ -naphthol, ⁇ -naphthol, dihydroxynaphthalene and formaldehyde or ketones under an acid catalyst, as described above
  • a phenol aralkyl resin such as a phenol aralkyl resin having a phenylene skeleton synthesized from phenols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl and a phenol aralkyl resin having a biphenylene skeleton Lukil resin, a phenol resin having a trisphenylmethane ske
  • amine-based curing agent examples include aliphatic polyamines such as diethylenetriamine (DETA), triethylenetetramine (TETA) and metaxylylenediamine (MXDA), diaminodiphenylmethane (DDM), m-phenylenediamine (MPDA) and diaminodiphenyl sulfone
  • DETA diethylenetriamine
  • TETA triethylenetetramine
  • MXDA metaxylylenediamine
  • DDM diaminodiphenylmethane
  • MPDA m-phenylenediamine
  • diaminodiphenyl sulfone In addition to aromatic polyamines such as (DDS), polyamine compounds containing dicyandiamide (DICY), organic acid dihydrazide and the like may be mentioned, and these may be used alone or in combination of two or more.
  • ⁇ Acid anhydride curing agent examples include alicyclic anhydrides such as hexahydrophthalic anhydride (HHPA), methyltetrahydrophthalic anhydride (MTHPA) and maleic anhydride, trimellitic anhydride (TMA) and pyromellitic anhydride Examples thereof include acids (PMDA), benzophenonetetracarboxylic acids (BTDA), and aromatic acid anhydrides such as phthalic anhydride. These may be used alone or in combination of two or more.
  • HHPA hexahydrophthalic anhydride
  • MTHPA methyltetrahydrophthalic anhydride
  • TMA trimellitic anhydride
  • pyromellitic anhydride examples thereof include acids (PMDA), benzophenonetetracarboxylic acids (BTDA), and aromatic acid anhydrides such as phthalic anhydride. These may be used alone or in combination of two or more.
  • mercaptan-based curing agent trimethylolpropane tris (3-mercaptobutyrate), trimethylolethane tris (3-mercaptobutyrate), etc. may be mentioned, and even if they are used alone, they may be used in combination of two or more. May be
  • ⁇ Other curing agent> Other curing agents include isocyanate compounds such as isocyanate prepolymers and blocked isocyanates, organic acids such as carboxylic acid-containing polyester resins, etc. These may be used alone or in combination of two or more. . Moreover, you may use combining 2 or more types of the hardening agent of a different system among the above-mentioned.
  • the ratio of the epoxy resin to the curing agent equivalent ratio that is, the ratio of the number of epoxy groups in the epoxy resin / the number of phenolic hydroxyl groups in the phenol resin-based curing agent is particularly
  • the range of 0.5 or more and 2 or less is preferable, and the range of 0.6 or more and 1.8 or less is more preferable, 0.8
  • the range of not less than 1.5 is the most preferable.
  • the epoxy resin composition can contain an inorganic filler.
  • the inorganic filler include fused silica such as fused and crushed silica and fused spherical silica, silica such as crystalline silica, alumina, aluminum hydroxide, silicon nitride, and aluminum nitride. These may be used alone or in combination of two or more. Among these, preferred are silicas such as fused and crushed silica, fused spherical silica, and crystalline silica, and more preferably fused spherical silica can be used.
  • the lower limit of the average particle diameter (D50) of the inorganic filler may be, for example, 0.01 ⁇ m or more, 1 ⁇ m or more, or 5 ⁇ m or more.
  • the flowability of the epoxy resin composition can be improved, and the moldability can be more effectively improved.
  • the upper limit of the average particle diameter (D50) of an inorganic filler is 50 micrometers or less, for example, Preferably it is 40 micrometers or less. Thereby, the occurrence of non-filling and the like can be reliably suppressed.
  • the inorganic filler of the present embodiment can include at least an inorganic filler having an average particle diameter (D50) of 1 ⁇ m or more and 50 ⁇ m or less. Thereby, the fluidity can be made better.
  • the average particle diameter (D50) of the inorganic filler is measured on a volume basis of the particle size distribution of particles using a commercially available laser diffraction type particle size distribution measuring apparatus (for example, SALD-7000 manufactured by Shimadzu Corporation), and its median The diameter (D50) can be an average particle diameter.
  • the said inorganic filler may use together the 2 or more types of filler of a different average particle diameter (D50), for example.
  • D50 average particle diameter
  • a filler having an average particle diameter of 0.01 ⁇ m or more and 1 ⁇ m or less and a filler having an average particle diameter of 1 ⁇ m to 50 ⁇ m or less improve the filling property of the epoxy resin composition. And may be used as an example.
  • the inorganic filler of the present embodiment from the viewpoint of further improving the filling property of the epoxy resin composition, for example, a first filler having an average particle diameter of 0.01 ⁇ m or more and 1 ⁇ m or less and an average particle diameter of 1 ⁇ m
  • the second filler may be larger than 15 ⁇ m
  • the third filler may be larger than 15 ⁇ m and 50 ⁇ m or less.
  • the lower limit of the content of the inorganic filler is, for example, preferably 70% by mass or more, more preferably 73% by mass or more, and more preferably 75% by mass, based on the total solid content of the epoxy resin composition. It is especially preferable that it is more than. Thereby, low moisture absorption and low thermal expansion can be improved, and the temperature cycle resistance and the reflow resistance of the semiconductor device and the other structures can be more effectively improved.
  • the upper limit value of the content of the inorganic filler is, for example, preferably 95% by mass or less, more preferably 93% by mass or less, based on the total solid content of the epoxy resin composition. It is particularly preferable that the content is less than or equal to mass%. This makes it possible to more effectively improve the flowability and the fillability at the time of molding of the epoxy resin composition.
  • the said epoxy resin composition can further contain a hardening accelerator as needed.
  • a hardening accelerator any curing accelerator may be used as long as it accelerates the crosslinking reaction of the epoxy resin and the curing agent, and those used for general epoxy resin compositions can be used.
  • curing accelerator examples include diazabicycloalkenes such as 1,8-diazabicyclo (5,4,0) undecene-7 and derivatives thereof; organic phosphines such as triphenylphosphine and methyl diphenylphosphine; Imidazole compounds such as imidazole (imidazole-based curing accelerator); tetra-substituted phosphonium tetra-substituted borates such as tetraphenyl phosphonium tetraphenyl borate and the like. These may be used alone or in combination of two or more.
  • imidazole-based curing accelerator examples include imidazole, 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole.
  • 2-phenyl-4-methylimidazole 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4 Diamino-6- [2′-methylimidazolyl (1 ′)]-ethyl-s-triazine, 2,4-diamino-6- [2′-undecylimidazolyl (1 ′)]-ethyl-s-triazine, 2 , 4-Diamino-6- [2′-ethyl-4-methylimidazoly
  • the lower limit of the content of the curing accelerator is, for example, preferably 0.20% by mass or more, and more preferably 0.40% by mass or more, with respect to the total solid content of the epoxy resin composition. It is especially preferable that it is 0.70 mass% or more.
  • the upper limit value of the content of the curing accelerator is, for example, preferably 3.0% by mass or less, and more preferably 2.0% by mass or less based on the total solid content of the epoxy resin composition. preferable.
  • content of a hardening accelerator below the said upper limit, the improvement of the fluidity
  • the said epoxy resin composition can contain a coupling agent as needed.
  • the coupling agent include various silane compounds such as epoxysilane, mercaptosilane, aminosilane, alkylsilane, ureidosilane, vinylsilane and methacrylsilane, titanium compounds, aluminum chelates and aluminum / zirconium compounds. Coupling agents can be used.
  • vinyltrichlorosilane vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris ( ⁇ -methoxyethoxy) silane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxy Silane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -methacryloxypropylmethyldiethoxysilane, ⁇ -methacryloxypropyltriethoxysilane , Vinyltriacetoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -anilinopropyltrimethoxysilane, ⁇ -an
  • silane compounds of epoxysilane, mercaptosilane, aminosilane, alkylsilane, ureidosilane or vinylsilane are more preferable.
  • a secondary aminosilane represented by phenylaminopropyltrimethoxysilane is particularly preferable.
  • the lower limit value of the content of the coupling agent is preferably 0.1% by mass or more, and more preferably 0.15% by mass or more based on the total solid content of the epoxy resin composition.
  • the upper limit value of the content of the coupling agent is preferably 1% by mass or less and more preferably 0.5% by mass or less based on the total solid content of the epoxy resin composition.
  • the said epoxy resin composition can contain the low stress agent as needed.
  • the low stress agent include silicone oil, silicone rubber, polyisoprene, polybutadiene such as 1,2-polybutadiene and 1,4-polybutadiene, styrene-butadiene rubber, acrylonitrile-butadiene rubber, polychloroprene, poly (oxypropylene), It may contain one or more selected from thermoplastic elastomers such as poly (oxytetramethylene) glycol, polyolefin glycol, poly- ⁇ -caprolactone, polysulfide rubber, and fluororubber.
  • containing at least one of silicone rubber, silicone oil, and acrylonitrile-butadiene rubber controls the elastic modulus within a desired range, and the temperature cycle resistance of the obtained semiconductor package and other structures.
  • silicone rubber silicone oil, and acrylonitrile-butadiene rubber controls the elastic modulus within a desired range, and the temperature cycle resistance of the obtained semiconductor package and other structures.
  • it can be selected as a particularly preferred embodiment.
  • content of the low stress agent whole is 0.05 mass% or more with respect to the total solid of an epoxy resin composition, and it is 0.10 mass% or more More preferable.
  • the content of the low stress agent is preferably 2% by mass or less, and more preferably 1% by mass or less, based on the total solid content of the epoxy resin composition.
  • the epoxy resin composition of the present embodiment can further contain other components, if necessary.
  • Other components include, for example, ion capturing agents such as hydrotalcite and aluminum-magnesium inorganic ion exchangers; colorants such as carbon black and bengala; natural waxes such as carnauba wax; montanic acid ester wax; diethanolamine / dimontanic acid Esters, synthetic waxes such as tolylene diisocyanate-modified oxidized waxes, higher fatty acids such as zinc stearate and metal salts thereof or mold release agents such as paraffin; various additives such as antioxidants can be mentioned. These additives may be blended appropriately.
  • the manufacturing method of the epoxy resin composition of this embodiment is demonstrated.
  • the method for producing the epoxy resin composition can include a lot sorting step and a mixing step. First, a plurality of epoxy resins a having different lots are prepared, and the number of chlorine-containing particles of the prepared epoxy resin a is measured using the above-described inspection method of chlorine-containing particles. Based on the obtained measurement results, an epoxy resin a containing chlorine-containing particles is selected from a plurality of lots and used as a raw material component (epoxy resin A) of the epoxy resin composition (lot selection step). An epoxy resin composition can be obtained by mixing other raw material components with the epoxy resin A (mixing step).
  • curing agent b and inorganic filler c are also subjected to lot selection in the same manner as epoxy resin a, and curing agent b and inorganic filler c containing chlorine-containing particles are used as raw materials. You may use as a component (hardener B and the inorganic filler C). Moreover, it is possible to add the method of controlling the quantity of the above-mentioned chlorine containing particle
  • the mixture is obtained by mixing by a known means. Furthermore, the mixture is melt-kneaded to obtain a kneaded product.
  • a kneading method for example, an extrusion kneader such as a single-screw kneading extruder or a twin-screw kneading extruder, or a roll kneader such as a mixing roll can be used, but a twin-screw kneading extruder is used. Is preferred.
  • the kneaded product can be made into powder, granules, tablets, or sheets.
  • a method of pulverizing a kneaded material by a pulverizing apparatus for example, a method of pulverizing a kneaded material by a pulverizing apparatus may be mentioned.
  • the kneaded material may be formed into a sheet and pulverized.
  • a grinding device for example, a hammer mill, a millstone type grinder, a roll crusher or the like can be used.
  • a die having a small diameter is installed at the outlet of a kneading apparatus, and a molten material in a molten state discharged from the dies is given a predetermined length by a cutter or the like. It is also possible to use a granulation method typified by a hot cut method of cutting into pieces. In this case, after obtaining a granular or powdery resin composition by a granulation method such as a hot cut method, it is preferable to carry out degassing while the temperature of the resin composition is not lowered so much.
  • the epoxy resin composition of the present embodiment can be used in various applications.
  • the epoxy resin composition of the present embodiment can be used for a sealing resin composition or a fixing resin composition.
  • a sealing resin composition (a sealing resin composition for sealing an electronic component) according to the present embodiment, an electronic component such as a semiconductor chip can be sealed, and it is used for the above semiconductor package Resin composition for encapsulating a semiconductor, resin composition for encapsulating an electronic control unit for automobile sealing a substrate on which an electronic component or the like is mounted, or for a sensor, for a sensor module, for a camera, for a camera module, a module with a display It is applicable to the resin composition for module sealing with dry cells and coin cells.
  • a resin composition for fixation which concerns on this embodiment, it can be used also for fixation of motor components, For example, it is applicable to the resin composition for stator core fixation, a stator fixation, etc.
  • the structure (for example, an electronic device) of the present embodiment is provided with a cured product of the above epoxy resin composition.
  • the structure include an electronic control unit in which a semiconductor package, a substrate on which electronic components and the like are mounted are sealed, a sensor, a sensor module, a camera, a camera module, a module with a display, a module with a dry cell / coin cell, a motor, etc. Can be mentioned.
  • FIG. 1 is a view showing a cross-sectional structure of an example of a semiconductor device using the epoxy resin composition of the present embodiment.
  • the semiconductor element 1 is fixed on the die pad 3 via the die bonding material curing body 2.
  • the electrode pads of the semiconductor element 1 and the lead frame 5 are connected by bonding wires 4.
  • the semiconductor element 1 is sealed by the cured body 6 of the epoxy resin composition of the present embodiment.
  • FIG. 2 is a view showing a cross-sectional structure of an example of a single-sided sealed type semiconductor device using the epoxy resin composition of the present embodiment.
  • the semiconductor element 1 is fixed on the solder resist 7 of the laminated body in which the layer of the solder resist 7 is formed on the surface of the substrate 8 via the die bonding material cured body 2.
  • the solder resist 7 on the electrode pad is removed by a developing method so that the electrode pad of the substrate 8 is exposed.
  • the electrode pads of the semiconductor element 1 and the electrode pads of the substrate 8 are connected by bonding wires 4. Only one side of the substrate 8 on which the semiconductor element 1 is mounted is sealed by the cured product 6 of the epoxy resin composition of the present embodiment.
  • the electrode pads on the substrate 8 are internally joined to the solder balls 9 on the non-sealing surface side on the substrate 8.
  • FIG. 3 is a schematic cross-sectional view showing an example of the structure (vehicle-mounted electronic control unit 10) of the present embodiment.
  • the in-vehicle electronic control unit 10 is used to control an engine, various in-vehicle devices, and the like.
  • the on-vehicle electronic control unit 10 includes, for example, a substrate 12, an electronic component 16 mounted on the substrate 12, and a sealing resin layer 14 for sealing the substrate 12 and the electronic component 16.
  • the substrate 12 has a connection terminal 18 for connecting to the outside on at least one side.
  • the on-vehicle electronic control unit 10 according to an example of the present embodiment is electrically connected to the mating connector via the connecting terminal 18 by fitting the connecting terminal 18 and the mating connector.
  • the substrate 12 is, for example, a wiring substrate provided with a circuit wiring on one or both of one surface and the other surface opposite to the one surface. As shown in FIG. 3, the substrate 12 has, for example, a flat plate shape. In the present embodiment, for example, an organic substrate formed of an organic material such as polyimide can be employed as the substrate 12.
  • the thickness of the substrate 12 is not particularly limited, but may be, for example, 0.1 mm or more and 5 mm or less, and preferably 0.5 mm or more and 3 mm or less.
  • a through hole 120 may be provided in the substrate 12, for example, penetrating the substrate 12 to connect one surface to the other surface.
  • the wiring provided on one surface of the substrate 12 and the wiring provided on the other surface are electrically connected via the conductor pattern provided in the through hole 120.
  • the conductive pattern is formed along the wall surface of through hole 120. That is, the conductive pattern in through hole 120 is formed in a cylindrical shape.
  • the void holes formed on the inner wall surface of the conductive pattern are filled with the cured product (sealing resin layer 14) of the epoxy resin composition of the present embodiment.
  • an electronic component 16 is mounted on one or both of one surface and the other surface of the substrate 12.
  • the electronic component 16 is not particularly limited as long as it can be mounted on a vehicle-mounted electronic control unit, and for example, a microcomputer may be mentioned.
  • the substrate 12 may be mounted, for example, on a metal base.
  • the metal base can function as a heat sink for dissipating heat generated from the electronic component 16, for example.
  • the on-vehicle electronic control unit 10 can be formed by integrally sealing and molding, for example, a metal base and the substrate 12 mounted on the metal base using an epoxy resin composition.
  • a metal material which comprises a metal base For example, iron, copper, and aluminum, and the alloy etc. which contain 1 or 2 types of these, etc. can be included.
  • the on-vehicle electronic control unit 10 may not have a metal base.
  • Colorant 1 carbon black (carbon # 5, manufactured by Mitsubishi Chemical Corporation)
  • Curing accelerator 1 represented by the following formula [Method of synthesizing curing accelerator 1] In a flask containing 1800 g of methanol, 249.5 g of phenyltrimethoxysilane and 384.0 g of 2,3-dihydroxynaphthalene were added and dissolved, and then 231.5 g of a 28% sodium methoxide-methanol solution was added dropwise while stirring at room temperature. Further, a solution of 503.0 g of tetraphenylphosphonium bromide prepared in advance in 600 g of methanol was added dropwise thereto under stirring at room temperature to precipitate crystals. The precipitated crystals were filtered, washed with water and vacuum dried to obtain the above-mentioned curing accelerator 1 of pinkish white crystals.
  • Hardening accelerator 2 Hardening accelerator 2 represented by the following formula
  • Coupling agent 1 N-phenyl-3-aminopropyltrimethoxysilane (CF-4083, manufactured by Toray Dow Corning)
  • Coupling agent 2 3-mercaptopropyltrimethoxysilane (S810, manufactured by Chisso)
  • Epoxy resin A Epoxy resin a1: phenol-aralkyl epoxy resin containing biphenylene skeleton (NC 3000 L, manufactured by Nippon Kayaku Co., Ltd.)
  • Epoxy resin a2 Bisphenol A epoxy resin (YL 6810, manufactured by Mitsubishi Chemical Corporation)
  • Epoxy resin a3 biphenyl type epoxy resin (YX4000K, manufactured by Mitsubishi Chemical Corporation)
  • Epoxy resin 4 Epoxy resin synthesized without using epichlorohydrin (glycidyl ether type liquid epoxy resin, manufactured by DIC EPICLON EXA-4880, total chlorine: 0 ppm)
  • Epoxy resin 5 Epoxy resin synthesized without using epichlorohydrin (alicyclic epoxy resin, manufactured by Daisel Co. EHPE 3150, total chlorine: 0 ppm)
  • Inorganic filler C Inorganic filler C, Inorganic filler c1: fused spherical silica (FB-100XFC, manufactured by Denka, average particle size 13 ⁇ m) Inorganic filler c2: fused spherical silica (MSV-SC3, manufactured by Ryumori, average particle diameter 19 ⁇ m) Inorganic filler c3: spherical silica (SD 2500-SQ, manufactured by Admatex, average particle size 0.5 ⁇ m) Inorganic filler c4: spherical silica (SC-2500-SQ, manufactured by Admatex Co., Ltd., average particle size 0.5 ⁇ m) Inorganic filler c5: fused spherical silica (FB-950FC, manufactured by Denka, average particle diameter 22 ⁇ m)
  • Flame retardant 1 Aluminum hydroxide (BE043, manufactured by Nippon Light Metal Co., Ltd.)
  • Flame retardant 2 Aluminum hydroxide (CL-303, manufactured by Sumitomo Chemical Co., Ltd.)
  • Hardening agent b1 biphenylene skeleton-containing phenol aralkyl resin (MEH-7851 SS, manufactured by Meiwa Kasei Co., Ltd.)
  • Hardening agent b2 Novolak type phenol resin (PR-HF-3, manufactured by Sumitomo Bakelite Co., Ltd.)
  • Ion capture agent Ion scavenger 1: Hydrotalcite (DHT-4H, manufactured by Kyowa Chemical Industry Co., Ltd.)
  • Ion trapping agent 2 Aluminum-magnesium inorganic ion exchanger (IXE-700F, manufactured by Toagosei Co., Ltd.)
  • Low stress agent 1 Acrylonitrile-butadiene copolymer compound (CTBN 1008SP, manufactured by PTI Japan Ltd.)
  • Low stress agent 2 Melt reactant A (silicone) obtained by the following synthesis method [Method of synthesizing molten reactant A] 66.1 parts by weight of a bisphenol A-type epoxy resin (JERB Epoxy Resins Co., Ltd., jER (registered trademark) YL 6810, softening point 45 ° C., epoxy equivalent 172) represented by the following formula (8) Then, 33.1 parts by weight of organopolysiloxane represented by the following formula (7) and 0.8 parts by weight of triphenylphosphine were added and melt mixed for 30 minutes to obtain a molten reactant A.
  • Low stress agent 3 Alkyl group-containing silicone (Silsoft 034, manufactured by Momentive)
  • Releasing agent 1 Montanic acid ester wax (WE-4, manufactured by Clariant Japan Ltd.)
  • Releasing agent 2 Diethanolamine / zimontanic acid ester (NC-133, manufactured by Ito Oil Co., Ltd.)
  • Releasing agent 3 Tolylene diisocyanate-modified oxidized wax (NPS-6010, manufactured by Nippon Seiwa Co., Ltd.)
  • Release agent 4 Stearic acid (SR-Sakura, manufactured by NOF Corporation)
  • Example 1 A plurality of epoxy resins a1 having different lots were prepared, and the number of chlorine-containing particles of the prepared epoxy resin a1 was measured using the following inspection method of chlorine-containing particles. Based on the obtained measurement results, an epoxy resin a1 containing a number of chlorine-containing particles shown in Table 2 was selected from a plurality of lots and used as a raw material component (epoxy resin A) of the epoxy resin composition .
  • the curing agent b1 was used as the curing agent B, and the inorganic fillers c1 and c3 were used as the inorganic filler C.
  • Example 2 A plurality of epoxy resins a2 having different lots were prepared, and the number of chlorine-containing particles of the prepared epoxy resin a2 was measured using the following inspection method of chlorine-containing particles. Based on the obtained measurement results, an epoxy resin a2 containing a number of chlorine-containing particles shown in Table 2 was selected from a plurality of lots and used as a raw material component (epoxy resin A) of the epoxy resin composition An epoxy resin composition was obtained in the same manner as Example 1 except for the above.
  • Example 3 An epoxy resin composition was obtained in the same manner as in Example 1 except that inorganic fillers c2 and c3 were used as the inorganic filler C.
  • Example 4 The same procedure as in Example 1 was repeated except that the solution obtained by dissolving in an organic solvent and filtering it with a 1 ⁇ m filter was used as a raw material component (curing agent B) for the same lot of curing agent b1 as in Example 1.
  • the epoxy resin composition was obtained.
  • Example 5 A plurality of epoxy resins a3 having different lots were prepared, and the number of chlorine-containing particles of the prepared epoxy resin a3 was measured using the following inspection method of chlorine-containing particles. Based on the obtained measurement results, an epoxy resin a3 containing a number of chlorine-containing particles shown in Table 2 was selected from a plurality of lots and used as a raw material component (epoxy resin A) of the epoxy resin composition .
  • the curing agent b1 was used as the curing agent B, and the inorganic fillers c4 and c5 were used as the inorganic filler C.
  • Example 6 The curing agent b2 is used in place of the curing agent b1 of Example 2, and the solution obtained by dissolving the solution in an organic solvent is filtered through a 1 ⁇ m filter for the curing agent b2 as a raw material component (curing agent B) An epoxy resin composition was obtained in the same manner as in Example 5 except that it was used.
  • Example 7 The solution obtained by dissolving in an organic solvent was filtered with a 1 ⁇ m filter for epoxy resin a3 of a lot different from Example 5 and the number of chlorines shown in Table 2 was measured using the following inspection method of chlorine-containing particles An epoxy resin composition was obtained in the same manner as in Example 5, except that the epoxy resin a3 containing the containing particles was used as a raw material component (epoxy resin A).
  • Comparative Example 1 An epoxy resin composition was obtained in the same manner as in Example 1 except that the epoxy resin 4 was used as the epoxy resin A.
  • Comparative Example 2 An epoxy resin composition was obtained in the same manner as in Example 5, except that the epoxy resin 5 was used as the epoxy resin A.
  • Comparative Example 3 The solution obtained by dissolving in an organic solvent was filtered through a 1 ⁇ m filter for epoxy resin a2 of a lot different from Example 2 and the number of chlorine-containing particles measured using the following method for inspecting chlorine-containing particles is 0 An epoxy resin composition was obtained in the same manner as in Example 2 except that the epoxy resin a2 was used as the raw material component (epoxy resin A).
  • the raw material component which comprises an epoxy resin composition or an epoxy resin composition was prepared.
  • the epoxy resin composition used what cooled and obtained the kneaded material which mixed and knead
  • 50 g of the sample of (1) is put into a cleaned 1000 ml container made of polypropylene, 300 ml of acetone is added, the container is covered, and using a shaker, room temperature 25 ° C., 300 reciprocations / minute Shake (mix) for 50 minutes.
  • the acetone to be used used what was filtered by the filter of 12 micrometers of mesh sizes.
  • the above acetone-washed filter was placed in a funnel set (filtering device).
  • the filter used was a nylon filter with an opening size of 75 ⁇ m, which was subjected to ultrasonic cleaning.
  • the container shaken in (2) was allowed to stand, and then the solution in the container was poured from the top of the funnel of (3) and suction filtered through a filter.
  • the funnel was removed and the residue on the filter was dried with suction.
  • the adhesive surface of the measurement sheet was attached to the filter surface of (5), and the residue was collected on the adhesive surface of the measurement sheet.
  • the measurement sheet of (6) was peeled off from the filter, and a composite photograph was created using a digital microscope for the entire surface of the adhesive surface. After adjusting the visual field magnification to be 50 times, the entire surface was observed, and the position where the residue was present was recorded and printed.
  • the organic substance of chlorine-containing particles 1A-1 is a mixture of epoxy resin and carbonate
  • the organic substance of chlorine-containing particles 1A-2 is a carbonate
  • the organic substance of chlorine-containing particles 2A-1 is an amide compound
  • Organic substances of 1 are carbonates
  • organic substances of chlorine-containing particles 5A-2 are carbonates and silicates
  • organic substances of chlorine-containing particles 1-4 are cellulose
  • organic substances of chlorine-containing particles 2-1 are cellulose
  • chlorine-containing particles 3- The organic substance of 4 was identified to contain cellulose.
  • the epoxy resin compositions of Examples 1 to 7 were found to be excellent in metal adhesion as compared with the epoxy resin compositions of Comparative Examples 1 to 3, because the adhesion to the Cu frame was improved.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Epoxy Resins (AREA)
  • Sealing Material Composition (AREA)

Abstract

Cette composition de résine époxy contient une résine époxy, un agent de durcissement et une charge inorganique, tout en contenant des particules contenant du chlore qui contiennent une substance organique.
PCT/JP2018/042951 2017-12-06 2018-11-21 Composition de résine époxy et dispositif à composants électroniques WO2019111707A1 (fr)

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CN201880079022.8A CN111433284B (zh) 2017-12-06 2018-11-21 环氧树脂组合物和电子装置
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CN111433284B (zh) 2021-01-05

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