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WO2025075065A1 - Composition polymérisable par voie thermique et cationique, son utilisation, procédé de polymérisation cationique l'utilisant, et stabilisant pour compositions polymérisables par voie thermique et cationique - Google Patents

Composition polymérisable par voie thermique et cationique, son utilisation, procédé de polymérisation cationique l'utilisant, et stabilisant pour compositions polymérisables par voie thermique et cationique Download PDF

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Publication number
WO2025075065A1
WO2025075065A1 PCT/JP2024/035366 JP2024035366W WO2025075065A1 WO 2025075065 A1 WO2025075065 A1 WO 2025075065A1 JP 2024035366 W JP2024035366 W JP 2024035366W WO 2025075065 A1 WO2025075065 A1 WO 2025075065A1
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carbon atoms
group
polymerizable composition
cationic polymerizable
thermally
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English (en)
Japanese (ja)
Inventor
亮輔 中所
智美 岡本
直樹 寺田
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Sanshin Chemical Industry Co Ltd
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Sanshin Chemical Industry Co Ltd
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Priority to JP2025520077A priority Critical patent/JP7748607B2/ja
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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
    • C08G59/68—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds

Definitions

  • Onium salts such as sulfonium salts, are widely used as cationic polymerization initiators.
  • Anion species derived from super strong acids such as tetrakis(pentafluorophenyl)borate and hexafluoroantimonate, are often used as the anion species contained in the onium salt, which allows the initiation temperature of cationic polymerization to be lowered. Lowering the polymerization initiation temperature is preferable in terms of suppressing shrinkage after curing, protecting electronic components, and reducing energy consumption.
  • Patent Document 1 describes a method for stabilizing an alicyclic epoxy resin, in which a sulfonium salt containing hexafluoroantimonate, hexafluorophosphate, tetrakis(pentafluorophenyl)borate or the like as an anion species is blended with an aromatic sulfide and a sulfonium salt containing methyl sulfate or ethyl sulfate as an anion species as a stabilizer to an alicyclic epoxy resin containing a sulfonium salt containing hexafluoroantimonate, hexafluorophosphate, tetrakis(pentafluorophenyl)borate or the like as a polymerization initiator.
  • the stabilizing effect is still insufficient, and it is sometimes difficult to achieve a long pot life.
  • Patent Document 2 describes the use of a sulfonium salt containing trifluoromethanesulfonate as an anion species as a polymerization initiator.
  • this polymerization initiator has the problem of having a high polymerization initiation temperature.
  • the present invention has been made to solve the above problems, and aims to provide a thermally cationic polymerizable composition that has a long pot life even when using a cationic polymerization initiator with a low polymerization initiation temperature, and uses thereof. It also aims to provide a cationic polymerization method that uses the thermally cationic polymerizable composition. It is also an object of the present invention to provide a stabilizer for a thermally cationic polymerizable composition that has a long pot life.
  • R f 1 to 7 are each independently a fluorine-containing group selected from the group consisting of a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluoroaryl group having 6 to 10 carbon atoms, a perfluoroalkyl-substituted aryl group having 7 to 14 carbon atoms, a perfluoroalkylsulfonyl group having 1 to 6 carbon atoms, and a perfluoroalkoxy group having 1 to 6 carbon atoms.
  • any of the thermally cationic polymerizable compositions may contain 0.001 to 1000 parts by mass of organic solvent (D) per 100 parts by mass of cationic polymerizable compound (A).
  • the organic solvent (D) may be an organic solvent (d1) capable of dissolving the same mass of cationic polymerization initiator (B) at 25°C, and may contain 10 to 1000 parts by mass of organic solvent (d1) per 100 parts by mass of cationic polymerization initiator (B).
  • the epoxy compound may be a monoepoxy compound having one epoxy group in one molecule, or a polyfunctional epoxy compound having two or more epoxy groups, or a mixture of these may be used.
  • a polyfunctional epoxy compound is preferable.
  • One molecule of a polyfunctional epoxy compound usually contains 2 to 7 epoxy groups. From the viewpoint of fluidity and suppression of unreacted epoxy groups, it is preferable that one molecule contains two epoxy groups.
  • alicyclic epoxy compounds are preferable, and in particular compounds having epoxycyclohexane groups are preferable. Therefore, compounds having two epoxycyclohexane groups in one molecule are particularly preferable, and a representative example is 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate.
  • R f group which is a strong electron-withdrawing group containing fluorine, is bonded to it to form a monovalent anion as a whole (X ⁇ ).
  • a plurality of Rf groups bonded to the same central element may be the same or different, but all of the bonded groups must be Rf groups.
  • a plurality of perfluoroalkyl groups, perfluoroalkylsulfonyl groups, and perfluoroalkoxy groups bonded to one central element may be bonded to each other to form a perfluoroalkylene group to form a ring.
  • a plurality of perfluoroalkyl groups, perfluoroalkylsulfonyl groups, and perfluoroalkoxy groups bonded to one central element may be bonded to each other to form a perfluoroalkylene group to form a ring.
  • the number of carbon atoms of the perfluoroalkyl group is preferably 1 to 4, more preferably 1 to 3.
  • Specific examples of the perfluoroalkyl group include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoronormalpropyl group, a heptafluoroisopropyl group, and a nonafluoro-t-butyl group.
  • the number of carbon atoms of the perfluoroaryl group is preferably 6 to 8, more preferably 6 to 7.
  • Specific examples of the perfluoroaryl group include a pentafluorophenyl group.
  • Suitable anions represented by "X - " include anions represented by the following formulas (1x) to (11x).
  • anions represented by the formulas (1x) to (10x) are preferred, anions represented by the formulas (1x) to (7x) are more preferred, and anions represented by the formulas (1x) to (2x) are even more preferred.
  • cationic polymerization initiator (B) which is the compound represented by the above formula (1)
  • various sulfonium salts commercially available as cationic polymerization initiators can be used.
  • it can also be produced by exchanging the anion using a commercially available sulfonium salt as a raw material.
  • the anion species in formula (2) is trifluoromethanesulfonate.
  • trifluoromethanesulfonate as the anion species of the stabilizer (C)
  • the increase in viscosity of the thermally cationic polymerizable composition at low temperatures can be effectively suppressed, and the composition can be kept in a low-viscosity liquid state, thereby extending the pot life.
  • the compound represented by formula (2) itself can act as a cationic polymerization initiator, but when combined with a more active cationic polymerization initiator (B), the increase in viscosity of the thermally cationic polymerizable composition during storage at low temperatures can be suppressed for a long period of time.
  • R 4 , R 5 and R 6 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 15 carbon atoms which may have a substituent, or an aralkyl group having 7 to 15 carbon atoms which may have a substituent.
  • R 4 , R 5 and R 6 may be the same group or may be different from each other.
  • the number of carbon atoms of the alkyl group is preferably 1 to 6, more preferably 1 to 4.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a normal propyl group, and an isopropyl group.
  • the number of carbon atoms of the aryl group is preferably 6 to 10, more preferably 6 to 8.
  • Specific examples of the aryl group include a 4-hydroxyphenyl group and a 4-acetoxyphenyl group.
  • the number of carbon atoms of the aralkyl group is preferably 7 to 11, more preferably 7 to 9.
  • Specific examples of the aralkyl group include a benzyl group, a 2-methylbenzyl group, a 4-methylbenzyl group, and a 1-naphthylmethyl group.
  • the thermally cationic polymerizable composition of the present invention contains 0.01 to 20 parts by mass of a cationic polymerization initiator (B) per 100 parts by mass of a cationic polymerizable compound (A), and contains 0.1 to 50 parts by mass of a stabilizer (C) per 100 parts by mass of the cationic polymerization initiator (B).
  • the content of stabilizer (C) per 100 parts by mass of cationic polymerization initiator (B) is less than 0.1 parts by mass, the storage stability of the thermal cationic polymerizable composition decreases and the pot life becomes shorter.
  • the content of stabilizer (C) is preferably 0.2 parts by mass or more, more preferably 0.4 parts by mass or more.
  • the content of stabilizer (C) per 100 parts by mass of cationic polymerization initiator (B) exceeds 50 parts by mass, the polymerization reaction at a relatively low temperature does not proceed sufficiently, and the hardness of the cured product may decrease or the amount of unreacted monomer may increase.
  • the content of stabilizer (C) is preferably 20 parts by mass or less, more preferably 10 parts by mass or less.
  • the thermal cationic polymerizable composition of the present invention may contain an organic solvent (D) in addition to the cationic polymerizable compound (A), the cationic polymerization initiator (B), and the stabilizer (C), and may contain 0.001 to 1000 parts by mass of the organic solvent (D) per 100 parts by mass of the cationic polymerizable compound (A).
  • an organic solvent By containing an organic solvent, it may be possible to reduce the viscosity and improve the coatability. In addition, it becomes easier to dissolve the cationic polymerization initiator (B) and the stabilizer (C) in the thermal cationic polymerizable composition.
  • the content of the organic solvent (D) may be 5 to 500 parts by mass, or 10 to 200 parts by mass per 100 parts by mass of the cationic polymerizable compound (A).
  • the content of the organic solvent (D) in the thermally cationic polymerizable composition may be less than 10 parts by mass per 100 parts by mass of the cationic polymerization initiator (B). This can suppress the generation of organic volatile components, and in some cases, the drying step can be omitted. Furthermore, it is preferable that the thermally cationic polymerizable composition is substantially free of organic solvent (D), which can suppress the generation of organic volatile components and also makes the drying step unnecessary. This point is particularly important in the manufacturing process of electronic components and semiconductors, where contamination of the working environment is undesirable.
  • the thermal cationic polymerizable composition of the present invention may contain other components other than the cationic polymerizable compound (A), cationic polymerization initiator (B), stabilizer (C), and organic solvent (D) to the extent that the effects of the present invention are not hindered.
  • Various other components can be added depending on the application, such as fillers, reinforcing fibers, conductive particles, colorants, photopolymerization initiators, ultraviolet absorbers, photosensitizers, antioxidants, flame retardants, leveling agents, silane coupling agents, radical polymerizable compounds, (meth)acrylic resins, polyurethane resins, polyamide resins, and polyester resins.
  • a preferred cationic polymerization method of the present invention is a method in which the thermally cationic polymerizable composition is optionally dried and then heated to cause cationic polymerization.
  • the thermally cationic polymerizable composition which is liquid at room temperature, is heated to cause cationic polymerization (curing reaction) to proceed, thereby obtaining a product (cured composition).
  • the thermal cationic polymerizable composition was prepared by blending the cationic polymerizable compound (A), the cationic polymerization initiator (B), and the stabilizer (C) at the user's factory where the composition was cured by heating.
  • the thermal cationic polymerizable composition by blending the cationic polymerizable compound (A), the cationic polymerization initiator (B), and the stabilizer (C) at the pharmaceutical manufacturer, transport it outdoors, and then optionally dry it before heating it to proceed with cationic polymerization. This allows pharmaceutical manufacturers to manufacture in bulk, eliminating the burden on users of operating and managing mixing equipment.
  • the thermally cationic polymerizable composition of the present invention has a longer pot life, while at the same time, as shown in the DSC curve of the examples ( Figure 1), the polymerization initiation temperature is lower than that of conventional stabilizers. This makes it possible to suppress unnecessary polymerization reactions at storage temperatures while suppressing increases in the polymerization initiation temperature, and thus makes it possible to achieve both long-term storage and low-temperature curing.
  • the heat generation initiation temperature of the thermally cationic polymerizable composition of the present invention is preferably 80°C or lower.
  • the heat generation initiation temperature is more preferably 78°C or lower, and even more preferably 76°C or lower.
  • the heat generation initiation temperature is usually 60°C or higher.
  • the electrical resistivity of the cured product of the thermal cationic polymerizable composition is reduced by adding a stabilizer, but the electrical resistivity of the cured product of the thermal cationic polymerizable composition of the present invention is less likely to decrease than that of the conventional stabilizer. Therefore, it is suitable for applications requiring high insulation.
  • the electrical resistivity of the cured product of the thermal cationic polymerizable composition of the present invention is preferably 3 ⁇ 10 7 ⁇ m or more, more preferably 4 ⁇ 10 7 ⁇ m or more.
  • the organic solvent (d1) is not used (Example 5)
  • the electrical resistivity is lower than that of the organic solvent and the conventional stabilizer.
  • the level is not a problem for general insulation, it is preferable to use them according to the application.
  • thermal cationic polymerizable composition is not particularly limited, but it is preferably used as a thermosetting liquid resin composition.
  • the thermal cationic polymerizable composition of the present invention can be cured at a relatively low temperature and has good adhesion to resins, metals, etc., so it is suitable as an adhesive or coating agent that makes use of such properties.
  • the adhesive may be any type that can bond multiple members, and includes various types of adhesives.
  • a composition containing conductive particles can be used as a conductive paste or an anisotropic conductive film (ACF).
  • ACF anisotropic conductive film
  • the coating agent may be any type that can cover the surface of a member, and includes various types of coating agents.
  • the thermal cationic polymerizable composition of the present invention can be used as a sealant, insulating material, resist material, etc.
  • the thermal cationic polymerizable composition of the present invention is also useful as a fiber reinforced plastic (FRP) or nanoimprint material. Since the thermal cationic polymerizable composition of the present invention can be cured at a relatively low temperature, thermal damage to electronic components, semiconductors, etc. can be suppressed. Furthermore, it is possible to reduce volatile organic solvents, so that it is also suitable for applications such as electronic components and semiconductors.
  • the thermally cationic polymerizable composition of the present invention which contains the new stabilizer (C)
  • the new stabilizer (C) has a longer pot life and can suppress an increase in the heat generation initiation temperature compared to conventional stabilizers.
  • the use of the compound represented by the formula (2) as a stabilizer for a thermally cationic polymerizable composition is itself a new thing. Therefore, the problem of the present invention is also solved by providing a stabilizer (C) for a thermally cationic polymerizable composition represented by the formula (2).
  • the present invention provides a novel and useful stabilizer.
  • Celloxide 2021P water, propylene carbonate (PC), methyl isobutyl ketone (MIBK), and propylene glycol monomethyl ether acetate (PGMAc) were used.
  • the solubility of the stabilizer (2a) was 100 [g/100 g-solv.] or more in water, PC, MIBK and PGMAc, and 25 [g/100 g-solv.] in "Celloxide 2021P".
  • S[g/100g-solv. ] 1/(Ws/100)
  • thermosetting 5.0 mg of the prepared thermal cationic polymerizable composition (thermosetting composition) was weighed out, and the temperature was raised from 30°C to 310°C at 10°C/min in a nitrogen gas flow of 40 mL/min using a Hitachi High-Technologies Corporation differential scanning calorimeter "X-DSC7000", to obtain a DSC curve.
  • the obtained DSC curve is shown in Figure 1.
  • heat generation was observed in the range of about 70 to about 250°C, and three heat generation peaks were observed. Of these, the first (lowest temperature) heat generation peak was determined as the first heat generation peak.
  • Example 2 In a 200 mL four-neck flask, 3.51 g (25 mmol) of 4-(methylthio)phenol, 3.85 g (25 mmol) of diethyl sulfate, and 25 mL of acetonitrile were placed and stirred at 40° C. for 24 hours. The resulting reaction solution was concentrated to obtain an intermediate, 4-hydroxyphenylmethylethylsulfonium ethyl sulfate. 4.3 g (25 mmol) of sodium trifluoromethanesulfonate and 85 mL of ethanol were placed in this intermediate and stirred at 25° C. for 24 hours.
  • Example 3 In a 200 mL four-neck flask, 3.51 g (25 mmol) of 4-(methylthio)phenol, 3.16 g (25 mmol) of benzyl chloride, and 25 mL of acetonitrile were placed and stirred at 40° C. for 24 hours. The resulting reaction solution was concentrated to obtain an intermediate, 4-hydroxyphenylmethylbenzylsulfonium chloride. Except for using this intermediate, the procedure was repeated in the same manner as in Example 2 to obtain 4-hydroxyphenylmethylbenzylsulfonium trifluoromethanesulfonate (formula (2c) below) as white crystals in a yield of 96%.
  • Example 5 0.2 mg of the stabilizer (2a) obtained in Example 1 was placed in a 30 mL screw tube, and 20 g of the cationically polymerizable compound "Celloxide 2021P" was added thereto, and the mixture was mixed and completely dissolved using a planetary centrifugal mixer "ARE-310". Subsequently, 20.0 mg of "San-Aid SI-B3A” (1a) was added as a polymerization initiator, and further mixed using the planetary centrifugal mixer to prepare a thermally cationically polymerizable composition that does not contain the solvent propylene carbonate. The obtained thermally cationically polymerizable composition was evaluated in the same manner as in Example 1, and the results are shown in Tables 1, 2, and FIG. 1.
  • Comparative Example 4 4-Hydroxyphenyldimethylsulfonium p-toluenesulfonate (formula (2h) below) was obtained in a yield of 89% in the same manner as in Comparative Example 2, except that 2.95 g of sodium methylsulfite was changed to 4.86 g of sodium p-toluenesulfonate.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une composition polymérisable par voie thermique et cationique qui contient un composé (A) polymérisable par voie cationique, un initiateur de polymérisation cationique (B), et un stabilisant (C) qui est représenté par la formule (2), 0,01 à 20 parties en masse de l'initiateur de polymérisation cationique (B) étant contenues par rapport à 100 parties en masse du composé (A) polymérisable par voie cationique, et 0,1 à 50 parties en masse du stabilisant (C) étant contenues par rapport à 100 parties en masse de l'initiateur de polymérisation cationique (B). Dans la formule (2), R4, R5 et R6 représentent chacun indépendamment un groupe alkyle facultativement substitué contenant de 1 à 10 atomes de carbone, un groupe aryle facultativement substitué contenant de 6 à 15 atomes de carbone, ou un groupe aralkyle facultativement substitué contenant de 7 à 15 atomes de carbone. Par conséquent, la présente invention concerne une composition polymérisable par voie thermique et cationique qui possède une longue durée de vie en pot, tout en utilisant un initiateur de polymérisation cationique dont la température d'initiation de polymérisation est basse.
PCT/JP2024/035366 2023-10-04 2024-10-03 Composition polymérisable par voie thermique et cationique, son utilisation, procédé de polymérisation cationique l'utilisant, et stabilisant pour compositions polymérisables par voie thermique et cationique Pending WO2025075065A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005008847A (ja) * 2003-05-28 2005-01-13 Jsr Corp 硬化性樹脂組成物、保護膜および保護膜の形成方法
JP2008266570A (ja) * 2007-03-22 2008-11-06 Jsr Corp 熱硬化性樹脂組成物、保護膜および保護膜の形成方法
JP2016009698A (ja) * 2014-06-23 2016-01-18 Jsr株式会社 硬化性樹脂組成物、保護膜、液晶表示素子および固体撮像素子
JP2019214673A (ja) * 2018-06-13 2019-12-19 三洋化成工業株式会社 活性エネルギー線硬化性組成物及びその硬化物
WO2020149360A1 (fr) * 2019-01-18 2020-07-23 積水化学工業株式会社 Produit durci et element d'affichage electroluminescent organique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004217551A (ja) * 2003-01-14 2004-08-05 Sanshin Chem Ind Co Ltd スルホニウム化合物
JP4999043B2 (ja) * 2006-02-13 2012-08-15 株式会社Ａｄｅｋａ スルホニウム塩化合物、カチオン重合開始剤および熱硬化性組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005008847A (ja) * 2003-05-28 2005-01-13 Jsr Corp 硬化性樹脂組成物、保護膜および保護膜の形成方法
JP2008266570A (ja) * 2007-03-22 2008-11-06 Jsr Corp 熱硬化性樹脂組成物、保護膜および保護膜の形成方法
JP2016009698A (ja) * 2014-06-23 2016-01-18 Jsr株式会社 硬化性樹脂組成物、保護膜、液晶表示素子および固体撮像素子
JP2019214673A (ja) * 2018-06-13 2019-12-19 三洋化成工業株式会社 活性エネルギー線硬化性組成物及びその硬化物
WO2020149360A1 (fr) * 2019-01-18 2020-07-23 積水化学工業株式会社 Produit durci et element d'affichage electroluminescent organique

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