WO2020054356A1 - Accélérateur de durcissement de résine époxy et composition de résine époxy - Google Patents

Accélérateur de durcissement de résine époxy et composition de résine époxy Download PDF

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Publication number
WO2020054356A1
WO2020054356A1 PCT/JP2019/032967 JP2019032967W WO2020054356A1 WO 2020054356 A1 WO2020054356 A1 WO 2020054356A1 JP 2019032967 W JP2019032967 W JP 2019032967W WO 2020054356 A1 WO2020054356 A1 WO 2020054356A1
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WIPO (PCT)
Prior art keywords
epoxy resin
group
curing accelerator
resin composition
represented
Prior art date
Application number
PCT/JP2019/032967
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English (en)
Japanese (ja)
Inventor
慶彦 赤澤
淳 舩山
Original Assignee
サンアプロ株式会社
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Priority to JP2020546809A priority Critical patent/JP7228597B2/ja
Publication of WO2020054356A1 publication Critical patent/WO2020054356A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • 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
    • C08G59/70—Chelates

Definitions

  • the present invention relates to an epoxy resin curing accelerator and an epoxy resin composition. More specifically, the present invention relates to an epoxy resin curing accelerator suitable for producing an epoxy resin-based encapsulant for electronic components such as semiconductor elements, and an epoxy resin composition containing the same.
  • the curability of the epoxy resin composition is good and the reliability of the semiconductor device is improved, and the flowability is good and the epoxy resin composition is sufficiently filled in the package, and the void is improved. It is an object of the present invention to provide an epoxy resin composition which is free from the possibility of occurrence of a resin.
  • the present invention provides an imidazolium salt (S) comprising an imidazolium cation (A) represented by the general formula (1) and an anion (B) represented by the general formula (2), (3) or (4).
  • the melting point of the imidazolium salt (S) is 170 ° C. or less; an epoxy resin curing accelerator (Q); and the epoxy resin curing accelerator (Q), an epoxy resin (E), And an epoxy resin composition containing a compound (P) having two or more phenolic hydroxyl groups in one molecule.
  • R1 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group or a butyl group
  • R2 and R3 are the same or different and represent a methyl group, an ethyl group, a propyl group or a butyl group
  • R4 and R5 are the same or different and represent a hydrogen atom, a methyl group or an ethyl group.
  • the group represented by -R6-R7-R8- and -R10-R11-R12- is a group formed by a divalent or higher proton donor releasing two protons. And these groups may be the same or different from each other.
  • R9 represents an aromatic hydrocarbon group which may have a substituent or an aliphatic hydrocarbon group which may have a substituent.
  • the group represented by -R13-R14-R15-, -R16-R17-R18- and -R19-R20-R21- is a group in which a divalent or higher-valent proton donor has two protons. These groups are constituted by groups that are released, and these groups may be the same or different from each other. ]
  • the group represented by -R22-R23-R24- and -R25-R26-R27- is a group formed by a divalent or higher proton donor releasing two protons. And these groups may be the same or different from each other. ]
  • the epoxy resin curing accelerator (Q) of the present invention has extremely high heat resistance of the imidazolium cation (A) and is stable. Therefore, the salt can be combined with the anion (B) represented by the general formula (2), (3) or (4) even at the compounding temperature at which the composition is heated and melted, and the acceleration of the curing reaction can be suppressed. Furthermore, since the anion portion forms a chelate structure, it has good thermal stability, and does not accelerate the curing reaction even at the compounding temperature at which the mixture of the epoxy resin, the curing agent and the curing accelerator is heated and melted. On the other hand, at an even higher curing temperature, the epoxy resin composition can be quickly decomposed, and the reaction between the epoxy resin and the curing agent can be promoted. Therefore, the curability of the epoxy resin composition is good and the reliability of the semiconductor device can be improved.
  • the epoxy resin curing accelerator (Q) has an imidazolium cation (A) and therefore has a relatively low melting point. That is, the melting point is close to or lower than the compounding temperature at which the mixture is heated and melted. From this, an epoxy resin composition having good fluidity can be designed. That is, by using the epoxy resin curing accelerator (Q), the curability of the epoxy resin composition is improved, the reliability of the semiconductor device is improved, the fluidity is improved, the epoxy resin composition is sufficiently filled in the package, and voids are formed. It is an epoxy resin composition that is unlikely to be produced, and is suitable for producing an epoxy resin-based sealing material for electronic components such as semiconductors.
  • the epoxy resin curing accelerator (Q) of the present invention comprises an imidazolium cation (A) represented by the general formula (1) and an anion (B) represented by the general formula (2), (3) or (4). Characterized by containing an imidazolium salt (S).
  • the imidazolium cation (A) is represented by the general formula (1), wherein R1 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group or a butyl group, and R2 and R3 are the same or different. Differently represents a methyl group, an ethyl group, a propyl group or a butyl group, and R4 and R5 are the same or different and represent a hydrogen atom, a methyl group or an ethyl group.
  • R1 is preferably a hydrogen atom from the viewpoint of curability of the epoxy resin composition. This is because imidazolium becomes a carbene compound in the process of curing the epoxy resin composition. Further, from the viewpoint of fluidity, R4 and R5 are preferably a hydrogen atom.
  • imidazolium cation (A) examples include 1-ethyl-3-methylimidazolium cation, 1-propyl-3-methylimidazolium cation, 1-butyl-3-methylimidazolium cation, 1-butyl-2 1,3-dimethylimidazolium cation, 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation, 1,2,3-trimethylimidazolium cation, 1,2,3,4-tetramethylimidazolium cation 1,3,4-trimethyl-2-ethylimidazolium cation, 1,3-dimethyl-2,4-diethylimidazolium cation, 1,2-dimethyl-3,4-diethylimidazolium cation, 1-methyl- 2,3,4-triethylimidazolium cation, 1,2,3,4-te La ethyl imidazolium cation,
  • the imidazolium cation (A) can be produced, for example, by a reaction using an alkyl carbonate of a quaternized amine cation, a reaction using a hydroxide of a quaternized amine cation, or the like.
  • the anion (B) is represented by the general formula (2), (3) or (4).
  • the group represented by -R6-R7-R8- and -R10-R11-R12- is a group formed by a divalent or higher proton donor releasing two protons. And these groups may be the same or different from each other.
  • R9 represents an aromatic hydrocarbon group which may have a substituent or an aliphatic hydrocarbon group which may have a substituent.
  • the group represented by -R13-R14-R15-, -R16-R17-R18- and -R19-R20-R21- is a group in which a divalent or higher-valent proton donor has two protons. These groups are constituted by groups that are released, and these groups may be the same or different from each other. ]
  • the group represented by -R22-R23-R24- and -R25-R26-R27- is a group formed by a divalent or higher proton donor releasing two protons. And these groups may be the same or different from each other. ]
  • R9 represents an aromatic hydrocarbon group which may have a substituent or an aliphatic hydrocarbon group which may have a substituent.
  • the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and an anthracenyl group.
  • the substituent include an alkyl group having 1 to 18 carbon atoms and a halogen atom.
  • the aliphatic hydrocarbon group include an alkyl group having 1 to 18 carbon atoms.
  • the substituent include a halogen atom.
  • the above-mentioned imidazolium cation (A), a chelate bond with an alkoxysilane (or boric acid, borate), and a silicon atom (or boron atom) are used.
  • a method of reacting the proton donor that can be formed with the proton donor at a fixed ratio may be used.
  • alkoxysilanes include, for example, phenyltrimethoxysilane, phenyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, and tetra Ethoxysilane and the like can be mentioned.
  • the melting point of the imidazolium salt (S) of the present invention is 170 ° C. or lower, preferably 120 ° C. or lower.
  • the lower limit is preferably ⁇ 50 ° C. or higher from the viewpoint of ease of handling.
  • the more preferable melting point is from -30 ° C to 120 ° C, more preferably from -20 ° C to 100 ° C, and most preferably from 0 ° C to 70 ° C. If the temperature exceeds 170 ° C., the viscosity increases and the fluidity deteriorates.
  • the epoxy resin composition of the present invention contains an epoxy resin (E), a compound (P) having two or more phenolic hydroxyl groups in one molecule, and the epoxy resin curing accelerator (Q).
  • the epoxy resin (E) is generally an oligomer or polymer having two or more epoxy groups in one molecule, and its molecular weight and molecular structure are not particularly limited. Examples thereof include a phenol novolak type epoxy resin and a cresol novolak type.
  • Epoxy resin hydroquinone type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, biphenyl type epoxy resin, stilbene type epoxy resin, triphenolmethane type epoxy resin, alkyl-modified triphenolmethane type epoxy resin, epoxy containing triazine nucleus Resin, dicyclopentadiene-modified phenol type epoxy resin, phenol aralkyl type epoxy resin having phenylene and / or biphenylene skeleton, naphthol type epoxy resin, naphthalene type epoxy resin, resin Ylene and / or naphthol aralkyl type epoxy resins. Having a biphenylene skeleton, it no problem is used singly or in admixture.
  • Examples of the epoxy resin (E) include those manufactured by DIC Corporation: HP-4032, HP-4700, HP-7200, HP-820, HP-4770, HP-5000, EXA-850, EXA-830, EXA- 1514, EXA-4850 series; manufactured by Nippon Kayaku Co., Ltd .: EPPN-201L, BREN-105, EPPN-502H, EOCN-1020, NC-2000-L, XD-1000, NC-7000L, NC-7300L, EPPN -501H, NC-3000; manufactured by Mitsubishi Chemical Corporation: XY-4000.
  • the compound (P) having two or more phenolic hydroxyl groups in one molecule includes all monomers, oligomers and polymers having two or more phenolic hydroxyl groups in one molecule, and the molecular weight and molecular structure are not particularly limited.
  • a naphthol aralkyl resin and a bisphenol compound which may be used singly or as a mixture.
  • Examples of the compound (P) having two or more phenolic hydroxyl groups include: HF series, MEH-7500 series, MEH-7800 series, MEH-7851 series, MEH-7600 series, MEH-8000 manufactured by Meiwa Kasei Corporation. Series: TriP-PA, BisP-TMC, BisP-AP, OC-BP, TekP-4HBPA, CyRS-PRD4, etc., manufactured by Honshu Chemical Industry Co., Ltd.
  • the amount of the epoxy resin curing accelerator (Q) is adjusted according to the reactivity of the epoxy resin and the curing agent, and is usually 1 to 25 parts by weight, preferably 2 to 20 parts by weight, per 100 parts by weight of the epoxy resin. It is.
  • the mixing ratio of the epoxy resin (E) and the compound (P) having two or more phenolic hydroxyl groups in one molecule is not particularly limited, either, but the compound ( The phenolic hydroxyl group of P) is preferably used in an amount of 0.5 to 2 equivalents, more preferably 0.7 to 1.5 equivalents.
  • the epoxy resin composition of the present invention preferably further contains an inorganic filler (H).
  • an inorganic filler H
  • the epoxy resin composition of the present invention is used for sealing electronic components such as semiconductor elements, for the purpose of improving the solder resistance of the obtained semiconductor device, the epoxy resin composition is incorporated into the epoxy resin composition.
  • the type is not particularly limited, and those generally used for a sealing material can be used.
  • the content of the inorganic filler (H) is not particularly limited, the total amount of the epoxy resin (E) and the compound (P) having two or more phenolic hydroxyl groups in one molecule per 100 parts by weight is as follows: It is preferably from 200 to 2400 parts by weight, more preferably from 400 to 1400 parts by weight.
  • the epoxy resin composition of the present invention further contains another functional compound (functional additive).
  • Functional additives include, for example, 3-glycidyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane and phenyltrimethoxysilane Coupling agents represented by alkoxysilanes, titanate esters, and aluminate esters; and coloring agents such as carbon black; brominated epoxy resins, antimony oxide, aluminum hydroxide, magnesium hydroxide, zinc oxide, and phosphorus.
  • Flame retardants such as system compounds; low-stress components such as silicone oil and silicone rubber; natural waxes such as carnauba wax; synthetic waxes such as polyethylene wax; higher fatty acids such as stearic acid and zinc stearate; metal salts of the higher fatty acids Release agents such as paraffin and paraffin; various additives such as magnesium, aluminum, titanium and bismuth-based ion catchers and bismuth antioxidants; and heat-resistant UP-modified compounds such as benzoxazine, cyanate ester and bismaleimide.
  • Low-stress components such as silicone oil and silicone rubber
  • natural waxes such as carnauba wax
  • synthetic waxes such as polyethylene wax
  • higher fatty acids such as stearic acid and zinc stearate
  • metal salts of the higher fatty acids Release agents such as paraffin and paraffin
  • various additives such as magnesium, aluminum, titanium and bismuth-based ion catchers and bismuth antioxidants
  • the epoxy resin composition of the present invention may contain a resin other than the epoxy resin (E) and the compound (P) having two or more phenolic hydroxyl groups in one molecule.
  • Other resins include an epoxy resin using an acid anhydride, a polyimide resin, a nanocomposite resin, a cyanate ester resin, and the like.
  • the epoxy resin composition of the present invention is obtained by uniformly mixing the above components and, if necessary, other additives and the like using a mixer, and further, a mixture obtained at room temperature, roll, kneader, co-kneader And kneading by heating using a kneader such as a twin screw extruder, and then cooling and pulverizing.
  • a kneader such as a twin screw extruder
  • the epoxy resin composition obtained above is a powder, it can be used in the form of a pressurized tablet by a press or the like in order to improve workability in use.
  • Examples of the use of the epoxy resin composition of the present invention include, for example, encapsulating various electronic components such as a semiconductor element, and when manufacturing a semiconductor device, a conventional method such as a transfer mold, a compression mold, and an injection mold. Curing molding can be performed by a molding method.
  • curing accelerators epoxy resin curing accelerators
  • ⁇ Method for producing imidazolium salt (S-7) 252 parts of pyrogallol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used in place of 2,3-dihydroxynaphthalene in the method for producing the imidazolium salt (S-1), and trimethoxyhexylsilane (in place of triethoxyphenylsilane) was used.
  • the imidazolium salt (S-7) represented by the following formula (s7) was obtained by using 206 parts (manufactured by Tokyo Chemical Industry Co., Ltd.) and removing the solvent with an evaporator instead of filtration. Note that a 28% methanol solution of sodium methoxide was not used.
  • the melting points of the imidazolium salts (S-1) to (S-7) and the salts (S'-1) to (S'-3) were measured by the following method. Table 1 shows the results. ⁇ Melting point> The sample was placed on a SUS test table, the temperature was gradually raised, and the melting temperature was read visually.
  • Epoxy resin 1 100 parts, manufactured by Nippon Kayaku Co., Ltd., trade name: NC3000 (softening point: 58 ° C., epoxy equivalent: 273); Phenolic resin-based curing agent: manufactured by Meiwa Kasei Co., Ltd., trade name: MEH-7500 (softening point) 33 parts of 110 ° C., hydroxyl equivalent 97); 7 parts of epoxy resin curing accelerator [imidazolium salt (S-1)]; 1000 parts of fused silica powder treated with 1% by weight of a silane coupling agent, 1.5 parts of carnauba wax Parts, 4 parts of antimony trioxide and 1 part of carbon black were uniformly pulverized and mixed, then melt-kneaded using a hot roll at 130 ° C. for 10 minutes, cooled and pulverized to obtain a sealing material.
  • the obtained epoxy resin composition was evaluated by the following method. Table 2 shows the results.
  • Examples 2 to 8 Comparative Examples 1 to 3 According to the formulation in Table 2, an epoxy resin composition was obtained in the same manner as in Example 1, and evaluated in the same manner as in Example 1. Table 2 shows the results. The raw materials used in other than Example 1 are shown below.
  • Epoxy resin 2 XY-4000H (manufactured by Mitsubishi Chemical Corporation) (softening point 80 ° C, epoxy equivalent 192)
  • Phenolic resin-based curing agent 2 MEH-7851SS (trade name: softening point 67 ° C, hydroxyl equivalent 203, manufactured by Meiwa Kasei Co., Ltd.)
  • the epoxy resin compositions of Examples 1 to 8 of the present invention have a large flow value of the sealant after melt-kneading, are excellent in fluidity, and are hardened, as compared with Comparative Examples. It can be seen that the torque is high and the curability is excellent.
  • Comparative Examples 1 and 2 use a curing accelerator having a low melting point, so that the flow value indicating fluidity is relatively large, but the curing torque indicating curability is low. Comparative Example 3 is the opposite, and Comparative Example does not have both fluidity and curability as in the example.
  • the epoxy resin curing accelerator (Q) of the present invention has good curability of the epoxy resin composition, enhances reliability of the semiconductor device, has good fluidity, sufficiently fills the package with the epoxy resin composition, and generates voids. It is an epoxy resin composition that does not have a risk of becoming, and is suitable for producing an epoxy resin-based sealing material for electronic components such as semiconductors.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention a pour objectif de fournir un accélérateur de durcissement d'époxy qui présente une résistance à la chaleur extrêmement élevée et stable, et dans lequel l'accélération d'une réaction de durcissement peut être supprimée ; et une composition de résine époxy qui augmente la fiabilité d'un dispositif à semi-conducteur et présente de bonnes propriétés de durcissement grâce à l'utilisation de l'accélérateur de durcissement d'époxy, la composition de résine époxy possédant une bonne fluidité et remplissant complètement l'intérieur d'un emballage, et des vides n'étant pas susceptibles de se produire dans la composition de résine époxy. La présente invention concerne un accélérateur de durcissement de résine époxy (Q) caractérisé en ce qu'il comporte un sel d'imidazolium (S) comprenant : un cation imidazolium (A) représenté par la formule générale (1) ; et un anion (B) représenté par la formule générale (2), (3), ou (4) ; le point de fusion du sel d'imidazolium (S) étant de 170 °C ou moins.
PCT/JP2019/032967 2018-09-13 2019-08-23 Accélérateur de durcissement de résine époxy et composition de résine époxy WO2020054356A1 (fr)

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Application Number Priority Date Filing Date Title
JP2020546809A JP7228597B2 (ja) 2018-09-13 2019-08-23 エポキシ樹脂硬化促進剤及びエポキシ樹脂組成物

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JP2018-171126 2018-09-13
JP2018171126 2018-09-13
JP2019098309 2019-05-27
JP2019-098309 2019-05-27

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020200393A (ja) * 2019-06-10 2020-12-17 サンアプロ株式会社 エポキシ樹脂硬化促進剤およびエポキシ樹脂組成物
US10906921B2 (en) * 2016-05-10 2021-02-02 Toyo Gosei Co., Ltd. Base generator, reagent, organic salt, composition, method for manufacturing device, cured film and device
WO2023182370A1 (fr) * 2022-03-25 2023-09-28 パナソニックＩｐマネジメント株式会社 Composition de résine époxy pour scellement et dispositif électronique

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JP2001253933A (ja) * 2000-03-09 2001-09-18 Sumitomo Bakelite Co Ltd 半導体封止用エポキシ樹脂成形材料及びこれを用いた半導体装置
JP2007119598A (ja) * 2005-10-28 2007-05-17 Sumitomo Bakelite Co Ltd 半導体封止用エポキシ樹脂組成物および半導体装置
JP2008081684A (ja) * 2006-09-28 2008-04-10 Sumitomo Bakelite Co Ltd 一液型エポキシ樹脂組成物
JP2010529271A (ja) * 2007-06-11 2010-08-26 ビーエーエスエフ ソシエタス・ヨーロピア エポキシ硬化のための触媒
JP2018104559A (ja) * 2016-12-27 2018-07-05 サンアプロ株式会社 エポキシ樹脂硬化促進剤

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Publication number Priority date Publication date Assignee Title
JP2001253933A (ja) * 2000-03-09 2001-09-18 Sumitomo Bakelite Co Ltd 半導体封止用エポキシ樹脂成形材料及びこれを用いた半導体装置
JP2007119598A (ja) * 2005-10-28 2007-05-17 Sumitomo Bakelite Co Ltd 半導体封止用エポキシ樹脂組成物および半導体装置
JP2008081684A (ja) * 2006-09-28 2008-04-10 Sumitomo Bakelite Co Ltd 一液型エポキシ樹脂組成物
JP2010529271A (ja) * 2007-06-11 2010-08-26 ビーエーエスエフ ソシエタス・ヨーロピア エポキシ硬化のための触媒
JP2018104559A (ja) * 2016-12-27 2018-07-05 サンアプロ株式会社 エポキシ樹脂硬化促進剤

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10906921B2 (en) * 2016-05-10 2021-02-02 Toyo Gosei Co., Ltd. Base generator, reagent, organic salt, composition, method for manufacturing device, cured film and device
JP2020200393A (ja) * 2019-06-10 2020-12-17 サンアプロ株式会社 エポキシ樹脂硬化促進剤およびエポキシ樹脂組成物
JP7283984B2 (ja) 2019-06-10 2023-05-30 サンアプロ株式会社 エポキシ樹脂硬化促進剤およびエポキシ樹脂組成物
WO2023182370A1 (fr) * 2022-03-25 2023-09-28 パナソニックＩｐマネジメント株式会社 Composition de résine époxy pour scellement et dispositif électronique

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JP7228597B2 (ja) 2023-02-24
TWI809189B (zh) 2023-07-21
TW202012374A (zh) 2020-04-01

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