WO2018074505A1 - 有機el表示素子用封止剤 - Google Patents

有機el表示素子用封止剤 Download PDF

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Publication number
WO2018074505A1
WO2018074505A1 PCT/JP2017/037654 JP2017037654W WO2018074505A1 WO 2018074505 A1 WO2018074505 A1 WO 2018074505A1 JP 2017037654 W JP2017037654 W JP 2017037654W WO 2018074505 A1 WO2018074505 A1 WO 2018074505A1
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WO
WIPO (PCT)
Prior art keywords
organic
display elements
sealing agent
meth
examples
Prior art date
Application number
PCT/JP2017/037654
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English (en)
French (fr)
Japanese (ja)
Inventor
山本 拓也
信烈 梁
範久 赤松
七里 徳重
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.)
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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 KR1020227014108A priority Critical patent/KR20220061267A/ko
Priority to KR1020187028712A priority patent/KR102392860B1/ko
Priority to JP2017556250A priority patent/JP6404494B2/ja
Priority to CN201780023757.4A priority patent/CN109076661B/zh
Publication of WO2018074505A1 publication Critical patent/WO2018074505A1/ja

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Classifications

    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/02Details
    • H05B33/04Sealing arrangements, e.g. against humidity
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80Constructional details
    • H10K59/87Passivation; Containers; Encapsulations
    • H10K59/873Encapsulations

Definitions

  • the present invention relates to an encapsulant for an organic EL display element that can be easily applied by an ink jet method, can provide an organic EL display element that is excellent in low outgassing properties and excellent in reliability.
  • organic electroluminescence (hereinafter, also referred to as “organic EL”) display element has a laminated structure in which an organic light emitting material layer is sandwiched between a pair of electrodes facing each other, and the organic light emitting material layer is formed from one electrode on the organic light emitting material layer.
  • organic EL organic electroluminescence
  • the organic EL display element performs self-emission, it has better visibility than a liquid crystal display element that requires a backlight, can be reduced in thickness, and can be driven by a DC low voltage. Has the advantage.
  • the upper limit of the volatility after 4 days at 25 ° C. is 1%.
  • the volatilization rate after 4 days at 25 ° C. is 1% or less, the obtained sealing agent for organic EL display elements has excellent low outgassing properties, and the obtained organic EL display elements have excellent reliability. It will be a thing.
  • a preferable upper limit of the volatilization rate after 4 days at 25 ° C. is 0.5%, and a more preferable upper limit is 0.1%.
  • the volatilization rate at 25 ° C. is most preferably 0%.
  • the viscosity, the surface tension, and the volatility after 4 days at 25 ° C. are selected and contained for the polymerizable compound, the polymerization initiator, and other components that may be contained, which will be described later.
  • the ratio By adjusting the ratio, the above-mentioned range can be obtained.
  • the volatilization rate after 4 days at 25 ° C. should be within the above range by adjusting the boiling point and molecular weight of the polymerizable compound described later, or using a hydrogen bonding component as the polymerizable compound. Can do.
  • Examples of the hydrogen bonding component include an —OH group, —NH 2 group, —NHR group (R represents an aromatic, aliphatic hydrocarbon, or a derivative thereof), —COOH group, —CONH 2 group. And polymerizable compounds having a functional group such as —NHOH group.
  • Examples of the hydrogen bonding component include polymerization having residues such as —R—O— bond, —NHCO— bond, —NH— bond, —CONHCO— bond, —NH—NH— bond in the molecule. And other compounds. Among these, a polymerizable compound having at least one of —OH group and —RO— bond is preferable.
  • an epoxy compound an oxetane compound, a vinyl ether compound etc. are mentioned, for example.
  • alicyclic epoxy resins are preferred.
  • examples of commercially available alicyclic epoxy resins include Celoxide 2000, Celoxide 2021P, Celoxide 2081, Celoxide 3000, Celoxide 8000 (all manufactured by Daicel), and Sunsizer EPS (manufactured by Shin Nippon Rika Kogyo Co., Ltd.). ) And the like.
  • the monofunctional (meth) acrylic compound examples include 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and (meth) acrylic.
  • the preferred lower limit of the content of the monofunctional (meth) acrylic compound in 100 parts by weight of the polymerizable compound is 20 parts by weight, and the preferred upper limit is 80. Parts by weight.
  • the content of the monofunctional (meth) acrylic compound is within this range, the obtained sealing agent for organic EL display elements is excellent due to low outgassing properties and the like.
  • the minimum with more preferable content of the said monofunctional (meth) acryl compound is 30 weight part, and a more preferable upper limit is 60 weight part.
  • the anion moiety is BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is substituted with at least two fluorine or trifluoromethyl groups
  • a sulfonium salt, a phosphonium salt, an ammonium salt, and the like are preferable.
  • sulfonium salt examples include triphenylsulfonium tetrafluoroborate and triphenylsulfonium hexafluoroantimonate.
  • Examples of commercially available photo radical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, and Lucin TPO (both benzoin methyl ether, benzoin methyl ether) Examples include ethyl ether and benzoin isopropyl ether (both manufactured by Tokyo Chemical Industry Co., Ltd.).
  • the transmittance at 400 nm after irradiating the cured product with ultraviolet rays for 100 hours is preferably 85% or more at an optical path length of 20 ⁇ m.
  • the transmittance after irradiating the ultraviolet rays for 100 hours is 85% or more, the transparency is high, the loss of light emission is small, and the color reproducibility is excellent.
  • a more preferable lower limit of the transmittance after irradiation with the ultraviolet rays for 100 hours is 90%, and a more preferable lower limit is 95%.
  • the light source for irradiating the ultraviolet rays a conventionally known light source such as a xenon lamp or a carbon arc lamp can be used.
  • the sealing agent for organic EL display elements of the present invention may have a moisture content of less than 0.5% when the cured product is exposed to an environment of 85 ° C. and 85% RH for 24 hours. preferable.
  • the moisture content of the cured product is less than 0.5%, the effect of preventing the deterioration of the organic light emitting material layer due to moisture in the cured product is excellent, and the obtained organic EL display element is excellent in reliability. It becomes.
  • a more preferable upper limit of the moisture content of the cured product is 0.3%.
  • Examples of the method for measuring the moisture content include a method of obtaining by a Karl Fischer method in accordance with JIS K 7251, and a method of obtaining a weight increment after water absorption in accordance with JIS K 7209-2.
  • cured material used for the measurement of the said moisture content is a photocurable sealing agent, it can obtain by irradiating 3000 mJ / cm ⁇ 2 > of ultraviolet rays with a wavelength of 365 nm with a LED lamp to a sealing agent, for example. If it is a thermosetting sealing agent, it can obtain by heating at 80 degreeC for 1 hour, for example.
  • Examples of the light irradiation means to the organic EL display element sealant of the present invention include simultaneous irradiation of various light sources, sequential irradiation with a time difference, combined irradiation of simultaneous irradiation and sequential irradiation, and the like. Any irradiation means may be used.
  • an encapsulant for an organic EL display element that can be easily applied by an ink jet method, can obtain an organic EL display element that is excellent in low outgassing properties and excellent in reliability. Can do.
  • the crucible containing Alq 3 was heated to form an organic light emitting material layer having a thickness of 600 ⁇ at a deposition rate of 15 ⁇ / s. Thereafter, the substrate on which the hole transport layer and the organic light emitting material layer are formed is transferred to another vacuum vapor deposition apparatus, and 200 mg of lithium fluoride is added to a tungsten resistance heating boat in the vacuum vapor deposition apparatus, and an aluminum wire is added to another tungsten boat. 1.0 g was added.
  • the obtained sealant for organic EL display element was alkali-washed with an ink-jet discharge device (“NanoPrinter500” manufactured by Microjet Co., Ltd.) with a droplet volume of 30 picoliters (manufactured by Asahi Glass Co., Ltd.). , “AN100”).
  • the ink jet discharge performance was evaluated by assuming that “ ⁇ ” indicates that the liquid droplets were normally discharged from the ink jet nozzle and landed on the substrate, and “X” indicates that the liquid droplets were not normally discharged.
  • IJH-30 manufactured by IJT was used as an inkjet coating head, and inkjet coating was performed without heating (head temperature 25 ° C.).

Landscapes

  • Electroluminescent Light Sources (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
PCT/JP2017/037654 2016-10-19 2017-10-18 有機el表示素子用封止剤 WO2018074505A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1020227014108A KR20220061267A (ko) 2016-10-19 2017-10-18 유기 el 표시 소자용 봉지제
KR1020187028712A KR102392860B1 (ko) 2016-10-19 2017-10-18 유기 el 표시 소자용 봉지제
JP2017556250A JP6404494B2 (ja) 2016-10-19 2017-10-18 有機el表示素子用封止剤
CN201780023757.4A CN109076661B (zh) 2016-10-19 2017-10-18 有机el显示元件用密封剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016205486 2016-10-19
JP2016-205486 2016-10-19

Publications (1)

Publication Number Publication Date
WO2018074505A1 true WO2018074505A1 (ja) 2018-04-26

Family

ID=62019492

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/037654 WO2018074505A1 (ja) 2016-10-19 2017-10-18 有機el表示素子用封止剤

Country Status (5)

Country Link
JP (3) JP6404494B2 (ko)
KR (2) KR102392860B1 (ko)
CN (1) CN109076661B (ko)
TW (1) TW201819450A (ko)
WO (1) WO2018074505A1 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019203180A1 (ja) * 2018-04-20 2019-10-24 積水化学工業株式会社 有機el表示素子用封止剤

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WO2020031941A1 (ja) * 2018-08-10 2020-02-13 三井化学株式会社 封止剤
CN112912407A (zh) 2018-12-18 2021-06-04 积水化学工业株式会社 固化性树脂组合物、固化物及有机el显示元件
CN111785845A (zh) * 2019-04-04 2020-10-16 上海和辉光电有限公司 薄膜封装材料及其制造方法、薄膜封装结构和电子器件

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JP2001163831A (ja) * 1999-12-10 2001-06-19 Mitsubishi Rayon Co Ltd (メタ)アクリル酸エステルの製造方法
KR100683803B1 (ko) * 2005-12-13 2007-02-20 삼성에스디아이 주식회사 유기 발광 소자용 투명 흡습막 형성용 조성물의 제조 방법및 이로부터 제조된 조성물로부터 얻은 흡습막을 구비한유기 발광 소자
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019203180A1 (ja) * 2018-04-20 2019-10-24 積水化学工業株式会社 有機el表示素子用封止剤

Also Published As

Publication number Publication date
KR20190064531A (ko) 2019-06-10
CN109076661A (zh) 2018-12-21
KR102392860B1 (ko) 2022-04-29
KR20220061267A (ko) 2022-05-12
JP2022027781A (ja) 2022-02-14
TW201819450A (zh) 2018-06-01
JP2018195593A (ja) 2018-12-06
JPWO2018074505A1 (ja) 2018-10-25
JP6985228B2 (ja) 2021-12-22
CN109076661B (zh) 2021-11-12
JP6404494B2 (ja) 2018-10-10

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