WO2019240079A1 - Composition de résine durcissable et dispositif à composant électronique - Google Patents

Composition de résine durcissable et dispositif à composant électronique Download PDF

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Publication number
WO2019240079A1
WO2019240079A1 PCT/JP2019/022928 JP2019022928W WO2019240079A1 WO 2019240079 A1 WO2019240079 A1 WO 2019240079A1 JP 2019022928 W JP2019022928 W JP 2019022928W WO 2019240079 A1 WO2019240079 A1 WO 2019240079A1
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Prior art keywords
group
curable resin
resin composition
epoxy resin
general formula
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PCT/JP2019/022928
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English (en)
Japanese (ja)
Inventor
中村　真也
正 石黒
大下　毅
遠藤　由則
Original Assignee
日立化成株式会社
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Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to JP2020525555A priority Critical patent/JP7302598B2/ja
Priority to SG11202012017VA priority patent/SG11202012017VA/en
Priority to KR1020207034779A priority patent/KR20210019004A/ko
Priority to CN201980039195.1A priority patent/CN112292425A/zh
Publication of WO2019240079A1 publication Critical patent/WO2019240079A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • 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
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • 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
    • 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
    • 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
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to a curable resin composition and an electronic component device.
  • the surface mounting type package is different from the conventional pin insertion type. That is, when the pins are attached to the wiring board, the conventional pin insertion type package is soldered from the back surface of the wiring board after the pins are inserted into the wiring board, so that the package is not directly exposed to high temperature.
  • the surface mount type package since the entire electronic component device is processed by a solder bath, a reflow device, or the like, the package is directly exposed to a soldering temperature (reflow temperature).
  • reflow temperature soldering temperature
  • the package absorbs moisture, moisture due to moisture absorption rapidly expands during soldering, and the generated vapor pressure acts as a peeling stress, and peeling occurs between the insert of the element, lead frame, etc., and the sealing material. This may cause package cracks, poor electrical characteristics, and the like. For this reason, it is desired to develop a sealing material that is excellent in adhesiveness to the insert, and thus excellent in solder heat resistance (reflow resistance).
  • a silane coupling agent has been studied as a modifier for the inorganic filler contained in the sealing material. Specifically, use of an epoxy group-containing silane coupling agent or amino group-containing silane coupling agent (for example, see Patent Document 1), use of a sulfur atom-containing silane coupling agent (for example, see Patent Document 2), etc. It is being considered.
  • the method using an epoxy group-containing silane coupling agent or an amino group-containing silane coupling agent may not have a sufficient effect of improving the adhesion of the lead frame surface to the metal.
  • a sulfur atom-containing silane coupling agent is used, there is a problem that the effect of improving the adhesion to metals (particularly, noble metals such as gold and silver) is not sufficient.
  • an object of the present invention is to provide a curable resin composition having excellent adhesion to a metal in a cured state, and an electronic component device including an element sealed thereby.
  • a curable resin composition comprising a curable resin and a compound represented by the following general formula (1).
  • R 1 to R 3 each independently represents a monovalent hydrocarbon group.
  • R 1 to R 3 each independently represents a monovalent hydrocarbon group.
  • R 4 to R 6 are each independently an aromatic hydrocarbon group, an aliphatic hydrocarbon group, an aliphatic hydrocarbon oxy group, an aromatic hydrocarbon oxy group, a hydroxyl group, a carboxy group, or a halogen atom.
  • An amino group, an aromatic hydrocarbon amino group, an aliphatic hydrocarbon amino group, a diaromatic hydrocarbon amino group, a dialiphatic hydrocarbon amino group, and an aromatic hydrocarbon aliphatic hydrocarbon amino group Is a monovalent group.
  • Each n is independently an integer of 0 to 5.
  • ⁇ 4> The curable resin composition according to any one of ⁇ 1> to ⁇ 3>, further including an inorganic filler.
  • ⁇ 5> The curable resin composition according to any one of ⁇ 1> to ⁇ 4>, wherein the curable resin contains an epoxy resin.
  • the epoxy resin is a biphenyl type epoxy resin, a stilbene type epoxy resin, a diphenylmethane type epoxy resin, a sulfur atom-containing type epoxy resin, a novolac type epoxy resin, a dicyclopentadiene type epoxy resin, a triphenylmethane type epoxy resin, Curable resin composition as described in ⁇ 5> containing at least 1 sort (s) chosen from the group which consists of a polymerization type epoxy resin and an aralkyl type epoxy resin.
  • the curable resin composition according to any one of ⁇ 1> to ⁇ 6>, further including a curing agent.
  • the curing agent includes an aralkyl type phenol resin, a dicyclopentadiene type phenol resin, a triphenylmethane type phenol resin, a copolymer type phenol resin of a benzaldehyde type phenol resin and an aralkyl type phenol resin, and a novolac type phenol resin.
  • the curable resin composition according to ⁇ 7> comprising at least one selected from the group.
  • the curing accelerator includes a compound represented by the following general formula (I-1).
  • R 1 to R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and two or more of R 1 to R 3 are bonded to each other to form a cyclic structure.
  • R 4 to R 7 are each independently a hydrogen atom, a hydroxyl group or an organic group having 1 to 18 carbon atoms, and two or more of R 4 to R 7 are bonded to each other to form a cyclic structure. It may be formed.
  • R 1 to R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and two or more of R 1 to R 3 are bonded to each other to form a cyclic structure.
  • R 4 to R 6 are each independently a hydrogen atom or an organic group having 1 to 18 carbon atoms, and two or more of R 4 to R 6 are bonded to each other to form a cyclic structure. May be. ⁇ 13> An electronic component device comprising: an element; and a cured product of the curable resin composition according to any one of ⁇ 1> to ⁇ 12> that seals the element.
  • a curable resin composition having excellent adhesion to a metal in a cured state, and an electronic component device including an element sealed thereby are provided.
  • the term “process” includes a process that is independent of other processes and includes the process if the purpose of the process is achieved even if it cannot be clearly distinguished from the other processes.
  • numerical ranges indicated using “to” include numerical values described before and after “to” as the minimum value and the maximum value, respectively.
  • an upper limit value or a lower limit value described in one numerical range may be replaced with an upper limit value or a lower limit value of another numerical range described.
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the content rate or content of each component in the composition is such that when there are a plurality of substances corresponding to each component in the composition, the plurality of substances present in the composition unless otherwise specified.
  • the particle size of each component in the composition is a mixture of the plurality of types of particles present in the composition unless there is a specific indication when there are a plurality of types of particles corresponding to each component in the composition.
  • a curable resin composition according to an embodiment of the present disclosure includes a curable resin and a compound represented by the following general formula (1) (hereinafter also referred to as a specific triazine compound).
  • a curable resin composition containing a specific triazine compound is excellent in adhesion to a metal (particularly a noble metal such as gold or silver) in a cured state. The reason is not clear, but it is presumed that the specific triazine compound in the cured product forms a coordinate bond with the metal.
  • the curable resin composition containing the specific triazine compound has excellent adhesion to a metal in a cured state, at least when used as a sealing material for a package including a lead frame whose surface material is a metal, Peeling between the frame and the sealing material is suppressed. For this reason, it is excellent in reflow resistance.
  • the specific triazine compound is a compound represented by the following general formula (1).
  • the specific triazine compound one kind may be used alone, or two or more kinds having different structures may be used.
  • R 1 to R 3 each independently represents a monovalent hydrocarbon group.
  • the structure of the monovalent hydrocarbon group represented by R 1 to R 3 is not particularly limited. For example, an aromatic hydrocarbon group and an aliphatic hydrocarbon group are mentioned.
  • Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
  • Examples of the aliphatic hydrocarbon group include a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms.
  • linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, Examples thereof include alkyl groups such as pentyl group, hexyl group, octyl group, decyl group and dodecyl group, allyl group and vinyl group.
  • alicyclic hydrocarbon group having 3 to 18 carbon atoms include a cycloalkyl group such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, and a cyclohexenyl group, an adamantyl group, a norbornyl group, and a dicyclopenta Nyl group etc. are mentioned.
  • the monovalent hydrocarbon group represented by R 1 to R 3 may have a substituent.
  • Substituents include aromatic hydrocarbon groups, aliphatic hydrocarbon groups, aliphatic hydrocarbon oxy groups, aromatic hydrocarbon oxy groups, hydroxyl groups, carboxy groups, halogen atoms, amino groups, aromatic hydrocarbon amino groups, aliphatic An aromatic hydrocarbon amino group, a diaromatic hydrocarbon amino group, a dialiphatic hydrocarbon amino group, an aromatic hydrocarbon aliphatic hydrocarbon amino group, and the like.
  • Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
  • Examples of the aliphatic hydrocarbon group include a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms.
  • Examples of the aromatic hydrocarbon oxy group include those in which an oxygen atom is bonded to an aromatic hydrocarbon group such as a phenyl group or a naphthyl group.
  • Examples of the aliphatic hydrocarbon oxy group include an oxygen atom in an aliphatic hydrocarbon group such as a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms. The combination is mentioned.
  • the number of carbon atoms of the monovalent hydrocarbon group represented by R 1 to R 3 is not particularly limited. For example, each independently preferably has 1 to 30 carbon atoms. When the monovalent hydrocarbon group represented by R 1 to R 3 has a substituent, the carbon atom contained in the substituent is also included in the “carbon number of monovalent carbon atom”.
  • At least one of the monovalent hydrocarbon groups represented by R 1 to R 3 is a phenyl group, and in one embodiment, the monovalent hydrocarbon represented by R 1 to R 3 All of the groups are phenyl groups.
  • the specific triazine compound may be a compound represented by the following general formula (2).
  • R 4 to R 6 are each independently an aromatic hydrocarbon group, an aliphatic hydrocarbon group, an aliphatic hydrocarbon oxy group, an aromatic hydrocarbon oxy group, a hydroxyl group, a carboxy group, a halogen atom, Selected from the group consisting of an amino group, an aromatic hydrocarbon amino group, an aliphatic hydrocarbon amino group, a diaromatic hydrocarbon amino group, a dialiphatic hydrocarbon amino group, and an aromatic hydrocarbon aliphatic hydrocarbon amino group.
  • Each n is independently an integer of 0 to 5.
  • each n is independently an integer of 1 to 3, and may be 2. In one embodiment, at least one of R 4 to R 6 in the general formula (2) is a hydroxyl group.
  • one or two of R 1 to R 3 in the general formula (1) are 2,4-dimethylphenyl groups. In one embodiment, two of R 1 to R 3 are 2,4-dimethylphenyl groups and one is a 2-hydroxy-4-n-octyloxyphenyl group.
  • Specific examples of the specific triazine compound include compounds having a structure represented by the following formula.
  • the amount of the specific triazine compound in the curable resin composition is not particularly limited. From the viewpoint of sufficiently obtaining the effect of improving adhesion to gold and silver, for example, the total of the curable resin contained in the curable resin composition and the curing agent used as necessary (hereinafter also referred to as “resin component”). ) It is preferable that it is 0.1 mass part or more with respect to 100 mass parts, It is more preferable that it is 1.0 mass part or more, It is further more preferable that it is 3.0 mass part or more. From the viewpoint of curability, for example, it is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and still more preferably 20 parts by mass or less with respect to 100 parts by mass of the resin component.
  • the curable resin is not particularly limited as long as it forms a three-dimensional crosslinked structure by a reaction, and may be thermosetting or photocurable. From the viewpoint of mass productivity, thermosetting is preferable.
  • the curable resin may be cured by self-polymerization or may be cured by a reaction with a curing agent, a crosslinking agent, or the like.
  • the functional group causing the reaction of the curable resin is not particularly limited, and examples thereof include cyclic ether groups such as epoxy groups and oxetanyl groups, hydroxyl groups, carboxy groups, amino groups, acryloyl groups, isocyanate groups, maleimide groups, and alkenyl groups. From the viewpoint of balance of properties as the sealing material, a curable resin containing a cyclic ether group is preferable, and a curable resin (epoxy resin) containing an epoxy group is more preferable.
  • the type of the epoxy resin is not particularly limited as long as it has two or more epoxy groups in one molecule.
  • at least one phenol selected from the group consisting of phenol compounds such as phenol, cresol, xylenol, resorcin, catechol, bisphenol A, and bisphenol F and naphthol compounds such as ⁇ -naphthol, ⁇ -naphthol, and dihydroxynaphthalene.
  • Novolak type epoxy resin (phenol novolak type epoxy resin, which is obtained by epoxidizing a novolak resin obtained by condensing or co-condensing an organic compound and an aliphatic aldehyde compound such as formaldehyde, acetaldehyde, propionaldehyde or the like under an acidic catalyst.
  • Orthocresol novolac type epoxy resin, etc.] obtained by condensing or cocondensing the above phenolic compound with an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde in the presence of an acidic catalyst.
  • Epoxidized triphenylmethane-type phenolic resin epoxidized novolak resin obtained by co-condensation of the above phenolic and naphtholic compounds with an aldehyde compound under an acidic catalyst
  • a diphenylidyl ether that is a diglycidyl ether such as bisphenol A or bisphenol F
  • a biphenyl type epoxy resin that is a diglycidyl ether of an alkyl-substituted or unsubstituted biphenol
  • Stilbene type epoxy resins that are ethers
  • sulfur atom-containing epoxy resins that are diglycidyl ethers such as bisphenol S
  • polymers such as butanediol, polyethylene glycol, and polypropylene glycol Epoxy resin that is a glycidyl ether of chols
  • Glycidyl ester type epoxy resin that is a glycidyl ester
  • biphenyl type epoxy resin stilbene type epoxy resin, diphenylmethane type epoxy resin, sulfur atom containing type epoxy resin, novolac type epoxy resin, dicyclopentadiene type epoxy from the viewpoint of balance between reflow resistance and fluidity
  • An epoxy resin selected from the group consisting of a resin, a triphenylmethane type epoxy resin, a copolymer type epoxy resin and an aralkyl type epoxy resin (these are referred to as “specific epoxy resins”) is preferable.
  • a specific epoxy resin may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the content is preferably 30% by mass or more, more preferably 50% by mass or more of the entire epoxy resin from the viewpoint of exhibiting the performance of the specific epoxy resin. .
  • epoxy resins biphenyl type epoxy resins, stilbene type epoxy resins, diphenylmethane type epoxy resins or sulfur atom-containing type epoxy resins are more preferable from the viewpoint of fluidity, and dicyclopentadiene type epoxy is preferable from the viewpoint of heat resistance.
  • the biphenyl type epoxy resin is not particularly limited as long as it is an epoxy resin having a biphenyl skeleton.
  • an epoxy resin represented by the following general formula (II) is preferable.
  • the 3, 3 ′, 5, 5 ′ positions when the positions where oxygen atoms are substituted in R 8 are the 4 and 4 ′ positions are methyl groups.
  • R 8 is a hydrogen atom
  • all the R 8 are hydrogen atoms 4,4'-bis (2,3-epoxypropoxy) biphenyl
  • the positions where oxygen atoms are substituted in R 8 are the 4 and 4 ′ positions, the 3, 3 ′, 5, 5 ′ positions are methyl groups
  • the other R YL-6121H which is a mixture when 8 is a hydrogen atom, is commercially available.
  • R 8 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aromatic group having 4 to 18 carbon atoms, which may be all the same or different.
  • n is an average value and represents a number from 0 to 10.
  • the stilbene type epoxy resin is not particularly limited as long as it is an epoxy resin having a stilbene skeleton.
  • an epoxy resin represented by the following general formula (III) is preferable.
  • 3, 9 ′, 5, 5 ′ positions are methyl groups when R 9 is substituted with oxygen atoms at positions 4 and 4 ′.
  • R 9 other than that is a hydrogen atom, and all of R 10 are hydrogen atoms, and three of the 3, 9 ′, 5, 5 ′ positions of R 9 are methyl groups, ESLV-210 (Sumitomo Chemical Co., Ltd., trade name), which is a mixture of the case where one is a t-butyl group, the other R 9 is a hydrogen atom, and all of R 10 are hydrogen atoms, etc. It is available as a commercial product.
  • R 9 and R 10 each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and all may be the same or different.
  • n is an average value and represents a number from 0 to 10.
  • the diphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin having a diphenylmethane skeleton.
  • an epoxy resin represented by the following general formula (IV) is preferable.
  • all of R 11 are hydrogen atoms, and 3, 3 when the positions where oxygen atoms are substituted in R 12 are the 4 and 4 ′ positions.
  • YSLV-80XY (Nippon Steel & Sumikin Chemical Co., Ltd., trade name) in which the ', 5,5'-position is a methyl group and the other R 12 is a hydrogen atom is commercially available.
  • R 11 and R 12 each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • n is an average value and represents a number from 0 to 10.
  • the sulfur atom-containing epoxy resin is not particularly limited as long as it is an epoxy resin containing a sulfur atom.
  • the epoxy resin represented with the following general formula (V) is mentioned.
  • the 3 and 3 'positions when the positions where oxygen atoms are substituted in R 13 are the 4 and 4' positions are t-butyl groups, YSLV-120TE (Nippon Steel & Sumikin Chemical Co., Ltd., trade name) in which the 6,6′-position is a methyl group and the other R 13 is a hydrogen atom is commercially available.
  • R 13 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and all may be the same or different.
  • n is an average value and represents a number from 0 to 10.
  • the novolac type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a novolac type phenol resin.
  • an epoxy resin obtained by epoxidizing a novolak-type phenol resin such as a phenol novolak resin, a cresol novolak resin, or a naphthol novolak resin using a method such as glycyridyl etherification is preferable, and is represented by the following general formula (VI)
  • An epoxy resin is more preferable.
  • R 14 are hydrogen atoms
  • R 15 is a methyl group
  • i 1, ESCN-190, ESCN-195 (Sumitomo Chemical Co., Ltd.) , trade name)
  • all R 14 is a hydrogen atom
  • R 14 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • R 15 represents a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • i each independently represents an integer of 0 to 3.
  • n is an average value and represents a number from 0 to 10.
  • the dicyclopentadiene type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a compound having a dicyclopentadiene skeleton as a raw material.
  • an epoxy resin represented by the following general formula (VII) is preferable.
  • R 16 represents a monovalent organic group having 1 to 18 carbon atoms, which may be all the same or different. i each independently represents an integer of 0 to 3. n is an average value and represents a number from 0 to 10.
  • the triphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin made from a compound having a triphenylmethane skeleton.
  • an epoxy resin obtained by glycidyl etherification of a triphenylmethane type phenol resin such as a novolak type phenol resin of a compound having a triphenylmethane skeleton and a compound having a phenolic hydroxyl group is preferable, and is represented by the following general formula (VIII). More preferred is an epoxy resin.
  • epoxy resins represented by the following general formula (VIII), 1032H60 (Mitsubishi Chemical Corporation, trade name), i is 0 and k is 0, EPPN-502H (Nippon Kayaku Co., Ltd., trade name) Etc. are available as commercial products.
  • R 17 and R 18 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • i is each independently an integer of 0 to 3
  • k is each independently an integer of 0 to 4.
  • n is an average value and represents a number from 0 to 10.
  • the copolymerization type epoxy resin obtained by epoxidizing a novolak resin obtained from a naphthol compound, a phenol compound, and an aldehyde compound is not particularly limited as long as it is an epoxy resin made from a compound having a naphthol skeleton and a compound having a phenol skeleton.
  • an epoxy resin obtained by glycidyl etherification of a novolac type phenol resin using a compound having a naphthol skeleton and a compound having a phenol skeleton is preferable, and an epoxy resin represented by the following general formula (IX) is more preferable.
  • R 19 to R 21 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • i is independently an integer of 0 to 3
  • j is independently of an integer of 0 to 2
  • k is independently of an integer of 0 to 4.
  • Each of l and m is an average value and is a number from 0 to 10, and (l + m) is a number from 0 to 10.
  • the terminal of the epoxy resin represented by the formula (IX) is one of the following formulas (IX-1) and (IX-2).
  • R 19 to R 21 are as defined for i, j and k, and R 19 to R 21 in formula (IX) are the same as the definitions for i, j and k. It is. n is 1 (when bonded via a methylene group) or 0 (when not bonded via a methylene group).
  • Examples of the epoxy resin represented by the general formula (IX) include a random copolymer containing l constituent units and m constituent units at random, an alternating copolymer containing alternating units, and a copolymer containing regular units. And a block copolymer contained in a block form. Any one of these may be used alone, or two or more may be used in combination.
  • epiklone HP-5000 represented by the following general formula, which is a methoxynaphthalene / cresol formaldehyde cocondensation type epoxy resin containing the following two structural units in random, alternating or block order: DIC Corporation, trade name) is also preferred.
  • n and m are each an average value and are a number from 0 to 10
  • (n + m) is a number from 0 to 10
  • n and m are each an average value
  • 1 to 9 (N + m) is a number from 2 to 10.
  • the aralkyl type epoxy resin is synthesized from at least one selected from the group consisting of phenol compounds such as phenol and cresol and naphthol compounds such as naphthol and dimethylnaphthol, and dimethoxyparaxylene, bis (methoxymethyl) biphenyl, or derivatives thereof. If it is an epoxy resin which uses a phenol resin as a raw material, it will not be specifically limited.
  • phenol compounds such as phenol and cresol and naphthol compounds
  • naphthol and dimethylnaphthol and dimethoxyparaxylene
  • dimethoxyparaxylene bis (methoxymethyl) biphenyl
  • An epoxy resin obtained by glycidyl etherification is preferable, and an epoxy resin represented by the following general formulas (X) and (XI) is more preferable.
  • R- 38 is a hydrogen atom, NC-3000S (Nippon Kayaku Co., Ltd., trade name), i is 0, R 38 CER-3000 (Nippon Kayaku Co., Ltd., trade name), in which an epoxy resin in which hydrogen atom is a hydrogen atom and an epoxy resin in which all R 8 in the general formula (II) are hydrogen atoms in a mass ratio of 80:20, is commercially available It is available as a product.
  • epoxy resins represented by the following general formula (XI), ESN-175 (Nippon Steel & Sumikin Chemical Co., Ltd., trade name) in which i is 0, j is 0, and k is 0 is commercially available. It is available as a product.
  • R 38 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • R 37 and R 39 to R 41 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • each i is independently an integer from 0 to 3
  • j is each independently an integer from 0 to 2
  • k is each independently an integer from 0 to 4
  • l is each independently an integer from 0 to 6.
  • Show. n is an average value and is independently a number from 0 to 10.
  • R 8 to R 21 and R 37 to R 41 in the above general formulas (II) to (XI) “all may be the same or different” means, for example, 8 to 8 in the formula (II) It means that all 88 R 8 may be the same or different.
  • the other R 9 to R 21 and R 37 to R 41 also mean that all the numbers contained in the formula may be the same or different.
  • R 8 to R 21 and R 37 to R 41 may be the same or different.
  • all of R 9 and R 10 may be the same or different.
  • the organic group having 1 to 18 carbon atoms is preferably an alkyl group or an aryl group.
  • n is an average value and is preferably independently in the range of 0 to 10.
  • n is 10 or less, the melt viscosity of the resin component does not become too high, the viscosity at the time of melt molding of the curable resin composition decreases, filling failure, deformation of the bonding wire (gold wire connecting the element and the lead) Etc. tend to be suppressed.
  • n is set in the range of 0-4.
  • the functional group equivalent of the curable resin (epoxy equivalent in the case of epoxy resin) is not particularly limited. From the viewpoint of balance of various properties such as moldability, reflow resistance and electrical reliability, the functional group equivalent of the curable resin is preferably 100 g / eq to 1000 g / eq, and preferably 150 g / eq to 500 g / eq. More preferably.
  • the softening point or melting point of the curable resin is not particularly limited. From the viewpoint of moldability and reflow resistance, the temperature is preferably 40 ° C to 180 ° C, and from the viewpoint of handleability when preparing the curable resin composition, it is more preferably 50 ° C to 130 ° C.
  • the content of the curable resin in the curable resin composition is preferably 0.5% by mass to 50% by mass from the viewpoint of strength, fluidity, heat resistance, moldability, and the like, and 2% by mass to 30% by mass. % Is more preferable.
  • the curable resin composition may contain a curing agent.
  • the type of the curing agent is not particularly limited, and can be selected according to the type of the curable resin, the desired characteristics of the curable resin composition, and the like.
  • Examples of the curing agent when the curable resin is an epoxy resin include a phenol curing agent, an amine curing agent, an acid anhydride curing agent, a polymercaptan curing agent, a polyaminoamide curing agent, an isocyanate curing agent, and a blocked isocyanate curing agent. It is done.
  • At least one selected from the group consisting of a phenol curing agent, an amine curing agent and an acid anhydride curing agent is preferable, and from the viewpoint of electrical reliability, a phenol curing agent is more preferable. preferable.
  • phenol curing agent examples include phenol resins and polyhydric phenol compounds having two or more phenolic hydroxyl groups in one molecule.
  • polyphenol compounds such as resorcin, catechol, bisphenol A, bisphenol F, substituted or unsubstituted biphenol; phenol, cresol, xylenol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol, etc.
  • an aralkyl type phenol resin a dicyclopentadiene type phenol resin, a triphenylmethane type phenol resin, a copolymer type phenol resin of a benzaldehyde type phenol resin and an aralkyl type phenol resin, and At least one selected from the group consisting of novolak-type phenolic resins (these are referred to as “specific phenol curing agents”) is preferable.
  • curing agent may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the content of the specific phenol curing agent is preferably 30% by mass or more, more preferably 50% by mass or more of the entire curing agent from the viewpoint of sufficiently exerting the performance. It is more preferable.
  • aralkyl type phenol resin examples include a phenol aralkyl resin and a naphthol aralkyl resin synthesized from a phenolic compound, dimethoxyparaxylene, bis (methoxymethyl) biphenyl and the like.
  • the aralkyl type phenol resin may be further copolymerized with another phenol resin.
  • Examples of the copolymerized aralkyl type phenol resin include a copolymer type phenol resin of a benzaldehyde type phenol resin and an aralkyl type phenol resin, a copolymer type phenol resin of a salicylaldehyde type phenol resin and an aralkyl type phenol resin, and a novolac type phenol resin. Examples thereof include copolymer type phenol resins with aralkyl type phenol resins.
  • the aralkyl type phenol resin is not particularly limited as long as it is a phenol resin synthesized from at least one selected from the group consisting of a phenol compound and a naphthol compound and dimethoxyparaxylene, bis (methoxymethyl) biphenyl, or a derivative thereof.
  • phenol resins represented by the following general formulas (XII) to (XIV) are preferable.
  • R 23 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • R 22 , R 24 , R 25 and R 28 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • R 26 and R 27 each represent a hydroxyl group or a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • i is each independently an integer from 0 to 3
  • j is each independently an integer from 0 to 2
  • k is each independently an integer from 0 to 4
  • p is each independently an integer from 0 to 4. is there.
  • n is an average value and is independently a number from 0 to 10.
  • phenol resins represented by the general formula (XIII), XL-225, XLC (Mitsui Chemicals, trade name), MEH-7800 (Maywa Kasei Co., Ltd.), where i is 0 and k is 0 (Trade name) etc. are commercially available.
  • the dicyclopentadiene type phenol resin is not particularly limited as long as it is a phenol resin obtained using a compound having a dicyclopentadiene skeleton as a raw material.
  • a phenol resin represented by the following general formula (XV) is preferable.
  • DPP Shin Nippon Petrochemical Co., Ltd., trade name
  • i is 0 is available as a commercial product.
  • R 29 represents a monovalent organic group having 1 to 18 carbon atoms, which may be all the same or different.
  • i each independently represents an integer of 0 to 3.
  • n is an average value and represents a number from 0 to 10.
  • the triphenylmethane type phenol resin is not particularly limited as long as it is a phenol resin obtained using a compound having a triphenylmethane skeleton as a raw material.
  • a phenol resin represented by the following general formula (XVI) is preferable.
  • phenol resins represented by the following general formula (XVI), MEH-7500 (Maywa Kasei Co., Ltd., trade name) in which i is 0 and k is 0 is commercially available.
  • R 30 and R 31 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • i is each independently an integer of 0 to 3
  • k is each independently an integer of 0 to 4.
  • n is an average value and is a number from 0 to 10.
  • the copolymeric phenol resin of the benzaldehyde type phenol resin and the aralkyl type phenol resin is not particularly limited as long as it is a copolymer type phenol resin of a phenol resin and an aralkyl type phenol resin obtained using a compound having a benzaldehyde skeleton as a raw material.
  • a phenol resin represented by the following general formula (XVII) is preferable.
  • phenol resins represented by the following general formula (XVII), HE-510 (Air Water Chemical Co., Ltd., trade name) in which i is 0, k is 0, and q is 0 is commercially available. It is available as a product.
  • R 32 to R 34 each represent a monovalent organic group having 1 to 18 carbon atoms, and may be all the same or different.
  • i is each independently an integer of 0 to 3
  • k is independently an integer of 0 to 4
  • q is independently an integer of 0 to 5.
  • l and m are average values, each independently a number from 0 to 11. However, the sum of l and m is a number from 1 to 11.
  • the novolak-type phenol resin is not particularly limited as long as it is a phenol resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of a phenol compound and a naphthol compound and an aldehyde compound under an acidic catalyst. .
  • a phenol resin represented by the following general formula (XVIII) is preferable.
  • phenolic resins represented by the following general formula (XVIII) Tamanols 758 and 759 (Arakawa Chemical Industries, Ltd., trade name) in which i is 0 and all R 35 are hydrogen atoms, HP-850N (Hitachi Chemical) Co., Ltd., trade name) etc. are available as commercial products.
  • R 35 represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms, which may be all the same or different.
  • R 36 represents a monovalent organic group having 1 to 18 carbon atoms, and each may be the same or different.
  • i each independently represents an integer of 0 to 3.
  • n is an average value and represents a number from 0 to 10.
  • R 22 to R 36 may be the same or different.
  • R 22 and R 23 may be the same or different, and all of R 30 and R 31 may be the same or different.
  • n is preferably in the range of 0 to 10. If it is 10 or less, the melt viscosity of the resin component does not become too high, the viscosity at the time of melt molding of the curable resin composition also decreases, and unfilled defects and bonding wire (gold wire connecting the element and the lead) are deformed. It becomes difficult to occur.
  • the average n per molecule is preferably set in the range of 0-4.
  • the functional group equivalent of the curing agent (hydroxyl equivalent in the case of a phenol curing agent) is not particularly limited. From the viewpoint of balance of various properties such as moldability, reflow resistance, and electrical reliability, it is preferably 70 g / eq to 1000 g / eq, and more preferably 80 g / eq to 500 g / eq. *
  • the softening point or melting point of the curing agent is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably 40 ° C to 180 ° C, and from the viewpoint of handleability during the production of the curable resin composition, it is more preferably 50 ° C to 130 ° C. *
  • the equivalent ratio between the curable resin and the curing agent is not particularly limited. From the viewpoint of reducing the amount of each unreacted component, it is preferably set in the range of 0.5 to 2.0, and more preferably in the range of 0.6 to 1.3. From the viewpoint of moldability and reflow resistance, it is more preferable to set it in the range of 0.8 to 1.2.
  • the curable resin composition may contain a curing accelerator.
  • the kind in particular of hardening accelerator is not restrict
  • the curing accelerator preferably contains a phosphonium compound.
  • the phosphonium compound include triphenylphosphine, diphenyl (p-tolyl) phosphine, tris (alkylphenyl) phosphine, tris (alkoxyphenyl) phosphine, tris (alkylalkoxyphenyl) phosphine, tris (dialkylphenyl) phosphine, Tris (trialkylphenyl) phosphine, tris (tetraalkylphenyl) phosphine, tris (dialkoxyphenyl) phosphine, tris (trialkoxyphenyl) phosphine, tris (tetraalkoxyphenyl) phosphine, trialkylphosphine, dialkylarylphosphine, alkyldiaryl Tertiary phosphine such as phosphin
  • a compound having a ⁇ bond such as a quin
  • a compound having intramolecular polarization obtained by reacting with a halogenated phenol compound of the above, followed by a dehydrohalogenation step; bonded to a tetrasubstituted phosphonium such as tetraphenylphosphonium, or a boron atom such as tetra-p-tolylborate Tetra-substituted phosphoniums and tetra-substituted borates having no phenyl group; salts of tetra-substituted phosphoniums with anions from which protons are eliminated from phenolic compounds, salts of tetra-substituted phosphoniums with anions from which protons are eliminated from carboxylic acid compounds, etc. Can be mentioned.
  • R 1 to R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and two or more of R 1 to R 3 are bonded to each other to form a cyclic structure.
  • R 4 to R 7 are each independently a hydrogen atom, a hydroxyl group or an organic group having 1 to 18 carbon atoms, and two or more of R 4 to R 7 are bonded to each other to form a cyclic structure. It may be formed.
  • hydrocarbon group having 1 to 18 carbon atoms described as R 1 to R 3 in the general formula (I-1) is an aliphatic hydrocarbon group having 1 to 18 carbon atoms and 6 to 18 carbon atoms. Contains some aromatic hydrocarbon groups.
  • the aliphatic hydrocarbon group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and still more preferably 4 to 6 carbon atoms.
  • the aliphatic hydrocarbon group having 1 to 18 carbon atoms is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms or an alicyclic hydrocarbon group having 3 to 18 carbon atoms. Also good. From the viewpoint of ease of production, it is preferably a linear or branched aliphatic hydrocarbon group.
  • linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, Examples thereof include alkyl groups such as pentyl group, hexyl group, octyl group, decyl group and dodecyl group, allyl group and vinyl group.
  • the linear or branched aliphatic hydrocarbon group may or may not have a substituent.
  • substituents examples include an alkoxy group such as a methoxy group, an ethoxy group, a butoxy group, and a t-butoxy group, an aryl group such as a phenyl group and a naphthyl group, a hydroxyl group, an amino group, and a halogen atom.
  • the linear or branched aliphatic hydrocarbon group may have two or more substituents, and the substituents in that case may be the same or different.
  • the total number of carbon atoms contained in the aliphatic hydrocarbon group and the substituent is preferably 1 to 18.
  • an unsubstituted alkyl group is preferable, an unsubstituted alkyl group having 1 to 8 carbon atoms is more preferable, and an n-butyl group, an isobutyl group, an n-pentyl group, an n-hexyl group, and an n-octyl group are preferable. More preferred are groups.
  • alicyclic hydrocarbon having 3 to 18 carbon atoms include cycloalkyl groups such as cyclopentyl group, cyclohexyl group and cycloheptyl group, and cycloalkenyl groups such as cyclopentenyl group and cyclohexenyl group.
  • the alicyclic hydrocarbon group may or may not have a substituent.
  • Substituents include alkyl groups such as methyl, ethyl, butyl, and tert-butyl groups, alkoxy groups such as methoxy, ethoxy, butoxy, and t-butoxy groups, and aryl groups such as phenyl and naphthyl groups.
  • the alicyclic hydrocarbon group may have two or more substituents, and the substituents in that case may be the same or different.
  • the total number of carbon atoms contained in the alicyclic hydrocarbon group and the substituent is preferably 3 to 18.
  • the position of the substituent is not particularly limited.
  • an unsubstituted cycloalkyl group is preferable, an unsubstituted cycloalkyl group having 4 to 10 carbon atoms is more preferable, and a cyclohexyl group, a cyclopentyl group, and a cycloheptyl group are further preferable.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms preferably has 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms.
  • the aromatic hydrocarbon group may or may not have a substituent.
  • Substituents include alkyl groups such as methyl, ethyl, butyl, and t-butyl groups, alkoxy groups such as methoxy, ethoxy, butoxy, and t-butoxy groups, and aryl groups such as phenyl and naphthyl groups. , Hydroxyl group, amino group, halogen atom and the like.
  • the aromatic hydrocarbon group may have two or more substituents, and the substituents in that case may be the same or different.
  • the total number of carbon atoms contained in the aromatic hydrocarbon group and the substituent is preferably 6 to 18.
  • the position of the substituent is not particularly limited.
  • aromatic hydrocarbon group having 6 to 18 carbon atoms include phenyl group, 1-naphthyl group, 2-naphthyl group, tolyl group, dimethylphenyl group, ethylphenyl group, butylphenyl group, and t-butyl. Examples thereof include a phenyl group, a methoxyphenyl group, an ethoxyphenyl group, a butoxyphenyl group, and a t-butoxyphenyl group.
  • the position of the substituent in these aromatic hydrocarbon groups may be any of the ortho, meta and para positions.
  • an unsubstituted aryl group having 6 to 12 carbon atoms or 6 to 12 carbon atoms including a substituent is preferable, and an unsubstituted carbon atom having 6 to 10 carbon atoms or a substituent is included.
  • An aryl group having a number of 6 to 10 is more preferable, and a phenyl group, a p-tolyl group, and a p-methoxyphenyl group are more preferable.
  • R 2 to R 3 out of R 1 to R 3 may be bonded to each other to form a cyclic structure” described as R 1 to R 3 in the general formula (I-1) means that R 1 to R 3 It means that 2 or 3 of them are bonded to form one divalent or trivalent hydrocarbon group as a whole.
  • R 1 to R 3 examples include alkylene groups such as ethylene, propylene, butylene, pentylene, and hexylene that can be bonded to a phosphorus atom to form a cyclic structure, alkenylene groups such as ethylenylene, propyleneylene, and butyleneylene, Substituents that can be bonded to a phosphorus atom to form a cyclic structure, such as an aralkylene group such as a methylenephenylene group, and an arylene group such as phenylene, naphthylene, and anthracenylene. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom, or the like.
  • alkylene groups such as ethylene, propylene, butylene, pentylene, and hexylene that can be
  • the “organic group having 1 to 18 carbon atoms” described as R 4 to R 7 in the general formula (I-1) has 1 to 18 carbon atoms and may be substituted or unsubstituted.
  • An aromatic hydrocarbon group, an aromatic hydrocarbon group, an aliphatic hydrocarbon oxy group, an aromatic hydrocarbon oxy group, an acyl group, a hydrocarbon oxycarbonyl group, and an acyloxy group is 1 to 18 carbon atoms and may be substituted or unsubstituted.
  • Examples of the aliphatic hydrocarbon group and aromatic hydrocarbon group include those described above as examples of the aliphatic hydrocarbon group and aromatic hydrocarbon group represented by R 1 to R 3 .
  • Examples of the aliphatic hydrocarbon oxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, 2-butoxy group, t-butoxy group, cyclopropyloxy group, cyclohexyloxy group, cyclopentyloxy group
  • An oxy group having a structure in which an oxygen atom is bonded to the above-described aliphatic hydrocarbon group such as an allyloxy group or a vinyloxy group, and these aliphatic hydrocarbon oxy groups are further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group. And those substituted with a group, a hydroxyl group, a halogen atom, and the like.
  • aromatic hydrocarbon oxy group examples include an oxy having a structure in which an oxygen atom is bonded to the above aromatic hydrocarbon group such as a phenoxy group, a methylphenoxy group, an ethylphenoxy group, a methoxyphenoxy group, a butoxyphenoxy group, and a phenoxyphenoxy group.
  • aromatic hydrocarbon oxy groups further substituted with an alkyl group, alkoxy group, aryl group, aryloxy group, amino group, halogen atom and the like.
  • acyl group formyl group, acetyl group, ethylcarbonyl group, butyryl group, cyclohexylcarbonyl group, aliphatic hydrocarbon carbonyl group such as allylcarbonyl, aromatic hydrocarbon carbonyl group such as phenylcarbonyl group, methylphenylcarbonyl group, etc.
  • aliphatic hydrocarbon carbonyl groups or aromatic hydrocarbon carbonyl groups are further substituted with an alkyl group, alkoxy group, aryl group, aryloxy group, amino group, halogen atom, and the like.
  • hydrocarbon oxycarbonyl group examples include aliphatic hydrocarbon oxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group, allyloxycarbonyl group, cyclohexyloxycarbonyl group, phenoxycarbonyl group, methylphenoxycarbonyl group, etc.
  • Aromatic hydrocarbon oxycarbonyl groups, these aliphatic hydrocarbon carbonyloxy groups or aromatic hydrocarbon carbonyloxy groups are further substituted with alkyl groups, alkoxy groups, aryl groups, aryloxy groups, amino groups, halogen atoms, etc. Things.
  • acyloxy group examples include an aliphatic hydrocarbon carbonyloxy group such as a methylcarbonyloxy group, an ethylcarbonyloxy group, a butylcarbonyloxy group, an allylcarbonyloxy group, a cyclohexylcarbonyloxy group, a phenylcarbonyloxy group, and a methylphenylcarbonyloxy group.
  • Aromatic hydrocarbon carbonyloxy group such as aliphatic hydrocarbon carbonyloxy group or aromatic hydrocarbon carbonyloxy group is further substituted with alkyl group, alkoxy group, aryl group, aryloxy group, amino group, halogen atom, etc. And the like.
  • R 4 to R 7 may combine with each other to form a cyclic structure” described as R 4 to R 7 in the general formula (I-1) means that 2 to 4 It means that R 4 to R 7 may combine to form one divalent to tetravalent organic group as a whole.
  • R 4 to R 7 in this case include alkylene groups such as ethylene, propylene, butylene, pentylene and hexylene, alkenylene groups such as ethylenylene, propyleneylene and butylene, aralkylene groups such as methylenephenylene, and arylenes such as phenylene, naphthylene and anthracenylene.
  • Substituents that can form a cyclic structure such as a group, and these oxy groups or dioxy groups. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom, or the like.
  • R 4 to R 7 in the general formula (I-1) are not particularly limited.
  • each may be independently selected from a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group.
  • an aryl group substituted with at least one selected from the group consisting of a hydrogen atom, a hydroxyl group, an unsubstituted or alkyl group and an alkoxy group, or a chain or cyclic alkyl group is preferable.
  • Examples of the aryl group that is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group and an alkoxy group include a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, and a p-methoxyphenyl group. Is mentioned.
  • Examples of the chain or cyclic alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, a t-butyl group, an octyl group, and a cyclohexyl group. From the viewpoint of curability, it is preferable that R 4 to R 7 are all hydrogen atoms, or that at least one of R 4 to R 7 is a hydroxyl group and the rest are all hydrogen atoms.
  • R 1 to R 3 are an alkyl group having 1 to 18 carbon atoms or a cycloalkyl group having 3 to 18 carbon atoms
  • R 4 to R 7 are All are hydrogen atoms, or at least one is a hydroxyl group and the rest are all hydrogen atoms.
  • all of R 1 to R 3 are alkyl groups having 1 to 18 carbon atoms or cycloalkyl groups having 3 to 18 carbon atoms
  • R 4 to R 7 are all hydrogen atoms, or at least one is a hydroxyl group And the rest are all hydrogen atoms.
  • the specific curing accelerator is preferably a compound represented by the following general formula (I-2).
  • R 1 to R 3 are each independently a hydrocarbon group having 1 to 18 carbon atoms, and two or more of R 1 to R 3 are bonded to each other to form a cyclic structure.
  • R 4 to R 6 are each independently a hydrogen atom or an organic group having 1 to 18 carbon atoms, and two or more of R 4 to R 6 are bonded to each other to form a cyclic structure. May be.
  • R 1 ⁇ R 6 in the formula (I-2) is the same as specific examples of R 1 ⁇ R 6, respectively, in formula (I-1), and preferred ranges are also the same.
  • specific curing accelerator examples include addition reaction product of triphenylphosphine and 1,4-benzoquinone, addition reaction product of tri-n-butylphosphine and 1,4-benzoquinone, tricyclohexylphosphine and 1,4-benzoquinone Addition reaction product of dicyclohexylphenylphosphine and 1,4-benzoquinone, addition reaction product of cyclohexyldiphenylphosphine and 1,4-benzoquinone, addition reaction product of triisobutylphosphine and 1,4-benzoquinone, tricyclopentylphosphine And 1,4-benzoquinone addition reaction product.
  • the specific curing accelerator can be obtained, for example, as an adduct of a tertiary phosphine compound and a quinone compound.
  • the third phosphine compound include triphenylphosphine, tributylphosphine, dibutylphenylphosphine, butyldiphenylphosphine, ethyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, and tris (4-ethylphenyl) phosphine.
  • the quinone compound examples include o-benzoquinone, p-benzoquinone, diphenoquinone, 1,4-naphthoquinone, anthraquinone and the like. From the viewpoint of moisture resistance and storage stability, p-benzoquinone is preferred.
  • the curable resin composition may contain a curing accelerator other than the phosphonium compound.
  • curing accelerators other than phosphonium compounds include 1,5-diazabicyclo [4.3.0] nonene-5 (DBN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU).
  • Cyclic amidine compounds such as diazabicycloalkene, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-heptadecylimidazole, etc .; derivatives of the cyclic amidine compounds; Phenol novolak salts of derivatives; these compounds include maleic anhydride, 1,4-benzoquinone, 2,5-toluquinone, 1,4-naphthoquinone, 2,3-dimethylbenzoquinone, 2,6-dimethylbenzoquinone, 2,3- Dimethoxy-5-methyl-1,4-benzoquinone, 2,3-dimethoxy-1, A compound having intramolecular polarization formed by adding a compound having a ⁇ bond, such as a quinone compound such as benzoquinone or phenyl-1,4-benzoquinone, diazophenylmethane, or the like; tetraphenylbor
  • the content of the specific curing accelerator is preferably 30% by mass or more of the entire curing accelerator, and preferably 50% by mass or more. More preferably, it is more preferably 70% by mass or more.
  • the amount thereof is preferably 0.1 to 30 parts by mass, preferably 1 to 15 parts by mass with respect to 100 parts by mass of the resin component. Is more preferable. It exists in the tendency which hardens
  • the amount of the curing accelerator is 30 parts by mass or less with respect to 100 parts by mass of the resin component, the curing rate is not too high and a good molded product tends to be obtained.
  • the curable resin composition may include an inorganic filler.
  • an inorganic filler when the curable resin composition is used as a sealing material for a semiconductor package, it is preferable to include an inorganic filler.
  • the type of inorganic filler is not particularly limited. Specifically, fused silica, crystalline silica, glass, alumina, calcium carbonate, zirconium silicate, calcium silicate, silicon nitride, aluminum nitride, boron nitride, beryllia, zirconia, zircon, fosterite, steatite, spinel, mullite , Inorganic materials such as titania, talc, clay and mica.
  • An inorganic filler having a flame retardant effect may be used. Examples of the inorganic filler having a flame retardant effect include aluminum hydroxide, magnesium hydroxide, composite metal hydroxide such as composite hydroxide of magnesium and zinc, zinc borate and the like.
  • fused silica is preferable from the viewpoint of reducing the linear expansion coefficient
  • alumina is preferable from the viewpoint of high thermal conductivity.
  • An inorganic filler may be used individually by 1 type, or may be used in combination of 2 or more type. Examples of the state of the inorganic filler include non-powder, beads spheroidized from the powder, and fibers.
  • the content is not particularly limited. From the viewpoint of fluidity and strength, it is preferably 30% by volume to 90% by volume of the entire curable resin composition, more preferably 35% by volume to 80% by volume, and 40% by volume to 70% by volume. More preferably.
  • the content of the inorganic filler is 30% by volume or more of the entire curable resin composition, characteristics such as thermal expansion coefficient, thermal conductivity, and elastic modulus of the cured product tend to be further improved.
  • the content of the inorganic filler is 90% by volume or less of the entire curable resin composition, an increase in the viscosity of the curable resin composition is suppressed, and the flowability is further improved and the moldability tends to be better. It is in.
  • the average particle size of the inorganic filler is not particularly limited.
  • the volume average particle size is preferably 0.2 ⁇ m to 10 ⁇ m, and more preferably 0.5 ⁇ m to 5 ⁇ m.
  • a volume average particle diameter is 0.2 micrometers or more.
  • the volume average particle diameter of the inorganic filler can be measured as a volume average particle diameter (D50) with a laser diffraction / scattering particle size distribution analyzer.
  • the volume average particle diameter of the curable resin composition or the inorganic filler in the cured product can be measured by a known method. For example, an inorganic filler is extracted from the curable resin composition or cured product using an organic solvent, nitric acid, aqua regia, etc., and sufficiently dispersed with an ultrasonic disperser to prepare a dispersion. Using this dispersion, the volume average particle size of the inorganic filler can be measured from the volume-based particle size distribution measured by a laser diffraction / scattering particle size distribution measuring apparatus.
  • the volume average particle size of the inorganic filler is measured from the volume-based particle size distribution obtained by observing the cross section obtained by embedding the cured product in a transparent epoxy resin and polishing with a scanning electron microscope. Can do. Furthermore, using a FIB apparatus (focused ion beam SEM) or the like, two-dimensional cross-sectional observation of the cured product is continuously performed, and the measurement can be performed by performing a three-dimensional structural analysis.
  • FIB apparatus focused ion beam SEM
  • the particle shape of the inorganic filler is preferably spherical rather than square, and the particle size distribution of the inorganic filler is preferably distributed over a wide range.
  • the curable resin composition may contain various additives such as a coupling agent, an ion exchanger, a release agent, a flame retardant, a colorant, and a stress relaxation agent exemplified below in addition to the components described above.
  • the curable resin composition may contain various additives well known in the art as needed in addition to the additives exemplified below.
  • a coupling agent may be included in order to improve the adhesion between the resin component and the inorganic filler.
  • the coupling agent include known coupling agents such as silane compounds such as epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, and vinyl silane, titanium compounds, aluminum chelate compounds, and aluminum / zirconium compounds. .
  • the amount of the coupling agent is preferably 0.05 parts by mass to 5 parts by mass with respect to 100 parts by mass of the inorganic filler. More preferably, it is 2.5 parts by mass.
  • the amount of the coupling agent is 0.05 parts by mass or more with respect to 100 parts by mass of the inorganic filler, the adhesion with the frame tends to be further improved.
  • the amount of the coupling agent is 5 parts by mass or less with respect to 100 parts by mass of the inorganic filler, the moldability of the package tends to be further improved.
  • the curable resin composition may include an ion exchanger.
  • an ion exchanger when a curable resin composition is used as a molding material for sealing, it is preferable to include an ion exchanger from the viewpoint of improving moisture resistance and high-temperature storage characteristics of an electronic component device including an element to be sealed. .
  • An ion exchanger in particular is not restrict
  • Specific examples include hydrotalcite compounds and hydrous oxides of at least one element selected from the group consisting of magnesium, aluminum, titanium, zirconium and bismuth.
  • An ion exchanger may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the hydrotalcite represented with the following general formula (A) is preferable.
  • the content is not particularly limited as long as the content is sufficient to capture ions such as halogen ions.
  • the amount is preferably 0.1 to 30 parts by mass, more preferably 1 to 15 parts by mass with respect to 100 parts by mass of the resin component.
  • the curable resin composition may contain a release agent from the viewpoint of obtaining good release properties from the mold during molding.
  • the release agent is not particularly limited, and conventionally known release agents can be used. Specific examples include higher fatty acids such as carnauba wax, montanic acid and stearic acid, higher fatty acid metal salts, ester waxes such as montanic acid esters, and polyolefin waxes such as oxidized polyethylene and non-oxidized polyethylene.
  • a mold release agent may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the amount thereof is preferably 0.01 to 15 parts by mass, more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the resin component.
  • the amount of the release agent is 0.01 parts by mass or more with respect to 100 parts by mass of the resin component, the release property tends to be sufficiently obtained.
  • the content is 15 parts by mass or less, better adhesiveness tends to be obtained.
  • the curable resin composition may contain a flame retardant.
  • the flame retardant is not particularly limited, and conventionally known flame retardants can be used. Specifically, an organic or inorganic compound containing a halogen atom, an antimony atom, a nitrogen atom or a phosphorus atom, a metal hydroxide, and the like can be given.
  • a flame retardant may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the amount is not particularly limited as long as the amount is sufficient to obtain a desired flame retardant effect.
  • the amount is preferably 1 part by mass to 300 parts by mass, more preferably 2 parts by mass to 150 parts by mass with respect to 100 parts by mass of the resin component.
  • the curable resin composition may further include a colorant.
  • a colorant include known colorants such as carbon black, organic dyes, organic pigments, titanium oxide, red lead, and bengara.
  • the content of the colorant can be appropriately selected according to the purpose and the like.
  • a coloring agent may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the curable resin composition may contain a stress relaxation agent such as silicone oil and silicone rubber particles. By including the stress relaxation agent, warpage deformation of the package and generation of package cracks can be further reduced.
  • a stress relaxation agent the well-known stress relaxation agent (flexible agent) generally used is mentioned.
  • thermoplastic elastomers such as silicone, styrene, olefin, urethane, polyester, polyether, polyamide, polybutadiene, NR (natural rubber), NBR (acrylonitrile-butadiene rubber), acrylic Rubber particles such as rubber, urethane rubber and silicone powder, core-shell such as methyl methacrylate-styrene-butadiene copolymer (MBS), methyl methacrylate-silicone copolymer, methyl methacrylate-butyl acrylate copolymer Examples thereof include rubber particles having a structure.
  • a stress relaxation agent may be used individually by 1 type, or may be used in combination of 2 or more type. Of these, silicone stress relieving agents are preferred.
  • silicone-based stress relaxation agent include those having an epoxy group, those having an amino group, and those obtained by modifying these with a polyether.
  • the method for preparing the curable resin composition is not particularly limited.
  • a general technique there can be mentioned a method in which components of a predetermined blending amount are sufficiently mixed by a mixer or the like, and then melt-kneaded by a mixing roll, an extruder or the like, cooled and pulverized. More specifically, for example, a method in which predetermined amounts of the above-described components are uniformly stirred and mixed, kneaded with a kneader, roll, extruder, etc., which has been heated to 70 ° C. to 140 ° C., cooled, and pulverized Can be mentioned.
  • the curable resin composition is preferably solid at room temperature and normal pressure (for example, 25 ° C. and atmospheric pressure).
  • the shape in particular when a curable resin composition is solid is not restrict
  • An electronic component device includes an element and a cured product of the above-described curable resin composition that seals the element.
  • Electronic component devices include lead frames, pre-wired tape carriers, wiring boards, glass, silicon wafers, organic substrates and other supporting members, active elements such as semiconductor chips, transistors, diodes, and thyristors, capacitors, and resistors. And an element portion obtained by mounting a passive element such as a coil) with a curable resin composition. More specifically, the element is fixed on the lead frame, the terminal portion of the element such as a bonding pad and the lead portion are connected by wire bonding, bump, etc., and then transferred by using a curable resin composition by transfer molding or the like.
  • DIP Downlink Package
  • PLCC Physical Leaded Chip Carrier
  • QFP Quad Flat Package
  • SOP Small Outline Package TS
  • SOJ Small Outline J-Lead TS
  • General resin-encapsulated IC such as Package
  • TQFP Thin Quad Flat Package
  • TCP Tape Carrier Package
  • COB Chip On Board
  • hybrid ICs multi-chip modules, etc., with the elements mounted on the surface of the support member with the wiring board connection terminals formed on the back, and formed on the elements and the support member by bump or wire bonding Examples thereof include BGA (Ball Grid Array), CSP (Chip Size Package), MCP (Multi Chip Package), etc., which have a structure in which the element is sealed
  • Examples of a method for sealing an electronic component device using a curable resin composition include a low-pressure transfer molding method, an injection molding method, and a compression molding method. Among these, the low-pressure transfer molding method is common.
  • Epoxy resin 1 biphenyl type epoxy resin having an epoxy equivalent of 196 and a melting point of 106 ° C.
  • Epoxy resin 2 styrene-modified phenol novolac type epoxy resin having an epoxy equivalent of 282 and a softening point of 59 ° C.
  • Epoxy resin 3 Methoxynaphthalene / cresol formaldehyde co-condensation type epoxy resin having an epoxy equivalent of 250 and a softening point of 58 ° C.
  • Epoxy resin 4 Bialkyl skeleton-containing aralkyl epoxy resin having an epoxy equivalent of 282 and a softening point of 56 ° C. (Nippon Kayaku Co., Ltd., trade name “NC-3000”)
  • Curing agent 1 phenol aralkyl resin having a hydroxyl equivalent weight of 176 and a softening point of 70 ° C.
  • Curing agent 2 Biphenyl skeleton type phenol aralkyl resin having a hydroxyl group equivalent of 199 and a softening point of 89 ° C. (Maywa Kasei Co., Ltd., trade name “MEH-7851”)
  • Triazine compound Triazine compound 1; 2- (4,6-bis- (2,4-dimethylphenyl) -1,3,5-triazin-2-yl) -5- (octyloxy) -phenol (Cytec, trade name “ UV-1164 ”) Triazine compound 2; 2- [4,6-bis (2,4-dimethylphenyl) -1,3,5-triazin-2-yl] -5- [3-[(2-ethylphenyl) oxy] -2 -Hydroxypropoxy] phenol (trade name “Tinuvin 405” manufactured by BASF) Triazine compound 3; 2,4,6-tris (2-hydroxy-4-hexyloxy-3-methylphenyl) -1,3,5-triazine (ADEKA Corporation, trade name “ADK STAB LA-F70”) Triazine compound 4; 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(hexyl
  • Curing accelerator addition reaction product of triphenylphosphine and 1,4-benzoquinone (inorganic filler) Spherical fused silica (average particle size 17.5 ⁇ m, specific surface area 3.8 m 2 / g) (Coupling agent) Epoxy silane ( ⁇ -glycidoxypropyltrimethoxysilane) (Coloring agent) Carbon black (Mitsubishi Chemical Corporation, trade name “MA-100”) (Release agent) Carnauba wax (Serarica NODA Corporation)
  • the epoxy resin molding material for sealing is molded into a disk having a diameter of 50 mm and a thickness of 3 mm under the above conditions, and immediately after molding, a Shore D hardness meter (HD-1120 (type D, manufactured by Ueshima Seisakusho Co., Ltd.) )).
  • Reflow resistance Seal an 80-pin flat package (QFP) (lead frame material: copper alloy, die pad top surface and lead-plated silver plated product) with external dimensions of 20 mm x 14 mm x 2 mm with a silicon chip measuring 8 mm x 10 mm x 0.4 mm It was molded under the above conditions using an epoxy resin molding material for fixing, and post-cured under the above conditions. The obtained package was humidified for 168 hours at 85 ° C. and 85% RH. Thereafter, a reflow process is performed at predetermined temperatures (250 ° C., 260 ° C., 270 ° C.) for 10 seconds, respectively, and the presence or absence of cracks inside the package is visually observed. Each was observed with Hitachi Construction Machinery Co., Ltd. (HYE-FOCUS). The reflow resistance was evaluated by the total number of packages in which either cracks or peeling occurred with respect to the number of test packages (10).
  • QFP 80-pin flat package
  • Examples 1 to 21 containing the triazine compounds 1 to 10 corresponding to the specific triazine compound are more adhesive to metal (silver) than the comparative examples 1 to 8 not containing the triazine compound. Improved and reflow resistance also improved. Comparative Examples 9 and 10 containing triazine compounds A and B that do not correspond to the specific triazine compound show improved adhesion to metal (silver) and reflow resistance compared to Comparative Examples 1 to 8 containing no triazine compound. There wasn't.

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

Abstract

Cette composition de résine durcissable contient une résine durcissable et un composé représenté par la formule générale (1). Dans la formule générale (1), R1 à R3 représentent chacun indépendamment un groupe hydrocarboné monovalent.
PCT/JP2019/022928 2018-06-12 2019-06-10 Composition de résine durcissable et dispositif à composant électronique WO2019240079A1 (fr)

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JP2020525555A JP7302598B2 (ja) 2018-06-12 2019-06-10 硬化性樹脂組成物及び電子部品装置
SG11202012017VA SG11202012017VA (en) 2018-06-12 2019-06-10 Curable resin composition and electronic component device
KR1020207034779A KR20210019004A (ko) 2018-06-12 2019-06-10 경화성 수지 조성물 및 전자 부품 장치
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WO2020153205A1 (fr) * 2019-01-23 2020-07-30 富士フイルム株式会社 Composition, feuille thermoconductrice et dispositif équipé d'une couche thermoconductrice
WO2021220726A1 (fr) * 2020-04-30 2021-11-04 昭和電工マテリアルズ株式会社 Composition de résine époxy pour encapsulation, dispositif à composants électroniques, et leur procédé de fabrication
WO2021230002A1 (fr) * 2020-05-15 2021-11-18 富士フイルム株式会社 Composition durcissable, matériau thermoconducteur, feuille thermoconductrice, dispositif à couche thermoconductrice, et composé
WO2022075453A1 (fr) * 2020-10-08 2022-04-14 昭和電工マテリアルズ株式会社 Composition de résine durcissable et dispositif à composant électronique
US20220306794A1 (en) * 2021-03-29 2022-09-29 Chang Chun Plastics Co. Ltd. Polyhydric phenol resin, glycidyl ether of polyhydric phenol resin, and uses thereof
WO2023032860A1 (fr) * 2021-08-30 2023-03-09 株式会社レゾナック Composition de résine durcissable, et dispositif de composant électronique

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Publication number Priority date Publication date Assignee Title
WO2020153205A1 (fr) * 2019-01-23 2020-07-30 富士フイルム株式会社 Composition, feuille thermoconductrice et dispositif équipé d'une couche thermoconductrice
JPWO2020153205A1 (ja) * 2019-01-23 2021-10-14 富士フイルム株式会社 組成物、熱伝導シート、熱伝導層付きデバイス
JP7221307B2 (ja) 2019-01-23 2023-02-13 富士フイルム株式会社 組成物、熱伝導シート、熱伝導層付きデバイス
WO2021220726A1 (fr) * 2020-04-30 2021-11-04 昭和電工マテリアルズ株式会社 Composition de résine époxy pour encapsulation, dispositif à composants électroniques, et leur procédé de fabrication
WO2021230002A1 (fr) * 2020-05-15 2021-11-18 富士フイルム株式会社 Composition durcissable, matériau thermoconducteur, feuille thermoconductrice, dispositif à couche thermoconductrice, et composé
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WO2022075453A1 (fr) * 2020-10-08 2022-04-14 昭和電工マテリアルズ株式会社 Composition de résine durcissable et dispositif à composant électronique
CN116349008A (zh) * 2020-10-08 2023-06-27 株式会社力森诺科 硬化性树脂组合物及电子零件装置
US20220306794A1 (en) * 2021-03-29 2022-09-29 Chang Chun Plastics Co. Ltd. Polyhydric phenol resin, glycidyl ether of polyhydric phenol resin, and uses thereof
US11629216B2 (en) * 2021-03-29 2023-04-18 Chang Chun Plastics Co., Ltd. Polyhydric phenol resin, glycidyl ether of polyhydric phenol resin, and uses thereof
WO2023032860A1 (fr) * 2021-08-30 2023-03-09 株式会社レゾナック Composition de résine durcissable, et dispositif de composant électronique

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TW202000767A (zh) 2020-01-01
CN112292425A (zh) 2021-01-29
TWI829708B (zh) 2024-01-21

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