WO2020149362A1 - Produit durci et element d'affichage electroluminescent organique - Google Patents

Produit durci et element d'affichage electroluminescent organique Download PDF

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Publication number
WO2020149362A1
WO2020149362A1 PCT/JP2020/001259 JP2020001259W WO2020149362A1 WO 2020149362 A1 WO2020149362 A1 WO 2020149362A1 JP 2020001259 W JP2020001259 W JP 2020001259W WO 2020149362 A1 WO2020149362 A1 WO 2020149362A1
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WO
WIPO (PCT)
Prior art keywords
weight
parts
organic
resin composition
cured product
Prior art date
Application number
PCT/JP2020/001259
Other languages
English (en)
Japanese (ja)
Inventor
俊隆 吉武
穣 末▲崎▼
真理子 安部
Original Assignee
積水化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 積水化学工業株式会社 filed Critical 積水化学工業株式会社
Priority to KR1020217012036A priority Critical patent/KR20210116423A/ko
Priority to JP2020512073A priority patent/JPWO2020149362A1/ja
Publication of WO2020149362A1 publication Critical patent/WO2020149362A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • 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
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants

Definitions

  • the present invention relates to a cured product that can be used for a sealing wall formed around a laminate having an organic light emitting material layer to suppress deterioration of performance of an in-plane sealant for an organic EL display element.
  • the present invention also relates to an organic EL display device having the cured product.
  • a resin composition for organic EL display element encapsulation is applied to a non-alkali glass having a length of 200 mm, a width of 200 mm, and a thickness of 1 mm so as to have a thickness of 10 ⁇ m. Then, irradiation with ultraviolet rays having a wavelength of 365 nm and an integrated light amount of 3000 mJ/cm 2 and/or heating at 100° C. for 30 minutes is performed to obtain a cured product of the resin composition for organic EL display element encapsulation on non-alkali glass. Form. The alkali-free glass on which the cured product has been formed is immersed in 10 g of the resin composition 1, 2 or 3 at 20° C.
  • the preferable lower limit of the content of the polyolefin in the total 100 parts by weight of the polyolefin and the curable resin described below is 10 parts by weight, and the preferable upper limit is 80 parts by weight.
  • the content of the polyolefin is 10 parts by weight or more, the obtained resin composition for organic EL display element encapsulation becomes more excellent in the moisture permeability of the cured product.
  • the content of the polyolefin is 80 parts by weight or less, the obtained resin composition for organic EL display element encapsulation becomes more excellent in coating property and adhesiveness.
  • the more preferable lower limit of the content of the polyolefin is 20 parts by weight, and the more preferable upper limit thereof is 70 parts by weight.
  • Examples of the (meth)acrylic compound include isobornyl (meth)acrylate, adamantyl (meth)acrylate, methylcyclohexyl (meth)acrylate, norbornylmethyl (meth)acrylate, and dicyclopenta(meth)acrylate.
  • Nyl dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, cyclodecyl (meth)acrylate, 4-t-butylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, etc.
  • the solubility at 20° C. in the liquid resin composition 1 the solubility at 20° C.
  • the content of the tackifying resin is preferably 0.01 parts by weight and 100 parts by weight with respect to 100 parts by weight of the total of the polyolefin and the curable resin.
  • the more preferable lower limit of the content of the tackifying resin is 0.2 parts by weight, and the more preferable upper limit thereof is 20 parts by weight.
  • photoradical polymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthone compounds, and the like.
  • Specific examples of the photoradical polymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, 1,2-(dimethylamino).
  • sulfonium salt examples include triphenylsulfonium tetrafluoroborate and triphenylsulfonium hexafluoroantimonate.
  • the content of the polymerization initiator has a preferable lower limit of 0.05 parts by weight and a preferable upper limit of 10 parts by weight with respect to 100 parts by weight of the total of the polyolefin and the curable resin.
  • the content of the polymerization initiator is 0.05 parts by weight or more, the obtained resin composition for organic EL display element encapsulation has more excellent curability.
  • the content of the polymerization initiator is 10 parts by weight or less, the curing reaction of the obtained resin composition for organic EL display element encapsulation does not become too fast, the workability becomes excellent, and the cured product becomes more uniform. It can be anything.
  • the more preferable lower limit of the content of the polymerization initiator is 1 part by weight, and the more preferable upper limit thereof is 3 parts by weight.
  • Examples of the surface modifier include silicone-based, acrylic-based, and fluorine-based agents.
  • Examples of commercially available surface modifiers include, for example, a surface modifier manufactured by Big Chemie Japan, a surface modifier manufactured by Kusumoto Kasei, and a surface modifier manufactured by AGC Seimi Chemical. Can be mentioned.
  • Examples of the surface modifier manufactured by Big Chemie Japan include BYK-300, BYK-302, and BYK-331.
  • Examples of the surface modifier manufactured by Kusumoto Chemicals include UVX-272.
  • Examples of the surface modifier manufactured by AGC Seimi Chemical Co., Ltd. include Surflon S-611.
  • the resin composition for encapsulating an organic EL display element according to the present invention is, as necessary, a curing retarder, a reinforcing agent, a softening agent, a plasticizer, a viscosity modifier, and an ultraviolet absorbing agent within a range that does not impair the object of the present invention.
  • a curing retarder e.g., a curing retarder, a reinforcing agent, a softening agent, a plasticizer, a viscosity modifier, and an ultraviolet absorbing agent within a range that does not impair the object of the present invention.
  • Various known additives such as agents and antioxidants may be contained.
  • the organic EL display element encapsulating resin compositions obtained in Examples 1 to 5 and Comparative Examples 1 to 3 were cured by heating at 100° C. for 30 minutes.
  • the organic EL display element encapsulating resin compositions obtained in Examples 6 to 8 and Comparative Examples 4 to 6 were cured by irradiating them with ultraviolet rays having a wavelength of 365 nm at 3000 mJ/cm 2 with a UV-LED irradiation device. ..
  • the alkali-free glass on which the cured product was formed was immersed in 10 g of the resin composition 1, 2, or 3 at 20° C. for 1 minute.
  • the alkali-free glass was taken out from the resin composition 1, 2, or 3 and immersed in 10 g of methanol at 20° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Theoretical Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un produit durci permettant de supprimer la détérioration des capacités d'un produit de scellement dans le plan pour un élément d'affichage électroluminescent organique, grâce à l'utilisation d'une paroi de scellement formée à la circonférence d'un produit stratifié possédant une couche de matériau luminescent organique. L'invention concerne également un élément d'affichage électroluminescent organique possédant ledit produit durci. Ce produit durci de composition de résine pour scellement d'un élément d'affichage électroluminescent organique contient une polyoléfine, une résine durcissable, et un initiateur de polymérisation et/ou un agent thermodurcissant. Ce produit durci se caractérise en ce que: le degré de solubilité à 20℃ par rapport à une composition (1) de résine liquide constituée de 70 parties en poids d'un composé époxy représenté par la formule générale (1), 30 parties en poids d'un composé oxétane représenté par la formule générale (2), 1,5 parties enpoids de diméthyl phényl (4-méthoxy benzyl) ammonium hexafluoroantimonate, et 0,2 partie en poids de benzylamine; le degré de solubilité à 20℃ par rapport à une composition (2) de résine liquide constituée de 70 parties en poids d'un composé époxy représenté par la formule générale (3), 30 parties en poids d'un composé oxétane représenté par la formule générale (2), 1 partie en poids de triphényl sulfonium trifluorométhane sulfonate, 0,5 partie en poids de 4-isopropyl-4'-méthyl diphényl iodium Tetrakis (pentafluorophényl) borate, et 0,2 partie en poids de benzylamine; et le degré de solubilité à 20℃ par rapport à une composition (3) de résine liquide constituée de 70 parties en poids d'un composé époxy représenté par la formule générale (3), 20 parties en poids d'un composé oxétane représenté par la formule générale (2), 10 parties en poids de diéthylène glycol diglycide éther, 1,5 parties en poids de diméthyl phényl (4- méthoxy benzyl) ammonium hexafluoroantimonate, et 0,2 partie en poids de benzylamine, sont tous les trois inférieurs ou égaux à 1% en poids.
PCT/JP2020/001259 2019-01-18 2020-01-16 Produit durci et element d'affichage electroluminescent organique WO2020149362A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020217012036A KR20210116423A (ko) 2019-01-18 2020-01-16 경화물 및 유기 el 표시 소자
JP2020512073A JPWO2020149362A1 (ja) 2019-01-18 2020-01-16 硬化物及び有機ｅｌ表示素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019007083 2019-01-18
JP2019-007083 2019-01-18

Publications (1)

Publication Number Publication Date
WO2020149362A1 true WO2020149362A1 (fr) 2020-07-23

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PCT/JP2020/001259 WO2020149362A1 (fr) 2019-01-18 2020-01-16 Produit durci et element d'affichage electroluminescent organique

Country Status (3)

Country Link
JP (1) JPWO2020149362A1 (fr)
KR (1) KR20210116423A (fr)
WO (1) WO2020149362A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014017524A1 (fr) * 2012-07-26 2014-01-30 電気化学工業株式会社 Composition de résine
JP2016066471A (ja) * 2014-09-24 2016-04-28 積水化学工業株式会社 有機エレクトロルミネッセンス表示素子封止用樹脂組成物、有機エレクトロルミネッセンス表示素子封止用樹脂シート、及び、有機エレクトロルミネッセンス表示素子
JP2018513891A (ja) * 2015-03-24 2018-05-31 エルジー・ケム・リミテッド 接着剤組成物
JP2018513889A (ja) * 2015-03-24 2018-05-31 エルジー・ケム・リミテッド 接着剤組成物
WO2018151002A1 (fr) * 2017-02-14 2018-08-23 積水化学工業株式会社 Composition de résine photodurcissable, agent d'étanchéité pour éléments d'affichage électroluminescents organiques, élément d'affichage électroluminescent organique, agent d'étanchéité pour dispositifs à points quantiques et dispositif à points quantiques

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6098091B2 (ja) 2012-09-26 2017-03-22 凸版印刷株式会社 有機エレクトロルミネッセンスパネルの製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014017524A1 (fr) * 2012-07-26 2014-01-30 電気化学工業株式会社 Composition de résine
JP2016066471A (ja) * 2014-09-24 2016-04-28 積水化学工業株式会社 有機エレクトロルミネッセンス表示素子封止用樹脂組成物、有機エレクトロルミネッセンス表示素子封止用樹脂シート、及び、有機エレクトロルミネッセンス表示素子
JP2018513891A (ja) * 2015-03-24 2018-05-31 エルジー・ケム・リミテッド 接着剤組成物
JP2018513889A (ja) * 2015-03-24 2018-05-31 エルジー・ケム・リミテッド 接着剤組成物
WO2018151002A1 (fr) * 2017-02-14 2018-08-23 積水化学工業株式会社 Composition de résine photodurcissable, agent d'étanchéité pour éléments d'affichage électroluminescents organiques, élément d'affichage électroluminescent organique, agent d'étanchéité pour dispositifs à points quantiques et dispositif à points quantiques

Also Published As

Publication number Publication date
KR20210116423A (ko) 2021-09-27
JPWO2020149362A1 (ja) 2021-11-25

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