WO2023162975A1 - 封止用樹脂組成物および半導体装置 - Google Patents

封止用樹脂組成物および半導体装置 Download PDF

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Publication number
WO2023162975A1
WO2023162975A1 PCT/JP2023/006237 JP2023006237W WO2023162975A1 WO 2023162975 A1 WO2023162975 A1 WO 2023162975A1 JP 2023006237 W JP2023006237 W JP 2023006237W WO 2023162975 A1 WO2023162975 A1 WO 2023162975A1
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Prior art keywords
resin composition
curing agent
plant
encapsulating resin
phenol
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PCT/JP2023/006237
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English (en)
French (fr)
Japanese (ja)
Inventor
正寛 岩井
祐介 田中
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Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Priority to KR1020247031984A priority Critical patent/KR20240154052A/ko
Priority to CN202380022705.0A priority patent/CN118742588A/zh
Priority to JP2023551185A priority patent/JP7477055B2/ja
Priority to EP23759976.6A priority patent/EP4488314A4/en
Publication of WO2023162975A1 publication Critical patent/WO2023162975A1/ja
Priority to JP2024059374A priority patent/JP2024094333A/ja
Anticipated expiration legal-status Critical
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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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W74/00—Encapsulations, e.g. protective coatings
    • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
    • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or 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
    • C08G59/40—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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W74/00—Encapsulations, e.g. protective coatings
    • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
    • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
    • H10W74/473—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins containing a filler

Definitions

  • the present invention relates to an encapsulating resin composition and a semiconductor device.
  • Thermosetting resin compositions are known as materials for sealing semiconductor packages and the like.
  • Patent Document 1 in an electronic device such as an engine control unit or an automatic transmission control unit used for automobiles, an electronic component included in the electronic device, a board on which the electronic component is mounted, and a board connected to the board The encapsulation resin used for encapsulating the terminals together is described.
  • a sealing resin composition comprising: [2] The encapsulating resin composition according to [1], wherein the phenolic curing agent obtained from a plant-derived raw material is a biomass-modified phenolic resin modified with a plant-derived unsaturated carbon chain-containing phenol. . [3] The encapsulating resin composition according to [1] or [2], wherein the curing agent (B) contains a phenolic curing agent obtained from a petroleum-derived raw material.
  • the encapsulating resin composition of the present invention it is possible to provide an encapsulating material that uses a plant-derived raw material, is friendly to the global environment, and has excellent practicality such as fluidity, curability, and electrical reliability. can.
  • FIG. 1 is a cross-sectional view showing the configuration of a semiconductor device according to an embodiment
  • FIG. 1 is a cross-sectional view showing the configuration of a semiconductor device according to an embodiment
  • FIG. 1 is a cross-sectional view showing the configuration of a semiconductor device according to an embodiment
  • the encapsulating resin composition of the present embodiment contains an epoxy resin (A) and a curing agent (B) containing a phenolic curing agent (B1) obtained from a plant-derived raw material.
  • the plant-derived phenol curing agent (B1) and the plant-derived epoxy resin (A2) contained in the epoxy resin (A), which will be described later, can be obtained from plant-derived phenols.
  • Plant-derived phenols include, for example, phenol (hydroxybenzene); benzenediol (dihydroxybenzene) such as catechol, resorcinol, and hydroquinone; Benzenetriols (trihydroxybenzenes) such as hydroxynol, phloroglucinol, pyroganols; Unsaturated carbon chain-containing phenols such as cashew oil and cardanol; Saturated carbon chain-containing phenols such as cardol, 2-methylcardol, anacardic acid; o-cresol, m-cresol, p-cresol, 2,4-dimethylphenol, 2,6-dimethylphenol, 2,3,6-trimethylphenol, 2,4,6-trimethylphenol, 5-isopropyl-2methyl Phenol, 4-isopropylphenol, 4-cyclohexylphenol, 4-phenylphenol, 3-pentadecylphenol, 3-pentadec
  • Derivatives include, for example, salts, hydrates, solvates and the like.
  • the cyclic compound may contain non-biomass-derived compounds and other components as impurities.
  • the method for producing plant-derived phenols includes, for example, step 1 of obtaining raw materials containing hydroxybenzoic acids from mixed sugar contained in plants, followed by a step of decarboxylating the hydroxybenzoic acids by biological or chemical reaction. 2 to obtain plant-derived phenols, and the like.
  • the method of step 2 includes, for example, WO2012/063860 as a biological reaction and decarboxylation with an acidic compound as a chemical reaction.
  • Epoxy resin (A) is a compound having two or more epoxy groups in one molecule, and may be any of monomer, oligomer and polymer.
  • epoxy resin (A) examples include crystalline epoxy resins such as biphenyl type epoxy resins, bisphenol type epoxy resins and stilbene type epoxy resins; novolac type epoxy resins such as phenol novolac type epoxy resins and cresol novolak type epoxy resins.
  • multifunctional epoxy resins such as trisphenylmethane epoxy resins and alkyl-modified triphenolmethane epoxy resins; phenol aralkyl epoxy resins such as phenylene skeleton-containing phenol aralkyl epoxy resins and biphenylene skeleton-containing phenol aralkyl epoxy resins; dihydroxynaphthalene type epoxy resins, naphthol-type epoxy resins such as epoxy resins obtained by glycidyl-etherifying a dimer of dihydroxynaphthalene; triazine nucleus-containing epoxy resins such as triglycidyl isocyanurate and monoallyl diglycidyl isocyanurate; dicyclopentadiene-modified phenol It is one or more selected from the group consisting of bridged cyclic hydrocarbon compound-modified phenol type epoxy resins such as type epoxy resins.
  • the epoxy resin (A) is preferably a trisphenylmethane type epoxy resin, a biphenylaralkyl type polyfunctional epoxy resin, an orthocresol type bifunctional epoxy resin, or a biphenyl type bifunctional epoxy resin. It is one or more selected from the group consisting of resins and bisphenol-type bifunctional epoxy resins.
  • the epoxy resin (A) is preferably tris(hydroxyphenyl)methane-type epoxy resin, biphenylene skeleton-containing phenol aralkyl-type epoxy resin, ortho-cresol novolac-type epoxy resin and 3,3',5,5' - One or more selected from the group consisting of tetramethylbiphenylglycidyl ether type epoxy resins.
  • the epoxy resin (A) can contain an epoxy resin (A1) obtained from petroleum-derived raw materials.
  • Examples of the epoxy resin (A1) include the epoxy resins described above.
  • an epoxy resin (A2) obtained by epoxidizing phenol obtained from a plant-derived raw material is preferable to include an epoxy resin (A2) obtained by epoxidizing phenol obtained from a plant-derived raw material.
  • the plant-derived epoxy resin (A2) is prepared by, for example, reacting a compound having a plant-derived phenolic hydroxyl group, such as the plant-derived phenols or the plant-derived phenol curing agent (B1), with epichlorohydrin or the like, thereby removing the phenolic hydroxyl group. It can be obtained by a process of substituting with a phenol glycidyl ether group.
  • the content of the epoxy resin (A) in the encapsulating resin composition is, with respect to the entire encapsulating resin composition, from the viewpoint of obtaining suitable fluidity during molding and improving filling properties and moldability.
  • the content is preferably 2% by mass or more, more preferably 3% by mass or more, and still more preferably 4% by mass or more.
  • the content of the epoxy resin (A) in the encapsulating resin composition is set to is preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 10% by mass or less.
  • the ratio (A1:A2) between the epoxy resin (A1) and the epoxy resin (A2) is preferably 10:90. to 90:10, more preferably 20:80 to 80:20.
  • the curing agent (B) contains a phenolic curing agent (B1) obtained from a plant-derived raw material.
  • the plant-derived phenol curing agent (B1) is obtained, for example, by a step of reacting the plant-derived phenols with plant-derived or petroleum-derived aldehydes in the presence of an acidic catalyst.
  • Plant-derived phenol curing agents (B1) include phenol novolac resins, cresol novolac resins, aromatic hydrocarbon formaldehyde resin-modified phenol resins, dicyclopentadiene phenol addition type resins, phenol aralkyl resins, biphenyl skeleton-containing phenol aralkyl resins, and naphthol.
  • Aralkyl resins trimethylolmethane resins, tetraphenylolethane resins, naphthol novolac resins, naphthol-phenol co-condensed novolak resins, naphthol-cresol co-condensed novolak resins, biphenyl-modified phenolic resins (polyvalent phenolic compounds), biphenyl-modified naphthol resins (polyhydric naphthol compounds with phenolic nuclei linked by bismethylene groups), aminotriazine-modified phenolic resins (polyhydric phenolic compounds with phenolic nuclei linked by melamine, benzoguanamine, etc.), trisphenolmethane type phenolic resin, biomass-modified phenolic resin, and the like.
  • a biomass-modified phenolic resin as the plant-derived phenolic curing agent (B1).
  • biomass-modified phenolic resin a known biomass-modified phenolic resin can be used as long as the effect of the present invention is achieved. preferable.
  • the above biomass-modified phenolic resin can be obtained, for example, by a process of reacting biomass derivatives, phenols and aldehydes.
  • This biomass derivative can be obtained, for example, by an addition reaction step in which a phenol is added to the double bond of the unsaturated carbon chain of the unsaturated carbon chain-containing phenol derived from the plant material.
  • the plant raw material is not particularly limited as long as it is a phenol containing an unsaturated carbon chain.
  • Saturated carboxylic acids such as cashew nut shell liquid (cashew oil) such as cardanol, curdle, methyl curdle and anacardic acid, sumac extracts such as urushiol, laccol and thithiol, and their purified products and unsaturated alkyl group-containing phenols; and the like. These may be used alone or in combination of two or more.
  • the biomass modification rate in the biomass-modified phenolic resin can be increased, and the heat resistance of the cured product can be improved.
  • phenolic hydroxyl group- and unsaturated alkyl group-containing phenols by using phenolic hydroxyl group- and unsaturated alkyl group-containing phenols, a biomass-modified phenolic resin having a high biomass introduction rate and excellent reactivity can be realized.
  • there is no easily decomposable functional group such as an ester group, so that a molded article composed of a cured product of biomass-modified phenolic resin can be made excellent in heat resistance.
  • the cashew oil is an oily liquid contained in cashew nut shells and contains anacardic acid, cardol, 2-methylcardol, cardanol, and the like.
  • the cashew oil may contain one or more selected from the group consisting of cardanol, cardol, and 2-methylcardol.
  • Refined cashew oil such as cardanol may also be used. These may be used alone or in combination of two or more.
  • the biomass-modified phenolic resin can contain a cashew-modified phenolic resin.
  • phenolic hydroxyl group-unsaturated alkyl group-containing phenols may include, for example, a phenol compound represented by the following general formula (1). These may be used alone or in combination of two or more.
  • R represents a linear unsaturated hydrocarbon group having 10 or more carbon atoms.
  • a hydrogen atom bonded to a benzene ring having a phenolic hydroxyl group may be substituted with a substituent.
  • R may be any of ortho-position, meta-position and para-position, and may be one or more, two or more, or three or more.
  • R in the above formula (1) represents a linear unsaturated hydrocarbon group having 10 or more carbon atoms, preferably a linear unsaturated hydrocarbon group having 10 to 20 carbon atoms, and a linear unsaturated hydrocarbon group having 12 to 20 carbon atoms.
  • An unsaturated hydrocarbon group is preferred, and a linear unsaturated hydrocarbon group having 12 to 18 carbon atoms is more preferred.
  • a linear unsaturated hydrocarbon group having 12 to 18 carbon atoms is more preferred.
  • the number of carbon atoms in the linear unsaturated hydrocarbon group is equal to or less than the upper limit of the above range, it becomes easier to dilute with an organic solvent.
  • the number of carbon atoms in the straight-chain unsaturated hydrocarbon group is at least the above lower limit, the flexibility tends to be improved.
  • This linear unsaturated hydrocarbon group may have one or more double bonds, may have two, or may have three.
  • substituents that substitute the hydrogen atoms bonded to the benzene ring having a phenolic hydroxyl group examples thereof include an acetyl group, a methyl group, and a hydroxyl group.
  • phenol compound represented by (1) above examples include 3-dodecenylphenol, 3-tridecenylphenol, 3-pentadecenylphenol, 5-tridecenylresorcinol, 5- pentadecenylresorcinol, cardanol, which is a phenol having a linear unsaturated hydrocarbon group with 15 carbon atoms at the meta position, cardol having a linear unsaturated hydrocarbon group with 15 carbon atoms and a hydroxyl group at the meta position, Linear unsaturated hydrocarbon groups having 15 carbon atoms, hydroxyl groups, and 2-methylcardol, which is a phenol having a methyl group at the ortho-position, and the like. Cardanol is preferably used in this embodiment.
  • Cardanol is a component contained in cashew nut shells, and is a compound having a structure represented by formula (2) consisting of a phenol moiety and a linear hydrocarbon moiety having 15 carbon atoms.
  • formula (2) consisting of a phenol moiety and a linear hydrocarbon moiety having 15 carbon atoms.
  • cardanol with different numbers of unsaturated bonds in the linear hydrocarbon moiety R, and these four components are usually a mixture. That is, it is a mixture of 3-pentadecylphenol, 3-pentadecylphenolmonoene, 3-pentadecylphenoldiene, and 3-pentadecylphenoltriene described in formula (2) below.
  • Cardanol-based cashew oil obtained by extraction and purification from cashew nut shell liquid can be used.
  • the phenol is added to the double bond of the unsaturated carbon chain-containing phenol derived from the plant raw material by heat treatment in the presence of an acidic catalyst.
  • a biomass derivative can be obtained.
  • the double bonds of the unsaturated carbon chains remaining in the unsaturated carbon chain-containing phenols can be reduced.
  • acidic catalysts include, but are not limited to, organic carboxylic acids such as oxalic acid and acetic acid; organic sulfonic acids such as benzenesulfonic acid, paratoluenesulfonic acid and methanesulfonic acid; alkyl sulfuric acids such as dimethyl sulfate and diethyl sulfate; Examples include Lewis acid acids such as aluminum, aluminum bromide, ferric chloride, zinc chloride, boron trifluoride, stannic chloride, antimony chloride, gallium chloride and gallium bromide, and inorganic acids such as sulfuric acid.
  • organic carboxylic acids such as oxalic acid and acetic acid
  • organic sulfonic acids such as benzenesulfonic acid, paratoluenesulfonic acid and methanesulfonic acid
  • alkyl sulfuric acids such as dimethyl sulfate and diethyl sulfate
  • Lewis acid acids
  • reaction temperature in the addition reaction step can be appropriately selected depending on the plant material, and may be, for example, 100°C to 200°C, preferably 120°C to 180°C.
  • the reaction time in the addition reaction step is not particularly limited and may be appropriately determined according to the reaction conditions, and may be, for example, 1 hour to 8 hours.
  • the acidic catalyst may be neutralized and removed as necessary, or the acidic catalyst may remain in the biomass derivative as it is. Further, depending on the product form after processing, excess unreacted phenols may be removed thereafter, or unreacted phenols may remain in the biomass derivative.
  • the phenol used in the addition reaction step may have, for example, a mononuclear, dinuclear, or trinuclear phenol ring, and may have one or two or more phenolic hydroxyl groups.
  • examples of the above phenols include, but are not limited to, phenol; cresols such as ortho-cresol, meta-cresol and para-cresol; 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, -xylenol, xylenol such as 3,5-xylenol; 2,3,5-trimethylphenol, 2-ethylphenol, 4-ethylphenol, 2-isopropylphenol, 4-isopropylphenol, n-butylphenol, isobutylphenol, tert- Alkylphenols such as butylphenol, hexylphenol, octylphenol, nonylphenol, phenylphenol, benzylphenol, cum
  • the step of obtaining a biomass-modified phenolic resin includes a step of reacting the obtained biomass derivative, phenols and aldehydes, thereby resulting in biomass-modified resin obtained by reacting the biomass derivative, phenols and aldehydes.
  • a reaction solution containing a phenolic resin can be obtained.
  • the step of obtaining a reaction solution can be performed under acidic conditions.
  • an acidic catalyst such as a known organic acid or inorganic acid can be used.
  • the step of obtaining a reaction solution can be performed under alkaline conditions.
  • an alkaline catalyst can be used.
  • a method for producing a novolak-type phenolic resin will be described. Among these, a novolak-type biomass-modified phenolic resin can be used from the viewpoint of strength.
  • a novolak-type biomass-modified phenolic resin obtained using cardanol has a structural unit represented by the following formula (3).
  • Q has a structure in which the phenol is added to the double bond of the unsaturated carbon chain of R in formula (2).
  • Aldehydes used in the step of obtaining the biomass-modified phenolic resin are not particularly limited, but examples include formaldehyde such as formalin and paraformaldehyde; trioxane, acetaldehyde, propionaldehyde, polyoxymethylene, chloral, hexamethylenetetramine, furfural, and glyoxal. , n-butyraldehyde, caproaldehyde, allylaldehyde, benzaldehyde, crotonaldehyde, acrolein, tetraoxymethylene, phenylacetaldehyde, o-tolualdehyde, salicylaldehyde and the like.
  • formaldehyde such as formalin and paraformaldehyde
  • trioxane acetaldehyde
  • propionaldehyde polyoxymethylene
  • chloral hexamethylenetetramine
  • furfural and
  • aldehydes may be used alone or in combination of two or more.
  • aldehydes can include formaldehyde or acetaldehyde, and formalin or paraformaldehyde can be used from the viewpoint of productivity and low cost.
  • the phenols described in the addition reaction step can be used. These may be used alone or in combination of two or more. Phenols used in each step may be of the same type or of different types.
  • the acidic catalyst used in synthesizing the novolak-type biomass-modified phenolic resin is not particularly limited, but examples include acids such as oxalic acid, hydrochloric acid, sulfuric acid, diethylsulfuric acid, p-toluenesulfonic acid, and metals such as zinc acetate. and salts, which can be used singly or in combination of two or more.
  • the amount of the acidic catalyst used is not particularly limited, but it can be 0.1% by mass or more and 10% by mass or less with respect to the entire biomass-modified phenolic resin.
  • reaction solvent in this embodiment, water may be used, but an organic solvent may also be used.
  • organic solvent a non-aqueous solvent can be used using a non-polar solvent.
  • organic solvents include alcohols, ketones, and aromatics.
  • alcohols include methanol, ethanol, propyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, and glycerin.
  • ketones include Acetone, methyl ethyl ketone, and the like
  • aromatics include toluene, xylene, and the like. These may be used alone or in combination of two or more.
  • the reaction temperature may be, for example, 40°C to 120°C, preferably 60°C to 110°C.
  • the reaction time is not particularly limited, and may be appropriately determined according to the type of starting materials, the molar ratio of the mixture, the amount and type of catalyst used, and the reaction conditions. As described above, a reaction solution containing a biomass-modified phenolic resin can be obtained.
  • a neutralization step of neutralizing the reaction solution may be performed.
  • a step of removing unreacted monomers (eg, unreacted phenols) by a demonomering step may be added after the above reaction.
  • the dehydration step may be performed simultaneously with the demonomerization step.
  • dehydration under reduced pressure may be used, but dehydration under normal pressure may also be used.
  • the degree of vacuum during dehydration under reduced pressure may be, for example, 110 torr or less, and more preferably 80 torr or less.
  • the dehydration time can be shortened, and a stable biomass-modified phenolic resin with little variation in resin properties can be obtained.
  • the water content in the biomass-modified phenolic resin can be reduced to 5% by weight or less by such a dehydration step.
  • these methods can sufficiently remove water, they may be combined with a step of using a known water remover such as a vacuum dryer or a thin film evaporator for further removal.
  • the biomass-modified phenol resin can be recovered and used as a plant-derived phenol curing agent (B1).
  • the plant-derived phenol curing agent (B1) contains more impurities such as ionic impurities than the petroleum-derived phenol curing agent. If this is one of the factors and the degree of biomass is increased, physical properties such as fluidity, curability, and electrical reliability are considered to decrease.
  • a phenolic curing agent obtained from a plant-derived raw material and by setting it to a predetermined composition it is possible to improve these physical properties while increasing the degree of biomass.
  • the curing agent (B) may contain a phenol curing agent (B2) obtained from a petroleum-derived raw material together with a plant-derived phenol curing agent (B1).
  • Phenolic resin (B2) includes, for example, phenols such as phenol novolac resin and cresol novolac resin, cresol, resorcinol, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol, ⁇ -naphthol, ⁇ -naphthol, and dihydroxynaphthalene.
  • Novolac resins obtained by condensation or co-condensation of phenols such as phenols and formaldehyde or ketones in the presence of an acidic catalyst, phenols having a biphenylene skeleton synthesized from the above phenols and dimethoxyparaxylene or bis(methoxymethyl)biphenyl Examples include aralkyl resins, phenol aralkyl resins such as phenol aralkyl resins having a phenylene skeleton, and phenol resins having a trisphenylmethane skeleton. These may be used alone or in combination of two or more.
  • the biomass degree of the cured body of the sealing resin composition of the present embodiment is within a predetermined range. (5% or more and 95% or less), for example, the phenol curing agent (B2) is preferably 0.5% by mass or more and 50 It can be contained in an amount of 1% by mass or more and 20% by mass or less, more preferably 1% by mass or less and 20% by mass or less.
  • the blending amount of the curing agent (B) and the epoxy resin (A) is 1 equivalent in total of the active groups in the curing agent (B) from the viewpoint of the effect of the present invention.
  • the amount of epoxy groups in the epoxy resin is 0.8 to 1.2 equivalents.
  • the active groups in the curing agent (B) refer to arylcarbonyloxy groups and phenolic hydroxyl groups in the resin structure.
  • the curing agent (B) is preferably 0.2% by mass or more and 15% by mass or less, more preferably 0.5% by mass or more and 10% by mass, relative to the entire encapsulating resin composition. Hereafter, it is more preferably used in an amount of 1.0% by mass or more and 7% by mass or less.
  • the obtained cured product can have more excellent dielectric properties and is further excellent in low dielectric loss tangent.
  • the encapsulating resin composition of the present embodiment can contain a curing accelerator (C).
  • the curing accelerator (C) is, for example, a phosphorus atom-containing compound such as an organic phosphine, a tetrasubstituted phosphonium compound, a phosphobetaine compound, an adduct of a phosphine compound and a quinone compound, an adduct of a phosphonium compound and a silane compound; 8-diazabicyclo[5.4.0]undecene-7, benzyldimethylamine, nitrogen atom-containing compounds such as amidines and tertiary amines, quaternary salts of the above amidines and amines exemplified by 2-methylimidazole; It may contain one or more selected from polyhydroxynaphthalene compounds such as 3-dihydroxynaphthalene.
  • a phosphorus atom-containing compound such as an organic phosphine, a tetrasubstituted phosphonium compound, a phosphobetaine compound, an ad
  • a phosphorus atom-containing compound from the viewpoint of improving curability.
  • tetrasubstituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, adducts of phosphonium compounds and silane compounds, etc. have latent properties. It is more preferable to include
  • the content of the curing accelerator (C) in the encapsulating resin composition is preferably 0.01 with respect to the entire encapsulating resin composition. % by mass or more, more preferably 0.05% by mass or more, and still more preferably 0.1% by mass or more.
  • the content of the curing accelerator (C) in the encapsulating resin composition is preferably is 2.0% by mass or less, more preferably 1.0% by mass or less, and still more preferably 0.5% by mass or less.
  • the encapsulating resin composition of the present embodiment can contain an inorganic filler (D).
  • the inorganic filler (D) those generally used in resin compositions for semiconductor encapsulation can be used. Moreover, the inorganic filler (D) may be surface-treated.
  • the inorganic filler (D) include silica such as fused silica, crystalline silica, and amorphous silicon dioxide; alumina; talc; titanium oxide; silicon nitride; and aluminum nitride. These inorganic fillers may be used alone or in combination of two or more.
  • the inorganic filler (D) preferably contains silica from the viewpoint of excellent versatility.
  • the shape of silica includes spherical silica, crushed silica, and the like.
  • the average diameter (D 50 ) of the inorganic filler (D) is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, and preferably 80 ⁇ m or less, from the viewpoint of improving moldability and adhesion. It is more preferably 50 ⁇ m or less, and still more preferably 40 ⁇ m or less.
  • the particle size distribution of the inorganic filler (D) is obtained by measuring the particle size distribution of the particles on a volume basis using a commercially available laser diffraction particle size distribution analyzer (eg, SALD-7000 manufactured by Shimadzu Corporation). can be obtained by
  • the maximum particle size of the inorganic filler (D) is preferably 10 ⁇ m or more, more preferably 20 ⁇ m or more, and preferably 100 ⁇ m or less, from the viewpoint of improving moldability and adhesion. It is preferably 80 ⁇ m or less.
  • the specific surface area of the inorganic filler (D) is preferably 1 m 2 /g or more, more preferably 3 m 2 /g or more, and preferably 20 m 2 /g or more, from the viewpoint of improving moldability and adhesion. 2 /g or less, more preferably 10 m 2 /g or less.
  • the content of the inorganic filler (D) in the encapsulating resin composition improves the low hygroscopicity and low thermal expansion of the encapsulating material formed using the encapsulating resin composition, and the obtained semiconductor device From the viewpoint of more effectively improving the moisture resistance reliability and reflow resistance of the entire sealing resin composition, it is preferably 50% by mass or more, more preferably 60% by mass or more, and still more preferably 65% by mass. % by mass or more.
  • the content of the inorganic filler (D) in the encapsulating resin composition is for example, it may be 97% by mass or less, preferably 95% by mass or less, and more preferably 90% by mass or less with respect to the entire composition.
  • the encapsulating resin composition of the present embodiment may contain components other than the components described above, such as silane coupling agents, fluidity imparting agents, release agents, ion trapping agents, low stress components, flame retardants, coloring agents, Various additives such as agents, antioxidants, etc. can be added as appropriate.
  • the encapsulating resin composition of the present embodiment is solid at room temperature (25° C.), and its shape can be selected according to the molding method of the encapsulating resin composition. , particulate such as granule; and sheet.
  • the respective components described above are mixed by known means, further melt-kneaded with a kneader such as a roll, kneader or extruder, cooled and then pulverized. method.
  • a kneader such as a roll, kneader or extruder
  • molding may be performed to obtain a particulate or sheet-like encapsulating resin composition.
  • a particulate encapsulating resin composition may be obtained by compression molding into a tablet.
  • a sheet-like encapsulating resin composition may be obtained by, for example, a vacuum extruder.
  • the degree of dispersion, fluidity, etc. of the resulting encapsulating resin composition may be appropriately adjusted.
  • the encapsulating resin composition of the present embodiment has excellent fluidity, and the spiral flow length measured under the following conditions is 100 cm or more and 250 cm or less, preferably 100 cm or more and 220 cm or less, more preferably 120 cm or more and 200 cm or less. , more preferably 155 cm or more and 180 cm or less, Thereby, the moldability of the encapsulating resin composition is excellent.
  • (conditions) Flow length measured by injecting the sealing resin composition into a spiral flow measurement mold according to EMMI-1-66 under the conditions of a mold temperature of 175 ° C., an injection pressure of 6.9 MPa, and a curing time of 120 seconds. is the spiral flow length.
  • the encapsulating resin composition of the present embodiment has excellent curability, and has a gel time at 175° C. of 10 seconds to 60 seconds, preferably 20 seconds to 50 seconds, more preferably 32 seconds to 45 seconds. is. As a result, the encapsulating resin composition has excellent filling properties, and the generation of unfilled portions can be suppressed.
  • the gel time can be measured by melting the resin composition on a hot plate heated to 175° C. and kneading it with a spatula until it becomes tack-free (gel time).
  • the bending strength of the cured product obtained by curing the encapsulating resin composition of the present embodiment at 175° C. for 2 minutes at room temperature of 25° C. is 80 MPa or more, preferably 100 MPa or more, more preferably 110 MPa or more. be able to. Although the upper limit is not particularly limited, it is 300 MPa or less.
  • the cured product obtained by curing the encapsulating resin composition of the present embodiment at 175°C for 2 minutes has a flexural modulus at room temperature of 25°C of 10,000 MPa or more, preferably 12,000 MPa or more, and more preferably 13,000 MPa or more. can do. Although the upper limit is not particularly limited, it is 30000 MPa or less.
  • the encapsulating resin composition of the present embodiment can provide a cured product having excellent mechanical strength because the cured product obtained from the composition has a flexural strength or a flexural modulus within the above range. In the present embodiment, for example, the above characteristics can be controlled by appropriately selecting the type and amount of each component contained in the encapsulating resin composition, the method of preparing the encapsulating resin composition, and the like. .
  • ⁇ Cured product> By curing the encapsulating resin composition of the present embodiment, it is possible to obtain a cured product that is obtained from a plant-derived raw material and that is friendly to the global environment.
  • the biomass degree of the hardened body can be 5% or more and 95% or less.
  • the encapsulating resin composition of the present embodiment can be used as a sealing material for various electronic components. etc.), stator cores in which coils are insulated (see Japanese Patent Application Laid-Open No. 2020-094092, etc.), automotive electronic control units (see International Publication WO2016/139985, etc.), sealing materials for semiconductor devices, etc. .
  • the permanent magnets are fixed to the rotor core by inserting the permanent magnets into holes provided in the rotor core and filling a space between the holes and the permanent magnets with a resin composition.
  • the tablet obtained by the method of the present invention can be used.
  • the tablet of the present invention as a sealing material, it becomes possible to increase the size of the rotor core and to produce a plurality of rotor cores simultaneously.
  • the stator core has a plurality of teeth, and coils are wound around the plurality of teeth. At this time, the coil needs to be insulated from the stator core, and can be insulated by interposing a sealing resin composition.
  • the resin composition of the present invention can be applied in the step of interposing the resin composition.
  • the semiconductor device is obtained by encapsulating a semiconductor element with a cured product of the encapsulating resin composition of the present embodiment described above.
  • semiconductor devices include integrated circuits, large-scale integrated circuits, transistors, thyristors, diodes, solid-state imaging devices, and the like.
  • the semiconductor element is preferably a so-called element that does not involve the input and output of light, excluding optical semiconductor elements such as light-receiving elements and light-emitting elements (light-emitting diodes, etc.).
  • the base material of a semiconductor device is, for example, a wiring board such as an interposer, or a lead frame. Also, the semiconductor element is electrically connected to the substrate by wire bonding, flip-chip bonding, or the like.
  • Examples of semiconductor devices obtained by encapsulating a semiconductor element by encapsulation molding using an encapsulating resin composition include MAP (Mold Array Package), QFP (Quad Flat Package), SOP (Small Outline Package), CSP (Chip Size Package), QFN (Quad Flat Non-leaded Package), SON (Small Outline Non-leaded Package), BGA (Ball Grid Array), LF-BGA (Lead Flame BGA), FCBGA (Flip Chip BGA), Types include MAPBGA (Molded Array Process BGA), eWLB (Embedded Wafer-Level BGA), Fan-In type eWLB, and Fan-Out type eWLB.
  • MAP Metal Array Package
  • QFP Quant Flat Package
  • SOP Small Outline Package
  • CSP Chip Size Package
  • QFN Quad Flat Non-leaded Package
  • SON Small Outline Non-leaded Package
  • BGA Ball Grid Array
  • LF-BGA Lead Flame BGA
  • the semiconductor device 100 shown in FIG. 1 includes a semiconductor element 20 mounted on a substrate 30 and a sealing material 50 sealing the semiconductor element 20 .
  • the encapsulating material 50 is composed of a cured product obtained by curing the encapsulating resin composition of the present embodiment described above.
  • FIG. 1 illustrates a case where the board 30 is a circuit board.
  • the board 30 is a circuit board.
  • a plurality of solder balls 60 are formed on the other surface of the substrate 30 opposite to the surface on which the semiconductor element 20 is mounted.
  • Semiconductor element 20 is mounted on substrate 30 and electrically connected to substrate 30 via wires 40 .
  • the semiconductor element 20 may be flip-chip mounted on the substrate 30 .
  • the wire 40 includes, but is not limited to, Ag wire, Ni wire, Cu wire, Au wire, and Al wire.
  • the wire 40 is Ag, Ni or Cu, or one or more of these. composed of an alloy containing
  • the sealing material 50 seals the semiconductor element 20 so as to cover, for example, the other surface of the semiconductor element 20 opposite to the surface facing the substrate 30 .
  • a sealing material 50 is formed so as to cover the other surface and the side surface of the semiconductor element 20 .
  • the encapsulating material 50 is composed of a cured product of the encapsulating resin composition described above. Therefore, in the semiconductor device 100, the adhesion between the sealing material 50 and the wire 40 is excellent, so that the semiconductor device 100 is highly reliable.
  • the encapsulating material 50 can be formed, for example, by encapsulating the encapsulating resin composition using a known method such as transfer molding or compression molding.
  • FIG. 2 is a cross-sectional view showing the configuration of the semiconductor device 100 according to this embodiment, and shows an example different from FIG.
  • the semiconductor device 100 shown in FIG. 2 uses a lead frame as the substrate 30 .
  • semiconductor element 20 is mounted, for example, on die pad 32 of substrate 30 and electrically connected to outer leads 34 via wires 40 .
  • the encapsulant 50 is composed of a cured product of the encapsulating resin composition of the present embodiment in the same manner as in the example shown in FIG.
  • the resulting resin had a softening point of 83° C., a free phenol content of 0.1%, and a biomass content of 31% excluding unreacted phenols. Also, the proportion of peaks derived from unsaturated bond hydrogen in alkyl chains determined by NMR was 0.1% or less with respect to the total integrated value of peaks derived from hydrogen bonded to carbon atoms.
  • Epoxy resin 1 cresol novolac type epoxy resin (manufactured by DIC, EPICLON-N660)
  • Epoxy resin 2 biphenyl type epoxy resin (manufactured by Mitsubishi Chemical Corporation, YX4000)
  • Epoxy resin 3 phenol aralkyl epoxy resin (manufactured by Nippon Kayaku Co., Ltd., NC-2000)
  • Epoxy resin 4 biphenyl aralkyl type epoxy resin (manufactured by Nippon Kayaku Co., Ltd., NC-3000)
  • Curing agent 1 (phenolic curing agent (B1)): novolak phenolic resin (PR-HF-3 manufactured by Sumitomo Bakelite Co., Ltd.)
  • Curing agent 2 (phenolic curing agent (B2)): biomass-modified phenolic resin obtained in Synthesis Example 1
  • Curing accelerator triphenylphosphine Silane coupling agent: N-phenylaminopropyltrimethoxysilane represented by the following formula (S1) (CF-4083 manufactured by Dow Toray Industries, Inc.)
  • HAST humidity resistance reliability
  • HTSL high temperature storage properties
  • the obtained semiconductor device was subjected to a HAST (Highly Accelerated Temperature and Humidity Stress Test) test in accordance with IEC68-2-66.
  • the test conditions were 130° C., 85% RH, applied voltage of 20 V, and treatment for 240 hours.
  • Four terminals per semiconductor device were observed for the presence or absence of open circuit defects, and a total of 20 circuits were observed for five semiconductor devices to measure the number of defective circuits.
  • a sample with 0 defects was marked with ⁇ , and a sample with 1 to 5 defects was marked with x.
  • the encapsulating resin compositions obtained in Comparative Example 1 and Examples 1 to 5 showed good results with 0 defects.
  • High temperature storage characteristics using a low pressure transfer molding machine (Daiichi Seiko Co., Ltd., GP-ELF), a mold temperature of 180 ° C., an injection pressure of 6.9 ⁇ 0.17 MPa, and a semiconductor under the conditions of 90 seconds.
  • a lead frame on which a semiconductor element (silicon chip) is mounted is molded by injecting an encapsulating resin composition into a 16-pin DIP (Dual Inline Package, lead frame made of 42 alloy, size 7 mm x 11 mm).
  • the semiconductor element is 5 x 9 mm x 0.35 mm thick.
  • the semiconductor element has an oxide layer with a thickness of 5 ⁇ m on the surface, and an aluminum wiring pattern with a line and space of 10 ⁇ m is formed on the surface.
  • the aluminum wiring pad portion on the element and the lead frame pad portion were bonded with a gold wire having a diameter of 25 ⁇ m).
  • the initial resistance values of 10 semiconductor devices which had been subjected to heat treatment at 175° C. for 4 hours as post curing were measured, and high temperature storage treatment was performed at 175° C. for 1000 hours. After the high-temperature treatment, the resistance value of the semiconductor device was measured, and the semiconductor device with 130% of the initial resistance value was regarded as defective. When x is displayed.
  • the semiconductor devices obtained using the resin compositions for semiconductor encapsulation of Comparative Example 1 and Examples 1 to 5 exhibited a good reliability of 0/10.
  • the encapsulating resin compositions of Examples according to the present invention contain a phenolic curing agent obtained from a plant-derived raw material, so that they have excellent fluidity, curability, and electrical reliability.
  • the curability and mechanical properties were equivalent to those of a conventional encapsulating resin composition containing only a petroleum-derived phenol curing agent.
  • semiconductor element 20 semiconductor element 30 substrate 32 die pad 34 outer lead 40 wire 50 sealing material 60 solder ball 100 semiconductor device

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)
PCT/JP2023/006237 2022-02-28 2023-02-21 封止用樹脂組成物および半導体装置 Ceased WO2023162975A1 (ja)

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JP2023551185A JP7477055B2 (ja) 2022-02-28 2023-02-21 封止用樹脂組成物および半導体装置
EP23759976.6A EP4488314A4 (en) 2022-02-28 2023-02-21 SEALING RESIN COMPOSITION AND SEMICONDUCTIVE DEVICE
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