WO2012132126A1 - 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法および電子注入輸送層用塗工液 - Google Patents

有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法および電子注入輸送層用塗工液 Download PDF

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Publication number
WO2012132126A1
WO2012132126A1 PCT/JP2011/078793 JP2011078793W WO2012132126A1 WO 2012132126 A1 WO2012132126 A1 WO 2012132126A1 JP 2011078793 W JP2011078793 W JP 2011078793W WO 2012132126 A1 WO2012132126 A1 WO 2012132126A1
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WO
WIPO (PCT)
Prior art keywords
organic
layer
metal
transporting layer
electron
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Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2011/078793
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English (en)
French (fr)
Japanese (ja)
Inventor
栄志 乙木
滋弘 上野
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dai Nippon Printing Co Ltd
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Dai Nippon Printing Co Ltd
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 Dai Nippon Printing Co Ltd filed Critical Dai Nippon Printing Co Ltd
Priority to EP11861994.9A priority Critical patent/EP2693506B1/en
Priority to US14/008,243 priority patent/US8969862B2/en
Priority to KR1020137027726A priority patent/KR20140015486A/ko
Priority to CN201180069665.2A priority patent/CN103460427B/zh
Publication of WO2012132126A1 publication Critical patent/WO2012132126A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/166—Electron transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes

Definitions

  • Patent Documents 2 and 3 it is described that an electron injection layer is formed by a coating method using a nonionic organometallic complex, a metal phthalocyanine, or an organometallic complex compound. There is no disclosure about its use. In any of Patent Documents 1 to 5, the relationship between the crystalline / amorphous state of the organic layer and device characteristics has not been studied.
  • the electron injecting and transporting layer may further contain an electron transporting organic compound.
  • the electron injecting and transporting layer contains an organic boron compound and an organic compound, a sufficient carrier balance can be maintained even if the thickness of the electron injecting and transporting layer is increased, so that a sufficient film thickness can be secured. Thus, it is easy to form a uniform film, and the film strength can be increased.
  • the driving voltage can be reduced by using an electron-transporting organic compound.
  • an organic compound having a hole blocking property in addition to the electron transporting property is added to the electron injecting and transporting layer, the charge recombination probability is improved, and the light emission efficiency can be improved.
  • the present invention also provides an anode, a light emitting layer formed on the anode, an electron injecting and transporting layer containing an organic boron compound formed on the light emitting layer, and a cathode formed on the electron injecting and transporting layer. And an electron injection transport layer forming step of forming an electron injection transport layer by applying a coating solution for an electron injection transport layer containing an organic boron compound and a solvent. Provided is a method for producing a characteristic organic EL element.
  • Anode used in the present invention may or may not have optical transparency, and is appropriately selected according to the light extraction surface. When light is extracted from the anode side, the anode becomes a transparent electrode.
  • Cathode The cathode used in the present invention may or may not have optical transparency, and is appropriately selected according to the light extraction surface. When light is extracted from the cathode side, the cathode becomes a transparent electrode.
  • the cathode preferably has a low resistance, and a metal material that is a conductive material is generally used, but an organic compound or an inorganic compound may be used.
  • a conductive material having a small work function is preferably used so that electrons can be easily injected.
  • metals such as Li, Ca, Mg, Al and In, Mg alloys such as MgAg, Al alloys such as AlLi, AlCa and AlMg, alkali metals and alkaline earths such as Li, Cs, Ba, Sr and Ca
  • An alloy such as a metal alloy can be used.
  • metals such as Au, Ag, Pd, Ni, and Cu can also be used.
  • the cathode film forming method and patterning method can be the same as the anode film forming method and patterning method.
  • the cathode is formed by a wet process, an expensive facility is not required unlike the dry process, which is advantageous in terms of cost.
  • the wet process for example, a method of applying a conductive paste in which metal particles such as Au, Ag, Pd, Ni, Cu, etc.
  • the melting point of the low melting point metal is preferably 30 ° C. higher than the glass transition temperature of the organic layer such as the light emitting layer, the electron injecting and transporting layer, the hole injecting and transporting layer, specifically 70 ° C. or more and 160 ° C. or less. Is preferred. If the melting point of the low melting point metal is higher than 30 ° C. higher than the glass transition temperature of the organic layer, the organic layer may be seriously damaged. Further, in order to use the organic EL element stably even in a high temperature environment such as in a midsummer car, the lower limit of the melting point of the metal or alloy constituting the electrode is practically 70 ° C.
  • Liquid metal is in a liquid state at room temperature (as a guideline, 5 ° C to 45 ° C) and is sufficient at a relatively low temperature of about 50 ° C even at room temperature or even when heated. That shows good fluidity.
  • the melting point of the liquid metal is preferably 50 ° C. or less.
  • the liquid metal can be formed by a wet process under heating at normal temperature or low temperature, and an electrode having an arbitrary shape can be formed by a wet process regardless of a dry process such as a vapor deposition method.
  • the thickness of the hole injecting and transporting layer is not particularly limited as long as the hole injecting function and the hole transporting function are sufficiently exerted.
  • the hole injecting and transporting layer has a thickness within the range of 0.5 nm to 1000 nm, particularly 10 nm to It is preferable to be in the range of 500 nm.
  • the method for forming the hole injecting and transporting layer can be the same as the method for forming the light emitting layer.
  • a partition wall may be formed on the substrate.
  • the cathode can be formed in a pattern without using a metal mask or the like.
  • a general partition material in an organic EL element can be used.
  • a photo-curable resin such as a photosensitive polyimide resin or an acrylic resin, a thermosetting resin, an inorganic material, or the like.
  • the partition wall may be subjected in advance to a surface treatment that changes the surface energy (wetting property).
  • the organic boron compound is decomposed at the time of film formation as in the vapor deposition method, or an impurity such as a decomposition product of the organic boron compound.
  • a crystal film can be obtained without being mixed. The crystal film is presumed to have improved electron transport properties due to the high order of atoms and molecules.
  • migration of decomposition products to the light emitting layer occurs during driving of the organic EL element, which may affect the light emission characteristics of the element.
  • Example 6 An organic EL device was produced in the same manner as in Example 1 except that the cathode was formed as shown below.
  • a metal (alloy) having a composition of Bi—Pb—Sn (50%: 25%: 25%) was melted to form a cathode having a thickness of 30 ⁇ m.
  • the metal having the above composition was formed by heating with a hot plate at 103 ° C., which is 10 ° C. higher than the melting point of the metal alloy, and melting the metal on the electron injecting and transporting layer.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2011/078793 2011-03-31 2011-12-13 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法および電子注入輸送層用塗工液 Ceased WO2012132126A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP11861994.9A EP2693506B1 (en) 2011-03-31 2011-12-13 Organic electroluminescent element and method for manufacturing organic electroluminescent element
US14/008,243 US8969862B2 (en) 2011-03-31 2011-12-13 Organic electroluminescent element, method for manufacturing organic electroluminescent element, and coating liquid for electron injection and transport layer
KR1020137027726A KR20140015486A (ko) 2011-03-31 2011-12-13 유기 일렉트로루미네센스 소자, 유기 일렉트로루미네센스 소자의 제조 방법 및 전자 주입 수송층용 도공액
CN201180069665.2A CN103460427B (zh) 2011-03-31 2011-12-13 有机电致发光元件、有机电致发光元件的制造方法及电子注入输送层用涂布液

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-078362 2011-03-31
JP2011078362A JP5655666B2 (ja) 2011-03-31 2011-03-31 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法および電子注入輸送層用塗工液

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WO2012132126A1 true WO2012132126A1 (ja) 2012-10-04

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US (1) US8969862B2 (enExample)
EP (1) EP2693506B1 (enExample)
JP (1) JP5655666B2 (enExample)
KR (1) KR20140015486A (enExample)
WO (1) WO2012132126A1 (enExample)

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WO2020158566A1 (ja) 2019-01-31 2020-08-06 大日本印刷株式会社 蒸着マスク群、電子デバイスの製造方法及び電子デバイス
EP4020585A1 (en) 2020-12-28 2022-06-29 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
EP4020584A1 (en) 2020-12-28 2022-06-29 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
EP4106029A1 (en) 2021-06-14 2022-12-21 Dai Nippon Printing Co., Ltd. Mask group, method of manufacturing organic device and organic device
EP4109576A2 (en) 2021-06-21 2022-12-28 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
EP4113621A1 (en) 2021-07-01 2023-01-04 Dai Nippon Printing Co., Ltd. Organic device and manufacturing method for organic device
US11793014B2 (en) 2020-06-03 2023-10-17 Dai Nippon Printing Co., Ltd. Electronic device, manufacturing method for electronic device, and deposition mask group

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JPWO2015152148A1 (ja) * 2014-03-31 2017-04-13 住友化学株式会社 有機エレクトロルミネッセンス素子
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US11649539B2 (en) 2019-01-31 2023-05-16 Dai Nippon Printing Co., Ltd. Deposition mask group, manufacturing method of electronic device, and electronic device
US11793014B2 (en) 2020-06-03 2023-10-17 Dai Nippon Printing Co., Ltd. Electronic device, manufacturing method for electronic device, and deposition mask group
EP4020584A1 (en) 2020-12-28 2022-06-29 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
EP4020585A1 (en) 2020-12-28 2022-06-29 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
US12219790B2 (en) 2020-12-28 2025-02-04 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
US12239006B2 (en) 2020-12-28 2025-02-25 Dai Nippon Printing Co., Ltd. Organic device having a first display area, and a second display area including a second electrode surrounding each of first and second adjacent transmission areas
EP4106029A1 (en) 2021-06-14 2022-12-21 Dai Nippon Printing Co., Ltd. Mask group, method of manufacturing organic device and organic device
US12410507B2 (en) 2021-06-14 2025-09-09 Dai Nippon Printing Co., Ltd. Mask group, method of manufacturing organic device and organic device
EP4109576A2 (en) 2021-06-21 2022-12-28 Dai Nippon Printing Co., Ltd. Organic device, group of masks, mask, and manufacturing method for organic device
EP4113621A1 (en) 2021-07-01 2023-01-04 Dai Nippon Printing Co., Ltd. Organic device and manufacturing method for organic device
US12453242B2 (en) 2021-07-01 2025-10-21 Dai Nippon Printing Co., Ltd. Organic device and manufacturing method for organic device

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JP2012212813A (ja) 2012-11-01
JP5655666B2 (ja) 2015-01-21
EP2693506B1 (en) 2019-02-27
KR20140015486A (ko) 2014-02-06
CN103460427A (zh) 2013-12-18
EP2693506A1 (en) 2014-02-05
US20140008638A1 (en) 2014-01-09
EP2693506A4 (en) 2014-11-19

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