WO2019188255A1 - Feuille de résine et procédé de fabrication associé - Google Patents

Feuille de résine et procédé de fabrication associé Download PDF

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Publication number
WO2019188255A1
WO2019188255A1 PCT/JP2019/010018 JP2019010018W WO2019188255A1 WO 2019188255 A1 WO2019188255 A1 WO 2019188255A1 JP 2019010018 W JP2019010018 W JP 2019010018W WO 2019188255 A1 WO2019188255 A1 WO 2019188255A1
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WO
WIPO (PCT)
Prior art keywords
resin composition
resin
resin sheet
composition layer
less
Prior art date
Application number
PCT/JP2019/010018
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English (en)
Japanese (ja)
Inventor
康貴 渡邉
裕介 根津
貴志 杉野
Original Assignee
リンテック株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by リンテック株式会社 filed Critical リンテック株式会社
Priority to CN201980022521.8A priority Critical patent/CN111918931A/zh
Priority to JP2020509851A priority patent/JPWO2019188255A1/ja
Priority to KR1020207024355A priority patent/KR20200135310A/ko
Publication of WO2019188255A1 publication Critical patent/WO2019188255A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/295—Organic, e.g. plastic containing a filler
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to a resin sheet used for sealing electronic components and a method for manufacturing the same.
  • an electronic component such as a semiconductor chip is sealed with a curable resin composition.
  • the electronic component is sealed by curing the resin composition.
  • a semiconductor device obtained by sealing an electronic component as described above may be exposed to high temperatures due to heat generation during use. Therefore, the hardened
  • Patent Document 1 discloses a resin composition containing a predetermined epoxy resin, a curing agent and a phosphate ester. In addition, the said resin composition is assumed that the electronic component is sealed by transfer molding.
  • the above-described resin composition for sealing an electronic component is formed into a sheet shape to form a resin sheet.
  • the resin composition hardly flows during sealing, thereby suppressing the occurrence of unevenness due to the flow and the movement of the electronic component.
  • the resin composition disclosed in Patent Document 1 seals electronic components by transfer molding and cannot be molded well into a sheet shape. Therefore, a resin sheet having good flame retardancy cannot be produced using the resin composition disclosed in Patent Document 1.
  • a cured product obtained by curing the resin composition has good adhesion to the electronic component and a substrate that supports the electronic component. It is required to have. In particular, even when a force that shears the cured product and the target that is in contact with the cured product is applied, the cured product has sufficient adhesive force to prevent the cured product from peeling from the target. Is required. In particular, such adhesive strength is required to be sufficiently maintained even after the obtained semiconductor device is subjected to a reliability test (such as a wet heat test).
  • Patent Document 1 Although the resin composition disclosed in Patent Document 1 is disclosed in the example of Cited Document 1 that the occurrence of cracks can be suppressed to some extent when the cured product is subjected to a reflow treatment under predetermined conditions, it has been described above. Adhesive strength sufficient to counter such shear forces cannot be achieved.
  • This invention is made
  • the present invention is a resin sheet used for sealing an electronic component, the resin sheet comprising a thermosetting resin, a thermoplastic resin, an inorganic filler, Provided is a resin sheet comprising a resin composition layer formed from a resin composition containing a flame retardant, wherein the flame retardant is an aromatic condensed phosphate ester that is liquid at room temperature (Invention 1). ).
  • the resin composition layer is formed from a resin composition containing an aromatic condensed phosphate ester that is liquid at room temperature as a flame retardant, whereby the resin composition A cured product obtained by curing the physical layer has excellent flame retardancy. Furthermore, the aromatic condensed phosphate ester that is liquid at room temperature exhibits good compatibility with other components contained in the resin composition, and thereby the cured layer formed by curing the resin composition layer has high uniformity. Thus, the cured product has excellent adhesive force with respect to an object with which the cured product is in contact.
  • the aromatic condensed phosphate ester has the following formula (1): (In the formula (1), n represents an integer of 1 or more and 5 or less, R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 represents a hydrogen atom or 1 carbon atom. Represents an alkyl group of ⁇ 5.) And the following formula (2) (In the formula (2), Ar represents a divalent aromatic hydrocarbon, and R 3 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.) It is preferable that at least 1 type of the compound represented by these is included (invention 2).
  • the aromatic condensed phosphate ester preferably has a viscosity at 25 ° C. of 5000 mPa ⁇ s or more and 30000 mPa ⁇ s or less (Invention 3).
  • the content of the flame retardant in the resin composition is preferably 0.5% by mass or more and 5.0% by mass or less (Invention 4).
  • the present invention is a method for producing the resin sheet (Invention 1 to 5), wherein a coating liquid containing the resin composition layer is applied onto a predetermined release sheet, whereby the resin composition layer
  • the manufacturing method of the resin sheet characterized by providing the process of forming is provided (invention 6).
  • the resin sheet of the present invention can form a cured product having excellent flame retardancy and excellent adhesive force. Moreover, according to the manufacturing method of this invention, such a resin sheet can be manufactured.
  • the resin sheet according to the present embodiment is used for sealing electronic components, and is formed from a resin composition containing a thermosetting resin, a thermoplastic resin, an inorganic filler, and a flame retardant.
  • a resin composition layer is provided.
  • the flame retardant is an aromatic condensed phosphate ester that is liquid at room temperature.
  • the resin composition in the present embodiment can be cured by heating because it contains a thermosetting resin.
  • the cured layer formed by curing the resin composition layer contains the above-described inorganic filler, and the formed cured layer exhibits good heat resistance and mechanical strength. Accordingly, the electronic component can be satisfactorily sealed by using the resin sheet according to the present embodiment.
  • the resin composition in this embodiment can maintain the sheet-like shape of the resin composition layer favorably by containing a thermoplastic resin. Therefore, the resin sheet in the present embodiment is excellent in handleability, and when using the resin sheet according to the present embodiment, the resin sheet is laminated on the electronic component without performing transfer molding. Sealing can be performed by a simpler operation.
  • the resin composition in the present embodiment contains an aromatic condensed phosphate ester that is liquid at room temperature as a flame retardant, so that the semiconductor device manufactured using the resin sheet according to the present embodiment generates heat during use. Even if the semiconductor device is placed in a high temperature environment, the formed hardened layer is difficult to burn and exhibits excellent flame retardancy.
  • the aromatic condensed phosphate ester flame retardant which is liquid at room temperature exhibits excellent compatibility with other components such as thermoplastic resins and thermosetting resins contained in the resin composition. Therefore, in the resin composition layer in the present embodiment, each component is uniformly mixed without aggregating the constituent components, and by curing the resin composition layer, a highly uniform cured layer is obtained. Can be formed. As a result, the adhesive force between the cured layer and the target that the cured layer contacts is improved, and the cured product is described above even when a force that shears the cured product and the target is applied. Peeling from the object is suppressed.
  • the resin composition in the present embodiment contains a thermoplastic resin
  • the flame retardant described above can exhibit excellent compatibility with the thermoplastic resin
  • the resin composition is a predetermined one.
  • the viscosity when the resin composition layer is heated for curing the resin composition layer, it becomes difficult for the flame retardant to bleed out from the resin composition layer. For this reason, a decrease in flame retardancy due to a decrease in the content of the flame retardant in the resin composition layer is suppressed, and an adverse effect on the semiconductor device due to the bleed-out flame retardant is also suppressed.
  • thermosetting resin is not particularly limited as long as the resin composition layer can be cured.
  • a resin usually contained in a sealing material is used. can do.
  • epoxy resin, phenol resin, melamine resin, urea resin, polyester resin, urethane resin, acrylic resin, polyimide resin, benzoxazine resin, phenoxy resin, acid anhydride compound, amine compound, naphthol resin, activity Examples include ester resins, benzoxazine resins, cyanate ester resins, and the like. These may be used alone or in combination of two or more. Among these, it is preferable to use an epoxy resin, a phenol resin, or a mixture thereof.
  • Epoxy resins generally have the property of forming a three-dimensional network when heated and forming a hardened product.
  • various known epoxy resins can be used. Specifically, glycidyl ethers of phenols such as bisphenol A, bisphenol F, resorcinol, phenyl novolac, cresol novolac; butanediol, polyethylene Glycidyl ethers of alcohols such as glycol and polypropylene glycol; Glycidyl ethers of carboxylic acids such as phthalic acid, isophthalic acid and tetrahydrophthalic acid; Alkyl glycidyl type epoxy resin; vinylcyclohexane diepoxide, 3,4-epoxycyclohexylmethyl-3,4-dicyclohexanecarboxylate, 2- (3,4-epoxy I) Cyclohexyl-5,5-spiro (3,4-epoxy) cyclohexane-m-d
  • an epoxy resin having a biphenyl skeleton, a triphenylmethane skeleton, a dicyclohexadiene skeleton, a naphthalene skeleton, or the like can also be used. These epoxy resins can be used alone or in combination of two or more.
  • glycidyl ether of bisphenol A bisphenol A type epoxy resin
  • epoxy resin having a biphenyl skeleton bisphenol A type epoxy resin
  • epoxy resin having a naphthalene skeleton naphthalene type epoxy resin
  • phenol resin examples include bisphenol A, tetramethyl bisphenol A, diallyl bisphenol A, biphenol, bisphenol F, diallyl bisphenol F, triphenylmethane phenol, tetrakisphenol, novolac phenol, cresol novolac resin, and biphenyl aralkyl skeleton.
  • Phenol (biphenyl type phenol) and the like can be mentioned, and among these, it is preferable to use biphenyl type phenol.
  • These phenol resins can be used individually by 1 type or in combination of 2 or more types.
  • an epoxy resin as curable resin it is preferable to use a phenol resin together from the viewpoint of reactivity with the epoxy resin.
  • the content of the thermosetting resin in the resin composition is preferably 10% by mass or more, particularly preferably 15% by mass or more, and further preferably 20% by mass or more. Further, the content is preferably 60% by mass or less, particularly preferably 50% by mass or less, and further preferably 40% by mass or less. When the content is 10% by mass or more, the resin composition layer is more sufficiently cured, and the electronic component can be more firmly sealed. Further, when the content is 60% by mass or less, curing at an unintended stage of the resin composition layer can be further suppressed, and the storage stability becomes more excellent.
  • thermoplastic resin is not particularly limited as long as it is suitable for forming the resin composition into a sheet.
  • thermoplastic resins include phenoxy resins, polyvinyl acetal resins, olefin resins, polyester resins, polyurethane resins, polyester urethane resins, amide resins, styrene resins, silane resins, rubber resins, etc. These may be used alone or in combination of two or more.
  • the phenoxy resin is not particularly limited.
  • bisphenol A type bisphenol F type, bisphenol A / bisphenol F copolymer type, bisphenol S type, bisphenol acetophenone type, novolac type, fluorene type, dicyclopentadiene type
  • Examples include norbornene type, naphthalene type, anthracene type, adamantane type, terpene type, trimethylcyclohexane type, biphenol type, and biphenyl type.
  • bisphenol A type phenoxy resin is preferably used.
  • the content of the thermoplastic resin in the resin composition is preferably 1% by mass or more, particularly preferably 3% by mass or more, and further preferably 5% by mass or more. Further, the content is preferably 30% by mass or less, particularly preferably 20% by mass or less, and further preferably 10% by mass or less. When the content is in the above range, it becomes easier to form the resin composition layer into a sheet shape.
  • the inorganic filler is not particularly limited as long as a desired mechanical strength can be imparted to a cured layer formed by curing the resin composition layer.
  • the inorganic filler include silica, alumina, glass, titanium oxide, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride,
  • Examples include fillers made of aluminum oxide borate whisker, boron nitride, crystalline silica, amorphous silica, mullite, cordierite, and other composite oxides, montmorillonite, smectite, etc., and these can be used alone. Alternatively, two or more kinds can be used in combination. Among these, it is preferable to use a silica filler.
  • the shape of the inorganic filler may be any of a granular shape, a needle shape, a plate shape, an indeterminate shape, etc., but among these, a spherical shape is preferable.
  • the average particle size of the inorganic filler is preferably 0.01 ⁇ m or more, particularly preferably 0.1 ⁇ m or more, and more preferably 0.3 ⁇ m or more.
  • the average particle size of the inorganic filler is preferably 3.0 ⁇ m or less, and particularly preferably 1.0 ⁇ m or less.
  • the average particle size of the inorganic filler in the present specification is a value measured by a dynamic light scattering method. For example, a particle size distribution measuring device (manufactured by Nikkiso Co., Ltd., product name “Nanotrack Wave-UT151”) is used. Can be measured.
  • the maximum particle size of the inorganic filler is preferably 0.05 ⁇ m or more, and particularly preferably 0.5 ⁇ m or more.
  • the maximum particle size is preferably 5 ⁇ m or less, particularly preferably 3 ⁇ m or less.
  • the maximum particle size of the inorganic filler in the present specification is a value measured by a dynamic light scattering method.
  • the particle size distribution measuring device manufactured by Nikkiso Co., Ltd., product name “Nanotrack Wave-UT151” is used. Can be measured.
  • the inorganic filler is surface-treated with the surface treating agent.
  • the dispersibility and filling property of the inorganic filler in the resin composition are improved.
  • the minimum coating area of the surface treatment agent is preferably less than 550 m 2 / g, particularly preferably 520 m 2 / g or less, and more preferably 450 m 2 / g or less.
  • the minimum covering area of the surface treatment agent is preferably 100 m 2 / g or more, particularly preferably 200 m 2 / g or more, and more preferably 300 m 2 / g or more.
  • Examples of the surface treatment agent include epoxy silane and vinyl silane. Among these, it is preferable to use epoxysilane.
  • Specific examples of the epoxy silane include, for example, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane and the like. Of these, 3-glycidoxypropyltrimethoxysilane is preferably used.
  • vinyl silane examples include vinyl triacetoxy silane, vinyl trimethoxy silane, vinyl triethoxy silane, vinyl trichloro silane, vinyl tris (2-methoxy ethoxy) silane, and the like. Among these, it is preferable to use vinyltrimethoxysilane.
  • the method for surface-treating the inorganic filler with the surface treatment agent is not particularly limited, and can be performed by a general method.
  • the untreated inorganic filler can be stirred at room temperature using a mixer, and after the surface treatment agent is sprayed thereon, the surface treatment can be performed by further stirring for a predetermined time.
  • the stirring time after spraying is preferably 5 minutes or more and 15 minutes or less, for example.
  • the inorganic filler may be taken out from the mixer and allowed to stand for one day or longer, or a slight heat treatment may be performed.
  • a mixer a well-known thing can be used, for example, blenders, such as a V blender, a ribbon blender, a bubble cone blender, a Henschel mixer, a mixer, such as a concrete mixer, a ball mill etc., Among these, a mixer is used. Is preferred.
  • the content of the inorganic filler in the resin composition is preferably 65% by mass or more, particularly preferably 70% by mass or more, and more preferably 72% by mass or more. Further, the content is preferably 95% by mass or less, particularly preferably 90% by mass or less, and further preferably 80% by mass or less.
  • the content of the inorganic filler is 65% by mass or more, the cured layer formed by curing the resin composition layer has better mechanical strength. Further, when the content of the inorganic filler is 95% by mass or less, the resin composition layer is easily cured, and it becomes possible to manufacture a semiconductor device having better quality by using the resin sheet. .
  • the flame retardant in the present embodiment is an aromatic condensed phosphate ester that is liquid at room temperature.
  • “normal temperature” usually means a temperature of 20 ° C. or higher and 30 ° C. or lower
  • “liquid at normal temperature” means that a flame retardant is dissolved in a solvent or mixed with a solvent under such a temperature environment. Without mentioning, it means that the flame retardant is in a liquid state or a fluid state.
  • the melting point of the aromatic condensed phosphate ester in the present embodiment is preferably 5 ° C. or less, particularly preferably ⁇ 5 ° C. or less, and further preferably ⁇ 15 ° C. or less.
  • the aromatic condensed phosphorus is used at the temperature when the resin sheet according to the present embodiment is stored and used, and at the temperature when the resin composition layer in the present embodiment is cured.
  • the acid ester can be maintained in a liquid state. This makes it easy to maintain good compatibility between the flame retardant and other components, and as a result, the cured layer formed by curing the resin composition layer in the present embodiment is more excellent for electronic components and substrates. It has an adhesive strength.
  • the lower limit of the melting point is not particularly limited, and is preferably, for example, ⁇ 50 ° C. or higher, particularly preferably ⁇ 40 ° C. or higher, and more preferably ⁇ 30 ° C. or higher.
  • the viscosity at 25 ° C. of the aromatic condensed phosphate ester in this embodiment is preferably 30000 mPa ⁇ s or less, particularly preferably 25000 mPa ⁇ s or less, and more preferably 20000 mPa ⁇ s or less.
  • the viscosity is 30000 mPa ⁇ s or less, it becomes easy to maintain good compatibility between the flame retardant and other components, and as a result, a cured layer formed by curing the resin composition layer in the present embodiment, It has better adhesion to electronic components and substrates.
  • the lower limit of the said viscosity does not specifically limit about the lower limit of the said viscosity, For example, it is preferable that it is 5000 mPa * s or more, It is especially preferable that it is 8000 mPa * s or more, Furthermore, it is preferable that it is 10000 mPa * s or more.
  • the vapor pressure at 25 ° C. of the aromatic condensed phosphate ester in the present embodiment is preferably 1.0 ⁇ 10 ⁇ 5 kPa or less, particularly preferably 5.0 ⁇ 10 ⁇ 6 kPa or less. Is preferably 1.0 ⁇ 10 ⁇ 6 kPa or less.
  • the vapor pressure is 1.0 ⁇ 10 ⁇ 5 kPa or less
  • the temperature at which the resin sheet according to the present embodiment is stored and used, and the resin composition layer in the present embodiment is cured.
  • the aromatic condensed phosphate ester becomes difficult to volatilize, and the bleedout of the flame retardant from the resin composition layer is effectively suppressed.
  • the reduction in flame retardancy due to such bleed-out is effectively suppressed, and the occurrence of adverse effects on the semiconductor device due to the flared-out flame retardant is also effectively suppressed.
  • n represents a positive integer
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Represents a group.
  • the compound represented by these is mentioned.
  • the compounds may be used alone, or in, n, at least one of R 1 and R 2 may be used in combination of two or more different compounds.
  • N in the above formula (1) is preferably 1 or more and 5 or less.
  • Preferred examples of the compound represented by the above formula (1) include compounds in which R 1 is all a hydrogen atom and R 2 is an alkyl group having 1 carbon atom (—CH 3 ), that is, Formula (3) (In formula (3), n represents a positive integer.)
  • the compound represented by these is mentioned.
  • the said compound may be used individually by 1 type, or may be used combining 2 or more types of compounds from which n differs.
  • N in the above formula (3) is preferably 1 or more and 5 or less.
  • the compound represented by the above formula (3) is superior in compatibility with other components in the resin composition, a cured layer obtained by curing the resin composition layer in this embodiment is an electronic component or It has better adhesion to the substrate.
  • the following formula (2) (In the formula (2), Ar represents a divalent aromatic hydrocarbon, and R 3 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.)
  • the compound represented by these is mentioned.
  • the said compound may be used individually by 1 type, or may be used combining 2 or more types of compounds from which R ⁇ 3 > differs.
  • aromatic hydrocarbon in the above formula (2) examples include benzene, naphthalene, anthracene, fluorene, phenanthrene and the like.
  • the content of the flame retardant in the resin composition is preferably 0.5% by mass or more, particularly preferably 1.0% by mass or more, and more preferably 2% by mass or more. Further, the content is preferably 10% by mass or less, particularly preferably 7% by mass or less, and further preferably 5% by mass or less.
  • the content of the flame retardant is 0.5% by mass or more
  • the cured layer obtained by curing the resin composition layer in the present embodiment easily exhibits excellent flame retardancy.
  • aggregation of the flame retardant in a resin composition layer can be effectively suppressed because content of a flame retardant is 10 mass% or less, As a result, a hardening layer is with respect to an electronic component or a board
  • the resin composition further contains a curing catalyst.
  • a curing catalyst examples include an imidazole curing catalyst, an amine curing catalyst, and a phosphorus curing catalyst.
  • imidazole-based curing catalyst examples include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1,2-dimethylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl -2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4,5-di (hydroxymethyl) imidazole, etc. From the perspective of sex It is preferred to use 2-ethyl-4-methylimidazole.
  • the amine-based curing catalyst include triazine compounds such as 2,4-diamino-6- [2′-methylimidazolyl- (1 ′)] ethyl-s-triazine, 1,8-diazabicyclo [5,4, 0] tertiary amine compounds such as undecene-7 (DBU), triethylenediamine, benzyldimethylamine, triethanolamine and the like.
  • DBU undecene-7
  • 2,4-diamino-6- [2'-methylimidazolyl- (1 ')] ethyl-s-triazine is preferable.
  • phosphorus curing catalyst examples include triphenylphosphine, tributylphosphine, tri (p-methylphenyl) phosphine, tri (nonylphenyl) phosphine, and the like.
  • the above-mentioned curing catalyst may be used alone or in combination of two or more.
  • the content of the curing catalyst in the resin composition is preferably 0.01% by mass or more, particularly preferably 0.05% by mass or more, and more preferably 0.1% by mass or more. preferable. Further, the content is preferably 2.0% by mass or less, particularly preferably 1.5% by mass or less, and further preferably 1.0% by mass or less. When the content is in the above range, the resin composition can be cured more favorably.
  • the resin composition in this embodiment may further contain a coloring material.
  • the resin composition contains a coloring material
  • the cured layer formed by curing the resin composition layer in the present embodiment is colored, and the concealability of the electronic component sealed by the cured layer is improved. At the same time, it is easy to perform laser marking on the cured layer.
  • the coloring material is not particularly limited as long as it can color the cured layer, and those generally used as pigments and dyes can be used.
  • the coloring material preferably has excellent insulating properties and is also excellent in the effect of blocking electromagnetic waves that induce malfunctions, and such a coloring material comprises an aliphatic hydrocarbon group for all carbon atoms. It is preferable to use a carbon-based material, an insulating metal compound, or the like in which the proportion of carbon atoms to be exceeded exceeds 3% by mass.
  • the carbon-based material described above is a carbon-based pigment from the viewpoint of being excellent in concealability, laser marking property, and insulation and easily achieving an effect of blocking electromagnetic waves that induce malfunction. *
  • Examples of the carbon-based material in which the proportion of carbon atoms constituting the aliphatic hydrocarbon group with respect to all carbon atoms exceeds 3% by mass include carbon filler, coke, charcoal, diamond, etc.
  • a carbon filler is preferable.
  • a carbon filler is an amorphous carbon substance having a structure in which conjugated systems of carbon atoms are mainly linked, but having a structure in which the conjugation of the carbon atoms is appropriately cut off by an aliphatic hydrocarbon group.
  • the coloring materials described above may be used alone or in combination of two or more.
  • the content of the coloring material in the resin composition is preferably 0.5% by mass or more, and particularly preferably 1.0% by mass or more.
  • the content is preferably 5% by mass or less, and particularly preferably 3% by mass or less.
  • the resin composition in the present embodiment may further contain a plasticizer, a stabilizer, a tackifier, a coupling agent, an antistatic agent, an antioxidant, and the like.
  • the thickness of the resin composition layer in the present embodiment is preferably 20 ⁇ m or more, particularly preferably 50 ⁇ m or more, and more preferably 100 ⁇ m or more.
  • the thickness of the resin composition layer is 1000 ⁇ m or less, preferably 500 ⁇ m or less, and particularly preferably 300 ⁇ m or less.
  • the thickness of the resin composition layer is 20 ⁇ m or more, the resin composition layer has excellent embedding properties with respect to electronic components.
  • the thickness of the resin composition layer is 1000 ⁇ m or less, it is easy to reduce the size and thin the semiconductor device manufactured using the resin sheet according to the present embodiment.
  • the resin sheet according to the present embodiment may include a release sheet laminated on at least one surface of the resin composition layer.
  • the configuration of the release sheet is arbitrary, and examples thereof include plastic films such as polyester films such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate, and polyolefin films such as polypropylene and polyethylene. It is preferable that a peeling treatment is performed on these peeling surfaces (surfaces in contact with the resin composition layer of the resin sheet).
  • the release agent used for the release treatment include silicone-based, fluorine-based, long-chain alkyl-based, alkyd-based, olefin-based, and rubber-based release agents.
  • the resin composition layer is laminated on a silicon mirror wafer, and the resin composition layer is cured to form a cured layer.
  • the shear adhesive strength of the layer to the above-mentioned wafer is preferably 30 N / 5 mm ⁇ or more, particularly preferably 35 N / 5 mm ⁇ or more, and more preferably 40 N / 5 mm ⁇ or more.
  • the resin composition in the present embodiment contains an aromatic condensed phosphate ester that is liquid at room temperature as a flame retardant, and the component is excellent in compatibility with other components contained in the resin composition. Thus, the obtained cured layer can easily achieve the above-described shear adhesive force.
  • the resin sheet according to the present embodiment makes it easy to form a cured layer having an excellent adhesive force with respect to the electronic component and the substrate that supports the electronic component.
  • the upper limit value of the shear adhesive force described above is not particularly limited. For example, it is preferably 140 N / 5 mm ⁇ or less, particularly preferably 120 N / 5 mm ⁇ or less, and more preferably 100 N / 5 mm ⁇ or less. It is preferable that Moreover, the shear adhesive force mentioned above is a shear adhesive force measured before putting a hardened layer on the wet heat conditions mentioned later. Further, the above-mentioned shear adhesive strength is measured in accordance with MIL-STD-883J (METHOD 20199.9), and details of the measuring method are as described later.
  • the resin composition layer is laminated on a silicon mirror wafer, and the cured body and the wafer are cured with respect to the cured layer obtained by curing the resin composition layer.
  • the shear adhesive strength to the above-mentioned wafer measured after being placed under a moist heat condition of 168 hours in an environment of 85 ° C. and a relative humidity of 85%, is preferably 25 N / 5 mm ⁇ or more, particularly 30 N / 5 mm ⁇ . It is preferable that it is above, and it is more preferable that it is 35N / 5mm ⁇ or more.
  • the obtained cured layer can easily achieve the above-described shear adhesive force. And when the hardened layer obtained achieves the above-mentioned shear adhesive force after wet heat conditions, the semiconductor device manufactured using the resin sheet according to the present embodiment has excellent heat resistance.
  • the upper limit value of the shear adhesive strength after the wet heat condition is not particularly limited, and is preferably, for example, 120 N / 5 mm ⁇ or less, particularly preferably 100 N / 5 mm ⁇ or less, and more preferably 80 N / 5 mm. It is preferable that it is below. Further, the above-mentioned shear adhesive strength after wet heat conditions is measured in accordance with MIL-STD-883J (METHOD 20199.9), and the details of the measurement method are as described later.
  • N / 5 mm ⁇ which is a unit representing the above-described shear adhesive force, means a force (N) per area of 5 mm ⁇ 5 mm.
  • Method for Producing Resin Sheet The method for producing a resin sheet according to the present embodiment is not particularly limited.
  • the method described above is performed by applying a coating liquid containing the above-described resin composition layer on a predetermined release sheet.
  • a method including a step of forming a resin composition layer hereinafter, sometimes referred to as “first manufacturing method” or a step of forming the resin composition layer by extruding the above-described resin composition.
  • first manufacturing method a step of forming a resin composition layer
  • second production method Method for producing a resin composition layer by extruding the above-described resin composition.
  • the resin sheet according to the present embodiment is preferably manufactured by the first manufacturing method among the methods described above.
  • the coating liquid used in the first production method is not particularly limited in its properties as long as it can be applied, and may contain a component for forming the resin composition layer as a solute. It may be contained as a dispersoid.
  • the solvent include organic solvents such as cyclohexanone, toluene, ethyl acetate, methyl ethyl ketone, acetone, and xylene.
  • a coating method of the coating liquid for example, a resin composition and, if desired, a coating liquid further containing a solvent or a dispersion medium are prepared, and a die coater or curtain is formed on the release surface of the release sheet.
  • a resin sheet can be produced by applying the coating solution with a coater, spray coater, slit coater, knife coater or the like to form a coating film and drying the coating film.
  • the said peeling sheet may peel as process material, and may protect the resin composition layer until it uses a resin sheet. Moreover, after laminating the resin composition layer on the electronic component, it may be peeled off from the resin composition layer before curing the resin composition layer, or the cured formed after curing the resin composition layer The layer may be peeled off.
  • the first manufacturing method may be performed after the step of forming the resin composition layer on the release sheet as described above, on the surface of the formed resin composition layer opposite to the release sheet described above.
  • a step of attaching the release sheet may be provided.
  • the resin sheet which has the structure of one release sheet / resin composition layer / other release sheet can be obtained.
  • at least one of the release sheets may be peeled off as a process material, or the resin composition layer may be protected until it is used for sealing.
  • the resin sheet according to the present embodiment is used for sealing electronic components.
  • the resin sheet according to the present embodiment is preferably used for sealing an electronic component in a method for manufacturing a semiconductor device, and further used for sealing an electronic component in a semiconductor mounting process of the method for manufacturing a semiconductor device. It is preferable.
  • the resin sheet according to this embodiment is used for sealing an electronic component, for example, the resin composition layer in the resin sheet with respect to the electronic component provided on a temporary fixing material such as a substrate or an adhesive sheet. After laminating
  • the resin composition layer is formed from a resin composition containing an aromatic condensed phosphate ester that is liquid at room temperature as a flame retardant.
  • a cured product obtained by curing is excellent in flame retardancy.
  • the aromatic condensed phosphate ester that is liquid at room temperature exhibits excellent compatibility with other components contained in the resin composition, and the resulting cured product is excellent for the object that the cured product contacts. Adhesive strength can be demonstrated. As a result, a semiconductor device having excellent performance can be manufactured using the resin sheet according to the present embodiment.
  • the above-described curing is preferably performed by heating the resin composition layer.
  • the heating temperature is preferably 100 ° C. or higher, and particularly preferably 120 ° C. or higher. Further, the temperature is preferably 240 ° C. or lower, and particularly preferably 200 ° C. or lower.
  • the heating time is preferably 15 minutes or more, and particularly preferably 20 minutes or more. In addition, the time is preferably 300 minutes or less, particularly preferably 100 minutes or less.
  • the above-described curing of the resin composition layer by heating is performed stepwise by a plurality of heat treatments.
  • the heating in this case is preferably performed in two or more times.
  • the temperature T1 is preferably 100 ° C. or higher and 130 ° C. or lower
  • the heat treatment time is preferably 15 minutes or longer and 60 minutes or shorter.
  • the temperature T2 is preferably 150 ° C. or higher and 220 ° C. or lower
  • the heat treatment time is preferably 30 minutes or longer and 120 minutes or shorter.
  • the release sheet is laminated on the electronic component and then cured before the resin composition layer is cured. You may peel from a resin composition layer, or after hardening a resin composition layer, you may peel from the formed cured layer.
  • the resin sheet according to this embodiment includes release sheets on both sides of the resin composition layer, one release sheet is peeled off, and the exposed surface of the exposed resin composition layer is laminated on the electronic component, and the other About a peeling sheet, you may peel in either before and after hardening of a resin composition layer.
  • Examples of the electronic components described above are not particularly limited as long as they are electronic components that are generally sealed, and examples thereof include semiconductor chips. Further, examples of the semiconductor device to be manufactured include a component built-in substrate, a semiconductor package, and the like, and a component built-in substrate is particularly preferable.
  • Examples 1 to 3 and Comparative Examples 1 to 3 The components shown in Table 1 were mixed and diluted with cyclohexanone to obtain a resin composition coating solution having a solid content concentration of 58% by mass.
  • the coating solution was applied at a coating speed of 2.0 m / min on the release surface of a release film (product name “SP-PET 382150”, manufactured by Lintec Co., Ltd.) on which one side was subjected to silicone release treatment, using a knife coater.
  • the obtained coating film was dried by heating in an oven at 50 ° C. for 1 minute, 70 ° C. for 1 minute, 90 ° C. for 1 minute, and 100 ° C. for 1 minute, and a resin composition having a thickness of 50 ⁇ m.
  • a resin sheet comprising a layer and a release film was obtained.
  • test piece was cured by heating in order at 100 ° C. for 30 minutes and at 190 ° C. for 2 hours to obtain a test piece for combustion test.
  • the obtained laminated body was made into a 10 mm square silicon mirror wafer under the conditions of 150 ° C., 300 gf and 3 seconds.
  • EDB65 product name “EDB65”
  • the resin composition layer was cured by sequentially heating the obtained sample at 100 ° C. for 30 minutes and at 190 ° C. for 2 hours to obtain a test piece for measuring shear adhesive force.
  • the resin sheet according to the present invention can be suitably used for sealing electronic components in a semiconductor mounting process.

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

Abstract

L'invention concerne une feuille de résine utilisée pour sceller un composant électronique et qui est pourvue d'une couche de composition de résine formée à partir d'une composition de résine contenant une résine thermodurcissable, d'une résine thermoplastique, d'une charge inorganique et d'un retardateur de flamme, composé d'un ester d'acide phosphorique condensé aromatique, à l'état liquide à température ambiante. La feuille de résine selon l'invention peut former un produit durci présentant une excellente ininflammabilité et une excellente puissance adhésive.
PCT/JP2019/010018 2018-03-26 2019-03-12 Feuille de résine et procédé de fabrication associé WO2019188255A1 (fr)

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CN201980022521.8A CN111918931A (zh) 2018-03-26 2019-03-12 树脂片及其制造方法
JP2020509851A JPWO2019188255A1 (ja) 2018-03-26 2019-03-12 樹脂シートおよびその製造方法
KR1020207024355A KR20200135310A (ko) 2018-03-26 2019-03-12 수지 시트 및 그 제조 방법

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US5521236A (en) * 1994-11-01 1996-05-28 Akzo Nobel N.V. Flame retarded stabilized polyester composition
JPH10251377A (ja) * 1997-03-12 1998-09-22 Hitachi Chem Co Ltd 封止用成形材料及び電子部品
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CN111918931A (zh) 2020-11-10

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